Synthesis of oleic-based primary glycol with high molecular weight for bio-based waterborne polyurethane

Wang, Li; Xiang, Jun; Wang, Songhang; Sun, Zhe; Wen, Jiating; Li, Jing; Zhong, Zheng; Fan, Haojun

doi:10.1016/j.indcrop.2021.114276

Cited by 18 publications

(14 citation statements)

References 43 publications

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“…The structure of oleic‐based primary glycol (OPG) was characterized by our earlier study 1 . The 1 H NMR spectra of methyl 10‐undecenoate (MU), chain‐extended methyl 10‐undecenoate (CEMU), and undecylenic‐based primary glycol (UPG) are presented in Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…The synthetic route and methods of oleic‐based primary glycol (OPG) were designed as reported by our earlier study, 1 as shown in Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

“…With the increasing concerns about the rapid consumption of world crude oil and soaring environmental problems, 1 enormous efforts have been engaged in exploring bio‐based monomers and polymers prepared from renewable biomass resources 2 . Vegetable oils are one of the most potential biomass resources among starch, chitosan, lignocellulosic, and protein because of their readily accessibility, inherent biodegradability, and diversity of functional groups, have been extensively applied in the production of several polymers 3,4 .…”

Section: Introductionmentioning

confidence: 99%

“…Man et al 14 obtained a bio‐based diol by amidation and used it to prepare linear BWPU, but the main chain (less than five carbon atoms) of the diol is too short to endow the designable properties of its soft segments. 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.…”

Section: Introductionmentioning

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: Resultsmentioning

confidence: 99%

“…The synthetic route and methods of oleic‐based primary glycol (OPG) were designed as reported by our earlier study, 1 as shown in Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

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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“…provide an effective platform for the preparation of value-added chemicals required for the synthesis of bio-based WPU. For example, Wang et al [6] synthesized a novel oleic-based primary glycol via Claisen condensation and thiol-ene photo-click reactions on the ester bond and carbon-carbon double bond of methyl oleate and used it as a substitute for petroleum-based diol to prepare bio-based WPU. Omrani et al [7] prepared a new type of carboxylic acid group-containing polyol through epoxy ring-opening and saponification of the carbon-carbon double bond and triglyceride bond of sunflower oil, respectively, which was further used as a hydrophilic chain extender to prepare biodegradable bio-based WPU.…”

Section: Introductionmentioning

confidence: 99%

High Water Resistance and Enhanced Mechanical Properties of Bio-Based Waterborne Polyurethane Enabled by in-situ Construction of Interpenetrating Polymer Network

Deng¹,

Lu²,

Liang³

et al. 2023

Journal of Renewable Materials

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In this study, acrylic acid was used as a neutralizer to prepare bio-based WPU with an interpenetrating polymer network structure by thermally induced free radical emulsion polymerization. The effects of the content of acrylic acid on the properties of the resulting waterborne polyurethane-poly (acrylic acid) (WPU-PAA) dispersion and the films were systematically investigated. The results showed that the cross-linking density of the interpenetrating network polymers was increased and the interlocking structure of the soft and hard phase dislocations in the molecular segments of the double networks was tailored with increasing the content of acrylic acid, leading to enhancement of the mechanical properties and water resistance of WPU-PAA films. Notably, with the increase in content of acrylic acid, the tensile strength, Young's modulus, and toughness of the WPU-PAA-110 film increased by 3 times, and 8 times, and 2.4 times compared with WPU-PAA-80, respectively. The WPU-PAA-100 film showed the best water resistance, and the water absorption rate at 96 h was only 3.27%. This work provided a new design scheme for constructing bio-based WPU materials with excellent properties.

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Biodegradability and Thermostability of Renewable Waterborne Polyurethane Synthesized from Trihydroxyl poly(L-malic acid)/glycol Based Polyols and Polycaprolactone Diol

Yu,

Song,

Niu

et al. 2023

J Polym Environ

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A biodegradable composite polyester-based waterborne polyurethane (L-AWPU) was synthesized by coupling L-malic acid and polyethylene glycol to obtain poly(L-malic acid ethylene glycol ester, PL-A) and polycaprolactone (PCL) as raw materials. The content of PL-A in polymer system was controlled to prepare L-AWPU with excellent biodegradable and thermostability properties. Compared to traditional PCL-WPU, the introduction of PL-A not only taking naturally degradable bio-based molecular chains into WPU, but also improving the branching degree of polyurethane molecular chains and formed intramolecular crosslinking structures due to the trifunctional hydroxyl group in malic acid. When the content of PL-A reached 20 wt%, the temperature of thermal weight loss (T5%) and maximum weight loss rate (T max ) of polyurethane coating increased from 237.93°C and 259.91°C to 333.86°C and 343.13°C, respectively. The establishment of intramolecular crosslinking structures and increase in molecular weight improved the thermal stability of polyurethane. The tensile strength

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Synthesis of oleic-based primary glycol with high molecular weight for bio-based waterborne polyurethane

Cited by 18 publications

References 43 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

High Water Resistance and Enhanced Mechanical Properties of Bio-Based Waterborne Polyurethane Enabled by in-situ Construction of Interpenetrating Polymer Network

Biodegradability and Thermostability of Renewable Waterborne Polyurethane Synthesized from Trihydroxyl poly(L-malic acid)/glycol Based Polyols and Polycaprolactone Diol

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