GB2346150A - Dye mixtures and their use for dyeing or printing cellulose acetate-containing fibre materials - Google Patents
Dye mixtures and their use for dyeing or printing cellulose acetate-containing fibre materials Download PDFInfo
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- GB2346150A GB2346150A GB0001184A GB0001184A GB2346150A GB 2346150 A GB2346150 A GB 2346150A GB 0001184 A GB0001184 A GB 0001184A GB 0001184 A GB0001184 A GB 0001184A GB 2346150 A GB2346150 A GB 2346150A
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- dye
- c4alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 239000000463 material Substances 0.000 title claims abstract description 26
- 238000004043 dyeing Methods 0.000 title claims abstract description 20
- 239000000835 fiber Substances 0.000 title claims abstract description 14
- 229920002301 cellulose acetate Polymers 0.000 title claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 243
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 claims description 7
- 229920002284 Cellulose triacetate Polymers 0.000 claims description 6
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 239000011436 cob Substances 0.000 claims 1
- 230000002209 hydrophobic effect Effects 0.000 abstract description 8
- 210000002268 wool Anatomy 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 238000010186 staining Methods 0.000 abstract description 2
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 description 17
- 239000004753 textile Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- -1 methoxy, ethoxy propoxy Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
This invention relates to dye mixtures, which comprise at least two dyes of formulae <EMI ID=1.1 HE=137 WI=157 LX=149 LY=664 TI=CF> <PC>and <EMI ID=1.2 HE=26 WI=66 LX=163 LY=2059 TI=CF> <PC>wherein the variables R<SB>1</SB> to R<SB>30</SB> are Hal, and A to E have the meanings defined in claim 1, and to the use of these mixtures for dyeing or printing semisynthetic hydrophobic cellulose acetate-containing fibre materials. These mixtures do not stain wool or cotton if present in blends with cellulose acetate (or effect only minor staining).
Description
1-21969/A 2346150 Dye mixtures and their use for dyeing or printing,,
cellulose acetate- containing fibre materials The present invention relates to mixtures of dyes', to their preparation and to their use for dyeing or printing cellulose acetate-containing fibre materials.
Dyes and dye mixtures for dyeing semisynthetic 'or synthetic hydrophobic cellulose acetatecontaining fibre materials, for example cellulose-'/2 acetate and cellulose triacetate, are known. However, it has been found that these dybs or the mixtures thereof do not always fully meet the highest requirements, especially with regard to reproducibility, susceptibility to the temperature of the dyebath or suitability for specific dyeing processes, in particular when a jigger or jet dyeing apparatus is used. There isthus a demand for novel dyes or dye mixtures which do not have these drawbacks.
Surprisingly, it has now been found that the mi.res of this invention substantially fulfil the above criteria.
Accordingly, this invention relates to a dye mixture, which comprises at least two dyes of formulae Ri R 3 0 N N = N ----- N / R 5 2 R 6 R2 R4 wherein R, is hydrogen, halogen, nitro or cyano, R2 is hydrogen, halogen, nitro or cyano, R3 is hydrogen, halogen or CI-C4alkoxy, R4 is hydrogen, Cl-C4alkylcarbonylamino, R5 is hydrogen; CI_C4alkyl which is unsubstituted'or substituted by hydroxy, cyano, CI_C4_ alkylcarbonyloxy, R6 is CI_C4alkyI which is unsubstituted or substitutd by hydroxy, cyano, Cl-C4alkyfcarbonylOXY, Cl-C4alkoxycarbonyl, NC R7 0== N=N-P-Hal N R8 OH NO 2 wherein R7 is Cl-C4alkyl, R8 is Cl-C4alkyl, and Hal is halogen, Wl- so 2-NH--Ci) NO 2 wherein the rings A and B may be further substituted, R -CO-NH N = N D 9 -Q-Z (4), HO wherein R9 is C1-C4alkyl and the rings C and D may be further substituted, R 30 N /RIO (5), \>- N = N-0- N \ R'.1ccS R11 29 wherein R10 is unsubstituted or hydroxy- or cyano-substituted CI-C4alkyl, R,j is unsubstituted or -0-COR12-substituted Cl-C4alkyl, wherein R12 is Cl-C4alkyl, R29 is nitro, C1-C4alkoxy or -S02CH3, and R30 is hydrogen or CI-C4alkyl, -3" R SR15 113 S -- / N N = N (6), R 14 R 16 wherein R13 is Cl-C4alkyl, R14 is Cl-C4alkyl, R15 is CI-C4alkyl, and R16 is Cl- C4alkyl or -NHCOR17, wherein R17 is Cl-C4alkyl, N's JR 18 N = N N \ R19 R 20 NO 2 wherein Rls is unsubstituted or hydroxy- or cyano-substitq'ted Cl-C4alkyl, R19 is unsubstituted or hydroxy- or Cl-C4alkoxycarbonyl-substituted Cl-04alkyl, and R20 is hydrogen, CI-C4alkyl or NHCOR17, R17 is CI-C4alkyl, NH 2 0 OH 1 1 (8), R 21 OH 0 NH 2 OH 0 NH 2 1 1 (9), R 21 NH 2 0 OH NH 2 0 NH2 I 1 (10), R21 OH 0 OH wherein R21 is halogen, R 22 R 1 24 ONON=N E N R23 R 25 wherein R22 is cyano, nitro or halogen, R23 is halogen, R24 is unsubstituted or hydroxy-substituted Cj- C4alkyl, and R25 is unsubstituted or hydroxy-substituted CI-C4alkyl, and the naphthyl ring E may be further substituted, and NO 2 IR 27 R 28 R 26 wherein R26 is C1-C4alkyl or the radical NHCOR17, wherein R1, is CI- C4alkyl, R27 is C1-C4alkyI or CjC4alkylcarbonyloxy-Cl-C4alkyl, and R213 is Cl-C4alkyl or Cl-C4alkylcarbonyloxy-Cl-C4alkyl.
The dye mixture defined above advantageously comprises at least one dye of formula (1).
CI-CAlkyl as such and as a radical in Cl-C4alky[carbonylamino or CIC"alky1carbonyloxy is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl.
CI-CAlkoxy as such or as a radical inCl-CAlkoycarbonyl is, for example, methoxy, ethoxy propoxy or butoxy.
Rl, R3, R22 and R23 defined as halogen are, for eample, bromo or, preferably, chloro. R2 and R21 defined as halogen are, for example, hloro or, preferably, bromo. Halogen in formula (2) is, for example, bromo or, :Preferably, chloro. R3 defined as Cl-C4alkoxy is preferably ethoxy and, more preferably, methoxy. R4 defined as Cl-C4alkylcarbonylamino is preferably propionylamino and, more preferably, acetylamino. R5, R6 and R10 defined as Cl-C4alkyf are propyl or isopropyl and, preferably, ethyl. R79 R9,1312, R16, R17l R20v R26 and R3o defined as C.1-C4alkyl are preferably ethyl and, more preferably, methyl. R8, Rill R151 R181 Rig, R27 and R28 defined as Cl-0.4alkyl are preferably methyl and, more preferably, ethyl. R13, R14, R24 and R25 defined as Cl-C4alkyl are proferably ethyl and, more preferably, propyl. R27 and R28 are preferably CI-C4alkyl. R29 is preferably nitro or the radical -S02CH3.
The Cl-C4alkyl radicals are usually substituted onp or twice with the substituents cited above.
Preferred dye mixtures are those, which comprise. at least two dyes of formulae NC CH 3 0 N = N Cl IN / H 3 CH2C/ OH NO 2 O-NH-P-SO2-NH--o (14), N02 H3C-CO-NH--aN N--J:] (15), HO N CH CH CN C CH CH O-COCH 2 2 \>-N N \ (16), 02 N"'C s 2 2- 3 CN CH CH -0-COCH / 2 2 3(17), 02N-6 N = W-a N \ CH2CH 2-0-COCH3 cl CH CH /23 (18), 02N-d-N = N-&N \ CH2CH2CN H3CH2CH2c SYSCH2CH3 \ N-Q-N = N-<\ I NN (19), H3CH2CH2cNHCOCH 3 cl cl / CH2-!CH(CH 3)-OH 02N N = N N (20), NHCOCH, CH20H -0-COCH 0 N N N-& / 2 3 (21), 2 N\ CH2CH2CN cl CH CH OH 0 N N / 2 2 (22), 2-6 N-&N \ CH20. H2CN N--s CH CH 2 3 N N--O-N \ r CH2CH2COOCH3 (23), N02 NH2 0 OH 1 (24), Br OH 0 NH2 OH 0 NH2 1 1 (25), Br NH2 0 OH NH2 0 NH2 1 1 (26), Br OH 0 OH NHCOCH 3 s CH2 CH 2 OH N-- r CH 2 CH 2 OH (27), N02 N02 OCH3 CH2 CH 3 0 N N = N N \ (28), CH2 CH3 Br NHCOCH 3 9 NO 2 CH CH(OH)-CH OH 0 N N N \1 N / 2 2 (29), CH 2-CH(OH)-CH OH 2 cl N02 \1 H 0 N N N N (30), CH 20H 2 OH 2 cl CN / CH 20H 3 0 N N N- N \ (31), CH 20H 3 Br NHCOCH2CH 3 CN CH CH 02 N-0-N N- N / 2: 3 (32), CH 2CH 3 CN NHCOCH 3 NO 2 OCH 3 / CH 2QH 2-0-COCH 3 2 N = N N \ (33), CH 2 QH 2-0-COCH 3 Br NHCOCH 3 NO 2 CH 2 CH 3 0 N N = N N\ (34), CH 2 CH 3 r NHCOCH 3 NO 2 CH 2 CH 3 (35), 0 N S N = N N\ CH2 CH3 NHCOCH 3 CH2 CH2 CN 02N N = N-aN/ (36), CH 2 CH 2-0-COCH 3 cl 0 N-0-N = N N / CH2 CH 2 OH (37), CH 2 CH 2 OH cl CH CH / 2 3 02 N-0-N = N- N \ CH 2 CH 3 (38), N NHCOCH 3 CH3 N N = N-&N / CH2CH,CN (39), H3CO2S"'CCS CH2CH3 IN N = N-& / CH2CH20H (40) and \>- N\ H3CO JCCS CH2CH3 N02 0 N" I S I N = N-&N / CH2CH20-COCH3 (41).
2 CH CH -0-COCH 2 2 3 The dyes of formulae (1) to (41) are known or can! be prepared by commonly known methods.
A particularly preferred dye mixture is that, which,comprises the dyes of formulae (23) and (41).
A particularly preferred dye mixture is that, which comprises the dyes of formulae (13), (14) and (15).
Another particularly preferred dye mixture is that, yvhich comprises the dyes of formulae (17), (18), (21) and (22).
A particularly preferred dye mixture is also that, which comprises the dyes of formulae (16), (17), (39) and (18).
A particularly preferred dye mixture is also that, wkich comprises the dyes of formulae (20), (19) and (39).
Also particularly preferred is a dye mixture, which omprises the dyes of formulae (23), (24), (25) and (26).
Another particularly preferred dye mixture is that, which comprises the dyes of formulae (32), (38), (23), (28), (33) and (27).
Also particularly preferred is a dye mixture, which comprises the dyes of formulae (29), (30), (23), (32), (28), (34) and (33).
Another particularly preferred dye mixture is that, which comprises the dyes of formulae (35), (27) and (28).
A particularly preferred dye mixture is also that, which comprises the dyes of formulae (29), (30), (28), (36), (32), (34), (33), (38) and (17).
Another particularly preferred dye mixture is that, which compdses the dyes of formulae (24), (25), (26), (30), (29), (23), (37), (13), (34) and (33).
Also particularly preferred is a dye mixture, which comprises the dyes of formulae (28), (30), (29), (13), (21), (22), (34), (33), (36), (32) and (38).
A particularly preferred dye mixture is also that, which comprises the dyes of formulae (16), (17), (18) and (40).
Another particularly preferred dye mixture is that, which compdses the dyes of formulae (19), (20) and (40).
A very particularly preferred dye mixture is that, which comprises 5 to 15 parts by weight of the dye of formula (13), 22 to 48 parts by weight of the dye of formula (14), and 12 to 37 parts by weight of the dye of formula (15).
Another very particularly preferred dye mixture is that, which comprises 12 to 39 parts by weight of the dye of formula (18), 5 to 18 parts by weight of the dye of formula (17), 15 to 36 parts by weight of the dye of formula (21), and 2 to 7 parts by weight of the dye of formula (22).
1 Also very particularly preferred is a dye mixture, vhich comprises 6 to 23 parts by weight of the dye of formula (18), 7 to 23 parts by weight of the dye of formula (17), 10 to 31 parts by weight of the dye of formula (30), and 6 to 23 parts by weight of the dye of formula (116)'.
Another very particularly preferred dye mixture i that, which comprises 7 to 22 parts by weight of the dye of formula (20)',, 12 to 44 parts by weight of the dye of formula (1 and 10 to 34 parts by weight of the dye of formula (3 ).
Likewise very particularly preferred is a dye mire, which comprises 9 to 24 parts by weight of the dye of formula (24), 9 to 24 parts by weight of the dye of formula (25):, 9 to 24 parts by weight of the dye of formula (26), and 10 to 28 parts by weight of the dye of formula (2d).
Also very particularly preferred is a dye mixture, thiclh comprises 4 to 19 parts by weight of the dye of formula (32),! 5 to 19 parts by weight of the dye of formula (38),' 6 to 21 parts by weight of the dye of formula (23)' 3 to 15 parts by weight of the dye of formula (33), 3 to 15 parts by weight of the dye of formula (28),' and 5 to 21 parts by weight of the dye of formula (27).i, Another very particularly preferred dye mixture is'that, which comprises 7 to 25 parts by weight of the dye of formula (29),'1 8 to 25 parts by weight of the dye of formula (30),;: 3 to 14 parts by weight of the dye of formula (23),'! 2 to 12 parts by weight of the dye of formula (32),i 1 to 8 parts by weight of the dye of formula (28), 2 to 10 parts by weight of the dye of formula (34),'and 1 to 6 parts by weight of the dye of formula (33).
Also very particularly preferred is a dye mixture, which comprises 15 to 54 parts by weight of the dye of formula (35), 10 to 35 parts by weight of the dye of formula (27), and 2 to 11 parts by weight of the dye of formula (28).
Likewise very particularly preferred is a dye mixture, which comprises 8 to 25 parts by weight of the dye of formula (29), 3 to 11 parts by weight of the dye of formula (30), 1 to 8 parts by weight of the dye of formula (28), 3 to 6 parts by weight of the dye of formula (36), 3 to 12 parts by weight of the dye of formula (32), 2 to 9 parts by weight of the dye of formula (34), 3 to 13 parts by weight of the dye of formula (33), 0.5 to 3 parts by weight of the dye of formula (117), and 4 to 13 parts by weight of the dye of formula (38)-.-- Also very particularly preferred is a dye mixture, which comprises 1.2 to 6 parts by weight of the dye of formula (24), 1.2 to 6 parts by weight of the dye of formula (25), 1.2 to 6 parts by weight of the dye of formula (26), 3 to 13 parts by weight of the dye of formula (30), 4 to 17 parts by weight of the dye of formula (29), 1 to 7 parts by weight of the dye of formula (23), 6 to 19 parts by weight of the dye of formula (37), 4 to 14 parts by weight of the dye of formula (13), 1 to 5 parts by weight of the dye of formula (34), and I to 7 parts by weight of the dye of formula (33).
Another very particularly preferred dye mixture is that, which comprises 2 to 9 parts by weight of the dye of formula (28), 2 to 10 parts by weight of the dye of formula (30), 3 to 13 parts by weight of the dye of formula (29), 2 to 9 parts by weight of the dye of formula (13), 2 to 10 parts by weight of the dye of formula (21), 0.3 to 3 parts by weight of the dye of formula (22) 1 to 6 parts by weight of the dye of formula (34), 1 to 7 parts by weight of the dye of formula (33), 2 to 11 parts by weight of the dye of formula (36); 2 to 11 parts by weight of the dye of formula (32),. and 2 to 11 parts by weight of the dye of formula (38). 1 The novel dye mixtures can be used as dyes for dyeing and printing semisynthetic hydrophobic, cellulose acetate-containing fibre materials, in particular textile matedals. Textile materials consisting of blended fabrics containing semlsynthetic hydrophobic, cellulose acetatecontaining textile materials and e.g. viscose or po,lyamide can also be dyed or printed by means of the dye mixtures of this invention.
Suitable semisynthetic hydrophobic, cellulose ace'tate-containing textile materials are especially cellulose-2'/2acetate-and cellulose triaq.;etate.
The novel compounds are applied to the textile moterials by known dyeing processes. Cellulose-2'/2acetate, for example, is preferably died in the temperature range from about 65 to 950C and cellulose triacetate in the tempera iure range from 65 to 1300C, preferably from 90 to 1250C.
The novel dye mixtures do not stain wool and cn simultaneously present in the dyebath or effect only minor staining (very good resist), so 1hat they can also readily be used for dyeing cellulose acetate/wool and cellulose acetate/co 11 u lose blends.
The novel dye mixtures are suitable for dyeing by ithe thermosol, pad steam, pad roll and pad jig process and for printing processes.
The cited textile material can be in a very wide range of forms of presentation, such as fibre, thread or nonwoven fabric, or wovens or knitgoods.
It is expedient to convert the novel dye mixtures, before use, into a dye formulation. This is done by milling the dye mixture to an average particle size of 0.1 to 10 microns. Milling can usefully be carried out in the presence of dispersahts. Typically, the dried dye mixture is milled with one or more than one dispersant, or kneaded in paste form with one or more than one dispersant, and thereafter dried under vacuum or by spray drying. Printing pastes and dyebaths can be prepared by adding water to the formulations so obtained. Suitable dispersants are those customarily used for dyeing with disperse dyes, for example the dispersants cited in EP-A-0 280 654.
However, the dyes can also be formulated singly, as described above, and then converted into the corresponding dye formulation by a simple blending process.
The amount of the dispersant(s) present in the dye formulation can range from 0 to 75 % by weight, based on the weight of the dye formulation.
The amount of the dye mixtures in the dye liquor depends on the desired shade. Amounts which have been found to be useful range from 0.01 to 15 % by weight, preferably from 0.02 to 10 % by weight, most preferably from 0. 1 to 5 % by-weight, based on the weight of the fibre material to be dyed.
The dye liquors can also contain other additives, for example dyeing auxiliaries, wetting agents and defoamers.
The dye liquors can also contain mineral acids, for example sulfuric acid or phosphoric acid, or, preferably, organic acids, for example fumaric acid or acetic acid and/or salts, such as ammonium acetate or sodium sulfates. The acids serve mainly to adjust the pH value of the dye liquors which is preferably from 4 to 7.
The customary thickeners will be used for pdnting, for example modified or nonmodified natural products, such as alginates, British gum, gum arabic, crystal gum, carob bean gum, tragacanth, carboxym ethyl cel I ulose, hydroxyethylce I I u lose, starch or synthetic products, for example polyac ryla m ides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.
The cited materials, especially the cellulose-2'/2acetate and cellulose triacetate, are dyed with the novel dye mixtures in level shades having very good end use properties, in particular good fastness to light, thermofixation, pleating, chlorinating and good fastness to wet treatments, such as fastness to water, sweat and washing; and the dyeings are also distin- guished by excellent fastness to rubbing. To be highlighted in particular is the good dye yield and good build-up of the novel dye mixtures.
The novel dye mixtures can also be readily used'for obtaining mixed shades in conjunction with other dyes.
In addition, the novel dye mixtures are also very $uitable for dyeing hydrophobic textile material from supercritical C02.
Further objects of the invention are the aforemen, tioned use of the dye mixtures of this invention and a process for dyeing or printing semisynthetic hydrophobic, cellulose acetate-containing fibre material, in particular textile mate rial'consisti ng of cellulose-2/2acetate and cellulose triacetate, which comprises applying the nvel dye mixture to said material or incorporating it therein. Other substrates which can be tr: ated by the process of this invention and preferred process conditions-have been discussed above in the more detailed description of the use of the novel dye mixtures. The definitions and preferred meanings mentioned for the dyes and dye mixtures apply to the dye mixtures Psed according to this invention.
This invention also relates to the semisynthetic, C.Ollulose acetatecontaining hydrophobic fibre material, preferably to textile material consising of cellulose-21/2acetate and cellulose triacetate, which is dyed or printed by the cited process.
This invention is illustrated in more detail by the folowing Examples. Parts and percentages are by weight, unless otherwise stated. TemperatiOres, are given in degrees Celsius. The relationship between parts by weight and parts by!. volume is the same as that of the gramme and the cubic centimetre.
Example 1:
In an AHIBA laboratory dyeing apparatus, a 10 g Oiece of a textile material consisting of cellulose-2'/2acetate is dipped at 400C into a liqudr containing 0.5 g/1 of a commercially available penetration acelerator (OCibaflow/CIR), U-17" 0.3 g/I of a commercially available dispersant (OAI'atePON conc.), and 0. 2 g of a dye formulation (A) containing 0.0122 g of the dye of formula NC CH O=% N=N Cl (13), 1 -P- H 3 CH21/ OH NO, 0.0484 g of the dye of formula &NH__Q_S02_NH_0 (14), N02 0.031 g of the dye of formula H3C-CO-NH_0_N=N_P__0 (15) and HO 0.1084 g of a commercially available dispersant Dispergator CC), which is adjusted to pH 6.0 with 80% fumaric acid. The liquor is then heated to 90"C at a heating rate of 1-20 C/minute and the textile material is dyed at this temperature for 60 minutes. The liquor is then cooled to 40 C and the dyed textile material is washed with warm and cold water and then dried. This gives a brilliant golden yellow dyeing having excellent end use fastness properties.
Examples 2 to 10:
The procedure of Example 1 is repeated, but replacing the 0.2 g of the dye formulation (A) used in that Example with the dye formulations (B) to (K) listed in Table 1 in the amounts stated there, which also yields dyeings having very good end use fastness properties.
-19'.
i i Table 1: 1
Dye formulation Composition of the dye formulation Amount Shade (B) 14.0 % by weight of the dye of formula (18), 0.1 g scarlet 6.9 % by weight of the dye of formula(l 7), 16.83 % by weight of the dye of formla (21), 2.97 % by weight of the dye of formula (22), and i 59.3 % by weight of a commercially vailable dispersant (C) 8.0 % by weight of the dye of formula'(1 8), 0.1 red 1 9.2 % by weight of the dye of formula'(1 7), (39), 12.0 % by weight of the dye of formuT 8.0 % by weight of the dye of formula (16), and 1 62.8 % by weight of a commercially ayailable dispersant (D) 8.3 % by weight of the dye of formula'(20), 0.1 g pink 15.2 % by weight of the dye of formu 19), 12.0 % by weight of the dye of formul (39), and 64.5 % by weight of a commercially aailable dispersant (E) 9.93 % by weight of the dye of formul; (24), 0.17 g blue 9.93 % by weight of the dye of formul (25), 9.93 % by weight of the dye of formull (26), 11.8 % by weight of the dye of formula (23), and 58.41 % by weight of a commercially ivailable dispersant (F) 5.9 % by weight of the dye of formula 32), 0.18 blue 6.5 % by weight of the dye of formula 7.1 % by weight of the dye of formula (23), 4.2 % by weight of the dye of formula 128), 4.5 % by weight of the dye of formula (33), 6.3 % by weight of the dye of formula 27), and alilable 65.5 % by weight of a commercially dispersant (G) 9.0 % by weight of the dye of formula 9), 0.45 g dark blue 9.6 % by weight of the dye of formula 30), 4.7 % by weight of the dye of formula 3), 3.6 % by weight of the dye of formula 2), 1.8 % by weight of the dye of formula 2.9 % by weight of the dye of formula (64), 1.7 % by weight of the dye of formula $3), and 66.7 % by weight of a commercially a#lable dispersant (H) 17.7 % by weight of the dye of formula (35), 0.15 g turquoise 12.6 % by weight of the dye of formula (27), 3.2 % by weight of the dye of formula (28), and 66.5 % by weight of a commercially available dispersant (1) 9.1 % by weight of the dye of formula (29), 0.45 g navy 4.2 % by weight of the dye of formula (30), 3.2 % by weight of the dye of formula (28), 2.3 % by weight of the dye of formula (36), 4.5 % by weight of the dye of formula (32), 3.8 % by weight of the dye of formula (34), 4.5 % by weight of the dye of formula (33), 5.0 % by weight of the dye of formula (38), 0.7 % by weight of the dye of formula (17), and 62.7 % by weight of a commercially available dispersant (J) 1.4 % by weight of the dye of formula (24), 0.45 black 1.4 % by weight of the dye of formula (25), 1.4 % by weight of the dye of formula (26), 4.6 % by weight of the dye of formula (30), 6.0 % by weight of the dye of formula (29), 1.8 % by weight of the dye of formula (23), 7.4 % by weight of the dye of formula (37), 5.1 % by weight of the dye of formula (13), 1.5 % by weight of the dye of formula (34), 1.7 % by weight of the dye of formula (33), and 67.7 % by weight of a commercially available dispersant (K) 2.7 % by weight of the dye of formula (28), 0.5 black 3.2 % by weight of the dye of formula (30), 4.1 % by weight of the dye of formula (29), 3.0 % by weight of the dye of formula (13), 2.72 % by weight of the dye of formula (21), 0.48 % by weight of the dye of formula (22), 1.5 % by weight of the dye of formula (34), 1.6 % by weight of the dye of formula (33), 3.5 % by weight of the dye of formula (36), 3.4 % by weight of the dye of formula (32), 3.7 % by weight of the dye of formula (38), and 70.1 % by weight of a commercially available dispersant -21
Claims (17)
1. A dye mixture, which comprises at least two cles of formula Ri R 3 /RS 0 N N=N-ON\ R6 R2 R 4 wherein R, is hydrogen, halogen, nitro or cyano, R2 is hydrogen, halogen, nitro or cyano, R3 is hydrogen, halogen or CI-C4alkoxy, R4 is hydrog6n, Cl-C4alkylcarbonylamino, R5 is hydrogen; CI-C4alkyl which is unsubstituted or substituted by hydroxy, cyano, Cl-C4alkylcarbonyloxy, Rr, , is CI-C4alkyl which is unsubstituted or su$stituted by hydroxy, cyano, CI-C4alkylcarbonyloxy, Cl-C4alkoxycarbonyl, NC R 7 0 ==='N N = N-P- Hal R 8 OH NO 2 wherein R7 is CI-C4alkyl, R8 is Cl-C4alkyl, and Hal is halogen, NH- S02- NH-(D NO 2 wherein the rings A and B may be further substit+d, R 9-CO-NH--&N = N-- wherein RqiS Cl-C4alkyl and the rings C and D may be further substituted, R 30 N JR10 -N = -0- N \ R29 S Ril wherein R10 is unsubstituted or hydroxy- or cyano-substituted Cl-C4alkyl, R11 is unsubstituted or -0-COR12-substituted Cl-C4alkyl, wherein R12 is Cl-C4alkyl, R29 is nitro, Cl-C4alkoxy or -S02CH3, and R30 is hydrogen or Cl-C4alkyl, R 13 SR15 I / N!Q- N = N-<\,N (6), R 14 N R 16 wherein R13 is Cl-C4alkyl, R14 is Cl-C4alkyl, R15 is Cl-C4alkyl, and R16 is Cl-C4alkyl or -NHCOR17, wherein R17 is Cl-C4alkyl, N-- S /R 18 N = N N \ r -P R 19 R 20 NO 2 wherein R18 is unsubstituted or hydroxy- or cyano-substityted CI-C4alkyl, Rig is unsubstituted or hydroxyor Cl-C4alkoxycarbonyl-substituted Cj-4alkyl, and R20 is hydrogen, C1-C4alkyl or NHCOR17, R17 is CI-C4alkyl, NH 2 0 OH 1 1 R 21 OH 0 NH2 OH 0 NH 2 R21 NH 2 0 OH NH 2 0 NHP R 21 OH 0 OH wherein R21 is halogen, R 22 /R 24 R 25 E R 23 wherein R22 is cyano, nitro or halogen, R23 is halogen, R24 Is unsubstituted or hydroxy-substituted CjC4alkyl, and R25 is unsubstituted or hydroxy-substi:tuted Cl-C4alkyl, and the naphthyl dng E may be further substituted, and N02 0 N" I S I N = N_p_N /R27 (12), 2 R28 R26 wherein R26 is Cl-C4alkyl or the radical NHCOR17, wherein R17 is ClC4alkyl, R27 is C1-C4alkyl or CjC4a[kylcarbonyloxy-Cl-C4alkyl, and R28 is Cl-C4alkyl or Cl-C4alkylcarbonyloxy-Cl-C4a[kyl.
2. A dye mixture according to claim 1, wherein in formula (12) R27 is ClC4alkyl and R28 is C, C4alkyl, and in formula (5) R29 is nitro or the radical -SO2CH3.
3. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of formulae NC CH3 0 =/\N N = N Cl OH N02 O_NH_P_SO2_NH__O (14) and N02 H3C_CO-NH_a N = N_P__O (15).
HO
4. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of formulae -25, CN CH2qH2_0-COCH3 (17), 02N-d-N N-aN\ CH2QH2-0-COCH3 Cl CH OH 2 3 02N-dIN 1-0,N\ CH GH CN 2. 2 Cl CH 2Q H2-0-COCH3 02N-6N N-&N\ CH2CH2CN (21) and C1 G / CH2 H20H 02N-< -N = N-O-N \ CH CH CN 2 2
5. A dye mixture according to either claim 1 or clom 2, which comprises the dyes of formulae .,CCN N = N-&N/ C ' H2CH2CN (16), 02N S C.H2CH2-0-COCH, CN CH CH -0-COCH / 2 2 3 (17), 02N-d-N = N-&N CH2CH2-0-COCH3 CIA 3 S"aN N = N-&N / CIA 2 CIA 2 CN (39) and H 3 CO 2 S CH2 CIA 3 Cl 0 N--6N = 1a / CH2 CIA 3 2 N \ CIA 2 CIA 2 CN
6. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of for- mulae H 3 CIA 2 CIA 2 C S SCH 2 CIA 3 N-1Z - N = N--<\ Y, H 3 CIA 2 CIA 2 C/ NHCOCH 3 NN (19), Cl Cl CIA -CH(CH,,)-OH 2 0 N N = N N (20) and 2 --O-H NHCOCH 3 CIA 3 S"aN CIA CIA CN N = N N / 2 2 (39).
\>- --b \ H 3 C02 S CIA 2 CIA 3
7. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of formulae N's / CH 2 CH 3 N = N__& N\ CH 2 CH 2COOCH 3 (23), N02 NH 2 0 OH Br (24), OH 0 NH 2 OH 0 NH2 (25) and Br NH 2 0 OH NH 2 0 NH2 Br (26).
OH 0 OH
8. A dye mixture according to either claim I or clah 2, which comprises the dyes of formulae N's / CH 2 CH 3 N=N-&N \ CH 2 CH 2 CQOCH 3 (23), NO 2 NHCOCH3 N's / CH 2CH20H N = N-6 N \ CH2CH20H (27), N02 N02 OCH3 CH CH 0 N N / 2 3 2 WON \ CH CH (28), 2 3 Br NHCOCH 3 CN CH CH 2 3 02N-0-N = N- N \ CH2CH3 (32), CN NHCOCH3 N02 OCH3 / CH2CH2-0-COCH3 0 N N = N N \ (33) and CH2CH2-0-COCH3 Br NHCOCH3 N02 0 N N = N- N / CH2CH3 (38).
CH2CH3 CN NHCOCH3
9. A dye mixture according to either claim I or claim 2, which comprises the dyes of formulae - 29 N 's CH 2 CH 3 CH 2 CH 2C I QOCH 3 (23), NO 2 NO 2 OCH3 / CH 20H 3 0 2 N-0-N=N-0-N \ CH 20H 3 (28), Br NHCOCH 3 NO 2 / CH 2-CH(OH)-CH 20H (29), CH 2-PH(OH)-CH 2 OH cl NO 2 H 0 N N N N \ CH 2 QH 2 OH (30), 2 cl CN CH CH 2 3 02 N N N N \ (32), CH 201H 3 CN NHCOCH 3 i NO 2 OCH 3 0 N N = N N / CH 2 CH 2-0-COCH 3 (33) and CH 2 CH 2-0-COCH 3 Br NHCOCH 3 NO 2 CH 2 CH 3 0 N N = N N \ (34).
CH 2 CH 3 Br NHCOCH3
10. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of formulae NHCOCH 3 __S CH 2 CH 2 OH eN N = N N / CH 2 CH 2 OH (27), N02 NO 2 OCH 3 CH CH 2 3 0 N N N N\ (28) and CH 2 CH 3 Br NHCOCH3 NO 2 CH CH / 2 3 0 N'J"'S N = N N \ (35).
)_ CH 2CH3 NHCOCH 3 -31 +
11. A dye mixture according to either claim 1 or Iaim 2, which comprises the dyes of for- mulae CN / CH 2PH2-0-COCH3 (17), 0 N-d- N N 2 CH2qH2_0-COCH, N02 OCH3 CH CH3 0 / 2; 0 N N N N \ (28), CH2qH3 Br NHCOCH3 N02 /CH 2-OH(OH)-CH20H 0 N N N N (29), CH2-OH(OH)-CH20H Cl N02 H 02N N N N \ CH 2G.H20H (30), C1 CN / CH12CH3 02N-N = N- N (32), CH2CH3 CNI NHCOCH3 I I NO 2 OCH.3 / CH 2 CH 2-0-COCH 3 02 N-N = N- N \ CH 2 CH 2-0-COCH 3 (33), Br NHCOCH 3 CH CH 2 3 0 N N = N N \ (34), CH 2 CH 3 Br NHCOCH3 CH 2 CH 2 CN 02 N_0_N=N_&N \ CH 2CH2-0-COCH3 (36) and N02 CH 2 CH 3 CH 2CH3 CN NHCOCH 3
12. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of for- mulae NC CH3 0 =:4\N N = N-P-Cl H 3 CH 2 OH NO 2 - 33 N-- s CH 2 CH 3 N N-0- N \ CH CH COOCH 2 2 3 (23), NO 2 NH 2 0 OH (24), Br OH 0 NH 2 OH 0 NH 2 (25), Br NH 2 0 OH NH 2 0 NH2 (26), Br OH 0 OH NO 2 / CH 2 -CH(OH)-CH 2 OH 0 N N N N 2 \ CH 4H(OH)-CH 2 OH (29), cl i N02 \1 H 0 N N = N N CH 2 CH 20H C1 NO 2 OCH 3 CH CH _O-COCH 2 2 3 02 N-0-N = N- N\ CH 2 CH 2-0-COCH3 (33), Br NFICOCH 3 NO 2 0 N N = N N / CH 2 CH 3 (34) and CH 2CH3 Br NHCOCH 3 Cl / CH 2CH20H 0 N N = N N (37).
CH 2 CH 2 OH Cl
13. A dye mixture according to either claim 1 or claim 2, which comprises the dyes of for- mulae NC CH 3 0 /N N = N_P_CI (13), H 3 CH 2d OH NO 2 cl / CH20H2-0-COCH3 (21), 02N-6-N = N-&N \ CH 20H2CN cl / CH2qH20H (22), 02N N = N-&N CH2qH2CN N02 OCH3 / CH2PH3 0 N N = N- N \ (28), CH20H3 Br NHCOCH3 N02 / CH2-OH(OH)-CH20H 0 N N N N \ CH2-OH(OH)-CH20H (29), 2 cl N02 0 N H \ CH20. H20H (30), cl CN 0 N / CH2CH, 2 N N--p- N (32), CH2CH3 CN NHCOCH3 NO 2 OCH 3 CH CH _O-COCH 2 2 3 02 N_ N=N-O-N N CH 2CH 2-0-COCH 3 Br NHCOCH3 NO 2 CH 2 CH 3 0 N N = N- N \ (34), CH2CH 3 Br NHCOCH3 CH 2 CH 2 CN 02 N-<D- N = N_<7 N N CH2CH2_O-COCH, (36) and NO 2 CH 2 CH 3 0 N IN = N N \ (38).
CH 2CH 3 CN NHCOCH3
14. Use of the dye mixture according to either claim 1 or claim 2 for dyeing or printing cellulose acetate-containing fibre materials.
15. A process for dyeing or printing cellulose acetate-containing fibre materials, wherein a dye mixture according to either claim 1 or claim 2 is applied to, or incorporated into, these materials.
16. A process according to claim 15, wherein the cellulose acetatecontaining fibre material is cell ulose-2'/2acetate or cellulose triacetate.
17. The fibre material dyed by the process according to either claim 14 or claim 15.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH00178/99A CH693506A5 (en) | 1999-02-01 | 1999-02-01 | Dye mixtures and their use for dyeing or printing cellulose-containing fiber materials. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB0001184D0 GB0001184D0 (en) | 2000-03-08 |
| GB2346150A true GB2346150A (en) | 2000-08-02 |
Family
ID=4181050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0001184A Withdrawn GB2346150A (en) | 1999-02-01 | 2000-01-20 | Dye mixtures and their use for dyeing or printing cellulose acetate-containing fibre materials |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH693506A5 (en) |
| DE (1) | DE10004071A1 (en) |
| FR (1) | FR2789083B1 (en) |
| GB (1) | GB2346150A (en) |
| IT (1) | IT1317750B1 (en) |
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| WO2004056925A1 (en) * | 2002-12-20 | 2004-07-08 | Clariant International Ltd | Dye compositions for dyeing or printing of fibre products comprising celluloseacetate |
| EP1457528A1 (en) * | 2003-03-12 | 2004-09-15 | Clariant International Ltd. | Dye mixtures for dyeing fibrous materials containing polyester fibres |
| CN101768376A (en) * | 2009-12-30 | 2010-07-07 | 浙江闰土股份有限公司 | Environment-friendly disperse dye composition |
| US20110027548A1 (en) * | 2008-03-28 | 2011-02-03 | Clariant Finance (Bvi) Limited | Influencing the Near Infrared Reflectance of Dyed Textile Materials |
| CN102245713A (en) * | 2008-12-11 | 2011-11-16 | 德司达染料德国有限责任公司 | Mixtures of disperse dyes |
| CN102634231A (en) * | 2012-03-27 | 2012-08-15 | 江苏之江化工有限公司 | Disperse red mix |
| CN102660145A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof |
| CN102863821A (en) * | 2012-10-17 | 2013-01-09 | 江苏之江化工有限公司 | Dispersing azo dye mixture |
| CN103194093A (en) * | 2013-03-29 | 2013-07-10 | 浙江龙盛集团股份有限公司 | Composition of blue to black disperse dyes |
| US8906116B2 (en) | 2008-12-11 | 2014-12-09 | Dystar Colours Distribution Gmbh | Mixtures of disperse dyes |
| CN104727164A (en) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | Use of disperse dye mixture for alkaline dyeing |
| CN104725896A (en) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | Disperse dyes mixture capable of alkaline dyeing |
| CN104788994A (en) * | 2015-03-16 | 2015-07-22 | 太湖亚太精化有限公司 | Dispersed azo dye mixture, product thereof, and use of product in printing and dyeing of hydrophobic synthetic materials |
| CN108264780A (en) * | 2017-12-31 | 2018-07-10 | 浙江龙盛化工研究有限公司 | A kind of disperse dye composition and dye preparations |
| CN109777150A (en) * | 2019-03-19 | 2019-05-21 | 上海贝通色彩科技有限公司 | A kind of acid dye composition for co-bathing dyeing |
| CN110776439A (en) * | 2019-11-06 | 2020-02-11 | 蓬莱嘉信染料化工股份有限公司 | Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100112304A1 (en) * | 2005-01-04 | 2010-05-06 | Helmut Sieber | Disperse azo dye mixtures |
| CN104710840B (en) * | 2013-12-31 | 2016-10-12 | 江苏吉华化工有限公司 | A kind of dispersion red dye composition |
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| EP0684290A2 (en) * | 1994-05-23 | 1995-11-29 | DyStar Japan Ltd. | Disperse dye compositions |
| WO1996016129A1 (en) * | 1994-11-21 | 1996-05-30 | Basf Aktiengesellschaft | Mixtures of azo dyes for black hues |
| EP0735110A1 (en) * | 1995-03-24 | 1996-10-02 | DyStar Japan Ltd. | Dye mixtures containing a hydroxypyridone azo dye |
| WO1997021773A1 (en) * | 1995-12-08 | 1997-06-19 | Basf Aktiengesellschaft | Dye mixtures for the dyeing or printing of cellulose acetate in shades of red |
| WO1997021772A1 (en) * | 1995-12-08 | 1997-06-19 | Basf Aktiengesellschaft | Dye mixtures for the dyeing or printing of cellulose acetate in shades of yellow |
| EP0802239A1 (en) * | 1996-04-19 | 1997-10-22 | Nippon Kayaku Kabushiki Kaisha | Disperse dye composition and method for dyeing hydrophobic fiber materials with the composition |
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| FR1291988A (en) * | 1960-06-09 | 1962-04-27 | Sandoz Sa | Stable dye preparations and dyeing processes |
| DE3004653A1 (en) * | 1980-02-08 | 1981-08-13 | Basf Ag, 6700 Ludwigshafen | NAVY BLUE DYE BLENDS |
| DE3821338A1 (en) * | 1988-06-24 | 1989-12-28 | Bayer Ag | BLENDS OF BLUE DISPERSION AZO DYES |
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- 1999-02-01 CH CH00178/99A patent/CH693506A5/en not_active IP Right Cessation
-
2000
- 2000-01-20 GB GB0001184A patent/GB2346150A/en not_active Withdrawn
- 2000-01-31 FR FR0001179A patent/FR2789083B1/en not_active Expired - Fee Related
- 2000-01-31 DE DE10004071A patent/DE10004071A1/en not_active Withdrawn
- 2000-02-01 IT IT2000MI000145A patent/IT1317750B1/en active
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Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101050598B1 (en) * | 2002-12-20 | 2011-07-19 | 클라리언트 파이넌스 (비브이아이)리미티드 | Dye composition for dyeing or printing fiber products comprising cellulose acetate |
| WO2004056925A1 (en) * | 2002-12-20 | 2004-07-08 | Clariant International Ltd | Dye compositions for dyeing or printing of fibre products comprising celluloseacetate |
| JP2006513308A (en) * | 2002-12-20 | 2006-04-20 | クラリアント インターナショナル リミティド | Dye composition for dyeing or printing textile products containing cellulose acetate |
| CN100415833C (en) * | 2002-12-20 | 2008-09-03 | 克莱里安特财务(Bvi)有限公司 | Dye compositions for dyeing or printing of fibre products comprising celluloseacetate |
| JP4809058B2 (en) * | 2002-12-20 | 2011-11-02 | クラリアント ファイナンス （ビーブイアイ） リミティド | Dye composition for dyeing or printing textile products containing cellulose acetate |
| EP1457528A1 (en) * | 2003-03-12 | 2004-09-15 | Clariant International Ltd. | Dye mixtures for dyeing fibrous materials containing polyester fibres |
| US20110027548A1 (en) * | 2008-03-28 | 2011-02-03 | Clariant Finance (Bvi) Limited | Influencing the Near Infrared Reflectance of Dyed Textile Materials |
| CN102245713A (en) * | 2008-12-11 | 2011-11-16 | 德司达染料德国有限责任公司 | Mixtures of disperse dyes |
| US8906116B2 (en) | 2008-12-11 | 2014-12-09 | Dystar Colours Distribution Gmbh | Mixtures of disperse dyes |
| CN102245713B (en) * | 2008-12-11 | 2014-03-12 | 德司达染料分销有限公司 | Mixtures of disperse dyes |
| CN101768376A (en) * | 2009-12-30 | 2010-07-07 | 浙江闰土股份有限公司 | Environment-friendly disperse dye composition |
| CN101768376B (en) * | 2009-12-30 | 2013-10-23 | 浙江闰土股份有限公司 | Environment-friendly disperse dye composition |
| CN102634231A (en) * | 2012-03-27 | 2012-08-15 | 江苏之江化工有限公司 | Disperse red mix |
| CN102660145A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof |
| CN102863821A (en) * | 2012-10-17 | 2013-01-09 | 江苏之江化工有限公司 | Dispersing azo dye mixture |
| CN103194093A (en) * | 2013-03-29 | 2013-07-10 | 浙江龙盛集团股份有限公司 | Composition of blue to black disperse dyes |
| CN103194093B (en) * | 2013-03-29 | 2014-10-15 | 浙江龙盛集团股份有限公司 | Composition of blue to black disperse dyes |
| CN104727164A (en) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | Use of disperse dye mixture for alkaline dyeing |
| CN104725896A (en) * | 2013-12-20 | 2015-06-24 | 上海安诺其集团股份有限公司 | Disperse dyes mixture capable of alkaline dyeing |
| CN104725896B (en) * | 2013-12-20 | 2017-02-01 | 上海安诺其集团股份有限公司 | Disperse dyes mixture capable of alkaline dyeing |
| CN104727164B (en) * | 2013-12-20 | 2018-04-27 | 上海安诺其集团股份有限公司 | A kind of application of the admixture of disperse dyes of alkali dyeing |
| CN104788994A (en) * | 2015-03-16 | 2015-07-22 | 太湖亚太精化有限公司 | Dispersed azo dye mixture, product thereof, and use of product in printing and dyeing of hydrophobic synthetic materials |
| CN108264780A (en) * | 2017-12-31 | 2018-07-10 | 浙江龙盛化工研究有限公司 | A kind of disperse dye composition and dye preparations |
| CN109777150A (en) * | 2019-03-19 | 2019-05-21 | 上海贝通色彩科技有限公司 | A kind of acid dye composition for co-bathing dyeing |
| CN110776439A (en) * | 2019-11-06 | 2020-02-11 | 蓬莱嘉信染料化工股份有限公司 | Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof |
| CN110776439B (en) * | 2019-11-06 | 2022-11-01 | 蓬莱嘉信染料化工股份有限公司 | Azo compound, preparation method and application thereof, dye composition, dye, preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2789083B1 (en) | 2006-08-18 |
| FR2789083A1 (en) | 2000-08-04 |
| ITMI20000145A0 (en) | 2000-02-01 |
| DE10004071A1 (en) | 2000-08-03 |
| ITMI20000145A1 (en) | 2001-08-01 |
| IT1317750B1 (en) | 2003-07-15 |
| GB0001184D0 (en) | 2000-03-08 |
| CH693506A5 (en) | 2003-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |