US4069199A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Metal salts of hindered piperidine carboxylic acids and stabilized compositions
Assignee: Novartis Corp
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Filing: 1975-09-22
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Granted: 1978-01-17
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Expires: 1995-09-22
Abstract
Abstract Compounds having the formula <IMAGE> WHEREIN R1 and R2 are lower alkyl or cycloalkyl, R3 is hydrogen, alkyl, methoxyethyl, alkenyl, propargyl, benzyl or alkyl substituted benzyl, R4 is lower alkylene, M is 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-tetramethyl-piperidin-4-ol and succinic acid to give O-mono(2,2,6,6-tetramethylpiperidin-4-ol)succinate. 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 20:18
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C09; C09K; C09K15/00; C09K15/04; C09K15/30
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
122 words
A compound of the formula ##STR8## 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 alkyl substituted benzyl, R 4 is straight- or branched-chain alkylene having 1 to 4 carbon atoms, M is a metal selected from the group consisting of barium, magnesium, calcium, sodium, copper, and potassium, and the value of z is the same as the available valence of M.
Claim 2
Dependent Claim
122 words
A compound of the formula ##STR8## 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 alkyl substituted benzyl, R 4 is straight- or branched-chain alkylene having 1 to 4 carbon atoms, M is a metal selected from the group consisting of barium, magnesium, calcium, sodium, copper, and potassium, and the value of z is 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
25 words
A compound according to claim 2 wherein R 4 is straight-chain alkylene having 1 to 4 carbon atoms, and M is barium, calcium or magnesium.
Claim 5
Dependent Claim
11 words
A compound according to claim 3 wherein R 3 is hydrogen.
Claim 6
Dependent Claim
11 words
A compound according to claim 3 wherein R 3 is methyl.
Claim 7
Dependent Claim
17 words
A compound according to claim 3 where in R 4 is straight-chain alkylene having 4 carbon atoms.
Claim 8
Dependent Claim
14 words
A compound according to claim 2 which is the copper (II) complex of O-mono(2,2,6,6-tetramethylpiperidin-4-ol)-succinate.
Claim 9
Dependent Claim
9 words
A compound according to claim 2 which is potassium[O-mono-(2,2,6,6-tetramethyl-piperidin-4-ol)succinate].
Claim 10
Dependent Claim
11 words
A compound according to claim 3 which is barium bis[O-mono(2,2,6,6-tetramethyl-piperidin-4-ol) glutarate].
Claim 11
Dependent Claim
11 words
A compound according to claim 3 which is calcium bis[O-mono(2,2,6,6-tetramethyl-piperidin-4-ol) glutarate].
Claim 12
Dependent Claim
11 words
A compound according to claim 3 which is magnesium bis[O-mono(2,2,6,6-tetramethyl-piperidin-4-ol) glutarate].
Claim 13
Dependent Claim
31 words
A composition of matter stabilized against ultraviolet deterioration which comprises a synthetic organic polymer normally subject to ultraviolet deterioration containing from 0.005 to 5% of the stabilizing compound of claim 1.
Claim 14
Dependent Claim
15 words
A composition of claim 12 which contains additionally 0.005 to 5% of a phenolic antioxidant.
Claim 15
Dependent Claim
15 words
A composition of claim 12 which contains additionally 0.005 to 5% of an organic phosphite.
Claim 16
Dependent Claim
47 words
A composition of claim 12 which contains additionally a. 0.005 to 5% of a phenolic antioxidant and b. a stabilizing amount of a UV absorber selected from the group consisting of hydroxy benzophenones, hydroxyphenyl benzotriazoles, aromatic esters of salicyclic acid and nickel amine complexes of thio bis-phenols.
Claim 17
Dependent Claim
13 words
A composition of claim 12 wherein the synthetic organic polymer is a polyolefin.
Claim 18
Dependent Claim
40 words
A composition of claim 13 which contains additionally 0.01 to 2% of a compound of the formula ##STR9## wherein R is an alkyl group having from 6 to 24 carbon atoms and n is an integer from 1 to 6.
Claim 19
Dependent Claim
10 words
A composition of claim 16 wherein the polyolefin is polypropylene.
Claim 20
Dependent Claim
24 words
A composition of claim 16 which contains additionally 0.005 to 5% of a phenolic antioxidant selected from n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate, di-n-octadecyl(3,5-di-t-butyl--4-hydroxybenzyl)phosphonate, pentaerythritoltetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.
Claim 21
Dependent Claim
38 words
A composition of claim 16 which contains additionally 0.005 to 5% of a phenolic antioxidant selected from n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, di-n-octadecyl(3,5-di-t-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(2'-hydroxy-5'-methylphenyl)-benzotriazole, and 2-hydroxy-4-n-octoxybenzophenone.
Claim 22
Dependent Claim
17 words
A composition of claim 16 wherein the stabilizing compound is the copper (II) complex of O-mono (2,2,6,6-tetramethyl-piperidin-4-ol)-succinate.
Claim 23
Dependent Claim
12 words
A composition of claim 16 wherein the stabilizing compound is potassium [O-mono-(2,2,6,6-tetramethyl-piperidin-4-ol)succinate].
Claim 24
Dependent Claim
13 words
A composition of claim 16 wherein the stabilizing compound is barium bis[O-mono(2,2,6,6-tetramethyl-piperidin-4-ol) glutarate].
Claim 25
Dependent Claim
13 words
A composition of claim 16 wherein the stabilizing compound is calcium bis[O-mono(2,2,6,6-tetramethyl-piperidine-4-ol) glutarate].
Claim 26
Dependent Claim
12 words
A composition of claim 16 wherein the stabilizing compound is magnesium bis[O-mono(2,2,6,6-tetramethyl-piperidin-4-ol)glurate].
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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) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |