Synthesis of a New Macromonomer from 2-(Dimethylamino)ethyl Methacrylate Bearing 1-(Isopropenylphenyl)-1,1-dimethylmethyl Isocyanate Group

• Published in: Macromolecular chemistry and physics Vol. 205; no. 5; pp. 645 - 655
• Main Authors: Boyer, Cyril, Boutevin, Gilles, Robin, Jean-Jacques, Boutevin, Bernard
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-03-2004; WILEY‐VCH Verlag; Wiley
• Subjects: 1-(isopropenylphenyl)-1; 1-dimethyl methyl isocyanate; 1‐(isopropenylphenyl)‐1,1‐dimethyl methyl isocyanate; 2-(dimethylamino)ethyl methacrylate; Applied sciences; copolymerization; Exact sciences and technology; macromonomers; Organic polymers; Physicochemistry of polymers; Polymerization; Preparation, kinetics, thermodynamics, mechanism and catalysts; reactivity ratio; Terpolymer; Radical telomerization; Organic isocyanate; Methacrylate polymer; Graft copolymer; End group; Solution copolymerization; Experimental study; Reactivity ratio; Macromer; Carbamoylation; Chemical modification; Mercaptoalcohol; Amine polymer; Preparation; Styrene; Hydroxyl group; Methacrylate copolymer; Radical copolymerization; Amine copolymer; Styrene(alpha-methyl) copolymer; Styrene copolymer
• ISSN: 1022-1352; 1521-3935
• DOI: 10.1002/macp.200300099

The telomerization of 2‐(dimethylamino)ethyl methacrylate (DMAEMA) with 2‐mercaptoethanol in acetonitrile shows that the telogen can react with the monomer by nucleophilic addition. It is to say that the tertiary amino group leads to nucleophilic addition rather than telomerization. The oligomers thus obtained were functionalized with 1‐(isopropenylphenyl)‐1,1‐dimethylmethyl isocyanate (TMI) in anhydrous toluene to afford macromonomers. These macromonomers were copolymerized with styrene and the r1, r2 ratio was determined according to Jaacks and Macret's methods. It was thereby demonstrated that the r1 value for this type of monomer is close to zero.
Structure of the model molecule.