Trehalose-incorporated polymer network by thiol-ene photopolymerization

Polymer Journal

Volumn 46, Issue 10, 2014, Pages 728-735

  Nagashima, Shohei ^a   Shimasaki, Toshiaki ^a   Teramoto, Naozumi ^a   Shibata, Mitsuhiro ^a  

^a CHIBA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATION; PHOTOPOLYMERIZATION; TENSILE STRENGTH;

FEED MOLAR RATIO; HIGH TRANSPARENCY; PEAK TEMPERATURES; PHOTOPOLYMERIZATIONS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; THIOL-ENE PHOTOPOLYMERIZATION; WEIGHT LOSS TEMPERATURES;

NUCLEAR MAGNETIC RESONANCE;

EID: 84926036915     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2014.53     Document Type: Article

References (25)

1. Newman, Y. M., Ring, S. G. & Colaco, C. The role of trehalose and other carbohydrates in biopreservation. Biotechnol. Genet. Eng. Rev. 11, 263-294 (1993).
2. Paiva, C. L. & Panek, A. D. Biotechnological applications of the disaccharide trehalose. Biotechnol. Annu. Rev. 2, 293-314 (1996).
3. Richards, A. B., Krakowka, S., Dexter, L. B., Schmid, H., Wolterbeck, A. P. M., Waalkens-Berendsen, D. H., Shigoyuki, A. & Kurimoto, M. Trehalose: A review of properties, history of use and human tolerance, and results of multiple safety studies. Food Chem. Toxicol. 40, 871-898 (2002).
4. Elbein, A. D., Pan, Y. T., Pastuszak, I. & Carroll, D. New insights on trehalose: A multifunctional molecule. Glycobiology 13, 17R-27R (2003).
5. Teramoto, N., Sachinvala, N. D. & Shibata, M. Trehalose and trehalose-based polymers for environmentally benign, biocompatible and bioactive materials. Molecules 13, 1773-1816 (2008).
6. Higashiyama, T. Novel functions and applications of trehalose. Pure Appl. Chem. 74, 1263-1270 (2002).
7. Teramoto, N., Arai, Y., Shibasaki, Y. & Shibata, M. A facile synthesis of a novel polyacetal containing trehalose residue in the main chain. Carbohydrate Polym. 56, 1-6 (2004).
8. Kukowka, S. & Mas̈lińska-Solich, J. S. a,a-Trehalose-based polyacetals and macrocyclic acetals. Carbohydrate Polym. 80, 711-719 (2010).
9. Teramoto, N., Unosawa, M., Matsushima, S. & Shibata, M. Synthesis and properties of thermoplastic alternating copolymers containing trehalose and siloxane units by hydrosilylation reaction. Polym. J. 39, 975-981 (2007).
10. Teramoto, N., Arai, Y. & Shibata, M. Thermo-reversible Diels-Alder polymerization of difurfurylidene trehalose and bismaleimides. Carbohydrate Polym. 64, 78-84 (2006).
11. Srinivasachari, S., Liu, Y., Prevette, L. E. & Reineke, T. M. Effect of trehalose click polymer length on pDNA complex stability and delivery efficacy. Biomaterials 28, 2885-2898 (2007).
12. Eissa, A. M. & Khosravi, E. Synthesis of a new smart temperature responsive glycopolymer via click-polymerization. Eur. Polym. J. 47, 61-69 (2011).
13. Teramoto, N. & Shibata, M. Trehalose-based thermosetting resins-1. Synthesis and thermal properties of trehalose vinylbenzyl ether. J. Appl. Polym. Sci. 91, 46-51 (2004).
14. Morgan, C. R., Magnotta, F. & Ketley, A. D. Thiol/ene photocurable polymers. J. Polym. Sci. Polym. Chem. Ed. 15, 627-645 (1977).
15. Hoyle, C. E., Lee, T. Y. & Roper, T. Thiol-enes: chemistry of the past with promise for the future. J. Polym. Sci. Part A 42, 5301-5338 (2004).
16. Dondoni, A. The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry. Angew. Chem. Int. Ed. 47, 8995-8997 (2008).
17. Nilsson, C., Simpson, N., Malkoch, M., Johansson, M. & Malmström, E. Synthesis and thiol-ene photopolymerization of allyl-ether functionalized dendrimers. J. Polym. Sci. Part A 46, 1339-1348 (2008).
18. Lowe, A. B. Thiol-ene 'click' reactions and recent applications in polymer and materials synthesis. Polym. Chem. 1, 17-36 (2010).
19. Ortiz, R. A., Martinez, A. Y. R., Valdéz, A. E. G. & Duarte, M. L. B. An effective method to prepare sucrose polymers by thiol-ene photopolymerization. Carbohydrate Polym. 78, 282-286 (2009).
20. Ortiz, R. A., Martinez, A. Y. R., Valdéz, A. E. G. & Duarte, M. L. B. Preparation of a crosslinked sucrose polymer by thiol-ene photopolymerization using dithiothreitol as comonomer. Carbohydrate Polym. 82, 822-828 (2010).
21. Sangermano, M., Colucci, G., Fragale, M. & Rizza, G. Hybrid organic-inorganic coatings based on thiol-ene systems. React. Funct. Polym. 69, 719-723 (2009).
22. Vilén, E. M. & Sandström, C. NMR study on the interaction of trehalose with lactose and its effect on the hydrogen bond interaction in lactose. Molecules 18, 9735-9754 (2013).
23. Fukazawa, Y. Investigation of trehalose in water splution by PMR. Kenkyu Hokoku-Kanagawa-Ken Kogyo Shikenjo 65, 42-46 (1994).
24. National Institute of Advanced Industrial Science and Technology (AIST). SDBS/RIODB/AIST, Spectral Database for Organic Compounds (SDBS). Available at: http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct-frame-top.cgi (last accessed 11 April 2014).
25. Taguet, A., Ameduri, B. & Dufresne, A. Crosslinking and characterization of commercially available poly(VDF-co-HFP) copolymers with 2,4,4-trimethyl-1,6-hexanediamine. Eur. Polym. J. 42, 549-2561 (2006).