Application
2-Carboxyethyl acrylate can be polymerized in solution or emulsion to produce acrylic, vinyl acrylic, or styrene acrylic polymers, which are distinguished by their low glass transition temperatures (<30°C) as homopolymers. Greater elasticity, as well as improved adhesion.
Preparation
Synthesis of 1-ethoxyethyl acrylate (EEA) and protected 2-carboxyethyl acrylate (proCEA)
EEA and proCEA were synthesized following a previously published procedure and distilled prior to use. For the synthesis of proCEA (Figure 1), phosphoric acid (109 mg, 1.11 mmol) was weighed into a dry round bottom flask in a glovebox and then taken outside the glovebox, taking care that the phosphoric acid stayed dry. 2-Carboxyethyl acrylate (80 g, 555 mmol) and ethyl vinyl ether (48 g, 666 mmol) were added and the reaction was stirred for two days at room temperature. Hydrotalcite (Mg6Al2(OH)16CO3·4H2O, ~1 g) was added, stirred for one hour and filtered off. Excess ethyl vinyl ether was removed under reduced pressure and the product was distilled under reduced pressure (80 °C, 1.3 mbar).
Figure 1 Synthesis of proCEA