Reactions between cellulose diacetate and alkenylsuccinic anhydrides and characterization of the reaction products |
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Authors: | Tsuyoshi Takihara Yutaka Yoshida Akira Isogai |
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Institution: | (1) Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan |
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Abstract: | Cellulose diacetate (CDA) with degree of substitution (DS) of 2.4 was dissolved in dimethylsulfoxide and reacted with octadecenyl
succinic anhydrides (OSAs) using 1-methylimidazole as a promoter. FT-IR and 1H-NMR analysis of the reaction products revealed that half-esterification occurred on residual hydroxyl groups of CDA by OSA,
providing CDA/octadecenyl succinic acid (OSAcid) half esters at yields of more than 90%. The effects of reaction time and
temperature on DS of CDA/OSAcid esters were studied in detail. The higher the reaction temperature, the higher the esterification
rate to form CDA/OSAcid half esters. The maximum DS values were 0.41 and 0.33 for CDA/n-OSAcid and CDA/i-OSAcid esters, respectively.
The original X-ray diffraction pattern of CDA changed with the introduction of OSAcid substituents into CDA, and CDA/OSAcid
esters seemed to have thermoplasticity, depending on DS and the chemical structure of the OSAcids. A soil-embedding test of
films of CDA and CDA/OSAcid esters indicated that the CDA/OSAcid esters that were prepared maintained the biodegradability
of the original CDA. |
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Keywords: | Alkenylsuccinic anhydride Biodegradation Cellulose diacetate DSC Half ester SEC-MALS Thermoplasticity X-ray diffraction |
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