Synthesis of new bio-based polycarbonates derived from terpene

Journal of Polymer Research

Volumn 19, Issue 12, 2012, Pages

  Xin, Yuanrong ^a   Uyama, Hiroshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Bio based polymers; Copolymerization; Melt polymerization; Polycarbonates; Terpene

Indexed keywords

COPOLYMERIZATION; GLASS; HIGH TEMPERATURE ENGINEERING; PHENOLS; PLASTICS INDUSTRY; POLYCARBONATES; TEMPERATURE; TERPENES; THERMAL ENGINEERING;

BIO-BASED POLYMERS; ENGINEERING PLASTICS; HIGH THERMAL STABILITY; MELT POLYMERIZATION; POLYMERIZATION PROCESS; POLYMERIZATION TEMPERATURE; REACTION PARAMETERS; RIGID MOLECULAR STRUCTURE;

GLASS TRANSITION;

EID: 84868281155     PISSN: 10229760     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10965-012-0015-2     Document Type: Article

References (43)

1. Bozell JJ (2008) Feedstocks for the future-biorefinery production of chemicals from renewable carbon. Clean 36:641-647
2. Williams CK, Hillmyer MA (2008) Polymers from renewable resources: a perspective for a special issue of polymer reviews. Polym Rev 48:1-10 (Pubitemid 351219978)
3. 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 (Pubitemid 39636064)
4. Corma A, Iborra S, Velty A (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411-2502 (Pubitemid 47033769)
5. 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
6. 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
7. 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
8. 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
9. 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 (Pubitemid 128586246)
10. 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
11. Alam M, Ashraf SM, Ahmad S (2008) Pyridine-poly(urethane ester amide) coatings from linseed oil. J Polym Res 15:343-350
12. Djordjevic I, Choudhury NR, Dutta NK, Kumar S (2009) Synthesis and characterization of novel citric acid-based polyester elastomers. Polymer 50:1682-1691
13. 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
14. DongW, 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
15. Jasinska L, Koning CE (2010) Unsaturated, biobased polyesters and their cross-linking via radical copolymerization. J Polym Sci A Polym Chem 48:2885-2895
16. 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
17. Desai SD, Emanuel AL, Sinha VK (2003) Biomaterial based polyurethane adhesive for bonding rubber and wood joints. J Polym Res 10:275-281
18. Lligadas G, Ronda JC, Galià M, Cádiz V (2010) Plant oils as platform chemicals for polyurethane synthesis: current state-ofthe-art. Biomacromolecules 11:2825-2835
19. 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
20. Oprea S (2012) Novel quinoline-based polyurethane elastomers. The effect of the hard segment structure in properties enhancement. J Polym Res 19:9697
21. Wang CS, Shieh JY (1999) Synthesis and flame retardancy of phosphorous containing polycarbonate. J Polym Res 6:149-154 (Pubitemid 30559041)
22. 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 (Pubitemid 32297308)
23. Haba O, Itakura I, Ueda M, Kuze S (1999) Synthesis of polycarbonate from dimethyl carbonate and bispheol-A through a nonphosgene process. J Polym Sci A Polym Chem 37:2087-2093
24. 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 (Pubitemid 46588644)
25. 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
26. 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
27. 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
28. 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
29. 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 byproduct CO2 as starting material. Green Chem 5:497-507 (Pubitemid 37443706)
30. 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
31. 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 (Pubitemid 44852437)
32. 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
33. Schmidhauser JC (1995) Patent JP 7-53430
34. Morikawa T, Fujii K (1998) Patent JP 8-198791
35. Firdaus M, Espinosa LM, Meier MAR (2011) Terpene-based renewable monomers and polymers via thiol-ene additions. Macromolecules 44:7253-7262
36. 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 (Pubitemid 44527091)
37. Kimura H, Murata Y, Matsumoto A, Hasegawa K, Ohtsuka K, Fukuda A (1999) New thermosetting resin from terpenediphenolbased benzoxazine and epoxy resin. J Appl PolymSci 74:2266-2273 (Pubitemid 32077600)
38. Serini V (2000) Polycarbonates. In: Ullmann's encyclopedia of industrial chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
39. Wielgosz Z, Dobkowski Z, Krajewski B (1972) Studies on polycarbonate preparation by the interfacial polycondensation method. Eur Polym J 8:1113-1119
40. Hersh SN, Choi KY (1990) Melt transesterification of diphenyl carbonate with bisphenol A in a batch reactor. J Appl Polym Sci 41:1033-1046 (Pubitemid 20734337)
41. 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
42. Güner FS, Yaǧci Y, Erciyes AT (2006) Polymers from triglyceride oils. Prog Polym Sci 31:633-670 (Pubitemid 44376410)
43. Xia Y, Larock RC (2010) Vegetable oil-based polymeric materials: synthesis, properties, and applications. Green Chem 12:1893-1909