US4233209A
Expired / Lapsed
US
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Hindered phenol hydrazones and compositions stabilized therewith
Assignee: BASF Corp
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Filing: 1978-11-15
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Granted: 1980-11-11
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Expires: 1998-11-15
Abstract
Abstract Hindered phenol hydrazones of the formula ##STR1## wherein R 1 and R 2 are alkyl of 1 to 8 carbons or R 1 can also be hydrogen, n is 1 to 6, R' is hydrogen or alkyl, R 3 is alkyl, phenyl, substituted phenyl, alkylenethioalkyl or alkylenethioether ester of a carboxylic acid or a group ##STR2## where T is a direct bond, alkylene, sulfur or oxygen interrupted alkylene or phenylene, said compounds being useful as diene rubber stabilizers.
Inventors
- 👤 Martin Dexter
- 👤 David H. Steinberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 02:27
CPC Classifications
C; C07; C07C; C07C251/00; C07C251/72; C07C243/00; C07C243/24; C07C243/26; C07C243/30; C07C243/32; C08; C08K; C08K5/00; C08K5/16; C08K5/29; C08K5/30; C08K5/36; C08K5/37; C08K5/372; C08K5/3725
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
201 words
A hindered phenol hydrazone of the formula ##STR9## wherein R 1 is hydrogen of a straight or branched chain alkyl of 1 to 8 carbon atoms, R 2 a straight or branched chain alkyl of 1 to 8 carbon atoms, n is an integer of 1 to 5, R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 3 is an alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted with 1 to 3 alkyl groups of 1 to 4 carbon atoms, or selected from an interrupted alkyl group of the formulae ##STR10## where p and t are independently integers of 1 to 18, R 4 is an alkyl group of 1 to 17 carbon atoms or an olefinic group of the formula --(CH 2 )--CH═CH(CH 2 ) y CH 3 where z and y are independently integers of 1 to 12, or R 3 is the group ##STR11## where T is a direct bond, alkylene of 1 to 6 carbon atoms, phenylene, alkylene interrupted with sulfur or oxygen of the formula --C a H 2a --X--C a H 2a -- where X is sulfur or oxygen and a is an integer of 1 to 6.
Claim 2
Dependent Claim
201 words
A hindered phenol hydrazone of the formula ##STR9## wherein R 1 is hydrogen of a straight or branched chain alkyl of 1 to 8 carbon atoms, R 2 a straight or branched chain alkyl of 1 to 8 carbon atoms, n is an integer of 1 to 5, R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, R 3 is an alkyl of 1 to 18 carbon atoms, phenyl or phenyl substituted with 1 to 3 alkyl groups of 1 to 4 carbon atoms, or selected from an interrupted alkyl group of the formulae ##STR10## where p and t are independently integers of 1 to 18, R 4 is an alkyl group of 1 to 17 carbon atoms or an olefinic group of the formula --(CH 2 )--CH═CH(CH 2 ) y CH 3 where z and y are independently integers of 1 to 12, or R 3 is the group ##STR11## where T is a direct bond, alkylene of 1 to 6 carbon atoms, phenylene, alkylene interrupted with sulfur or oxygen of the formula --C a H 2a --X--C a H 2a -- where X is sulfur or oxygen and a is an integer of 1 to 6.
Claim 3
Dependent Claim
43 words
A compound of claim 1 wherein R 1 and R 2 are branched chain alkyl groups, both ortho to the hydroxy, n is 2, R 3 is an interrupted alkyl group where p is 2 to 6 and t is 8 to 18.
Claim 4
Dependent Claim
14 words
A compound of claim 2 wherein R 1 and R 2 are tert-butyl groups.
Claim 5
Dependent Claim
10 words
The compound of claim 1 which is n-dodecylthio-2-methylpropanal-3'-(3",5"-di-t-butyl-4"-hydroxyphenyl) propionyl hydrazone.
Claim 6
Dependent Claim
10 words
The compound of claim 1 which is n-dodecylthiopropanal-3-(3',5'-t-butyl-4'-hydroxyphenyl) propionyl hydrazone.
Claim 7
Dependent Claim
10 words
The compound of claim 1 which is oleoylethylthio-2-methylpropanal-3'-(3",5"-di-t-butyl-4"-hydroxyphenyl) propionyl hydrazone.
Claim 8
Dependent Claim
32 words
A compound of claim 1 wherein R 1 and R 2 are branched chain alkyl groups, both ortho to the hydroxy, n is 2 and R 3 is hydrogen, alkyl or phenyl.
Claim 9
Dependent Claim
15 words
A compound of claim 1 wherein R 1 and R 2 are tert- butyl groups.
Claim 10
Dependent Claim
9 words
The compound of claim 8 which is n-dodecylal-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl hydrazone.
Claim 11
Dependent Claim
9 words
The compound of claim 8 which is isovaleral-3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl hydrazone.
Claim 12
Dependent Claim
34 words
A compound of claim 1 wherein R 1 and R 2 are branched chain alkyl groups, both ortho to the hydroxy, n is 2 and R 3 is a group of the formula ##STR12##
Claim 13
Dependent Claim
14 words
A compound of claim 11 wherein R 1 and R 2 are tert-butyl groups.
Claim 14
Dependent Claim
38 words
A polymer composition comprising a polymer selected from the group consisting of polymonoolefin resins and diene rubbers stabilized against thermal and oxidative degradation by incorporation therein of 0.01 to 5% by weight of a compound of claim 1.
Claim 15
Dependent Claim
20 words
A composition of claim 13 wherein said polymer is a rubber selected from polybutadiene, styrene-butadiene copolymer, acrylonitrile-butadiene-styrene copolymer and polyisoprene.
Claim 16
Dependent Claim
10 words
A composition of claim 14 wherein said rubber is polybutadiene.
Claim 17
Dependent Claim
12 words
A composition of claim 14 wherein the hydrazone stabilizer is 3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionyl (n-tridecylthio-2-methylpropanal)hydrazone.
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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) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |