US5100940A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polymeric compositions stabilized with hindered phenolic N-(amido)imides
Assignee: Arkema Inc
•
Filing: 1991-08-20
•
Granted: 1992-03-31
•
Expires: 2011-08-20
Abstract
Abstract Phenolic N-(amido)imides are provided which are useful as antioxidant stabilizers for organic materials, including a large variety of synthetic polymers, typically subject to thermooxidative degradation. The antioxidant effectiveness of the phenolic N-(amido)imide stabilizers is enhanced by the deactivating potential of the amido-imide moiety towards metals or metal ions that frequently contaminate polymer compositions and serve to catalyze thermal degradation.
Inventors
- 👤 Jerome Wicher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:25
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D207/00; C07D207/46; C07D207/50; C07D209/56; C07D209/58; C07D209/72; C07D209/76; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
243 words
A composition comprising a polymer and about 0.01% to about 10% of a compound having the following Formula I: ##STR6## wherein R 1 is t-alkyl of 4 to 8 carbons or cycloalkyl of 3 to 6 carbons; R 2 is hydrogen, alkyl of 1 to 8 carbons, t-alkyl of 4 to 8 carbons or cycloalkyl of 3 to 6 carbons; R 3 is hydrogen, lower alkyl of 1 to 6 carbons, phenyl or a phenol having the formula ##STR7## R 4 , R 5 , R 6 and R 7 are independently hydrogen, lower alkyl of 1 to 6 carbons or phenyl; R 8 is a substituted or unsubstituted aliphatic diradical of 2 to 64 carbons, a substituted or unsubstituted alicyclic diradical of 3 to 12 carbons or a substituted or unsubstituted alibicyclic diradical of 5 to 18 carbons, with the proviso that the R 8 diradical has valence locants on adjacent carbons, wherein substituents for R 8 are alkyl of 1 to 24 carbons, alkoxy of 1 to 24 carbons, alkylthio of 1 to 24 carbons, alkenyl of 2 to 24 carbons, oxydialkyl of 2 to 24 carbons, thiodialkyl of 2 to 24 carbons, acyloxy of 2 to 24 carbons, alkoxycarbonyl of 2 to 24 carbons, cycloaliphatic of 3 to 12 carbons, dialkylaminocarbonyl of 3 to 41 carbons or phenyl; x is an integer from 0 to 6; y is an integer from 0 to 10; and z is 0 to 1.
Claim 2
Dependent Claim
243 words
A composition comprising a polymer and about 0.01% to about 10% of a compound having the following Formula I: ##STR6## wherein R 1 is t-alkyl of 4 to 8 carbons or cycloalkyl of 3 to 6 carbons; R 2 is hydrogen, alkyl of 1 to 8 carbons, t-alkyl of 4 to 8 carbons or cycloalkyl of 3 to 6 carbons; R 3 is hydrogen, lower alkyl of 1 to 6 carbons, phenyl or a phenol having the formula ##STR7## R 4 , R 5 , R 6 and R 7 are independently hydrogen, lower alkyl of 1 to 6 carbons or phenyl; R 8 is a substituted or unsubstituted aliphatic diradical of 2 to 64 carbons, a substituted or unsubstituted alicyclic diradical of 3 to 12 carbons or a substituted or unsubstituted alibicyclic diradical of 5 to 18 carbons, with the proviso that the R 8 diradical has valence locants on adjacent carbons, wherein substituents for R 8 are alkyl of 1 to 24 carbons, alkoxy of 1 to 24 carbons, alkylthio of 1 to 24 carbons, alkenyl of 2 to 24 carbons, oxydialkyl of 2 to 24 carbons, thiodialkyl of 2 to 24 carbons, acyloxy of 2 to 24 carbons, alkoxycarbonyl of 2 to 24 carbons, cycloaliphatic of 3 to 12 carbons, dialkylaminocarbonyl of 3 to 41 carbons or phenyl; x is an integer from 0 to 6; y is an integer from 0 to 10; and z is 0 to 1.
Claim 3
Dependent Claim
188 words
The composition according to claim 1 wherein R 1 is t-alkyl or 4 to 5 carbons; R 2 is hydrogen, alkyl of 1 to 8 carbons or t-alkyl of 4 to 5 carbons; R 3 is hydrogen, lower alkyl of 1 to 5 carbons or a phenol having the formula ##STR8## R 4 , R 5 , R 6 and R 7 are independently hydrogen or lower alkyl of 1 to 5 carbons; R 8 is a substituted or unsubstituted aliphatic diradical of 2 to 24 carbons, a substituted or unsubstituted alicyclic diradical of 5 to 7 carbons or a substituted or unsubstituted alibicyclic diradical of 7 to 12 carbons, wherein substituents for R 8 are alkyl of 1 to 16 carbons, alkoxy of 1 to 16 carbons, alkylthio of 1 to 16 carbons, alkenyl of 2 to 17 carbons, oxydialkyl of 2 to 17 carbons, thiodialkyl of 2 to 17 carbons, acyloxy of 2 to 17 carbons, alkoxycarbonyl of 2 to 17 carbons or cycloaliphatic of 5 to 8 carbons; x is an integer from 0 to 4; and y is an integer from 0 to 6.
Claim 4
Dependent Claim
155 words
The composition according to claim 2 wherein R 1 is t-butyl; R 2 is hydrogen, alkyl of 1 to 4 carbons or t-butyl; R 3 is hydrogen or a phenol having the formula ##STR9## R 4 , R 5 , R 6 and R 7 are independently hydrogen or mehtyl; R 8 is a substituted or unsubstituted aliphatic diradical of 2 to 20 carbons, a substituted or unsubstituted alicyclic diradical of 6 carbons or a substituted or unsubstituted alibicyclic diradical of 7 or 8 carbons, wherein substituents for R 8 are alkyl of 1 to 16 carbons, alkoxy of 1 to 16 carbons, alkylthio of 1 to 16 carbons, alkenyl of 2 to 17 carbons, oxydialkyl of 2 to 17 carbons, thiodialkyl of 2 to 17 carbons, acyloxy of 2 to 17 carbons, alkoxycarbonyl of 2 to 17 carbons or cycloaliphatic of 5 to 6 carbons; x is 3; and y and z are 0.
Claim 5
Dependent Claim
30 words
The composition according to claim 1 wherein the compound is selected from the group consisting of: N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-octadecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-hexadecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-hexadecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-dodecylsuccinimide N-[3-(3,5-di-t-butyl-4'-hydroxyphenyl)-propanamido]-2-octadecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-octadecylsuccinimide N-[3-(3,5-di-t-butyl-2-hydroxyphenyl)-propanamido]-2-octadecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-isododecylsuccinimide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2,3-dicarboximide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2,3-dicarboximide N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-4-methylhexahydrophthalimide, N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]-2-tetradecylsuccinimide and N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)-propanamido]maleimide.
Claim 6
Dependent Claim
47 words
The composition according to claim 1 further comprising a co-stabilizer selected from the group consisting of an organo-sulfur co-stabilizer, an organo-phosphorous co-stabilizer, a metal alkanoate co-stabilizer and combinations thereof, the co-stabilizer being present in an amount effective to enhance the stabilization of the polymer against thermooxidative degradation.
Claim 7
Dependent Claim
47 words
The composition according to claim 1 further comprising a co-stabilizer selected from the group consisting of beta-(n-octadecylthio)-ethyl-3-(n-octadecylthio)cyclohexane, beta-(n-octadecylthio)ethyl-4-(n-octadecylthio)cyclohexane, a metal alkanoate, a dialkylthiodipropionate, an organic phosphite and combinations thereof, the co-stabilizer being present in an amount effective to enhance the stabilization of the polymer against thermooxidative degradation.
Claim 8
Dependent Claim
11 words
The composition of claim 1 wherein the polymer is a polyolefin.
Claim 9
Dependent Claim
11 words
The composition of claim 5 wherein the polymer is a polyolefin.
Claim 10
Dependent Claim
11 words
The composition of claim 6 wherein the polymer is a polyolefin.
References Cited (Backward Citations)
US3888824A
Cited
US4038247A
Cited
US3706798A
Cited
US3734884A
Cited
US3933736A
Cited
US3956331A
Cited
US4145556A
Cited
US4514533A
Cited
US4520146A
Cited
DE3500058A1
Cited
US4801749A
Cited
US4874803A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-03-31 | 1995-09-30 | 1996-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-03-31 | 1999-09-30 | 2000-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-03-31 | 2003-09-30 | 2004-03-31 | $7700.00 | Window Closed / Lapsed |