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Dissertation - Junyoung Seo.pdf (8.45 MB)

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D-Glucaric Acid Based Polymers and Crosslinker: Polyesters Bearing Pendent Hydroxyl Groups and Dissolvable Chemically Crosslinked Gels

Seo, Junyoung
http://orcid.org/0000-0003-3806-7983
http://rave.ohiolink.edu/etdc/view?acc_num=akron1563550430288194

Abstract Details

2019, Doctor of Philosophy, University of Akron, Polymer Engineering.
D-Glucaric acid (GA) is one of the “Top 12 value-added building blocks” according to the U.S. Department of Energy. GA is an aldaric acid derived from a sugar compound that is found in a variety of vegetables and fruits. Monopotassium D-glucaric acid (K-GA) is the most-used commercial form, which is produced by oxidation of D-glucose. This dicarboxylic capped biomaterial provides a promising starting material to synthesize polymers such as polyamides and polyesters. However, K-GA is not able to be used directly for the reaction with other substances. For example, the poor solubility of K-GA makes it impossible to polymerize in an organic solvent. In addition, the hydroxyl groups of K-GA could cause undesired side reactions during the polymerization. In Chapter II, K-GA was modified by neutralization with tetrabutylammonium hydroxide (TBA-OH) in order to improve the solubility of K-GA. This modified GA, bis(tetrabutylammonium) D-glucarate (TBA-GA), was soluble in various organic solvents. Furthermore, the hydroxyl groups of GA were not required to be protected for the polymerization. The polyesters bearing pendent hydroxyl groups were successfully synthesized by TBA-GA with various dihalide compounds, which have ester linkages and hydroxyl groups on their main chains. In addition, the hydroxyl groups of the polyesters were transformed to acetyl groups via acetylation with acetic anhydride, which highlights the possibility of these polymers being used for applications via modification of the hydroxyl groups. The molecular weight, melting temperature and glass transition temperature depend on the dihalide compounds used for the polymerization. Another monomer was prepared by adipic acid (AA) that has the same chemical structure as the modified GA except for the hydroxyl groups. Compared to AA-based polyesters, GA-based polyesters had low thermal stabilities due to their functional groups on the polymer chains. In chapter III, GA-based crosslinker was prepared by esterification of TBA-GA with 4-vinylbenzyl chloride (VBn-Cl). This crosslinker, bis(4-vinylbenzyl) D-glucarate (VBn-GA), had two reactive double bonds that were able to be incorporated into two different chains to make three-dimensional network polymers. In addition, hydroxyl groups and ester linkages of VBn-GA gave the unique properties to the crosslinked polymers. In order to study the effect of GA-based crosslinker, crosslinked gels were prepared by photo-polymerization of acrylic acid (AAc) with VBn-GA. Other crosslinkers, bis(4-vinylbenzyl) adipate (VBn-AA) and 1,4-butanediol diacrylate (BDDA), were also used to prepare crosslinked PAAc gels in order to compare with the PAAc gel crosslinked by VBn-GA. The swelling behaviors of these crosslinked gels were investigated by soaking in pH 4, 7, and 10 buffer solutions. While the gels crosslinked by VBn-AA and BDDA had equilibrium swellings, the gel crosslinked by VBn-GA was dissolved completely in the solutions. In addition, the degradable behavior was studied by using the PAAc gels crosslinked by combinational crosslinkers, BDDA and VBn-GA, where the Mooney-Rivlin and the Flory-Rehner equations were employed to determine the crosslink density of the gels.
Kevin Cavicchi (Advisor)
Bryan Vogt (Committee Chair)
Thein Kyu (Committee Member)
Toshikazu Miyoshi (Committee Member)
Chrys Wesdemiotis (Committee Member)
303 p.
Materials Science; Polymer Chemistry; Polymers
glucaric acid; polyester; pendent hydroxyl groups; crosslinker; dissolvable gel

Recommended Citations

Citations

  • Seo, J. (2019). D-Glucaric Acid Based Polymers and Crosslinker: Polyesters Bearing Pendent Hydroxyl Groups and Dissolvable Chemically Crosslinked Gels [Doctoral dissertation, University of Akron]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=akron1563550430288194

    APA Style (7th edition)

  • Seo, Junyoung. D-Glucaric Acid Based Polymers and Crosslinker: Polyesters Bearing Pendent Hydroxyl Groups and Dissolvable Chemically Crosslinked Gels . 2019. University of Akron, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=akron1563550430288194.

    MLA Style (8th edition)

  • Seo, Junyoung. "D-Glucaric Acid Based Polymers and Crosslinker: Polyesters Bearing Pendent Hydroxyl Groups and Dissolvable Chemically Crosslinked Gels ." Doctoral dissertation, University of Akron, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=akron1563550430288194

    Chicago Manual of Style (17th edition)

akron1563550430288194
137
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