Irgacure 2959-functionalized poly(ethyleneimine)s as improved photoinitiators: enhanced water solubility, migration stability and visible-light operation

Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) ( M w = 1800 g mol...

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Bibliographic Details
Published in:Polymer chemistry 2021-05, Vol.12 (18), p.2772-2785
Main Authors: Eren, Tugce Nur, Kariksiz, Neslihan, Demirci, Gozde, Tuncel, Duygu, Okte, Neren, Yagci Acar, Havva, Avci, Duygu
Format: Article
Language:English
Subjects:
Biocompatibility
Biomedical materials
Charge transfer
Complex formation
Conversion
Fourier transforms
Free radical polymerization
Free radicals
Photoinitiators
Photopolymerization
Polyethyleneimine
Polymer chemistry
Polymerization
Solubility
Stability
Toxicity
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Summary:Two novel water soluble polymeric photoinitiators (PPIs) (PEI-I2959 and PEI-I2959-Ts) for free radical polymerization have been synthesized by introducing 2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone (Irgacure 2959 or I2959) functionality into branched poly(ethyleneimine) ( M w = 1800 g mol −1 ). These PPIs show an excellent water-solubility of 35-45 g L −1 , thus exceeding the solubility of I2959 by 7-9-fold. PPIs show strong absorbance at 274 nm ( ∼ 2-3 times larger than that of I2959); and less prominent peaks at 320 and 380 nm for PEI-I2959 and PEI-I2959-Ts, respectively, in water. The aza-Michael addition (∼10% conversion) and high photopolymerization efficiencies (90-100% conversion) under both UV and visible light are obtained by photo-differential scanning calorimetry (photo-DSC) and Real-Time Fourier Transform Infrared (RT-FTIR) spectroscopy. The photopolymerization mechanisms involve charge transfer complex formation, verified by absorption studies and enabling visible light polymerization; and a Type I mechanism. PEI-I2959-Ts exhibits 8 times higher migration stability than I2959 due to its high molecular weight. In tests against NIH/3T3 and L929 mouse embryonic fibroblast cells using the MTT cell viability assay, the non-cytotoxicity of PEI-I2959-Ts is shown and PEI-I2959 shows reasonable cell viability at lower concentrations, indicating that PPIs have potential usage in biomaterials. I2959-functionalized PEI based PPIs with 7-9 times higher water solubility than I2959, visible light activation, dual-curing properties and migration stability were synthesized.
ISSN:1759-9954
1759-9962
DOI:10.1039/d1py00298h