Synthesis of a Novel Bio-Oil-Based Hyperbranched Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Chen, Jie; Nie, Xiaoan; Jiang, Jianchun

doi:10.1021/acsomega.0c00119

Cited by 33 publications

(28 citation statements)

References 26 publications

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“…In 2020, Chen et al [ 56 ] synthesized a hyperbranched ester plasticizer using soybean oil (SOHE) and mixed it with PVC for studying thermal and mechanical properties. The new compound exhibited good thermal stability in comparison to DOP, but T g was significantly higher (61.89 °C for SOHE and 41.46 °C for DOP, respectively).…”

Section: New Secondary Plasticizersmentioning

confidence: 99%

“…The introduction of a secondary plasticizer to a PVC blend can result in the presence of synergistic interactions between the blend components that could influence the properties of the final product. There are several reports describing the situation when a part of the primary plasticizer was replaced by a secondary plasticizer [ 54 , 55 , 56 ]. Due to the interactions between these two compounds, the plastics could adopt better properties, particularly good migration resistance and enhanced mechanical properties compared to a material with only the primary plasticizer.…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, they have a distinct tendency to migrate because of their high volatility. The intermediate effect of this in most cases is obtained when a high molecular weight secondary plasticizer, usually polymeric macromolecule with an excellent migration resistance, is added to the mixture, partially replacing the primary one [ 56 , 57 , 58 ]. Because of its higher molecular weight (according to Wypych a polymeric plasticizer should have an average MW > 2000 g/mol [ 18 ]), the plasticizer migration from the plastics is reduced.…”

Section: Introductionmentioning

confidence: 99%

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Recent Attempts in the Design of Efficient PVC Plasticizers with Reduced Migration

2021

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This paper reviews the current trends in replacing commonly used plasticizers in poly(vinyl chloride), PVC, formulations by new compounds with reduced migration, leading to the enhancement in mechanical properties and better plasticizing efficiency. Novel plasticizers have been divided into three groups depending on the replacement strategy, i.e., total replacement, partial replacement, and internal plasticizers. Chemical and physical properties of PVC formulations containing a wide range of plasticizers have been compared, allowing observance of the improvements in polymer performance in comparison to PVC plasticized with conventionally applied bis(2-ethylhexyl) phthalate, di-n-octyl phthalate, bis(2-ethylhexyl) terephthalate and di-n-octyl terephthalate. Among a variety of newly developed plasticizers, we have indicated those presenting excellent migration resistance and advantageous mechanical properties, as well as those derived from natural sources. A separate chapter has been dedicated to the description of a synergistic effect of a mixture of two plasticizers, primary and secondary, that benefits in migration suppression when secondary plasticizer is added to PVC blend.

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Section: New Secondary Plasticizersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Recent Attempts in the Design of Efficient PVC Plasticizers with Reduced Migration

2021

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“…where E ∆T g = plasticizing efficiency of BHE, and ∆T g = the reduction in Tg from PVC to plasticized PVC films. The plasticizing performance of PVC materials was evaluated via tensile strength and elongation at break, which were detected according to GB/T 1040.1-2006 (Beijing, China) and at room temperature using an E43.104 Universal Testing Machine (MTS Instrument Corp., Shenzhen, China) [20].…”

Section: Characterizationmentioning

confidence: 99%

Preparation of Biomass-Based Ester End-Capped Hyperbranched Poly(ether)s via Facile One-Pot Reaction and Their Performance as Non-Toxic Plasticizers

Shu

Jia

2020

Polymers

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The aim of this study was to develop a facile one-pot reaction for the synthesis of biomass-based hyperbranched poly(ether)s end-capped as acetate esters (BHE) for use as a sustainable, safe and feasible plasticizer for flexible poly(vinyl chloride) (PVC) materials. BHE is completely miscible with PVC but shows weaker plasticizing effect than dioctyl phthalate (DOP) (E∆Tg value of BHE reaches 64.8%). PVC plasticized with BHE displays greater thermal stability than that of PVC or PVC plasticized with DOP materials. BHE improves the thermal stability and flexibility of PVC materials. As a plasticizer, BHE displays lower solvent extractability and greater volatilization resistance than DOP. Acute oral toxicity indicates that BHE has toxic doses of 5 g/kg, suggesting that BHE is non-toxic.Polymers 2020, 12, 913 2 of 11 exceed 69 mg/kg, which is lower than the amount of DOP that migrates from plasticized polymer products. DOP can migrate from products via volatilization and enter the human body through human respiration [5]. It is estimated that 500,000 pounds of phthalates was released to the environment from US manufacturing facilities in 1997 [6].In order to overcome the toxicity and poor migration resistance of phthalates, a series of alternative plasticizers were prepared. The strategies to prevent plasticizer migration from PVC products mainly include internal plasticized method such as covalently attaching plasticizer onto the PVC matrix [7]; making surface modifications such as gamma irradiation, ultraviolet irradiation and plasma treatment [8]; and adding nanoparticles or ionic liquid [9,10]. These alternative plasticizers include CO 2 -based polycarbonate [11], cardanol-based epoxidized plasticizers [1], epoxidized vegetable oil [12], glycerol/adipic acid hyperbranched poly(ester)s [13], and so on. Glycerol/adipic acid hyperbranched poly(ester)s are thermally stable, are fully compatible with a PVC matrix, provide effective plasticization at acceptable levels, display low migratory potential and do not accelerate degradative dehydrochlorination [13]. However, there are very few reports on the acute oral toxicity of the plasticizers for PVC.Developing bio-based products is highly important because of their low cost, reproducibility and biodegradability [14][15][16]. In this study, we synthesized biomass-based hyperbranched poly(ether)s end-capped as acetate esters (BHE) via a facile one-pot reaction using triethyl citrate as raw material. The obtained BHE, with a larger relative molecular mass and a higher branching degree, is a potential plasticizer that could overcome the shortcoming of the poor migration resistance of lower relative molecular mass plasticizers, such as triethyl citrate and phthalate plasticizers. The plasticization and migration resistance of PVC materials plasticized with BHE were investigated and compared with those of DOP. The plasticizing mechanism was explored with regards to the shift of infrared absorption peaks of ester groups and the generation of hydrogen bonds via fourier transf...

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“…Hence, the price of vegetable oil-based plasticizers is much higher than that of phthalates, which has become an obstacle to industrialization. Not only vegetable oils, but also the other bio-based raw materials such as lactic acid, 24 tartaric acid, 25 isosorbide, 26,27 dehydroabietic acid, 28 and glycerin 9,30 could also be used to prepare sustainable plasticizers. Similarly, these plasticizers have a common drawback that the cost of them are so high, making it difficult to industrialize production.…”

Section: Introductionmentioning

confidence: 99%

An efficient plasticizer based on waste cooking oil: Structure and application

Liu

Shen

Wai

et al. 2020

J of Applied Polymer Sci

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Recently, phthalates have been continuously banned in numerous fields by many countries. Therefore, the development of sustainable and efficient plasticizers has become particularly urgent. The waste cooking oil was used as the main raw materials in this study to synthesize an efficient plasticizer (acetylated-fatty acid methyl ester-trimellitic acid ester, AC-FAME-TAE). The structure of AC-FAME-TAE was characterized by FT-IR and 1 H NMR. The performance of the poly(vinyl chloride) (PVC) plasticized by AC-FAME-TAE was tested and compared with those of the PVC plasticized with di-2-ethylhexyl phthalate (DOP) and EFAME (epoxy fatty acid methyl ester), respectively. DSC results indicated that AC-FAME-TAE had excellent plasticizing efficiency for PVC. The mechanical properties of PVC plasticized by AC-FAME-TAE were as comparable as PVC plasticized by DOP from the results of tensile test. In addition, the PVC plasticized by AC-FAME-TAE had excellent thermal stability and solvent resistance by the results of leaching test and TGA.

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Synthesis of a Novel Bio-Oil-Based Hyperbranched Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Cited by 33 publications

References 26 publications

Recent Attempts in the Design of Efficient PVC Plasticizers with Reduced Migration

Recent Attempts in the Design of Efficient PVC Plasticizers with Reduced Migration

Preparation of Biomass-Based Ester End-Capped Hyperbranched Poly(ether)s via Facile One-Pot Reaction and Their Performance as Non-Toxic Plasticizers

An efficient plasticizer based on waste cooking oil: Structure and application

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