Citation: YIN Zhigang, LIU Zhenzhen, QIAN Hengyu, WANG Zaifeng, ZHAO Xile, PENG Lifang. Synthesis of a Polymerizable Dye Monomer and Its Application in Dyeing Polyurethane Leather[J]. Chinese Journal of Applied Chemistry, ;2017, 34(6): 649-655. doi: 10.11944/j.issn.1000-0518.2017.06.160394 shu

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

School of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, China

Corresponding author: YIN Zhigang, yinck@zzuli.edu.cn
Received Date: 28 September 2016
Revised Date: 21 December 2016
Accepted Date: 12 February 2017

Fund Project: Zhengzhou University of Light Industry, The Fourth Batch of College Students Innovative Experimental Project funds 2015005National Undergraduate Innovation and Entrepreneurship Training Program 2015005National Undergraduate Innovation and Entrepreneurship Training Program 201410462028

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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.
- p-phenylenediamine,
- acetylation,
- diazo coupling reaction,
- azo-compound,
- red polyurethane,
- color transfer
1. [1]
  Li J, Wang X Y, Liang X G. Modification of Nucleic Acids by Azobenzene Derivatives and Their Applications in Biotechnology and Nanotechnology[J]. Chem-Asian J, 2014,9(12):3344-3358. doi: 10.1002/asia.v9.12
2. [2]
  Seki T. Dynamic Photoresponsive Functions in Organized Layer Systems Comprised of Azobenzene-containing Polymers[J]. Polym J, 2004,36(6):435-454. doi: 10.1295/polymj.36.435
3. [3]
  QIN Chuanguang, LI Yang, LI Hailiang. New Development in Synthesis of Aromatic azo Derivatives[J]. Chinese J Org Chem, 2013,33:444-457.
4. [4]
  Fujiwara M, Imura T. Photo Induced Membrane Separation for Water Purification and Desalination Using Azobenzene Modified Anodized Alumina Membranes[J]. ACS Nano, 2015,9(6):5705-5712. doi: 10.1021/nn505970n
5. [5]
  Hvilsted S, Ramanujam P S. The Azobenzene Optical Storage Puzzle-demands on the Polymer Scaffold[J]. Monatsh Chem, 2001,132(1):43-51. doi: 10.1007/s007060170143
6. [6]
  WANG Dongrui, WANG Xiaogong. Graphene/the New Research Progress of Azo Hybrid Materials[J]. Sci Sin Chim, 2012,42(5):636-643.
7. [7]
  WANG Yongqiang, WANG Jian, YU Huazhong. The Photoelectrochemical Response of Azobenzene Self-assembled Monolayers on Gold Surface[J]. Chem J Chinese Univ, 1996,17(7):1130-1135.
8. [8]
  Zollinger H. Color Chemistry-Synthesis, Properties, and Applications of Organic Dyes and Pigments[M]. WU Zuwang, CHEGN Lvbai, ZHANG Zhuangyu Trans. Beijing:Chemical Industry Press, 2005:2-267(in Chinese).
9. [9]
  HOU Yufen. Dye Chemistry[M]. Beijing:Chemical Industry Press, 1994:7-39(in Chinese).
10. [10]
  ZHANG Yue, QIANG Xihuai, NIU Ze. Polyurethane Dyestuff with High Color Fastness[J]. China Leather, 2015,44(3):22-25.
11. [11]
  CHEN Wei, WU Jinjing, CHEN Xin. Progress in the Study on the Control of Color Waterborne Polyurethane for Synthetic Leather[J]. Guangzhou Chem Ind, 2015,43(21):22-23. doi: 10.3969/j.issn.1001-9677.2015.21.006
12. [12]
  HE Jinxin. Dye Chemistry[M]. Beijing:China Textile Industry Press, 2009:37-40(in Chinese).
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