Novel synthetic route of a trehalose-based linear polymer by ring opening of two epoxy groups with aliphatic diamine

Carbohydrate Polymers

Volumn 59, Issue 2, 2005, Pages 217-224

  Teramoto, Naozumi ^a   Abe, Yusuke ^a   Enomoto, Akihito ^a   Watanabe, Dai ^a   Shibata, Mitsuhiro ^a  

^a CHIBA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Epoxide; Renewable resources; Thermal properties; Trehalose

Indexed keywords

ACETONE; CATALYSIS; DIFFERENTIAL SCANNING CALORIMETRY; GLASS TRANSITION; MOLECULAR WEIGHT; ORGANIC SOLVENTS; PLASTICIZERS; POLYSACCHARIDES; SYNTHESIS (CHEMICAL); THERMODYNAMIC PROPERTIES; THERMOGRAVIMETRIC ANALYSIS;

ALIPHATIC DIAMINES; EPOXIDES; LINEAR POLYMERS; RENEWABLE RESOURCES; TREHALOSE;

ORGANIC POLYMERS;

EID: 12444344839     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2004.09.010     Document Type: Article

References (27)

1. H.H. Baer, and B. Radatus Preparation of some partially protected, α,α-trehalose-type disaccharides having the d-altro configuration Carbohydrate Research 128 1984 165 174
2. P.C. Bell, M. Bergsma, I.P. Dolbnya, W. Bras, M.C.A. Stuart, A.E. Rowan, M.C. Feiters, and J.B.F.N. Engberts Transfection mediated by gemini surfactants: Engineered escape from the endosomal compartment Journal of American Chemical Society 125 2003 1551 1558
3. J. Choi, A.F. Yee, and R.M. Laine Organic/inorganic hybrid composites from cubic silsesquioxanes. Epoxy resins of octa(dimethylsiloxyethylcyclohexylepoxide) silsesquioxane Macromolecules 36 2003 5666 5682
4. A.A.J. Feast, W.G. Overend, and N.R. Williams Branched-chain sugars. Part V. Structure and reactivity of anhydro-sugars. Part VI. The synthesis of branched-chain deoxysugars Journal of Chemical Society 1965 7378 7388
5. M.L. Fielden, C. Perrin, A. Kremer, M. Bergsma, M.C. Stuart, P. Camilleri, and J.B.F.N. Engberts Sugar-based tertiary amino gemini surfactants with a vesicle-to-micelle transition in the endosomal pH range mediated efficient transfection in vitro European Journal of Biochemistry 268 2001 1269 1279
6. C. Fringant, J. Desbrières, and M. Rinaudo Physical properties of acetylated starch-based materials: Relation with their molecular characteristics Polymer 37 1996 2663 2673
7. R. Garçon, C. Clerk, J.-P. Gesson, J. Bordado, T. Nunes, S. Caroço, P.T. Gomes, M.E. Minas da Piedade, and A.P. Rauter Synthesis of novel polyurethanes from sugars and 1,6-hexamethylene diisocyanate Carbohydrate Polymers 45 2001 123 127
8. S. Hanessian, and N.R. Plessas The reaction of O-benzylidene sugars with N-bromosuccinimide. III. Application to the synthesis of aminodeoxy and deoxy sugars of biological importance Journal of Organic Chemistry 34 1969 1045 1053
9. A. Hartwig, and M. Sebald Preparation and properties of elastomers based on a cycloaliphatic diepoxide and poly(tetrahydrofuran) European Polymer Journal 39 2003 1975 1981
10. K. Hashimoto, S. Wibullcksanakul, and M. Okada Macromolecular synthesis from saccharic lactones. polyaddition of d-glucaro- and d-mannaro-1,4:6,3- dilactones with diisocyanates and hydrolyzability of the resulting polyurethanes having dilactone rings in the main chains Journal of Polymer Science, Part A: Polymer Chemistry 33 1995 1495 1503
11. D. Horton, and D.H. Hutson Developments in the chemistry of thio sugars Advances in Carbohydrate Chemistry 21 1966 123 196
12. L. Hough, P.A. Munroe, and A.C. Richardson Chemical modification of trehalose. Part V. The synthesis of mono- and di-epoxides Journal of Chemical Society (C) 1971 1090 1094
13. A. Isogai, A. Ishizu, and J. Nakano Thermal and structural properties of tri-O-substituted cellulose ethers Journal of Applied Polymer Science 30 1985 345 353
14. Kubota, M., Sugimoto, T., & Miyake, T. (1999). Non-reducing saccharide and its production and use. US Patent, US 5908767.
15. K. Kurita, N. Masuda, S. Aibe, K. Murakami, S. Ishii, and S. Nishimura Synthetic carbohydrate polymers containing trehalose residues in the main chain: Preparation and characteristic properties Macromolecules 27 1994 7544 7549
16. S.-H. Lee, and N. Shiraishi Plasticization of cellulose diacetate by reaction with maleic anhydride, glycerol, and citrate esters during melt processing Journal of Applied Polymer Science 81 2001 243 250
17. J. Maslinska-Solich Condensation and polycondensation of terephthaldehyde with methyl d-hexopyranosides Macromolecular Bioscience 1 2001 312 321
18. F.M. Menger, and J.S. Keiper Gemini surfactant Angewandte Chemie International Edition 39 2000 1906 1920
19. M. Okada, K. Tachikawa, and K. Aoi Biodegradable polymers based on renewable resources. II. Synthesis and biodegradability of polyesters containing furan rings Journal of Polymer Science, Part A: Polymer Chemistry 35 1997 2729 2737
20. O.-J. Park, D.-Y. Kim, and J.S. Dordick Enzyme-catalyzed synthesis of sugar-containing monomers and linear polymers Biotechnology and Bioengineering 70 2000 208 216
21. M. Shibata, M. Asahina, N. Teramoto, and R. Yosomiya Chemical modification of pullulan by isocyanate compounds Polymer 42 2001 59 64
22. M.D. Soucek, O.L. Abu-Shanab, C.D. Anderson, and S. Wu Kinetic modeling of the crosslinking reaction of cycloaliphatic epoxides with carboxyl functionalized acrylic resins: Hammett treatment of cycloaliphatic epoxides Macromolecular Chemistry and Physics 199 1998 1035 1042
23. N. Teramoto, Y. Shibasaki, Y. Arai, and M. Shibata A facile synthesis of a novel polyacetal containing trehalose residue in the main chain Carbohydrate Polymers 56 2004 1 6
24. M. Tokizawa, H. Okada, N. Wakabayashi, T. Kimura, and H. Fukutani Preparation and cured properties of novel cycloapliphatic epoxy resins Journal of Applied Polymer Science 50 1993 627 635
25. H. Uyama, E. Klegraf, S. Wada, and S. Kobayashi Regioselective polymerization of sorbitol and divinyl sebacate using lipase catalyst Chemistry Letters 2000 800
26. I.A. Wolff, D.W. Olds, and G.E. Hilbert Triesters of corn starch, amylose, and amylopectin Industrial and Engineering Chemistry 43 1951 911 914
27. M. Xie, and Z. Wang Synthesis and properties of a novel cycloaliphatic epoxide Macromolecular Rapid Communications 22 2001 620 623