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Evaluation of 3-Allyl-5-vinylveratrole in Latex Copolymerization with an Acrylic Monomer from High Oleic Soybean Oil

  • Yehor Polunin
    Yehor Polunin
    Department of Coatings and Polymeric Materials, North Dakota State University, Dep. 2760, Fargo, North Dakota 58108-6050, United States
  • Timothy J. Burns
    Timothy J. Burns
    Department of Chemistry and Biochemistry, North Dakota State University, Dep. 2735, Fargo, North Dakota 58105-6050, United States
  • Eric M. Serum
    Eric M. Serum
    Department of Chemistry and Biochemistry, North Dakota State University, Dep. 2735, Fargo, North Dakota 58105-6050, United States
  • Mukund P. Sibi*
    Mukund P. Sibi
    Department of Chemistry and Biochemistry, North Dakota State University, Dep. 2735, Fargo, North Dakota 58105-6050, United States
    *Email: [email protected]. Phone: +1-701-231-8251. Fax: +1-701-231-8831.
  • , and 
  • Andriy Voronov*
    Andriy Voronov
    Department of Coatings and Polymeric Materials, North Dakota State University, Dep. 2760, Fargo, North Dakota 58108-6050, United States
    *Email: [email protected]. Phone: +1-701-231-9563.
Cite this: ACS Sustainable Chem. Eng. 2021, 9, 20, 7003–7011
Publication Date (Web):May 6, 2021
https://doi.org/10.1021/acssuschemeng.1c00663
Copyright © 2021 American Chemical Society

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    Abstract

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    Renewable 3-allyl-5-vinylveratrole (AVV) has been evaluated and classified as a biobased cross-linkable vinyl monomer in free-radical chain polymerization. AVV can be readily synthesized in four steps from vanillin, a compound available from lignin. Retained during macromolecular backbone formation, allylic unsaturation can be utilized in post-polymerization cross-linking and contribute to polymer network formation. The glass-transition temperature of the homopolymer from AVV (Tg = 77 °C) indicates that incorporating its fragments into copolymers might considerably change the intermolecular interactions and physicochemical properties of the resulting materials. Reactivity ratios (r1, r2) obtained in AVV copolymerization with styrene and calculated Qe parameters of AVV confirm that this monomer copolymerization is described with the classical Mayo–Lewis equation. In this work, latexes from AVV and a renewable acrylic monomer from high oleic soybean oil were synthesized using the miniemulsion process. When the resulting biobased latex films are oxidatively cured, thermomechanical properties of the latex network are determined by the cross-link density, controlled by the ratio of “rigid” and “soft” fragments of AVV and the high oleic soybean oil-based monomer, respectively. Depending on the monomer ratio in the feed, polymeric materials with essentially different viscoelastic behaviors were obtained. Being a structural analogue to styrene, 3-allyl-5-vinylveratrole may function as its renewable replacement in free-radical polymerization, particularly in sustainable latexes. Assuming a variety of plant/vegetable oil-based acrylic monomers available, combining such monomers with AVV can become a promising platform for controlling properties of biobased latex polymer networks and their performance.

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    • Experimental details on AVV homopolymer characterization (PDF)

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    Cited By

    This article is cited by 4 publications.

    1. Sara Dalle Vacche, Samantha Molina-Gutiérrez, Giuseppe Ferraro, Vincent Ladmiral, Sylvain Caillol, Patrick Lacroix-Desmazes, Yves Leterrier, Roberta Bongiovanni. Biobased Composites from Eugenol- and Coumarin-Derived Methacrylic Latex and Hemp Nanocellulose: Cross-Linking via [2 + 2] Photocycloaddition and Barrier Properties. ACS Sustainable Chemistry & Engineering 2024, 12 (23) , 8741-8751. https://doi.org/10.1021/acssuschemeng.4c01365
    2. Wei Liu, Mei Wu, Chuqing Ma, Cheng Liu, Xiaoying Zhang, Zhong Wang, Zhongkai Wang. Efficient Miniemulsion Polymerization of Plant Oil-Based Acrylate Monomer toward Waterborne Epoxy Resins. ACS Sustainable Chemistry & Engineering 2022, 10 (40) , 13301-13309. https://doi.org/10.1021/acssuschemeng.2c02403
    3. Elena Rigo, Vincent Ladmiral, Sylvain Caillol, Patrick Lacroix-Desmazes. Recent advances in radical polymerization of bio-based monomers in aqueous dispersed media. RSC Sustainability 2023, 1 (4) , 788-813. https://doi.org/10.1039/D3SU00097D
    4. Guohao Guan, Tong Gao, Xuejun Wang, Tao Lou. A cost-effective anionic flocculant prepared by grafting carboxymethyl cellulose and lignosulfonate with acrylamide. Cellulose 2021, 28 (17) , 11013-11023. https://doi.org/10.1007/s10570-021-04232-8