新型聚乳酸纤维专用染料的合成与应用研究
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摘要
论文根据染料和纤维相亲相容具有高亲和力的原理,针对聚乳酸纤维的疏水特性设计合成了分子结构中含有不同疏水官能团的疏水性染料:同时针对传统分散染料在聚乳酸纤维上日晒牢度较低的问题,设计合成了分子中含有光稳定性官能团的耐晒染料。期待这些染料在聚乳酸纤维上具有高竭染率和色牢度,从而达到提高其应用性能的目的。
论文分别以1-硝基蒽醌和1,5-二氯蒽醌为起始原料与不同疏水结构的胺反应,合成了两个系列的烷氨基蒽醌染料。同时,以2-氯-4-硝基苯胺为原料,经过亚硝酸钠/浓硫酸体系重氮化后,与具有不同疏水官能团的苯胺偶合,合成了七支(2'-氯-4'-硝基)偶氮苯染料。在丙酮溶液中培养了五支偶氮染料的单晶,并用X射线分析了单晶的结构。利用核磁共振氢谱、质谱和红外光谱表征了这些染料的分子结构。
1-氨基蒽醌经过亚硝酸钠/浓硫酸/氟硼酸体系重氮化后,分别与取代吡唑啉酮偶合,合成了三支1-(吡唑啉酮基)偶氮蒽醌黄色染料。同时为了改善染料与纤维的亲和力,1-氨基蒽醌重氮化后又与1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮偶合,然后经过氯化、胺解,合成了四支新型的含有疏水烷基链的磺酰胺型偶氮蒽醌黄色染料。用红外光谱、核磁共振氢谱、质谱和元素分析表征了这些染料的分子结构,核磁共振氢谱表明这些偶氮染料均以稳定的腙体结构存在。
论文选择上述合成的代表性染料,利用高温高压竭染法对染料在聚乳酸纤维上的染色性能进行研究。结果表明,向染料分子中引入适当的疏水烷基链能够有效地改善染料与聚乳酸纤维的亲和力,从而明显提高在纤维上的竭染率。具有不同疏水官能团的偶氮染料3-2与聚乳酸纤维具有良好的相亲性,在纤维上的竭染率都在97%以上。偶氮蒽醌染料在聚乳酸纤维上具有优异的日晒牢度,全部在6级以上。
Dyes always show high affinity with fibers if they are compatible with each other. According to this theory,the hydrophobic dyes bearing different hydrophobic functional groups are designed and synthesized for hydrophobic polylactide fiber in this thesis.And the lightfast dyes with photostable functional group are also designed and synthesized for polylactide fiber based on the low light fastness of the thraditonal commercial dyes on polylactide fiber.It is expected that these dyes have high exhaustions and color fastness on polylactide fabrics.
Two series of anthraquinone dyes are synthesized by the reaction of different amines with 1-nitroanthraquinone and 1,5-dichloroanthraquinone,respectively.Also,seven (2'-chloro-4'-nitro)azobenzene dyes are synthesized via diazotization in NaNO_2/H_2SO_4 by using 2-chloro-4-nitroaniline as raw material.Five single crystals of the azo dyes are obtained in acetone and analyzed by X-ray.The structures of these dyes are also characterized by FTIR, ~1H NMR and mass spectrometry.
Three yellow azo anthraquinone dyes are synthesized from 1-aminoanthraquinone via diazotization in NaNO_2/H_2SO_4/HBF_4 and coupling with pyrazolones.In order to improve dye affinity with polylactide fiber,four novel yellow azo anthraquinone dyes with hydrophobic alkyl chains are also synthesized in four steps from 1-aminoanthraquinone and 1-(4'-sulfo)-phenyl-3-methyl-pyrazolone-5.Their structures are also characterized by FTIR, ~1H NMR,mass spectrometry and elemental analysis.~1H NMR results indicate that these azo dyes exist in the tautomer of hydrazone.
Representative dyes of each series are selected to apply to polylactide fabrics in high-temperature exhaust dyeing.It is shown from the dyeing results that the introduction of proper hydrophobic alkyl chains to the dye molecules can markedly increase the dye exhaustions on polylactide fabric,resulting from the improvement of dye affinity with polylactide fiber.And hydrophobic azo dyes 3-2 show high affinity with polylactide fiber, resulting in their exhaustions higher than 97%on polylactide fabrics.It is also found that all azo anthraquinone dyes have excellent light fastness on polylactide fabric,over 6 ratings.
论文分别以1-硝基蒽醌和1,5-二氯蒽醌为起始原料与不同疏水结构的胺反应,合成了两个系列的烷氨基蒽醌染料。同时,以2-氯-4-硝基苯胺为原料,经过亚硝酸钠/浓硫酸体系重氮化后,与具有不同疏水官能团的苯胺偶合,合成了七支(2'-氯-4'-硝基)偶氮苯染料。在丙酮溶液中培养了五支偶氮染料的单晶,并用X射线分析了单晶的结构。利用核磁共振氢谱、质谱和红外光谱表征了这些染料的分子结构。
1-氨基蒽醌经过亚硝酸钠/浓硫酸/氟硼酸体系重氮化后,分别与取代吡唑啉酮偶合,合成了三支1-(吡唑啉酮基)偶氮蒽醌黄色染料。同时为了改善染料与纤维的亲和力,1-氨基蒽醌重氮化后又与1-(4'-磺酸基)苯基-3-甲基-5-吡唑啉酮偶合,然后经过氯化、胺解,合成了四支新型的含有疏水烷基链的磺酰胺型偶氮蒽醌黄色染料。用红外光谱、核磁共振氢谱、质谱和元素分析表征了这些染料的分子结构,核磁共振氢谱表明这些偶氮染料均以稳定的腙体结构存在。
论文选择上述合成的代表性染料,利用高温高压竭染法对染料在聚乳酸纤维上的染色性能进行研究。结果表明,向染料分子中引入适当的疏水烷基链能够有效地改善染料与聚乳酸纤维的亲和力,从而明显提高在纤维上的竭染率。具有不同疏水官能团的偶氮染料3-2与聚乳酸纤维具有良好的相亲性,在纤维上的竭染率都在97%以上。偶氮蒽醌染料在聚乳酸纤维上具有优异的日晒牢度,全部在6级以上。
Dyes always show high affinity with fibers if they are compatible with each other. According to this theory,the hydrophobic dyes bearing different hydrophobic functional groups are designed and synthesized for hydrophobic polylactide fiber in this thesis.And the lightfast dyes with photostable functional group are also designed and synthesized for polylactide fiber based on the low light fastness of the thraditonal commercial dyes on polylactide fiber.It is expected that these dyes have high exhaustions and color fastness on polylactide fabrics.
Two series of anthraquinone dyes are synthesized by the reaction of different amines with 1-nitroanthraquinone and 1,5-dichloroanthraquinone,respectively.Also,seven (2'-chloro-4'-nitro)azobenzene dyes are synthesized via diazotization in NaNO_2/H_2SO_4 by using 2-chloro-4-nitroaniline as raw material.Five single crystals of the azo dyes are obtained in acetone and analyzed by X-ray.The structures of these dyes are also characterized by FTIR, ~1H NMR and mass spectrometry.
Three yellow azo anthraquinone dyes are synthesized from 1-aminoanthraquinone via diazotization in NaNO_2/H_2SO_4/HBF_4 and coupling with pyrazolones.In order to improve dye affinity with polylactide fiber,four novel yellow azo anthraquinone dyes with hydrophobic alkyl chains are also synthesized in four steps from 1-aminoanthraquinone and 1-(4'-sulfo)-phenyl-3-methyl-pyrazolone-5.Their structures are also characterized by FTIR, ~1H NMR,mass spectrometry and elemental analysis.~1H NMR results indicate that these azo dyes exist in the tautomer of hydrazone.
Representative dyes of each series are selected to apply to polylactide fabrics in high-temperature exhaust dyeing.It is shown from the dyeing results that the introduction of proper hydrophobic alkyl chains to the dye molecules can markedly increase the dye exhaustions on polylactide fabric,resulting from the improvement of dye affinity with polylactide fiber.And hydrophobic azo dyes 3-2 show high affinity with polylactide fiber, resulting in their exhaustions higher than 97%on polylactide fabrics.It is also found that all azo anthraquinone dyes have excellent light fastness on polylactide fabric,over 6 ratings.
引文
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