Piperonyl methacrylate: Copolymerizable coinitiator for adhesive compositions. (December 2018)

• Record Type: Journal Article
• Authors: Moreira, Andressa Goicochea; Cuevas-Suárez, Carlos Enrique; da Rosa, Wellington Luiz de Oliveira; Ogliari, Aline Oliveira; Petzhold, Cesar Liberato; Piva, Evandro; Ogliari, Fabrício Aulo; Lima, Giana da Silveira
• Is Part Of: Journal of dentistry. Volume 79(2018:Dec.)
• Page Start: 31
• Page End: 38
• Publication Date: 2018-12
• Subjects: Dental adhesive -- Coinitiator -- Hydrogen donor -- Type II photoinitiation system -- Photopolymerization; Dentistry -- Periodicals; Dentistry -- Periodicals; Dentisterie -- Périodiques; Electronic journals; 617.6005
• DOI: 10.1016/j.jdent.2018.09.006
• Languages: English
• ISSNs: 0300-5712

Abstract

Graphical abstract: Highlights: The synthesis of piperonyl methacrylate (PipM) is described. PipM was evaluated as coinitiator for photosensitive dental adhesives. Rate of polymerization and degree of CC conversion were improved. PipM is a feasible alternative to tertiary amines as coinitiator. Abstract: Objectives: This study describes the synthesis of piperonyl methacrylate (PipM) and evaluates its effect when used as coinitiator in the photoinitiated radical polymerization of experimental adhesive resins. Methods: PipM was synthetized through an esterification reaction and characterized by FTIR and 1 H NMR spectroscopy. Adhesive resins containing camphorquinone as photoinitiator and PipM or ethyl-4-dimethyl amine benzoate (EDAB) as coinitiators were formulated. Scotchbond Multipurpose (SBMP) adhesive was used as commercial reference. All materials were analyzed for polymerization kinetics, flexural strength, elastic modulus, water sorption/solubility, shear bond strength to bovine enamel and dentin, characterization of hybrid layer by scanning electron microscopy (SEM), microbiological direct contact test, and cytotoxicity. Results: The adhesive with PipM presented higher degree of conversion and lower sorption/solubility when compared with other groups. Shear bond strength to enamel and dentin were similar for PipM and EDAB materials. The percentage of cellular viability was close to 100% and similar in the experimental groups and the commercial reference. Conclusions: PipM presented similar or superior performance to the tertiary amine used as control, representing a potential alternative coinitiator for photopolymerizable dental materials. Clinical significance: PipM could be potentially useful in the formulations of adhesive systems with enhanced chemical properties, which could mean improvement in the longevity of composite resin restorations.