Synthesis of a hydrophilic phosphonic acid monomer for dental materials

Mou, Liyuan; Singh, Gurdial; Nicholson, John W.

doi:10.1039/a909877a

Cited by 44 publications

(36 citation statements)

References 8 publications

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“…[17] In contrast, homopolymers with a number-average molecular weight of 11 400 g Á mol À1 were formed by the free-radical polymerisation of APA-3 in the presence of 2,2 0 -azoisobutyronitrile (AIBN) after 24 h. Furthermore, methacrylates (MA) of hydroxyl alkyl phosphonates have been mentioned in the context with dental materials, for example, 2-(methacryloyloxy)-ethylphosphonic acid (MAPA-1) [19] or the difunctional monomer MAPA-2 ( Figure 5). [20] However, these monomers are not hydrolytically stable, because they undergo hydrolysis if water is present, and form methacrylic acid. Furthermore, in recent patents, the synthesis of a number of hydrolytically stable methacrylamide phosphonic acids (MAPA) as MAMPA-1 [21] and MAMPA-2 [22] or acrylic ether dihydrogen phosphates (AEDHP) as AEDHP-1 and AEDHP-2 [23] (Figure 6) are described.…”

Section: New Phosphorous-containing Adhesive Monomers With Improved Hmentioning

confidence: 99%

Recent Developments of New Components for Dental Adhesives and Composites

Moszner¹,

Salz²

2007

Macro Materials & Eng

204

110

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The currently used commercial self‐etching enamel‐dentin adhesives and restoratives composites are mainly based on a mixture of various monofunctional and cross‐linking dimethacrylates. New developments of enamel‐dentin adhesives concern the improvement of technique insensitivity and storage stability. Improvements of restorative composites are focused on the reduction of the polymerisation shrinkage, as well as the improvement of wear resistance, biocompatibility, and processing properties. In the past five years, many research efforts have been carried out to develop new monomers and tailor‐made components for filling materials, such as fillers or initiators. New phosphonic acid ether acrylates and cross‐linking bis(acrylamide)s enable the preparation of self‐etching enamel‐dentin adhesives with improved storage stability. With free‐radically polymerisable cyclic monomers, such as bicyclic cyclopropyl acrylates or cyclic allyl sulfides, low‐shrinkage storage‐stable restorative composites could be prepared. In case of the cationic polymerisable cyclic monomers, like siloxane‐based cycloaliphatic epoxides, the lower curing rate, stronger exothermic effect and lower curing depth compared to dimethacrylate‐based composites presently prevent their dental application. Designed methacrylates with tailor‐made properties and sol‐gel polycondensates can also contribute to the improvement of the currently used restorative composites. Radical polymerisable dental materials are initiated by light curing and by redox initiator systems. Under acidic conditions amine containing initiator systems are deactivated by acid‐base reaction. Non amine‐based initiators have to be developed for acidic monomer containing dental materials. The use of discrete nano‐filler particles mainly concerns the reinforcement and, in some cases, the increase of X‐ray opacity of composite filling materials.magnified image

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Section: New Phosphorous-containing Adhesive Monomers With Improved Hmentioning

confidence: 99%

Recent Developments of New Components for Dental Adhesives and Composites

Moszner¹,

Salz²

2007

Macro Materials & Eng

204

110

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“…Secondary reactions have been suggested to provide additional chemical bonding to the hard dental tissues. [1][2][3][4] The basic F-Al-Si-based inorganic fillers in selfadhesive cements are able to react with the monomers with acid functionalities. 1,5 The dominant setting reaction, however, occurs via free-radical polymerization, initiated either by light or a redox system that allows resin polymerization in an acidic environment.…”

Section: Introductionmentioning

confidence: 99%

Dual and Self-curing Potential of Self-adhesive Resin Cements as Thin Films

Moraes

Boscato²,

Jardim³

et al. 2011

Operative Dentistry

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In this study, the dual- and self-curing potential of self-adhesive resin cements (SARCs) as thin, clinically-relevant cement films was investigated. The SARCs tested were: BisCem (BSC; Bisco), Maxcem Elite (MXE; Kerr), RelyX Unicem clicker (UNI; 3M ESPE), seT capsule (SET; SDI), and SmartCem 2 (SC2; Dentsply Caulk). The conventional cement RelyX ARC (3M ESPE) was tested as a reference. The degree of conversion (DC) as a function of time was evaluated by real-time Fourier transform infrared spectroscopy with an attenuated total reflectance (ATR) device. The cements were either photoactivated for 40 seconds (dual-cure mode) or not photoactivated (self-cure mode). The cement film thickness was 50 ± 10 μm. The DC (%) was evaluated 1, 5, 10, 15, 20, 25, and 30 minutes after placing the cement on the ATR cell. Data for DC as a function of time were analyzed by two-way repeated measures analysis of variance (ANOVA). DC values at 30 minutes for the self- and dual-cure modes were submitted to one-way ANOVA. Post hoc comparisons were performed using the Student-Newman-Keuls test (p<0.05). The rate and the extent of conversion were lower for the SARCs compared with the conventional cement. Means ± standard deviations (SD) for the dual-cure mode at 30 minutes were: 75 ± 5 (ARC)a, 73 ± 8 (SET)a, 61 ± 4 (MXE)b, 51 ± 9 (BSC)c, 51 ± 4 (UNI)c, and 48 ± 3 (SC2)c, while in the self-cure mode means and SD were 62 ± 6 (ARC)a, 54 ± 3 (MXE)b, 40 ± 6 (SC2)c, 35 ± 2 (UNI)c, 35 ± 3 (SET)c, and 11 ± 3 (BSC)d. The DC for the dual-cure mode was generally higher than the self-cure, irrespective of the time. Discrepancies in DC between the dual- and self-cure modes from 11% to 79% were observed. In conclusion, SARCs may present slower rate of polymerization and lower final DC than conventional resin cements, in either the dual- or self-cure mode.

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“…[19][20][21][22] The incorporation of phosphonic acid into acrylic monomers used in the dental industry can promote both biocompatibility and adhesion to the teeth, because of the formation of calcium phosphonates and phosphonate complexes. 21,[23][24][25] Phosphonates, corresponding anions of phosphonic acid, have strong interactions with and adsorb very powerfully onto mineral surfaces. 26 Phosphonic acid-based polymers have also found several applications such as chelating agents for heavy metal salts, 27,28 ion-exchange resins, 29 and fuel cell membranes.…”

Section: Introductionmentioning

confidence: 99%