摘要
分散染料最早被称为醋纤染料,是在20世纪二十年代初,为适应醋酯纤维发展而出现在市场上的。随着聚酰胺、聚丙烯腈,特别是聚酯纤维的发展,分散染料有了迅速的发展。目前分散染料已成为合成纤维,特别是聚酯纤维染色和印花的主要染料。在偶氮分散染料中,为了改进色光鲜艳度,丰富染料色谱,除在染料分子上引入各种取代基团外,还引入一些杂环化合物作为重氮组分或偶合组分,制造出一系列杂环偶氮型分散染料。杂环偶氮染料有着普通染料所没有的特殊性能,如荧光性能、光学性能、温致变色和光敏性能等。吲哚-2-酮属于五元杂环类化合物,是重要的医药和农药中间体。吲哚-2-酮类衍生物在医药中做为药效基团有着广泛的应用。但将吲哚-2-酮结构引入分散染料中的研究至今鲜见报道。如果将吲哚-2-酮结构引入到分散染料中,合成出具有杂环深色效应的分散染料,将是很有意义的事情。本论文成功地合成出了吲哚-2-酮化合物,并制备出了一系列含吲哚-2-酮结构的单偶氮分散染料,并研究了这些染料的后处理工艺和染色性能。全文共包括四部分,各部分内容分别如下。
第一部分为染料中间体吲哚-2-酮化合物的合成。以苯胺为原料,经过Friedel-Crafts烷基化法、Wolff-Kishner-黄鸣龙两步还原和Wolff-Kishner-黄鸣龙一锅还原三种方法合成出了吲哚-2-酮化合物(4a-4f),研究了这三种合成方法各自的影响因素,找到了合成吲哚-2-酮化合物的最佳工艺条件。实验结果表明,硫酸钠在制备中间产物N-异亚硝基乙酰苯胺(2a-2f)的反应中除了起到盐析效果,促进产物的析出外,还可以起到平衡反应体系电荷的作用。当硫酸钠的用量在340g/L时,中间产物2a-2f的产率均最高,达80%以上；由化合物N-异亚硝基乙酰苯胺(2a-2f)制备靛红化合物(3a-3f)时,当浓硫酸脱水关环温度在85-90℃之间时,产物靛红(3a-3f)的产率最大,达90%以上。当关环温度较低时,原料反应不剧烈,脱水关环不够,产物产率较低,温度太高,副产物增多；在用苯胺和氯乙酰氯制备中间体N-氯乙酰基苯胺(2＇a-2＇f)时,采用冰醋酸作为反应体系时,产物(2＇a-2＇f)产率最高,达94%以上。比较三种合成吲哚-2-酮化合物(4a-4f)方法发现,采用靛红经黄鸣龙还原法制备吲哚-2-酮化合物产率较高,特别是采用二缩三乙二醇作为溶剂,不经中间产物腙的分离而直接一锅还原法,产物产率都在80%以上。
第二部分为含吲哚-2-酮结构分散染料的合成。选择吲哚-2-酮(4a)、5-溴吲哚-2-酮(4b)和5-氟吲哚-2-酮(4c)为原料,经过与间硝基苯甲醛的克诺文格尔缩合,硝基还原和重氮化偶合反应,合成出了12种含吲哚-2-酮结构的单偶氮分散染料A1-A4、B1-B4和C1-C4。主要研究了各中间和最终产物的合成工艺,并对产物A1-A4、B1-B4和C1-C4的结构进行了氢核磁共振确认。研究结果表明,以氨水为醛基保护试剂,采用间接硝化法合成间硝基苯甲醛,产率可达99%；用离子液体DBUBr(溴化1,8-二氮杂环[5,4,0]十一烯-7)作为催化剂制备3-(3-硝基-苯基亚甲基)-吲哚-2-酮化合物(5a-5c)时,产率最高,达95%以上；若不采用催化剂,使用微波法合成时,产率达到90%；当采用浓盐酸和冰醋酸作为溶剂,氯化亚锡为还原剂对化合物5a-5c进行还原时,3-(3-氨基-苯基亚甲基)-吲哚-2-酮(6a-6c)的产率最高,达75%以上。制备单偶氮分散染料A1-A4时,采用亚硝酸钠/浓盐酸法、亚硝酰硫酸法、亚硝酸钠/浓硫酸三种重氮化方法所得的产率都较接近,均在80%左右,而制备染料B1-B4和C1-C4时,采用亚硝酰硫酸和混酸的方法进行重氮化偶合后的产率达80%以上,明显高于其他两种重氮化方法的产率。
第三部分为分散染料的光学性质和后处理工艺研究。主要研究了所合成分散染料的最大吸收波长与结构的关系、分散剂种类、分散剂用量及球磨时间对球磨时染料粒径大小和粒径分布的影响。实验结果表明,含吲哚-2-酮单偶氮分散染料A1-A4、B1-B4和C1-C4在420-460 nm有主要吸收波峰。从染料A1到染料A4,单偶氮化合物的最大吸收波长随偶合组分苯胺上N的取代基变化而逐渐增大；从染料B1到染料B4,染料Cl到染料C4,单偶氮化合物最大吸收波长随偶合组分苯胺上N的取代基变化而逐渐减小。分散剂对染料的球磨效果的影响很重要。分散剂NNO和木质素磺酸钠的用量比为1:2时,染料的平均粒径在1μm左右,粒径分布指数(DPI)也最小,染料粒径分布的更加均匀；当分散剂与染料的质量比为1：1时,染料的粒径及粒径分布最小；随着球磨时间的延长,染料的粒径和粒径分布指数不断减小。当球磨48h后,染料的粒径为0.5 um以下。
染料(A1-A4、B1-B4、C1-C4)的最佳球磨工艺为：含染料1%的水溶液在20℃小球磨36小时,其中分散剂(NNO和木质素磺酸钠的用量比为1：2)和染料用量为1：1,球磨机转速为1000 Hz。经过球磨后,各染料具有良好的高温稳定性和离心稳定性,高温高压染色匀染性良好,标准方差S均小于1,达到达到合格纺织品要求。
第四部分为分散染料的染色性能研究。主要研究了12种染料对涤纶织物的热熔染色性能、高温高压染色性能和其对醋酯纤维的染色性能,并对这12种染料对涤纶纤维的染色动力学和热力学进行了研究。研究结果表明,染料(A1-A4、B1-B4、C1-C4)对涤纶织物的热熔染色固色率很好,各项色牢度良好,达到合格纺织品要求。其中,染料A1-A4的热熔固色率都高于85%,染料B1-B4的热熔固色均在75-80%之间,染料C1-C4的染色固色率均在80%左右。染料(A1-A4、B1-B4和C1-C4)对涤纶织物的高温高压染色上染百分率都达70%以上,且各项色牢度良好；分散染料A1-A4、B1-B4和C1-C4的递深性良好；染料A1-A4的上染速率最快阶段为染色时间为40-80 mmin；染料B1-B4其上染速率最快阶段为染色时间为60-100 mmin；染料C1-C4其上染速率最快阶段为染色时间为40-100 min。染料A1-A4在染色40 min时即接近染色平衡,而染料B1-B4、C1-C4在染色时间为60 min方可接近染色平衡。染料A1、B1和Cl的染色速率常数要分别要高于染料A2-A4,B2-B3和C2-C4。染料在纤维上的浓度与染料在染浴中的浓度表现出很好的线性关系,染料在涤纶上吸附属于Nernst分配型吸附,即非定位吸附。随着染色温度的升高,有更多的染料吸附在纤维上,染料在纤维上的分布系数增加。
染料A1-A4,B1-B4和C1-C4对醋酯纤维的上染率达到90%以上。染料对醋酯纤维有良好的移染性能,染色匀染良好,染色过程不易出现色花和色差现象。染色后织物色牢度良好,干、湿摩擦牢度和皂洗均在4-5级以上。除了染料A1、A2和C1耐升华牢度为4-5级,其余染料的耐升华牢度均为5级；耐日晒牢度均在7-8以上。
Disperse dyes, which named cellulose acetate dyes, appeared in market in period of 1920s for the development of cellulose acetate fiber. With the development of PA, PAN, especially PET fiber, disperse dyes developed rapidly. Now disperse dyes are mainly dyes for PET dyeing and printing. In azo disperse dyes, for the purpose of promoting shade brilliance and enriching color spectrum, besides some substitute groups were introduced into dye structure, some heterocyclic compounds were introduced into dye structure as diazo component or coupling component to synthesize some heterocyclic azo disperse dyes. Heterocyclic azo disperse dyes contains some special properties, which common dyes don't have, such as fluorescence property, optical property, thermochromic property and photosensitivity. Indolin-2-one belongs to Five-membered heterocyclic and is an important medical and pesticide intermediate. Indolin-2-one derivatives were widely used as pharmacophore in medicine. There is rarely research on introduction indolin-2-one into disperse dyes. In this article, indolin-2-one compounds were synthesized successfully and a series of disperse dyes containing indolin-2-one structure prepared, the post-treatment process and the dyeing properties of these dyes were studied. The article contains four parts, and each section is described below.
In the first part, indolin-2-one compounds (4a-4f) were synthesized with anilines as raw material, via three methods which were Friedel-Crafts alkylation, Wolff-Kishner-Huang Ming-long tow-step reduction and Wolff-Kishner-Huang Ming-long one-pot reduction. Effect factors of these three synthesis methods were studied and the optimal process to synthesize indolin-2-one compounds was found. The results showed that, besides arose salting-out effect and accelerate product precipitation, sodium sulfate played an important role on the balance of electric charge in reaction system when intermediate N-isonitrosacetanilide (2a-2f) was preparing. The yield of intermediates 2a-2f was highest and reached 80% and over when amount of sodium sulfate was 340g/L. Isatin compounds (3a-3f) was prepared from compounds N-isonitrosacetanilide (2a-2f). When dehydration and cyclization temperature of concentrated sulfuric acid is 85-90℃,the yield of Isatin compounds (3a-3f) was highest and reached 90% and over. When cyclization temperature was too low, raw material didn't react completely, so the yield was low. When reaction temperature was too high, the amount of by-products increased. During the preparation of intermediates 2-chloro-N-phenyl-acetamide(2' a-2' f) with anilines and Chloroacetyl Chloride, acetic acid was the optimum react medium, the yield of products (2'a-2'f) was 94% and over. By comparing three synthesis methods of indolin-2-one compounds (4a-4f), it showed that the yield was high and reached 80% and over when synthesis was performed via isatin and Huang Ming-long reduction, especially with triethylene glycol as react solvent and one-pot reduction without separation of intermediates hydrazone compounds.
The second part is about the synthesis of disperse dyes with indolin-2-one structure.12 monoazo disperse dyes (Al-A4、B1-B4、C1-C4), which contain indolin-2-one structure, were synthesized with indolin-2-one(4a), 5-bromoindolin-2-one (4b),5-fluoroindolin-2-one (4c) as raw materials. The synthesis course contained Knoevenagel condensation with 3-nitrobenzaldehyde, nitro reduction, diazotization-coupling reaction. The synthesis process of intermediates and final products was mainly researched. The structure of products (Al-A4、B1-B4、C1-C4) was affirmed by H'NMR. The results showed that 3-nitrobenzaldehyde could be synthesized by an indirect nitrification with ammonia as protective agent for aldehyde group and the yield reached 99%. With ionic liquid DBUBr (1,8-Diazabicyclo[5,4,0]undec-7-ene bromide) as a catalyst, the yield of 3-(3-nitrobenzylidene)indolin-2-one compounds (5a-5c) are highest and reached 95% and over. Without catalyst, the yield of 3-(3-nitrobenzylidene)indolin-2-one compounds (5a-5c) by microwave synthesis method reached 90%. When compounds (5a-5c) were reduced by stannous chloride and with concentrate hydrochloric acid/acetic acid as react solvent, the yields of compounds 3-(3-aminobenzylidene)indolin-2-one (6a-6c) were maximal and reached 75% and over.When synthesis the monoazo disperse dyes A1-A4, the yield of three diaz diazotization-coupling methods (sodium nitrite/ concentrate hydrochloric acid, nitrosyl sulfuric acid/ mixed acid, sodium nitrite/ concentrate sulfuric acid) were almost equal and approached 80%. On the other hand, during the synthesis of monoazo disperse dyes B1-B4 and C1-C4, the yield of nitrosyl sulfuric acid/ mixed acid was higher than that of other two methods and above 80%.
That third part is about the optical property and post-treatment of disperse dyes. The synthesized disperse dyes were milled and the effect of dispersant kinds and amounts, milling time on dyes particle sizes and particle size distributions was studied. The research result showed that monoazo disperse dyes(A1-A4, B1-B4, C1-C4) with indolin-2-one structure have optical absorption property at wave range 420～460nm. The maximal absorption wave length of dyes A1-A4 increased gradually when N-substituted groups of aniline changed. From dye B1 to dye B4, dye C1 to dye C4, the maximal absorption wave length of dyes decreased gradually while N-substituted groups of aniline changed. Dispersant plays an important role on milling effect of dyes. When the mass ratio of Dispersant NNO and sodium lingosulfonate was 1:2, the average particle size was near lum, the particle size was more level and particle size distribution index was minimal. When the mass ratio of Dispersant and dyes was 1:1, the average particle size and distribution index was minimal. The average particle size and distribution index decreased with the milling time extension, after milled 48 hours, the particle size was under 0.5 um. The optimal milling process of dyes (Al-A4、B1-B4、C1-C4) was established. Aqueous solution of 1% dye was milled at 20℃for 36 hours, the ratio of dispersant and dye was 1:1, dispersant was composed by NNO and sodium lignosulfonate with ratio 1:2, the frequency of milling machine was 1000Hz. After milled, the dyes have good high temperature dispersivity and centrifugal stability. The level property of milled dyes in high temperature and pressure dyeing process was fine and the mean square error was lesser than 1. The dyed fabrics reached eligible textile request.
The fourth part is about the dyeing properties of disperse dyes. The pad-dry-cure dyeing property, high temperature and pressure dyeing property of these 12 kinds of dyes on PET fabrics were investigated, as well as their dyeing property on acetate cellulose fiber. Dyeing kinetics and dyeing thermodynamics of 12 kinds of dyes on PET fabrics were research as well. The results showed that the fixation rate and color fastnesses of dyes (A1-A4, B1-B4, C1-C4) on PET fabrics with pad-dry-cure dyeing were good. The pad-dry-cure dyeing fixation of dyes A1-A4 were over 85%, dyes B1-B4 between 75% and 80%, dyes C1-C4 near 85%. The exhaustion percent of dyes (A1-A4、B1-B4、C1-C4) on PET fabrics with high temperature and pressure dyeing were over 70%, and the color fastnesses were good. The build up property of dyes (A1-A4、B1-B4、C1-C4) are good. The fastest stage of dyeing rate of dyes A1-A4 was 40-80 min, dyes B1-B4 60-100 min, dyes C1-C4 40-100 min.
The chemical structure of dye molecules exerts an influence on the dye sorption properties. After dyeing dynamic research, it was found that dyes A1-A4 approached dyeing equilibrium after dyeing 40 min, dyes B1-B4 and C1-C4 60 min. The dyeing rate constant of dyes A1, B1 and C1 were bigger than those of dyes A2-A4, B2-B3 and C2-C4 respectively.
With the dyeing thermodynamics research, it found that the concentration of dyes on fiber and the concentration of dyes in dyebath manifested good linear relation. The adsorption of dyes on PET fiber was Nernst distribution adsorption, namely non-orientation adsorption. With the increase of dyeing temperature, more dyes adsorbed on fiber and the distribution coefficient increased.
The exhaustion percents of dyes A1-A4, B1-B4 and C1-C4 on acetate cellulose fiber were over 90%, the migration and level property of dyes on acetate cellulose fiber was good. After dyeing, the color fastnesses of fabric were good, the dry and wet rubbing fastness, soap fastness were 4-5 grade and over, the sublimation fastness of dyes were 5 grade except dyes A1, A2 and C1 were 4-5 grade, the light fastness of dyes reached 7-8 grade.
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