Water-soluble triazine black dyes from cellulose reactive groups and suitable for use in inks

Claim 2

A water soluble dye, free from cellulose reactive groups, of the formula: ##STR10## wherein R 1 is --(C a H 2a O) m (C b H 2b O) n H, R 2 is H or --(C a H 2a O) m (C b H 2b O) n H, or R 1 and R 2 together with the nitrogen atom form a morpholine ring, a and b are different and are from 2 to 8, m is from 1 to 10,

Claim 3

n is from 0 to 9, g is 1/2 or 1, p is 1 or 2, L is chromium, cobalt, copper or a mixture thereof, M is H, ammonium, or an alkali metal, Q is H or SO 3 M, T is H or C 1-4 -alkyl, D is a phenylazo or naphthylazo group each of which is unsubstituted or substituted by a group selected from sulphonate; carboxylate; C 1-4 -alkyl; C 1-4 -alkoxy; ureido; mono-and di-C 1-4 -alkylamino; aminosulphonyl; mono- and di-C 1-4 -alkylaminosulphonyl; aminocarbonyl; mono- and di-C 1-4 -alkylaminocarbonyl; phenylamino; C 1-4 -alkylcarbonylamino; hydroxy; nitro and halogen, E is H, C 1-4 -alkyl, halogen and aminosulphonyl, B and F are H, provided that: when p=1 X is selected from (i) NR 1 R 2 ; (ii) NR 3 R 4 ; (iii) OR 3 ; and (iv) a monoazo chromophore, derived from a benzene or naphthalene diazo component and a benzene, naphthalene or mono-heterocyclic coupling component and linked to the triazine group through a group --NR 5 -- in which R 5 is selected from H, C 1-4 -alkyl and phenyl; and R 3 and R 4 are each independently selected from H, C 1-4 -alkyl, phenyl, naphthyl and phenyl or naphthyl substituted by a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, ureido, mono- and di-C 1-4 -alkylamino, nitro, phenylamino, halogen, carboxylate, sulphonate, hydroxy and unsubstituted and mono- and di-alkylamino-sulphonyl and carbonyl; and and when p=2 X is --NR 3 --Z--NR 3 --; and Z is selected from C 1-6 -alkylene; phenylene; biphenylene; C 1-4 -alkylenephen-4-ylene; C 1-6 -alkylene, phenylene, biphenylene or C 1-4 -alkylenephen-4-ylene interrupted by a group selected from CH 2 , O, S, NR 3 and SO 2 ; and C 1-6 -alkylene; phenylene, biphenylene; C 1-4 -alkylene-phen-4-ylene; C 1-6 -alkylene, phenylene, biphenylene or C 1-4 -alkylenephen-4-ylene interrupted by a group selected from CH 2 , O, S, NR 3 and SO 2 and substituted by a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 4 -alkyl-carbonylamino, ureido, mono- and di-C 1-4 -alkylamino, nitro, phenylamino, halogen, carboxylate, sulphonate, hydroxy NH 2 SO 2 --, NH 2 CO-- and mono- and di-alkylamino-sulphonyl and carbonyl.

Claim 4

n is from 0 to 9, g is 1/2 or 1, p is 1 or 2, L is chromium, cobalt, copper or a mixture thereof, M is H, ammonium, or an alkali metal, Q is H or SO 3 M, T is H or C 1-4 -alkyl, D is a phenylazo or naphthylazo group each of which is unsubstituted or substituted by a group selected from sulphonate; carboxylate; C 1-4 -alkyl; C 1-4 -alkoxy; ureido; mono-and di-C 1-4 -alkylamino; aminosulphonyl; mono- and di-C 1-4 -alkylaminosulphonyl; aminocarbonyl; mono- and di-C 1-4 -alkylaminocarbonyl; phenylamino; C 1-4 -alkylcarbonylamino; hydroxy; nitro and halogen, E is H, C 1-4 -alkyl, halogen and aminosulphonyl, B and F are H, provided that: when p=1 X is selected from (i) NR 1 R 2 ; (ii) NR 3 R 4 ; (iii) OR 3 ; and (iv) a monoazo chromophore, derived from a benzene or naphthalene diazo component and a benzene, naphthalene or mono-heterocyclic coupling component and linked to the triazine group through a group --NR 5 -- in which R 5 is selected from H, C 1-4 -alkyl and phenyl; and R 3 and R 4 are each independently selected from H, C 1-4 -alkyl, phenyl, naphthyl and phenyl or naphthyl substituted by a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, ureido, mono- and di-C 1-4 -alkylamino, nitro, phenylamino, halogen, carboxylate, sulphonate, hydroxy and unsubstituted and mono- and di-alkylamino-sulphonyl and carbonyl; and and when p=2 X is --NR 3 --Z--NR 3 --; and Z is selected from C 1-6 -alkylene; phenylene; biphenylene; C 1-4 -alkylenephen-4-ylene; C 1-6 -alkylene, phenylene, biphenylene or C 1-4 -alkylenephen-4-ylene interrupted by a group selected from CH 2 , O, S, NR 3 and SO 2 ; and C 1-6 -alkylene; phenylene, biphenylene; C 1-4 -alkylene-phen-4-ylene; C 1-6 -alkylene, phenylene, biphenylene or C 1-4 -alkylenephen-4-ylene interrupted by a group selected from CH 2 , O, S, NR 3 and SO 2 and substituted by a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 4 -alkyl-carbonylamino, ureido, mono- and di-C 1-4 -alkylamino, nitro, phenylamino, halogen, carboxylate, sulphonate, hydroxy NH 2 SO 2 --, NH 2 CO-- and mono- and di-alkylamino-sulphonyl and carbonyl.

Claim 5

A dye according to claim 1 wherein NR 1 R 2 is selected from hydroxyethyamino, di(hydroxyethyl)amino and morpholino.

Claim 6

A dye according to claim 1 wherein X is NR 3 R 4 or OR 3 and R 3 is H or C 1-4 -alkyl and R 4 is selected from H, C 1-4 -alkyl and phenyl or naphthyl carrying a sulphonic acid group, SO 3 M, or phenyl or naphthyl carrying a sulphonic acid group and a group selected from C 1-4 -alkyl, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, ureido, mono- & di-C 1-4 -alkylamino, phenylamino, nitro, halogen, carboxylate, sulphonate and hydroxy.

Claim 7

A dye according to claim 3 wherein X is selected from NH 2 , OCH 3 , 3-sulpho-4-nitrophenylimino, 3,5-disulphophenylimino, 2-methyl-5-sulphophenylimino, 3-sulphophenylimino and 2-sulpho-5-methylphenylimino.

Claim 8

A dye according to claim 1 wherein X is a monoazo chromophore linked to the triazine group through a group --NR 5 --, in which the chromophore is selected from phenylazobenzene, phenylazo-naphthalene, naphthylazobenzene, naphthylazonaphthalene carrying two or three sulphonic acid groups and phenylazobenzene, phenylazo-naphthalene, naphthylazobenzene, naphthylazonaphthalene carrying two or three sulphonic acid groups and a group selected from C 1-4 -alkyl, nitro, C 1-4 -alkoxy, C 1-4 -alkylcarbonylamino, ureido, halogen, hydroxy, mono- & di-C 1-4 -alkylamino and phenylamino.

Claim 9

A dye according to claim 5 wherein X is selected from 5-hydroxy-6-(2-sulphophenylazo)-7-sulphonaphth-2-ylimino.

Claim 10

A dye according to claim 1 wherein Z is selected from ethylene, hexamethylene, --SO 2 CH 2 --, --(CH 2 ) 2 O(CH 2 ) 2 --, --C 2 H 4 SO 2 C 2 H 4 , 2,2'-disulpho-4,4'-diiminostilben-4,4'-ylene, stilben-4,4'ylene, 4-(eth-2-ylene)phenylene, phen-1,4-ylene, phen-1,4-ylenesulphonyl, 2,2'-disulphodiphen-4,4'-ylene, diphen-4,4'-ylene, diphen-4,4'-ylene ether and di(phen-4,4'-ylene)methane.

Claim 11

A dye according to claim 1 wherein X is selected from hydroxyethylamino, di(hydroxyethyl)amino and morpholino.

Claim 12

A dye according to claim 1 carrying 5 or 6 sulphonic acid groups.

Claim 13

The dye according to claim 1 wherein R 1 is hydroxyethyl; R 2 , B, F and T are H; Q is SO 3 Na; p=1; L is copper; q=1; E is CH 3 ; D is 2,5-disulphophenylazo (Na salt); X is 2-methyl-5-sulphophenylamino (Na salt) and M is Na.

Claim 14

The dye according to claim 1 wherein R 1 is hydroxyethyl, R 2 , T, B & F are H, E is CH 3 , M is K, L is copper, Q is SO 3 K, q=1, p=1, D is 2,5-disulphophenylazo (K salt) and X is 5-hydroxy-6-(2-sulphophenyl-azo)-7-sulpho-naphth-2-ylimino (K salt).

Claim 15

The dye according to claim 1 wherein R 1 is hydroxyethyl; R 2 , B, F, Q and T are H; E is CH 3 ; D is 2,5-disulphophenylazo (K salt); M is K; L is copper; q=1, p=1 and X is 5-hydroxy-6-(2-sulphophenylazo)-7-sulpho-naphth-2-ylamino (K salt).

Claim 16

A mixture of a dye according to claim 1 and a dye of the formula: ##STR11## wherein R 1 , R 2 , p, Q, M, and X are as defined in claim 1; B 1 , D 1 , E 1 , F 1 and G 1 , are selected from H; --SO 3 M; NHCOCH 3 ; --COOM; mono- and di-C 1-4 -alkylamino; C 1-4 -alkyl; C 1-4 -alkoxy; ureido; hydroxy; nitro and halogen or B 1 and D 1 form a second benzene ring fused to ring A which is unsubstituted or substituted by a group selected from H; --SO 3 M; NHCOCH 3 ; --COOM; mono- and di-C 1-4 alkylamino; C 1-4 -alkyl; C 1-4 -alkoxy; ureido; hydroxy; nitro and halogen, provided that neither F 1 nor G 1 is hydroxy; and J is selected from: ##STR12## wherein T is H, alkyl or phenyl; W is an acyl group selected from the group consisting of aminocarbonyl, aminosulphonyl, C 1-4 -alkylcarbonyl, C 1-4 alkylsulphonyl, phenylcarbonyl and phenylsulphonyl; and V is alkyl or alkoxy.

Claim 17

A mixture of the dye of claim 10 and the dye according to claim 13 wherein J is 1-hydroxy-3-sulpho-6-imino-naphth-2-yl (Na salt); B 1 & D 1 form a second benzene ring fused to Ring A' and carrying an SO 3 Na group in the position adjacent to the point where D 1 is attached to Ring A; E 1 , F 1 & R 2 are H; R 1 is hydroxyethyl; p=1; X is 4,4'-dimino-2,2'-disulphodiphenyl (Na salt) and G 1 is SO 3 Na.