Synthesis and characterization of copolyanhydrides of carbohydrate-based galacteric acid and adipic acid

Tuomas Mehtiö (Corresponding Author), Leena Nurmi, Virpi Rämö, Hannu Mikkonen, Ali Harlin

    Research output: Contribution to journalArticleScientificpeer-review

    9 Citations (Scopus)

    Abstract

    A series of copolyanhydrides, consisting of 2,3,4,5-tetra-O-acetylgalactaric acid (AGA) and adipic acid (AA) as monomer units, was polymerized. Synthesis of AGA monomer consisted of two steps. First, O-acetylation of galactaric acid secondary hydroxyl groups was performed using acetic anhydride as a reagent. Acetic anhydride was then further used as a reagent in the synthesis of diacetyl mixed anhydride of AGA. Polymerizations were conducted as bulk condensation polymerization at 150°C. Thermal properties of the copolymers varied depending on monomer composition. Increase in the AGA content had a clear increasing effect on the Tg. A similar increasing effect was observed in Tm. The degree of crystallinity decreased as AGA content increased. There was a slightly lowering tendency in the molecular weights of the obtained polymers when the AGA content in the polymerization mixtures increased. The described synthesis route shows that bio-based aldaric acid monomers are potential candidates for the adjustment of thermal properties of polyanhydrides.
    Original languageEnglish
    Pages (from-to)102-110
    JournalCarbohydrate Research
    Volume402
    DOIs
    Publication statusPublished - 2015
    MoE publication typeA1 Journal article-refereed

    Keywords

    • biopolymers
    • biodegradable
    • polyanhydrides
    • polycondensation
    • synthesis
    • renewable resources
    • acetylation

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