US4191683A
Expired / Lapsed
US
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Derivatives of 4-aminopiperidine as stabilizers for polymers
Assignee: Sankyo Co Ltd
•
Filing: 1977-11-21
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Granted: 1980-03-04
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Expires: 1997-11-21
Abstract
Abstract Derivatives of sterically hindered 4-aminopiperidines are effective as light-stabilizers for organic polymers, especially for polyolefins. The piperidine ring is substituted with at least five alkyl groups, preferably methyl and ethyl groups. The 4-amino group is substituted with mono- or divalent acyl groups. The nitrogen in 1-position may also be substituted with a monovalent organic substituent. The compounds can be synthesized starting from higher homologs of acetone in sequence of several reaction steps.
Inventors
- 👤 Heimo Brunetti
- 👤 Jean Rody
- 👤 Nobuo Soma
- 👤 Tomoyuki Kurumada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 23:48
CPC Classifications
C; C07; C07D; C07D221/00; C07D221/02; C07D221/20; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C07D211/68; C07D211/72; C07D211/74; C07D211/76; C07D211/92; C07D211/94; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/576; C07F9/59; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
238 words
A compound of the formula ##STR15## a mixture of isomers thereof, or an acid addition salt thereof wherein n is 1 to 3 X is hydrogen, methyl, benzyl, aliphatic acyl having 1 to 4 carbon atoms or 2-hydroxyethyl, R 7 is hydrogen, alkyl having 1 to 12 carbon atoms benzyl, or, if n is 2 and Y is alkylene having 2 to 10 carbon atoms, R 7 is hydrogen or acetyl, Y, if n is 1, represents hydrogen, --CH 2 CH 2 OH, --CO--R 13 wherein R 13 is hydrogen, alkyl having 1 to 7 carbon atoms, alkenyl having 2 or 3 carbon atoms or phenyl, --CONH-R 15 wherein R 15 is alkyl having 1 to 18 carbon atoms or phenyl, --SO 2 R 16 wherein R 16 is methyl, phenyl or pary-methylphenyl, --CO--R 12 --COOH wherein R 12 is --CH 2 CH 2 --, --CH═CH-- or o-phenylene, or Y and R 7 together with the N-atom to which they are attached form a succinimide, maleimide or phthalimide ring, if n is 2, Y represents --CO--, --CO--CO--, --CO--R 18 --CO-- wherein R 18 is alkylene having 1 to 8 carbon atoms or phenylene or --CONH--R 19 --NHCO-- wherein R 19 is alkylene having 2 to 6 carbon or tolylene, and if R 7 is hydrogen or acetyl, Y may also be alkylene having 2 to 6 carbon atoms, and, if n is 3, Y represents the 1,3,5-triazine-2,4,6-triyl residue.
Claim 2
Dependent Claim
238 words
A compound of the formula ##STR15## a mixture of isomers thereof, or an acid addition salt thereof wherein n is 1 to 3 X is hydrogen, methyl, benzyl, aliphatic acyl having 1 to 4 carbon atoms or 2-hydroxyethyl, R 7 is hydrogen, alkyl having 1 to 12 carbon atoms benzyl, or, if n is 2 and Y is alkylene having 2 to 10 carbon atoms, R 7 is hydrogen or acetyl, Y, if n is 1, represents hydrogen, --CH 2 CH 2 OH, --CO--R 13 wherein R 13 is hydrogen, alkyl having 1 to 7 carbon atoms, alkenyl having 2 or 3 carbon atoms or phenyl, --CONH-R 15 wherein R 15 is alkyl having 1 to 18 carbon atoms or phenyl, --SO 2 R 16 wherein R 16 is methyl, phenyl or pary-methylphenyl, --CO--R 12 --COOH wherein R 12 is --CH 2 CH 2 --, --CH═CH-- or o-phenylene, or Y and R 7 together with the N-atom to which they are attached form a succinimide, maleimide or phthalimide ring, if n is 2, Y represents --CO--, --CO--CO--, --CO--R 18 --CO-- wherein R 18 is alkylene having 1 to 8 carbon atoms or phenylene or --CONH--R 19 --NHCO-- wherein R 19 is alkylene having 2 to 6 carbon or tolylene, and if R 7 is hydrogen or acetyl, Y may also be alkylene having 2 to 6 carbon atoms, and, if n is 3, Y represents the 1,3,5-triazine-2,4,6-triyl residue.
Claim 3
Dependent Claim
21 words
A compound as claimed in claim 1 wherein R 7 is hydrogen, alkyl having 1 to 12 carbon atoms or benzyl.
Claim 4
Dependent Claim
13 words
A compound as claimed in claim 1 wherein X is hydrogen or methyl.
Claim 5
Dependent Claim
36 words
A compound as claimed in claim 1 wherein Y, if n is 1, represents hydrogen, and if n is 2 and R 7 is hydrogen or acetyl, Y represents alkylene having 2 to 6 carbon atoms.
Claim 6
Dependent Claim
10 words
A compound as claimed in claim 1 which is N,N'-bis-(2,6-diethyl-2,3,6-trimethyl-4-piperidyl)-oxalamide.
Claim 7
Dependent Claim
10 words
A compound as claimed in claim 1 which is N,N'-bis(2,6-diethyl-2,3,6-trimethyl-4-piperidyl)-adipamide.
Claim 8
Dependent Claim
10 words
A compound as claimed in claim 1 which is N,N'-bis-(2,6-diethyl-2,3,6-trimethyl-4-piperidyl)-hexamethylenediamine.
Claim 9
Dependent Claim
117 words
A compound of the formula I ##STR16## a mixture of isomers thereof, or an acid addition salt thereof wherein X is hydrogen or aliphatic acyl having 1 to 4 carbon atoms, R 7 is hydrogen or alkyl having 1-12 carbon atoms, Y, if n is 1, represents hydrogen, --CO-R 13 wherein R 13 is hydrogen, alkyl having 1 to 7 carbon atoms or phenyl, or --CONH-R 15 wherein R 15 is alkyl having 1-18 carbon atoms or phenyl, and, if n is 2, Y represents --CO--, --CO--CO--, or --CO--R 18 --CO-- wherein R 18 is alkylene having 1-8 carbon atoms, with the proviso that only one of R 7 and Y is hydrogen when n is 1.
Claim 10
Dependent Claim
117 words
A compound of the formula I ##STR16## a mixture of isomers thereof, or an acid addition salt thereof wherein X is hydrogen or aliphatic acyl having 1 to 4 carbon atoms, R 7 is hydrogen or alkyl having 1-12 carbon atoms, Y, if n is 1, represents hydrogen, --CO-R 13 wherein R 13 is hydrogen, alkyl having 1 to 7 carbon atoms or phenyl, or --CONH-R 15 wherein R 15 is alkyl having 1-18 carbon atoms or phenyl, and, if n is 2, Y represents --CO--, --CO--CO--, or --CO--R 18 --CO-- wherein R 18 is alkylene having 1-8 carbon atoms, with the proviso that only one of R 7 and Y is hydrogen when n is 1.
Claim 11
Dependent Claim
1 words
4-Dodecylamino-2,6-diethyl-2,3,6-trimethylpiperidine.
Claim 12
Dependent Claim
1 words
4-Dodecylamino-2,6-diethyl-2,3,6-trimethylpiperidine.
Claim 13
Dependent Claim
1 words
4-Amino-2,6-diethyl-2,3,6-trimethylpiperidine.
Claim 14
Dependent Claim
1 words
4-Amino-2,6-diethyl-2,3,6-trimethylpiperidine.
Claim 15
Dependent Claim
48 words
A composition of matter stabilized agains light-induced deterioration comprising an organic polymer, normally subject to deterioration by light, and from 0.01 go 5.0 percent by weight of a compound of formula I as claimed in claim 1, a mixture of isomers thereof or an acid addition salt thereof.
Claim 16
Dependent Claim
20 words
A composition as claimed in claim 11 wherein the organic polymer is a polyolefin or a styrene homo- or copolymer.
Claim 17
Dependent Claim
17 words
A composition as claimed in claim 11 wherein the organic polymer is a polyurethane or a polyamide.
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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) | 1983-03-04 | 1983-09-03 | 1984-03-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-03-04 | 1987-09-03 | 1988-03-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-03-04 | 1991-09-03 | 1992-03-04 | $7700.00 | Window Closed / Lapsed |