SYNTHESIS OF POLY (2-HYDROXY ETHYL ACRYLATE) THROUGH ATOM TRANSFER RADICAL POLYMERIZATION (ATRP)
Vásquez D., Chinea C.Polymers Laboratory, Central University of Venezuela
ATRP Components
Abstract
Details of the work in progress of the synthesis of poly(2-hydroxy ethyl acrylate) through atom transfer radical polymerization (ATRP) in solution. It is proposed α-haloesters as initiators; and copper(I) chloride complexes with diimine ligands as the catalyst. All components are synthesized for this project.
Iniciators
α-haloesters are good initiators for acrylates in general due to their structural resemblance and fast initiation rates. The followings were prepared and used in this project:
- Methyl 2-bromo propionate
- Methyl 2-bromo-2-methylpropianate
Introduction
Transition metal complexes
Copper with multydentate nitrogen ligands is reported to be the best cathalyst for acrylates. Copper(I) chloride complexes with the next ligands variations were prepared:
The poly(2-hydroxy ethyl acrylate) is a biocompatible hydrogel suitable for medical applications. For these applications, it requires to be synthesized via living radical polymerization to achieve low cost production, low polydispersity and control of the polymer structure. The use of ATRP will achieve that while also using a robust method that withstands impurities. The success of ATRP as method depends on the components used and their proportion. On this work in progress, we will evaluate new promising ATRP componets. In addition, we plan to optimize the synthesis by modifying the temperature of the process as well as the ATRP components and proportions.
- 1,10-Phenantroline
- 2-N,3-N-Dibenzulbutane-2,3-diimine
- 2,6-[1-(2-isopropyl phenyl amino) ethyl] pyridine
Monomer
Well-defined and functional poly(2-hydroxy ethyl acrylate) has been obtained via ATRP. Once polymerized, it is a biocompatible hydrogel ideal for drug delivery systems, burn dressings and soft tissue substitutes. It has poor mechanical properties, but its optical qualities are excellent for applications like contact lenses and artificial corneas.
Methodology and process description
As shown in scheme 1, the radical or active species are produced through a redox process catalyzed by the transition metal complex.
Scheme 1: ATRP general mechanism.
The polymer chains grow by the addition of intermediates radicals to monomers. Termination of the polymer chains should be less than 5% if well-controlled. The current project is undergoing the characterization of the synthesized components. The starting polymerizations conditions are being tested:
The polymerizations are being prepared in amber ampoules with an argon atmosphere. The solvents proposed are water, ethanol, and dimethyl sulfoxide.
References
SYNTHESIS OF POLY (2-HYDROXY ETHYL ACRYLATE) THROUGH ATRP
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Created on January 21, 2021
Details of the current work in progress of the synthesis of poly(2-hydroxy ethyl acrylate) through ATRP in solution. The componets proposed are α-haloesters as initiators and copper(I) chloride complexes with diimine ligands. All the components were synthesized for this project.
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Transcript
SYNTHESIS OF POLY (2-HYDROXY ETHYL ACRYLATE) THROUGH ATOM TRANSFER RADICAL POLYMERIZATION (ATRP)
Vásquez D., Chinea C.Polymers Laboratory, Central University of Venezuela
ATRP Components
Abstract
Details of the work in progress of the synthesis of poly(2-hydroxy ethyl acrylate) through atom transfer radical polymerization (ATRP) in solution. It is proposed α-haloesters as initiators; and copper(I) chloride complexes with diimine ligands as the catalyst. All components are synthesized for this project.
Iniciators
α-haloesters are good initiators for acrylates in general due to their structural resemblance and fast initiation rates. The followings were prepared and used in this project:
Introduction
Transition metal complexes
Copper with multydentate nitrogen ligands is reported to be the best cathalyst for acrylates. Copper(I) chloride complexes with the next ligands variations were prepared:
The poly(2-hydroxy ethyl acrylate) is a biocompatible hydrogel suitable for medical applications. For these applications, it requires to be synthesized via living radical polymerization to achieve low cost production, low polydispersity and control of the polymer structure. The use of ATRP will achieve that while also using a robust method that withstands impurities. The success of ATRP as method depends on the components used and their proportion. On this work in progress, we will evaluate new promising ATRP componets. In addition, we plan to optimize the synthesis by modifying the temperature of the process as well as the ATRP components and proportions.
Monomer
Well-defined and functional poly(2-hydroxy ethyl acrylate) has been obtained via ATRP. Once polymerized, it is a biocompatible hydrogel ideal for drug delivery systems, burn dressings and soft tissue substitutes. It has poor mechanical properties, but its optical qualities are excellent for applications like contact lenses and artificial corneas.
Methodology and process description
As shown in scheme 1, the radical or active species are produced through a redox process catalyzed by the transition metal complex.
Scheme 1: ATRP general mechanism.
The polymer chains grow by the addition of intermediates radicals to monomers. Termination of the polymer chains should be less than 5% if well-controlled. The current project is undergoing the characterization of the synthesized components. The starting polymerizations conditions are being tested:
The polymerizations are being prepared in amber ampoules with an argon atmosphere. The solvents proposed are water, ethanol, and dimethyl sulfoxide.
References