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US4590268A
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Process for the preparation of 1-diorganocarbamoyl-polyalkylpiperidines
Assignee: BASF Corp
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Filing: 1983-05-02
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Granted: 1986-05-20
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Expires: 2003-05-02
Abstract
Abstract Compounds containing a group of the formula I ##STR1## in which R is H or C 1 -C 4 -alkyl, R 1 is H, CN, an acyloxy group or a free valency and R 2 and R 3 are organic radicals can be prepared in a simple manner from the corresponding compounds containing a group of the formula Ia ##STR2## by stepwise reaction with phosgene and a secondary amine R 2 --NH--R 3 in the presence of a molar amount of a base. The N-diorganocarbamoyl compounds containing the group I are outstanding light stabilizers, in particular for organic polymers. They can be converted by secondary reactions into other compounds which contain the group I and which are not accessible by direct phosgenation. Many of the products thus obtainable by phosgenation or conversion are novel compounds.
Inventors
- 👤 Friedrich Karrer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 17:02
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/20; C07D295/215; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58; C07D211/60; C07D211/62; C07D211/66; C07D211/68; C07D211/72; C07D211/74; C07D471/00; C07D471/02; C07D471/10; C07D491/00; C07D491/02; C07D491/10; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
210 words
A process for the preparation of compounds of the formula II ##STR36## wherein m is an integer from 1 to 4; R is hydrogen or C 1 -C 4 alkyl; R 1 is hydrogen, C 2 -C 12 alkoxy, C 2 -C 20 alkanoyloxy, benzoyloxy, C 3 -C 25 carbamoyloxy or CN; R 2 is C 1 -C 18 -alkyl, C 3 -C 12 -alkoxyalkyl, C 2 -C 8 -hydroxyalkyl, C 3 -C 12 -alkenyl, C 7 -C 14 -aralkyl, C 6 -C 14 aryl, C 7 -C 14 -alkaryl, C 3 -C 7 -cycloalkyl or 2,2,6,6-tetramethylpiperidin-4-yl; R 3 has one of the meanings of R 2 or R 2 and R 3 , together with the N atom to which they are bonded, form a piperidine, pyrrolidine, morpholine, piperidine or 4-alkylpiperidine ring; and R 4 is hydrogen or an m-valent organic radical, or R 1 and R 4 together are oxo-oxygen or a divalent organic radical; by reacting a compound of the formula IIa ##STR37## with phosgene in an inert solvent in the presence of a molar amount of a base, and subsequently reacting the product with a secondary amine of the formula R 2 --NH--R 3 , also in the presence of a molar amount of a base.
Claim 2
Dependent Claim
210 words
A process for the preparation of compounds of the formula II ##STR36## wherein m is an integer from 1 to 4; R is hydrogen or C 1 -C 4 alkyl; R 1 is hydrogen, C 2 -C 12 alkoxy, C 2 -C 20 alkanoyloxy, benzoyloxy, C 3 -C 25 carbamoyloxy or CN; R 2 is C 1 -C 18 -alkyl, C 3 -C 12 -alkoxyalkyl, C 2 -C 8 -hydroxyalkyl, C 3 -C 12 -alkenyl, C 7 -C 14 -aralkyl, C 6 -C 14 aryl, C 7 -C 14 -alkaryl, C 3 -C 7 -cycloalkyl or 2,2,6,6-tetramethylpiperidin-4-yl; R 3 has one of the meanings of R 2 or R 2 and R 3 , together with the N atom to which they are bonded, form a piperidine, pyrrolidine, morpholine, piperidine or 4-alkylpiperidine ring; and R 4 is hydrogen or an m-valent organic radical, or R 1 and R 4 together are oxo-oxygen or a divalent organic radical; by reacting a compound of the formula IIa ##STR37## with phosgene in an inert solvent in the presence of a molar amount of a base, and subsequently reacting the product with a secondary amine of the formula R 2 --NH--R 3 , also in the presence of a molar amount of a base.
Claim 3
Dependent Claim
33 words
A process according to claim 1, wherein 0.9-1.2 mols of phosgene, at least one mol of the secondary amine and at least 2 mols of a base are used per mol of IIA.
Claim 4
Dependent Claim
15 words
A process according to claim 1, wherein a tertiary amine is used as the base.
Claim 5
Dependent Claim
18 words
A process according to claim 1, wherein the entire reaction is carried out at temperatures below 40° C.
Claim 6
Dependent Claim
11 words
A process according to claim 1 in which R is hydrogen.
Claim 7
Dependent Claim
12 words
A process according to claim 1 in which R 1 is hydrogen.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-05-19 | 1989-11-18 | 1990-05-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-19 | 1993-11-18 | 1994-05-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-19 | 1997-11-18 | 1998-05-20 | $7700.00 | Window Closed / Lapsed |