CN108864732B - 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 - Google Patents
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 Download PDFInfo
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- 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
- C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
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- 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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Abstract
本发明涉及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，化合物的结构式如下：
Description
技术领域
本发明属于偶氮染料领域，特别涉及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。
背景技术
基于作为重氮化组分的氨基邻苯二甲酰亚胺的偶氮染料已广泛应用。然而，已经发现使用目前已知的染料得到的染色品或印刷品并不能在所有情况下都满足今天的需要。仍需要一种具有耐升华、耐汗渍的综合性能优异的染料。
发明内容
本发明所要解决的技术问题是提供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，该化合物克服了现有技术中染料耐升华、耐汗渍性能不足的问题。
本发明提供了一种含甲磺酰胺基团的偶氮染料化合物，所述化合物的结构式如下：
其中，
R1、R2、R3分别是C1-C4的直链或支链的烷基；
R4是C1-C4的直链或支链的烷基或苯基；
X和Y分别独立的是卤素、氢、氰基或硝基。
优选的，所述R1、R2、R3分别是甲基、乙基或丁基；R4是甲基或苯基。
更有选的，所述R1、R2分别是乙基；R4是甲基。
优选的，所述X为氢，Y为Cl、Br、氰基或硝基；或者X为Cl、Br、氰基或硝基，Y为氢。
最优选的，所述化合物的结构式如下：
本发明还提供了一种含甲磺酰胺基团的偶氮染料化合物的制备方法，包括如下步骤：将式II化合物
重氮化并偶联至式III化合物
其中，
R1、R2、R3分别是C1-C4的直链或支链的烷基；
R4是C1-C4的直链或支链的烷基或苯基；
X和Y分别独立的是卤素、氢、氰基或硝基。
通常，通式(II)化合物的重氮化以已知的方式进行，例如在用如盐酸或硫酸使其呈酸性的水性介质中使用亚硝酸钠，或者在稀释的硫酸、磷酸、或者乙酸与丙酸的混合物中使用亚硝酰基硫酸。优选的温度范围在0℃与15℃之间。
同样，将重氮化的化合物偶联至通式(III)的化合物通常也以已知的方式进行，例如在酸性、水性、水性-有机或有机介质中，特别有利地在低于10℃的温度下进行。所用的酸特别是硫酸、乙酸或丙酸。
通式(II)和(III)的化合物是已知的，并能够通过已知的方法制备。
本发明还提供了一种含甲磺酰胺基团的偶氮染料化合物的应用，应用于疏水性材料或含有疏水性材料的混纺材料染色或印花。
本发明还提供了一种含有含甲磺酰胺基团的偶氮染料化合物的染料组合物，包含至少一个式I的化合物和至少一种除式I以外的染料化合物。
本发明还提供了一种染料组合物的应用，应用于疏水性材料或含有疏水性材料的混纺材料染色或印花。
本发明还提供了一种含有如权利要求1所述的偶氮染料化合物和分散剂的染料。
所述疏水性材料为涤纶、锦纶、氨纶、丙纶、氯纶或腈纶。
所述的混纺材料是疏水性材料与其它棉毛、丝、麻等到天然纤维混合纺纱织成的纺织材料，包括例如涤棉、毛粘混纺、羊兔毛混纺等。
本发明的式(I)化合物或含有式(I)化合物的染料组合物在用于疏水性材料的染色和印花的使用过程中，需要加入助剂，所述助剂为分散染料复配时常用的分散剂、扩散剂及其他表面活性剂等。优选的助剂包括下列之一或其混合物：萘磺酸甲醛缩合物、木质素磺酸盐、烷基萘磺酸甲醛缩合物。如甲基萘磺酸甲醛缩合物(分散剂MF)、萘磺酸甲醛缩合物(扩散剂NNO)、苄基萘磺酸甲醛缩合物(扩散剂CNF)、木质素磺酸钠(木质素83A、85A)等。通常，加入助剂的重量与式(I)化合物或含有式(I)化合物的组合物的重量之比为0.6～4.8:1。
有益效果
本发明化合物具有优异的耐汗、耐摩擦色牢度，耐水洗、耐升华和拼白色牢度。即便染色浓度提高时，获得的纺织品的色牢度也十分优秀。在染色和印花疏水性材料具有良好的应用前景。所得染色物和印花物色光鲜艳，提升力好。
具体实施方式
下面结合具体实施例，进一步阐述本发明。应理解，这些实施例仅用于说明本发明而不用于限制本发明的范围。此外应理解，在阅读了本发明讲授的内容之后，本领域技术人员可以对本发明作各种改动或修改，这些等价形式同样落于本申请所附权利要求书所限定的范围。
实施例1
步骤1
150ml三口烧瓶中加入硫酸112g，搅拌，60℃以下慢慢加入27g的式II-1化合物，搅拌至澄清，然后降温至5～10℃慢慢加入亚硝酰硫酸(40％)31.5g，加完5～10℃保温重氮3小时，待偶合。
步骤2
1000ml烧杯内加入500g冰水混合物，搅拌，加入氨基磺酸2.5g，在5℃下慢慢加入式(III-1)化合物33g，然后慢慢加入上述步骤1的偶合组分，加完在10℃左右保温反应5～6小时，直接升温至65℃，搅拌，保温1小时，过滤，水洗至中性，柱层析分离，得式(I-1)化合物50g，HPLC纯度>90％。1H-NMR(DMSO，300MHz)：1.15(9H，m)，3.22(3H，s)，3.40(2H，m)，3.46(2H，m)，3.52(4H，m)，3.63(4H，m)，4.18(2H，t)，6.41(1H，d)，6.20(1H，d)，7.58(1H，d),8.02(1H，d),8.23(1H，d),10.2(1H，s)。
实施例2
根据实施例1的方法，合成下列化合物
表1
实施例3
将上述实施例I-1～I-9的化合物与MF混合，干燥，制得的分散染料组合物，用水分别配制成质量百分比浓度为1％和3％的分散染料悬浮液，吸取20ml分散染料悬浮液与80m的水混合，用醋酸调节染浴pH到5，然后升温到60℃，同时分别放入2g涤纶纤维进行高温高压染色，在35分钟内升温到130℃，保温30分钟，冷却到80℃取样。
实施例4
采用GBT3920-2008的方法测试根据实施例3制备的染色布样的耐摩擦牢度，牢度用级别表示。如表2所示，本发明化合物的染料摩擦牢度非常优秀，而且当染色浓度提升，摩擦牢度也非常优秀。
表2
实施例5
采用GB/T 14576-2009的方法测试根据实施例3制备的染色布样的耐汗渍牢度，牢度用级别表示。如表3所示，本发明化合物的染料耐汗牢度非常优秀，而且当染色浓度提升，耐汗牢度也非常优秀。
表3
实施例5
采用GBT 31127-2014的方法，测试根据实施例3制备的染色布样，取1％和3％浓度印染的布样，测试拼白牢度。如表4所示，本发明化合物的染料具有非常优秀的拼白牢度。
表4
实施例6
采用GBT3921-2008的方法测试根据实施例3制备的染色布样的耐水洗牢度。如表5所示，本发明化合物的染料具有非常优秀的水洗牢度。
表5
实施例7
采用GB/T6152-1997方法测试根据实施例3制备的染色布样的升华牢度。如表5所示，本发明化合物的染料具有非常优秀的升华牢度。
表6
Claims (6)
1.一种含甲磺酰胺基团的偶氮染料化合物，其特征在于：所述化合物的结构式如下：
2.一种如权利要求1所述的含甲磺酰胺基团的偶氮染料化合物的应用，其特征在于：应用于疏水性材料或含有疏水性材料的混纺材料染色或印花。
3.一种含有如权利要求1所述的含甲磺酰胺基团的偶氮染料化合物的染料组合物，包含至少一个式I-1或式I-4的化合物和至少一种除式I-1或式I-4以外的染料化合物。
4.一种如权利要求3所述的染料组合物的应用，其特征在于：应用于疏水性材料或含有疏水性材料的混纺材料染色或印花。
5.一种含有如权利要求1所述的偶氮染料化合物和分散剂的染料。
6.根据权利要求2或4的应用，其特征在于：所述疏水性材料为涤纶、锦纶、氨纶、丙纶、氯纶或腈纶。
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| GB1459346A (en) * | 1973-07-02 | 1976-12-22 | Eastman Kodak Co | Disperse phthalimidyl azo aniline dyes |
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