Recyclable, Biobased Photoresins for 3D Printing Through Dynamic Imine Exchange

Karen P. Cortés-Guzmán; Ankit R. Parikh; Marissa L. Sparacin; Ashele K. Remy; Lauren Adegoke; Chandani Chitrakar; Melanie Ecker; Walter E. Voit; Ronald A. Smaldone

doi:10.1021/acssuschemeng.2c03541

Recyclable, Biobased Photoresins for 3D Printing Through Dynamic Imine Exchange

Karen P. Cortés-Guzmán, Ankit R. Parikh, Marissa L. Sparacin, Ashele K. Remy, Lauren Adegoke, Chandani Chitrakar, Melanie Ecker, Walter E. Voit, Ronald A. Smaldone

Soft Materials and Membranes

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

Transimination reactions are highly effective dynamic covalent reactions to enable reprocessability in thermosets, as they can undergo exchange without the need for catalysts, by exposing the materials to external stimuli such as heat. In this work, a series of five biobased vanillin-derived resin formulations consisting of vanillin acrylate with vanillin methacrylate-functionalized Jeffamines were synthesized and 3D-printed using digital light projection (DLP). The resulting thermosets displayed a range of mechanical properties (Young's modulus 2.05-332 MPa), which allow for an array of applications. The materials we obtained have self-healing abilities, which were characterized by scratch healing tests. Additionally, dynamic transimination reactions enable these thermosets to be reprocessed when thermally treated above their glass transition temperatures under high pressures using a hot press. Due to the simple synthetic procedures and the readily available commercial Jeffamines, these materials will aid in promoting a shift to materials with predominantly biobased content and help drift away from polymers made from non-renewable resources.

Original language	English
Pages (from-to)	13091-13099
Number of pages	9
Journal	ACS Sustainable Chemistry and Engineering
Volume	10
Issue number	39
DOIs	https://doi.org/10.1021/acssuschemeng.2c03541
State	Published - Oct 3 2022

Funding

K.P.C.G. acknowledges the Consejo Nacional de Ciencia y Tecnología (CONACYT, Mexican Council of Science and Technology) for doctoral fellowship. We also acknowledge the Advanced Polymer Research Laboratory (APRL) at UT Dallas for access to facilities for the thermal characterization of polymers. A.R.P. acknowledges scientific and internship support from the U.S. Food and Drug Administration. R.A.S. acknowledges support from UT Dallas and the Army Research Laboratory (W911NF-18-2-0035) and the American Chemical Society Petroleum Research Fund (PRF#61360- ND10).

Keywords

3D printing
biobased thermoset
covalent adaptable networks
dynamic covalent chemistry
imine
photocuring
self-healing
thermally reprocessable
vanillin
vitrimer

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10.1021/acssuschemeng.2c03541

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title = "Recyclable, Biobased Photoresins for 3D Printing Through Dynamic Imine Exchange",

abstract = "Transimination reactions are highly effective dynamic covalent reactions to enable reprocessability in thermosets, as they can undergo exchange without the need for catalysts, by exposing the materials to external stimuli such as heat. In this work, a series of five biobased vanillin-derived resin formulations consisting of vanillin acrylate with vanillin methacrylate-functionalized Jeffamines were synthesized and 3D-printed using digital light projection (DLP). The resulting thermosets displayed a range of mechanical properties (Young's modulus 2.05-332 MPa), which allow for an array of applications. The materials we obtained have self-healing abilities, which were characterized by scratch healing tests. Additionally, dynamic transimination reactions enable these thermosets to be reprocessed when thermally treated above their glass transition temperatures under high pressures using a hot press. Due to the simple synthetic procedures and the readily available commercial Jeffamines, these materials will aid in promoting a shift to materials with predominantly biobased content and help drift away from polymers made from non-renewable resources.",

keywords = "3D printing, biobased thermoset, covalent adaptable networks, dynamic covalent chemistry, imine, photocuring, self-healing, thermally reprocessable, vanillin, vitrimer",

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AU - Cortés-Guzmán, Karen P.

AU - Parikh, Ankit R.

AU - Sparacin, Marissa L.

AU - Remy, Ashele K.

AU - Adegoke, Lauren

AU - Chitrakar, Chandani

AU - Ecker, Melanie

AU - Voit, Walter E.

AU - Smaldone, Ronald A.

PY - 2022/10/3

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N2 - Transimination reactions are highly effective dynamic covalent reactions to enable reprocessability in thermosets, as they can undergo exchange without the need for catalysts, by exposing the materials to external stimuli such as heat. In this work, a series of five biobased vanillin-derived resin formulations consisting of vanillin acrylate with vanillin methacrylate-functionalized Jeffamines were synthesized and 3D-printed using digital light projection (DLP). The resulting thermosets displayed a range of mechanical properties (Young's modulus 2.05-332 MPa), which allow for an array of applications. The materials we obtained have self-healing abilities, which were characterized by scratch healing tests. Additionally, dynamic transimination reactions enable these thermosets to be reprocessed when thermally treated above their glass transition temperatures under high pressures using a hot press. Due to the simple synthetic procedures and the readily available commercial Jeffamines, these materials will aid in promoting a shift to materials with predominantly biobased content and help drift away from polymers made from non-renewable resources.

AB - Transimination reactions are highly effective dynamic covalent reactions to enable reprocessability in thermosets, as they can undergo exchange without the need for catalysts, by exposing the materials to external stimuli such as heat. In this work, a series of five biobased vanillin-derived resin formulations consisting of vanillin acrylate with vanillin methacrylate-functionalized Jeffamines were synthesized and 3D-printed using digital light projection (DLP). The resulting thermosets displayed a range of mechanical properties (Young's modulus 2.05-332 MPa), which allow for an array of applications. The materials we obtained have self-healing abilities, which were characterized by scratch healing tests. Additionally, dynamic transimination reactions enable these thermosets to be reprocessed when thermally treated above their glass transition temperatures under high pressures using a hot press. Due to the simple synthetic procedures and the readily available commercial Jeffamines, these materials will aid in promoting a shift to materials with predominantly biobased content and help drift away from polymers made from non-renewable resources.

KW - 3D printing

KW - biobased thermoset

KW - covalent adaptable networks

KW - dynamic covalent chemistry

KW - imine

KW - photocuring

KW - self-healing

KW - thermally reprocessable

KW - vanillin

KW - vitrimer

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JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

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ER -

Recyclable, Biobased Photoresins for 3D Printing Through Dynamic Imine Exchange

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