Blue to green disperse dyes for synthetic fiber material

Claim 2

A dye of Formula (1): ##STR22## wherein: D is a group of Formula (2): ##STR23## or a group of Formula (3): ##STR24## or a group of Formula (4): ##STR25## or a group of Formula (4C): ##STR26## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted, --SO 2 alkyl, --SO 2 aryl or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; and R 4 is an electron withdrawing group; R 6 is optionally substituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl or aryl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; Ring B is unsubstituted or substituted by from 1 to 3 groups; provided that when R 1 and R 2 are both n-octyl, Ring A is unsubstituted, and also provided that: (a) when D is a group of Formula (2) and R 1 and R 2 are both allyl that R 4 is not --CN; and (b) when D is a group of Formula (3) that R 1 and R 6 are different, R 1 represents unsubstituted alkyl, cycloalkyl or alkenyl, and R 6 represents unsubstituted alkyl; or (c) at least one of R 1 and R 6 is branched chain alkyl.

Claim 3

A dye according to claim 1 in which D is a group of Formula (3); R 3 is --H, C 1-4 -alkyl, C 2-3 -alkenyl or phenylC 1-3 -alkyl; R 4 is --CN, --SO 2 F, --COOR 5 , --CON(R 5 ) 2 , --SO 2 R 5 in which R 5 is --H, C 1-8 -alkyl, C 4-8 -cycloalkyl, phenyl, C 2-3 -alkenyl or phenylC 1-3 -alkyl; R 6 is C 1-6 -alkyl; W is oxygen; Ring A is unsubstituted or is substituted in the 2-position.

Claim 4

A dye according to claim 2 in which R 3 is --H, R 4 is --CN and W is oxygen.

Claim 5

A synthetic textile material selected from the group consisting of polyester, polyamide, polyurethane elastomers, cellulose acetate and triacetate and blends containing polyester-cotton, polyester-wool and polyester-viscose when dyed with any of the dyes of claim 1 or mixtures thereof.

Claim 6

A mixture of two or more dyes of Formula (1): ##STR27## wherein D is a group of Formula (2): ##STR28## or a group of Formula (3): ##STR29## or a group of Formula (4): ##STR30## or a group of Formula (4C): ##STR31## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; R 4 is an electron withdrawing group; and R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 represents unsubstituted alkyl, cycloalkyl, aryl, alkenyl or aralkyl R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups.

Claim 7

A mixture of two or more dyes of Formula (1): ##STR27## wherein D is a group of Formula (2): ##STR28## or a group of Formula (3): ##STR29## or a group of Formula (4): ##STR30## or a group of Formula (4C): ##STR31## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; R 4 is an electron withdrawing group; and R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 represents unsubstituted alkyl, cycloalkyl, aryl, alkenyl or aralkyl R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups.

Claim 8

A mixture of one or more dyes of Formula (1): ##STR32## and one or more different dyes of Formula (11): ##STR33## wherein: D is a group of Formula (2): ##STR34## or a group of Formula (3): ##STR35## or a group of Formula (4): ##STR36## or a group of Formula (4C): ##STR37## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; and R 4 is an electron withdrawing group; R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 represents unsubstituted alkyl, cycloalkyl, aryl, alkenyl or aralkyl R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 9

A mixture of one or more dyes of Formula (1): ##STR32## and one or more different dyes of Formula (11): ##STR33## wherein: D is a group of Formula (2): ##STR34## or a group of Formula (3): ##STR35## or a group of Formula (4): ##STR36## or a group of Formula (4C): ##STR37## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; and R 4 is an electron withdrawing group; R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 represents unsubstituted alkyl, cycloalkyl, aryl, alkenyl or aralkyl R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 10

A mixture of two or more pyrrolidone dyes of Formula (11): ##STR38## Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; W is oxygen or sulphur; R 4 is an electron withdrawing group; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 11

A mixture of two or more pyrrolidone dyes of Formula (11): ##STR38## Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; W is oxygen or sulphur; R 4 is an electron withdrawing group; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 12

A mixture of dyes comprises two or more dyes of Formula (11) ##STR39## in which W is oxygen, R 4 is --CN, R 13 is --H, R 12 is n--C 3 H 7 , n--C 4 H 9 or n--C 5 H 11 and R 14 is --(CH 2 ) 3 phenyl, n--C 3 H 7 , n--C 4 H 9 or n--CH 5 H 11 .

Claim 13

A mixture of dyes comprises two or more dyes of Formula (11) ##STR39## in which W is oxygen, R 4 is --CN, R 13 is --H, R 12 is n--C 3 H 7 , n--C 4 H 9 or n--C 5 H 11 and R 14 is --(CH 2 ) 3 phenyl, n--C 3 H 7 , n--C 4 H 9 or n--CH 5 H 11 .

Claim 14

A process for the coloration of synthetic textile materials or fibre blends thereof which comprises applying to the synthetic textile material a dye of Formula (1) or mixtures thereof: ##STR40## wherein: D is a group of Formula (2): ##STR41## or a group of Formula (3): ##STR42## or a group of Formula (4): ##STR43## or a group of Formula (4C): ##STR44## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; and R 4 is an electron withdrawing group; R 6 is optionally substituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; Ring B is unsubstituted or substituted by from 1 to 3 groups; provided (a) that when D is a group of Formula (2) and R 1 and R 2 are both allyl that R 4 is not --CN or (b) that when D is a group of Formula (3) that R 1 and R 6 are different, R 1 represents unsubstituted alkyl, cycloalkyl or alkenyl, and R 6 represents unsubstituted alkyl or (c) that at least one of R 1 and R 6 is branched chain alkyl and provided further that when R 1 and R 2 are both n-octyl, Ring A is unsubstituted.

Claim 15

A process for the coloration of synthetic textile materials or fibre blends thereof which comprises applying to the synthetic textile material a dye of Formula (1) or mixtures thereof: ##STR40## wherein: D is a group of Formula (2): ##STR41## or a group of Formula (3): ##STR42## or a group of Formula (4): ##STR43## or a group of Formula (4C): ##STR44## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; and R 4 is an electron withdrawing group; R 6 is optionally substituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; Ring B is unsubstituted or substituted by from 1 to 3 groups; provided (a) that when D is a group of Formula (2) and R 1 and R 2 are both allyl that R 4 is not --CN or (b) that when D is a group of Formula (3) that R 1 and R 6 are different, R 1 represents unsubstituted alkyl, cycloalkyl or alkenyl, and R 6 represents unsubstituted alkyl or (c) that at least one of R 1 and R 6 is branched chain alkyl and provided further that when R 1 and R 2 are both n-octyl, Ring A is unsubstituted.

Claim 16

A process for the coloration of synthetic textile materials of fibre blends thereof which comprises applying to the synthetic textile material a mixture which comprises applying to the synthetic textile material a mixture of dyes of Formula (1) and Formula (11): ##STR45## wherein: D is a group of Formula (2): ##STR46## or a group of Formula (3): ##STR47## or a group of Formula (4): ##STR48## or a group of Formula (4C): ##STR49## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; R 4 is an electron withdrawing group; and R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 is unsubstituted; R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 17

A process for the coloration of synthetic textile materials of fibre blends thereof which comprises applying to the synthetic textile material a mixture which comprises applying to the synthetic textile material a mixture of dyes of Formula (1) and Formula (11): ##STR45## wherein: D is a group of Formula (2): ##STR46## or a group of Formula (3): ##STR47## or a group of Formula (4): ##STR48## or a group of Formula (4C): ##STR49## R 1 is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted; R 2 is optionally substituted C 7-20 -alkyl; or R 1 and R 2 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; R 3 is alkyl, alkenyl or aralkyl each of which may be optionally substituted or --COR in which R is --H or alkyl, phenyl, cycloalkyl or aralkyl each of which may be optionally substituted or --H; R 4 is an electron withdrawing group; and R 6 is unsubstituted C 1-6 -alkyl; or R 1 and R 6 together with the nitrogen atom to which they are attached form a pyrrolidino or piperidino ring; provided that when D is a group of Formula (3), R 1 is unsubstituted; R 7 , R 8 , R 9 and R 10 each independently is alkyl, cycloalkyl, aryl, alkenyl or aralkyl each of which may be optionally substituted or --H; W is oxygen or sulphur; Z is N--R 11 in which R 11 is --H or optionally substituted alkyl; Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; and Ring B is unsubstituted or substituted by from 1 to 3 groups; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 18

A process for the coloration of synthetic textile materials or fibre blends thereof which comprises applying to the synthetic textilen material a mixture of dyes of Formula (11): ##STR50## Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; W is oxygen or sulphur; R 4 is an electron withdrawing group; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 19

A process for the coloration of synthetic textile materials or fibre blends thereof which comprises applying to the synthetic textilen material a mixture of dyes of Formula (11): ##STR50## Ring A is unsubstituted apart from the --NR 1 R 2 group or is substituted by from 1 to 4 further groups; W is oxygen or sulphur; R 4 is an electron withdrawing group; R 12 and R 14 are each independently alkyl, alkenyl, alkoxyalkyl, alkenyloxyalkyl, aryloxyalkyl, aralkyl, alkoxycarbonylalkyl or aryloxyalkoxycarbonylalkyl; and R 13 is --H, alkyl, alkenyl, aralkyl, alkoxycarbonylalkyl, aryloxyalkoxycarbonylalkyl or cyanoalkyl.

Claim 20

A process according to any one of claims 10 to 11 in which the synthetic textile material is a polyester or fibre blend thereof.