Synthesis of Dialklyaminoalkyl Phosphonic Acid and Bis(dialklyaminoalkyl) Phosphinic Acid Derivatives

디알킬아미노알킬 포스폰산과 비스-디알킬아미노알킬 포스핀산 유도체의 합성

  • Chung, Yeong-Jin (Department of Fire Protection Engineering, Kangwon National University) ;
  • Jin, Eui (Fire & Disaster Prevention Research Center, Kangwon National University)
  • 정영진 (강원대학교 소방방재공학과) ;
  • 진의 (강원대학교 소방방재연구센터)
  • Published : 2012.12.10


Six kinds of new aminoalkyl phosphonic acid or aminoalkyl phosphinic acid derivatives with mono-dialkylamino, or di-dialkylamino functional groups in the molecule were synthesized and their smoke densities were tested. The aminoalkyl phposphonic acid or aminoalkyl phosphinic acid derivatives were synthesized with quantitative yields of 90~98.6% by one step reaction of the phosphorus acid or hypo phosphorous acid with amine and aldehyde. The smoke density was measured by the ASTM E 662 method. Values of the smoke density were obtained from 224.5 to 256.6. The smoke density of the compounds with two aminoalkyl structures decreased more than that of compounds with one aminoalkyl structure. In addition, there was no correlation between the smoke density and the number of carbon atoms in the alkyl group attached to the amino group.


  1. M. I. Kabachnik and T. J. Medved, Cehm. Abstr., 47, 2724 (1953).
  2. M. I. Kabachnik, C.A.57, 7293d (1962).
  3. G. L. Nelson, Fire and Polymers, American Chemical Society, Washington DC. (1990).
  4. M. Lewis, S. M. Altas, and E. M. Pearce, Flame-Retardant Polymer Materials, Plenum Press, New York (1975).
  5. S. J. Park, S. W. Song, J. R. Lee, B. G. Min, and J. S. Shin, J. Korean, Ind. Eng. Chem., 15, 41 (2004).
  6. Y. J. Chung, H. M. Lim, E. Jin, and J. K. Oh, Appl. Chem. Eng., 22, 439 (2011).
  7. M. L. Hardy, Polym. Degrad. Stab., 64, 545 (1999).
  8. Y. Tanaka, Epoxy Resin Chemistry and Technology, Marcel Dekker, New York (1988).
  9. Korean Patent 2010-0128046 (2010).
  10. H. Y. Ma and Z. P. Fang, Thermochimica Acta, 543, 130 (2012).
  11. Korean Patent 2011-34978 (2011).
  12. ASTM E 662, Test method for Specific Optical Density of Smoke Generated by Solid Materials (2009).
  13. ISO 5660-2, Reaction-to-Fire Tests-Heat Release, Smoke Production and Mass Loss Rate-Part 2 : Smoke Production Rate (Dynamic measurement) (2002).
  14. D. H. Lee, W. S. Jung, D. S. Park, and S. O. Kim, Smoke Density Characteristics of the FRP Composite Panel for Railcars, Proceeding of 2012 Spring Annual Conference, KIFSE, 505 (2002).
  15. E. K. Fields, J. Am. Chem. Soc., 74, 1528 (1952).
  16. M. I. Kabachnik and T. J. Medved, Dokl. Akad. Nauk. SSSR., 83, 689 (1952).
  17. V. S. Abramov and V. I. Brabanov, Zh. Obsch. Khim., 36, 1830 (1966).
  18. A. N. Pudovik and J. P. Kitaev, Zh. Obshch. Khim., 467, 22 (1952).
  19. M. I. Kabachnik, Z. Chem., 1, 289 (1961).