应用化学 ›› 2017, Vol. 34 ›› Issue (6): 649-655.DOI: 10.11944/j.issn.1000-0518.2017.06.160394

• 研究论文 • 上一篇    下一篇

一种反应型染料的合成及其在聚氨酯革染色中的应用

尹志刚(),刘珍珍,钱恒玉,赵喜乐,彭丽芳,袁奇   

  1. 郑州轻工业学院材料与化学工程学院 郑州 450002
  • 收稿日期:2016-09-28 接受日期:2017-02-12 出版日期:2017-05-31 发布日期:2017-05-31
  • 通讯作者: 尹志刚
  • 基金资助:
    国家级大学生创新创业训练计划项目(201410462028,2015005)郑州轻工业学院第四批大学生创新实验项目(2015005)资助

Synthesis of a Polymerizable Dye Monomer and Its Application in Dyeing Polyurethane Leather

YIN Zhigang(),LIU Zhenzhen,QIAN Hengyu,WANG Zaifeng,ZHAO Xile,PENG Lifang,YUAN Qi   

  1. School of Material and Chemical Engineering,Zhengzhou University of Light Industry,Zhengzhou 450002,China
  • Received:2016-09-28 Accepted:2017-02-12 Published:2017-05-31 Online:2017-05-31
  • Contact: YIN Zhigang
  • Supported by:
    Supported by National Undergraduate Innovation and Entrepreneurship Training Program(No.201410462028, No.2015005), Zhengzhou University of Light Industry, The Fourth Batch of College Students Innovative Experimental Project funds(No.2015005)

摘要:

针对传统聚氨酯色浆中色基与聚氨酯结合力弱(分子间力),导致成品革色牢度差、色迁移严重等技术难题,本文设计合成了一种反应型彩色二元醇:在四氢呋喃介质中,控制n(对苯二胺)∶n(乙酸酐)=1.00∶0.95, 0~5 ℃下,用乙酸酐将对苯二胺单酰化反应15 h,得到对氨基乙酰苯胺(产率85%),经重氮化,与过量摩尔分数为5% N-苯基二乙醇胺偶合制得了一种含两个端羟甲基的偶氮化合物4-乙酰基胺基-4'-N,N-二羟乙氨基偶氮苯(产率82%);将其与聚酯二元醇、聚醚二元醇以不同比例混合,与双异氰酸酯预聚、扩链后形成红色聚氨酯树脂色浆,在离型纸上铺展成膜,其断裂增长率443.0%,断裂相对强度125.5 g,色迁移量21.4 μg,进口同类产品形成膜后的断裂增长率、断裂相对强度与色迁移量分别为442.2%、125.3 g和29.2 μg.合成产品优于同类进口产品。

关键词: 对苯二胺, 乙酰化, 重氮化偶合反应, 偶氮化合物, 红色聚氨酯, 色迁移

Abstract:

In order to solve poor color fastness and serious color transfer of the traditional color polyurethane leather because of weak interaction(intermolecular force) between polyurethane and color base. A kind of reactive color diol was synthesized as follows:p-aminoacetanilide with a yield of 85% was prepared by acylation of p-phenylenediamine with acetic anhydride in tetrahydrofuran at 0~5 ℃ for 15 h, during which the molar ratio of p-phenylenediamine to acetic anhydride was 1.00∶0.95. Then its diazonium salt was coupled with an excess molar fraction of 5% N-phenyl-diethanolamine to obtain 4-acetylamino-4'-N,N-dihydroxyethylamino azobenzene with yield of 82%. The reactive color diol was mixed with polyester or polyether diol in different proportions, followed by prepolymering, chain extension with diisocyanate to form polyurethane resin color paste whose crack-growth rate, relative breaking strength, and color transfer are 443%, 125.5 g and 21.4 μg, respectively, when spreaded into a film. And those of the similar film obtained from import diol are 442.2%, 125.3 g and 29.2 μg, respectively, indicating that the synthetic color diol is superior to the imported product.

Key words: p-phenylenediamine, acetylation, diazo coupling reaction, azo-compound, red polyurethane, color transfer