聚马来酸型和羟甲基型大分子染料的设计合成及应用
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摘要
本文设计合成了聚马来酸型和羟甲基型两类大分子染料,并将其应用于棉纤维的染色。所合成的大分子染料分子结构中含有多个活性基团,具有同一分子链上含有多个活性基团的优势,从而实现高的染色固色率。
论文首先以对硝基苯胺为重氮组分,分别与对甲苯酚、N-乙基-3-氨甲酰基-4-甲基-6-羟基-2-吡啶酮、1-(2’,5’-二氯-4’-磺酸基苯基)-3-甲基-5-毗唑啉酮偶合制备了3支小分子偶氮型发色体CY1-NO2、CY2-NO2和CY3-NO2,然后分别在乙醇/水、甲苯/水混合溶剂和水介质中,用硫化钠还原发色体结构中的硝基,得到氨基发色体CY1-NH2、CY2-NH2和CY3-NH2。采用IR、MS、1HNMR等对上述发色体进行了结构表征。
以过氧化苯甲酰为引发剂,在甲苯中合成了聚马来酸酐(PMA)。将发色体CY1-NH2、CY2-NH2和CY3-NH2分别与PMA反应,合成了3支发色体含量为30%的聚马来酸型大分子染料。将PMA与氨水反应得到了以酰胺为主的产物,与尿素高温固相反应得到了以酰亚胺为主的产物,即采用不同的酰胺化试剂、不同的反应条件可得到酰胺或酰亚胺结构。以此为依据,分别对所合成的3支聚马来酸型大分子染料(PMA-DY1、PMA-DY2和PMA-DY3)以及本团队所合成的2支聚马来酸型大分子染料(PMA-DY4和PMA-DY5)进行了酰胺化和酰亚胺化改性,再与甲醛反应得到羟甲基型大分子染料。利用IR、1H NMR等对上述含羧酸基团和羟甲基基团的大分子染料进行了结构表征。
以偶氮二异丁腈为引发剂,在四氢呋喃中合成了马来酸酐-丙烯酰胺共聚物(MA-AAm);采用IR、凝胶渗透色谱(GPC)等对MA-AAm共聚物进行了结构表征。针对马来酸酐与丙烯酰胺共聚时,随着马来酸酐用量的增加,马来酸酐利用率下降及聚合物收率低的问题,论文通过对聚合残液的8次循环利用,马来酸酐单体利用率由35.7%提高至90.2%,聚合物收率由47.8%提高至近60%,并且聚合物中马来酸酐含量基本不变(～42%)。将发色体CY4-NH2(4-((4'-氨基苯基)偶氮基)-1-苯基-3-甲基-5-毗唑啉酮)与MA-AAm共聚物反应,发色体含量为11.4%。
研究了两类大分子染料的溶解性能及耐酸碱稳定性,结果表明,在pH>7时均具有较好的水溶性,不含水溶性基团的DY1、DY2和DY4系列染料能溶于常用的极性有机溶剂；室温时,大分子染料在pH 3-10能够稳定存在。剥色实验证明两类大分子染料与棉纤维以共价键结合。考察了两类大分子染料轧染染色棉纤维的各项牢度及撕裂强度,结果表明,均达到了染料应用的要求。经羟甲基型大分子染料染色后的棉纤维释放甲醛含量小于75 mg/kg,符合国标GB 18401-2003《国家纺织产品基本安全技术规范》。
In this thesis, polymaleic acid dyes and hydroxymethyl polymeric dyes for cotton fiber were designed and synthesized. As polymeric dyes contain multiple reactive groups, high fixation could be achieved through covalent bonds between polymeric dyes and cotton after dyeing and fixation.
CY1-NO2, CY2-NO2 and CY3-NO2 were synthesized by diazotization and coupling reaction by using p-nitroaniline as diazo component, and p-cresol,3-aminoformyl-l-ethyl-6-hydroxy-4-methyl-2-pyridone, and 1-(2',5'-dichloro-4'-sulfo-phenyl)-3-methyl-5-pyrazolone as coupling compounds. CY1-NH2, CY2-NH2 and CY3-NH2 were prepared by reduction of CY1-NO2, CY2-NO2 and CY3-NO2 with sodium sulfide in ethanol/water, toluene/water and water, respectively. And their structures were characterized by IR,1H NMR and API-ES mass spectroscopy.
Polymaleic anhydride (PMA) was prepared in toluene initiated with benzoyl peroxide (BPO). Three polymaleic acid dyes with grafting ratio of 30% were synthesized by the reaction of PMA with CY1-NH2, CY2-NH2 and CY3-NH2, respectively. Amide was formed when ammonia reacted with PMA and imide was formed if urea was used. It proved that, amide or imide could be formed when using different agents under different reaction conditions. Based on this method, polymeric dyes with amide and imide groups were prepared derived from PMA-DY1, PMA-DY2 and PMA-DY3 synthesized in this thesis and PMA-DY4 and PMA-DY5 prepared by our research team, then the reaction with HCHO was carried out to prepare hydroxymethyl polymeric dyes. The structures of polymeric dyes were characterized by IR and 1H NMR.
Poly(maleic anhydride-acrylamide) (MA-AAm) was synthesized in tetrahydrofuran with azodiisobutyronitrile as free radical initiator. The structures of MA-AAm were characterized by FT-IR and GPC. In order to solve the problems of declining of utilization ratio of MA and of the yield of MA-AAm with the increase of dosage of MA, a technique for recycling use of polymerization residue was designed. The utilization ratio of MA and the yield of the copolymer were enhanced, and the content of MA within the copolymer did not change much. CY4-NH2 (4-((4'-aminophenyl)-azo)-1-phenyl-3-methyl-5-pyrazolone) was used to react with the copolymer of MA-AAm. The grafting ratio of CY4-NH2 was only 11.4%.
The solubility and the stability at different pH of two kinds of polymeric dyes were studied. It showed that, all polymeric dyes had good water-solubility when pH was above 7. DY1, DY2 and DY4 not containing water-soluble groups could dissolve in polar organic solvents. Aqueous solution of polymaleic acid dyes and hydroxymethyl polymeric dyes possessed good stability when pH was 3-10 at room temperature. Covalent bonds between polymeric dyes and cotton fibers were investigated by color stripping. Dip-pad dyeing method was used for all the dyes synthesized. The colorfastness on cotton and tear strength of the dyed cotton fibers were measured. The results showed that these polymeric dyes were suitable for dyeing cotton fibers. Formaldehyde released from the cotton fibers dyed with hydroxymethyl polymeric dyes was less than 75 mg/kg, it conformed to the requirements of national standard GB 18401-2003 (National general safety technical code for textiles products).
论文首先以对硝基苯胺为重氮组分,分别与对甲苯酚、N-乙基-3-氨甲酰基-4-甲基-6-羟基-2-吡啶酮、1-(2’,5’-二氯-4’-磺酸基苯基)-3-甲基-5-毗唑啉酮偶合制备了3支小分子偶氮型发色体CY1-NO2、CY2-NO2和CY3-NO2,然后分别在乙醇/水、甲苯/水混合溶剂和水介质中,用硫化钠还原发色体结构中的硝基,得到氨基发色体CY1-NH2、CY2-NH2和CY3-NH2。采用IR、MS、1HNMR等对上述发色体进行了结构表征。
以过氧化苯甲酰为引发剂,在甲苯中合成了聚马来酸酐(PMA)。将发色体CY1-NH2、CY2-NH2和CY3-NH2分别与PMA反应,合成了3支发色体含量为30%的聚马来酸型大分子染料。将PMA与氨水反应得到了以酰胺为主的产物,与尿素高温固相反应得到了以酰亚胺为主的产物,即采用不同的酰胺化试剂、不同的反应条件可得到酰胺或酰亚胺结构。以此为依据,分别对所合成的3支聚马来酸型大分子染料(PMA-DY1、PMA-DY2和PMA-DY3)以及本团队所合成的2支聚马来酸型大分子染料(PMA-DY4和PMA-DY5)进行了酰胺化和酰亚胺化改性,再与甲醛反应得到羟甲基型大分子染料。利用IR、1H NMR等对上述含羧酸基团和羟甲基基团的大分子染料进行了结构表征。
以偶氮二异丁腈为引发剂,在四氢呋喃中合成了马来酸酐-丙烯酰胺共聚物(MA-AAm);采用IR、凝胶渗透色谱(GPC)等对MA-AAm共聚物进行了结构表征。针对马来酸酐与丙烯酰胺共聚时,随着马来酸酐用量的增加,马来酸酐利用率下降及聚合物收率低的问题,论文通过对聚合残液的8次循环利用,马来酸酐单体利用率由35.7%提高至90.2%,聚合物收率由47.8%提高至近60%,并且聚合物中马来酸酐含量基本不变(～42%)。将发色体CY4-NH2(4-((4'-氨基苯基)偶氮基)-1-苯基-3-甲基-5-毗唑啉酮)与MA-AAm共聚物反应,发色体含量为11.4%。
研究了两类大分子染料的溶解性能及耐酸碱稳定性,结果表明,在pH>7时均具有较好的水溶性,不含水溶性基团的DY1、DY2和DY4系列染料能溶于常用的极性有机溶剂；室温时,大分子染料在pH 3-10能够稳定存在。剥色实验证明两类大分子染料与棉纤维以共价键结合。考察了两类大分子染料轧染染色棉纤维的各项牢度及撕裂强度,结果表明,均达到了染料应用的要求。经羟甲基型大分子染料染色后的棉纤维释放甲醛含量小于75 mg/kg,符合国标GB 18401-2003《国家纺织产品基本安全技术规范》。
In this thesis, polymaleic acid dyes and hydroxymethyl polymeric dyes for cotton fiber were designed and synthesized. As polymeric dyes contain multiple reactive groups, high fixation could be achieved through covalent bonds between polymeric dyes and cotton after dyeing and fixation.
CY1-NO2, CY2-NO2 and CY3-NO2 were synthesized by diazotization and coupling reaction by using p-nitroaniline as diazo component, and p-cresol,3-aminoformyl-l-ethyl-6-hydroxy-4-methyl-2-pyridone, and 1-(2',5'-dichloro-4'-sulfo-phenyl)-3-methyl-5-pyrazolone as coupling compounds. CY1-NH2, CY2-NH2 and CY3-NH2 were prepared by reduction of CY1-NO2, CY2-NO2 and CY3-NO2 with sodium sulfide in ethanol/water, toluene/water and water, respectively. And their structures were characterized by IR,1H NMR and API-ES mass spectroscopy.
Polymaleic anhydride (PMA) was prepared in toluene initiated with benzoyl peroxide (BPO). Three polymaleic acid dyes with grafting ratio of 30% were synthesized by the reaction of PMA with CY1-NH2, CY2-NH2 and CY3-NH2, respectively. Amide was formed when ammonia reacted with PMA and imide was formed if urea was used. It proved that, amide or imide could be formed when using different agents under different reaction conditions. Based on this method, polymeric dyes with amide and imide groups were prepared derived from PMA-DY1, PMA-DY2 and PMA-DY3 synthesized in this thesis and PMA-DY4 and PMA-DY5 prepared by our research team, then the reaction with HCHO was carried out to prepare hydroxymethyl polymeric dyes. The structures of polymeric dyes were characterized by IR and 1H NMR.
Poly(maleic anhydride-acrylamide) (MA-AAm) was synthesized in tetrahydrofuran with azodiisobutyronitrile as free radical initiator. The structures of MA-AAm were characterized by FT-IR and GPC. In order to solve the problems of declining of utilization ratio of MA and of the yield of MA-AAm with the increase of dosage of MA, a technique for recycling use of polymerization residue was designed. The utilization ratio of MA and the yield of the copolymer were enhanced, and the content of MA within the copolymer did not change much. CY4-NH2 (4-((4'-aminophenyl)-azo)-1-phenyl-3-methyl-5-pyrazolone) was used to react with the copolymer of MA-AAm. The grafting ratio of CY4-NH2 was only 11.4%.
The solubility and the stability at different pH of two kinds of polymeric dyes were studied. It showed that, all polymeric dyes had good water-solubility when pH was above 7. DY1, DY2 and DY4 not containing water-soluble groups could dissolve in polar organic solvents. Aqueous solution of polymaleic acid dyes and hydroxymethyl polymeric dyes possessed good stability when pH was 3-10 at room temperature. Covalent bonds between polymeric dyes and cotton fibers were investigated by color stripping. Dip-pad dyeing method was used for all the dyes synthesized. The colorfastness on cotton and tear strength of the dyed cotton fibers were measured. The results showed that these polymeric dyes were suitable for dyeing cotton fibers. Formaldehyde released from the cotton fibers dyed with hydroxymethyl polymeric dyes was less than 75 mg/kg, it conformed to the requirements of national standard GB 18401-2003 (National general safety technical code for textiles products).
引文
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