Hyperbranched polyglycerol nanoparticles based multifunctional, nonmigrating hindered phenolic macromolecular antioxidants: Synthesis, characterization and its stabilization effect on poly(vinyl chloride)

Kasza, György; Stumphauser, Tímea; Nádor, Attila; Osváth, Zsófia; Szarka, Györgyi; Domján, Attila; Mosnáček, Jaroslav; Iván, Béla

doi:10.1016/j.polymer.2017.07.061

Cited by 21 publications

(8 citation statements)

References 76 publications

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“…A large amount of plasticizers are applied in poly(vinyl chloride) (PVC) processing as additive to obtain the desired flexible PVC products, which can be used in a variety of applications, such as packaging, medical devices, coatings, and films. − Over 500 kinds of plasticizers have become commercialized . Phthalates, for example, dioctyl phthalate (DOP), are the most important commercial plasticizers for PVC and occupy more than 80% of the total plasticizer consumption, attributing to their outstanding plasticizing effect and relatively low price. , However, it is reported that phthalates have high risk of toxic and biological effects on human, − which limits their application, particularly in a field with high requirements for health-sensible or environmental applications such as children toys and medical devices. − In addition, phthalates have the environmental impact for easily diffusing into the environment from the PVC matrix, which also reduces the durable performance of PVC products. − Moreover, petroleum shortages have aroused comprehensive research studies on chemicals obtained from renewable resources, − such as plant oils. − Many alternative plasticizers based on plant oil have been reported and used in environmental PVC materials. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Tung-Oil-Based Triglycidyl Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Chen

Wang

et al. 2017

ACS Sustainable Chem. Eng.

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A tung-oil-derived renewable plasticizer, tung-maleic triglycidyl esters (TMTE), was prepared and incorporated into poly(vinyl chloride) (PVC) for the first time. The chemical structure was studied by Fourier transform infrared (FTIR), 1 H nuclear magnetic resonance (NMR), and 13 C NMR. The plasticizing effects of TMTE replacement of dioctyl phthalate (DOP) in soft PVC films were researched. Thermal stability, thermal degradation performance, dynamic mechanical property, and mechanical properties of pure PVC and PVC films were investigated with thermogravimetric analysis (TGA), TGA-FTIR, TGA-mass spectrometry, dynamic mechanical analysis, and mechanical test. The results showed that PVC films plasticized with the TMTE exhibited increased thermal stability, plasticizing effect, compatibility, and flexibility. When 30 phr (parts per hundred parts of resin) DOP was substituted with TMTE in PVC blends, glass transition temperature (T g ) dropped from 41.46 to 40.18 °C, the initial decomposition temperature (T i ), 10% and 50% mass loss temperatures (T 10 and T 50 ), had maximum increases of 8.0, 20.0, and 27.5 °C, respectively. The interaction between TMTE and PVC molecule was also discussed. Furthermore, the extraction, exudation, and volatility resistance of plasticizers were carried out and analyzed by solubility parameters, the results of which revealed the migration stabilities of PVC films were promoted with the increasing amount of TMTE.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Tung-Oil-Based Triglycidyl Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Chen

Wang

et al. 2017

ACS Sustainable Chem. Eng.

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“…The migration rates of BHA and BHT in 50% ethanol at 40 °C are presented in Figure 6 b. BHA and BHT have equal polarities, but BHA is released faster than BHT. This is because BHT has a higher molecular weight and volume (because of two –C(CH 3 ) 3 groups) [ 44 ]. As shown in Figure 6 a, the migration potentials of BHA and BHT were the same, even at 40 °C.…”

Section: Resultsmentioning

confidence: 99%

“…BHA and BHT have equal polarities, but BHA is released faster than BHT. This is because BHT has a higher molecular weight and volume (because of two -C(CH 3 ) 3 groups) [44]. As shown in Figure 6a, the migration potentials of BHA and BHT were the same, even at 40 • C. Overall, the migration of BHT was higher than that of BHA.…”

Section: Migration Experiments and Safety Assessmentmentioning

confidence: 88%

Functional and Antioxidant Properties of Plastic Bottle Caps Incorporated with BHA or BHT

Wang

Lin

et al. 2021

Materials

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In this study, we prepared new antioxidant active plastic bottle caps by incorporating butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT) and 2% (w/w) white masterbatch in high-density polyethylene (HDPE). Fourier-transform infrared (FT-IR) spectrometry revealed that the antioxidants and HDPE were uniformly mixed with noncovalent bonding. In addition, the differential scanning calorimetry (DSC) test revealed that the change in melting point and initial extrapolation temperature of the antioxidant active caps was not significant. Sensory evaluation and removal torque tests validated the suitability of the antioxidant active plastic bottle caps in industrial application. The antioxidant activity increased with a greater concentration of BHA and BHT incorporated in both antioxidant active caps (p < 0.05) and with more impact on the BHA cap compared to BHT cap in terms of antioxidant activity. Migration experiments for 10 days at 40 °C and 2 h at 70 °C showed that active antioxidants in the plastic bottle cap were more easily released into fatty foods and milk products that are highly sensitive to oxidation, and the migration of BHA and BHT did not exceed the maximum amount specified in (EC) No 1333/2008 (<200 mg/kg). As such, the antioxidant active plastic bottle caps inhibited oxidation, thereby ensuring higher food quality.

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“…The longer the aging time, the more obvious the superiority. Kasza et al 27 successfully synthesized a new high molecular antioxidant HbPG‐l‐AoxAc by functionalizing hyperbranched polyglycerol (HbPG) with sterically hindered phenolic antioxidant containing BHT moiety. The results showed that the stability efficiency of multifunctional polymer antioxidant HbPG‐l‐AoxAc was equivalent to that of Irganox1010 used in industry, exhibiting high inhibitory migration ability compared to low molecular weight antioxidant.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of new macromolecular hindered phenol antioxidants of polyamide 6

Jiang

Liu

Zou

et al. 2021

J of Applied Polymer Sci

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The two macromolecular antioxidants, P(3,5-di-tert-butyl-4-hydroxy cinnamic acid-alt-N-phenylmaleimide) (PCN) and P(3-butene-1-yl-3,5-ditert-butyl À4-hydroxyphenyl propionate-alt-N-phenylmaleimide) (PPN) were designed and synthesized via free radical copolymerization. The structures of the resulting PCN and PPN antioxidants were characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy ( 1 H NMR), and gel permeation chromatography. In addition, the effect of the two macromolecular antioxidants on the thermal oxidation aging resistance of polyamide 6 (PA6) was studied. According to the analysis of differential scanning calorimetry, thermogravimetric analysis, dynamic mechanical analysis, dynamic viscosity, and the mechanical property of PA6 and its blends, these two types of macromolecular antioxidants protected the molecular chain of PA6 from breaking, protected the crystallization of PA6 and maintained the stability of PA6 crystal form, improved the activation energy of thermal degradation and thermal stability of PA6, enhanced the strength and elasticity of PA6 and maintained the mechanical properties of PA6 during aging to a certain extent.

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Hyperbranched polyglycerol nanoparticles based multifunctional, nonmigrating hindered phenolic macromolecular antioxidants: Synthesis, characterization and its stabilization effect on poly(vinyl chloride)

Cited by 21 publications

References 76 publications

Synthesis of Tung-Oil-Based Triglycidyl Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Synthesis of Tung-Oil-Based Triglycidyl Ester Plasticizer and Its Effects on Poly(vinyl chloride) Soft Films

Functional and Antioxidant Properties of Plastic Bottle Caps Incorporated with BHA or BHT

Synthesis and application of new macromolecular hindered phenol antioxidants of polyamide 6

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