US3953402A
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US
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Age resistant polymers of ditertiary alkyl-4-hydroxyaryl acrylate and dienes
Assignee: Goodyear Tire and Rubber Co
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Filing: 1970-07-20
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Granted: 1976-04-27
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Expires: 1990-07-20
Abstract
Abstract Antioxidants such as 3,5-di tert.butyl-4-hydroxyphenyl acrylate and 3,5-di tert.butyl-4-hydroxyphenyl methacrylate, age resistant polymers having age resistors physically combined therewith and age resistant polymeric compositions prepared by emulsion free radical polymerization techniques involving the use of said age resistors as monomers.
Inventors
- 👤 Richard H. Kline
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 01:58
CPC Classifications
C; C08; C08F; C08F236/00; C08F236/02; C08F236/04
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
164 words
A process of preparing an age resistant polymeric composition comprising polymerizing in an emulsion free radical polymerization system, a monomer system containing at least one phenolic monomer having the following structural formula: ##EQU5## wherein R and R 1 are tertiary alkyl radicals having from 4 to 8 carbon atoms, R 2 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, carboxymethyl radical and carbalkoxymethyl radicals and wherein R 3 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, phenyl and substituted phenyl radicals having located in the para position at least one radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and alkoxy radicals having 1 to 2 carbon atoms, carboxyl radical and carbalkoxy radicals, and wherein the monomer system contains at least 40 parts by weight of diene monomer per 100 parts by weight of total monomer in the monomer system.
Claim 2
Dependent Claim
164 words
A process of preparing an age resistant polymeric composition comprising polymerizing in an emulsion free radical polymerization system, a monomer system containing at least one phenolic monomer having the following structural formula: ##EQU5## wherein R and R 1 are tertiary alkyl radicals having from 4 to 8 carbon atoms, R 2 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, carboxymethyl radical and carbalkoxymethyl radicals and wherein R 3 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, phenyl and substituted phenyl radicals having located in the para position at least one radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and alkoxy radicals having 1 to 2 carbon atoms, carboxyl radical and carbalkoxy radicals, and wherein the monomer system contains at least 40 parts by weight of diene monomer per 100 parts by weight of total monomer in the monomer system.
Claim 3
Dependent Claim
15 words
The process according to claim 1 wherein the diene monomer is a conjugated diene monomer.
Claim 4
Dependent Claim
15 words
The process according to claim 2 wherein the diene monomer is a conjugated 1,3-diene monomer.
Claim 5
Dependent Claim
31 words
The process according to claim 3 wherein the monomer system contains 0.10 to 10.0 parts by weight of at least one phenolic monomer per 100 parts by weight of total monomer.
Claim 6
Dependent Claim
75 words
The process according to claim 1 wherein the monomer system is comprised of from 50 to 99.9 parts of at least one conjugated diene monomer, 0 to 49.9 parts of at least one compound selected from that group consisting of vinyl monomers and vinylidene monomers and 0.10 to 10.0 parts by weight of at least one phenolic monomer according to claim 1, all parts being by weight per 100 parts by weight of total monomer.
Claim 7
Dependent Claim
81 words
The process according to claim 5 wherein R 2 is selected from the group consisting of hydrogen, methyl, a carboxymethyl radical and carbalkoxymethyl radicals having the following structural formula: ##EQU6## wherein R 4 is an alkyl radical having 1 to 4 carbon atoms and R 3 is selected from the group consisting of hydrogen, a carboxyl radical, phenyl and carbalkoxy radicals having the following structural formula: ##EQU7## wherein R 5 is an alkyl radical having from 1 to 4 carbon atoms.
Claim 8
Dependent Claim
23 words
The process according to claim 6 wherein R 4 and R 5 are selected from the group consisting of methyl and ethyl radicals.
Claim 9
Dependent Claim
15 words
The process according to claim 7 wherein R and R 1 are tertiary butyl radicals.
Claim 10
Dependent Claim
49 words
The process according to claim 1 wherein the emulsion free radical polymerization system contains an initiator system comprised of at least one initiator selected from the group consisting of aralkyl peroxides, aliphatic peroxides, aromatic acyl peroxides, perester peroxides, aralkyl hydroperoxides, aliphatic hydroperoxides, persulfate initiators, perborate initiators and perphosphate initiators.
Claim 11
Dependent Claim
23 words
The process according to claim 1 wherein the emulsion free radical polymerization system contains an initiator system comprised of a reduction/oxidation initiator system.
Claim 12
Dependent Claim
161 words
A polymer containing segmeric units, at least a portion of said units being comprised of at least one of the age resistant segmeric entities having the following structural formula: ##EQU8## wherein R and R 1 are tertiary alkyl radicals having from 4 to 8 carbon atoms, R 2 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, carboxymethyl radical and carbalkoxymethyl radicals and wherein R 3 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, phenyl and substituted phenyl radicals having located in the para position at least one radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and alkoxy radicals having 1 to 2 carbon atoms, carboxyl radical and carbalkoxy radicals, and wherein the polymer contains at least 40 parts by weight of the segmeric form of a diene monomer per 100 parts by weight of the polymer.
Claim 13
Dependent Claim
161 words
A polymer containing segmeric units, at least a portion of said units being comprised of at least one of the age resistant segmeric entities having the following structural formula: ##EQU8## wherein R and R 1 are tertiary alkyl radicals having from 4 to 8 carbon atoms, R 2 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, carboxymethyl radical and carbalkoxymethyl radicals and wherein R 3 is selected from the group consisting of hydrogen; alkyl radicals having from 1 to 4 carbon atoms, phenyl and substituted phenyl radicals having located in the para position at least one radical selected from the group consisting of alkyl radicals having 1 to 4 carbon atoms and alkoxy radicals having 1 to 2 carbon atoms, carboxyl radical and carbalkoxy radicals, and wherein the polymer contains at least 40 parts by weight of the segmeric form of a diene monomer per 100 parts by weight of the polymer.
Claim 14
Dependent Claim
28 words
The polymer according to claim 11 wherein the age resistant segmeric entity comprises 0.10 part to 10.0 parts by weight per 100 parts by weight of the polymer.
Claim 15
Dependent Claim
44 words
The polymer according to claim 11 wherein the segmeric form of the diene monomer is present at a level of at least 50 parts by weight per 100 parts by weight of the polymer and wherein the diene monomer is a conjugated 1,3-diene monomer.
Claim 16
Dependent Claim
12 words
The polymer according to claim 13 wherein the polymer is a solid.
Claim 17
Dependent Claim
65 words
The polymer according to claim 14 wherein the polymer contains from 0.10 part to 10.0 parts by weight per 100 parts by weight of polymer of the age resistant segmeric unit and correspondingly 90 parts to 99.9 parts by weight of at least one segmeric form of at least one comonomer selected from the group consisting of conjugated 1,3-diene monomers, vinyl monomers and vinylidene monomers.
Claim 18
Dependent Claim
24 words
The polymer according to claim 15 wherein the polymer contains at least 50 percent by weight of at least one segmeric form of 1,3-butadiene.
Claim 19
Dependent Claim
74 words
The polymer according to claim 11 wherein the polymer contains 50 to 99.9 parts by weight of the segmeric form of at least one diene monomer, 0 to 49.9 parts by weight of at least one compound selected from the group consisting of vinyl monomers and vinylidene monomers and 0.10 to 5.0 parts by weight of at least one monomeric age resistor, all parts being by weight per 100 parts by weight of polymer.
Claim 20
Dependent Claim
20 words
The polymer according to claim 14 wherein the polymer possesses a number average molecular weight of from 60,000 to 500,000.
Claim 21
Dependent Claim
30 words
The polymer according to claim 14 wherein the polymer possesses a number average molecular weight of at least 60,000 and has a macro gel content of less than 50 percent.
Claim 22
Dependent Claim
81 words
The polymer according to claim 15 wherein R 2 is selected from the group consisting of hydrogen, methyl, a carboxymethyl radical and carbalkoxymethyl radicals having the following structural formula: ##EQU9## wherein R 4 is an alkyl radical having 1 to 4 carbon atoms and R 3 is selected from the group consisting of hydrogen, a carboxyl radical, phenyl and carbalkoxy radicals having the following structural formula: ##EQU10## wherein R 5 is an alkyl radical having from 1 to 4 carbon atoms.
Claim 23
Dependent Claim
23 words
The polymer according to claim 20 wherein R 4 and R 5 are selected from the group consisting of methyl and ethyl radicals.
Claim 24
Dependent Claim
15 words
The polymer according to claim 21 wherein R and R 1 are tertiary butyl radicals.
Claim 25
Dependent Claim
22 words
The process according to claim 1 wherein the phenolic monomer is selected from the group consisting of 3,5-di-t-butyl-4-hydroxyphenyl methacrylate and 3,5-di-t-butyl-4-hydroxyphenyl acrylate.
Claim 26
Dependent Claim
31 words
The polymer according to claim 11 wherein R and R 1 are tertiary butyl, R 2 is selected from the group consisting of hydrogen and methyl and R 3 is hydrogen.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-27 | 1979-10-27 | 1980-04-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-27 | 1983-10-27 | 1984-04-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-27 | 1987-10-27 | 1988-04-27 | $7700.00 | Window Closed / Lapsed |