The Synthesis of New Type II Polymeric Photoinitiator (thioxantone) via Atom Transfer Radical Polymerization and Their Curing and Migration Studies


Kandirmaz E., Gençoğlu E. N., Apohan N.

MACROMOLECULAR RESEARCH, cilt.27, ss.756-763, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1007/s13233-019-7107-3
  • Dergi Adı: MACROMOLECULAR RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.756-763
  • Anahtar Kelimeler: polymeric photoinitiator, photopolymerization, thioxanthone, migration, flexographic varnish, IN-CHAIN THIOXANTHONE, FOOD-PACKAGING MATERIALS, AMINE, MACROPHOTOINITIATOR, ACID
  • Marmara Üniversitesi Adresli: Evet

Özet

Polymeric photoinitiators are widely used in ultraviolet (UV)-curable printing inks because of their low migration behavior. In this study, a new phenylphosphine oxide-polystyrene-thioxanthone (PPO-PSt-TX) polymeric photoinitiator was synthesized. Bis[(4-hydroxy)phenyl]phenyl phosphine oxide (BHPPO) that was synthesized by Grignard technique, was functionalized with 2-bromopropionyl bromide (atom transfer radical polymerization (ATRP) initiator) and then used in styrene polymerization. The bromine end-capped polystyrene was then reacted with 2-thioxanthone-thioacetic acid and final polymeric photoinitiator PPO-PSt-TX was obtained. Proton nuclear magnetic resonance (1H NMR), attenuated total reflectance- Fourier transform infrared spectroscopy (ATR-FTIR), gel permeation chromatography (GPC) and ultraviolet-visible spectroscopy (UV-Vis) confirmed the obtained structure. The curing characteristic of PPO-PSt-TX was compared with a standard flexographic printing varnish formulation containing thioxanthone (TX). The photopolymerization kinetics were determined by photo differential scanning calorimetry (Photo-DSC). The conversion of methylmethacrylate polymerization by using macrophotoinitiator is 78%. The migration behavior of PPO-PSt-TX was identified with liquid chromatography-mass spectrometry (LC-MS). It was shown that PPOPSt- TX macro photoinitiator is suitable for flexographic varnish and the migration level of photoinitiator is reduced by using polymeric photoinitiator.