US4292195A
Expired / Lapsed
US
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Non-fugitive antioxidants
Assignee: Goodrich Corp
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Filing: 1977-05-16
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Granted: 1981-09-29
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Expires: 1997-05-16
Abstract
Abstract Antioxidant compositions as described which are the reaction products of a mixture of (a) at least one compound selected from compounds having the formula ##STR1## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar--NH--Ar--O--R.sup.3 (FORMULA II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 2 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule. Optionally, the mixture also may contain (c) one or more co-reactants for the polyepoxide such as acids, alcohols, phenols and amines, and the products obtained from these mixtures can be reacted further with acid anhydrides to modify the properties. These reaction products are useful as antioxidants in rubbers, plastics, oils, greases, etc., and they are particularly useful as stabilizers for rubbers and plastics since the rubbers and plastics containing such compositions present a high degree of resistance to the adverse effects of oxidative aging even when said rubbers and plastics are subjected to solvents which normally would extract a significant portion of conventional antioxidants.
Inventors
- 👤 Roger E. Morris
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:10
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C09; C09K; C09K15/00; C09K15/04; C09K15/20; C09K15/28
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
147 words
A composition useful as an antioxidant which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR10## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 2 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 2
Dependent Claim
147 words
A composition useful as an antioxidant which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR10## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 2 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 3
Dependent Claim
12 words
The composition of claim 1 wherein the polyepoxide is a polyether polyepoxide.
Claim 4
Dependent Claim
21 words
The composition of claim 2 wherein the polyether polyepoxide is a glycidyl polyether of a polyhydric alcohol or a polyhydric phenol.
Claim 5
Dependent Claim
12 words
The composition of claim 1 wherein the polyepoxide is a cyclic polyepoxide.
Claim 6
Dependent Claim
17 words
The composition of claim 1 wherein the polyepoxide comprises a mixture of a polyepoxide and a monoepoxide.
Claim 7
Dependent Claim
11 words
The composition of claim 5 wherein the monoepoxide is an epihalohydrin.
Claim 8
Dependent Claim
47 words
The composition of claim 1 wherein the antioxidant compound (a) in the mixture has the formula ##STR11## wherein R 4 is hydrogen, A 2 N or AO wherein A is an alkyl or substituted alkyl group, and R and R 1 are as defined in claim 1.
Claim 9
Dependent Claim
14 words
The composition of claim 7 wherein R, R 1 and R 4 are hydrogen.
Claim 10
Dependent Claim
19 words
The composition of claim 7 wherein R and R 4 are hydrogen and R 1 is an alkyl group.
Claim 11
Dependent Claim
39 words
The composition of claim 7 wherein R and optionally R 1 are hydroxy oxyalkylene radicals having the formula --(R.sup.5 --O.sub.n)--H wherein R 5 is ethylene or 1,2-propylene, n varies from one to about 20, and R 4 is hydrogen.
Claim 12
Dependent Claim
48 words
The composition of claim 1 wherein the mixture also contains (c) one or more co-reactants for the polyepoxide selected from the group consisting of organic carboxylic acids, dicarboxylic acid monoesters, dicarboxylic acids, alcohols, thioalcohols, phenols, thiophenols, aliphatic monoamines, aliphatic diamines, mercaptoacids, mercaptoacid esters, alkylthiocarboxylic acids and arylthiocarboxylic acids.
Claim 13
Dependent Claim
20 words
The composition of claim 11 wherein the co-reactant is a saturated or unsaturated carboxylic acid or a mercaptoacid or ester.
Claim 14
Dependent Claim
13 words
The composition of claim 12 wherein the acid is acrylic or methacrylic acid.
Claim 15
Dependent Claim
22 words
The composition of claim 8 wherein the polyepoxide is a glycidyl ether of an aliphatic polyhydroxy compound or an alkylene bis-phenol compound.
Claim 16
Dependent Claim
15 words
The composition of claim 14 wherein the polyepoxide is a diglycidyl ether of 1,4-butylene glycol.
Claim 17
Dependent Claim
17 words
The composition of claim 14 wherein the polyepoxide is the diglycidyl ether of a 4,4'-alkylene bis-phenol compound.
Claim 18
Dependent Claim
28 words
A composition useful as an antioxidant which comprises the reaction product of claim 1 further reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
Claim 19
Dependent Claim
28 words
A composition useful as an antioxidant which comprises the reaction product of claim 7 further reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
Claim 20
Dependent Claim
13 words
The composition of claim 18 wherein the anhydride is maleic or succinic anhydride.
Claim 21
Dependent Claim
176 words
An aqueous rubber latex comprising water, 100 parts by weight of rubber polymer and from about 0.01 to about 10 parts by weight, based on the weight of the rubber polymer, of an antioxidant composition which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR12## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 3 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 22
Dependent Claim
176 words
An aqueous rubber latex comprising water, 100 parts by weight of rubber polymer and from about 0.01 to about 10 parts by weight, based on the weight of the rubber polymer, of an antioxidant composition which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR12## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 3 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 23
Dependent Claim
14 words
The latex of claim 20 wherein the rubber polymer is a diene rubber polymer.
Claim 24
Dependent Claim
17 words
The latex of claim 21 wherein the diene rubber contains at least 45% of a conjugated diene.
Claim 25
Dependent Claim
22 words
The latex of claim 22 wherein the diene rubber is a rubbery polymer of a diene having 4 to 8 carbon atoms.
Claim 26
Dependent Claim
16 words
The latex of claim 22 wherein the diene rubber is a copolymer of butadiene and acrylonitrile.
Claim 27
Dependent Claim
48 words
The latex of claim 20 wherein the mixture also contains (c) one or more co-reactants for the polyepoxide selected from the group consisting of organic carboxylic acids, dicarboxylic acid monoesters, dicarboxylic acids alcohols, thioalcohols, phenols, thiophenols, aliphatic monoamines, aliphatic diamines, mercaptoacids, mercaptoacid esters, alkylthiocarboxylic acids and arylthiocarboxylic acids.
Claim 28
Dependent Claim
24 words
The latex of claim 20 wherein the reaction product further is reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
Claim 29
Dependent Claim
24 words
The latex of claim 25 wherein the reaction product further is reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
Claim 30
Dependent Claim
164 words
A vulcanizate of a rubber polymer stabilized against attack by atmospheric oxygen by the inclusion therein of an effective amount of a composition which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR13## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 2 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 31
Dependent Claim
164 words
A vulcanizate of a rubber polymer stabilized against attack by atmospheric oxygen by the inclusion therein of an effective amount of a composition which comprises the reaction product of a mixture of (a) at least one compound selected from compounds having the formula ##STR13## wherein each Ar is an aromatic group, and R and R 1 are each independently hydrogen, alkyl, substituted alkyl, oxyalkylene or --C(O)--R 2 --COOH groups wherein R 2 is an alkylene or alkenylene group, with the proviso that at least one of the R and R 1 groups must be hydrogen or a group containing at least one substituent reactive with an epoxy group, and Ar-NH-Ar-O-R.sup.3 (II) wherein Ar is as defined above and R 3 is hydrogen, or a substituted alkyl group containing at least one substituent reactive with an epoxy group, or --C(O)--R 2 --COOH wherein R 2 is an alkylene or alkenylene group, and (b) at least one polyepoxide having at least 2 epoxy groups per molecule.
Claim 32
Dependent Claim
14 words
The vulcanizate of claim 28 wherein the rubber polymer is a diene rubber polymer.
Claim 33
Dependent Claim
18 words
The vulcanizate of claim 29 wherein the diene rubber polymer contains at least 45% of a conjugated diene.
Claim 34
Dependent Claim
22 words
The vulcanizate of claim 30 wherein the diene rubber is a rubber polymer of a diene having 4 to 8 carbon atoms.
Claim 35
Dependent Claim
16 words
The vulcanizate of claim 30 wherein the diene rubber is a copolymer of butadiene and acrylonitrile.
Claim 36
Dependent Claim
22 words
The vulcanizate of claim 28 wherein from about 0.01 to about 10 parts of the antioxidant is included into the rubber polymer.
Claim 37
Dependent Claim
54 words
The vulcanizate of claim 28 wherein the mixture used to form the reaction product also contains (c) one or more co-reactants for the polyepoxide selected from the group consisting of organic carboxylic acids, dicarboxylic acid monoesters, dicarboxylic acids alcohols, thioalcohols, phenols, thiophenols, aliphatic monoamines, aliphatic diamines, mercaptoacids, mercaptoacid esters, alkylthiocarboxylic acids and arylthiocarboxylic acids.
Claim 38
Dependent Claim
24 words
The vulcanizate of claim 28 wherein the reaction product further is reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
Claim 39
Dependent Claim
24 words
The vulcanizate of claim 34 wherein the reaction product further is reacted with a dicarboxylic anhydride in a molar ratio of up to 1:2.
References Cited (Backward Citations)
US3696851A
Cited
US4051067A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-28 | 1985-03-30 | 1985-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-28 | 1989-03-30 | 1989-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-28 | 1993-03-30 | 1993-09-29 | $7700.00 | Window Closed / Lapsed |