Triester–amide based on thiophene and ricinoleic acid as an innovative primary plasticizer for poly(vinyl chloride)

Satavalekar, Sneha D.; Savvashe, Prashant; Mhaske, S. T.

doi:10.1039/c6ra20098b

Cited by 15 publications

(5 citation statements)

References 21 publications

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“…The same molecular mass plasticizers with a higher branched chain will provide more excellent plasticizing properties than linear plasticizers. 37 In this study, molecular structure DOP and ECTR have higher branched chains than ECR and ECMR, as seen from Figure 7a−d, which was more effective to reduce the T g of PVC films, thus giving a higher plasticizing efficiency. In addition, the long branched chain of ECR and ECMR may tangle with PVC and produce an anti-plasticization effect on PVC films.…”

Section: Resultsmentioning

confidence: 61%

“…The plasticizing mechanism of rosin-based plasticizers can be explained according to mathematical models for plasticization, which was reported by Mauritz and Storey. , In the theory, the decrease of T g was caused by branched chain movement. The same molecular mass plasticizers with a higher branched chain will provide more excellent plasticizing properties than linear plasticizers . In this study, molecular structure DOP and ECTR have higher branched chains than ECR and ECMR, as seen from Figure a–d, which was more effective to reduce the T g of PVC films, thus giving a higher plasticizing efficiency.…”

Section: Resultsmentioning

confidence: 65%

“…As seen from Figure 6, thermal degradation processes of all PVC films have two stages; the first stage is at around 260−350 °C, which is attributed to pyrolysis of PVC dechlorination. 36,37 The second stage at around 400−540 °C is due to the destruction of chains and forms cross-linking, cyclization, and cleavage compounds. 38 TGA data of all PVC films are summarized in Table S2.…”

Section: Resultsmentioning

confidence: 99%

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Designing Rosin-Based Plasticizers: Effect of Differently Branched Chains on Plasticization Performance and Solvent Resistance of Flexible Poly(vinyl chloride) Films

Jia

Zhang

et al. 2019

ACS Omega

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In the present study, we report a strategy to prepare rosin-based plasticizers with differently branched chains, which have the same benzene ring and similar alkane structure compared to phthalate plasticizers. Castor oil methyl ester, cardanol, and triethyl citrate were reacted with the chemical structure of rosin-based plasticizers. Rosin-based plasticizers with differently branched chains as alternative plasticizers for preparing phthalate-free flexible poly(vinyl chloride) films. All rosin-based plasticizers exhibited more excellent solvent extraction performance than phthalate plasticizers in four different solvents. The plasticizing efficiency of rosin-based plasticizers containing triethyl citrate groups reached 85.5%. The relationships between plasticizing efficiency, thermal stability, solvent resistance, tensile properties, and relative molecular mass of the branched chains of rosin-based plasticizers were investigated.

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Section: Resultsmentioning

confidence: 61%

Section: Resultsmentioning

confidence: 65%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Designing Rosin-Based Plasticizers: Effect of Differently Branched Chains on Plasticization Performance and Solvent Resistance of Flexible Poly(vinyl chloride) Films

Jia

Zhang

et al. 2019

ACS Omega

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“…The thermal properties of plasticized PVC films show that first step of the two-step thermal degradation starts from 260 to 350 °C, which is ascribed to the pyrolysis of PVC chlorination. , The second step of the degradation starts from 400 to 540 °C owing to the demolition of chains, forms cross-linking, cyclization, and scission compounds . Conversely, with the addition of ECMR into the PVC matrix, the thermal stability of the PVC films reduces with the enhancement of ECMR.…”

Section: Need Of Plasticizersmentioning

confidence: 99%

Recent Developments of Biobased Plasticizers and Their Effect on Mechanical and Thermal Properties of Poly(vinyl chloride): A Review

Kumar

2019

Ind. Eng. Chem. Res.

116

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Plasticized poly(vinyl chloride) (PVC) has been extensively utilized globally, with various applications in construction, piping, wiring and cable, installation, flooring, nonfood packing, windows, doors, and more. Phthalates have been the most commonly employed plasticizers for PVC, but some of these plasticizers demonstrate many toxic effects on the environment and human beings, which consequently limits the use of phthalate plasticizers. Growing awareness of the effects of plasticizers on the environment and the depletion of petroleum-based resources has made the development of an alternative biobased plasticizer for PVC formulation necessary. Recently, there has been an increased consciousness of the use of natural resource-based plasticizers instead of phthalates in PVC production, because they are eco-friendly in nature. This review paper covers the utilization of traditional and biobased plasticizers for PVC plasticization, and their effect on environmental, mechanical, and thermal properties has been reported.

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“…Dioctyl phthalate (DOP), the mainly used plasticizer of PVC in China, is a toxic substance that migrates to the environment from the PVC substrate and then causes profound impact on human health. 2 Though some nontoxic plasticizers are prepared (e.g., oleate plasticizers, 3 ricinoleate plasticizer, 4 ester-amide based on ricinoleic acid, 5 triester-amide based on thiophene and ricinoleic acid 6 ), the preparation methods are still limited owing to the problem of plasticizer migration. Therefore, it is very important to inhibit the migration and precipitation of plasticizers.…”

Section: Introductionmentioning

confidence: 99%

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

Deng

Jia

et al. 2022

ACS Omega

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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.

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Triester–amide based on thiophene and ricinoleic acid as an innovative primary plasticizer for poly(vinyl chloride)

Abstract: The synthesized triester amide (THPRABA) gives an alternative to the phthalate plasticizers.

Cited by 15 publications

References 21 publications

Designing Rosin-Based Plasticizers: Effect of Differently Branched Chains on Plasticization Performance and Solvent Resistance of Flexible Poly(vinyl chloride) Films

Designing Rosin-Based Plasticizers: Effect of Differently Branched Chains on Plasticization Performance and Solvent Resistance of Flexible Poly(vinyl chloride) Films

Recent Developments of Biobased Plasticizers and Their Effect on Mechanical and Thermal Properties of Poly(vinyl chloride): A Review

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

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