CN1346850A - 水溶性单偶氮染料、其制备和用途 - Google Patents
水溶性单偶氮染料、其制备和用途 Download PDFInfo
- Publication number
- CN1346850A CN1346850A CN01140729A CN01140729A CN1346850A CN 1346850 A CN1346850 A CN 1346850A CN 01140729 A CN01140729 A CN 01140729A CN 01140729 A CN01140729 A CN 01140729A CN 1346850 A CN1346850 A CN 1346850A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- hydrogen
- formula
- dyeing
- preparation
- 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
- 239000000975 dye Substances 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 5
- 239000000463 material Substances 0.000 claims abstract description 23
- 238000004043 dyeing Methods 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 238000007639 printing Methods 0.000 claims abstract description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 5
- -1 2-hydroxyethoxy Chemical group 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052728 basic metal Inorganic materials 0.000 claims description 3
- 150000003818 basic metals Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000006012 2-chloroethoxy group Chemical group 0.000 abstract description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 239000011737 fluorine Substances 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005518 carboxamido group Chemical group 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 239000012752 auxiliary agent Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009950 felting Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-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
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 229940044197 ammonium sulfate Drugs 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/16—Naphthol-sulfonic acids
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
一种式(1)的染料、其制备方法及其用于染色和印染含甲酰胺基材料的用途:其中M是氢、铵、碱金属或等当量的碱土金属;X是磺酰基或－COCH2O－;R1、R2和R3相互独立地为氢,卤素,例如氟、氯或溴,未取代或被氯或羟基取代的C1－C4烷氧基,例如2－氯乙氧基或2－羟基乙氧基,和磺基在相对于NH基的3或4位。
Description
本发明涉及新颖的水溶性单偶氮染料、其制备方法和用于染色和印染含甲酰胺基的材料，尤其是含甲酰胺基的纤维材料的用途。
专利DE-B 728 485，DE-B 731677，DE-B 731 770和GB 483442中描述了用于天然和合成的含甲酰胺基纤维材料，例如毛、丝或聚酰胺纤维如尼龙6或尼龙66的单偶氮染料。但是，这些染料具有一定的性能缺陷，例如耐湿牢度和耐汗渍牢度以及耐光牢度都不能令人满意。
对于本发明，已经发现式(I)的染料意想不到地具有更好的耐湿牢度和耐汗渍牢度以及耐光牢度。
因此本发明提供式(1)的染料：
其中X 是磺酰基或-COCH2O-；M 是氢、铵、碱金属或等当量的碱土金属；R1、R2和R3相互独立地为氢，卤素，例如氟、氯或溴，未取代或被氯或羟基取代的C1-C4烷基，例如2-氯乙基或2-羟基乙基，未取代或被氯或羟基取代的C1-C4烷氧基，例如2-氯乙氧基或2-羟基乙氧基，和磺基在相对于NH基的3或4位。
本发明染料的优选实施方案是式(2)的染料：
其中M 是氢、铵、碱金属或等当量的碱土金属；X 是磺酰基或-COCH2O-和R1和R2相互独立地为氢、氯或C1-C4烷基，和磺基在相对于NH基的3或4位。
本发明染料特别的优选实施方案是X为-COCH2O-和R1和R2相互独立地为氢或氯的式(2)染料；也可以是X为磺酰基和R1和R2为氢或甲基的式(2)染料，在每一种情况下磺基都在相对于NH基的3或4位。
本发明的染料可以通过常规方法制备，例如，按此目的所需要的比例，以本领域技术人员熟知的方式通过常规的重氮化和偶合反应制备。
例如，制备式(5)的偶合组份可以从式(3)的化合物开始，使其与式(4)的酰基氯缩合：其中M、X、R1、R2和R3同上述定义。
通过将式(6)的胺重氮化，并将该产物偶合到式(5)的偶合组分上，可得到式(1)的染料。
可以借助通常用于水溶性化合物的常规方法把本发明的式(1)化合物从含水合成溶液或悬浮液中沉淀并分离出来，例如用电解质如氯化钠或氯化钾使其从反应介质中沉淀出来，或者将反应溶液或悬浮液蒸发浓缩，例如通过喷雾干燥。
本发明的染料可以以固体或液体制剂的形式存在。它们通常包括水溶性染料中惯用的电解质盐，例如氯化钠、氯化钾、和硫酸钠，它们还可以包括惯用于酸性染料的离子标准化剂，例如萘磺酸-甲醛缩合物，或者惯用于酸性染料的非离子标准化剂，例如糊精，和惯用于商品染料的助剂。
通常本发明的染料为粉末或颗粒形式，以染料粉末或制品计，染料含量为10-90％重量，优选为30-80％重量。
本发明的染料具有有价值的性能。它们可以通过常规方法用于含甲酰胺基材料的染色或印染，所述材料的例子是合成和天然聚酰胺和聚氨酯，尤其是纤维形式的，例如羊毛和其它动物的毛发、丝、尼龙6，6和尼龙6、尼龙11，片状材料例如皮革或膜如聚酰胺的膜，或者块状物例如聚酰胺和聚氨酯。
优选使用纤维形式的材料，尤其是纺织纤维，例如机织织物或卷或绕成一定型式的纱。本发明的染料在该材料上产生红色染色，该染色具有高亮度和均染性，也具有良好的全面坚牢度，例如耐湿牢度和耐汗渍牢度，以及非常好的耐光牢度。
因此，本发明也提供了本发明的染料用于染色或印染这些材料的用途，以及用本发明的染料作为着色剂以常规方法对此类材料染色或印染的方法。
本发明的染料可以用水溶性染料领域熟知的施用技术施用并固着到上述基质上，尤其是上述纤维材料上。
例如，可以以大浴比用浸染法由它们得到具有非常好的坚牢度的染色。染色优选在水浴中进行，温度为70-110℃下，如果需要温度可以高达130℃，并加压，如果需要可以存在常规染色助剂。一种可能的方法是把材料引入温浴中，缓慢将该浴加热到所需要的染色温度，并在该温度下完成染色过程。
另外，对进行不毡合性或低毡合性整理(例如参看H.Rath，纺织化学教科书(Lehrbuch der Textilchemie)，Springer-Verlag，第3版(1972)，第295-299页，尤其是用Hercosett方法进行的整理(第298页)；J.Soc.Dyers and Colourists 1972，93-99，和1975，33-44)过的羊毛的染色具有非常好的坚牢性。
这里对羊毛的染色可以在酸性介质中以常规方法进行。例如，为了得到所需要的pH，可以将醋酸和/或硫酸铵或者醋酸和醋酸铵或醋酸钠加入到染浴中。为了得到具有可接受的均染性的染色，可以适当地加入常规的均染助剂，例如基于烷芳基胺或磺化的烷基胺与环氧乙烷的反应产物的均染助剂。例如，本发明的染料优选最初在酸性染浴中经浸染过程。
这里所述的方法也可以用于对由其它天然聚酰胺组成的纤维材料和由合成的聚酰胺组成的纤维材料进行染色。
通常，将要染色的材料引入温度约40℃的染浴中，在其中搅拌一段时间，然后把染浴调节到所需要的弱酸性-优选，弱醋酸性-pH值，实际染色在70-110℃下进行。优选在沸腾温度下，或者在封闭的染色设备中，在高达106℃下进行染色。
由于本发明染料的水溶性非常好，因此它们也可以有效地用于常规的连续染色方法。而且，本发明的染料很容易与其它染料结合。
当本发明的染料用于印染含甲酰胺基材料例如羊毛、丝、尼龙6，6和尼龙6时，由该染料按常规方法得到的印花浆可以借助已知技术施用并固着，例如用102℃的饱和蒸汽，该印花浆尤其还包括：增溶剂，例如基于脂肪醇乙氧基化物的增溶剂，和增稠剂，例如基于半乳甘露聚糖衍生物的增稠剂。
下面通过实施例说明本发明。除非另有说明，百分数均以重量计。
实施例1重氮化：
把200.6g 2-邻-甲苯氧基苯胺(99.2％)溶解在900ml水和280ml30％的盐酸中。加入1000g冰之后有部分胺的盐酸盐沉淀。在0-5℃下，于30分钟内，滴加231ml亚硝酸钠溶液(300g/l)，并将该混合物搅拌1小时。加入少量氨基磺酸溶液破坏过量的亚硝酸盐。偶合：
把991g 1-(N-2，4-二氯苯氧基乙酰基)氨基-8-羟基萘-4，6-二磺酸(55％)在5500ml水中搅拌。用约5ml氢氧化钠溶液(400g/l)将pH值调节至7。加入27.5g碳酸氢钠之后，在30分钟内泵送重氮溶液，在此过程中通过滴加190ml氢氧化钠溶液(400g/l)使pH保持在8.5-9。加入696g氯化钠之后，把该混合物在室温下搅拌3小时。过滤分离染料，在50℃下真空干燥后，得到932g干染料(A)，它可以将羊毛染成亮红色。
如果用常规的偶合组分(5)代替实施例1中所述的偶合组分，得到下表中所列的染料，它们把羊毛和尼龙染成亮红色：
| 实施例 | X | R1 | R2 | R3 | -SO3H的位置 |
| 2 | -COCH2O- | 2-Cl | 4-Cl | H | 3 |
| 3 | -COCH2O- | 2-Cl | H | H | 4 |
| 4 | -COCH2O- | 2-Cl | H | H | 3 |
| 5 | -COCH2O- | H | H | H | 4 |
| 6 | -COCH2O- | H | H | H | 3 |
| 7 | -COCH2O- | H | 4-CH3 | H | 4 |
| 8 | -COCH2O- | H | 4-CH3 | H | 3 |
| 9 | -COCH2O- | H | 4-OCH3 | H | 4 |
| 10 | -COCH2O- | H | 4-OCH3 | H | 3 |
| 11 | -SO2- | H | H | H | 4 |
| 12 | -SO2- | H | H | H | 3 |
| 13 | -SO2- | H | 4-CH3 | H | 4 |
| 14 | -SO2- | H | 4-CH3 | H | 3 |
Claims (6)
1、一种式(1)的染料：
其中
M 是氢、铵、碱金属或等当量的碱土金属；
X 是磺酰基或-COCH2O-；
R1、R2和R3相互独立地为氢，卤素，未取代或被氯或羟基取代的C1-C4烷基，未取代或被氯或羟基取代的C1-C4烷氧基，和磺基在相对于NH基的3或4位上。
2、权利要求1的染料，其中X为-COCH2O-，和R1和R2为氢或氯，和R3为氢。
3、权利要求1的染料，其中X为磺酰基，和R1为氢，和R2为氢或甲基，和R3为氢。
4、权利要求1-3中的一项或多项的染料的制备方法，从式(3)的化合物开始，并使其与式(4)的酰基氯缩合，得到式(5)的偶合组分，
其中M、X、R1、R2和R3的定义同上，
将式(6)的胺重氮化，并将该产物偶合到式(5)的偶合组分上。
5、权利要求1-3至少一项的染料用于染色和印染含甲酰胺基的材料的用途。
6、一种染色和印染含甲酰胺基的材料的方法，该方法包括，在pH为3-7和温度为70-110℃下，把权利要求1-3至少一项的染料以溶解形式施用到该材料上。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10047234.6 | 2000-09-23 | ||
| DE10047234A DE10047234A1 (de) | 2000-09-23 | 2000-09-23 | Wasserlösliche Monoazofarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1346850A true CN1346850A (zh) | 2002-05-01 |
| CN100400602C CN100400602C (zh) | 2008-07-09 |
Family
ID=7657397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011407298A Expired - Lifetime CN100400602C (zh) | 2000-09-23 | 2001-09-21 | 水溶性单偶氮染料、其制备和用途 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6365721B1 (zh) |
| EP (1) | EP1191069B1 (zh) |
| JP (1) | JP4750981B2 (zh) |
| KR (1) | KR100754632B1 (zh) |
| CN (1) | CN100400602C (zh) |
| AT (1) | ATE390464T1 (zh) |
| CA (1) | CA2354680C (zh) |
| DE (2) | DE10047234A1 (zh) |
| ES (1) | ES2303823T3 (zh) |
| HK (1) | HK1046292B (zh) |
| PT (1) | PT1191069E (zh) |
| TW (1) | TW576856B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107001811B (zh) | 2014-11-25 | 2019-09-27 | 富士胶片株式会社 | 染色用着色组合物、印花用着色组合物、印花方法、喷墨印花用油墨及被染色的布帛 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR677327A (fr) * | 1928-10-15 | 1930-03-06 | Geigy Ag J R | Procédé de préparation de colorants monoazoïques |
| US1824686A (en) * | 1929-07-04 | 1931-09-22 | Geigy Ag J R | Manufacture of monoazo-dyestuffs |
| DE614405C (de) * | 1933-12-24 | 1935-06-07 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Monoazofarbstoffen |
| US2785158A (en) * | 1952-07-31 | 1957-03-12 | Ursula B Piepenbrink | Monoazo dyestuffs |
| EP0041239A3 (de) * | 1980-06-04 | 1982-05-12 | Ciba-Geigy Ag | Stabile konzentrierte flüssige Zubereitungen von metallfreien Farbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
-
2000
- 2000-09-23 DE DE10047234A patent/DE10047234A1/de not_active Withdrawn
-
2001
- 2001-08-03 CA CA002354680A patent/CA2354680C/en not_active Expired - Lifetime
- 2001-09-15 ES ES01122159T patent/ES2303823T3/es not_active Expired - Lifetime
- 2001-09-15 DE DE50113777T patent/DE50113777D1/de not_active Expired - Lifetime
- 2001-09-15 PT PT01122159T patent/PT1191069E/pt unknown
- 2001-09-15 AT AT01122159T patent/ATE390464T1/de active
- 2001-09-15 EP EP01122159A patent/EP1191069B1/de not_active Expired - Lifetime
- 2001-09-17 JP JP2001281024A patent/JP4750981B2/ja not_active Expired - Fee Related
- 2001-09-18 US US09/956,173 patent/US6365721B1/en not_active Expired - Lifetime
- 2001-09-20 TW TW090123228A patent/TW576856B/zh not_active IP Right Cessation
- 2001-09-21 CN CNB011407298A patent/CN100400602C/zh not_active Expired - Lifetime
- 2001-09-22 KR KR1020010058849A patent/KR100754632B1/ko active IP Right Grant
-
2002
- 2002-10-30 HK HK02107848.7A patent/HK1046292B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4750981B2 (ja) | 2011-08-17 |
| ES2303823T3 (es) | 2008-09-01 |
| HK1046292A1 (en) | 2003-01-03 |
| ATE390464T1 (de) | 2008-04-15 |
| DE10047234A1 (de) | 2002-04-11 |
| CA2354680A1 (en) | 2002-03-23 |
| CN100400602C (zh) | 2008-07-09 |
| KR100754632B1 (ko) | 2007-09-05 |
| TW576856B (en) | 2004-02-21 |
| PT1191069E (pt) | 2008-06-09 |
| DE50113777D1 (de) | 2008-05-08 |
| HK1046292B (zh) | 2009-07-03 |
| KR20020023674A (ko) | 2002-03-29 |
| EP1191069A2 (de) | 2002-03-27 |
| JP2002146221A (ja) | 2002-05-22 |
| EP1191069B1 (de) | 2008-03-26 |
| CA2354680C (en) | 2009-02-03 |
| US6365721B1 (en) | 2002-04-02 |
| EP1191069A3 (de) | 2003-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2019020122A1 (zh) | 一种活性藏青至黑色染料组合物及染料制品 | |
| JP2003518188A (ja) | 反応性染料混合物 | |
| CN100400602C (zh) | 水溶性单偶氮染料、其制备和用途 | |
| US5136028A (en) | Reactive azo dyes | |
| CN105199427A (zh) | 一种多偶氮活性染料化合物及其制备方法 | |
| EP0675171B1 (de) | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung | |
| US3502644A (en) | Mono- and disazo dyestuffs containing a diazine or triazine group | |
| US4297278A (en) | Pentakis-and heptakis-azoxy dyestuffs | |
| EP0586331A2 (de) | Verfahren zum Färben von synthetischen Polyamidfasermaterialien | |
| US4485042A (en) | Dyestuff containing at least three azo bridges | |
| DE2729240A1 (de) | Azo-reaktivfarbstoffe | |
| US3580901A (en) | Maroon disazo dyes for polyamide fibers | |
| KR100368989B1 (ko) | 반응성 주황색 염료 | |
| JP3011994B2 (ja) | 反応性染料，その製造法，およびその使用 | |
| DE2829711A1 (de) | Azoraktivfarbstoffe | |
| DE1544442A1 (de) | Verfahren zur Herstellung neuer Azofarbstoffe | |
| DE3941395A1 (de) | Reaktivfarbstoffe mit triazin- und chlorbutinylanker | |
| US20030195341A1 (en) | Reactive trisazo dyes | |
| WO1997008246A1 (en) | Mixtures of disazo reactive dyes | |
| US4067865A (en) | Water-soluble diazotized amino azo dyestuff coupled with an amino-phenyl or -naphthyl component | |
| DE1544440C3 (de) | Reaktive Azofarbstoffe und ihre Verwendung | |
| JPS6212831B2 (zh) | ||
| DE1112225B (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE75571C (de) | Verfahren zur Darstellung von Azofarbstoffe aus aromatisch substituirten ai <Z4-Naph-, tylaminsulfosäuren | |
| DE19821347A1 (de) | Wasserlösliche halogentriazinhaltige Azoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1046292 Country of ref document: HK |
|
| ASS | Succession or assignment of patent right |
Owner name: DYSTAR COLOURS DISTRIBUTION GMBH Free format text: FORMER OWNER: DYSTAR TEXTILFARBEN GMBH + CO. DEUTXCHLAND KG Effective date: 20121107 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20121107 Address after: Frankfurt, Germany Patentee after: DyStar Textilfarben GmbH & Co. Deutschland KG Address before: Frankfurt, Germany Patentee before: Dystar Textilfarben GmbH & Co. Deutxchland KG |
|
| CX01 | Expiry of patent term |
Granted publication date: 20080709 |
|
| CX01 | Expiry of patent term |