Mass Spectrometric Characterization of a New 2‐Hydroxypropyl‐β‐cyclodextrin Derivative Bearing Methacrylic Moieties and Its Copolymerization with 1‐Vinyl‐2‐pyrrolidone

Abstract

AbstractThe characterization of a new cyclodextrin (CD) derivative, developed by Wacker Chemie GmbH under the name βW7‐MAHP and consisting of methacrylic moieties attached to hydroxypropyl‐β‐CD units, was investigated in terms of molecular structure and reactivity. The structural study was performed using a matrix‐assisted laser‐desorption ionization time‐of‐flight (MALDI‐TOF) mass spectrometry analysis, which revealed that βW7‐MAHP is a mixture of at least 60 identified compounds. The substituent nature was determined from the two successive chemical modifications performed on β‐CD (hydroxypropylation with propylene oxide followed by the reaction with glycidyl methacrylate). Furthermore, each reaction resulted in a mixture of compounds having different numbers of substituents because of the polyfunctionality of the β‐CD molecule (14 secondary and 7 primary OH groups). Only 50 wt.‐% of the mixture consisted of polymerizable components among which a small proportion contained two or more methacrylic residues. The polymerizability of βW7‐MAHP was studied, and the reactivity ratios in the copolymerization with 1‐vinyl‐2‐pyrrolidinone were estimated. Soluble copolymers were obtained for monomer compositions having a βW7‐MAHP fraction less than 60 mol‐% whereas for higher amounts cross‐linked gels were produced.MALDI‐TOF mass spectrum of βW7‐MAHP.magnified imageMALDI‐TOF mass spectrum of βW7‐MAHP.