Stabilizer mixtures

Info

Publication number: 20050131115
Type: Application
Filed: Feb 4, 2005
Publication Date: Jun 16, 2005
Inventor: Francois Gugumus (Allschwil)
Application Number: 11/051,455

Abstract

A stabilizer mixture containing the components (A), (B) and (C) wherein component (A) is for example a compound of the formula (A-1) wherein A1 is hydrogen or C1-C4alkyl, A2 is a direct bond or C1-C10alkylene, and n1 is a number from 2 to 50; component (B) is a low molecular weight sterically hindered amine compound containing a group of the formula (I) or (II); and component (C) is a high molecular weight sterically hindered amine compound containing a group of the formula (I); with the proviso that components (A), (B) and (C) are different.

Description

Description

The present invention relates to a stabilizer mixture containing a specific sterically hindered amine ester or amide, a low molecular weight sterically hindered amine and a high molecular weight sterically hindered amine.

Stabilizer mixtures containing blends of sterically hindered amines are for example described in U.S. Pat. No. 4,692,468, U.S. Pat. No. 4,863,981, U.S. Pat. No. 5,719,217, U.S. Pat. No. 5,919,399, U.S. Pat. No. 5,965,643, U.S. Pat. No. 5,980,783, U.S. Pat. No. 6,015,849 and U.S. Pat. No. 6,020,406.

The present Invention relates to a stabilizer mixture containing the components (A), (B) and (C) wherein component (A) is a compound of the formula (A-1)
wherein

A₁is hydrogen or C₁-C₄alkyl,
A₂is a direct bond or C₁-C₁₀alkylene, and
n₁is a number from 2 to 50;
at least one compound of the formulae (A-2-a) and (A-2-b)
wherein n₂and n₂* are a number from 2 to 50;
a compound of the formula (A-3)
wherein
A₃and A₄independently of one another are hydrogen or C₁-C₈alkyl, or A₃and A₄together form a C₂-C₁₄alkylene group, and
the variables n₃independently of one another are a number from 1 to 50; or
a compound of the formula (AA)
wherein
n₄is a number from 2 to 50,
A₅is hydrogen or C₁-C₄alkyl,
the radicals A₆and A₇independently of one another are C₁-C₄alkyl or a group of the formula (a-I)
wherein A₈is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl,
with the proviso that at least 50% of the radicals A₇are a group of the formula (a-I);
component (B) is a low molecular weight sterically hindered amine compound containing a group of the formula (I) or (II); and
component (C) is a high molecular weight sterically hindered amine compound containing a group of the formula (I);
with the proviso that components (A), (B) and (C) are different.

Preferably the compounds of component (B) have a molecular weight up to 1,000 g/mol, for example 155 to 800 g/mol or 155 to 1,000 g/mol or 300 to 800 g/mol or 300 to 1,000 g/mol.

Preferred high molecular weight sterically hindered amine compounds (component (C)) are those having a molecular weight of more than 1,000 g/mol, preferably from more than 1,000 up to 100,000 g/mol, e.g. up to 50,000 g/mol or up to 20,000 g/mol. A molecular weight of 1,500 to 15,000 g/mol or 1,500 to 5,000 g/mol is especially preferred. A preferred molecular weight of component (B) is also from more than 800 up to 100,000 g/mol, e.g. up to 50,000 g/mol or up to 20,000 g/mol. A molecular weight of more than 800 up to 15,000 g/mol or more than 800 up to 5,000 g/mol is also preferred.

The compounds of the formulae (A-2-a) and (A-2-b) can also be applied as a mixture wherein these two compounds may be present in a weight ratio of 1:20 to 20:1, preferably 1:10 to 10:1.

Component (B) is preferably
a compound of the formula (B-1)
in which

E₁is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl,
m₁is 1, 2 or 4,
if m₁is 1, E₂is C₁-C₂₅alkyl,
if m₁is 2, E₂is C₁-C₁₄alkylene or a group of the formula (b-I)
wherein
E₃is C₁-C₁₀alkyl or C₂-C₁₀alkenyl, E₄is C₁-C₁₀alkylene, and
E₅and E₆independently of one another are C₁-C₄alkyl, cyclohexyl or methylcyclohexyl, and
if m₁is 4, E₂is C₄-C₁₀alkanetetrayl;
a compound of the formula (B-2)
in which
two of the radicals E₇are —COO—(C₁-C₂₀alkyl), and
two of the radicals E₇are a group of the formula (b-II)
with E₈having one of the meanings of E₁;
a compound of the formula (B-3)
in which
E₉and E₁₀together form C₂-C₁₄alkylene,
E₁₁is hydrogen or a group -Z₁-COO-Z₂,
Z₁is C₂-C₁₄alkylene, and
Z₂is C₁-C₂₄alkyl, and
E₁₂has one of the meanings of E₁;
a compound of the formula (B-4)
wherein
the radicals E₁₃independently of one another have one of the meanings of E₁,
the radicals E₁₄independently of one another are hydrogen or C₁-C₁₂alkyl, and
E₁₅is C₁-C₁₀alkylene or C₃-C₁₀alkylidene;
a compound of the formula (B-5)
wherein
the radicals E₁₆independently of one another have one of the meanings of E₁;
a compound of the formula (B-6)
in which
E₁₇is C₁-C₂₄alkyl, and
E₁₈has one of the meanings of E₁;
a compound of the formula (B-7)
in which
E₁₉, E₂₀and E₂₁independently of one another are a group of the formula (b-III)
wherein E₂₂has one of the meanings of E₁;
a compound of the formula (B-8)
wherein
the radicals E₂₃independently of one another have one of the meanings of E₁, and E₂₄is hydrogen, C₁-C₁₂alkyl or C₁-C₁₂alkoxy;
a compound of the formula (B-9)
wherein
m₂is 1, 2 or 3,
E₂₅has one of the meanings of E₁, and
when m₂is 1, E₂₆is a group
when m₂is 2, E₂₆is C₂-C₂₂alkylene, and
when m₂is 3, E₂₆is a group of the formula (b-IV)
wherein the radicals E₂₇independently of one another are C₂-C₁₂alkylene, and the radicals E₂₈independently of one another are C₁-C₁₂alkyl or C₅-C₁₂cycloalkyl; or
a compound of the formula (B-10)
wherein
the radicals E₂₉independently of one another have one of the meanings of E₁, and E₃₀is C₂-C₂₂alkylene, C₅-C₇cycloalkylene, C₁-C₄alkylenedi(C₅-C₇cycloalkylene), phenylene or phenylenedi(C₁-C₄alkylene).

Component (C) is preferably
a compound of the formula (C-1)
in which

R₁, R₃, R₄and R₅independently of one another are hydrogen, C₁-C₁₂alkyl, C₅-C₁₂cycloalkyl, C₁-C₄-alkyl-substituted C₅-C₁₂cycloalkyl, phenyl, phenyl which is substituted by —OH and/or C₁-C₁₀alkyl; C₇-C₉phenylalkyl, C₇-C₉phenylalkyl which is substituted on the phenyl radical by —OH and/or C₁-C₁₀alkyl; or a group of the formula (c-I)
R₂is C₂-C₁₈alkylene, C₅-C₇cycloalkylene or C₁-C₄alkylenedi(C₅-C₇cycloalkylene), or
the radicals R₁, R₂and R₃, together with the nitrogen atoms to which they are bonded, perform a 5- to 10-membered heterocyclic ring, or
R₄and R₅, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring,
R₆is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl, and
b₁is a number from 2 to 50,
with the proviso that at least one of the radicals R₁, R₃, R₄and R₅is a group of the formula (c-I);
a compound of the formula (C-2)
wherein
R₇and R₁₁independently of one another are hydrogen or C₁-C₁₂alkyl,
R₈, R₉and R₁₀independently of one another are C₂-C₁₀alkylene, and
X₁, X₂, X₃, X₄, X₅, X₆, X₇and X₈independently of one another are a group of the formula (c-II),
in which
R₁₂is hydrogen, C₁-C₁₂alkyl, C₅-C₁₂cycloalkyl, C₁-C₄alkyl-substituted C₅-C₁₂cycloalkyl, phenyl, —OH— and/or C₁-C₁₀alkyl-substituted phenyl, C₇-C₉phenylalkyl, C₇-C₉phenylalkyl which is substituted on the phenyl radical by —OH and/or C₁-C₁₀alkyl; or a group of the formula (c-I) as defined above, and
R₁₃has one of the meanings of R₆;
a compound of the formula (C-3)
in which
R₁₄is C₁-C₁₀alkyl, C₅-C₁₂cycloalkyl, C₁-C₄alkyl-substituted C₅-C₁₂cycloalkyl, phenyl or C₁-C₁₀alkyl-substituted phenyl,
R₁₅is C₃-C₁₀alkylene,
R₁₆has one of the meanings of R₆, and
b₂is a number from 2 to 50;
a compound of the formula (C-4)
in which
R₁₇and R₂₁independently of one another are a direct bond or a —N(X₉)—CO—X₁₀—CO—N(X₁₁)— group, where X₉and X₁₁independently of one another are hydrogen, C₁-C₈alkyl, C₅-C₁₂cycloalkyl, phenyl, C₇-C₉phenylalkyl or a group of the formula (c-I),
X₁₀is a direct bond or C₁-C₄alkylene,
R₁₈has one of the meanings of R₆,
R₁₉, R₂₀, R₂₃and R₂₄independently of one another are hydrogen, C₁-C₃₀alkyl, C₅-C₁₂cycloalkyl or phenyl,
R₂₂is hydrogen, C₁-C₃₀alkyl, C₅-C₁₂cycloalkyl, phenyl, C₇-C₉phenylalkyl or a group of the formula (c-I), and
b₃is a number from 1 to 50;
a compound of the formula (C-5)
in which
R₂₅, R₂₆, R₂₇, R₂₈and R₂₉independently of one another are a direct bond or C₁-C₁₀alkylene,
R₃₀has one of the meanings of R₆, and
b₄is a number from 1 to 50; or
a product (C-6) obtainable by reacting a product, obtained by reaction of a polyamine of the formula (C-6-1) with cyanuric chloride, with a compound of the formula (C-6-2)
H₂N—(CH₂)_b′₅—NH—(CH₂)_b″₅—NH—(CH₂)_b′″₅—NH₂ (C-6-1)
in which
b′₅, b″₅and b′″₅independently of one another are a number from 2 to 12,
R₃₁is hydrogen, C₁-C₁₂alkyl, C₅-C₁₂cycloalkyl, phenyl or C₇-C₉phenylalkyl, and
R₃₂has one of the meanings of R₆.

Examples of alkyl having up to 30 carbon atoms are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl and triacontyl. One of the preferred definitions of A₈, E₁, E₈, E₁₂, E₁₃, E₁₆, E₁₈, E₂₂, E₂₃, E₂₅, E₂₉, R₆, R₁₃, R₁₆, R₁₈, R₃₀and R₃₂is C₁-C₄alkyl, especially methyl. R₃₁is preferably butyl.

Examples of alkoxy having up to 18 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, decyloxy, dodecyloxy, tetradecyloxy, hexadecyloxy and octadecyloxy. One of the preferred meanings of E₁is octoxy. E₂₄is preferably C₁-C₄alkoxy and one of the preferred meanings of R₆is propoxy.

Examples of C₅-C₁₂cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and cyclododecyl. C₅-C₈Cycloalkyl, especially cyclohexyl, is preferred.

C₁-C₄Alkyl-substituted C₅-C₁₂cycloalkyl is for example methylcyclohexyl or dimethylcyclohexyl.

Examples of C₅-C₁₂cycloalkoxy are cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclodecyloxy and cyclododecyloxy. C₅-C₈Cycloalkoxy, in particular cyclopentoxy and cyclohexoxy, is preferred.

—OH— and/or C₁-C₁₀alkyl-substituted phenyl is for example methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl or 3,5-di-tert-butyl-4-hydroxyphenyl.

Examples of C₇-C₉phenylalkyl are benzyl and phenylethyl.

C₇-C₉Phenylalkyl which is substituted on the phenyl radical by —OH and/or by alkyl having up to 10 carbon atoms is for example methylbenzyl, dimethylbenzyl, trimethylbenzyl, tert-butylbenzyl or 3,5-di-tert-butyl-4-hydroxybenzyl.

Examples of alkenyl having up to 10 carbon atoms are allyl, 2-methallyl, butenyl, pentenyl and hexenyl. Allyl is preferred. The carbon atom in position 1 is preferably saturated.

Examples of acyl containing not more than 8 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl, acryloyl, methacryloyl and benzoyl. C₁-C₈Alkanoyl, C₃-C₈alkenyl and benzoyl are preferred. Acetyl and acryloyl are especially preferred.

Examples of alkylene having up to 22 carbon atoms are methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene and decamethylene.

An example of C₃-C₁₀alkylidene is the group

An example of C₄-C₁₀alkanetetrayl is 1,2,3,4-butanetetrayl.

An example of C₅-C₇cycloalkylene is cyclohexylene.

An example of C₁-C₄alkylenedi(C₅-C₇cycloalkylene) is methylenedicyclohexylene.

An example of phenylenedi(C₁-C₄alkylene) is methylene-phenylene-methylene or ethylene-phenylene-ethylene.

Where the radicals R₁, R₂and R₃, together with the nitrogen atoms to which they are attached, form a 5- to 10-membered heterocyclic ring, this ring is for example

A 6-membered heterocyclic ring is preferred.

Where the radicals R₄and R₅, together with the nitrogen atom to which they are attached, form a 5- to 10-membered heterocyclic ring, this ring is for example 1-pyrrolidyl, piperidino, morpholino, 1-piperazinyl, 4-methyl-1-piperazinyl, 1-hexahydroazepinyl, 5,5,7-trimethyl-1-homopiperazinyl or 4,5,5,7-tetramethyl-1-homopiperazinyl. Morpholino is particularly preferred.

One of the preferred definitions of R₁₉and R₂₃is phenyl.

R₂₆is preferably a direct bond.

n₁, n₂, n₂* and n₄are preferably a number from 2 to 25, in particular 2 to 20.

n₃is preferably a number from 1 to 25, in particular 1 to 20.

b₁and b₂are preferably a number from 2 to 25, in particular 2 to 20.

b₃and b₄are preferably a number from 1 to 25, in particluar 1 to 20.

b′₅and b′″₅are preferably 3 and b″₅is preferably 2.

The compounds described above as components (A), (B) and (C) are essentially known and commercially available. All of them can be prepared by known processes.

The preparation of the compounds of component (A) is disclosed for example in U.S. Pat. No. 4,233,412, U.S. Pat. No. 4,340,534, WO-A-98/51,690 and EP-A-1,803.

The preparation of the compounds of component (B) is disclosed for example in U.S. Pat. No. 5,679,733, U.S. Pat. No. 3,640,928, U.S. Pat. No. 4,198,334, U.S. Pat. No. 5,204,473, U.S. Pat. No. 4,619,958, U.S. Pat. No. 4,110,306, U.S. Pat. No. 4,110,334, U.S. Pat. No. 4,689,416, U.S. Pat. No. 4,408,051, SU-A-768,175 (Derwent 88-138,751/20), U.S. Pat. No. 5,049,604, U.S. Pat. No. 4,769,457, U.S. Pat. No. 4,356,307, U.S. Pat. No. 4,619,956, U.S. Pat. No. 5,182,390, GB-A-2,269,819, U.S. Pat. No. 4,292,240, U.S. Pat. No. 5,026,849, U.S. Pat. No. 5,071,981, U.S. Pat. No. 4,547,538 and U.S. Pat. No. 4,976,889.

The preparation of the compounds of component (C) is disclosed for example in U.S. Pat. No. 4,086,204, U.S. Pat. No. 6,046,304, U.S. Pat. No. 4,331,586, U.S. Pat. No. 4,108,829, U.S. Pat. No. 5,051,458, WO-A-94/12,544 (Derwent 94-177,274/22), DD-A-262,439 (Derwent 89-122,983/17), U.S. Pat. No. 4,857,595, U.S. Pat. No. 4,529,760 and U.S. Pat. No. 4,477,615 and CAS 136,504-96-6.

The product (C-6) can be prepared analogously to known processes, for example by reacting a polyamine of formula (C-6-1) with cyanuric chloride in a molar ratio of from 1:2 to 1:4 in the presence of anhydrous lithium carbonate, sodium carbonate or potassium carbonate in an organic solvent such as 1,2-dichloroethane, toluene, xylene, benzene, dioxane or tert-amyl alcohol at a temperature of from −20° C. to +10° C., preferably from −10° C. to +10° C., in particular from 0° C. to +10° C., for from 2 to 8 hours, followed by reaction of the resultant product with a 2,2,6,6-tetramethyl-4-piperidylamine of the formula (C-6-2). The molar ratio of the 2,2,6,6-tetramethyl-4-piperidylamine to polyamine of the formula (C-6-1) employed is for example from 4:1 to 8:1. The quantity of the 2,2,6,6-tetramethyl-4-piperidylamine can be added in one portion or in more than one portion at intervals of a few hours.

The molar ratio of polyamine of the formula (C-6-1) to cyanuric chloride to 2,2,6,6-tetramethyl-4-piperidylamine of the formula (C-6-2) is preferably from 1:3:5 to 1:3:6.

The following example indicates one way of preparing a preferred product (C-6-a).

EXAMPLE

23.6 g (0.128 mol) of cyanuric chloride, 7.43 g (0.0426 mol) of N,N′-bis[3-aminopropyl]ethylenediamine and 18 g (0.13 mol) of anhydrous potassium carbonate are reacted at 5° C. for 3 hours with stirring in 250 ml of 1,2-dichloroethane. The mixture is warmed at room temperature for a further 4 hours. 27.2 g (0.128 mol) of N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine are added and the resultant mixture is warmed at 60° C. for 2 hours. A further 18 g (0.13 mol) of anhydrous potassium carbonate are added and the mixture is warmed at 60° C. for a further 6 hours. The solvent is removed by distillation under a slight vacuum (200 mbar) and replaced by xylene. 18.2 g (0.085 mol) of N-(2,2,6,6-tetramethyl-4-piperidyl)butylamine and 5.2 g (0.13 mol) of ground sodium hydroxide are added, the mixture is heated at reflux for 2 hours and, for a further 12 hours, the water formed during the reaction is removed by azeotropic distillation. The mixture is filtered. The solution is washed with water and dried over Na₂SO₄. The solvent is evaporated and the residue is dried at 120-130° C. in vacuo (0.1 mbar). The desired product is obtained as a colourless resin.

In general, the product (C-6) can for example be represented by a compound of the formula (C-6-α), (C-6-β) or (C-6-γ). It can also be in the form of a mixture of these three compounds.

A preferred meaning of the formula (C-6-α) is

A preferred meaning of the formula (C-6-β) is

A preferred meaning of the formula (C-6-γ) is

In the above formulae (C-6-α) to (C-6-γ), b₅is preferably 2 to 20, in particular 2 to 10.

Component (A) is preferably TINUVIN 622 (RTM), HOSTAVIN N 30 (RTM) or FERRO AM 806 (RTM).

Component (B) is preferably DASTIB 845 (RTM), TINUVIN 770 (RTM), TINUVIN 765 (RTM), TINUVIN 144 (RTM), TINUVIN 123 (RTM), ADK STAB LA 52 (RTM), ADK STAB LA 57 (RTM), ADK STAB LA 62 (RTM), ADK STAB LA 67 (RTM), HOSTAVIN N 20 (RTM), HOSTAVIN N 24 (RTM), SANDUVOR 3050 (RTM), DIACETAM 5 (RTM), SUMISORB TM 61 (RTM), UVINUL 4049 (RTM), SANDUVOR PR 31 (RTM), GOODRITE UV 3034 (RTM), GOODRITE UV 3150 (RTM), GOODRITE UV 3159 (RTM), GOODRITE 3110 x 128 (RTM) or UVINUL 4050 H (RTM).

Component (C) is preferably CHIMASSORB 944 (RTM), CHIMASSORB 2020 (RTM), CYASORB UV 3346 (RTM), CYASORB UV 3529 (RTM), DASTIB 1082 (RTM), CHIMASSORB 119 (RTM), UVASIL 299 (RTM), UVASIL 125 (RTM), UVASIL 2000 (RTM), UVINUL 5050 H (RTM), LICHTSCHUTZSTOFF UV 31 (RTM), LUCHEM HA B 18 (RTM), ADK STAB LA 63 (RTM), ADK STAB LA 68 (RTM) or UVASORB HA 88 (RTM).

The meanings of the terminal groups which saturate the free valences in the compounds of the formulae (A-1), (A-2-a), (A-2-b), (A-4), (C-1), (C-3), (C-4), (C-5), (C-6-α), (C-6-β) and (C-6-γ) depend on the processes used for their preparation. The terminal groups can also be modified after the preparation of the compounds.

If the compounds of the formula (A-1) are prepared, for example, by reacting a compound of the formula
in which A₁is hydrogen or methyl, with a dicarboxylic acid diester of the formula Y—OOC-A₂-COO—Y, in which Y is, for example, methyl, ethyl or propyl, and A₂is as defined above, the terminal group bonded to the 2,2,6,6-tetramethyl-4-oxypiperidin-1-yl radical is hydrogen or —CO-A₂COO—Y, and the terminal group bonded to the diacyl radical is —O—Y or

In the compounds of the formula (A-2-a), the terminal group bonded to the nitrogen can be, for example, hydrogen and the terminal group bonded to the 2-hydroxypropylene radical can be, for example, a
group.

In the compounds of the formula (A-2-b), the terminal group bonded to the dimethylene radical can be, for example, —OH, and the terminal group bonded to the oxygen can be, for example, hydrogen. The terminal groups can also be polyether radicals.

In the compounds of the formula (A-4), the end group bonded to the —CH₂— residue can be, for example, hydrogen and the end group bonded to the —CH(CO₂A₇) residue can be, for example, —CH═CH—COOA₇.

If the compounds of the formula (C-1) are prepared by reacting a compound of the formula
in which X is, for example, halogen, in particular chlorine, and R₄and R₅are as defined above, with a compound of the formula
in which R₁, R₂and R₃are as defined above, the terminal group bonded to the diamino radical is hydrogen or
and the terminal group bonded to the triazine radical is X or

If X is halogen, it is advantageous to replace this, for example, by —OH or an amino group when the reaction is complete. Examples of amino groups which may be mentioned are pyrrolidin-1-yl, morpholino, —NH₂, —N(C₁-C₈)alkyl)₂and —NR(C₁-C₈alkyl), in which R is hydrogen or a group of the formula (c-I).

The compounds of the formula (C-1) also cover compounds of the formula
wherein R₁, R₂, R₃, R₄, R₅and b₁are as defined above and R₄* has one of the meanings of R₄and R₅* has one of the meanings of R₅.

One of the particularly preferred compounds of the formula (C-1) is

The preparation of this compound is described in Example 10 of U.S. Pat. No. 6,046,304.

In the compounds of the formula (C-3), the terminal group bonded to the silicon atom can be, for example, (R₁₄)₃Si—O—, and the terminal group bonded to the oxygen can be, for example, —Si(R₁₄)₃.

The compounds of the formula (C-3) can also be in the form of cyclic compounds if b₂is a number from 3 to 10, i.e. the free valences shown in the structural formula then form a direct bond.

In the compounds of the formula (C-4), the terminal group bonded to the 2,5-dioxopyrrolidine ring is, for example, hydrogen, and the terminal group bonded to the —C(R₂₃)(R₂₄)— radical is, for example,

In the compounds of the formula (C-5), the terminal group bonded to the carbonyl radical is, for example,
and the terminal group bonded to the oxygen radical is, for example,

In the compounds of the formulae (C-6-α), (C-6-β) and (C-6-γ), the terminal group bonded to the triazine radical is, for example, Cl or a
group, and the terminal group bonded to the amino radical is, for example, hydrogen or a
group.

A₈is preferably hydrogen, C₁-C₄alkyl, C₁-C₁₀alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.

E₁, E₈, E₁₂, E₁₃, E₁₆, E₁₈, E₂₂, E₂₃, E₂₅and E₂₉are preferably hydrogen, C₁-C₄alkyl, C₁-C₁₀alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.

R₆, R₁₃, R₁₆, R₁₈, R₃₀and R₃₂are preferably hydrogen, C₁-C₄alkyl, C₁-C₁₀alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.

A₈, E₁, E₈, E₁₂, E₁₃, E₁₆, E₁₈, E₂₂, E₂₃, E₂₅, E₂₉, R₆, R₁₃, R₁₆, R₁₈, R₃₀and R₃₂are in particular hydrogen or methyl and E₁and R₆additionally are C₁-C₈alkoxy.

According to a preferred embodiment,

A₁is hydrogen or methyl,
A₂is a direct bond or C₂-C₆alkylene, and
n₁is a number from 2 to 25;
n₂and n₂* are a number from 2 to 25;
A₃and A₄independently of one another are hydrogen or C₁-C₄alkyl, or A₃and A₄together form a C₉-C₁₃alkylene group, and
the variables n₃independently of one another are a number from 1 to 25;
n₄is a number from 2 to 25,
A₅and A₆independently of one another are C₁-C₄alkyl, and
A₇is C₁-C₄alkyl or a group of the formula (a-I)
with the proviso that at least 50% of the radicals A₇are a group of the formula (a-I).

According to a further preferred embodiment

m₁is 1, 2 or 4,
if m₁is 1, E₂is C₁₂-C₂₀alkyl,
if m₁is 2, E₂is C₂-C₁₀alkylene or a group of the formula (b-I)
E₃is C₁-C₄alkyl,
E₄is C₁-C₆alkylene, and
E₅and E₆independently of one another are C₁-C₄alkyl, and
if m₁is 4, E₂is C₄-C₈alkanetetrayl;
two of the radicals E₇are —COO—(C₁₀-C₁₅alkyl), and
two of the radicals E₇are a group of the formula (b-II);
E₉and E₁₀together form C₉-C₁₃alkylene,
E₁₁is hydrogen or a group -Z₁-COO-Z₂,
Z₁is C₂-C₆alkylene, and
Z₂is C₁₀-C₁₆alkyl;
E₁₄is hydrogen, and
E₁₅is C₂-C₆alkylene or C₃-C₅alkylidene;
E₁₇is C₁₀-C₁₄alkyl;
E₂₄is C₁-C₄alkoxy;
m₂is 1, 2 or 3,
when m₂is 1, E₂₆is a group
when m₂is 2, E₂₆is C₂-C₆alkylene, and
when m₂is 3, E₂₆is a group of the formula (b-IV)
the radicals E₂₇independently of one another are C₂-C₆alkylene, and
the radicals E₂₈independently of one another are C₁-C₄alkyl or C₅-C₈cycloalkyl; and
E₃₀is C₂-C₈alkylene.

According to another preferred embodiment

R₁and R₃independently of one another are a group of the formula (c-I),
R₂is C₂-C₈alkylene,
R₄and R₅independently of one another are hydrogen, C₁-C₁₂alkyl, C₅-C₈cycloalkyl or a group of the formula (c-I), or the radicals R₄and R₅, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring, and
b₁is a number from 2 to 25;
R₇and R₁₁independently of one another are hydrogen or C₁-C₄alkyl,
R₈, R₉and R₁₀independently of one another are C₂-C₄alkylene, and
X₁, X₂, X₃, X₄, X₅, X₆, X₇and X₈independently of one another are a group of the formula (c-II),
R₁₂is hydrogen, C₁-C₄alkyl, C₅-C₈cycloalkyl or a group of the formula (c-I);
R₁₄is C₁-C₄alkyl,
R₁₅is C₃-C₆alkylene, and
b₂is a number from 2 to 25;
R₁₇and R₂₁independently of one another are a direct bond or a group —N(X₉)—CO—X₁₀—CO—N(X₁₁)—,
X₉and X₁₁independently of one another are hydrogen or C₁-C₄alkyl,
X₁₀is a direct bond,
R₁₉and R₂₃are C₁-C₂₅alkyl or phenyl,
R₂₀and R₂₄are hydrogen or C₁-C₄alkyl,
R₂₂is C₁-C₂₅alkyl or a group of the formula (c-I), and
b₃is a number from 1 to 25;
R₂₅, R₂₆, R₂₇, R₂₈and R₂₉independently of one another are a direct bond or C₁-C₄alkylene, and
b₄is a number from 1 to 25;
b′₅, b″₅and b′″₅independently of one another are a number from 2 to 4, and
R₃₁is hydrogen, C₁-C₄alkyl, C₅-C₈cycloalkyl, phenyl or benzyl.

A particularly preferred embodiment of this invention relates to a stabilizer mixture wherein component (A) is a compound of the formula (A-1-a), (A-2-a), (A-2-b), (A-3-a) or (A-4-a);
wherein n₁is a number from 2 to 20;
wherein n₂and n₂* are a number from 2 to 20;
wherein the variables n₃independently of one another are a number from 1 to 20;
wherein n₄is a number from 2 to 20, and
at least 50% of the radicals A₇are a group of the formula (a-I)
wherein A₈is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl,
and the remaining radicals A₇are ethyl;
component (B) is a compound of the formula (B-1-a), (B-1-b), (B-1-c), (B-1-d), (B-2-a), (B-3-a), (B-3-b), (B-4-a), (B-4-b), (B-5), (B-6-a), (B-7), (B-8-a), (B-9-a), (B-9-b), (B-9-c) or (B-10-a);
wherein E₁is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl;
in which two of the radicals E₇are —COO—C₁₃H₂₇and
two of the radicals E₇are
and E₈has one of the meanings E₁;
wherein E₁₂has one of the meanings of E₁;
wherein E₁₃has one of the meanings of E₁;
wherein E₁₆has one of the meanings of E₁,
wherein E₁₈has one of the meanings of E₁;
in which E₁₉, E₂₀and E₂₁independently of one another are a group of the formula (b-III)
wherein E₂₂has one of the meanings of E₁;
wherein E₂₃has one of the meanings of E₁;
wherein E₂₅has one of the meanings of E₁;
wherein E₂₉has one of the meanings of E₁;
component (C) is a compound of the formula (C-1-a), (C-1-b), (C-1-c), (C-1-d), (C-2-a), (C-3-a), (C-4-a), (C-4-b), (C-4-c) or (C-5-a) or a product (C-6-a);
wherein b₁is a number from 2 to 20 and R₆is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl;
wherein R₁₃has one of the meanings of R₆,
wherein b₂is a number from 2 to 20 and R₁₆has one of the meanings of R₆;
wherein b₃is a number from 1 to 20 and R₁₈has one of the meanings of R₆;
wherein b₄is a number from 1 to 20 and R₃₀has one of the meanings of R₆;
a product (C-6-a) obtainable by reacting a product, obtained by reaction of a polyamine of the formula (C-6-1-a) with cyanuric chloride, with a compound of the formula (C-6-2-a)
H₂N—(CH₂)₃—NH—(CH₂)₂—NH—(CH₂)₃—NH₂ (C-2-1-a)
in which R₃₂has one of the meanings of R₆.

A particularly preferred embodiment of this invention also relates to a stabilizer mixture wherein component (A) is a compound of the formula (A-1-a) wherein n, is a number from 2 to 20, or a compound of the formula (A-2-a) or (A-2-b) wherein n₂and n₂* are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E, is hydrogen and component (C) is a compound of the formula (C-1-a) wherein b, is a number from 2 to 20 and RB is hydrogen, or a compound of the formula (C-1-b) wherein R₆is hydrogen or propoxy and b, is a number from 2 to 20, or a compound of the formula (C-1 d) wherein R₆is hydrogen or methyl and b₁is a number from 2 to 20, or a compound of the formula (C-2-a) wherein R₁₃is methyl, or a compound of the formula (C-3-a) wherein R₁₆is hydrogen and b₂is a number from 2 to 20, or a compound of the formula (C-4-a) wherein R₁₈is hydrogen and b₃is a number from 1 to 20, or a product (C-6-a).

A further particularly preferred embodiment of this invention relates to a stabilizer mixture wherein component (A) is a compound of the formula (A-1-a) wherein n₁is a number from 2 to 20, or a compound of the formula (A-2-a) or (A-2-b) wherein n₂and n₂* are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E₁is hydrogen and component (C) is a compound of the formula (C-1-a) wherein b₁is a number from 2 to 20 and Re is hydrogen.

Examples of stabilizer mixtures according to the present invention are the following combinations of commercial products:

1. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+TINUVIN 770 (RTM)
2. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+TINUVIN 765 (RTM)
3. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+TINUVIN 144 (RTM)
4. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+TINUVIN 123 (RTM)
5. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
6. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+HOSTAVIN N 24 (RTM)
7. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+DIACETAM 5 (RTM)
8. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+ADK STAB LA 52 (RTM)
9. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+ADK STAB LA 57 (RTM)
10. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+ADK STAB LA 62 (RTM)
11. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+ADK STAB LA 67 (RTM)
12. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+GOODRITE UV 3034 (RTM)
13. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+GOODRITE UV 3150 (RTM)
14. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+GOODRITE UV 3159 (RTM)
15. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
16. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+UVINUL 4049 (RTM)
17. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
18. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
19. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+SUMISORB TM 61 (RTM)
20. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+SANDUVOR 3050 (RTM)
21. TINUVIN 622 (RTM)+CHIMASSORB 944 (RTM)+SANDUVOR PR-31 (RTM)
22. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+TINUVIN 770 (RTM)
23. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+TINUVIN 765 (RTM)
24. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+TINUVIN 144 (RTM)
25. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+TINUVIN 123 (RTM)
26. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
27. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+HOSTAVIN N 24 (RTM)
28. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+DIACETAM 5 (RTM)
29. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+ADK STAB LA 52 (RTM)
30. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+ADK STAB LA 57 (RTM)
31. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+ADK STAB LA 62 (RTM)
32. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+ADK STAB LA 67 (RTM)
33. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+GOODRITE UV 3034 (RTM)
34. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+GOODRITE UV 3150 (RTM)
35. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+GOODRITE UV 3159 (RTM)
36. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
37. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+UVINUL 4049 (RTM)
38. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
39. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
40. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+SUMISORB TM 61 (RTM)
41. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+SANDUVOR 3050 (RTM)
42. TINUVIN 622 (RTM)+CHIMASSORB 119 (RTM)+SANDUVOR PR-31 (RTM)
43. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+TINUVIN 770 (RTM)
44. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+TINUVIN 765 (RTM)
45. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+TINUVIN 144 (RTM)
46. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+TINUVIN 123 (RTM)
47. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
48. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+HOSTAVIN N 24 (RTM)
49. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+DIACETAM 5 (RTM)
50. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+ADK STAB LA 52 (RTM)
51. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+ADK STAB LA 57 (RTM)
52. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+ADK STAB LA 62 (RTM)
53. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+ADK STAB LA 67 (RTM)
54. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+GOODRITE UV 3034 (RTM)
55. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+GOODRITE UV 3150 (RTM)
56. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+GOODRITE UV 3159 (RTM)
57. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
58. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+UVINUL 4049 (RTM)
59. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
60. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
61. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+SUMISORB TM 61 (RTM)
62. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+SANDUVOR 3050 (RTM)
63. TINUVIN 622 (RTM)+CHIMASSORB 2020 (RTM)+SANDUVOR PR-31 (RTM)
64. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+TINUVIN 770 (RTM)
65. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+TINUVIN 765 (RTM)
66. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+TINUVIN 144 (RTM)
67. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+TINUVIN 123 (RTM)
68. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
69. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+HOSTAVIN N 24 (RTM)
70. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+DIACETAM 5 (RTM)
71. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+ADK STAB LA 52 (RTM)
72. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+ADK STAB LA 57 (RTM)
73. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+ADK STAB LA 62 (RTM)
74. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+ADK STAB LA 67 (RTM)
75. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+GOODRITE UV 3034 (RTM)
76. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+GOODRITE UV 3150 (RTM)
77. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+GOODRITE UV 3159 (RTM)
78. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
79. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+UVINUL 4049 (RTM)
80. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
81. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
82. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+SUMISORB TM 61 (RTM)
83. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+SANDUVOR 3050 (RTM)
84. TINUVIN 622 (RTM)+CYASORB UV 3346 (RTM)+SANDUVOR PR-31 (RTM)
85. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+TINUVIN 770 (RTM)
86. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+TINUVIN 765 (RTM)
87. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+TINUVIN 144 (RTM)
88. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+TINUVIN 123 (RTM)
89. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
90. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+HOSTAVIN N 24 (RTM)
91. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+DIACETAM 5 (RTM)
92. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+ADK STAB LA 52 (RTM)
93. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+ADK STAB LA 57 (RTM)
94. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+ADK STAB LA 62 (RTM)
95. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+ADK STAB LA 67 (RTM)
96. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+GOODRITE UV 3034 (RTM)
97. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+GOODRITE UV 3150 (RTM)
98. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+GOODRITE UV 3159 (RTM)
99. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
100. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+UVINUL 4049 (RTM)
101. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
102. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
103. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+SUMISORB TM 61 (RTM)
104. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+SANDUVOR 3050 (RTM)
105. TINUVIN 622 (RTM)+UVASIL 299 (RTM)+SANDUVOR PR-31 (RTM)
106. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+TINUVIN 770 (RTM)
107. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+TINUVIN 765 (RTM)
108. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+TINUVIN 144 (RTM)
109. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+TINUVIN 123 (RTM)
110. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
111. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+HOSTAVIN N 24 (RTM)
112. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+DIACETAM 5 (RTM)
113. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+ADK STAB LA 52 (RTM)
114. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+ADK STAB LA 57 (RTM)
115. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+ADK STAB LA 62 (RTM)
116. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+ADK STAB LA 67 (RTM)
117. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM), +GOODRITE UV 3034 (RTM)
118. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+GOODRITE UV 3150 (RTM)
119. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+GOODRITE UV 3159 (RTM)
120. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
121. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+UVINUL 4049 (RTM)
122. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
123. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
124. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+SUMISORB TM 61 (RTM)
125. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+SANDUVOR 3050 (RTM)
126. TINUVIN 622 (RTM)+UVASORB HA 88 (RTM)+SANDUVOR PR-31 (RTM)
127. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+TINUVIN 770 (RTM)
128. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+TINUVIN 765 (RTM)
129. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+TINUVIN 144 (RTM)
130. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+TINUVIN 123 (RTM)
131. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
132. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+HOSTAVIN N 24 (RTM)
133. TINUVIN 622 (RTM)+UVINUL 505 H (RTM)+DIACETAM 5 (RTM)
134. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+ADK STAB LA 52 (RTM)
135. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+ADK STAB LA 57 (RTM)
136. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+ADK STAB LA 62 (RTM)
137. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+ADK STAB LA 67 (RTM)
138. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+GOODRITE UV 3034 (RTM)
139. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+GOODRITE UV 3150 (RTM)
140. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+GOODRITE UV 3159 (RTM)
141. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
142. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+UVINUL 4049 (RTM)
143. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
144. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
145. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+SUMISORB TM 61 (RTM)
146. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+SANDUVOR 3050 (RTM)
147. TINUVIN 622 (RTM)+UVINUL 5050 H (RTM)+SANDUVOR PR-31 (RTM)
148. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+TINUVIN 770 (RTM)
149. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+TINUVIN 765 (RTM)
150. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+TINUVIN 144 (RTM)
151. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+TINUVIN 123 (RTM)
152. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
153. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+HOSTAVIN N 24 (RTM)
154. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+DIACETAM 5 (RTM)
155. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+ADK STAB LA 52 (RTM)
156. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+ADK STAB LA 57 (RTM)
157. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+ADK STAB LA 62 (RTM)
158. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+ADK STAB LA 67 (RTM)
159. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+GOODRITE UV 3034 (RTM)
160. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+GOODRITE UV 3150 (RTM)
161. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+GOODRITE UV 3159 (RTM)
162. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
163. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+UVINUL 4049 (RTM)
164. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
165. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
166. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+SUMISORB TM 61 (RTM)
167. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+SANDUVOR 3050 (RTM)
168. TINUVIN 622 (RTM)+LICHTSCHUTZSTOFF UV 31 (RTM)+SANDUVOR PR-31 (RTM)
169. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+TINUVIN 770 (RTM)
170. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+TINUVIN 765 (RTM)
171. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+TINUVIN 144 (RTM)
172. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+TINUVIN 123 (RTM)
173. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
174. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+HOSTAVIN N 24 (RTM)
175. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+DIACETAM 5 (RTM)
176. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+ADK STAB LA 52 (RTM)
177. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+ADK STAB LA 57 (RTM)
178. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+ADK STAB LA 62 (RTM)
179. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+ADK STAB LA 67 (RTM)
180. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+GOODRITE UV 3034 (RTM)
181. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+GOODRITE UV 3150 (RTM)
182. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+GOODRITE UV 3159 (RTM)
183. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
184. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+UVINUL 4049 (RTM)
185. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
186. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
187. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+SUMISORB TM 61 (RTM)
188. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+SANDUVOR 3050 (RTM)
189. TINUVIN 622 (RTM)+DASTIB 1082 (RTM)+SANDUVOR PR-31 (RTM)
190. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+TINUVIN 770 (RTM)
191. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+TINUVIN 765 (RTM)
192. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+TINUVIN 144 (RTM)
193. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+TINUVIN 123 (RTM)
194. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
195. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+HOSTAVIN N 24 (RTM)
196. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+DIACETAM 5 (RTM)
197. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+ADK STAB LA 52 (RTM)
198. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+ADK STAB LA 57 (RTM)
199. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+ADK STAB LA 62 (RTM)
200. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+ADK STAB LA 67 (RTM)
201. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+GOODRITE UV 3034 (RTM)
202. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+GOODRITE UV 3150 (RTM)
203. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+GOODRITE UV 3159 (RTM)
204. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
205. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+UVINUL 4049 (RTM)
206. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
207. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
208. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+SUMISORB TM 61 (RTM)
209. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+SANDUVOR 3050 (RTM)
210. TINUVIN 622 (RTM)+LUCHEM HA B 18 (RTM)+SANDUVOR PR-31 (RTM)
211. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+TINUVIN 770 (RTM)
212. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+TINUVIN 765 (RTM)
213. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+TINUVIN 144 (RTM)
214. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+TINUVIN 123 (RTM)
215. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
216. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+HOSTAVIN N 24 (RTM)
217. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+DIACETAM 5 (RTM)
218. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+ADK STAB LA 52 (RTM)
219. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+ADK STAB LA 57 (RTM)
220. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+ADK STAB LA 62 (RTM)
221. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+ADK STAB LA 67 (RTM)
222. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+GOODRITE UV 3034 (RTM)
223. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+GOODRITE UV 3150 (RTM)
224. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+GOODRITE UV 3159 (RTM)
225. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+compound of the formula (B-9-a) wherein E₂₆is hydrogen
226. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+UVINUL 4049 (RTM)
227. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
228. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
229. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+SUMISORB TM 61 (RTM)
230. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+SANDUVOR 3050 (RTM)
231. TINUVIN 622 (RTM)+ADK STAB LA 63 (RTM)+SANDUVOR PR-31 (RTM)
232. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+TINUVIN 770 (RTM)
233. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+TINUVIN 765 (RTM)
234. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+TINUVIN 144 (RTM)
235. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+TINUVIN 123 (RTM)
236. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
237. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+HOSTAVIN N 24 (RTM)
238. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+DIACETAM 5 (RTM)
239. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+ADK STAB LA 52 (RTM)
240. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+ADK STAB LA 57 (RTM)
241. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+ADK STAB LA 62 (RTM)
242. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+ADK STAB LA 67 (RTM)
243. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+GOODRITE UV 3034 (RTM)
244. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+GOODRITE UV 3150 (RTM)
245. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+GOODRITE UV 3159 (RTM)
246. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
247. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+UVINUL 4049 (RTM)
248. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
249. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
250. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+SUMISORB TM 61 (RTM)
251. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+SANDUVOR 3050 (RTM)
252. TINUVIN 622 (RTM)+ADK STAB LA 68 (RTM)+SANDUVOR PR-31 (RTM)
253. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+TINUVIN 770 (RTM)
254. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+TINUVIN 765 (RTM)
255. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+TINUVIN 144 (RTM)
256. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+TINUVIN 123 (RTM)
257. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+compound of the formula (B-3-a) wherein E₁₂is hydrogen
258. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+HOSTAVIN N 24 (RTM)
259. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+DIACETAM 5 (RTM)
260. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+ADK STAB LA 52 (RTM)
261. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+ADK STAB LA 57 (RTM)
262. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+ADK STAB LA 62 (RTM)
263. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+ADK STAB LA 67 (RTM)
264. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+GOODRITE UV 3034 (RTM)
265. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+GOODRITE UV 3150 (RTM)
266. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+GOODRITE UV 3159 (RTM)
267. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+compound of the formula (B-9-a) wherein E₂₅is hydrogen
268. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+UVINUL 4049 (RTM)
269. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+compound of the formula (B-10-a) wherein E₂₉is hydrogen
270. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+compound of the formula (B-1-a) wherein E₁is hydrogen
271. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+SUMISORB TM 61 (RTM)
272. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+SANDUVOR 3050 (RTM)
273. TINUVIN 622 (RTM)+CYASORB UV 3529 (RTM)+SANDUVOR PR-31 (RTM)

Further examples of stabilizer mixtures are those wherein in the above combinations 1 to 273 the commercial product TINUVIN 622 (RTM) is replaced by a compound of the formula (A-2-a) and/or (A-2-b)
wherein n₂and n₂* are a number from 2 to 20.

Additional examples of stabilizer mixtures are those wherein in the above combinations 1 to 273 the commercial product TINUVIN 622 (RTM) is replaced by a compound of the formula
wherein n₄is a number from 2 to 20, and
at least 50% of the radicals A₇are a group of the formula
and the remaining radicals A₇are ethyl.

Combinations of particular interest are number 1 and the corresponding combination wherein TINUVIN 622 (RTM) is replaced by a compound of the formula (A-2-a) and/or (A-2-b), number 85 and the corresponding combination wherein UVASIL 299 (RTM) is replaced by UVASIL 125 (RTM) or UVASIL 2000 (RTM), as well as number 22, 43, 64, 106, 127 and 253.

Further combinations of particular interest are numbers 1, 4, 5, 17 and 23.

The commercial product TINUVIN 622 (RTM) corresponds to the compound of the formula (A-1-a).

The commercial product TINUVIN 770 (RTM) corresponds to the compound of the formula (B-1-b) wherein E₁is hydrogen.

The commercial product TINUVIN 765 (RTM) corresponds to the compound of the formula (B-1-b) wherein E₁is methyl.

The commercial product TINUVIN 123 (RTM) corresponds to the compound of the formula (B-1-b) wherein E₁is octyloxy.

The commercial product TINUVIN 144 (RTM) corresponds to the compound of the formula (B-1-c) wherein E₁is methyl.

The commercial product ADK STAB LA 57 (RTM) corresponds to the compound of the formula (B-1-d) wherein E₁is hydrogen.

The commercial product ADK STAB LA 52 (RTM) corresponds to the compound of the formula (B-1-d) wherein E₁is methyl.

The commercial product ADK STAB LA 67 (RTM) corresponds to the compound of the formula (B-2-a) wherein E₈is hydrogen.

The commercial product ADK STAB LA 62 (RTM) corresponds to the compound of the formula (B-2-a) wherein E₁is methyl.

The commercial product HOSTAVIN N 24 (RTM) corresponds to the compound of the formula (B-3-b) wherein E₁₂is hydrogen.

The commercial product SANDUVOR 3050 (RTM) corresponds to the compound of the formula (B-3-b-1) shown below, wherein E₁₂is hydrogen.

The commercial product DIACETAM 5 (RTM) corresponds to the compound of the formula (B-4-a) wherein E₁₃is hydrogen.

The commercial product SUMISORB TM 61 corresponds to the compound of the formula (B-4-b) wherein E₁₃is hydrogen.

The commercial product UVINUL 4049 (RTM) corresponds to the compound of the formula (B-5) wherein E₁₆is hydrogen.

The commercial product SANDUVOR PR 31 (RTM) corresponds to the compound of the formula (B-8-a) wherein E₂₃is methyl.

The commercial product GOODRITE 3034 (RTM) corresponds to the compound of the formula (B-9-b) wherein E₂₅is hydrogen.

The commercial product GOODRITE 3150 (RTM) corresponds to the compound of the formula (B-9-c) wherein E₂₅is hydrogen.

The commercial product GOODRITE 3159 (RTM) corresponds to the compound of the formula (B-9-c) wherein E₂₅is methyl.

The commercial product CHIMASSORB 944 (RTM) corresponds to the compound of the formula (C-1-a) wherein R₆is hydrogen.

The commercial product CHIMASSORB 2020 (RTM) corresponds to the compound of the formula (C-1-b) wherein R₆is hydrogen.

The commercial product DASTIB 1082 (RTM) corresponds to the compound of the formula (C-1-c) wherein R₆is hydrogen.

The commercial product CYASORB UV 3346 (RTM) corresponds to the compound of the formula (C-1-d) wherein R₆is hydrogen.

The commercial product CYASORB UV 3529 (RTM) corresponds to the compound of the formula (C-1-d) wherein R₆is methyl.

The commercial product CHIMASSORB 119 (RTM) corresponds to the compound of the formula (C-2-a) wherein R₁₃is methyl.

The commercial product UVASIL 299 (RTM) corresponds to the compound of the formula (C-3-a) wherein R₁₆is hydrogen.

The commercial product UVINUL 5050 H (RTM) corresponds to the compound of the formula (C-4-a) wherein R₁₈is hydrogen.

The commercial product LICHTSCHUTZSTOFF UV 31 (RTM) corresponds to the compound of the formula (C₄-b) wherein R₁₈is hydrogen.

The commercial product LUCHEM HA B 18 (RTM) corresponds to the compound of the formula (C-4-c) wherein R₁₈is hydrogen.

The commercial product ADK STAB LA 68 (RTM) corresponds to the compound of the formula (C-5-a) wherein R₃₀is hydrogen.

The commercial product ADK STAB LA 63 (RTM) corresponds to the compound of the formula (C-5-a) wherein R₃₀is methyl.

The commercial product UVASORB HA 88 (RTM) corresponds to the product (C-6-a) wherein R₃₂is hydrogen.

The compound of the formula (B-3-b-1) has the following structure:

The stabilizer mixture according to this invention is suitable for stabilizing organic materials against degradation induced by light, heat or oxidation. Examples of such organic materials are the following:

1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for instance of cyclopentene or norbornene, polyethylene (which optionally can be crosslinked), for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HMW), high density and ultrahigh molecular weight polyethylene (HDPE-UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE).

Polyolefins, i.e. the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different, and especially by the following, methods:

- a) radical polymerisation (normally under high pressure and at elevated temperature).
- b) catalytic polymerisation using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and/or aryls that may be either π- or σ-coordinated.

These metal complexes may be in the free form or fixed on substrates, typically on activated magnesium chloride, titanium(III) chloride, alumina or silicon oxide. These catalysts may be soluble or insoluble in the polymerisation medium. The catalysts can be used by themselves in the polymerisation or further activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa of the Periodic Table. The activators may be modified conveniently with further ester, ether, amine or silyl ether groups. These catalyst systems are usually termed Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).

2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP/HDPE, PP/LDPE) and mixtures of different types of polyethylene (for example LDPE/HDPE).

3. Copolymers of monoolefins and diolefins with each other or with other vinyl monomers, for example ethylene/propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene/but-1-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers and their copolymers with carbon monoxide or ethylene/acrylic acid copolymers and their salts (ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene-norbornene; and mixtures of such copolymers with one another and with polymers mentioned in 1) above, for example polypropylene/ethylene-propylene copolymers, LDPE/ethylene-vinyl acetate copolymers (EVA), LDPE/ethylene-acrylic acid copolymers (EAA), LLDPE/EVA, LLDPE/EAA and alternating or random polyalkylene/carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides.

4. Hydrocarbon resins (for example C₅-C₉) including hydrogenated modifications thereof (e.g. tackifiers) and mixtures of polyalkylenes and starch.

5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

6. Copolymers of styrene or α-methylstyrene with dienes or acrylic derivatives, for example styrene/butadiene, styrene/acrylonitrile, styrene/alkyl methacrylate, styrene/butadiene/alkyl acrylate, styrene/butadiene/alkyl methacrylate, styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate; mixtures of high impact strength of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene/propylene/diene terpolymer; and block copolymers of styrene such as styrene/butadiene/styrene, styrene/isoprene/styrene, styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene.

7. Graft copolymers of styrene or α-methylstyrene, for example styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (or methacrylonitrile) on polybutadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; styrene and maleimide on polybutadiene; styrene and alkyl acrylates or methacrylates on polybutadiene; styrene and acrylonitrile on ethylene/propylene/diene terpolymers; styrene and acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate/butadiene copolymers, as well as mixtures thereof with the copolymers listed under 6), for example the copolymer mixtures known as ABS, MBS, ASA or AES polymers.

8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated copolymer of isobutylene-isoprene (halobutyl rubber), chlorinated or sulfo-chlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers, especially polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride/vinylidene chloride, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate copolymers.

9. Polymers derived from α,β-unsaturated acids and derivatives thereof such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, impact-modified with butyl acrylate.

10. Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers, for example acrylonitrile/butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide copolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.

11. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or acetals thereof, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as their copolymers with olefins mentioned in 1) above.

12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers.

13. Polyacetals such as polyoxymethylene and those polyoxymethylenes which contain ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene oxides with styrene polymers or polyamides.

15. Polyurethanes derived from hydroxyl-terminated polyethers, polyesters or polybutadienes on the one hand and aliphatic or aromatic polyisocyanates on the other, as well as precursors thereof.

16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromatic polyamides starting from m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic or/and terephthalic acid and with or without an elastomer as modifier, for example poly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or with polyethers, e.g. with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems).

17. Polyureas, polyimides, polyamide-imides, polyetherimids, polyesterimids, polyhydantoins and polybenzimidazoles.

18. Polyesters derived from dicarboxylic acids and diols and/or from hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate, polyalkylene naphthalate (PAN) and polyhydroxybenzoates, as well as block copolyether esters derived from hydroxyl-terminated polyethers; and also polyesters modified with polycarbonates or MBS.

19. Polycarbonates and polyester carbonates.

20. Polysulfones, polyether sulfones and polyether ketones.

21. Crosslinked polymers derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol/formaldehyde resins, urea/formaldehyde resins and melamine/formaldehyde resins.

22. Drying and non-drying alkyd resins.

23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinking agents, and also halogen-containing modifications thereof of low flammability.

24. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates.

25. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, isocyanates, isocyanurates, polyisocyanates or epoxy resins.

26. Crosslinked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, e.g. products of diglycidyl ethers of bisphenol A and bisphenol F, which are crosslinked with customary hardeners such as anhydrides or amines, with or without accelerators.

27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetates, cellulose propionates and cellulose butyrates, or the cellulose ethers such as methyl cellulose; as well as rosins and their derivatives.

28. Blends of the aforementioned polymers (polyblends), for example PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/ABS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS, PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO, PBT/PC/ABS or PBT/PET/PC.

29. Naturally occurring and synthetic organic materials which are pure monomeric compounds or mixtures of such compounds, for example mineral oils, animal and vegetable fats, oil and waxes, or oils, fats and waxes based on synthetic esters (e.g. phthalates, adipates, phosphates or trimellitates) and also mixtures of synthetic esters with mineral oils in any weight ratios, typically those used as spinning compositions, as well as aqueous emulsions of such materials.

30. Aqueous emulsions of natural or synthetic rubber, e.g. natural latex or latices of carboxylated styrene/butadiene copolymers.

This invention therefore additionally relates to a composition comprising an organic material subject to degradation induced by light, heat or oxidation and the stabilizer mixture described herein above.

A further embodiment of the present invention is a method for stabilizing an organic material against degradation induced by light, heat or oxidation, which comprises incorporating into the organic material the stabilizer mixture described herein above.

The organic material is preferably a synthetic polymer, in particular from one of the above groups. Polyolefins are preferred and polyethylene, polypropylene, a polyethylene copolymer and a polypropylene copolymer are particularly preferred.

The components (A), (B) and (C) may be added to the organic material to be stabilized either individually or mixed with one another.

Each of the components (A), (B) and (C) may be present in the organic material in an amount of preferably 0.005 to 5%, in particular 0.01 to 1% or 0.05 to 1%, relative to the weight of the organic material.

The weight ratio of the components (A):(B) or (A):(C) is preferably 10:1 to 1:100, in particular 10:1 to 1:10 or 5:1 to 1:5. Further examples for the weight ratio are also 1:1 to 1:10, for example 1:2 to 1:5.

The above components can be incorporated into the organic material to be stabilized by known methods, for example before or during shaping or by applying the dissolved or dispersed compounds to the organic material, if necessary with subsequent evaporation of the solvent. The components can be added to the organic material in the form of a powder, granules or a masterbatch, which contains these components in, for example, a concentration of from 2.5 to 25% by weight.

If desired, the components (A), (B) and (C) can be blended with each other before incorporation in the organic material. They can be added to a polymer before or during the polymerization or before the crosslinking.

The materials stabilized according to this invention can be used in a wide variety of forms, for example as films, fibres, tapes, moulding compositions, profiles or as binders for paints, adhesives or putties.

The stabilized material may additionally also contain various conventional additives, for example:

1. Antioxidants

1.1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the side chains, for example 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6-(1′-methylundec-1′-yl)phenol, 2,4-dimethyl-6-(1′-methylheptadec-1′-yl)phenol, 2,4-dimethyl-6-(1′-methyltridec-1′-yl)phenol and mixtures thereof.

1.2. Alkylthiomethylphenols, for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol.

1.3. Hydroquinones and alkylated hydroquinones, for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenyl stearate, bis(3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

1.4. Tocopherols, for example α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures thereof (vitamin E).

1.5. Hydroxylated thiodiphenyl ethers, for example 2,2′-thiobis(6-tert-butyl-4-methylphenol), 2,2′-thiobis(4-octylphenol), 4,4′-thiobis(6-tert-butyl-3-methylphenol), 4,4′-thiobis(6-tert-butyl-2-methylphenol), 4,4′-thiobis(3,6-di-sec-amylphenol), 4,4′-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide.

1.6. Alkylidenebisphenols, for example 2,2′-methylenebis(6-tert-butyl-4-methylphenol), 2,2′-methylenebis(6-tert-butyl-4-ethylphenol), 2,2′-methylenebis[4-methyl-6-(α-methylcyclohexyl)-phenol], 2,2′-methylenebis(4-methyl-6-cyclohexylphenol), 2,2′-methylenebis(6-nonyl-4-methylphenol), 2,2′-methylenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(4,6-di-tert-butylphenol), 2,2′-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2′-methylenebis[6-(α-methylbenzyl)-4-nonylphenol], 2,2′-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4′-methylenebis(2,6-di-tert-butylphenol), 4,4′-methylenebis(6-tert-butyl-2-methylphenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethylene glycol bis[3,3-bis(3′-tert-butyl-4′-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methyl-phenyl)dicyclopentadiene, bis[2-(3′-tert-butyl-2′-hydroxy-5′-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate, 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis-(5-tert-butyl-4-hydroxy2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane.

1.7. O-, N- and S-benzyl compounds, for example 3,5,3′,5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.

1.8. Hydroxybenzylated malonates, for example dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, di-octadecyl-2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)malonate, di-dodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate.

1.9. Aromatic hydroxybenzyl compounds, for example 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)phenol.

1.10. Triazine compounds, for example 2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxy-phenylpropionyl)-hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate.

1.11. Benzylphosphonates, for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.

1.12. Acylaminophenols, for example 4-hydroxylauranilide, 4-hydroxystearanilide, octyl N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate.

1.13. Esters of β-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1.14. Esters of β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane; 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]-undecane.

1.15. Esters of β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols, e.g. with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N′-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane.

1.17. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid e.g. N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylenediamide, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)trimethylenediamide, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N′-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard®XL-1, supplied by Uniroyal).

1.18. Ascorbic acid (vitamin C).

1.19. Aminic antioxidants, for example N,N′-di-isopropyl-p-phenylenediamine, N,N′-di-sec-butyl-p-phenylenediamine, N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine, N,N′-bis(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N′-bis(1-methylheptyl)-p-phenylenediamine, N,N′-dicyclohexyl-p-phenylenediamine, N,N′-diphenyl-p-phenylenediamine, N,N′-bis(2-naphthyl)-p-phenylenediamine, N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, N-(1-methylheptyl)-N′-phenyl-p-phenylenediamine, N-cyclohexyl-N′-phenyl-p-phenylenediamine, 4-(p-toluenesulfamoyl)diphenylamine, N,N′-dimethyl-N,N′-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p,p′-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylaminophenol, bis(4-methoxyphenyl)amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N,N,N′,N′-tetramethyl-4,4′-diaminodiphenylmethane, 1,2-bis[(2-methylphenyl)amino]ethane, 1,2-bis(phenylamino)propane, (o-tolyl)biguanide, bis[4-(1′,3′-dimethylbutyl)phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of mono- and dialkylated tert-butyl/tert-octyldiphenylamines, a mixture of mono- and dialkylated nonyldiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of mono- and dialkylated isopropyl/isohexyldiphenylamines, a mixture of mono- and dialkylated tert-butyldiphenylamines, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, a mixture of mono- and dialkylated tert-butyl/tert-octylphenothiazines, a mixture of mono- and dialkylated tert-octylphenothiazines, N-allylphenothiazine, N,N,N′,N′-tetraphenyl-1,4-diaminobut-2-ene, N,N-bis(2,2,6,6-tetramethylpiperid-4-yl-hexamethylenediamine, bis(2,2,6,6-tetramethylpiperid-4-yl)sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6-tetramethylpiperidin-4-ol.

2. UV Absorbers and Light Stabilisers

2.1. 2-(2′-Hydroxyphenyl)benzotriazoles, for example 2-(2′-hydroxy-5′-methylphenyl)benzotriazole, 2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)benzotriazole, 2-(5′-tert-butyl-2′-hydroxyphenyl)benzotriazole, 2-(2′-hydroxy-5′-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole, 2-(3′,5′-di-tert-butyl-2′-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-methylphenyl)-5-chlorobenzotriazole, 2-(3′-sec-butyl-5′-tert-butyl-2′-hydroxyphenyl)benzotriazole, 2-(2′-hydroxy-4′-octyloxyphenyl)benzotriazole, 2-(3′,5′-di-tert-amyl-2′-hydroxyphenyl)benzotriazole, 2-(3′,5′-bis(α,α-dimethylbenzyl)-2′-hydroxyphenyl)benzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)-5-chlorobenzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3′-tert-butyl-5′-[2-(2-ethylhexyloxy)carbonylethyl]-2′-hydroxyphenyl)benzotriazole, 2-(3′-dodecyl-2′-hydroxy-5′-methylphenyl)benzotriazole, 2-(3′-tert-butyl-2′-hydroxy-5′-(2-isooctyloxycarbonylethyl)phenylbenzotriazole, 2,2′-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzotriazole-2-ylphenol]; the transesterification product of 2-[3′-tert-butyl-5′-(2-methoxycarbonylethyl)-2′-hydroxyphenyl]-2H-benzotriazole with polyethylene glycol 300; [R—CH₂CH₂—COO—CH₂CH₂₂, where R=3′-tert-butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl, 2-[2′-hydroxy-3′-(α,α-dimethylbenzyl)-5′-(1,1,3,3-tetramethylbutyl)phenyl]-benzotriazole; 2-[2′-hydroxy-3′-(1,1,3,3-tetramethylbutyl)-5′-(α,α-dimethylbenzyl)phenyl]benzotriazole.

2.2. 2-Hydroxybenzophenones, for example the 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2′,4′-trihydroxy and 2′-hydroxy-4,4′-dimethoxy derivatives.

2.3. Esters of substituted and unsubstituted benzoic acids, for example 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butylhydroxybenzoate.

2.4. Acrylates, for example ethyl α-cyano-β,β-diphenylacrylate, isooctyl α-cyano-β,β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate and N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline.

2.5. Nickel compounds, for example nickel complexes of 2,2′-thiobis[4-(1,1,3,3-tetramethylbutyl)phenol], such as the 1:1 or 1:2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibutyldithiocarbamate, nickel salts of the monoalkyl esters, e.g. the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, e.g. of 2-hydroxy-4-methylphenylundecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.

2.6. Oxamides, for example 4,4′-dioctyloxyoxanilide, 2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide, 2,2′-didodecyloxy-5,5′-di-tert-butoxanilide, 2-ethoxy-2′-ethyloxanilide, N,N′-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2′-ethoxanilide and its mixture with 2-ethoxy-2′-ethyl-5,4′-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and p-ethoxy-disubstituted oxanilides.

2.7. 2-(2-Hydroxyphenyl)-1,3,5-triazines, for example 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyloxypropoxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxaphenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-dodecyloxypropoxy)phenyl]-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)phenyl-4,6-diphenyl-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypropoxy)phenyl]-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxypropyloxy]phenyl}-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine.

3. Metal deactivators, for example N,N′-diphenyloxamide, N-salicylal-N′-salicyloyl hydrazine, N,N′-bis(salicyloyl)hydrazine, N,N′-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N,N′-diacetyladipoyl dihydrazide, N,N′-bis(salicyloyl)oxalyl dihydrazide, N,N′-bis(salicyloyl)thiopropionyl dihydrazide.

4. Phosphites and phosphonites, for example triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tris(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite, tris(2,4-di-tert-butylphenyl)phosphite, diisodecyl pentaerythritol diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, bis(2,4-dicumylphenyl)pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)pentaerythritol diphosphite, bis(2,4,6-tris(tert-butylphenyl)pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis(2,4-di-tert-butylphenyl) 4,4′-biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocin, bis(2,4-di-tert-butyl-6-methylphenyl)methyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-dioxaphosphocin, 2,2′,2″-nitrilo-[triethyltris(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite], 2-ethylhexyl(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite, 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphirane.

The following phosphites are especially preferred:

Tris(2,4-di-tert-butylphenyl)phosphite (Irgafos®168, Ciba-Geigy), tris(nonylphenyl) phosphite,

5. Hydroxylamines, for example N,N-dibenzylhydroxylamine, N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxylamine, N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derived from hydrogenated tallow amine.

6. Nitrones, for example N-benzyl-alpha-phenylnitrone, N-ethyl-alpha-methylnitrone, N-octyl-alpha-heptylnitrone, N-lauryl-alpha-undecylnitrone, N-tetradecyl-alpha-tridecylnitrone, N-hexadecyl-alpha-pentadecylnitrone, N-octadecyl-alpha-heptadecylnitrone, N-hexadecyl-alpha-heptadecylnitrone, N-octadecyl-alpha-pentadecylnitrone, N-heptadecyl-alpha-heptadecylnitrone, N-octadecyl-alpha-hexadecylnitrone, nitrone derived from N,N-dialkylhydroxylamine derived from hydrogenated tallow amine.

7. Thiosynergists, for example dilauryl thiodipropionate or distearyl thiodipropionate.

8. Peroxide scavengers, for example esters of β-thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis(β-dodecylmercapto)propionate.

9. Polyamide stabilisers, for example copper salts in combination with iodides and/or phosphorus compounds and salts of divalent manganese.

10. Basic co-stabilisers, for example melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium, palmitate, antimony pyrocatecholate or zinc pyrocatecholate.

11. Nucleating agents, for example inorganic substances, such as talcum, metal oxides, such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals; organic compounds, such as mono- or polycarboxylic acids and the salts thereof, e.g. 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; polymeric compounds, such as ionic copolymers (ionomers). Especially preferred are 1,3:2,4-bis(3′,4′-dimethylbenzylidene)sorbitol, 1,3:2,4-di(paramethyldibenzylidene)sorbitol, and 1,3:2,4-di(benzylidene)sorbitol.

12. Fillers and reinforcing agents, for example calcium carbonate, silicates, glass fibres, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.

13. Other additives, for example plasticisers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow-control agents, optical brighteners, flameproofing agents, antistatic agents and blowing agents.

14. Benzofuranones and indolinones, for example those disclosed in U.S. Pat. No. 4,325,863; U.S. Pat. No. 4,338,244; U.S. Pat. No. 5,175,312; U.S. Pat. No. 5,216,052; U.S. Pat. No. 5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or EP-A-0591102 or 3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]-benzofuran-2-one, 3,3′-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]phenyl)benzofuran-2-one], 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyloxyphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one, 3-(2,3-dimethylphenyl)-5,7-di-tert-butylbenzofuran-2-one.

The weight ratio of the total amount of components (A), (B) and (C) to the total amount of the conventional additives can be, for example, 100:1 to 1:100 or 10:1 to 1:10.

The examples below illustrate the invention in greater detail. All percentages and parts are by weight, unless stated otherwise.

Light Stabilizers Used in the Following Examples 1 to 4:

TINUVIN 791 (RTM):

Mixture of TINUVIN 770 (RTM) and CHIMASSORB 944 (RTM) in a weight ratio of 1:1.
Compound (B-1-a-1):
TINUVIN 770 (RTM):
TINUVIN 765 (RTM):
TINUVIN 123 (RTM):
TINUVIN 144 (RTM):
ADK STAB LA 57 (RTM):
HOSTAVIN N 20 (RTM):
SANDUVOR 3050 (RTM):
HOSTAVIN N 24 (RTM):
UVINUL 4049 H (RTM),
Compound (B-6-a-1):
SANDUVOR PR 31 (RTM):
GOODRITE UV 3034 (RTM):
GOODRITE UV 3150 (RTM):
Compound (B-10-a-1):
CHIMASSORB 944 (RTM):
CYASORB UV 3346 (RTM):
CYASORB UV 3529 (RTM):
DASTIB 1082 (RTM):
CHIMASSORB 119 (RTM):
UVASIL 299 (RTM):
UVASIL 2000 (RTM):

A mixture of UVASIL 299 (RTM) and polypropylene.
UVINUL 5050 H (RTM):
LICHTSCHUTZSTOFF UV 31 (RTM:
ADK STAB LA 68 (RTM):
ADK STAB LA 63 (RTM):
TINUVIN 622 (RTM)
Mixture (A-2):

Mixture of the compounds (A-2-a) and (A-2-b) in a weight ratio of 4:1

EXAMPLE 1 Light Stabilization of Polypropylene Homopolymer Films

100 parts of unstabilized polypropylene powder (melt flow index: 3.8 g/10 min at 230° C. and 2160 g) are homogenized at 200° C. for 10 min in a Brabender plastograph with 0.05 parts of pentaerythrityl-tetrakis{3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate}, 0.05 parts of tris{2,4-di-tert-butylphenyl}phosphite, 0.1 parts of Ca stearate, 0.25 parts of titanium dioxide (Anatase) and the stabilizer mixture indicated in Table 1. The material thus obtained is compression molded in a laboratory press between two aluminum foils for 6 min at 260° C. to a 0.5 mm thick film which is cooled immediately to room temperature in a water-cooled press. Samples of 60 mm×25 mm are cut out of these 0.5 mm films and are exposed in a WEATHER-OMETER Ci 65 (black panel temperature 63±2° C., without water-spraying).

Periodically, these samples are removed from the exposure apparatus and their carbonyl content is measured with an infrared spectrophotometer. The exposure time corresponding to formation of a carbonyl absorbance of 0.1 is a measure for the efficiency of the stabilizer mixture. The values obtained are summarized in Table 1.

TABLE 1 Time in hours until Stabilizer mixture 0.1 carbonyl absorbance Control 220 0.20% of TINUVIN 791 (RTM) (=prior art) 4 595 0.10% of TINUVIN 622 (RTM) plus >5 500 0.05% of CHIMASSORB 944 (RTM) plus 0.05% of TINUVIN 770 (RTM) 0.10% of the mixture (A-2) plus >5 500 0.05% of CHIMASSORB 944 (RTM) plus 0.05% of TINUVIN 770 (RTM)

EXAMPLE 2 Light Stabilization of Polyethylene HD Films

100 parts of unstabilized high density polyethylene powder (density: 0.964 g cm⁻³, melt flow index: 5.0 g/10 min at 190° C. and 2160 g) are homogenized at 180° C. for 10 min in a Brabender plastograph with 0.03 parts of octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 0.1 parts of Ca stearate, 0.25 parts of titanium dioxide (Anatase) and the stabilizer mixture indicated in Table 2. The material thus obtained is compression molded in a laboratory press between two aluminum foils for 6 min at 210° C. to a 0.5 mm thick film which is cooled immediately to room temperature in a water-cooled press. Samples of 60 mm×25 mm are cut out of these 0.5 mm films and are exposed in a WEATHER-OMETER Ci 65 (black panel temperature 63±2° C., without water-spraying).

Periodically, these samples are removed from the exposure apparatus and their carbonyl content is measured with an infrared spectrophotometer. The exposure time corresponding to formation of a carbonyl absorbance of 0.1 is a measure for the efficiency of the stabilizer mixture. The values obtained are summarized in Table 2.

TABLE 2 Time in hours until Stabilizer mixture 0.1 carbonyl absorbance Control 465 0.20% of TINUVIN 791 (RTM) (=prior art) 3 175 0.10% of the mixture (A-2) plus 4 815 0.05% of CHIMASSORB 944 (RTM) plus 0.05% of TINUVIN 770 (RTM)

EXAMPLE 3 Light Stabilization of Polypropylene Homopolymer Films

100 parts of unstabilized polypropylene powder (melt flow index: 2.4 g/10 minutes at 230° C. and 2160 g) are homogenized at 200° C. for 10 minutes in a Brabender plastograph with 0.05 parts of pentaerythrityl tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), 0.05 parts of tris{2,4-di-tert-butylphenyl}phosphite, 0.1 parts of Ca stearate, 0.25 parts of titanium dioxide (anatase) and the light stabilizer system indicated in Tables 3A and 3B. The material thus obtained is compression molded in a laboratory press between two aluminum foils for 6 minutes at 260° C. to a 0.5 mm thick film which is cooled immediately to room temperature in a water-cooled press. Samples of 60 mm×25 mm are cut out of these 0.5 mm films and are exposed in a WEATHER-OMETER Ci 65 (black panel temperature 63±2° C.; without water-spraying).

Periodically, these samples are removed from the exposure apparatus and their carbonyl content is measured with an infrared spectrophotometer.

The exposure time (T_0.1) corresponding to the formation of a carbonyl absorbance of 0.1 is a measure for the efficiency of the light stabilizer system. The values obtained are summarized in the following Tables 3A and 3B.

TABLE 3A T_0.1in hours Light stabilizer system in combination with T_0.1in hours TINUVIN 622 (RTM) The amount of the The amount of the light stabilizers light stabilizers Light stabilizer system used is 0.075% each*). used is 0.05% each*). Without 235 — TINUVIN 770 (RTM) plus 2700 2980 CHIMASSORB 944 (RTM) TINUVIN 770 (RTM) plus 2495 3035 CHIMASSORB 119 (RTM) TINUVIN 770 (RTM) plus 3130 3510 CYASORB UV 3529 (RTM) TINUVIN 770 (RTM) plus 2790 3295 UVINUL 5050 H (RTM) TINUVIN 770 (RTM) plus 3285 3610 DASTIB 1082 (RTM) TINUVIN 770 (RTM) plus 2670 2915 ADK STAB LA 63 (RTM) TINUVIN 770 (RTM) plus 2725 3425 ADK STAB 68 (RTM) TINUVIN 770 (RTM) plus 2320 3155 LICHTSCHUTZSTOFF UV 31 (RTM)
*)The overall concentration of the light stabilizers is 0.15%.

TABLE 3B T_0.1in hours Light stabilizer system in combination with T_0.1in hours TINUVIN 622 (RTM) The amount of the The amount of the light stabilizers light stabilizers Light stabilizer system used is 0.075% each*). used is 0.05% each*). Without 235 — CHIMASSORB 944 (RTM) plus 2280 3150 TINUVIN 144 (RTM) CHIMASSORB 944 (RTM) plus 2245 2870 TINUVIN 123 (RTM) CHIMASSORB 944 (RTM) plus 2530 3170 HOSTAVIN N 20 (RTM) CHIMASSORB 944 (RTM) plus 2855 3020 GOODRITE UV 3034 (RTM) CHIMASSORB 944 (RTM) plus 2320 2765 GOODRITE UV 3150 (RTM) CHIMASSORB 944 (RTM) plus 2780 3435 Compound (B-6-a-1) CHIMASSORB 944 (RTM) plus 2925 3265 UVINUL 4049 H (RTM) CHIMASSORB 944 (RTM) plus 2965 3385 Compound (B-10-a-1) CHIMASSORB 944 (RTM) plus 2805 3130 Compound (B-1-a-1) CHIMASSORB 944 (RTM) plus 2030 2550 SANDUVOR 3050 (RTM) CHIMASSORB 944 (RTM) plus 2400 2890 SANDUVOR PR-31 (RTM)
*)The overall concentration of the light stabilizers is 0.15%.

EXAMPLE 4 Light Stabilization of Polypropylene Homopolymer Films

100 parts of unstabilized polypropylene powder (melt flow index: 3.8 g/10 minutes at 230° C. and 2160 g) are homogenized at 200° C. for 10 minutes in a Brabender plastograph with 0.05 parts of pentaerythrityl tetrakis{3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate}, 0.05 parts of tris{2,4-di-tert-butylphenyl}phosphite, 0.1 parts of Ca stearate, 0.25 parts of titanium dioxide (anatase) and the light stabilizer system indicated in Tables 4A, 4B, 4C and 4D. The material thus obtained is compression molded in a laboratory press between two aluminum foils for 6 minutes at 26000 to a 0.5 mm thick film which is cooled immediately to room temperature in a water-cooled press. Samples of 60 mm×25 mm are cut out of these 0.5 mm films and are exposed in a WEATHER-OMETER Ci 65 (black panel temperature 63±2° C.; without water-spraying).

Periodically, these samples are removed from the exposure apparatus and their carbonyl content is measured with an infrared spectrophotometer.

The exposure time (T_0.1) corresponding to the formation of a carbonyl absorbance of 0.1 is a measure for the efficiency of the light stabilizer system. The values obtained are summarized in the following Tables 4A, 4B, 4C and 4D.

TABLE 4A T_0.1in hours Light stabilizer system in combination with TINUVIN 622 (RTM) T_0.1in hours The amount of the stabilizers The amount of the of the light stabilizer system light stabilizers is 0.09% each and the amount Light stabilizer system used is 0.1% each*). of TINUVIN 622 (RTM) is 0.02%*). Without 310 TINUVIN 770 (RTM) plus 4520 5525 CHIMASSORB 944 (RTM) TINUVIN 770 (RTM) plus 4935 6255 CHIMASSORB 119 (RTM) TINUVIN 770 (RTM) plus 5980 >6930 CYASORB UV 3346 (RTM) TINUVIN 770 (RTM) plus 5365 >6930 UVASIL 299 HM (RTM) TINUVIN 770 (RTM) plus 5785 6805 UVASIL 2000 (RTM) TINUVIN 770 (RTM) plus 6010 6675 CYASORB UV 3529 (RTM) TINUVIN 770 (RTM) plus 2720 3225 UVINUL 5050 H (RTM)
*)The overall concentration of the light stabilizers is 0.2%.

TABLE 4B T_0.1in hours Light stabilizer system in combination with Mixture (A-2) T_0.1in hours The amount of the stabilizers of The amount of the the light stabilizer system is light stabilizers 0.075% each and the amount Light stabilization system used is 0.1% each*). of Mixture (A-2) is 0.05%*). Without 310 — TINUVIN 770 (RTM) plus 4520 5475 CHIMASSORB 944 (RTM) TINUVIN 770 (RTM) plus 2720 3370 UVINUL 5050 H (RTM)
*)The overall concentration of the light stabilizers is 0.2%.

TABLE 4C T_0.1in hours Light stabilizer system in combination with TINUVIN 622 (RTM) T_0.1in hours The amount of the stabilizers of The amount of the the light stabilizer system is light stabilizers 0.075% each and the amount Light stabilizer system used is 0.1% each*). of TINUVIN 622 (RTM) is 0.05%*). Without 315 — CHIMASSORB 944 (RTM) plus 3775 4585 TINUVIN 765 (RTM) CHIMASSORB 944 (RTM) plus 3485 3990 TINUVIN 144 (RTM) CHIMASSORB 944 (RTM) plus 3055 3365 TINUVIN 123 (RTM) CHIMASSORB 944 (RTM) plus 3335 4325 HOSTAVIN N 20 (RTM) CHIMASSORB 944 (RTM) plus 2795 3315 HOSTAVIN N 24 (RTM) CHIMASSORB 944 (RTM) plus 4065 5110 ADK STAB LA 57 (RTM) CHIMASSORB 944 (RTM) plus 2725 3635 ADK STAB LA 62 (RTM) CHIMASSORB 944 (RTM) plus 3045 3485 ADK STAB LA 67 CHIMASSORB 944 (RTM) plus 3300 4115 GOODRITE UV 3150 (RTM) CHIMASSORB 944 (RTM) plus 4230 5125 Compound (B-6-a-1) CHIMASSORB 944 (RTM) plus 3745 4730 Compound (B-10-a-1) CHIMASSORB 944 (RTM) plus 2695 3280 SANDUVOR 3050 (RTM) CHIMASSORB 944 (RTM) plus 2835 4070 SANDUVOR PR-31 (RTM)
*)The overall concentration of the light stabilizers is 0.2%.

TABLE 4D T_0.1in hours Light stabilizer system in combination with Mixture (A-2) T_0.1in hours The amount of the stabilizers The amount of the of the light stabilizer system light stabilizers is 0.075% each and the amount Light stabilizer system used is 0.1% each*). of Mixture (A-2) is 0.05%*). Without 315 — CHIMASSORB 944 (RTM) plus 3775 4715 TINUVIN 765 (RTM) CHIMASSORB 944 (RTM) plus 2835 3350 SANDUVOR PR-31 (RTM)
*)The overall concentration of the light stabilizers is 0.2%.

A further embodiment of this invention relates to a second stabilizer mixture containing

(1) a component (AA-1) or (AA-2) as defined in the following, and
(2) a component (B) or (C) as defined above.

The general disclosure described above also relates to this second stabilizer mixture (which is also useful for stabilizing an organic material against degradation induced by light, heat or oxidation) in appropriate manner.

The compounds of component (AA-1) are described for example in U.S. Pat. No. 4,609,698 which is incorporated by reference herein.

The compounds of component (AA-2) are described for example in EP-A-1,803 which is also incorporated by reference herein. Preferred compounds of component (AA-2) are FERRO AM 806 (RTM) or KOKANOX (RTM).

The weight ratio of the component (AA-1) or (AA-2) to the component (B) or (C) is preferably 10:1 to 1:100, in particular 10:1 to 1:10 or 5:1 to 1:5. Further examples for the weight ratio are also 1:1 to 1:10 such as 1:2 to 1:5.

The component (AA-1) or (AA-2) as well as the component (B) or (C) may be present in the material to be stabilized in an amount of preferably 0.005 to 5%, in particular 0.01 to 1% or 0.05 to 1%, relative to the weight of said material.

Component (AA-1) is a compound of the formula (AA-1-I) or (AA-1-II)
wherein

n₁₀₀is a number from 1 to 3, preferably 2;
the radicals R₁₀₁independently of one another are C₂-C₁₈alkylene, C₄-C₈alkenylene, C₄-C₂₀monooxaalkylene, C₄-C₂₀polyoxaalkylene, C₅-C₈cycloalkylene, C₇-C₁₀cycloalkylene-dialkylene, C₈-C₂₀phenylene-dialkylene or a group of the formula
m₁₀₀is an integer from 2 to 10;
X₁₀₀is a group —O— or —NR₁₀₅—;
Y₁₀₀is C₂-C₁₂alkylene, C₄-C₁₂alkylene interrupted by one or two —O— or —NH— groups; cyclohexylene, cyclohexylene-dimethylene, phenylene or phenylene-Z₁₀₀-phenylene with Z₁₀₀being —O—, —CH₂— or —SO₂—;
the radicals R₁₀₂independently of one another are a direct bond, C₁-C₁₈alkylene, C₂-C₆alkenylene, C₅-C₈cycloalkylene, C₅-C₈cycloalkenylene, phenylene, C₇-C₁₂phenylenealkylene or a group of the formula
p₁₀₀is 1 or 2;
E₁₀₀is hydrogen, C₁-C₈alkyl, cyclohexyl, benzyl or an acyl group of the formula R₁₀₇—CO—, R₁₀₈—O—CO— or (R₁₀₉)(R₁₁₀)N—CO—;
E′₁₀₀is a group R₁₁₁O— or (R₁₁₂)(R₁₁₃)N—;
R₁₀₃is hydrogen, C₁-C₆alkyl, C₂-C₇alkoxymethyl, phenoxymethyl or tolyloxymethyl,
R₁₀₄is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl, preferably hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy or cyclohexyloxy, in particular hydrogen or methyl;
R₁₀₅is hydrogen, C₁-C₁₂alkyl, cyclohexyl, phenyl, benzyl, phenylethyl or C₁-C₈acyl;
R₁₀₆is C₂-C₁₂alkylene, C₄-C₈alkenylene or xylylene;
R₁₀₇is C₁-C₁₂alkyl, C₂-C₅alkenyl, C₅-C₈cycloalkyl, phenyl, C₇-C₁₂phenylalkyl or a group of the formula (AA-1-III)
R₁₀₈is C₁-C₁₂alkyl, allyl, cyclohexyl or phenyl;
R₁₀₉is hydrogen, C₁-C₈alkyl, allyl, cyclohexyl, phenyl or C₇-C₁₀alkylphenyl,
R₁₁₀is C₁-C₈alkyl, allyl, cyclohexyl, phenyl or C₇-C₁₀alkylphenyl; or
R₁₀₉and R₁₁₀together with the N atom to which they are attached form a 5-membered to 7-membered heterocyclic ring;
R₁₁₁is C₁-C₁₂alkyl, C₃-C₅alkenylmethyl, C₅-C₈cyloalkyl, phenyl, C₇-C₁₀alkylphenyl, C₇-C₁₂phenylalkyl, C₃-C₁₂alkoxyalkyl, a group —(CH₂CH₂O)_m₁₀₀—CH₃, a group of the formula (AA-1-III) or a group of the formula (AA-1-IV);
R₁₁₂is C₁-C₁₂alkyl, allyl, cyclohexyl, phenyl, benzyl, C₃-C₁₂alkoxyalkyl, C₄-C₁₂dialkylaminoalkyl, a group of the formula (AA-1-III) or a group of the formula (AA-1-V);
R₁₁₃is hydrogen, C₁-C₁₂alkyl, allyl, cyclohexyl or a group of the formula (III); with the proviso that at least one of the radicals R₁₀₁, R₁₀₂, E₁₀₀and E′₁₀₀contains a group of the formula
and
with the proviso that the repeating units in each of the formulae (AA-1-I) and (AA-1-II) can be identical or different.

Component (AA-2) is a compound of the formula (AA-2-I)
in which

n₂₀₀and n₂₀₁are independently of one another a number from 1 to 50;
R₂₀₁is hydrogen or C₁-C₄alkyl;
X₂₀₁is —O— or >N—R₂₀₂;
R₂₀₂is hydrogen, C₁-C₁₂alkyl, cyclohexyl, phenyl, benzyl, phenylethyl or C₁-C₈acyl;
Y₂₀₁is C₁-C₄alkyl or a group of the formula (AA-2-II);
R₂₀₃is hydrogen, C₁-C₈alkyl, O., —OH, —CH₂CN, C₁-C₁₈alkoxy, C₅-C₁₂cycloalkoxy, C₃-C₆alkenyl, C₇-C₉phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C₁-C₄alkyl; or C₁-C₈acyl, preferably hydrogen, C₁-C₄alkyl, C₁-C₈alkoxy or cyclohexyloxy, in particular hydrogen or methyl;
Z₂₀₀is ethylene or a group of the formula (AA-2-III)
R₂₀₄is hydrogen or C₁-C₄alkyl;
X₂₀₂has one of the meanings of X₂₀₁;
Y₂₀₂is C₁-C₁₈alkyl or a group of the formula (AA-2-II);
with the provisos that the repeating units in the formula (AA-2-I) have a block or random distribution and that each of the repeating units
in the formula (AA-2-I) can be identical or different, and
with the proviso that at least 2%, preferably at least 5%, of the repeating units in the formula (AA-2-I) contain a group of the formula (AA-2-II).

In the compounds of the formula (AA-2-I), the end groups are for example hydrogen or a group —CH═C(R₂₀₁)—CO—X₂₀₁—Y₂₀₁.

All stabilizer mixtures described in this application are further useful as light stabilizers for coatings. A use in combination with an UV absorber is preferred. Suitable coatings are for example described in U.S. Pat. No. 6,117,997, column 26, line 55 to column 32, line 21.

The example below illustrates the use of the second stabilizer mixtures. All percentages and parts are by weight, unless stated otherwise.

EXAMPLE A Light Stabilization of Polypropylene Homopolymer Films

100 parts of unstabilized polypropylene powder (melt flow index: 3.2 g/10 min at 230° C. and 2160 g) are homogenized at 200° C. for 10 min in a Brabender plastograph with 0.05 parts of pentaerythrityl-tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate), 0.05 parts of tris(2,4-di-tert-butylphenyl)phosphite, 0.1 parts of Ca stearate, 0.25 parts of titanium dioxide (Anatase) and the stabilizer mixture indicated in Tables 3a and 3b. The material thus obtained is compression molded in a laboratory press between two aluminum foils for 6 min at 260° C. to a 0.5 mm thick film which is cooled immediately to room temperature in a water-cooled press. Samples of 60 mm×25 mm are cut out of these 0.5 mm films and are exposed in a WEATHER-OMETER Ci 65 (black panel temperature 63±2° C., without water-spraying).

Periodically, these samples are removed from the exposure apparatus and their carbonyl content is measured with an infrared spectrophotometer. The exposure time corresponding to formation of a carbonyl absorbance of 0.1 is a measure for the efficiency of the stabilizer mixture. The values obtained are summarized in Tables 3a and 3b.

TABLE 3a Time in hours until Stabilizer mixture 0.1 carbonyl absorbance 0.05% of (AA-1-II-1-A) and 1585 0.05% of TINUVIN 770 (RTM) 0.05% of (AA-1-II-2-A) and 2485 0.05% of TINUVIN 770 (RTM) 0.05% of (AA-1-II-3-A) and 2415 0.05% of TINUVIN 770 (RTM) 0.05% of (AA-1-II-4-A) and 2100 0.05% of TINUVIN 770 (RTM) 0.05% of (AA-1-II-5-A) and 1895 0.05% of TINUVIN 770 (RTM)

TABLE 3b Time in hours until Stabilizer mixture 0.1 carbonyl absorbance 0.05% of (AA-2-I-3-A) and 2125 0.05% Of TINUVIN 770 (RTM)

Stabilizers Used:
with the sum of n₂₀₀and n₂₀₁being a number from 2 to 20.

Claims

1. A stabilizer mixture containing the components (A), (B) and (C) wherein component (A) is

a compound selected from the group consisting of a compound of the formula (A-1)

wherein

A1 is hydrogen or C1-C4alkyl,

A2 is a direct bond or C1-C10alkylene, and

n1 is a number from 2 to 50;

at least one compound of the formula (A-2-a) or (A-2-b)

wherein

n2 and n2* are a number from 2 to 50;

component (B) is a low molecular weight sterically hindered amine compound selected from the group consisting of compound of the formula (B-1)

in which

E1 is hydrogen, C1-C8alkyl, O., —OH, —CH2CN, C1-C18alkoxy, C5-C12cycloalkoxy, C3-C6alkenyl, C7-C9phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; or C1-C8acyl,

m1 is 1, 2 or 4,

if m1 is 1, E2 is C1-C25alkyl,

if m1 is 2, E2 is C1-C14alkylene or a group of the formula (b-I)

wherein

E3 is C1-C10alkyl or C2-C10alkenyl, E4 is C1-C10alkylene, and

E5 and E6 independently of one another are C1-C4alkyl, cyclohexyl or methylcyclohexyl, and

if m1 is 4, E2 is C4-C10alkanetetrayl:

a compound of the formula (B-2)

in which

two of the radicals E7 are —COO—(C1-C20alkyl), and

two of the radicals E7 are a group of the formula (b-II)

with E8 having one of the meanings of E1;

a compound of the formula (B-3)

in which

E9 and E10 together form C2-C14alkylene,

E11 is hydrogen or a group -Z1-COO-Z2,

Z1 is C2-C14alkylene, and

Z2 is C1-C24alkyl, and

E12 has one of the meanings of E1;

a compound of the formula (B-4)

wherein

the radicals E13 independently of one another have one of the meanings of E1,

the radicals E14 independently of one another are hydrogen or C1-C12alkyl, and

E15 is C1-C10alkylene or C3-C10alkylidene;

a compound of the formula (B-5)

wherein

the radicals E16 independently of one another have one of the meanings of E1;

a compound of the formula (B-6)

in which

E17 is C1-C24alkyl, and

E18 has one of the meanings of E1;

a compound of the formula (B-7)

in which

E19, E20 and E21 independently of one another are a group of the formula (b-III)

wherein E22 has one of the meanings of E1;

a compound of the formula (B-8)

wherein

the radicals E23 independently of one another have one of the meanings of E1,

and E24 is hydrogen, C1-C12alkyl or C1-C12alkoxy;

a compound of the formula (B-9)

wherein

m2 is 1, 2 or 3,

E25 has one of the meanings of E1, and

when m2 is 1, E26 is a group

when m2 is 2, E26 is C2-C22alkylene, and

when m2 is 3, E26 is a group of the formula (b-IV)

wherein the radicals E27 independently of one another are C2-C12alkylene, and the radicals E28 independently of one another are C1-C12alkyl or C5-C12cycloalkyl; or

a compound of the formula (B-10)

wherein

the radicals E29 independently of one another have one of the meanings of E1, and E30 is C2-C22alkylene, C5-C7cycloalkylene, C1-C4alkylenedi(C5-C7cycloalkylene), phenylene or phenylenedi(C1-C4alkylene); and

component (C) is a high molecular weight sterically hindered amine compound selected from the group consisting of the formula (C-1)

in which

R1, R3, R4 and R5 independently of one another are hydrogen, C1-C12alkyl, C5-C12cycloalkyl, C1-C4-alkyl-substituted C5-C12cycloalkyl, phenyl, phenyl which is substituted by —OH and/or C1-C10alkyl; C7-C9phenylalkyl, C7-C9phenylalkyl which is substituted on the phenyl radical by —OH and/or C1-C10alkyl; or a group of the formula (c-I)

R2 is C2-C18alkylene, C5-C7cycloalkylene or C1-C4alkylenedi(C5-C7cycloalkylene), or the radicals R1, R2 and R3, together with the nitrogen atoms to which they are bonded, perform a 5- to 10-membered heterocyclic ring, or

R4 and R5, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring,

R6 is hydrogen, C1-C8alkyl, O., —OH, —CH2CN, C1-C18alkoxy, C5-C12cycloalkoxy. C3-C6alkenyl, C7-C9phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; or C1-C8acyl, and b1 is a number from 2 to 50,

with the proviso that at least one of the radicals R1, R3, R4 and R5 is a group of the formula (c-I);

a compound of the formula (C-2)

wherein

R7 and R11 independently of one another are hydrogen or C1-C12alkyl,

R8, R9 and R10 independently of one another are C2-C10alkylene, and

X1, X2, X3, X4, X5, X6, X7 and X8 independently of one another are a group of the formula (c-II).

in which

R12 is hydrogen, C1-C12alkyl, C5-C12cycloalkyl, C1-C4alkyl-substituted C5-C12cycloalkyl, phenyl, —OH— and/or C1-C10alkyl-substituted phenyl, C7-C9phenylalkyl. C7-C9phenylalkyl which is substituted on the phenyl radical by —OH and/or C1-C10alkyl; or a group of the formula (c-I) as defined above, and

R13 has one of the meanings of R6;

a compound of the formula (C-3)

in which

R14 is C1-C10alkyl, C5-C12cycloalkyl, C1-C4alkyl-substituted C5-C12cycloalkyl, phenyl or C1-C10alkyl-substituted phenyl,

R15 is C3-C10alkylene,

R16 has one of the meanings of R6, and

b2 is a number from 2 to 50:

a compound of the formula (C-4)

in which

R17 and R21 independently of one another are a direct bond or a —N(X9)—CO—X10—CO—N(X11)— group, where X9 and X11 independently of one another are hydrogen, C1-C8alkyl, C5-C12cycloalkyl, phenyl, C7-C9phenylalkyl or a group of the formula (c-I).

X10 is a direct bond or C1-C4alkylene,

R18 has one of the meanings of R6,

R19, R20, R23 and R24 independently of one another are hydrogen, C1-C30alkyl, C5-C12cycloalkyl or phenyl,

R22 is hydrogen, C1-C30alkyl, C5-C12cycloalkyl, phenyl, C7-C9phenylalkyl or a group of the formula (c-I), and

b3 is a number from 1 to 50;

a compound of the formula (C-5)

in which

R25, R26, R27, R28 and R29 independently of one another are a direct bond or C1-C10alkylene,

R30 has one of the meanings of R6, and

b4 is a number from 1 to 50; or

a product (C-6) obtainable by reacting a product, obtained by reaction of a polyamine of the formula (C-6-1) with cyanuric chloride, with a compound of the formula (C-6-2)

H2N—(CH2)b′5—NH—(CH2)b″5—NH—(CH2)b′″5—NH2 (C-6-1)

in which

b′5, b″5 and b′″5 independently of one another are a number from 2 to 12,

R31 is hydrogen, C1-C12alkyl, C5-C12cycloalkyl, phenyl or C7-C9phenylalkyl, and

R32 has one of the meanings of R6.

2-3. (canceled)

4. A stabilizer mixture according to claim 1 wherein

A1 is hydrogen or methyl,

A2 is a direct bond or C2-C6alkylene, and

n1 is a number from 2 to 25;

n2 and n2* are a number from 2 to 25.

5. A stabilizer mixture according to claim 1 wherein

m1 is 1, 2 or 4,

if m1 is 1, E2 is C12-C20alkyl,

if m1 is 2, E2 is C2-C10alkylene or a group of the formula (b-I)

E3 is C1-C4alkyl,

E4 is C1-C6alkylene, and

E5 and E6 independently of one another are C1-C4alkyl, and

if m1 is 4, E2 is C4-C8alkanetetrayl;

two of the radicals E7 are —COO—(C10-C15alkyl), and

two of the radicals E7 are a group of the formula (b-II);

E9 and E10 together form C9-C13alkylene,

E11 is hydrogen or a group -Z1-COO-Z2,

Z1 is C2-C6alkylene, and

Z2 is C10-C16alkyl;

E14 is hydrogen, and

E15 is C2-C6alkylene or C3-C5alkylidene;

E17 is C10-C14alkyl;

E24 is C1-C4alkoxy;

m2 is 1, 2 or 3,

when m2 is 1, E26 is a group

when m2 is 2, E26 is C2-C6alkylene, and

when m2 is 3, E26 is a group of the formula (b-IV)

the radicals E27 independently of one another are C2-C6alkylene, and

the radicals E28 independently of one another are C1-C4alkyl or C5-C8cycloalkyl; and

E30 is C2-C8alkylene.

6. A stabilizer mixture according to claim 1 wherein

R1 and R3 independently of one another are a group of the formula (c-I),

R2 is C2-C8alkylene,

R4 and R5 independently of one another are hydrogen, C1-C12alkyl, C5-C8cycloalkyl or a group of the formula (c-I), or the radicals R4 and R5, together with the nitrogen atom to which they are bonded, form a 5- to 10-membered heterocyclic ring, and

b1 is a number from 2 to 25;

R7 and R11 independently of one another are hydrogen or C1-C4alkyl,

R8, R9 and R10 independently of one another are C2-C4alkylene, and X1, X2, X3, X4, X5, X6, X7 and X8 independently of one another are a group of the formula (c-II),

R12 is hydrogen, C1-C4alkyl, C5-C8cycloalkyl or a group of the formula (c-I);

R14 is C1-C4alkyl,

R15 is C3-C6alkylene, and

b2 is a number from 2 to 25;

R17 and R21 independently of one another are a direct bond or a group —N(X9)—CO—X10—CO—N(X11)—,

X9 and X11 independently of one another are hydrogen or C1-C4alkyl,

X10 is a direct bond,

R19 and R23 are C1-C25alkyl or phenyl,

R20 and R24 are hydrogen or C1-C4alkyl,

R22 is C1-C25alkyl or a group of the formula (c-I), and

b3 is a number from 1 to 25;

R25, R26, R27, R28 and R29 independently of one another are a direct bond or C1-C4alkylene, and

b4 is a number from 1 to 25;

b′5, b″5 and b′″5 independently of one another are a number from 2 to 4, and

R31 is hydrogen, C1-C4alkyl, C5-C8cycloalkyl, phenyl or benzyl.

7. A stabilizer mixture according to claim 1 wherein

component (A) is a compound selected from the group consisting of formula (A-1-a), (A-2-a) and (A-2-b);

wherein n1 is a number from 2 to 20;

wherein n2 and n2* are a number from 2 to 20;

component (B) is a compound selected from the group consisting of formula (B-1-a), (B-1-b), (B-1-c), (B-1-d), (B-2-a), (B-3-a), (B-3-b), (B-4-a), (B-4-b), (B-5), (B-6-a), (B-7), (B-8-a), (B-9-a), (B-9-b), (B-9-c) and (B-10-a);

wherein E1 is hydrogen, C1-C8alkyl, O., —OH, —CH2CN, C1-C18alkoxy, C5-C12cycloalkoxy, C3-C6alkenyl, C7-C9phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; or C1-C8acyl;

in which two of the radicals E7 are —COO—C13H27 and

two of the radicals E7 are

and E8 has one of the meanings of E1;

wherein E12 has one of the meanings of E1;

wherein E13 has one of the meanings of E1;

wherein E16 has one of the meanings of E1;

wherein E18 has one of the meanings of E1;

in which E19, E20 and E21 independently of one another are a group of the formula (b-II)

wherein E22 has one of the meanings of E1;

wherein E23 has one of the meanings of E1;

wherein E25 has one of the meanings of E1;

wherein E29 has one of the meanings of E1; and

component (C) is a compound selected from the group consisting of formula (C-1-a), (C-1-b), (C-1-c), (C-1-d), (C-2-a), (C-3-a), (C-4-a), (C-4-b), (C-4-c) or (C-5-a) and a product (C-6-a);

wherein b1 is a number from 2 to 20 and R6 is hydrogen, C1-C8alkyl, O., —OH, —CH2CN, C1-C18alkoxy, C5-C12cycloalkoxy, C3-C6alkenyl, C7-C9phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; or C1-C8acyl;

wherein R13 has one of the meanings of R6,

wherein b2 is a number from 2 to 20 and R16 has one of the meanings of R6;

wherein b3 is a number from 1 to 20 and R18 has one of the meanings of R6;

wherein b4 is a number from 1 to 20 and R30 has one of the meanings of R6;

a product (C-6-a) obtainable by reacting a product, obtained by reaction of a polyamine of formula (C-6-1-a) with cyanuric chloride, with a compound of e formula (C-6-2-a)

H2N—(CH2)3—NH—(CH2)2—NH—(CH2)3—NH2 (C-6-1-a)

in which R32 has one of the meanings of R6.

8. (canceled)

9. A stabilizer mixture according to claim 1 wherein E1, E8, E12, E13, E16, E18, E22, E23, E25 and E29 are hydrogen, C1-C4alkyl, C1-C10alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.

10. A stabilizer mixture according to claim 1 wherein R6, R13, R16, R18, R30 and R32 are hydrogen, C1-C4alkyl, C1-C10alkoxy, cyclohexyloxy, allyl, benzyl or acetyl.

11. A stabilizer mixture according to claim 7 wherein E1, E8, E12, E13, E16, E18, E22, E23, E25, E29, R6, R13, R16, R18, R30 and R32 are hydrogen or methyl and E1 and R6 additionally are C1-C8alkoxy.

12. A stabilizer mixture according to claim 7 wherein component (A) is a compound selected from the group consisting of the formula (A-1-a) wherein n1 is a number from 2 to 20, and a compound of the formula (A-2-a) or (A-2-b) wherein n2 and n2* are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E1 is hydrogen and component (C) is a compound selected from the group consisting of the formula (C-1-a) wherein b1 is a number from 2 to 20 and R6 is hydrogen, a compound of the formula (C-1-b) wherein R6 is hydrogen or propoxy and b1 is a number from 2 to 20, a compound of the formula (C-1-d) wherein R6 is hydrogen or methyl and b1 is a number from 2 to 20, a compound of the formula (C-2-a) wherein R13 is methyl, a compound of the formula (C-3-a) wherein R16 is hydrogen and b2 is a number from 2 to 20, a compound of the formula (C-4-a) wherein R18 is hydrogen and b3 is a number from 1 to 20, and a product (C-6-a).

13. A stabilizer mixture according to claim 7 wherein component (A) is a compound selected from the group consisting of the formula (A-1-a) wherein n1 is a number from 2 to 20, and a compound of the formula (A-2-a) or (A-2-b) wherein n2 and n2* are a number from 2 to 20, component (B) is a compound of the formula (B-1-b) wherein E1 is hydrogen and component (C) is a compound of the formula (C-1-a) wherein b1 is a number from 2 to 20 and R6 is hydrogen.

14. A stabilizer mixture according to claim 7 wherein

component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E1 being hydrogen and component (C) is a compound of the formula (C-1-a) with R6 being hydrogen; or

component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E1 being octyloxy and component (C) is a compound of the formula (C-1-a) with R6 being hydrogen; or

component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-3-a) with E12 being hydrogen and component (C) is a compound of the formula (C-1-a) with R6 being hydrogen; or

component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-10-a) with E29 being hydrogen and component (C) is a compound of the formula (C-1-a) with R6 being hydrogen; or

component (A) is a compound of the formula (A-1-a), component (B) is a compound of the formula (B-1-b) with E1 being methyl and component (C) is a compound of the formula (C-2-a) with R13 being methyl.

15. A composition comprising an organic material subject to degradation induced by light, heat or oxidation and a stabilizer mixture according to claim 1.

16. A composition according to claim 15 wherein the organic material is a synthetic polymer.

17. A composition according to claim 15 wherein the organic material is a polyolefin.

18. A composition according to claim 15 wherein the organic material is polyethylene, polypropylene, a polyethylene copolymer or a polypropylene copolymer.

19. A method for stabilizing an organic material against degradation induced by light, heat or oxidation, which comprises incorporating into the organic material a stabilizer mixture according to claim 1.

20-27. (canceled)

28. A stabilizer mixture according to claim 1 wherein the product (C-6) is represented by a compound of the formula (C-6-α, (C-6-β or (C-6-γ), or a mixture of these three compounds

wherein the radicals R31 and R32 are as defined in claim 1 and b5 is 2 to 20.

29. A stabilizer mixture according to claim 1 wherein the product (C-6) is represented by the compound of the formula

wherein b5 is 2 to 20.