Synthesis and polymerization of functional monomer precursors

Journal of Macromolecular Science - Reviews in Macromolecular Chemistry and Physics

Volumn 37, Issue 1, 1997, Pages 1-59

  Dasgupta, Arnab ^a,b   Sivaram, Swaminathan ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b Tala Res Devmt and Design Centre   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346004959     PISSN: 07366574     EISSN: None     Source Type: Journal    
DOI: 10.1080/15321799708014732     Document Type: Article

References (165)

1. J. A. Kuczkowski and J. G. Gillick, Rubber Chem Technol., 57, 621 (1984); J. Pospisil, Adv. Polym. Sci., 101, 65 (1991).
2. J. A. Kuczkowski and J. G. Gillick, Rubber Chem Technol., 57, 621 (1984); J. Pospisil, Adv. Polym. Sci., 101, 65 (1991).
3. A. Hirao and S. Nakahama, Prog. Polym. Sci., 15, 299 (1990).
4. J. Dunogues, Bull. Soc. Chim. Fran., 659 (1987).
5. J. M. Hay and D. Lyon, Nature, 216, 790 (1967).
6. F. L. Marten, Encycl. Polym. Sci. Eng. 2nd Ed.; Ed. J. I. Kroschwitz, 17, 167 (1985) and references 3-6 therein.
7. H. C. Haas, E. S. Smerson, and N. W. Schuler, J. Polym. Sci., 22, 219 (1956).
8. K. Fujii, T. Mochizuki, S. Imoto, J. Ukida, and M. Matsumoto, Makromol. Chem., 51, 225 (1962).
9. K. Noro, Polyvinyl Alcohol, J. Wiley, London, p. 147 (1973).
10. U. S. Pat. 3,689,469 (Sept. 5, 1972), H. K. Inskip and R. L. Adelman (to E. I. DuPont, DeNemours & Co., Inc.)
11. U.S. Pat. 4,618,648 (Oct. 21, 1986) F. L. Marten (to Air Products and Chemicals Inc.)
12. U.S. Pat. 4,675,360 (June 23, 1987) F. L. Marten (to Air Products and Chemicals Inc.)
13. U.S. Pat. 4,708,999 (Nov. 24, 1987) F. L. Marten (to Air Products and Chemicals Inc.)
14. K. E. Uhrich, E. Reichmanis, S. A. Haffner, and J. M. Komateni, Macromolecules, 27, 4936 (1994).
15. R. H. Still and A. Whitehead, J. Appl. Polym. Sci., 21, 1199 (1977).
16. C. S. Marvel and N. S. Rao, J. Polym. Sci., 4, 703 (1949).
17. M. Kato and H. Kamogawa, J. Polym. Sci., A-1, 4, 2771 (1966).
18. M. Kato, Ibid., 7, 2175 (1969).
19. C. G. Overberger, J. C. Salamone, and S. J. Yaroslavsky, J. Am. Chem. Soc., 89, 6231 (1967).
20. F. Danusso, P. Ferruti, and C. G. Marabelli, Chim. Ind. (Milan), 47, 493 (1965).
21. K. Nakayama, T. Hatakeyama, and H. Hatakeyama, Polymer, 22, 473 (1981); Ibid., 24, 871 (1983).
22. K. Nakayama, T. Hatakeyama, and H. Hatakeyama, Polymer, 22, 473 (1981); Ibid., 24, 871 (1983).
23. D. Bellus, P. Slama, P. Hrdkovic, Z. Manasek, and L. Durisinova, J. Polym. Sci., (C), 22, 629 (1969).
24. J. M. J. Frechet, E. Eichiler, H. Ito, and C. G. Wilson, Polymer, 24, 995 (1983).
25. P. Ferruti and A. Fere, J. Polym. Sci., A-1, 9, 3671 (1971).
26. H. Manami and S. Nishizaki, Kogyo Kagakuzasshi, 63, 366 (1960).
27. A. D. Jenkins, K. Petrak, G. A. F. Roberts, and D. R M. Walton, Eur. Polym. J., 11, 653 (1975).
28. N. Madit, F. Bonfils, L. Giral, C. Montginoul, R. Sagnes, and F. Schue, Makromol. Chem., 192, 1467 (1991).
29. K. E. Uhrich, E. Reichmanis, and O. Nalamasu, Chemistry of Materials, 6, 287 (1994).
30. G. Hardy, J. Varga, K. Nytrac, I. Tsajlik, and L. Zubonyai, Vysokoml. Soedin, 6, 758 (1964) and references therein.
31. W. H. Daly and S. Chotiwana, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 22(1), 164 (1982).
32. W. H. Daly and S. J. Moulay, J. Polym. Sci., Polym. Symp., 74, 227 (1986).
33. K.-D. Ahn, D.-I. Koo, and C. G. Wilson, Polymer, 36(13), 2621 (1995).
34. A. Hirao, K. Takenaka, S. Pakirisamy, K. Yamaguchi, and S. Nakahama, Makromol. Chem., 186, 1157 (1985).
35. A. Hirao, K. Kitamura, K. Takenaka, and S. Nakahama, Macromolecules, 26, 4995 (1993).
36. T. Tuschka, K. Naito, and B. Rickborn, J. Org. Chem., 48, 70 (1983).
37. R. J. Moss and B. Rickborn, Ibid., 49, 3694 (1984).
38. E. J. Corey and A. Venkataeswaralu, J. Am. Chem. Soc., 94, 6190 (1972).
39. L. A. Carpino and A. C. Sau, J. Chem. Soc. Chem. Comm., 514 (1979).
40. A. Hirao, K. Takenaka, K. Yamaguchi, S. Nakahama, and N. Yamazaki, Polym. Commun., 24, 339 (1983).
41. A. Hirao, A. Yamamoto, K. Takenaka, K. Yamaguchi, and S. Nakahama, Polymer, 28, 303, (1987).
42. G. A. Russel, D. E. Gregonis, A. S. D. Visser, and J. D. Andrade in Hydrogels for Medical and Related Applications, ACS Symposium Series, Ser. No. 31, Am. Chem. Soc., Washington, D.C., 139 (1976).
43. A. Hirao, H. Kato, K. Yamaguchi, and S. Nakahama, Macromolecules, 19, 1294 (1986).
44. H. Mori, O. Wakisaka, A. Hirao, and S. Nakahama, Macromol. Chem., 195(9), 3213 (1994).
45. R. Fayt, R. Forte, C. Jacobs, R. Jerome, T. Ouhadi, Ph. Teyssie, and S. K. Vershney, Macromolecules, 23, 2618 (1990).
46. H. Mori, A. Hirao, and S. Nakahama, Ibid., 27(1), 35 (1994).
47. K. Oguchi, K. Sanui, N. Ogata, Y. Takahashi, and T. Nakada, Polym. Eng. Sci., 30, 449 (1990).
48. T. Ishizone, A. Mochizuki, A. Hirao, and S. Nakahama, Macromolecules, 28, 3787 (1995).
49. T. Higashimura and S. Okamura, paper presented at the 3rd symposium on Poly(vinyl alcohol), Osaka, Oct. 1963.
50. S. Murahashi, H. Yuki, T. Sano, U. Yonemura, H. Tadokoro, and Y. Chatani, J. Polym. Sci., 62, 577 (1962).
51. K. Fujii, Kobunshi Kagaku, 19, 120 (1962).
52. S. Okamura, T. Kodama, and T. Higashimura, Makromol. Chem., 53, 180 (1962).
53. S. Murahashi, S. Nozakura, and M. Sumi, J. Polym. Sci. (B), 3, 245 (1965).
54. K. Fujii, T. Mochizuki, S. Imoto, J. Ukida, and M. Matsumoto, J. Polym. Sci., A2, 2327 (1964).
55. K. Fujii and J. Ukida, Makromol. Chem., 65, 74 (1963).
56. T. Higashimura, K. Ebara, and S. Aoshima, J. Polym. Sci. (A), 27, 2937 (1989).
57. O. W. Webster, W. R. Herder, D. Y. Sogah, W. B. Farnham, and T. V. RajanBabu, J. Am. Chem. Soc., 105, 5706 (1983).
58. O. W. Webster, Encycl. Polym. Sci. Engg., Ed. J. I. Kroschwitz, 7, 580 (1985); O. W. Webster and D. Y. Sogah, in: Comprehensive Polymer Science, Eds. G. Allen, J. C. Bevington, Pergamon Press, 4, 163 (1989).
59. O. W. Webster, Encycl. Polym. Sci. Engg., Ed. J. I. Kroschwitz, 7, 580 (1985); O. W. Webster and D. Y. Sogah, in: Comprehensive Polymer Science, Eds. G. Allen, J. C. Bevington, Pergamon Press, 4, 163 (1989).
60. R. P. Quirk and G. P. Bidinger, Polym. Bull., 22, 63 (1989); A. H. E. Muller, Makromol. Chimie Macromol. Symp., 32, 87 (1990).
61. R. P. Quirk and G. P. Bidinger, Polym. Bull., 22, 63 (1989); A. H. E. Muller, Makromol. Chimie Macromol. Symp., 32, 87 (1990).
62. O. W. Webster and D. Y. Sogah, Recent Advances in Mechanistic and Synthetic Aspects of Polymerization, Eds. M. Fontanille and A. Guyot NATO ASI Series 3 (1987).
63. D. Y. Sogah and W. R. Hertler, J. Polym. Sci. Polym. Lett., 21, 927, (1983).
64. D. Y. Sogah, W. R. Hertler, O. W. Webster, and G. M. Cohen, Macromolecules, 20, 1473 (1987).
65. D. Y. Sogah and O. W. Webster, in Ref. 58, p. 61.
66. B. Charleux and C. Pichot, Polymer, 34, 195 (1993).
67. G. Wulff, P. Birnbrich, and A. Hansen, Angew. Chem. Int. Ed. Engl., 27, 1158 (1988).
68. G. Wulff and A. Hansen, Angew. Chem. Int. Ed. Engl., 25, 560 (1986).
69. G. Wulff and P. Birnbrich, Chem. Ber., 125, 473 (1992).
70. J. Shen and D. Y. Sogah, Macromolecules, 27, 6996 (1994).
71. F. Bandermann and F. Witkowski, Makromol. Chem., 190, 2173 (1989).
72. P. Boettcher, Makromol. Chem., Macromol. Symp., 13/14, 193 (1988).
73. Y. Kawakamie, T. Aoki, and Y. Yamashita, Polym. Bull., 18, 473 (1987).
74. G. Wulffand P. Birnbrich, Makromol. Chem., 194, 1569 (1993).
75. T. C. Chung, Macromolecules, 21, 865 (1988).
76. S. Ramakrishnan, E. Berluche, and T. C. Chung, Ibid., 23, 978 (1990).
77. T. C. Chung and D. Rhubright, Ibid., 24, 970 (1991).
78. T. C. Chung, S. Ramakrishnan, and M. W. Kim, Ibid., 23, 3536 (1990).
79. S. Ramakrishnan and T. C. Chung, Ibid., 24, 2675 (1991).
80. S. Ramakrishnan and T. C. Chung, Ibid., 23, 4519 (1990); T. C. Chung, J. Mol. Cata. 76, 15 (1992).
81. S. Ramakrishnan and T. C. Chung, Ibid., 23, 4519 (1990); T. C. Chung, J. Mol. Cata. 76, 15 (1992).
82. M. Imoto, M. Kinoshita, and T. Irie, Kogyo Kagaku Zasshi, 72, 1210 (1969).
83. S. Nakazawa, M. Kinoshita, and M. Imoto, Ibid., 70, 1452 (1967).
84. R. Kroker and H. Ringsdorf, Makromol. Chem., 121, 240 (1969).
85. K. Gollmer and H. Ringsdorf, Kolloid. Z. Polym., 216/217, 325 (1967).
86. T. K. Dykstra and D. A. Smith, Makromol. Chem., 134, 209 (1970).
87. C. G. Overberger, H. Ringsdorf, and N. Weinshankar, Ibid., 64, 126 (1963); J. Org. Chem., 27, 4331 (1962).
88. C. G. Overberger, H. Ringsdorf, and N. Weinshankar, Ibid., 64, 126 (1963); J. Org. Chem., 27, 4331 (1962).
89. T. Nakai, K. Shioya, and M. Okawara, Makromol. Chem., 108, 95 (1967).
90. A. A. Oswald and T. J. Wallace, in: The Chemistry of Organic Sulfur Compounds, Vol. 2, N. Kharash and C. Y. Meyers, Eds. Pergamon Press, New York, 1966, Chap. 8.
91. M. S. Kharasch, A. T. Read, and F. R. Mayo, Chem. Ind. (Lond.), 57, 792 (1938).
92. B. Giese and K. Jay, Chem. Ber., 112, 304 (1979).
93. S. Nazakura, Y. Yamamoto, and S. Murahashi, Polym. J., 5, 55 (1973).
94. K. Yamaguchi, T. Kato, A. Hirao, and S. Nakahama, Makromol. Chem., Rapid Commun., 8, 203 (1987).
95. A. Hirao, H. Shione, S. Wakabayashi, S. Nakahama, and K. Yamaguchi, Macromolecules, 27, 1835 (1994).
96. C. Giradand J. M. Conia, Tetrahedron Lett., 3327 (1974).
97. C. Girad, P. Amice, J. P. Barnier, and J. M. Conia, Ibid., 3329 (1974).
98. P. Brownbridge, Synthesis, 1, 85 (1983).
99. E. W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, London (1988).
100. J. Penelle and S. Verraver, Makromol. Chem., Rapid Commun., 14, 563 (1993).
101. J. Penelle, S. Verraver, P. Raucq, and J. Marchand-Brynaert, Macromol. Chem. Phys., 196, 857 (1995).
102. J. Penelle, A. B. Padias, H. K. Hall, Jr., and H. Tanaka, Adv. Polym. Sci., 102, 73 (1992).
103. H. Tanaka, Trends Polym. Sci., 1, 361 (1993).
104. H. G. Viehe, R. Merenyi, L. Stella, and Z. Janousek, Acc. Chem. Res., 18, 148 (1985).
105. M. Kamachi, M. Kohno, Y. Kuwae, and S. Nozakura, Polym. J. (Tokyo), 14, 749 (1982).
106. H. Tanaka, T. Kameshima, K. Sasai, T. Suto, and T. Ota, Makromol. Chem., 192, 427 (1991).
107. K. Nagai, K. Asada, K. Chiba, and N. Kuramoto, J. Polym. Sci. Polym. Chem., 27, 3779 (1989).
108. K. Nagai, K. Chiba, K. Asada, K. Masui, and N. Kuramoto, Ibid., 28, 2195 (1990).
109. K. Asada, N. Kuramoto, and K. Nagai, Ibid., 28, 2845 (1990).
110. K. Nagai, K. Asada, and N. Kuramoto, Polym. Prepr. Jpn., 38, 328 (1989).
111. J. Penelle, V. Mayne, and C. Wynants, Eur. Polym. J., 30, 295 (1994).
112. R. Kato, K. Takenaka, A. Hirao, S. Nakahama, and Y. Ishino, Polym. Prepr. Jap., 37, 104 (1988).
113. A. Hirao, Y. Ishino, and S. Nakahama, Makromol. Chem., 187, 141 (1986).
114. F. E. Ziegler and K. W. Fowler, J. Org. Chem., 41, 1564 (1976).
115. F. E. Ziegler, I. Chliwner, K. W. Fowler, S. J. Kanfer, S. J. Kudo, and N. D. Sinha, J. Am. Chem. Soc., 102, 790 (1980).
116. A. Hirao and S. Nakahama, Macromolecules, 20, 2968 (1987).
117. A. Hirao, K. Kato, and S. Nakahama, Ibid., 25, 535 (1992).
118. T. Hirabayashi, T. Itoh, and K. Yokota, Polym. J., 20, 1041 (1988).
119. T. Hirabayashi, T. Kawasaki, and K. Yokota, Ibid., 22, 287 (1990).
120. J. Shen and D. Y. Sogah, Macromolecules, 27, 6996 (1994).
121. K. Yamaguchi, A. Hirao, K. Suzuki, K. Takenaka, S. Nakahama, and N. Yamazaki, J. Polym. Sci., Polym. Lett., 21, 395 (1983).
122. K. Suzuki, K. Yamaguchi, A. Hirao, and S. Nakahama, Macromolecules, 22, 2607 (1989).
123. K. Suzuki, A. Hirao, and S. Nakahama, Makromol. Chem., 190, 2893 (1989).
124. A. J. Chapman and N. C. Billingham, Eur. Polym. J., 16, 21 (1980).
125. A. Chapman and A. D. Jenkins, J. Polym. Sci., Polym. Chem. Ed., 15, 3075 (1977).
126. M. Camail, P. Durand, B. Gedoux, A. Margaillan, and J. L. Vernet, Eur. Polym. J., 28, 335 (1992).
127. D. A. Mixon, A. E. Novembre, W. W. Tai, C. W. Jurgensen, J. Frackoviak, and L. E. Trimble, J. Vac. Sci. Technol. B., 11, 2834 (1993).
128. M. Kamachi, M. Kurihara, and J. K. Stille, Macromolecules, 5, 161 (1972).
129. M. Kurihara, M. Kamachi, and J. K. Stille, J. Polym. Sci., Polym. Chem., 11, 587 (1973).
130. Y. Morishima, T. Hashimoto, Y. Itoh, M. Kamachi, and S. Nozakura, Makromol. Chem. Rapid Commun., 2, 507 (1981).
131. M. A. Doherty and T. E. Hogen-Esch, Makromol. Chem., 187, 61 (1986).
132. D. E. Bugner, Polym. Prepr. ACS. Div. Polym. Chem., 27(2), 57 (1983).
133. T. Ishizone, H. Kurosawa, A. Hirao, and S. Nakahama, Macromol. Chem., 195, 3173 (1994).
134. Y. Ishino, A. Hirao, and S. Nakahama, Macromolecules, 19, 2307 (1986).
135. A. Hirao, Y. Ishino, and S. Nakahama, Ibid., 21, 561 (1988).
136. A. I. Meyers and E. D. Mihelich, Angew. Chem. Int. Ed. Engl., 15, 270 (1976).
137. M. Reuman and A. I. Meyers, Tetrahedron, 41, 837 (1985).
138. W. E. Parham and L. S. Jones, J. Org. Chem., 41, 2704 (1976).
139. P. Beak, M. Baillargeon, and L. G. Carter, Ibid., 43, 4255 (1978).
140. R. Schecker, D. Seebach, and W. Lubosch, Helv. Chim. Acta., 61, 512 (1978).
141. T. Ishizone, A. Hirao, and S. Nakahama, Macromolecules, 22, 2895 (1989).
142. T. Ishizone, H. Kurosawa, A. Hirao, and S. Nakahama, Macromol. Chem., 195, 3213 (1994).
143. J. Mykytiuk, S. P. Armes, and N. C. Billingham, Polym. Bull., 29, 139 (1992).
144. S. P. Rannard, N. C. Billingham, S. P. Armes, and J. Mykytiuk, Eur. Polym. J., 29, 407 (1993).
145. A. Caron, C. Bunel, C. Braud, and M. Vert, Polymer, 32, 2659 (1991).
146. W. T. Thomas and D. W. Wang, Encycl. Polym. Sci. Engg., Ed. J. I. Kroschwitz, 1, 169 (1985).
147. Refs. 97, 118, 120, 121, 132, 133 in Ref. 140.
148. A. Dasgupta and S. Sivaram, Macromolecules, 27, 1665 (1994).
149. A. Dasgupta and S. Sivaram, Macromol. Chem. Phys., 195, 3361 (1994).
150. A. Dasgupta, Eur. Polym. J., 32, 475 (1996).
151. G. Saini, A. Leoni, and S. Franco, Makromol. Chem., 144, 2355 (1971); C. I. Simionescu, K. G. Sik, S. Dumitriu, E. Comounita, and M. Pastravanu, Polym. Bull. (Berlin), 15, 503 (1986).
152. G. Saini, A. Leoni, and S. Franco, Makromol. Chem., 144, 2355 (1971); C. I. Simionescu, K. G. Sik, S. Dumitriu, E. Comounita, and M. Pastravanu, Polym. Bull. (Berlin), 15, 503 (1986).
153. A. Dasgupta, B. Garnaik, and S. Sivaram, unpublished results.
154. A. Matsumoto, Y. Oki, and T. Otsu, Polym. J., 24, 679 (1992).
155. A. Matsumoto, Y. Oki, and T. Otsu, Ibid., 25, 237 (1993).
156. H. Yamaguchi, T. Doiuchi, and K. Kawamoto, Macromolecules, 18, 2120 (1984).
157. T. Oishi, K. Kagawa, and M. Fujimoto, Ibid., 26, 24 (1993).
158. H. Yamaguchi, T. Iwama, T. Hayashi, and T. Doiuchi, Makromol. Chem., 191, 1243 (1991).
159. (a) F. Ciardelli, Encycl. Polym. Sci. Engg., Ed. J. I. Kroschwitz, 10, 463 (1987).
160. (b) O. Tsutomo and F. J. Minoruu, J. Polym. Sci., Polym. Chem. Ed., 22, 2789 (1984).
161. B. B. De, S. Sivaram, and P. K. Dhal, Polymer, 33, 1756 (1992).
162. B. B. De, S. Sivaram, and P. K. Dhal, J. Macromol. Sci., Pure Appl. Chem., A32 (2), 227 (1995).
163. E. Seymour and J. M. J. Frechet, Tetrahedron Lett., 1149 (1976).
164. G. Wulff and P. K. Dhal, Macromolecules, 21, 571 (1988).
165. A. Hirao and S. Nakahama, Ibid., 20, 571 (1987).