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Hindered piperidine carboxylic acids, metal salts thereof and stabilized compositions

Assignee: Novartis Corp
•
Filing: 1975-09-22
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Granted: 1978-05-16
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Expires: 1995-09-22
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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-tetramethylpiperidin-4-ol and sebacic acid to give o-mono(2,2,6,6-tetramethylpiperidin-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 2026-11-03 07:14
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; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/232

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 154 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 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 3, M is a metal selected from the group consisting of barium, calcium, magensium, sodium, potassium and copper, and the value of z is the same as the valence of M.
Claim 2
Dependent Claim 154 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 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 3, M is a metal selected from the group consisting of barium, calcium, magensium, sodium, potassium and copper, and the value of z is the same as the 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 62 words
A compound according to claim 2 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 or 2, M is barium, calcium or magnesium, and z has a value of 1 or 2.
Claim 5
Dependent Claim 53 words
A compound according to claim 2 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 or 2, and M is sodium or potassium.
Claim 6
Dependent Claim 10 words
A compound according to claim 3 wherein M is barium
Claim 7
Dependent Claim 10 words
A compound according to claim 3 wherein M is calcium.
Claim 8
Dependent Claim 18 words
A compound according to claim 3 wherein R 4 is straight-chain alkylene having 5 to 8 carbon atoms.
Claim 9
Dependent Claim 31 words
A compound according to claim 3 wherein R 4 is the group (CH 2 ) m Y(CH 2 ) n and Y, m and n are as defined in claim 3.
Claim 10
Dependent Claim 9 words
A compound according to claim 3 which is o-mono(2,2,6,6-tetramethyl-piperidin-4-ol)sebacate.
Claim 11
Dependent Claim 10 words
A compound according to claim 3 which is barium bis[o-mono(2,2,6,6-tetramethylpiperidin-4-ol)sebacate].
Claim 12
Dependent Claim 10 words
A compound according to claim 3 which is calcium bis[o-mono(2,2,6,6-tetramethylpiperidin-4-ol)sebacate].
Claim 13
Dependent Claim 10 words
A compound according to claim 3 which is magnesium bis[o-mono(2,2,6,6-tetramethylpiperidin-4-ol)sebacate].
Claim 14
Dependent Claim 58 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 according to claim 1, (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 15
Dependent Claim 58 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 according to claim 1, (b) 0 to 5% of a phenolic antioxidant, (c) 0 to 5% of a phosphite co-stabilizer, and (d) 0 to 5% of a U.V. absorber.
Claim 16
Dependent Claim 12 words
A composition of claim 13 wherein the organic material is a polyolefin.
Claim 17
Dependent Claim 10 words
A composition of claim 15 wherein the polyolefin is polypropylene.

References Cited (Backward Citations)

US3120540A Cited
US3640928A Cited
US3840494A Cited
US3920661A Cited
US4031095A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-05-15 1981-11-14 1982-05-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-05-15 1985-11-14 1986-05-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-05-15 1989-11-14 1990-05-16 $7700.00 Window Closed / Lapsed

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