CN1165162A - 单偶氮基吡啶酮染料的混合物 - Google Patents
单偶氮基吡啶酮染料的混合物 Download PDFInfo
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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
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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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
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- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
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- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/922—Polyester fiber
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Abstract
本专利叙述了染料混合物，此混合物含有A)通式(1)的染料和B)通式(2)的染料，其中各基团如说明书中定义。此染料混合物适用于染料和印花纺织纤维材料，使染色成品具有良好的综合性能。
Description
本发明涉及单偶氮基吡啶酮染料混合物，其制备和用于纺织纤维材料的染色或印花。
单偶氮基吡淀酮染料及其用于合成纤维材料的染色是众所周知的，例如，从EP-A-O440072中就已知道。然而，已经发现，这些染料并不总是能完全满足最高要求的。因此，需要新的染料和染料混合物，这些染料和染料混合物特别可显示出较好的上染、提升或耐洗性能。
现已发现，本发明的混合物在纤维上能高度上染，并具有良好的提升性，产生的染色物品耐光、耐升华和耐洗涤。
因此，本发明涉及的染料混合物含有：
A)通式(1)染料式中，R1是C1-C4烷基，
R2是(CH2)nO-R5，
R5与R1无关，是C1-C4烷基，
n是数字1，2或3，以及
B)通式(2)的染料，式中，R3和R4相互无关，各是C1-C4烷基。
通式(1)和(2)中的C1-C4烷基是甲基、乙基、异丙基、正丙基、异丁基、正丁基、仲丁基或叔丁基。
优选的染料混合物含有R1为甲基的通式(1)的染料。
进一步优选的染料混合物含有R5是甲基、乙基或异丙基的通式(1)的染料。
同样是优选的染料混合物含有R3是甲基的通式(2)的染料。
进一步优选的染料混合物含有R4是甲基或乙基的通式(2)的染料。
特别优选的染料混合物含有R1是甲基、R5是甲基、乙基或异丙基和n是2或3的染料(1)的染料。
同样特别优选的染料混合物含有R3是甲基和R4是甲基或乙基的通式(2)的染料。
尤其优选的染料混合物含有R1是甲基，R5是甲基，乙基或异丙基，n是2或3的通式(1)的染料和R3是甲基和R4是甲基或乙基的通式(2)的染料。
本发明染料混合物中(A)和(B)染料的比例可以在宽范围内变化，例如从5∶1直到1∶5。(A)和(B)染料比为3∶1到1∶3的染料混合物是优选的。(A)与(B)比为1∶1的染料混合物是特别优选的。
列于表1中的通式(1)的染料(A)和通式(2)的染料(B)的下列染料混合物是特别优选的：表1
| 通式(1)的染料(A) | 通式(2)的染料(B) | |||
| 染料混合物号 | R1 | R2 | R3 | R4 |
| 1 | CH3 | (CH2)3OCH3 | CH3 | CH3 |
| 2 | CH3 | (CH2)3OC2H5 | CH3 | CH3 |
| 3 | CH3 | (CH2)3OCH(CH3)2 | CH3 | CH3 |
| 4 | CH3 | (CH2)2OCH3 | CH3 | CH3 |
| 5 | CH3 | (CH2)3OCH3 | CH3 | C2H5 |
| 6 | CH3 | (CH2)3OC2H5 | CH3 | C2H5 |
| 7 | CH3 | (CH2)3OCH(CH3)2 | CH3 | C2H5 |
| 8 | CH3 | (CH2)2OCH3 | CH3 | C2H5 |
| 9 | CH3 | (CH2)3OCH3 | CH3 | n-C3H7 |
| 10 | CH3 | (CH2)3OCH3 | CH3 | n-C4H9 |
| 11 | CH3 | (CH2)3OCH(CH3)2 | CH3 | n-C3H7 |
| 12 | CH3 | (CH2)3OCH(CH3)2 | CH3 | n-C4H9 |
| 13 | CH3 | (CH2)3OCH(CH3)2 | CH3 | CH2-CH(CH3)2 |
| 14 | C2H5 | (CH2)3OCH3 | CH3 | C2H5 |
| 15 | C2H5 | (CH2)3OCH(CH3)2 | CH3 | C2H5 |
| 16 | CH3 | (CH2)3OCH3 | C2H5 | CH3 |
| 17 | CH3 | (CH2)3OCH(CH3)2 | C2H5 | C2H5 |
| 18 | CH3 | (CH2)3OCH3 | n-C4H9 | C2H5 |
| 19 | n-C4H9 | (CH2)3OCH3 | CH3 | C2H5 |
| 20 | C2H5 | (CH2)3OCH3 | C2H5 | C2H5 |
本发明还涉及含通式(1)和(2)染料的染料混合物的制备方法。例如，本发明的染料混合物可以通过通式(1)和(2)的染料以所要求的比例相互混合而制得，或通过重氮化通式(3)的重氮成分而制得：
式中，R1是C1-C4烷基，并将产物偶联到通式(4)和(4a)的两种偶联成分的混合物上
式中，R2如通式(1)中所定义，和式中，R4如通式(2)中所定义。
含有通式(1)和(2)的染料的本发明的染料混合物可以用于染色和印花半合成的、特别是疏水合成的纤维材料，特别是纺织材料。含有这些半合成或疏水合成纺织材料的混纺织物的纺织材料可借助本发明的染料混合物染色或印花。
半合成纺织材料具体讲是2醋酸纤维素和三醋酸纤维素。
疏水合成纺织材料，具体讲含有线型的芳族聚酯，例如由对苯二甲酸和二醇，具体的为乙二醇生成的聚酯，或由对苯二甲酸和1，4双(羟甲基)环己烷缩合得到的聚酯；聚碳酸酯，例如由α，α-二甲基4，4’-二羟基-二苯基甲烷和光气生成的聚碳酸酯，以及以聚氯乙烯和聚酰胺为基础的纤维。
本发明的染料混合物通过已知的染色方法施加到纺织材料。例如，聚酯纤维材料的染色是在80℃-140℃的温度并在常规的阴离子或非离子分散剂，如果合适，还有常规的溶胀剂(载体)存在下由水分散液用上染法进行。2醋酸纤维素的染色优选是在约65-85℃进行，三醋酸纤维素的染色是在高达115℃温度下进行。
在染料浴中同时存在羊毛和棉花时，本发明的染料混合物不着色或仅轻微着色(良好的防染)，所以，本发明的染料混合物也可用于染色聚酯/羊毛和聚酯/纤维素混纺织物。
本发明的染料混合物适于上染法和热溶胶法染色以及适用于印花。上染法是优选的。水溶液比取决于设备情况，基材和组成。然而，可以在宽范围内选择，例如1∶4-1∶100，但优选范围是1∶6-1∶25。
提到的纺织材料可以是各种加工形式，例如纤维、纱线或无纺布，以及织物或针织品。
在使用前，最好将本发明的染料混合物转化为染料制剂。为此，将染料混合物研磨，使得染料混合物的粒子平均大小为0.1-10微米。研磨可以在分散剂存在下进行。例如，干燥过的染料混合物同分散剂一起研磨，或同分散剂以糊的形式捏和，然后真空干燥或喷雾干燥。这样得到的制剂在加水后可以制得印染浆料和染色浴。
如果是印花，使用常用的增稠剂，例如改性的或未改性的天然产品，如藻酸盐、不列颠树胶、阿拉伯树胶、结晶树胶、角豆粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或合成产品，如聚丙烯酰胺、聚丙烯酸或其共聚物，或聚乙烯醇。
本发明的染料混合物赋予上述提到的材料特别是聚酯材料良好的使用耐牢性的均匀黄色或金黄色，特别如对光和升华的牢度好。应该强调耐水洗。本发明的染色料还有优良的吸尽和聚染性。
本发明的染料混合物还可以用于特别是同其它染料一起制备混合色调，或同适宜的红染料和蓝染料一起进行三色染色。
本发明还涉及本发明的染料混合物的上述使用，并涉及对半合成或疏水的合成纤维材料，特别是纺织材料的染色或印花方法。此方法包括将本发明的染料混合物施于上述材料，并将其嵌入材料中。上述疏水的纤维材料优选是纺织聚酯材料。可用本发明方法处理的被染物和优选的染料条件将在本发明染料混合物应用的更详细的解释中加以讨论。
本发明还涉及由上述方法染色和印花的疏水纤维材料，优选为聚酯纺织材料。
下面的各实施例用来解释本发明。在这些实施例中，除非加以指出外，份是指重量份，百分数是指重量百分数。温度是摄氏度。重量份与体积份的关系如同克与立方厘米的关系一样。实施例1
将33.6份2-硝基-4-甲氧基苯胺在220份水中的悬浮液冷至10-15℃，逐滴加入60份32％的盐酸。然后在15分钟内加入55份4当量的亚硝酸钠溶液，经充分搅拌，将反应混合物的温度保持在约15℃。当加入完成后，再将混合物搅拌1小时，用少量氨基磺酸将过量的亚硝酸盐破坏。得到的重氮化混合物缓慢流进一溶液中，此溶液为冷至约5-10℃的20.7份N-乙基-3-氰基-4-甲基-5-羟基吡啶酮，24.3份的N-异丙氧基丙基-3-氰基-4-甲基-5-羟基吡啶酮和16.3份的30％的氢氧化钠水溶液溶于200份水中形成的溶液。在加入重氮化混合物中时，用30％的氢氧化钠水溶液将pH保持恒定在5-6。随后将桔红色悬浮液在15-20℃再搅拌约1小时。将沉淀经吸滤过滤，用水漂洗，在70℃下真空干燥。得到78.4份染料混合物No.7。此染料混合物将聚酯染色成牢固的亮金黄色调，特别是耐水洗性好。实施例2
染料混合物1-6和8-20依序列于表1，这些染料混合物也可将聚酯染成牢固的亮金黄色，特别耐水洗。所用的方法类似于实施例1中所叙述的方法，或混合通式(1)和(2)两种染料。实施例3
将100克聚酯纤维以溶液比1∶20浸入室温下含有下列成分的溶液中：1克No.7的染料混合物，1克/升硫酸铵和0.5克/升市场购得的匀染剂，此溶液已将pH用80％甲酸调至4.5-5。然后将此溶液加热，首先以3℃/分钟的加热速度加热到60℃，然后再用2℃/分钟的速度加热到13℃。
染色在130℃进行60分钟。然后将溶液冷到40℃，将染色后的聚酯织物用水洗，然后在含有5毫升/升30％氢氧化钠溶液、2克/升85％的连二亚硫酸钠和1克/升的市场购得洗涤剂的浴中在70-80℃下洗20分钟。完成的染色织物再用水洗，并干燥得到具有优秀耐水洗牢度的亮金黄色的染色物。
Claims (11)
1.一种染料混合物，含有
A)通式(1)的染料式中，R1是C1-C4烷基，R2是(CH2)nO-R5基团，R5与R1无关，是C1-C4烷基，n是数字1，2或3，以及
B)通式(2)的染料
式中，R3和R4无关，各是C1-C4烷基。
2.权利要求1的染料混合物，其中，R1是甲基。
3.权利要求1或2的染料混合物，其中，R4是甲基或乙基。
4.权利要求1-3中任一的染料混合物，其中，R3是甲基。
5.权利要求1-4的任一染料混合物，其中，R5是甲基、乙基或异丙基。
6.权利要求1的染料混合物，其中，R1和R3是甲基，R4是甲基或乙基，R5是甲基、乙基或异丙基，和n是2或3。
7.权利要求1-6中任一项的染料混合物，其中，通式(1)和(2)的染料比为3∶1-1∶3。
8.制备权利要求1的染料混合物的方法，此方法包括将通式
的重氮成分重氮化，通式(3)中R1是C1-C4烷基，此方法还包括将产物偶联到通式(4)和(4a)
的两种偶联成分的混合物上，在通式(4)中，R2是(CH2)nO-R5，R5是C1-C4烷基，以及n是数字1，2或3，式中R4是C1-C4烷基。
9.权利要求1的染料混合物用于染色或印花半合成的或合成的疏水纤维材料，特别是纺织材料。
10.染色或印染半合成或合成的疏水纤维材料，特别是纺织材料的方法，此方法包括将权利要求1的染料混合物施于上述材料或将染料混合物嵌于材料中。
11.按照权利要求10染色或印花的疏水纤维材料，优选是聚酯纺织材料。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH330595 | 1995-11-22 | ||
| CH3305/95 | 1995-11-22 | ||
| CH3305/1995 | 1995-11-22 |
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| Publication Number | Publication Date |
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| CN1165162A true CN1165162A (zh) | 1997-11-19 |
| CN1076034C CN1076034C (zh) | 2001-12-12 |
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| US (1) | US5935274A (zh) |
| EP (1) | EP0776948B1 (zh) |
| JP (1) | JP3880109B2 (zh) |
| CN (1) | CN1076034C (zh) |
| DE (1) | DE59607408D1 (zh) |
| ES (1) | ES2161342T3 (zh) |
| HK (1) | HK1005548A1 (zh) |
| TW (1) | TW375642B (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI470035B (zh) * | 2008-12-11 | 2015-01-21 | Dystar Colours Distrib Gmbh | 分散性染料之混合物 |
| CN108047752A (zh) * | 2017-12-29 | 2018-05-18 | 东营安诺其纺织材料有限公司 | 一种分散黄的生产工艺 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7168084B1 (en) | 1992-12-09 | 2007-01-23 | Sedna Patent Services, Llc | Method and apparatus for targeting virtual objects |
| US8906116B2 (en) * | 2008-12-11 | 2014-12-09 | Dystar Colours Distribution Gmbh | Mixtures of disperse dyes |
| JP5727321B2 (ja) * | 2011-07-15 | 2015-06-03 | 株式会社日本触媒 | ピリドンアゾ化合物 |
| CN105102547A (zh) * | 2013-01-14 | 2015-11-25 | 德司达染料分销有限公司 | 高湿牢度快速分散染料混合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1256093A (en) * | 1968-06-27 | 1971-12-08 | Ici Ltd | Water-insoluble monoazo dyestuffs |
| EP0085823B1 (de) * | 1982-02-10 | 1986-02-05 | Ciba-Geigy Ag | Farbstoffmischung, Verfahren zu ihrer Herstellung und Verwendung zum Färben und Bedrucken von hydrophobem Textilmaterial |
| US5038415A (en) * | 1989-01-10 | 1991-08-13 | Sumitomo Chemical Company, Limited | Disperse dye composition useful for dyeing of printing hydrophobic fiber materials: mixture of pyridone mono-azo dyes and optionally a quino-phthalone |
| DE4002482A1 (de) | 1990-01-29 | 1991-08-01 | Cassella Ag | Verfahren zum faerben und bedrucken von mischgeweben aus polyester und natuerlichen fasermaterialien |
| US5288680A (en) * | 1990-02-09 | 1994-02-22 | Cassella Aktiengesellschaft | Process for the preparation of finished dyeings which are fast to thermomigration: orange-dyed polyester fabrics |
| DE4003887A1 (de) * | 1990-02-09 | 1991-08-14 | Cassella Ag | Verfahren zur herstellung ausgeruesteter, thermomigrierechter faerbungen |
| DE4329762A1 (de) * | 1993-09-03 | 1995-03-09 | Cassella Ag | Verfahren zum Färben von Polyester und polyesterhaltigen Textilmaterialien |
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1996
- 1996-10-19 TW TW085112805A patent/TW375642B/zh not_active IP Right Cessation
- 1996-11-13 DE DE59607408T patent/DE59607408D1/de not_active Expired - Lifetime
- 1996-11-13 EP EP96810780A patent/EP0776948B1/de not_active Expired - Lifetime
- 1996-11-13 ES ES96810780T patent/ES2161342T3/es not_active Expired - Lifetime
- 1996-11-15 JP JP30428896A patent/JP3880109B2/ja not_active Expired - Fee Related
- 1996-11-20 CN CN96121730A patent/CN1076034C/zh not_active Expired - Lifetime
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- 1998-03-18 US US09/056,652 patent/US5935274A/en not_active Expired - Lifetime
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI470035B (zh) * | 2008-12-11 | 2015-01-21 | Dystar Colours Distrib Gmbh | 分散性染料之混合物 |
| CN108047752A (zh) * | 2017-12-29 | 2018-05-18 | 东营安诺其纺织材料有限公司 | 一种分散黄的生产工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW375642B (en) | 1999-12-01 |
| CN1076034C (zh) | 2001-12-12 |
| JP3880109B2 (ja) | 2007-02-14 |
| EP0776948A1 (de) | 1997-06-04 |
| ES2161342T3 (es) | 2001-12-01 |
| HK1005548A1 (en) | 1999-01-15 |
| EP0776948B1 (de) | 2001-08-01 |
| JPH09165529A (ja) | 1997-06-24 |
| US5935274A (en) | 1999-08-10 |
| DE59607408D1 (de) | 2001-09-06 |
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