Restricted accessResearch articleFirst published online 2010-03
Synthesis and Characterization of Isophthalic Polyesters and Copolyesters based on 2,4-Dihydroxybenzophenone and 4,4’-(hexafluoroisopropylidene)diphenol
Two aromatic isophthalic polyesters and three copolyesters were synthesized by interfacial polycondensation using 2,4-dihydroxybenzophenone (2,4-DBP) and 4,4'-(hexafluoroisopropylidene)diphenol (HFD) with isophthaloyl chloride (ISO). All polymers were soluble in common chlorinated solvents. These aromatic polyesters and copolyesters were characterized by infrared and nuclear magnetic resonance spectroscopy. Their thermal, dynamic mechanical and physical properties were also determined. The glass transition temperature, onset of decomposition, and thermal stability of the homopolymer, poly(hexafluoroisopropilydene)isophthalate (HFD/ISO), were higher than those of homopolymer poly(2,4-benzophenone)isophthalate (2,4-DBP/ISO). The thermal properties of the copolyesters HFD/ ISO-co-DBP/ISO depend upon the amounts of HFD/ISO moiety present in the copolymer. Physical properties of the copolyesters were intermediate between those of the homopolyesters and depend upon the concentration of comonomers present in the copolyester.
Bier, G. ( 1974). Polyarylates (Polyesters from Aromatic Dicarboxylic Acids and Bisphenols), Polymer, 15: 527.
2.
Maresca, L.M. , Robeson, L.M. and Nargolis, J.M. (1985). Engineering Thermoplastics: Properties and Applications, Ed. Marcel Dekker , New York, Chapter 10, pp. 255-282.
3.
Arroyo, M. and Olabisi, O. ( 1997). Handbook of Thermoplastics, Ed. Marcel Dekker, New York, pp. 599- 608.
4.
Ober, C.K.Jin, J.I.; Lenz, R.W. (1984). Liquid Crystal Polymers with Flexible Spacers in the Main Chain, Adv. Polym. Sci. , 59: 103-146.
5.
Bucio, E., Lara-Estevez, J.C.I., Ruiz-Treviño, F.A. and Acosta-Huerta, A. ( 2006). Synthesis and Characterization of New Polyesters Derived from Diphenols and Aromatic Diacids Chlorides, Polym. Bull. , 56: 163-170.
Hsiao,S.-H. and Chang, H.-Y. (1995). Synthesis and Properties of Aromatic Polyesters and Brominated Polyesters Derived from α,α'-bis(4-hydroxyphenyl)-1,4(or 1,3)-diisopropylbenzene, J. Polym. Res., 2: 99- 108.
8.
Bucio, E., Fitch, J.W., Venumbaka, S.R. and Cassidy, P.E. ( 2005). Synthesis and Properties of Aliphatic Spirodilactam Diphenol Containing Polyesters, Polymer, 46: 3971-3974.
9.
Loría-Bastarrachea, M.I., Vázquez-Torres , H. and Aguilar-Vega, M. (2002). Synthesis and Characterization of Aromatic Polyesters and Copolyesters from 4,4'-(1-hydroxyphenylidene)diphenol and 4,4'-(9fluorenylidene)diphenol, J. Appl. Polym. Sci., 86: 2515-2522.
10.
Liaw, D.J. , Liaw, B.Y., Hsu, J.J. and Cheng, Y.C. (2000). Synthesis and Characterization of New Soluble Polyesters Derived from Various Cardo Bisphenols by Solution Polycondensation, J. Polym. Sci.; Part A: Polym. Chem., 38: 4451-4456.
11.
Vibhute, S.S., Joshi, M.D., Wadgaonkar, P.P., Patil, A.S. and Maldar, N.N. (1997). Synthesis and Characterization of New Cardo Polyesters, J. Polym. Sci. Part A: Polym. Chem. , 35: 3227-3234.
12.
Jeong, H.J., Kakimoto, M. and Imai, Y. ( 1991). Synthesis and Characterization of Novel Polyarylates from 2,5-bis(4-hydroxyphenyl)-3,4-diphenylfuran and Aromatic Diacid Chlorides , J. Polym. Sci.; Part A: Polym. Chem., 29: 1293-1299.
13.
Yang, C.P., Oishi, Y., Kakimoto, M. and Imai, Y. ( 1990). Preparation and Properties of Polyarylates from 5-t-butylisophthaloyl Chloride and Various Bisphenols, J. Polym. Sci.; Part A: Polym. Chem., 28: 1353- 1359.
14.
Tamami, B., Yeganeh, H. and Kohmereh, G.A. ( 2004). Synthesis and Characterization of Novel Polyesters Derived from 4-aryl-2,6-bis(4-chlorocarbonyl phenyl) Pyridines and Various Aromatic Diols, Eur. Polym. J., 40: 1651-1657.
15.
Hsiao, S.H. and Chiang, H.W. ( 2004). Synthesis and Properties of New Fluorinated Polyarylates Derived from 1,1-bis(4-hydroxyphenyl)-1-phenyl-2,2,2-trifluoroethane and Aromatic Diacid Chlorides, Eur. Polym. J., 40: 1691-1697.
16.
Imai, Y. and Tassavori, S. ( 1984). Preparation and Properties of Aromatic Polyesters and Copolyesters Containing Phenylindane Unit, J. Polym. Sci.: Part A: Polym. Chem., 22: 1319-1325.
17.
Pessan, L.A. and Koros W.J. (1993). Isomer Effects on Transport Properties of Polyesters Based on Bisphenol-A, J. Polym. Sci.; Part A: Polym. Chem., 9: 1245.
18.
Kane, K.M. , Wells L.A. and Cassidy, P. (1991).Synthesis and Properties of Hexafluoroisopropylidene-containing Polyarylates and Copolyarylates, High Perform. Polym., 3: 191-203.
19.
Zhao, Z., Wu, X., Lin, Y. and McLean, J. ( 1994). Morphological Studies of Bisphenol Series Thermotropic Liquid Crystalline Wholly Aromatic Copolyesters, J. Appl. Polym. Sci., 52: 1529.
20.
He, Z. and Mitchell, G.R. (1994). Crystallization of Random Aromatic Copolyesters Containing Flexible Spacer Chains and Side-groups , Polymer, 25: 1322.
21.
Ghosal, K. , Freeman, B.D., Chern, R.T., Alvarez, J.C., de la Campa, J.G., Lozano, A.E. and de Abajo, J. (1995). Gas Separation Properties of Aromatic Polyamides with Sulfone Groups, Polymer, 36: 793-800.
22.
Morgan, P.W. ( 1965). Condensation Polymers by Interfacial and Solution Methods , Interscience, New York.
23.
Odian, G. ( 1991). Principles of Polymerization, Interscience , New York.
24.
Mitchell, G.R. and Windle, A.H. (1984). Structure of Polystyrene Glasses, Polymer, 25: 906.
25.
Bruma M., Fitch, J.W. and Cassidy, P.E. ( 1996). Hexafluoroisopropylidene Containing Polymers for High-Performance Applications, Rev. Macromol. Chem. Phys., 36: 119-159.
26.
Loría-Bastarrachea, M.I.D. (2004). Síntesis, caracterización y medición de las propiedades de transporte de películas de copoliésteres aromáticos, MSc Thesis, Centro de Investigación Científica de Yucatán , pág 45, Mérida, Yucatán, México.
27.
Carrera-Figueiras, C. (2005). Propiedades de transporte y separación de gases en membranas obtenidas de copoliamidas aromáticas y la relación con su estructura, PhD thesis, Centro de Investigación Científica de Yucatán, pág 38, Mérida, Yucatán , México.
28.
Teplyakov, V.V., Paul, D.R., Bespalova, N.B. and Finkelshtein , E.S. (1992). Gas Permeation in a Fluorine-containing Polynorbornene, Macromolecules , 25: 4218-4219.
