通过活性自由基聚合方法合成具有反应性官能侧基的嵌段/星形聚合物的研究
摘要
本文通过原子转移自由基(ATRP)和氮氧自由基可控聚合(NMP)活性聚合方法有效地控制聚合物分子链结构，合成了一系列具有功能性侧基的活性嵌段共聚物和星形聚合物。
通过ATRP方法合成了聚甲基丙烯酸烯丙醇酯PAMA、聚甲基丙烯酸三甲氧基硅烷-γ-丙酯PMOPS、甲基丙烯酸烯丙酯和甲基丙烯酸丁酯无规共聚物P(AMA-r-BMA)、甲基丙烯酸烯丙酯和甲基丙烯酸三甲氧基硅烷-γ-丙酯无规共聚物P(AMA-r-MOPS)以及嵌段共聚物P(AMA-b-MOPS)。在聚合中，烯丙基和可以裂解的有机硅氧烷基团保留了下来，成功的将双键和有机硅氧烷引入到大分子侧基中。这个过程在一般的自由基聚合中是无法实现的。通过在聚合物中引入甲基丙烯酸三甲氧基硅烷-γ-丙酯单元，再经溶胶／凝胶化过程可制得纳米杂化材料。
本文在HTEMPO控制下合成了分子量窄分布(分布系数1.1-1.2)的苯乙烯和乙烯基吡咯烷酮嵌段共聚物P(St-b-NVP)和苯乙烯和丙烯酸-2-羟乙酯嵌段共聚物P(St-b-HEA)。由此嵌段共聚物可以在极性和非极性溶剂中自组装成核-壳型纳米胶束，并通过多异氰酸酯将核交联，合成多臂单分散星形分子。该星形聚合物的分子量多数在五十万左右，最高可达一百万，分子量分布系数为1.5左右。
用FT-IR、GPC和NMR等仪器对所合成的聚合物分子结构进行了表征；并用透射电镜(TEM)研究了星形聚合物微观形态结构。
Atom transfer radical polymerization (ATRP) and nitroxide-mediated polymerization (NMP) were employed to control the macromolecular chain structure efficiently. In this paper we synthesize a series of living block copolymers and star polymers with functional side groups.
Poly(allyl methacrylate), Poly( Y -Methacryloxypropyl trimethoxysilane), Poly(allyl methacrylate -r- n -butyl methacrylate) and Poly(allyl methacrylate )-b-Poly( Y -Methacryloxypropyl trimethoxysilane ) were synthesized via ATRP method. Allyl and organic-silicanoxane were survived in these processes and successfully introduced into macromolecular chain as side groups, which could not be achieved in traditional free radical polymerization. Silica-polymer nanohybrid can be prepared by Sol-Gel process as the presence of the Y -Methacryloxypropyl trimethoxysilane monomer unit.
Poly (styrene)-b-Poly (N-vinylpyrrolidone) and Poly (Styrene)-b-Poly (2-Hydroxyethyl acrylate) with significantly low polydispersities(l.1-1.2) were synthesized under the control of HTEMPO. Block copolymer can be self-assemblied into nanoscalled micella in polar and nonpolar solvents. Star polymers were formed after core cross-linking of these block copolymers by diisocyanate. Molecular weight of the star polymers is about 500 thousand ,even 1 million, and its PDI( per disperse index) is approximately 1.5.
These polymers were analyzed with FT-IR, GPC and NMP. The micro morphology of star polymers were studied from their TEM pictures.
通过ATRP方法合成了聚甲基丙烯酸烯丙醇酯PAMA、聚甲基丙烯酸三甲氧基硅烷-γ-丙酯PMOPS、甲基丙烯酸烯丙酯和甲基丙烯酸丁酯无规共聚物P(AMA-r-BMA)、甲基丙烯酸烯丙酯和甲基丙烯酸三甲氧基硅烷-γ-丙酯无规共聚物P(AMA-r-MOPS)以及嵌段共聚物P(AMA-b-MOPS)。在聚合中，烯丙基和可以裂解的有机硅氧烷基团保留了下来，成功的将双键和有机硅氧烷引入到大分子侧基中。这个过程在一般的自由基聚合中是无法实现的。通过在聚合物中引入甲基丙烯酸三甲氧基硅烷-γ-丙酯单元，再经溶胶／凝胶化过程可制得纳米杂化材料。
本文在HTEMPO控制下合成了分子量窄分布(分布系数1.1-1.2)的苯乙烯和乙烯基吡咯烷酮嵌段共聚物P(St-b-NVP)和苯乙烯和丙烯酸-2-羟乙酯嵌段共聚物P(St-b-HEA)。由此嵌段共聚物可以在极性和非极性溶剂中自组装成核-壳型纳米胶束，并通过多异氰酸酯将核交联，合成多臂单分散星形分子。该星形聚合物的分子量多数在五十万左右，最高可达一百万，分子量分布系数为1.5左右。
用FT-IR、GPC和NMR等仪器对所合成的聚合物分子结构进行了表征；并用透射电镜(TEM)研究了星形聚合物微观形态结构。
Atom transfer radical polymerization (ATRP) and nitroxide-mediated polymerization (NMP) were employed to control the macromolecular chain structure efficiently. In this paper we synthesize a series of living block copolymers and star polymers with functional side groups.
Poly(allyl methacrylate), Poly( Y -Methacryloxypropyl trimethoxysilane), Poly(allyl methacrylate -r- n -butyl methacrylate) and Poly(allyl methacrylate )-b-Poly( Y -Methacryloxypropyl trimethoxysilane ) were synthesized via ATRP method. Allyl and organic-silicanoxane were survived in these processes and successfully introduced into macromolecular chain as side groups, which could not be achieved in traditional free radical polymerization. Silica-polymer nanohybrid can be prepared by Sol-Gel process as the presence of the Y -Methacryloxypropyl trimethoxysilane monomer unit.
Poly (styrene)-b-Poly (N-vinylpyrrolidone) and Poly (Styrene)-b-Poly (2-Hydroxyethyl acrylate) with significantly low polydispersities(l.1-1.2) were synthesized under the control of HTEMPO. Block copolymer can be self-assemblied into nanoscalled micella in polar and nonpolar solvents. Star polymers were formed after core cross-linking of these block copolymers by diisocyanate. Molecular weight of the star polymers is about 500 thousand ,even 1 million, and its PDI( per disperse index) is approximately 1.5.
These polymers were analyzed with FT-IR, GPC and NMP. The micro morphology of star polymers were studied from their TEM pictures.
引文
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2 Morton, M.; Helminiak, T. E.; Gadkary, S. D.; Bueche, F. J. Polym. Sci,1962, 51, 411
3 郭清泉；林淑英；陈焕钦 材料科学与工程学报 2003，21(3)，446
4 薛联宝；金关泰 阴离子聚合的理论和应用 中国友谊出版公司 1988
5 张兴英 高分子化学 中国轻工业出版社 2000(第一版)
6 a)Craig J. Hawker, Anton W. Bosman, and Eva Harth Chem. Rev. 2001, 101,36613688
b) Krzysztof Matyjaszewski and Jiarthui Xia Chem. Rev. 2001, 101, 29212990
7 Guohua Deng and Yongming Chen Macromolecules 2004, 37, 18-26
8 Grubbs, R. B.; Hawker, C. J.; Dao J.; Fre'chet, J. M. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 270.
9 Hawker, C. J.; Fre'chet, J. M. J.; Grubbs, R. B.; Dao J. J. Am. Chem. Soc. 1995, 117, 10763.
10 Tao He, Gen-Hua Zheng, and Cai-yuan Pan Macromolecules 2003, 36,5960-5966
11 Geoges MK, Veregin R P N, el al. Free radical polymerization for narrow polydispersity resins Macromol, 1993, 26(20): 5316-5320
12 Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117,5614
13 J Chiefary, Y K Chong, F Ercole et al. Macromolecules, 1998, 31(16): 5559～5562
14 Krzysztof Matyjaszewski and Jianhui Xia Chem. Rev. 2001, 101, 29212990
15 Macromo]ecuIes. 1993. 26(11); 2987——2988
16 Geoges MK, Veregin R P N, el al. Free radical polymerization for narrow polydispersity resins Macromol, 1993, 26(20): 5316-5320
17 Geoges MK, Veregin RP N, el al.. Narrow molecular weight resins by a free-radical polymerization process. Macromol, 1993, 26(11): 2987-2988
18 张慰盛 高分子通报 1993，1，29
19 Geores M K, Veregin H P N. Pivotal role of nitroxide concentration in stable free radical polyriztion of acrylates. J Am Cbem, Soc, Div Polym Mater Sci Eng, 1993, 68: 6-10
20 Odell, Veregin R P N, et al. Characteristic of the stable free radical
polymerization of Styrene in the presence of 2-fluoro-1-methylpyridiniump-toluene sulfonate. Macromol, 1997, 30(8): 2232-2237
21 潘祖仁 高分子化学 北京 化工出版社 2003(第三版)
22 Veregin R P N, Odell P G, Michalak L M, Georges M K. Macromolecules, 1996,29(8): 2746-2754
23 Veregin R P N, Odell P G, Michalak L M, Georges M K. Macromolecules, 1996,29(10): 3346-3352
24 孙玉凤；杨万泰；周亨近 北京化工大学学报 1997，24(2)，19
25 杨晓敏；许守军；丘坤元 高分子通报 1996，3，166
26 Ando、T、; Kato, Kamigaite、M; Sawamoto、,M,Macromolecules 1996, 29, 1072
27 Curran, D. P. Synthesis, 1998, 489
28 Lokaj. J.: Vlcek, P.: Kriz, J, Macromolecules 1997. 30.7644
29 张兆斌；应圣康 合成橡胶工业 1999-05-15，22(3)，135
30 陈小平：丘坤元 化学进展 2001，13(3)，224．
31 王晓松；应圣康合成橡胶工业 1998—05—15，21(3)，129
32 Didier Benoit, Vladimir Chaplinski, Rebecca Braslau, and Craig J. Hawker,J. Am. Chem. Soc. 1999, 121, 3904-3920
33 Bernard Boutevin and Yves Hervaud Macromolecules 2002, 35, 6511-6516
34 Bernard Boutevin and Yves Hervaud Macromolecules 2002, 35, 6511-6516
35 Didier Benoit, Vladimir Chaplinski, Rebecca Braslau, and Craig J. Hawker,J. Am. Chem. Soc. 1999. 121, 3904-3920
36 黎宝恩；卢江 中山大学学报(自然科学版) 2001，40(5)，68
37 Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
38 Krzysztof Matyjaszewski and Jianhui Xia Chem. Rev. 2001, 101, 29212990Atom Transfer Ra Vlcek, P.: Kriz,J,Macromolecules 1997. 30. 7644
39 Controlled Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society: Washington, DC, 1998; Vol. 685
40 Wang, J. S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614.
41 Wang, J. -S.; Matyjaszewski, K. Macromolecules 1995, 28, 7901.
42 Jin-shan Wang Matyjaszewski, K. Macromol. 1995, 28(22); 7572-7573
43 张文华，作亚君，吴平平，韩哲文，功能高分子学报，1997，10(1)：1—6
44 Yoshiki, N; Scott. G. G: Matyjaszewski, K.Poly.Prep1996,37(1): 577-578
45 蒋晓慧 胡星琪 西华师范大学学报(自然科学版)2003 24(3)
46 袁金颖；楼旭东：潘才元 化学通报 2000，3，10
47 傅志峰；杨万泰 北京化工大学学报 2000，27(3)，91
48 袁金颖；楼旭东；潘才元 化学通报 2000，3，10
49 李鲲；郭建华；韩哲文 高分子学报 2004(2)
50 刘晓亚；陶友华；江明 江南大学学报(自然科学板)2002 1 3
51 Tsolakis, P. K.; Koulouri, E. G.; Kallitsis, J. K. Macromolecules
52 Koulouri, E. G.; Kallitsis, J. K.; Hadziioannou, G. Macromolecules 1999, 32,6242.
53 袁金颖；楼旭东；潘才元 化学通报 2000，3，10
54 袁金颖；王延梅；潘才元 功能高分子学报 2001，14(1)，57
55 Tsolakis, P. K.; Koulouri, E. G.; Kallitsis, J. K. Macromolecules
56 Koulouri, E. G.; Kallitsis, J. K.; Hadziioannou, G. Macromolecules1999, 32,6242.
57 Boutevin, B.; Cals, J.; Pietrasanta, Y. Eur. Polym. J. 1975, 12,225
58 Destarac, M.; Matyjaszewski, K.; Boutevin, B. Macromol. Chem. Phys. 2000,201,265.
59 Destarac, M.; Bessiere, J.-M.; Boutevin, B. J. Polym. Sci., Part
60 Boutevin, B. J. Polym. Sci., Part A: Polym. Chem. 2000, 38,3235
61 Tong, J. -D.; Ni, S.; Winnik, M. A. Macromolecules 2000, 33, 1482.
62 Tong, J. -D.; Zhou, C.; Ni, S.; Winnik, M. A. Macromolecules 2001, 34, 696.
63 Kasko, A, M; Heintz, A. M; Pugh, C. Macromolecules 1998, 31, 256-271
64 Ueda, J; Kamigaito, M; Sawamoto, M. Macromolecules 1998, 31, 557-562
65 Haddleton, D. M.; Waterson, C. Macromolecules 1999, 32, 8732-8739
Pyun, J.; Matyjaszewski, K. Macromolecules 2000, 33, 217
Matyjaszewski, K.; Miller, P. J.; Pyun, J.; Kickelbick, G.;Diamanti, S.Macromolecules 1999, 32, 6526.
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