Self-Plasticized PVC Prepared by Introducing Fatty Acid to the PVC with Triglycidyl Isocyanurate as an Intermediate Bridge

Abstract

The phthalate-free self-plasticization of poly(vinyl chloride) (PVC) conforms to the concept of green chemistry. In this work, phthalate-free, biocontaining, self-plasticized PVC with nonmigration (4-an-TG-X-PVC; X = R, P, or O) was prepared by covalent attachment of ricinoleic acid, palmitic acid, and oleic acid, respectively, to the PVC matrix with 4-aminothiophenol and triglycidyl isocyanurate (TGIC) as intermediate bridges. 4-Aminothiophenol and TGIC acted as the nucleophilic reagent and the thermally stable substance, respectively. The 4-an-TG-X-PVC was observed by diverse characterization methods. Specifically, Fourier transform infrared spectra, 1 H nuclear magnetic resonance, gel permeation chromatography, and migration stability tests proved the successful synthesis of 4-an-TG-X-PVC. Compared to the neat PVC, the mechanical property of 4-an-TG-X-PVC is better. The glass transition temperature (T g ) of PVC is 81.24 °C, while that of 4-an-TG-X-PVC decreased to 41.88, 31.49, and 46.91 °C. The 4-an-TG-X-PVC showed higher elongation at break and lower tensile strength than neat PVC. Simultaneously, the thermal property of 4-an-TG-X-PVC got a boost. Thermogravimetry−infrared and thermogravimetry−mass spectrometry showed that 4-an-TG-X-PVC released less HCl than neat PVC in a thermal environment. Discoloration experiments demonstrated that 4-an-TG-P-PVC had better heat stabilization and better color than 4-an-TG-O-PVC and 4-an-TG-R-PVC. This work provides a viable solution to the dependence on phthalates, reduced human health and ecological risks, and endowed PVC with improved thermal stability and nonmigration performance.

Upcycling poly(vinyl chloride) waste tubes: Studies of thermal stability and kinetics of films made of waste polyvinylchloride tube at the initial steps of degradation

“…Also, we underscore that the thermal degradation of wPVCf was not a single‐step reaction as reported by many researchers, for example, Refs. 1,6,17,22,25,43,46. The constancy of the values of E a , in this case, refers to a multi‐step reaction whose rate is dominated or limited by one of the slowest steps.…”

Chlorinated plastics offer unique opportunities and challenges in upcycling

“…70 To tackle this issue, covalently bonded internal plasticization became one of the most common, and fast growing, areas of PVC functionalization research. In one example, PVC that was modified with 4-aminothiophenol through nucleophilic substitution was reacted with a fatty acid-triglycidyl isocyanurate complex to produce covalently plasticized PVC 71 (Fig. 6).…”

“…Illustration of the mechanism of internal plasticization of thiol‐modified PVC using fatty acid–triglycidyl isocyanurate complex and the mechanism of HCl absorption by epoxy groups. Reprinted from Deng et al 71 . Copyright (2022), with permission from the American Chemical Society.…”

Investigation and effect of PVC and PVTMS on sintering, physical and mechanical features of chipboard wood

“…Furthermore, in nano-composites, the binding energy of the C 1s peak associated with C-Cl bonds in PVC is typically lower than that of the C 1s peak associated with C-C bonds, reflecting the different chemical environments of these carbon atoms [35]. [36]. Also, the binding energy values for Cl 2p in PVC are also around 284.3 eV and reflect the chemical environment of the chlorine atoms bonded to carbon atoms in the polymer chain [37], [38].…”