低分子量含氟聚合物的制备、官能化及特性

李东翰; 齐士成; 张孝阿; 廖明义

doi:10.7536/PC151208

化学进展 ›› 2016, Vol. 28 ›› Issue (5) :673-685 DOI: 10.7536/PC151208

综述与评论

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低分子量含氟聚合物的制备、官能化及特性

^1*

作者信息 +

Preparation, Functionalization and Properties of Low Molecular Fluoropolymers

Li Donghan¹, Qi Shicheng², Zhang Xiaoa², Liao Mingyi^1*

Author information +

文章历史 +

摘要

低分子量含氟聚合物是重要的新型功能材料,在国防工业中占有特殊地位。同时,作为高科技战略物资,近年来逐渐成为研究热点。本文对低分子量含氟聚合物的制备方法、官能化及特性进行了综述,重点介绍了低分子量含氟聚合物的制备和官能化方法的研究进展,并总结和详细介绍了低分子量含氟聚合物的特性,最后对该领域的前景和发展方向进行了展望。

Abstract

Low molecular fluoropolymers have a special status in the defense industry as the important new functional materials. Meanwhile, as high-tech strategic materials, they have attracted more attention. Low molecular fluoropolymers, not only have excellent performance of traditional fluoropolymers, but also have irreplaceable characteristics. In the present study, the preparation, functionalization, and properties of low molecular fluoropolymers are reviewed. The study highlights the research progress in the preparation and functionalization methods. The properties of low molecular fluoropolymers are also summarized. Finally, the future development of low molecular fluoropolymers is prospected.

Contents
1 Introduction
2 Preparation methods of low molecular fluoropolymers
2.1 Copolymerization method
2.2 Oligomerization method
2.3 ITP method
2.4 Functional initiator method
2.5 Oxidative degradation method
3 Functionalization methods of low molecular fluoropolymers
3.1 Functional monomer method
3.2 Functional group transformation method
3.3 Functional monomer and group transformation method
4 Properties of low molecular fluoropolymers
4.1 Processing property
4.2 Physical property
5 Conclusion and outlook

Graphical abstract

关键词

低分子量含氟聚合物 / 制备 / 官能化 / 特性

Key words

low molecular fluoropolymers / preparation / functionalization / properties

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李东翰, 齐士成, 张孝阿, 廖明义. 低分子量含氟聚合物的制备、官能化及特性[J]. 化学进展, 2016, 28(5): 673-685 DOI:10.7536/PC151208

Li Donghan, Qi Shicheng, Zhang Xiaoa, Liao Mingyi. Preparation, Functionalization and Properties of Low Molecular Fluoropolymers[J]. Progress in Chemistry, 2016, 28(5): 673-685 DOI:10.7536/PC151208

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参考文献

原文顺序 | 出版日期 | 本文引用

[1] Maclachlan J D. Polym-Plast. Tech. Eng. 1978, 11: 41.
[2] Ameduri B, Boutevin B. Well-Architectured Fluoropolymers: Synthesis, Properties and Applications, Amsterdam: Elsevier, 2004. 7.
[3] Calabrese L, Alenza A. Composites Science and Technology, 2003, 63: 851.
[4] Hardman H V, Hardman K V. USP 2349549, 1941.
[5] Seligman K L, Uraneck D. USP 2877212, 1959.
[6] 梁滔(Liang T), 魏绪玲(Wei X L), 龚光碧(Gong G B). 合成橡胶工业(China Synthetic Rubber Industry), 2011, 5: 398.
[7] 梁滔(Liang T), 魏绪玲(Wei X L), 张惠怡(Zhang H Y), 刘栓祥(Liu S X). 高分子通报(Polymer Bulletin), 2012, 4: 11.
[8] 罗延龄(Luo Y L). 弹性体(Elastomerics), 1998, 2: 50.
[9] Gallagher G A. USP 3069401, 1962.
[10] Robert C. Klingender. Handbook of Specialty Elastomers. NY: CRC Press, 2008. 133.
[11] Ross E W, Gary J R, Hoover S. Modern Fluoroelastomers, 1997, 422.
[12] Albert L M. Fluoroelastomers Handbook. NY: William Andrew Publishing, 2006. 37.
[13] Ameduri B. Chemical Reviews, 2009, 109: 6632.
[14] 杨晓勇(Yang X Y). 高分子通报(Polymer Bulletin), 2014, 5: 10.
[15] Kuangsen S, Richard L. Journal of the American Chemical Society, 1995, 117: 4276.
[16] 蔡树铭(Cai S M). 化工新型材料(New Chemical Materials), 1999, 2: 31.
[17] Masatoshi A, Huang H S. Organo-Flnorine Industry, 2001, 4: 30.
[18] Ni Z Y, Wang S Q. Organo-Flnorine Industry, 2006, 2: 47.
[19] Ameduri B. Macromolecules. 2010, 43: 10163.
[20] Lee J, Yandek G R. Polymer, 2005, 46: 12511.
[21] Stephens W D, McIntosh C R, Taylor C O. Journal of Polymer Science Part A-1, 1968, 6: 1037.
[22] Kuczko W, Joseph A. Rubber World, 1995, 212: 19.
[23] Carenza M, Lora S, Pezzin G. Radiation Physics and Chemistry, 1990, 35: 172.
[24] Kazuo K. USP 5663251, 1997.
[25] Reinhard A. USP 4338237, 1982.
[26] Tang P L. USP 6512063, 2003.
[27] Kaino M, Kanenori S, Wada M. CN 103732681A, 2012.
[28] Ameduri B, Boutevin B. Journal of Fluorine Chemistry, 2000, 104: 53.
[29] Howell J L, Hofmann M A, Waterfeld A, Sipyagin A M, Friesen C M, Thrasher J S. Journal of Fluorine Chemistry, 1998, 89: 131.
[30] Velichkova R S, Christova D C.Progress in Polymer Science, 1995, 20: 819.
[31] Chen T, Zhu J, Li B, Guo S, Yuan Z, Sun P, Ding D, Shi A. Macromolecules, 2005, 38: 4030.
[32] Ameduri B, Boutevin G, Kostov. Prog. Polym. Sci., 2001, 26: 105.
[33] Nakagawa S, Ihara K, Sogabe T.USP 4513129, 1985.
[34] Conti R, John N, Richard L, Brian D, Jeffrey F, Debra K.USP 4877839, 1989.
[35] 山边正显(Yamanabe J), 陈芝秀(Chen Z X). 橡胶参考资料(China Rubber Resources), 1996, 12: 26.
[36] Zheng H Z. Organo-Flnorine Industry, 2006, 1: 58.
[37] Gareth H, Patrick E C, Ken J, Theodore D. Fluoropolymers Part 1: Synthesis. NY: Kluwer Academic Publisher, 2002.191.
[38] Wang D X, Du Y S. Organo-Flnorine Industry, 2001, 2: 23.
[39] Graham D P. Journal of Organic Chemistry, 1966, 31: 955.
[40] Dmowski W, Flowers W T, Haszeldine R N. Journal of Fluorine Chemistry, 1977, 9: 94.
[41] Dresdner R D, Tlumac F N, Young J A. Journal of Organic Chemistry, 1965, 30: 3524.
[42] Ohsaka Y, Tohzuka T. USP 4296265, 1981.
[43] Anello L G, Sweeney R F. USP 4377717, 1983.
[44] Ozawa M, Komatsu T, Matsuoka K. USP 4042638,1981.
[45] Prokop R A. USP 5254774, 1993.
[46] Millauer H, Schwertfeger W, Siegemund G. Angewandte Chemie International Edition, 1985, 24: 161.
[47] Arbogast F L, USP 3412148, 1968.
[48] Siegemund G, Finke M. CN 90100159.7, 1990.
[49] Kruse A, Siegemund G, Schwertfeger W. CN 88107738, 1988.
[50] 孙元宝(Sun Y B), 魏贤勇(Wei X Y), 邱贞慧(Qiu Z H), 费逸伟(Fei Y W).精细石油化工进展(Advances in Fine Petrochemicals), 2003, 3: 6.
[51] Hanford W E, Wilmington, Joyce R M. USP 2440800, 1942.
[52] 朱璟(Zhu J). 天津大学博士学位论文(Doctoral Dissertation of Tianjin University), 2013.
[53] Boutevin B, David G, Boyer C. Advances in Polymer Science, 2007, 206: 131.
[54] Haszeldine R N. Nature, 1951, 167: 139.
[55] Abdellatif M, Ameduri B, Boutevin B, Chambers R D, Caporiccio G, Wright A P. Journal of Fluorine Chemistry, 1995,74: 59.
[56] Boutevin B. Journal of Polymer Science Part A: Polymer Chemistry, 2000, 38: 3235.
[57] Lahiouhel D, Ameduri B, Boutevin B. Journal of Fluorine Chemistry, 2001, 107: 81.
[58] Ameduri B. Chemical Reviews, 2009, 109: 6632.
[59] Haszeldine R N. Journal of the Chemical Society, 1949: 2856.
[60] Haszeldine R N. Journal of the Chemical Society, 1950: 3037.
[61] Haszeldine R N. Journal of the Chemical Society, 1953: 3761.
[62] Murray H, Glenside, Milton B.USP 3156732, 1964.
[63] Murray H, Milton B, Francis E L. Journal of the American Chemical Society, 1957, 79: 2549.
[64] Tatemoto H. USP 4158678, 1979.
[65] Boyer C, Valade D, Sauguet L, Ameduri B, Boutevin B. Macromolecules, 2005, 38: 10353.
[66] David G, Boyer C, Tonnar J, Ameduri B, Lacroix P, Boutevin B. Chemical Reviews, 2006, 106: 3936.
[67] Sawada H, Tashima T, NishiyamY, Kikuchi M, Goto Y, Kostov G, Ameduri B. Macromolecules, 2011, 44: 1114.
[68] Ameduri B, Boutevin B. Topics in Current Chemistry, 1997, 192: 165.
[69] Gondi S R, Vogt A P, Sumerlin B S. Macromolecules, 2007, 40: 474.
[70] Ameduri B, Ladaviere C, Delolme F, Boutevin B. Macromolecules, 2004, 37: 7602.
[71] Tatemoto M, Morita S. EP 27721, 1981.
[72] Tatemoto M, Morita S. USP 4361678, 1982.
[73] Hung M H. USP 5231154, 1993.
[74] Rice D E. USP 3457245, 1969.
[75] Rice D E. USP 3461155, 1969.
[76] Rice D E, Sandberg C L. USP 3438953, 1969.
[77] Boutevin B, Robin J J. Advances in Polymer Science, 1992, 102: 105.
[78] Ameduri B, Boutevin B. Advances in Polymer Science, 1992, 102: 133.
[79] Sokolov S V, Skoblikova V I, Purtseladze V I. USP 5739233, 1998.
[80] Liang L K, Lu S, Wei Y Y, Wang Q. Macromolecules, 2007, 40: 4121.
[81] Zhang Z C, Wang Z, Chung T C. Macromolecules, 2007, 40: 5235.
[82] Xu A H, Yuan W Z, Zhang H, Wang L, Li H, Zhang Y M. Polymer International, 2012, 61: 901.
[83] 徐安厚 (Xu A H).上海交通大博士学位论文(Doctoral Dissertation of Shanghai Jiao Tong University), 2011.
[84] Anilkumar R, Burton D J. Tetrahedron Letters, 2003, 44: 6661.
[85] Kirsch P. Modern Fluoroorganic Chemistry Synthesis, Reactivity, Applications. Darmstadt: WILEY-VCH Verlag GmbH & Co. KGaA, 2004.13.
[86] Schmiegel W W. Angewandte Makromolekulare Chemie, 1979, 77: 39.
[87] Mitra S, Siahkali A G, Kingshott P. Polymer Degradation and Stability, 2004, 83: 195.
[88] Cluff E F, Hundred B. USP 3147314, 1964.
[89] Moggi G, Bonardelli P, Chiodini G, Conti S. USP 4742126, 1988.
[90] Caporiccio G, Gornowicz G. USP 5395886, 1995.
[91] Coggio W D, Pham T D. USP 5733981, 1998.
[92] Coggio W D, Dietz T M, Fronek D R, Fukushi T, Nelson C J, Parker D S, Pham T D, Yamanaka K K. USP 6080487, 2000.
[93] Chiang L C, Lin J T, Tatsu H, Kogan L M, Skornyakov A S, Zapevalova T Y, Blagodatova O V, Sokolov S V. USP 5986038, 1999.
[94] Zhuravlev M V, Blagodatova O V, Kokotin I V, Barinov O V, Lebedev N V, Gubanov V A. RUP 2452746, 2012.
[95] Mizuide F, Tatsu H, Sokolov S V. USP 6329471, 2001.
[96] 刘煜(Liu Y), 李吉明(Li J M), 李娟(Li J),齐士成(Qi S C). 合成橡胶工业(Synthetic Rubber Industry), 2011, 34: 232.
[97] 李娟(Li J),吕亚非(Lu Y F), 齐士成(Qi S C). 合成橡胶工业(China Synthetic Rubber Industry), 2014, 3: 188.
[98] Li J, Lu Y F, Liu Y, Li Y, Zhang X A, Qi S C. Polymer-Plastics Technology and Engineering, 2014, 53: 46.
[99] Ameduri B, Boutevin B, Nouiri M, Talbi M.Journal of Fluorine Chemistry, 1995, 74, 2: 191.
[100] Kostov G, Ameduri B, Sergeeva T, Dolbier W R, Winter R, Gard G L. Macromolecules, 2005, 38: 8316.
[101] Taguet A, Sauguet L, Ameduri B, Boutevin B. Journal of Fluorine Chemistry, 2007, 128: 619.
[102] Maurizio P, Emma B, Giuseppe E, Stefano R. Journal of Fluorine Chemistry, 1999, 95: 71.
[103] Guiot J, Ameduri B, Boutevin B, Lannuzel T. Journal of Polymer Science Part A: Polymer Chemistry, 2006, 44: 3896.
[104] Robinson M I, Kochi J K. Macromolecules, 1983, 16: 526.
[105] Zaggia A, Ameduri B. Current Opinion in Colloid & Interface Science, 2012, 17: 188.
[106] Tasdelen M A, Kahveci M U, Yagci Y. Progress in Polymer Science, 2011, 36: 455.
[107] Hirao A, Hayashi M. Acta Polymerica, 1999, 50: 219.
[108] Jerome R, Henrioulle G M, Boutevin B, Robin J J. Progress in Polymer Science, 1991, 16: 837.
[109] Yukishige K, Eiichiro Y, Sanae M, Norio Y. Journal of Fluorine Chemistry, 1998, 91: 147.
[110] Saint L R, Manseri A, Ameduri B, Lebret B, Vignane P. Macromolecules, 2002, 35: 1524.
[111] Chalathorn C, Xu K, Huang H, Wan Q. Journal of Polymer Science Part A: Polymer Chemistry, 2010, 48: 4800.
[112] Bhaskar K J, Mariappan P. Journal of Organic Chemistry, 1991, 56: 5964.
[113] Tale R H, Patil K M, Dapurkar S E. Tetrahedron Letter, 2003, 44: 3427.
[114] Li D H,Liao M Y, Qi S C. Basic Research of Elastomers. Guangzhou: Polymer Bulletin, 2015. 90.
[115] 李娟(Li J), 吕亚非(Lu Y F), 游维涛(You W T), 郭琳琳(Guo L L), 刘辰(Liu C), 张孝阿(Zhang X A), 齐士成(Qi S C). 高分子学报(Acta Polymerica Sinica), 2013, 11: 1430.
[116] Qi S C, Li J, Lu Y F, Zhang X A, Wang J D, Li Y P, Li Y, Jiang S L, Yuan R P. CN 201310081168.5, 2013.
[117] Qi S C, Li J, Lu Y F, Zhang X A, Wang J D, Li Y P, Li Y, Jiang S L, Yuan R P. CN 103183763A, 2013.
[118] Balaguk J, Ameduri B, Boutevin B, Caporiccio G. Journal of Fluorine Chemistry, 1995,73: 237.
[119] Balaguk J, Ameduri B, Boutevin B, Caporiccio G. Journal of Fluorine Chemistry, 1995,74: 49.
[120] Hung M H, Ameduri B, Boyer C A. EP 2203489, 2010.
[121] Souzy R, Boutevin B, Ameduri B. Macromolecules, 2012, 4: 3145.
[122] Hung M H, Ameduri B, Boutevin B, Soules A. USP 8247614, 2012.
[123] Brosse J C, Derouet D, Epaillard F, Soutif J C. Polymer Science, 1986, 81: 169.
[124] 任文坛(Ren W T), 张勇(Zhang Y), 彭宗林(Peng Z L), 张隐西(Zhang Y X). 橡胶科技市场(Rubber Science and Technology Market), 2006, 6: 16.
[125] Patil Y, Alaaeddine A, Ono T, Ameduri B. Macromolecules, 2013, 46: 3092.
[126] Taguet A, Ameduri B, Dufresne A. European Polymer Journal, 2006, 42: 2549.
[127] 梁滔(Liang T), 王洪山(Wang H S), 高阳光(Gao Y G), 龚光碧(Gong G B), 魏绪玲(Wei X L). 合成橡胶工业(China Synthetic Rubber Industry), 2010, 6: 482.
[128] Timperley C M, Arbon R E, Bird M. Journal of Fluorine Chemistry, 2003, 121: 23.
[129] 张玉龙 (Zhang Y L), 孙敏 (Sun M). 橡胶品种与性能手册(Handbook of Rubber Variety and Performance).北京: 化学工业出版社(Beijing: Chemical Industry Press), 2006. 220.
[130] Abdul K M, Bhowmick A K. Polymer Degradation and Stability. 2003, 79: 283.
[131] 于清 (Yu Q). 橡胶原材料手册,第二版(Handbook of Rubber Raw Materials, 2nd ed). 北京: 化学工业出版社(Beijing: Chemical Industry Press), 2007. 207.
[132] Vijayakumar G, Karthick S N, Paramasivam R, Ilamaran C. Polymer-Plastics Technology and Engineer, 2012, 51: 1427.
[133] Abdelhamida M I, Aboelwafaa A M, Elhadidya H, Habiba A. International Journal of Polymeric Materials and Polymeric Biomaterial, 2012, 61: 505.