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US4956408A Expired / Lapsed US ⏱️ 0.0 years remaining

Complex acrylates as stabilizer for conjugated diene/monovinyl aromatic copolymers

Assignee: Phillips Petroleum Co
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Filing: 1988-06-13
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Granted: 1990-09-11
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Expires: 2008-06-13
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Abstract

Abstract A conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer is stabilized by the addition of a complex acrylate, in combination with at least one of an alkyl thiopropionate, an organic phosphite and a non-acrylate substituted hindered phenolic compound.

Inventors

  • 👤 Ronald D. Mathis
  • 👤 Alonzo G. Kitchen
  • 👤 Frank J. Szalla

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 03:16
CPC Classifications
C; C08; C08L; C08L9/00; C08L9/06; C08K; C08K5/00; C08K5/04; C08K5/13; C08K5/134

Claims Analysis

Total Claims: 29
Claim 1
Independent Claim 148 words
A method for stabilizing a polymeric composition comprising a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50, which method comprises: incorporating in said copolymer effective amounts of a complex acrylate of the formula ##STR3## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms; and an organic phosphite of the formula (RO).sub.3 P; and a non-acrylate substituted hindered phenolic compound.
Claim 2
Independent Claim 148 words
A method for stabilizing a polymeric composition comprising a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50, which method comprises: incorporating in said copolymer effective amounts of a complex acrylate of the formula ##STR3## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms; and an organic phosphite of the formula (RO).sub.3 P; and a non-acrylate substituted hindered phenolic compound.
Claim 3
Dependent Claim 38 words
A method in accordance with claim 1 wherein the conjugated diene is butadiene and the monovinyl substituted aromatic hydrocarbon is styrene and wherein the weight ratio of said butadiene to said styrene in said copolymer is about 24:76.
Claim 4
Dependent Claim 26 words
A method in accordance with claim 1 wherein said complex acrylate is incorporated in an amount in the range of about 0.05 to about 1.5 phr.
Claim 5
Dependent Claim 15 words
A method in accordance with claim 1 wherein said complex acrylate is 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butyl phenyl acrylate.
Claim 6
Independent Claim 150 words
A method for stabilizing a polymeric composition comprising a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50, which method comprises: incorporating in said copolymer effective amounts of a complex acrylate of the formula ##STR4## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms; and an alkyl thiopropionate of the formula wherein R 4 is an alkyl group having 4-20 carbon atoms.
Claim 7
Independent Claim 150 words
A method for stabilizing a polymeric composition comprising a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50, which method comprises: incorporating in said copolymer effective amounts of a complex acrylate of the formula ##STR4## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms; and an alkyl thiopropionate of the formula wherein R 4 is an alkyl group having 4-20 carbon atoms.
Claim 8
Dependent Claim 26 words
A method in accordance with claim 5 wherein said alkyl thiopropionate is present in an amount in the range of about 0.05 to about 1.5 phr.
Claim 9
Dependent Claim 13 words
A method in accordance with claim 6 wherein said alkylthiopropionate is pentaerythritol tetrakis(3-laurylthiopropionate).
Claim 10
Dependent Claim 26 words
A method in accordance with claim 1 wherein said organic phosphite is present in an amount in the range of about 0.05 to about 2.0 phr.
Claim 11
Dependent Claim 29 words
A method in accordance with claim 1 wherein said non-acrylate substituted hindered phenolic compound is present in an amount in the range of about 0.05 to about 0.5 phr.
Claim 12
Dependent Claim 14 words
A method in accordance with claim 8 wherein said organic phosphite is tris(nonylphenyl) phosphite.
Claim 13
Dependent Claim 17 words
A method in accordance with claim 9 wherein said non-acrylate substituted hindered phenolic compound is n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate.
Claim 14
Independent Claim 100 words
A method for stabilizing a polymeric composition comprising a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, which comprises incorporating in said copolymer an amount in the range of from 0.05 to about 1.5 phr of 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butyl phenyl acrylate, an amount in the range of 0.05 to 2.0 phr of tris(nonylphenyl) phosphite, and an amount in the range of 0.05-0.5 phr of a compound selected from the group consisting of n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, and tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl) propionyloxymethyl] methane.
Claim 15
Independent Claim 100 words
A method for stabilizing a polymeric composition comprising a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, which comprises incorporating in said copolymer an amount in the range of from 0.05 to about 1.5 phr of 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butyl phenyl acrylate, an amount in the range of 0.05 to 2.0 phr of tris(nonylphenyl) phosphite, and an amount in the range of 0.05-0.5 phr of a compound selected from the group consisting of n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, and tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl) propionyloxymethyl] methane.
Claim 16
Dependent Claim 195 words
A composition of matter consisting essentially of an intimate mixture of a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50; a complex acrylate of the formula ##STR5## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms, and wherein said acrylate is present in an amount in the range of about 0.05 to about 1.5 phr; an organic phosphite, wherein said organic phosphite is present in an amount in the range of about 0.05 to about 2.0 phr; and a non-acrylate substitute hindered phenolic compound, wherein said non-acrylate substituted hindered phenolic compound is present in an amount in the range of about 0.05 to about 0.5 phr.
Claim 17
Dependent Claim 195 words
A composition of matter consisting essentially of an intimate mixture of a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of about 5:95 to about 50:50; a complex acrylate of the formula ##STR5## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms, and wherein said acrylate is present in an amount in the range of about 0.05 to about 1.5 phr; an organic phosphite, wherein said organic phosphite is present in an amount in the range of about 0.05 to about 2.0 phr; and a non-acrylate substitute hindered phenolic compound, wherein said non-acrylate substituted hindered phenolic compound is present in an amount in the range of about 0.05 to about 0.5 phr.
Claim 18
Dependent Claim 45 words
A composition in accordance with claim 13 wherein said conjugated diene is butadiene and said monovinyl substituted aromatic hydrocarbon is styrene and wherein the weight ratio of said butadiene to said styrene in said copolymer is in the range of about 5:95 to about 50:50.
Claim 19
Dependent Claim 14 words
A composition in accordance with claim 13 wherein said complex acrylate is 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)4-methyl-6-t-butylphenyl acrylate.
Claim 20
Dependent Claim 12 words
A composition in accordance with claim 13 wherein said phosphite is tris(nonylphenyl)phosphite.
Claim 21
Dependent Claim 26 words
A composition in accordance with claim 13 wherein said non-acrylate substituted hindered phenolic compound is selected from the group consisting of n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate and tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl) propionyloxymethyl]methane.
Claim 22
Dependent Claim 163 words
A composition of matter consisting essentially of an intimate mixture of a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of bout 5:95 to about 50:50; a complex acrylate of the formula ##STR6## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms, and wherein said acrylate is present in an amount in the range of about 0.05 to about 1.5 phr; and an alkyl thiopropionate of the formula ##STR7## wherein R 4 is an alkyl group having 4-20 carbon atoms.
Claim 23
Dependent Claim 163 words
A composition of matter consisting essentially of an intimate mixture of a conjugated diene/monovinyl substituted aromatic hydrocarbon copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of conjugated diene to monovinyl substituted aromatic hydrocarbon in said copolymer is in the range of bout 5:95 to about 50:50; a complex acrylate of the formula ##STR6## and R 1 , R 2 and R 3 are the same or different and are selected from the group consisting of hydrogen, alkyl residues having from 1 to 16 carbon atoms, aryl residues, cycloalkyl residues having from 5 to 9 carbon atoms, and alkyl substituted aryl residues having from 7 to 12 carbon atoms, and wherein said acrylate is present in an amount in the range of about 0.05 to about 1.5 phr; and an alkyl thiopropionate of the formula ##STR7## wherein R 4 is an alkyl group having 4-20 carbon atoms.
Claim 24
Dependent Claim 26 words
A composition in accordance with claim 18 wherein said alkyl thiopropionate is present in an amount in the range of about 0.05 to about 1.5 phr.
Claim 25
Dependent Claim 14 words
A composition in accordance with claim 19 wherein said alkyl thiopropionate is pentaerythritol tetrakis(3-laurylthiopropionate).
Claim 26
Dependent Claim 73 words
A composition comprising an intimate mixture of a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, and 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butylphenyl acrylate in an amount in the range of about 0.05 to about 1.5 phr, and pentaerythritol tetrakis(3-laurylthiopropionate) in an amount in the range of about 0.05 to about 1.5 phr.
Claim 27
Dependent Claim 73 words
A composition comprising an intimate mixture of a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, and 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butylphenyl acrylate in an amount in the range of about 0.05 to about 1.5 phr, and pentaerythritol tetrakis(3-laurylthiopropionate) in an amount in the range of about 0.05 to about 1.5 phr.
Claim 28
Dependent Claim 89 words
A composition comprising an intimate mixture of a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, and 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butylphenyl acrylate in an amount in the range of about 0.05 to about 1.5 phr, and n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate in an amount in the range of about 0.05 to about 0.5 phr, and tris(nonylphenyl) phosphite in an amount in the range of about 0.05 to about 2.0 phr.
Claim 29
Dependent Claim 89 words
A composition comprising an intimate mixture of a butadiene/styrene copolymer wherein said copolymer is selected from the group consisting of linear or branched block, tapered block or random block copolymers, wherein the weight ratio of butadiene to styrene is about 24:76, and 2-(2-hydroxy-3-t-butyl-5-methylbenzyl)-4-methyl-6-t-butylphenyl acrylate in an amount in the range of about 0.05 to about 1.5 phr, and n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate in an amount in the range of about 0.05 to about 0.5 phr, and tris(nonylphenyl) phosphite in an amount in the range of about 0.05 to about 2.0 phr.

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