交联染色用交联剂的合成及应用性能研究
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摘要
交联染色能够实现染料在纤维上的超高固色率,染色纤维具有良好的染色牢度和部分整理效果,具有实现染色绿色化的发展趋势。
本文设计了聚乙二醇二缩水甘油醚全新的Williamson醚化合成路线,合成了聚乙二醇二缩水甘油醚环氧树脂2-1a-d,结果表明Williamson醚化反应制备的2-1a-c具有理想的环氧取代度,其中2-1b的环氧取代度接近2.0,该合成路线具有收率高,环氧取代度高,路线简单,成本低的优点。
本文以生物质资源蔗糖为原料,通过烯丙基醚化反应制备了烯丙基蔗糖。在烯丙基醚化中选择了氢氧化钠为蔗糖活化碱剂和烯丙基氯为烯丙基醚化试剂,代替了价格昂贵的氢化钠和烯丙基溴,成本降低到只有原来的1/10。详细地考察了活化温度和活化时间以及反应温度和反应时间、溶剂用量对烯丙基醚化反应的影响。利用双氧水和乙酸在硫酸催化室温下制备了过氧乙酸。通过过氧乙酸对烯丙基蔗糖环氧化反应制备了蔗糖环氧树脂2-2。考察了双氧水与烯丙基双键配比、反应温度和反应时间对环氧化反应的影响。
将聚乙二醇二缩水甘油醚环氧树脂和蔗糖环氧树脂交联剂2-1a-d、2-2用于蓝色四乙烯五胺和黄色聚乙烯胺染料的交联固色。交联固色采用浸轧工艺。交联固色的结果表明,环氧树脂交联剂在棉织物和丝绸上的交联固色率达到了97%和99%。
本文利用三聚氯氰的氨解和醇解反应合成了阴离子水溶性交联剂3-1、3-2、3-3、3-4和非离子型水溶性交联剂3-5a-d。利用~1HNMR、IR和MS表征了交联剂分子的结构。
将所合成的阴离子水溶性三聚氯氰型交联剂3-1、3-2、3-3、3-4和非离子型水溶性交联剂3-5a-d用于蓝色四乙烯五胺和黄色聚乙烯胺交联染料的交联固色。交联固色的结果表明,三聚氯氰型交联剂在棉织物和丝绸上的交联固色率达到99%。综合各种因素,在阴离子水溶性三聚氯氰交联剂中3-1和非离子交联剂中3-5b具有更优异的性能。
利用DMF剥色方法、IR谱图证实了交联剂与交联染料和纤维之间确实发生了交联反应生成了共价键,通过对棉和丙纶交联固色的差异和粗略的数学计算分析,合理的交联染色结合方式是交联染料之间通过交联剂结合后再与纤维形成共价键。研究了不同交联剂浓度下,交联染色织物的折皱回复性能和拉伸强力,结果表明交联染色后织物在一定的交联剂浓度下具有一定的防皱整理功能,而强力也随着交联程度的增加而下降。通过对二氯均三嗪活性基的假一级水解动力学计算和水解套用次数的研究,发现交联固色条件下,交联剂分子的水解很微弱,说明交联染色具有很好的工业前景。
Crosslinking dyeing can reach high dye fixation on fiber, and dyed fiber has good fastness and finishing property to some degree, which results in its green dyeing trend.In this thesis, a new Williamson etherification route was proposed to prepare polyethylene glycol diglycidyl ether 2-1a-d. The results of DS of epoxy group showed Williamson etherification route yielded polyethylene glycol diglycidyl ether 2-1a-c with ideal DS of epoxy group, especially 2-1b with DS about 2.0. The new synthesis route has many merits, such as high yield, high DS of epoxy group, simple procedure, and lower cost.Allylsucrose was prepared by allyl etherification from sucrose which is biomass resource. Activating alkali and allyl etherification reagent were well-chosen. Acceptable product was obtained when sodium hydroxide replaced sodium hydride and allyl chloride replaced allyl bromide, which results in that the cost was decrease 90%. A lot reaction factors, involving activation temperature, activation time, reaction temperature, reaction time, the amount of solvent, were investigated in detail. Peroxyacetic acid was prepared from hydrogen peroxide and acetic acid in the presence of sulfuric acid at room temperature. Sucrose epoxy resin 2-2 was prepared by epoxidation using peroxyacetic acid. The effect of the ratio of hydrogen peroxide to double bond of allyl group, reaction temperature and reaction time on epoxidation was investigated.Polyethylene glycol diglycidyl ether 2-la-d and sucrose epoxy resin 2-2 were applied in crosslinking dyeing of the blue tetraethylene pentamine dye and the yellow polyvinylamine dye on cotton and silk. The dip-pad process was employed as fixation procedure. The results of dye fixations demonstrated that the fixation of the epoxy resin crosslinkers reached 97% and 99% on cotton and silk respectively.Ammonolysis reaction of cyanuric chloride was employed to synthesis anionic water-soluble crosslinkers 3-1, 3-2, 3-3 and 3-4, and alcoholysis reaction of cyanuric chloride was employed to prepare nonionic water-soluble crosslinker 3-5a-d. The structures of cyanuric chloride-based crosslinkers were characterized by IR, ~1H NMR and MS spectroscopy.Anionic and nonionic cyanuric chloride-based crosslinkers 3-1, 3-2, 3-3, 3-4 and 3-5a-d were used in crosslinking dyeing of the blue tetraethylene pentamine dye and the yellow polyvinylamine dye on cotton and silk. The dye fixations of the both dyes reached 99% on
cotton and silk. In view of many factors, crosslinker 3-1 has the advantage over other anionic crosslinkers, and crosslinker 3-5b is the best one among these nonionic crosslinkers.The covalent bond among fiber, the crosslinking dyes and crosslinkers was revealed by DMF bleeding method and IR spectra of fiber, dyed fiber and crosslinking dyed fiber. The fixation comparison of the blue dye on cotton and polypropene, and imprecise mathematical calculation, indicated that reasonable linkage among them was covalent bond which was formed by a macro-dye formed from many dye molecules at first linked to fiber by crosslinkers. Crease-proof performance and tensile strength retention of crosslinking dyed fabrics were studied under different concentrations of crosslinkers. The results revealed crosslinking dyed fabrics was endowed with crease-proof properties to some degree, and the strength of fabrics was decreased due to crosslink. The hydrolysis of crosslinkers was testified to be very weak by the calculation of hydrolysis kinetics of dichloro-s-triazine and reuse times of crosslinkers, which indicated that crosslinking dyeing was promising process in this field.
本文设计了聚乙二醇二缩水甘油醚全新的Williamson醚化合成路线,合成了聚乙二醇二缩水甘油醚环氧树脂2-1a-d,结果表明Williamson醚化反应制备的2-1a-c具有理想的环氧取代度,其中2-1b的环氧取代度接近2.0,该合成路线具有收率高,环氧取代度高,路线简单,成本低的优点。
本文以生物质资源蔗糖为原料,通过烯丙基醚化反应制备了烯丙基蔗糖。在烯丙基醚化中选择了氢氧化钠为蔗糖活化碱剂和烯丙基氯为烯丙基醚化试剂,代替了价格昂贵的氢化钠和烯丙基溴,成本降低到只有原来的1/10。详细地考察了活化温度和活化时间以及反应温度和反应时间、溶剂用量对烯丙基醚化反应的影响。利用双氧水和乙酸在硫酸催化室温下制备了过氧乙酸。通过过氧乙酸对烯丙基蔗糖环氧化反应制备了蔗糖环氧树脂2-2。考察了双氧水与烯丙基双键配比、反应温度和反应时间对环氧化反应的影响。
将聚乙二醇二缩水甘油醚环氧树脂和蔗糖环氧树脂交联剂2-1a-d、2-2用于蓝色四乙烯五胺和黄色聚乙烯胺染料的交联固色。交联固色采用浸轧工艺。交联固色的结果表明,环氧树脂交联剂在棉织物和丝绸上的交联固色率达到了97%和99%。
本文利用三聚氯氰的氨解和醇解反应合成了阴离子水溶性交联剂3-1、3-2、3-3、3-4和非离子型水溶性交联剂3-5a-d。利用~1HNMR、IR和MS表征了交联剂分子的结构。
将所合成的阴离子水溶性三聚氯氰型交联剂3-1、3-2、3-3、3-4和非离子型水溶性交联剂3-5a-d用于蓝色四乙烯五胺和黄色聚乙烯胺交联染料的交联固色。交联固色的结果表明,三聚氯氰型交联剂在棉织物和丝绸上的交联固色率达到99%。综合各种因素,在阴离子水溶性三聚氯氰交联剂中3-1和非离子交联剂中3-5b具有更优异的性能。
利用DMF剥色方法、IR谱图证实了交联剂与交联染料和纤维之间确实发生了交联反应生成了共价键,通过对棉和丙纶交联固色的差异和粗略的数学计算分析,合理的交联染色结合方式是交联染料之间通过交联剂结合后再与纤维形成共价键。研究了不同交联剂浓度下,交联染色织物的折皱回复性能和拉伸强力,结果表明交联染色后织物在一定的交联剂浓度下具有一定的防皱整理功能,而强力也随着交联程度的增加而下降。通过对二氯均三嗪活性基的假一级水解动力学计算和水解套用次数的研究,发现交联固色条件下,交联剂分子的水解很微弱,说明交联染色具有很好的工业前景。
Crosslinking dyeing can reach high dye fixation on fiber, and dyed fiber has good fastness and finishing property to some degree, which results in its green dyeing trend.In this thesis, a new Williamson etherification route was proposed to prepare polyethylene glycol diglycidyl ether 2-1a-d. The results of DS of epoxy group showed Williamson etherification route yielded polyethylene glycol diglycidyl ether 2-1a-c with ideal DS of epoxy group, especially 2-1b with DS about 2.0. The new synthesis route has many merits, such as high yield, high DS of epoxy group, simple procedure, and lower cost.Allylsucrose was prepared by allyl etherification from sucrose which is biomass resource. Activating alkali and allyl etherification reagent were well-chosen. Acceptable product was obtained when sodium hydroxide replaced sodium hydride and allyl chloride replaced allyl bromide, which results in that the cost was decrease 90%. A lot reaction factors, involving activation temperature, activation time, reaction temperature, reaction time, the amount of solvent, were investigated in detail. Peroxyacetic acid was prepared from hydrogen peroxide and acetic acid in the presence of sulfuric acid at room temperature. Sucrose epoxy resin 2-2 was prepared by epoxidation using peroxyacetic acid. The effect of the ratio of hydrogen peroxide to double bond of allyl group, reaction temperature and reaction time on epoxidation was investigated.Polyethylene glycol diglycidyl ether 2-la-d and sucrose epoxy resin 2-2 were applied in crosslinking dyeing of the blue tetraethylene pentamine dye and the yellow polyvinylamine dye on cotton and silk. The dip-pad process was employed as fixation procedure. The results of dye fixations demonstrated that the fixation of the epoxy resin crosslinkers reached 97% and 99% on cotton and silk respectively.Ammonolysis reaction of cyanuric chloride was employed to synthesis anionic water-soluble crosslinkers 3-1, 3-2, 3-3 and 3-4, and alcoholysis reaction of cyanuric chloride was employed to prepare nonionic water-soluble crosslinker 3-5a-d. The structures of cyanuric chloride-based crosslinkers were characterized by IR, ~1H NMR and MS spectroscopy.Anionic and nonionic cyanuric chloride-based crosslinkers 3-1, 3-2, 3-3, 3-4 and 3-5a-d were used in crosslinking dyeing of the blue tetraethylene pentamine dye and the yellow polyvinylamine dye on cotton and silk. The dye fixations of the both dyes reached 99% on
cotton and silk. In view of many factors, crosslinker 3-1 has the advantage over other anionic crosslinkers, and crosslinker 3-5b is the best one among these nonionic crosslinkers.The covalent bond among fiber, the crosslinking dyes and crosslinkers was revealed by DMF bleeding method and IR spectra of fiber, dyed fiber and crosslinking dyed fiber. The fixation comparison of the blue dye on cotton and polypropene, and imprecise mathematical calculation, indicated that reasonable linkage among them was covalent bond which was formed by a macro-dye formed from many dye molecules at first linked to fiber by crosslinkers. Crease-proof performance and tensile strength retention of crosslinking dyed fabrics were studied under different concentrations of crosslinkers. The results revealed crosslinking dyed fabrics was endowed with crease-proof properties to some degree, and the strength of fabrics was decreased due to crosslink. The hydrolysis of crosslinkers was testified to be very weak by the calculation of hydrolysis kinetics of dichloro-s-triazine and reuse times of crosslinkers, which indicated that crosslinking dyeing was promising process in this field.
引文
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