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化学进展 2011, Vol. 23 Issue (6): 1181-1188 前一篇   后一篇

• 综述与评论 •

非异氰酸酯聚氨酯合成与应用

黄耀成1, 梁丽芸1, 任旭2, 谭必恩1*   

  1. 1. 华中科技大学化学与化工学院 材料化学与服役失效湖北省重点实验室 武汉 430074;
    2. 深圳市天旭东科技有限公司 深圳518172
  • 收稿日期:2010-09-01 修回日期:2010-11-01 出版日期:2011-06-24 发布日期:2011-05-29
  • 作者简介:e-mail: bien.tan@mail.hust.edu.cn
  • 基金资助:

    教育部新世纪优秀人才支持计划项目(NCET-10-0389)资助

Nonisocyanate Polyurethanes and Their Applications

Huang Yaocheng1, Liang Liyun1, Ren Xu2, Tan Bien1*   

  1. 1. Hubei Key Laboratory of Materials Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China;
    2. Shenzhen Tianxudong Keji Co., Ltd, Shenzhen 518172, China
  • Received:2010-09-01 Revised:2010-11-01 Online:2011-06-24 Published:2011-05-29

聚氨酯是一种重要的高分子材料,但其关键原料异氰酸酯有毒和湿敏的缺点限制了其应用前景。环碳酸酯化合物与伯胺反应是制备得到聚氨酯的一条新途径,用这种方法合成的非异氰酸酯聚氨酯(NIPU),其羟基氨基甲酸酯基形成分子内氢键而具有比传统聚氨酯更好的耐水解性和机械性能。本文介绍了NIPU的合成机理,总结了环碳酸酯的合成方法,综述了环碳酸酯齐聚物及NIPU的合成和应用的研究进展,探讨了NIPU未能实现大规模的商业化应用的原因,并展望了未来的研究方向。

Polyurethane (PU) is one of the most important polymer materials due to its excellent properties, such as durability, impact resistance, stress relaxation, tear resistance and adhesion. However, isocyanate, which is a key monomer for conventional PU, has some drawbacks such as high toxicity and sensitivity to moisture. Also, urethane group is poorly resistant to hydrolysis.The reaction between cyclic carbonates and primary amines is a promising nonisocyanate route to produce PU. Nonisocyanate polyurethanes (NIPUs) produced by this method are more resistant to hydrolysis and have better mechanical properties due to the formation of intramolecular hydrogen bonds within the hydrourethane groups. In this paper, the formation mechanism of NIPUs is introduced. The synthesis methods of cyclic carbonate group and its catalyst systems are summarized. The progress of synthesis of cyclic carbonate oligomers and NIPUs as well as their applications are reviewed. Also, the reasons why NIPUs have not yet been widely commercially available and the research prospects are discussed.

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[1] Shalati M D, McBee J H, DeGooyer W J, Thys F, van der Ven L, Leijzer R T M. Prog. Org. Coat., 2003, 48(2/4): 236-250
[2] 霍 W ·K, 卡皮诺 L ·A, 克罗耶M ·V, 鲁特J ·M, 汤姆科R ·F. CN 1729260, 2006
[3] 周庆丰( Zhou Q F ), 潘明旺( Pan M W ), 袁金凤( Yuan J F ), 张留成( Zhang L C ). 化学通报( Chemistry ), 2006, 69: 1-9
[4] Kihara N, Hara N, Endo T. J. Org. Chem., 1993, 58(23): 6198-6202
[5] Kihara N, Kushida Y, Endo T. J. Polym. Sci., Part A: Polym. Chem., 1996, 34(11): 2173-2179
[6] Steblyanko A, Choi W, Sanda F, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2000, 38(13): 2375-2380
[7] Ochiai B, Inoue S, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2005, 43(24): 6282-6286
[8] Garipov R M, Sysoev V A, Mikheev V V, Zagidullin A I, Deberdeev R Y, Irzhak V I, Berlin A A. Dokl. Phys. Chem., 2003, 393(1): 289-292
[9] Clements J H. Ind. Eng. Chem. Res., 2003, 42(4): 663-674
[10] North M, Pasquale R. Angew. Chem. Int. Ed., 2009, 48(16): 2946-2948
[11] Meléndez J, North M, Pasquale R. Eur. J. Inorg. Chem., 2007, 2007(21): 3323-3326
[12] 任旭( Ren X ). CN 101584994, 2009
[13] Shim H L, Udayakumar S, Yu J I, Kim I, Park D W. Catal. Today, 2009, 148(3/4): 350-354
[14] 亢茂青( Kang M Q ), 李振荣( Li Z R ), 赵雨花( Zhao Y H ), 王军威( Wang J W ), 王心葵( Wang X K ). CN 101260232, 2008
[15] Türün O, Kayaman-Apohan N, Kahraman M V, Mencelo lu Y, Güngr A. J. Sol-Gel Sci. Technol., 2008, 47(3): 290-299
[16] 谭必恩( Tan B E ), 黄耀成( Huang Y C ), 梁丽芸( Liang L Y ), 任旭( Ren X ). CN 101775137, 2010
[17] Figovsky O L, Shapovalov L D. 26th FATIPEC Congress. Dresden: 2002, 325-332
[18] Stroganov I V, Stroganov V F. Polym. Sci. Ser. C, 2007, 49(3): 258-263
[19] Tomita H, Sanda F, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2001, 39(6): 851-859
[20] Kim M R, Kim H S, Park D W, Lee J K. React. Kinet. Catal. Lett., 2001, 72(2): 373-381
[21] Paddock R L, Nguyen S T. J. Am. Chem. Soc., 2001, 123(46): 11498-11499
[22] Sun J, Fujita S I, Arai M. J. Organomet. Chem., 2005, 690(15): 3490-3497
[23] Xiao L F, Li F W, Xia C G. Appl. Catal. A: Gen., 2005, 279(1/2): 125-129
[24] Lee E H, Ahn J Y, Dharman M M, Park D W, Park S W, Kim I. Catal. Today, 2008, 131(1/4): 130-134
[25] Kiso Y, Matsunaga Y, Imagawa M. US 4880942, 1989
[26] 袁中顺( Yuan Z S ), 汪猛( Wang M ), 刘成学( Liu C X ), 顾尧( Gu Y ), 贺文媛( He W Y ). CN 101367933, 2009
[27] Tamami B, Sohn S, Wilkes G L. J. Appl. Polym. Sci., 2004, 92(2): 883-891
[28] Javni I, Doo P H, Petrovic Z S. J. Appl. Polym. Sci., 2008, 108(6): 3867-3875
[29] Doll K M, Erhan S Z. Green Chem., 2005, 7(12): 849-854
[30] Kim M R, Kim H S, Ha C S, Park D W, Lee J K. J. Appl. Polym. Sci., 2001, 81(11): 2735-2743
[31] Suzuki A, Nagai D, Ochiai B, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2004, 42(23): 5983-5989
[32] Ohrbom W H, December T S, Harris P J. US 5856382, 1999
[33] Figovsky O L, Shapovalov L D. US 7232877 B2, 2007
[34] Park H Y, Lee D W, Lee H S, Lim D O, Park D W. React. Kinet. Catal. Lett., 2003, 79(2): 245-255
[35] Ochiai B, Hatano Y, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2009, 47(12): 3170-3176
[36] O'Brien J L, Beavers E M, Park E. US 2979514, 1961
[37] Jana S, Yu H, Parthiban A, Chai C L L. J. Polym. Sci., Part A: Polym. Chem., 2010, 48(7): 1622-1632
[38] Golden J H, Chew B G M, Zax D B, DiSalvo F J, Frechet J M J, Tarascon J M. Macromolecules, 1995, 28(9): 3468-3470
[39] Webster D C, Crain A L. Prog. Org. Coat., 2000, 40(1/4): 275-282
[40] Han L, Park S-W, Park D-W. Energy Environ. Sci., 2009, 2(12): 1286-1292
[41] Zhu Z, Einset A G, Yang C-Y, Chen W-X, Wnek G E. Macromolecules, 1994, 27(15): 4076-4079
[42] Rokicki G, Kowalczyk T, Glinski M. Polym. J., 2000, 32(5): 381-390
[43] Al-Azemi T F, Bisht K S. Polymer, 2002, 43(8): 2161-2167
[44] Miyagawa T, Shimizu M, Sanda F, Endo T. Macromolecules, 2005, 38(19): 7944-7949
[45] Darensbourg D J, Moncada A I. Macromolecules, 2010, 43(14): 5996-6003
[46] Tomita H, Sanda F, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2001, 39(6): 860-867
[47] Tomita H, Sanda F, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2001, 39(1): 162-168
[48] Whelan J M, Cotter R J. US 3072613, 1963
[49] Huo L, Li T, Guo J. J. Macromol. Sci., Pure Appl. Chem., 2010, 47(5): 457-460
[50] Ochiai B, Satoh Y, Endo T. J. Polym. Sci., Part A: Polym. Chem., 2009, 47(18): 4629-4635
[51] Tomita H, Sanda F, Endo T. Macromolecules, 2001, 34(22): 7601-7607
[52] Li Z, Zhao Y, Yan S, Wang X, Kang M, Wang J, Xiang H. Catal. Lett., 2008, 123(3): 246-251
[53] Parzuchowski P G, Jurczyk-Kowalska M, Ryszkowska J, Rokicki G. J. Appl. Polym. Sci., 2006, 102(3): 2904-2914
[54] 任旭( Ren X ). CN 101812175, 2009
[55] 刘晓国( Liu X G ), 黄禹( Huang Y ). 广州大学学报(自然科学版) ( Journal of Guangzhou University, Natural Science Edition ), 2010, 9(9): 36-40
[56] Figovsky O L, Shapovalov L D. Polymers and Adhesives in Microelectronics and Photonics. Potsdam: Institute of Electrical and Electronics Engineers Inc., 2001, 257-264
[57] Webster D C, Su C H J, Foster C H. US 5567527, 1996
[58] Ramesh S, Lessek P, Bremser W. US 6403709, 2002
[59] Yang L, Ruhoff P J, Hung R, Stenson P. WO 97/23516, 1997
[60] Ochiai B, Satoh Y, Endo T. Green Chem., 2005, 7: 765-767
[61] Webster D C. US 6339129, 2002
[62] Ohrbom W H, Herrel P A. US 6812300, 2004

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摘要

非异氰酸酯聚氨酯合成与应用