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N-Piperidyl lactam light stabilizers

Assignee: BASF Corp
•
Filing: 1983-10-21
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Granted: 1984-09-18
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Expires: 2003-10-21
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Abstract

Abstract Compounds of the formula (L--T) g --E (I) or (L--T--G) h --Q (II), where L is a lactam group, T is a substituted 4-piperidinyl hindered amine moiety and E or Q are selected linking or terminal groups, are effective light stabilizers for polyolefins and other organic polymers.

Inventors

  • 👤 Roger F. Malherbe

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 05:09
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/04; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C07D401/14; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 429 words
A light stabilizer compound of the formula I or II (L--T).sub.g --E (I) or (L--T--G).sub.h --Q (II) wherein L is a lactam group of the formula ##STR8## n is 0 to 3, T is a group of the formula ##STR9## with L attached to the 4-position of the piperidinyl ring, R 1 is hydrogen or alkyl of 1 to 5 carbon atoms, g is 1 or 2, when g is 1, E is hydrogen, oxygen, hydroxyl, alkyl of 1 to 12 carbon atoms, alkenyl with 3 to 8 carbon atoms, propargyl, benzyl, cyano, hydroxyalkyl of 2 to 4 carbon atoms, alkanoyl of 2 to 10 carbon atoms, alkenoyl of 3 to 4 carbon atoms, benzoyl, alkoxy of 1 to 8 carbon atoms, alkanoyloxy of 2 to 10 carbon atoms, alkenoyloxy of 3 to 4 carbon atoms, benzoyloxy, when g is 2, E is a straight- or branched-chain alkylene of 2 to 6 carbon atoms, styrolene, 2-butenylene or alkylenearylenealkylene of 8 to 15 carbon atoms; or G is G 1 or G 2 , G 1 is ##STR10## R 2 is hydrogen, alkyl of 1 to 2 carbon atoms or phenyl, G 2 is --CH 2 COO--, where T is attached to the methylene carbon atom of G 1 or G 2 , h is 1 to 4, when h is 1 and G is G 1 , Q is alkanoyl of 2 to 10 carbon atoms, benzoyl, or the group ##STR11## R 3 is alkyl of 1 to 8 carbon atoms, R 4 is branched alkyl of 3 to 8 carbon atoms, when h is 2 and G is G 1 , Q is carbonyl, oxalyl or alkanedioyl of 3 to 12 carbon atoms, when h is 3 and G is G 1 , Q is alkanetrioyl of 6 to 10 carbon atoms, when h is 4, and G is G 1 Q is alkanetetroyl of 8 to 12 carbon atoms, when h is 1 and G is G 2 , Q is alkyl of 1 to 12 carbon atoms, or the group T--E where E is as defined above when g is 1, when h is 2 and G is G 2 , Q is alkylene of 2 to 12 carbon atoms, cycloalkylene of 6 to 8 carbon atoms, 3-oxapentamethylene, 1,4-cyclohexylenedimethylene or the group --T--CH 2 CH 2 --, when h is 3 and G is G 2 , Q is alkanetriyl of 3 to 8 carbon atoms, or when h is 4 and G is G 2 , Q is alkanetetrayl of 4 to 10 carbon atoms.
Claim 2
Dependent Claim 429 words
A light stabilizer compound of the formula I or II (L--T).sub.g --E (I) or (L--T--G).sub.h --Q (II) wherein L is a lactam group of the formula ##STR8## n is 0 to 3, T is a group of the formula ##STR9## with L attached to the 4-position of the piperidinyl ring, R 1 is hydrogen or alkyl of 1 to 5 carbon atoms, g is 1 or 2, when g is 1, E is hydrogen, oxygen, hydroxyl, alkyl of 1 to 12 carbon atoms, alkenyl with 3 to 8 carbon atoms, propargyl, benzyl, cyano, hydroxyalkyl of 2 to 4 carbon atoms, alkanoyl of 2 to 10 carbon atoms, alkenoyl of 3 to 4 carbon atoms, benzoyl, alkoxy of 1 to 8 carbon atoms, alkanoyloxy of 2 to 10 carbon atoms, alkenoyloxy of 3 to 4 carbon atoms, benzoyloxy, when g is 2, E is a straight- or branched-chain alkylene of 2 to 6 carbon atoms, styrolene, 2-butenylene or alkylenearylenealkylene of 8 to 15 carbon atoms; or G is G 1 or G 2 , G 1 is ##STR10## R 2 is hydrogen, alkyl of 1 to 2 carbon atoms or phenyl, G 2 is --CH 2 COO--, where T is attached to the methylene carbon atom of G 1 or G 2 , h is 1 to 4, when h is 1 and G is G 1 , Q is alkanoyl of 2 to 10 carbon atoms, benzoyl, or the group ##STR11## R 3 is alkyl of 1 to 8 carbon atoms, R 4 is branched alkyl of 3 to 8 carbon atoms, when h is 2 and G is G 1 , Q is carbonyl, oxalyl or alkanedioyl of 3 to 12 carbon atoms, when h is 3 and G is G 1 , Q is alkanetrioyl of 6 to 10 carbon atoms, when h is 4, and G is G 1 Q is alkanetetroyl of 8 to 12 carbon atoms, when h is 1 and G is G 2 , Q is alkyl of 1 to 12 carbon atoms, or the group T--E where E is as defined above when g is 1, when h is 2 and G is G 2 , Q is alkylene of 2 to 12 carbon atoms, cycloalkylene of 6 to 8 carbon atoms, 3-oxapentamethylene, 1,4-cyclohexylenedimethylene or the group --T--CH 2 CH 2 --, when h is 3 and G is G 2 , Q is alkanetriyl of 3 to 8 carbon atoms, or when h is 4 and G is G 2 , Q is alkanetetrayl of 4 to 10 carbon atoms.
Claim 3
Dependent Claim 16 words
A compound according to claim 1, where in the group L, n is 2 or 3.
Claim 4
Dependent Claim 10 words
A compound according to claim 2 wherein n is 2.
Claim 5
Dependent Claim 17 words
A compound according to claim 1, where in the group T, R 1 is hydrogen or methyl.
Claim 6
Dependent Claim 11 words
A compound according to claim 4 wherein R 1 is hydrogen.
Claim 7
Dependent Claim 32 words
A compound according to claim 1 wherein, when g is 1, E is hydrogen, oxygen, hydroxyl, alkyl of 1 to 4 carbon atoms, allyl, 2-hydroxyethyl, acetyl, propargyl, benzyl, cyano, benzoyl or benzoyloxy.
Claim 8
Dependent Claim 16 words
A compound according to claim 1 wherein, when g is 2, E is ethylene or p-xylylene.
Claim 9
Dependent Claim 11 words
A compound according to claim 1 wherein R 2 is hydrogen.
Claim 10
Dependent Claim 33 words
A compound according to claim 1 wherein, when h is 1 and G is G 1 , Q is acetyl or the group ##STR12## where R 3 and R 4 are each tert-butyl.
Claim 11
Dependent Claim 26 words
A compound according to claim 1 wherein, when h is 2 and G is G 1 , Q is alkanedioyl of 6 to 10 carbon atoms.
Claim 12
Dependent Claim 35 words
A compound according to claim 1 wherein, when h is 1 and G is G 2 , Q is alkyl of 1 to 4 carbon atoms or the group T--E as defined in claim 1.
Claim 13
Dependent Claim 34 words
A compound according to claim 1 wherein, when h is 2 and G is G 2 , Q is alkylene of 2 to 8 carbon atoms or the group --T--CH 2 CH 2 --.
Claim 14
Dependent Claim 9 words
A compound according to claim 1 which is N-(2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.
Claim 15
Dependent Claim 9 words
A compound according to claim 1 which is N-(1-allyl-2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.
Claim 16
Dependent Claim 9 words
A compound according to claim 1 which is di-[2-[4-(2-oxo-1-azepinyl)-2,2,6,6-tetramethylpiperidin-1-yl]ethyl]sebacate.
Claim 17
Dependent Claim 10 words
A compound according to claim 1 which is 1,2,2,6,6-pentamethylpiperidin-4-yl 4-(2-oxo-1-azepinyl)-2,2,6,6-tetramethylpiperdin-1-ylacetate.
Claim 18
Dependent Claim 9 words
A compound according to claim 1 which is N-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.
Claim 19
Dependent Claim 9 words
A compound according to claim 1 which is N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.
Claim 20
Dependent Claim 27 words
A composition of matter comprising an organic material subject to light-induced deterioration stabilized with from 0.05 to 5% by weight of a compound according to claim 1.
Claim 21
Dependent Claim 14 words
A composition according to claim 19 in which the organic material is a polyolefin.
Claim 22
Dependent Claim 14 words
A composition according to claim 20 in which the polyolefin is polyethylene or polypropylene.
Claim 23
Dependent Claim 11 words
A composition according to claim 19 wherein the compound is N-(2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.
Claim 24
Dependent Claim 30 words
A method of stabilizing an organic material subject to light-induced deterioration which comprises adding to said material from 0.05 to 5% by weight of a compound according to claim 1.
Claim 25
Dependent Claim 14 words
A method according to claim 23 in which the organic material is a polyolefin.
Claim 26
Dependent Claim 14 words
A method according to claim 24 in which the polyolefin is polyethylene or polypropylene.
Claim 27
Dependent Claim 11 words
A method according to claim 23 wherein the compound is N-(2,2,6,6-tetramethylpiperidin-4-yl)-epsilon-caprolactam.

References Cited (Backward Citations)

US3000880A Cited
US3684765A Cited
US3850877A Cited
US4014887A Cited
US4033928A Cited
US4371644A Cited
US4309541A Cited
US4309546A Cited
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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) 1987-09-18 1988-03-19 1988-09-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-09-18 1992-03-19 1992-09-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-09-18 1996-03-19 1996-09-18 $7700.00 Window Closed / Lapsed

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