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ARS Home » Southeast Area » New Orleans, Louisiana » Southern Regional Research Center » Cotton Chemistry and Utilization Research » Research » Publications at this Location » Publication #133711
Title: Synthesis & Biological, Physical, & Adhesive Properties of Epoxy Sucroses

Author
item Sachinvala, Navzer
item WINSOR, DAVID - NEW ENGLAND PRINTED TAPE
item White, Leslie
item LITT, MORTON - CASE WESTERN RESERVE UNIV

Submitted to: Polymer Preprints
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/1/2002
Publication Date: 11/15/2002
Citation: Sachinvala, N.D., Winsor, D.L., White, L.A., Litt, M.H. 2002. Synthesis & Biological, Physical, & Adhesive Properties of Epoxy Sucroses. Polymer Preprints. 43(2):997-998.

Interpretive Summary: Despite its abundance, low price, purity, and versatility, raw sugar is not an industrial starting material for making adhesives, coatings, plastics, and composites. Furthermore, sucrose-based chemicals are not widely available in plastics, adhesives, coatings, and composites industries. People incorrectly perceive that many steps and expensive chemicals and protocols are needed to make sucrose-based epoxies for commercial use. In this work we show that raw sugar dissolved in aqueous media was converted to three different types epoxy derivatives. When combined with a hardener, sucrose-based epoxies can be formulated to make flexible materials, tough materials, or very hard materials. This work shows new industrial uses for raw sugar, and demonstrates that raw sugar can be converted by environmentally benign methods to materials that produce plastics, adhesives, coatings, and composites. In addition, our materials design and characterization methods will provide new information to industrial and academic scientists who want to design and thoroughly characterize monomers and polymers from sugar.

Technical Abstract: Raw sugar was converted in two steps to epoxy allyl sucroses (EAS), epoxy crotyl sucroses (ECS), and epoxy methallyl sucroses (EMS) respectively, in 82, 91, and 91.5 % overall yields. EAS, ECS, and EMS are regio and diastereo isomeric epoxy monomers that are liquids at room temperature. The average number of epoxy groups per sucrose and epoxy equivalent weights of EAS, ECS, EMS by carbon-13 NMR were 3.2 and 223, 7.3 and 122, and 5.6 and 174; and glass transition temperatures (Tgs) by differential scanning calorimetry (DSC) were ¿51, -28, and ¿28, degrees C, respectively. By Maron Ames tests using Salmonella Typhimurium strains TA-98 and TA-100, with and without metabolic activation, EAS and ECS were non-cytotoxic and non-mutagenic, and EMS was borderline cytotoxic. In their comparison diglycidyl ether of bisphenol-A (DGEBA) was both cytotoxic and mutagenic using TA-100 and not with TA-98. With diethylene triamine (DETA) EAS, ECS, EMS, and DGEBA cured at 97, 146, 75, and 97 degrees C respectively, and their average break stresses by Instron® (ASTM D1002-94) were 939, 1366, 1143, and 1030. Finally, moduli between 20 and 150 degrees C by dynamic mechanical analysis (DMA) changed by 73, 5, 26, and 20 fold for EAS, ECS, EMS, and DGEBA, respectively.