Stabilizers for synthetic polymers comprising 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester, .beta.-thioalkyl propionic acid ester and phenol
First Claim
1. A stabilizer composition for organic polymeric materials comprising:
- (a) aβ
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;
(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and
(c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR150## wherein;
R1 is selected from the group consisting of ##STR151## Y is selected from the group consisting of hydrogen and O;
R6 is lower alkyl having from one to two carbon atoms;
n is selected from the group consisting of 1, 2, 3 and 4; and
Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR152## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene alkarylidene;
tris (N,N'"'"',N"-alkylene) cyanuric acid;
bis (N,N'"'"'-alkylene) piperazine;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene.
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Abstract
Stabilizers for organic polymeric materials are provided, comprising a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester having the general formula: ##STR1## wherein: R1 is selected from the group consisting of ##STR2## Y is selected from the group consisting of hydrogen and O; R6 is lower alkyl having from one to two carbon atoms;
n is selected from the group consisting of 1, 2, 3 and 4; and
Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR3## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene; aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene; heterocycloalkyl, heterocycloalkylene, heterocycloalkylidene; cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkylene, cycloalkalkyl, cycloalkalkenyl, and cycloalkalkenylene, and amino- and hydroxy-substituted such radicals; a β-thioalkyl propionic acid ester of a polyhydric alcohol, and a phenolic antioxidant.
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Citations
36 Claims
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1. A stabilizer composition for organic polymeric materials comprising:
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(a) aβ
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR150## wherein;
R1 is selected from the group consisting of ##STR151## Y is selected from the group consisting of hydrogen and O;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR152## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene alkarylidene;
tris (N,N'"'"',N"-alkylene) cyanuric acid;
bis (N,N'"'"'-alkylene) piperazine;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24)
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25. A polyvinyl chloride resin composition having improved resistance to deterioration when heated at 350°
- F., comprising a polyinyl chloride resin formed at least in part of the recurring group ##STR164## and having a chlorine content in excess of 49% where X is either hydrogen or chlorine; and
an amount to enhance the resistance to deterioration of the resin of a stabilizer composition comprising;(a) aβ
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR165## wherein;
R1 is selected from the group consisting of ##STR166## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR167## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalk alkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene. - View Dependent Claims (26, 27)
- F., comprising a polyinyl chloride resin formed at least in part of the recurring group ##STR164## and having a chlorine content in excess of 49% where X is either hydrogen or chlorine; and
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28. An olefin polymer composition having improved resistance to deterioration comprising an olefin polymer selected from the group consisting of polymers of alpha-olefins having from two to six carbon atoms and polystyrene, and an amount to enhance the resistance of the polymer to deterioration of a stabilizer composition comprising:
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(a) a β
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR168## wherein;
R1 is selected from the group consisting of ##STR169## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR170## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene. - View Dependent Claims (29, 30)
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31. An acrylonitrile-butadiene-styrene polymer having improved resistance to deterioration when heated at 300°
- F. comprising an acrylonitrile-butadiene-styrene polymer and an amount to enhance its resistance to deterioration of a stabilizer composition comprising;
(a) a β
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR171## wherein;
R1 is selected from the group consisting of ##STR172## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR173## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene.
- F. comprising an acrylonitrile-butadiene-styrene polymer and an amount to enhance its resistance to deterioration of a stabilizer composition comprising;
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32. A polyester resin composition having improved resistance to deterioration comprising a linear polyester resin and an amount to enhance the resistance of the polymer to deterioration of a stabilizer coposition comprising:
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(a) a β
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR174## wherein;
R1 is selected from the group consisting of ##STR175## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR176## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene.
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33. An ethylene-vinyl acetate copolymer composition having improved resistance to deterioration comprising an ethylene-vinyl acetate copolymer and an amount to enhance the resistance of the polymer to deterioration of a stabilizer composition comprising:
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(a) a β
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR177## wherein;
R1 is selected from the group consisting of ##STR178## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR179## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene.
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34. A polyurethane resin composition having improved resistance to deterioration comprising a polyurethane resin and an amount sufficient to improve resistance to deterioration of the resin of a stabilizer composition comprising:
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(a) a β
-thioalkyl propionic acid ester of a polyhydric alcohol in an amount of from about 10 to about 35 parts by weight;(b) a phenolic antioxidant in an amount of from about 10 to about 35 parts by weight; and (c) a 2,2,6,6-tetramethyl-4-piperidyl carboxylic acid ester in an amount from about 90 to about 35 parts by weight and having the general formula;
##STR180## wherein;
R1 is selected from the group consisting of ##STR181## Y is selected from the group consisting of hydrogen and O.sup.. ;
R6 is lower alkyl having from one to two carbon atoms;n is selected from the group consisting of 1, 2, 3 and 4; and Z is an organic radical having a valence from 1 to 4, the valence positions being taken by ##STR182## groups, and from one to about twenty carbon atoms, and selected from the group consisting of alkyl, alkenyl, alkylene, alkenylene, alkylidene;
aryl, arylene, aralkyl, aralkylene, aralkylidene, alkaryl, alkarylene, alkarylidene;
cycloalkyl, cycloalkenyl, cycloalkylene, cycloalkenylene, cycloalkylidene, alkcycloalkyl, alkcycloalkenyl, alkcycloalkenylene, alkcycloalkylene, cycloalkalkyl, cycloalkalkylene, cycloalkalkenyl, cycloalkalkenylene, aminoalkylene, nitriloalkylene, hydroxyalkylene and alkylhydroxyphenalkylene.
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35. An olefin polymer composition having improved resistance to deterioration comprising an olefin polymer selected from the group consisting of polymers of alpha-olefins having from two to six carbon atoms and polystyrene, and an amount to enhance the resistance of the polymer to deterioration of a stabilizer composition comprising tetrakis (methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate)methane in an amount from about 10 to about 35 parts by weight, 1,2,3-tris(lauryl mercaptopropionate) propane in an amount of from about 10 to about 35 parts by weight, and the piperidyl compound:
- ##STR183## in an amount from about 90 to about 35 parts by weight.
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36. A polyurethane resin composition having improved resistance to deterioration comprising a polyurethane resin and an amount to enhance the resistance of the polymer to deterioration of a stabilizer composition comprising 2,6-di-tert-butyl-p-cresol in an amount from about 10 to about 35 parts by weight, 1,3,5,-tris-(ethyl(lauryl mercapto propionate))isocyanurate in an amount of from about 10 to about 35 parts by weight, and tris-(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate in an amount from about 90 to about 35 parts by weight.
Specification