Epoxy fatty acid ester plasticizers. Preparation and properties

Greenspan, Frank P.; Gall, Ralph J.

doi:10.1007/bf02630763

Cited by 20 publications

(10 citation statements)

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“…hardness at 75 ± 2. 6 Modulus 100% elongation at 1500 =fc 100 p.s.i. d Modulus 100% elongation at 1300 ± 100 p.s.i.…”

Section: Methodsmentioning

confidence: 99%

“…They are primary plasticizers and show excellent compatibility at high concentration use levels with no evidence of bleed after prolonged exposure to light. As combination stabilizer-plasticizers they are applicable to a wide range of vinyl resin formulations and products-e. g., hose, toys, flooring, packaging, film, and foam 'X'he epoxy plasticizers, widely used in vinyl resin processing, are epoxy fatty acid esters (5,6,72,73), prepared by epoxidation of unsaturated fatty acid esters of mono-and polyhydric alcohols. A new series, alkyl epoxyhexahydrophthalates, has been developed in these laboratories in a broad program of research on epoxy plasticizers.…”

Section: Vinyl Epoxy Plasticizersmentioning

confidence: 99%

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Vinyl Epoxy Plasticizers -The Epoxyhexahydrophthalates"

Greenspan¹,

Gall²

1958

Ind. Eng. Chem.

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The alkyl epoxyhexahydrophthalates represent a new class of improved epoxy plasticizers with built-in stabilizing properties, protecting poly(viny1 chloride) resins against degradation caused by heat and light. They are primary plasticizers and show excellent compatibility at high concentration use levels with no evidence of bleed after prolonged exposure to light.As combination stabilizer-plasticizers they are applicable to a wide range of vinyl resin formulations and products-e. g., hose, toys, flooring, packaging, film, and foam THE epoxy plasticizers, widely used in vinyl resin processing, are epoxy fatty acid esters (5, 6, 72, 13)) prepared by epoxidation of unsaturated fatty acid esters of mono-and polyhydric alcohols. A new series, alkyl epoxyhexahydrophthalates, has been developed in these laboratories in a broad program of research on epoxy plasticizers. The epoxyhexahydrophthalates combine the excellent stabilizing properties of the epoxy fatty acid esters with the good over-all plasticizing properties of the phthalates. They are compatible with poly(viny1 chloride) at primary use levels and show no evidence of bleed, sometimes observed with specific epoxy fatty acid ester plasticizers at high use levels, after prolonged exposure to ultraviolet or diffused light. ExperimentalThe epoxyhexahydrophthalate esters (4, 70) can be prepared by epoxidation of the corresponding unsaturated tetrahydrophthalic acid esters with preformed peracetic acid or by in situ techniques (2,3, 7,9) employing hydrogen peroxide.The reaction can be represented schematically as:The tetrahydrophthalate esters were made by esterifying n-butyl, n-hexyl, isooctyl, and n-decyl alcohols (Enjay Co., Inc.) with tetrahydrophthalic anhydride (National Aniline Division) in the presence of an acid catalyst, water-washed, and vacuum-distilled.The in situ epoxidation process (8) is illustrated below for the preparation of di-2-ethylhexylepoxyhexahydrophthalate.One hundred grams of di-2-ethylhexyltetrahydrophthalate (Union Carbide Chemicals) and 20 grams of benzene were weighed into a three-necked flask equipped with a reflux condenser, thermometer, and a mechanical stirrer; 7.7 grams of glacial acetic acid and 1.

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“…hardness at 75 ± 2. 6 Modulus 100% elongation at 1500 =fc 100 p.s.i. d Modulus 100% elongation at 1300 ± 100 p.s.i.…”

Section: Methodsmentioning

confidence: 99%

Section: Vinyl Epoxy Plasticizersmentioning

confidence: 99%

Vinyl Epoxy Plasticizers -The Epoxyhexahydrophthalates"

Greenspan¹,

Gall²

1958

Ind. Eng. Chem.

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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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“…The resin catalysts are of particular appeal for the epoxidation of polyunsaturated esters (e.g., soybean oil) giving higher conversions (7) to epoxide than either sulfuric or alkane sulfonic acids. At the optimum catalyst level of 25%, resin catalyst systems are uneconomical because of the high cost of resin.…”

Section: Discussionmentioning

confidence: 99%