Synthesis of Network Polymers by Means of Addition Reactions of Multifunctional-Amine and Poly(ethylene glycol) Diglycidyl Ether or Diacrylate Compounds.

Naofumi Naga,Tamaki Nakano,Kensuke Mori,Hassan Nageh,Mitsusuke Sato

doi:10.3390/polym12092047

Naofumi Naga, Tamaki Nakano + Show 3 more

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https://doi.org/10.3390/polym12092047

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Journal: Polymers	Publication Date: Sep 8, 2020
Citations: 18	License type: CC BY 4.0

Affiliation: Hokkaido University, Shibaura Institute of Technology

Abstract

Addition reactions of multi-functional amine, polyethylene imine (PEI) or diethylenetriamine (DETA), and poly(ethylene glycol) diglycidyl ether (PEGDE) or poly(ethylene glycol) diacrylate (PEGDA), have been investigated to obtain network polymers in H2O, dimethyl sulfoxide (DMSO), and ethanol (EtOH). Ring opening addition reaction of the multi-functional amine and PEGDE in H2O at room temperature or in DMSO at 90 °C using triphenylphosphine as a catalyst yielded gels. Aza-Michael addition reaction of the multi-functional amine and PEGDA in DMSO or EtOH at room temperature also yielded corresponding gels. Compression test of the gels obtained with PEI showed higher Young’s modulus than those with DETA. The reactions of the multi-functional amine and low molecular weight PEGDA in EtOH under the specific conditions yielded porous polymers induced by phase separation during the network formation. The morphology of the porous polymers could be controlled by the reaction conditions, especially monomer concentration and feed ratio of the multi-functional amine to PEGDA of the reaction system. The porous structure was formed by connected spheres or a co-continuous monolithic structure. The porous polymers were unbreakable by compression, and their Young’s modulus increased with the increase in the monomer concentration of the reaction systems. The porous polymers absorbed various solvents derived from high affinity between the polyethylene glycol units in the network structure and the solvents.

Highlights

Network structure, such as molecular and geometric structures, in chemically synthesized gels strongly affects their properties
We describe the synthesis of gels by addition reaction of PEI or DETA, as the multi-functional monomer, and polyethylene glycol diglycidyl ether (PEGDE) using the ring opening addition reaction [25] (Scheme 1) or polyethylene glycol diacrylate (PEGDA) using the aza-Michael addition reaction [26] (Scheme 2)
The network polymers with a poly(ethylene glycol) (PEG) unit were successfully synthesized by ring opening addition reactions conventional multi-functional amines, PEI or DETA, with PEGDE

Summary

Introduction

Network structure, such as molecular and geometric structures, in chemically synthesized gels strongly affects their properties. We have been developing several types of gels synthesized by addition reactions between multi-functional monomers as “joint unit” sources. The gels formed a homogeneous network structure with extremely narrow mesh size distribution, and their mesh size could be controlled by the molecular length of the bi-functional monomers. Those gels were too fragile to evaluate their mechanical properties. We have been trying to synthesize the gels with high mechanical properties using conventional addition reactions of generic chemicals and solvents. Prior to the development of the ionic conducting gels, we investigated a basic study of the molecular design of organogels with the PEG unit based on the joint and linker concept.

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