Partitioning of 2-Carboxyethyl Acrylate between Water and Vinyl Monomer Phases Applied to Emulsion Polymerization: Comparisons with Hydroxy Acrylate and Other Vinyl Acid Functional Monomers

Abstract

In an extension of our recent studies on the distribution of vinyl acid (AA and MAA) and hydroxy (meth)acrylate monomers in emulsion polymerization systems, we report the distribution behavior of 2-carboxyethyl acrylate (CEA) between water and various nonfunctional monomers. Similar to that previously reported for AA and MAA, the distribution of CEA strongly depends upon the hydrogen-bond-acceptor characteristics of the nonfunctional monomer organic phase. The logarithm of the distribution coefficients for CEA correlate linearly with the molar volume of (meth)acrylate monomers. The CEA molecule is a replica of 2-hydroxyethyl acrylate (HEA) with a different functional group. Evaluation of the distribution behaviors of CEA and HEA allows for a direct comparison of the carboxyl and hydroxyl moieties in determining the distributions. The strong dipole moment of the hydroxy group makes HEA significantly more polar than CEA. Also, comparisons of the distribution behaviors of CEA with those for AA and MAA allow us to understand the combined effect of the ester and carboxylic acid groups in CEA on the overall polarity of these vinyl acid monomers and their distribution behaviors.

Homo- and Copolymer Hydrogels Based on N-Vinylformamide: An Investigation of the Impact of Water Structure on Controlled Release

“…Its molecular structure, which includes a carboxyl group, is expected to have interesting properties with different water/monomer distribution characteristics from the more traditional AA and MAA functional monomers. Additionally, CEA contains an ester group, making it a vinyl acid monomer with two carbonyl groups, providing a direct molecular comparison to functional vinyl monomers with −COOH and −OH end groups [ 24 ]. The copolymerization of HEA and CEA with NVF has the ability to display interesting behavior.…”

Modification of Cellulose Nanocrystals With 2-Carboxyethyl Acrylate in the Presence of Epoxy Resin for Enhancing its Adhesive Properties

“…It has better physical bonding with metal surfaces or other functional materials and may give better strength to the substrate. Furthermore, as an organic monomer, 2-carboxyethyl acrylate is used with CNCs for enhancing their mechanical strength (Kim et al, 2007;Tripathi et al, 2015;Naseer et al, 2021;Awais et al, 2022).…”

Modification of cellulose nanocrystals with 2-carboxyethyl acrylate in the presence of epoxy resin to enhance its adhesive property

“…2-carboxyethyl acrylate as an organic monomer which was used with CNCs to measure the mechanical strength. [20,21] Over the past decade, CNCs has been considered as a potentially natural nanomaterial and attracted researcher's attention for its wide applications. The scattering and accumulation in polar solvents in a series of hashes attracted for optical and structural properties.…”