Abstract
In this work, a bio-based polycarbonate has been synthesized successfully from terpene diphenol and diphenyl carbonate by melt polymerization without using any catalysts. The polymerization process involves no usage of toxic phosgene. The reaction parameters such as monomer feed ratio, polymerization temperature and time have been systematically examined. A little excess of diphenyl carbonate for terpene diphenol affords the highest molecular weight. The chemical structure of the product is identified by 1H NMR and FT-IR. The DSC analysis shows that the glass transition temperature of the present bio-based polycarbonate is much higher than that of a conventional bisphenol A-based polycarbonate due to the rigid molecular structure of terpene diphenol. In addition, a series of copolycarbonates with adjustable glass transition temperature are prepared from terpene diphenol and bisphenol A. The present polycarbonate and copolycarbonates with high thermal stability synthesized via an environmental benign process have large potential for bio-based engineering plastics in various industrial fields.
Similar content being viewed by others
References
Bozell JJ (2008) Feedstocks for the future-biorefinery production of chemicals from renewable carbon. Clean 36:641–647
Williams CK, Hillmyer MA (2008) Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polym Rev 48:1–10
Jenck JF, Agterberg F, Droescher MJ (2004) Products and processes for a sustainable chemistry industry: a review of achievements and prospects. Green Chem 6:544–556
Corma A, Iborra S, Velty A (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411–2502
Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO, Klaas MR, Schäfer HJ, Schneider MP (2000) New synthesis with oils and fats as renewable raw materials for the chemical industry. Angew Chem Int Ed 39:2206–2224
Liu CC, Chang KY, Wang YJ (2010) A novel biodegradable amphiphilic diblock copolymers based on poly(lactic acid) and hyaluronic acid as biomaterials for drug delivery. J Polym Res 17:459–469
Xu H, Teng C, Mao Z, Yu M (2012) Study on the preparation and properties of lactic acid based copolymer. J Polym Res 19:9960
Luo SH, Wang QF, Xiong JF, Wang ZY (2012) Synthesis of biodegradable material poly(lactic acid-co-sorbitol) via direct melt polycondensation and its reaction mechanism. J Polym Res 19:9962
Fan XD, Deng Y, Waterhouse J, Pfromm P (1998) Synthesis and characterization of polyamide resins from soy-based dimer acids and different amides. J Appl Polym Sci 68:305–314
Bou JJ, Iribarren I, Muñoz-Guerra S (1994) Synthesis and properties of stereoregular polyamides derived from L-tartaric acid: poly[(2S, 3S)-2, 3-Dimethoxybutylene alkanamide]s. Macromolecules 27:5263–5270
Alam M, Ashraf SM, Ahmad S (2008) Pyridine-poly(urethane ester amide) coatings from linseed oil. J Polym Res 15:343–350
Djordjevic I, Choudhury NR, Dutta NK, Kumar S (2009) Synthesis and characterization of novel citric acid-based polyester elastomers. Polymer 50:1682–1691
Miao S, Zhang S, Su Z, Wang P (2008) Chemoenzymatic synthesis of oleic acid-based polyesters for use as highly stable biomaterials. J Polym Sci A Polym Chem 46:4243–4248
Dong W, Li H, Chen M, Ni Z, Zhao J, Yang H (2011) Biodegradable bio-based polyesters with controllable photo-crosslinkability, thermal and hydrolytic stability. J Polym Res 18:1239–1247
Jasinska L, Koning CE (2010) Unsaturated, biobased polyesters and their cross-linking via radical copolymerization. J Polym Sci A Polym Chem 48:2885–2895
Hashimoto K, Hashimoto N, Kamaya T, Yoshioka J, Okawa H (2011) Synthesis and properties of bio-based polyurethanes bearing hydroxyl groups derived from alditols. J Polym Sci A Polym Chem 49:976–985
Desai SD, Emanuel AL, Sinha VK (2003) Biomaterial based polyurethane adhesive for bonding rubber and wood joints. J Polym Res 10:275–281
Lligadas G, Ronda JC, Galià M, Cádiz V (2010) Plant oils as platform chemicals for polyurethane synthesis: current state-of-the-art. Biomacromolecules 11:2825–2835
Palaskar DV, Boyer A, Cloutet E, Alfos C, Cramail H (2010) Synthesis of biobased polyurethane from oleic and ricinoleic acids as the renewable resources via the AB-type self-condensation approach. Biomacromolecules 11:1202–1211
Oprea S (2012) Novel quinoline-based polyurethane elastomers. The effect of the hard segment structure in properties enhancement. J Polym Res 19:9697
Wang CS, Shieh JY (1999) Synthesis and flame retardancy of phosphorous containing polycarbonate. J Polym Res 6:149–154
Woo BG, Choi KY, Song KH, Lee SH (2001) Melt polymerization of bisphenol-A and diphenyl carbonate in a semibatch reactor. J Appl Polym Sci 80:1253–1266
Haba O, Itakura I, Ueda M, Kuze S (1999) Synthesis of polycarbonate from dimethyl carbonate and bispheol-A through a non-phosgene process. J Polym Sci A Polym Chem 37:2087–2093
Fukuoka S, Tojo M, Hachiya H, Aminaka M, Hasegawa K (2007) Green and sustainable chemistry in practice: development and industrialization of a novel process for polycarbonate production form CO2 without using phosgene. Polym J 39:91–114
Okuyama K, Sugiyama J, Nagahata R, Asai M, Ueda M, Takeuchi K (2003) Direct synthesis of polycarbonate from carbon monoxide and bisphenol A catalyzed by Pd-carbene complex. Macromolecules 36:6953–6955
Kim J, Gracz HS, Roberts GW, Kisrow DJ (2008) Spectroscopic analysis of poly(bisphenol A carbonate) using high resolution 13C and 1H NMR. Polymer 49:394–404
Hammani S, Moulai-Mostefa N, Benyahia L, Tassin JF (2012) Effects of composition and extrusion parameters on the morphological development and rheological properties of PP/PC blends. Co-continuity investigation. J Polym Res 19:9940
Sweileh BA, Al-Hiari YM (2006) Synthesis and thermal properties of polycarbonates based on bisphenol A by single-phase organic solvent polymerization. J Polym Res 13:181–191
Fukuoka S, Kawamura M, Komiya K, Tojo M, Hachiya H, Hasegawa K, Aminaka M, Okamoto H, Fukawa I, Konno S (2003) A novel non-phosgene polycarbonate production process using by-product CO2 as starting material. Green Chem 5:497–507
Wu R, Al-Azemi TF, Bisht KS (2008) Functionalized polycarbonate derived from tartaric acid: enzymatic ring-opening polymerization of a seven-membered cyclic carbonate. Biomacromolecules 9:2921–2928
Mei H, Zhong Z, Long F, Zhuo R (2006) Synthesis and characterization of novel glycerol-derived polycarbonate with pendant hydroxyl groups. Macromol Rapid Commun 27:1894–1899
Xia H, Suo ZY, Qiang GJ, Chang CJ (1995) Synthesis, characterization, and degradation of a novel L-tyrosine-derived polycarbonate for potential biomaterial applications. J Appl Polym Sci 110:2168–2178
Schmidhauser JC (1995) Patent JP 7-53430
Morikawa T, Fujii K (1998) Patent JP 8-198791
Firdaus M, Espinosa LM, Meier MAR (2011) Terpene-based renewable monomers and polymers via thiol-ene additions. Macromolecules 44:7253–7262
Satoh K, Sugiyama H, Kamigaito M (2006) Biomass-derived heat-resistant alicyclic hydrocarbon polymers: poly(terpenes) and their hydrogenated derivatives. Green Chem 8:878–882
Kimura H, Murata Y, Matsumoto A, Hasegawa K, Ohtsuka K, Fukuda A (1999) New thermosetting resin from terpenediphenol-based benzoxazine and epoxy resin. J Appl Polym Sci 74:2266–2273
Serini V (2000) Polycarbonates. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Wielgosz Z, Dobkowski Z, Krajewski B (1972) Studies on polycarbonate preparation by the interfacial polycondensation method. Eur Polym J 8:1113–1119
Hersh SN, Choi KY (1990) Melt transesterification of diphenyl carbonate with bisphenol A in a batch reactor. J Appl Polym Sci 41:1033–1046
Darensbourg DJ, Wilson SJ (2011) Synthesis of poly(indene carbonate) from indene oxide and carbon dioxide—a polycarbonate with a rigid backbone. J Am Chem Soc 133:18610–18613
Güner FS, Yağci Y, Erciyes AT (2006) Polymers from triglyceride oils. Prog Polym Sci 31:633–670
Xia Y, Larock RC (2010) Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem 12:1893–1909
Acknowledgment
We acknowledge the gift of TPD from Yasuhara Chemical Co., Ltd.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(PDF 430 kb)
Rights and permissions
About this article
Cite this article
Xin, Y., Uyama, H. Synthesis of new bio-based polycarbonates derived from terpene. J Polym Res 19, 15 (2012). https://doi.org/10.1007/s10965-012-0015-2
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10965-012-0015-2