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US3625874A
Expired / Lapsed
US
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Phenol-cyclic polyolefin reaction products as stabilizers for polymers
Assignee: Goodyear Tire and Rubber Co
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Filing: 1968-02-19
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Granted: 1971-12-07
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Expires: 1988-02-19
Abstract
Abstract Reaction products of monocyclic and bicyclic diolefins with phenols as age resistors for polymers.
Inventors
- 👤 Kirkwood S Cottman
- 👤 William S Hollingshead
- 👤 Ronald B Spacht
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 23:05
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/13; C08G; C08G65/00; C08G65/002; C08G65/005; C08G65/34; C08G65/38; C08G8/00; C08G8/28; C08G8/30
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
29 words
The reaction product of claim 1 wherein (B) is selected from the group consisting of (a) cyclooctadienes and alkylated cycloocatadienes and (b) compounds conforming to the following structural formulas:
Claim 2
Dependent Claim
14 words
An olefin polymer containing, in an antioxidant amount, the reaction product of claim 1.
Claim 3
Dependent Claim
14 words
An olefin polymer containing, in an antioxidant amount, the reaction product of claim 2.
Claim 4
Dependent Claim
248 words
The olefin polymer according to claim 3 wherein the phenol is selected from the group consisting of phenol o,m,p-cresol o,m,p-isopropyl phenol o,m,p-pRopyl phenol o,m,p-ethyl phenol o,m,p-methoxy phenol phenol o,m,p-ethoxy phenol o,m,p-propoxy phenol p-butyl phenol p-hexyl phenol p-octyl phenol, and p-dodecyl phenol, the monocyclic unsaturated hydrocarbon is selected from the group consisting of 1,4-cycloheptadiene 2-methyl-cycloheptadiene-1,4 4-methyl-cycloheptadiene-1,4 1,3-dimethyl-cycloheptadiene-1,4 1,5-dimethyl-cycloheptadiene-1,4 1,3- cycloheptadiene 1-methyl- cycloheptadiene-1,3 3-methyl cycloheptadiene-1,3 1,4-dimethyl-cycloheptadiene-1,3 1,3-cyclooctadiene 3-methyl-cyclooctadiene-1,3 1,3-dimethyl-cyclooctadiene-1,3 1,4-cyclooctadiene 5-methyl-cyclooctadiene-1,4 1,5-dimethyl-cyclooctadiene-1,4 1,5-cyclooctadiene 3-methyl-cyclooctadiene-1,5 1,4-diemthyl-cyclooctadiene-1,5 1,5-cyclododecadiene 1,7-cyclododecadiene, and 1,5,9,-cyclododecatriene, the bicyclic unsaturated hydrocarbon is selected from the group consisting of bicyclo(2.2.1)-2,5-heptadiene 2-methyl bicyclo( 2.2.1)-2,5-heptadiene 3-methyl bicyclo(2.2.1-2,5-heptadiene 4-methyl bicyclo( 2.2.1-2,5-heptadiene 2,4-dimethyl bicyclo(2.2.1)2,5-heptadiene bicyclo( 3.4.0.)nonadiene-2,7 bicyclo( 3.4.0)-7-methyl nonadiene-2,7 bicyclo3.4.0)-8-methylnonadiene -2,7 bicyclo( 3.4.0)-6-methyl-nonadiene-2,7 (3.4.0-9-methyl-nonadiene-2,7 bicyclo(3.4.0)3,8-dimethyl nonadiene-2,7 bicyclo( 3.4.0)-3,7-dimethyl nonadiene-2,7 bicyclo( 2.4.0octadiene-2,6 bicyclo( 2.4.0-5-methyl octadiene-2,6 bicyclo( 2.4.0-6-methyl octadiene-2,6 bicyclo( 2.4.0)-7-methyl octadiene-2,6 bicyclo( 2.4.0)-5,7-dimethyl octadiene-2,6 spiro( 4.4)nonadiene-2,6 spiro( 4.4)-6-methyl nonadiene-2,6 spiro( 4.4)-6-methyl nonadiene-2,6 spiro( 4.4)-3,7-dimethyl nonadiene-2,6 spiro( 4.4)-2,6-dimethyl nonadiene-2,6 bicyclo( 3.3.0)octadiene-2,6 bicyclo( 3.3.0)-6-methyl octadiene-2,6 bicyclo( 3.3.0)-7-methyl octadiene-2,6 bicyclo(3.3.0)-2,5-dimethyl octadiene-2,6and bicyclo( 3.3.0)-2,6-dimethyl octadiene-2,6 and the tertiary olefin is selected from the group consisting of isobutylene 2-methyl-1-butene 2-methyl-1-pentene 2-methyl-2-pentene 2-methyl-1-hexene 2-methyl -2-hexene, and diisobutylene, and wherein the molar ratio of the diolefin to the phenol is 3:1 to 1:5 and the reaction between the phenol and diolefin is conducted at a temperature between 80* C. and 150* C., wherein the Friedel-Craft-type catalyst is selected from the group consisting of boron trifluoride and complexes based on boron trifluoride and wherein the subsequent reaction with the tertiary olefin is conducted at a temperature between 60* C. and 80* C.
Claim 5
Dependent Claim
20 words
The olefin polymer according to claim 3 wherein (B) is a bicyclic unsaturated hydrocarbon conforming to the following structural formula
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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) | 1974-12-06 | 1975-06-07 | 1975-12-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1978-12-06 | 1979-06-07 | 1979-12-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1982-12-06 | 1983-06-07 | 1983-12-07 | $7700.00 | Window Closed / Lapsed |