US4093586A
Expired / Lapsed
US
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Pyrrolidine dicarboxylic acids and esters and stabilized compositions
Assignee: Novartis Corp
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Filing: 1976-03-18
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Granted: 1978-06-06
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Expires: 1996-03-18
Abstract
Abstract Compounds having the formula ##STR1## wherein X is alkyl, hydrogen, hydroxyl, oxygen radical, alkenyl, CH 2 CH 2 OCH 3 or CH 2 C.tbd.CH; R 1 is alkyl or phenethyl; and R 2 is alkyl, Are good light stabilizers. These compounds are prepared for example, from acetonlyacetone, an appropriate amine hydrochloride and sodium cyanide to give N-substituted 2,5-dimethyl-2,5-dicyanopyrrolidines which are coverted by standard techniques to the corresponding dicarboxylic acid. These esters are prepared by alkylation of appropriate alkali metal salts.
Inventors
- 👤 John F. Stephen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:01
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C09; C09K; C09K15/00; C09K15/04; C09K15/30; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
61 words
A compound having the formula ##STR7## wherein X is hydrogen, hydroxyl, O, alkyl having 1 to 12 carbons, CH 2 CH 2 OCH 3 , alkenyl having 3 to 4 carbons or CH 2 C.tbd.CH; R 1 is hydrogen, alkyl having 1 to 20 carbons or phenethyl; and R 2 are the same or different alkyls having 1 to 7 carbons.
Claim 2
Dependent Claim
61 words
A compound having the formula ##STR7## wherein X is hydrogen, hydroxyl, O, alkyl having 1 to 12 carbons, CH 2 CH 2 OCH 3 , alkenyl having 3 to 4 carbons or CH 2 C.tbd.CH; R 1 is hydrogen, alkyl having 1 to 20 carbons or phenethyl; and R 2 are the same or different alkyls having 1 to 7 carbons.
Claim 3
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is hydrogen.
Claim 4
Dependent Claim
12 words
A compound of claim 1 wherein R 1 is alkyl or phenethyl.
Claim 5
Dependent Claim
16 words
A compound of claim 1 wherein R 1 is alkyl having 4 to 20 carbon atoms.
Claim 6
Dependent Claim
10 words
A compound of claim 3 wherein R 2 is methyl.
Claim 7
Dependent Claim
9 words
The compound of claim 1 which is N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylic acid.
Claim 8
Dependent Claim
9 words
The compound of claim 1 which is di-n-dodecyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 9
Dependent Claim
8 words
The compound of claim 1 which is 2,5-dimethyl-2,5-dicarbomethoxypyrrolidine-1-oxyl.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is 2,5-dimethyl-3,5-dicarbomethoxy-N-hydroxy-pyrrolidine.
Claim 11
Dependent Claim
9 words
The compound of claim 1 which is dimethyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 12
Dependent Claim
9 words
The compound of claim 1 which is di-n-butyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 13
Dependent Claim
9 words
The compound of claim 1 which is di-n-octyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 14
Dependent Claim
8 words
The compound of claim 1 which is di(2-ethylhexyl)-N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 15
Dependent Claim
9 words
The compound of claim 1 which is diphenethyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 16
Dependent Claim
9 words
The compound of claim 1 which is di-n-octadecyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 17
Dependent Claim
24 words
A composition of matter stabilized against degradation which comprises a synthetic organic polymer subject to ultraviolet light degradation and a compound of claim 1.
Claim 18
Dependent Claim
10 words
A composition of claim 16 wherein R 1 is hydrogen.
Claim 19
Dependent Claim
12 words
A composition of claim 16 wherein R 1 is alkyl or phenethyl.
Claim 20
Dependent Claim
16 words
A composition of claim 16 wherein R 1 is alkyl having 4 to 20 carbon atoms.
Claim 21
Dependent Claim
10 words
A composition of claim 18 wherein R 2 is methyl.
Claim 22
Dependent Claim
11 words
A composition of claim 16 wherein the stabilizer is di-n-octyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 23
Dependent Claim
11 words
A composition of claim 16 wherein the stabilizer is di(2-ethylhexyl) -N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 24
Dependent Claim
11 words
A composition of claim 16 wherein the stabilizer is di-n-dodecyl N-methyl-2,5-dimethylpyrrolidine-2,5-dicarboxylate.
Claim 25
Dependent Claim
11 words
A composition of claim 16 wherein the stabilizer is di-n-octadecyl N-methyl-2,5-di-methylpyrrolidine-2,5-dicarboxylate.
Claim 26
Dependent Claim
13 words
A composition of claim 16 wherein the synthetic organic polymer is a polyolefin.
Claim 27
Dependent Claim
10 words
A composition of claim 25 wherein the polyolefin is polypropylene.
Claim 28
Dependent Claim
40 words
A composition of claim 25 which contains additionally 0.01 to 2% of a compound of a formula ##STR8## wherein R is an alkyl group having from 6 to 24 carbon atoms and n is an integer from 1 to 6.
Claim 29
Dependent Claim
16 words
A composition of claim 25 which contains additionally 0.005 to 5% of a hindered phenolic antioxidant.
Claim 30
Dependent Claim
24 words
A composition of claim 25 which contains additionally 0.005 to 5% of a hindered phenolic antioxidant and a stabilizing amount of a UV absorber.
Claim 31
Dependent Claim
24 words
A composition of claim 28 which contains additionally 0.005 to 5% of a phenolic antioxidant selected from n-octadecyl β(3,5-di-t-butyl-4-hydroxyphenyl)propionate, di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzyl-phosphonate, pentaerythritol tetrakis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.
Claim 32
Dependent Claim
40 words
A composition of claim 29 which contains additionally (a) 0.005 to 5% of a phenolic antioxidant selected from n-octadecyl β--(3,5-di-t-butyl-4-hydroxyphenyl)propionate, di-n-octadecyl-3,5-di-tert-butyl-4-hydroxybenzyl-phosphonate, pentaerythritol tetrakis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate, and (b) a stabilizing amount of a UV absorber selected from 2(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-hydroxy-4-n-octoxybenzophenone, and 2(2'-hydroxy-5'-methylphenyl)-benzotriazole.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-05 | 1981-12-05 | 1982-06-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-05 | 1985-12-05 | 1986-06-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-05 | 1989-12-05 | 1990-06-06 | $7700.00 | Window Closed / Lapsed |