US4307012A
Expired / Lapsed
US
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Polymeric alkylbenzenoid hydroquinoid antioxidants
Assignee: Standard Oil Co
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Filing: 1979-12-17
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Granted: 1981-12-22
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Expires: 1999-12-17
Abstract
Abstract Compositions of oxidizable organic materials having stabilizing amounts of polymeric alkylbenzenoid hydroquinoid antioxidants of from about 500 to about 50,000 molecular weight, and polymers which are the reaction products of a hydroquinone compound and a polymeric monohydroxy alkylbenzenoid compound.
Inventors
- 👤 Carl Serres, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:24
CPC Classifications
C; C09; C09K; C09K15/00; C09K15/04; C09K15/06; C09K15/08; A; A23; A23B; A23B2/00; A23B2/70; A23B2/725; A23B2/729; C08; C08G; C08G61/00; C08G61/02; C08G65/00; C08G65/34; C08G65/48; C08G85/00; C08G85/004; C08L; C08L101/00
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
275 words
A composition comprising a polymer of a polymeric alkylaromatic hydroquinoid compound and an oxidizable organic material normally subject to adverse effects by oxygen, selected from the group consisting of lipids including animal and vegetable fats and oils, polymers, mineral oils and gasoline, wherein the oxidizable organic material is stabilized against oxidative degradation by a stabilizing amount of the polymer, said polymer having the structure ##STR11## (a) P is selected from the group consisting of (i) ##STR12## where R is selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms, Ar is substituted and unsubstituted and is selected from the group consisting of benzenoid ring moieties of 6 to 24 carbon atoms, said substituents being one or more alkyl groups of 1 to 26 carbon atoms, and (ii) substituted and unsubstituted aromatic moieties comprising phenyl moieties, substituents of said substituted aromatic moieties comprising one or more alkyl groups of 1 to 26 carbon atoms; (b) Y is selected from the group consisting of --CH 2 --, --O--, --S--, --CH(CH 3 )--, --C(CH 3 ) 2 --and phenyl moieties; (c) R' is selected from the group consisting of an alkyl group of 1 to 26 carbon atoms, and an aromatic moiety selected from the group consisting of a benzenoid group of 6 to 24 carbon atoms, the said aromatic moiety being substituted and unsubstituted, said substituents being one or more alkyl groups of 1 to 26 carbon atoms; (d) R" and R"' are independently selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms. (e) n is an integer from 2 to 200.
Claim 2
Dependent Claim
275 words
A composition comprising a polymer of a polymeric alkylaromatic hydroquinoid compound and an oxidizable organic material normally subject to adverse effects by oxygen, selected from the group consisting of lipids including animal and vegetable fats and oils, polymers, mineral oils and gasoline, wherein the oxidizable organic material is stabilized against oxidative degradation by a stabilizing amount of the polymer, said polymer having the structure ##STR11## (a) P is selected from the group consisting of (i) ##STR12## where R is selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms, Ar is substituted and unsubstituted and is selected from the group consisting of benzenoid ring moieties of 6 to 24 carbon atoms, said substituents being one or more alkyl groups of 1 to 26 carbon atoms, and (ii) substituted and unsubstituted aromatic moieties comprising phenyl moieties, substituents of said substituted aromatic moieties comprising one or more alkyl groups of 1 to 26 carbon atoms; (b) Y is selected from the group consisting of --CH 2 --, --O--, --S--, --CH(CH 3 )--, --C(CH 3 ) 2 --and phenyl moieties; (c) R' is selected from the group consisting of an alkyl group of 1 to 26 carbon atoms, and an aromatic moiety selected from the group consisting of a benzenoid group of 6 to 24 carbon atoms, the said aromatic moiety being substituted and unsubstituted, said substituents being one or more alkyl groups of 1 to 26 carbon atoms; (d) R" and R"' are independently selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms. (e) n is an integer from 2 to 200.
Claim 3
Dependent Claim
123 words
The composition of claim 1 wherein the said polymeric alkyl aromatic hydroquinoid compound is the reaction product of (A) a polymeric aromatic compound comprising said P and Y, (B) an acyl compound R'COX wherein X is selected from the group consisting of halogen, an --OH group and an acid anhydride group of R'COO--, and (C) a hydroquinone compound having at least one replaceable ring hydrogen, and wherein the mole ratio of said aromatic polymer of A to said acyl compound of B is 1:1, the hydroquinone compound of (C) is present in excess, n is an integer of 2 to 200, and the molecular weight of said polymeric alkyl aromatic hydroquinoid compound is within the range of from about 500 to about 50,000.
Claim 4
Dependent Claim
31 words
The composition of claim 2 wherein said hydroquinone compound is selected from the group consisting of 1,4-dihydroxybenzene; 2,3- or 2,5- or 2,6-dimethyl-1,4-dihydroxybenzene; 2-ethyl-1,4-dihydroxybenzene; 2-t-butyl-1, 4-dihydroxybenzene; 2-methyl-5-t-butyl-1, 4-dihydroxybenzene; 2-(2-phenylethyl)-1,4-dihydroxybenzene; and 2,4-di(2(4-vinyl) phenylethyl)-1,4-dihydroxybenzene.
Claim 5
Dependent Claim
42 words
The composition of claim 2 wherein said polymeric alkyl aromatic hydroquinoid compound is the reaction product of (A) a polymeric aromatic compound selected from the group consisting of polystyrene, poly(alpha-methylstyrene), poly(vinyltoluene), poly(2-vinylnaphthalene and poly(2,6-dimethylphenylene oxide), (B) acetyl chloride and (C) tert-butyl hydroquinone.
Claim 6
Dependent Claim
14 words
The said composition of claim 4 wherein said polymeric aromatic compound polymer is polystyrene.
Claim 7
Dependent Claim
12 words
The said composition of claim 4 wherein said aromatic compound is poly(alpha-methylstyrene).
Claim 8
Dependent Claim
13 words
The said composition of claim 4 wherein said polymeric aromatic compound is poly(vinyltoluene).
Claim 9
Dependent Claim
14 words
The said composition of claim 4 wherein said polymeric aromatic compound is poly(2,6-dimethyl-phenylene oxide).
Claim 10
Dependent Claim
29 words
The composition of claim 1 wherein the said stabilizing amount of said polymer is within the range of from about 2 to 50,000 parts per million, basis oxidizable material.
Claim 11
Dependent Claim
35 words
The composition of claim 1 wherein the oxidizable organic material comprises at least one member selected from the group consisting of lard, sunflower oil, soybean oil, safflower oil, cottonseed oil, peanut oil, and corn oil.
Claim 12
Dependent Claim
19 words
The composition of claim 1 wherein R is selected from the group consisting of hydrogen and a methyl moiety.
Claim 13
Dependent Claim
11 words
The composition of claim 1 wherein Ar is a benzene moiety.
Claim 14
Dependent Claim
13 words
The said composition of claim 4 wherein said polymeric aromatic compound is poly(2-vinylnaphthalene).
Claim 15
Dependent Claim
234 words
An alkyl aromatic hydroquinoid compound of the formula ##STR13## wherein (a) P is selected from the group consisting of (i) ##STR14## wherein R is selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms, Ar is substituted and unsubstituted and is selected from the group consisting of benzenoid ring moieties of 6 to 24 carbon atoms, said substituents being one or more alkyl groups of 1 to 26 carbon atoms, and (ii) substituted and unsubstituted aromatic moieties comprising phenyl moieties, substituents of said substituted aromatic moieties comprising one or more alkyl groups of 1 to 26 carbon atoms; (b) Y is selected from the group consisting of --CH 2 --,--O--,--S--,--CH(CH 3 )--,--C(CH 3 ) 2 -- and phenyl moieties; (c) R' is selected from the group consisting of an alkyl group of 1 to 26 carbon atoms, and an aromatic moiety selected from the group consisting of a benzenoid moiety of 6 to 24 carbon atoms, the said aromatic moiety being substituted and unsubstituted, said substituents being one or more alkyl groups of 1 to 26 carbon atoms; (d) R" and R"' are independently selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms. (e) n is an integer from 2 to 200 and the molecular weight of said compound is within the range of from about 500 to 50,000.
Claim 16
Dependent Claim
234 words
An alkyl aromatic hydroquinoid compound of the formula ##STR13## wherein (a) P is selected from the group consisting of (i) ##STR14## wherein R is selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms, Ar is substituted and unsubstituted and is selected from the group consisting of benzenoid ring moieties of 6 to 24 carbon atoms, said substituents being one or more alkyl groups of 1 to 26 carbon atoms, and (ii) substituted and unsubstituted aromatic moieties comprising phenyl moieties, substituents of said substituted aromatic moieties comprising one or more alkyl groups of 1 to 26 carbon atoms; (b) Y is selected from the group consisting of --CH 2 --,--O--,--S--,--CH(CH 3 )--,--C(CH 3 ) 2 -- and phenyl moieties; (c) R' is selected from the group consisting of an alkyl group of 1 to 26 carbon atoms, and an aromatic moiety selected from the group consisting of a benzenoid moiety of 6 to 24 carbon atoms, the said aromatic moiety being substituted and unsubstituted, said substituents being one or more alkyl groups of 1 to 26 carbon atoms; (d) R" and R"' are independently selected from the group consisting of hydrogen and an alkyl group of 1 to 26 carbon atoms. (e) n is an integer from 2 to 200 and the molecular weight of said compound is within the range of from about 500 to 50,000.
Claim 17
Dependent Claim
22 words
The compound of claim 14 wherein Ar is selected from the group consisting of phenyl, naphthyl, biphenyl, diphenylmethane, diphenylether, and diphenylsulfide moieties.
Claim 18
Dependent Claim
31 words
The compound of claim 14 wherein P is ##STR15## --CH 2 --, Ar is phenyl, R and R" are hydrogen, R"' is a tertiarybutyl group and R' is a methyl group.
Claim 19
Dependent Claim
27 words
The compound of claim 14 wherein the said hydroquinone compound is selected from the group consisting of 1,4-dihydroxybenzene; 2,3-or-2,5-, or 2,6-dimethyl-1,4-dihydroxybenzene; 2-ethyl-1,4-dihydroxybenzene; 2-t-butyl-1,4-dihydroxybenzene; 2-methyl-5-t-butyl-1,4-dihydroxybenzene; 2-(2-phenylethyl)-1,4-dihydroxybenzene; and 2,4-di(2-(4-vinyl)phenethyl)-1,4-dihydroxybenzene.
Claim 20
Dependent Claim
39 words
The compound of claim 14 wherein the said hydroquinoid compound is the reaction product of (A) an aromatic compound selected from the group consisting of polystyrene, poly(alphamethylstyrene), poly(vinyltoluene, poly(2-vinylnaphthalene and poly(2,6-dimethylphenylene oxide), (B) acetyl chloride and (C) tert-butyl hydroquinone.
Claim 21
Dependent Claim
12 words
The compound of claim 18 wherein said polymeric aromatic compound is polystyrene.
Claim 22
Dependent Claim
12 words
The compound of claim 18 wherein said polymeric aromatic compound is poly(2-vinylnaphthalene).
Claim 23
Dependent Claim
13 words
The compound of claim 18 wherein said polymeric aromatic compound is poly(alpha-methyl styrene).
Claim 24
Dependent Claim
12 words
The compound of claim 18 wherein said polymeric aromatic compound is poly(vinyltoluene).
Claim 25
Dependent Claim
13 words
The compound of claim 18 wherein said polymeric aromatic compound is poly(2,6-dimethyl-phenylene oxide).
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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) | 1984-12-21 | 1985-06-22 | 1985-12-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-12-21 | 1989-06-22 | 1989-12-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-12-21 | 1993-06-22 | 1993-12-22 | $7700.00 | Window Closed / Lapsed |