Effect on adhesion of new polymerization initiator systems comprising 5-monosubstituted barbituric acids, aromatic sulfinate amides, andtert-butyl peroxymaleic acid in dental adhesive resin

Abstract

To develop a multipurpose dental adhesive resin, the effects of polymerization initiator systems comprising 5-monosubstituted barbituric acid (5-MSBA), aromatic sulfinate amide (ASA), and tert-butyl peroxymaleic acid (t-BPMA) with 4-acryloxyethyltrimellitic acid (4-AET) or its anhydride (4-AETA) on adhesion and curing time were investigated. Tensile bond strength values of a NiOCr alloy are affected by the inclusion of t-BPMA, and the optimum concentration of t-BPMA in a 5-MSBA-ASA-t-BPMA-type initiator system was found to be 0.5-2.0 wt %, and it was noteworthy that the correlation between the tensile bond strength and curing time on the t-BPMAconcentration showed a highly negative correlation of a benzenesulfinate morphoride (BSMo) series adhesive: r ϭ Ϫ0.957, and a p-toluenesulfinate morphoride (p-TSMo) series adhesive: r ϭ Ϫ0.949. The combination of 1-cyclohexyl-5-ethylbarbiturioc acid (CEBA) with ASA provides a high level of tensile bond strength to the NiOCr alloy, and the optimum concentration of CEBA in a CEBA-ASA-t-BPMA-type initiator and the bond strength values were found to be 0.75 wt % CEBA: 52.3 MPa (with BSMo), and 1.0 wt % CEBA: 50.9 MPa (with p-TSMo), respectively. It was suggested that 5-MSBA, ASA, and t-BPMA and their combinations provided the environment where 4-AETA exhibited good bonding performance with increasing wettability to metal without interference of a charge-transfer complex derived from a polymerization initiator system such as benzoyl peroxide (BPO)-amine.

Single-bottle adhesives behave as permeable membranes after polymerization. I. In vivo evidence

“…The presence of these water droplets may also interfere with bonding of indirect restorations by inducing emulsion polymerisation of the coupling hydrophobic resin cements 16,42 and was thought to be a contributing factor in the incompatibility between dual/auto-cured composites/resin cements and simplified self-etch adhesives, under the condition that then adverse acid-base reaction between the acidic monomers and basic tertiary amines was offset via the inclusion of ternary catalytic systems. 43 The transudation of dentinal fluid through simplified self-etch adhesives has also been demonstrated in vivo, using a similar technique as that employed in the present study (Chersoni et al, unpublished results).…”

Effect of oxygen inhibition in two-step self-etch systems on surface free energy and dentin bond strength with a chemically cured resin composite

“…One polymerization initiator commonly used with chemically cured resin composites is a redox initiator system consisting of benzoyl peroxide (BPO) and nucleophilic tertiary amines. Aromatic tertiary amines (electron acceptors) react with the acidic groups (electron donors) of adhesive monomers, forming charge-transfer complexes that impede free-radical generation, resulting in incomplete polymerization of chemically cured resin composites (27). To overcome this incompatibility, use of BPO-aromatic tertiary amine-p-toluenesulfinic acid sodium salts with an acidic phosphate monomer has been proposed (28).…”

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

“…amine (π acceptor) can react with an acidic group, i.e., phosphoric acid, phosphonic acid, or carboxylic acid group (π donor) in adhesive monomers to form chargetransfer complexes (CT complexes) 22,23) or undesirable quaternary ammonium salt 4) (Fig. 1).…”

“…Since tertiary amines (i.e., PIDAA and EDAB) accelerated the photopolymerization process 15,18) , it was probable that QTX performed a hydrogen abstraction initiation mechanism similar to that of CQ/tertiary amine system. It was thus anticipated that tertiary amines (π acceptor) could react with acidic groups (π donor) (i.e., phosphoric acid, phosphonic acid, and carboxyl groups) of adhesive monomers to form undesirable quaternary ammonium salts 4) or chargetransfer complexes (CT complexes) with adverse effects 22,23) on initiation reactivity and adhesion.…”