Methacrylates apolar solvents

For example, a proline-based chiral ligand was attached to a vinyl-substituted monomer (Fig. 42.15) by reacting vinylbenzoyl chloride with the amine functionality of the ligand [106]. As mentioned previously, the apolar Merrifield resin as a support is not swollen in polar solvents. Hence, in order to match the polarity of the resin with that of the typically used substrates in enantioselective hydrogenation, the functionalized monomer was copolymerized with polar units of methacrylic acid 2-hydroxyethyl ester. 

Apparently, because of the (necessarily) poor solubility of the dye in the organic solvent, the dye-endgroup ion-pair must be formed in the water-solvent interface. Because of the apolar nature of polystyrene, few endgroups actually come to this interface and, therefore, the ion-pair formation is not quantitative. As the polymer-polymer interaction increases at higher concentrations, the extent of ion-pair formation decreases. This explanation was confirmed recently by experiments of Huber and Thies (13) on the adsorption of toluene-soluble polymers at the toluene-water interface. They conclude that polystyrene has little affinity for this interface but that poly(methyl methacrylate) adsorbs significantly... 

---