Hydrophilic polymeric acylphospine oxide photoinitiators/crosslinkers for in vivo blue-light photopolymerization.
Three vinyl-functionalized phosphine oxide photoinitiating monomers have been synthesized: 4-vinylbenzoyldiphenylphosphine oxide (VBPO), 2,6-dimethyl-4-vinylbenzoyldiphenylphosphine oxide (DMVBPO), and 2,4,6-trimethylbenzoylphenyl-4-vinylphenylphosphine oxide (TMBVPO). VBPO was copolymerized with vinylpyrrolidone or vinyl acetate (PPI-1a) and dimethylacrylamide (PPI-1b). DMVBPO and TMBVPO were both copolymerized with dimethylacrylamide (PPI-2 and PPI-3, respectively). The choice of vinylphosphine oxide and comonomer(s) had a significant influence on the properties of the resulting PPI. PPI-1a was not stable in solution in 2-hydroxyethyl methacrylate (HEMA), whereas the VBPO-dimethylacrylamide (DMA) copolymer (PPI-1b) was stable in HEMA but not stable in aqueous solutions. PPI-2 was both soluble and stable in water up to 22 months. PPI-1a was as effective as trimethylbenzoyldiphenylphosphine oxide (TPO, BASF Lucirin). PPI-2 was more effective in the polymerization of HEMA/water mixtures than PPI-3. PPI-2 and PPI-3 acted as self-cross-linking species, resulting in the formation of hydrogels; PPI 3 was more effective in this. PPI-2 was very effective in forming hydrogels based on poly(ethylene glycol) diacrylate.
de Groot
J H
JH
Pharmacia Van Swietenlaan 5, 9728 NX Groningen, The Netherlands. jacqueline.degroot@pharmacia.com
Dillingham
K
K
Deuring
H
H
Haitjema
H J
HJ
van Beijma
F J
FJ
Hodd
K
K
Norrby
S
S
D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry; D003432:Cross-Linking Reagents; D020100:Hydrogels / Q000138:chemical synthesis; D008027:Light; D010087:Oxides; D010720:Phosphines / Q000737:chemistry* / Q000528:radiation effects*; D010777:Photochemistry; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility
D001672:Biocompatible Materials; D003432:Cross-Linking Reagents; D020100:Hydrogels; D010087:Oxides; D010720:Phosphines; D011108:Polymers