CN115850991A - 高湿快速分散染料及其混合物 - Google Patents
高湿快速分散染料及其混合物 Download PDFInfo
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- CN115850991A CN115850991A CN202211356472.1A CN202211356472A CN115850991A CN 115850991 A CN115850991 A CN 115850991A CN 202211356472 A CN202211356472 A CN 202211356472A CN 115850991 A CN115850991 A CN 115850991A
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- Prior art keywords
- chr
- alkyl
- coo
- phenyl
- benzyl
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- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000012950 rattan cane Nutrition 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 229940080263 sodium dichloroacetate Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010294 sodium orthophenyl phenol Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LUPNKHXLFSSUGS-UHFFFAOYSA-M sodium;2,2-dichloroacetate Chemical compound [Na+].[O-]C(=O)C(Cl)Cl LUPNKHXLFSSUGS-UHFFFAOYSA-M 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229920006304 triacetate fiber Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
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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
- C09B29/06—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
- C09B29/081—Amino benzenes free of acid groups characterised by the amino group substituted amino group unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino
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- 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
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- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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- 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
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- 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
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- 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
- C09B29/083—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino having -N< (in a ring)
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- 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)
- C09B29/3634—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 heterocyclic rings
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- 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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Abstract
本发明公开了高湿快速分散染料及其混合物。所述分散染料的结构式如式(I)所示。本发明还公开所述分散染料的制备方法和应用。本发明提供的分散偶氮染料及其混合物,能够提供具有改进的牢度性能的染色,尤其是染色后的聚酯或聚酯与其他纤维的混纺物的耐湿和耐光牢度,并且此类染料对纤维具有高亲和力,这反映在良好的提升性能上。
Description
本发明涉及分散偶氮染料及其混合物。
具有改善的牢度性能,特别是耐洗牢度的分散染料越来越受到关注。
具有2,4,6-二硝基-卤素重氮组分(a)作为结构单元的分散染料是公知的,并且是大多数红色,尤其是紫色和蓝色分散染料以及这些染料的混合物的基础。
如式(a)所示的染料及其制备方法是已知的,并且在各种专利中具有描述,如:GB2030169,DE 4335261,DE 3112427,DE 2818653,WO 2005/056690或EP 0 240 902,但是在耐光和耐湿性能方面具有缺陷。卤素是氟的式(a)所示染料很少有举例说明。
如式(b)所示的替代型式2,4,5-二硝基-卤素也是已知的,例如参见WO 2005/056690或WO 2005/040283。它们与特殊的偶联组分结合能够得到具有改进的牢度性能的染料。
尽管如此,对于在染色的聚酯或聚酯与其他纤维如纤维素,尼龙,弹性纤维和羊毛的混纺物中能够提供改进的牢度性能的分散染料仍然有需求。
令人惊奇的是,现已发现2,4,5-二硝基-氟-苯胺作为重氮组分转化的分散偶氮染料及其混合物,能够提供具有改进的牢度性能的染色,尤其是染色后的聚酯或聚酯与其他纤维的混纺物的耐湿和耐光牢度,并且此类染料对纤维具有高亲和力,这反映在良好的提升性能上。大约35年前,这类化合物中的一种,具有下式:
已经在Monatshefte für Chemie 111,(1980),p.529-533中,作为生产可用作酚类TLC检测的化合物的中间体公开。
本发明涉及式(I)所示染料及其混合物
其中
X为氢或卤素
K为芳族或杂芳族偶联组分
优选的K选自由如下基团组成的群组:氨基苯,萘-1-基,萘-2-基,喹啉或任何其它N-杂环稠环系统,其各自可以是未取代的或取代的,以及苯酚或萘酚-基,其各自可以是未取代的或取代的。
通常,优选其中X不是氢的染料。然而,存在许多优选的结构,其中X是氢。因此,在下文中,其中优选实施例详细描述为,例如“X是氢或卤素”或者“X是氢,溴或氯”,这种表述是指所有不同的亚类,即X为氢的亚类,X不为氢而是任何其它的亚类,以及所述的亚类,其中X是任何所提到过的,例如卤素。
优选的式(I)所示染料,其中
X为氢或卤素,
K为式(2)所示基团
其中各自独立的
R1为氢,未取代的或取代的C1-C4-烷基,未取代的或取代的C1-C4-烷氧基,氯,溴,苄氧基或–O-(CH2)n-A1-C1-C4-烷基,
R2为氢,羟基,未取代的或取代的C1-C4-烷基,未取代的C1-C4-烷氧基,氯,溴,酰氧基,酰氨基(例如NHCO-(CH2)n-A1-C1-C4-烷基)或烷基-磺酰基氨基(例如NHSO2-(CH2)n-A1-C1-C4-烷基),
其中n为1至4,A1为O,O-CO,O-CO-O或CO-O,
R3和R4为未取代的或取代的C1-C4-烷基,未取代的或取代的苯基,未取代或取代的苄基,
或者R1和R3一起形成5-或6-元脂族,杂脂族,芳族或杂芳族的环,
其中5-或6-元环是未取代的或取代的。
X为氢的染料形成一组优选的染料。X不为氢的染料形成另一组优选的染料。还有一组优选的染料是,其中X为卤素,特别是Br或Cl。
更加优选的是式(II)所示染料
其中各自独立的X为氢,氯或溴,
R1为氢,羟基,C1-C4-烷基,溴,氯或C1-C4-烷氧基,
R2为氢,羟基,羧基,C1-C4-烷基,C1-C4-烷氧基,卤素,酰氧基,酰氨基(例如NHCO-C1-C4-烷基,NHCO-芳基,NHCO-苄基)或磺酰基氨基(例如NHSO2-C1-C4-烷基),
R3和R4为氢,C1-C4-烷基,(CH2)n-苯基,CH2-CH=CH2,(CH2)n-OH,(CH2)n-O-(C1-C4)-烷基,(CH2)n-O-苯基,(CH2)n-O-苄基,(CH2)n-O-(CH2)m-OH,(CH2)n-O-(CH2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)m-O-苯基,(CH2)n-O-(CH2)m-O-苄基,(CH2)n-COOH,(CH2)n-COO-(C1-C4)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C4)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C4)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-(CH2)p-(C1-C4)-烷基,CHR2-(CH2)p苯基,CHR2-CH=CH2,CHR2-(CH2)p-OH,CHR2-(CH2)p-O-(C1-C4)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-O-(C1-C4)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,(CH2)n-O-(CH2)p-(CHR2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-苯基,(CH2)n-O-(CH2)p-(CHR2)m-O-苄基,CHR2-(CH2)p-COOH,CHR2-(CH2)p-COO-(C1-C4)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,(CH2)n-COO(CH2)p-(CHR2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-苯基,CHR2-(CH2)p-O-CO-苄基,CHR2-(CH2)p-2-糠基,COO-CHR2-(CH2)p-2-脱氢吡喃基,CHR2-(CH2)p-O-(CH2)n-2-糠基,CHR2-(CH2)p-O-(CH2)n-2-脱氢吡喃基,
其中所有的苄基和苯基环均可以被C1-C4-烷基,C1-C4-烷氧基,卤素,硝基,氰基或COOR2所取代,
n为1至4,
m为1至4,
P为0至3。
进一步更加优选的是式(II)所示染料,其中各自独立的X为氢,氯或溴,
R1为氢,甲基或甲氧基,
R2为氢,羟基,COOH,COO-C1-C2-烷基,C1-C2-烷基,C1-C2-烷氧基,氯,溴,-NHCO-C1-C2-烷基,-NHCO-芳基,-NHCO-苄基,-NHSO2-C1-C2-烷基或–NHSO2-芳基,
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)2-O-(CH2)m-O-苯基,(CH2)2-O-(CH2)m-O-苄基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-CH=CH2,CHR2-(CH2)p-O-(C1-C2)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-O-(C1-C2)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基,CHR2-(CH2)p-O-CO-苯基或CHR2-(CH2)p-O-CO-苄基,
n为1或2,
m为1或2,
p为0或1。
最优选的是式(II)所示染料,其中各自独立的X为氢,氯或溴,
R1为氢,甲基或甲氧基,
R2为氢,羟基,COOH,COO-(C1-C2)-烷基,(C1-C2)-烷基,氯,溴,–NHCO-(C1-C2)-烷基,–NHSO2-(C1-C2)-烷基,
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,COO-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-糠基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)-O-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)p-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基or CHR2-(CH2)p-O-CO-苯基,
n为1或2,
m为1或2,
p为0或1。
本发明另一种优选的技术方案是式(III)所示染料
其中各自独立的X为氢,氯或溴,
R1为氢,C1-C4-烷基,溴,氯或C1-C4-烷氧基,
R5为氢或C1-C4-烷基,
R3和R4为氢,C1-C4-烷基,(CH2)n-苯基,CH2-CH=CH2,(CH2)n-OH,(CH2)n-O-(C1-C4)-烷基,(CH2)n-O-苯基,(CH2)n-O-苄基,(CH2)n-O-(CH2)m-OH,(CH2)n-O-(CH2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)m-O-苯基,(CH2)n-O-(CH2)m-O-苄基,(CH2)n-COOH,(CH2)n-COO-(C1-C4)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C4)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C4)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基CHR2-(CH2)p-(C1-C4)-烷基,CHR2-(CH2)p-苯基,CHR2-CH=CH2,CHR2-(CH2)p-OH,CHR2-(CH2)p-O-(C1-C4)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-O-(C1-C4)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COOH,CHR2-(CH2)p-COO-(C1-C4)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,(CH2)n-COO(CH2)p-(CHR2)m-CO-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-苯基,(CH2)n-O-(CH2)p-(CHR2)m-O-苄基,CHR2-(CH2)p-O-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-苯基,CHR2-(CH2)p-O-CO-苄基,COO-CHR2-(CH2)p-2-糠基,COO-CHR2-(CH2)p-2-脱氢吡喃基,CHR2-(CH2)p-O-(CH2)n-2-糠基或CHR2-(CH2)p-O-(CH2)n-2-脱氢吡喃基,
其中所有的苄基和苯基环均可以被(C1-C4)-烷基,(C1-C4)-烷氧基,卤素,硝基,氰基或COOR2所取代,
n为1至4,
m为1至4,
p为0至3。
更加优选的是式(III)所示染料,其中各自独立的X为氢,氯或溴,
R1为氢,甲基或甲氧基,
R5为甲基或乙基,
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)2-O-(CH2)m-O-苯基,(CH2)2-O-(CH2)m-O-苄基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,-(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-CH=CH2,CHR2-(CH2)p-O-(C1-C2)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-O-(C1-C2)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基,CHR2-(CH2)p-O-CO-苯基或CHR2-(CH2)p-O-CO-苄基,
n为1或2,
m为1或2,
p为0或1。
进一步更加优选的是式(III)所示染料,其中各自独立的X为氢,氯或溴,
R1为氢,甲基或甲氧基,
R5为甲基,
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,COO-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-糠基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)-O-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)p-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基或CHR2-(CH2)p-O-CO-苯基,
n为1或2,
m为1或2,
p为0或1。
本发明还提供了式(I)所示染料及其混合物的制备方法,包括:
a)式(IV)或(V)的重氮化
其中X如上述所定义
b)将步骤a)中获得的重氮盐与式(2)所示化合物偶联。
式(IV)和式(V)化合物的重氮化,可分别通过本领域技术人员已知的重氮化方法进行,优选通过在酸性介质中使用亚硝酸钠或亚硝基硫酸,所述的酸性介质采用无机酸例如盐酸,硫酸或磷酸或其混合物,或者有机酸如乙酸或丙酸或其混合物。无机酸与有机酸的混合物也可以有利地使用。
由式(IV)或(V)的化合物重氮化获得的重氮盐与式(2)所示化合物的偶联反应可通过已知的方法进行。
式(2)所示化合物是已知的并且可商购获得,或者可以通过本领域技术人员已知的常见化学反应合成,例如在化学百科全书文献例如Ullmann's Encylobedia ofIndustrial Chemistry,Houben-Weyl,其他科学文献和众多专利中所公开的方法。
通过类比,本发明中使用的所有物质均可如所述进行合成。
本发明的染料可以单独使用或者与根据本发明的其它染料和/或其它物质的混合使用。
因此,包含如上所述的一种或多种染料的化学组合物也是本发明的一个方面。
由上述两种或多种染料组成的化学组合物形成本发明的另一个优选方面。
当本发明的染料或染料混合物用于染色时,通过分散剂和润湿剂以常规方式将染料/染料混合物分散在水性介质中,以制备用于染色的染浴或用于纺织品印花的印花浆。
因此,包含上述染料或染料混合物的用于染色的水性分散体也构成本发明的一个方面。
分散剂的典型例子是木质素磺酸盐,萘磺酸/甲醛缩合物和苯酚/甲酚/对氨基苯磺酸/甲醛缩合物,润湿剂的典型例子是可被磺化或磷酸化的烷基芳基乙氧基化物,其它可能出现的成分的典型例子是无机盐,除尘剂如矿物油或壬醇,有机液体和缓冲剂。基于染料/染料混合物的重量,分散剂的含量可以在30至500%。基于染料/染料混合物的重量,可以使用含量为0至5%的除尘剂。
本发明的染料和染料混合物非常适合于疏水性材料的染色和印花,所获得的染色和印花成品的具有显著的均匀色调和高色牢度。显著的特征包括良好的洗涤和接触牢度,以及优异的颜色提升性能,特别是对聚酯和聚酯-氨纶材料。
因此,本发明还提供了本发明的染料和染料混合物用于疏水性材料染色和印花的用途,并且提供了在常规操作中染色或印花此类材料的方法,其中本发明的染料混合物用作着色剂。
上述疏水材料可以是合成或半合成来源的。合适的材料包括,例如次乙酸纤维素,三乙酸纤维素,聚酰胺,聚丙交酯,以及,特别是高分子量聚酯。由高分子量聚酯制成的材料进一步特别是指那些基于聚对苯二甲酸乙二醇酯或聚对苯二甲酸丙二醇酯的。还涵盖例如混纺织物和混纺纤维,如聚酯-棉或聚酯-氨纶。疏水性合成材料可以采取膜或片状或丝状构造的形式,并且可以是已经加工形成例如纱线或编织或针织的纺织材料。优选纤维纺织材料,其也可以例如以微纤维的形式存在。
根据本发明提供的用途的染色可以常规方式进行,优选由水分散体,任选地在载体存在下,于80至约110℃之间通过竭染法,或于110至140℃下在染色高压釜中通过HT法进行,并且还可通过所谓的热固法,其中织物用染色液浸轧,随后在约180至230℃固色。
上述材料的印花可以已知的方式进行,通过将本发明的染料混合物掺入印花浆中,随后对织物作印花处理以固定染料,任选地在载体存在下,于180至230℃下,采用HT蒸汽,加压蒸汽或干热。
合适的工艺条件可以选自以下:
(i)竭染:在pH为4至8.5,温度为125至140℃下实施10至120分钟,并且压力为1至2巴,任选地加入螯合剂;
(ii)连续式染色:在pH为4至8.5,温度为190至225℃下实施15秒至5分钟,任选地加入迁移抑制剂;
(iii)直接印花法:在pH为4至6.5,温度为160至185℃下高温蒸煮4至15分钟,或者在温度为190至225℃下用干热烘烤固色15秒至5分钟,或者在120至140℃,1至2巴的条件下压蒸10至45分钟,任选地加入染料重量5至100%的润湿剂和增稠剂(例如藻酸盐);
(iv)拔染印花(通过将染料浸轧到纺织材料上,干燥以及套印):在pH为4至6.5的条件下排,任选地加入迁移抑制剂和增稠剂;
(v)载体法染色:在pH为4至7.5,温度为95至100℃的条件下,使用载体如甲基萘,二苯胺或2-苯基苯酚,任选地加入螯合剂;以及
(vi)对于乙酸酯,三乙酸酯和尼龙在pH为4至7.5下进行常压染色,对于乙酸酯在温度为约85℃下,对于三乙酸酯和尼龙在温度为约90℃下实施15至90分钟,任选地加入螯合剂。
对于在染色液,浸轧液或印花浆中使用,本发明的染料混合物处于非常细微的细分状态。染料的精细细分以已知的方式来完成,通过将它们与分散剂一起在液体介质(优选水)中打浆,并使混合物经受剪切力的作用,初始存在的染料颗粒被机械粉碎至一定程度,从而获得最佳比表面积,并且染料的沉降非常低。该操作在合适的磨机中进行,例如球磨机或砂磨机。染料的粒度通常在0.1和5μm之间,优选约1μm。
在研磨操作中使用的分散剂可以是非离子或阴离子的。非离子分散剂是,例如:环氧烷烃(如环氧乙烷或环氧丙烷)与可烷基化的化合物(如脂肪醇,脂肪胺,脂肪酸,酚,醇酚和羧酰胺)的反应产物。阴离子分散剂是,例如:木素磺酸盐,烷基或烷基芳基磺酸盐,或者烷基芳基聚乙二醇醚硫酸盐。
对于大多数应用,以这种方式获得的染料制剂是可倾倒的。因此,在这些情况下,对染料含量和分散剂含量具有限定。一般来说,将分散体调节至使染料含量不超过50wt%,并且分散剂含量不超过约25wt%。出于经济原因,染料含量通常不低于15wt%。
所述的分散体也可以包含其它助剂,例如作为氧化剂的那些,如间硝基苯磺酸钠,或者杀菌剂,如邻苯基苯酚钠和五氯苯酚钠,尤其是已知的“酸供体”,如丁内酯,一氯乙酰胺,氯乙酸钠,二氯乙酸钠,3-氯丙酸的钠盐,硫酸的单酯如十二烷基硫酸盐,还有乙氧基化和丙氧基化醇的硫酸酯,例如丁基乙二醇硫酸酯。
以这种方式获得的染料分散体用于制备染色液和印花浆有很大优势。
在某些使用领域中,优选粉末制剂。这些粉末包括所述的染料,分散剂和其它助剂,如润湿剂,氧化剂,防腐剂和防尘剂,以及上述“酸供体”。
一种制备粉末形式的染料制剂的优选方法包括,从上述液体染料分散体中除去液体,通过例如真空干燥,冷冻干燥或通过在鼓式干燥器上干燥,但优选通过喷雾干燥。
染色液是通过用染色介质(优选用水)稀释所需量的上述染料制剂进行制备,以达到例如使染色浴比为5:1至50:1的程度。另外,染色液通常与其它的染色助剂如分散剂,润湿剂和固定助剂混合。添加有机和无机酸例如乙酸,琥珀酸,硼酸或磷酸以设定pH为4至5,优选4.5。加入足够量的缓冲体系对已设定的pH进行缓冲是有利的。一种有利的缓冲体系,例如乙酸/乙酸钠体系。
当染料混合物用于纺织品印花时,将所需量的上述染料制剂以常规方式与增稠剂,以及任选的其他助剂一起捏合以形成印刷浆,所述的增稠剂例如碱金属藻酸盐或类似物,所述的其它助剂例如如固定促进剂,润湿剂和氧化剂。
本发明还提供了通过喷墨法用于数字纺织品印花的油墨,其包含本发明的染料混合物。
本发明的油墨优选为水性的,并且基于油墨的总重量,包含例如0.1wt%至50wt%本发明的染料混合物,优选1wt%至30wt%,更优选1wt%至15wt%。此外,它们具体包含0.1wt%至20wt%的分散剂。合适的分散剂是本领域技术人员已知的,可商购获得,并且包括例如:磺化或磺甲基化的木质素,芳族磺酸和甲醛的缩合产物,取代或未取代的苯酚和甲醛的缩合产物,聚丙烯酸酯和相应的共聚物,改性聚氨酯,以及环氧烷与可烷基化的化合物(例如脂肪醇,脂肪胺,脂肪酸,羧酰胺和未取代或取代的苯酚)的反应产物。
本发明的油墨还可以包含常用的添加剂,例如粘度调节剂,以在20至50℃的温度范围内将粘度设定在1.5至40.0mPas的范围内。优选的油墨具有1.5至20mPas的粘度,并且特别优选的油墨具有1.5至15mPas的粘度。
合适的粘度调节剂包括流变添加剂,例如聚乙烯基己内酰胺,聚乙烯吡咯烷酮及其共聚物,聚醚多元醇,缔合增稠剂,聚脲,藻酸钠,改性半乳甘露聚糖,聚醚脲,聚氨酯和非离子纤维素醚。
所述油墨还可以包含常规助剂,例如用于抑制真菌和细菌生长的物质,基于油墨的总重量,其含量为0.01wt%至1wt%。
这种合适的印花或配制助剂的综述更详细地给出在例如EP 1 735 385中。
与常规纺织品印花的印花油墨已经包含所有必需的化学品相比,在数字或喷墨印花中,必须在单独的预处理步骤中将助剂施加到纺织品基材上。
染料也可以使用超临界二氧化碳施加到纺织材料上,在这种情况下,染料配制剂可以任选地省去。
合成纺织材料可以优选选自芳族聚酯,特别是聚对苯二甲酸乙二醇酯,聚酰胺,特别是聚己二酰己二胺。也可以选择次级醋酸纤维素,三醋酸纤维素和天然纺织材料,特别是纤维素材料和羊毛。特别优选的纺织材料是芳香族聚酯或其与任何所述纺织材料纤维的纤维混纺物。特别优选的纤维混纺物包括聚酯纤维素,如聚酯-棉和聚酯-羊毛。纺织材料或其混纺物可以是细丝,松散纤维,纱线或者机织或针织织物的形式。
特别地,在聚酯纤维中,不仅普通的聚酯纤维(常规旦尼尔纤维),而且微纤维(细旦尼尔纤维,其小于0.6旦尼尔)均可作为能够使用本发明的染料混合物成功染色的纤维。
通常所有种类的纤维都可被染色,因此含有以化学和/或物理结合形式的上述染料混合物的纤维及包含所述纤维的混纺物构成本发明的另一方面,所述的纤维选自如下群组:合成纤维材料,尼龙材料,尼龙-6,尼龙-6.6和芳族聚酰胺纤维,植物纤维,种子纤维,棉花,有机棉,木棉,椰壳纤维;韧皮纤维,亚麻,大麻,黄麻,洋麻,苎麻,藤;叶纤维,剑麻,赫纳昆纤维,芭蕉纤维;秸秆纤维,竹纤维;动物纤维,羊毛,有机羊毛,蚕丝,羊绒羊毛,羊驼毛纤维,马海毛,安哥拉纤维以及毛皮和皮革材料;人造,再生和再循环的纤维,纤维素纤维;纸纤维,纤维素再生纤维,粘胶人造丝纤维,乙酸酯和三乙酸酯纤维,以及莱赛尔纤维。
下面的实施例用于说明本发明。除非另有说明,份和百分比均按重量计。重量份和体积份之间的关系是千克与升的关系。
实施例:
中间体1:
将192ml(2Mol)间位3-氟-苯胺加入到200ml甲苯胺中并搅拌。
将该混合物加热至50℃,加入203ml(2.1Mol)乙酸酐,同时保持温度在50至60℃。2小时后,真空浓缩反应混合物。将剩余的物质与1000ml过滤的冷水混合,并在真空条件下干燥,得到292g中间体1。
中间体2:
在-5至0℃下,将137.9g(0.9Mol)中间体1缓慢加入到259g HNO3和630g H2SO4的混合物中。该混合物在0至5℃下搅拌1小时,然后加入到搅拌下的4升冰/水的混合物中,通过过滤分离并在真空条件下干燥,得到140g中间体2
中间体3:
将140g中间体2加入到545ml 50%H2SO4中,并在搅拌下加热3小时至100℃。将该混合物加入到5l冰/水中,通过过滤分离并在真空条件下干燥,得到107g中间体3
中间体3的其它合成方法参见:(Organic Letters,14(10),2504-2507;2012/Journal of Organic Chemistry,27,1910-11;1962/Bioorganic&Medicinal ChemistryLetters,21(14),4189-4192;2011)
中间体4:
将38.8g(0.193mol)中间体3溶解在200ml乙酸中,并加入40ml 37%HCl。将混合物在25℃下搅拌,并缓慢加入21ml 35%H2O2。将该混合物在25~30℃下搅拌3天,然后倒入1000ml冰/水中,通过过滤分离并在真空条件下干燥,得到39.5g中间体4
中间体5:
将38.8g(0.193mol)中间体3溶于200ml乙酸中,并在25℃下缓慢加入11.6ml(0.22Mol)溴。将该混合物在25至30℃下搅拌3天,然后倒入1000ml冰/水中,通过过滤分离并在真空条件下干燥,得到48.1g中间体5
偶联组分(K)/(2)和(2a)
用于分散染料是众所周知的,并且记载于化学百科全书文献如Ullmann'sEncylobedia of Industrial Chemistry,Houben-Weyl,其它科学文献和众多专利中。因此,仅给出少数偶联组分的详细合成。
偶联体1:
通过在5%HCl水溶液中搅拌将80g Zn粉末活化,过滤并用水洗涤。将54g(0.3Mol)3-氨基-4-甲氧基乙酰苯胺在250ml乙酸和25ml水和35.2g(0.3Mol)甲基乙酰乙酸酯(CH3COCH2COOCH3)中搅拌。在25℃下向该混合物中加入活化的Zn粉末。反应开始后温度升高,并在80至90℃保持12小时。在真空下蒸除乙酸,加入300ml水和300ml CH2Cl2。用氨溶液将pH调节至7,并强烈混合两相,在相分离后,分离出有机相。
水相用100ml CH2Cl2萃取,合并有机相,用水洗涤,MgSO4干燥并真空蒸发,得到39.2g偶联体1。
染料实施例1:
重氮化:
将8.8g中间体3与85ml乙酸/丙酸(60/40)混合并冷却至0℃。在0℃下缓慢加入8.0ml亚硝基硫酸。将该混合物在0℃下搅拌4小时,过量的亚硝酸盐被酰胺磺酸破坏。
偶联:
将9.4g 3-(N,N-二乙基)-氨基乙酰苯胺与140ml甲醇和10g乙酸钠和2g尿素混合,并冷却至5℃。向该混合物中缓慢加入重氮化物,并在5℃下将反应混合物搅拌30分钟。加入100ml水,通过过滤分离所得产物。用乙醇重结晶并在真空条件下干燥后,得到10.6g染料。
本发明的染料进一步配以分散剂,用玻璃珠研磨并通过喷雾干燥法干燥,在分散染料的典型染色条件下,在例如聚酯或聚酯混纺物上给出深紫色染色或印花,具有非常好的色牢度性能。
实施例2:
重氮化:
将8.8g中间体5与85ml乙酸/丙酸(60/40)混合并冷却至0℃。在0℃下缓慢加入8.0ml亚硝基硫酸。将该混合物在0℃下搅拌4小时,过量的亚硝酸盐被酰胺磺酸破坏。
偶联:
将11.04g 3-(N,N-二丙基)甲磺酰基甲胺(N-(3-二丙基氨基-苯基)甲磺酰胺)与140ml甲醇和10g乙酸钠和2g尿素混合,并冷却至5℃。向该混合物中缓慢加入重氮化物,将反应混合物在5℃下搅拌30分钟。加入100ml水,通过过滤分离所得产物。用丙酮重结晶并在真空条件下干燥后,得到10.6g实例2-染料。
该本发明所得染料配以分散剂,用玻璃珠研磨并通过喷雾干燥法干燥,在分散染料的典型染色条件下,在例如聚酯或聚酯混纺物上给出深紫色染色或印花,具有非常好的色牢度性能。
实施例3~5:
使用以下环化/取代的偶联体(偶联体2至4)和重氮组分中间体3或中间体5,也可以按照实施例1的方法制备高耐洗染料。
将聚酯染成深红色,
将聚酯染成深红蓝色调(所谓红蓝色调即带红色的蓝色调),
将聚酯染成深蓝红色调(所谓蓝红色调即带蓝色的红色调)。
式(IIa)所示实施例6~63
可按照实施例1或2的方法进行制备
使用中间体3作为重氮组分,和式(2)所示偶联组分,如下:
式(IIb)所示实施例64~95
可按照实施例1或2的方法进行制备
使用中间体4或中间体5作为重氮组分,和式(2)所示偶联组分,如下:
式(IIc)所示实施例96~202
即结构通式(II)中的R2是NHCO-R5,并且其中R5是烷基,即式(II)的R2是NHCO-(C1-C2)-烷基,
其可按照实施例1或2的方法进行制备
使用中间体3作为重氮组分,和式(2a)所示偶联组分,如下:
式(III)所示实施例203~312
可按照实施例1或2的方法进行制备
使用中间体4或中间体5作为重氮组分,和式(2a)所示偶联组分,如下:
Claims (15)
2.根据权利要求1所述的染料,具有式(II)所示的结构
其中各自独立的
X为氢,氯或溴;
R1为氢,羟基,C1-C4-烷基,溴,氯或C1-C4-烷氧基;
R2为羟基,酰氨基或烷基磺酰基氨基;
R3和R4为氢,C1-C4-烷基,(CH2)n-苯基,CH2-CH=CH2,(CH2)n-OH,(CH2)n-O-(C1-C4)-烷基,(CH2)n-O-苯基,(CH2)n-O-苄基,(CH2)n-O-(CH2)m-OH,(CH2)n-O-(CH2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)m-O-苯基,(CH2)n-O-(CH2)m-O-苄基,(CH2)n-COOH,(CH2)n-COO-(C1-C4)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C4)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C4)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-(CH2)p-(C1-C4)-烷基,CHR2-(CH2)p苯基,CHR2-CH=CH2,CHR2-(CH2)p-OH,CHR2-(CH2)p-O-(C1-C4)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-O-(C1-C4)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,(CH2)n-O-(CH2)p-(CHR2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-苯基,(CH2)n-O-(CH2)p-(CHR2)m-O-苄基,CHR2-(CH2)p-COOH,CHR2-(CH2)p-COO-(C1-C4)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,(CH2)n-COO(CH2)p-(CHR2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-苯基,CHR2-(CH2)p-O-CO-苄基,CHR2-(CH2)p-2-糠基,COO-CHR2-(CH2)p-2-脱氢吡喃基,CHR2-(CH2)p-O-(CH2)n-2-糠基,CHR2-(CH2)p-O-(CH2)n-2-脱氢吡喃基;
其中所有的苄基和苯基环均可以被C1-C4-烷基,C1-C4-烷氧基,卤素,硝基,氰基或COOR2所取代;
n为1至4;
m为1至4;
P为0至3。
3.根据权利要求2所述的染料,具有式(II)所示的结构,其中各自独立的
X为氢,氯或溴;
R1为氢,甲基或甲氧基;
R2为羟基,-NHCO-C1-C2-烷基,-NHCO-芳基,-NHCO-苄基或-NHSO2-C1-C2-烷基;
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)2-O-(CH2)m-O-苯基,(CH2)2-O-(CH2)m-O-苄基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-CH=CH2,CHR2-(CH2)p-O-(C1-C2)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-O-(C1-C2)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基,CHR2-(CH2)p-O-CO-苯基或CHR2-(CH2)p-O-CO-苄基;
n为1或2;
m为1或2;
p为0或1。
4.根据权利要求2所述的染料,具有式(II)所示的结构,其中各自独立的
X为氢,氯或溴;
R1为氢,甲基或甲氧基;
R2为羟基,–NHCO-(C1-C2)-烷基或–NHSO2-(C1-C2)-烷基;
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,COO-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-糠基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)-O-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)p-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基或CHR2-(CH2)p-O-CO-苯基;
n为1或2;
m为1或2;
p为0或1。
5.根据权利要求1所述的染料,具有式(III)所示的结构
其中各自独立的
X为氢,氯或溴;
R1为氢,C1-C4-烷基,溴,氯或C1-C4-烷氧基;
R5为氢或C1-C4-烷基;
R3和R4为氢,C1-C4-烷基,(CH2)n-苯基,CH2-CH=CH2,(CH2)n-OH,(CH2)n-O-(C1-C4)-烷基,(CH2)n-O-苯基,(CH2)n-O-苄基,(CH2)n-O-(CH2)m-OH,(CH2)n-O-(CH2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)m-O-苯基,(CH2)n-O-(CH2)m-O-苄基,(CH2)n-COOH,(CH2)n-COO-(C1-C4)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C4)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C4)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基CHR2-(CH2)p-(C1-C4)-烷基,CHR2-(CH2)p-苯基,CHR2-CH=CH2,CHR2-(CH2)p-OH,CHR2-(CH2)p-O-(C1-C4)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-OH,CHR2-(CH2)p-O-(CH2)m-O-(C1-C4)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COOH,CHR2-(CH2)p-COO-(C1-C4)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C4)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,(CH2)n-COO(CH2)p-(CHR2)m-CO-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-(C1-C4)-烷基,(CH2)n-O-(CH2)p-(CHR2)m-O-苯基,(CH2)n-O-(CH2)p-(CHR2)m-O-苄基,CHR2-(CH2)p-O-CO-(C1-C4)-烷基,CHR2-(CH2)p-O-CO-苯基,CHR2-(CH2)p-O-CO-苄基,COO-CHR2-(CH2)p-2-糠基,COO-CHR2-(CH2)p-2-脱氢吡喃基,CHR2-(CH2)p-O-(CH2)n-2-糠基或CHR2-(CH2)p-O-(CH2)n-2-脱氢吡喃基;
其中所有的苄基和苯基环均可以被(C1-C4)-烷基,(C1-C4)-烷氧基,卤素,硝基,氰基或COOR2所取代;
n为1至4;
m为1至4;
p为0至3。
6.根据权利要求5所述的式(III)所示染料,其中各自独立的
X为氢,氯或溴;
R1为氢,甲基或甲氧基;
R5为甲基或乙基;
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)2-O-(CH2)m-O-苯基,(CH2)2-O-(CH2)m-O-苄基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,-(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-COO(CH2)m-CO-苄基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,(CH2)n-O-CO-苄基,COO-(CH2)n-2-糠基,COO-(CH2)n-2-脱氢吡喃基,(CH2)m-O-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-脱氢吡喃基,CHR2-CH=CH2,CHR2-(CH2)p-O-(C1-C2)-烷基,CHR2-(CH2)p-O-苯基,CHR2-(CH2)p-O-苄基,CHR2-(CH2)p-O-(CH2)m-O-(C1-C2)-烷基,CHR2-(CH2)p-O-(CH2)m-O-苯基,CHR2-(CH2)p-O-(CH2)m-O-苄基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)p-COO-苯基,CHR2-(CH2)p-COO-苄基,CHR2-(CH2)p-CN,CHR2-(CH2)p-COO(CH2)m-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-COO(CH2)m-CO-苄基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基,CHR2-(CH2)p-O-CO-苯基或CHR2-(CH2)p-O-CO-苄基;
n为1或2;
m为1或2;
p为0或1。
7.根据权利要求5所述的式(III)所示染料,其中各自独立的
X为氢,氯或溴;
R1为氢,甲基或甲氧基;
R5为甲基;
R3和R4为氢,C1-C2-烷基,(CH2)-苯基,CH2-CH=CH2,(CH2)2-O-(C1-C2)-烷基,(CH2)2-O-苯基,(CH2)2-O-苄基,(CH2)2-O-(CH2)m-O-(C1-C2)-烷基,(CH2)n-COO-(C1-C2)-烷基,(CH2)n-COO-苯基,(CH2)n-COO-苄基,(CH2)n-CN,(CH2)n-COO(CH2)m-CO-(C1-C2)-烷基,(CH2)n-COO(CH2)m-CO-苯基,(CH2)n-O-CO-(C1-C2)-烷基,(CH2)n-O-CO-苯基,COO-(CH2)n-2-糠基,(CH2)m-O-(CH2)n-2-糠基,CHR2-(CH2)p-COO-(C1-C2)-烷基,CHR2-(CH2)-O-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)p-CO-(C1-C2)-烷基,CHR2-(CH2)p-COO(CH2)m-CO-苯基,CHR2-(CH2)p-O-CO-(C1-C2)-烷基或CHR2-(CH2)p-O-CO-苯基;
n为1或2;
m为1或2;
p为0或1。
9.包含一种或多种根据权利要求1至7任一项所述的染料的化学组合物。
10.由两种或多种根据权利要求1至7任一项所述的染料组成的化学组合物。
11.包含一种或多种根据权利要求1至7任一项所述的染料的用于染色的水性分散体。
12.根据权利要求1至7任一项所述的染料用于疏水性材料染色和印花的方法。
13.用于数字纺织品印花的油墨,其包含根据权利要求1至7任一项所述的染料。
14.根据权利要求1至7任一项所述的染料,根据权利要求9或10所述的化学组合物,或者根据权利要求11所述的水性分散体,在纤维及其混纺物的染色中的应用,所述的纤维选自如下群组:合成纤维材料;植物纤维;动物纤维;人造,再生和再循环的纤维。
15.含有一种或多种以化学和/或物理结合形式的根据权利要求1至7任一项所述的染料的纤维及包含所述纤维的混纺物,所述的纤维选自如下群组:合成纤维材料;植物纤维;动物纤维;人造,再生和再循环的纤维。
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PCT/EP2015/070764 WO2016041849A1 (en) | 2014-09-15 | 2015-09-10 | High wet fast disperse dyes and mixtures thereof |
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EP3461861B1 (en) * | 2017-10-02 | 2020-07-15 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures |
CN108864751B (zh) * | 2018-08-07 | 2020-04-14 | 江苏之江化工有限公司 | 一种高上色高水洗牢度蓝黑混合物 |
CN108947765A (zh) * | 2018-08-15 | 2018-12-07 | 江苏常源新材料科技有限公司 | 一种双重氮化反应一步合成邻二溴苯的方法 |
CN109487579B (zh) * | 2018-11-19 | 2021-01-26 | 浙江乐高实业股份有限公司 | 超细旦聚酯纤维短流程印染方法 |
EP3715423B1 (en) * | 2019-03-27 | 2022-05-11 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures of n-[4-(5-fluoro-2,4-dinitro-phenylazo)-phenyl]-amine derivatives and n-[4-(4-nitro-phenylazo)-phenyl]-amine derivatives |
EP3715424A1 (en) | 2019-03-27 | 2020-09-30 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures of n-[4-(5-thiocyanato-2,4-dinitro-phenylazo)-phenyl]-amine derivatives and n-[4-(4-nitro-phenylazo)-phenyl]-amine derivatives |
CN110835473B (zh) * | 2019-11-27 | 2022-02-01 | 上海鸿源鑫创材料科技有限公司 | 一种分散染料组合物、染料制品及其应用 |
CN110804324B (zh) * | 2019-11-27 | 2021-04-30 | 浙江龙盛化工研究有限公司 | 一种分散染料组合物、染料制品及其应用 |
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TW201612253A (en) | 2016-04-01 |
KR102276269B1 (ko) | 2021-07-12 |
ES2619424T3 (es) | 2017-06-26 |
EP2995653A1 (en) | 2016-03-16 |
MX2017003365A (es) | 2017-06-28 |
JP2017532391A (ja) | 2017-11-02 |
WO2016041849A1 (en) | 2016-03-24 |
KR20170056504A (ko) | 2017-05-23 |
EP3060608A1 (en) | 2016-08-31 |
JP2020073679A (ja) | 2020-05-14 |
PT3060608T (pt) | 2017-03-17 |
JP7516043B2 (ja) | 2024-07-16 |
TWI617625B (zh) | 2018-03-11 |
BR112016030138A8 (pt) | 2021-05-04 |
US20170306154A1 (en) | 2017-10-26 |
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CN107075268A (zh) | 2017-08-18 |
US10301474B2 (en) | 2019-05-28 |
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