A Solvent-Free and Scalable Method To Prepare Soybean-Oil-Based Polyols by Thiol–Ene Photo-Click Reaction and Biobased Polyurethanes Therefrom

Abstract

A solvent-free and scalable method was developed for the preparation of soybean-oil-based polyols by a thiol–ene photo-click reaction with a homemade photochemical reactor. The effect of reaction parameters, including photoinitiators, reaction time, molar ratios of thiols to carbon–carbon double bonds, and power of the mercury lamp, on the structures of the resulting polyols was investigated. The mechanism of the thiol–ene photo-click reaction was also discussed. On the basis of these novel polyols, several polyurethanes were prepared using different diisocyanates (aliphatic, cycloaliphatic, and aromatic isocyanate) and characterized. The resulting polyurethane films possess good performance, including the highest glass transition temperature of 41.3 °C, tensile strength of 15.7 MPa, and elongation at break of 471.0%.

Castor oil‐based polyols with gradually increasing functionalities for biopolyurethane synthesis

“…Castor oil, thiols, and photo initiators (DMPA) were placed in quartz tubes sealed with rubber septa. The thiol‐to‐oil ratio was decided at a molar ratio of 4/1, optimized by the works of Feng et al . After 24 h of reaction time, the products were collected and washed with water and brine for at least five times.…”

“…Thiol‐ene click chemistry is a facile and efficient method for the synthesis of multifunctional materials . Due to its simple reaction conditions, stereoselectivity, high rate and high yield, thiol‐ene reactions have attracted the attention of many researches for the utilization of plant oils as feedstock for biopolymers . Türünç and Meier .…”

“…Desroches et al . and Feng et al . have optimized the grafting of 2‐mecaptoethanol on to rapeseed oil and soybean oil, respectively, to yield plant oil‐based polyols.…”

Bio-based reactive diluents as sustainable replacements for styrene in MAESO resin

“…[7][8][9] Among them, soybean oils are one of the most widely investigated platform chemicals to replace petroleum-based chemical in the preparation of biobased thermosets because of their abundant availability, sustainability, and relatively low cost. [10][11][12] Soybean oils are composed of approximately 99% of triglycerides. Soybean oils contain mainly ve fatty acids: palmitic acid (10%), stearic acid (4%), oleic acid (18%), linolenic acid (13%), and linoleic acid (55%).…”

Recent Advancement in Plant Oil Derived Polyol‐Based Polyurethane Foam for Future Perspective: A Review

“…synthesized rigid PUF using SO into a continuous micro‐flow system equipped with self‐designed oil–water separators. Feng et al . synthesized SOP using solvent‐free process using thiolene photoclick reaction.…”