CN101287803A - 铬络合物染料 - Google Patents

铬络合物染料 Download PDF

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CN101287803A
CN101287803A CNA2006800266494A CN200680026649A CN101287803A CN 101287803 A CN101287803 A CN 101287803A CN A2006800266494 A CNA2006800266494 A CN A2006800266494A CN 200680026649 A CN200680026649 A CN 200680026649A CN 101287803 A CN101287803 A CN 101287803A
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chromium complex
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R·努瑟
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/16—Monoazo compounds containing chromium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0055—Mixtures of two or more disazo dyes
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    • C09D11/32—Inkjet printing inks characterised by colouring agents
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    • 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
    • D06P1/10—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 containing metal
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    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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Abstract

本发明涉及新型1:2铬络合物染料、其制备方法及其在染色或印刷包含羟基或包含氮的纤维材料中的用途。本发明涉及一种式(I)的1:2铬络合物染料、其制备及其在染色或印刷包含羟基或包含氮的纤维材料中的用途，其中所有的取代基如权利要求书所定义。

Description

铬络合物染料
本发明涉及新型1∶2铬络合物染料、其制备方法及其在染色或印刷包含羟基或包含氮的纤维材料中的用途。
本发明涉及一种式(I)的1∶2铬络合物染料及其混合物和/或其盐：
Figure A20068002664900041
其中
R1为H、Cl、Br或-NO2；
R2为H、Cl、Br、-NO2、-SO2NH2或-SO3H；
R3为O(CH2)nOR4或(CH2)nOR4；
R4为H、直链C1-4烷基、支链C3-4烷基或-SO3H；
n为1、2、3或4；和
Ka+为阳离子。
所述直链或支链烷基可被取代或未被取代。合适的取代基可例如为羟基、卤素例如Cl或Br或磺基。
在优选的式(I)化合物中，R4为H、C1-3烷基或-SO3H，n为1、2、3或4，优选R4为H或C1-3烷基，n为1、2、3或4。
在优选的式(I)化合物中，R3在氮原子的对位。
在优选的式(I)化合物中，R1独立表示H或NO2，优选R1表示NO2。
在优选的式(I)化合物中，R2独立表示NO2或SO2NH2，优选R2表示NO2。
在更优选的式(I)化合物中，R4为H、CH3或CH2CH3，n为2、3或4。
在更优选的式(I)化合物中，R4为H，n为2。
合适的阳离子K为碱金属、碱土金属、铵、链烷醇铵或烷基铵阳离子。例如在一价阳离子的情况下，K还可为多于一种阳离子。相应的阳离子的实例有钠、锂或铵阳离子或单-、二-或三乙醇铵阳离子。
本发明的其他实施方案为一种制备式(I)化合物的方法，所述方法包括使式(II)的偶氮化合物
Figure A20068002664900051
与式(III)的1∶1铬络合物反应，
Figure A20068002664900052
其中R1、R2、R3和R4如上定义。
式(II)的偶氮化合物与式(III)的1∶1铬络合物的反应例如在含水介质中，在例如40℃-130℃，特别是70℃-100℃下，在pH例如为8-14，特别是pH为10-13下进行。所述反应最好在中和无机酸的试剂或碱性试剂存在下，例如在碱金属碳酸盐、碱金属乙酸盐或碱金属氢氧化物存在下进行，优选钠作为碱金属。
式(II)和(III)的化合物为已知的或可通过与已知方法类似的方法制得。
式(II)化合物可通过常规的重氮化和偶合反应制得。重氮化通常通过亚硝酸在无机酸水溶液中，于低温，例如0℃-20℃下进行，偶合最好进行在碱性pH，例如pH为8-12下进行。
式(III)的1∶1铬络合物可因此根据常规的镀铬方法制得，其中所述反应可使用铬盐例如在含水介质中、适当的情况下在加压下、在例如90℃-130℃下进行。铬盐例如为乙酸铬(III)、硝酸铬(III)、氯化铬(III)、水杨酸铬(III)或特别是硫酸铬(III)。
本发明的其他实施方案为一种染色或印刷包含羟基或包含氮的纤维材料的方法。
纤维材料优选为天然存在的聚酰胺纤维材料(例如丝或特别是羊毛)或合成的聚酰胺纤维材料(例如聚酰胺6或聚酰胺6，6或含羊毛或含聚酰胺的混纺织物)。合成的聚酰胺纤维材料为本文特别感兴趣的。
上述纤维材料可为多种加工形式，例如为纤维、纱、织造织物或针织织物形式，特别是地毯形式。
染色或印刷可在常规的染色或印刷设备中进行。染液或印浆可包含其他添加剂，例如润湿剂、消泡剂、流平剂或影响纺织品性能的试剂例如软化剂、提供阻燃整饰或防污、防水和防油试剂的添加剂以及水-软化剂和天然存在或合成的增稠剂例如藻酸盐和纤维素醚。
在优选的印刷法中，使用扎染法，例如扎染-汽蒸、扎染-热固化、扎染-干燥、扎染-分批、扎染-筛分和扎染-辊卷。或者可使用喷墨法进行印刷。
本发明的式(I)的1∶2铬络合物染料得到具有良好综合性能的均匀染色。本发明的式(I)的1∶2铬络合物染料还适合用作染色混合物的组分。
以下实施例用于说明本发明。除非另外说明，否则百分比为重量百分比，温度为摄氏度。
实施例1a
将195份4-羟基-7-[(4-(2′-羟基乙氧基)苯基)氨基]-萘-2-磺酸溶解于600份水和45份30％的氢氧化钠溶液中。随后在25℃下加入50份脲。在30分钟内加入由99.5份2-氨基-4，6-二硝基-1-羟基苯和125体积份4N的亚硝酸钠溶液的混合物形成的重氮盐溶液(0-5℃，pH为1)。在偶合反应过程中，通过连续加入30％的氢氧化钠溶液使pH保持为9-10。反应结束时，将制得的产物盐析，吸滤。这样制得的化合物具有式1的结构。
Figure A20068002664900071
将吸滤后仍潮湿的残余物加至4000份水、65份甲酸和125份硫酸铬(III)的混合物中，随后在130℃和2巴压力下搅拌5小时。反应完成后，通过常规的方法分离形成的1∶1-铬络合物，随后过滤。产物具有式2的结构。
实施例1b
于75-80℃和pH为8-9下，将149.3份通过常规的方法制得的具有式3结构的单偶氮化合物悬浮于3000份水中。
Figure A20068002664900081
搅拌下，向该混合物中加入318份通过实施例1a的方法制得的具有式(2)结构的1∶1铬络合物。
Figure A20068002664900082
这时通过加入30％的氢氧化钠溶液使pH保持为10。反应完成后，使用常规的方法将所得到的1∶2铬络合物盐析，过滤，随后于60℃下真空干燥。终产物与式(4)一致，
将羊毛和合成聚酰胺染成蓝色色调。这样得到的染色具有优异的耐光性和耐湿性。
实施例2-15
表1公开了根据与实施例1a-1b类似的方法，使用相应的原料形成的几种染料(式(5)的取代基)。在所有的情况下，制得的染料将羊毛和合成聚酰胺染成蓝色色调，且这样得到的染色具有优异的耐光性和耐湿性。
表1
  实施例   R1   R2   R3
  2   -NO2   -NO2   -CH2CH2OH
  3   -NO2   -SO2NH2   -CH2OH
  4   -H   -NO2   -CH2CH2CH2OH
  5   -H   -NO2   -CH2CH2CH2CH2OH
  6   -NO2   -NO2   -OCH2CH2OCH3
  7   -NO2   -NO2   -OCH2CH2OCH2CH3
  8   -NO2   -SO2NH2   -OCH2CH2OCH3
  9   -NO2   -SO2NH2   -OCH2CH2OCH2CH3
  10   -NO2   -NO2   -OCH2CH2OSO3H
  11   -NO2   -SO2NH2   -OCH2CH2OH
  12   -Cl   -NO2   -OCH2CH2OH
  13   -NO2   -Cl   -OCH2CH2OH
  14   -H   -Cl   -OCH2CH2OCH3
  15   -H   -NO2   -OCH2CH2OCH2CH3
应用实施例A
于40℃下，将由2000份水、1份基于乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱阳离子活性流平剂、1.5份实施例1的染料组成，并用0.5份40％的乙酸将pH调节至6的染浴加至100份尼龙-6织物中。于40℃下10分钟后，以1℃/分钟的速率将染浴加热至98℃，随后沸腾45-60分钟。接着在15分钟内冷却至70℃。将染色物从染浴中移开，依次用热水和冷水漂洗，随后干燥。结果是得到具有非常高耐光性的灰色聚酰胺。
应用实施例B
于40℃下，将由4000份水，1份基于硫酸化的乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱两性流平剂、2份实施例1的染料组成，并用0.5份40％的乙酸将pH调节至6的染浴加至100份羊毛织物中。于40℃下10分钟后，以1℃/分钟的速率将染浴加热至沸腾，持续沸腾45-60分钟。接着在20分钟内冷却至70℃。将染色物从染浴中移开，依次用热水和冷水漂洗，随后干燥。结果是得到具有非常高耐光性的灰色羊毛。
应用实施例C
使用50℃的由以下物质组成的染浴扎染100份织造尼龙-6材料：
40份实施例1的染料，
100份脲，
20份基于丁二醇的非离子增溶剂，
15-20份乙酸(将pH调节至4)，
10份基于乙氧基化的氨基丙基脂肪酰胺且对染料具有亲和力的弱阳离子活性流平剂，和
810-815份水(组成1000份扎染液)。
将这样浸渍的材料卷起，随后在蒸汽室中在85-98℃饱和蒸汽条件下停留3-6小时以固色。接着依次用热水和冷水漂洗染色物，随后干燥。结果是得到具有良好均匀性和良好耐光性的灰色尼龙。
应用实施例D
用每1000份包含以下物质的染液扎染由尼龙-6组成且具有合成基础织物的纺织短切长毛绒片材料：
2份               实施例1的染料；
4份               市售的基于角豆粉醚的增稠剂；
2份               高级烷基酚的非离子环氧乙烷加成物；
1份               60％的乙酸。
随后使用每1000份包含以下组分的印浆印刷：
20份              市售的烷氧基化的脂肪烷基胺(置换产物)；
20份              市售的基于角豆粉醚的增稠剂。
在100℃饱和蒸汽中固定印刷6分钟，漂洗，随后干燥。结果是得到具有灰色和白色图案的均色覆盖材料。

Claims (7)

1.一种式(I)的1∶2铬络合物染料及其混合物和/或其盐
其中
R1为H、Cl、Br或-NO2；
R2为H、Cl、Br、-NO2、-SO2NH2或-SO3H；
R3为O(CH2)nOR4或(CH2)nOR4；
R4为H、直链C1-4烷基、支链C3-4烷基或-SO3H；
n为1、2、3或4；和
Ka+为阳离子。
2.权利要求1的式(I)的1∶2铬络合物染料及其混合物和/或其盐，其中R3在氮原子的对位，R4为H、CH3或CH2CH3，n为2、3或4。
3.权利要求1的式(I)的1∶2铬络合物染料，其中R1表示H或NO2，R2表示NO2或SO2NH2。
4.一种制备权利要求1、2或3的式(I)化合物的方法，其特征在于使式(II)的偶氮化合物
Figure A20068002664900031
与式(III)的1∶1铬络合物反应，
Figure A20068002664900032
其中R1、R2、R3和R4如上定义。
5.一种制备喷墨油墨的方法，所述方法包括使用权利要求1、2或3的染料或染料的混合物。
6.一种染色或印刷包含羟基或包含氮的纤维材料的方法，其中使用式(I)化合物、其盐或其混合物进行染色或印刷。
7.一种包含羟基或包含氮的纤维材料，其特征在于使用权利要求1、2或3中定义的化合物、其盐或其混合物染色或印刷所述纤维材料。
CN2006800266494A 2005-07-21 2006-07-17 铬络合物染料 Expired - Fee Related CN101287803B (zh)

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CN102516795A (zh) * 2011-12-09 2012-06-27 青岛双桃精细化工（集团）有限公司 一种蓝色染料的制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8391999B2 (en) * 2010-06-09 2013-03-05 Taiwan Semiconductor Manufacturing Company, Ltd. Auto device skew manufacturing
US11905424B2 (en) 2019-04-01 2024-02-20 General Electric Company Fabrication of chromium metal mixtures in the form of core-shell nanoparticles
KR20230049541A (ko) 2021-10-06 2023-04-13 이승주 자동 차량 방향 전환장치

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH452747A (de) * 1965-07-09 1968-03-15 Sandoz Ag Verfahren zur Herstellung von 1:2-Metallkomplexfarbstoffen
FR1486227A (fr) * 1965-07-09 1967-06-23 Sandoz Sa Colorants à complexe métallifère 1:2, leurs procédés de fabrication et leurs applications
CH573949A5 (zh) 1972-06-28 1976-03-31 Sandoz Ag
CH616953A5 (zh) 1975-08-27 1980-04-30 Sandoz Ag
CH649775A5 (de) 1979-09-25 1985-06-14 Sandoz Ag Wasserloesliche, anionische chromkomplexe, deren herstellung und verwendung.
JPS59159855A (ja) * 1983-03-03 1984-09-10 バスフ　アクチェン　ゲゼルシャフト スルホンアミド基及びアミノ基を含有しない金属錯化合物染料
US5283325A (en) 1984-04-27 1994-02-01 Sandoz Ltd. 1:2 chromium and cobalt complexes of monoazo compounds having further unsubstituted or substituted nitro-2-hydroxyphenyl diazo component radicals and 6- or 7-acyl-amino-1-hydroxy-3-sulfonaphthalene coupling component radicals
DE3514387C2 (de) 1984-04-27 2003-12-24 Clariant Finance Bvi Ltd 1:2-Metallkomplex-azoverbindungen, ihre Herstellung und Verwendung
DE3433951A1 (de) * 1984-09-15 1986-03-27 Basf Ag, 6700 Ludwigshafen Unsymmetrische 1:2-chromkomplexfarbstoffe
DE3805746C2 (de) 1987-03-05 2003-04-10 Clariant Finance Bvi Ltd 1:2-Chromkomplexfarbstoffe
CH685119A5 (de) 1992-06-24 1995-03-31 Sandoz Ag Asymmetrische 1:2-Metallkomplex-azoverbindungen.
EP0718374B1 (de) * 1994-12-21 2002-03-06 Ciba SC Holding AG 1:2-Chromkomplexfarbstoffe enthaltende Farbstoffmischungen und 1:2 Chromkomplexfarbstoffe
GB9604816D0 (en) 1996-03-07 1996-05-08 Clariant Finance Bvi Ltd Organic compounds
US5738013A (en) * 1996-05-14 1998-04-14 New England Science & Specialty Products, Inc. Method of making a lithographic printing plate with an ink jet fluid material
WO1998054264A1 (de) 1997-05-29 1998-12-03 Clariant Finance (Bvi) Limited 1:2-chromkomplexfarbstoffe, deren herstellung und verwendung
AU762999B2 (en) * 1998-08-14 2003-07-10 Clariant Finance (Bvi) Limited 1:2 chromium complex dyes, their production and use
DE60214747T2 (de) * 2001-10-17 2007-09-13 Clariant Finance (Bvi) Ltd., Road Town 1:2 metallkomplexfarbstoffe, deren zusammensetzungen, deren herstellung und deren verwendung

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102516795A (zh) * 2011-12-09 2012-06-27 青岛双桃精细化工（集团）有限公司 一种蓝色染料的制备方法
CN102516795B (zh) * 2011-12-09 2014-04-02 青岛双桃精细化工（集团）有限公司 一种蓝色染料的制备方法

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KR20080028944A (ko) 2008-04-02
BRPI0613688B1 (pt) 2016-10-18
ATE431383T1 (de) 2009-05-15
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JP2009501823A (ja) 2009-01-22
JP5091134B2 (ja) 2012-12-05
US20090263630A1 (en) 2009-10-22
ES2326693T3 (es) 2009-10-16
WO2007009966A2 (en) 2007-01-25
WO2007009966A3 (en) 2007-04-05
MX2008000783A (es) 2008-02-21
ZA200710412B (en) 2009-08-26
PT1910473E (pt) 2009-08-05
BRPI0613688A2 (pt) 2011-01-25
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US7906632B2 (en) 2011-03-15
EP1910473B1 (en) 2009-05-13

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