Glycidyl Esters of Aliphatic Acids

Kester, E. B.; Gaiser, C. J.; Lazar, Monique

doi:10.1021/jo01194a010

Cited by 37 publications

(10 citation statements)

References 3 publications

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“…Therefore, we explored the esterification of sebacoyl chloride by glycidol in toluene as a way to synthesize diglycidyl sebacate (Fig. 2) [36]. We found that the side reaction, ring-opening of the epoxide moiety by HCl, could be efficiently prevented using excessive triethylamine (5×) as an acceptor of HCl and lowering the reaction temperature to −15 °C.…”

Section: Resultsmentioning

confidence: 99%

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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Polyesters with free functional groups allow facile modifications with biomolecules, which can lead to versatile biomaterials that afford controlled interactions with cells and tissues. Efficient synthesis of functionalizable polyesters is still a challenge that greatly limits the availability and widespread applications of biofunctionalized synthetic polymers. Here we report a simple route to prepare a functionalizable polyester, poly(sebacoyl diglyceride) (PSeD) bearing free hydroxyl groups. The key synthetic step is an epoxide ring-opening polymerization, instead of the traditional polycondensation, that produces poly(glycerol sebacate) (PGS) [1]. PSeD has a more defined structure with mostly linear backbone, more free hydroxyl groups, higher molecular weight, and lower polydispersity than PGS. Crosslinking PSeD with sebacic acid yields a polymer five times tougher and more elastic than cured PGS. PSeD exhibits good cytocompatibility in vitro. Furthermore, functionalization by glycine proceeds with high efficiency. This versatile synthetic platform can offer a large family of biodegradable, functionalized polymers with tunable physiochemical and biological properties useful for a wide range of biomedical applications.

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Section: Resultsmentioning

confidence: 99%

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

et al. 2010

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“…Carefully dried and finely powdered soaps resulted in greater yields of glycidyl esters of FAs. [51] A low solubility of soap in EPCH suggested that a phase transfer catalyst would be useful to accelerate the reaction. With CTAB catalyst, the consumption of soap was completed within half an hour under reflux condition.…”

Section: Physical Propertiesmentioning

confidence: 99%

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Wang¹,

Schuman²

2013

Express Polym. Lett.

155

118

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Abstract. Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been synthesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxidized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF 3 catalyst or anhydride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

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“…Glycidyl esters of aliphatic acids could be prepared by reacting dry soaps of aliphatic acid with epichlorohydrin or by the phase-transfer method. 23 However, the preparation of anhydrous soaps was very slow and difficult due to foaming and caking. The phase-transfer method used toluene as a solvent and produced a lot of waste water from washing of the organic phase.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Preparation of biobased epoxies using tung oil fatty acid-derived C21 diacid and C22 triacid and study of epoxy properties

et al. 2013

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Glycidyl Esters of Aliphatic Acids

Cited by 37 publications

References 3 publications

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

A functionalizable polyester with free hydroxyl groups and tunable physiochemical and biological properties

Vegetable oil-derived epoxy monomers and polymer blends: A comparative study with review

Preparation of biobased epoxies using tung oil fatty acid-derived C21 diacid and C22 triacid and study of epoxy properties

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