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Silicone Structurants for Soybean Oil: Foams, Elastomers, and Candles
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    Research Article

    Silicone Structurants for Soybean Oil: Foams, Elastomers, and Candles
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    • Cody B. Gale
      Cody B. Gale
      Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W., Hamilton, ON Canada, L8S 4M1
      More by Cody B. Gale
    • Brandon Chin
      Brandon Chin
      Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W., Hamilton, ON Canada, L8S 4M1
      More by Brandon Chin
    • Chetan Tambe
      Chetan Tambe
      Department of Chemical Engineering and Material Science, Michigan State University, 428 S. Shaw Lane #2100, East Lansing, Michigan 48824, United States
      More by Chetan Tambe
    • Daniel Graiver
      Daniel Graiver
      Department of Chemical Engineering and Material Science, Michigan State University, 428 S. Shaw Lane #2100, East Lansing, Michigan 48824, United States
    • Michael A. Brook*
      Michael A. Brook
      Department of Chemistry and Chemical Biology, McMaster University, 1280 Main St. W., Hamilton, ON Canada, L8S 4M1
      *E-mail: [email protected]
    Other Access OptionsSupporting Information (3)

    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2019, 7, 1, 1347–1352
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    https://doi.org/10.1021/acssuschemeng.8b05047
    Published November 19, 2018
    Copyright © 2018 American Chemical Society

    Abstract

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    Soybean oil-derived polyurethanes, while much greener than those derived from isocyanates, have a problematic combustion profile; concerns exist about the nitrogen-containing compounds found in the smoke. Silicones typically burn cleanly to form an insulating silica layer upon combustion. We have examined the ability of silicones to convey improved thermal stability to soybean oil. The oil was modified via an ene reaction to incorporate an alkoxysilane functionality that was used in a subsequent Piers–Rubinsztajn reaction with silicones to create foams and elastomers. Cross-linked materials with densities ranging from ∼0.6 to 0.9 g/mL and containing up 76% by weight soybean oil were prepared. The addition of varying amounts of a linear PDMS chain extender allowed for control of the modulus (0.04–0.32 MPa). Cross-linking rapidly occurred, <60 s for full cure. Foams were produced without the need for external blowing agents, due to the generation of methane as a byproduct of the Piers–Rubinsztajn reaction. The soybean oil/silicone materials burned cleanly and without dripping, as shown in particular with the elastomer containing 76 wt % soybean oil. The external surfaces of the objects, after combustion, were rigid silica-rich structures.

    Copyright © 2018 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.8b05047.

    • Additional formulations leading to very soft elastomers; SEM of additional foams; NMR data showing the extractable is unreacted 1 (PDF)

    • Video 1: A soybean oil elastomer flammability test (MOV)

    • Video 2: Polyurethane foam sample flammability test (MOV)

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    Citation Statements
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    This article is cited by 13 publications.

    1. Anjuli M. Szawiola, Benoit H. Lessard, Hasan Raboui, Timothy P. Bender. Use of Piers–Rubinsztajn Chemistry to Access Unique and Challenging Silicon Phthalocyanines. ACS Omega 2021, 6 (41) , 26857-26869. https://doi.org/10.1021/acsomega.1c02738
    2. Adrien Lusterio, Miguel Melendez-Zamudio, Michael A. Brook. Aminosilicones without Protecting Groups: Using Natural Amines. Industrial & Engineering Chemistry Research 2021, 60 (10) , 3830-3838. https://doi.org/10.1021/acs.iecr.1c00201
    3. Slawomir Rubinsztajn, Julian Chojnowski, Urszula Mizerska. Tris(pentafluorophenyl)borane-catalyzed Hydride Transfer Reactions in Polysiloxane Chemistry—Piers–Rubinsztajn Reaction and Related Processes. Molecules 2023, 28 (16) , 5941. https://doi.org/10.3390/molecules28165941
    4. Olga V. Filippova, Aleksey V. Maksimkin, Tarek Dayyoub, Dmitry I. Larionov, Dmitry V. Telyshev. Sustainable Elastomers for Actuators: “Green” Synthetic Approaches and Material Properties. Polymers 2023, 15 (12) , 2755. https://doi.org/10.3390/polym15122755
    5. Jinfeng Cao, Cong Gui, Shengyu Feng. Porous recyclable sponges with controllable and durable shape memory. Materials Advances 2023, 4 (4) , 1075-1080. https://doi.org/10.1039/D2MA00953F
    6. Miguel Melendez-Zamudio, Erin Donahue-Boyle, Yang Chen, Michael A. Brook. Acrylated soybean oil: a key intermediate for more sustainable elastomeric materials from silicones. Green Chemistry 2023, 25 (1) , 280-287. https://doi.org/10.1039/D2GC04073E
    7. Hetian Gao, Andrew Battley, Erin M. Leitao. The ultimate Lewis acid catalyst: using tris(pentafluorophenyl) borane to create bespoke siloxane architectures. Chemical Communications 2022, 58 (54) , 7451-7465. https://doi.org/10.1039/D2CC00441K
    8. Chuanhui Gao, Yiliang Gao, Sikai Wang, Yajie Dong, Yumin Wu, Yuetao Liu, Chuanxing Wang. Self-healing unsaturated polyester sensor based on multiple hydrogen bonds. European Polymer Journal 2022, 175 , 111301. https://doi.org/10.1016/j.eurpolymj.2022.111301
    9. Qian Zhang, Zhiwei Guo, Yujie Yang, Yanxiang Li, Chuanfang Yang, Wangliang Li. The impact of SiO2 nanoparticles on the dilational viscoelastic properties of water-nonionic surfactant-fuel interface. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2022, 643 , 128757. https://doi.org/10.1016/j.colsurfa.2022.128757
    10. Julien Peyrton, Luc Avérous. Structure-properties relationships of cellular materials from biobased polyurethane foams. Materials Science and Engineering: R: Reports 2021, 145 , 100608. https://doi.org/10.1016/j.mser.2021.100608
    11. Minghao Yi, Xunjun Chen, Peter S. Shuttleworth, Lewen Tan, Yunqing Ruan, Yixin Xu, Jiefeng Zheng, Shufang Wu, Sen Hu, Simin Xie, Zhixing Guan, Guoqiang Yin, Yingde Cui. Facile fabrication of eugenol-containing polysiloxane films with good optical properties and excellent thermal stability via Si–H chemistry. Journal of Materials Chemistry C 2021, 9 (25) , 8020-8028. https://doi.org/10.1039/D0TC05279E
    12. Jinfeng Cao, Yan Wang, Dengxu Wang, Ruixue Sun, Mengdong Guo, Shengyu Feng. A Super‐Amphiphilic 3D Silicone Sponge with High Porosity for the Efficient Adsorption of Various Pollutants. Macromolecular Rapid Communications 2021, 42 (7) https://doi.org/10.1002/marc.202000603
    13. Yingying Liu, Xin Wang, Shengyu Feng. Nonflammable and Magnetic Sponge Decorated with Polydimethylsiloxane Brush for Multitasking and Highly Efficient Oil–Water Separation. Advanced Functional Materials 2019, 29 (29) https://doi.org/10.1002/adfm.201902488

    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2019, 7, 1, 1347–1352
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acssuschemeng.8b05047
    Published November 19, 2018
    Copyright © 2018 American Chemical Society

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