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US5204473A Expired / Lapsed US ⏱️ 0.0 years remaining

O-substituted N-hydroxy hindered amine stabilizers

Assignee: Novartis Corp
•
Filing: 1992-05-12
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Granted: 1993-04-20
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Expires: 2012-05-12
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Abstract

Abstract Hindered amines based on various 2,2,6,6-tetraalkylated nitrogen-containing heterocyclic moieties wherein the hindered nitrogen atom on the ring is substituted with OR 1 substituents and the 4-position of the ring is substituted with a variety of groups, are effective as light stabilizers in diverse substrate systems.

Inventors

  • 👤 Roland A. E. Winter
  • 👤 James P. Galbo
  • 👤 Raymond Seltzer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 18:18
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/14; C07D211/00; C07D211/92; C07D211/94; C07D491/00; C07D491/02; C07D491/10; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C08K5/3467; C08K5/3477; C08K5/3492; C08K5/34926

Claims Analysis

Total Claims: 43
Claim 1
Independent Claim 1219 words
A compound corresponding to the formulae ##STR12## wherein R is hydrogen or methyl, R 1 is independently C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 5 -C 8 cycloalkenyl, C 5 -C 12 cycloalkyl, C 6 -C 10 bicycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, or C 7 -C 9 aralkyl substituted by alkyl or C 6 -C 10 aryl; m is 2-4, when m is 2, R 2 is C 1 -C 12 alkylene, C 4 -C 12 alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, or of a dicarbamic acid, ##STR13## wherein D 3 and D 4 are independently hydrogen, an alkyl radical containing up to 8 carbon atoms, an C 6 -C 10 aryl or an C 7 -C 9 aralkyl or 3,5-di-tert-butyl-4-hydroxybenzyl radical, D 5 is hydrogen, or an alkyl or alkenyl radical containing up to 18 carbon atoms, and d is 0-20; when m is 4, R 2 is a trivalent acyl radical of an aliphatic, unsaturated aliphatic, cycloaliphatic, or aromatic tricarboxylic acid; when m is 4, R 2 is a tetravalent acyl radical of a saturated or unsaturated aliphatic or aromatic tetracarboxylic acid, p is 1, 2 or 3, R 3 is hydrogen, C 1 -C 12 alkyl, C 5 C 7 cycloalkyl, C 7 -C 8 aralkyl, C 2 -C 18 alkanoyl, C 3 -C 5 alkenoyl or benzoyl; when p is 1, R 4 is hydrogen, C 1 -C 18 alkyl C 5 C 7 cycloalkyl, C 2 -C 8 alkenyl unsubstituted or substituted by a cyano, carbonyl or carbamide group, C 6 -C 10 aryl, C 7 -C 9 aralkyl, glycidyl, a group of the formula --CH 2 --CH(OH)--Z or of the formula --CO--Z-- or --CONH--Z wherein Z is hydrogen, methyl or phenyl; or a group of the formulae ##STR14## or R 3 and R 4 together when p is 1 can be alkylene of 4 to 6 carbon atoms or 2-oxapolyalkylene or the cyclic acyl radical of an aliphatic or aromatic 1,2- or 1,3-dicarboxylic acid, when p is 2, R 4 is a direct bond or is C 1 -C 12 alkylene, C 6 -C 12 arylene, xylylene, a --CH 2 CH(OH)--CH 2 group, or a group --CH 2 --CH(OH)--CH 2 --O--X--O--CH 2 --CH(OH)--CH 2 -- wherein X is C 2 -C 10 alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene; or, provided that R 3 is not alkanoyl, alkenoyl or benzoyl, R 4 can also be a divalent acyl radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or of a dicarbamic acid, or can be the group --CO--; or R 4 is ##STR15## where T 8 and T 9 are independently hydrogen, alkyl of 1 to 18 carbon atoms, or T 8 and T 9 together are alkylene of 4 to 6 carbon atoms or 3-oxapentamethylene, when p is 3, R 4 is 2,4,6-triazinyl, n is 1 or 2, when n is 1, R 5 and R' 5 are independently C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 7 -C 12 aralkyl, or R 5 is also hydrogen, or R 5 and R' 5 together are C 2 -C 8 alkylene or C 2 -C 8 hydroxyalkylene or C 4 -C 22 acyloxyalkylene; when n is 2, R 5 R' 5 together are (--CH 2 ) 2 C(CH 2 --) 2 ; R 6 is hydrogen, C 1 -C 12 alkyl, allyl, benzyl, glycidyl or C 2 -C 6 alkoxyalkyl; when n is 1, R 7 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl, C 7 -C 9 aralkyl, C 5 -C 7 cycloalkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 6 -C 10 aryl, glycidyl, a group of the formula --(CH 2 ) t --COO--Q or of the formula --(CH 2 ) t --O--CO--Q wherein t is 1 or 2, and Q is C 1 -C 4 alkyl or phenyl; or when n is 2, R 7 is C 2 -C 12 alkylene, C 6 -C 12 arylene, a group --CH 2 CH(OH)--CH 2 --O--X--O--CH 2 --CH(OH)--CH 2 -- wherein X is C 2 -C 10 alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene, or a group --CH 2 CH(OZ')CH 2 --(OCH 2 --CH(OZ')CH 2 ) 2 -- wherein Z' is hydrogen, C 1 -C 18 alkyl, allyl, benzyl, C 2 -C 12 alkanoyl or benzoyl; Q 1 is --N(R 8 )-- or --O--; E is C 1 -C 3 alkylene, the group --CH 2 --CH(R 9 )--O-- wherein R 9 is hydrogen, methyl or phenyl, the group --(CH 2 ) 3 --NH-- or a direct bond; R 10 is hydrogen or C 1 -C 18 alkyl, R 8 is hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 7 -C 12 aralkyl, cyanoethyl, C 6 -C 10 aryl, the group --CH 2 --CH(R 9 )--OH wherein R 9 has the meaning defined above; a group of the formula ##STR16## or a group of the formula ##STR17## wherein G is C 2 -C 6 alkylene or C 6 -C 12 arylene; or R 8 is a group --E--CO--NH--CH 2 --OR 10 ; T 3 is ethylene or 1,2-propylene, or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate; k is 2 to 100; T 4 has the same meaning as R 4 when p is 1 or 2, T 5 is methyl, T 6 is methyl or ethyl, or T 5 and T 6 together are tetramethylene or pentamethylene, M and Y are independently methylene or carbonyl; T 7 is the same as R 7 , T 10 and T 11 are independently alkylene of 2 to 12 carbon atoms, or T 11 is ##STR18## T 12 is piperazinyl, --NR 11 --(CH 2 ) d --NR 11 -- or ##STR19## where R 11 is the same as R 3 and is also ##STR20## a, b and c are independently 2 or 3, and f is 0 or 1, e is 2, 3 or 4; T 13 is the same as R 2 with the proviso that T 13 cannot be hydrogen when n is 1; E 1 and E 2 , being different, each are --CO-- or --N(E 5 ) where E 5 is hydrogen, C 1 -C 12 alkyl or alkoxycarbonylalkyl of 4 to 22 carbon atoms; E 3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms, E 4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or E 3 and E 4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by up to four alkyl groups of 1 to 4 carbon atoms, and E 6 is an aliphatic or aromatic tetravalent radical, and with the proviso that in formula B when R 1 is alkyl, R 3 is not hydrogen.
Claim 2
Dependent Claim 1219 words
A compound corresponding to the formulae ##STR12## wherein R is hydrogen or methyl, R 1 is independently C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 5 -C 8 cycloalkenyl, C 5 -C 12 cycloalkyl, C 6 -C 10 bicycloalkyl, C 6 -C 10 aryl, C 7 -C 9 aralkyl, or C 7 -C 9 aralkyl substituted by alkyl or C 6 -C 10 aryl; m is 2-4, when m is 2, R 2 is C 1 -C 12 alkylene, C 4 -C 12 alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, or of a dicarbamic acid, ##STR13## wherein D 3 and D 4 are independently hydrogen, an alkyl radical containing up to 8 carbon atoms, an C 6 -C 10 aryl or an C 7 -C 9 aralkyl or 3,5-di-tert-butyl-4-hydroxybenzyl radical, D 5 is hydrogen, or an alkyl or alkenyl radical containing up to 18 carbon atoms, and d is 0-20; when m is 4, R 2 is a trivalent acyl radical of an aliphatic, unsaturated aliphatic, cycloaliphatic, or aromatic tricarboxylic acid; when m is 4, R 2 is a tetravalent acyl radical of a saturated or unsaturated aliphatic or aromatic tetracarboxylic acid, p is 1, 2 or 3, R 3 is hydrogen, C 1 -C 12 alkyl, C 5 C 7 cycloalkyl, C 7 -C 8 aralkyl, C 2 -C 18 alkanoyl, C 3 -C 5 alkenoyl or benzoyl; when p is 1, R 4 is hydrogen, C 1 -C 18 alkyl C 5 C 7 cycloalkyl, C 2 -C 8 alkenyl unsubstituted or substituted by a cyano, carbonyl or carbamide group, C 6 -C 10 aryl, C 7 -C 9 aralkyl, glycidyl, a group of the formula --CH 2 --CH(OH)--Z or of the formula --CO--Z-- or --CONH--Z wherein Z is hydrogen, methyl or phenyl; or a group of the formulae ##STR14## or R 3 and R 4 together when p is 1 can be alkylene of 4 to 6 carbon atoms or 2-oxapolyalkylene or the cyclic acyl radical of an aliphatic or aromatic 1,2- or 1,3-dicarboxylic acid, when p is 2, R 4 is a direct bond or is C 1 -C 12 alkylene, C 6 -C 12 arylene, xylylene, a --CH 2 CH(OH)--CH 2 group, or a group --CH 2 --CH(OH)--CH 2 --O--X--O--CH 2 --CH(OH)--CH 2 -- wherein X is C 2 -C 10 alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene; or, provided that R 3 is not alkanoyl, alkenoyl or benzoyl, R 4 can also be a divalent acyl radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or of a dicarbamic acid, or can be the group --CO--; or R 4 is ##STR15## where T 8 and T 9 are independently hydrogen, alkyl of 1 to 18 carbon atoms, or T 8 and T 9 together are alkylene of 4 to 6 carbon atoms or 3-oxapentamethylene, when p is 3, R 4 is 2,4,6-triazinyl, n is 1 or 2, when n is 1, R 5 and R' 5 are independently C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 7 -C 12 aralkyl, or R 5 is also hydrogen, or R 5 and R' 5 together are C 2 -C 8 alkylene or C 2 -C 8 hydroxyalkylene or C 4 -C 22 acyloxyalkylene; when n is 2, R 5 R' 5 together are (--CH 2 ) 2 C(CH 2 --) 2 ; R 6 is hydrogen, C 1 -C 12 alkyl, allyl, benzyl, glycidyl or C 2 -C 6 alkoxyalkyl; when n is 1, R 7 is hydrogen, C 1 -C 12 alkyl, C 3 -C 5 alkenyl, C 7 -C 9 aralkyl, C 5 -C 7 cycloalkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 6 alkoxyalkyl, C 6 -C 10 aryl, glycidyl, a group of the formula --(CH 2 ) t --COO--Q or of the formula --(CH 2 ) t --O--CO--Q wherein t is 1 or 2, and Q is C 1 -C 4 alkyl or phenyl; or when n is 2, R 7 is C 2 -C 12 alkylene, C 6 -C 12 arylene, a group --CH 2 CH(OH)--CH 2 --O--X--O--CH 2 --CH(OH)--CH 2 -- wherein X is C 2 -C 10 alkylene, C 6 -C 15 arylene or C 6 -C 12 cycloalkylene, or a group --CH 2 CH(OZ')CH 2 --(OCH 2 --CH(OZ')CH 2 ) 2 -- wherein Z' is hydrogen, C 1 -C 18 alkyl, allyl, benzyl, C 2 -C 12 alkanoyl or benzoyl; Q 1 is --N(R 8 )-- or --O--; E is C 1 -C 3 alkylene, the group --CH 2 --CH(R 9 )--O-- wherein R 9 is hydrogen, methyl or phenyl, the group --(CH 2 ) 3 --NH-- or a direct bond; R 10 is hydrogen or C 1 -C 18 alkyl, R 8 is hydrogen, C 1 -C 18 alkyl, C 5 -C 7 cycloalkyl, C 7 -C 12 aralkyl, cyanoethyl, C 6 -C 10 aryl, the group --CH 2 --CH(R 9 )--OH wherein R 9 has the meaning defined above; a group of the formula ##STR16## or a group of the formula ##STR17## wherein G is C 2 -C 6 alkylene or C 6 -C 12 arylene; or R 8 is a group --E--CO--NH--CH 2 --OR 10 ; T 3 is ethylene or 1,2-propylene, or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate; k is 2 to 100; T 4 has the same meaning as R 4 when p is 1 or 2, T 5 is methyl, T 6 is methyl or ethyl, or T 5 and T 6 together are tetramethylene or pentamethylene, M and Y are independently methylene or carbonyl; T 7 is the same as R 7 , T 10 and T 11 are independently alkylene of 2 to 12 carbon atoms, or T 11 is ##STR18## T 12 is piperazinyl, --NR 11 --(CH 2 ) d --NR 11 -- or ##STR19## where R 11 is the same as R 3 and is also ##STR20## a, b and c are independently 2 or 3, and f is 0 or 1, e is 2, 3 or 4; T 13 is the same as R 2 with the proviso that T 13 cannot be hydrogen when n is 1; E 1 and E 2 , being different, each are --CO-- or --N(E 5 ) where E 5 is hydrogen, C 1 -C 12 alkyl or alkoxycarbonylalkyl of 4 to 22 carbon atoms; E 3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said naphthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms, E 4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, or E 3 and E 4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by up to four alkyl groups of 1 to 4 carbon atoms, and E 6 is an aliphatic or aromatic tetravalent radical, and with the proviso that in formula B when R 1 is alkyl, R 3 is not hydrogen.
Claim 3
Dependent Claim 13 words
The compounds of formulae (A), (B), (J) and (K) according to claim 1.
Claim 4
Dependent Claim 29 words
The compound of formula A according to claim 2, wherein m is 2 and R 2 is an acyl radical of an aliphatic dicarboxylic acid having 2-18 C atoms.
Claim 5
Dependent Claim 16 words
The compound of claim 3, wherein said acid is succinic, sebacic, phthalic, isophthalic or terephthalic acid.
Claim 6
Dependent Claim 16 words
The compound of claim 3, wherein R 1 is C 1 -C 12 alkyl or cyclohexyl.
Claim 7
Dependent Claim 46 words
The compound of claim 1 selected from the group consisting of di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, alpha,alpha'-(di-1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yl oxy)-p-xylene, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, alpha,alpha'-(di-1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-p-xylene di-(1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, di-(1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, di-(1-benzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) diethylmalonate, di-[1-(alpha-methylbenzyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] phthalate, di-[1-(alpha-methylbenzyloxy)-2,2,6,6-tetramethylpiperidine-4-yl] sebacate, di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-alpha-methylbenzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) terephthalate, di-(1-alpha-methylbenzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate, di-(1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-cumyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 8-alpha-methylbenzyloxy-7,7,9,9-tetramethyl-8-aza-1,4-dioxaspiro[4.5]decane 3,15-di-alpha-methylbenzyloxy-2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diazatrispiro-5.2.2.5.2.2.]heneicosane,
Claim 8
Dependent Claim 57 words
15-dicyclohexyloxy-2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diazatrispiro[5.2.2.5.2.2.]heneicosane, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) (3,5-di-t-butyl-4-hydroxybenzyl)-n-butylmalonate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) (3,5-di-t-butyl-4-hydroxybenzyl)-n-butylmalonate, poly-{[6-(1,1,3,3-tetramethylbutyl)-imino]-1,3,5-triazine-2,4-diyl] [2-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]-hexamethylene-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]}, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-alpha-methylbenzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-octadecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, 1-cyclohexyloxy-4-(n-dodecylamino)-2,2,6,6-tetramethylpiperidine, 1-alpha-methylbenzyloxy-4-(n-dodecylamino)-2,2,6,6-tetramethylpiperidine, 1-alpha-methylbenzyloxy-4-(n-butylamino)-2,2,6,6-tetramethylpiperidine, N,N'-di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine, 1-cyclohexyloxy-4-(n-butylamino)-2,2,6,6-tetramethylpiperidine, di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-decyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-dodecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-[1-(1-methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] sebacate, di-[1-(2-cyclohexen-1-yloxy)-2,2,6,6-tetramethylpiperidin-4-yl] sebacate, di-(1-t-butoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, 4-acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, 4-amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, N,N'-bis[1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl]succinamide, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)terephthalate, bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]sebacamide, bis[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl]-N-n-butyl]sebacamide, 1,6-bis[N,N'-di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-acetylamino]hexane, bis(1-cyclooctyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-decahydronaphthalenyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-cyclododecyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, N,N',N",N"'-tetrakis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine
Claim 9
Dependent Claim 57 words
15-dicyclohexyloxy-2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diazatrispiro[5.2.2.5.2.2.]heneicosane, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) (3,5-di-t-butyl-4-hydroxybenzyl)-n-butylmalonate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) (3,5-di-t-butyl-4-hydroxybenzyl)-n-butylmalonate, poly-{[6-(1,1,3,3-tetramethylbutyl)-imino]-1,3,5-triazine-2,4-diyl] [2-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]-hexamethylene-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]}, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-alpha-methylbenzyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-octadecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, 1-cyclohexyloxy-4-(n-dodecylamino)-2,2,6,6-tetramethylpiperidine, 1-alpha-methylbenzyloxy-4-(n-dodecylamino)-2,2,6,6-tetramethylpiperidine, 1-alpha-methylbenzyloxy-4-(n-butylamino)-2,2,6,6-tetramethylpiperidine, N,N'-di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine, 1-cyclohexyloxy-4-(n-butylamino)-2,2,6,6-tetramethylpiperidine, di-(1-nonyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate, di-(1-decyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-dodecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-[1-(1-methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidin-4-yl] sebacate, di-[1-(2-cyclohexen-1-yloxy)-2,2,6,6-tetramethylpiperidin-4-yl] sebacate, di-(1-t-butoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, 4-acetamido-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, 4-amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, N,N'-bis[1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl]succinamide, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)terephthalate, bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]sebacamide, bis[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl]-N-n-butyl]sebacamide, 1,6-bis[N,N'-di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-acetylamino]hexane, bis(1-cyclooctyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)succinate, bis(1-decahydronaphthalenyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-cyclododecyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, N,N',N",N"'-tetrakis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine
Claim 10
Dependent Claim 10 words
4,6-tris[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-t-octylamino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-morpholino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine, N,N',N",N"'-tetrakis{2,4-bis[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine, 2,4,6-tris[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylamino]-1,3,5-triazine, N,N'-bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}hexamethylene diamine,
Claim 11
Dependent Claim 10 words
4,6-tris[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-t-octylamino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-morpholino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine, N,N',N",N"'-tetrakis{2,4-bis[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine, 2,4,6-tris[N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylamino]-1,3,5-triazine, N,N'-bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}hexamethylene diamine,
Claim 12
Dependent Claim 41 words
4-bis[N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-n-butylamino-1,3,5-triazine, N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}hexamethylene diamine, 1,6-bis[N,N'-bis{2,4-bis[N-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}](N,N'-dimethyl)hexanediamine, N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}piperazine, N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinimide, bis-(1-norbornyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis-(1-tricyclo[5.2.1.0 2 ,6 ]decyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-dodecyl succinimide, tetrakis (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)hydrazinedicarboxylate, bis[N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]oxamide, and bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]oxamide.
Claim 13
Dependent Claim 41 words
4-bis[N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-diethylamino-1,3,5-triazine, 2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-6-n-butylamino-1,3,5-triazine, N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}hexamethylene diamine, 1,6-bis[N,N'-bis{2,4-bis[N-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}](N,N'-dimethyl)hexanediamine, N,N'-bis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}piperazine, N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinimide, bis-(1-norbornyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, bis-(1-tricyclo[5.2.1.0 2 ,6 ]decyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide, N-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-dodecyl succinimide, tetrakis (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, tetrakis (1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate, di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate, (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)hydrazinedicarboxylate, bis[N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]oxamide, and bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N-n-butyl]oxamide.
Claim 14
Dependent Claim 6 words
Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate according to claim 1.
Claim 15
Dependent Claim 6 words
Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate according to claim 1.
Claim 16
Dependent Claim 6 words
Di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate according to claim 1.
Claim 17
Dependent Claim 5 words
3,15-Dicyclohexyloxy-2,2,4,4,14,14,16,16-octamethyl-7,11,18,21-tetraoxa-3,15-diazatrispiro[5.2.2.5.2.2.]heneicosane according to claim 1.
Claim 18
Dependent Claim 6 words
Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate according to claim 1.
Claim 19
Dependent Claim 6 words
Di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate according to claim 1.
Claim 20
Dependent Claim 6 words
(1-Methoxy-2,2,6,6-tetramethylpiperidin-4-yl) (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate according to claim 1.
Claim 21
Dependent Claim 6 words
Di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate according to claim 1.
Claim 22
Dependent Claim 6 words
Di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate according to claim 1.
Claim 23
Dependent Claim 6 words
Di-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4yl) succinate according to claim 1.
Claim 24
Dependent Claim 6 words
Di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) isophthalate according to claim 1.
Claim 25
Dependent Claim 6 words
Di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate according to claim 1.
Claim 26
Dependent Claim 6 words
Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) phthalate according to claim 1.
Claim 27
Dependent Claim 6 words
Di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) terephthalate according to claim 1.
Claim 28
Dependent Claim 6 words
Di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) terephthalate according to claim 1.
Claim 29
Dependent Claim 6 words
Poly-{[6-(1,1,3,3-tetramethylbutyl)-imino]-1,3,5-triazine-2,4-diyl] [2-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]-hexamethylene-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidyl)-imino]} according to claim 1.
Claim 30
Dependent Claim 6 words
Poly-{[6-(1,1,3,3-tetramethylbutyl)-imino]-1,3,5-triazine-2,4-diyl] [2-(1-methoxy-2,2,6,6-tetramethylpiperidyl)imino]-hexamethylene-[4-(1-methoxy-2,2,6,6-tetramethylpiperidyl)-imino]} according to claim 1.
Claim 31
Dependent Claim 5 words
N,N',N",N"'-tetrakis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine according to claim 1.
Claim 32
Dependent Claim 5 words
N,N',N",N"'-tetrakis{2,4-bis[N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazin-6-yl}-3,3'-ethylenediiminodipropylamine according to claim 1.
Claim 33
Dependent Claim 5 words
2,4,6-tris[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-1,3,5-triazine according to claim 1.
Claim 34
Dependent Claim 6 words
N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinimide according to claim 1.
Claim 35
Dependent Claim 7 words
N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide according to claim 1.
Claim 36
Dependent Claim 7 words
N-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide according to claim 1.
Claim 37
Dependent Claim 7 words
N-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) n-dodecyl succinimide according to claim 1.
Claim 38
Dependent Claim 6 words
N-(1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-dodecyl succinimide according to claim 1.
Claim 39
Dependent Claim 6 words
Tetrakis (1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate according to claim 1.
Claim 40
Dependent Claim 6 words
Tetrakis (1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate according to claim 1.
Claim 41
Dependent Claim 6 words
Tetrakis (1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate according to claim 1.
Claim 42
Dependent Claim 6 words
Tetrakis (1-heptyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate according to claim 1.
Claim 43
Dependent Claim 6 words
Di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate according to claim 1.

References Cited (Backward Citations)

US4344876A Cited
US4691015A Cited
US4547537A Cited
US4774275A Cited

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