CN116694102A - 具有n,n-二乙基-6-氨基苯并噻唑结构的偶氮型分散染料及其制备方法和应用 - Google Patents
具有n,n-二乙基-6-氨基苯并噻唑结构的偶氮型分散染料及其制备方法和应用 Download PDFInfo
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- CN116694102A CN116694102A CN202310691314.XA CN202310691314A CN116694102A CN 116694102 A CN116694102 A CN 116694102A CN 202310691314 A CN202310691314 A CN 202310691314A CN 116694102 A CN116694102 A CN 116694102A
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- 239000000986 disperse dye Substances 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 238000004043 dyeing Methods 0.000 claims abstract description 48
- 239000000975 dye Substances 0.000 claims abstract description 28
- 239000000835 fiber Substances 0.000 claims abstract description 19
- 229920000742 Cotton Polymers 0.000 claims abstract description 16
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229920000728 polyester Polymers 0.000 claims abstract description 13
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 12
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000008878 coupling Effects 0.000 claims abstract description 8
- 238000010168 coupling process Methods 0.000 claims abstract description 8
- 238000005859 coupling reaction Methods 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims description 27
- 239000012954 diazonium Substances 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 11
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001989 diazonium salts Chemical class 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 238000006149 azo coupling reaction Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
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- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
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- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 42
- 239000004744 fabric Substances 0.000 abstract description 25
- 239000001569 carbon dioxide Substances 0.000 abstract description 21
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 21
- 239000000047 product Substances 0.000 abstract description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
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- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
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- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
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- 239000002243 precursor Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229940079101 sodium sulfide Drugs 0.000 description 2
- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
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- 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes
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- C—CHEMISTRY; METALLURGY
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
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Abstract
本发明公开了具有N,N‑二乙基‑6‑氨基苯并噻唑结构的偶氮型分散染料及其制备方法和应用，属于染料合成技术领域。本发明首先对2‑氨基‑6‑硝基苯并噻唑进行重氮化，重氮化溶液与N,N‑二乙基苯胺的偶合得到重氮偶合产物，对合成的重氮偶合产物进行硝基还原得到N,N‑二乙基‑6‑氨基苯并噻唑分散染料，在N,N‑二乙基‑6‑氨基苯并噻唑分散染料上接枝均三嗪活性基团，得到最终产物N,N‑二乙基苯并噻唑均三嗪活性分散染料，该分散染料在超临界二氧化碳染色过程中，染料吸附在溶胀后的纤维表面并扩散进入其内部，完成对涤纶织物的上染；同时利用活性分散染料中的活性基团与棉纤维的‑OH形成氢键结合，从而实现对涤/棉65/35的同色拼染。
Description
技术领域
本发明属于染料合成技术领域，具体涉及用于超临界二氧化碳无水染色的具有N,N-二乙基-6-氨基苯并噻唑结构的偶氮型分散染料及其制备方法和应用。
背景技术
超临界状态下，二氧化碳具有与气体相似的黏度和与液体相似的密度，表现出向基质的高扩散性能与对低极性物质的强溶解能力，从而使其在纺织染色领域极具应用价值。研究发现，利用超临界二氧化碳流体溶解低极性染料进行纺织材料染色，无需水介质添加即可实现染料对纤维的快速高上染率染色；染色结束后，可以省去水洗、烘干工序，明显缩短了染色流程，降低了生产能耗；同时，未尽染染料能够在分离装置内通过相态转变与二氧化碳流体分离，从而完成染料和二氧化碳的循环利用，显示出零排放无污染的染色特点。因此，作为传统水介质染色技术的潜在替代技术，超临界二氧化碳流体染色一直受到国内外学者的广泛关注。
涤棉纤维兼具了涤和棉两种纤维的优良特性，但是棉纤维的存在导致常规分散染料无法对其进行有效上染，因此，研究开发可用于涤棉纤维染色的新的分散染料和活性分散染料成为当前亟待研究的重要课题。
发明内容
为解决上述问题，本发明的目的是提供了一种适用于超临界二氧化碳涤棉混纺织物同色无水拼染的N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料及其制备方法和应用，以提高涤棉混纺织物的染色效果，实现涤棉混纺织物的一浴法无助剂染色。
为了实现本发明的目的，本发明提供如下技术方案：
本发明提供具有N,N-二乙基-6-氨基苯并噻唑结构的偶氮型染料，所述的染料包括N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料，N,N-二乙基-6-氨基苯并噻唑分散染料的结果如式I所示，N,N-二乙基苯并噻唑均三嗪活性分散染料的结构式如式II所示；
本发明另一方面提供上述的偶氮型染料的制备方法，包括以下步骤：
(1)2-氨基-6-硝基苯并噻唑的重氮化：将2-氨基-6-硝基苯并噻唑溶解在混酸溶液中，冷却至0-5℃，加入HNO2，搅拌反应1-5h，得到一种澄清的淡黄色重氮盐III溶液；
(2)重氮盐III与N,N-二乙基苯胺的偶合：将N,N-二乙基苯胺溶于碱性溶液中，滴加重氮盐III溶液，将pH值调节到酸性，在0-5℃下反应2-5h，抽滤，干燥，得到重氮偶合产物IV；
(3)重氮偶合产物IV的硝基还原：将重氮偶合产物IV完全溶解于醇溶液中，在40～80℃下搅拌，逐滴加入溶有硫化钠和碳酸氢钠的水溶液，回流反应2-5h，冷却，抽滤，得到分散染料I；
(4)分散染料I接枝均三嗪活性基团：将分散染料I加入有机溶剂中，加入缚酸剂，0-5℃下搅拌至完全溶解，滴加含有1～2倍当量三聚氯氰的有机溶剂，调节pH至6.5～7.5，搅拌反应2～5h，得到活性分散染料II；
基于上述技术方案，进一步地，步骤(1)中所述的混酸溶液是由体积比为2:1～1:2的浓硫酸和浓磷酸混合而成；HNO2与2-氨基-6-硝基苯并噻唑的摩尔比为2:1～1:1。
基于上述技术方案，进一步地，步骤(2)中碱性溶液为NaOH溶液、KOH溶液中的一种或两种的混合溶液；N,N-二乙基苯胺与重氮盐III的摩尔比为1:1。
基于上述技术方案，进一步地，步骤(3)中醇溶液为甲醇、乙醇、丙醇中的一种或两种以上的混合溶液；硫化钠、碳酸氢钠与重氮偶合产物IV的摩尔比均为2:1～1:1。
基于上述技术方案，进一步地，步骤(4)中所述的有机溶剂所述的有机溶剂包括四氢呋喃；缚酸剂包括二乙胺，缚酸剂与分散染料I的摩尔比为2:1～1:1。
基于上述技术方案，进一步地，步骤(2)和步骤(4)中所述烘干的条件为：40～80℃烘干10～24h。
本发明还提供所述的偶氮型染料在超临界CO2无水染色中的应用。
基于上述技术方案，进一步地，以超临界CO2流体为染色介质，采用所述的N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料中的一种或两种组合对待染纺织品进行染色。
基于上述技术方案，进一步地，待染纺织品为纤维素纤维、蛋白质纤维、化学纤维中的一种或两种以上形成的混纺织物。
基于上述技术方案，进一步地，所述纤维素纤维为棉纤维、麻纤维，所述蛋白质纤维为毛纤维、丝纤维，所述化学纤维为涤纶。
基于上述技术方案，进一步地，所述染色具体过程为：将0.5-2.5％(o.w.f)的染料置于染料釜内，再将待染纺织品置于染色釜内，于80-150℃、16-25MPa的条件下染色40-150min。
与现有技术相比，本发明的有益效果为：
本发明合成的N,N-二乙基-6-氨基苯并噻唑分散染料在超临界体系下对涤纶织物具有较高的上染性；接枝三聚氯氰合成N,N-二乙基苯并噻唑活性分散染料在超临界体系下对纯棉织物具有更好的上染性；在超临界体系下采用上述两种染料对涤/棉(65/35)织物进行一浴法拼染，获得了较好的染色效果，本发明合成的带有二氯均三嗪活性基团结构的偶氮型(活性)分散染料，可满足棉、麻、毛等天然纤维的反应着色要求，特别是对涤棉等混纺纤维材料具有良好的上染性及透染性能，且染色产品耐洗牢度和耐擦牢度均可达4-5级以上。
附图说明
图1为N,N-二乙基-6-氨基苯并噻唑分散染料(A1)和N,N-二乙基苯并噻唑均三嗪活性分散染料(A2)的红外光谱图。
图2为N,N-二乙基-6-氨基苯并噻唑分散染料(A1)和N,N-二乙基苯并噻唑均三嗪活性分散染料(A2)的紫外吸收光谱。
图3为N,N-二乙基-6-氨基苯并噻唑分散染料(A1)和N,N-二乙基苯并噻唑均三嗪活性分散染料(A2)的标准吸收曲线。
图4为N,N-二乙基-6-氨基苯并噻唑分散染料(A1)和N,N-二乙基苯并噻唑均三嗪活性分散染料(A2)的热重分析图。
图5为N,N-二乙基-6-氨基苯并噻唑分散染料核磁氢谱图。
图6为N,N-二乙基-6-氨基苯并噻唑分散染料核磁碳谱图。
图7为N,N-二乙基苯并噻唑均三嗪活性分散染料核磁氢谱图。
图8为N,N-二乙基苯并噻唑均三嗪活性分散染料核磁碳谱图。
具体实施方式
下述非限定性实施例可以使本领域的普通技术人员更全面地理解本发明，但不以任何方式限制本发明。
实施例1
本实施例提供一种N,N-二乙基苯并噻唑均三嗪活性分散染料的合成方法，包括以下步骤：
(1)将2-氨基-6-硝基苯并噻唑(2.25g，0.01mol)溶解在含有11mL硫酸(98％)和17mL磷酸(80％)的混合溶液中，将混合物加热至78℃,搅拌3h。将亮黄色溶液冷却至0-5℃。此后，将亚硝酸钠(0.69g,0.01mol)溶解在5mL硫酸(98％)中以生成亚硝酸，将其逐滴添加到上述混合物中，在搅拌下反应3h，反应后通过添加尿素去除多余的亚硝酸，并使用淀粉KI试纸检测，直至淀粉KI试纸1-2s内不变色，得到一种澄清的淡黄色重氮盐溶液；
(2)将N,N-二乙基苯胺(1.49g，0.01mol)溶于氢氧化钠溶液(50mL，0.8mol/L)中，将重氮盐溶液缓慢添加到其中，通过添加30％(w/v)氢氧化钠溶液，将混合物的pH值调节到弱酸性，在0-5℃下反应2.5-3h，抽滤得到固体产物，在60℃真空干燥箱中干燥24h，得到重氮偶合染料母体1.69g(75％)；合成路线如下：
(3)取重氮偶合染料母体(3.55g，0.01mol)完全溶解于乙醇中，在60℃下搅拌。将九水硫化钠(2.4g,0.01mol)和碳酸氢钠(0.88g，0.01mol)溶10mL水中，逐滴添加到上述溶液中，回流反应3-4h，得到N,N-二乙基-6-氨基苯并噻唑分散染料；合成路线如下：
(4)称取N,N-二乙基-6-氨基苯并噻唑分散染料(1.627g，0.005mol)溶于100mL四氢呋喃中，加入0.52mL(0.005mol)二乙胺作为缚酸剂，0-5℃下搅拌15min至完全溶解，将三聚氯氰(0.92g，0.005mol)溶解于四氢呋喃中，滴加到上述溶液中，通过二乙胺调节pH＝7，冰浴条件下快速搅拌反应3h，得到N,N-二乙基苯并噻唑均三嗪活性分散染料；合成路线如下：
本实施例合成的N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料的紫外吸收光谱、红外光谱、标准吸收曲线、热重分析图、核磁氢谱图和核磁碳谱图分别如图1-8所示，由图1可以看出，N,N-二乙基-6-氨基苯并噻唑分散染料最大吸收峰在335nm处出现，N,N-二乙基苯并噻唑均三嗪活性分散染料最大吸收峰在353nm处出现，表明成功合成了N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料。
实施例2
一种涤纶织物超临界二氧化碳无水染色方法：将2％(o.w.f)的N,N-二乙基-6-氨基苯并噻唑分散染料置于染料釜中，将待染涤纶织物置于染色釜中，以超临界二氧化碳流体为染色介质，于120℃、24MPa的条件下进行染色120min，所得染色织物K/S值最大为20.30，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
实施例3
一种纯棉织物超临界二氧化碳无水染色方法：将2％(o.w.f)的N,N-二乙基苯并噻唑均三嗪活性分散染料置于染料釜中，将待染纯棉织物置于染色釜中，以超临界二氧化碳流体为染色介质，于110℃、24MPa的条件下进行染色120min，所得染色织物K/S值最大为9.05，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
实施例4
一种涤/棉(65/35)织物超临界二氧化碳无水染色方法：将质量比为1：1的2％(o.w.f)的N,N-二乙基-6-氨基苯并噻唑及N,N-二乙基苯并噻唑均三嗪活性分散染料置于染料釜中，将待染涤/棉(65/35)织物置于染色釜中，以超临界二氧化碳流体为染色介质，于120℃、24MPa的条件下进行拼色染色100min，所得染色织物K/S值最大为15.45，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
实施例5
一种麻织物超临界二氧化碳无水染色方法：将2％(o.w.f)的N,N-二乙基苯并噻唑均三嗪活性分散染料置于染料釜中，将待麻织物置于染色釜中，以超临界二氧化碳流体为染色介质，于120℃、24MPa的条件下进行染色120min。染色织物K/S为11.36，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
实施例6
一种丝织物超临界二氧化碳无水染色方法：将2％(o.w.f)的N,N-二乙基苯并噻唑均三嗪活性分散染料置于染料釜中，将待丝织物置于染色釜中，以超临界二氧化碳流体为染色介质，于120℃、24MPa的条件下进行染色120min。染色织物K/S为13.32，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
实施例7
一种毛织物超临界二氧化碳无水染色方法：将2％(o.w.f)的N,N-二乙基苯并噻唑均三嗪活性分散染料置于染料釜中，将待毛织物置于染色釜中，以超临界二氧化碳流体为染色介质，于120℃、24MPa的条件下进行染色120min。染色织物K/S为10.58，耐水洗色牢度及耐摩擦色牢度均可达4-5级以上。
对于任何熟悉本领域的技术人员而言，在不脱离本发明技术方案范围情况下，都可利用上述揭示的技术内容对本发明技术方案作出许多可能的变动和修饰，或修改为等同变化的等效实施例。因此，凡是未脱离本发明技术方案的内容，依据本发明的技术实质对以上实施例所做的任何简单修改、等同变化及修饰，均应仍属于本发明技术方案保护的范围内。
Claims (10)
1.一种具有N,N-二乙基-6-氨基苯并噻唑结构的偶氮型染料，其特征在于，所述的染料包括N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料，N,N-二乙基-6-氨基苯并噻唑分散染料的结果如式I所示，N,N-二乙基苯并噻唑均三嗪活性分散染料的结构式如式II所示；
2.权利要求1所述的偶氮型染料的制备方法，其特征在于，包括以下步骤：
(1)2-氨基-6-硝基苯并噻唑的重氮化：将2-氨基-6-硝基苯并噻唑溶解在混酸溶液中，冷却至0-5℃，加入HNO2，搅拌反应1-5h，得到一种澄清的淡黄色重氮盐III溶液；
(2)重氮盐III与N,N-二乙基苯胺的偶合：将N,N-二乙基苯胺溶于碱性溶液中，滴加重氮盐III溶液，将pH值调节到酸性，在0-5℃下反应2-5h，抽滤，干燥，得到重氮偶合产物IV；
(3)重氮偶合产物IV的硝基还原：将重氮偶合产物IV完全溶解于醇溶液中，在40～80℃下搅拌，逐滴加入溶有硫化钠和碳酸氢钠的水溶液，回流反应2-5h，冷却，抽滤，得到分散染料I；
(4)分散染料I接枝均三嗪活性基团：将分散染料I加入有机溶剂中，加入缚酸剂，0-5℃下搅拌至完全溶解，滴加含有1～2倍当量三聚氯氰的有机溶剂，调节pH至6.5～7.5，搅拌反应2～5h，得到活性分散染料II；
3.根据权利要求2所述的制备方法，其特征在于，步骤(1)中所述的混酸溶液是由体积比为2:1～1:2的浓硫酸和浓磷酸混合而成；HNO2与2-氨基-6-硝基苯并噻唑的摩尔比为2:1～1:1。
4.根据权利要求2所述的制备方法，其特征在于，步骤(2)中碱性溶液为NaOH溶液、KOH溶液中的一种或两种的混合溶液；N,N-二乙基苯胺与重氮盐III的摩尔比为1:1。
5.根据权利要求2所述的制备方法，其特征在于，步骤(3)中醇溶液为甲醇、乙醇、丙醇中的一种或两种以上的混合溶液；硫化钠、碳酸氢钠与重氮偶合产物IV的摩尔比均为2:1～1:1。
6.根据权利要求2所述的制备方法，其特征在于，步骤(4)中所述的有机溶剂所述的有机溶剂包括四氢呋喃；缚酸剂包括二乙胺，缚酸剂与分散染料I的摩尔比为2:1～1:1。
7.权利要求1所述的偶氮型染料在超临界CO2无水染色中的应用。
8.根据权利要求7所述的应用，其特征在于，以超临界CO2流体为染色介质，采用所述的N,N-二乙基-6-氨基苯并噻唑分散染料和N,N-二乙基苯并噻唑均三嗪活性分散染料中的一种或两种组合对待染纺织品进行染色。
9.根据权利要求8所述的应用，其特征在于，待染纺织品为纤维素纤维、蛋白质纤维、化学纤维中的一种或两种以上形成的混纺织物；所述纤维素纤维为棉纤维、麻纤维，所述蛋白质纤维为毛纤维、丝纤维，所述化学纤维为涤纶。
10.根据权利要求8所述的应用，其特征在于，所述染色具体过程为：将0.5-2.5％(o.w.f)的染料置于染料釜内，再将待染纺织品置于染色釜内，于80-150℃、16-25MPa的条件下染色40-150min。
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