Bio-based healable non-isocyanate polyurethanes driven by the cooperation of disulfide and hydrogen bonds

Dong, Jincheng; Liu, Binyuan; Ding, Huining; Shi, Junbin; Ning, Liu; Dai, Bin; Kim, Il

doi:10.1039/d0py01249a

Cited by 72 publications

(61 citation statements)

References 56 publications

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“…Upon completion, the organic layer was rotary evaporated and dried overnight in a vacuum oven to collect pure CSBO with a brown color. 22,33 Preparation of CSBO−MDA PHUs. The preparation method of CSBO−MDA PHUs is simple.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Fully Bio-Based Polyhydroxyurethanes with a Dynamic Network from a Terpene Derivative and Cyclic Carbonate Functional Soybean Oil

Liu

Yang

Wang

et al. 2021

ACS Sustainable Chem. Eng.

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Polyhydroxyurethanes (PHUs), polyurethanes with excellent properties, are cured without poisonous isocyanate. The carbamate groups in the structure can undergo bond exchange in the presence of amino groups to improve their reprocessing and recyclability. As the demand for more "sustainable" polymers increases, research has focused on replacing fossil materials with renewable alternatives. 1,8-Menthane diamine (MDA) derived from turpentine is a potential raw material for curing with cyclic-carbonated soybean oil (CSBO) for preparing fully bio-based PHUs without solvents and catalysts. The amino groups from MDA facilitate bond exchange under autocatalysis in PHUs, and the rigid structure improves the thermal and mechanical properties of PHUs. PHUs with different cyclic carbonate/amino ratios are characterized to explain the importance of MDA in the performance of PHUs. Dynamic covalent bond exchange was studied through stress relaxation, which results in self-healing, recyclability, reprocessing, and shape memory. The mechanical properties and thermal stability can be almost completely recovered (>85%) after reprocessing several times, indicating that the network will be repaired by bond exchange. This work provides a promising strategy to utilize sustainable feedstocks for designing fully bio-based non-isocyanate polyurethanes and reveals the effect of the structure on the material properties.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Fully Bio-Based Polyhydroxyurethanes with a Dynamic Network from a Terpene Derivative and Cyclic Carbonate Functional Soybean Oil

Liu

Yang

Wang

et al. 2021

ACS Sustainable Chem. Eng.

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“…Furthermore, cystamine, S 2 ((CH 2 ) 2 ‐NH 2 ) 2 , has been integrated in the development of self‐healable polyhydroxyurethanes. [ 89,90 ] For example, isocyanate‐free PUU containing backbone aliphatic disulfide linkages was synthesized by the polyaddition of a carbonated soybean oil with isophorondiamine and cystamine. The formed PUU materials had self‐healing efficiency up to 98% at room temperature.…”

Section: Incororation Of Dynamic Covalent Chemistriesmentioning

confidence: 99%

Dynamic Covalent Polyurethane Network Materials: Synthesis and Self‐Healability

Nellepalli

Patel

2021

Macromol. Rapid Commun.

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Polyurethane (PU) has not only been widely used in the daily lives, but also extensively explored as an important class of the essential polymers for various applications. In recent years, significant efforts have been made on the development of self‐healable PU materials that possess high performance, extended lifetime, great reliability, and recyclability. A promising approach is the incorporation of covalent dynamic bonds into the design of PU covalently crosslinked polymers and thermoplastic elastomers that can dissociate and reform indefinitely in response to external stimuli or autonomously. This review summarizes various strategies to synthesize self‐healable, reprocessable, and recyclable PU materials integrated with dynamic (reversible) Diels–Alder cycloadduct, disulfide, diselenide, imine, boronic ester, and hindered urea bond. Furthermore, various approaches utilizing the combination of dynamic covalent chemistries with nanofiller surface chemistries are described for the fabrication of dynamic heterogeneous PU composites.

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“…SMPU can be regarded as a block copolymer of a soft segment and a carbamatebased hard segment [24,25]. There are many hydrogen bonds between hard segments, which bind the movement of hard segments and make the hard segments tend to aggregate, while the soft segments can deform greatly [26][27][28][29]. Although the compatibility between the two chains is poor, it can be connected by a chemical bond, which makes polyurethane form a microphase separation structure [30,31].…”

Section: Introductionmentioning

confidence: 99%

The effect of promoting hydrogen bond aggregation based on PEMTC on the mechanical properties and shape memory function of polyurethane elastomers

et al. 2022

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In this work, small molecule diols named PEMTC were synthesized from isophorone diisocyanate, N-(2-hydroxyethyl)acrylamide and trimethylolpropane by a semi-directional method. PEMTC (2-(prop-2-enamido)ethyl N-{3-[({[2-ethyl-3-hydroxy-2(hydroxymethyl)propoxy]carbonyl}amino)methyl]-3,5,5-trimethylcyclohexyl}carbamate) contains hydrogen bond active site and light-initiated C=C. We introduced it as a branch chain block into poly(ε-caprolactone) (PCL). By feeding and monitoring the reaction process, we synthesized a large number of polyurethane elastomers, hydrogen bonds PCL-based elastomer (HPE), which contain a large number of dynamic hydrogen bonds. Under UV irradiation, PEMTC can make HPE molecules aggregate and cross-link, improve the degree of internal hydrogen bonding interaction of HPE materials and endow HPE materials with good elasticity, toughness, heat resistance and shape memory ability. After 270 nm UV irradiation, the elongation at break of HPE materials decreased from 607.14–1463.95% to 426.60–610.36%, but the strength at break of HPE materials increased from 3.36–13.52 to 10.28–41.52 MPa, and the toughness increased from 16.36–129.71 to 40.48–172.22 MJ m −3 . In addition, the highest shape fixation rate of HPE after UV irradiation was 98.0%, and the recovery rate was 93.7%.

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Bio-based healable non-isocyanate polyurethanes driven by the cooperation of disulfide and hydrogen bonds

Abstract: A series of isocyanate-free polyurethanes (NIPUs), showing intrinsic thermo-healing performance, have been synthesized from sustainable vegetable oil-based cyclic carbonates and bio-resourced amines. The bio-based contents of the NIPUs are higher...

Cited by 72 publications

References 56 publications

Fully Bio-Based Polyhydroxyurethanes with a Dynamic Network from a Terpene Derivative and Cyclic Carbonate Functional Soybean Oil

Fully Bio-Based Polyhydroxyurethanes with a Dynamic Network from a Terpene Derivative and Cyclic Carbonate Functional Soybean Oil

Dynamic Covalent Polyurethane Network Materials: Synthesis and Self‐Healability

The effect of promoting hydrogen bond aggregation based on PEMTC on the mechanical properties and shape memory function of polyurethane elastomers

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