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Limonene-Based Epoxy: Anhydride Thermoset Reaction Study.

ABSTRACT: The development of epoxy thermosets from renewable resources is of paramount importance in a sustainable development context. In this paper, a novel bio-based epoxy monomer derived from limonene was synthesized without epichlorohydrine and characterized. In fact, this paper depicts the synthesis of bis-limonene oxide (bis-LO). However, intern epoxy rings generally exhibit a poor reactivity and allow reaction with anhydride. Therefore, we used a reaction model with hexahydro-4-methylphthalic anhydride to compare reactivity of terminal and interepoxy functions. We also studied the influence of methyl group on intern epoxy functions. Furthermore, the influence of epoxy:anhydride stoichiometry and initiator amount was studied. These studies allow to propose an optimized formulation of bis-LO. Finally, a bis-LO-based thermoset was obtained and characterized.

SUBMITTER: Couture G

PROVIDER: S-EPMC6278336 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Limonene-Based Epoxy: Anhydride Thermoset Reaction Study.

Couture Guillaume G Granado Lérys L Fanget Florent F Boutevin Bernard B Caillol Sylvain S

Molecules (Basel, Switzerland) 20181023 11

The development of epoxy thermosets from renewable resources is of paramount importance in a sustainable development context. In this paper, a novel bio-based epoxy monomer derived from limonene was synthesized without epichlorohydrine and characterized. In fact, this paper depicts the synthesis of bis-limonene oxide (bis-LO). However, intern epoxy rings generally exhibit a poor reactivity and allow reaction with anhydride. Therefore, we used a reaction model with hexahydro-4-methylphthalic anhy ...[more]

PMID: 30360571

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Project description:Photoresists (or photo-resins) are the main and most important raw material used for lithography techniques such as deep X-ray (DXRL), ultraviolet (UVL), deep-UV (DUVL), and extreme UV (EUVL). In previous work, we showed how complicated could be the synthesis of the resins used to produce photoresist. In this study, we follow up on the strategy of tuning deep and macro levels of properties to formulate photo-resins. They were developed from a primary basis, using epoxy resins, a solvent, and a photoinitiator in several concentrations. The formulations were evaluated initially by the UVL technique, using a squared pattern of 2.3 mm2. The most suitable compositions were then studied in a pattern structure varying from 50 down to 1 µm width, applying UVL and DUVL. The patterned structures were compared with the chemical composition of the photo-resins. Considering the deep level of properties, polydispersion, and epoxidation degree were evaluated. Regarding the macro level of properties, the concentration of photoinitiator was studied. Promising results have been achieved with the control of the deep and macro levels methodology. By means of UV lithography, it was possible to note, for a large feature size above 2.0 mm2, the formulations presented good quality structures with a broad range of epoxidation degrees and photoinitiator concentrations, respectively from 3 to 100% (mol·molpolymer-1) and from 10 to 40% (mol·molpolymer-1). For structures smaller than 50 µm width, the composition of the photo-resins may be restricted to a narrow range of values regarding the formulation. The results indicate that the polydispersion of the oligomers might be a significant property to control. There is a tendency to better outcome with a low polydispersity (resins P1 and P2). Regarding UV and deep-UV irradiation, the best results were achieved with UV. Nevertheless, for DUV, the sensitivity seems to be more intense, leading to well-defined structures with over-exposure effects.

Dataset Information

Limonene-Based Epoxy: Anhydride Thermoset Reaction Study.

Publications

Limonene-Based Epoxy: Anhydride Thermoset Reaction Study.

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