Simple synthesis of Biphosphonates with Excellent Flameproofing Properties

Yang Cao; Weiwei Zhang; Xufeng Yang; Jinfei Yang; Huizhen Zhi

Korean Chemical Engineering Research, Vol.52, No.2, 187-190, April, 2014

Export Citation

Simple synthesis of Biphosphonates with Excellent Flameproofing Properties

Yang Cao, Weiwei Zhang, Xufeng Yang, Jinfei Yang, and Huizhen Zhi^†

School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, 210046, China

E-mail:

Four excellent halogen-free biphosphonate flame retardants (EBDMP, EBDEP, MBDMP, MBDEP) were synthesized through polycondensation and Arbuzov rearrangement reactions without using any solvents. The products were characterized by ESI-MS, FT-IR and 1H NMR. The application of EBDEP in polyurethane soft foam was studied and the results illustrated its excellent flame-proofing properties

Keywords:Flame Retardants;Biphosphonates;Synthesize;Polycondensation

[References]

Lassiaz S, Galarneau A, Trens P, Labarre D, Mutin H, Brunel D, New J. Chem., 34, 1424 (2010)
Vasiljevic J, Hadzic S, Jerman I, Cerne L, Tomsic B, Medved J, Godec M, Orel B, Simoncic B, "Study of Flame-retardant Finishing of Cellulose Fibres: Organic-inorganic Hybrid Versus Conventional Organophosphonate", Polym. Degrad. Stabi., 2013, doi/10.1016/.
Lin HJ, Liu SR, Han LJ, Wang XM, Bian YJ, Dong LS, Polym. Degrad. Stabi., 98(7), 1389 (2013)
Kohler J, Keul H, Moller M, Chem. Commun., 47, 8148 (2011)
Evano G, Tadiparthi K, Couty F, Chem. Commun., 47(1), 179 (2011)
Murugavel R, Singh MP, New J. Chem., 34(9), 1846 (2010)
Bourbigot S, Duquesne S, J. Mater. Chem., 17, 2283 (2007)
Bourbigot S, Fontaine G, Polym. Chem., 1, 1413 (2010)
Lim H, Chang JY, J.Mater. Chem., 20, 749 (2010)
Wu MS, Chen RY, Huang Y, Chin. J Org. Chem., 24(5), 485 (2004)
Jansa P, Holy A, Dracinsky M, Baszczyoski O, Cesnek M, Janeba Z, Green Chem., 13, 882 (2011)
Masuda K, Sakiyama N, Tanaka R, Noguchi K, Tanaka K, J. Am. Chem. Soc., 133(18), 6918 (2011)
Zhuang RQ, Xu J, Cai ZS, Org. Lett, 13(8), 2110 (2011)
Ashkenazi N, Segall Y, Chen R, J. Org. Chem., 75(6), 1917 (2010)
Rueping M, Zhu SQ, Koenigs RM, Chem. Commun., 47(30), 8679 (2011)
Negrell-Guirao C, Boutevin B, David G, Fruchier A, Sonnier R, Lopez-Cuesta J, Polym. Chem., 2, 236 (2011)
Song PA, Xu LH, Guo ZH, Zhang Y, Fang ZP, J. Mater. Chem., 18, 5083 (2008)
Song PA, Liu H, Shen Y, Du BX, Fang ZP, Wu Y, J. Mater. Chem., 19, 1305 (2009)
Zhuo DX, Gu AJ, Liang GZ, Hu JT, Yuan L, Chen X X, J. Mater. Chem., 21, 6584 (2011)
Brebu M, Sakata Y, Green Chem., 8, 984 (2006)
Bhaskar T, Hosokawa A, Muto A, Tsukahara Y, Yamauchi T, Wada YJ, Green Chem., 10, 739 (2008)
Mosurkal R, Kirby R, Muller WS, Green Chem, 13, 659 (2011)
Song PA, Zhao LP, Cao ZH, Fang ZP, J. Mater. Chem., 21, 7782 (2011)
Wilkie CA, Chigwada G, Gilman Sr.JW, J. Mater.Chem., 16, 2023 (2006)
Shi YM, Li LJ, J. Mater. Chem., 21, 3277 (2011)
Ranganathan T, Cossette P, Emrick T, J. Mater. Chem., 20, 3681 (2010)
Urbanczyk L, Bourbigot S, Calberg C, Detrembleur C, Jerome C, Boschini F, Alexandre M, J. Mater. Chem., 20, 1567 (2010)
Tai QL, Hu Y, Yuen RKK, Song L, Lu HD, J. Mater. Chem., 21, 6621 (2011)
Liu YL, Hsiue GH, Chiu YS, Jeng RJ, Perng LH, J. Appl. Polym. Sci., 61(4), 613 (1996)

[Referenced By]

[1] Lassiaz S, Galarneau A, Trens P, Labarre D, Mutin H, Brunel D, New J. Chem., 34, 1424 (2010)

[2] Vasiljevic J, Hadzic S, Jerman I, Cerne L, Tomsic B, Medved J, Godec M, Orel B, Simoncic B, "Study of Flame-retardant Finishing of Cellulose Fibres: Organic-inorganic Hybrid Versus Conventional Organophosphonate", Polym. Degrad. Stabi., 2013, doi/10.1016/.

[3] Lin HJ, Liu SR, Han LJ, Wang XM, Bian YJ, Dong LS, Polym. Degrad. Stabi., 98(7), 1389 (2013)

[4] Kohler J, Keul H, Moller M, Chem. Commun., 47, 8148 (2011)

[5] Evano G, Tadiparthi K, Couty F, Chem. Commun., 47(1), 179 (2011)

[6] Murugavel R, Singh MP, New J. Chem., 34(9), 1846 (2010)

[7] Bourbigot S, Duquesne S, J. Mater. Chem., 17, 2283 (2007)

[8] Bourbigot S, Fontaine G, Polym. Chem., 1, 1413 (2010)

[9] Lim H, Chang JY, J.Mater. Chem., 20, 749 (2010)

[10] Wu MS, Chen RY, Huang Y, Chin. J Org. Chem., 24(5), 485 (2004)

[11] Jansa P, Holy A, Dracinsky M, Baszczyoski O, Cesnek M, Janeba Z, Green Chem., 13, 882 (2011)

[12] Masuda K, Sakiyama N, Tanaka R, Noguchi K, Tanaka K, J. Am. Chem. Soc., 133(18), 6918 (2011)

[13] Zhuang RQ, Xu J, Cai ZS, Org. Lett, 13(8), 2110 (2011)

[14] Ashkenazi N, Segall Y, Chen R, J. Org. Chem., 75(6), 1917 (2010)

[15] Rueping M, Zhu SQ, Koenigs RM, Chem. Commun., 47(30), 8679 (2011)

[16] Negrell-Guirao C, Boutevin B, David G, Fruchier A, Sonnier R, Lopez-Cuesta J, Polym. Chem., 2, 236 (2011)

[17] Song PA, Xu LH, Guo ZH, Zhang Y, Fang ZP, J. Mater. Chem., 18, 5083 (2008)

[18] Song PA, Liu H, Shen Y, Du BX, Fang ZP, Wu Y, J. Mater. Chem., 19, 1305 (2009)

[19] Zhuo DX, Gu AJ, Liang GZ, Hu JT, Yuan L, Chen X X, J. Mater. Chem., 21, 6584 (2011)

[20] Brebu M, Sakata Y, Green Chem., 8, 984 (2006)

[21] Bhaskar T, Hosokawa A, Muto A, Tsukahara Y, Yamauchi T, Wada YJ, Green Chem., 10, 739 (2008)

[22] Mosurkal R, Kirby R, Muller WS, Green Chem, 13, 659 (2011)

[23] Song PA, Zhao LP, Cao ZH, Fang ZP, J. Mater. Chem., 21, 7782 (2011)

[24] Wilkie CA, Chigwada G, Gilman Sr.JW, J. Mater.Chem., 16, 2023 (2006)

[25] Shi YM, Li LJ, J. Mater. Chem., 21, 3277 (2011)

[26] Ranganathan T, Cossette P, Emrick T, J. Mater. Chem., 20, 3681 (2010)

[27] Urbanczyk L, Bourbigot S, Calberg C, Detrembleur C, Jerome C, Boschini F, Alexandre M, J. Mater. Chem., 20, 1567 (2010)

[28] Tai QL, Hu Y, Yuen RKK, Song L, Lu HD, J. Mater. Chem., 21, 6621 (2011)

[29] Liu YL, Hsiue GH, Chiu YS, Jeng RJ, Perng LH, J. Appl. Polym. Sci., 61(4), 613 (1996)