Synthesis and photochemical reaction of novelp-alkylcalix[6]arene derivatives containing acryloyl or methacryloyl groups

Abstract

Novel polyfunctional (meth)acrylates with a calixarene backbone [calixarene (meth)acrylates] were synthesized in good yields by certain reactions of p-methylcalix[6]arene (1a) or p-tert-butylcalix[6]arene (1b) with (meth)acrylate derivatives such as acryloyl chloride, methacryloyl chloride, (2-methacryloxy)ethyl isocyanate, and glycidyl methacrylate. Polyfunctional acrylate 6a having poly(oxyethylene) spacer chain between 1a and acrylate groups was also synthesized by the reaction of the poly(oxyethylene) modified 1a with acrylic acid. Calixarene acrylate 6a was liquid at room temperature, although the other calixarene (meth)acrylates were solid at room temperature. The initial decomposition temperature (IDT) of the resulting calixarene (meth)acrylates was measured by the thermogravimetric analysis to evaluate the thermal stability, and it was found that some of the IDTs of the calixarene acrylates were over 400°C. This means that calixarene (meth)acrylates have very good thermal stability. The photopolymerization of the resulting some calixarene (meth)acrylates with (2-phenyoxy)ethyl acrylate as a reactive diluent in the presence of photoinitiator proceeded smoothly upon irradiation with UV light. Therefore, polyfunctional (meth)acrylates with a calixarene backbone can be expected to be novel and thermally stable photoreactive acrylate oligomers. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3071–3078, 1999