Acyclic Divalent Chalcogen Single Bonded Directly To The Ring Phosphorus (e.g., Cyclic Phosphites, Etc.) Patents (Class 558/78)
  • Patent number: 5717126
    Abstract: Phosphorus-containing calixarenes of the general formula I ##STR1## and a process for their preparation are described. Additionally, a process for the preparation of aldehydes by the hydroformylation of C.sub.3 -C.sub.20 -olefins by means of rhodium or ruthenium carbonyl complexes, in which the phosphorus-containing calixarenes of the formula I are used as ligands, is described.
    Type: Grant
    Filed: August 7, 1995
    Date of Patent: February 10, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rocco Paciello, Michael Roper, Heinz-Josef Kneuper, Ernst Langguth, Peter Michael Lorz
  • Patent number: 5631392
    Abstract: The invention relates to a process for preparing an aldehyde compound by hydroformylation of an ethylenically unsaturated organic compound, using a catalyst system which includes a Group VIII metal and a novel bidentate phosphite ligand. The bidentate phosphite ligand has a chemical structure according to formula (1), ##STR1## wherein R.sup.1 and R.sup.3 are respectively substituted or unsubstituted organic groups which may be the same or different, and wherein R.sup.2 is a substituted or unsubstituted tetravalent organic group.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: May 20, 1997
    Assignees: DSM N.V., E.I. Du Pont de Nemours and Company
    Inventors: Carolina B. Hansen, Antonius J. J. M. Teunissen
  • Patent number: 5625090
    Abstract: The new crystalline modification of 1,1',1"-nitrilo{triethyl-tris-[2,2'-methylene-bis(4,6-di-tert-butylphenyl) ]phosphite} is obtained by crystallizing said compound from the melt at elevated temperatures. This crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene. The instant crystalline form exhibits better handling characteristics, apparent density, flowability, meterability, storage and hydrolytic stability than the prior art powdery product.
    Type: Grant
    Filed: November 2, 1995
    Date of Patent: April 29, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum
  • Patent number: 5618961
    Abstract: A diphosphite is provided derived from phosphorous trihalide, tetra alkyl hindered bisphenol, and a neoalkyl diol. The phosphites exhibit improved stability and are useful as thermal oxidative stabilizers for thermoplastic compositions.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: April 8, 1997
    Assignee: General Electric Company
    Inventor: James A. Mahood
  • Patent number: 5618962
    Abstract: A diphosphite is provided derived from phosphorous trihalide, tetra alkyl hindered bisphenol, and a neoalkyl diol. The phosphites exhibit improved stability and are useful as thermal oxidative stabilizers for thermoplastic compositions.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: April 8, 1997
    Assignee: General Electric Company
    Inventor: James A. Mahood
  • Patent number: 5594053
    Abstract: An stabilized thermoplastic composition comprising a stabilizing amount of a phosphite of the formula: ##STR1## R.sub.1 is independently selected from the group consisting of alkyl groups having from 1 to 9 carbon atoms, Y is independently selected from the group consisting of hydrogen, halogen, or alkyl; and the --O--X groups are positioned at the respective ortho- or para- positions with respect to the diphenyl linkage, the remaining ortho- and para- positions with respect to the --O--X linkage being occupied by R.sub.1 whereby the --0--X groups are hindered by the presence of at least one R.sub.1 group; R.sup.
    Type: Grant
    Filed: January 22, 1996
    Date of Patent: January 14, 1997
    Assignee: General Electric Company
    Inventors: Roger W. Avakian, Vaikunth S. Prabhu, William P. Enlow, Carloss L. Gray
  • Patent number: 5523448
    Abstract: A diphosphite is provided derived from phosphorous trihalide, tetra alkyl hindered bisphenol, and a neoalkyl diol. The phosphites exhibit improved stability and are useful as thermal oxidative stabilizers for thermoplastic compositions.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: June 4, 1996
    Assignee: General Electric Company
    Inventor: James A. Mahood
  • Patent number: 5512621
    Abstract: The alpha crystalline modification of 2,2',2"-nitrilo triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite! is obtained by crystallizing said compound from selected solvents, preferably from a mixture of an aromatic hydrocarbon solvent and a lower alkanol.The alpha crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: April 30, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum, Paul A. Odorisio
  • Patent number: 5489636
    Abstract: The new amorphous modification of 1,1',1"-nitrilo{tri-2-propyl-tris-[2,2'-ethylidene-bis(4,6-di-tert-butylph enyl)]phosphite } is obtained by cooling rapidly said compound from the melt to ambient temperature.This amorphous form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: February 6, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor
  • Patent number: 5489635
    Abstract: The new crystalline modification of 1,1',1"-nitrilo{tri-2-propyl-tris[2,2'-ethylidene-bis(4,6-di-tert-butylphe nyl)]phosphite} is obtained by crystallizing said compound from the melt at elevated temperatures.This crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: February 6, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor
  • Patent number: 5486641
    Abstract: The beta crystalline form of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl) phosphite] is obtained by the thermal treatment of the phosphite compound at 125.degree. C. in the absence of any solvent.The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: January 23, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor
  • Patent number: 5475042
    Abstract: Novel cyclic pyrophosphite of formula I ##STR1## are prepared from the corresponding 6-chloro and 6-oxo phosphepins or phosphocins. The cyclic pyrophosphites are effective process stabilizers for organic materials subject to thermal, oxidative or actinic induced degradation, particularly polyolefins and especially polypropylene.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: December 12, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Sai P. Shum, Stephen D. Pastor, Andrea R. Smith
  • Patent number: 5464889
    Abstract: Neoalkyl phosphite provided which exhibit improved levels of stability. The phosphites are hindered and are useful in stabilizing thermoplastic compositions.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: November 7, 1995
    Assignee: General Electric Company
    Inventor: James A. Mahood
  • Patent number: 5438086
    Abstract: A class of hydrolytically stable bis(aralkylphenyl)pentaerythritol diphosphites is disclosed, which is suitable as an antioxidant additives in polyolefins, particularly, in polypropylene. The diphosphites are of low volatility, have a high thermal decomposition temperature and resist yellowing when blended into a polyolefin base. A preferred diphosphite is bis(2,4-dicumylphenyl)pentaerythritol diphosphite.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: August 1, 1995
    Inventors: Donald R. Stevenson, Satyanarayana Kodali
  • Patent number: 5414033
    Abstract: Novel compounds of the formula I and formula II ##STR1## in which R and R.sub.1, independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl or together with the carbon atom to which they are attached form a 3,4-dehydrocyclohexylidene ring,R.sub.2 is hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.3 is C.sub.1 -C.sub.8 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4, R.sub.5 and R.sub.6, independently of one another, are hydrogen or C.sub.1 -C.sub.4 alkyl, when alkyl, R.sub.4, R.sub.5 and R.sub.6 together containing 1 to 4 carbon atoms, andR.sub.7 and R.sub.8 are hydrogen or together an additional direct bond, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: May 9, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Nesvadba
  • Patent number: 5414028
    Abstract: Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I ##STR1## where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.
    Type: Grant
    Filed: February 17, 1994
    Date of Patent: May 9, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Joseph E. Babiarz
  • Patent number: 5382701
    Abstract: A method for producing a potassium paradiphenyl phosphino sulfonate ligand which comprises reacting potassium diphenyl phosphide with a lithium salt of para-chloro benzenesulfonic acid in the presence of tetrahydrofuran at elevated temperatures.
    Type: Grant
    Filed: November 18, 1993
    Date of Patent: January 17, 1995
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Elena N. Suciu, Joel R. Livingston, Jr., Edmund J. Mozeleski
  • Patent number: 5362898
    Abstract: A bis(pentaerythritol phosphate alcohol) alkylphosphonate compound, such as one comprising an alkyl group of from about one to four carbon atoms, preferably bis(pentaerythritol phosphate alcohol) methylphosphonate, is a flame retardant compound. Such a compound can be prepared by the transesterification of a diphenyl alkyl phosphonate carrying the desired alkyl group with pentaerythritol phosphate alcohol. An alternative process of preparation comprises the reaction of pentaerythritol phosphate alcohol, a trialkylamine, and an alkylphosphonic dihalide.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: November 8, 1994
    Assignee: Akzo Nobel nv
    Inventor: Jeffrey E. Telschow
  • Patent number: 5334739
    Abstract: The alpha crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl) O"phosphite] is obtained by crystallizing said compound from selected solvents, preferably from a mixture of an aromatic hydrocarbon solvent and a lower alkanol.The alpha crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: August 2, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum, Paul A. Odorisio
  • Patent number: 5331031
    Abstract: The gamma crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite] is obtained by crystallizing or recrystallizing said compound from an alkanol of 4 to 8 carbon atoms.The gamma crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: July 19, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum, Paul A. Odorisio
  • Patent number: 5326801
    Abstract: New organic phosphites of a specific formula are used as stabilizers for polymers and other organic materials.
    Type: Grant
    Filed: July 28, 1992
    Date of Patent: July 5, 1994
    Assignee: Himont Incorporated
    Inventors: Marco Foa, Sauro Strologo
  • Patent number: 5326802
    Abstract: The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tertbutyl-1,1'-biphenyl-2,2 '-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures.The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: July 5, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum
  • Patent number: 5300617
    Abstract: A method for producing a potassium para-diphenyl phosphino sulfonate ligand which comprises reacting potassium diphenyl phosphide with a lithium salt of para-chloro benzenesulfonic acid in the presence of tetrahydrofuran at elevated temperatures.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: April 5, 1994
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Elena N. Suciu, Joel R. Livingston, Jr., Edmund J. Mozeleski
  • Patent number: 5298541
    Abstract: A process for the preparation of aryl phosphonites of the formula V ##STR1## wherein the radicals and n are defined in the disclosure. The invention further relates to a plastic molding composition, in particular a polyolefin molding composition containing aryl phosphonites of the formula V.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: March 29, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Bohshar, Hans-Jerg Kleiner, Gerhard Pfahler
  • Patent number: 5280057
    Abstract: There are disclosed novel compounds of formula I ##STR1## wherein n is 0, 1 or 2, R and R.sub.1 are each independently of the other C.sub.1 -C.sub.4 alkyl or, when taken together, are a 2,3-dehydropentamethylene radical,R.sub.2 is C.sub.1 -C.sub.4 alkyl or C.sub.5 -C.sub.6 cycloalkyl, andR.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.5 -C.sub.6 cycloalkyl, R.sub.4, R.sub.5, R.sub.6 and R.sub.7, if n=1, are each independently of one another hydrogen or C.sub.1 -C.sub.4 alkyl, or, if n=0 and if n=2, are hydrogen,as stabilisers for protecting organic materials against thermal, oxidative or light-induced degradation.
    Type: Grant
    Filed: January 13, 1993
    Date of Patent: January 18, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Nesvadba
  • Patent number: 5276076
    Abstract: The amorphous solid modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2, 2'-diyl)phosphite] is obtained by melting said compound and rapidly cooling the melt.The amorphous solid is an effective process stabilizer for polyolefins, particularly polypropylene.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: January 4, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, Sai P. Shum
  • Patent number: 5239103
    Abstract: 3,7,9-Trioxa-1-aza-2,8-diphosphaspiro[4.5]decanes of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, alkyl, cycloalkyl, bicycloalkyl, tricycloalkyl or aryl; or can be halogen when n or m is zero,R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently hydrogen, alkyl, aralkyl or aryl;X and Y are independently --O--, --S-- or --NR.sub.16 -- where R.sub.16 is alkyl, cycloalkyl, alkenyl, aryl or aralkyl;W and Z are independently O or S; andn, m, o and p are independently zero or 1, are effective in stabilizing organic materials against the deleterious effects of oxygen, heat and/or actinic radiation.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: August 24, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Paul A. Odorisio, Sai P. Shum, Stephen D. Pastor
  • Patent number: 5162548
    Abstract: New organic phosphites of the formula ##STR1## are used as stabilizers for polymers and other organic materials. The definition of groups R, R', and R.sub.1 may be found in the disclosure.
    Type: Grant
    Filed: November 19, 1991
    Date of Patent: November 10, 1992
    Assignee: Himont Incorporated
    Inventors: Marco Foa', Sauro Strologo
  • Patent number: 5142083
    Abstract: Hydrolytically stable phosphite compositions for melt flow and color stabilization of thermoplastics may be prepared from crude tetrahydroabietyl alcohol. The phosphites may be prepared by reacting said alcohol with an organophosphite, such as by transesterification. Other synthesis techniques may also be used.
    Type: Grant
    Filed: July 16, 1991
    Date of Patent: August 25, 1992
    Assignee: General Electric Company
    Inventor: William P. Enlow
  • Patent number: 5137950
    Abstract: The present invention provides an improved process for making diphosphaspiroundecanes and product-by-process, wherein the process comprises reacting a hydroxyl-substituted organic compound, phosphorous trichloride and pentaerythritol to form an organic-substituted diphosphaspiroundecane such that formation of said organic-substituted diphosphaspiroundecane takes place in the presence of a tri-n-alkylamine having n-alkyl moieties such that each n-alkyl moiety has at least three carbon atoms. The present invention is also directed to bis-3,9-(2,6-di-t-alkyl-4-alkylphenoxy)-2,4,8,10-tetroxa-3,9-diphosphaspri o[5.5]undecanes and polymer compositions containing an effective amount of same.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: August 11, 1992
    Assignee: Borg-Warner Specialty Chemicals, Inc.
    Inventors: Stephen J. Hobbs, Kevin J. Sheehan, William P. Enlow
  • Patent number: 5103035
    Abstract: Bis(alkylphenyl)pentaerythritol diphosphite is produced by forming a reaction mass from phosphorous trichloride, pentaerythritol, a chlorinated hydrocarbon solvent and a heterocyclic tertiary amine catalyst followed by the addition of an alkylphenol to the reaction mass. The process further features the use of mild conditions.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: April 7, 1992
    Assignee: Ethyl Corporation
    Inventors: Hassan Y. Elnagar, Kestutis A. Keblys
  • Patent number: 5075482
    Abstract: 3,7,9-Trioxa-1-aza-2,8-diphosphaspiro[4.5]decanes of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, alkyl, cycloalkyl, bicycloalkyl, tricycloalkyl or aryl; or can be halogen when n or m is zero,R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently hydrogen, alkyl, aralkyl or aryl;X and Y are independently --O-- --S--, or --NR.sub.16 -- where R.sub.16 is alkyl, cycloalkyl, alkenyl, aryl or aralkyl;W and Z are independently O or S; andn, m, o and p are independently zero or 1, are effective in stabilizing organic materials against the deleterious effects of oxygen, heat and/or actinic radiation.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: December 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Raymond Seltzer, Paul A. Odorisio, Sai P. Shum, Stephen D. Pastor
  • Patent number: 5059710
    Abstract: This invention relates to novel ionic phosphites and the use thereof as ligands in homogenous transition metal catalyzed processes, especially hydroformylation.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: October 22, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Anthony G. Abatjoglou, David R. Bryant
  • Patent number: 5023285
    Abstract: A composition is provided which comprises a 3,9-bis (2,4,6-tri-t-alkylphenoxy)-2,4,8,10-tetroxa-3,9-diphosphaspiro[5.5]undecan e, and polymer compositions are provided which include a polymer and an effective amount of one or more 3,9-bis(2,4,6-tri-t-alkylphenoxy)-2,4,8,10-tetroxa-3,9-diphosphaspiro[5.5] undecane.
    Type: Grant
    Filed: July 25, 1988
    Date of Patent: June 11, 1991
    Assignee: G E Specialty Chemicals
    Inventor: William E. Horn
  • Patent number: 4956406
    Abstract: Disclosed are novel bis-cyclic phosphite compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from hydrogen, alkyl, aralkyl, aryl, carboxy, alkoxycarbonyl or halogen;each R.sup.2 is independently selected from hydrogen, alkyl, aralkyl, alkoxy, aryl, carboxyl, alkoxycarbonyl or halogen;each R.sup.3 and R.sup.4 is alkyl; andA is 1,3- or 1,4-phenylene.Also disclosed are synthetic polymeric materials stabilized with one or more of the above compounds.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: September 11, 1990
    Assignee: Eastman Kodak Company
    Inventors: Garry L. Myers, Richard H. S. Wang
  • Patent number: 4929654
    Abstract: Disclosed are novel cyclic phosphite compounds having the formula ##STR1## wherein each R.sup.1 is independently selected from hydrogen, alkyl, aralkyl, aryl, carboxy, alkoxycarbonyl or halogen;each R.sup.2 is independently selected from hydrogen, alkyl, aralkyl, alkoxy, aryl, carboxy, alkoxycarbonyl or halogen;R.sup.3 is (a) hydrogen, alkyl, cyclohexyl or aryl when n is 1; (b) alkylene, cyclohexylene, cyclohexylenedialkylene, arylene or a divalent group having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined above and A.sup.2 is 1,3- or 1,4-phenylene when n is 2; (c) alkanetriyl when n is 3; or alkanetetrayl when n is 4;n is 1, 2, 3 or 4; andA.sup.1 is 1,3-phenylene.Also disclosed are synthetic polymeric materials stabilized with one of the above compounds and phosphite chloride compounds from which the above compounds are prepared.
    Type: Grant
    Filed: October 4, 1988
    Date of Patent: May 29, 1990
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Garry L. Myers
  • Patent number: 4888371
    Abstract: Bis(2,6-di tert butyl-4-branched propyl or butyl phenyl)-pentaerythritol spiro phosphites are provided having the formula: ##STR1## wherein R is a branched propyl or butyl group, such as isopropyl, iso-butyl, or sec-butyl, as well as synthetic resin compositions having enhanced resistance to deterioration upon exposure to the heat and light comprising such as bis(2,6-di-t-butyl-4-branched propyl or butyl phenyl)pentaerythritol spiro phosphites.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: December 19, 1989
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Kenji Tajima, Tetsuo Tsuboi, Ryozo Arata
  • Patent number: 4885401
    Abstract: Transition metal-bis-phosphite catalyzed carbonylation processes, especially hydroformylation, as well as transition metal-bis-phosphite compositions, bis-phosphite ligands and transition metal-bis-phosphite catalysts.
    Type: Grant
    Filed: March 31, 1988
    Date of Patent: December 5, 1989
    Assignee: Union Carbide Corporation
    Inventors: Ernst Billig, Anthony G. Abatjoglou, David R. Bryant
  • Patent number: 4855345
    Abstract: Compounds of the formula I ##STR1## in which n is 1, 2 or 3, R.sup.1 is C.sub.1 -C.sub.5 -alkyl, cyclohexyl or .alpha.-methylcyclohexyl and, if n is 1, X is a group of the formula II or III ##STR2## in which R.sup.2 and R.sup.3 independently of one another are C.sub.1 -C.sub.8 -alkyl or cyclohexyl, Y is a direct bond, --S--, >S.dbd.O or a radical --CR.sup.4 R.sup.5 -- in which R.sup.4 is hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.5 -C.sub.8 -cycloalkyl, phenyl or benzyl and R.sup.5 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and Z is 1,2-alkylene or 1,3-alkylene having not more than 15 carbon atoms or o-phenylene, and, if n is 2, X is a group of the formula IV or V ##STR3## in which R.sup.6 is methyl or ethyl, and, if n is 3, X is a phosphorus atom, are suitable for stabilizing organic material against light-induced and/or thermo-oxidative degradation.
    Type: Grant
    Filed: June 10, 1987
    Date of Patent: August 8, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Siegfried Rosenberger, Hans-Rudolf Meier
  • Patent number: 4739090
    Abstract: A process for preparing diaryl pentaerythritol diphosphites by reaction of phosphorous trichloride, pentaerythritol and an alkyl phenol having the formula ##STR1## wherein: R.sub.1 is selected from the group consisting of tertiary alkyl having from about four to about eight carbon atoms and cyclohexyl; andR.sub.2 and R.sub.3 are each selected from the group consisting of hydrogen and alkyl having from one to about eight carbon atoms;in the presence of a catalyst selected from the group consisting of amines; quaternary ammonium salts; amides of carboxylic acids; amides of oxygen acids of phosphorus; ureas; thioureas; and quaternary phosphonium salts.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: April 19, 1988
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Kenji Tajima, Masayuki Takahashi, Kazunori Nishikawa, Takashi Takeuchi
  • Patent number: 4694094
    Abstract: New organic compounds containing a phosphorus heterocycle of the phosphonite type, in which the phosphorus atom is connected on the one hand to an oxygen atom and on the other hand to an oxygen, sulphur or nitrogen atom, characterized by comprising two of such heterocycles, the two phosphorus atoms being connected by a hydrocarbon group. Preparation of these diphosphonites by the action of a tetrahalogeno- or tetraminodiphosphine upon a diol or an alcohol carrying a phenol, thiol, enol, acid or amine function.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: September 15, 1987
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Sylvain Juge, Yvonne Legras
  • Patent number: 4692540
    Abstract: The present invention relates to a process for the preparation of pentaerythritol esters of phosphorous acid derivatives by reacting pentaerythritol with a phosphorous trihalide and a phenol in the presence of a quaternary salt or a polyether.The use of such catalysts is not only able to improve the yield, but also makes it possible for the entire process to be carried out in one step by adding the phenol at the start of the reaction of pentaerythritol with the phosphorous halide.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: September 8, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Hugo Illy, Bjorn Schliebs, Wilhelm Hess
  • Patent number: 4692539
    Abstract: Pentaerythritol diphosphites corresponding to the formula ##STR1## being useful for stabilizing organic materials against thermal, oxidative and actinic degradation and a process for the preparation thereof.
    Type: Grant
    Filed: October 24, 1986
    Date of Patent: September 8, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: John D. Spivack
  • Patent number: 4673701
    Abstract: Alkylidene bisphenol phosphites and phosphates having 2,2,6,6-tetramethyl piperidinyl groups are provided having the formula: ##STR1## wherein: R.sub.1 is alkyl having from one to about twelve carbon atoms;R.sub.2, R.sub.3 and R.sub.4 are each selected from the group consisting of hydrogen and alkyl having from one to about twelve carbon atoms;m is 0 or 1;n is 0 or 1;X is selected from the group consisting of ##STR2## wherein: R.sub.5 is selected from the group consisting of hydrogen, oxyl O.sup.2, alkyl having from one to about twelve carbon atoms; arylalkyl having from seven to about eighteen carbon atoms; 2,3-epoxypropyl, acyl having from one to about eight carbon atoms and ##STR3## in which R.sub.6 is selected from the group consisting of hydrogen, alkyl having from one to about twelve carbon atoms and phenyl, and Y.sub.1 is selected from the group consisting of hydrogen; acyl having from one to about twelve carbon atoms; and ##STR4## Z.sub.1 is selected from the group consisting of ##STR5## wherein R.
    Type: Grant
    Filed: December 28, 1984
    Date of Patent: June 16, 1987
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Ryozo Arata
  • Patent number: 4670492
    Abstract: Cyclic bis and tris phosphites are provided having the formula: ##STR1## wherein: A is selected from the group consisting of sulfur; oxygen; alkylidene having from one to about six carbon atoms; cycloalkylidene having from three to about eight carbon atoms; and phenyl and alkyl phenyl alkylidene having from seven to about fourteen carbon atoms;R is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; and phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;R.sub.1 is selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; and phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;n is 2 or 3;R.sub.2 is ##STR2## wherein: m=0 when n is 2; and 1 when n is 3;R.sub.3, R.sub.4, R.sub.5, R.sub.
    Type: Grant
    Filed: October 22, 1985
    Date of Patent: June 2, 1987
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Tohru Haruna, Etsuo Tobita
  • Patent number: 4665211
    Abstract: An improved transesterification process for preparing bis-(2,4-dialkylphenyl) pentaerythritol phosphates using n-alkanes or cycloalkanes as solvents to provide high spiro/cage isomer ratios.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: May 12, 1987
    Assignee: Borg-Warner Chemicals, Inc.
    Inventors: Gary V. Marlin, James F. York