US4056507A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hindered piperidine carboxylic acids, metal salts thereof and stabilized compositions
Assignee: Novartis Corp
•
Filing: 1975-11-19
•
Granted: 1977-11-01
•
Expires: 1995-11-19
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, alkyl-thio-alkyl or alkyl-oxo-alkyl, 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-tetramethyl-piperidin-4-ol and sebacic acid to give o-mono(2,2,6,6-tetramethyl-piperidin-4-ol)sebacate. 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
2026-10-29 05:20
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58; C09; C09K; C09K15/00; C09K15/04; C09K15/30
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
202 words
A composition of matter comprising a synthetic organic polymer normally subject to ultraviolet deterioration stabilized with 0.005 to 5% of a stabilizer having 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 5 to 8 carbon atoms, or the group (CH 2 ) m Y(CH 2 ) n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 3, M is hydrogen or a metal selected from the group consisting of barium, nickel, manganese, calcium, zinc, iron, sodium, cobalt, tin and dialkyl tin, and z has a value of from 1 to 4, the value of z being the same as the available valence of M said stabilizer bing incorporated into the synthetic organic polymer after polymerization.
Claim 2
Dependent Claim
202 words
A composition of matter comprising a synthetic organic polymer normally subject to ultraviolet deterioration stabilized with 0.005 to 5% of a stabilizer having 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 5 to 8 carbon atoms, or the group (CH 2 ) m Y(CH 2 ) n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 3, M is hydrogen or a metal selected from the group consisting of barium, nickel, manganese, calcium, zinc, iron, sodium, cobalt, tin and dialkyl tin, and z has a value of from 1 to 4, the value of z being the same as the available valence of M said stabilizer bing incorporated into the synthetic organic polymer after polymerization.
Claim 3
Dependent Claim
15 words
The composition of claim 1 which contains additionally 0.005 to 5% of a phenolic antioxidant.
Claim 4
Dependent Claim
46 words
The composition of claim 1 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 thiobis-phenols.
Claim 5
Dependent Claim
51 words
The composition of claim 1 which contains additionally a. 0.005 to 5% of a phenolic antioxidant, and b. 0.01 to 2% of a thio co-stabilizer 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 6
Dependent Claim
13 words
The composition of claim 1 wherein the synthetic organic polymer is a polyolefin.
Claim 7
Dependent Claim
10 words
The composition of claim 5 wherein the polyolefin is polypropylene.
Claim 8
Dependent Claim
29 words
The composition of claim 5 which contains additionally 0.005 to 5% of a phenolic antioxidant selected from the group consisting of n-octadecyl 3-(3,5-di-t-butyl-4-hydroxyphneyl propionate, di-n-octadecyl(3,5-di-t-butyl-4-hydroxybenzyl) phosphonate, pentaerythritol-tetrakis[3,5-di-t-butyl-4-hydroxyphenyl)propionate] and tris-(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.
Claim 9
Dependent Claim
47 words
The composition of claim 5 which contains additionally a. 0.005 to 5% of a phenolic antioxidant selected from the group consisting of 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 the group consisting of 2(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzatriazole, 2(2'-hydroxy-5'-methylphenyl)-benzotriazole, and 2-hydroxy-4-n-octoxybenzophenone.
Claim 10
Dependent Claim
14 words
The composition of claim 5 wherein R 1 and R 2 are each methyl.
Claim 11
Dependent Claim
61 words
The composition of claim 9 wherein R 4 is straight-chain alkylene having 5 to 8 carbon atoms, or the group (Ch 2 ) m Y(Ch 2 ) n where Y is oxygen or sulfur and m and n independently of each other are 1 to 2, M is hydrogen, nickel or manganese, and Z has a value of 1 or 2.
Claim 12
Dependent Claim
9 words
The composition of claim 10 wherein M is nickel.
Claim 13
Dependent Claim
9 words
The composition of claim 10 wherein M is hydrogen.
Claim 14
Dependent Claim
17 words
The composition of claim 10 wherein R 4 is straight-chain alkylene having 5 to 8 carbon atoms.
Claim 15
Dependent Claim
29 words
The composition of claim 10 wherein R 4 is the group (Ch 2 ) m Y(CH 2 ) n is Y, m and n are defined in claim 24.
Claim 16
Dependent Claim
10 words
The composition of claim 5 wherein the stabilizer is o-mono(2,2,6,6-tetramethyl-piperidin-4-ol)sebacate.
Claim 17
Dependent Claim
12 words
The composition of claim 5 wherein the stabilizer is nickel bis[o-mono(2,2,6,6-tetramethylpiperidin-4-ol) sebacate].
Claim 18
Dependent Claim
11 words
The composition of claim 5 wherein the stabilizer is o-mono(1,2,2,6,6-pentamethyl piperidin-4-ol)diglycolate.
Claim 19
Dependent Claim
12 words
The composition of claim 5 wherein the stabilizer is nickel bis[o-mono(1,2,2,6,6-pentamethylpiperidin-4-ol) diglycolate].
Claim 20
Dependent Claim
154 words
A compound of the formula ##STR10## 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 or 4 carbon atoms, propargyl, benzyl, or alkyl substituted benzyl, R 4 is straight- or branched-chain alkylene having 5 to 8 carbon atoms, or the group (CH 2 ) m Y(CH 2 ) n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 2, M is hydrogen or a metal selected from the group consisting of barium, calcium, and sodium, and the value of z is the same as the available valence of M.
Claim 21
Dependent Claim
154 words
A compound of the formula ##STR10## 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 or 4 carbon atoms, propargyl, benzyl, or alkyl substituted benzyl, R 4 is straight- or branched-chain alkylene having 5 to 8 carbon atoms, or the group (CH 2 ) m Y(CH 2 ) n wherein Y is oxygen or sulfur and m and n independently of each other are an integer of from 1 to 2, M is hydrogen or a metal selected from the group consisting of barium, calcium, and sodium, and the value of z is the same as the available valence of M.
Claim 22
Dependent Claim
15 words
A compound according to claim 19 wherein R 1 and R 2 are each methyl.
Claim 23
Dependent Claim
56 words
A compound according to claim 20 wherein R 4 is straight-chain alkylene having 5 to 8 carbon atoms, or the group (CH 2 ) m Y(CH 2 ) n wherein Y is oxygen or sulfur and m and n independently of each other are 1 and 2, and z has a value of 1 or 2.
Claim 24
Dependent Claim
10 words
A compound according to claim 21 wherein M is hydrogen.
Claim 25
Dependent Claim
18 words
A compound according to claim 20 wherein R 4 is straight-chain alkylene having 5 to 8 carbon atoms.
Claim 26
Dependent Claim
34 words
A compound according to claim 21 wherein R 4 wherein R 4 is the group (CH 2 ) m Y(CH 2 ) n and Y, m and n are as defined in claim 35.
Claim 27
Dependent Claim
9 words
A compound according to claim 21 which is o-mono-(2,2,6,6-tetramethyl-piperidin-4-ol)sebacate.
Claim 28
Dependent Claim
11 words
A compound according to claim 21 which is o-mono (1,2,2,6,6-pentamethyl piperidin-4-ol)diglycolate.
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) | 1980-10-31 | 1981-05-02 | 1981-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-31 | 1985-05-02 | 1985-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-31 | 1989-05-02 | 1989-11-01 | $7700.00 | Window Closed / Lapsed |