← Back to Patent Explorer
US3625874A Expired / Lapsed US ⏱️ 0.0 years remaining

Phenol-cyclic polyolefin reaction products as stabilizers for polymers

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1968-02-19
•
Granted: 1971-12-07
•
Expires: 1988-02-19
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

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 21:29
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

References Cited (Backward Citations)

US2864868A Cited
US3124555A Cited
GB691043A Cited
US2801981A Cited
US2852568A Cited
US2952662A Cited
US3383362A Cited
FR1474754A Cited
US3431310A Cited

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

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag