CN1711319A - 邻苯二甲酰亚胺－偶氮染料,其制备方法和其应用 - Google Patents
邻苯二甲酰亚胺－偶氮染料,其制备方法和其应用 Download PDFInfo
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- CN1711319A CN1711319A CNA2003801029505A CN200380102950A CN1711319A CN 1711319 A CN1711319 A CN 1711319A CN A2003801029505 A CNA2003801029505 A CN A2003801029505A CN 200380102950 A CN200380102950 A CN 200380102950A CN 1711319 A CN1711319 A CN 1711319A
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- -1 2-ethoxyethyl Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 12
- 238000007639 printing Methods 0.000 claims abstract description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
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- 229920000742 Cotton Polymers 0.000 description 1
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000012954 diazonium 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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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
-
- 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
-
- 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
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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
-
- 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
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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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN radicals
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- 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
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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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- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
本发明涉及式(1)的染料，其中R1是2－甲氧基乙基，2－乙氧基乙基或2－(2－乙氧基乙氧基)乙基；R2是C1－C6烷基，其是未取代的，或被一个或多个羟基、卤原子、C1－C4烷氧基，C2－C8烷氧基烷氧基、C1－C4烷基－COO－基或C1－C4烷基－OCO－基取代的；R3是甲基，羟基，卤素，－NH－SO2－R5或－NH－CO－R6，其中R5是甲基或乙基和R6是甲基，乙基，甲氧基甲基或2－甲氧基乙基；和R4是乙基或正丙基；本发明还涉及这些染料的制备方法和它们在半合成和尤其是合成的疏水纤维材料，更尤其是纺织材料的染色或印染。
Description
本发明涉及具有一种N-烷基-邻苯二甲酰亚胺重氮基组分和一种苯胺偶合组分的分散染料，这些染料的制备方法和这些染料在半合成和尤其是合成的疏水纤维材料，更尤其是纺织材料的染色或印染中的应用。
具有N-烷基-邻苯二甲酰亚胺重氮基组分和苯胺偶合组分的偶氮分散染料已知很长时间了，并用于疏水纤维材料的染色。然而已经证实，用目前所知的这些染料产生的染色或印染无法满足今天所有情况的要求，尤其是在耐洗性和耐汗湿性方面。因而，需要显示出良好耐洗性的新型染料。
现已令人惊异地发现，本发明的染料在极大的程度上符合上面提出的标准。
因而，本发明涉及产生具有高度耐洗和耐汗湿性的染色的分散染料，这些染料在排气和热溶胶过程及在织物印染中均具有优良的结构(或组成)。该染料也适合于拔染。
本发明的染料相应于下式
式中R1是2-甲氧基乙基，2-乙氧基乙基或2-(2-乙氧基乙氧基)乙基；R2是C1-C6烷基，此烷基是未取代的或被一个或多个羟基、卤原子、C1-C4烷氧基、C2-C8烷氧基烷氧基、C1-C4烷基-COO-基或C1-C4烷基-OCO-基取代的；R3是甲基，羟基，卤素，-NH-SO2-R5或NH-CO-R6，其中R5是甲基或乙基和R6是甲基，乙基，甲氧基甲基或2-甲氧基乙基；和R4是乙基或正丙基。
C1-C6烷基作为R2可以是例如甲基，乙基，正丙基，异丙基，正丁基，异丁基，仲丁基，叔丁基，正戊基，新戊基或正己基。
作为R3的卤素是氟，溴或优选氯。
R1和R2优选具有相同含意。
R1优选是2-甲氧基乙基。
R3优选是-NH-CO-R6。
R6优选是甲基。
R4优选是乙基。
特别优选式(1a)，(1b)和(1c)的染料
本发明还涉及式(1)的染料的制备方法，在该方法中，下式的邻苯二甲酰亚胺
其中R4如上所定义，在酸性范围内进行硝化，例如如OrganicSynthesis，Collective Volume 2，(a Revised Edition of Annual VolumesX-XIX)，J.Wiley & Sons第459页中所述，然后将得到的硝基化合物例如按照Journal of Organic Chemistry
32(1967)第1923页第3段所指出的方法进行烷基化，以及例如通过如Bull.Soc.Chim.de France1957，第569页所述进行还原处理，转化成下式的中间体
式(3)的中间体按照通常已知的方法在酸性介质中单卤化，然后重氮化和偶合至式(4)的化合物
其中R1，R2和R3如上所定义，然后用氰基取代卤素取代基。
卤化的进行，例如通过式(3)的化合物首先在乙酸中与乙酸钠反应，然后在同样的介质中与溴反应，生成相应的一溴化合物。
重氮化也是用本来已知的方法，例如与亚硝酸钠在酸盐，例如含盐酸或含硫酸的水介质中进行。不过，重氮化也可以用其他重氮化试剂进行，例如用亚硝基硫酸。在重氮化时，在反应介质中可存在另外的酸，例如磷酸，硫酸，乙酸，丙酸或盐酸，或所述各酸的混合物，例如丙酸和乙酸的混合物。在温度-10-30℃，例如-10℃至室温进行重氮化是有利的。
重氮化的化合物与式(4)的偶联成分的偶合同样在已知的方式下进行，例如在酸性的，水或水-有机介质中，优选温度从-10-30℃，特别是低于10℃进行。所用酸的实例是盐酸，乙酸，丙酸，硫酸和磷酸。
获得最终染料的反应通过在单卤化合物中按照本来已知的方法，例如应用CuCN或CuCN和碱金属氰化物的混合物在溶剂中(所述溶剂例如是二甲基甲酰胺，二甲基亚砜，二甲基乙酰胺，N-甲基吡啶烷酮，环丁砜或吡啶)的氰基置换来进行。
重氮组分和式(4)的偶合组分是已知的或可以用本来已知的方法制备。
本发明还涉及含有至少两种式(1)的不同结构的偶氮染料的染料混合物。
含有式(1)的两种结构不同的偶氮染料的染料混合物是优选的。
按照本发明的包含式(1)的至少两种结构不同的偶氮染料的染料混合物可以例如通过简单地混合各别染料制备。
在本发明的染料混合物中各染料的量可在很宽的范围内变化，例如从95∶5-5∶95重量份，尤其是70∶30-30∶70重量份，更尤其是在含有本发明的两种偶氮染料的染料混合物中从55∶45-45∶55重量份的各染料。
本发明的染料和染料混合物可用于半合成的和，尤其是合成的疏水纤维材料，更尤其是纺织材料的染色或印染。由含有上述半合成或合成的疏水纤维材料构成的织物材料同样可用本发明的染料或染料混合物进行染色或印染。
适合的半合成纤维材料特别是2乙酸纤维素和三乙酸纤维素。
合成的疏水纤维材料特别由线性芳族聚酯，例如对苯二酸和二元醇的聚酯，所述二元醇尤其是乙二醇，或对苯二酸和1，4-二(羟甲基)环己烷的缩合产物；或聚碳酸酯，例如α，α-二甲基-4，4-二羟基-二苯基甲烷和碳酰氯的聚碳酸酯，或基于聚氯乙烯和基于聚酰胺的纤维构成。
将本发明的染料和染料混合物施于纤维材料是按照已知的染色操作进行。例如，聚酯纤维的染色是用来自在通常的阴离子或非离子分散剂和任选的通常的溶胀剂(载体)存在下的水分散体的排气过程于80-140℃进行。2乙酸纤维素的染色优选于65-85℃进行，而三乙酸纤维素优选于65-115℃进行。
但是本发明的染料和染料混合物不能使染料浴中存在的羊毛和棉花同时着色，或仅使这类材料轻微着色(很好的保留)，以致它们也可以令人满意地用于聚酯/羊毛和聚酯/纤维素性纤维混合织物的染色。
本发明的染料和染料混合物适合于按照热溶法、排气法和印刷法进行染色。
所述的纤维材料可以是各种操作形式，例如纤维、纱或无纺形式，纺织品或针织品形式。
本发明的染料或染料混合物在使用之前转化为染料制剂是有利的。因此，将该染料磨碎，使其颗粒尺寸平均为0.1-10微米。研磨可以在分散剂的参与下进行。例如，将干燥的染料与分散剂一起研磨或与分散剂一起捏和成浆状物，然后在真空中或通过微粒化干燥。如此得到的制剂可以在加入水之后应用，以制备印染浆和染色浴。
对于印染，通常的增稠剂可以应用，例如改性或未改性的天然产物，例如藻酸盐、糊精、阿拉伯树胶、刺梧桐结晶胶、刺槐豆粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或合成产品，例如聚丙烯酰胺、聚丙烯酸或它们的共聚物或聚乙烯醇。
本发明的染料和染料混合物使上面指出的材料，尤其是聚酯材料具有同等程度的色调，这种色调具有优良的实用坚牢度，如尤其是良好的耐光性，耐热固化性，耐折叠性，耐氯和耐湿，如耐水、耐汗湿和耐洗涤；最终的染色还显示出极优良的耐磨性。特别应提及的是所得染色的优良的耐汗湿性，尤其是耐洗性。
本发明的染料和染料混合物也可令人满意地用于与其他染料一起配制混合的色调。
此外，本发明的染料和染料混合物还特别适合于来自超临界CO2的疏水纤维材料的染色。
本发明还涉及本发明的染料和染料混合物的上述应用，以及半合成或合成的疏水纤维材料，尤其是纺织材料的染色或印染方法，该方法包括将本发明的染料施用于已指明的材料或将其掺入到材料中。已指明的疏水纤维材料尤其是纺织的聚酯材料。另外的可用本发明的方法处理的底材以及优选的工艺操作条件在上文中较详细解释本发明的染料的应用时已经知道了。
本发明还涉及已用上述方法染色或印染的疏水纤维材料，尤其是聚酯纺织材料。本发明的染料也适合于现代记录方法，例如热转移印刷。
下面的实施例用于说明本发明。在各实施例中，份数是重量份数，百分数是重量百分数，除非另外指明。给出的温度是摄氏度。重量份数和体积份数之间的关系是与克和立方厘米之间的关系相同的。
I.制备实施例
实施例1.1
A.将5.5ml 96％硫酸放入一个实验室反应装置中。在搅拌下滴加1.3ml冰-水，同时用冰浴冷却。然后在内温25℃下将2.7g式(5a)的化合物
引入。将如此得到的悬浮液搅拌10分钟。然后将1.85ml的40％亚硝基硫酸在10分钟的过程内滴加到其中，同时在18-20℃冷却，并在该温度下搅拌2小时。
将在60ml冰-水中的1ml 32％盐酸引入到一个250ml的实验室反应装置中。将6.5g 48％的用25ml乙酸稀释的式(4a)化合物的水溶液在搅拌
下加入。然后在10分钟的过程内加入重氮盐溶液，同时引入约50g的冰，以使内温为0-5℃。
将如此得到的红色悬浮液于0-5℃搅拌1小时，用吸滤法滤出，用去离子水洗涤并干燥。得到4.8g(理论产率的88％)式(6a)化合物。
熔点：175-178℃
外观：黄棕-红
B.将2.23g式(6a)的化合物和10ml二甲基亚砜放入100ml的实验室反应装置，并于室温(RT)搅拌10分钟。然后引入0.17g氰化钠和0.30g氰化亚铜(I)，将所得混合物于室温搅拌10分钟。然后将温度升至70-75℃。在该温度下搅拌反应混合物2小时。冷却至60℃后滴加5ml水，用抽滤法过滤出悬浮体，用温水(50℃)洗涤并干燥。
得到1.8g(理论产率的73％)式(1a)的化合物。
熔点：200-203℃
外观：紫色
下述染料同样适合于半合成或合成的疏水纤维材料的染色，它们可类似于实施例I.1制备(表1)：
表1：
| R1 | R2 | R3 |
| -CH2CH2OCH3 | -CH2CH2OCH3 | -CH3 |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -C2H5 | -NH-CO-CH3 |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -CH2CH2OCH3 | -NH-CO-C2H5 |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| R1 | R2 | R3 |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -CH2CH2OCH3 | -NH-SO2-CH3 |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -CH2CH2OCH3 | -NH-SO2-CH3 |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| R1 | R2 | R3 |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -CH2CH2OCH3 | -NH-CO-CH2OCH3 |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
| ″ | -CH2CH2OCH3 | -OH |
| ″ | -C2H5 | ″ |
| ″ | -CH2CH2CH3 | ″ |
| ″ | -CH2COOCH3 | ″ |
| ″ | -CH2COOC2H5 | ″ |
| ″ | -CH(CH3)-COOCH3 | ″ |
| ″ | -CH(CH3)-COOC2H5 | ″ |
| ″ | -CH2CH2COOCH3 | ″ |
| ″ | -CH2CH2COOC2H5 | ″ |
| ″ | -CH2CH2O-CO-CH3 | ″ |
| ″ | -CH2CH2O-CO-C2H5 | ″ |
| ″ | 苄基 | ″ |
II.应用实施例
实施例II.1
将1重量份的式(1a)染料
在砂磨机中与17重量份的水和2重量份的商购二萘甲烷二磺酸盐型分散剂一起研磨，并转变为5％水分散体。应用此制剂，通过在130℃下的高温排气过程在聚酯纤维上产生0.1％染色(基于染料和基质)，进行还原清洗。如此得到的紫色染色具有极优的坚牢度性质，特别是杰出的耐洗性。
当用热溶胶法(10g/l染料，液体涂布量50％，固定温度210℃)进行聚酯纤维染色时，可以得到同样良好的坚牢度性质。
Claims (12)
1.一种式(1)的染料
式中R1是2-甲氧基乙基，2-乙氧基乙基或2-(2-乙氧基乙氧基)乙基；R2是C1-C6烷基，其是未取代或被一个或多个羟基、卤原子、C1-C4烷氧基、C2-C8烷氧基烷氧基、C1-C4烷基-COO-基或C1-C4烷基-OCO-基取代的；R3是甲基，羟基，卤素，-NH-SO2-R5或-NH-CO-R6，其中R5是甲基或乙基和R6是甲基，乙基，甲氧基甲基或2-甲氧基乙基；和R4是乙基或正丙基。
2.权利要求1的染料，其中R1和R2相同。
3.权利要求1或2的染料，其中R1是2-甲氧基乙基。
4.前述权利要求任一项的染料，其中R3是-NH-CO-R6。
5.权利要求4的染料，其中R6是甲基。
6.前述权利要求任一项的染料，其中R4是甲基。
7.权利要求1的式(1a)、(1b)或(1c)的染料
8.一种制备权利要求1的式(1)染料的方法，其中将式(2)的邻苯二甲酰亚胺
其中R4如权利要求1中所定义，在酸性范围内硝化，然后将得到的硝基化合物和通过还原处理转变成式(3)的中间体
式(3)的中间体在酸性介质中进行单卤化，然后重氮化，与式(4)的化合物偶合
其中R1，R2和R3如权利要求1中所定义，然后用氰基取代卤素取代基。
9.一种含有权利要求1的式(1)的两种不同结构的染料的染料混合物。
10.一种染色或印染半合成或合成的疏水纤维材料的方法，其中权利要求1的染料或权利要求9的染料混合物施涂于所指出的材料上或掺入其中。
11.权利要求1的式(1)的染料在半合成的或，尤其是合成的疏水纤维材料，更尤其是纺织材料的染色或印染中的用途。
12.一种用权利要求10的方法染色或印染的半合成或，尤其是合成的疏水纤维材料，更尤其是纺织材料。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104403348A (zh) * | 2014-11-18 | 2015-03-11 | 李百春 | 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法 |
| CN104448894A (zh) * | 2014-11-18 | 2015-03-25 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
| CN104448893A (zh) * | 2014-11-18 | 2015-03-25 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
| CN105602278A (zh) * | 2016-01-28 | 2016-05-25 | 俞杏英 | 一种蓝色分散染料单体化合物及其制备方法和应用 |
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| CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
| CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
| CN109054429A (zh) * | 2018-07-06 | 2018-12-21 | 浙江万丰化工有限公司 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
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| JP2002019260A (ja) | 2000-07-04 | 2002-01-23 | Seiko Epson Corp | 記録方法 |
| CN1317337C (zh) * | 2004-12-28 | 2007-05-23 | 浙江龙盛集团股份有限公司 | 一种红色单偶氮染料组合物 |
| EP2337820B1 (en) * | 2008-10-21 | 2013-05-15 | Huntsman Advanced Materials (Switzerland) GmbH | Azo dyes, a process for the preparation thereof and the use thereof |
| PT2513229E (pt) | 2009-12-16 | 2014-07-14 | Huntsman Adv Mat Switzerland | Corantes azo dispersos, um processo para o seu fabrico e o seu uso |
| EP2754696A1 (en) | 2013-01-15 | 2014-07-16 | DyStar Colours Distribution GmbH | AOX-free navy and black disperse dye mixtures |
| PT2943537T (pt) | 2013-01-14 | 2019-02-15 | Dystar Colours Distrib Gmbh | Misturas de corantes com humidade elevada e dispersão rápida |
| CN103965094B (zh) * | 2013-01-31 | 2016-07-06 | 江苏道博化工有限公司 | N-甲基-4-氨基-5-溴-邻苯二甲酰亚胺的合成方法 |
| CN104448892B (zh) * | 2014-11-18 | 2017-04-05 | 李百春 | 一种高水洗牢度和升华牢度的宝蓝分散染料及其制备方法 |
| TWI707002B (zh) * | 2016-05-25 | 2020-10-11 | 瑞士商杭斯曼高級材料公司 | 分散偶氮染料、其製備方法及其用途 |
| EP3461861B1 (en) | 2017-10-02 | 2020-07-15 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures |
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| US3980634A (en) * | 1973-07-02 | 1976-09-14 | Eastman Kodak Company | Phthalimidyl-azo aniline type compounds and polyester fibers dyed therewith |
| JPS5818470B2 (ja) * | 1974-09-06 | 1983-04-13 | 三菱化学株式会社 | ゴウセイセンイルイ ノ センシヨクホウホウ |
| EP0051563B1 (de) * | 1980-10-30 | 1985-04-24 | Ciba-Geigy Ag | Monoazoverbindungen |
| DE59104277D1 (de) * | 1990-02-19 | 1995-03-02 | Ciba Geigy Ag | Phthalimidyl-Azofarbstoffe. |
| JPH06329930A (ja) * | 1993-05-06 | 1994-11-29 | Ciba Geigy Ag | アゾ染料 |
| US6008332A (en) * | 1994-02-11 | 1999-12-28 | Ciba Specialty Chemicals Corporation | Phthalimidylazo dyes, process for their preparation and the use thereof |
| TW328094B (en) | 1994-02-11 | 1998-03-11 | Ciba Sc Holding Ag | Phthalimidylazo dyes, process for their preparation and the use thereof |
| TWI243192B (en) * | 1998-12-31 | 2005-11-11 | Ciba Sc Holding Ag | Phthalimidyl azo pigments, method for producing same and utilization thereof |
| PT1358274E (pt) | 2001-02-07 | 2011-04-05 | Huntsman Adv Mat Switzerland | Corante à base de ftalimidilo azo, processo para a sua preparação e uso do mesmo |
| CZ20032382A3 (cs) * | 2001-02-07 | 2003-11-12 | Ciba Specialty Chemicals Holding Inc. | Ftalimidylová azobarviva, způsob jejich přípravy a jejich použití |
-
2003
- 2003-11-04 AU AU2003276247A patent/AU2003276247A1/en not_active Abandoned
- 2003-11-04 WO PCT/EP2003/012282 patent/WO2004044058A1/en active Application Filing
- 2003-11-04 US US10/533,010 patent/US20060101594A1/en not_active Abandoned
- 2003-11-04 KR KR1020057008394A patent/KR101035841B1/ko not_active IP Right Cessation
- 2003-11-04 EP EP03810962.5A patent/EP1560883B1/en not_active Expired - Lifetime
- 2003-11-04 CN CNB2003801029505A patent/CN100379825C/zh not_active Expired - Lifetime
- 2003-11-04 JP JP2004550922A patent/JP4589726B2/ja not_active Expired - Lifetime
- 2003-11-10 TW TW092131377A patent/TWI338021B/zh not_active IP Right Cessation
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2008
- 2008-03-31 US US12/059,344 patent/US20080184499A1/en not_active Abandoned
-
2010
- 2010-12-09 US US12/964,053 patent/US20110078863A1/en not_active Abandoned
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2014
- 2014-03-18 US US14/217,903 patent/US20140196224A1/en not_active Abandoned
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104403348A (zh) * | 2014-11-18 | 2015-03-11 | 李百春 | 一种高水洗牢度和升华牢度的紫色分散染料及其制备方法 |
| CN104448894A (zh) * | 2014-11-18 | 2015-03-25 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
| CN104448893A (zh) * | 2014-11-18 | 2015-03-25 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
| CN104448894B (zh) * | 2014-11-18 | 2016-08-24 | 昌邑福莱蒽特精细化工有限公司 | 高水洗牢度和升华牢度的分散绿光蓝染料及其制备方法 |
| CN104448893B (zh) * | 2014-11-18 | 2017-04-05 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和升华牢度的红色分散染料及其制备方法 |
| CN105602278A (zh) * | 2016-01-28 | 2016-05-25 | 俞杏英 | 一种蓝色分散染料单体化合物及其制备方法和应用 |
| CN105647224A (zh) * | 2016-01-28 | 2016-06-08 | 俞杏英 | 一种邻苯二甲酰亚胺-偶氮分散染料单体化合物及其制备方法和应用 |
| CN107722663A (zh) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | 一种偶氮染料化合物及其制备方法和应用 |
| CN108864732A (zh) * | 2018-07-06 | 2018-11-23 | 浙江万丰化工有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
| CN109054429A (zh) * | 2018-07-06 | 2018-12-21 | 浙江万丰化工有限公司 | 一种含乙酰胺基团的偶氮染料化合物及其制备方法和应用 |
| CN108864732B (zh) * | 2018-07-06 | 2020-05-05 | 浙江万丰化工股份有限公司 | 一种含甲磺酰胺基团的偶氮染料化合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20060101594A1 (en) | 2006-05-18 |
| EP1560883B1 (en) | 2013-07-10 |
| WO2004044058A1 (en) | 2004-05-27 |
| US20140196224A1 (en) | 2014-07-17 |
| KR20050075390A (ko) | 2005-07-20 |
| CN100379825C (zh) | 2008-04-09 |
| JP2006505662A (ja) | 2006-02-16 |
| KR101035841B1 (ko) | 2011-05-20 |
| US20110078863A1 (en) | 2011-04-07 |
| US20080184499A1 (en) | 2008-08-07 |
| EP1560883A1 (en) | 2005-08-10 |
| AU2003276247A1 (en) | 2004-06-03 |
| TW200420672A (en) | 2004-10-16 |
| JP4589726B2 (ja) | 2010-12-01 |
| TWI338021B (en) | 2011-03-01 |
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