Kinetic evaluation of reactivity of bisphenol A derivatives as radical scavengers for methacrylate polymerization.
The reactivity of bisphenol A (BPA), diethylstilbestrol (DEST) 2,2'-biphenol (22'BP), 4,4'-biphenol (44'BP) and hydroquinone (HQ) as radical scavengers was examined in 2,2'-azobisisobutyronitrile (AIBN)- and benzoyl peroxide (BPO)-induced methyl methacrylate (MMA) polymerization with respect to kinetic considerations. The initial rate of polymerization (IRP) was found to decrease in the order: 44'BP > BPA, DEST > 22'BP >> HQ, while the stoichiometric factor (n) of free radicals trapped by phenolic moiety decreased in the order: 44'BP (2.3) > HQ (2.0) > BPA, DEST (1.8) >> 22'BP (0.8). It was found that BPA was a more highly efficient inhibitor than HQ and that HQ acts as a retarder at higher concentrations in the BPO system. The high activity of BPA indicated that BPA is probably oxidized by a radical interaction in the dental resin system.
Kadoma
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Y
Division of Biofunctional Molecules, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Japan.
Fujisawa
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S
D001559:Benzhydryl Compounds; D001585:Benzoyl Peroxide / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry / Q000378:metabolism*; D017438:Bisphenol A-Glycidyl Methacrylate / Q000737:chemistry*; D004054:Diethylstilbestrol / Q000737:chemistry / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism*; D006873:Hydroquinones / Q000737:chemistry / Q000378:metabolism*; D007700:Kinetics; D009570:Nitriles / Q000737:chemistry; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry / Q000378:metabolism*; D010895:Pit and Fissure Sealants / Q000737:chemistry*; D011108:Polymers; D000098826:Bisphenol A Compounds
D001559:Benzhydryl Compounds; D001585:Benzoyl Peroxide; D001713:Biphenyl Compounds; D017438:Bisphenol A-Glycidyl Methacrylate; D004054:Diethylstilbestrol; D016166:Free Radical Scavengers; D006873:Hydroquinones; D009570:Nitriles; D010636:Phenols; D010895:Pit and Fissure Sealants; D011108:Polymers; C004526:azobis(isobutyronitrile); C006780:bisphenol A; D000098826:Bisphenol A Compounds; C038764:2,2'-biphenol; C027439:4,4'-dihydroxybiphenyl; C031927:hydroquinone