CN100400602C - 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
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- 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 12
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 4
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- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
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- 125000005518 carboxamido group Chemical group 0.000 abstract 1
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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
- 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
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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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
- 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
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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氨基材料的用途：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氨基的材料，尤其是含甲酰氨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氨基纤维材料，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氨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氨基材料例如羊毛、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 | R<sup>1</sup> | R<sup>2</sup> | R<sup>3</sup> | -SO<sub>3</sub>H的位置 |
| 2 | -COCH<sub>2</sub>O- | 2-Cl | 4-Cl | H | 3 |
| 3 | -COCH<sub>2</sub>O- | 2-Cl | H | H | 4 |
| 4 | -COCH<sub>2</sub>O- | 2-Cl | H | H | 3 |
| 5 | -COCH<sub>2</sub>O- | H | H | H | 4 |
| 6 | -COCH<sub>2</sub>O- | H | H | H | 3 |
| 7 | -COCH<sub>2</sub>O- | H | 4-CH<sub>3</sub> | H | 4 |
| 8 | -COCH<sub>2</sub>O- | H | 4-CH<sub>3</sub> | H | 3 |
| 9 | -COCH<sub>2</sub>O- | H | 4-OCH<sub>3</sub> | H | 4 |
| 10 | -COCH<sub>2</sub>O- | H | 4-OCH<sub>3</sub> | H | 3 |
| 11 | -SO<sub>2</sub>- | H | H | H | 4 |
| 12 | -SO<sub>2</sub>- | H | H | H | 3 |
| 13 | -SO<sub>2</sub>- | H | 4-CH<sub>3</sub> | H | 4 |
| 14 | -SO<sub>2</sub>- | H | 4-CH<sub>3</sub> | H | 3 |
Claims (5)
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-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R1和R2为氢或氯，和R3为氢。
3.权利要求1或2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如权利要求1或2所定义，
将式(6)的胺重氮化，并将该产物偶合到式(5)的偶合组分上。
4.权利要求1或2的染料用于染色和印染含甲酰氨基的材料的用途。
5.一种染色和印染含甲酰氨基的材料的方法，该方法包括，在pH为3-7和温度为70-110℃下，把权利要求1或2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 CN1346850A (zh) | 2002-05-01 |
| CN100400602C true CN100400602C (zh) | 2008-07-09 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| 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 |
|---|---|---|---|---|
| EP3225663B1 (en) | 2014-11-25 | 2018-10-31 | Fujifilm Corporation | Coloring composition for dyeing, coloring composition for printing, printing method, inkjet printing ink, and dyed fabric |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1824686A (en) * | 1929-07-04 | 1931-09-22 | Geigy Ag J R | Manufacture of monoazo-dyestuffs |
| US1893244A (en) * | 1928-10-15 | 1933-01-03 | Firm J R Geigy S A | 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 AT AT01122159T patent/ATE390464T1/de active
- 2001-09-15 PT PT01122159T patent/PT1191069E/pt unknown
- 2001-09-15 ES ES01122159T patent/ES2303823T3/es not_active Expired - Lifetime
- 2001-09-15 EP EP01122159A patent/EP1191069B1/de not_active Expired - Lifetime
- 2001-09-15 DE DE50113777T patent/DE50113777D1/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
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2002
- 2002-10-30 HK HK02107848.7A patent/HK1046292B/zh not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1893244A (en) * | 1928-10-15 | 1933-01-03 | Firm J R Geigy S A | Manufacture of monoazo-dyestuffs |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4750981B2 (ja) | 2011-08-17 |
| JP2002146221A (ja) | 2002-05-22 |
| PT1191069E (pt) | 2008-06-09 |
| HK1046292A1 (en) | 2003-01-03 |
| TW576856B (en) | 2004-02-21 |
| ES2303823T3 (es) | 2008-09-01 |
| EP1191069A3 (de) | 2003-12-03 |
| KR20020023674A (ko) | 2002-03-29 |
| CN1346850A (zh) | 2002-05-01 |
| CA2354680C (en) | 2009-02-03 |
| CA2354680A1 (en) | 2002-03-23 |
| KR100754632B1 (ko) | 2007-09-05 |
| EP1191069B1 (de) | 2008-03-26 |
| ATE390464T1 (de) | 2008-04-15 |
| HK1046292B (zh) | 2009-07-03 |
| US6365721B1 (en) | 2002-04-02 |
| EP1191069A2 (de) | 2002-03-27 |
| DE50113777D1 (de) | 2008-05-08 |
| DE10047234A1 (de) | 2002-04-11 |
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