Synthesis and characterization of novel diglycidyl methacrylate-based macromonomers on isosorbide for dental composites

Zhila Vazifehasl; Salar Hemmati; Mohammadreza Zamanloo; Mehdi Jaymand

Macromolecular Research, Vol.21, No.4, 427-434, April, 2013

DOI10.1007/s13233-013-1038-1 Export Citation

Synthesis and characterization of novel diglycidyl methacrylate-based macromonomers on isosorbide for dental composites

Zhila Vazifehasl^{1, 2}, Salar Hemmati^{1, 3}, Mohammadreza Zamanloo², and Mehdi Jaymand^{4, †}

¹Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran
²Department of Applied Chemistry, Faculty of Science, University of Mohaghegh Ardabili, Ardabil, Iran
³, Iran
⁴Research Center for Pharmaceutical Nanotechnology, Tabriz University of Medical Sciences, Tabriz, Iran

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A new strategy for the synthesis of dimethacrylate-based macromonomers on isosorbide via a ring opening reaction is suggested. For this purpose, ethylene glycol derivatives (mono, di, and tri) were firstly monobrominated, and their hydroxyl groups were protected as tetrahydropyranyl (THP) ethers. Then, the reaction of isosorbide with obtained alkylation reagents were carried out in the presence of NaH/N,N-dimethylformamide (DMF) to provide alkylated isosorbide derivatives. Deprotection of tetrahydropyranyl groups was accomplished under acidic conditions at room temperature and series of new diols from isosorbide were thus prepared in high yields. Eventually, the reaction of new diols with glycidyl methacrylate, which afforded new dimethacrylates containing an isosorbide skeleton, was linked to mono, di, and tri-ethylene glycol moieties. The chemical structures of all samples as representatives were characterized by Fourier transform infrared (FTIR), 13C and 1H nuclear magnetic resonance (NMR) spectroscopy.

Keywords:isosorbide;ethylene glycol derivatives;glycidyl methacrylate;ring opening;macromonomer;crosslinking agent;dental composites

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[2] Abenhaim D, Loupy A, Munnier L, Tamion R, Marsais F, Queguiner G, Carbohydr. Res., 261, 255 (1994)

[3] Claffey DJ, Casey MF, Finan PA, Carbohydr. Res., 339, 2433 (2004)

[4] Stoss P, Hemmer R, Adv. Carbohydr. Chem. Biochem., 49, 92 (1991)

[5] Rose M, Palkovits R, ChemSusChem, 5, 167 (2012)

[6] Lin Q, Pasatta J, Long TE, J. Polym. Sci. A: Polym. Chem., 41(16), 2512 (2003)

[7] Zhang B, Zheng Y, Lu H, Liq. Cryst., 32, 357 (2005)

[8] Chavan NN, Mater. Sci. Appl., 2, 1520 (2011)

[9] Van-Buu ON, Aupoix A, Vo-Thanh G, Tetrahedron, 65, 2260 (2009)

[10] Carcedo C, Dervisi A, Fallis AI, Ooi L, Malik AKM, Chem. Commun., 10, 1236 (2004)

[11] Kumar S, Ramachandran U, Tetrahedron, 61, 4141 (2005)

[12] Chatti S, Bortolussi M, Loupy A, Tetrahedron Lett., 41, 3367 (2000)

[13] Wang J, Zhang C, Qu Z, Hou Y, Chen B, Wu P, J. Chem. Res., 1, 294 (1999)

[14] Naik S, Gopinath R, Patel BK, Tetrahedron Lett., 42, 7679 (2001)

[15] Jung YJ, Park ES, Lee JH, Yoon CM, Bull. Korean Chem. Soc., 23, 791 (2002)

[16] Badalassi F, Klein G, Crotti P, Reymond JL, Eur. J. Org. Chem., 12, 2557 (2004)

[17] Mendez PS, Cachau RE, Seoane G, Ventura ON, THEOCHEM., 904, 21 (2009)

[18] Osterkamp F, Wehlan H, Koert U, Wiesner M, Raddatz P, Goodman SL, Tetrahedron, 55, 10713 (1999)

[19] Denmark SE, Barsanti PA, Beutner GL, Wilson TW, Adv. Synth. Catal., 349, 567 (2007)

[20] Chiniwalla P, Bai YQ, Elce E, Shick R, McDougall WC, Allen SAB, Kohl PA, J. Appl. Polym. Sci., 89(2), 568 (2003)

[21] Ghaemy M, Heidaripour M, Barghamadi M, J. Appl. Polym. Sci., 106(3), 1917 (2007)

[22] Sheela MS, Selvy KT, Krishnan VK, Pal SN, J. Appl. Polym. Sci., 42, 561 (1991)

[23] Sahin G, Albayrak AZ, Sarayli Z, Avci D, J. Polym. Sci. A: Polym. Chem., 44(23), 6775 (2006)

[24] Domingo C, Arcs RW, Lopez-Macipe A, Osorio R, guez-Clemente RR, Murtra J, Fanovich MA, Toledano M, J. Biomed. Mater. Res., 56, 297 (2001)

[25] Chowdhury NA, Wakasa K, Priyawan R, Yamaki M, J. Mater. Sci. -Mater. Med., 6, 400 (1995)

[26] Krishnan VK, Lizymol PP, Nair SP, J. Appl. Polym. Sci., 74(3), 735 (1999)

[27] Atta AM, El-Ghazawy RAM, Farag RK, Abdel-Azim AAA, React. Funct. Polym., 66(9), 931 (2006)

[28] Atta AM, El-Ghazawy RA, Farag RK, Abdel-Azim AA, J. Polym. Res., 13, 257 (2006)

[29] Zhou MH, Cho W, Polym. Int., 50, 1193 (2001)

[30] Atta AM, Arndt KF, Polym. Int., 50, 1360 (2001)

[31] Mark JE, Erman B, in Performance of Plastics, Brostow W, Ed., Hanser, Munich-Cincinnati, 2000, Chap. 17.

[32] Czech Z, Polym. Int., 52, 347 (2003)

[33] Jaymand M, Polym. J., 43, 901 (2011)

[34] Bogdal D, Pielichowski J, Boron A, J. Appl. Polym. Sci., 66(12), 2333 (1997)

[35] Kluger R, Alagic A, Bioorganic Chem., 32, 451 (2004)