Novel, highly efficient polymeric benzophenone photoinitiator containing coinitiator moieties for photopolymerization

Abstract

A novel polymeric photoinitiator P(MPBP‐co‐DMAEMA), bearing side‐chain benzophenone (BP) and coinitiator amine, was synthesized through free radical copolymerization of a polymerizable photoinitiator, 4‐[(4‐maleimido)phenoxy]benzophenone (MPBP), and a polymerizable coinitiator amine, N, N‐dimethylaminoethyl methacrylate (DMAEMA). In order to find out the influences of coinitiator amine on photopolymerization, a polymeric coinitiator amine, P(DMAEMA), was also synthesized for comparison. FT‐IR, 1H NMR, and GPC analyses confirm the structures of polymers. The UV‐Vis spectra of polymeric photoinitiator P(MPBP‐co‐DMAEMA) and polymerizable photoinitiator MPBP are similar, and both exhibit high red‐shifted maximal absorption as compared with BP. The photopolymerization of 1,6‐hexanediol diacrylate (HDDA) and trimethylolpropane triacrylate (TMPTA), initiated by MPBP/DMAEMA, MPBP/P(DMAEMA), and P(MPBP‐co‐DMAEMA) systems, was studied by photo‐DSC. The results indicate that P(MPBP‐co‐DMAEMA) is most efficient for the polymerization of both HDDA and TMPTA, and MPBP/P(DMAEMA) is the least efficient of the three photoinitiating systems. Copyright © 2009 John Wiley & Sons, Ltd.

Moving Towards a Finer Way of Light-Cured Resin-Based Restorative Dental Materials: Recent Advances in Photoinitiating Systems Based on Iodonium Salts

“…However, the polymerization rate significantly increases when tertiary amines as co-initiators of radical photopolymerization are used. Amines such as ethyl-4-dimethylaminobenzoate (EDAB/EDMAB), 2-(dimethylamino)ethyl methacrylate (DMAEMA), N,N-dimethylptoluidine, N-phenylglycine (NPG), dimethylbenzoate are used as photosensitizers for CQ [ 120 , 121 , 122 , 123 , 124 , 125 , 126 , 127 ]. However, among these compounds, ethyl-4-dimethylaminobenzoate (EDB) is the most popular co-initiator in dental materials due to its high efficiency and low basicity.…”

Synthesis of New Polyether Ether Ketone Derivatives with Silver Binding Site and Coordination Compounds of Their Monomers with Different Silver Salts

“…The precipitated product was filtered, washed thoroughly with water, and dried to give product (2): 7.8 g (27%). 1 To a solution of (2) (11 g, 50 mmol) in dry dichloromethane (100 mL) at 0˝C under an argon atmosphere, oxalyl chloride (8.8 mL, 92 mmol) was dropwise added, followed by a few drops of dimethylformamide. The ice bath was removed, the reaction was heated to reflux for 12 h, and then cooled down.…”

“…The aqueous phase was washed twice with 50 mL of diethylether. Finally the combined organic phases were washed with 50 mL of diluted sodium hydroxide solution, then water, dried and evaporated to give product (3): 14.1 g (95%) 1 Compound (3) (25 mg, 0.084 mmol), 4-pyridylboronic acid (15.5 mg, 0.126 mmol), tetrakis(triphenylphosphine)palladium(0) (10 mg, 0.008 mmol) and potassium carbonate (50 mg, 0.36 mmol) in dimethylformamide (3.5 mL) and water (0.5 mL) were mixed together under inert conditions. The reaction was heated to 160˝C for 10 min using microwave irradiation.…”

“…The expected product (5) gives white needles of complex (5a) suitable for X-ray measurement. 1 In a 2-necked flask equipped with a stirrer, air condenser and argon inlet, product (4) and hydroquinone derivatives (5 for PEEKN5, 6 for PEEKN6 or 7 for PEEKN7) (Scheme 2) were added in a 1:1 ratio with diphenylsulphone as solvent and potassium carbonate (1.05 equiv.). The mixture was heated to 200˝C for 30 min, then to 250˝C for 30 min, and finally to 300˝C for 30 min.…”

“…Benzophenone is a widely used organic compound, for example, as a photo-initiator [ 1 ] in inks [ 2 ] and imaging. One of its derivatives is used as a monomer for the preparation of polyether ether ketone ( PEEK ) [ 3 ], which is a thermoplastic polymer with good mechanical and chemical properties [ 4 , 5 ].…”