Patent US4031068A successfully refreshed from Google Patents.
US4031068A
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Non-migratory sulfonyl azide antioxidants
Assignee: Uniroyal Chemical Co Inc
•
Filing: 1976-07-26
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Granted: 1977-06-21
•
Expires: 1996-07-26
Abstract
Abstract Antioxidants containing a sulfonyl azide moiety react with polymers having carbon-hydrogen bonds thereby becoming non-extractable and non-migratory.
Inventors
- 👤 Stephen E. Cantor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 09:58
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/36; C08K5/43; C08F; C08F8/00; C08F8/34; C09; C09K; C09K15/00; C09K15/04; C09K15/28
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
185 words
A sulfonyl azide antioxidant of the formula ##STR8## wherein: R 1 is alkyl of from 1 to 12 carbon atoms, cyclohexyl, C 7 -C 10 alkyl-cyclohexyl, benzyl, or C 8 -C 11 alkylbenzyl; R 2 is hydrogen or has one of the values assigned to R 1 , with the proviso that R 1 and R 2 together have at least 2 carbon atoms; g has a value of from 0 to 5; X is a divalent bridge member selected from --CH 2 O--, --CH 2 NH--, or ##STR9## m and n are each 1 or 2; and Z is, depending on the values of m and n, a divalent, trivalent or tetravalent group selected from: a. an alkylene group of from 2 to 5 carbon atoms when each of m and n is 1, b. a divalent or trivalent benzene group when n is 1 and m is 1 or when m is 1 and n is 2, and c. a divalent, trivalent or tetravalent group selected from naphthylene, diphenyl ether, and benzene groups when each of m and n is 1 or 2.
Claim 2
Dependent Claim
185 words
A sulfonyl azide antioxidant of the formula ##STR8## wherein: R 1 is alkyl of from 1 to 12 carbon atoms, cyclohexyl, C 7 -C 10 alkyl-cyclohexyl, benzyl, or C 8 -C 11 alkylbenzyl; R 2 is hydrogen or has one of the values assigned to R 1 , with the proviso that R 1 and R 2 together have at least 2 carbon atoms; g has a value of from 0 to 5; X is a divalent bridge member selected from --CH 2 O--, --CH 2 NH--, or ##STR9## m and n are each 1 or 2; and Z is, depending on the values of m and n, a divalent, trivalent or tetravalent group selected from: a. an alkylene group of from 2 to 5 carbon atoms when each of m and n is 1, b. a divalent or trivalent benzene group when n is 1 and m is 1 or when m is 1 and n is 2, and c. a divalent, trivalent or tetravalent group selected from naphthylene, diphenyl ether, and benzene groups when each of m and n is 1 or 2.
Claim 3
Dependent Claim
12 words
An antioxidant as in claim 1 in which R 1 is alkyl.
Claim 4
Dependent Claim
12 words
An antioxidant as in claim 1 in which R 2 is alkyl.
Claim 5
Dependent Claim
21 words
An antioxidant as in claim 1 in which R 1 and R 2 are alkyl having 3 to 8 carbon atoms.
Claim 6
Dependent Claim
17 words
An antioxidant as in claim 1 in which R 1 and R 2 are C 4 alkyl.
Claim 7
Dependent Claim
16 words
An antioxidant as in claim 1 in which R 1 and R 2 are tertiary alkyl.
Claim 8
Dependent Claim
16 words
An antioxidant as in claim 1 in which R 1 and R 2 are tertiary butyl.
Claim 9
Dependent Claim
11 words
An antioxidant as in claim 1 in which g is zero.
Claim 10
Dependent Claim
11 words
An antioxidant as in claim 1 in which g is 1.
Claim 11
Dependent Claim
13 words
An antioxidant as in claim 1 in which X is --CH 2 O--.
Claim 12
Dependent Claim
13 words
An antioxidant as in claim 1 in which X is --CH 2 NH--.
Claim 13
Dependent Claim
11 words
An antioxidant as in claim 1 in which X is ##STR10##
Claim 14
Dependent Claim
11 words
An antioxidant as in claim 1 in which n is 1.
Claim 15
Dependent Claim
11 words
An antioxidant as in claim 1 in which m is 1.
Claim 16
Dependent Claim
13 words
An antioxidant as in claim 1 in which n and m are 1.
Claim 17
Dependent Claim
11 words
An antioxidant as in claim 1 in which Z is phenylene.
Claim 18
Dependent Claim
8 words
The antioxidant of claim 1 which is N-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl]-N'-(4-azidosulfonylphenyl)urea.
Claim 19
Dependent Claim
8 words
The antioxidant of claim 1 which is 3,5-di-tert-butyl-4-hydroxybenzyl-4-azidosulfonylcarbanilate.
Claim 20
Dependent Claim
8 words
The antioxidant of claim 1 which is 2-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionoxy]ethyl-4-azidosulfonylcarbanilate.
Claim 21
Dependent Claim
43 words
A method of protecting from oxidative deterioration a polymer, normally subject to oxidative deterioration, said polymer having a carbon-hydrogen bond, comprising mixing with the said polymer, in an amount effective to protect said polymer against oxidative deterioration, an antioxidant as in claim 1.
Claim 22
Dependent Claim
50 words
A method as in claim 20 in which the resulting mixture of polymer and antioxidant is subjected to elevated temperature whereby the antioxidant is chemically bound to the polymer at the said carbon-hydrogen bond and said antioxidant resists extraction from the polymer by organic solvents that normally dissolve the antioxidant.
Claim 23
Dependent Claim
21 words
A method as in claim 20 in which R 1 and R 2 are alkyl having 3 to 8 carbon atoms.
Claim 24
Dependent Claim
16 words
A method as in claim 22 in which R 1 and R 2 are tertiary alkyl.
Claim 25
Dependent Claim
16 words
A method as in claim 23 in which R 1 and R 2 are tertiary butyl.
Claim 26
Dependent Claim
13 words
A method as in claim 20 in which X is --CH 2 O--.
Claim 27
Dependent Claim
13 words
A method as in claim 20 in which X is --CH 2 NH--.
Claim 28
Dependent Claim
11 words
A method as in claim 20 in which X is ##STR11##
Claim 29
Dependent Claim
13 words
A method as in claim 20 in which the said antioxidant is N-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)-ethyl]-N'-(4-azidosulfonylphenyl)urea.
Claim 30
Dependent Claim
13 words
A method as in claim 20 in which the said antioxidant is 3,5-di-tert-butyl-4-hydroxybenzyl-4-azidosulfonylcarbanilate.
Claim 31
Dependent Claim
13 words
A method as in claim 20 in which the said antioxidant is 2-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionoxy]ethyl-4-azidosulfonylcarbanilate.
Claim 32
Dependent Claim
26 words
A method as in claim 21 in which the said polymer is a vulcanizable elastomeric composition, and the said heating occurs during vulcanization of the elastomer.
Claim 33
Dependent Claim
16 words
A method as in claim 31 in which the said elastomer is an ethylene-propylene-non-conjugated diene terpolymer.
Claim 34
Dependent Claim
15 words
A method as in claim 31 in which the said elastomer is a butadiene-acrylonitrile copolymer.
Claim 35
Dependent Claim
14 words
A method as in claim 31 in which the said elastomer is natural rubber.
Claim 36
Dependent Claim
26 words
A method as in claim 21 in which the said polymer is a thermoplastic resin and the said heating occurs during shaping of the said thermoplastic.
Claim 37
Dependent Claim
13 words
A method as in claim 35 in which the said thermoplastic is polyethylene.
Claim 38
Dependent Claim
13 words
A method as in claim 35 in which the said thermoplastic is polypropylene.
Claim 39
Dependent Claim
8 words
The product of the method of claim 21.
Claim 40
Dependent Claim
8 words
The product of the method of claim 22.
Claim 41
Dependent Claim
8 words
The product of the method of claim 23.
Claim 42
Dependent Claim
8 words
The product of the method of claim 24.
Claim 43
Dependent Claim
8 words
The product of the method of claim 25.
Claim 44
Dependent Claim
8 words
The product of the method of claim 26.
Claim 45
Dependent Claim
8 words
The product of the method of claim 27.
Claim 46
Dependent Claim
8 words
The product of the method of claim 28.
Claim 47
Dependent Claim
8 words
The product of the method of claim 29.
Claim 48
Dependent Claim
8 words
The product of the method of claim 30.
Claim 49
Dependent Claim
8 words
The product of the method of claim 31.
Claim 50
Dependent Claim
8 words
The product of the method of claim 32.
Claim 51
Dependent Claim
8 words
The product of the method of claim 33.
Claim 52
Dependent Claim
8 words
The product of the method of claim 34.
Claim 53
Dependent Claim
8 words
The product of the method of claim 35.
Claim 54
Dependent Claim
8 words
The product of the method of claim 36.
Claim 55
Dependent Claim
8 words
The product of the method of claim 37.
References Cited (Backward Citations)
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US3298975A
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US3652599A
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US3859261A
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US3763118A
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US3991131A
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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) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |