A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP

Pan, Siyu; Hou, Delong; Chang, Jinming; Xu, Zhaoyi; Wang, Songhang; Yan, Sunxian; Zeng, Qi; Wang, Zhonghui; Chen, Yi

doi:10.1039/c9gc03077h

Cited by 35 publications

(19 citation statements)

References 27 publications

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“…In addition, PVC resin and the plasticizers are thermodynamically incompatible, so the plasticizers are inclined to migrate from the PVC coating, shorting the service life of PVC artificial materials. This is particularly true for many halogen-free intrinsically flame-retardant plasticizers in that they usually display weak interaction with PVC matrix despite of flame retardancy [3,16]. Herein, chlorinating FAME yielded a bio-plasticizer with two chlorine moieties that displayed strong polar interaction with PVC, and thus the migration of CFAME could be significantly suppressed compared with other chlorinefree substitutes.…”

Section: Resultsmentioning

confidence: 99%

A simple approach with scale-up potential towards intrinsically flame-retardant bio-based co-plasticizer for PVC artificial materials

Wang

Chang

et al. 2020

J Leather Sci Eng

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As an imitation of genuine leather, polyvinyl chloride (PVC) artificial materials are versatile, but suffers from being flammable due to the presence of large amounts of combustible plasticizers. Under such circumstance, intrinsically flame-retardant plasticizers displaying dual functions have been a subject of intensive research interest. However, previous strategies attempting to covalently attach flame-retardant moiety to plasticizers invariably required either expensive starting materials or laborious and tedious procedures, ultimately limiting their scale-up application in industry. In addition, driven by escalating demand of halogen-free flame retardants worldwide from an environmental health perspective, previously reported intrinsically flame-retardant plasticizers were mainly halogenfree, less attractive in PVC artificial material industry simply because PVC itself is a halogen-containing polymer. Here, we report an approach to introduce chlorine moieties into unsaturated fatty acid methyl ester by a simple addition reaction occurring on carbon-carbon double bonds, yielding a chlorine-containing, intrinsically flameretardant bio-plasticizer. When combined with di-(2-ethylhexyl) phthalate (DOP) in PVC formulations, the chlorinated fatty acid methyl ester is qualified as a co-plasticizer while conferring flame retardancy upon the PVC coatings. This approach involves only a one-step procedure that employs renewable fatty acid methyl esters and cheap chlorine gas as raw materials, thus being of great potential to enable intrinsically flame-retardant bioplasticizers on a large scale to manufacture functional PVC artificial materials for application in fire-prone scenarios.

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Section: Resultsmentioning

confidence: 99%

A simple approach with scale-up potential towards intrinsically flame-retardant bio-based co-plasticizer for PVC artificial materials

Wang

Chang

et al. 2020

J Leather Sci Eng

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“…There is a corresponding relationship between the MSD value and the diffusion coefficient ( D ). The diffusion coefficient in the process of kinetic simulation can reflect the migration ability of RA molecules in collagen . The greater the binding effect of diffusing particles in the medium, the smaller the diffusion coefficient.…”

Section: Methodsmentioning

confidence: 99%

“…The diffusion coefficient in the process of kinetic simulation can reflect the migration ability of RA molecules in collagen. 37 The greater the binding effect of diffusing particles in the medium, the smaller the diffusion coefficient. The diffusion coefficients of RA, RA-OH, RA-NH 2 , and RA-COOH in collagen can be calculated by the Einstein relation.…”

Section: ■ Introductionmentioning

confidence: 99%

Relationship between the Structure of Modified Ricinoleic Acids via the Thiol–Ene Click Reaction and the Fogging Value of Fatliquored Leather

Zhang

Liu

et al. 2022

ACS Sustainable Chem. Eng.

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Herein, hydroxylated, aminated, and carboxylated ricinoleic acids (RA-OH, RA-NH 2 , RA-COOH) are individually prepared via facile and efficient thiol−ene click reactions with renewable ricinoleic acid and commercially available sulfhydryl compounds as raw materials. The resulting modified ricinoleic acids are subsequently used as natural oils to prepare environmentally friendly fatliquors for automotive interior leather of a low fogging value. Further, the influence of the molecular structure of the three modified ricinoleic acids on the fogging value and free grease content of the fatliquored leather is systematically studied by molecular dynamics simulation theoretical predictions and regular experimental characterization. The introduction of −OH, −NH 2 , and −COOH to ricinoleic acid can increase its ability to form strong intermolecular interactions with leather collagen fibers, as confirmed by the E binding values from molecular dynamics simulations. The interaction strength of modified ricinoleic acids and leather collagen is in the order RA-OH > RA-COOH > RA-NH 2 > RA, leading to a low migration rate of modified ricinoleic acids and an obvious lubricating effect on the collagen fibers. Among them, RA-OH shows the strongest intermolecular interaction with leather collagen and is difficult to migrate from the collagen matrix; thus, the RA-OH fatliquored leather exhibits the lowest fogging value of 6.38 mg, the lowest free grease content of 12.36%, and excellent softness and physical and mechanical properties. Overall, a combination of renewable ricinoleic acids with "green" thiol−ene click reactions provides a new strategy for the preparation of sustainable fatliquors for automotive interior leather of a low fogging value, and the wastewater after fatliquoring is also biodegradable, all of which contribute to the sustainable development of the fatliquors in the leather industry.

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“…To date, many natural resources such as vegetable oil, − rosin, and cardanol , have been utilized as feedstocks for synthesis of nontoxic and biodegradable plasticizers. Among the resources, vegetable oil is considered as an ideal feedstock as a result of its bargain price, environmentally friendly properties, and easy modification.…”

Section: Introductionmentioning

confidence: 99%

“…Among the resources, vegetable oil is considered as an ideal feedstock as a result of its bargain price, environmentally friendly properties, and easy modification. Pan et al developed a family of ester-branched plasticizers derived from vegetable oil featured with low cytotoxicity, biodegradability, and renewability, and they could be used as sustainable alternatives for DOP. Green plasticizers for PVC were synthesized through the ring-opening reaction between epoxidized soybean oil and acid anhydride .…”

Section: Introductionmentioning

confidence: 99%

Waste Fatty Acid-Based Methyl Tetraglycol Ester Derived from Dimer Acid Manufacturing as an Efficient and Biodegradable Plasticizer for Poly(vinyl chloride)

Tan

Wang

et al. 2021

ACS Sustainable Chem. Eng.

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Increasing evidence has shown that plasticizer pollution and waste fatty acid contamination are serious environmental issues in our daily lives. Herein, an environmental friendly plasticizer (waste momomer fatty acid-based methyl tetraglycol ester, WMA-MTE) was designed and prepared via the direct esterification of waste momomer fatty acid derived from dimer acid manufacturing and methyl tetraglycol. The resulting WMA-MTE was used as a potential alternative for toxic petro-based dioctyl phthalate (DOP) in plasticizing poly(vinyl chloride) (PVC). The properties of plasticized PVC including low temperature capability, tensile properties, thermal stability, and migration resistance were dependent on the content of WMA-MTE. Among them, the overall performances of PVC plasticized with 100% WMA-MTE (PVC/WMA-MTE) were better than others, which could be attributed to the excellent abilities of oxethyl units in WMA-MTE in both improving the compatibility and flexibility. Importantly, WMA-MTE could be biodegraded only by being buried in soil. All the above results suggest that WMA-MTE is an attractive alternative to DOP in the PVC industry.

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A potentially general approach to aliphatic ester-derived PVC plasticizers with suppressed migration as sustainable alternatives to DEHP

Abstract: A potentially general and green approach based on Claisen condensation that enabled low-migrating aliphatic ester-derived PVC plasticizers as sustainable alternatives to DEHP was reported.

Cited by 35 publications

References 27 publications

A simple approach with scale-up potential towards intrinsically flame-retardant bio-based co-plasticizer for PVC artificial materials

A simple approach with scale-up potential towards intrinsically flame-retardant bio-based co-plasticizer for PVC artificial materials

Relationship between the Structure of Modified Ricinoleic Acids via the Thiol–Ene Click Reaction and the Fogging Value of Fatliquored Leather

Waste Fatty Acid-Based Methyl Tetraglycol Ester Derived from Dimer Acid Manufacturing as an Efficient and Biodegradable Plasticizer for Poly(vinyl chloride)

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