Epoxy Fatty Acid Ester Plasticizers

Greenspan, Frank P.; Gall, Ralph J.

doi:10.1021/ie50528a048

Cited by 34 publications

(12 citation statements)

References 5 publications

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“…As PVC exposed to heat and/or light, the HCl evolved which may cause the development of undesirable color and rapid deterioration of the polymer (Greenspan and Gall, 1953;Swern, 1955). Plasticizers are additives integrated into rigid polymeric material to improve their flexibility, workability, and distensibility, thereby increasing the plastic utility in numerous applications.…”

Section: Stabilizer/plasticizer For Rubber and Pvcmentioning

confidence: 99%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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SUMMARY:The highly strained ring in epoxides makes these compounds very versatile intermediates. Epoxidized vegetable oils are gaining a lot of attention as renewable and environmentally friendly feedstock with various industrial applications such as plasticizers, lubricant base oils, surfactants, etc. Numerous papers have been published on the development of the epoxidation methods and the number is still growing. This review reports the synthetic approaches and applications of epoxidized vegetable oils. KEYWORDS: Epoxidation; Renewable feedstock; Unsaturated fatty acids; Vegetable Oils RESUMEN:Modificación del doble enlace olefínico en ácidos grasos insaturados y en derivados de aceites vegetales via epoxidación: Revisión. La alta tensión del anillo en los epóxidos hace que estos compuestos intermediarios sean muy versátiles. Los aceites vegetales epoxidados están ganando mucha atención como materia prima renovable y respetuosa con el medio ambiente con diversas aplicaciones industriales, tales como plastificantes, aceites base para lubricantes, tensioactivos, etc. Por esta razón, se han publicado numerosos trabajos sobre el desarrollo de métodos de epoxidación y el número todavía es creciente. Esta revisión aporta información sobre enfoques sintéticos y aplicaciones de aceites vegetales epoxidados.

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Section: Stabilizer/plasticizer For Rubber and Pvcmentioning

confidence: 99%

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

et al. 2017

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“…Due to its high molecular weight (~1000 g mol −1 ), Epoxy Soybean Oil (ESBO) has limited compatibility with PVC and will exude at high concentrations. Reduction of the molecular weight of ESBO by transesterification with alkyl alcohols was shown to provide compounds with good plasticizing properties but higher volatility due to the molecular heterogeneity of the soybean oil (Greenspan and Gall, 1953, 1956).…”

Section: Resultsmentioning

confidence: 99%

Castor Epoxy Fatty Acid Alkyl Ester Estolides as Bioplasticizers for Poly(Vinyl Chloride)

Stolp

Graß

Kodali

2020

J Americ Oil Chem Soc

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Epoxy fatty acid alkyl ester estolides were synthesized from castor oil to be used as biobased plasticizers for poly(vinyl chloride) (PVC) as a safer replacement for phthalate plasticizers. Initially, castor oil was transesterified with methanol or n‐butanol to quantitatively yield castor fatty acid alkyl esters. Acetylation of hydroxyl function with acetic anhydride led to the formation of estolide. The unsaturation was epoxidized, resulting in a bifunctional epoxy fatty acid alkyl ester estolide. The bioplasticizers were compounded with PVC and were evaluated for their functionality and compared with commercial phthalate plasticizer diisononyl phthalate (DINP) and nonphthalate 1,2‐cyclohexanoic acid diisononyl ester (DINCH). The bioplasticizers showed excellent gelation, efficiency, and compatibility, as well as plastisol viscosity and thermal properties, comparable to or better than the plastisols prepared with commercial controls DINP and DINCH. The volatility of the methyl ester was inferior to the butyl ester. Both compounds showed low water resistance properties. Further evaluation of the butyl ester under tropical conditions of high temperature and humidity confirmed limited compatibility. This indicates that the castor epoxy fatty acid ester estolides would be better suited for applications that do not come in contact with water for prolonged periods, such as flooring, artificial leather, wiring, or wall coverings.

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“…in the presence of lactic acid, carboxylic acids) and the epoxy groups open up in the presence of higher oxydative stress, oxygen bridges are formed between FAs and plastification may ocur [42,43]. Chemically hydroxy FAs have been synthesized by peracid oxidation of unsaturated fatty acids or direct oxidation of the double bond with reagents such as hydrogen peroxide to give vicinal diols [44,45]. Occurrence of plastification in unsaturated fatty acids with long chains under high oxydative stress cause opacification and geloid appearance in silicone oils.…”

Section: Discussionmentioning

confidence: 99%

“…Unsaturated FAs can produce hydroxy-epoxy FA esters in high concentration of hydrogen peroxide in low pH [44]. Panretinal scatter photocoagulation had been completed during surgery in Group A patients.…”

Section: Discussionmentioning

confidence: 99%

The Effect of Different Retina Diseases on Cholesterol and Fatty Acid Content of Silicone Oil From Vitrectomized Eyes

Güngel¹,

Tekkeli

2016

J. Chil. Chem. Soc.

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The differences of cholesterol and fatty acid content of silicone oils that were removed from vitrectomized eyes due to different retinal diseases were investigated. The silicone oils were removed from 25 cases after 4-8 months and classified in two groups; Group A consists of 11 patients who had undergone pars plana vitrectomy combined with phacoemulsification and intraocular lens implantation due to diabetic tractional retinal detachment and Group B consists of 14 patients who was treated for phakic primary rhegmatogenous retinal detachment. The removed material from vitrectomized eyes in Group A was opacified and gelatinous on the other hand in Group B it was transparent. Hexan extracts were prepared from liquid and emulsified phases. The extracts were taken into vials, after that, hexane was removed. The chemical structure of each extracted material was investigated by spectroscopic techniques. The concentration of unsaturated fatty acids (FAs) in both groups were compared statistically. In conclusion, in Group A, epoxy and hydroxy-epoxy FAs were determined. The mean amount of unsaturated FAs in Group A was significantly lower than Group B. Cholesterol was not detected in any samples. The type of FAs in removed silicone oils may differ depending on the oxidative stress of retina.

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Epoxy Fatty Acid Ester Plasticizers

Cited by 34 publications

References 5 publications

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Modification of olefinic double bonds of unsaturated fatty acids and other vegetable oil derivatives via epoxidation: A review

Castor Epoxy Fatty Acid Alkyl Ester Estolides as Bioplasticizers for Poly(Vinyl Chloride)

The Effect of Different Retina Diseases on Cholesterol and Fatty Acid Content of Silicone Oil From Vitrectomized Eyes

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