Bis(2-ethylhexyl) succinate in mixtures with epoxidized soybean oil as bio-based plasticizers for poly(vinylchloride)

Abstract

Mixtures of bis(2‐ethylhexyl) succinate and epoxidized soybean oil (ESO) have been evaluated as bio‐based plasticizers for poly(vinylchloride). The rate of absorption of the bioplasticizers and their mixtures in the polymer was fast and, unlike that of petroleum‐derived plasticizers, did not vary significantly with molecular weight. These bio‐derived plasticizers and their mixtures were compatible with the polymer even at high loadings. The succinate was the most volatile and efficient plasticizer, but on heat aging of the polymer compositions, it also had the greatest deleterious effects. Diffusion coefficients and apparent activation energies of formulations containing bioplasticizer mixtures were controlled by the more volatile succinate. Mixtures comprising up to 50 wt% of the succinate yielded acceptably high‐tensile properties after thermal aging as well as better plasticization efficiency than the epoxy bioplasticizer. Although the succinate resulted in inferior volume resistivity of the polymer compositions, improvements were obtained with increasing proportions of the epoxidized derivative in plasticizer mixtures. Melt state viscosity‐shear rate curves of compositions containing dioctyl succinate (DOS) were similar to those made with two of the petroleum‐derived plasticizers, but a DOS/ESO mixture yielded extended non‐Newtonian behavior at low‐shear rates. POLYM. ENG. SCI., 55:634–640, 2015. © 2014 Society of Plastics Engineers

Thermal and mechanical properties of bio-based plasticizers mixtures on poly (vinyl chloride)

“…As a result, the chain mobility and thus the flexibility of the compounds are reduced, although the increase in tensile strength and decrease in elongation at break with ESO plasticizer may be attributed to its high viscosity. Reduction in tensile strength with an increase in ATBC or ISB content (60 phr) possibly result from a high plasticization efficiency compared to the one of other plasticizers [33] , which allows facile sliding of polymer chains past each other [32] . Hence, compounds of ATBC/ESOME (40/20) and ISB/ESOME (50/10) give the highest elongation at break 858% and 871% respectively.…”

Epoxidized linolenic acid salts as multifunctional additives for the thermal stability of plasticized PVC

“…The two mixtures were then combined, heated to 95°C and thoroughly mixed in the same manner stated previously. This temperature is above the glass transition temperature of unplasticized PVC (83°C) which facilitated the efficient absorption of the additive by the PVC. This two pot‐blending technique of the plasticizer with the PVC afforded the complete uptake and uniform distribution of the additives.…”

“…The soybean oil has a high content of nonconjugated double bonds that are easily epoxidized using standard and inexpensive reagents. Similar to the already mentioned phthalate plasticizers, ESO has been shown to be sufficiently compatible with PVC and an effective plasticizer, but only when used in combination with mixed metal soap as heat stabilizer to prevent acid‐catalyzed oxirane ring opening …”

“…The general approach has been to develop additives which can promote substitution reactions incorporating more stable substituents on the polymer backbone to retard or prevent elimination processes, and/or simply sequester the generated HCl via neutralization processes to promote long‐term stability . These additives include metal salts of fatty acids and molecules containing epoxide functionalities . Traditional metal carboxylate additives, such as Ca and Zn stearates, have been synergistically used to slow the unzipping process.…”

Synthesis and characterization of castor oil-based polymeric surfactants

“…A useful reaction for the modification of vegetable oils is the epoxidation of double bonds. Epoxidized soybean oil (ESO) provided commercially at reasonable cost has been used as a raw material for synthesis of new polymers [14][15][16][17][18][19] . According to the literature, ring-opening reaction of ESO with different alcohols was achieved using dry Amberlyst 15 as a catalyst [20] .…”