US4139520A
Expired / Lapsed
US
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Compositions stabilized with hindered piperidine carboxylic acids or metal salts thereof
Assignee: BASF Corp
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Filing: 1977-05-26
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Granted: 1979-02-13
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Expires: 1997-05-26
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
2026-10-26 01:48
CPC Classifications
C; C07; C07F; C07F3/00; C07F3/003; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/92; C07D211/94
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
250 words
A composition of matter stabilized against ultraviolet deterioration which comprises a synthetic organic polymer normally subject to ultraviolet deterioration containing from (a) 0.005% to 5% of a stabilizing compound of the formula ##STR12## 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-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, nickel, manganese, calcium, copper, zinc, magnesium, sodium, potassium, 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, (b) 0 to 5% of a phenolic antioxidant, (c) 0 to 5% of a thio co-stabilizer, and (d) 0 to 5% of a U.V. absorber.
Claim 2
Dependent Claim
250 words
A composition of matter stabilized against ultraviolet deterioration which comprises a synthetic organic polymer normally subject to ultraviolet deterioration containing from (a) 0.005% to 5% of a stabilizing compound of the formula ##STR12## 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-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, nickel, manganese, calcium, copper, zinc, magnesium, sodium, potassium, 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, (b) 0 to 5% of a phenolic antioxidant, (c) 0 to 5% of a thio co-stabilizer, and (d) 0 to 5% of a U.V. absorber.
Claim 3
Dependent Claim
17 words
A composition of claim 1 wherein R 1 and R 2 in the stabilizer are each methyl.
Claim 4
Dependent Claim
16 words
A composition of claim 2 wherein M in the stabilizer is selected from hydrogen or nickel.
Claim 5
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)cyclohexane-1,2-dicarboxylate].
Claim 6
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)cyclohex-4-ene-1,2-dicarboxylate].
Claim 7
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)-dodecene-1-yl-succinate].
Claim 8
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate].
Claim 9
Dependent Claim
10 words
The composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)phthalate].
Claim 10
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is Ni(II)bis[O-mono(2,2,6,6-tetramethylpiperidin-4-ol)maleate].
Claim 11
Dependent Claim
22 words
A composition of claim 1 wherein R 4 of the stabilizer is 1,2-disubstituted cycloalkylene or cycloalkenylene having 4 to 6 carbon atoms.
Claim 12
Dependent Claim
22 words
A composition of claim 1 wherein R 4 of the stabilizer is 2,3-disubstituted dicycloalkylene or bicycloalkenylene having 7 to 8 carbon atoms.
Claim 13
Dependent Claim
17 words
A composition of claim 1 wherein R 4 of the stabilizer is 1,2-, 1,3- or 1,4-disubstituted phenylene.
Claim 14
Dependent Claim
20 words
A composition of claim 1 wherein R 4 of the stabilizer is straight-chain alkenylene of 2 to 4 carbon atoms.
Claim 15
Dependent Claim
31 words
A composition of claim 1 wherein R 4 of the stabilizer is straight-chain alkylene of 1 to 4 carbon atoms substituted by alkyl or alkenyl of 1 to 18 carbon atoms.
Claim 16
Dependent Claim
9 words
A composition of claim 1 wherein the stabilizer O-mono-(2,2,6,6-tetramethylpiperidin-4-ol)cyclohexane-1,2-dicarboxylate.
Claim 17
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate.
Claim 18
Dependent Claim
11 words
A composition of claim 1 wherein the stabilizer is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)2-dodecene-1-yl succinate.
Claim 19
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)maleate.
Claim 20
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)cyclohex-4-ene-1,2-dicarboxylate.
Claim 21
Dependent Claim
10 words
A composition of claim 1 wherein the stabilizer is O-mono(2,2,6,6-tetramethylpiperidin-4-ol)phthalate.
Claim 22
Dependent Claim
12 words
A composition of claim 1 wherein the organic material is a polyolefin.
Claim 23
Dependent Claim
10 words
A composition of claim 21 wherein the polyolefin in polypropylene.
Claim 24
Dependent Claim
250 words
A composition of matter stabilized against ultraviolet deterioration which comprises a synthetic organic polymer normally subject to ultraviolet deterioration containing from (a) 0.005% to 5% of a stabilizing compound having the formula ##STR13## 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-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, nickel, manganese, calcium, copper, zinc, magnesium, sodium, potassium, 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, (b) 0 to 5% of a phenolic antioxidant, (c) 0 to 5% of a phosphite co-stabilizer and (d) 0 to 5% of a UV absorber.
Claim 25
Dependent Claim
250 words
A composition of matter stabilized against ultraviolet deterioration which comprises a synthetic organic polymer normally subject to ultraviolet deterioration containing from (a) 0.005% to 5% of a stabilizing compound having the formula ##STR13## 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-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, nickel, manganese, calcium, copper, zinc, magnesium, sodium, potassium, 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, (b) 0 to 5% of a phenolic antioxidant, (c) 0 to 5% of a phosphite co-stabilizer and (d) 0 to 5% of a UV absorber.
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) | 1982-02-12 | 1982-08-14 | 1983-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-12 | 1986-08-14 | 1987-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-12 | 1990-08-14 | 1991-02-13 | $7700.00 | Window Closed / Lapsed |