Tuning the hydrophobicity of bio-based waterborne polyurethane by leveraging a diol derived from oleic acid

Wang, Li; Gao, Qiang; Li, Jing; Jiang, Licheng; Wang, Songhang; Fan, Haojun; Chen, Yi; Yan, Jun; Xiang, Jun

doi:10.1016/j.indcrop.2022.115400

Cited by 18 publications

(8 citation statements)

References 41 publications

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“…For OPG-based BWPU, there are hydrophobic dangling chains besides the main alkane chains. Further, these dangling chains can migrate onto the surface of BWPU films in film formation process, 15,32 which greatly decreases the surface energy and prevents water molecules from entering the interior. Therefore, the dangling chains enhanced the hydrophobicity and waterresistance of the BWPU.…”

Section: Effect Of Dangling Chains On Hydrophobic Propertiesmentioning

confidence: 99%

“…In our previous study, 1 an oleic‐based primary glycol (OPG) with accurate M w , long main‐chain, and short side‐chain structure was prepared by a Claisen condensation followed by a thiol‐ene click reaction, and successfully utilized to prepare BWPU with tunable properties. In addition, our recent work 15 demonstrated that the diol with long alkane‐chain structure including main and dangling chains decreased the hydrophilicity of prepolymer, affecting the emulsifying state and emulsion properties of WPU. Generally, the side chains in the soft segments of WPU are easier to move than the main chains 16,17 .…”

Section: Introductionmentioning

confidence: 98%

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confidence: 99%

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The missing piece: Effect of dangling chains on the synthesis and properties of bio‐based waterborne polyurethane

Wang

Luo

Gao

et al. 2023

Journal of Polymer Science

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Bio‐based polyols derived from vegetable oils generally contain the dangling chains, which have recently attracted significant attention due to their influence on the preparation and performance of the waterborne polyurethane. Herein, a novel undecylenic‐based primary glycol (UPG) without dangling chains synthesized and the oleic‐based primary glycol (OPG) with dangling chains reported by our previous work were used to prepare straight‐chain and dangling‐chain bio‐based waterborne polyurethane (BWPU), respectively, to study the difference between the two diols and the effects of dangling chains on the synthesis and performance of BWPU. First, the UPG without dangling chains displayed higher activation energy (Ea/Eo = 77.72/80.56 kJ mol−1) and longer reaction end point of prepolymer (240 min), indicating relatively lower reactivity to isocyanate. In addition, the dangling chains were found to influence the dispersion stability of BWPU, and the minimum dosage of DMPA for maintaining dispersion stability was 6.5 wt% for OPG but 5.5 wt% for UPG. The average particle size of BWPU is greater for OPG than for UPG with the same DMPA content. Finally, performance studies revealed that dangling‐chain BWPU showed higher hydrophobicity, extensibility, and low temperature resistance, but lower thermal stability (Td5%) and tensile strength. This work comprehensively clarified the effects of linear and branched bio‐based polyols on the synthesis and properties of BWPU, and provided guidance for the development and application of bio‐based polyols and BWPU coatings.

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Section: Effect Of Dangling Chains On Hydrophobic Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

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The missing piece: Effect of dangling chains on the synthesis and properties of bio‐based waterborne polyurethane

Wang

Luo

Gao

et al. 2023

Journal of Polymer Science

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“…Due to the existence of a large number of hydrophilic units in WPU, the hydrophobicity and mechanical properties of waterborne polyurethane are relatively poor and limit its wide applications. Therefore, enhancing the hydrophobicity and mechanical properties for the waterborne polyurethane is the meaningful point attracted by the researchers for studying the environmentally friendly and outstanding waterborne polyurethane to expand their application prospects [9,10].…”

Section: Introductionmentioning

confidence: 99%

Study of a Novel Fluorine-Containing Polyether Waterborne Polyurethane with POSS as a Cross-Linking Agent

Deng

Zhang

et al. 2023

Polymers

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Waterborne polyurethane are more eco-friendly materials due to lower volatile organic compounds (VOCs, mainly isocyanates) content than the alternative materials. However, these rich hydrophilic groups polymers have not yet reached good mechanical properties, durability and hydrophobicity behaviors. Therefore, hydrophobic waterborne polyurethane has become a research hotspot, attracting significant attention. In this work, firstly, a novel fluorine-containing polyether P(FPO/THF) was synthesized by cationic ring-opening polymerization of 2-(2,2,3,3-tetrafluoro-propoxymethyl)-oxirane (FPO) and tetrahydrofuran (THF). Secondly, fluorinated polymer P(FPO/THF), isophorone diisocyanate (IPDI) and hydroxy-terminated polyhedral oligomeric silsesquioxane (POSS-(OH)8) were used to prepare a new fluorinated waterborne polyurethane (FWPU). Hydroxy-terminated POSS-(OH)8 was used as a cross-linking agent, while dimethylolpropionic acid (DMPA) and triethylamine (TEA) were used as a catalyst. Four kinds of waterborne polyurethanes (FWPU0, FWPU1, FWPU3, FWPU5) were obtained by adding different contents of POSS-(OH)8 (0%, 1%, 3%, 5%). The structures of the monomers and polymers were verified by 1H NMR and FT-IR, and the thermal stabilities of various waterborne polyurethanes were analyzed by thermogravimetric analyzer (TGA) and differential scanning calorimetry (DSC). As the results, the thermal analysis showed that the FWPU performed the good thermal stability and the glass transition temperature could reach at about −50 °C. The FWPU1 film exhibited that the elongation at break was 594.4 ± 3.6% and the tensile strength at break was 13.4 ± 0.7 MPa, elucidating that the FWPU1 film developed the excellent mechanical properties relative to the alternative FWPUs. Further, the FWPU5 film performed the promising properties, including the higher surface roughness of FWPU5 film (8.41 nm) obtained by the atomic force microscope (AFM) analysis, and the higher value of water contact angle (WCA) at 104.3 ± 2.7°. Those results illustrated that the novel POSS-based waterborne polyurethane FWPU containing a fluorine element could develop the excellent hydrophobicity and mechanical properties.

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“…5,9,10,[15][16][17] However, the value of specific vegetable oil-derived substances like oleic acid remains limited. Huang et al 12 and Wang et al 18 reported the use of oleic acid as a polyol for the synthesis of PUs. Xiong et al 19 also used oleic acid ester derivatives as raw materials for polyurethane synthesis.…”

mentioning

confidence: 99%

Synthesis and characterization of green urethane non‐isocyanate from oleic acid for wood composite application

Ghozali,

Bakhri,

Triwulandari

et al. 2023

J of Applied Polymer Sci

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Conventional polyurethane (PU) is usually synthesized by a reaction between isocyanate and polyol. The use of isocyanate compounds is associated with significant health and environmental problems. Therefore, it is necessary to develop an environmentally friendly alternative method for manufacturing PUs without isocyanate routes. The aim of this research work was to synthesize green urethane from oleic acid, which included the following three stages: the synthesis of epoxidized oleic acid (EOA), the synthesis of carbonated oleic acid (COA), and the synthesis of green urethane from oleic acid (UOA). The resulting product was characterized by Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR) analyses, and by determining the iodine number, oxirane number, and hydroxyl value. The results of FTIR and NMR showed that EOA was successfully synthesized. The optimum COA synthesis process was obtained on TBAB catalyst usage of 1% (wt/wt) at 140°C for 48 h with a 500‐rpm stirring rate and CO2 gas flow rate of 0.2 mL/min with the resulting COA oxirane value of 0.00. The optimum condition of UOA synthesis through the aminolysis process resulted in the use of LiCl of 19.8% (wt/wt) at 70°C for 3 h with a stirring speed of 1200 rpm with a UOA hydroxyl number generated of 237.93 mg/mL.

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Tuning the hydrophobicity of bio-based waterborne polyurethane by leveraging a diol derived from oleic acid

Cited by 18 publications

References 41 publications

The missing piece: Effect of dangling chains on the synthesis and properties of bio‐based waterborne polyurethane

The missing piece: Effect of dangling chains on the synthesis and properties of bio‐based waterborne polyurethane

Study of a Novel Fluorine-Containing Polyether Waterborne Polyurethane with POSS as a Cross-Linking Agent

Synthesis and characterization of green urethane non‐isocyanate from oleic acid for wood composite application

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