CH617956A5 - Process for preparing disazo dyes - Google Patents
Process for preparing disazo dyes Download PDFInfo
- Publication number
- CH617956A5 CH617956A5 CH1430275A CH1430275A CH617956A5 CH 617956 A5 CH617956 A5 CH 617956A5 CH 1430275 A CH1430275 A CH 1430275A CH 1430275 A CH1430275 A CH 1430275A CH 617956 A5 CH617956 A5 CH 617956A5
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- Prior art keywords
- hydrogen
- alkyl
- methyl
- formula
- dyes
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- 239000000975 dye Substances 0.000 title claims description 37
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 aminoazo Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 8
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 244000154870 Viola adunca Species 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- CFCXQQUQLZIZPI-UHFFFAOYSA-N 2-amino-3,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(N)C(S(O)(=O)=O)=C1 CFCXQQUQLZIZPI-UHFFFAOYSA-N 0.000 description 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 description 1
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 1
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000005406 washing 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/04—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal
- D06P1/06—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes not containing metal containing acid groups
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Gegenstand der Erfindung ist die Herstellung von Disazo- Qf^ The invention relates to the production of Disazo-Qf ^
farbstoffen, welche in Form der freien Säure der Formel 55 / 3 dyes, which are in the form of the free acid of the formula 55/3
<wH®2 <wH®2
> >
60 60
(IV) (IV)
(oder dementsprechende co-N-Methansulfonsäuren) (or corresponding co-N-methanesulfonic acids)
b5 kuppelt und gegebenenfalls den Sulfonylmethylrest abspaltet. Geeignete Amine der Formel III sind beispielsweise: 3-Aminobenzolsulfonsäure, 4-Aminobenzolsulfonsäure, 2-Amino-5 -methylbenzolsulfonsäure, 2-Amino-3,5-dimethyl- b5 couples and optionally cleaves the sulfonylmethyl radical. Suitable amines of the formula III are, for example: 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 2-amino-5-methylbenzenesulfonic acid, 2-amino-3,5-dimethyl-
3 3rd
617 956 617 956
benzolsulfonsäure, 2-Amino-5-chlorbenzolsulfonsäure, 2-Amino-5-nitrobenzolsulfonsäure, 4-Amino-2,5-dichlorbenzol-sulfonsäure, 2-Nitroanilin, 3-Nitroanilin, 4-Nitroanilin, 2-Chloranilin, 5-Amino-2-methylbenzolsulfonsäure, 5-Amino-2-chlorbenzolsulfonsäure, 3-Amino-4-methoxybenzolsulfon- 5 säure, 4-Chloranilin. benzenesulfonic acid, 2-amino-5-chlorobenzenesulfonic acid, 2-amino-5-nitrobenzenesulfonic acid, 4-amino-2,5-dichlorobenzenesulfonic acid, 2-nitroaniline, 3-nitroaniline, 4-nitroaniline, 2-chloroaniline, 5-amino- 2-methylbenzenesulfonic acid, 5-amino-2-chlorobenzenesulfonic acid, 3-amino-4-methoxybenzenesulfonic acid, 4-chloroaniline.
Als Kupplungskomponenten geeignete Amine der Formel IV sind beispielsweise: Amines of the formula IV which are suitable as coupling components are, for example:
2-Methoxy-5-methylanilin, 2,5-Dimethoxyanilin, 2,5-Di-äthoxyanilin und 2-Methoxyanilin, gegebenenfalls in Form ihrer m cü-N-Methansulfonsäure. 2-methoxy-5-methylaniline, 2,5-dimethoxyaniline, 2,5-di-ethoxyaniline and 2-methoxyaniline, optionally in the form of their m cü-N-methanesulfonic acid.
Die Farbstoffe eignen sich besonders zum Färben von Polyamiden wie Poly-e-Caprolactam oder Kondensationsprodukten aus Adipinsäure und Hexamethylendiamin. The dyes are particularly suitable for dyeing polyamides such as poly-e-caprolactam or condensation products from adipic acid and hexamethylene diamine.
Die Farbstoffe sind weiterhin zum Färben von Leder ge- i s eignet. The dyes are also suitable for dyeing leather.
Die Färbungen zeichnen sich durch gute Wasser-, Wasch-und Schweissechtheit sowie gute Lichtechtheit aus. Die Farbstoffe können in Form der freien Säure oder deren Salzen, insbesondere der Alkalisalze (vorzugsweise Natrium- 20 The dyeings are distinguished by good fastness to water, washing and sweat, and good fastness to light. The dyes can be in the form of the free acid or its salts, in particular the alkali salts (preferably sodium 20
oder Lithiumsalze) oder der Ammoniumsalze, eingesetzt werden. or lithium salts) or the ammonium salts.
Beispiel 1 example 1
20,1 g 2-Amino-3,5-dimethylbenzolsuIfonsäure werden in ^ 300 cm3 Wasser von 70° C gelöst und mit 6,9 g Natriumnitrit versetzt. Diese Lösung lässt man zu einer Mischung von 28 cm3 Salzsäure mit 19° Bé, 100 cm3 Wasser und 170 g Eis laufen. Man rührt 1 Stunde bei 20° C nach. Der Nitritüberschuss wird in üblicher Weise mit Amidosulfonsäure zerstört. In die so erhal- -w tene Diazoniumsalzlösung lässt man eine Lösung von 15 g 2-Methoxy-5-methylanilin in einem Gemisch von 100 cm3 Wasser und 15,4 cm3 Salzsäure 19° Bé eintropfen, wobei die Temperatur durch Eiszugabe auf 20 bis 25° C gehalten wird. Dann wird langsam eine wässrige Lösung von 43 g kristallisiertem " 20.1 g of 2-amino-3,5-dimethylbenzenesulfonic acid are dissolved in ^ 300 cm3 of water at 70 ° C. and mixed with 6.9 g of sodium nitrite. This solution is run to a mixture of 28 cm3 hydrochloric acid with 19 ° Bé, 100 cm3 water and 170 g ice. The mixture is stirred at 20 ° C for 1 hour. The excess nitrite is destroyed in the usual way with sulfamic acid. A solution of 15 g of 2-methoxy-5-methylaniline in a mixture of 100 cm3 of water and 15.4 cm3 of hydrochloric acid 19 ° Bé is added dropwise to the diazonium salt solution thus obtained, the temperature being brought to 20 to 25 by adding ice ° C is maintained. Then an aqueous solution of 43 g of crystallized "
Natriumacetat zugegeben, bis der pH-Wert von 4,5 erreicht ist. Das Reaktionsgemisch wird 16 Stunden nachgerührt. Danach wird mit 28 cm3 Salzsäure sauer gestellt (pH 1,5) und der Aminoazofarbstoff abfiltriert. Sodium acetate added until pH 4.5 is reached. The reaction mixture is stirred for 16 hours. It is then acidified with 28 cm3 of hydrochloric acid (pH 1.5) and the aminoazo dye is filtered off.
Der feuchte Filterkuchen wird in einem Gemisch von 40 270 cm3 Wasser (40° C) und 10 cm3 Natronlauge von 40° Bé gelöst, mit 2,5 g A-Kohle versetzt und geklärt. Die geklärte Lösung wird mit 6,9 g Natriumnitrit versetzt und zu einem Gemisch von 300 cm3 Wasser, 35 cm3 Salzsäure 19° Bé und 170 g Eis gegeben. Man rührt 3 Stunden (Temperatur 5° C) 45 nach und zerstört dann den Nitritüberschuss mit Amidosulfonsäure. The moist filter cake is dissolved in a mixture of 40 270 cm3 water (40 ° C) and 10 cm3 sodium hydroxide solution at 40 ° Bé, mixed with 2.5 g activated carbon and clarified. The clarified solution is mixed with 6.9 g of sodium nitrite and added to a mixture of 300 cm3 of water, 35 cm3 of hydrochloric acid 19 ° Bé and 170 g of ice. The mixture is stirred for 3 hours (temperature 5 ° C.) 45 and then the excess nitrite is destroyed with amidosulfonic acid.
In diese Diazoniumsalzlösung lässt man eine wässrige Lösung von 2-Amino-8-hydroxynaphthalin-6-sulfonsäure (pH 6,5) einlaufen. Dann wird das Kupplungsgemisch durch Zugabe 50 von ca. 150 cm3 Natriumacetatlösung 20% auf pH 4,5 gestellt. Man rührt 16 Stunden bei 5 bis 10° C nach. An aqueous solution of 2-amino-8-hydroxynaphthalene-6-sulfonic acid (pH 6.5) is run into this diazonium salt solution. The coupling mixture is then adjusted to pH 4.5 by adding 50% of approximately 150 cm 3 of sodium acetate solution 20%. The mixture is stirred at 5 to 10 ° C for 16 hours.
Zur Isolierung des Farbstoffs wird auf 80° C erhitzt, mit 30 cm3 Natronlauge 40° Bé und 200 g Kochsalz versetzt. Der so erhaltene Farbstoff färbt Polyamidfasern violett. ss To isolate the dye, it is heated to 80 ° C, mixed with 30 cm3 of sodium hydroxide solution at 40 ° Bé and 200 g of table salt. The dye obtained in this way dyes polyamide fibers violet. ss
Beispiel 2 Example 2
17,3 g 4-Aminobenzolsulfonsäure werden in üblicher Weise mit 6,9 g Natriumnitrit diazotiert und mit 14,1 g 2-Methoxy-5- ;,0 methylanilin sauer gekuppelt. Das Kupplungsgemisch wird nach 16-stündigem Rühren auf 50° C erhitzt, mit Salzsäure von 19° Bé angesauert und der auskristallisierte Aminoazofarbstoff abfiltriert. 17.3 g of 4-aminobenzenesulfonic acid are diazotized in a conventional manner with 6.9 g of sodium nitrite and acid-coupled with 14.1 g of 2-methoxy-5-; 0, methylaniline. After stirring for 16 hours, the coupling mixture is heated to 50 ° C., acidified with hydrochloric acid of 19 ° Be and the crystallized aminoazo dye is filtered off.
Der feuchte Filterkuchen des Aminoazofarbstoffs wird in ,5 einem Gemisch von 250 cm3 Wasser und 11 cm3 Natronlauge bei 80° C gelöst und mit 7,2 g Natriumnitrit in üblicher Weise diazotiert. The moist filter cake of the aminoazo dye is dissolved in a mixture of 250 cm3 of water and 11 cm3 of sodium hydroxide solution at 80 ° C. and diazotized with 7.2 g of sodium nitrite in the usual way.
25,1 g 2-Amino-8-hydroxynaphthalin-6-sulfonsäure werden in 300 cm3 Wasser und 25 cm3 Sodalösung (20%) gelöst. Diese Lösung lässt man zu einem Gemisch von 100 cm3 Wasser, 100 g Eis und 15 cm3 Salzsäure von 19° Bé laufen, wobei die 2-Amino-8-hydroxynaphthalin-6-sulfonsäure fein verteilt ausfällt. 25.1 g of 2-amino-8-hydroxynaphthalene-6-sulfonic acid are dissolved in 300 cm3 of water and 25 cm3 of soda solution (20%). This solution is allowed to run to a mixture of 100 cm3 of water, 100 g of ice and 15 cm3 of hydrochloric acid at 19 ° Bé, the 2-amino-8-hydroxynaphthalene-6-sulfonic acid precipitating in finely divided form.
In diese Mischung lässt man die Diazoniumsalzlösung des Aminomonoazofarbstoffs innerhalb einer Stunde zulaufen. Dann wird bei 5 bis 10° C mit ca. 150 cm3 Natriumacetatlösung 20% auf pH 4,5 gestellt. Nach 16-stündigem Rühren wird durch langsame Zugabe von ca. 40 g Natriumbicarbonat auf pH 5,5 bis 6 gestellt und weitere 2 Stunden gerührt. The diazonium salt solution of the aminomonoazo dye is run into this mixture within one hour. Then at 5 to 10 ° C with about 150 cm3 sodium acetate 20% to pH 4.5. After stirring for 16 hours, the pH is adjusted to 5.5 to 6 by slowly adding about 40 g of sodium bicarbonate, and the mixture is stirred for a further 2 hours.
Zur Isolierung des Farbstoffs wird auf 80° C erhitzt, mit 30 cm3 Natronlauge 40° Bé und 200 g Salz versetzt. Der filtrierte und getrocknete Farbstoff färbt Polyamidfasern rotstichig blau. To isolate the dye, the mixture is heated to 80 ° C., 30 cm 3 of sodium hydroxide solution 40 ° Bé and 200 g of salt are added. The filtered and dried dye dyes polyamide fibers reddish blue.
Beispiele 3 bis 29 Examples 3 to 29
Verfährt man ähnlich wie in den beiden vorstehenden Beispielen, verwendet jedoch die in nachstehender Tabelle aufgeführten Aminoazofarbstoffe als Diazokomponenten, so erhält man nach dem sauren Kuppeln auf 7-Säure ebenfalls wertvolle Disazofarbstoffe, die synthetische Polyamidfasern in den angegebenen Farbtönen färben. If the procedure is similar to that of the two examples above, but using the aminoazo dyes listed in the table below as diazo components, then valuable disazo dyes are obtained after acid coupling to 7-acid, which dye synthetic polyamide fibers in the specified shades.
Tabelle table
Nr. Aminoazofarbstoff No aminoazo dye
Farbton des Disazofarbstoffs Hue of the disazo dye
OCH, OCH,
j j
NH2 rotstichig blau NH2 reddish blue
H03s H03s
CHt CHt
0ch3 0ch3
4 H03s-{3>-N=N^NH2 blau 4 H03s- {3> -N = N ^ NH2 blue
OCH, OCH,
5 blauviolett 5 blue violet
CH^ CH ^
CHi CHi
Cl Cl
OCH, OCH,
HO^S-^ ^-N=N-^ y-NH£ grünstichig blau HO ^ S- ^ ^ -N = N- ^ y-NH £ greenish blue
Cl CH, Cl CH,
617 956 617 956
4 4th
Nr. Aminoazofarbstoff No aminoazo dye
Farbton des Nr. Aminoazofarbstoff Hue of the no aminoazo dye
Disazofarbstoffs Disazo dye
Farbton des Disazofarbstoffs cl och3 Hue of disazo dye cl och3
7 HO^S-^ ^-N=N-^ N^-NH£ grünstichig blau cl och3 7 HO ^ S- ^ ^ -N = N- ^ N ^ -NH £ greenish blue cl och3
14 14
°2N^r^N=N"^/'1 ° 2N ^ r ^ N = N "^ / '1
ch, ch,
grünstichig blau greenish blue
Cl Cl
15 15
och3 och3
■nh, ■ nh,
rotstichig dunkelblau ch, reddish dark blue ch,
9 C1-//\V-N=N-V ^VnHo rotstichig blau ch3 9 C1 - // \ V-N = N-V ^ VnHo reddish blue ch3
10 10th
y-NH^ blauviolett y-NH ^ blue violet
11 H03S^N=N^yNH2 bIau 11 H03S ^ N = N ^ yNH2 blue
Cl Cl
12 12
dunkelblau dark blue
16 ch3-<^) n=n ^ ^—NH^rotstichig blau ch- 16 ch3 - <^) n = n ^ ^ —NH ^ reddish blue ch-
ho3S ho3S
17 C1_/~\_N=N_^ \-NH0 rotstichigblau ch- 17 C1_ / ~ \ _N = N_ ^ \ -NH0 reddish blue ch-
18 18th
ch, och, 3 3 ch, och, 3 3
55 55
ch, ch,
13 13
^N=N^p-NH2 ^ N = N ^ p-NH2
ch, ch,
rotstichig dunkelblau reddish dark blue
19 19th
65 65
blau blue
5 5
617 956 617 956
Nr. Aminoazofarbstoff No aminoazo dye
20 20th
Farbton des Nr. Aminoazofarbstoff Disazofarbstoffs Hue of the No Aminoazo Dye Disazo Dye
'26 '26
grünstichig blau greenish blue
Farbton des Disazofarbstoffs Hue of the disazo dye
Cl 0C2H5 Cl 0C2H5
(7^N=N-(^~^NH2 g^nstichig blau dc^H5 (7 ^ N = N - (^ ~ ^ NH2 g ^ nstichig blue dc ^ H5
21 21st
22 22
Cl oc2h5 Cl oc2h5
och, oh
y-NH y-NH
och, oh
2 grünstichig blau oc2H5 2 greenish blue oc2H5
C1 _^7^N=NH^~VNH?grünstichiSblau C1 _ ^ 7 ^ N = NH ^ ~ VNH? Greenish blue
0C2H^ 0C2H ^
9C2H5 9C2H5
23 23
h^S^n=N-^nh2 h ^ S ^ n = N- ^ nh2
0c2h5 0c2h5
24 24th
oc2h5 oc2h5
29 29
blau 35 blue 35
grünstichig blau greenish blue
25 ho,s 25 ho, p
3 W/ Cl blaugrün oc2h5 3 W / Cl teal green oc2h5
50 50
55 55
Cl ^N=N-^^Jy-NH2 OCH, Cl ^ N = N - ^^ Jy-NH2 OCH,
grünstichig blau greenish blue
Färbebeispiele a) 0,1 g des Farbstoffs aus Beispiel 1 werden in 100 ml Wasser heiss gelöst. Man setzt der Lösung 5 ml 10%ige Ammo-niumacetatlösung zu und verdünnt mit Wasser auf ein Volumen von 500 ml. Dyeing examples a) 0.1 g of the dye from Example 1 are dissolved in 100 ml of hot water. 5 ml of 10% ammonium acetate solution are added to the solution and the mixture is diluted with water to a volume of 500 ml.
Zu dieser Lösung gibt man 10 g Polyamidgewebe, bringt das Färbebad innerhalb von 20 Minuten zum Kochen, setzt 4 ml 10%ige Essigsäure zu und hält eine Stunde auf Kochtemperatur. Danach wird gespült und bei 70-80° C getrocknet. 10 g of polyamide fabric are added to this solution, the dye bath is brought to a boil within 20 minutes, 4 ml of 10% acetic acid are added and the mixture is kept at the boiling temperature for one hour. It is then rinsed and dried at 70-80 ° C.
b) 100 g frisch gegerbtes und neutralisiertes Chromnarbenleder werden in einer Flotte von 250 ml Wasser von 65° C und 1 g des nach Beispiel 19 dargestellten Farbstoffes während 30 Minuten im Färbefass gewalkt, im gleichen Bade mit 2 g eines anionischen Fettlickers auf sulfonierter Traubasis während weiteren 30 Minuten behandelt, und das Leder in der üblichen Art getrocknet und zugerichtet. Man erhält ein sehr egal gefärbtes Leder in einer blauen Nuance. b) 100 g of freshly tanned and neutralized chrome grain leather are drummed in a liquor of 250 ml of water at 65 ° C and 1 g of the dye shown in Example 19 for 30 minutes in the dyeing kettle, in the same bath with 2 g of an anionic fat liquor based on sulfonated grape treated for a further 30 minutes, and the leather dried and finished in the usual way. You get a leather of a very different color in a blue shade.
C C.
Claims (5)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742453209 DE2453209C2 (en) | 1974-11-09 | 1974-11-09 | Disazo dyes, process for their preparation and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617956A5 true CH617956A5 (en) | 1980-06-30 |
Family
ID=5930424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1430275A CH617956A5 (en) | 1974-11-09 | 1975-11-05 | Process for preparing disazo dyes |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR7507347A (en) |
| CH (1) | CH617956A5 (en) |
| DE (1) | DE2453209C2 (en) |
| ES (1) | ES442417A1 (en) |
| FR (1) | FR2290474A1 (en) |
| GB (1) | GB1477084A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323498A (en) * | 1976-07-28 | 1982-04-06 | Sandoz Ltd. | Carbocyclic disazo compounds containing a 2-amino-8-hydroxy-5- or 6-sulfo-naphthalene-2 coupling component radical |
| DE2732356A1 (en) * | 1976-07-28 | 1978-02-02 | Sandoz Ag | ANIONIC DISAZO COMPOUNDS, METHOD OF MANUFACTURING AND USE |
| US5663309A (en) * | 1994-12-12 | 1997-09-02 | Ciba-Geigy Corporation | Diazo dyes having a phenylene group as the middle component and a naphthalene group as the terminal diazo component |
| MX2008015256A (en) | 2006-06-25 | 2008-12-15 | Clariant Finance Bvi Ltd | Acid dyes. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2058816C3 (en) * | 1970-11-30 | 1975-02-06 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Water-soluble disazo dye, process for its preparation and its use for dyeing leather and fur |
-
1974
- 1974-11-09 DE DE19742453209 patent/DE2453209C2/en not_active Expired
-
1975
- 1975-10-13 GB GB4182375A patent/GB1477084A/en not_active Expired
- 1975-11-05 CH CH1430275A patent/CH617956A5/en not_active IP Right Cessation
- 1975-11-07 ES ES442417A patent/ES442417A1/en not_active Expired
- 1975-11-07 FR FR7534200A patent/FR2290474A1/en active Granted
- 1975-11-07 BR BR7507347A patent/BR7507347A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7507347A (en) | 1976-08-10 |
| FR2290474A1 (en) | 1976-06-04 |
| FR2290474B3 (en) | 1979-06-29 |
| ES442417A1 (en) | 1977-04-01 |
| GB1477084A (en) | 1977-06-22 |
| DE2453209C2 (en) | 1983-02-03 |
| DE2453209A1 (en) | 1976-05-13 |
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