阳离子/ATRP合成异丁烯/丙烯酸叔丁酯共聚物研究
|
摘要
聚异丁烯具有一些优良、独特的性能如耐氧化、耐高温、耐化学腐蚀性和独特的橡胶性能等，因而具有重要的工业应用价值。但是异丁烯结构的特殊性，缺少功能性基团，使功能性异丁烯共聚物的合成受到了限制。解决这一问题的一个方法是将阳离子聚合和其它的活性／可控聚合方法如阴离子聚合、自由基聚合等相结合。自由基聚合可选用的单体广泛，近年来活性／可控自由基聚合又得到了很大发展，因此将活性阳离子聚合与活性／可控自由基聚合相结合，可极大拓宽聚异丁烯大分子的设计范围，获得预定结构和性能的嵌段、接枝共聚物。
本文的研究思路是把阳离子聚合和原子转移自由基聚合相结合，合成新型的异丁烯共聚物。
1．利用苯甲基氯(Ph-CH_2Cl)作为引发剂，CuBr／PMDETA组成催化体系进行丙烯酸叔丁酯和苯乙烯的原子转移自由基聚合，获得聚丙烯酸叔丁酯-b-聚苯乙烯嵌段共聚物，但用所获得的聚丙烯酸叔丁酯-b-聚苯乙烯嵌段共聚物大分子引发剂很难引发异丁烯的阳离子聚合。
2．以酰基化试剂α-溴代丙酰溴对异丁烯和对甲基苯乙烯的阳离子二元共聚物中的p-甲基苯乙烯单元进行Friedel-Crafts酰基化取代反应，获得大分子引发剂。以所得大分子引发剂引发丙烯酸叔丁酯的原子转移自由基聚合制得了梳状异丁烯-p-甲基苯乙烯接枝丙烯酸叔丁酯共聚物。所得产物用FTIR、~1H NMR、~(13)C NMR和GPC等进行了表征，结果表明，
Polyisobutylene has a number of interesting propertises such as high thermal, oxidative,chemical stability, and is a very important industry material. However, its usefulness in various applications is limited by the absence of functionality. One possible way to solve the problem is to combine the cationic polymerization with other "living'/controlled polymerizations such as living anionic polymerization and living radical polymerization, which can broaden the design of macro polyisobutylene, affording graft copolymers and block copolymes.
Here we try to combine the catonic polymerization and atom transfer radical polymerization(ATRP) to get new functional polyisobutylene.The procedure of this paper is as follows:
1. Polytert-butyl acrylate-block-polystyrene-Cl was synthesized via atom transfer radical polymerizaiton(ATRP) technique which was initiated by the system of ph-CH_2Cl/Cu/ N,N,N',N'N"- pentamethyl diethylenetriamine(PMDETA), however it failed to initiate the monomer isobutylene as a macroinitiator.
本文的研究思路是把阳离子聚合和原子转移自由基聚合相结合，合成新型的异丁烯共聚物。
1．利用苯甲基氯(Ph-CH_2Cl)作为引发剂，CuBr／PMDETA组成催化体系进行丙烯酸叔丁酯和苯乙烯的原子转移自由基聚合，获得聚丙烯酸叔丁酯-b-聚苯乙烯嵌段共聚物，但用所获得的聚丙烯酸叔丁酯-b-聚苯乙烯嵌段共聚物大分子引发剂很难引发异丁烯的阳离子聚合。
2．以酰基化试剂α-溴代丙酰溴对异丁烯和对甲基苯乙烯的阳离子二元共聚物中的p-甲基苯乙烯单元进行Friedel-Crafts酰基化取代反应，获得大分子引发剂。以所得大分子引发剂引发丙烯酸叔丁酯的原子转移自由基聚合制得了梳状异丁烯-p-甲基苯乙烯接枝丙烯酸叔丁酯共聚物。所得产物用FTIR、~1H NMR、~(13)C NMR和GPC等进行了表征，结果表明，
Polyisobutylene has a number of interesting propertises such as high thermal, oxidative,chemical stability, and is a very important industry material. However, its usefulness in various applications is limited by the absence of functionality. One possible way to solve the problem is to combine the cationic polymerization with other "living'/controlled polymerizations such as living anionic polymerization and living radical polymerization, which can broaden the design of macro polyisobutylene, affording graft copolymers and block copolymes.
Here we try to combine the catonic polymerization and atom transfer radical polymerization(ATRP) to get new functional polyisobutylene.The procedure of this paper is as follows:
1. Polytert-butyl acrylate-block-polystyrene-Cl was synthesized via atom transfer radical polymerizaiton(ATRP) technique which was initiated by the system of ph-CH_2Cl/Cu/ N,N,N',N'N"- pentamethyl diethylenetriamine(PMDETA), however it failed to initiate the monomer isobutylene as a macroinitiator.
引文
[1] 张洪敏，候元雪．活性聚合[M] 北京：中国石化出版社，1998．15-18
[2] Gauthier M, Moiler M. Uniform highly branched polymers by anionic grafting: arborescent graft polymers [J]. Macromolecular., 1991,24:4548-4553
[3] Barrie J A, Rezanian Ⅰ. The anionic synthesis and characterization of poly(styrene-g-ethylene oxide) copolymers[J]. Polymer, 1987, 28(7): 1217-1220
[4] Selb J, Gaillot Y. Graft copolymers:l.Synthesis and characterization of poly(styrene-g-2-vinylpyridine)[J]. Polymer, 1979, 20(10): 1259-1267
[5] Pitikailis M, Sloula S, Pospas S. Linking reactions of living polymers with bromomethylbenzene derivatives: Synthesis and characterization of star homopolymers and graft copolymers with polyelectrolyte branches[J]. J.Polym.Sci.Part A: Polym Chem., 1999,37(23): 4337-4350
[6] Pitsikalis M, Woodward J, Pitsikalis M. Micellization of model graft copolymers in dilute solution[J]. Macromolecular, 1997,30(18): 5384-5389
[7] Candau F, Arfkar T F. Synthesis and characterization of polystyrene-poly(ethylene oxide) graft copolymers[J]. Polymer, 1977,18(12): 1253-1257
[8] Parmell J, Polystyrenes of known structure: Part 2. Comb-shaped molecules[J]. Polymer, 1971 12(9): 558-578
[9] Takaki M, Asami R, Ichikawa M. Coupling reaction between living polystyrene and poly(chloromethylstyrene)[J]. Macromolecular, 1977, 10(4): 850-855
[10] Price C, Woods D. Synthesis and solution behaviour of polystyrene-g-polyisoprene copolymers[J]. Polymer, 1973, 14(3): 82-86
[11] Selb J, Gallot Y. Graft copolymers: 1. Synthesis and characterization of poly(styrene-g-2-vinylpyridine)[J]. Polymer, 1979,20(10): 1259-1267
[12] Selb J, Gallot Y. Graft copolymers: 3. Synthesis and characterization of poly (styrene-g-4 vinylpyridine)[J]. Polymer, 1979,20(10): 1273-1280
[13] Deffieux A, Schappaccher M. Synthesis and characterization of star and comb polystyrenes using Isometric poly(chloroethyl vinyl ether) oligomers as reactive backbone[J]. Macromolecular, 1999, 32(6): 1797-1802
[14] Zhang H M, Ruchensten E. Graft, block-graft and star-shaped copolymers by an in situ coupling reaction[J]. Macromolecular, 1998, 31 (15): 4753-4759
[15] Takaki M, Asami R, Mizuno M. Anionic grafting reaction on living polystyrene with poly(p-vinylstyrene oxide) and its styrene copolymer[J]. Macromolecular.1977,10(4): 845-850
[16] Schappacher M, Defieux A. New comblike copolymers of controlled structure and dimensions obtained by grafting by polystyryllithium onto poly(chloroethyl vinyl ether) chains[J]. Macromol. Chem.Phys., 1997, 198(12): 3953-3961
[17] Schappacher M, Billaoud C, Poulo C. Synthesis, dimensions and solution properties of linear and macrocyclic poly(chloroethyl vinyl ether)-g-polystyrene comblike polymers[J].Macromol. Chem.Phys., 1999 200(10): 2377-2386
[18] Sang W R, Akira H. Anionic synthesis of well-defined poly(m-halomethylstyrene)s and??branched polymers via graft-onto methodology[J]. Macromolecular 2000, 33(13): 4765-4771
[19] Ruchenstein E, Zhang H M. Well-defined graft copolymers based on the selective living anionic polymerization of the bifunctional monomer 4-(Vinylphenyl)-1-butene[J]. Macromolecular, 1999, 32(19): 6082-6087
[20] Ruckenstein E, Zhang H M. A successive route to amphiphilic graft copolymers with a hydrophilic poly(3-hydroxypropyl methacrylate) backbone and hydrophobic polystyrene side chains[J]. J.Polym.Sci.Part A: Polym Chem., 2000, 38(8): 1195-1202
[21] Cirtanen J, Baron C, Tenbu H. Grafting of poly(N-isopropylacrylamide) with poly(ethylene oxide) under various reaction conditions[J]. Macromolecular, 2000, 33(2): 336-341
[22] Ma Y H, Cao T, Webber S E. Polymer micelles from poly(acrylic acid)-grafl-polystyrene[J]. Macromolecular, 1998, 31(6): 1773-1778
[23] Hans G, Matyjaszewiski K. Graft eopolymers by atom transfer polymerization[J]. Macro.Symp., 2002,177(1): 1-15
[24] 袁金颖，楼旭东，潘才元．原子转移自由基聚合反应及其进展[J]．化学通报，2000，3：10-16
[25] Matyjaszewski K, Beers K L, Kern A, etl.. Hydrogels by atom transfer radical polymerization. I. Poly(N-vinylpyrrolidinone-g-styrene) via the macromonomer method [J]. J. Polym. Sci. Part A:Polym.Chem., 1998,36(5): 823-830
[26] Faquan Z, Shen Y, Zhu S, etl. Synthesis and characterization of comb-branched polyeledtrolytes. 1. preparation of cationic macromonomer of 2-(dimethylamino)ethyl methacrylate by atom transfer radical polymerization[J]. Macromolecules, 2000,33: 1628-1635
[27] Shinoda, H, Miller P J, Matyjaszewski K. Improving the structural control of graft copolymers by combining ATRP with the macromonomer method[J]. Mcromolecules, 2001,34(10): 3186-3194
[28] Roos SG, Muller A, Matyjaszewski. K. Copolymerization of n-butyl acrylate with methyl methacrylate and PMMA macromonomers: comparison of reactivity ratios in conventional and atom transfer radical copolymerization[J]. Macromolecules, 1999, 32(25): 8331-8335
[29] Grubbs R B, Hawker C, Dao J, etl.. A tandem, approach to graft and dendritic graft copolymers based on "living" free radical polymerizations[J]. J.Angew. Chem. And Ed. Engl., 1997,36(3): 270-272
[30] Matyjaszewski K, Beers K L, Kern A, etl.. Hydrogels by atom transfer radical polymerization. I. Poly(N-vinylpyrrolidinone-g-styrene) via the macromonomer method [J] J. Polym. Sci. A, Polym. Chem. 1998,36(5): 823-830
[31] Pan Q, Liu S, Xie J, etl. Synthesis and characterization of block-graft copolymers composed of poly(styrene-b-ethylene-co-propylene) and poly(ethyl methylacrylate) by atom transfer radical polymerization[J]. J. Polym. SCI. Part A: Polym. Chem.,1997,37(15): 2699-2702
[32] Crivello J V, Conlon D A. Polydimethylsiloxane-vinyl block polymers. I. The synthesis of polydimethylsiloxane macroinitiators containing thermolyzable bis(silyl pinacolate) groups in their backbones [J] J. Polym. Sci .Part A: Polym. Chem.,. 1986,24(6): 1197-1125
[33] Yoshiki N, Pater J. Miller. Development of novel attachable initiators for atom transfer??radical polymerization, synthesis of block and graft copolymers from poly(dimethylsiloxane) macroinitiators[J]. Polymer, 1998,39(21 ): 5163-5170
[34] Sugizaki T, Kashio M, Kimura A. etl. Graft polymerization of polysilsesquioxane containing chloromethylphenyl groups by atom transfer radical polymerization[J]. Polym.Sci.PartA: Polym.Chem.;2004(l 7),42,4212-4221
[35] Tamds,F.,Bela Ivan. Marta,B. Polyisobutylene-grafi-polystyrene by quasiliving atom transfer radical polymerization of styrene from poly (isobutylene-co-pmethylstyrene-co-p-bromomethylstyrene) [J] Macromol. Rapid. Commun. 1998.19,479-483
[36] Masar B. Janata, M, Vlcek,P, Toman, L. Kurkova, D. Atom transfer radical polymerization grafting of highly functionalized polystyrene and poly(4-Methylstyrene) macroinitiators with tert-butyl acrylate [J] J.Polym.Appl.Sci. 2002, 86, 2930 - 2936
[37] Coskum M. Mehmet M.T. Grafting of poly(styrene-co-p-chloromethyl styrene) with ethyl methacrylate via atom transfer radical polymerization catalyzed by CuCl/1,2-dipiperidinoethane [J] J . Polym. Sci. Part A: Polym. Chem. 2003, 41 (5) : 668-673
[38] Biack, N, Mesut,O, Graft copolymerization of butyl acrylate and 2-ethyl hexyl acrylate from labile chlorines of poly(vinyl chloride) by atom transfer radical polymerization [J] J.Polym.Sci.: PartA : Polym.Chem. 2003,41 (21) :3457-3462
[39] Paik H-J,Gaynor S.G.;Matyjaszewski K. Synthesis and characterization of graft copolymers of poly(vinyl chloride) with styrene and (meth)acrylates by atom transfer radical polymerization [J] Macromol. Rapid Commun. 1998,19(1 ):47-52
[40] 程斌，马育红．聚异丁烯、丁基橡胶[M]．碳四碳五烯烃工学．北京：化学工业出版社，1998．379
[41] Kenndy J P, Ivan B. Designed polymers by carbocationic macromolecular engineering: Theory and practice[M]. New York: Hanser, 1992
[42] Matyjaszewski K. Cationic polymerization: Mechanisms, synthesis and applications[M]. New York: Macrel Dekker Inc. 1996
[43] Szwar M. Ionic polymerization fundmentals[M]. New York: Hanser,1996
[44] Koichi Hatada, Tasuki Kitayama. Otto Vogl. Macromolecular design of polymeric materials [A]. Marcel Dekker Inc, New York, 1997
[45] Cheradame H, Habimana J C, Rousset E, et al. Syhthesis of polymers containing pesudohalide groups by cationic polymerization(9): Azido end-capped poly(2-methylpropene) by polymerization initiated by the system Lewis acid-2-azido-2-phenylpropanel [J] Macomol. 1993,27(3): 631-637
[46] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126
[47] Storey R F, Shoemake K A. Poly(styren-b-isobutene) multiarm star-block copolymers [J]. J Poly Sci Chem Ed, 1999,37(11):1629-1635
[48] Omura N, Lubnin A V, Kennnedy J P. Multiarm star polyisobutylenes[A]. In Faust R, Shaffer T D. Cationic Polymeriztion Fundamentals & Applications. ACS Series 665, Washington D C, 1998.178
[49] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126[50] Kenndy J P, Ivan B. Designed polymers by carbocationic macromolecular engineering: Theory and practice[M]. New York: Hanser, 1992
[51] Koichi Hatada, Tasuki Kitayama. Otto Vogl. Macromolecular design of polymeric materials [A]. Marcel Dekker Inc, New York, 1997
[52] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126
[53] Puskas J E, Wilds C J. Multiarm-star polyisobutylene by living carbocationic polymerization [J] J Poly Sci, Part A: Polym Chem, 1998, 36(1): 85
[54] Freche J M, Henmi M, Gitsow I, et al. Self-condensing viny polymerization: An approach to dendritic materials [J]. Science, 1995,269(5 227): 1 080
[55] Zeng Fanwen, Zimmerman S C. Dendriems in supramolecular chemistry from molecular recognition to self-assenbly [J]. Chem Rev. 1997,97(5): 1 681
[56] KitayamaT, Nishiura t, Hatada K. PMMA-block-polyisobutylene-block-PMMA prepared with α,ω-dilithiated polyisobutylene and its characterization [J] Poly Bull, 1991,26,513-520
[57] Kennedy J P, Price J L, Koshimura K. Novel thermoplastic elastomer triblocks of a soft polyisobutylene midblock connected to two hard PMMA stereocomplex outer blocks [J] Macromol. 1991,24(25):6567-6571
[58] Gorda K R, Peiffer D G, Chung T C. Synthesis and Characterization of Polyisobutylene-Polycaprolactone Block Copolymers [J] Poly Commun,1990,31(7):286-289
[59] Feldthusen J , Ivan B, Muller H A. Synthesis of Linear and Star-Shaped Block Copolymers of Isobutylene and Methacrylates by Combination of Living Cationic and Anionic Polymerizations [J] Macromol. 1998,31(3):578-585
[60] Faust R, Kwon Y. Synthesis and Characterization of Poly(isobutylene-b-pivalolactone) Diblock and Poly(pivalolactone-b-isoburylene-b-pivalolactone) Triblock Copolymers [J] Macromol. 2002,35(9):3348-3357
[61] Coca S,Matyjaszewski J P. Block Copolymers by Transformation of 'Living' Carbocationic into "Living" Radical Polymerization. II.ABA-Type Block Copolymers Comprising Rubbery Polyisobutene Middle Segment [J]J Polym Sci, Part A: Poly Chem, 1997,35:3595-3601
[62] Jankova K, Kops J, Xiaoyi C, Gao B, Batsberg W. Synthesis of poly(styrene-b-isobutylene-b-styrene) triblock copolymer by ATRP, [J] Polym Bull 1998,41:639-644
[63] Ivan B, Xiaoyi C, Kops J, Batsberg W. Synthesis of 1-chloro-l-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization, [J] Macromol. Rapid Commun. 1998,19:15-19
[64] Zheng Feng, Kennedy J P. Novel Block Ionomers. I. Synthesis and Characterization of Polyisobutylene-Based Block Anionomers [J] J Polym Sci, Part A: Polym Chem, 2002, 40: 3662-3678
[65] Nuyken O,Sanchez J R, Voit B,Synthesis of amphiphilic graft copolymers by ring-opening polymerization of 2-methyl-2-oxazoline initiated by poly [isobutene-co-(p,m-chloromethylstyrene)] macroinitiators, [J] Macromol. Rapid Commun. 1997,18:125-131.
[66] Truelsen J, Kops J, Batsberg W, Synthesis by ATRP of triblock copoiymers with densely grafted styrenic end blocks from a polyisobutylene macroinitiator, [J] Macromol. Rapid Commun. 2000,21:98-102
[67] Hong S C, Pakula T, Matyjaszewski K, Preparation of Polyisobutene-graft-Poly(methyl methacrylate) and Polyisobutene-graft-Polystyrene with Different Compositions and Side Chain Architectures through Atom Transfer Radical Polymerization (ATRP), [J] Macromol. Chem. Phys. 2001,202:3392-3402
[1] Coca S, Matyjaszewski K. Block copolymers by transformation of"iiving" carbocationic into "living" radical polymerization [J]. Macromolecules, 1997, 30(9): 2808-2810
[2] Coca S, Matyjaszewski K. Block copolymers by transformation of "living"carbocationic into "living" radical polymerization. Ⅱ. ABA-Type block copolymers comprising rubbery polyisobutene middle segment [J]. J Polym Sci, Part A: Polym. Chem, 1997, 35(16):3595-3601
[3] Iva'n B, Chen X, Kops J, et al. Synthesis of l-chloro-l-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization [J]. Macromol Rapid Cornmun, 1998, 19(1): 15-19
[4] Iva'n B, Chen X, Kops J, et al. Block copolymers of styrene and p-acetoxystyrene with polyisobutylene by combination of living carbocationic and atom transfer radical polymerizations [J]. Macromol Rapid Commun, 1998, 19(11): 585-589
[5] Coca S, Matyjaszewski K, Block Copolymers by Transformation of "Living" Carbocationic into "Living" Radical Polymerization [J] Macromol. 1997, 30: 2808-2810
[6] 刘燕飞， 万小龙，应圣康，_活性_原子转移自由基聚合向活性正离子开环聚合转化制备苯乙烯_2_甲基_2_噁唑[J]合成橡胶工业，1998，21：305
[7] 刘燕飞，万小龙，应圣康，利用四氢呋喃的正离子开环聚合反应实现ATRP聚合物的卤端基转化[J] 合成橡胶工业，1998，21：306
[8] Zheng F, Kennedy P. Novel block ionomers. Ⅰ. synthesis and characterization of polyisobutylene-based block anionomers [J]. J Polym Sci, Part A: Polym Chem, 2002, 40(21): 3679-3691
[9] Zheng F, Kennedy P. Novel block ionomers Ⅱ. synthesis and characterization of polyisobutylene-based block cationomers [J]. J Polym Sci Part A: Polym Chem, 2002, 40(21): 3662-3678
[10] Iva'n B, Fonagy T, Szesztay M. Polyisobutylene-graft-polystyrene by quasiliving atom transfer radical polymerization of styrene from poly(isobutylene-co-pmethylstyrene-co-p-bromomethylstyrene) [J]. Macromol Rapid Commun. 1998, 19(9): 479-483
[11] Sung. C, H, Matyjaszewski K. Preparation of polyisobutene-grafl-Poly(methyl methacrylate) and polyisobutene-graft-polystyrene with different compositions and side chain architectures through atom transfer radical polymerization (ATRP) [J]. Macromol Chem Phys. 2001,202(17): 3392-3402
[12] Janata M, Bohumil T, Petr, P, et al. Atom Transfer Radical Polymerization Grafting of Highly Functionalized Polystyrene and Poly(4-Methylstyrene) Macroinitiators with tert-Butyl Acrylate [J] Journal of Applied Polymer Science, 2002, 86, 2930-2936
[13] Lubin A, Orszagh Ⅰ, Kennedy J. P. The microstructure of poly(isobutylene-co-p-methylstyrene) by NMR spectroscopy [J]. J Macromol Sci Pure Appl Chem, 1995, A32 (11): 1809-1830
[14] Abhimanyu O P, Donald N S, Bruce M N. Functional polymers-modern synthetic methods??and novel structures [C] ACS symp ser, 1998, 704, 184-198
[15] 徐寿昌有机化学[M]．北京：高等教育出版社，1993，131-132
[16] Janata M, Bohumil T, Petr, P, et ai. Multifunctional ATRP macroinitiators for the synthesis of graft copolymers, [J]. React funct polym, 2002, 50(1): 67-75
[17] John R, Charles R, Timothy D. Characterization of signals in the solution IH NMR spectrum of poly(isobutylene-co-p-methylstyrene) and their utility [J]. J Polym Sci, Part A: Polym Chem, 2000, 38(9): 1680-1686
[2] Gauthier M, Moiler M. Uniform highly branched polymers by anionic grafting: arborescent graft polymers [J]. Macromolecular., 1991,24:4548-4553
[3] Barrie J A, Rezanian Ⅰ. The anionic synthesis and characterization of poly(styrene-g-ethylene oxide) copolymers[J]. Polymer, 1987, 28(7): 1217-1220
[4] Selb J, Gaillot Y. Graft copolymers:l.Synthesis and characterization of poly(styrene-g-2-vinylpyridine)[J]. Polymer, 1979, 20(10): 1259-1267
[5] Pitikailis M, Sloula S, Pospas S. Linking reactions of living polymers with bromomethylbenzene derivatives: Synthesis and characterization of star homopolymers and graft copolymers with polyelectrolyte branches[J]. J.Polym.Sci.Part A: Polym Chem., 1999,37(23): 4337-4350
[6] Pitsikalis M, Woodward J, Pitsikalis M. Micellization of model graft copolymers in dilute solution[J]. Macromolecular, 1997,30(18): 5384-5389
[7] Candau F, Arfkar T F. Synthesis and characterization of polystyrene-poly(ethylene oxide) graft copolymers[J]. Polymer, 1977,18(12): 1253-1257
[8] Parmell J, Polystyrenes of known structure: Part 2. Comb-shaped molecules[J]. Polymer, 1971 12(9): 558-578
[9] Takaki M, Asami R, Ichikawa M. Coupling reaction between living polystyrene and poly(chloromethylstyrene)[J]. Macromolecular, 1977, 10(4): 850-855
[10] Price C, Woods D. Synthesis and solution behaviour of polystyrene-g-polyisoprene copolymers[J]. Polymer, 1973, 14(3): 82-86
[11] Selb J, Gallot Y. Graft copolymers: 1. Synthesis and characterization of poly(styrene-g-2-vinylpyridine)[J]. Polymer, 1979,20(10): 1259-1267
[12] Selb J, Gallot Y. Graft copolymers: 3. Synthesis and characterization of poly (styrene-g-4 vinylpyridine)[J]. Polymer, 1979,20(10): 1273-1280
[13] Deffieux A, Schappaccher M. Synthesis and characterization of star and comb polystyrenes using Isometric poly(chloroethyl vinyl ether) oligomers as reactive backbone[J]. Macromolecular, 1999, 32(6): 1797-1802
[14] Zhang H M, Ruchensten E. Graft, block-graft and star-shaped copolymers by an in situ coupling reaction[J]. Macromolecular, 1998, 31 (15): 4753-4759
[15] Takaki M, Asami R, Mizuno M. Anionic grafting reaction on living polystyrene with poly(p-vinylstyrene oxide) and its styrene copolymer[J]. Macromolecular.1977,10(4): 845-850
[16] Schappacher M, Defieux A. New comblike copolymers of controlled structure and dimensions obtained by grafting by polystyryllithium onto poly(chloroethyl vinyl ether) chains[J]. Macromol. Chem.Phys., 1997, 198(12): 3953-3961
[17] Schappacher M, Billaoud C, Poulo C. Synthesis, dimensions and solution properties of linear and macrocyclic poly(chloroethyl vinyl ether)-g-polystyrene comblike polymers[J].Macromol. Chem.Phys., 1999 200(10): 2377-2386
[18] Sang W R, Akira H. Anionic synthesis of well-defined poly(m-halomethylstyrene)s and??branched polymers via graft-onto methodology[J]. Macromolecular 2000, 33(13): 4765-4771
[19] Ruchenstein E, Zhang H M. Well-defined graft copolymers based on the selective living anionic polymerization of the bifunctional monomer 4-(Vinylphenyl)-1-butene[J]. Macromolecular, 1999, 32(19): 6082-6087
[20] Ruckenstein E, Zhang H M. A successive route to amphiphilic graft copolymers with a hydrophilic poly(3-hydroxypropyl methacrylate) backbone and hydrophobic polystyrene side chains[J]. J.Polym.Sci.Part A: Polym Chem., 2000, 38(8): 1195-1202
[21] Cirtanen J, Baron C, Tenbu H. Grafting of poly(N-isopropylacrylamide) with poly(ethylene oxide) under various reaction conditions[J]. Macromolecular, 2000, 33(2): 336-341
[22] Ma Y H, Cao T, Webber S E. Polymer micelles from poly(acrylic acid)-grafl-polystyrene[J]. Macromolecular, 1998, 31(6): 1773-1778
[23] Hans G, Matyjaszewiski K. Graft eopolymers by atom transfer polymerization[J]. Macro.Symp., 2002,177(1): 1-15
[24] 袁金颖，楼旭东，潘才元．原子转移自由基聚合反应及其进展[J]．化学通报，2000，3：10-16
[25] Matyjaszewski K, Beers K L, Kern A, etl.. Hydrogels by atom transfer radical polymerization. I. Poly(N-vinylpyrrolidinone-g-styrene) via the macromonomer method [J]. J. Polym. Sci. Part A:Polym.Chem., 1998,36(5): 823-830
[26] Faquan Z, Shen Y, Zhu S, etl. Synthesis and characterization of comb-branched polyeledtrolytes. 1. preparation of cationic macromonomer of 2-(dimethylamino)ethyl methacrylate by atom transfer radical polymerization[J]. Macromolecules, 2000,33: 1628-1635
[27] Shinoda, H, Miller P J, Matyjaszewski K. Improving the structural control of graft copolymers by combining ATRP with the macromonomer method[J]. Mcromolecules, 2001,34(10): 3186-3194
[28] Roos SG, Muller A, Matyjaszewski. K. Copolymerization of n-butyl acrylate with methyl methacrylate and PMMA macromonomers: comparison of reactivity ratios in conventional and atom transfer radical copolymerization[J]. Macromolecules, 1999, 32(25): 8331-8335
[29] Grubbs R B, Hawker C, Dao J, etl.. A tandem, approach to graft and dendritic graft copolymers based on "living" free radical polymerizations[J]. J.Angew. Chem. And Ed. Engl., 1997,36(3): 270-272
[30] Matyjaszewski K, Beers K L, Kern A, etl.. Hydrogels by atom transfer radical polymerization. I. Poly(N-vinylpyrrolidinone-g-styrene) via the macromonomer method [J] J. Polym. Sci. A, Polym. Chem. 1998,36(5): 823-830
[31] Pan Q, Liu S, Xie J, etl. Synthesis and characterization of block-graft copolymers composed of poly(styrene-b-ethylene-co-propylene) and poly(ethyl methylacrylate) by atom transfer radical polymerization[J]. J. Polym. SCI. Part A: Polym. Chem.,1997,37(15): 2699-2702
[32] Crivello J V, Conlon D A. Polydimethylsiloxane-vinyl block polymers. I. The synthesis of polydimethylsiloxane macroinitiators containing thermolyzable bis(silyl pinacolate) groups in their backbones [J] J. Polym. Sci .Part A: Polym. Chem.,. 1986,24(6): 1197-1125
[33] Yoshiki N, Pater J. Miller. Development of novel attachable initiators for atom transfer??radical polymerization, synthesis of block and graft copolymers from poly(dimethylsiloxane) macroinitiators[J]. Polymer, 1998,39(21 ): 5163-5170
[34] Sugizaki T, Kashio M, Kimura A. etl. Graft polymerization of polysilsesquioxane containing chloromethylphenyl groups by atom transfer radical polymerization[J]. Polym.Sci.PartA: Polym.Chem.;2004(l 7),42,4212-4221
[35] Tamds,F.,Bela Ivan. Marta,B. Polyisobutylene-grafi-polystyrene by quasiliving atom transfer radical polymerization of styrene from poly (isobutylene-co-pmethylstyrene-co-p-bromomethylstyrene) [J] Macromol. Rapid. Commun. 1998.19,479-483
[36] Masar B. Janata, M, Vlcek,P, Toman, L. Kurkova, D. Atom transfer radical polymerization grafting of highly functionalized polystyrene and poly(4-Methylstyrene) macroinitiators with tert-butyl acrylate [J] J.Polym.Appl.Sci. 2002, 86, 2930 - 2936
[37] Coskum M. Mehmet M.T. Grafting of poly(styrene-co-p-chloromethyl styrene) with ethyl methacrylate via atom transfer radical polymerization catalyzed by CuCl/1,2-dipiperidinoethane [J] J . Polym. Sci. Part A: Polym. Chem. 2003, 41 (5) : 668-673
[38] Biack, N, Mesut,O, Graft copolymerization of butyl acrylate and 2-ethyl hexyl acrylate from labile chlorines of poly(vinyl chloride) by atom transfer radical polymerization [J] J.Polym.Sci.: PartA : Polym.Chem. 2003,41 (21) :3457-3462
[39] Paik H-J,Gaynor S.G.;Matyjaszewski K. Synthesis and characterization of graft copolymers of poly(vinyl chloride) with styrene and (meth)acrylates by atom transfer radical polymerization [J] Macromol. Rapid Commun. 1998,19(1 ):47-52
[40] 程斌，马育红．聚异丁烯、丁基橡胶[M]．碳四碳五烯烃工学．北京：化学工业出版社，1998．379
[41] Kenndy J P, Ivan B. Designed polymers by carbocationic macromolecular engineering: Theory and practice[M]. New York: Hanser, 1992
[42] Matyjaszewski K. Cationic polymerization: Mechanisms, synthesis and applications[M]. New York: Macrel Dekker Inc. 1996
[43] Szwar M. Ionic polymerization fundmentals[M]. New York: Hanser,1996
[44] Koichi Hatada, Tasuki Kitayama. Otto Vogl. Macromolecular design of polymeric materials [A]. Marcel Dekker Inc, New York, 1997
[45] Cheradame H, Habimana J C, Rousset E, et al. Syhthesis of polymers containing pesudohalide groups by cationic polymerization(9): Azido end-capped poly(2-methylpropene) by polymerization initiated by the system Lewis acid-2-azido-2-phenylpropanel [J] Macomol. 1993,27(3): 631-637
[46] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126
[47] Storey R F, Shoemake K A. Poly(styren-b-isobutene) multiarm star-block copolymers [J]. J Poly Sci Chem Ed, 1999,37(11):1629-1635
[48] Omura N, Lubnin A V, Kennnedy J P. Multiarm star polyisobutylenes[A]. In Faust R, Shaffer T D. Cationic Polymeriztion Fundamentals & Applications. ACS Series 665, Washington D C, 1998.178
[49] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126[50] Kenndy J P, Ivan B. Designed polymers by carbocationic macromolecular engineering: Theory and practice[M]. New York: Hanser, 1992
[51] Koichi Hatada, Tasuki Kitayama. Otto Vogl. Macromolecular design of polymeric materials [A]. Marcel Dekker Inc, New York, 1997
[52] Puskas J E. Star-branched and hyperbranched polyisobutylenes [J]. Macromol Symp, 1998, 132:117-126
[53] Puskas J E, Wilds C J. Multiarm-star polyisobutylene by living carbocationic polymerization [J] J Poly Sci, Part A: Polym Chem, 1998, 36(1): 85
[54] Freche J M, Henmi M, Gitsow I, et al. Self-condensing viny polymerization: An approach to dendritic materials [J]. Science, 1995,269(5 227): 1 080
[55] Zeng Fanwen, Zimmerman S C. Dendriems in supramolecular chemistry from molecular recognition to self-assenbly [J]. Chem Rev. 1997,97(5): 1 681
[56] KitayamaT, Nishiura t, Hatada K. PMMA-block-polyisobutylene-block-PMMA prepared with α,ω-dilithiated polyisobutylene and its characterization [J] Poly Bull, 1991,26,513-520
[57] Kennedy J P, Price J L, Koshimura K. Novel thermoplastic elastomer triblocks of a soft polyisobutylene midblock connected to two hard PMMA stereocomplex outer blocks [J] Macromol. 1991,24(25):6567-6571
[58] Gorda K R, Peiffer D G, Chung T C. Synthesis and Characterization of Polyisobutylene-Polycaprolactone Block Copolymers [J] Poly Commun,1990,31(7):286-289
[59] Feldthusen J , Ivan B, Muller H A. Synthesis of Linear and Star-Shaped Block Copolymers of Isobutylene and Methacrylates by Combination of Living Cationic and Anionic Polymerizations [J] Macromol. 1998,31(3):578-585
[60] Faust R, Kwon Y. Synthesis and Characterization of Poly(isobutylene-b-pivalolactone) Diblock and Poly(pivalolactone-b-isoburylene-b-pivalolactone) Triblock Copolymers [J] Macromol. 2002,35(9):3348-3357
[61] Coca S,Matyjaszewski J P. Block Copolymers by Transformation of 'Living' Carbocationic into "Living" Radical Polymerization. II.ABA-Type Block Copolymers Comprising Rubbery Polyisobutene Middle Segment [J]J Polym Sci, Part A: Poly Chem, 1997,35:3595-3601
[62] Jankova K, Kops J, Xiaoyi C, Gao B, Batsberg W. Synthesis of poly(styrene-b-isobutylene-b-styrene) triblock copolymer by ATRP, [J] Polym Bull 1998,41:639-644
[63] Ivan B, Xiaoyi C, Kops J, Batsberg W. Synthesis of 1-chloro-l-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization, [J] Macromol. Rapid Commun. 1998,19:15-19
[64] Zheng Feng, Kennedy J P. Novel Block Ionomers. I. Synthesis and Characterization of Polyisobutylene-Based Block Anionomers [J] J Polym Sci, Part A: Polym Chem, 2002, 40: 3662-3678
[65] Nuyken O,Sanchez J R, Voit B,Synthesis of amphiphilic graft copolymers by ring-opening polymerization of 2-methyl-2-oxazoline initiated by poly [isobutene-co-(p,m-chloromethylstyrene)] macroinitiators, [J] Macromol. Rapid Commun. 1997,18:125-131.
[66] Truelsen J, Kops J, Batsberg W, Synthesis by ATRP of triblock copoiymers with densely grafted styrenic end blocks from a polyisobutylene macroinitiator, [J] Macromol. Rapid Commun. 2000,21:98-102
[67] Hong S C, Pakula T, Matyjaszewski K, Preparation of Polyisobutene-graft-Poly(methyl methacrylate) and Polyisobutene-graft-Polystyrene with Different Compositions and Side Chain Architectures through Atom Transfer Radical Polymerization (ATRP), [J] Macromol. Chem. Phys. 2001,202:3392-3402
[1] Coca S, Matyjaszewski K. Block copolymers by transformation of"iiving" carbocationic into "living" radical polymerization [J]. Macromolecules, 1997, 30(9): 2808-2810
[2] Coca S, Matyjaszewski K. Block copolymers by transformation of "living"carbocationic into "living" radical polymerization. Ⅱ. ABA-Type block copolymers comprising rubbery polyisobutene middle segment [J]. J Polym Sci, Part A: Polym. Chem, 1997, 35(16):3595-3601
[3] Iva'n B, Chen X, Kops J, et al. Synthesis of l-chloro-l-phenylethyl-telechelic polyisobutylene, a new potential macroinitiator by living cationic polymerization [J]. Macromol Rapid Cornmun, 1998, 19(1): 15-19
[4] Iva'n B, Chen X, Kops J, et al. Block copolymers of styrene and p-acetoxystyrene with polyisobutylene by combination of living carbocationic and atom transfer radical polymerizations [J]. Macromol Rapid Commun, 1998, 19(11): 585-589
[5] Coca S, Matyjaszewski K, Block Copolymers by Transformation of "Living" Carbocationic into "Living" Radical Polymerization [J] Macromol. 1997, 30: 2808-2810
[6] 刘燕飞， 万小龙，应圣康，_活性_原子转移自由基聚合向活性正离子开环聚合转化制备苯乙烯_2_甲基_2_噁唑[J]合成橡胶工业，1998，21：305
[7] 刘燕飞，万小龙，应圣康，利用四氢呋喃的正离子开环聚合反应实现ATRP聚合物的卤端基转化[J] 合成橡胶工业，1998，21：306
[8] Zheng F, Kennedy P. Novel block ionomers. Ⅰ. synthesis and characterization of polyisobutylene-based block anionomers [J]. J Polym Sci, Part A: Polym Chem, 2002, 40(21): 3679-3691
[9] Zheng F, Kennedy P. Novel block ionomers Ⅱ. synthesis and characterization of polyisobutylene-based block cationomers [J]. J Polym Sci Part A: Polym Chem, 2002, 40(21): 3662-3678
[10] Iva'n B, Fonagy T, Szesztay M. Polyisobutylene-graft-polystyrene by quasiliving atom transfer radical polymerization of styrene from poly(isobutylene-co-pmethylstyrene-co-p-bromomethylstyrene) [J]. Macromol Rapid Commun. 1998, 19(9): 479-483
[11] Sung. C, H, Matyjaszewski K. Preparation of polyisobutene-grafl-Poly(methyl methacrylate) and polyisobutene-graft-polystyrene with different compositions and side chain architectures through atom transfer radical polymerization (ATRP) [J]. Macromol Chem Phys. 2001,202(17): 3392-3402
[12] Janata M, Bohumil T, Petr, P, et al. Atom Transfer Radical Polymerization Grafting of Highly Functionalized Polystyrene and Poly(4-Methylstyrene) Macroinitiators with tert-Butyl Acrylate [J] Journal of Applied Polymer Science, 2002, 86, 2930-2936
[13] Lubin A, Orszagh Ⅰ, Kennedy J. P. The microstructure of poly(isobutylene-co-p-methylstyrene) by NMR spectroscopy [J]. J Macromol Sci Pure Appl Chem, 1995, A32 (11): 1809-1830
[14] Abhimanyu O P, Donald N S, Bruce M N. Functional polymers-modern synthetic methods??and novel structures [C] ACS symp ser, 1998, 704, 184-198
[15] 徐寿昌有机化学[M]．北京：高等教育出版社，1993，131-132
[16] Janata M, Bohumil T, Petr, P, et ai. Multifunctional ATRP macroinitiators for the synthesis of graft copolymers, [J]. React funct polym, 2002, 50(1): 67-75
[17] John R, Charles R, Timothy D. Characterization of signals in the solution IH NMR spectrum of poly(isobutylene-co-p-methylstyrene) and their utility [J]. J Polym Sci, Part A: Polym Chem, 2000, 38(9): 1680-1686
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |