Non-halogenated Flame Retardant Handbook. Группа авторов

retardants have not escaped environmentalist concerns and there are a growing number of academic publications that detect organophosphorus flame retardants in the environment. However, it would be an error to say that phosphorus flame retardants are found more often because they replace halogens. Mostly relatively mobile organophosphorus flame retardants that were detected have been in use for at least half a century. Specific organophosphorus compounds raised sufficient concerns to warrant their discontinuance, but this was not generic to the entire class. Following the general trend of the flame-retardant industry towards polymeric and reactive products which show less negative effects to the final products and minimal exposure to humans and the environment, phosphorus flame retardants will follow this general strategy. Trends in the research and development of phosphorus flame retardants have been in the direction of less volatile, less toxic, and more stable compounds, and where feasible, in the direction of built-in phosphorus structures. At the same time, the existing phosphorus flame retardants are finding increased exploitation in the form of mixtures with synergists and adjuvants.

      References

      1. Georlette, P., Simons, J., Costa, L., Halogen-containing Fire-Retardant Compounds, in: Fire Retardancy of Polymeric Materials, A.F. Grand and C.A. Wilkie (Eds.), pp. 245–284, Marcel Dekker, 2000.

      2. Levchik, S.V., Phosphorus-based FRs, in: Non-halogenated Flame Retardant Handbook, A.B. Morgan and C.A. Wilkie (Eds.), pp. 17–74, Wiley, New York, 2014.

      3. Levchik, S.V. and Weil, E.D., A review of recent progress in phosphorus-based flame retardants, J. Fire Sci., 24, 345, 2006.

      4. Levchik, S.V. and Weil, E.D., Developments in phosphorus flame retardants, in: Advances in Fire Retardant Materials, A.R. Horrocks and D. Price (Eds.), pp. 41–66, Woodhead, Boca Raton, FL, 2008.

      5. Hoerold, S., Phosphorus-based and intumescent flame retardants, in: Polymer Green Flame Retardants, C.D. Papaspyrides and P. Kiliaris (Eds.), pp. 221–254, Elsevier, Amsterdam, 2014.

      6. Joseph, P. and Ebdon, J.R., Phosphorus-based flame retardants, in: Fire Retardancy of Polymeric Materials, C.A. Wilkie and A.B. Morgan (Eds.), CRC Press, Boca Raton, FL, pp. 107–127, 2009.

      7. Jain, P., Choudhary, V., Varma, I.K., Flame Retarding Epoxies with Phosphorus, J. Macromol. Sci., Polym. Rev., C42, 139, 2002.

      8. Schartel, B., Phosphorus-based flame retardancy mechanisms - old hat or a starting point for future development? Materials, 3, 4710, 2010.

      9. Flammability: A New Look at Age-old Problem. Dimensions, Tech. News Bull. NBS, 58, 6, 130, 1974.

      10. I. Sakon, Red phosphorus flame retardant and nonflammable resinous composition containing the same, US Patent 4879067, assigned to Rinkagaku Kogyo, November 7, 1989.

      11. Uske, K. and Ebenau, A., A plea for red phosphorus. flame-retardant polyamides, Kunststoffe Int., 9, 130, 2013.

      12. Y. Kinose, A. Inoue, T. Nagayama, Modified red phosphorus, method of producing the same, decolorized red phosphorus composition and flame-retardant polymer composition, US Patent 7045561, assigned to Nippon Chemical, May 16, 2006.

13. A. Koenig, T. Erdmann, M. Roth, K. Uske, J. Engelmann, A. Ebenau, M. Klatt, Pale-colored flame-retardant polyamides, US Patent 9388341, assigned to BASF, July 12, 2016.

      14. P. Baierweck, D. Zeltner, G. Heiner, K. Ulmerich, K. Muehlbach, M. Gall, Flameproofed black polyamide molding materials, US Patent 5405890, assigned to BASF, April 11, 1995.

      15. Weil, E.D., Formulation and modes of action of red phosphorus, in: Proc. BCC Conf. Recent Advances in Flame Retardancy of Polymeric Materials, Stamford, CT, May 2000.

      16. M. Wagner, W. Podszun, H. Peerling, Microencapsulation of red phosphorus, US Patent 6846854, assigned to Bayer, January 25, 2005.

      17. M. Suzuki, K. Hironaka, J. Haruhara, Fire-retardant resin compositions, European Patent 0978540, assigned to Teijin, December 7, 2005.

      18. S. Hoerold and J. Laubner, Stabilized red phosphorus material and a process for its preparation, US Patent 6645625, November 11, 2003.

      19. W. Nielinger, K.H. Herrmann, D. Michael, Stabilized red phosphorus and its use for flameproofing thermoplastic polyamide molding compositions, US Patent 4550133, assigned to Bayer, October 29, 1985.

      20. Y. Bonin and J. LeBlanc, Fire-resistant polyamide compositions, US Patent 4985485, assigned to Rhone-Poulenc, January 15, 1991.

      21. Gatti, N., New red phosphorus masterbatches find new application areas in thermoplastics, Plast. Add. Compound., 34, April 2002.

      22. Huggard, M.T., Phosphorus flame retardants – activation ‘synergists, in: Proc. BCC Conf. Recent Advances in Flame Retardancy of Polymeric Materials, Stamford, CT, May 1992.

      23. M.-K. Lim, Fire-retardant composition of an alloy of polyamide and polyester resins, US Patent 9765217, assigned to Rhodia, September 19, 2017.

      24. A. Koenig, S. Xue, K. Uske, M. Roth, Flame-retardant thermoplastic molding composition, US Patent 8629206, assigned to BASF, January 14, 2014.

      25. M. Roth, M. Heussler, K. Uske, C. Minges, Polyamide with phosphorus and Al phosphonates, PCT Patent Application WO 2018/234429, assigned to BASF, December 27, 2018.

      26. M. Roth, K. Uske, C. Minges, Glow wire resistant polyamides, US Patent 9828503, assigned to BASF, November 28, 2017.

      27. Alfonso, G.C., Costa, G., Pasolini, M., Russo, S., Ballistreri, A., Montaudo, G., Puglisi, C., Flame-resistant polycaproamide by anionic polymerization of e-caprolactam in the presence of suitable flame-retardant agents, J. Appl. Polym. Sci., 31, 1373, 1986.

      28. Levchik, S.V., Levchik, G.F., Balabanovich, A.I., Camino, G., Costa, L., Mechanistic study of combustion performance and thermal decomposition behaviour of nylon 6 with added halogen-free fire retardants, Polym. Degrad. Stab., 54, 217, 1996.

29. Suebsaeng, T., Wilkie, C.A., Burger, V.T., Carter, J., Brown, C.E., Solid products from thermal decomposition of polyethylene terephthalate: investigation by CP/MAS 13C-NMR and Fourier Transform-IR spectroscopy, J. Appl. Polym. Sci., 22, 945, 1984.

      30. Schartel, B., Kunze, R., Neubert, D., Red phosphorus-controlled decomposition for fire retardant PA 66, J. Appl. Polym. Sci., 83, 2060, 2002.

      31. Kuper, G., Hormes, J., Sommer, K., Macromol. Chem. Phys., In situ x-ray absorption spectroscopy at the k-edge of red phosphorus in polyamide 6,6 during a thermo-oxidative degradation, 195, 1741, 1994.

      32. Levchik, S.V., Weil, E.D., Lewin, M., Thermal Decomposition of Aliphatic Nylons, Polym. Int., 48, 532, 1999.

      33. Granzow, A., Account. Chem. Res., Flame retardation by phosphorus compounds, 11, 177, 1978.

      34. Peters, E.N., J. Appl. Polym. Sci., Flame-retardant thermoplastics. I. polyethylene - red phosphorus, 24, 1457, 1979.

      35. Gatti, N. and Costanzi, S., Is red phosphorus an effective solution for flame proofing polyolefin articles?, in: Flame Retardants 2004, pp. 133–138, Interscience Communication, London, 2004.

      36. Wu, Q., Lu, J., Qu, B., Polym. Int., Preparation and characterization of microcapsulated red phosphorus and its flame-retardant mechanism in halogen-free flame retardant polyolefins, 52, 1326, 2003.

      37. K. Yamauchi, H. Matsuoka, H. Matsumoto, T. Inoue, Flame retardant resin composition, US Patent 6136892, assigned to Toray, October 24, 2000.

      38. S. Oishi, M. Yoshi, W. Hiraishi, Magnesium hydroxide particles, process for producing the same, and resin composition containing the particles, US Patent 6676920, assigned to Kyowa, January 13, 2004.

      39. Savas, L.A., Deniz, T.K., Tayfun, U., Dogan, M., Effect of microcapsulated red phosphorus on flame retardant, thermal and mechanical properties of thermoplastic polyurethane composites