CN101044211B - 活性染料、其制备方法和用途 - Google Patents
活性染料、其制备方法和用途 Download PDFInfo
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- CN101044211B CN101044211B CN200580035446.7A CN200580035446A CN101044211B CN 101044211 B CN101044211 B CN 101044211B CN 200580035446 A CN200580035446 A CN 200580035446A CN 101044211 B CN101044211 B CN 101044211B
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- 238000002360 preparation method Methods 0.000 title description 4
- 239000000463 material Substances 0.000 claims abstract description 39
- 238000004043 dyeing Methods 0.000 claims abstract description 29
- 239000000835 fiber Substances 0.000 claims abstract description 17
- 239000004952 Polyamide Substances 0.000 claims abstract description 10
- 229920002647 polyamide Polymers 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 28
- 238000007639 printing Methods 0.000 claims description 17
- 239000000123 paper Substances 0.000 claims description 14
- 239000002657 fibrous material Substances 0.000 claims description 9
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000007641 inkjet printing Methods 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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- -1 C2-C4alkanoylamino Chemical class 0.000 abstract description 26
- 229910052736 halogen Inorganic materials 0.000 abstract description 15
- 150000002367 halogens Chemical class 0.000 abstract description 14
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052804 chromium Inorganic materials 0.000 abstract description 11
- 239000011651 chromium Substances 0.000 abstract description 11
- 125000000020 sulfo group Chemical class O=S(=O)([*])O[H] 0.000 abstract description 11
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 5
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- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract description 3
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- 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 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
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- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
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- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000011033 desalting Methods 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
- 239000004627 regenerated cellulose Substances 0.000 description 1
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- 239000013535 sea water Substances 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
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- 238000001291 vacuum drying Methods 0.000 description 1
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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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4416—Metal complex azo dyes
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- D06P3/008—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using reactive dyes
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- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
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Abstract
式(1)的活性染料,其中R1是氢或未被取代的或取代的C1-C4烷基,(R2)s表示s个相同或不同的取代基,选自卤素、硝基、未被取代或被卤素取代的C1-C4烷基、C2-C4烷酰胺基、C1-C4烷基磺酰基、氨甲酰基、磺酰胺基和磺基基团,Me是铬、钴或铁,X是氯,T是下式纤维反应性基团(R3)0-2表示0-2个相同或不同的的取代基,选自卤素、C1-C4烷基、C1-C4烷氧基和磺基基团,Z是乙烯基或-CH2-CH2-U基团,且U是一个在碱性条件下可脱除的基团,Q是一个-CH(Hal)-CH2-Hal或-C(Hal)=CH2基团,Hal是卤素,s是数字0、1、2或3,和m、n、r和q彼此独立地为数字0或1,特别适用于浸染合成聚酰胺纤维材料,同时染色或印刷产品具有良好耐湿性能。-NH-(CH2)2-3-SO2-Z (2a)-NH-(CH2)2-3-O-(CH2)2-3-SO2-Z (2b)
Description
本发明涉及新颖的活性染料、其制备方法和它们在浸染或印刷纺织纤维材料方面的用途。
近来,随着活性染料在染色方面的使用,人们对染色质量和染色工艺的经济性提出了更高的要求。因此,不断需要新的、性能(特别是应用性能)得到改进的活性染料。
现在,染色工艺不仅要求活性染料具有充分的直接染色性能,同时还要求能够很容易地洗脱未固色的染料。它们还应具有良好的着色率和高的反应性能,特别是能够提供具有高固色度的染色。目前已知的染料还不能满足所有这些性能的要求。
迄今为止,只有用酸性染料才能完成在聚酰胺上的深黑染色,然而在高温下这种染色不耐湿。只有用活性染料才能在获得永久耐湿性的同时实现深染色。
因此,本发明解决的根本问题就是要找到印染纤维材料,特别是浸染合成聚酰胺纤维材料时能大幅提高上述典型性能的新颖的活性染料。该新颖染料应具有高固色率和高纤维-染料结合稳定性的特征。特别是该染料应使染色具有多种良好的固色性能,例如耐光和耐湿性。
已经发现,用此处和其后定义的新颖染料可在很大程度上解决上述提出的问题。
因此本发明涉及下式活性染料
其中
R1是氢或未被取代的或取代的C1-C4烷基,
(R2)s表示s个相同或不同的取代基,选自卤素、硝基、未被取代或被卤素取代的C1-C4烷基、C2-C4烷酰胺基、C1-C4烷基磺酰基、氨甲酰基、磺酰胺基和磺基基团,
Me是铬、钴或铁,
X是氯,
T是下式纤维反应性基团
-NH-(CH2)2-3-SO2-Z (2a),
-NH-(CH2)2-3-O-(CH2)2-3-SO2-Z (2b),
(R3)0-2表示0-2个相同或不同的取代基,选自卤素、C1-C4烷基、C1-C4烷氧基和磺基基团,
Z是乙烯基或-CH2-CH2-U基团,且U是一个在碱性条件下可脱除的基团,
Q是一个-CH(Hal)-CH2-Hal或-C(Hal)=CH2基团,
Hal是卤素,
s是数字0、1、2或3和
m、n、r和q彼此独立地为数字0或1。
在式(2c)的基团中,Me是甲基和Et是乙基。除氢之外,所述的基团适于作为氮原子的取代基。
R1和R3彼此独立地是C1-C4烷基,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、叔丁基或异丁基,优选甲基或乙基,特别优选为甲基。在R1情况下,所提及的烷基基团可以是未被取代的或是被例如羟基、磺基、硫酸根合、氰基、羧基、C1-C4烷氧基或苯基,优选被羟基、硫酸根合、C1-C4烷氧基或苯基所取代。对R1来说,优选相应的未被取代的基团。
R2是C1-C4烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或异丁基,优选甲基或乙基,特别优选为甲基。所提及的烷基可以是未被取代的或是被卤素例如氟、氯、溴,优选被氟或氯单或多取代的烷基。
R3是C1-C4烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基或异丁氧基,优选甲氧基或乙氧基,特别优选为甲氧基。
R2和R3彼此独立地是卤素,例如氟、氯或溴,优选氯。
R2是C2-C4烷酰胺基,例如乙酰胺基或丙酰胺基,优选乙酰胺基。
R2是C1-C4烷基磺酰基,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基或正丁基磺酰基,优选甲基磺酰基或乙基磺酰基。
R2表示对应于式-CONH2基团的氨甲酰基。
R2表示对应于式-SO2NH2基团的磺酰胺基。
R1优选为氢。
优选地,(R2)s表示s个相同或不同的取代基,选自卤素、硝基、C2-C4烷酰胺基和磺基,特别是选自硝基和磺基,更特别地是选自硝基基团。
优选地,(R3)0-2表示0-2个相同或不同的取代基,选自C1-C4烷基、C1-C4烷氧基和磺基,特别是选自甲基、甲氧基和磺基基团。
R3特别优选为氢。
T优选式(2c)、(2d)、(2e)或(2f)基团,特别优选式(2c)或(2d)基团,更特别优选(2c)基团。
式(2f)所示的纤维反应性基团中的Hal优选为氯或溴,特别优选为溴。
离去基团U是,例如-Cl、-Br、-F、-OSO3H、-SSO3H、-OCO-CH3、-OPO3H2、-OCO-C6H5、-OSO2-C1-C4烷基或-OSO2-N(C1-C4烷基)2。优选U是式-Cl、-OSO3H、-SSO3H、-OCO-CH3、-OCO-C6H5或-OPO3H2基团,特别优选-Cl或-OSO3H基团。
因此,适合的基团Z的实例有乙烯基、β-溴乙基或β-氯乙基、β-乙酰氧基乙基、β-苯甲酰氧基乙基、β-磷酸乙基、β-硫酸根合乙基和β-硫代硫酸根合乙基。Z优选为乙烯基、β-氯乙基或β-硫酸根合乙基,特别优选为乙烯基。
s优选是数字1、2或3,特别是数字1或2和更特别的是数字1。
M优选是数字1。
n优选是数字0。
q优选是数字0。
r优选是数字1。
Me优选是铬。
式(2c)基团优选为下式基团
其中Z具有上面所给的定义及优选含义。
优选下式活性染料
其中
R1、R2、X、T和s分别具有上面所给的定义及优选含义且,特别地,R1是氢,R2是硝基,X是氯,T是上述式(2c)基团,特别是式(2c’)或(2c”)基团,Z是乙烯基、β-硫酸根合乙基或β-氯乙基,特别是乙烯基,和s是数字1或2,特别是1。
本发明的染料通过如下步骤制备
(i)采用合适的铬、钴或铁化合物,由式
化合物制备得到式
1∶2金属络合物染料,和
(ii)在第一步缩合步骤中,将步骤(i)得到的式(5)1∶2金属络合物染料与式
氰尿酰卤进行缩合,和
(iii)在第二步缩合步骤中,将步骤(ii)得到的式
初级缩合产物与式
T-H (8)
化合物进行缩合,或
(iv)将步骤(i)得到的式(5)1∶2金属络合物染料与式
化合物进行缩合,
R1、R2、Me、X、T、m、n、r、s和q分别具有上面所给的定义及优选含义。
合适的式(6)氰尿酰卤为氰尿酰氯。
式(9)化合物是已知的或者可用类似于已知工艺的方法来制备,例如将式(6)的氰尿酰卤与式(8)化合物进行缩合,式(8)中的T具有上面所给的定义及优选含义。
式(5)的1∶2铬络合物染料是已知的或用类似的化合物来得到,例如将式
1∶1的铬络合化合物与式(4)的偶氮化合物反应,其中R1、(R2)S、m、n、r、s和q分别具有前文所给的定义及优选含义。
式(10)1∶1的铬络合化合物与式(4)的偶氮化合物的反应可在例如含水介质中,40-130℃,特别是70-100℃的温度下,以及pH为8-14,特别是10-13的条件下进行。存在无机酸中和物或碱性介质更有利于该反应的进行,例如碱金属碳酸盐、碱金属醋酸盐或碱金属氢氧化物的存在有利于反应的进行,优选的碱金属为钠。
在按照步骤(i)制备金属络合物的过程中,除了得到式(5)的1∶2金属络合物以外,通常还会得到其配位异构体式(5a)。
除了本发明文本中以通式形式公开的金属络合物如式(1)、(1a)、(5)和(7)外,还认为该公开包括了相应的配位异构体。
式(3)、(4)、(8)和(10)化合物是已知的或者可用类似于已知工艺的方法来获得。
例如,依照常规的铬处理工艺可获得式(10)的1∶1铬络合化合物,其中与铬盐的反应可在例如含水介质中,任选一定的压力下,在例如90-130℃的温度下进行。合适的铬盐有,例如醋酸铬(III)、硝酸铬(III)、氯化铬(III)、水杨酸铬(III)和硫酸铬(III)。
依照常规的重氮化和耦合反应可获得式(3)或(4)化合物。重氮化反应通常是在硝酸作用下,于低温例如0-20℃及无机酸水溶液中进行,同时碱性pH值例如pH8-12有利于耦合反应。
式(3)、(4)重氮化合物的1∶2钴或铁络合物染料是已知的或者可用类似于已知工艺的方法来获得。
1∶2铬或1∶2钴络合物染料可采用例如类似于GB-A-716 753、GB-A-719 274、GB-A-745 641和GB-A-851 861中提及的方法来获得。1∶2铁络合物染料可采用例如类似于US 5 376 151中提及的方法来获得。
缩合反应按照本来就有的已知方式来进行,通常是在例如0-50℃和pH2-10下于水溶液中进行。
步骤(ii)中式(5)1∶2金属络合物染料与式(6)氰尿酰卤的缩合反应优选在0-5℃和pH3-6下进行。步骤(iii)中式(7)初级缩合产物式(8)化合物的缩合反应优选在0-30℃和pH 4-6下进行。步骤(iv)中式(5)1∶2金属络合物染料与式(9)的化合物缩合反应优选在20-50℃和pH4-6下进行。
另外,可任选将最后的产物进行转化反应。此种转化反应有,例如用稀氢氧化钠溶液进行处理,将可乙烯基化的反应基团T(Z或Q)转变成它的乙烯基形式,例如将β-硫酸根合乙基磺酰基或β-氯乙基磺酰基基团转变成乙烯基磺酰基团,或将α,β-二卤代丙酰胺基团转变成α-卤代丙烯酰胺基团。此类反应本身是已知的。转化反应通常在中性到碱性介质中,于例如20-70℃和pH6-14下进行。
式(1)的活性染料包含磺基基团,其中每个磺基可以是游离的磺酸形式,但优选是其盐的形式,例如钠盐、锂盐、钾盐或铵盐,或有机胺盐如三乙醇铵盐。
式(1)的活性染料可进一步包含添加剂例如氯化钠或糊精。
本发明的式(1)活性染料可任选进一步包含辅佐剂,如改进操作或增加储存稳定性的辅佐剂如缓冲剂、分散剂或防尘剂。这些辅佐剂对本领域技术人员来说是已知的。
本发明的活性染料适用于对例如含羟基或含氮的纤维材料染色或印花。可提及的纤维材料的实例有丝绸、羊毛、各种纤维素纤维材料和聚氨酯,以及聚酰胺纤维。纤维素纤维材料有,例如天然的纤维素纤维如棉、亚麻和大麻,还有纤维素和再生纤维素。本发明的活性染料还适用于对含羟基的纤维混合织物染色或印花,如棉与聚酯纤维或聚酰胺纤维的混合织物。
优选对天然或合成聚酰胺纤维材料染色或印花,特别是合成聚酰胺纤维材料如聚酰胺6(聚-ε-己内酰胺)、聚酰胺6,6(聚己二酰己二胺)、聚酰胺7、聚酰胺6,12(聚十二烷二酰己二胺)、聚酰胺11或聚酰胺12、带有聚酰胺6,6或聚酰胺6的共聚酰胺例如六亚甲基二胺、ε-己内酰胺和脂肪酸的聚合物以及脂肪酸、六亚甲基二胺和间苯二甲酸的聚合物或脂肪酸、六亚甲基二胺和2-甲基五亚甲基二胺或2-乙基四亚甲基二胺的聚合物。此外,本发明的式(1)活性染料还适用于对由合成聚酰胺与羊毛混合而成的纤维或纱线染色或印花。
本发明方法还方便地适用于对合成聚酰胺微纤染色或印花。微纤意指由各纤度小于1丹尼尔(1.1dTex)的细丝组成的纤维材料。此类微纤是已知的并通常采用熔融纺丝的方法来制备。
所述的纺织材料可以是范围很广的各种处理形式的材料,例如纤维、纱线、机织布或是编织布和编织毯形式。
用式(1)活性染料进行印染时可采用惯常的印染方法。除了包括水和染料,染色液和印刷浆中还可进一步包括添加剂如浸润剂、防泡沫剂、均染剂或影响纺织材料性能的试剂如柔软剂、阻燃整理剂或防污、防水、防油剂以及水软化剂和天然或合成的增稠剂如藻酸盐和纤维素酯。
对于编织毯材料,印刷方法如置换印刷或隔离浸染是很重要的。
优选采用浸染法,特别是按照抽提法来进行,在浸染编织毯时也可按照连续法来进行。
浸染优选在pH值2-7,特别是2.5-5.5,更特别是3-4.5的条件下进行。浸液比的选择范围可以很宽,例如从1∶5到1∶50,优选1∶5到1∶30。浸染优选在80-130℃,特别是85-120℃的条件下进行。
使用式(1)活性染料可以得到具有多种良好性能的均染效果,例如具有良好的耐氯、耐摩擦、耐湿、耐湿摩、耐洗、耐水、耐海水和耐汗性能以及良好的耐光性能。它们还有上色均匀、亲和性好、反应性高、固色力好和上色能力非常强的特点。本发明的染料具有良好的水溶性,且易于与其它染料混合。
本发明的式(1)染料还适用作记录系统使用的色料。此类记录系统有,例如用于纸张或织物打印的市售喷墨打印机,或书写工具如钢笔或圆珠笔,特别是喷墨打印机。为此目的,首先要将本发明的染料制成适于记录系统使用的形式。适用的形式例如有水性墨水,其中包含了作为色料的本发明染料。可采用常规方法来制备墨水,即在所需量的水中将各组分混合在一起。
基材有上述提到的含羟基基团或含氮的纤维材料,特别是天然或合成的聚酰胺纤维材料。纤维材料优选纺织纤维材料。
基材也可以是纸张和塑料薄膜。
可提及的纸张实例有市售的喷墨打印纸、相纸、光面纸、塑料涂敷纸,如Epson喷墨打印纸、Epson相纸、Epson光面纸、Epson光面膜、HP专用喷墨打印纸、Encad光面相纸和IIford相纸。塑料膜有,例如透明膜或不透明膜。特别合适的塑料膜是例如3M透明膜。
根据使用性质,例如是印刷纺织品还是印刷纸张,可能需要对墨水的性能如粘度或其它物理性能,特别是对所用基材的亲合力有影响的性能进行相应的调整。
水性墨水应优选使用盐含量较低的染料,即染料中盐的总含量应少于颜料重量的0.5wt%。可采用例如膜分离工序如超滤、反向渗透或透析等对由于制备和/或后续加入稀释剂而造成的盐含量相对较高的染料进行脱盐处理。
优选墨水中染料的总含量为墨水总重量的1-35wt%,特别是1-30wt%,优选为1-20wt%。在这种情况下,优选的下限是1.5wt%,更优选的是2wt%,特别优选的是3wt%。
墨水中还可以包含易与水混合的有机溶剂,例如C1-C4醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、叔丁醇或异丁醇;酰胺如二甲基甲酰胺或二甲基乙酰胺;酮或酮醇如丙酮或二丙酮醇;醚如四氢呋喃或二噁烷;含氮杂环化合物如N-甲基-2-吡咯烷酮或1,3-二甲基-2-咪唑烷酮;聚亚烷基二醇如聚乙二醇或聚丙二醇;C2-C6-亚烷基二醇和硫代二醇如乙二醇、丙二醇、丁二醇、三甘醇、硫二甘醇、己二醇和二乙二醇;其它多元醇如丙三醇或1,2,6-己三醇;以及多羟基醇的C1-C4烷基醚如2-甲氧基乙醇、2-(2-甲氧基乙氧基)乙醇、2-(2-乙氧基乙氧基)乙醇、2-[2-(2-甲氧基乙氧基)乙氧基]乙醇或2-[2-(2-乙氧基乙氧基)乙氧基]乙醇;优选N-甲基-2-吡咯烷酮、二乙二醇、丙三醇或特别是1,2-丙二醇,通常有机溶剂的量为墨水总量的2-30wt%,特别是5-30wt%,优选为10-25wt%。
另外,墨水中还可以含有增溶剂,如ε-己内酰胺。
墨水中可以含有来自天然或合成的增稠剂,与其它添加剂一起用于调节墨水的粘度。
可提及的增稠剂的实例包括市售的藻酸盐增稠剂、淀粉醚或洋槐豆粉醚,特别是藻酸钠本身或它与改姓纤维素如甲基纤维素、乙基纤维素、羧甲基纤维素、羟乙基纤维素、甲基羟乙基纤维素、羟丙基纤维素或羟丙基甲基纤维素的混合物,尤其优选它与20-25wt%羧甲基纤维素的混合物。还可提及的合成增稠剂的实例有,例如基于聚(甲基)丙烯酸或聚(甲基)丙烯酰胺的那些增稠剂,以及分子量为例如2000-20,000的聚亚烷基二醇如聚乙二醇或聚丙二醇、或由环氧乙烷和环氧丙烷形成的混合聚亚烷基二醇。
墨水中这些增稠剂的含量为墨水总重量的0.01-2wt%,特别是0.01-1wt%,优选为0.01-0.5wt%。
墨水中还可以包含缓冲物质如硼砂、硼酸盐、磷酸盐、聚磷酸盐或柠檬酸盐。可提及的实例包括硼砂、硼酸钠、四硼酸钠、磷酸二氢钠、磷酸氢二钠、三聚磷酸钠、五聚磷酸钠和柠檬酸钠。特别是它们的使用量为墨水总重量的0.1-3wt%,优选0.1-1wt%,以便使墨水的pH值为例如4-9,特别是5-8.5。
作为进一步的添加剂,墨水中可以包含表面活性剂或润湿剂。
适合的表面活性剂包括市售的阴离子表面活性剂或非离子表面活性剂。本发明墨水中的润湿剂有,例如尿素、乳酸钠(优选采用50%-60%的水溶液形式)与丙三醇和/或丙二醇的混合物,用量优选为0.1-30wt%,特别是2-30wt%。
优选墨水的粘度为1-40mPa·s,特别是1-20mPa·s,更特别的是1-10mPa·s。
此外,墨水还可另外包括惯用添加剂,如防沫剂或特别是抑制真菌和/或细菌生长的防腐剂。此类添加剂的使用量通常为墨水总重量的0.01-1wt%。
防腐剂可采用产甲醛剂,例如多聚甲醛和三噁烷(特别是甲醛浓度约为30-40wt%的水溶液)、咪唑化合物如2-(4-噻唑基)苯并咪唑、噻唑化合物如1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮、碘化合物、腈、酚、卤代烷基硫代化合物或吡啶衍生物,特别是1,2-苯并异噻唑啉-3-酮或2-正辛基-异噻唑啉-3-酮。适合的防腐剂是例如在二丙二醇中的浓度为20wt%的1,2-苯并异噻唑啉-3-酮溶液(ProxelGXL)。
在采用喷墨印刷方法时,墨水的细小液滴以受控方式经喷嘴喷射到基材上。用于此目的的主要是连续喷墨方法和按需喷墨方法。对于连续喷墨方法,液滴是连续产生的,印刷操作不需要的那部分液滴则被排入一个容器并循环使用。另一方面,对于按需喷墨方法,液滴根据需要而产生并用于印刷,即只有当印刷操作需要时才产生液滴。可通过例如一个压电喷墨头或通过热能(墨泡喷射)来影响液滴的产生。优选采用压电喷墨头并依据连续喷墨的方法来印刷。
因此,本发明还涉及包含本发明式(1)染料的水性墨水,以及用喷墨印刷方法印刷各种基材,特别是纺织纤维材料时该墨水的用途,上面指出的定义和优选适用于这些染料、墨水和基材。
以下实施例用于说明本发明。除非另外指明,否则温度按摄氏度给出,份数为重量份数,百分数指重量百分数wt%。重量份数指的是以千克/升比率表示的体积份数。
实施例1:
(a)将26.4份游离酸形式的对应于式
的化合物在100份水中进行搅拌。在浆液中加入约50份冰使其冷却到0℃,用氢氧化钠水溶液将pH值调节到4,用冰冷却使其温度维持在0℃。将所得溶液缓慢加入到在20份水、约80份冰和0.2份Na2HPO412H2O中混有18.2份氰尿酰氯的浆液中,加入氢氧化钠水溶液使pH值维持在3并加入冰使温度维持在0℃。得到包含下式化合物的悬浮液,
该式显示化合物呈游离酸形式。
(b)在一个高压釜中,将43份游离酸形式、对应于式
的化合物与550份水、15份甲酸和6.8份醋酸铬(III)一起制成浆液,并在100-105℃的温度下加热20小时。压力约为3巴。冷却到室温后,过滤出沉淀物,用水洗涤,并在50℃的温度下真空干燥。得到游离酸形式、对应于式
(c)将按常规工艺由重氮化的4-硝基-2-氨基苯酚和2-氨基-8-萘酚-6-磺酸制得的、游离酸形式的对应于式
的38.8份单偶氮染料,与47份根据(b)所获得的铬络合物在600份水中一起进行搅拌,直到成为均相然后加热到70℃。加入2N的氢氧化钠溶液使pH值为8.0-8.5并保持在该范围。然后继续在上述温度搅拌,直到在所得的透明溶液中检测不出两种起始反化合应物为止。得到游离酸形式、对应于式
(d)让透明溶液冷却到50℃,加入盐酸将水溶液pH调节到5左右,然后将根据(a)得到的悬浮液缓慢加入,加入氢氧化钠水溶液使pH值维持在5。为了使反应完全,进一步搅拌2小时,并在pH值6-7的条件下透析脱除溶液中的盐分,蒸发浓缩干燥。得到游离酸形式、对应于式
实施例2:
在室温与pH值为11的条件下,用氢氧化钠处理实施例1所得的染料水溶液约2小时。透析脱除所得溶液中的盐分,并蒸发浓缩。得到游离酸形式的对应于式
的染料及其配位异构体(λmax=572nm)。用式(102)染料在含氨基纤维上进行染色,所得深黑染色甚至不需要后固色工序就具有非常好的永久耐湿性能,特别是使用欧洲专利申请No.03 104 150.2所描述的染色工艺进行染色时。
实施例3-6:
可采用实施例1和2中所描述的类似方法来得到式
(λmax=570nm)
和
(λmax=570nm)的染料以及相应的丙烯酸盐和乙烯基化合物形式的染料(除了以结构式形式公开的式(103)和(104)染料,本公开还包括了相应的配位异构体)。
实施例7:
在0-2℃的温度下,用10-15分钟的时间将4.7份氰尿酰氯悬浮在47份冰、23份水和0.025份Na2HPO4×12H2O中。然后,在0-2℃的温度下,用45分钟的时间,加入22.3份实施例1(c)中得到染料溶液,加入冰使温度维持在0-2℃,并通过加入2N的氢氧化钠溶液使pH值保持在5-6。然后在0-2℃以及pH不变的情况下搅拌40分钟。得到游离酸形式、对应于式
(b)将8.2份游离酸形式的对应于式
的化合物溶于140份水中。将如此得到的溶液用45分钟的时间逐滴加入到(a)步所得的溶液中。在加入过程中,用2N的氢氧化钠溶液使pH值保持在6。透析脱除反应溶液中的盐分并蒸发浓缩。得到游离酸形式的、对应于式
实施例8:
在室温与pH值为11的条件下,用氢氧化钠处理实施例7所得的染料水溶液约2小时。透析脱除所得溶液中的盐分并蒸发浓缩。得到游离酸形式的对应于式
实施例9-12:
可采用实施例7和8中所描述的类似方法来得到式
(λmax=574nm)
和
(λmax=574nm)的染料以及相应的丙烯酸盐和乙烯基化合物形式的染料(除了以通式形式公开的式(107)和(108)染料,本公开还包括了相应的配位异构体)。
浸染工序1:
将10份聚酰胺6,6纤维材料(Helanca tricot)在500份用醋酸将pH调到3的含水液体中进行浸染。实施例8的染料的比例为纤维重量的2%。在98℃下的浸染时间为30-90分钟。然后取出被浸染的纤维材料,用水漂洗,并在pH 10-11.5、70-90℃下用苏打水洗涤20-30分钟以除去未固色的染料。再用水漂洗,并在醋酸溶液中酸化到pH 4,然后干燥纤维材料。得到耐湿性能卓越的深黑浸染。
浸染工序2:
在一个染色设备中,于40℃的温度下,用1.5升含有3g甲酸、0.4g润湿剂和0.7g均染剂的液体,处理70g由72%聚酰胺微纤和28%弹性纤维组成的混合织物10分钟。液体的pH为2.9。然后加入3.8g预先溶解在少量水中的实施例2的染料。将欲浸染的材料于40℃下在染色液中处理5分钟,然后加热到100℃并在该温度下浸染20分钟。接着加入14g氯化钙,然后再浸染40分钟。浸染后,用1.5升含有2g 1,6-六亚甲基二胺的后处理溶液在70-90℃处理纤维材料20分钟。然后漂洗材料并用常规方法进行整理。得到固色性能非常好的深色均染。
为了进一步提高固色性能,还可增加后固色步骤或碱性后处理。对于碱性后处理,是将染色后的纤维材料在60-80℃,在含有2g/l苏打且pH为9.2的新鲜溶液中处理20分钟。
浸染工序3:
用每1000份染色液中含有3份实施例2染料以及1份市售增稠剂、1份非离子润湿剂和使染料溶液pH为5.0时所需量的拧檬酸的染色液,来连续浸染聚酰胺6,6编织毯材料。然后将编织毯材料在蒸汽中于100℃下固色5分钟,并用惯常方法进行清洗和干燥。编织毯材料具有固色性能非常好的均匀深黑染色。
浸染工序4:
用醋酸(80%)将每100份水中含有1.6份实施例2的染料、0.5份硫酸钠和2份醋酸钠的染色液的pH值调到4.5,然后在30℃下,于搅拌中加入10份羊毛针织纱线。用45分钟将染色液加热到沸腾,并在该沸腾温度下再保持45-70分钟。然后取出染好的材料,用冷水彻底漂洗并干燥。得到固色性能非常好的深黑色浸染。
印刷工序I:
(a)用含有30g/l碳酸钠和50g/l尿素的液体(70%液体浓度)对丝光棉缎进行轧卷染色并干燥。
(b)通过一个按需喷墨头(墨泡喷射),用含有
-15wt%实施例2的(102)式活性染料,
-15wt%1,2-丙二醇和
-70wt%水
的水性墨水对步骤(a)的预处理棉缎进行印刷。
使印刷完全干燥并于102℃下在饱和蒸汽中固色8分钟,冷漂洗,在沸腾下洗涤,再漂洗并干燥。
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PCT/EP2005/055120 WO2006042802A1 (en) | 2004-10-19 | 2005-10-10 | Reactive dyes, their preparation and their use |
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TWI500707B (zh) * | 2009-01-21 | 2015-09-21 | Huntsman Adv Mat Switzerland | 反應性染料,其裝備及用途 |
JP5639348B2 (ja) * | 2009-06-18 | 2014-12-10 | 旭化成せんい株式会社 | ポリアミド繊維とポリウレタン繊維との混用糸条又は布帛の染色品 |
CN103030994A (zh) * | 2010-08-27 | 2013-04-10 | 天津德凯化工股份有限公司 | 一种用于染色纯棉的染料活性兰 |
CN102391677B (zh) * | 2011-07-07 | 2015-10-21 | 天津德凯化工股份有限公司 | 黑色活性染料的制备方法 |
US9346958B2 (en) * | 2012-06-05 | 2016-05-24 | Huntsman International Llc | Reactive dyes, their preparation and their use |
CN103725041B (zh) * | 2013-12-31 | 2017-02-22 | 浙江亿得化工有限公司 | 酸性染料和凹印油墨及其制备方法及应用 |
CN104140714A (zh) * | 2014-07-18 | 2014-11-12 | 浙江亿得化工有限公司 | 一种新型酸性油墨及其制备方法和直接印花工艺 |
KR101807362B1 (ko) * | 2015-10-20 | 2017-12-11 | 주식회사 효성 | 염색성이 개선된 폴리우레탄 또는 폴리우레탄우레아 탄성사 및 이의 제조방법 |
CN105602286B (zh) * | 2016-03-17 | 2017-12-12 | 浙江瑞华化工有限公司 | 一种黑色活性染料组合物及其制备方法和用途 |
CN105647238B (zh) * | 2016-03-17 | 2017-08-08 | 浙江瑞华化工有限公司 | 一种灰色活性染料组合物及其制备方法和用途 |
JP2020128448A (ja) * | 2017-06-16 | 2020-08-27 | コニカミノルタ株式会社 | インクジェット捺染インク及びインクジェット捺染方法 |
CN108912724B (zh) * | 2018-05-31 | 2020-11-10 | 上海青石化学有限公司 | 一种不对称金属络合黑色染料及其制备方法 |
CN109575630B (zh) * | 2018-11-20 | 2020-04-10 | 浙江劲光实业股份有限公司 | 一种红棕色活性染料的制备方法 |
EP3772529B1 (en) * | 2019-08-05 | 2023-04-19 | Sanko Tekstil Isletmeleri San. Ve Tic. A.S. | Ph-sensitive dyes for textile materials, a process for their preparation and uses thereof |
CN113200931B (zh) * | 2021-04-29 | 2022-05-13 | 浙江理工大学上虞工业技术研究院有限公司 | 反应性耐光汗复合牢度增进剂及其制备方法 |
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US2943084A (en) * | 1957-08-14 | 1960-06-28 | Ciba Ltd | New chromiferous monoazo-dyestuffs |
US4206306A (en) * | 1967-04-19 | 1980-06-03 | Bayer Aktiengesellschaft | Reactive phthalocyanine dyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule |
GB2034343A (en) * | 1978-09-29 | 1980-06-04 | Bayer Ag | Reactive dyestuffs |
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US20080083073A1 (en) | 2008-04-10 |
EP1802709B1 (en) | 2012-01-11 |
RU2402582C2 (ru) | 2010-10-27 |
BRPI0518230A2 (pt) | 2008-11-11 |
JP4638503B2 (ja) | 2011-02-23 |
KR100954509B1 (ko) | 2010-04-27 |
CN101044211A (zh) | 2007-09-26 |
US7678161B2 (en) | 2010-03-16 |
ES2378384T3 (es) | 2012-04-11 |
WO2006042802A1 (en) | 2006-04-27 |
EP1802709A1 (en) | 2007-07-04 |
KR20070068464A (ko) | 2007-06-29 |
WO2006042802A9 (en) | 2007-07-26 |
BRPI0518230B1 (pt) | 2016-12-27 |
JP2008517128A (ja) | 2008-05-22 |
ATE541013T1 (de) | 2012-01-15 |
RU2007118536A (ru) | 2008-11-27 |
BRPI0518230B8 (pt) | 2023-05-16 |
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