Synthesis of poly vinyl chloride/chlorinated polypropylene-active natural substance derivatives for potential packaging materials application. Tannic acid, menthol and lipoic acid

Hazer, Baki̇; Ashby, Richard D.

doi:10.1016/j.foodchem.2022.134475

Cited by 15 publications

(15 citation statements)

References 45 publications

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“…In our recent article, 39 GC-MS analysis was applied to ensure that there was no diffusion of the attached natural substance from the tannic acid, menthol, and lipoic acid functionalized PVC into the oxidized linseed oil. There was no trace of the natural substances in the oxidized linseed oil based on the GC chromatograms.…”

Section: Resultsmentioning

confidence: 99%

“…37 Previously, we synthesized novel derivatives of poly(vinyl chloride) (PVC) and chlorinated polypropylene (PP-Cl) using tannic acid, lipoic acid, and menthol for potential active food packaging materials applications. In those studies we carried out coupling reactions between the chloride pendant groups of PP-Cl and PVC with some carboxylic acid/hydroxyl groups of tannic acid, 38,39 lipoic acid, and menthol. 39 In this present work, we report the results from additional bioactive natural substance functionalized PVC utilizing vanillic (van), caffeic (caff), coumaric (coum), and cinnamic (cinn) acids together with naringin (ning).…”

Section: Introductionmentioning

confidence: 99%

“…In those studies we carried out coupling reactions between the chloride pendant groups of PP-Cl and PVC with some carboxylic acid/hydroxyl groups of tannic acid, 38,39 lipoic acid, and menthol. 39 In this present work, we report the results from additional bioactive natural substance functionalized PVC utilizing vanillic (van), caffeic (caff), coumaric (coum), and cinnamic (cinn) acids together with naringin (ning). The synthesis and characterization of novel PVC-van, PVC-caff, PVC-coum, PVC-cinn, and PVCning derivatives and the results of the inhibitory effects of these functionalized polymers on the autoxidation of linseed oil are described.…”

Section: Introductionmentioning

confidence: 99%

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Poly(vinyl chloride) Derived Food Packaging Applications with Antioxidative and Anticancer Properties

Hazer

Karahaliloğlu

Ashby

2023

ACS Food Sci. Technol.

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Novel poly(vinyl chloride) (PVC) polymer derivatives based on the natural antioxidants vanillic acid, cinnamic acid, coumaric acid, caffeic acid, and naringin were prepared and characterized for their chemical structures, molecular weights, thermal and mechanical properties, and antioxidant characteristics toward linseed oil. Oxidation delay times (induction periods) were prolonged from 1 to 6 days beyond the pristine PVC, with the naringin-based derivative being the most effective. Biological activities of the PVC derivatives were determined and showed the substituted PVC polymers effectively inhibited the formation of reactive oxygen species (ROS) in the MCF-7 cell line according to the following sequence: cinnamic acid ≥ caffeic acid ≥ vanillic acid = naringin ≥ coumaric acid, with only a minimal effect on healthy L929 cells. These results indicate that the derivatives produced in this study have potential applications as active packaging materials for food and as antibacterial/anticancer biomaterials in areas such as tissue engineering.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Poly(vinyl chloride) Derived Food Packaging Applications with Antioxidative and Anticancer Properties

Hazer

Karahaliloğlu

Ashby

2023

ACS Food Sci. Technol.

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“…Similarly, tannic acid, lipoic acid, and menthol functionalized polyvinyl chlorides show oxidation delaying time up to 29 days (Hazer & Ashby, 2023). The amount of iodine (mg) that reacts with the double bonds in 100 g of plant oil.…”

Section: Reaction Vesselmentioning

confidence: 99%

Macro peroxide initiators based on autoxidized unsaturated plant oils: Block/graft copolymer conjugates for nanotechnology and biomedical applications

Hazer

2023

J Americ Oil Chem Soc

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The autoxidation of unsaturated fatty acids and their esters is one of the most important reactions in food and biological systems. Autoxidation is a type of reaction between air oxygen and unsaturated plant oils. This reaction starts with a hydrogen abstraction on the methylene group adjacent double bond, leaving a radical onto the carbon atom. Molecular oxygen attacks this radical leading to produce peroxide and hydroperoxide derivatives of the oligomerized unsaturated plant oils. Because peroxide groups thermally cleave to produce free radicals, hydroperoxide derivatives of unsaturated plant oil oligomers can be used in the free radical polymerization of vinyl monomers leading to the related block/graft copolymers. The obtained copolymers combined with the biodegradable natural plant oil gain superior properties such as biodegradability and softness. In this review article, the in vitro autoxidation of well‐known unsaturated plant oils‐soybean oil, linseed oil, and castor oil and some related unsaturated fatty acids‐oleic acid, linoleic acid, and ricinoleic acid was carried out under atmospheric conditions with or without exposing white light. Because the autoxidized unsaturated oil/fatty acids contain peroxide/hydroperoxide groups (they are referred to as macro peroxide initiators) that they are used in the free radical polymerization of vinyl monomers to obtain block/graft copolymers. The improved polymerization conditions, characterization, and applications of the obtained products will be discussed.

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“…As one of the important polymers in the world, the annual output of polyvinyl Chloride (PVC) is second only to polyethylene (PE), and it is favored by people in the fields of automobile manufacturing, building decoration, children’s toys, and outdoor protective materials [ 1 , 2 , 3 , 4 ].Additionally, the PVC derivatives also have been used as active packaging materials [ 5 , 6 ]. The reason is that PVC has good mechanical properties, acid and alkali resistance, insulation, flame retardant, and so on.…”

Section: Introductionmentioning

confidence: 99%

Synergistic Effect of Two Plasticizers on Thermal Stability, Transparency, and Migration Resistance of Zinc Arginine Stabilized PVC

Shi

Yao

et al. 2022

Polymers

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The effect of different plasticizers on thermal stability, transparency, and migration resistance of the PVC stabilized with zinc arginine [Zn(Arg)2] was investigated. The thermal stability, migration resistance, and transparency of PVC with tributyl citrate (TBC) were better than PVC with dioctyl phthalate (DOP) characterized by oven aging method, migration test, and near infrared-visible-ultraviolet spectrophotometer. At the same time, the longer the carbon chain in citric acid esters, the better the thermal stability and transparency of PVC sample. The hydroxyl group in citric acid esters is helpful to improve the thermal stability of PVC samples. However, the elongation at break and Tg value of PVC containing DOP were very close to those of PVC containing TBC. The calculation results of Hansen solubility parameters also illustrated that DOP had better compatibility with PVC than TBC. Therefore, the excellent transparency and thermal stability of TBC plasticized PVC were attributed to the good compatibility between TBC and Zn(Arg)2, which was verified by the solubility test. Lastly, the mixture of dioctyl terephthalate (DOTP) and TBC was used as plasticizers for Zn(Arg)2 stabilized PVC. When the ratio of TBC and DOTP was 1:1, the transparency, thermal stability, and migration resistance of Zn(Arg)2 stabilized PVC samples were better than those of PVC plasticized by DOP or TBC alone. The mechanism was that the compatibility between Zn(Arg)2 and PVC was greatly improved by the synergetic effect of TBC and DOTP, resulting in the improvement of thermal stability, migration resistance, and transparency of PVC samples.

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Synthesis of poly vinyl chloride/chlorinated polypropylene-active natural substance derivatives for potential packaging materials application. Tannic acid, menthol and lipoic acid

Cited by 15 publications

References 45 publications

Poly(vinyl chloride) Derived Food Packaging Applications with Antioxidative and Anticancer Properties

Poly(vinyl chloride) Derived Food Packaging Applications with Antioxidative and Anticancer Properties

Macro peroxide initiators based on autoxidized unsaturated plant oils: Block/graft copolymer conjugates for nanotechnology and biomedical applications

Synergistic Effect of Two Plasticizers on Thermal Stability, Transparency, and Migration Resistance of Zinc Arginine Stabilized PVC

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