CN1082528C - 分散染料 - Google Patents
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- CN1082528C CN1082528C CN97117683A CN97117683A CN1082528C CN 1082528 C CN1082528 C CN 1082528C CN 97117683 A CN97117683 A CN 97117683A CN 97117683 A CN97117683 A CN 97117683A CN 1082528 C CN1082528 C CN 1082528C
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- 239000000986 disperse dye Substances 0.000 title abstract 2
- 239000000975 dye Substances 0.000 claims abstract description 49
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 239000000463 material Substances 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 229920000728 polyester Polymers 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
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- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000012954 diazonium Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
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- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 4
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
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- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 229920002678 cellulose Polymers 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 239000004375 Dextrin Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
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- 239000000305 astragalus gummifer gum Substances 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
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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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
- C09B29/0816—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR
- C09B29/0817—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)- substituted by -COOR having N(-aliphatic residue-COOR)2 as substituents
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/56—Preparing azo dyes on the material
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
下式的分散染料，其中R1是氯或溴，R2是甲基或乙基，和R3是甲基或乙基。染料特别适合于染色或印染聚酯纤维纺织材料。
Description
本发明涉及分散染料，它们的制备方法以及它们在染色或印染半合成或合成疏水性纤维材料的使用。
分散染料，即，不含水溶性基团的染料，在现有技术中是已知的且已用于染色疏水性的纺织材料。然而，经常是所得的染料不能足够快地进行热移动。这种问题特别容易发生在红色到棕色的色泽内。
本发明的目的在于提供分散染料。借助这些分散染料可获得能进行快速热移动的染色而且它在尽染和热溶染色方法以及纺织印染过程中都具有良好的提升能力。这类染料还适用于拔染印花。
本发明的染料与下式一致
其中R1是氯或溴，R2是甲基或乙基，和R3是甲基或乙基。R1优选氯。R2优选甲基。R3优选甲基。特别优选的是下式的染料
通式(1)的染料可通过本身已知的方法来制备，即方便地将下式的化合物重氮化
并将此化合物的重氮鎓盐偶合到下式的偶合组分上
其中R1，R2，和R3如通式(1)所定义。
通式(2)化合物的重氮化作用是以本身已知的方式，例如在酸，典型的为盐酸或硫酸含水介质中用亚硝酸钠进行的。然而重氮化作用也可用其它重氮剂来进行，方便地是用亚硝基硫酸。重氮化作用的反应介质可含有附加的酸，典型得是磷酸，硫酸，乙酸，丙酸，盐酸或这些酸的混合物，例如磷酸和乙酸的混合物。重氮化作用可方便地在-10℃-30℃，优选-10℃-室温的温度范围内进行。
通式(2)的重氮化化合物对通式(3)的偶合组分的偶合同样以已知的方式方便地在酸，水溶液或含水-有机介质中进行，优选在范围为-10℃-30℃内，最优选低于10℃的温度下。合适的酸包括盐酸，乙酸，硫酸或磷酸。重氮化作用和偶合可典型地在同样的反应介质中进行。
通式(2)的重氮组分和通式(3)的偶合组分是已知的或能以本身已知的方式来制备的。
通式(1)的新型染料可用于染色和印染半合成和优选地合成疏水性纤维材料，特别是纺织材料。从含有如半合成或合成疏水性纤维材料的混纺物制造的纺织材料也可用新型的染料采染色或印染。
半合成纺织材料尤其是纤维素二代乙酸酯和纤维三乙酸酯。
合成疏水性纺织材料主要由线性芳香聚酯，典型地从对苯二酸和二醇类(特别是1，2-亚乙基二醇)或对苯二酸和1，4-双(羟甲基)环己烷得到的缩合物；由聚碳酸酯，典型地来自α，α-二甲基-4，4′-二羟基二苯基甲烷和光气，或由基于聚氯乙烯和聚酰胺的纤维组成。
新型的染料用已知的染色方法施用于纺织材料。典型地聚酯纤维材料在通常的阴或阳离子分散剂和可有可无的通常的溶胀剂存在下，在80-140℃的温度范围内由尽染工艺从含水分散液中染色。
优选地纤维素二代乙酸酯在65-85℃的温度范围内染色，和纤维三乙酸酯在最高115℃的温度下染色。
新型染料不能使同时存在于染池中的羊毛和棉花染色或只有少量的染色(极好的防染性)所以它们能够随时用于染色聚酯/羊毛和聚酯/纤维混纺物。
新型染料适合于热溶染色工艺，尽染和印花。尽染工艺是优选的。浴比取决与所使用的装置，底物和存在形式。然而，它可以从很宽的范围中选择，比如从1∶4-1∶100，但优选1∶6-1∶25。
纺织材料可以以任可形式存在，如纤维，线或非织造织物，或织物或针织物。
在使用前，将这种新型染料转化成染料配制剂是有利的。这可通过将染料研磨成平均粒径为0.1-10μm来实现。研磨工艺可在分散剂存在的情况下进行。典型的是，干燥染料与分散剂一起研磨，或以糊状形式与分散剂捏和，此后真空干燥或喷雾干燥。将水添加到所获得的配方中来制备印染浆料和染色浴。
传统的增稠剂被用来印染。此类增稠剂的典型例子是藻酸盐，糊精，阿拉伯树胶，结晶树胶，角豆树胶，黄蓍胶，羧甲基纤维素，羟乙基纤维素，淀粉或合成产物，包括聚丙烯酰胺，聚丙烯酸或其共聚物，或聚乙烯醇。
被列举的材料，尤其聚酯材料，用这种新型染料染成具有良好最终使用特性，特别具有良好的耐光照牢度和耐升华牢度的棕色色泽。特别值得一提的是具有极其良好的耐洗牢度和耐热移动特性。新型的染料也具有良好的排气性和累加性。
新型染料也可随时用来获得与其它染料相结合的混合色泽。
本发明的进一步目的是上述提到的本发明染料的使用和染色或印染半合成或合成疏水性纤维材料(优选纺织材料)的工艺，它包括将此新型染料作用于所说的材料或将染料引入其中。所列举的疏水性纤维材料优选聚酯纺织材料。可按本发明的工艺处理的其它的底物，优选的工艺条件已经在有关该新型染料的使用的详细描述中讨论。
按照本工艺染色或印染的疏水性纤维材料，优选聚酯纺织材料也可构成本发明的目的。
通式(1)的新型染料也适合于现代搭色法，例如热转移印染。
本发明由下面的实施例进行更详细的描述，其中，除非有另外的说明，份数和百分比按重量计。温度以摄氏度给出。重量份数和体积份数的关系和克与立方厘米的关系相同。
实施例1
在20-30℃的温度下将41.4重量份的2，6-二氯-4-硝基苯胺添加到138重量份的92％的硫酸中。此反应混合物在30℃下搅拌直到获得清晰的溶液。经20分钟向此反应混合物中滴加63.5重量份的亚硝基硫酸并且在25-30℃下连续搅拌90分钟。随后经90分钟将所得的重氮基溶液中滴加到由在130重量份乙酸中的61.7重量份的(N-3-乙酰氨基苯基)-N-甲酯基甲基氨基乙酸甲酯组成的溶液中，反应温度通过添加冰而保持在5-15℃。当向重氮溶液的添加过程完成时，混合物再搅拌1小时。
经50分钟向此混合物中滴加370重量份的30％NaOH水溶液，温度通过添加冰而保持在40℃。所得的沉淀物通过抽吸过滤来收集并用水洗涤，在干燥后获得101重量份的熔点为170-173℃的通式(1a)的棕色染料。这种染料将聚酯纺织材料染色成具有良好耐牢度特性，特别是耐热转移牢度和耐光牢度的棕色色泽。
实施例2-8
表1所列染料可用与实施例1的说明大致类似的方法制备。它们也将聚酯纺织材料染色成具有良好耐牢度特性，特别是耐热转移牢度和耐光牢度的棕色色泽。表1
| 实施例号 | R1 | R2 | R3 |
| 2 | Cl | C2H5 | CH3 |
| 3 | Cl | CH3 | C2H5 |
| 4 | Cl | C2H5 | C2H5 |
| 5 | Br | CH3 | CH3 |
| 6 | Br | C2H5 | CH3 |
| 7 | Br | CH3 | C2H5 |
| 8 | Br | C2H5 | C2H5 |
Claims (8)
1.下式的染料
其中R1是氯或溴，R2是甲基或乙基，和R3是甲基或乙基。
2.根据权利要求1的染料，其中R1是氯。
3.根据权利要求1或2中任意一项的染料，其中R2是甲基。
4.根据权利要求1的染料，其中R3是甲基。
5.具有下式的权利要求1的染料
6.制备根据权利要求1的通式(1)的染料的方法，它包括将下式的化合物重氮化
其中R1是氯或溴，并将此化合物的重氮盐偶合到下式的偶合组分上
其中R2是甲基或乙基，和R3是甲基或乙基。
7.权利要求1所要求的染料用于染色或印染半合成或合成疏水性纤维材料的用途。
8.根据权利要求7的用途，用于染色或印染聚酯纤维材料。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208896 | 1996-08-26 | ||
| CH2088/96 | 1996-08-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1176977A CN1176977A (zh) | 1998-03-25 |
| CN1082528C true CN1082528C (zh) | 2002-04-10 |
Family
ID=4225616
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97117683A Expired - Fee Related CN1082528C (zh) | 1996-08-26 | 1997-08-25 | 分散染料 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5869628A (zh) |
| EP (1) | EP0826741B1 (zh) |
| JP (1) | JP4171090B2 (zh) |
| KR (1) | KR19980018951A (zh) |
| CN (1) | CN1082528C (zh) |
| DE (1) | DE59702493D1 (zh) |
| ES (1) | ES2152074T3 (zh) |
| TW (1) | TW474971B (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0952190B1 (de) * | 1998-04-23 | 2003-06-04 | Ciba SC Holding AG | Dispersionsfarbstoffe |
| TW522163B (en) * | 1998-04-23 | 2003-03-01 | Ciba Sc Holding Ag | Dye, coupling component and processes for the preparation of the same |
| US7348592B2 (en) | 2004-11-29 | 2008-03-25 | The United States Of America As Represented By The Secretary Of The Navy | Carbon nanotube apparatus and method of carbon nanotube modification |
| MX2012007149A (es) * | 2009-12-23 | 2012-11-12 | Colourtex Ind Ltd | Colorantes azoicos dispersos. |
| US8506652B2 (en) * | 2009-12-23 | 2013-08-13 | Colourtex Industries Limited | Disperse dyes |
| CN102277012B (zh) * | 2011-04-29 | 2014-10-29 | 浙江闰土股份有限公司 | 一种分散枣红染料组合物 |
| KR101321427B1 (ko) * | 2011-11-21 | 2013-10-28 | 한국전기연구원 | 결상 보호용 3상 컨버터 시스템 및 그 제어방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0555179A1 (de) * | 1992-02-03 | 1993-08-11 | Ciba-Geigy Ag | Azofarbstoffe |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2373700A (en) * | 1940-06-29 | 1945-04-17 | Eastman Kodak Co | Azo compounds and material colored therewith |
| CH435500A (de) * | 1962-09-24 | 1967-05-15 | Ici Ltd | Verfahren zur Herstellung neuer Dispersionsfarbstoffe |
| US3637652A (en) * | 1962-09-24 | 1972-01-25 | Ici Ltd | Disperse monoazo dyestuffs |
| GB1519594A (en) * | 1974-10-31 | 1978-08-02 | Ici Ltd | Mass colouration of polyesters |
| CH636369A5 (de) * | 1978-09-19 | 1983-05-31 | Sandoz Ag | Faerbestabile mischungen von dispersionsfarbstoffen. |
| JPS55116754A (en) * | 1979-03-05 | 1980-09-08 | Mitsui Toatsu Chem Inc | Monoazo compound, its preparation, and dyeing of synthetic fiber |
| TW233304B (zh) * | 1992-04-02 | 1994-11-01 | Hoechst Mitsubishi Kasei | |
| JPH06329930A (ja) * | 1993-05-06 | 1994-11-29 | Ciba Geigy Ag | アゾ染料 |
-
1997
- 1997-08-19 EP EP97810581A patent/EP0826741B1/de not_active Expired - Lifetime
- 1997-08-19 DE DE59702493T patent/DE59702493D1/de not_active Expired - Lifetime
- 1997-08-19 ES ES97810581T patent/ES2152074T3/es not_active Expired - Lifetime
- 1997-08-20 JP JP22323897A patent/JP4171090B2/ja not_active Expired - Fee Related
- 1997-08-25 KR KR1019970040453A patent/KR19980018951A/ko not_active Application Discontinuation
- 1997-08-25 TW TW086112170A patent/TW474971B/zh not_active IP Right Cessation
- 1997-08-25 CN CN97117683A patent/CN1082528C/zh not_active Expired - Fee Related
- 1997-08-26 US US08/918,883 patent/US5869628A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0555179A1 (de) * | 1992-02-03 | 1993-08-11 | Ciba-Geigy Ag | Azofarbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| KR19980018951A (ko) | 1998-06-05 |
| EP0826741A1 (de) | 1998-03-04 |
| US5869628A (en) | 1999-02-09 |
| JP4171090B2 (ja) | 2008-10-22 |
| CN1176977A (zh) | 1998-03-25 |
| ES2152074T3 (es) | 2001-01-16 |
| EP0826741B1 (de) | 2000-10-18 |
| JPH1088015A (ja) | 1998-04-07 |
| DE59702493D1 (de) | 2000-11-23 |
| TW474971B (en) | 2002-02-01 |
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