Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring

Martos, Alba; Soto, Marc; Schäfer, Hannes; Koschek, Katharina; Marquet, Jordi; Sebastián, Rosa M.

doi:10.3390/polym12020254

Open AccessArticle

Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring

by

Alba Martos

¹,

Marc Soto

²

,

Hannes Schäfer

²,

Katharina Koschek

²

,

Jordi Marquet

^1,* and

Rosa M. Sebastián

^1,*

¹

Department of Chemistry, Universitat Autònoma de Barcelona and Centro de Innovación en Química (ORFEO-CINQA), Cerdanyola del Vallés, 08193 Barcelona, Spain

²

Fraunhofer Institute for Manufacturing Technology and Advanced Materials IFAM, Adhesive Bonding Technology and Surfaces, Wiener Strasse 12, 28359 Bremen, Germany

^*

Authors to whom correspondence should be addressed.

Polymers 2020, 12(2), 254; https://doi.org/10.3390/polym12020254

Submission received: 18 December 2019 / Revised: 14 January 2020 / Accepted: 17 January 2020 / Published: 21 January 2020

(This article belongs to the Special Issue Thermosets II)

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Abstract

It is possible to control the crosslink density of polymers derived from monobenzoxazines by switching the type of substituents in the phenolic ring and their relative position with respect to the phenol group. We prepared several substituted monobenzoxazines in the para and meta positions of the phenolic ring and studied how these substituents affected the polymerization temperature of monomers and the thermal stability of the final polymers and, more extensively, how they affected the crosslink network of the final polymers. Gel content and dynamic mechanical analysis confirm that ortho- and para-orienting substituents in the meta position generate highly crosslinked materials compared to para ones. This fact can lead to the design of materials with highly crosslinked networks based on monobenzoxazines, simpler and more versatile monomers than the commercial bisbenzoxazines currently in use.

Keywords: monobenzoxazines; para and meta phenols; thermosets; crosslinking; thermal stability; gel content; phenolic catalyst; differential scanning calorimetry; dynamic mechanical analysis

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MDPI and ACS Style

Martos, A.; Soto, M.; Schäfer, H.; Koschek, K.; Marquet, J.; Sebastián, R.M. Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring. Polymers 2020, 12, 254. https://doi.org/10.3390/polym12020254

AMA Style

Martos A, Soto M, Schäfer H, Koschek K, Marquet J, Sebastián RM. Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring. Polymers. 2020; 12(2):254. https://doi.org/10.3390/polym12020254

Chicago/Turabian Style

Martos, Alba, Marc Soto, Hannes Schäfer, Katharina Koschek, Jordi Marquet, and Rosa M. Sebastián. 2020. "Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring" Polymers 12, no. 2: 254. https://doi.org/10.3390/polym12020254

APA Style

Martos, A., Soto, M., Schäfer, H., Koschek, K., Marquet, J., & Sebastián, R. M. (2020). Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring. Polymers, 12(2), 254. https://doi.org/10.3390/polym12020254

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Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring

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