US4348524A
Expired / Lapsed
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Amide derivatives of polyalkylpiperidines
Assignee: BASF Corp
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Filing: 1981-03-17
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Granted: 1982-09-07
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Expires: 2001-03-17
Abstract
Abstract Compounds of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2 and R, R 1 , R 2 , Z and X are as defined in claim 1, and also salts of these compounds, are valuable light stabilizers for organic materials, especially for polymers. The compounds of the formula I can be prepared from the corresponding 4-sec.-aminopiperidines by reaction with cyclic dicarboxylic acid anhydrides and appropriate further reactions.
Inventors
- 👤 Friedrich Karrer
- 👤 Paul Moser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:13
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
398 words
A compound of the formula I ##STR54## in which m is 0 or 1 and n is 1 or 2, X is --OH, --OR 3 or --N(R 4 )(R 5 ), R is hydrogen or CH 3 , R 1 , if n is 1, is C 1 -C 18 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 5 -methoxyalkyl, C 5 -C 8 -cycloalkyl, C 6 -C 7 -cycloalkylmethyl, unsubstituted C 7 -C 12 -aralkyl or C 7 -C 12 -aralkyl substituted by C 1 -C 4 -alkyl and/or hydroxyl, or phenyl, 2-cyanoethyl, 2-alkoxy(C 1 -C 4 )-carbonylethyl or a group of the formula II or III ##STR55## and if n is 2 is C 2 -C 12 -alkylene, C 2 -C 12 -alkylene interrupted by one or more --O-- or --N(R 7 )-- or C 6 -C 18 -cycloalkylene, R 2 is hydrogen, an oxyl radical, C 1 -C 12 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 5 -alkenyl, propargyl, benzyl or acetyl, Z is a group ##STR56## R 3 is C 1 -C 12 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 10 -alkoxyalkyl, C 3 -C 5 -alkenyl, benzyl, cyclohexyl or a radical of the formula III, R 4 is hydrogen, C 1 -C 12 -alkyl, C 3 -C 5 -alkenyl, benzyl or cyclohexyl and R 5 is hydrogen, C 1 -C 12 -alkyl, allyl, C 2 -C 4 -hydroxyalkyl, cyclohexyl or a radical of the formula III, or R 4 and R 5 together with the N atom to which they are bonded form a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 6 is hydrogen or methyl, R 7 is methyl or one of the acyl radicals --CO--(CH 2 ) m --Z--CO--X, R 8 is hydrogen or C 1 -C 18 -alkyl and R 9 is hydrogen, C 1 -C 18 -alkyl or C 3 -C 12 -alkenyl or phenyl, or R 8 and R 9 together with the two carbon atoms to which they are bonded form a saturated or unsaturated, at least 5-membered, carbocyclic ring, and R 10 and R 11 independently of one another are hydrogen or methyl, or a salt of such a compound with a mineral acid, sulfonic acid or organic phosphoric acid, or a salt of a compound of the formula I in which X is --OH with a monovalent to trivalent metal.
Claim 2
Dependent Claim
398 words
A compound of the formula I ##STR54## in which m is 0 or 1 and n is 1 or 2, X is --OH, --OR 3 or --N(R 4 )(R 5 ), R is hydrogen or CH 3 , R 1 , if n is 1, is C 1 -C 18 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 5 -methoxyalkyl, C 5 -C 8 -cycloalkyl, C 6 -C 7 -cycloalkylmethyl, unsubstituted C 7 -C 12 -aralkyl or C 7 -C 12 -aralkyl substituted by C 1 -C 4 -alkyl and/or hydroxyl, or phenyl, 2-cyanoethyl, 2-alkoxy(C 1 -C 4 )-carbonylethyl or a group of the formula II or III ##STR55## and if n is 2 is C 2 -C 12 -alkylene, C 2 -C 12 -alkylene interrupted by one or more --O-- or --N(R 7 )-- or C 6 -C 18 -cycloalkylene, R 2 is hydrogen, an oxyl radical, C 1 -C 12 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 5 -alkenyl, propargyl, benzyl or acetyl, Z is a group ##STR56## R 3 is C 1 -C 12 -alkyl, C 2 -C 4 -hydroxyalkyl, C 3 -C 10 -alkoxyalkyl, C 3 -C 5 -alkenyl, benzyl, cyclohexyl or a radical of the formula III, R 4 is hydrogen, C 1 -C 12 -alkyl, C 3 -C 5 -alkenyl, benzyl or cyclohexyl and R 5 is hydrogen, C 1 -C 12 -alkyl, allyl, C 2 -C 4 -hydroxyalkyl, cyclohexyl or a radical of the formula III, or R 4 and R 5 together with the N atom to which they are bonded form a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, R 6 is hydrogen or methyl, R 7 is methyl or one of the acyl radicals --CO--(CH 2 ) m --Z--CO--X, R 8 is hydrogen or C 1 -C 18 -alkyl and R 9 is hydrogen, C 1 -C 18 -alkyl or C 3 -C 12 -alkenyl or phenyl, or R 8 and R 9 together with the two carbon atoms to which they are bonded form a saturated or unsaturated, at least 5-membered, carbocyclic ring, and R 10 and R 11 independently of one another are hydrogen or methyl, or a salt of such a compound with a mineral acid, sulfonic acid or organic phosphoric acid, or a salt of a compound of the formula I in which X is --OH with a monovalent to trivalent metal.
Claim 3
Dependent Claim
15 words
A compound according to claim 1, of the formula I, in which R is hydrogen.
Claim 4
Dependent Claim
46 words
A compound according to claim 1, of the formula I, in which n is 1 and R 1 is C 2 -C 12 -alkyl, or n is 2 and R 1 is C 2 -C 12 -alkylene, or C 4 -C 10 -alkylene interrupted by --O--.
Claim 5
Dependent Claim
25 words
A compound according to claim 1, of the formula I, in which R 2 is hydrogen, C 1 -C 4 -alkyl, allyl, benzyl or acetyl.
Claim 6
Dependent Claim
15 words
A compound according to claim 1, of the formula I, in which m is nought.
Claim 7
Dependent Claim
44 words
A compound according to claim 5, of the formula I, in which m is 0 and Z is a --CH═CH-- or --CH 2 --CH(R 9 )-- group, in which R 9 is hydrogen or alkyl, or Z is a 1,2-phenylene, 1,2-cyclohexylene or 1,2,3,6-tetrahydro-1,2-phenylene radical.
Claim 8
Dependent Claim
26 words
A compound according to claim 1, of the formula I, in which X is --OH or --OR 3 and R 3 is alkyl, allyl or benzyl.
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) | 1985-09-06 | 1986-03-08 | 1986-09-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-09-06 | 1990-03-08 | 1990-09-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-09-06 | 1994-03-08 | 1994-09-07 | $7700.00 | Window Closed / Lapsed |