Synthesis of Gallic Acid-Derived Plasticizers for Polyvinyl Chloride Featuring Excellent Plasticization, Thermo-Stability, and Migration Resistance

Abstract

The development of a facile and environmental strategy for manufacturing a natural aromatic-derived plasticizer for poly(vinyl chloride) (PVC) featuring excellent plasticization, UVshielding, and thermostability, together with migration resistance, is still a challenge. Herein, a series of gallic acid-derived polypropylene glycol monomethyl ether esters with natural aromatic rings (TGPME-n, n = 1, 2, or 3 referring to the number of methylethoxy units in the structure of TGPME-n) were developed as plasticizers for PVC via the simple esterification of gallic acid with polypropylene glycol monomethyl ether and sequent etherification with epichlorohydrin in a one-pot process without any HCl generation. Extensive experiments showed that the performances of PVC blended with TGPME-n were highly dependent on the number of methylethoxy units from TGPME-n, where the performances of PVC plasticized by TGPME-n with more methylethoxy units were better than those of TGPME-n bearing one. Benefiting from the strong interaction of aromatic and polar groups (epoxy, ethoxy, and ester groups) in TGPME-n with a PVC skeleton, plasticization, low temperature resistance, thermal stability, transparency, and UV-shielding as well as migration resistance of PVC plasticized by TGPME-3 with maximum methylethoxy units were superior to those of PVC blended with dioctyl phthalate (DOP), implying that TGPME-3 could be used as an attractive alternative to totally replace the toxic DOP. This study provides a simple and feasible strategy to fabricate a highly efficient natural aromatic-derived plasticizer for the PVC industry.

Biodegradable Hydrogenated Dimer Acid-Based Plasticizers for PLA with Excellent Plasticization, Thermal Stability and Gas Resistance

“…From the photos, the transparency of PLA/HDA-2 n is obviously better than that of PLA/DOTP, which indicates that the compatibility of HDA-2 n with a PLA carrier is better than that of the traditional plasticizer, DOTP. With an increase in the number of ethoxy units, the transparency of plasticized PLA samples increased continuously, which was also consistent with a previous report [ 34 ].…”

“…Migration resistance tests adhered to the GB/T3830-2008 standard [ 34 ], submerging the sample (20 × 20 × 1 mm) in an n-hexane solution at 23 ± 2 °C and 50 ± 10% humidity. Samples were dried at 50 °C for 6 h, and the mass loss rate was determined via Equation (1): where W before and W after represent the weight of the PLA samples before and after the test, respectively, and x represents the initial concentration of plasticizer in the PLA sample, testing five samples per set.…”

“…Migration resistance tests adhered to the GB/T3830-2008 standard [34], submerging the sample (20 × 20 × 1 mm) in an n-hexane solution at 23 ± 2 • C and 50 ± 10% humidity. Samples were dried at 50 • C for 6 h, and the mass loss rate was determined via Equation (1): Migration degree = W before − W after W before × x ×100%…”

Synthesis of bio‐based plasticizer from custard apple seed oil for PVC application

“…This slight elevation could be attributed to the potential incompatibility of ECASO at higher loadings in the PVC sheet. 7,25,26 The study demonstrated that the addition of ECASO as a plasticizer in PVC systems effectively reduced the T g , indicating enhanced plasticization. An optimal DOP: ECASO ratio of around 40:60 appeared to maximize the plasticizing effect.…”