Colorant mixtures

Abstract

The present invention relates to a colorant mixture comprising (A) at least one blue- or black-dyeing disperse dye of formula ##STR00001## wherein R.sub.1 denotes hydrogen or halogen, R.sub.2 and R.sub.3 are each independently of the other hydrogen; C.sub.1-C.sub.8-alkyl which is unsubstituted or substituted with hydroxy, cyano, C.sub.1-C.sub.4alkoxy or halogen; —(CH.sub.2).sub.n—O—(CH.sub.2).sub.mR.sub.4, wherein R.sub.4 denotes hydrogen or C.sub.1-C.sub.8-alkyl, n is a number from 2 to 6 and m is a number from 0 to 6; C.sub.5-C.sub.24aryl which is unsubstituted or substituted with hydroxy, carboxy, cyano, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4alkoxy or halogen; or C.sub.6-C.sub.30aralkyl which is unsubstituted or substituted with hydroxy, cyano, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.8alkoxy groups or halogen; and (B) at least one yellow-, orange- or red-dyeing disperse dye, solvent dye, vat dye or pigment; and to the use thereof in dyeing or printing cellulose or cellulose blend fibre materials.

Claims

1. A colorant mixture comprising: (A) at least one blue- or black-dyeing disperse dye of formula ##STR00013## wherein R.sub.1 denotes hydrogen or halogen, and R.sub.2 and R.sub.3 are each independently of the other phenyl, tolyl or 2-phenylethyl; and (B) a dye of formula (2) or (3) ##STR00014## wherein X denotes —O—, —S— or —NHCO—, R.sub.2 and R.sub.3 are as defined above, and R.sub.5 is CF.sub.3 or —CN.

2. A colorant mixture according to claim 1 comprising as component (A) a dye of formula (1), wherein R.sub.1 denotes hydrogen.

3. A colorant mixture according to claim 1 comprising as component (A) a dye of formula (1), wherein at least one of R.sub.2 and R.sub.3 is tolyl.

4. A colorant mixture according to claim 1 comprising as component (B) a dye of formula (201) ##STR00015##

5. A colorant mixture according to claim 1 comprising as component (B) a dye of formula (301) ##STR00016##

6. A colorant mixture according to claim 1 comprising, based on the total weight of components (A)+(B), 30-99% by weight of component (A) and 1-70% by weight of component (B).

7. A process for dyeing or printing cotton, polyester or cotton/polyester blend fibre material, wherein a colorant mixture according to claim 1 is applied to the said material or incorporated into it.

8. A process according to claim 7, wherein the colorant mixture is applied by screen-printing.

9. A process according to claim 7, wherein the dye is applied by inkjet-printing.

10. A process according to claim 7, characterised in that the fibre material is treated in any sequence with water, a water-soluble organic solvent having a boiling point greater than 150° C. and the colorant mixture.

11. A process according to claim 10, characterised in that the fibre material in a first step is treated with the water-soluble organic solvent having a boiling point greater than 150° C. and subsequently is printed with an aqueous ink comprising the colorant mixture.

12. A cotton, polyester or cotton/polyester blend fibre material, dyed or printed by the process according to claim 7.

Description

I. PREPARATION EXAMPLES

(1) I. 1 Dyestuff of Formula (101)

(2) ##STR00008##

(3) To 174 parts of sulfuric acid (96%) maintained at 5-10° C. are added 20 parts of water over a period of 10 minutes. Over a period of 20 minutes at 10-20° C., 21.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole are then added to the reaction mixture. After stirring for 3 hours at 10-15° C., the reaction mixture is cooled down to 0-5° C. and 36.4 parts of nitrosylsulfuric acid (40%) are added over 45 minutes. This reaction mixture (A) is stirred for 4.5 hours at 5-7° C. In the meantime, to 200 parts of acetic acid (100%) are added 21.1 parts of 2,6-bis-(3-methoxypropylamino)-3-cyano-4-methylpyridine at room temperature over a period of 10 minutes, after which 7.5 parts of sulfuric acid are added, followed by 35 parts of ice/water mixture and the mixture is stirred for 5 minutes. After cooling down to 5-7° C., 252 parts of the previous reaction mixture (A) are added over a period of 45 minutes. At the same time, 200 parts of acetic acid and 35 parts of water are added and the temperature is kept at 5-7° C. The reaction mixture so obtained is cooled down to 0-5° C. and 300 parts of sodium hydroxide solution (4N) are added over 2 hours whilst maintaining the reaction temperature at 0-5° C. The reaction mixture is stirred for an additional 3 hours at 0-5° C., then the temperature is allowed to rise slowly to 20° C. with stirring, after which 300 parts of sodium hydroxide solution (4N) are added at 20-25° C. over a period of 2 hours. Filtration of the reaction mixture and washing with water affords 191 parts of the crude filter cake.

(4) I. 2 Dyestuff of Formula (102)

(5) ##STR00009##

(6) To 174 parts of sulfuric acid (96%) maintained at 5-10° C. are added 20 parts of water over a period of 10 minutes. Over a period of 20 minutes at 10-20° C., 21.5 parts of 3-amino-5-nitro-2,1-benzoisothiazole are then added to the reaction mixture. After stirring for 3 hours at 10-15° C., the reaction mixture is cooled down to 0-5° C. and 36.4 parts of nitrosylsulfuric acid (40%) are added over 45 minutes. This reaction mixture (A) is stirred for 4.5 hours at 5-7° C. In the meantime, to 200 parts of acetic acid (100%) are added 23.8 parts of 2,6-bis-(p-tolylamino)-3-cyano-4-methylpyridine at room temperature over a period of 10 minutes, after which 7.5 parts of sulfuric acid are added, followed by 35 parts of ice/water mixture and the mixture is stirred for 5 minutes. After cooling down to 5-7° C., 252 parts of the previous reaction mixture (A) are added over a period of 45 minutes. At the same time, 200 parts of acetic acid and 35 parts of water are added and the temperature is kept at 5-7° C. The reaction mixture so obtained is cooled down to 0-5° C. and 300 parts of sodium hydroxide solution (4N) are added over 2 hours whilst maintaining the reaction temperature at 0-5° C. The reaction mixture is stirred for an additional 3 hours at 0-5° C., then the temperature is allowed to rise slowly to 20° C. with stirring, after which 300 parts of sodium hydroxide solution (4N) are added at 20-25° C. over a period of 2 hours. Filtration of the reaction mixture and washing with water affords 162 parts of the crude filter cake.

(7) Differential Scanning Calorimetry: decomposition>220° C.

(8) λ.sub.max=639 nm (λ.sub.max=wavelength of the absorption maximum, measured in DMF)

(9) TABLE-US-00001 Elemental Analysis: theory found C 62.9% 62.3% H 4.1% 4.2% N 21.0% 20.0% S 6.0% 5.9%

(10) .sup.1H-NMR (CDCl.sub.3, 250 MHz): δ=9.035 (s, 1H), 8.22 (d, 1H), 7.78 (d, 1H), 7.62-7.16 (m, 8H), 2.83 (s, 3H), 2.42 (s, 3H), 2.41 (s, 3H)

(11) I. 3 Dyestuffs of Formulae (103) and (104)

(12) ##STR00010##

(13) Example I. 1 is repeated by using a mixture of 2-phenylamino-6-(2-phenylethylamino)-3-cyano-4-methylpyridine and 2-(2-phenylethylamino)-6-phenylamino-3-cyano-4-methylpyridine as coupling component instead of 2,6-bis-(3-methoxypropylamino)-3-cyano-4-methylpyridine.

(14) λ.sub.max=598 nm (λ.sub.max=wavelength of the absorption maximum, measured in DMF)

(15) TABLE-US-00002 Elemental Analysis: theory found C 62.9% 62.7% H 4.1% 4.1% N 21.0% 20.6% S 6.0% 6.0%

(16) Examples I. 3 to I. 191

(17) As described in Example I. 1, the following dyestuffs can be prepared in an analogous manner:

(18) TABLE-US-00003 Ex. R1 R.sub.2 R.sub.3 I.4 H phenyl phenyl I.5 H mesityl mesityl I.6 H 2,4-dimethylphenyl 2,4-dimethylphenyl I.7 H o-tolyl o-tolyl I.8 H sec-butyl p-tolyl I.9 H p-tolyl sec-butyl I.10 H t-butyl p-tolyl I.11 H p-tolyl t-butyl I.12 H n-butyl p-tolyl I.13 H p-tolyl n-butyl I.14 H i-propyl p-tolyl I.15 H p-tolyl i-propyl I.16 H n-propyl p-tolyl I.17 H p-tolyl n-propyl I.18 H ethyl p-tolyl I.19 H p-tolyl ethyl I.20 H H p-tolyl I.21 H p-tolyl H I.22 H methyl p-tolyl I.23 H p-tolyl methyl I.24 H 3-methoxypropyl p-tolyl I.25 H p-tolyl 3-methoxypropyl I.26 H 3-ethoxypropyl p-tolyl I.27 H p-tolyl 3-ethoxypropyl I.28 H 2-(2-methoxyethoxy)ethyl p-tolyl I.29 H p-tolyl 2-(2-methoxyethoxy)ethyl I.30 H sec-butyl mesityl I.31 H mesityl sec-butyl I.32 H t-butyl mesityl I.33 H mesityl t-butyl I.34 H n-butyl mesityl I.35 H mesityl n-butyl I.36 H i-propyl mesityl I.37 H mesityl i-propyl I.38 H n- propyl mesityl I.39 H mesityl n-propyl I.40 H ethyl mesityl I.41 H mesityl ethyl I.42 H H mesityl I.43 H mesityl H I.44 H methyl mesityl I.45 H mesityl methyl I.46 H 3-methoxypropyl mesityl I.47 H mesityl 3-methoxypropyl I.48 H 3-ethoxypropyl mesityl I.49 H mesityl 3-ethoxypropyl I.50 H 2-(2-methoxyethoxy)ethyl mesityl I.51 H mesityl 2-(2-methoxyethoxy)ethyl I.52 H sec-butyl 2,4-dimethylphenyl I.53 H 2,4-dimethylphenyl sec-butyl I.54 H t-butyl 2,4-dimethylphenyl I.55 H 2,4-dimethylphenyl t-butyl I.56 H n-butyl 2,4-dimethylphenyl I.57 H 2,4-dimethylphenyl n-butyl I.58 H i-propyl 2,4-dimethylphenyl I.59 H 2,4-dimethylphenyl i-propyl I.60 H n- propyl 2,4-dimethylphenyl I.61 H 2,4-dimethylphenyl n-propyl I.62 H ethyl 2,4-dimethylphenyl I.63 H 2,4-dimethylphenyl ethyl I.64 H H 2,4-dimethylphenyl I.65 H 2,4-dimethylphenyl H I.66 H methyl 2,4-dimethylphenyl I.67 H 2,4-dimethylphenyl methyl I.68 H 3-methoxypropyl 2,4-dimethylphenyl I.69 H 2,4-dimethylphenyl 3-methoxypropyl I.70 H 3-ethoxypropyl 2,4-dimethylphenyl I.71 H 2,4-dimethylphenyl 3-ethoxypropyl I.72 H 2-(2-methoxyethoxy)ethyl 2,4-dimethylphenyl I.73 H 2,4-dimethylphenyl 2-(2-methoxyethoxy)ethyl I.74 H sec-butyl o-tolyl I.75 H o-tolyl sec-butyl I.76 H t-butyl o-tolyl I,.77 H o-tolyl t-butyl I.78 H n-butyl o-tolyl I.79 H o-tolyl n-butyl I.80 H i-propyl o-tolyl I.81 H o-tolyl i-propyl I.82 H n-propyl o-tolyl I.83 H o-tolyl n-propyl I.84 H ethyl o-tolyl I.85 H o-tolyl ethyl I.86 H H o-tolyl I.87 H o-tolyl H I.88 H methyl o-tolyl I.89 H o-tolyl methyl I.90 H 3-methoxypropyl o-tolyl I.91 H o-tolyl 3-methoxypropyl I.92 H 3-ethoxypropyl o-tolyl I.93 H o-tolyl 3-ethoxypropyl I.94 H 2-(2-methoxyethoxy)ethyl o-tolyl I.95 H o-tolyl 2-(2-methoxyethoxy)ethyl I.96 Br phenyl phenyl I.97 Br mesityl mesityl I.98 Br 2,4-dimethylphenyl 2,4-dimethylphenyl I.99 Br o-tolyl o-tolyl I.100 Br sec-butyl p-tolyl I.101 Br p-tolyl sec-butyl I.102 Br t-butyl p-tolyl I.103 Br p-tolyl t-butyl I.104 Br n-butyl p-tolyl I.105 Br p-tolyl n-butyl I.106 Br i-propyl p-tolyl I.107 Br p-tolyl i-propyl I.108 Br n- propyl p-tolyl I.109 Br p-tolyl n-propyl I.110 Br ethyl p-tolyl I.111 Br p-tolyl ethyl I.112 Br H p-tolyl I.113 Br p-tolyl H I.114 Br methyl p-tolyl I.115 Br p-tolyl methyl I.116 Br 3-methoxypropyl p-tolyl I.117 Br p-tolyl 3-methoxypropyl I.118 Br 3-ethoxypropyl p-tolyl I.119 Br p-tolyl 3-ethoxypropyl I.120 Br 2-(2-methoxyethoxy)ethyl p-tolyl I.121 Br p-tolyl 2-(2-methoxyethoxy)ethyl I.122 Br sec-butyl mesityl I.123 Br mesityl sec-butyl I.124 Br t-butyl mesityl I.125 Br mesityl t-butyl I.126 Br n-butyl mesityl I.127 Br mesityl n-butyl I.128 Br i-propyl mesityl I.129 Br mesityl i-propyl I.130 Br n- propyl mesityl I.131 Br mesityl n-propyl I.132 Br ethyl mesityl I.133 Br mesityl ethyl I.134 Br H mesityl I.135 Br mesityl H I.136 Br methyl mesityl I.137 Br mesityl methyl I.138 Br 3-methoxypropyl mesityl I.139 Br mesityl 3-methoxypropyl I.140 Br 3-ethoxypropyl mesityl I.141 Br mesityl 3-ethoxypropyl I.142 Br 2-(2-methoxyethoxy)ethyl mesityl I.143 Br mesityl 2-(2-methoxyethoxy)ethyl I.144 Br sec-butyl 2,4-dimethylphenyl I.145 Br 2,4-dimethylphenyl sec-butyl I.146 Br t-butyl 2,4-dimethylphenyl I.147 Br 2,4-dimethylphenyl t-butyl I.148 Br n-butyl 2,4-dimethylphenyl I.149 Br 2,4-dimethylphenyl n-butyl I.150 Br i-propyl 2,4-dimethylphenyl I.151 Br 2,4-dimethylphenyl i-propyl I.152 Br n- propyl 2,4-dimethylphenyl I.153 Br 2,4-dimethylphenyl n-propyl I.154 Br ethyl 2,4-dimethylphenyl I.155 Br 2,4-dimethylphenyl ethyl I.156 Br H 2,4-dimethylphenyl I.157 Br 2,4-dimethylphenyl H I.158 Br methyl 2,4-dimethylphenyl I.159 Br 2,4-dimethylphenyl methyl I.160 Br 3-methoxypropyl 2,4-dimethylphenyl I.161 Br 2,4-dimethylphenyl 3-methoxypropyl I.162 Br 3-ethoxypropyl 2,4-dimethylphenyl I.163 Br 2,4-dimethylphenyl 3-ethoxypropyl I.164 Br 2-(2-methoxyethoxy)ethyl 2,4-dimethylphenyl I.165 Br 2,4-dimethylphenyl 2-(2-methoxyethoxy)ethyl I.166 Br sec-butyl o-tolyl I.167 Br o-tolyl sec-butyl I.168 Br t-butyl o-tolyl I.169 Br o-tolyl t-butyl I.170 Br n-butyl o-tolyl I.171 Br o-tolyl n-butyl I.172 Br i-propyl o-tolyl I.173 Br o-tolyl i-propyl I.174 Br n- propyl o-tolyl I.175 Br o-tolyl n-propyl I.176 Br ethyl o-tolyl I.177 Br o-tolyl ethyl I.178 Br H o-tolyl I.179 Br o-tolyl H I.180 Br methyl o-tolyl I.181 Br o-tolyl methyl I.182 Br 3-methoxypropyl o-tolyl I.183 Br o-tolyl 3-methoxypropyl I.184 Br 3-ethoxypropyl o-tolyl I.185 Br o-tolyl 3-ethoxypropyl I.186 Br 2-(2-methoxyethoxy)ethyl o-tolyl I.187 Br o-tolyl 2-(2-methoxyethoxy)ethyl I.188 H phenyl 2-phenylethyl I.189 H 2-phenylethyl phenyl I.190 Br phenyl 2-phenylethyl I.191 Br 2-phenylethyl phenyl

II. APPLICATION EXAMPLES

(19) The following dyes are used in the Application Examples:

(20) ##STR00011## ##STR00012##

(21) The procedure described in WO2005/024123 is carried out using the disperse dyes according to the invention and the thus obtained printed fabrics exhibit very good light fastness, wash fastness and rubbing fastness. The dispersion formulation is variable according to the dyes' properties and can be modified accordingly by the skilled artisan.

Example II. 1

(22) A cotton/polyester fabric (Reference Nr. 7-3014, CO/PES 33/67, fixed, bleached, mercerized, 208 g/m.sup.2, 30/30 tex) is padded at room temperature with an aqueous formulation containing 200 g/l of MACROGOL 400 EF (PEG, average molecular weight M.sub.w=400, supplied by Brenntag), 40 g/l PREPAJET UNI (inkjet auxiliary, polyacrylic acid derivative, supplied by Huntsman) and 1 g/l ALBATEX AR (leveling agent, supplied by Huntsman) with a pick-up rate of 70-85%. After drying at 80-100° C. for 10 min, the thus prepared fabric is printed by ink-jet with an aqueous ink containing 3.3% by weight of a disperse dye of formula (101), 6.1% by weight of a disperse dye of formula (201), 1.6% by weight of a disperse dye of formula (401), 15% by weight of glycerol (85%) 16.7% by weight of a mixture of commercial water-soluble dispersants, and 57.3% by weight of deionized water.

(23) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(24) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(25) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 2

(26) The same procedure as described in Example II. 1 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(27) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(28) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 3

(29) A polyester fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) is padded in a standard procedure for subsequent inkjet printing, with an aqueous formulation based on PREPAJET UNI (inkjet auxiliary, polyacrylic acid derivative, supplied by Huntsman). The thus prepared fabric is printed by ink-jet with the same inkjet ink as used in Example II. 1 and Example II. 2.

(30) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(31) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 4

(32) The same procedure as described in Example II. 1 is applied using an aqueous ink containing 4.3% by weight of a disperse dye of formula (102), 2.7% by weight of a disperse dye of formula (201), 20.2% by weight of glycerol (85%) 6.3% by weight of a mixture of commercial water-soluble dispersants, 0.2% by weight of a commercial tenside, and 66.3% by weight of deionized water.

(33) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(34) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(35) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 5

(36) The procedure described in Example II. 4 is applied to a cotton fabric (Reference Nr. 1-3011, CO-cretonne bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(37) Similarly to cotton/polyester, very deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(38) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 6

(39) Standard screen printing paste (flat bed or rotary) is applied according to a method similar to that described in WO2005/024123. Fixing and washing conditions are similar to those mentioned in Examples II. 1-II. 5. Viscosity is adapted to the relevant flat bed and rotary screen printing method.

(40) A stock paste P1 containing 84.9% by weight of deionized water, 10.0% by weight of Macrogol 400 EF, 5.0% by weight of a commercial thickener, and 0.1% by weight of a reduction inhibitor

(41) is prepared.

(42) A cotton/polyester fabric (Reference Nr. 7-3014, CO/PES 33/67, fixed, bleached, mercerized, 208 g/m.sup.2, 30/30 tex) is screen printed at room temperature with a printing paste containing 84.5% by weight of stock paste P1, 7.6% by weight of a dispersion containing 17.7% of disperse dye of formula (201), 6.7% by weight of a dispersion containing 15% of disperse dye of formula (101) and 1.2% by weight of a dispersion containing 19.2% of disperse dye of formula (401)

(43) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(44) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(45) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 7

(46) The same procedure as described in Example II. 6 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(47) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(48) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 8

(49) The same procedure as described in Example 11.6 or Example 11.7 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(50) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(51) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 9

(52) The same procedure as described in Example II. 6 is applied using a printing paste containing 85.2% by weight of stock paste P1, 3.4% by weight of a dispersion containing 15% of disperse dye of formula (301), 5.3% by weight of a dispersion containing 15% of disperse dye of formula (101), 5.3% by weight of a dispersion containing 19.2% of disperse dye of formula (401) and 0.8% by weight of deionized water

(53) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(54) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(55) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 10

(56) The same procedure as described in Example II. 9 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(57) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(58) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 11

(59) The same procedure as described in Example II. 9 or Example II. 10 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(60) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(61) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 12

(62) The same procedure as described in Example II. 6 is applied using a printing paste containing 85.4% by weight of stock paste P1, 1.3% by weight of a dispersion containing 17.7% of disperse dye of formula (201) and 13.3% by weight of a dispersion containing 15% of disperse dye of formula (102)

(63) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(64) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(65) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 13

(66) The same procedure as described in Example II. 12 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(67) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(68) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 14

(69) The same procedure as described in Example II. 12 or Example II. 13 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(70) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(71) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 15

(72) The same procedure as described in Example II. 6 is applied using a printing paste containing 85.2% by weight of stock paste P1, 1.5% by weight of a dispersion containing 15% of disperse dye of formula (301) and 13.3% by weight of a dispersion containing 15% of disperse dye of formula (102)

(73) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(74) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(75) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 16

(76) The same procedure as described in Example II. 15 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(77) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(78) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 17

(79) The same procedure as described in Example II. 15 or Example II. 16 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(80) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(81) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 18

(82) The same procedure as described in Example II. 6 is applied using a printing paste containing 80.7% by weight of stock paste P1, 1.3% by weight of a dispersion containing 22.6% of disperse dye of formula (201) and 18% by weight of a dispersion containing 15% of disperse dye of formula (102)

(83) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(84) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(85) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 19

(86) The same procedure as described in Example II. 18 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(87) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(88) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 20

(89) The same procedure as described in Example II. 18 or Example II. 19 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(90) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(91) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 21

(92) The same procedure as described in Example II. 6 is applied using a different quality cotton/polyester fabric (Reference No 7-3011, CO/PES 35/65) and using a printing paste containing disperse dye of formula (201), disperse dye of formula (103) and disperse dye of formula (104).

(93) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(94) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(95) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

Example II. 22

(96) The same procedure as described in Example II. 21 is applied to a cotton fabric (Reference Nr. 1-3011, CO-crettone bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(97) Similarly to cotton/polyester, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(98) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 23

(99) The same procedure as described in Example II. 21 or Example II. 22 is applied to a PES fabric (Reference Nr. 5-3208, fixed, 90 g/m.sup.2) instead of a cotton/polyester fabric, and using a standard stock paste for PES printing which does not contain any Macrogol 400 EF.

(100) Similarly to cotton/polyester and cotton, very deep black prints of very high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained on cotton/polyester fabric.

(101) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 24

(102) The same procedure as described in Example II. 1 is applied using a different quality cotton/polyester fabric (Reference No 7-3011, CO/PES 35/65) and using an aqueous ink containing

(103) 3.41% by weight of disperse dye of formula (201),

(104) 2.59% by weight of a mixture of disperse dye of formula (103) and disperse dye of formula (104),

(105) 25.50% by weight of glycerol (85%)

(106) 6.06% by weight of a mixture of commercial water-soluble dispersants,

(107) 2.96% by weight of a polyethylene glycol,

(108) 1% by weight of a commercial tenside,

(109) 0.23% by weight of a commercial bactericide agent, and

(110) 58.25% by weight of deionized water.

(111) After drying at 80-100° C. for 10 min, the printed fabric is fixed at 200° C. for 90 s. After cooling down, the printed fabric is rinsed with cold soft water and finally washed with a solution of 1 g/l commercial tenside, rinsed and dried.

(112) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(113) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 25

(114) The procedure described in Example II. 24 is applied to a cotton fabric (Reference Nr. 1-3011, CO-cretonne bleached, 135 g/m.sup.2, 30/30 tex) instead of a cotton/polyester fabric.

(115) Similarly to cotton/polyester, very deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are 690 obtained on cotton/polyester fabric.

(116) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or is fixed with superheated steam at 180° C. for 8 min.

Example II. 26

(117) The same procedure as described in Example II. 3 is applied using the aqueous ink described in Example II. 24.

(118) Deep black prints of high color strength having good all-round fastness properties, especially wash fastness, rubbing fastness and light fastness, are obtained.

(119) Similar results and properties are obtained if the dried print is fixed at lower temperature with longer fixation time or if it is fixed with superheated steam at 180° C. for 8 min.

(120) TABLE-US-00004 TABLE 2 Color Coordinates and color depth measured according to the norm CIELAB 1976/DIN 6174, with D65/10 (Illuminant/Observer) L C* H RD Example # (Lightness) a* b* (Chroma) (Hue) (Reference Depth) Example II.1 28.07 −5.32 −4.13 6.74 217.84 1.40 Example II.2 21.72 −0.71 −5.47 5.51 262.57 2.13 Example II.3 24.94 −3.80 −3.07 4.89 218.93 1.80 Example II.4 25.01 −3.25 −0.10 3.25 181.76 1.81 Example II.5 23.13 0.42 −0.03 0.42 355.44 2.01 Example II.6 23.27 −2.73 −1.59 3.16 210.29 2.07 Example II.7 24.17 0.96 −6.74 6.81 278.14 1.69 Example II.8 23.80 −2.66 −3.50 4.40 232.83 1.96 Example II.9 21.87 −0.18 −2.58 2.58 265.95 2.14 Example II.10 22.45 −0.79 −5.35 5.41 261.63 1.98 Example II.11 23.27 1.82 −5.04 5.35 289.84 1.80 Example II.12 21.76 0.96 −2.35 2.54 292.20 2.17 Example II.13 21.42 2.59 −4.78 5.44 298.42 2.09 Example II.14 23.52 −4.11 −7.27 8.35 240.51 1.87 Example II.15 21.11 1.72 0.48 1.79 15.48 2.39 Example II.16 21.76 2.02 −1.06 2.28 332.24 2.17 Example II.17 21.81 −2.23 −4.08 4.65 241.34 2.14 Example II.18 20.96 2.72 −2.91 3.98 313.07 2.23 Example II.19 20.79 0.80 −1.04 1.31 307.53 2.41 Example II.20 20.68 2.71 −2.28 3.54 319.90 2.31 Example II.21 24.06 −2.12 −0.37 2.16 189.26 1.98 Example II.22 25.15 −1.90 −0.18 1.91 158.35 1.79 Example II.23 23.01 −2.94 −1.81 3.46 211.57 2.14