Radical polymerization of new functional monomer: methacryloyl isocyanate containing 3-chloro-1-propanol

• Published in: Reactive & functional polymers 2000-02, Vol.43 (1), p.211-219
• Main Authors: Liaw, Der-Jang, Sang, Hui-Chuan
• Format: Article
• Language: English
• Subjects: 3-Chloro-1-propanol; Applied sciences; Carbazoyl group; Copolymerization; Exact sciences and technology; Methacryloyl isocyanate; Organic polymers; Physicochemistry of polymers; Polymer modification; Polymerization; Preparation, kinetics, thermodynamics, mechanism and catalysts; Radical polymerization; Solvent effect
• ISSN: 1381-5148
• DOI: 10.1016/S1381-5148(99)00052-8

A new functional monomer, methacryloyl isocyanate, containing 3-chloro-1-propanol (CPL-MAI), was prepared in a reaction of methacryloyl isocyanate (MAI) with 3-chloro-1-propanol (CPL) at low temperature and was characterized by IR, 1H and 13C NMR spectra. Radical polymerization of CPL-MAI was studied in terms of the rate of polymerization, solvent effect, copolymerization, polymer modification and thermal properties. The rate of polymerization of CPL-MAI has been found to be smaller than that of styrene under the same conditions. Copolymerization of CPL-MAI (M 1) with styrene (M 2) in tetrahydrofuran (THF) was studied at 60°C. The monomer reactivity ratio was calculated to be r 1=0.26 and r 2=0.33 according to the method of Fineman–Ross. Poly(CPL-MAI) was easily modified by reacting with the sodium salt of carbazole leading to a displacement of 49% conversion. The TG curve for poly(CPL-MAI) is in two stages and shows two maxima peaks at 206 and 416°C.