聚马来酸（酯）大分子染料的合成及应用研究
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摘要
本文以聚马来酸酐为大分子骨架设计合成了新型聚马来酸大分子染料及聚马来酸酯大分子染料,并将两类大分子染料应用于棉纤维和涤纶纤维的染色,对其染色工艺进行了深入研究。
论文以对硝基苯胺与聚马来酸酐反应生成聚马来酸酐-co-N-(4-硝基苯基)琥珀酰亚胺,将硝基通过保险粉还原成氨基合成了大分子中间体聚马来酸-co-N-(4-氨基苯基)琥珀酰亚胺,将其重氮化后分别与1-(4'-磺酸基苯基)-3-甲基-5-吡唑啉酮、苯甲酰H酸和H酸单偶氮发色体偶合合成黄色、红色和蓝色聚马来酸大分子染料PMA-DY1、 PMA-DR1和PMA-DB1。以H酸与聚马来酸酐反应合成了大分子中间体聚马来酸-co-N-[1-(8-羟基-3,6-二磺酸基)萘基)]琥珀酰亚胺,以其为偶合组份,分别与苯胺、对氨基苯磺酸、对硝基苯胺、对甲氧基苯胺、对氰基苯胺、2-氨基噻唑、5-氨基苯并咪唑酮重氮盐偶合合成红色及紫色聚马来酸大分子染料PMA-DR2～6和PMA-DP1～2;与2-氨基-5-硝基噻唑、3-氨基-5-硝基苯并异噻唑重氮盐偶合合成蓝色聚马来酸大分子染料PMA-DB2～3。采用FT-IR、1H NMR谱图表征了大分子染料的结构,并测定了大分子染料中发色体的含量及大分子染料在水中的溶解度。
论文以3-(N,N-二乙基)氨基苯胺与聚马来酸酐反应合成了大分子中间体聚马来酸酐-co-N-(3-二乙胺基苯基)琥珀酰亚胺,以其为偶合组份,分别与对硝基苯胺、邻氰基对硝基苯胺、2-氰基-4-硝基-6-溴苯胺、3-氨基-5-硝基苯并异噻唑重氮盐偶合合成含微水溶性发色体的橙色、红色和紫色聚马来酸大分子染料PMA-DO1、PMA-DR7～8和PMA-DP3,并测定了大分子染料中发色体的含量；以1-甲氨基-4-溴蒽醌与对苯二胺通过乌尔曼缩合反应合成蒽醌系蓝色发色体CB2,再与聚马来酸酐反应合成蓝色聚马来酸酐大分子染料PMA-DB4。论文将所合成的含微水溶性发色体的聚马来酸(酐)大分子染料与不同种类的醇发生酯化反应合成疏水性的聚马来酸酯大分子染料,并对其酯化度进行了测定,采用FT-IR、1HNMR谱图表征了聚马来酸酯大分子染料的结构。
论文研究了聚马来酸及聚马来酸酯大分子染料分别在棉纤维和涤纶纤维上的染色方法。在固色剂硝酸锌和双氰胺的作用下,含水溶性发色体的聚马来酸大分子染料在棉纤维上的固色率均超过98%,水洗变色牢度可达4-5级,湿摩擦牢度可达3-4级；利用聚马来酸酯大分子染料与涤纶纤维的结构相似性,采用涂料染色工艺对涤纶进行染色,酯化度超过30%的聚马来酸酯大分子染料在涤纶纤维上于室温下就能达到非常好的染色效果,干湿摩擦牢度分别可达4-5级和4级,且染色布样柔软,手感良好。
In this thesis, new polymaleic acid dyes and polymaleic ester dyes were designed and synthesized based on poly(maleic anhydride)(PMA). The two kinds of dyes were applied for dyeing cotton and polyester fabrics and the dyeing processes were researched in detail.
Poly(maleic anhydride-co-(N-p-nitrophenyl)succinimide)(PMA-NO2) was synthesized by the reaction of PMA and4-nitroaniline. The nitro group in PMA-NO2was reduced by sodium dithionite, the resulting poly(maleic acid-co-(N-p-aminophenyl)succinimide)(PMA-NH2) was diazotized and coupled with1-(4'-sulfophenyl)-3-methyl-5-pyrazolone, N-benzoyl H acid and H acid-containing mono azo dye to synthesize yellow, red and blue polymaleic acid dyes PMA-DY1, PMA-DR1and PMA-DB1, respectively. Poly(maleic acid-co-(N-(1-(8-hydroxyl-3,6-disulfonic acid-naphthyl)succinimide))(PMA-H) was synthesized by reaction of PMA and H acid. PMA-H was coupled with aniline, sulfanilic acid,4-nitroaniline,4-methoxyaniline,2-aminothiazole,4-aminobenzonitrile and5-amino-1,3-dihydro-2H-benzimidazole-2-one diazo salts to synthesize red and purple polymaleic acid dyes PMA-DR2-6and PMA-DP1～2, respectively; while PMA-H was coupled with2-amino-5-nitrothiazole and3-amino-5-nitrobenzoisothiazole diazo salts to synthesize blue polymaleic acid dyes PMA-DB2-3, respectively. The structures of the polymaleic acid dyes were characterized by FT-IR and1H NMR. The grafting ratio of chromophore was determined by UV-vis standard curves, and the solubility of polymaleic acid dyes in water was determined.
Poly(maleic anhydride-co-(N-(3-diethylamino-phenyl)succinimide)(PMA-N1) was synthesized by the reaction of PMA and3-amino-N,N-diethylaniline, then PMA-N1was coupled with4-nitroaniline,2-cyano-4-nitro aniline,2-amino-3-bromo-5-nitrobenzonitrile and3-amino-5-nitrobenzoisothiazole diazo salts to synthesize orange, red and purple polymaleic acid dyes PMA-DO1, PMA-DR7～8and PMA-DP3, which contain water insoluble chromophores, respectively. The grafting ratio of the chromophore was determined by UV-vis standard curves. Blue chromophore CB2was synthesized by the Ulmann reaction between1-bromo-4-(methylamino)anthraquinone and p-phenylenediamine, then it reacted with PMA to synthesize blue polymaleic acid dye PMA-DB4. After that, the polymaleic acid dyes were esterified by different kinds of alcohols to synthesize polymaleic ester dyes. Esterification of the polymaleic ester dyes was determined and the structures were characterized by FT-IR and1H NMR.
The dyeing processes of the polymaleic acid dyes which cotain water soluble chromphores on cotton was researched, and polymaleic ester dyes which cotain water insoluble chromphores on polyester fabrics were also researched. The fixation ratio of polymaleic acid dyes on cotton could reach as high as98%when Zn(NO3)2and DICY were used as fixation agents. The wash fastness could reach grade4-5, and wet rub fastness could reach grade3-4. When the esterification degree of polymaleic ester dyes was up to30%, the dyeing properties were very good even at room temperature using a pigment dyeing process, due to the high affinity among polymaleic ester dyes, polyacrylate adhesives and polyester fabric. The dry and wet rub fastness could reach grade4-5and grade4, respectively. Also, the stiffness of dyed fabrics could be controlled by altering the monomer ratio in polyacrylate adhesives, and the dyeing fabrics feel good.
论文以对硝基苯胺与聚马来酸酐反应生成聚马来酸酐-co-N-(4-硝基苯基)琥珀酰亚胺,将硝基通过保险粉还原成氨基合成了大分子中间体聚马来酸-co-N-(4-氨基苯基)琥珀酰亚胺,将其重氮化后分别与1-(4'-磺酸基苯基)-3-甲基-5-吡唑啉酮、苯甲酰H酸和H酸单偶氮发色体偶合合成黄色、红色和蓝色聚马来酸大分子染料PMA-DY1、 PMA-DR1和PMA-DB1。以H酸与聚马来酸酐反应合成了大分子中间体聚马来酸-co-N-[1-(8-羟基-3,6-二磺酸基)萘基)]琥珀酰亚胺,以其为偶合组份,分别与苯胺、对氨基苯磺酸、对硝基苯胺、对甲氧基苯胺、对氰基苯胺、2-氨基噻唑、5-氨基苯并咪唑酮重氮盐偶合合成红色及紫色聚马来酸大分子染料PMA-DR2～6和PMA-DP1～2;与2-氨基-5-硝基噻唑、3-氨基-5-硝基苯并异噻唑重氮盐偶合合成蓝色聚马来酸大分子染料PMA-DB2～3。采用FT-IR、1H NMR谱图表征了大分子染料的结构,并测定了大分子染料中发色体的含量及大分子染料在水中的溶解度。
论文以3-(N,N-二乙基)氨基苯胺与聚马来酸酐反应合成了大分子中间体聚马来酸酐-co-N-(3-二乙胺基苯基)琥珀酰亚胺,以其为偶合组份,分别与对硝基苯胺、邻氰基对硝基苯胺、2-氰基-4-硝基-6-溴苯胺、3-氨基-5-硝基苯并异噻唑重氮盐偶合合成含微水溶性发色体的橙色、红色和紫色聚马来酸大分子染料PMA-DO1、PMA-DR7～8和PMA-DP3,并测定了大分子染料中发色体的含量；以1-甲氨基-4-溴蒽醌与对苯二胺通过乌尔曼缩合反应合成蒽醌系蓝色发色体CB2,再与聚马来酸酐反应合成蓝色聚马来酸酐大分子染料PMA-DB4。论文将所合成的含微水溶性发色体的聚马来酸(酐)大分子染料与不同种类的醇发生酯化反应合成疏水性的聚马来酸酯大分子染料,并对其酯化度进行了测定,采用FT-IR、1HNMR谱图表征了聚马来酸酯大分子染料的结构。
论文研究了聚马来酸及聚马来酸酯大分子染料分别在棉纤维和涤纶纤维上的染色方法。在固色剂硝酸锌和双氰胺的作用下,含水溶性发色体的聚马来酸大分子染料在棉纤维上的固色率均超过98%,水洗变色牢度可达4-5级,湿摩擦牢度可达3-4级；利用聚马来酸酯大分子染料与涤纶纤维的结构相似性,采用涂料染色工艺对涤纶进行染色,酯化度超过30%的聚马来酸酯大分子染料在涤纶纤维上于室温下就能达到非常好的染色效果,干湿摩擦牢度分别可达4-5级和4级,且染色布样柔软,手感良好。
In this thesis, new polymaleic acid dyes and polymaleic ester dyes were designed and synthesized based on poly(maleic anhydride)(PMA). The two kinds of dyes were applied for dyeing cotton and polyester fabrics and the dyeing processes were researched in detail.
Poly(maleic anhydride-co-(N-p-nitrophenyl)succinimide)(PMA-NO2) was synthesized by the reaction of PMA and4-nitroaniline. The nitro group in PMA-NO2was reduced by sodium dithionite, the resulting poly(maleic acid-co-(N-p-aminophenyl)succinimide)(PMA-NH2) was diazotized and coupled with1-(4'-sulfophenyl)-3-methyl-5-pyrazolone, N-benzoyl H acid and H acid-containing mono azo dye to synthesize yellow, red and blue polymaleic acid dyes PMA-DY1, PMA-DR1and PMA-DB1, respectively. Poly(maleic acid-co-(N-(1-(8-hydroxyl-3,6-disulfonic acid-naphthyl)succinimide))(PMA-H) was synthesized by reaction of PMA and H acid. PMA-H was coupled with aniline, sulfanilic acid,4-nitroaniline,4-methoxyaniline,2-aminothiazole,4-aminobenzonitrile and5-amino-1,3-dihydro-2H-benzimidazole-2-one diazo salts to synthesize red and purple polymaleic acid dyes PMA-DR2-6and PMA-DP1～2, respectively; while PMA-H was coupled with2-amino-5-nitrothiazole and3-amino-5-nitrobenzoisothiazole diazo salts to synthesize blue polymaleic acid dyes PMA-DB2-3, respectively. The structures of the polymaleic acid dyes were characterized by FT-IR and1H NMR. The grafting ratio of chromophore was determined by UV-vis standard curves, and the solubility of polymaleic acid dyes in water was determined.
Poly(maleic anhydride-co-(N-(3-diethylamino-phenyl)succinimide)(PMA-N1) was synthesized by the reaction of PMA and3-amino-N,N-diethylaniline, then PMA-N1was coupled with4-nitroaniline,2-cyano-4-nitro aniline,2-amino-3-bromo-5-nitrobenzonitrile and3-amino-5-nitrobenzoisothiazole diazo salts to synthesize orange, red and purple polymaleic acid dyes PMA-DO1, PMA-DR7～8and PMA-DP3, which contain water insoluble chromophores, respectively. The grafting ratio of the chromophore was determined by UV-vis standard curves. Blue chromophore CB2was synthesized by the Ulmann reaction between1-bromo-4-(methylamino)anthraquinone and p-phenylenediamine, then it reacted with PMA to synthesize blue polymaleic acid dye PMA-DB4. After that, the polymaleic acid dyes were esterified by different kinds of alcohols to synthesize polymaleic ester dyes. Esterification of the polymaleic ester dyes was determined and the structures were characterized by FT-IR and1H NMR.
The dyeing processes of the polymaleic acid dyes which cotain water soluble chromphores on cotton was researched, and polymaleic ester dyes which cotain water insoluble chromphores on polyester fabrics were also researched. The fixation ratio of polymaleic acid dyes on cotton could reach as high as98%when Zn(NO3)2and DICY were used as fixation agents. The wash fastness could reach grade4-5, and wet rub fastness could reach grade3-4. When the esterification degree of polymaleic ester dyes was up to30%, the dyeing properties were very good even at room temperature using a pigment dyeing process, due to the high affinity among polymaleic ester dyes, polyacrylate adhesives and polyester fabric. The dry and wet rub fastness could reach grade4-5and grade4, respectively. Also, the stiffness of dyed fabrics could be controlled by altering the monomer ratio in polyacrylate adhesives, and the dyeing fabrics feel good.
引文
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