Preparation of cardanol based epoxy plasticizer by click chemistry and its action on poly(vinyl chloride)

Abstract

In recent years, the using of reproducible resource and economical and efficient synthesis method has got wide concern. Herein, an environmental-friendly plasticizer originated from cardanol was synthesized by click chemistry. First, the cardanol sulfide (CS) was obtained by click chemistry reaction between the double bond of the side chain of cardanol and mercaptoethanol. The degree of the click reaction was estimated to reach 84.7% by testing the content of sulfur. Then, the epoxidation of the hydroxyl was performed to get cardanol based epoxy plasticizer (CEP) in the presence of epichlorohydrin. The epoxy value was 0.32. The structure of CS and CEP was confirmed by FT-IR and NMR techniques. A Haake torque rheometer was used to research the action of CEP on polyvinyl chloride (PVC). Results showed that it possessed favorable plasticization effect and stabilization effect on PVC. CEP had good heat stabilization in PVC, and could decrease the T g of PVC significantly. Moreover, CEP could increase the tensile strength of PVC when in a small amount, and could increase the plasticity of PVC when in a larger quantity significantly. The characteristics of volatile, migration and solvent extraction of PVC plasticized by CEP is similar to by dioctyl phthalate (DOP). V C 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44890.

Mechanical and barrier properties of polyvinyl chloride plasticized with dioctyl phthalate, epoxidized soybean oil, and epoxidized cardanol

“…They also observed no migration of the self‐plasticized PVC films against PVC/DOP system where 15.7% of DOP leached into n‐hexane. Yao et al [ 16 ] prepared cardanol based epoxy plasticizer (CEP) by click chemistry and studied its action on PVC. They observed that CEP could increase the tensile strength of PVC when used in a small amount and could increase the plasticity of PVC when used in larger quantity.…”

Cardanol Groups Grafted on Poly(vinyl chloride)—Synthesis, Performance and Plasticization Mechanism

“…Peaks appeared at δ 5.41 ppm, which were associated with protons of hydroxyl groups. The signal of the olefin groups appeared at δ 5.44 ppm, and the signals of the protons for the benzene rings could be observed at δ 6.71, δ 6.82 and δ 7.18 ppm [ 19 , 21 , 22 ]. In comparison to the 1 H NMR spectrum of cardanol, a new signal appeared at δ 4.75 ppm, which was attributed to the protons of methylene groups connected to alkynyl groups.…”

Clicking Biobased Polyphenols: A Sustainable Platform for Aromatic Polymeric Materials

“…Cardanol can be converted into a polyol or a polyamine through a straightforward reaction with 2‐mercaptoethanol or cysteine hydrochloride, respectively . The resulting polyol‐ and polyamine‐based cardanols were further used in the synthesis of PURs.…”