Oxidative degradation of thermosets based on thioketal cleavable linkages in aqueous environment
- Author
- Mohamed Abdelrahim (UGent) , Jun Zhang, Quan Gao, Wael A. Zordok, Ji Liu and Jin Geng
- Organization
- Abstract
- Thermosets are rigid, infusible, and unmolded materials containing three-dimensional (3D) cross-linked structures. They are considered a fundamental pillar in the international economy, which are produced by 65 million tons annually. The responsive cross-linking moieties provide the thermosets characterized with outstanding phys-icochemical properties such as stiffness, degradability, and chemical and thermal resistance. We prepared degradable thermoset materials using thioketal (TK) cross-linkers, which underwent main-chain or side change degradation in the presence of hydrogen peroxide in water. TK cross-linkers at different concentrations (5, 10, and 20% wt %) were polymerized with 2-hydroxyethyl acrylate (HEA) or with 2-hydroxyethyl methacrylate (HEMA) and 1-vinyl-2-pyrrolidone (PD) to produce cross-linked poly-(HEA) and poly(HEMA-PD) by free radical polymerization, respectively. The resultant polymer materials completely degraded in hydrogen peroxide/water (3-30%, vol). Using isophorone diisocyanate, we also produced degradable polyurethane based on TK-bearing diol. We prepared a 3D degradable thermoset using the Direct-Ink-Writing (DIW) 3D printing technology, which was charged by diethylene glycol diacrylate (15%, wt %) and a prepolymer (isophorone diisocyanate terminated by acrylate moieties) containing diol-thioketal linkage (15%, wt %). Finally, we found that TK-poly(HEA) underwent microbial degradation by Lactobacillus jensenii at 37 degrees C, which indicates a benign eco-friendly effect.
- Keywords
- Organic Chemistry, Polymers and Plastics, Process Chemistry and Technology, thermosets, thioketal, biodegradation, hydrogen peroxide, polyurethane, MECHANISMS, LIPASE, BONDS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01GQA6SZK3JVMVZ62EKS8ZDSEZ
- MLA
- Abdelrahim, Mohamed, et al. “Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment.” ACS APPLIED POLYMER MATERIALS, vol. 4, no. 10, 2022, pp. 7812–22, doi:10.1021/acsapm.2c01357.
- APA
- Abdelrahim, M., Zhang, J., Gao, Q., Zordok, W. A., Liu, J., & Geng, J. (2022). Oxidative degradation of thermosets based on thioketal cleavable linkages in aqueous environment. ACS APPLIED POLYMER MATERIALS, 4(10), 7812–7822. https://doi.org/10.1021/acsapm.2c01357
- Chicago author-date
- Abdelrahim, Mohamed, Jun Zhang, Quan Gao, Wael A. Zordok, Ji Liu, and Jin Geng. 2022. “Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment.” ACS APPLIED POLYMER MATERIALS 4 (10): 7812–22. https://doi.org/10.1021/acsapm.2c01357.
- Chicago author-date (all authors)
- Abdelrahim, Mohamed, Jun Zhang, Quan Gao, Wael A. Zordok, Ji Liu, and Jin Geng. 2022. “Oxidative Degradation of Thermosets Based on Thioketal Cleavable Linkages in Aqueous Environment.” ACS APPLIED POLYMER MATERIALS 4 (10): 7812–7822. doi:10.1021/acsapm.2c01357.
- Vancouver
- 1.Abdelrahim M, Zhang J, Gao Q, Zordok WA, Liu J, Geng J. Oxidative degradation of thermosets based on thioketal cleavable linkages in aqueous environment. ACS APPLIED POLYMER MATERIALS. 2022;4(10):7812–22.
- IEEE
- [1]M. Abdelrahim, J. Zhang, Q. Gao, W. A. Zordok, J. Liu, and J. Geng, “Oxidative degradation of thermosets based on thioketal cleavable linkages in aqueous environment,” ACS APPLIED POLYMER MATERIALS, vol. 4, no. 10, pp. 7812–7822, 2022.
@article{01GQA6SZK3JVMVZ62EKS8ZDSEZ,
abstract = {{Thermosets are rigid, infusible, and unmolded materials containing three-dimensional (3D) cross-linked structures. They are considered a fundamental pillar in the international economy, which are produced by 65 million tons annually. The responsive cross-linking moieties provide the thermosets characterized with outstanding phys-icochemical properties such as stiffness, degradability, and chemical and thermal resistance. We prepared degradable thermoset materials using thioketal (TK) cross-linkers, which underwent main-chain or side change degradation in the presence of hydrogen peroxide in water. TK cross-linkers at different concentrations (5, 10, and 20% wt %) were polymerized with 2-hydroxyethyl acrylate (HEA) or with 2-hydroxyethyl methacrylate (HEMA) and 1-vinyl-2-pyrrolidone (PD) to produce cross-linked poly-(HEA) and poly(HEMA-PD) by free radical polymerization, respectively. The resultant polymer materials completely degraded in hydrogen peroxide/water (3-30%, vol). Using isophorone diisocyanate, we also produced degradable polyurethane based on TK-bearing diol. We prepared a 3D degradable thermoset using the Direct-Ink-Writing (DIW) 3D printing technology, which was charged by diethylene glycol diacrylate (15%, wt %) and a prepolymer (isophorone diisocyanate terminated by acrylate moieties) containing diol-thioketal linkage (15%, wt %). Finally, we found that TK-poly(HEA) underwent microbial degradation by Lactobacillus jensenii at 37 degrees C, which indicates a benign eco-friendly effect.}},
author = {{Abdelrahim, Mohamed and Zhang, Jun and Gao, Quan and Zordok, Wael A. and Liu, Ji and Geng, Jin}},
issn = {{2637-6105}},
journal = {{ACS APPLIED POLYMER MATERIALS}},
keywords = {{Organic Chemistry,Polymers and Plastics,Process Chemistry and Technology,thermosets,thioketal,biodegradation,hydrogen peroxide,polyurethane,MECHANISMS,LIPASE,BONDS}},
language = {{eng}},
number = {{10}},
pages = {{7812--7822}},
title = {{Oxidative degradation of thermosets based on thioketal cleavable linkages in aqueous environment}},
url = {{http://doi.org/10.1021/acsapm.2c01357}},
volume = {{4}},
year = {{2022}},
}
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