Atom Transfer Radical Polymerization of Secondary Amine Containing Methacrylate Monomer

doi:10.6023/cjoc201509039

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (2): 412-416.DOI: 10.6023/cjoc201509039 Previous Articles Next Articles

Notes

含有仲氨基团的甲基丙烯酸酯单体的原子转移自由基聚合研究

简祖凯^a, 杨阳^b, 郎美东^a, 李永军^b

a 华东理工大学材料科学与工程学院超细材料制备与应用教育部重点实验室上海 200237;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2015-09-19 修回日期:2015-10-16 发布日期:2015-10-26
通讯作者: 郎美东, 李永军 E-mail:mdlang@ecust.edu.cn;liyongjun78@sioc.ac.cn
基金资助:
国家自然科学基金(No. 21204098)资助项目

Atom Transfer Radical Polymerization of Secondary Amine Containing Methacrylate Monomer

Jian Zukai^a, Yang Yang^b, Lang Meidong^a, Li Yongjun^b

a Key Laboratory for Ultrafine Materials of Ministry of Education, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2015-09-19 Revised:2015-10-16 Published:2015-10-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21204098)

1. Atom Transfer Radical Polymerization of Secondary Amine Containing Methacrylate Monomer.PDF(760KB)

Abstract

Radical polymer poly(2,2,6,6-tetramethylpiperidinyloxy-4-yl methacrylate) (PTMA), a potential cathode materials, was prepared by radical polymerization of 2,2,6,6-tetramethylpiperidin-4-yl methacrylate (TMPM) containing secondary amine group, followed by oxidation into radical polymer. However, the living radical polymerization of TMPM was hindered by its secondary amine group. The optimized atom transfer radical polymerization condition for TMPM via screening various initiators and catalyst systems was reported, and poly(2,2,6,6-tetramethylpiperidin-4-yl methacrylate)s with different molecular weight were prepared.

Key words: methacrylate, secondary amine, atom transfer radical polymerization

Cite this article

Jian Zukai, Yang Yang, Lang Meidong, Li Yongjun. Atom Transfer Radical Polymerization of Secondary Amine Containing Methacrylate Monomer[J]. Chin. J. Org. Chem., 2016, 36(2): 412-416.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Arico, A. S.; Bruce, P.; Scrosati, B.; Tarascon, J. M.; Van Schalkwijk, W. Nat. Mater. 2005, 4, 366.
[2] Bruce, P. G.; Scrosati, B.; Tarascon, J. M. Angew. Chem., Int. Ed. 2008, 47, 2930.
[3] Aricò, A. S.; Bruce, P.; Scrosati, B.; Tarascon, J. M.; Van Schalkwijk, W. Nat. Mater. 2005, 4, 366.
[4] Poizot, P.; Dolhem, F. Energy Environ. Sci. 2011, 4, 2003.
[5] Liang, Y.; Tao, Z.; Chen, J. Adv. Energy Mater. 2012, 2, 742.
[6] Nakahara, K.; Iwasa, S.; Satoh, M.; Morika, Y.; Iriyama, J.; Suguro, M.; Hasegawa, E. Chem. Phys. Lett. 2002, 359, 351.
[7] Zhao, R. R.; Zhu, L. M.; Yang, H. X. Prog. Chem. 2011, 23, 302 (in Chinese). (赵瑞瑞, 朱利敏, 杨汉西, 化学进展, 2011, 23, 302.)
[8] Deng, L. F.; Li, X. H.; Xiao, L. X.; Zhang, Y. H. Acta Polym. Sin. 2004, (1), 8 (in Chinese). (邓凌峰, 李新海, 肖立新, 张云河, 高分子学报, 2004, (1), 8.)
[9] Guo, W.; Yin, Y. X.; Xin, S.; Guo, Y. G.; Wan, L. J. Energy Environ. Sci. 2012, 5, 5221.
[10] Rostro, L.; Baradwaj, A. G..; MuLLer, A. R. MRS Commun. 2015, 5, 257.
[11] Bertrand, O.; Ernould, B.; Boujioui, F.; Vlad, A.; Gohy, J. F. Polym. Chem. 2015, 6, 6067.
[12] Sukegawa, T.; Masuko, I.; Oyaizu, K.; Nishide, H. Macromolecules 2014, 47, 8611.
[13] Janoschka, T.; Teichler, A.; Krieg, A.; Hager, M. D.; Schubert, U. S. J. Polym. Sci., Part A: Polym. Chem. 2012, 50, 1394.
[14] Wang, Y. H.; Hung, M. K.; Lin, C. H.; Lin, H. C.; Lee, J. T. Chem. Commun. 2011, 47, 1249.
[15] Hauffman, G.; Rolland, J.; Bourgeois, J. P.; Vlad, A.; Gohy, J. F. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 101.
[16] Kurosaki, T.; Lee, K. W.; Okawara, M. J. Polym. Sci., Part A: Polym. Chem. 1972, 10, 3295.
[17] Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921.
[18] Pintauer, T.; Matyjaszewski, K. Coord. Chem. Rev. 2005, 249, 1155.
[19] Zhang, X. H.; Li, H. Q.; Li, L. T.; Lu, G. L.; Zhang, S.; Gu. L. N.; Xia, Y. Y.; Huang, X. Y. Polymer 2008, 49, 3393.

含有仲氨基团的甲基丙烯酸酯单体的原子转移自由基聚合研究

Atom Transfer Radical Polymerization of Secondary Amine Containing Methacrylate Monomer

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 10

Recommended Articles

Metrics

Comments

[1]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[2]	Linlin Li, Xiaoyu Chen, Congcong Pei, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu. Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B₂pin₂/D₂O System [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2319-2325.
[3]	Fu Jianhua, Wang Zhaoyang, Huo Jingpei, Tan Yuehe, Zeng Ronghua . Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines [J]. Chin. J. Org. Chem., 2012, 32(01): 104-112.
[4]	FU Jian-Hua, WANG Chao-Yang, HAO Zhi-Feng, HUO Jing-Pei. Syntheses and Characterization of 5-Alkoxy-4-cycloamino-3- halo-5H-furan-2-one [J]. Chin. J. Org. Chem., 2011, 31(9): 1460-1467.
[5]	ZHANG Hua-Cheng, LIU Zhao-Na, XIN Fei-Fei, LI Yue-Ming, KONG Li, HAO Ai-You. Atom Transfer Radical Polymerization Based on Cyclodextrin [J]. Chin. J. Org. Chem., 2011, 31(11): 1761-1772.
[6]	WANG JIN;XU HENGFENG;ZHOU XUNJUN;DU SHAOBIN. Aminoalkylation of benzotriazole: Synthesis of secondary amines [J]. Chin. J. Org. Chem., 1992, 12(2): 198-201.
[7]	KUANG RONGZE;RUAN SUMEI;CHENG YIZHI. Asymmetric addition of thiophenol to chalcone catalyzed by chiral β- hydroxy amines [J]. Chin. J. Org. Chem., 1990, 10(6): 507-512.
[8]	LU PING;LI JIANQING;LI GONGHANG;ZHOU XUNJUN. Synthesis of secondary amines in the presence of sodium hydrogentelluride [J]. Chin. J. Org. Chem., 1986, 6(6): 447-448.
[9]	ZHOU XUNJUN;LU PING. The method for reducing imines by sodium hydrogntelluride [J]. Chin. J. Org. Chem., 1986, 6(1): 60-61.
[10]	ZENG BAIFEI;WU BAOZHU;SHEN SHOUPENG;WU LINSHENG. Piezoelectricity and molecular motion of poly(vinylidene-fluoride)blends [J]. Chin. J. Org. Chem., 1985, 5(3): 261-263.