Synthesis and Properties of Benzocyclobutene-Functionalized Thermosetting Polycarbonate

doi:10.6023/cjoc201604013

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (10): 2442-2448.DOI: 10.6023/cjoc201604013 Previous Articles Next Articles

Articles

含苯并环丁烯基团的热固性聚碳酸酯的合成及性能研究

李智勇^a,b, 曹卫国^a, 孙晶^b, 房强^b

a 上海大学化学系上海 200444;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2016-04-07 修回日期:2016-05-30 发布日期:2016-06-02
通讯作者: 曹卫国,E-mail:wgcao@staff.shu.edu.cn;孙晶,E-mail:sunjing@sioc.ac.cn;房强,E-mail:qiangfang@sioc.ac.cn E-mail:wgcao@staff.shu.edu.cn;sunjing@sioc.ac.cn;qiangfang@sioc.ac.cn
基金资助:
国家自然科学基金基金（No.21374131，21574146，21504103），上海市自然科学基金（No.15ZR1449200）资助项目.

Synthesis and Properties of Benzocyclobutene-Functionalized Thermosetting Polycarbonate

Li Zhiyong^a,b, Cao Weiguo^a, Sun Jing^b, Fang Qiang^b

a Department of Chemistry, Shanghai University, Shanghai 200444;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2016-04-07 Revised:2016-05-30 Published:2016-06-02
Supported by:
Project supported by the Natural Science Foundation of China (NSFC, No.21374131, 21574146 and 21504103) and the Science and Technology Commission of Shanghai Municipality (15ZR1449200).

1. Synthesis and Properties of Benzocyclobutene-Functionalized Thermosetting Polycarbonate.PDF(661KB)

Abstract

A novel benzocyclobutene (BCB)-functionalized polycarbonate was synthesized. This polymer showed good solu-bility in organic solvents and could be processed by solution method. After cured at high temperature, the polymer exhibited high thermostability with 5% weight loss temperature of 451℃ and a char yield of 33% at 1000℃ in nitrogen. The cured polymer showed good hydrophobicity with water uptake of 0.21% after immersion in boiling water for 24 h. Moreover, a copolymer and poly(bisphenol A carbonate) were synthesized by bisphenol A monomer to study the influence of the existence of BCB groups on the properties of the aromatic polycarbonate. The results of comparative study showed that BCB groups can effectively improve the thermostability and hydrophoblicity of aromatic polycarbonates.

Key words: polycarbonate, benzocyclobutene, synthesis, thermosetting polymer

Cite this article

Li Zhiyong, Cao Weiguo, Sun Jing, Fang Qiang. Synthesis and Properties of Benzocyclobutene-Functionalized Thermosetting Polycarbonate[J]. Chin. J. Org. Chem., 2016, 36(10): 2442-2448.

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[1] Bendler, J. T.; Boyles, D. A.; Edmondson, C. A.; Filipova, T.; Fontanella, J. J.; Westgate, M. A.; Wintersgill, M. C. Macromolecules 2013, 46, 4024.
[2] Yoonessi, M.; Gaier, J. R. ACS Nano 2010, 4, 7211.
[3] Tamarit-López, J.; Morais, S.; Bañuls, M.; Puchades, R.; Ma-quieira, Á. Anal. Chem. 2010, 82, 1954.
[4] Zhou, J.; Lubineau, G. ACS Appl. Mater. Interfaces 2013, 5, 6189.
[5] Méndez-Liñán, L.; López-Garzón, F. J.; Domingo-García, M.; Pérez-Mendoza, M. Energy Fuels 2010, 24, 3394.
[6] Moon, S. I.; Extrand, C. W. Ind. Eng. Chem. Res. 2009, 48, 8961.
[7] Lyu, M.-Y.; Lee, J. S.; Pae, Y. J. Appl. Polym. Sci. 2001, 80, 1814.
[8] Baick, I. H.; Yang, W. J.; Ahn, Y. G.; Song, K. H.; Choi, K. Y. J. Appl. Polym. Sci. 2015, 132, 41609.
[9] Awwad, S. H.; Filipova, T. S.; Boyles, D. A. Polym. Prepr. 2011, 52(1), 368.
[10] Laughner, M. K.; Farah, H. WO 9215643, 1992[Chem. Abdtr. 1993, 118, 256003].
[11] Boyles, D. A.; Filipova, T. S.; Bendler, J. T.; Longbrake, G.; Reams, J. Macromolecules 2005, 38, 3622.
[12] Filipova, T. S.; Boyles, D. A.; Schroeder, M. J.; Fontanella, J. J.; Wintersgill, M. C.; Edmondson, C. A.; Bendler, J. T. Polym. Prepr. 2009, 50(2), 543.
[13] Delassus, S. L.; Howell, B. A. Macromolecules 1994, 27, 1307.
[14] Tian, S.; Sun, J.; Jin, K.; He, F.; Zheng, S.; Fang, Q. ACS Appl. Mater. Interfaces 2014, 6, 20437.
[15] Hahn, S. F.; Martin, S. J.; Mckelvy, M. L.; Patrick, D. W. Macro molecules 1993, 26, 3870.
[16] Marks, M. J.; Erskine, J. S.; McCrery, D. A. Macromolecules 1994, 27, 4114.
[17] Wang, J.; Piskun, I.; Craig, S. L. ACS Macro Lett. 2015, 4, 834.
[18] Cheng, Y.; Yang, J.; Jin, Y.; Deng, D.; Xiao, F. Macromolecules 2012, 45, 4085.
[19] He, F.; Yuan, C.; Li, K.; Diao, S.; Jin, K.; Wang, J.; Tong, J.; Ma, J.; Fang, Q. RSC Adv. 2013, 3, 23128.
[20] Ma, B.; Lauterwasser, F.; Deng, L.; Zonte, C. S.; Kim, B. J.; Fréchet, J. M. J. Chem. Mater. 2007, 19, 4827.
[21] Walker, K. A.; Markoski, L. J.; Moore, J. S. Macromolecules 1993, 26, 3713.
[22] Wang, Y.; Sun, J.; Jin, K.; Wang, J.; Yuan, C.; Tong, J.; Diao, S.; He, F.; Fang, Q. RSC Adv. 2014, 4, 39884.
[23] Chae, J. Arch. Pharm. Res. 2008, 31, 305.
[24] Kampouris, E. M. J. Chem. Soc. 1965, 2651.
[25] Yang, J.; Liu, S.; Zhu, F.; Huang, Y.; Li, B.; Zhang, L. J. Polym. Sci., Part A:Polym. Chem. 2011, 49, 381.

含苯并环丁烯基团的热固性聚碳酸酯的合成及性能研究

Synthesis and Properties of Benzocyclobutene-Functionalized Thermosetting Polycarbonate

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