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US4414408A Expired / Lapsed US ⏱️ 0.0 years remaining

Phenolic antioxidants

Assignee: Goodyear Tire and Rubber Co
•
Filing: 1982-02-16
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Granted: 1983-11-08
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Expires: 2002-02-16
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Abstract

Abstract Two antioxidants functioning by different mechanisms are combined chemically into one molecule, allowing optimization of their antioxidant properties.

Inventors

  • 👤 Kirkwood S. Cottman

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 11:09
CPC Classifications
C; C09; C09K; C09K15/00; C09K15/04; C07; C07C; C07C323/00

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 270 words
Compounds comprising the reaction product of a polyphenolic compound having the formula ##STR4## with an ester forming compound of the general formula ##STR5## which are then joined through a sulfur atom to form compounds having a general formula selected from the group consisting of ##STR6## wherein Z is a phenoxy radical derived from a polyphenolic compound having structural formula (A) and wherein R 1 and R 2 are the same or different radicals selected from the group consisting of hydrogen, alkyl radicals containing from 1 to 16 carbon atoms, cycloalkyl radicals containing from 5 to 8 carbon atoms, aralkyl radicals containing from 7 to 12 carbon atoms and unsubstituted aryl radicals containing from 6 to 12 carbon atoms, X is the same or different radical selected from the group consisting of (1) cyclic dienes with non-adjacent carbon to carbon double bonds within the ring structure having from 5 to 20 carbon atoms from which the divalent species are prepared and (2) divalent species selected from the group consisting of --S--, ##STR7## --O--, --CH 2 -- and --S--S-- and wherein n is selected from the group consisting of 0 and integers from 1 to 5 and wherein R 3 is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 2 carbon atoms, R 4 is selected from the group consisting of hydrogen, alkyl radicals having from 1 to 4 carbon atoms, aralkyl radicals having from 7 to 9 carbon atoms, substituted or unsubstituted aryl radicals having from 6 to 8 carbon atoms and wherein V is selected from the group consisting of chlorine, iodine and bromine.
Claim 2
Dependent Claim 270 words
Compounds comprising the reaction product of a polyphenolic compound having the formula ##STR4## with an ester forming compound of the general formula ##STR5## which are then joined through a sulfur atom to form compounds having a general formula selected from the group consisting of ##STR6## wherein Z is a phenoxy radical derived from a polyphenolic compound having structural formula (A) and wherein R 1 and R 2 are the same or different radicals selected from the group consisting of hydrogen, alkyl radicals containing from 1 to 16 carbon atoms, cycloalkyl radicals containing from 5 to 8 carbon atoms, aralkyl radicals containing from 7 to 12 carbon atoms and unsubstituted aryl radicals containing from 6 to 12 carbon atoms, X is the same or different radical selected from the group consisting of (1) cyclic dienes with non-adjacent carbon to carbon double bonds within the ring structure having from 5 to 20 carbon atoms from which the divalent species are prepared and (2) divalent species selected from the group consisting of --S--, ##STR7## --O--, --CH 2 -- and --S--S-- and wherein n is selected from the group consisting of 0 and integers from 1 to 5 and wherein R 3 is selected from the group consisting of hydrogen and alkyl radicals having from 1 to 2 carbon atoms, R 4 is selected from the group consisting of hydrogen, alkyl radicals having from 1 to 4 carbon atoms, aralkyl radicals having from 7 to 9 carbon atoms, substituted or unsubstituted aryl radicals having from 6 to 8 carbon atoms and wherein V is selected from the group consisting of chlorine, iodine and bromine.
Claim 3
Dependent Claim 28 words
Compounds as described in claim 1 wherein R 1 is an alkyl radical having from 1 to 2 carbon atoms and is para to a phenolic hydroxyl group.
Claim 4
Dependent Claim 39 words
Compounds as described in claim 1 wherein the polyphenolic compounds are treated with from one mole to 0.1 mole of ester forming compound per functional hydroxyl group, more preferably at least one functional hydroxyl group per polyphenolic molecule esterified.
Claim 5
Dependent Claim 32 words
Compounds as described in claim 1 wherein the polyphenolic compounds are selected from the group consisting of 2,6-bis-(2-hydroxy-3-tert.butyl-5-methylbenzyl)-4-methylphenol; 2,2'-methylene-bis-(4-methyl-6-tert.butyl phenol); 2,2'-methylene-bis-(4-ethyl-6-tert.butylphenol); 2,2'-thio-bis-(4-methyl-6-tert.butylphenol); 2-(3,5-ditert.butyl 4-hydroxybenzyl)-4-methylphenol; 2-(3,5-ditert.butyl-4-hydroxybenzyl) phenol; 2-(3,5-ditert.butyl-4-hydroxybenzyl)-5-methylphenol, 2,6-bis-(2-hydroxy-3-tert.butyl-5-ethylbenzyl)-4-ethyl phenol and 2-(3,5-ditert.butyl-4-hydroxybenzyl)-4-isopropyl phenol.
Claim 6
Dependent Claim 37 words
Compounds as described in claim 1 wherein the cyclic dienes are selected from the group consisting of 1,5-cyclooctadiene; cyclopentadiene; bicyclo[2.2.1]-2,5-heptadiene; dicyclopentadiene; pentacyclo [8.2.1.1 4 .spsp.9 7 .0 2 .spsp.9 9 .0 3 .spsp.9 8 ]-tetradeca-5,11-diene, and 1,5,9-cyclododecadiene.
Claim 7
Dependent Claim 23 words
Compounds as described in claim 1 wherein the ester forming compounds are selected from the group consisting of acryloyl chloride and methacryloyl chloride.
Claim 8
Dependent Claim 27 words
Compounds as described in claim 1 wherein R 4 is selected from the group consisting of alkyl radicals having from 1 to 2 carbon atoms and phenyl.

References Cited (Backward Citations)

US2894022A Cited
US2943076A Cited
US3773812A Cited
US3459787A Cited
US3637809A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-11-07 1987-05-09 1987-11-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-11-07 1991-05-09 1991-11-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-11-07 1995-05-09 1995-11-08 $7700.00 Window Closed / Lapsed

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