Compounds useful as pigments containing one or more 2,2,6,6-tetraalkylpiperidine groups

Claim 2

A polymeric composition comprising a polymeric material pigmented with a pigment of formula I or II ##STR35## in which R is hydrogen, C 1-8 alkyl, C 3-10 alkenyl, phenyl, phenyl-C 1-4 alkyl or --COR 5a where R 5a is hydrogen, --C(R 10a )═CH 2 , C 1-6 alkyl, phenyl, --COOC 1-4 alkyl or --NR 21 R 22 , where R 10a is hydrogen or C 1-4 alkyl; R 21 is hydrogen, C 1-12 alkyl, C 5-6 cycloalkyl, phenyl, phenylC 1-4 alkyl or C 1-12 alkylphenyl and R 22 is C 1-12 alkyl or hydrogen; each R 1 independently is --CH 3 or --CH 2 (C 1-4 alkyl) or both groups R 1 form a group --(CH 2 ) 5--; each R 2 independently is --CH 3 or --CH 2 (C 1-4 alkyl) or both groups R 2 form a group --(CH 2 ) 5 --; R 4 is a direct bond or a bridging group and R 5 is hydrogen or C 1-4 alkyl, or R 4 and R 5 together with the carbon atom to which they are attached form an isocyclic or heterocyclic bridging group; R 6 is --NH 2 , mono or di--C 1-4 alkylamino, C 1-2 alkylcarbonylamino, benzoylamino, hydrogen, OH or --CO--C 1-4 alkyl or --CO--C 1-4 alkoxy and R 7 is hydrogen or C 1-4 alkyl, or R 6 or R 7 together with the carbon atom to which they are attached form an isocyclic or heterocyclic ring; R 8 is a direct bond or a bridging group; D is a residue of a pigment; and n is an integer from 1 to 4 inclusive.

Claim 3

A composition according to claim 1, in which D is a pigment residue of the azo, perinone, perylene, quinophthalone, isoindolinone, dioxazine, acetoacetylamine, phthalocyanine or pyrrolo-pyrrole series.

Claim 4

A composition according to claim 1, in which D is D' where D' is a group of formula III to VIII when monovalent ##STR36## or D' is a group of formula IX to XV, when divalent ##STR37## or D' is a group of the formula XVI, when trivalent ##STR38## or D' is a group of the formula XVII, when tetravalent ##STR39## in which D 1 is 1,3- or 1,4-phenylene, unsubstituted or mono or di-substituted by substituents selected from the group consisting of chloro, bromo, C 1-2 alkyl, C 1-2 alkoxy, carboxy or C 1-4 alkoxycarbonyl; or 1,4, -1,5- or 1,8-anthraquinone, unsubstituted or mono or disubstituted by substituents selected from the group consisting of chloro, bromo, hydroxy, C 1-3 alkoxy or acylamino; D 2 is phenyl, unsubstituted or substituted by one to three substituents, selected by the group consisting of chloro (max. 2), bromo (max. 2), C 1-2 alkoxy (max 2), C 1-4 alkoxy carbonyl (max 2) and acylamino (max 1); D 3 is a 4,4'-diphenylene group, unsubstituted or substituted by one to four substituents selected from chloro, bromo, C 1-2 alkyl and C 1-2 alkoxy or is a group of formula ##STR40## where the starred atoms are attached to the azo in a group of formula VIII K 1 is a group of any one of formula K 1a to K 1f ##STR41## where the starred atom is attached to the azo group of IV or X; and R 16 is --O-- or --NH--; K 2 is a group of any one of formula K 2a to K 2c ##STR42## K 3 is a group of any one of formula K 3a to K 3g ##STR43## in which R 10 is hydrogen, chloro, bromo, C 1-3 alkoxycarbonyl, C 1-2 alkyl, C 1-2 alkoxy or nitro; R g is 1,4-phenylene, unsubstituted or substituted by one or two groups selected from chloro, bromo, methyl or C 1-2 alkoxy; -4,4'-diphenylene; 1,4- or 1,5-naphthylene or a group of the formula ##STR44## where A is --CH 2 --, --NHCO--, --NHCONH--, --NH--CO--CO--NH-- or ##STR45## R 11 is methyl, --COOH or --COOC 1-4 alkyl; and R 17 is --OH, methyl or unsubstituted phenyl.

Claim 5

A composition according to claim 1 wherein the pigment is of the formula XX ##STR46## in which R, R 1 and R 2 are as defined in claim 2; either both groups R 20 are of formula (e) or both groups R 20 are of formula (f) ##STR47## where the starred atom is attached to the --NH group; R 13 is hydrogen, chloro, bromo, methyl, ethyl, C 1-2 alkoxy or C 1-4 alkoxycarbonyl; R 14 is hydrogen, chloro, bromo or methyl; R 15 is --CO--NH*--, --CO--O*-- or --SO 2 NH*--; the starred group being attached to the 2,2,6,6-tetraalkyl-piperidine group. R 18 is 1,4-phenylene, unsubstituted or substituted by 1 or 2 groups selected from chloro, bromo, methyl, ethyl, methoxy and ethoxy; 4,4'-diphenylene, each phenylene group being unsubstituted or substituted by 1 or 2 groups selected from chloro, bromo, methyl, ethyl, methoxy and ethoxy; or unsubstituted 1,4- or 1,5-naphthalene.

Claim 6

A polymeric composition according to claim 1 in which the polymeric material is polypropylene or polyethylene.

Claim 7

A composition according to claim 1 wherein, when R 4 is a bridging group, it is *--NHCO--, *--NHSO 2 -, *--NH--CO--O--, *--NH--COCH 2 O--, *--NHCOCO--, --NHCOCONH--, *--NHCOCOO--, *--OCO--, *--OSO 2 --, *--OCOCO--, --OCO--CO--O--, *--OCONH-- or *--OCOCONH--, where the starred atom is attached to the piperidine ring; when R 4 and R 5 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (a) or (b) ##STR48## in which the starred atom is attached to D; when R 6 and R 7 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (c) or (d) ##STR49## where R 12 is hydrogen, C 1-4 alkyl or C 1-4 alkoxycarbonyl-C 1-3 alkyl; and when R 8 is a bridging group, it is --CO--, --CH 2 *CO--, --OCH 2 *CO-- or --SO 2 --, where the starred atom is attached to the piperidine ring.

Claim 8

A composition according to claim 2 wherein, when R 4 is a bridging group, it is *--NHCO--, *--NHSO 2 --, *--NH--CO--O--, *--NH--COCH 2 O--, *--NHCOCO--, --NHCOCONH--, *--NHCOCOO--, *--OCO--, *--OSO 2 --, *--OCOCO--, --OCO--CO--O--, *--OCONH-- or *--OCOCONH--, where the starred atom is attached to the piperidine ring. when R 4 and R 5 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (a) or (b) ##STR50## in which the starred atom is attached to D; when R 6 and R 7 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (c) or (d) ##STR51## where R 12 is hydrogen, C 1-4 alkyl or C 1-4 alkoxycarbonyl-C 1-3 alkyl; and when R 8 is a bridging group, it is --CO--, --CH 2 *CO--, --OCH 2 *CO-- or --SO 2 --, where the starred atom is attached to the piperidine ring.

Claim 9

A composition according to claim 3 wherein, when R 4 is a bridging group, it is *--NHCO--, *--NHSO 2 --, *--NH--CO--O--, *--NH--COCH 2 O--, *--NHCOCO--, --NHCOCONH--, *--NHCOCOO--, *--OCO--, *--OSO 2 --, *--OCOCO--, --OCO--CO--O--, *--OCONH-- or *--OCOCONH--, where the starred atom is attached to the piperidine ring. when R 4 and R 5 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (a) or (b) ##STR52## in which the starred atom is attached to D; when R 6 and R 7 together with the carbon atom to which they are attached form a heterocyclic or isocyclic ring, this ring is a group of formula (c) or (d) ##STR53## where R 12 is hydrogen, C 1-4 alkyl or C 1-4 alkoxycarbonyl-C 1-3 alkyl; and when R 8 is a bridging group, it is --CO--, --CH 2 *CO--, --OCH 2 *CO-- or --SO 2 --, where the starred atom is attached to the piperidine ring.

Claim 10

A composition according to claim 3 wherein, in any acylamino substituent on D 1 or D 2 , the acyl group is --COC 1-4 alkyl or --COC 1-4 alkoxy.

Claim 11

A composition according to claim 4 wherein each R 1 and each R 2 is methyl and R is R' where R' is hydrogen, methyl, formyl, C 1-4 alkylcarbonyl or --CO--CO--OC 1-4 alkyl.

Claim 12

A composition according to claim 6 wherein R is R' where R' is hydrogen, methyl, formyl, C 1-4 alkylcarbonyl or --CO--CO--OC 1-4 alkyl; each R 1 and R 2 is methyl; R 4 is R' 4 and R 5 is R' 5 where either R' 4 is a direct bond, --NH--CO-- or --NH--CO--CH 2 --O-- and R' 5 is hydrogen or R' 4 and R' 5 together with the carbon atom to which they are attached form a group of formula (a) or (b); R 6 is R' 6 and R 7 is R' 7 where either R' 6 is --NH 2 , mono- or di- C 1-4 alkylamino, C 1-2 alkylcarbonylamino or benzoylamino and R' 7 is hydrogen or R' 6 and R' 7 together with the carbon atom to which they are attached form a group of formula (c) or (d); and R 8 is R' 8 where R' 8 is a direct bond or --CO--, --CH 2 CO--, --OCH 2 CO-- or --SO 2-- .

Claim 13

A composition according to claim 7 wherein, R is R' where R' is hydrogen, methyl, formyl, C 1-4 alkylcarbonyl or --CO--CO--OC 1-4 alkyl; each R 1 and R 2 is methyl; R 4 is R' 4 and R 5 is R' 5 where either R' 4 is a direct bond, --NH--CO-- or --NH--CO--CH 2 --O-- and R' 5 is hydrogen or R' 4 and R' 5 together with the carbon atom to which they are attached form a group of formula (a) or (b); R 6 is R' 6 and R 7 is R' 7 where either R' 6 is --NH 2 , mono- or di- C 1-4 alkylamino, C 1-2 alkylcarbonylamino or benzoylamino and R' 7 is hydrogen or R' 6 and R' 7 together with the carbon atom to which they are attached form a group of formula (c) or (d); and R 8 is R' 8 is a direct bond or --CO--, --CH 2 CO--, --OCH 2 CO-- or --SO 2 --.

Claim 14

A composition according to claim 8 wherein, R is R'where R'is hydrogen, methyl, formyl, C 1-4 alkylcarbonyl or --CO--CO--OC 1-4 alkyl; each R 1 and R 2 is methyl; R 4 is R' 4 and R 5 is R' 5 where either R' 4 is a direct bond, --NH--CO-- or --NH--CO--CH 2 --O-- and R' 5 is hydrogen or R' 4 and R' 5 together with the carbon atom to which they are attached form a group of formula (a) or (b); R 6 is R' 6 and R 7 is R' 7 where either R' 6 is --NH 2 , mono- or di- C 1-4 alkylamino, C 1-2 alkylcarbonylamino or benzoylamino and R' 7 is hydrogen or R' 6 and R' 7 together with the carbon atom to which they are attached form a group of formula (c) or (d); and R 8 is R' 8 where R' 8 is a direct bond or --CO--, --CH 2 CO--, --OCH 2 CO-- or --SO 2-- .

Claim 15

A composition according to claim 9 wherein, R is R' where R' is hydrogen, methyl, formyl, C 1-4 alkylcarbonyl or --CO--CO--OC 1-4 alkyl; each R 1 and R 2 is methyl; R 4 is R' 4 and R 5 is R' 5 where either R' 4 is a direct bond, --NH--CO-- or --NH--CO--CH 2 --O-- and R' 5 is hydrogen or R' 4 and R' 5 together with the carbon atom to which they are attached form a group of formula (a) or (b); R 6 is R' 6 and R 7 is R' 7 where either R' 6 is --NH 2 , mono- or di- C 1-4 alkylamino, C 1-2 alkylcarbonylamino or benzoylamino and R' 7 is hydrogen or R' 6 and R' 7 together with the carbon atom to which they are attached form a group of formula (c) or (d); and R 8 is R' 8 where R' 8 is a direct bond or --CO--, --CH 2 CO--, --OCH 2 CO-- or --SO 2 --.

Claim 16

A composition according to claim 13 wherein R 10 is R' 10 where R' 10 is hydrogen, methyl, chloro, bromo, C 1-2 alkoxy (max. 1 on a phenyl ring) or C 1-3 alkoxycarbonyl (max. 1 on a phenyl ring).

Claim 17

A composition according to claim 14 wherein R 10 is R' 10 where R' 10 is hydrogen, methyl, chloro, bromo, C 1-2 alkoxy (max. 1 on a phenyl ring) or C 1-3 alkoxycarbonyl (max. 1 on a phenyl ring).

Claim 18

A composition according to claim 3 wherein the pigment is of the formula ##STR54##

Claim 19

A composition according to claim 4 wherein the pigment is of the formula ##STR55##

Claim 20

A composition according to claim 4 wherein the pigment is of the formula ##STR56##

Claim 21

A composition according to claim 4 wherein the pigment is of the formula ##STR57##

Claim 22

A composition according to claim 4 wherein R 14 , when it is other than hydrogen, is para to R 13 ; and R 15 is attached to the phenyl ring para to R 13 when R 14 is hydrogen and para to the azo moiety when R 14 is other than hydrogen.

Claim 23

A composition according to claim 4 wherein R 13 is chloro, methoxy or C 1-2 alkoxycarbonyl, R 14 is hydrogen or chloro, and R 15 is --CO--NH-- or --SO 2 NH--.

Claim 24

A composition according to claim 21 wherein R 13 is chloro, methoxy or C 1-2 alkoxycarbonyl, R 14 is hydrogen or chloro, and R 15 is --CO--NH-- or --SO 2 NH--.

Claim 25

A composition according to claim 1 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 26

A composition according to claim 3 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 27

A composition according to claim 4 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 28

A composition according to claim 8 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 29

A composition according to claim 9 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 30

A composition according to claim 10 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride, natural rubber or synthetic leather.

Claim 31

A composition according to claim 14 where the polymeric material is polyethylene, polypropylene, polystyrene, polyvinylchloride natural rubber or synthetic leather.

Claim 32

A composition according to claim 1 wherein the pigment is present in an amount sufficient to stabilize the polymeric material against the effects of U.V. light.

Claim 33

A composition according to claim 4 wherein the pigment is present in an amount sufficient to stabilize the polymeric material against the effects of U.V. light.

Claim 34

A composition according to claim 26 wherein the pigment is present in an amount sufficient to stabilize the polymeric material against the effects of U.V. light.

Claim 35

A composition according to claim 30 wherein the pigment is present in an amount sufficient to stabilize the polymeric material against the effects of U.V. light.