Synthesis and photopolymerization of new triphenylamine-based oxiranes

• Published in: Designed monomers and polymers Vol. 10; no. 2; pp. 105 - 118
• Main Authors: Andruleviciute, V., Lazauskaite, R., Grazulevicius, J.V.
• Format: Journal Article
• Language: English
• Published: Lieden Taylor & Francis Group 01.01.2007; VSP
• Subjects: Applied sciences; Exact sciences and technology; IODONIUM SALT; IRON-ARENE COMPLEX; OXIRANE; PHOTOPOLYMERIZATION; Physicochemistry of polymers; Polymerization; Polymers and radiations; SYNTHESIS; TRIPHENYLAMINE; Ring opening polymerization; iron-arene complex; Aminoalcohol; Temperature effect; Cationic polymerization; Experimental study; Reaction rate; Alcohol polymer; oxirane; Diamine; Synthesis; triphenylamine; Amine polymer; Photopolymerization; iodonium salt; Preparation; Tertiary amine; Glycidyl ether polymer; Monomer; Chemical reactivity
• ISSN: 1385-772X; 1568-5551; 1568-5551
• DOI: 10.1163/156855507780378267

Synthesis and cationic photopolymerization of new triphenylamine-based oxiranes, i.e., 4-[(oxiranylmethoxy) methyl] triphenylamine, 4-hydroxymethyl-4′-(2-oxiranylmethoxymethyl) triphenylamine and 4-[4-(oxiranylmethoxymethyl) phenylphenylamino]-4′-(diphenylamino) biphenyl are reported. Di-(tert-butylphenyl) iodonium tetrafluoroborate (BPIT), diphenyliodonium tetrafluoroborate (DPIT) and (η 5 -2,4-cyclopentadien-1-yl) [1,2,3,4,5-η)-(1-methylethyl) benzene]-iron (+)-hexafluorophosphate (−1) (Irgacure 261) were used as photoinitiators. These photopolymerizations give products with a degree of polymerization varying between 4 and 108. The photopolymerization of the triphenylamine based hydroxyl group containing oxirane apparently occurs by activated monomer mechanism in its final stage. Photopolymerization of 4-[(oxiranylmethoxy) methyl] triphenylamine was studied in more detail. The influence of photoinitiator, temperature, and photoinitiator concentration on the rate of polymerization and conversion limit is discussed.