Publication number: 20190153197
Abstract: A novel flame retardant-stabilizer combination for thermoplastic polymers, comprising as component A 20 to 99% by weight of a dialkylphosphinic salt of the formula (I) and/or of a diphosphinic salt of the formula (II) and/or polymers thereof in which R1, R2 are the same or different and are each C1-C6-alkyl, linear or branched; R3 is C1-C10-alkylene, linear or branched, C6-C10-arylene, C7-C20-alkylarylene or C7-C20-arylalkylene; M is Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base; m is 1 to 4; n is 1 to 4; x is 1 to 4, as component B 1 to 80% by weight of a salt of the phosphorous acid with the general formula (III) [HP(?O)O2]2?Mm+ (III) in which M is Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na and/or K and m is 1 to 4, as component C 0 to 30% by weight of a nitrogen-containing synergist and/or of a phosphorus/nitrogen flame retardant, as component D 0 to 10% by weight of a zinc salt and/or of a basic or amphoteric oxide, hydroxide, carbo
Type:
Application
Filed:
November 15, 2018
Publication date:
May 23, 2019
Applicant:
CLARIANT INTERNATIONAL LTD
Inventors:
Werner KRAUSE, Harald BAUER, Martin SICKEN, Sebastian HÖROLD, Wolfgang WANZKE, Elke SCHLOSSER
Patent number: 9279085
Abstract: The invention relates to a method for producing monofunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester thereof, whereupon said alkylphosphonous acid, the salt or ester (II) thereof is reacted with compounds containing C?C, C?O, or C?N double bonds to obtain compounds of type (III), wherein R1, R2, R3, R4, R5, R6 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, X represents, inter alia, H, C1-C18-alkyl, C6-C18-aryl, and/or Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K, H, and wherein A represents OH, NH2, NHR, NR2, or O—CO—R8, and W represents a mineral acid, carboxylic acid, Lewis acid, or organic acid, wherein n is a whole or a fractional number from 0 to 4, and catalyst A represents transition metals and/or transition metal compo
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
March 8, 2016
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
Patent number: 9018413
Abstract: The invention relates to a method for producing monocarboxy-functionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to obtain an alkylphosphonous acid, the salt or ester (II) thereof, and b) the obtained alkylphosphonous acid, the salt or ester (II) thereof is reacted with an oxidizing agent or with an oxidizing agent and water or with oxygen and water in the presence of a catalyst B to obtain the alkylphosphonic acid derivative (III), wherein R1, R2, R3, R4 are identical or different from each other and independently represent, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, X and Y are identical or different from each other and independently represent H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogenous base, and catalysts A and B are transition met
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
April 28, 2015
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Patent number: 8889772
Abstract: The invention relates to a method for producing mixtures of alkylphosphonous acid and dialkylphosphinic acid salts, characterized in that a) a phosphinic acid source (I) is reacted with olefins (II) in the presence of a catalyst A to obtain a mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or salts or esters thereof, and b) the thus obtained mixture of alkylphosphonous acid (III) and dialkylphosphinic acid (IV) or the salts or esters thereof is reacted with metal compounds of Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na, K and/or a protonated nitrogen base to obtain the corresponding mixtures of alkylphosphonous acid salt (V) and dialkylphosphinic acid salt (VI) of said metals and/or a nitrogen compound, (V) (VI), wherein Y represents Mg, Ca, AI, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Li, Na; K and/or a nitrogen compound and n represents ¼, ?, ½, 1.
Type:
Grant
Filed:
April 20, 2011
Date of Patent:
November 18, 2014
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Sebastian Hoerold, Werner Krause, Martin Sicken
Patent number: 8772519
Abstract: The invention relates to a process for preparing mono-allyl-functionalized dialkylphosphinic acids, esters and salts with allylic compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, or salt or ester thereof (II), b) the alkylphosphonous acid, or salt or ester thereof (II) thus formed is reacted with allylic compounds of the formula (V) in the presence of a catalyst B and of a base to give a mono-allyl-functionalized dialkylphosphinic acid derivative (III), where R1, R2, R3, R4, R5, R6, R7, R8, R9 are the same or different and are each independently, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, and X is H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst syst
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
July 8, 2014
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Patent number: 8664418
Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the alkylphosphonic acid thus obtained, salt or ester (II) thereof is reacted with an ?,?-unsaturated carboxylic acid derivative (V) to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X and Y are the same or different and stand independently of each other for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed b
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
March 4, 2014
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
Patent number: 8614267
Abstract: The invention relates to a method for producing mono-hydroxyfunctionalized dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield a mono-hydroxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed by transition metals and/or transition metal compound
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
December 24, 2013
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken