CN1729253A - 邻苯二甲酰亚胺偶氮染料、制备它们的方法和它们的用途 - Google Patents
邻苯二甲酰亚胺偶氮染料、制备它们的方法和它们的用途 Download PDFInfo
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- 239000000975 dye Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 23
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- 230000008569 process Effects 0.000 title abstract description 6
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- 238000004043 dyeing Methods 0.000 claims abstract description 18
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- -1 2-ethoxyethyl Chemical group 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Chemical group 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Chemical group 0.000 claims abstract description 5
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- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 20
- 230000008878 coupling Effects 0.000 claims description 8
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- 238000005859 coupling reaction Methods 0.000 claims description 8
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- 125000001246 bromo group Chemical group Br* 0.000 claims 1
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- DAJBOBFEKRAZPE-UHFFFAOYSA-N 5-amino-6-bromo-2-butylisoindole-1,3-dione Chemical class NC1=C(Br)C=C2C(=O)N(CCCC)C(=O)C2=C1 DAJBOBFEKRAZPE-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 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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- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012954 diazonium Substances 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 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
- C09B29/0025—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
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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)
- C09B29/3634—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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- 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
- C09B29/34—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
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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
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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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/30—Woven fabric [i.e., woven strand or strip material]
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及一种式(I)的染料,其中R1是C1-C12烷基或-CnH2n-(OCH2CH2) m-OR3,n是从2至8的整数,m是从0到4的整数,R3是C1-C12烷基、C6-C24芳基或C6-C24芳烷基,R2是甲基、乙基、正丙基、正丁基、2-甲氧基乙基或2-乙氧基乙基,X是卤素,而Y是氢、氯或溴,和制备它们的方法以及它们在给半合成的,尤其是合成的疏水性纤维材料,更尤其是纺织材料染色或者印花中的应用。
Description
本发明涉及含有N-烷基-邻苯二甲酰亚胺重氮组分和吡啶酮偶联组分的分散体染料、制备这些染料的方法,以及它们在给半合成的,尤其是合成的疏水性纤维材料,更尤其是纺织材料染色或者印花中的应用。
很长时间以前人们就知道含有N-烷基邻苯二甲酰亚胺重氮组分和吡啶酮偶联组分的分散的偶氮染料,并且它们可用于疏水性纤维材料的染色。然而,已经发现使用目前已知的染料得到的染色或者印花并不能在任何场合都能满足今天的要求,特别是关于耐洗度和耐汗度的要求。因此需要新的染料,尤其是具有好的耐洗度的染料。
如今已令人惊讶地发现,根据本发明的染料在很大程度上满足上述给定的标准。
相应地,本发明涉及分散染料,得到的染色具有高的耐洗度和耐汗度,而且,此外它具有在排气和热溶胶处理以及在织物印花方面都好的组合特性。该染料也适合于拔染印花。
根据本发明的与下式对应的染料:
其中R1是C1-C12烷基或-CnH2n-(OCH2CH2)m-OR3,n是从2至8的整数,m是从0到4的整数,R3是C1-C12烷基、C6-C24芳基或C6-C24芳烷基,R2是甲基、乙基、正丙基、正丁基、2-甲氧基乙基或2-乙氧基乙基,X是卤素,而Y是氢、氯或溴。
作为R1和R3的C1-C12烷基可以例如是甲基、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、正己基、正辛基、正癸基或正十二碳烷基。
作为R3,C6-C24芳基例如是苯基、甲苯基、2,4,6-三甲苯基、2,4,6-三异丙基苯基、萘基和蒽基。
合适的C6-C24芳烷基例如是苯甲基和2-苯基乙基。
优选其中R1是甲基、乙基或正丁基的式(1)的染料。
R2优选是正丁基。
作为X,卤素是氟、氯或优选是溴。
Y优选是氢。
特别优选式(1a)、(1b)和(1c)的染料
本发明还涉及制备式(1)的染料的方法,该方法包括在酸性范围内硝化下式的邻苯二甲酰亚胺:
其中R2定义如上,在例如J.WIley & Sons的Organic Synthesis,Collective Volume 2,(Annual Volumes X-XIX的修订版)中的第459页所述,然后例如依照Journal of Organic Chemistry
32(1967)第1923页第3段所描述的方法将得到的硝基化合物烷基化,并且例如在如Bull.Soc.Chim.de France
1957第569页中描述的还原处理以后,转化成下式的中间体
在酸性介质中卤化式(3)的中间体,然后进行重氮化反应,并与式(4)的吡啶酮化合物偶联
其中R1定义如上。
可以这样进行卤化反应,例如在乙酸中使式(3)化合物首先与乙酸钠反应,然后在同样的介质中与溴反应形成相应的一溴化物。
同样地,以本身已知的方法进行重氮化反应,例如在酸例如含盐酸或含硫酸的含水介质中与亚硝酸钠反应。然而,还可使用其它的重氮化试剂,例如使用亚硝基硫酸进行重氮化反应。在重氮化反应中,在反应介质中还可以存在另外的酸例如磷酸、硫酸、乙酸、丙酸、盐酸或这些酸的混合物例如丙酸和乙酸的混合物。在从-10℃到30℃,例如从-10℃到室温的温度下进行重氮化反应是有利的。
对已被重氮化的化合物与式(4)的偶合组分的偶联反应同样地按照已知的方法进行偶联,例如在酸、水溶液或含水的有机介质中,有利的是在-10到30℃,特别是在低于10℃的温度下进行反应。
所用的酸的例子是盐酸、乙酸、丙酸、硫酸和磷酸。
重氮组分和式(4)的偶合组分是已知的或按照本身已知的方法制备得到。
本发明还涉及包括至少两个在结构上不同的式(1)偶氮染料的染料混合物。
根据本发明,包括至少两个在结构上不同的式(1)偶氮染料的该染料混合物可以通过简单地混合单个的染料而制备得到。
根据本发明,染料混合物中单个的染料的量可以在一较宽的范围内改变,例如在根据本发明的包括两个偶氮染料的染料混合物中单个的染料在从95∶5至5∶95重量份,尤其是从70∶30至30∶70重量份,更尤其是从55∶45到45∶55重量份的范围内变化。
根据本发明,染料和染料混合物可以被用来染色或印花半合成的,尤其是合成的疏水性纤维物质,更尤其是纺织材料。由包含这样的半合成的或合成的疏水性纤维物质的混纺织物组成的纺织材料也可以使用根据本发明的染料或染料混合物进行染色或者印花。
可以考虑的半纤维材料特别是纤维素21/2-醋酸酯和三乙酸纤维素。
合成的疏水性纤维物质特别是由下列物质组成:线状的芳香族聚酯例如对苯二甲酸和二元醇尤其是乙二醇的聚酯,或对苯二甲酸和1,4-二羟甲基环己烷的缩合产物;聚碳酸酯例如α,α-二甲基-4,4-二羟基-二苯基甲烷和光气的聚碳酸酯,以及基于聚氯乙烯或基于聚酰胺的纤维。
依照已知的染色方法将根据本发明的染料和染料混合物应用到纤维材料上。例如在通常的阴离子的或非离子的分散剂存在下,和任选的通常的膨胀剂(载体)存在下,在从80到140℃的温度下,将聚酯纤维物质在从一种含水分散体中排气法中被染色。纤维素21/2-醋酸酯优选在从65到85℃的温度下被染色,和三乙酸纤维素优选在从65到115℃的温度下被染色。
根据本发明的染料和染料混合物染色不会将同时存在于染液中的羊毛以及棉花染色,或者对这样的材料只是稍微染色(很好的保留性),以便它们也可以被满意地用于聚酯/羊毛和聚酯/纤维素纤维混纺织物的染色。
根据本发明的染料和染料混合物适合按照热溶胶工艺进行染色,按照排气工艺进行印刷加工。
在这些工艺中,所述纤维材料可以以各种各样的加工形式出现,例如以纤维、纱或者非纺织的、编织的或者针织物的形式出现。
有利的是在使用之前,将根据本发明的染料或者染料混合物转换成一种染料制剂。基于这个目的,研磨染料以便其粒径平均在0.1到10微米。可以在分散剂存在下进行研磨。例如:将干燥的染料和分散剂放在一起磨或者与分散剂一起揉成一浆糊形式,然后在真空中干燥或者通过喷雾法干燥。在搀水以后,所得到的制剂可用于制备印染浆和染液。
为了进行印花,将使用通常的增稠剂,例如修饰的或者未修饰的天然产品,例如藻酸盐、糊精、阿拉伯树胶、结晶树胶、槐豆粉、黄蓍胶、羧甲基纤维素、羟乙基纤维素、淀粉或者合成制品,例如聚丙烯酰胺、聚丙烯酸或者它们的共聚物,或聚乙烯醇。根据本发明,将染料和染料混合物传递到所述材料,尤其是聚酯材料,使色度均衡,具有很好的内在的使用牢度特性例如,尤其是好的耐光度、耐热度、耐褶裥牢度、耐氯牢度和耐湿度,例如对水、出汗和对洗涤的牢度;已经结束染色进一步的特征是有很好的耐磨度。
应该特别强调的是所得到的染料具有对汗,尤其是对洗涤具有好的牢固特性。
根据本发明的染料和染料混合物也可以令人满意地和其它的染料一起产生混合色调。
此外,根据本发明的染料和染料混合物也非常适合于对从超临界二氧化碳获得的疏水性纤维材料进行染色。
本发明涉及根据本发明的染料和染料混合物的上述用途和用于染色或者印花半合成的或者合成的疏水性纤维材料,尤其是纺织材料的方法,其中根据本发明的染料被用于所述材料或者掺入其中。所述疏水性纤维材料优选是织物聚酯材料。进一步的,在对根据本发明的染料的用途更详细的说明里,可以发现上文中的可以通过本发明的方法和优选的工艺操作条件处理的基质。
本发明还涉及通过所述方法染色或者印花的疏水性纤维材料,优选聚酯纺织品。
此外,根据本发明的染料适合于现代复制工艺,例如热转移(thermo transfer)印刷。
下述的实施例用来阐明本发明。除非另有指明,在其中份是重量份,百分比是重量百分比。所给的温度是摄氏温度。重量份和体积份之间的关系如同克和立方厘米之间的关系。
I.制备实施例
实施例1.1:
A.重氮化反应
将5毫升的96%硫酸转移到一个实验室反应装置中。在搅拌下,慢慢地滴加2.7毫升的冰水以使内部温度是25-30℃。然后,在20分钟以内,引入3.0克4-氨基-5-溴-N-丁基邻苯二甲酰亚胺。在内部温度为25-30℃时搅拌所得的悬浮液10分钟。然后,在15分钟以内,在内部温度为20-25℃时滴加1.75毫升的40%亚硝基硫酸,并在该温度下搅拌2小时。
B.偶联
从Surfynol 104E(2,4,7,9-四甲基-5-癸炔-4,7-二醇)的150毫升水溶液取出3滴转到一带有pH计的实验室反应装置中。在搅拌下引入1.8克1-乙基-3-氰基-4-甲基-6-羟基-2-吡啶酮。然后加入3毫升的10%NaOH(pH=10-12)。将所得到的溶液冷却到10℃,在大约30分钟以内滴加重氮盐的溶液,以便内部温度是10-15℃,通过滴加70毫升的10%NaOH使pH值维持在2-3。在10-15℃搅拌所得到的黄色悬浮液1小时。用抽吸器滤去固体,用去离子水洗涤并且干燥。得到4.7g(理论的86%)下式化合物:
熔点:>150℃
外观:黄-绿色
类似于实施例I.1,可以制取下列染料,它们同样地适合对半合成品或合成的疏水性纤维物质染色(表1):
表1:
X | Y | R1 | R2 |
BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | HHHHHHHHHHHHHHHHHHHHHHHHH | CH3CH3CH3CH3CH3CH3C2H5C2H5C2H5C2H5C2H5C2H5n-C3H7n-C3H7n-C3H7n-C3H7n-C3H7n-C3H7n-C4H9n-C4H9n-C4H9n-C4H9n-C4H9n-C4H9-CH2CH2OCH3 | CH3C2H5n-C3H7n-C4H9-CH2CH2OCH3-CH2CH2OC2H5CH3C2H5n-C3H7n-C4H9-CH2CH2OCH3-CH2CH2OC2H5CH3C2H5n-C3H7n-C4H9-CH2CH2OCH3-CH2CH2OC2H5CH3C2H5n-C3H7n-C4H9-CH2CH2OCH3-CH2CH2OC2H5CH3 |
II.应用实施例
实施例II.1:
在砂磨机上将1重量份的下式染料与17重量份的水和2重量份的市场上可买到的二萘甲基二磺酸盐型分散剂一起研磨,并转变成5%的水分散体。
使用那个配方,在130℃使用高温排放方法在编织的聚酯织物上产生1%的染色(以染料和基材为基础),并还原清除。以这种方式得到的紫色染色具有很好的内在-使用牢固特性,尤其是极好的耐洗度。
当编织的聚酯织物用热溶法被染色(10克/升的染料、吸收液体50%,固定温度210℃)时,可以达到同样好的牢固特性。
Claims (11)
2、一种根据权利要求1的式(1)染料,其中R1是甲基、乙基或正丁基。
3、根据权利要求1或者权利要求2的式(1)的染料,其中R2是正丁基。
4、根据前面任一项权利要求的式(1)的染料,其中X是溴。
5、根据前面任一项权利要求的式(1)的染料,其中Y是氢。
8、一种染料混合物,它包括至少两个在结构上不同的权利要求1的式(1)染料。
9、用于给半合成品或合成的疏水性纤维物质染色或印花的方法,其中将根据权利要求1的式(1)的染料或根据权利要求8的染料混合物应用于所述物质或掺入其中。
10、根据权利要求1的式(1)染料在给半合成的,尤其是合成的疏水性纤维物质,更尤其是纺织品染色或印花中的用途。
11、通过权利要求9的方法被染色或被印花的半合成的或尤其是合成的疏水性纤维物质,更尤其是纺织材料。
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CN104479395A (zh) * | 2014-11-18 | 2015-04-01 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和高日晒牢度的分散染料及其制备方法 |
CN114437564A (zh) * | 2022-02-28 | 2022-05-06 | 浙江万丰化工股份有限公司 | 一种高牢度分散染料组合物及其应用 |
CN116396625A (zh) * | 2022-06-30 | 2023-07-07 | 浙江龙盛集团股份有限公司 | 一种分散橙染料组合物及其制品 |
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DE102006054088A1 (de) * | 2006-11-16 | 2008-05-21 | Siemens Ag | Messvorrichtung und Messverfahren zum Inspizieren einer Oberfläche eines Substrates |
WO2009118260A1 (en) * | 2008-03-25 | 2009-10-01 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Azopyridone disperse dyes, their preparation and use |
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 |
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 |
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TWI243192B (en) * | 1998-12-31 | 2005-11-11 | Ciba Sc Holding Ag | Phthalimidyl azo pigments, method for producing same and utilization thereof |
CN1289607C (zh) | 2001-02-07 | 2006-12-13 | 西巴特殊化学品控股有限公司 | 苯邻二甲酰亚胺基偶氮染料、其制备方法及其用途 |
RU2288242C2 (ru) | 2001-02-07 | 2006-11-27 | Циба Спешиалти Кемикэлз Холдинг Инк. | Фталимидилазокрасители, способ их получения и их применение |
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CN104479395A (zh) * | 2014-11-18 | 2015-04-01 | 杭州福莱蒽特精细化工有限公司 | 一种高水洗牢度和高日晒牢度的分散染料及其制备方法 |
CN114437564A (zh) * | 2022-02-28 | 2022-05-06 | 浙江万丰化工股份有限公司 | 一种高牢度分散染料组合物及其应用 |
CN114437564B (zh) * | 2022-02-28 | 2024-04-02 | 浙江万丰化工股份有限公司 | 一种高牢度分散染料组合物及其应用 |
CN116396625A (zh) * | 2022-06-30 | 2023-07-07 | 浙江龙盛集团股份有限公司 | 一种分散橙染料组合物及其制品 |
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US20060046596A1 (en) | 2006-03-02 |
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