Skip to main content

The synthesis, manufacture and characterization of cyanate ester monomers

  • Chapter
Chemistry and Technology of Cyanate Ester Resins

Abstract

Cyanate ester monomers polymerize by a cyclotrimerization reaction to a cyanurate (often referred to as an striazine) linked network polymer as depicted in Scheme 2.1.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 379.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  1. Grigat, E. and Pütter, R. (1967) Angew. Chem. Internat. Edit., 6, 206.

    CAS  Google Scholar 

  2. Grigat, E. (1972) Angew. Chem. Internat. Edit., 11, 949.

    CAS  Google Scholar 

  3. Jensen, K.A., Due, M., Holm, A. and Wentrup, C. (1966) Acta Chem. Scand., 20, 2091.

    CAS  Google Scholar 

  4. Jensen, K.A. and Holm, A. (1977) In The Chemistry of Cyanates and Their Thio Derivatives, Part 1, ed. Patai, S. Wiley, New York pp. 569–617.

    Google Scholar 

  5. Martin, D. (1967) Z. Chem., 7, 123.

    CAS  Google Scholar 

  6. Pankratov, V.A., Vinogradova, S.V. and Korshak, V.V. (1977) Russ. Chem. Rev., 46, 278.

    Google Scholar 

  7. Graver, R.B. (1986) In High Performance Polymers: Their Origin and Development, eds. Seymour, R.B. and Kirshenbaum, G.S. Elsevier, New York, (1986) pp. 309–316.

    Google Scholar 

  8. Stroh, R. and Gerber, H. (1960) Angew. Chem. 72, 1000.

    Google Scholar 

  9. Grigat, E. and Pütter, R. (1963) German Patent 1,195,764.

    Google Scholar 

  10. Grigat, E. and Pütter, R. (1964) Chem. Ber., 97, 3012.

    CAS  Google Scholar 

  11. Jensen, K.A. and Holm, A. (1964) Acta Chem. Scand., 18, 826.

    CAS  Google Scholar 

  12. Martin, D. (1964) Angew Chem., 76, 303.

    CAS  Google Scholar 

  13. Kubens, R., Schulthesis, H., Wolf, W. and Grigat, E. (1968) Kunststoffe 58, 827.

    CAS  Google Scholar 

  14. Weirauch, K.K., Gemeinhardt, P.G. and Baren, A.L. (1976) Soc. Plast. Eng. Preprints, 22, 317.

    CAS  Google Scholar 

  15. Gaku, M., Suzuki, K. and Ikeguchi, N. (1977) Proc. Elec. Electronic Insul. Conf., 13, 11.

    CAS  Google Scholar 

  16. Shimp, D.A., Christenson, J.R. and Ising, S.J. (1991) Cyanate Ester Resins — Chemistry, Properties and Applications, Technical Bulletin, Ciba, Ardsley, NY.

    Google Scholar 

  17. Bogan, G.W., Lyssy, M.E., Monnerat, G.A. and Woo, E.P. (1988) SAMPE J., 24, 19.

    CAS  Google Scholar 

  18. Groving, N. and Holm, A. (1965) Acta Chem. Scand., 19, 1768.

    CAS  Google Scholar 

  19. Hedayatullah, M. and Denivelle, L. (1963) C.R. Acad. Sci. Paris, 256, 4029.

    Google Scholar 

  20. Grigat, E. and Pütter, R. (1964) Chem. Ber., 97, 3018.

    CAS  Google Scholar 

  21. Hageman, H.A. (1953) Org. React., 7, 198.

    Google Scholar 

  22. Pankratov, V.A., Frenkel, Ts.M., Vinogradova, S.V., Bondarev, V.B. and Korshak, V.V. (1974) Izv. Akad. Nauk SSSR, Ser. Khim., 1414.

    Google Scholar 

  23. Shimp, D.A. (1986) Am. Chem. Soc.: Poly. Mat. Sci. Eng. Preprints, 54, 107.

    CAS  Google Scholar 

  24. Cooley, J.H. and Evain, E.J. (1989) Synthesis, 1.

    Google Scholar 

  25. Grigat, E. and Pütter, R. (1971) US Patent 3,553,244.

    Google Scholar 

  26. Glemser, O. (1965) Handbook of Preparative Inorganic Chemistry. Academic Press, New York, pp. 662–666.

    Google Scholar 

  27. Martin, D. and Bauer, M. (1983) Org. Synth., 61, 35.

    CAS  Google Scholar 

  28. Kauer, J.C. and Henderson, W.W. (1964) J. Am. Chem. Soc., 86, 4732.

    CAS  Google Scholar 

  29. Loudas, B.L. and Vogel, H.A. (1973) US Patent 3,733,349.

    Google Scholar 

  30. Snow, A.W. and Griffith, J.R. (1980) J. Fluorine Chem., 15, 471.

    CAS  Google Scholar 

  31. Meyer, K.-H., Burkhardt, C. and Bottenbruch, L. (1976) US Patent 3,994,949.

    Google Scholar 

  32. Rottloff, G., Sundernann, R., Grigat, E. and Pütter, R. (1977) US Patent 4,028,393.

    Google Scholar 

  33. Craig, W.M. (1992) US Patent 5,162,574.

    Google Scholar 

  34. Murry, D.J. and Woo, E.P. (1988) US Patent 4,748,270.

    Google Scholar 

  35. Jensen, K.A. (1934) Z. anorg. allgem. Chem., 221, 11.

    CAS  Google Scholar 

  36. Jensen, K.A., Anthoni, U. and Holm, A. (1969) Acta Chem. Scand.,23, 1916.

    CAS  Google Scholar 

  37. Jensen, K.A., Holm, A. and Thorkilsen, B. (1964) Acta Chem. Scand., 18, 825.

    CAS  Google Scholar 

  38. Jensen, K.A., Due, M. and Holm, A. (1965) Acta Chem. Scand., 19, 438.

    CAS  Google Scholar 

  39. Martin, D. (1964) Angew. Chem. Int. Edn., 3, 311.

    Google Scholar 

  40. Martin, D. (1964) Chem. Ber., 97, 2689.

    CAS  Google Scholar 

  41. Martin, D. (1965) Tetrahedron Lett., 2829.

    Google Scholar 

  42. Martin, D. and Mucke, U. (1965) Chem. Ber., 98, 2059.

    CAS  Google Scholar 

  43. Martin, D. (1965) Ger. (East) Patent 37487.

    Google Scholar 

  44. Mol Percent Impurity by Differential Scanning Calorimetry. ASTM E 928-83.

    Google Scholar 

  45. Bauer, M. and Bauer, J. (1989) Makromol. Chem. Symp., 30, 1.

    CAS  Google Scholar 

  46. Bauer, M., Bauer, J. and Much, H. (1986) Acta Polym., 37, 221.

    CAS  Google Scholar 

  47. Shimp, D.A. and Tompkins, P.T. (1992) Joint Southeastern-Middle Atlantic Regional Meeting, Arlington, VA, Dec. 9.

    Google Scholar 

  48. Fang, T. (1990) Macromolecules, 23, 4553.

    CAS  Google Scholar 

  49. Barton, J.M., Greenfield, D.C.L., Hamerton, I. and Jones, J.R. (1991) Polymer Bull. 25, 475.

    CAS  Google Scholar 

  50. Fyfe, C.A., Niu, J., Rettig, S.J., Burlinson, N.E., Reidsema, C.M., Wang, D.W. and Poliks, M. (1992) Macromolecules, 25, 6289.

    CAS  Google Scholar 

  51. Gupta, A.M. and Macosko, C.W. (1993) Macromolecules, 26, 2455.

    CAS  Google Scholar 

  52. Radeglia, R., Storek, W., Engelhardt, G., Ritsehl, F., Lippmaa, E., Pehk, T., Mägi, M. and Martin, D. (1973) Org. Magn. Resonance, 5, 419.

    CAS  Google Scholar 

  53. Chew, K.F., Derbyshire, W., Logan, N., Norbury, A.H. and Sinha, A.I.P. (1970) J. Chem. Soc. D, 1708.

    Google Scholar 

  54. Hoyer, H. (1960) Chem. Ber., 94, 1042.

    Google Scholar 

  55. Martin, D. (1964) Chem. Ber., 97, 2689.

    CAS  Google Scholar 

  56. Bauer, M., Bauer, J. and Kühn, G. (1986) Acta Polym., 37, 218.

    CAS  Google Scholar 

  57. Groving, N. and Holm, A. (1965) Acta Chem. Scand., 19, 443.

    CAS  Google Scholar 

  58. Reich, P. and Martin, D. (1965) Chem. Ber., 98, 2063.

    CAS  Google Scholar 

  59. Cercena, J.L. (1984) Ph.D. Dissertation, Department of Chemistry, University of Connecticut.

    Google Scholar 

  60. Simon, S.L. and Gillham, J.K. (1993) J. Appl. Poly. Sci., 47, 461.

    CAS  Google Scholar 

  61. Davies, J.M.R., Hamerton, I., Jones, J.R., Povey, D.C. and Barton, J.M. (1990) J. Cryst. Spectros. Res., 20, 287.

    Google Scholar 

  62. Armistead, J.P. and Snow, A.W. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 457.

    CAS  Google Scholar 

  63. Smith, A.L. (1979) Applied Infrared Spectroscopy, Wiley, New York, p. 251.

    Google Scholar 

  64. Bauer, J., Bauer, M., Kuban, R.-J. and Schulz, B. (1987) Acta Polym., 38, 655.

    CAS  Google Scholar 

  65. Al-Mahdi, A.A.K., and Ubbelohde, A.R. (1953) Proc. Roy. Soc. A, 220, 143.

    CAS  Google Scholar 

  66. Andrews, J.N. and Ubbelohde, A.R. (1955) Proc. Roy. Soc., A, 228, 435.

    CAS  Google Scholar 

  67. Snow, A.W. and Armistead, J.P. (1991) Dilatometry on Thermoset Resins. NRL Memorandum Report 6848, NTIS ADA239276.

    Google Scholar 

  68. Shimp, D.A. and Craig, W.M. Jr (1989) 34th Int. SAMPE Symp. Exhib. 34, 1336.

    CAS  Google Scholar 

  69. Bauer, M., Bauer, J. and Garske, B. (1986) Acta Polym., 37, 604.

    CAS  Google Scholar 

  70. Osei-Owusu, A., Martin, G.C. and Gotro, J. (1991) Polym. Eng. Sci., 31, 1604.

    CAS  Google Scholar 

  71. Georjon, O., Galy, J. and Pascault, J.-P. (1993) J. Appl. Polym. Sci., 49, 1441.

    CAS  Google Scholar 

  72. Stutz, H. and Mertes, J. (1993) J. Polym. Sci., Part A, 31, 2031.

    CAS  Google Scholar 

  73. Bonetskaya, A.K., Kravchenko, M.A., Frenkel, Ts.M., Pankratov, V.A., Korshak, V.V. and Vinogradova, S.V. (1981) Vysokomol. Soed. A23, 1494.

    CAS  Google Scholar 

  74. Lebedev, B.V., Aron, B.M., Kiparisova, Ye.G., Rabinovich, I.B., Pankratov, V.A., Vinogradova, S.V. and Korshak, V.V. (1975) Vysokomol. Soed. A17, 2694.

    CAS  Google Scholar 

  75. Bauer, M. and Krüger, R.-P. (1986) Acta Polym., 37, 654.

    Google Scholar 

  76. Bauer, M. and Rodekirch, G. (1986) Acta Polym., 37, 654.

    Google Scholar 

  77. Kohn, J., Albert, E.C., Wilchek, M. and Langer, R. (1986) Anal. Chem., 58, 3184.

    CAS  Google Scholar 

  78. Krespan, C. (1969) J. Org. Chem., 34, 1278.

    CAS  Google Scholar 

  79. Forbes, G.S. and Anderson, H.H. (1940) J. Am. Chem. Soc., 62, 761.

    CAS  Google Scholar 

  80. Eaborn, C., Lickiss, P.D., Marquina-Chidsey, G. and Thorli, E.Y. (1982) J. Chem. Soc., Chem. Commun., 1326.

    Google Scholar 

  81. Eaborn, C., El-Kaddar, Y.Y. and Lickiss, P.D. (1983) J. Chem. Soc., Chem. Commun., 1450.

    Google Scholar 

  82. Eaborn, C., El-Kaddar, Y.Y. and Lockiss, P.D. (1992) , 198–200, 337.

    Google Scholar 

  83. Köhler, H., Menzel, R., Köhler, M. and Jäger, L. (1987) Z. Chem., 27, 294.

    Google Scholar 

  84. Korshak, V.V., Vinogradova, S.V. and Pankratov, V.A. (1971) Izv. Akad. Nauk SSSR, Ser. Khim., 890.

    Google Scholar 

  85. Shimp, D.A. and Ising, S.J. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 504.

    CAS  Google Scholar 

  86. Martin, D., Brause, W. and Radeglia, R. (1970) J. Prakt. Chem., 312, 797.

    CAS  Google Scholar 

  87. Snow, A.W. and Armistead, J.P. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 508.

    CAS  Google Scholar 

  88. Martin, D. and Brause, W. (1970) J. Prakt. Chem., 312, 789.

    CAS  Google Scholar 

  89. Kohn, J. and Langer, R. (1986) Biomaterials, 7, 176.

    CAS  Google Scholar 

  90. AroCy ® Cyanate Ester Safety and Handling Bulletin, (1993) Ciba-Geigy Corp., New York.

    Google Scholar 

  91. Osei-Owusu, A., Martin, G.C, Poliks, M.D., Balko, J.W. and Gotro, J.T. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 449.

    CAS  Google Scholar 

  92. Cozzens, R.F., Walter, P. and Snow, A.W. (1987) J. Appl. Polym. Sci., 34, 601.

    CAS  Google Scholar 

  93. Shimp, D.A. and Ising, S.J. (1990) 35th Int. SAMPE Symp. Exhib., 35, 1045.

    CAS  Google Scholar 

  94. Jarvie, D.A. (1988) 33rd Int. SAMPE Symp., 33, 1405.

    CAS  Google Scholar 

  95. Bogan, G.W., Lyssy, M.E., Monnerat, G.A. and Woo, E.P. (1988) SAMPE J., 24, 19.

    CAS  Google Scholar 

  96. Yang, P.C., Pickelman, D.M. and Woo, E.P. (1990) 35th Int. SAMPE Symp., 35, 1131.

    CAS  Google Scholar 

  97. Das, S., Prevorsek, D.C. and Debona, B.T. (1989) 21st Int. SAMPE Tech. Conf., 21, 972.

    CAS  Google Scholar 

  98. Das, S., Prevorsek, D.C. and Debona, B.T. (1990) Modern Plastics, 72.

    Google Scholar 

  99. Das, S. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 506.

    CAS  Google Scholar 

  100. Armistead, J.P. and Snow, A.W. (1990) Polym. Preprints, 31(2) 537.

    CAS  Google Scholar 

  101. Delano, C.B. and Harrison, E.S. (1975) 20th Nat. SAMPE Symp. Exhib. 20, 243.

    CAS  Google Scholar 

  102. Hergenrother, P.M., Harrison, E.S. and Gosnell, R.B. (1978) 23rd Nat. SAMPE Symp., 23, 506.

    CAS  Google Scholar 

  103. Shimp, D.A., Christenson, J.R. and Ising, S.J. (1989) SPE/Case Western Conf. High Temp. Polym.Cleveland, OH, Society of Plastics Engineers, pp. 127–140

    Google Scholar 

  104. Mormann, W. and Zimmermann, J. (1992) Polym. Mat. Sci. Eng. Preprints, 66, 498.

    CAS  Google Scholar 

  105. Vinogradova, S.V., Pankratov, V.A., Puchin, A.G. and Korshak, V.V. (1971) Izv. Akad. Nauk SSSR, Ser. Khim., 837.

    Google Scholar 

  106. Hedayatullah, M. (1967) Bull. Soc. Chim. France, 422.

    Google Scholar 

  107. Holland, W.R. and Fang, T. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 500.

    CAS  Google Scholar 

  108. Snow, A.W., Griffith, J.R., Soulen, R.L., Greathouse, J.A. and Lodge, J.K. (1992) Am. Chem. Soc.: Polym. Mat. Sci. Eng. Preprints, 66, 466.

    CAS  Google Scholar 

  109. Hamerton, I., Jones, J.R., Povey, D.C., Smith, G.W. and Barton, J.M. (1992) J. Cryst. Spec. Res., 22, 101.

    CAS  Google Scholar 

  110. Barton, J.M., Hamerton, I. and Jones, J.R. (1992) Polym. Int. 29, 145.

    CAS  Google Scholar 

  111. Loudas, B.L. and Vogel, H.A. (1971) US Patent 3,595,900.

    Google Scholar 

  112. Chaplin, A., Hamerton, I., Howlin, B.J. and Barton, J.M. (1994) Macromolecules, in press.

    Google Scholar 

  113. Huang, S.J., Feldman, J.A. and Cercena, J.L. (1989) Polym. Preprints, 30(1), 348.

    CAS  Google Scholar 

  114. Barclay, G.G., Ober, C.K., Papathomas, K.I. and Wang, D.W. (1991) Polym. Preprints, 32(3), 337.

    CAS  Google Scholar 

  115. Wang, Y.-H., Hong, V.Y.-L. and Hong, J.-L. (1993) J. Polym., 34, 1970.

    CAS  Google Scholar 

  116. Cox, R.J., Summa, W.J. and Wang, D.W. (1988) US Patent 4,745,215.

    Google Scholar 

  117. Brand, R.A. and Harrison, E.S. (1979) NASA-CR-3185, CASD-NAS-012, Avail. NTIS.

    Google Scholar 

  118. Papathomas, K.I. and Wang, D.W. (1992) J. Appl. Polym. Sci., 44, 1267.

    CAS  Google Scholar 

  119. Godschalx, J.P., Murray, D.J. and Mendoza, A. (1988) US Patent 4,782,178.

    Google Scholar 

  120. Hefner, R.E. Jr, (1987) US Patent 4,683,276.

    Google Scholar 

  121. Bauer, M., Bauer, J. and Kühn, G. (1986) Acta Polym. 37, 715.

    CAS  Google Scholar 

  122. Cercena, J.L. and Huang, S.J. (1984) Polym. Preprints, 25(1), 114.

    CAS  Google Scholar 

  123. Korshak, V.V., Pankratov, V.A., Adkadskii, A.A., Puchin, A.G. and Vinogradova, S.V. (1974) Vysokomol. Soed. A16(5), 981.

    CAS  Google Scholar 

  124. Mumby, S.J. (1989) J. Electronic Mat., 18, 241.

    CAS  Google Scholar 

  125. Cordova, D.S. and Collier, L.S. (1992) 37th Int. SAMPE Symp., 37, 1406.

    CAS  Google Scholar 

  126. Speak, S.C., Sitt, H. and Fuse, R.H. (1991) 36th Int. SAMPE Symp., 36, 336.

    CAS  Google Scholar 

  127. Bauer, J. and Bauer, M. (1990) J. Macromol. Sci. Chem., A27, 97.

    Google Scholar 

  128. Shimp, D.A. and Wentworth, J.E. (1992) 37th Int. SAMPE Symp., 37, 293.

    CAS  Google Scholar 

  129. Pankratov, V.A., Maiorova, A.A., Korshak, V.V. and Vinogradova, S.V. (1975) Vysokomol. Soed., A17, 2189.

    CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1994 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Snow, A.W. (1994). The synthesis, manufacture and characterization of cyanate ester monomers. In: Hamerton, I. (eds) Chemistry and Technology of Cyanate Ester Resins. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-1326-7_2

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-1326-7_2

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4577-3

  • Online ISBN: 978-94-011-1326-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics