2，4-二（氨基蒽醌）均三嗪衍生的还原染料的研究
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摘要
在纤维着色方面,尽管还原染料的用量下降了不少,但它仍然占有很重要的地位,因为还原染料具有优良的各项牢度性能,尤其是其耐日晒、耐水洗及氯漂等性能更是优越,所以今后还原染料在染料市场上的份额至少还会保持在目前的水平上,甚至会由于棉在市场上消耗量的逐年增加而有少量增加。因此,目前还没有一支染料能够真正替代还原染料。
本文对还原蓝66进行结构剖析和合成,并同时顾及还原染料新品种的开发,主要工作有:
1)对商品染料还原蓝66进行分离提纯和裂解,应用元素分析、质谱、核磁红外等手段推断出还原蓝66的结构,并经合成验证表明推断正确。
2)以2-乙基蒽醌为原料,经硝化、氧化、二次硝化、还原等反应合成了还原蓝66的中间体1,4-二氨基-2-乙酰基蒽醌,其中2-乙基蒽醌的硝化首次采用有机溶剂法,氧化反应则采用发烟硫酸代替目前使的氧化剂Na_2Cr_2O_7/H_2SO_4,硝基化合物的还原采用催化加氢的方法,有效的防止了含铬废水的排放,降低了污染,同时还对二硝化地反应机理进行了探讨;以苯代三聚氰胺为原料,经水解、氯代反应合成了中间体苯代三聚氯氰,产物结构通过质谱、核磁共振、红外等分析确认正确,在此基础上合成了还原蓝66,并完成了中试,合成路线不同于BASF公司的传统路线。
3)以α-氨基蒽醌或β-氨基蒽醌为原料,分别与苯代三聚氯氰、三聚氯氰及苯胺、对氨基苯甲醚、2-氨基噻唑等缩合合成了10只氨基蒽醌均三嗪型黄色还原染料,测试了其牢度及应用性能。
4)以1-氨基-2-溴-4-羟基蒽醌为原料,分别与双酚 A、对苯二酚等进行williamson醚缩合,合成了两只红色染料,结构经核磁共振及红外光谱确认,该化合物结构未见报道。对其耐升华牢度测试表明,其升华牢度较高。
In the coloration of cellulosic fibres, although the total number of vat dyes on the market has diminished, vat dyes (including indigo) hold a large part of the dyestuff market. The situation of vat dyes will remain constant in the near future mainly because vat dyes yield coloured fibres of excellent all-round fastness, particularly to light, washing and chlorine bleaching, even the consumption of vat dyes will increase a little with increasing of the cotton consumption. Thus, at present, there is no true alternative to this class of dye.Vat Blue 66 was analyzed and synthesized and some novel vat dyes were synthesized, the following work is done in this paper.1) Vat Blue 66 was separated and its structure was determined by MS, NMR, IR and element analysis.2) From 2-ethylanthraquinone, 1,4-diamino-2-acetylanthraquinone was prepared via nitration, oxidation, re-nitration, reduction and so on. In this process the nitration of 2-ethylanthraquinone was first achieved in the organic solvent and its product was oxidized by oleum instead of Na_2Cr_2O_7/H_2SO_4 used in the industry recently. The nitration compounds were reduced by nickel as catalyst. All of these made the wastewater containing chromium prevented and the pollution were decreased greatly. 2-phenyl-4,6-dichloro-1,3,5-triazine was synthesized via hydrolyzationd and chlorination used 2-phenyl-4,6- diamino-1,3,5-triazine as raw material. Their structures were confirmed by MS, 1~H NMR and IR. Following these processes, which were different from that of the BASF, Vat Blue 66 was synthesized and industrialized.3) Ten yellow vat dyes were prepared by α-aminoanthraquinone or β-amino anthraquinone reacting with 2-phenyl-4,6-dichloro-1,3,5-triazine, 2,4,6-trichloro-1,3,5-triazine, aniline, p-methoxyaniline, 2-aminothiazole and so on. Their application properties were measured and would likely tend to industrialize.4) Two red dyes were prepared by 1 -amino-2-bromo-4-hydroxyanthraquinone reacting with 4,4'-dihydroxydiphenyl propane, hydroquinone and their structures, which were not reported before, were confirmed by 1~H NMR and IR. The fastness to sublimation of them was good.
本文对还原蓝66进行结构剖析和合成,并同时顾及还原染料新品种的开发,主要工作有:
1)对商品染料还原蓝66进行分离提纯和裂解,应用元素分析、质谱、核磁红外等手段推断出还原蓝66的结构,并经合成验证表明推断正确。
2)以2-乙基蒽醌为原料,经硝化、氧化、二次硝化、还原等反应合成了还原蓝66的中间体1,4-二氨基-2-乙酰基蒽醌,其中2-乙基蒽醌的硝化首次采用有机溶剂法,氧化反应则采用发烟硫酸代替目前使的氧化剂Na_2Cr_2O_7/H_2SO_4,硝基化合物的还原采用催化加氢的方法,有效的防止了含铬废水的排放,降低了污染,同时还对二硝化地反应机理进行了探讨;以苯代三聚氰胺为原料,经水解、氯代反应合成了中间体苯代三聚氯氰,产物结构通过质谱、核磁共振、红外等分析确认正确,在此基础上合成了还原蓝66,并完成了中试,合成路线不同于BASF公司的传统路线。
3)以α-氨基蒽醌或β-氨基蒽醌为原料,分别与苯代三聚氯氰、三聚氯氰及苯胺、对氨基苯甲醚、2-氨基噻唑等缩合合成了10只氨基蒽醌均三嗪型黄色还原染料,测试了其牢度及应用性能。
4)以1-氨基-2-溴-4-羟基蒽醌为原料,分别与双酚 A、对苯二酚等进行williamson醚缩合,合成了两只红色染料,结构经核磁共振及红外光谱确认,该化合物结构未见报道。对其耐升华牢度测试表明,其升华牢度较高。
In the coloration of cellulosic fibres, although the total number of vat dyes on the market has diminished, vat dyes (including indigo) hold a large part of the dyestuff market. The situation of vat dyes will remain constant in the near future mainly because vat dyes yield coloured fibres of excellent all-round fastness, particularly to light, washing and chlorine bleaching, even the consumption of vat dyes will increase a little with increasing of the cotton consumption. Thus, at present, there is no true alternative to this class of dye.Vat Blue 66 was analyzed and synthesized and some novel vat dyes were synthesized, the following work is done in this paper.1) Vat Blue 66 was separated and its structure was determined by MS, NMR, IR and element analysis.2) From 2-ethylanthraquinone, 1,4-diamino-2-acetylanthraquinone was prepared via nitration, oxidation, re-nitration, reduction and so on. In this process the nitration of 2-ethylanthraquinone was first achieved in the organic solvent and its product was oxidized by oleum instead of Na_2Cr_2O_7/H_2SO_4 used in the industry recently. The nitration compounds were reduced by nickel as catalyst. All of these made the wastewater containing chromium prevented and the pollution were decreased greatly. 2-phenyl-4,6-dichloro-1,3,5-triazine was synthesized via hydrolyzationd and chlorination used 2-phenyl-4,6- diamino-1,3,5-triazine as raw material. Their structures were confirmed by MS, 1~H NMR and IR. Following these processes, which were different from that of the BASF, Vat Blue 66 was synthesized and industrialized.3) Ten yellow vat dyes were prepared by α-aminoanthraquinone or β-amino anthraquinone reacting with 2-phenyl-4,6-dichloro-1,3,5-triazine, 2,4,6-trichloro-1,3,5-triazine, aniline, p-methoxyaniline, 2-aminothiazole and so on. Their application properties were measured and would likely tend to industrialize.4) Two red dyes were prepared by 1 -amino-2-bromo-4-hydroxyanthraquinone reacting with 4,4'-dihydroxydiphenyl propane, hydroquinone and their structures, which were not reported before, were confirmed by 1~H NMR and IR. The fastness to sublimation of them was good.
引文
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