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Synthesis of a novel highly hindered spiroorthocarbonate and the study of its efficiency to eliminate the shrinkage in the photopolymerization of an epoxycycloaliphatic resin

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Abstract

This work involved the synthesis of a highly bulky spiroorthocarbonate with the aim of reducing or eliminating the shrinkage produced in the cationic polymerization of an epoxy resin. The dicyclododecanyl spiroorthocarbonate SOC CD was prepared in five stages. A cyclododecanyl epoxy-ester, was first prepared using cyclododecanone as the starting material. Then, this compound was hydrolyzed to the corresponding carboxylic acid. This acid was decarboxylated to produce a cyclododecanyl aldehyde that was then reacted with formaldehyde in basic solution to obtain the cyclododecane 1,1-diyl dimethanol. The desired SOC CD compound was finally obtained by transesterification of the diol with tetraethylorthocarbonate. Then, SOC CD was added as an antishrinking additive to the 3,4-epoxycyclohexylmethyl-3′, 4′-epoxycyclohexancarboxylate resin. It was found that the presence of this compound did not influence the photopolymerization rate, but it increased the level of conversion when added at 8 mol %. The volume change study revealed that by adding a concentration as low as 4 mol % of SOC CD, shrinkage was completely suppressed obtaining a volumetric expansion of 0.68 %. Upon increasing the concentration of the additive to 8 mol % the expansion increased to 3.39 %.

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Acknowledgments

The authors thank the Mexican National Council of Science and Technology (CONACYT) for funding project 151489. Assistance in the analysis of samples by Guadalupe Mendez, José Luis Saucedo, Francisco Zendejo, Sergio Zertuche and Rodrigo Cedillo, is gratefully acknowledged.

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Authors and Affiliations

  1. Centro de Investigación en Química Aplicada, Blvd Enrique Reyna 140, Saltillo, Coahuila, 25294, Mexico

    Ricardo Acosta Ortiz, Aida Esmeralda Garcia Valdez, Rafael Aguirre Flores, Rosa Ivet Lozano Palacios & María Lydia Berlanga Duarte

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  1. Ricardo Acosta Ortiz
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  2. Aida Esmeralda Garcia Valdez
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  3. Rafael Aguirre Flores
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  4. Rosa Ivet Lozano Palacios
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  5. María Lydia Berlanga Duarte
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Correspondence to Ricardo Acosta Ortiz.

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Acosta Ortiz, R., Garcia Valdez, A.E., Aguirre Flores, R. et al. Synthesis of a novel highly hindered spiroorthocarbonate and the study of its efficiency to eliminate the shrinkage in the photopolymerization of an epoxycycloaliphatic resin. J Polym Res 22, 163 (2015). https://doi.org/10.1007/s10965-015-0814-3

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  • DOI: https://doi.org/10.1007/s10965-015-0814-3

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