EP0601971A1 - Procédé de teinture ou d'impression par trichromie - Google Patents
Procédé de teinture ou d'impression par trichromie Download PDFInfo
- Publication number
- EP0601971A1 EP0601971A1 EP93810813A EP93810813A EP0601971A1 EP 0601971 A1 EP0601971 A1 EP 0601971A1 EP 93810813 A EP93810813 A EP 93810813A EP 93810813 A EP93810813 A EP 93810813A EP 0601971 A1 EP0601971 A1 EP 0601971A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- dye
- formula
- hydrogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000004043 dyeing Methods 0.000 title claims abstract description 27
- 239000000975 dye Substances 0.000 claims abstract description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 239000001000 anthraquinone dye Substances 0.000 claims abstract description 24
- 239000004952 Polyamide Substances 0.000 claims abstract description 13
- 229920002647 polyamide Polymers 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 sulpho group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 37
- 238000004040 coloring Methods 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 239000001048 orange dye Substances 0.000 claims description 4
- 239000001043 yellow dye Substances 0.000 claims description 4
- 125000002785 azepinyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 7
- 239000000835 fiber Substances 0.000 abstract description 3
- 239000002253 acid Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OGMABSIGOGLLIM-DQSJHHFOSA-N CCN(Cc1cccc(S(O)(=O)=O)c1)c(cc1C)ccc1/N=N\c(cc1)cc(C#N)c1C#N Chemical compound CCN(Cc1cccc(S(O)(=O)=O)c1)c(cc1C)ccc1/N=N\c(cc1)cc(C#N)c1C#N OGMABSIGOGLLIM-DQSJHHFOSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/16—Wool using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8209—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing amide groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- the present invention relates to a process for trichromatic dyeing or printing of natural and synthetic polyamide fiber materials with at least one blue-coloring, sulfo-containing anthraquinone dye, at least one red-dyeing azo dye and at least one yellow-colored or orange-dyeing azo dye.
- the object underlying the present invention was to find a method for dyeing or printing natural and synthetic polyamide fiber materials with dyes suitable for combination according to the trichromatic principle.
- the dyeings obtained in this way fulfill the tasks set.
- the dyeings obtained are distinguished by a uniform color structure with constant shade in different concentrations and good combinability.
- the present invention relates to a process for trichromatic dyeing or printing of natural or synthetic polyamide fiber materials, which is characterized in that at least one blue-coloring anthraquinone dye of the formula wherein R1, R2, R3 and R4 are independently hydrogen or C1-C6 alkyl, the sum of the carbon atoms of the radicals R1, R2, R3 and R4 being 4, 5 or 6 and the sulfo group in the anthraquinone dye of the formula (1) being bonded in the 6 or 7 position, together with at least one red-coloring dye of the formula wherein R5 is phenyl or cyclohexyl and R6 is C1-C4-alkyl, or the radicals R5 and R6 together with the nitrogen atom connecting them form an azepinyl ring, and at least one of the yellow or orange-colored dyes of the formulas (3), (4) and ( 5) wherein R7, R8 and R10 are independently hydrogen, C1-C4-alkyl, C
- Trichromatic is to be understood as the additive color mixture of suitably selected yellow or orange, red and blue coloring dyes, with which any desired shade of the visible color spectrum can be adjusted by a suitable choice of the proportions of the dyes.
- C1-C6 alkyl for R1, R2, R3 and R4 in formula (1) e.g. Methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl and straight-chain or branched pentyl or hexyl are also suitable.
- the C1-C4 alkyl radicals are preferred.
- the anthraquinone dyes of the formula (1) are generally used as mixtures of isomers, the individual isomers differing only in the sulfo group bonded in the 6- or 7-position; however, the individual isomers can also be used as individual dyes.
- R6, R7, R8, R9, R10, B1, B2, E1, X, W2 and W3 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl into consideration.
- R7, R8, R10, B1, B2, E1 and W2 for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy.
- C2-C4-alkanoylamino for example acetylamino, propionylamino or butyrylamino, especially acetylamino.
- R7, R8, R10 and W2 for example fluorine or bromine and especially chlorine come into consideration.
- C2-C4-hydroxyalkyl radical for X is a straight-chain or branched hydroxyalkyl radical, such as the ⁇ -hydroxyethyl, ⁇ -hydroxypropyl, ⁇ -hydroxybutyl or the ⁇ -ethyl- ⁇ -hydroxyethyl radical.
- W4 is a C1-C8 alkyl residue, it is e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and straight-chain or branched pentyl, hexyl, heptyl or octyl.
- W1 as phenylsulfonyl and W3 as phenyl can be unsubstituted in the phenyl ring or by C1-C4-alkyl, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, C1-C4-alkoxy, such as methoxy , Ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy, or by halogen, such as Fluorine, bromine or especially chlorine, may be substituted.
- C1-C4-alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl
- C1-C4-alkoxy such as methoxy , Ethoxy, propoxy, isopropoxy, butoxy,
- the anthraquinone dyes of the formula (1) used are preferably those in which R2 and R3 are independently methyl or ethyl and R4 is hydrogen or methyl.
- the radical R 1 in the anthraquinone dye of the formula (1) is preferably isopropyl or sec-butyl, in particular isopropyl.
- Anthraquinone dyes of the formula (1) in which R1 is isopropyl, R2 and R3 are independently methyl or ethyl and R4 is hydrogen or methyl are particularly preferred for the process according to the invention.
- the sum of the carbon atoms of the radicals R1, R2, R3 and R4 in the anthraquinone dye of the formula (1) is preferably the number 5.
- Anthraquinone dyes of the formula (1) in which R1 is isopropyl, R2 and R3 are methyl and R4 is hydrogen are very particularly preferred.
- a dye of the formula is preferably used as the red-coloring dye of the formula (2) or in particular a dye of the formula (6) or (7) and preferably a dye of the formula (6).
- the yellow or orange coloring dyes of the formula (3) are preferably dyes containing sulfo groups.
- yellow or orange coloring dyes of the formula (4) are preferably used in which B1 and B2 are independently C1-C Alkyl-alkyl or C1-C4-alkoxy, E1 is hydrogen and X is C1-C4-alkyl, especially the dye of formula
- yellow or orange coloring dyes of the formula (5) are preferably used in which W1 phenylsulfonyl, W2 hydrogen, halogen or C1-C4-alkyl, W3 optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or halogen-substituted phenyl and W4 is hydrogen, especially the dye of the formula
- a dye of the formula (3) in which R7 is hydrogen, R8 and R9 are C1-C4-alkyl, R10 is sulfo and n is the number 1, or a dye of the formula (4 ), in which B1 and B2 are independently C1-C4-alkyl or C1-C4-alkoxy, E1 is hydrogen and X is C1-C4-alkyl, or a dye of the formula (5), in which W1 is phenylsulfonyl, W2 is hydrogen, halogen or C1-C4-alkyl, W3 is phenyl optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or halogen and W und is hydrogen.
- an anthraquinone dye of the formula (1) is used together with a red-coloring dye of the formula (6) or (7) and a yellow or orange-coloring dye of the formula (9) or (11), where the meanings and preferences given above apply to the anthraquinone dye of the formula (1).
- the present invention further provides dye mixtures which comprise at least one anthraquinone dye of the formula (1) together with at least one red-coloring dye of the formula (2) and at least one yellow or orange-coloring dye of the formulas (3), (4) and (5 ) contain.
- the meanings and preferences given above apply to the dyes of the formulas (1), (2), (3), (4) and (5).
- the dyes of the formulas (1), (2), (3), (4) and (5) used in the process according to the invention for trichromatic dyeing or printing are known or can be prepared analogously to known dyes.
- the anthraquinone dyes are obtained analogously to the information in GB-A-1,438,354.
- the dyes used in the process according to the invention for trichromatic dyeing or printing are either in the form of their free sulfonic acid or preferably as their salts.
- suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine.
- suitable salts include the sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
- the dyes used in the process according to the invention can contain further additives such as e.g. Table salt or dextrin included.
- the process according to the invention for trichromatic dyeing or printing can be applied to the customary dyeing or printing processes.
- the dyeing liquors or printing pastes can contain other additives, for example wetting agents, anti-foaming agents, leveling agents or agents which influence the property of the textile material, such as e.g. Plasticizers, flame retardants or dirt, water and oil repellents, water softeners and natural or synthetic thickeners such as Alginates and cellulose ethers.
- the process according to the invention for trichromatic dyeing or printing is also for dyeing from short liquors, such as e.g. suitable for continuous dyeing processes or discontinuous and continuous foam coloring processes.
- the dyes used in the process according to the invention are distinguished in trichromatic dyeing or printing by uniform color build-up, good absorption behavior, good constancy of shades even in different concentrations, good fastness properties and in particular by very good combinability.
- the process according to the invention for trichromatic dyeing or printing is suitable for dyeing or printing both natural polyamide materials such as wool, such as in particular of synthetic polyamide materials, such as polyamide 6 or polyamide 6.6, and is suitable for dyeing or printing wool and synthetic polyamide blended fabrics or yarns.
- the textile material mentioned can be in a wide variety of processing forms, such as as fiber, yarn, woven or knitted fabric and in particular in the form of carpets.
- parts represent parts by weight.
- the temperatures are degrees Celsius.
- the relationship between parts by weight and parts by volume is the same as that between grams and cubic centimeters.
- the dyeing time at a temperature of 98 ° C is 30 to 90 minutes.
- the dyed polyamide fiber material is then removed and rinsed and dried as usual.
- a piece of fabric dyed in a brown shade that does not show any streakiness due to the material is obtained.
- the anthraquinone dyes of the formulas (101), (104), (105) and (106) listed in the above examples are each used as isomer mixtures, the individual isomers differing only in the position of the sulfo group in the 6- or 7-position; the mixing ratio of the two isomers is approximately 1: 1.
- the individual isomers can also be used as individual dyes.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH3719/92 | 1992-12-03 | ||
CH371992 | 1992-12-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0601971A1 true EP0601971A1 (fr) | 1994-06-15 |
EP0601971B1 EP0601971B1 (fr) | 1997-03-12 |
Family
ID=4262037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93810813A Expired - Lifetime EP0601971B1 (fr) | 1992-12-03 | 1993-11-24 | Procédé de teinture ou d'impression par trichromie |
Country Status (5)
Country | Link |
---|---|
US (1) | US5399183A (fr) |
EP (1) | EP0601971B1 (fr) |
JP (1) | JPH06212576A (fr) |
DE (1) | DE59305745D1 (fr) |
ES (1) | ES2099409T3 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6443998B1 (en) | 2000-04-14 | 2002-09-03 | Shaw Industries, Inc. | Trichromatic fiber dyeing processes and compositions thereof |
DE102011079114A1 (de) * | 2011-07-14 | 2013-01-17 | Tesa Se | Klebeband mit textilem Träger für die Kabelbandagierung |
CN104447429B (zh) * | 2014-12-25 | 2016-10-05 | 北京泛博化学股份有限公司 | 环保酸性可拔色黄色染料化合物、应用及合成方法 |
CN105753750B (zh) * | 2016-02-16 | 2017-10-24 | 北京泛博清洁技术研究院有限公司 | 裘皮用酸性可拔白黄色染料化合物及其合成与应用方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2197940A1 (fr) * | 1972-08-29 | 1974-03-29 | Ciba Geigy Ag | |
EP0052578A2 (fr) * | 1980-10-16 | 1982-05-26 | Ciba-Geigy Ag | Composés monoazoiques |
EP0127579A1 (fr) * | 1983-05-25 | 1984-12-05 | Ciba-Geigy Ag | Procédé de teinture ou d'impression en trois couleurs |
US4840643A (en) * | 1988-03-16 | 1989-06-20 | Crompton & Knowles Corporation | Trichromatic combination of dyes for nylon |
EP0425434A2 (fr) * | 1989-10-23 | 1991-05-02 | Ciba-Geigy Ag | Mélanges de colorants et leur utilisation |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3271290D1 (en) * | 1981-12-29 | 1986-07-03 | Ciba Geigy Ag | Process for trichromatic dyeing or printing |
DE3363254D1 (en) * | 1982-04-08 | 1986-06-05 | Ciba Geigy Ag | Process for trichromatic dyeing or printing |
US4579561A (en) * | 1984-01-31 | 1986-04-01 | Crompton And Knowles Corporation | Process for trichromatic dyeing polyamide fibers |
US4652269A (en) * | 1984-11-08 | 1987-03-24 | Ciba-Geigy Corporation | Process for the continuous trichromatic dyeing of synthetic polyamide materials: including a blue anthraquinone reactive dye |
DE59004453D1 (de) * | 1989-03-10 | 1994-03-17 | Ciba Geigy | Farbstoffmischung und deren Verwendung. |
GB2236542B (en) * | 1989-10-06 | 1992-04-15 | Sandoz Ltd | Dye mixtures and their use in trichromatic dyeing processes |
-
1993
- 1993-11-24 ES ES93810813T patent/ES2099409T3/es not_active Expired - Lifetime
- 1993-11-24 EP EP93810813A patent/EP0601971B1/fr not_active Expired - Lifetime
- 1993-11-24 DE DE59305745T patent/DE59305745D1/de not_active Expired - Fee Related
- 1993-11-24 US US08/157,852 patent/US5399183A/en not_active Expired - Fee Related
- 1993-11-29 JP JP5297939A patent/JPH06212576A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2197940A1 (fr) * | 1972-08-29 | 1974-03-29 | Ciba Geigy Ag | |
GB1438354A (en) * | 1972-08-29 | 1976-06-03 | Ciba Geigy Ag | Anthraquinone dyestuffs their manufacture and their use |
EP0052578A2 (fr) * | 1980-10-16 | 1982-05-26 | Ciba-Geigy Ag | Composés monoazoiques |
EP0127579A1 (fr) * | 1983-05-25 | 1984-12-05 | Ciba-Geigy Ag | Procédé de teinture ou d'impression en trois couleurs |
US4840643A (en) * | 1988-03-16 | 1989-06-20 | Crompton & Knowles Corporation | Trichromatic combination of dyes for nylon |
EP0425434A2 (fr) * | 1989-10-23 | 1991-05-02 | Ciba-Geigy Ag | Mélanges de colorants et leur utilisation |
Also Published As
Publication number | Publication date |
---|---|
DE59305745D1 (de) | 1997-04-17 |
US5399183A (en) | 1995-03-21 |
ES2099409T3 (es) | 1997-05-16 |
JPH06212576A (ja) | 1994-08-02 |
EP0601971B1 (fr) | 1997-03-12 |
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