EP0601971A1 - Process for trichromic dyeing or printing - Google Patents
Process for trichromic dyeing or printing 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
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- 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)
Abstract
Description
Die vorliegende Erfindung betrifft ein Verfahren zum Trichromie-Färben oder -Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien mit mindestens einem blaufärbenden, sulfogruppenhaltigen Anthrachinonfarbstoff, mindestens einem rotfärbenden Azofarbstoff und mindestens einem gelb- oder organgefärbenden Azofarbstoff.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.
Die der vorliegenden Erfindung zugrundeliegende Aufgabe war es, ein Verfahren zum Färben oder Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien mit zur Kombination nach dem Trichromie-Prinzip geeigneten Farbstoffen zu finden.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.
Es wurde nun gefunden, dass man diese Aufgabe erfindungsgemäss durch das nachfolgend beschriebene Verfahren lösen kann. Die so erhaltenen Färbungen genügen den gestellten Aufgaben. Insbesondere zeichnen sich die erhaltenen Färbungen durch einen gleichmässigen Farbaufbau bei gleichzeitiger Nuancenkonstanz in verschiedenen Konzentrationen und eine gute Kombinierbarkeit aus.It has now been found that this object can be achieved according to the invention by the method described below. The dyeings obtained in this way fulfill the tasks set. In particular, the dyeings obtained are distinguished by a uniform color structure with constant shade in different concentrations and good combinability.
Gegenstand der vorliegenden Erfindung ist ein Verfahren zum Trichromie-Färben oder -Bedrucken von natürlichen oder synthetischen Polyamidfasermaterialien, welches dadurch gekennzeichnet ist, dass man mindestens einen blaufärbenden Anthrachinonfarbstoff der Formel
worin R₁, R₂, R₃ und R₄ unabhängig voneinander Wasserstoff oder C₁-C₆-Alkyl sind, wobei die Summe der Kohlenstoffatome der Reste R₁, R₂, R₃ und R₄ die Zahl 4, 5 oder 6 ist und die Sulfogruppe im Anthrachinonfarbstoff der Formel (1) in der bezeichneten 6-oder 7-Position gebunden ist,
zusammen mit mindestens einem rotfärbenden Farbstoff der Formel
worin R₅ Phenyl oder Cyclohexyl und R₆ C₁-C₄-Alkyl ist, oder die Reste R₅ und R₆ zusammen mit dem sie verbindenden Stickstoffatom einen Azepinylring bilden, und mindestens einem der gelb- oder orangefärbenden Farbstoffe der Formeln (3), (4) und (5)
worin R₇, R₈ und R₁₀ unabhängig voneinander Wasserstoff, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₂-C₄-Alkanoylamino, Halogen oder Sulfo sind, R₉ Wasserstoff oder C₁-C₄-Alkyl bedeutet und n die Zahl 1, 2, 3 oder 4 ist,
worin B₁, B₂ und E₁ Wasserstoff, C₁-C₄-Alkyl oder C₁-C₄-Alkoxy und X geradkettiges oder verzweigtes C₁-C₄-Alkyl oder geradkettiges oder verzweigtes C₂-C₄-Hydroxyalkyl bedeuten,
worin W₁ gegebenenfalls im Phenylring durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder Halogen substituiertes Phenylsulfonyl, W₂ Wasserstoff, Halogen, C₁-C₄-Alkyl oder C₁-C₄-Alkoxy, W₃ C₁-C₄-Alkyl oder gegebenenfalls durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder Halogen substituiertes Phenyl und W₄ Wasserstoff oder C₁-C₈-Alkyl ist, verwendet.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, C₁-C₁-alkoxy, C₂-C₄-alkanoylamino, halogen or sulfo, R₉ is hydrogen or C₁-C₄-alkyl and n is the number 1, 2, Is 3 or 4,
in which B₁, B₂ and E₁ are hydrogen, C₁-C Alkyl-alkyl or C₁-C₄-alkoxy and X are straight-chain or branched C₁-C₄-alkyl or straight-chain or branched C₂-C₄-hydroxyalkyl,
wherein W₁ in the phenyl ring optionally substituted by C₁-C₄-alkyl, C₁-C₄-alkoxy or halogen, phenylsulfonyl, W₂ hydrogen, halogen, C₁-C₄-alkyl or C₁-C₄-alkoxy, W₃ C₁-C₄-alkyl or optionally by C₁- C₄-alkyl, C₁-C₄-alkoxy or halogen-substituted phenyl and W₄ is hydrogen or C₁-C₈-alkyl is used.
Unter Trichromie ist die additive Farbmischung passend gewählter gelb- bzw. orange-, rot- und blaufärbender Farbstoffe zu verstehen, mit denen jede gewünschte Nuance des sichtbaren Farbspektrums durch geeignete Wahl der Mengenverhältnisse der Farbstoffe eingestellt werden kann.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.
Als C₁-C₆-Alkyl kommen für R₁, R₂, R₃ und R₄ in Formel (1) z.B. Methyl, Aethyl, Propyl, Isopropyl, Butyl, Isobutyl, sek.-Butyl, tert.-Butyl sowie geradkettiges oder verzweigtes Pentyl oder Hexyl in Betracht. Bevorzugt sind hierbei die C₁-C₄-Alkylreste.As 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.
Die Anthrachinonfarbstoffe der Formel (1) werden in der Regel als Isomerengemische eingesetzt, wobei sich die einzelnen Isomeren lediglich hinsichtlich der in 6- oder 7-Position gebundenen Sulfogruppe unterscheiden; es können aber auch die einzelnen Isomeren als Einzelfarbstoffe eingesetzt werden.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.
Als C₁-C₄-Alkyl kommen für R₆, R₇, R₈, R₉, R₁₀, B₁, B₂, E₁, X, W₂ und W₃ Methyl, Aethyl, Propyl, Isopropyl, Butyl, Isobutyl, sek.-Butyl oder tert.-Butyl in Betracht.As C₁-C₄ alkyl for 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.
Als C₁-C₄-Alkoxy kommen für R₇, R₈, R₁₀, B₁, B₂, E₁ und W₂ beispielsweise Methoxy, Aethoxy, Propoxy, Isopropoxy, Butoxy, sek.-Butoxy, Isobutoxy oder tert.-Butoxy in Betracht.As C₁-C₄-alkoxy for R₇, R₈, R₁₀, B₁, B₂, E₁ and W₂, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tert-butoxy.
Als C₂-C₄-Alkanoylamino kommen für R₇, R₈ und R₁₀ beispielsweise Acetylamino, Propionylamino oder Butyrylamino, insbesondere Acetylamino, in Betracht.As C₂-C₄-alkanoylamino for R₇, R₈ and R₁₀, for example acetylamino, propionylamino or butyrylamino, especially acetylamino.
Als Halogen kommen für R₇, R₈, R₁₀ und W₂ beispielsweise Fluor oder Brom und insbesondere Chlor in Betracht.As halogen for R₇, R₈, R₁₀ and W₂, for example fluorine or bromine and especially chlorine come into consideration.
Als C₂-C₄-Hydroxyalkylrest kommt für X ein geradkettiger oder verzweigter Hydroxyalkylrest in Betracht, wie beispielsweise der β-Hydroxyäthyl-, β-Hydroxypropyl-, β-Hydroxybutyl- oder der α-Aethyl-β-hydroxyäthylrest.As a C₂-C₄-hydroxyalkyl radical for X is a straight-chain or branched hydroxyalkyl radical, such as the β-hydroxyethyl, β-hydroxypropyl, β-hydroxybutyl or the α-ethyl-β-hydroxyethyl radical.
Bedeutet W₄ einen C₁-C₈-Alkykest, so handelt es sich z.B. um Methyl, Aethyl, Propyl, Isopropyl, Butyl, Isobutyl, sek.-Butyl, tert.-Butyl, sowie um geradkettiges oder verzweigtes Pentyl, Hexyl, Heptyl oder Octyl.If 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 als Phenylsulfonyl sowie W₃ als Phenyl können im Phenylring unsubstituiert oder durch C₁-C₄-Alkyl, wie Methyl, Aethyl, Propyl, Isopropyl, Butyl, Isobutyl, sek.-Butyl oder tert.-Butyl, C₁-C₄-Alkoxy, wie Methoxy, Aethoxy, Propoxy, Isopropoxy, Butoxy, sek.-Butoxy, Isobutoxy oder tert.-Butoxy, oder durch Halogen, wie z.B. Fluor, Brom oder insbesondere Chlor, substituiert sein.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.
Als Anthrachinonfarbstoffe der Formel (1) verwendet man bevorzugt solche, worin R₂ und R₃ unabhängig voneinander Methyl oder Aethyl sind und R₄ Wasserstoff oder Methyl ist.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.
Der Rest R₁ im Anthrachinonfarbstoff der Formel (1) ist vorzugsweise Isopropyl oder sek.-Butyl, insbesondere Isopropyl.The radical R 1 in the anthraquinone dye of the formula (1) is preferably isopropyl or sec-butyl, in particular isopropyl.
Für das erfindungsgemässe Verfahren besonders bevorzugt sind Anthrachinonfarbstoffe der Formel (1), worin R₁ Isopropyl ist, R₂ und R₃ unabhängig voneinander Methyl oder Aethyl sind und R₄ Wasserstoff oder Methyl bedeutet.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.
Die Summe der Kohlenstoffatome der Reste R₁, R₂, R₃ und R₄ im Anthrachinonfarbstoff der Formel (1) ist vorzugsweise die Zahl 5.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.
Ganz besonders bevorzugt sind Anthrachinonfarbstoffe der Formel (1), worin R₁ Isopropyl ist, R₂ und R₃ Methyl sind und R₄ Wasserstoff bedeutet.Anthraquinone dyes of the formula (1) in which R₁ is isopropyl, R₂ and R₃ are methyl and R₄ is hydrogen are very particularly preferred.
Als rotfärbenden Farbstoff der Formel (2) verwendet man bevorzugt einen Farbstoff der Formel
oder
insbesondere einen Farbstoff der Formel (6) oder (7) und vorzugsweise einen Farbstoff der Formel (6).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).
Vorzugsweise handelt es sich bei den gelb- oder orangefärbenden Farbstoffen der Formel (3) um sulfogruppenhaltige Farbstoffe.The yellow or orange coloring dyes of the formula (3) are preferably dyes containing sulfo groups.
Als gelb- oder orangefärbende Farbstoffe der Formel (3) verwendet man bevorzugt solche, worin R₇ Wasserstoff ist, R₈ und R₉ C₁-C₄-Alkyl sind, R₁₀ Sulfo bedeutet und n die Zahl 1 ist, insbesondere den Farbstoff der Formel
Als gelb- oder orangefärbende Farbstoffe der Formel (4) verwendet man bevorzugt solche, worin B₁ und B₂ unabhängig voneinander C₁-C₄-Alkyl oder C₁-C₄-Alkoxy sind, E₁ Wasserstoff und X C₁-C₄-Alkyl ist, insbesondere den Farbstoff der Formel
Als gelb- oder orangefärbende Farbstoffe der Formel (5) verwendet man bevorzugt solche, worin W₁ Phenylsulfonyl, W₂ Wasserstoff, Halogen oder C₁-C₄-Alkyl, W₃ gegebenenfalls durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder Halogen substituiertes Phenyl und W₄ Wasserstoff ist, insbesondere den Farbstoff der Formel
Besonders bevorzugt verwendet man als gelb- oder orangefärbenden Farbstoff einen Farbstoff der Formel (3), worin R₇ Wasserstoff ist, R₈ und R₉ C₁-C₄-Alkyl sind, R₁₀ Sulfo bedeutet und n die Zahl 1 ist, oder einen Farbstoff der Formel (4), worin B₁ und B₂ unabhängig voneinander C₁-C₄-Alkyl oder C₁-C₄-Alkoxy sind, E₁ Wasserstoff und X C₁-C₄-Alkyl ist, oder einen Farbstoff der Formel (5), worin W₁ Phenylsulfonyl, W₂ Wasserstoff, Halogen oder C₁-C₄-Alkyl, W₃ gegebenenfalls durch C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder Halogen substituiertes Phenyl und W₄ Wasserstoff ist.It is particularly preferred to use 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.
Ganz besonders bevorzugt verwendet man als gelb- oder orangefärbenden Farbstoff einen Farbstoff der Formel (9), (10) oder (11).It is very particularly preferred to use a dye of the formula (9), (10) or (11) as the yellow or orange dye.
Von besonderem Interesse als gelb- oder orangefärbende Farbstoffe sind die Farbstoffe der Formeln (3) und (5), für welche die oben angegebenen Bedeutungen und Bevorzugungen gelten, insbesondere die Farbstoffe der Formeln (9) und (11).Of particular interest as yellow or orange dyes are the dyes of the formulas (3) and (5), for which the meanings and preferences given above apply, in particular the dyes of the formulas (9) and (11).
In einer ganz besonders bevorzugten Ausführungsform des erfindungsgemässen Verfahrens verwendet man einen Anthrachinonfarbstoff der Formel (1) zusammen mit einem rotfärbenden Farbstoff der Formel (6) oder (7) und einem gelb- oder orangefärbenden Farbstoff der Formel (9) oder (11), wobei für den Anthrachinonfarbstoff der Formel (1) die oben angegebenen Bedeutungen und Bevorzugungen gelten.In a very particularly preferred embodiment of the process according to the invention, 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).
Einen weiteren Gegenstand der vorliegenden Erfindung stellen Farbstoffmischungen dar, welche mindestens einen Anthrachinonfarbstoff der Formel (1) zusammen mit mindestens einem rotfärbenden Farbstoff der Formel (2) und mindestens einem gelb- oder orangefärbenden Farbstoff der Formeln (3), (4) und (5) enthalten. Hierbei gelten für die Farbstoffe der Formeln (1), (2), (3), (4) und (5) die oben angegebenen Bedeutungen und Bevorzugungen.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).
Die in dem erfindungsgemässen Verfahren zum Trichromie-Färben oder -Bedrucken verwendeten Farbstoffe der Formeln (1), (2), (3), (4) und (5) sind bekannt oder können in Analogie zu bekannten Farbstoffen hergestellt werden. So können z.B. die Anthrachinonfarbstoffe analog den Angaben der GB-A-1,438,354 erhalten werden.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. For example, the anthraquinone dyes are obtained analogously to the information in GB-A-1,438,354.
Die in dem erfindungsgemässen Verfahren zum Trichromie-Färben oder -Bedrucken verwendeten Farbstoffe liegen entweder in der Form ihrer freien Sulfonsäure oder vorzugsweise als deren Salze vor.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.
Als Salze kommen beispielsweise die Alkali-, Erdalkali- oder Ammoniumsalze oder die Salze eines organischen Amins in Betracht. Als Beispiele seien die Natrium-, Lithium-, Kalium- oder Ammoniumsalze oder das Salz des Mono-, Di- oder Triäthanolamins genannt.Examples of suitable salts are the alkali, alkaline earth or ammonium salts or the salts of an organic amine. Examples include the sodium, lithium, potassium or ammonium salts or the salt of mono-, di- or triethanolamine.
Die in dem erfindungsgemässen Verfahren verwendeten Farbstoffe können weitere Zusätze wie z.B. Kochsalz oder Dextrin enthalten.The dyes used in the process according to the invention can contain further additives such as e.g. Table salt or dextrin included.
Das erfindungsgemässe Verfahren zum Trichromie-Färben oder -Bedrucken kann auf die üblichen Färbe- bzw. Druckverfahren angewendet werden. Die Färbeflotten oder Druckpasten können ausser Wasser und den Farbstoffen weitere Zusätze, beispielsweise Netzmittel, Antischaummittel, Egalisiermittel oder die Eigenschaft des Textilmaterials beeinflussende Mittel wie z.B. Weichmachungsmittel, Zusätze zum Flammfestausrüsten oder schmutz-, wasser- und öl-abweisende Mittel sowie wasserenthärtende Mittel und natürliche oder synthetische Verdicker, wie z.B. Alginate und Celluloseäther, enthalten.The process according to the invention for trichromatic dyeing or printing can be applied to the customary dyeing or printing processes. In addition to water and the dyes, 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.
Das erfindungsgemässe Verfahren zum Trichromie-Färben oder -Bedrucken ist auch zum Färben aus Kurzflotten, wie z.B. bei Kontinuefärbeverfahren oder diskontinuierlichen und kontinuierlichen Schaumfärbeverfahren, geeignet.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.
Die in dem erfindungsgemässen Verfahren verwendeten Farbstoffe zeichnen sich beim Trichromie-Färben oder -Bedrucken durch gleichmässigen Farbaufbau, gutes Aufziehverhalten, guten Nuancenkonstanz auch in verschiedenen Konzentrationen, gute Echtheiten sowie insbesondere durch sehr gute Kombinierbarkeit aus.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.
Das erfindungsgemässe Verfahren zum Trichromie-Färben oder -Bedrucken eignet sich zum Färben oder Bedrucken sowohl von natürlichen Polyamidmaterialien wie z.B. Wolle, wie insbesondere von synthetischen Polyamidmaterialien, wie z.B. Polyamid 6 oder Polyamid 6.6, und ist geeignet zum Färben oder Bedrucken von Woll- und synthetischem Polyamid-Mischgeweben oder -Garnen.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.
Das genannte Textilmaterial kann dabei in den verschiedensten Verarbeitungsformen vorliegen, wie z.B. als Faser, Garn, Gewebe oder Gewirke und insbesondere in Form von Teppichen.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.
Es werden egale Färbungen mit guten Allgemeinechtheiten, insbesondere guter Reib-, Nass-, Nassreib- und Lichtechtheit erhalten.Level dyeings with good general fastness properties, in particular good rub, wet, wet rub and light fastness are obtained.
In den folgenden Beispielen stehen Teile für Gewichtsteile. Die Temperaturen sind Celsiusgrade. Die Beziehung zwischen Gewichtsteilen und Volumenteilen ist dieselbe wie diejenige zwischen Gramm und Kubikzentimeter.In the following examples, 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.
Man färbt 10 Teile Polyamid-6.6 Fasermaterial (Helancatrikot) in 200 Teilen einer wässrigen Flotte, die 2 g/l Natriumacetat enthält und mit Essigsäure auf pH 5 gestellt wird. Als Farbstoffe werden 0,15% des blaufärbenden Farbstoffs der in Form der freien Säure der Formel
entspricht, 0,42% des rotfärbenden Farbstoffs der in Form der freien Säure der Formel
entspricht und 0,62% des gelbfärbenden Farbstoffs der in Form der freien Säure der Formel
entspricht, verwendet, wobei sich die Mengenangaben auf das Fasergewicht beziehen.10 parts of polyamide-6.6 fiber material (Helancatrikot) are dyed in 200 parts of an aqueous liquor which contains 2 g / l of sodium acetate and is adjusted to pH 5 with acetic acid. 0.15% of the blue-coloring dye is in the form of the free acid of the formula
corresponds to 0.42% of the red-coloring dye in the form of the free acid of the formula
corresponds to and 0.62% of the yellowing dye in the form of the free acid of the formula
corresponds, used, the quantities refer to the fiber weight.
Die Färbedauer bei einer Temperatur von 98°C beträgt 30 bis 90 Minuten. Das gefärbte Polyamidfasermaterial wird anschliessend herausgenommen und wie üblich gespült und getrocknet Man erhält ein in einem braunen Farbton völlig egal gefärbtes Gewebestück, das keinerlei materialbedingte Streifigkeit aufweist.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.
Wenn man wie in Beispiel 1 angegeben vorgeht, jedoch anstelle von 0,15% des Farbstoffs der Formel (101) eine äquimolare Menge des in Form der freien Säure angegebenen Farbstoffs der Formel
oder
verwendet, so werden ebenfalls in einem braunen Farbton egal gefärbte Gewebestücke erhalten.If the procedure is as described in Example 1, but instead of 0.15% of the dye of the formula (101), an equimolar amount of the dye of the formula given in the form of the free acid
or
used, so pieces of tissue dyed no matter the color obtained are also obtained in a brown shade.
Wenn man wie in Beispiel 1 angegeben vorgeht, jedoch anstelle von 0,15% des Farbstoffs der Formel (101) 0,18% des Farbstoffs der Formel (101) und anstelle von 0,62% des Farbstoffs der Formel (103) 0,17% des in Form der freien Säure der Formel
entsprechenden Farbstoffs verwendet, so wird ebenfalls ein in einem braunen Farbton egal gefärbtes Gewebestück erhalten.If the procedure is as described in Example 1, but instead of 0.15% of the dye of the formula (101) 0.18% of the dye of the formula (101) and instead of 0.62% of the dye of the formula (103) 0, 17% of that in the form of the free acid of the formula
Appropriate dye is used, so a piece of tissue dyed in a brown shade is also obtained.
Die in den obigen Beispielen aufgeführten Anthrachinonfarbstoffe der Formeln (101), (104), (105) und (106) werden jeweils als Isomerenmischungen eingesetzt, wobei sich die einzelnen Isomeren lediglich hinsichtlich der Stellung der Sulfogruppe in 6- oder 7-Position unterscheiden; das Mischungsverhältnis der beiden Isomeren beträgt ca. 1:1. Anstelle der Isomerenmischungen können jedoch auch die einzelnen Isomeren als Einzelfarbstoffe eingesetzt werden.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. Instead of the isomer mixtures, however, the individual isomers can also be used as individual dyes.
Claims (12)
zusammen mit mindestens einem rotfärbenden Farbstoff der Formel
und mindestens einem der gelb- oder orangefärbenden Farbstoffe der Formeln (3), (4) und (5)
together with at least one red-coloring dye of the formula
and at least one of the yellow or orange coloring dyes of the formulas (3), (4) and (5)
zusammen mit mindestens einem rotfarbenden Farbstoff der Formel
und mindestens einem der gelb- oder orangefärbenden Farbstoffe der Formeln (3), (4) und (5)
together with at least one red-colored dye of the formula
and at least one of the yellow or orange coloring dyes of the formulas (3), (4) and (5)
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|---|---|---|---|
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| CH3719/92 | 1992-12-03 |
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|---|---|
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| EP0601971B1 EP0601971B1 (en) | 1997-03-12 |
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| EP (1) | EP0601971B1 (en) |
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| CN104447429B (en) * | 2014-12-25 | 2016-10-05 | 北京泛博化学股份有限公司 | Environment protection acidic can pulling color Yellow dye compound, application and synthetic method |
| CN105753750B (en) * | 2016-02-16 | 2017-10-24 | 北京泛博清洁技术研究院有限公司 | Fur acidity can dawn Yellow dye compound and its synthesis and application process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2197940A1 (en) * | 1972-08-29 | 1974-03-29 | Ciba Geigy Ag | |
| EP0052578A2 (en) * | 1980-10-16 | 1982-05-26 | Ciba-Geigy Ag | Monoazo compounds |
| EP0127579A1 (en) * | 1983-05-25 | 1984-12-05 | Ciba-Geigy Ag | Trichromatic dyeing or printing process |
| US4840643A (en) * | 1988-03-16 | 1989-06-20 | Crompton & Knowles Corporation | Trichromatic combination of dyes for nylon |
| EP0425434A2 (en) * | 1989-10-23 | 1991-05-02 | Ciba-Geigy Ag | Dyestuff mixtures and their use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE20099T1 (en) * | 1981-12-29 | 1986-06-15 | Ciba Geigy Ag | PROCESS FOR TRICHROMIC DYING OR PRINTING. |
| EP0092512B1 (en) * | 1982-04-08 | 1986-04-30 | 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 (en) * | 1989-03-10 | 1994-03-17 | Ciba Geigy | Dye mixture and its use. |
| GB2236542B (en) * | 1989-10-06 | 1992-04-15 | Sandoz Ltd | Dye mixtures and their use in trichromatic dyeing processes |
-
1993
- 1993-11-24 US US08/157,852 patent/US5399183A/en not_active Expired - Fee Related
- 1993-11-24 ES ES93810813T patent/ES2099409T3/en not_active Expired - Lifetime
- 1993-11-24 DE DE59305745T patent/DE59305745D1/en not_active Expired - Fee Related
- 1993-11-24 EP EP93810813A patent/EP0601971B1/en not_active Expired - Lifetime
- 1993-11-29 JP JP5297939A patent/JPH06212576A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2197940A1 (en) * | 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 (en) * | 1980-10-16 | 1982-05-26 | Ciba-Geigy Ag | Monoazo compounds |
| EP0127579A1 (en) * | 1983-05-25 | 1984-12-05 | Ciba-Geigy Ag | Trichromatic dyeing or printing process |
| US4840643A (en) * | 1988-03-16 | 1989-06-20 | Crompton & Knowles Corporation | Trichromatic combination of dyes for nylon |
| EP0425434A2 (en) * | 1989-10-23 | 1991-05-02 | Ciba-Geigy Ag | Dyestuff mixtures and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06212576A (en) | 1994-08-02 |
| DE59305745D1 (en) | 1997-04-17 |
| US5399183A (en) | 1995-03-21 |
| EP0601971B1 (en) | 1997-03-12 |
| ES2099409T3 (en) | 1997-05-16 |
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