CN1210552A - 纤维活性染料 - Google Patents

纤维活性染料 Download PDF

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CN1210552A
CN1210552A CN97192194A CN97192194A CN1210552A CN 1210552 A CN1210552 A CN 1210552A CN 97192194 A CN97192194 A CN 97192194A CN 97192194 A CN97192194 A CN 97192194A CN 1210552 A CN1210552 A CN 1210552A
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dyeing
fibre
formula
reactive dye
printing
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CN1085233C (zh
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P·多斯瓦尔德
R·瓦尔德
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Clariant Finance BVI Ltd
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing 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
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08Azo dyes
    • C09B62/085Monoazo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/70Material containing nitrile groups
    • D06P3/708Material containing nitrile groups using reactive dyes
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916Natural fiber dyeing
    • Y10S8/918Cellulose textile
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92Synthetic fiber dyeing
    • Y10S8/924Polyamide fiber

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本申请涉及式(Ⅰ)化合物以及制备该化合物的方法,其中R、Q和X的定义见申请书。该化合物可作为纤维活性染料用于使含有羟基或含有氮的有机基底进行染色或印染。

Description

纤维活性染料
本发明涉及纤维活性染料、制备该染料的方法以及它们在染色或印染含有羟基或含有氮的有机基底(organic substrates)中的应用。
本发明提供了式(Ⅰ)化合物或其盐的纤维活性染料,
当式(Ⅰ)纤维活性染料为其盐的形式时,与磺基相结合的阳离子不是关键性的,并且可以是在纤维活性染料方面常用的任一非发色的阳离子,条件是该相应的盐实质上是水可溶的。所述阳离子的实例有碱金属阳离子,例如钾或钠离子和铵阳离子如一、二、三和四-甲基铵阳离子或一、二、三和四乙基铵阳离子。该阳离子可以是相同的或不同的,即该化合物可以为混合盐形式。
式(Ⅰ)纤维活性染料显示出与其他已知染料良好的配伍性。因此,它可以与其他染料混合形成能够用来染色或印染合适基底的组合物。所述其他染料必须与式(Ⅰ)化合物是可配伍的,即它们必须具有类似的染色或印染性质例如不退色性质。
因此另一方面,本发明提供了含有式(Ⅰ)纤维活性染料的染色或印染组合物。
在优选的染色或印染组合物中,式(Ⅰ)纤维活性染料与选自合适的酞菁染料混合的某些蓝染料混合。尤其是含有式(Ⅰ)纤维活性染料和铜酞菁(更具体地说和C.I.Blue 207)的组合物。
含有纤维活性染料和铜酞菁的印染组合物迄今仍因本技术领域中称为催化退色而蒙受损失,从而铜酞菁催化了纤维活性染料色泽的选择性退色。令人遗憾的结果是:当暴露于日光之下时,用所述组合物着色的任一基底呈现有利于铜酞菁蓝色的印染组合物的色泽逐渐和迅速的丧失。而含有式(Ⅰ)纤维活性染料和铜酞菁的印染组合物在所述退色倾向方面显示出明显的减小。
本发明的染色或印染组合物优选含有其重量比为2∶1的式(Ⅰ)纤维活性染料和铜酞菁。该印染组合物的其他物质包括水,因此,100份重量的染色或印染组合物中有N份染料和100-N份水。
另一方面,本发明也提供了制备式(Ⅰ)纤维活性染料或其盐的方法,该方法包括下述步骤:使式(Ⅱ)化合物与三嗪(Ⅲ)反应,
该方法优选在水介质中于3~40℃(最好于5~10℃)和pH4~10(最好在pH6~8)进行。
式(Ⅰ)纤维活性染料可以按照已知的方法进行分离,例如盐析、过滤和任意在真空和略升温下干燥。
根据所述反应和/或分离条件,式(Ⅰ)纤维活性染料可以按含有例如1个或多个上述阳离子的游离酸或盐的形式或混合盐的形式得到。应用常用的方法,可以将式(Ⅰ)纤维活性染料从盐的形式或混合盐的形式转变成游离酸的形式,或者反之亦然。
用本技术领域专业人员熟知的合成方法从熟知的常用的起始原料,可以得到化合物(Ⅱ)和(Ⅲ),这里无需进一步地讨论。
式(Ⅰ)纤维活性染料可用作为纤维活性染料用于染色或印染含有羟基或含有氮的有机基底。优选的基底有皮革和纤维材料,包括天然或合成的聚酰胺类,以及特别是天然的或再生纤维素,例如棉花、粘胶纤维和人造棉织物。最优选的基底为含有棉花的纺织材料。
因此再一方面,本发明提供了应用式(Ⅰ)纤维活性染料或其盐作为纤维活性染料使含有羟基或含有氮的有机基底进行染色或印染。
染色或印染可以按照在纤维活性染料方面常用的已知方法进行。
在优选的染色方法中,应用在60-100℃,最好在80-100℃浸染法。式(Ⅰ)纤维活性染料具有良好的抽出和固定效率(exhaust和fixationyields)。此外,任一非固定的染料容易从基底中被洗去。
在优选的印染方法中,应用轧染方法例如轧蒸法、浸轧焙固法、浸轧烘干法、浸轧一堆放回苏工艺、浸轧卷染法、轧卷法。另外,可以应用喷墨法进行印染。
用上述纤维活性染料得到的染色或印染物具有良好的耐湿性和耐光性。它们对氧化剂例如加氯水、次氯酸盐、过氧化物和过硼酸盐的洗涤用洗涤剂也具有良好的抵抗性。此外,用上述式(Ⅰ)纤维活性染料得到的染色或印染物对酸水解作用具有很好的稳定性,例如当与稀乙酸接触进行染色时仅引起不染色的伴随纤维轻微的着色。
用染料混合物得到的染色或印染物显示出良好的不退色性,它与单独用式(Ⅰ)化合物得到的不退色性是类似的。
现在用下述实施例详细说明本发明。实施例1
于搅拌下将23份4-乙酰氨基-2-氨基苯磺酸的150份水、7份亚硝酸钠、49份盐酸(30%)和115份冰混合在一起。30分钟后用少许氨基磺酸中和过量的亚硝酸钠,于搅拌下向生成的溶液中加入17.9份1-乙基-5-氨基甲酰基-6羟基-4-甲基吡啶酮的100份水和12份氢氧化钠(30%)。30分钟后,加入69份盐酸(30%),并将得到的混合物于75~80℃加热4-5小时。然后将混合物冷却并过滤,得到式(Ⅱ)化合物,为橙色固体,
将27.5份1-氨基-苯2,4-二磺酸混悬于300份水中。用23份氢氧化钠(30%)使该混悬液溶解。向生成的溶液中加入20.5份2,4,6-三氯三嗪的100份水和200份冰,反应介质保持在5℃,并加入6份碳酸氢钠使pH保持在4.5~5。将得到的溶液加到按上述方法得到的式(Ⅱ)化合物的200份水中。用30份氢氧化钠(30%)将混合物调节至pH7。然后于5~10℃将混合物搅拌3~4小时。反应完成后将式(Ⅰ)化合物经过滤分离并于真空下干燥。
Figure A9719219400071
化合物(Ⅰ)可使棉花染成淡绿黄色。该印染物具有优良的耐光和耐湿性质并可对抗氧化影响。应用实施例A
制备具有下述成分的混合物
40份实施例1染料
100份尿素
330份水
500份4%藻酸钠增稠剂
10份1-硝基苯-3-磺酸钠
20份碳酸钠
1000份组合物
按照常用的印染方法将以上得到的组合物应用于棉花纤维。然后使印染的纤维干燥并于102-104℃蒸汽固定4-8分钟。
然后将染色的纤维于流动的冷水和热水中漂洗,其后再在热水中洗涤3分钟。在流动的热水中漂洗和离心之后将染色物干燥。得到的淡绿黄色染色物显示出良好的耐湿和耐光性质,并对氧化的影响具有良好的稳定性。应用实施例B
制备具有下述成分的混合物
100份尿素
315份水
450份4%藻酸钠增稠剂(Lamitex L10 10%)
10份1-硝基苯-3-磺酸钠
25份碳酸钠
900份组合物
  +由以下成分组成的印染组合物
32份实施例1染料
16份蓝色染料C.I.Blue 207
52份水
按照应用实施例A所述方法将得到的上述组合物应用于棉花纤维。
得到的亮绿色印染物具有良好的耐湿和耐光性质,并对氧化的影响具有良好的稳定性。此外,该印染物还对催化退色具有抵抗性。

Claims (11)

1.具有式(Ⅰ)的纤维活性染料或其盐,
Figure A9719219400021
其中R代表氢原子或者未取代或取代的烷基,X代表卤原子和Q代表CN或CONH2基团。
2.权利要求1所述的下式纤维活性染料,
3.权利要求1所述的纤维活性染料,其中-SO3H基团处于氨基的对位。
4.含有式(Ⅰ)纤维活性染料和铜酞菁的染色或印染组合物。
5.权利要求4所述染色或印染组合物,其中所述铜酞菁为C.I.Blue207。
6.权利要求4或5所述染色或印染组合物,其中式(Ⅰ)纤维活性染料与铜酞菁的重量比为2∶1。
7.生成权利要求1定义的式(Ⅰ)纤维活性染料或其盐的方法,该方法包括使式(Ⅱ)化合物与三嗪(Ⅲ)反应, 其中R、X和Q同上定义。
8.权利要求1定义的式(Ⅰ)纤维活性染料在使含有羟基或含有氮的有机基底进行染色或印染中的应用。
9.权利要求4-6中任何一项定义的染色或印染组合物在使含有羟基或含有氮的有机基底进行印染中的应用。
10.用权利要求1定义的式(Ⅰ)纤维活性染料染色的含有羟基或含有氮的有机基底。
11.用权利要求4-6所述染色或印染组合物印染的含有羟基或含有氮的有机基底。
CN97192194A 1996-02-12 1997-02-06 纤维活性染料 Expired - Fee Related CN1085233C (zh)

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GB9602787.5 1996-02-12
GBGB9602787.5A GB9602787D0 (en) 1996-02-12 1996-02-12 Organic compounds

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EP (1) EP0880559B1 (zh)
JP (1) JP4138877B2 (zh)
KR (1) KR100486992B1 (zh)
CN (1) CN1085233C (zh)
AT (1) ATE195963T1 (zh)
AU (1) AU712094B2 (zh)
BR (1) BR9707493A (zh)
CA (1) CA2244106C (zh)
DE (1) DE69702963T2 (zh)
ES (1) ES2150217T3 (zh)
GB (1) GB9602787D0 (zh)
HK (1) HK1018705A1 (zh)
ID (1) ID15925A (zh)
MX (1) MX9806227A (zh)
PT (1) PT880559E (zh)
TR (1) TR199801529T2 (zh)
WO (1) WO1997030125A1 (zh)
ZA (1) ZA971187B (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102876072A (zh) * 2012-09-20 2013-01-16 天津德凯化工股份有限公司 一种黄色活性染料及其制备方法
CN104559317A (zh) * 2014-04-28 2015-04-29 无锡润新染料有限公司 一种复合活性嫩黄染料组合物

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TW446734B (en) * 1997-12-11 2001-07-21 Ciba Sc Holding Ag Process for dyeing or printing and novel reactive dyes
FR2831177B1 (fr) 2001-10-22 2005-02-18 Rhodia Elect & Catalysis Dispersion colloidale et poudre colorees de cerium ou de cerium et de titane, de zirconium, d'aluminium ou d'une terre rare, leur procede de preparation et leur utilisation
GB0208444D0 (en) * 2002-04-12 2002-05-22 Clariant Int Ltd Composition for printing recording materials
CN100506816C (zh) * 2005-12-30 2009-07-01 明德国际仓储贸易(上海)有限公司 黄色染料化合物及其墨水组成物

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102876072A (zh) * 2012-09-20 2013-01-16 天津德凯化工股份有限公司 一种黄色活性染料及其制备方法
CN104559317A (zh) * 2014-04-28 2015-04-29 无锡润新染料有限公司 一种复合活性嫩黄染料组合物

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AU712094B2 (en) 1999-10-28
CA2244106A1 (en) 1997-08-21
ID15925A (id) 1997-08-21
JP2000504765A (ja) 2000-04-18
EP0880559A1 (en) 1998-12-02
ATE195963T1 (de) 2000-09-15
AU1721897A (en) 1997-09-02
US6042621A (en) 2000-03-28
MX9806227A (es) 1998-11-30
BR9707493A (pt) 1999-07-27
KR100486992B1 (ko) 2005-06-16
JP4138877B2 (ja) 2008-08-27
HK1018705A1 (en) 1999-12-30
ES2150217T3 (es) 2000-11-16
KR19990082446A (ko) 1999-11-25
GB9602787D0 (en) 1996-04-10
CN1085233C (zh) 2002-05-22
ZA971187B (en) 1998-11-23
DE69702963D1 (de) 2000-10-05
WO1997030125A1 (en) 1997-08-21
EP0880559B1 (en) 2000-08-30
CA2244106C (en) 2005-09-20
TR199801529T2 (xx) 1998-10-21
DE69702963T2 (de) 2000-12-28
PT880559E (pt) 2001-01-31

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