US4191829A
Expired / Lapsed
US
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Hindered piperidine carboxylic acids and metal salts thereof
Assignee: BASF Corp
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Filing: 1978-04-25
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Granted: 1980-03-04
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Expires: 1998-04-25
Abstract
Abstract Compounds having the formula ##STR1## wherein R 1 and R 2 are lower alkyl or cycloalkyl, R 3 is hydrogen, alkyl, methoxyethyl, alkenyl, propargyl, benzyl or alkyl substituted benzyl, R 4 is alkylene of 1 to 4 carbon atoms substituted with alkyl or alkenyl of 1 to 18 carbon atoms, alkenylene of 1 to 4 carbon atoms, cycloalkylene, cycloalkenylene, bicycloalkylene, bicycloalkenylene, or phenyllene, M is hydrogen or a metal, and z has a value of from 1 to 4, are good light stabilizers. The carboxylic acids are prepared for example, from 2,2,6,6-tetramethylpiperidin-4-ol and cyclohexane-1,2-dicarboxylic anhydride to give (O-mono (2,2,6,6-tetramethylpiperidin-4-ol)cyclohexane(1,2-dicarboxylate. The metal salts of the acids are readily prepared by reacting the acids or their salts with a reactive form of the metal or metal complex.
Inventors
- 👤 Chester E. Ramey
- 👤 John J. Luzzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 07:58
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/92; C07D211/94; C07F; C07F3/00; C07F3/003; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
194 words
A compound of the formula ##STR12## wherein R 1 and R 2 independently of each other are straight-or branched-chain alkyl having from 1 to 6 carbon atoms, or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group, R 3 is hydrogen, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 to 4 carbon atoms propargyl, benzyl, or benzyl substituted with one or two methyl groups, R 4 is straight-chain alkenylene of 2 to 4 carbon atoms, 1,2-disubstituted cycloalkylene or cycloalkenylene having 4 to 6 carbon atoms, 2,3-disubstituted bicycloalkylene or bicycloalkenylene having 7 to 8 carbon atoms or 1,2-, 1,3- or 1,4-disubstituted phenylene, or a straight-chain alkylene of 1 to 4 carbon atoms substituted by alkyl or alkenyl of 1 to 18 carbon atoms, provided that the straight-chain alkylene substituted by alkyl has more than 8 carbon atoms, M is hydrogen or a metal selected from the group consisting of barium, calcium, magnesium, sodium, potassium, and z has a value of from 1 to 4, the value of z being the same as the available valence of M.
Claim 2
Dependent Claim
194 words
A compound of the formula ##STR12## wherein R 1 and R 2 independently of each other are straight-or branched-chain alkyl having from 1 to 6 carbon atoms, or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group, R 3 is hydrogen, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 to 4 carbon atoms propargyl, benzyl, or benzyl substituted with one or two methyl groups, R 4 is straight-chain alkenylene of 2 to 4 carbon atoms, 1,2-disubstituted cycloalkylene or cycloalkenylene having 4 to 6 carbon atoms, 2,3-disubstituted bicycloalkylene or bicycloalkenylene having 7 to 8 carbon atoms or 1,2-, 1,3- or 1,4-disubstituted phenylene, or a straight-chain alkylene of 1 to 4 carbon atoms substituted by alkyl or alkenyl of 1 to 18 carbon atoms, provided that the straight-chain alkylene substituted by alkyl has more than 8 carbon atoms, M is hydrogen or a metal selected from the group consisting of barium, calcium, magnesium, sodium, potassium, and z has a value of from 1 to 4, the value of z being the same as the available valence of M.
Claim 3
Dependent Claim
15 words
A compound according to claim 1 wherein R 1 and R 2 are each methyl.
Claim 4
Dependent Claim
20 words
A compound according to claim 1 wherein R 4 is 1,2-disubstituted cycloalkylene or cycloalkenylene having 4 to 6 carbon atoms.
Claim 5
Dependent Claim
20 words
A compound according to claim 1 wherein R 4 is 2,3-disubstituted bicycloalkylene or bicycloalkenylene having 7 to 8 carbon atoms.
Claim 6
Dependent Claim
15 words
A compound according to claim 1 wherein R 4 is 1,2-, 1,3- or 1,4-disubstituted phenylene.
Claim 7
Dependent Claim
18 words
A compound according to claim 1 wherein R 4 is straight-chain alkenylene of 2 to 4 carbon atoms.
Claim 8
Dependent Claim
29 words
A compound according to claim 1 wherein R 4 is straight-chain alkylne of 1 to 4 carbon atoms substituted by alkyl or alkenyl of 1 to 18 carbon atoms.
Claim 9
Dependent Claim
10 words
A compound according to claim 2 wherein M is hydrogen.
Claim 10
Dependent Claim
9 words
A compound according to claim 2 which is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)cyclohexane-1,2-dicarboxylate.
Claim 11
Dependent Claim
10 words
A compound according to claim 2 which is O-mono (2,2,6,6-tetramethylpiperidin-4-ol)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate.
Claim 12
Dependent Claim
11 words
A compound according to claim 2 which is O-mono (2,2,6,6-tetramethylpiperidin-4-ol)-2-dodecene-1-yl succinate.
Claim 13
Dependent Claim
10 words
A compound according to claim 2 which is O-mono (2,2,6,6-tetramethylpiperidin-4-ol)maleate.
Claim 14
Dependent Claim
9 words
A compound according to claim 2 which is O-mono-(2,2,6,6-tetramethylpiperdin-4-ol)cyclohex-4-ene-1,2-dicarboxylate.
Claim 15
Dependent Claim
9 words
A compound according to claim 2 which is O-mono-(2,2,6,6-tetramethylpiperidin-4-ol)phthalate.
Claim 16
Dependent Claim
9 words
A compound of claim 2 wherein M is sodium.
Claim 17
Dependent Claim
9 words
A compound of claim 2 wherein M is potassium.
Claim 18
Dependent Claim
9 words
A compound of claim 2 wherein M is calcium.
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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 |