1-Vinyl-2-(hydroxymethyl)imidazole (2) is synthesized by a procedure described in the literature. Corresponding copolymers with upper critical solution temperature (UCST)-type transitions in water and high-glass transition temperatures (Tg ) are prepared by free radical copolymerization with N-vinylimidazole (1). Depending on the copolymer composition, the cloud point can be varied between 19 and 41 °C. As the copolymer composition is identical with the monomer feed ratio, the cloud point can be easily tuned in the desired range. Furthermore, a distinctive pH-dependence and salt effect can be observed.

An N‐vinylimidazole‐based monomer carrying an adamantyl group, (1‐vinyl‐2‐yl)methyl­adamantan‐1‐ylcarbamate (3), is synthesized. The terpolymerization with N‐vinylimidazole (4) and 1‐vinyl‐2‐(hydroxymethyl)imidazole (2) yields terpolymers (5a–b) with high upper critical solution temperature (UCST)‐type transitions in water. The solubility can be influenced by the addition of various amounts of randomly methylated β‐cyclodextrin (RAMEB‐CD). It is found that supramolecular host/guest interaction clearly controls the solution behavior.

1-Vinyl-2-(methoxymethyl)imidazole ( 6 ), 1-vinyl-2-(ethoxymethyl)imidazole ( 7 ), 1-vinyl-2-(propoxy methyl)imidazole ( 8 ), and 1-vinyl-2-(butoxymethyl)imidazole ( 9 ) are synthesized through the etherifi cation of 1-vinyl-2-(hydroxymethylimidazole) ( 1 ) with corresponding alkyl halides ( 2-5 ). Corresponding homopolymers ( 10-13 ) are synthesized via free radical polymerization and investigated concerning their temperature-dependent solubility in water. The homopolymer 11 shows a lower critical solution temperature (LCST) behavior with a cloud point of 23 °C. Through copolymerization of 7 with N -vinylimidazole ( 14 ), the cloud point is varied up to 42 °C.