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Polymer Synthesis/Polymer Catalysis pp 59–86Cite as

N-benzyl and N-alkoxy pyridinium salts as thermal and photochemical initiators for cationic polymerization

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Part of the book series: Advances in Polymer Science ((POLYMER,volume 127))

Abstract

Cationic polymerizations induced by thermally and photochemically latent N-benzyl and N-alkoxy pyridinium salts, respectively, are reviewed. N-Benzyl pyridinium salts with a wide range of substituents of phenyl, benzylic carbon and pyridine moiety act as thermally latent catalysts to initiate the cationic polymerization of various monomers. Their initiation activities were evaluated with the emphasis on the structure-activity relationship. The mechanisms of photoinitiation by direct and indirect sensitization of N-alkoxy pyridinium salts are presented. The indirect action can be based on electron transfer reactions between pyridinium salt and (a) photochemically generated free radicals, (b) photoexcited sensitizer, and (c) electron rich compounds in the photoexcited charge transfer complexes. N-Alkoxy pyridinium salts also participate in ascorbate assisted redox reactions to generate reactive species capable of initiating cationic polymerization. The application of pyridinium salts to the synthesis of block copolymers of monomers polymerizable with different mechanisms are described.

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5 References

  1. Kennedy JP (1982) Carbocationic polymerization. Wiley Interscience, New York

    Google Scholar 

  2. Crivello JV (1991) In: Dietliker K (ed) Chemistry & technology of UV & EB formulation for coatings, inks & paints. SITA Technology, London, Chap III

    Google Scholar 

  3. Crivello JV, Lam JHW (1980) J Polym Sci Polym Chem Ed 18: 2677

    Article  CAS  Google Scholar 

  4. Crivello JV, Lam JHW (1980) J Polym Sci Polym Chem Ed 18: 2967

    Google Scholar 

  5. Crivello JV, Lam JHW (1979) Macromolecules 10: 1307

    Article  Google Scholar 

  6. Crivello JV (1984) Adv Polym Sci 62, 1

    CAS  Google Scholar 

  7. Endo T, Uno H (1985) J Polym Sci Polym Lett Ed 23, 359

    Article  CAS  Google Scholar 

  8. Kikkawa A, Takata T, Endo T (1991) Makromol Chem 192, 655

    Article  CAS  Google Scholar 

  9. Hamazu F, Akashi, Koizumi, Takata T, Endo T (1991) J Polym Sci Polym Chem 29, 1675

    Article  CAS  Google Scholar 

  10. Hamazu F, Akashi, Koizumi, Takata T, Endo T (1991) J Polym Sci Polym Chem 29, 1845

    Article  CAS  Google Scholar 

  11. Park J, Kihara N, Ikeda T, Endo T (1993) J Polym Sci Polym Chem Ed 31, 1083

    CAS  Google Scholar 

  12. Hamazu F, Akashi, Koizumi, Takata T, Endo T (1991) J Polym Sci Polym Chem 31, 1023

    Article  Google Scholar 

  13. Hamazu F, Akashi, Koizumi, Takata T, Endo T (1992) J. Photopolym Sci Techn 5, 247

    CAS  Google Scholar 

  14. Hamazu F, Akashi, Koizumi, Takata T, Endo T (1992) Makromol Chem Rapid Commun 13, 203

    Article  CAS  Google Scholar 

  15. Morio K, Murase H, Tsuciya H, Endo T (1986) J Appl Polym Sci 32, 5727

    Article  CAS  Google Scholar 

  16. Lin MP, Ikeda T, Endo T (1992) J Polym Sci Polym Chem 30, 2576

    Google Scholar 

  17. Lin MP, Hayashi Y, Ikeda T, Endo T (1992) J Polym Mat Sci 27, 2992

    Google Scholar 

  18. Yagci Y, Denizligil S, McArdle C (1995) Polymer, 36, 3093

    Article  Google Scholar 

  19. Schelesinger SI (1974) Photogr Sci Eng 18, 387

    Google Scholar 

  20. Crivello JV (1989) Radiation Curing Workshop, ACS Meeting Dallas April

    Google Scholar 

  21. Takata T, Takuma K, Endo T (1993) Makromol Chem, Rapid Commun 14, 203

    Article  CAS  Google Scholar 

  22. Takuma K, Takata T, Endo T (1993) J Photopolym Sci Techn 6, 67

    CAS  Google Scholar 

  23. Takuma K, Takata T, Endo T (1993) Macromolecules 26, 862

    Article  CAS  Google Scholar 

  24. Uno H, Endo T (1988) J Polym Sci Polym Lett Ed 26, 453

    Article  CAS  Google Scholar 

  25. Lee SB, Takata T, Endo T (1989) Chem Let 1861

    Google Scholar 

  26. Lee SB, Takata T, Endo T (1991) Macromolecules 24, 2689

    Article  CAS  Google Scholar 

  27. Nakano S, Endo T (1993) Prog Org Coatings 22, 862

    Article  Google Scholar 

  28. Uno H, Takata T, Endo T (1988) Chem Let 935

    Google Scholar 

  29. Lee SB, Takata, Endo T (1990) Macromolecules 23, 431

    Article  CAS  Google Scholar 

  30. Nakano S, Endo T (1995) J Polym Sci Polym Chem Ed 33, 505

    CAS  Google Scholar 

  31. Yagci Y, Schnabel W (1994) Macromol Symp 84, 115

    Google Scholar 

  32. Roloff A, Meir K, Riediker (1986) Pure Appl Chem 58, 1267

    CAS  Google Scholar 

  33. Meir K, Zwifel H (1986) J Radiat Curing 13, 26

    Google Scholar 

  34. Berner G, Kirchmayer R, Rist G, Rutsch W (1986) J Radiat Curing 13(4), 10

    CAS  Google Scholar 

  35. Fouassiser JP, Burr D (1990) Macromolecules 23, 3615

    Article  Google Scholar 

  36. Hayase S, Onishi Y, Suzuki S, Wada M (1986) Macromolecules 19, 968

    Article  CAS  Google Scholar 

  37. Abdoul Rasoul FM, Ledwith A, Yagci Y (1978) Polymer 19, 1219

    Article  Google Scholar 

  38. Bottcher A, Hasebe K, Hizal G, Yagci Y, Stelberg P, Schnabel W (1991) Polymer 32, 2289

    Article  Google Scholar 

  39. Lange NA (1985) In: Dean JA (ed.) Lange's Handbook of Chemistry, 13th ed., McGraw Hill, New York, pp 5–60

    Google Scholar 

  40. March J (1985) In: Advanced Organic Chemistry, 3rd ed.; Wiley-Interscience, New York, p 248

    Google Scholar 

  41. Uno H, Takata T, Endo T (1989) Macromolecules 22, 2502

    Article  CAS  Google Scholar 

  42. Lee SB, Lee SD, Takata T, Endo T (1991) Synthesis 5, 368

    Article  Google Scholar 

  43. Gruber HF (1992) Prog Polym Sci 17, 953

    Article  CAS  Google Scholar 

  44. Pappas SP (1985) UV Curing Science and Technology, Vol. II, Technology Marketing Corp., Norwalk, CT

    Google Scholar 

  45. Allen NS (1989) Photopolymerizaton and Photoimaging Science and Technology, Elsevier, New York, pp 55–75

    Google Scholar 

  46. Reichard C (1966) Chem Ber 99, 1769

    Google Scholar 

  47. Yagci Y, Kornowski A, Schnabel W (1992) J Polym Sci Polym Chem Ed 30, 1987

    CAS  Google Scholar 

  48. Yagci Y, Kornowski A, Masonne K, Schanabel W (1991) Pending Patent Application, DE-P 4103906.8, Feb.

    Google Scholar 

  49. Yagci Y, Schnabel W (1993) Macromol Reports, A30 (Suppl. 3 & 4) 175

    CAS  Google Scholar 

  50. Bottcher A, Schanabel W, Yagci Y (1990) Pending Patent Application DE-P 4003925, Feb.

    Google Scholar 

  51. Yagci Y, Schnabel W (1987) Makromol Chem, Rapid Commun 8, 209

    Article  CAS  Google Scholar 

  52. Yagci Y, Schnabel W (1988) Makromol Chem, Macromol Symp 13–14, 161

    Google Scholar 

  53. Yagci Y, Borberly B, Schnabel W (1989) Eur Polym J 25, 129

    Article  CAS  Google Scholar 

  54. Scanio JC, Encinas MV, George MV (1974) J Chem Soc Perkin Trans. 2, 1, 724

    Google Scholar 

  55. Hyde P, Ledwith A (1974) J Chem Soc Perkin Trans, 1768

    Google Scholar 

  56. Yagci Y, Denizligil S (1995) J Polym Sci, Polym Chem Ed 33, 1461

    Article  CAS  Google Scholar 

  57. Johnen N, Kobayashi S, Yagci Y, Schnabel W (1993) Polym Bull 30, 279

    Article  CAS  Google Scholar 

  58. Kitamura T, Koboyashi S, Tanuguchi H (1986) J Am Chem Soc 108, 2641

    Article  CAS  Google Scholar 

  59. Yagci Y, Kminek I, Schnabel W (1992) Eur Polym J 28, 387

    Article  CAS  Google Scholar 

  60. Michl J, Downing JW, Karatsu T, McKinley AJ, Poggy G, Wallraff GM, Sooriyakumaran R, Miller RD (1988) Pure & Appl Chem 60, 959

    CAS  Google Scholar 

  61. West R, Wolf AR, Peterson PJ (1986) J Radiat Curing 13, 35

    CAS  Google Scholar 

  62. Kminek I, Yagci Y, Schnabel W (1992) Polym Bull 29, 277

    Article  CAS  Google Scholar 

  63. Yagci Y, Kminek I, Schnabel W (1993) Polymer 34, 426

    Article  CAS  Google Scholar 

  64. Yagci Y, Lukac I, Schnabel W (1993) Polymer 34, 1130

    Article  CAS  Google Scholar 

  65. Rehm D, Weller A (1969) Bunsenges Phys Chem 73, 834

    CAS  Google Scholar 

  66. Dossow D, Hizal G, Zhu QQ, Yagci Y, Schnabel W (1995) Polymer submitted

    Google Scholar 

  67. Ohtsuka T, Yamamoto, Hayashi K (1988) J Polym Sci Polym Lett Ed, 26, 481

    Article  CAS  Google Scholar 

  68. Hizal G, Yagci Y, Schnabel W (1994) Polymer 35, 2428

    Article  CAS  Google Scholar 

  69. Crivello JV, Lam JHW (1981) J Polym Sci Polym Chem Ed 19, 539

    Article  CAS  Google Scholar 

  70. Onen A, Yagci Y (1995) in preparation

    Google Scholar 

  71. Kayaman N, Onen A, Yagci Y, Schnabel W (1994) Polym Bull 32, 589

    Article  CAS  Google Scholar 

  72. Onen A, Yagci Y (1990) J Macromol Sci Chem A27 743

    CAS  Google Scholar 

  73. Onen A, Yagci Y (1990) Angew Makromol Chem 181, 191

    Article  CAS  Google Scholar 

  74. Yagci Y, Onen A (1991) J Macromol Sci Chem A28, 129

    CAS  Google Scholar 

  75. Yagci Y, Onen A, Schnabel W (1991) Macromolecules 24, 4620

    Article  CAS  Google Scholar 

  76. Onen A, Yagci Y (1992) Eur Polym J 28, 721

    Article  CAS  Google Scholar 

  77. Serhatli IE, Galli G, Chiellini E, Yagci Y (1995) Polym Bull, 34, 539

    Article  CAS  Google Scholar 

  78. Hizal G, Yagci Y, Schnabel W (1994) Polymer 35, 4443

    Article  CAS  Google Scholar 

  79. Hizal G, Sarman A, Yagci Y (1995) Polym Bull 35, 567

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Istanbul Technical University, 80626, Maslak, Istanbul, Turkey

    Yusuf Yagci

  2. Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuda-Cho, Midori-Ku, 226, Yokohama, Japan

    Takeshi Endo

Authors
  1. Yusuf Yagci
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  2. Takeshi Endo
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© 1997 Springer-Verlag

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Yagci, Y., Endo, T. (1997). N-benzyl and N-alkoxy pyridinium salts as thermal and photochemical initiators for cationic polymerization. In: Polymer Synthesis/Polymer Catalysis. Advances in Polymer Science, vol 127. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0103629

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  • DOI: https://doi.org/10.1007/BFb0103629

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-61288-9

  • Online ISBN: 978-3-540-68444-2

  • eBook Packages: Springer Book Archive

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