Volume change in the polymerization of spirocyclic monomers: Causes, effects, and applications

Journal of Macromolecular Science, Part C

Volumn 32, Issue 2, 1992, Pages 135-181

  Brady, Robert F ^a  

^a NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84948253988     PISSN: 15321797     EISSN: 15205746     Source Type: Journal    
DOI: 10.1080/15321799208021424     Document Type: Article

References (165)

1. W. J. Bailey and R. L. Sun, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 13(1), 281 (1972).
2. K. J. Ivin and T. Saegusa (eds.), Ring Opening Polymerization, Elsevier, Lausanne, 1984.
3. J. E. McGrath (ed.), Ring-Opening Polymerization (Am. Chem. Soc. Symp. Ser. 286), 1985.
4. A. V. Tobolsky, F. Leonard, and G. P. Roeser, J. Polym. Sci., 3(4), 604 (1948).
5. I. S. Klaus and W. S. Knowles, J. Appl. Polym. Sci., 10, 887 (1966).
6. H. L. Parry and H. A. Mackay, Proc. Soc. Plast. Ind.,(Thirteenth Meeting, Chicago), 1955, Section 13-A, p. 1.
7. S. G. Croll, J. Coat. Technol., 51(648), 64 (1979).
8. R. J. Farris, J. Rheol., 28(4), 347 (1984).
9. Method D-792-86, “Standard Method for Specific Gravity (Relative Density) and Density of Plastics by Diplacement,” in Annual Book of ASTM Standards, Vol. 8.01, American Society for Testing and Materials, Philadelphia, 1989.
10. Method D-1505-85, “Standard Test Method for Density of Plastics by the Density Gradient Technique,” in Annual Book of ASTM Standards, Vol. 8.01, American Society for Testing and Materials, Philadelphia, 1989.
11. T. J. Dearlove and J. C. Ulicny, J. Appl. Polym. Sci., 22, 2523 (1978).
12. K. F. Arndt and A. Schwanz, Plaste Kautsch., 36(12), 435 (1989); Chem. Abstr., 122, 159667a (1990).
13. A. J. Bush, Mod. Plast., 35, 143 (1958).
14. R. N. Sampson and J. P. Lesnik, Ibid., 35, 150 (1958).
15. A. Hijikata, K. Soho, K. Kataoka, and T. Ota, Proc. Symp, Mech. Behav. Mater., 2, 379 (1974).
16. M. Shimbo, M. Ochi, and K. Arai, J. Coat. Technol., 57(728), 93 (1985).
17. M. Shimbo, M. Ochi, and K. Arai, Ibid., 56(713), 45 (1984).
18. P. W. K. Lam and M. R. Piggott, J. Mater. Sci., 24, 4068 (1989).
19. A. R. Plepys and R. J. Farris, Polymer, 31, 1932 (1990).
20. V. P. Parks and A. J. Durelli, J. Appl. Mech. 37, 504 (1965).
21. P. S. Theocaris and S. A. Paipetis, J. Strain Anal., 8, 286 (1973).
22. P. S. Theocaris and E. Marketos, Fibre Sci. Technol., 3, 21 (1970).
23. A. Saarnak, E. Nilsson, and L. O. Kornum, J. Oil. Colour Chem. Assoc., 59, 427 (1976).
24. J. T. Lim, W. Bailey, and M. R. Piggott, SAMPE Q., 15(4), 25 (1984).
25. H. Dannenberg, Soc. Plast. Eng. J., 21, 669 (1965).
26. T. S. Chow, C. A. Liu, and R. C. Penwell, J. Polym. Sci., Polym. Phys. Ed., 14, 1311 (1976).
27. W. J. Bailey, J. Macromol. Sci. -Chem., A9(5), 849 (1975).
28. T. Yokozawa, M. Sato, and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 28, 1841 (1990).
29. W. J. Bailey, P. M. Lindley, and Z.-F. Zheng, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 31(2), 63 (1990).
30. W. J. Bailey and Z.-F. Zheng, J. Polym. Sci., Polym. Chem. Ed., 29, 437 (1991).
31. W. J. Bailey, U. S. Patent 4,387,215 (June 7, 1983); Chem. Abstr., 99, 88757e (1983).
32. N. Tsubokawa, S. Ohshima, Y. Sone, and T. Endo, Polym. J., 18(11), 851 (1986).
33. W. J. Bailey and K. Saigo, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 21(1), 4 (1980).
34. K. Saigo, W. J. Bailey, T. Endo, and M. Okawara, J. Polym. Sci., Polym. Chem. Ed., 21, 1435 (1983).
35. T. Endo and H. Uno, J. Polym. Sci., Polym. Lett. Ed., 23, 359 (1985).
36. T. Endo, M. Okawara, and W. J. Bailey, Polym. J., 13(7), 715 (1981).
37. T. Endo, M. Cai-Song, M. Okawara, and W. J. Bailey, Ibid., 14(6), 485 (1982).
38. Y. Yokoyama, A. B. Padias, E. A. Bratoeff, and H. K. Hall Jr., Macromolecules, 15, 11 (1982).
39. T. Endo, K. Saigo, and W. J. Bailey, J. Polym. Chem., Polym. Lett. Ed., 18, 457 (1980).
40. H. Uno, A. Nakazawa, T. Takata, and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 28, 693 (1990).
41. W. J. Bailey, K. No, C.-Y. Pan, K. Saigo, J. Stansbury, S.-R. Tan, and J. Zhou, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 26(1), 50 (1985).
42. W. J. Bailey, M. J. Amone, B. Issari, Y.-N. Lin, K. No, C.-Y. Pan, K. Saigo, J. Stansbury, S.-R. Tan, C. Wu, N. Yamazaki, and J. Zhou, Polym. Mater. Sci. Eng., 54, 23(1986).
43. Anon., Chem. Eng. News, 64(19), 21 (May 12, 1986).
44. M. Reisch, Ibid., 67(34), 12 (August 21, 1989).
45. T. Endo, H. Katsuki, and W. J. Bailey, Makromol. Chem., 177, 3231 (1976).
46. T. Endo and W. J. Bailey, Ibid., 176, 2897 (1975).
47. T. Endo and H. Arita, Makromol. Chem., Rapid Commun., 6, 137 (1985).
48. T. Endo, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 31(2), 62 (1990).
49. H. Tagoshi and T. Endo, J. Polym. Sci., Polym. Lett. Ed., 27, 409 (1989).
50. H. Tagoshi and T. Endo, Macromolecules, 22, 3834 (1989).
51. S. Komatsu, T. Takata, and T. Endo, Ibid., 24, 2132 (1991).
52. A. M. Sikes and R. F. Brady Jr., J. Polym. Sci., Polym. Chem. Ed., 28, 2533 (1990).
53. A. M. Sikes and R. F. Brady Jr., Polym. Mater. Sci. Eng., 60, 614 (1989).
54. R. F. Brady Jr. and A. M. Sikes, Polym. Bull., 22, 521 (1989).
55. V. Liska, Plast. Hmoty Kauc, 8(6), 167 (1971); Chem. Abstr., 75, 98997b (1971).
56. Hitachi Chemical Co., Ltd., Japanese Kokai Tokkyo Koho JP 59 53,527 [84 53,527] (March 28, 1984); Chem. Abstr., 101, 152900k (1984)
57. Hitachi Chemical Co., Ltd., Japanese Kokai Tokkyo Koho JP 60 31,524 [85 31,524] (February 18, 1985); Chem. Abstr., 103, 23837n (1985).
58. Hitachi Chemical Co., Ltd., Japanese Kokai Tokkyo Koho JP 60 58,423 [85 58,423] (April 4, 1985); Chem. Abstr., 103, 54960b (1985).
59. L. F. Fieser, J. Am. Chem. Soc., 53, 3546 (1931).
60. R. F. Brady Jr. and A. M. Sikes, Macromolecules, 24, 688 (1991).
61. A. M. Sikes and R. F. Brady Jr., Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 31(1), 358 (1990).
62. A. M. Sikes and R. F. Brady Jr., Polym. Mater. Sci. Eng., 62, 597 (1990).
63. R. F. Brady Jr. and F. E. Simon, J. Polym. Sci., Polym. Chem. Ed., 25, 231(1987).
64. R. F. Brady Jr. and F. E. Simon, Proceedings, Fifth International Symposium on Ring Opening Polymerization, Blois, France, 1986, p. C133.
65. W. J. Bailey, Makromol. Chem. Macromol. Symp., 6, 81 (1986).
66. W. J. Bailey, Polym. J., 17(1), 85 (1985).
67. W. J. Bailey and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 14, 1735 (1976).
68. T. Endo and W. J. Bailey, J. Polym. Sci., Polym. Lett. Ed., 13, 193 (1975).
69. J. W. Stansbury and W. J. Bailey, Polym. Mater. Sci. Eng., 59, 402 (1988).
70. M. S. Cohen and M. Dunkel, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 31(2), 58 (1990).
71. T. Endo and W. J. Bailey, J. Polym. Chem., Polym. Chem. Ed., 13, 2525 (1975).
72. T. Endo, M. Okawara, N. Yamazaki, and W. J. Bailey, Ibid., 19, 1283 (1981).
73. T. Endo and W. J. Bailey, J. Polym. Sci., Polym. Lett. Ed., 18, 25 (1980).
74. H. Fukuda, M. Hirota, T. Endo, M. Okawara, and W. J. Bailey, J. Polym. Sci., Polym. Chem. Ed., 20, 2935 (1982).
75. T. Endo, M. Okawara, K. Saigo, and W. J. Bailey, Ibid., 18, 771 (1980).
76. T. Endo, N. Kitamura, T. Takata, and T. Nishikubo, J. Polym. Sci., Polym. Lett. Ed., 26, 517 (1988).
77. J.-I. Sugiyama, T. Yokozawa, and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 28, 3529 (1990).
78. H. Tagoshi and T. Endo, Ibid., 27, 1415 (1989).
79. H. Tagoshi and T. Endo, Ibid., 27, 4169 (1989).
80. H. Tagoshi and T. Endo, J. Polym. Sci., Polym. Lett. Ed., 26,77 (1988).
81. L. J. Mathias and S. H. Kusefoglu, Macromolecules, 20, 2039 (1987).
82. L. J. Mathias and S. H. Kusefoglu, J. Polym. Sci., Polym. Lett. Ed., 25, 451 (1987).
83. L. J. Mathias, S. H. Kusefoglu, and J. E. Ingram, Macromolecules, 21, 545 (1988).
84. L. J. Mathias, R. M. Warren, and S. Huang, Ibid., 24, 2036 (1991).
85. R. F. Colletti, R. J. Halley, and L. J. Mathias, Ibid., 24, 2043 (1991).
86. L. J. Mathias and C. W. Dickerson, Ibid., 24, 2048 (1991).
87. J. W. Stansbury, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 37(1), 503 (1990).
88. J. W. Stansbury, Macromolecules, 24, 2029 (1991).
89. E. Grigat, Angew. Chem., 84,1008 (1972); Angew. Chem., Int. Ed. Engl., 11(11), 949 (1972).
90. E. Grigat, H. D. Schimke, and R. Puetter (to Farbenfabriken Bayer A.G.), German Patent 1,190,184 (April 1, 1965); Chem. Abstr., 63, 5849b (1965).
91. V. V. Korshak, V. A. Pankratov, A. A. Ladovskaya, and S. V. Vinogradova, J. Polym. Sci., Polym. Chem. Ed., 16, 1697 (1978).
92. D. A. Shimp, Polym. Mater. Sci. Eng., 54, 107 (1986).
93. A. K. Bonetskaya, M. A. Kravchenko, Ts. M. Frenkel, V. A. Pankratov, S. V. Vinogradova, and V. V. Korshak, Dokl. Akad. Nauk SSSR, 212(6), 1353 (1973); Chem. Abstr., 80, 71133h (1974).
94. W. J. Bailey, H. Iwama, and R. Tsushima, J. Polym. Sci., Polym. Symp., 56, 117 (1976).
95. W. J. Bailey, R. L. Sun, H. Katsuki, T. Endo, H. Iwama, R. Tsushima, K. Saigou, and J. M. Bitritto, in Ring-Opening Polymerization (T. Saegusa and E. Goethals, eds.), (Am. Chem. Soc. Symp. Ser. 59), 1977, p. 38.
96. J. W. Stansbury, Polym. Prepr., Am. Chem. Soc. Div. Polym. Chem., 31(2), 59 (1990).
97. Y. Wang, and C.-Y. Pan, Ibid., 31(2), 661 (1990).
98. S. Sakai, T. Fujinami, and S. Sakurai, J. Polym. Sci., Polym. Lett. Ed., 11, 631 (1973).
99. Y. K. Han and S. K. Choi, J. Polym. Sci., Polym. Chem. Ed., 21, 353 (1983).
100. C.-Y. Pan, S.-X. Lu, and W. J. Bailey, Makromol. Chem., 188, 1651 (1987).
101. S. Chikaoka, T. Takata, and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 28, 3101 (1990).
102. S. Chikaoka, T. Takata, and T. Endo, Macromolecules, 24, 331 (1991).
103. T. Takata, K. Amachi, K. Kitazawa, and T. Endo, Ibid., 22, 3188 (1989).
104. T. Takata, M. Igarashi, and T. Endo, J. Polym. Sci., Polym. Chem. Ed., 29, 781 (1991).
105. K. Matyjaszewski, Ibid., 22, 29 (1984).
106. J. Kops, S. Hvilsted, and H. Spanggaard, Pure Appl. Chem., 53(9), 1777 (1981).
107. D. A. Tirrell, in Polym. Sci. Technol., 25 (New Monomers and Polymers), (L.-H. Lee, ed.), Plenum Press, New York, 1984, p. 431.
108. H. Ishida and J. Nigro, Polym. Mater. Sci. Eng., 59, 859 (1988).
109. G. Wisanrakkit and J. K. Gillham, J. Coat. Technol., 62(783), 35 (1990).
110. Y. Tanaka and H. Kakiuchi, J. Polym. Sci., Part A, 2, 3405 (1964).
111. G. C. Stevens, J. Appl. Polym. Sci., 26, 4259 (1981).
112. M. Shimbo, N. Nishitani, and T. Takahama, Ibid., 29, 1709 (1984).
113. M. Shimbo, M. Ochi, and Y. Shigeta, Ibid., 26, 2265 (1981).
114. W. Fisch, W. Hofmann, and R. Schmid, Ibid., 13, 295 (1969).
115. K. P. Pang and J. K. Gillham, Ibid., 37, 1969 (1989).
116. M. Ochi, K. Yamashita, M. Yoshizumi, and M. Shimo, Ibid., 38, 789 (1989).
117. K. P. Pang and J. K. Gillham, Ibid., 39, 909 (1990).
118. M. Shimbo, M. Ochi, T. Inamura, and M. Inoue, J. Mater. Sci., 20, 2965 (1985).
119. M. Ochi, S. Zhu and M. Shimbo, Polymer, 27, 1569 (1986).
120. M. Ochi, M. Shimbo, M. Saga, and N. Takashima, J. Polym. Sci., Polym. Phys. Ed., 24, 2185 (1986).
121. J. B. Enns and J. K. Gillham, J. Appl. Polym. Sci., 28, 2831 (1983).
122. T. D. Chang, S. H. Carr, and J. O. Brittain, Polym. Eng. Sci., 22, 1213 (1982).
123. N. Hata and J. Kumanotani, J. Appl. Polym. Sci., 15, 2371 (1971).
124. V. B. Gupta and C. B. Swaran, Ibid., 41, 2533 (1990).
125. F. W. Billmeyer Jr., Textbook of Polymer Science, Wiley, New York, 1984, p. 321.
126. J. A. Schroeder, P. A. Madsen, and R. T. Foister, Polymer, 28(5), 929 (1987).
127. J. M. Charlesworth, Polym. Eng. Sci., 28(4), 221 (1988).
128. J. M. Charlesworth, J. Macromol. Sci. -Phys., B26( 1), 105 (1987).
129. J. M. Charlesworth, Polym Eng. Sci., 28(4), 230 (1988).
130. R. Simha and R. F. Boyer, J. Chem. Phys., 37, 1003 (1962).
131. M. R. Piggott, Polym. Prepr., Am. Chem. Soc., Div. Polym. Chem., 31(2), 59 (1990).
132. K. P. Pang and J. K. Gillham, J. Appl. Polym. Sci., 39, 909 (1990).
133. G. Wisanrakkit, J. K. Gillham, and J. B. Enns, Ibid., 41, 1895 (1990).
134. G. Wisanrakkit and J. K. Gillham, Ibid., 41, 2885 (1990).
135. B. L. Burton and C. A. Swartz, Polym. Mater. Sci. Eng., 57, 201 (1987).
136. A. Apicella and L. Nicolais, Adv. Polym. Sci., 72, 69 (1985).
137. S. G. Croll, J. Coat. Technol., 51(659), 49 (1979).
138. J. W. Prane, Polym. News, 11, 367 (1986).
139. H. Pingsheng, Z. Zhiqiang, and P. Caiyuan, J. Mater. Sci., 24, 1528 (1989).
140. R. F. Schappert (to PPG Industries, Inc.), U.S. Patent 4,739,019 (April 19, 1988).
141. D. C. Sayles (to the United States of America), U.S. Patent 4,574,132 (March 4, 1986).
142. T. Nakatani, Y. Fujimoto, K. Kimura, and H. Kato (to Toa Gosei Chemical Industry Co., Ltd.), Japan Kokai Tokkyo Koho JP 61 264,016 [86 264,016], (November 21, 1986); Chem.Abstr., 111, 234324w (1990).
143. S. G. Croll, J. Coat. Technol., 50(638), 33 (1978).
144. S. G. Croll, J. Appl. Polym. Sci., 23, 847 (1979).
145. S. G. Croll, J. Oil. Colour Chem. Assoc., 63, 230 (1980).
146. S. G. Croll, J. Coat. Technol., 55(672), 85 (1981).
147. K. Sato, Prog. Org. Coat., 8, 143 (1980).
148. C. H. Hare, J. Protect. Coat. Linings, 3(9), 38 (1986).
149. C. L. Bauer, R. J. Farris, and M. S. Vratsanos, in Polym. Sci. Technol., 37(Adhesives, Sealants, and Coatings for Space and Harsh Environments), (L.-H. Lee, ed.), Plenum Press, New York, 1988, p. 361.
150. M. S. Cohen, C. Bluestein, R. Kozic, and D. Fergesen, Polym. Mater. Sci. Eng., 54, 12 (1986).
151. E. L. Rodriguez, J. Mater. Sci. Lett., 8, 116 (1989).
152. M. R. Piggott, J. Mater. Sci., 13, 1709 (1978).
153. M. R. Piggott, P. W. K. Lam, J. T. Lim, and M. S. Woo, Compos. Sci. Technol., 23, 247 (1985).
154. M. R. Piggott and T. Pyshnov, Polym. Muter. Sci. Eng., 54, 18 (1986).
155. P. Lam and M. R. Piggott, J. Muter. Sci., 24, 4427 (1989).
156. B. F. Howell, Influence of Expanding Monomer on Carbon Fiber Reinforced Epoxy Composites, Report DTRC-SME-90/20. David Taylor Research Center, Annapolis, Maryland, June 1990.
157. P. S. Chua and M. R. Piggott, Compos. Sci. Technol., 22, 107 (1985).
158. P. S. Chua and M. R. Piggott, Ibid., 22, 185 (1985).
159. P. S. Chua and M. R. Piggott, Ibid., 22, 245 (1985).
160. B. L. Burton, Proc. Int. SAMPE Tech. Conf., 19, 653 (1987).
161. L. Penn, F. Bystry, W. Karp, and S. Lee, in Molecular Characterization of Composite Interfaces, Plenum Press, New York, 1985, p. 93.
162. V. P. Thompson, E. F. Williams, and W. J. Bailey, J. Dent. Res., 58, 522 (1979).
163. W. J. Bailey, M. J. Amone, and B. Issari, Polym. Muter. Sci. Eng., 59, 825 (1988).
164. G. W. Bogan, M. E. Lyssy, G. A. Monnerat, and E. P. Woo, Soc. Adv. Muter. Process Eng. J., 24(6), 19 (1988).
165. F. S. Nichols and R. G. Flowers, Znd. Eng. Chem., 42, 292 (1950).