Synthesis and characterization of polycarbonates by melt phase interchange reactions of alkylene and arylene diacetates with alkylene and arylene diphenyl dicarbonates

Molecules

Volumn 15, Issue 5, 2010, Pages 3661-3682

  Sweileh, Bassam A ^a   Al Hiari, Yusuf M ^a   Kailani, Mohammad H ^a   Mohammad, Hani A ^b  

^a UNIVERSITY OF JORDAN   (Jordan)

^b UNIVERSITY OF PETRA   (Jordan)

Author keywords

Diacetates; Diphenyl dicarbonate; Interchange reactions; Polycarbonates; Polycondensation; Synthesis

Indexed keywords

ALKENE; AROMATIC HYDROCARBON; CARBOXYLIC ACID; POLYCARBONATE; POLYCARBOXYLATE CEMENT;

ARTICLE; CHEMISTRY; SYNTHESIS; VISCOSITY;

ALKENES; CARBOXYLIC ACIDS; HYDROCARBONS, AROMATIC; POLYCARBOXYLATE CEMENT; VISCOSITY;

EID: 77952804667     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15053661     Document Type: Article

References (44)

1. Brunelle, D.J. Polycarbonates. In Encyclopedia of Polymer Science and Technology, 3rd ed.; Mark, H.F., Ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2004; Volume 7, pp. 397-426.
2. Deshpande, M.M.; Jadhav, A.S.; Gunari, A.A.; Sehra, J.C.; Sivaram, S. Polycarbonate synthesis by melt phase carbonate-ester interchange reaction of bisphenol-A diacetate with Dimethyl carbonate. J. Polym. Sci. A Polym. Chem. 1995, 33, 701-705.
3. Clagett, D.; Shafer, S. Polycarbonates. In Comprehensive Polymer Science; Allen, G., Bevington, J.C., Eds.; Pregman Press: Oxford, UK, 1989; Volume 5, pp. 345-356.
4. Freitag, D.; Grigo, U.; Müller, P.; Nouvertne, W. Polycarbonates. In Encyclopedia of Polymer Science and Engineering; Mark, H.F., Overberger, C.G., Menges, G., Kroschwilz, J.I., Eds.; Wiley: New York, NY, USA, 1987; Volume 11, pp. 648-718.
5. Pokharkar, V.; Sivaram, S. Poly(alkylene carbonate)s by the carbonate interchange reaction of aliphatic diols with dimethyl carbonate: Synthesis and characterization. Polymer 1995, 36, 4851-4854.
6. Park, J.H.; Hyun, J.C.; Kim, W.N.; Kim, S.R.; Ryu, S.C. Extensional and complex viscosities of linear and branched polycarbonates. Macromol. Res. 2002, 10, 135-139.
7. Liu, Z.; Cunha, A.M.; Yi, X.-S.; Bernado, A.C. Key properties to understand the performance of polycarbonate reprocessed by injection molding. J. Appl. Polym. Sci. 2000, 77, 1393-1400.
8. Jones, R.O.; Ballone, P. A combined density functional and Monte Carlo study of polycarbonate. Mat. Res. Soc. Symp. Proc. 2001, AA3.1/1-AA3.1/12, 677.
9. Liaw, D.J.; Chang, P. Synthesis and characterization of aromatic and brominated aromatic polycarbonates by two-phase-transfer-catalyzed polycondensation of bisphenols with trichloromethyl chloroformate. J. Appl. Polym. Sci. 1997, 63, 195-204.
10. Kricheldorf, H.; Luebbers, D. Polymers of carbonic acid. 3. Thermotropic polycarbonates derived from 4, 4P′-dihydroxybiphenyl and various diphenols. Macromolecules 1990, 23, 2656-2662.
11. Lee, J.; Song, C.; Kim, J.-I.; Kim, J.-H. Preparation of aromatic polycarbonates nanoparticles using supercritical carbon dioxide. J. Nanopart. Res. 2002, 4, 53-59.
12. Ballistreri, A.; Montaudo, G.; Scamporrino, E.; Puglisi, C.; Vitalini, D.; Ucinella, S. Intumescent flame retardants of polymers. IV. The polycarbonate- aromatic sulfonates system. J. Polym. Sci. A Polym. Chem. 1988, 26, 2113-2127.
13. Martin, E.H.; Brittain, J. A convenient laboratory preparation of aromatic polycarbonate. Polym. Bull. 2002, 47, 517-520.
14. Haba, O.; Itakura, I.; Ueda, M.; Kuze, S. Synthesis of polycarbonate from dimethyl carbonate and bisphenol-A through a nonphosgene process. J. Polym. Sci. Part A Polym. Chem. 1999, 37, 2087-2093.
15. Skupinska, J.; Kuczynska, L.; Wielgosz, Z. Aromatic polycarbonates by direct synthesis from bisphenol A and carbon monoxide. React. Kinet. Catal. Lett. 2003, 80, 269-276.
16. Fraitag, D.; Fengler, G.; Morbitzer, L. Routes to new aromatic polycarbonates with special material properties. Angew. Chem. Int. Ed. Engl. 1991, 30, 1598-1610.
17. Kim, W.B.; Joshi, U.A.; Lee, J.S. Making polycarbonates without employing phosgene: An overview on catalytic chemistry of intermediate and precursor syntheses for polycarbonate. Ind. Eng. Chem. Res. 2004, 43, 1897-1914 and references therein.
18. Ono, Y. Dimethyl carbonate for environmentally benign reactions. Catal. Today 1997, 35, 15-25.
19. Kricheldorf, H.; Lee, S.; Bettina, W. Polymers of carbonic acid, 12 spontaneous and hematin-initiated polymerizations of trimethylene carbonate and neopentylene carbonate. Macromol. Chem. Phys. 1996, 197, 1043-1054.
20. Thorat, S.D.; Philips, P.J.; Semenov, V.; Gakh, A. Physical properties of aliphatic polycarbonates made from CO2 and epoxides. J. Appl. Polym. Sci. 2003, 89, 1163-1176.
21. Vorgdanis, L.; Martens, B.; Uchtmann, H.; Hensel, F.; Heitz, W. Synthetic and thermodynamic investigations in the polymerization of ethylene carbonate. Makromol. Chem. 1990, 191, 465-472.
22. Sweileh, B.A.; Al-Hiari, Y.M.; Aiedeh, K.M. A new, nonphosgene route to poly(bisphenol A carbonate) by melt-phase interchange reactions of alkylene diphenyl dicarbonates with bisphenol A. J. Appl. Polym. Sci. 2008, 110, 2278-2292.
23. Sun, S.; Chang, T. Studies on the thermotropic liquid crystalline polycarbonates. III. Synthesis and properties of fully aromatic liquid-crystalline polycarbonates. J. Polym. Sci. Part A Polym. Chem. 1993, 31, 2711-2719.
24. Sun, S.-J.; Chang, T.-C. Studies on the thermotropic crystalline polycarbonates. II. Synthesis and properties of fully aromatic liquid crystalline polycarbonates. J. Polym. Sci. Part A Polym. Chem. 1993, 31, 2237-2243.
25. Sun, S.J.; Li, C.H.; Chang, T.C. Studies on the Thermotropic crystalline polycarbonates. I. synthesis and properties of thermotropic liquid crystalline poly (azomethine carbonates). Eur. Polym. J. 1993, 29, 951-955.
26. De Backer, C.; Ottenburgs, R.; Van Beylen, M.; Saymn, C. Synthesis and liquid- crystalline properties of thermotropic homopolycarbonates. Macromol. Chem. Phys. 1995, 196, 1495-1514.
27. De Backer, C.; Ottenburgs, R.; Van Beylen, M.; Saymn, C. Synthesis and liquid crystalline properties of thermotropic copolycarbonates. Macromol. Chem. Phys. 1996, 197, 443-466.
28. Sato, M.; Kurosawa, K.; Nakatsuchi, K.; Okhatsu, Y. Synthesis and liquid-crystalline properties of thermotropic homo- and copolycarbonates. J. Polym. Sci. A Polym. Chem. 1988, 26, 3077-3088.
29. Sato, M.; Tomihisa, N.; Komatsu, F.; Yahata, T.; Shoji, Y. Synthesis and liquid-crystalline properties of Thermotropic copolycarbonates composed of biphenyl and diphenylpropane moieties. Euro. Polym. J. 1990, 26, 467-470.
30. Sato, M.; Muraki, K.; Mukaida, K-I. Thermotropic liquid crystalline semirigid polycarbonates based on diphenyl ether and benzophenone units. Macromolecules 1994, 27, 4577-4582.
31. Sato, M.; Tada, Y.; Goto, Y.; Mukaida, K. Semi-rigid thermotropic liquid-crystalline copolycarbonates comprising main-chain hexafluoropentane segments. Macromol. Rap. Comm. 1995, 16, 139-146.
32. Sato, M.; Muraki, K.; Mukaida, K.-I. Synthesis and thermal properties of semi-rigid homo-, co-and terpolycarbonates containing naphthalene rings. Euro. Polym. J. 1995, 31, 867-873.
33. Liaw, D.-J.; Chang, P. Synthesis and characterization of copolycarbonates from melt transesterfication. Polymer 1996, 37, 2857-2863.
34. Liaw, D.-J.; Chen, P.-C. Preparation and polyesters derived from 4,4'-sulfonyl dibenzoyl chloride by solution polycondensation. J. Polym. Sci. Part. A Polym. Chem. 1996, 34, 885-891.
35. Tomoki, H.; Hirosuke, K. Halogen-free solventless manufacture of polyesters and polycarbonate-polyesters with excellent physical properties. Jpn. Kokai Tokkyo Koho JP 09235362, 1997.
36. Kouichi, K.; Shigeki, K.; Noriyuki, K.; Masaya, O. Producing a transparent polycarbonate with heat and water resistance. Eur. Pat. Appl. EP 488182, 1992.
37. Tatsuya, S.; Tsutomu, Y. Phosgene-free manufactre of high-molecular- weight polycarbonates. Jpn. Kokai Tokkyo Koho JP 02284917, 1990.
38. Yoshitaka, N.; Yoshiyuki, Y. Preparation of aromatic poycarbonates without using phosgene. Jpn. Kokai Tokkyo Koho JP 02166119,1990.
39. Barry, H. Production of polycarbonates. Eur. Pat. Appl. EP 299773, 1989.
40. Al-Hamouz, O.C.S.; Sweileh, B.A.; Al-Salah, H.A. Synthesis and characterization of polycarbonates by melt-phase interchange reactions with alkylene and arylene diphenyl dicarbonates. J. Appl. Polym. Sci. 2006, 102, 3597-3609.
41. Li, X.Y.; Yee, A.F. Design of mechanically robust high-Tg polymers: Physical properties of glassy poly(ester carbonate)s with cyclohexylene rings in the backbone. Macromolecules 2003, 36, 9421-9429.
42. Sweileh, B.A.; Al-Hiari, Y.M. Synthesis and thermal properties of polycarbonates based on bisphenol A by single-phase organic solvent polymerization. J. Polym. Res. 2006, 13, 181-191.
43. Berti, C.; Bonora, V.; Pilati, F. Reactive blending of poly(ethylene terephthalate) and polycarbonate. 1. A reappraisal of the reactions occurring during melt-mixing. Makromol. Chem. 1992, 193, 1665-1677.
44. Liaw, D.-J.; Chang, P. Synthesis and characterization of polycarbonates based on bisphenol S by melt transesterification. J. Polym. Sci. Part A Polym. Chem. 1997, 35, 2453-2460.