A Simple Method for the Preparation of Functionalized Steric Hindered Methacrylic Acid Esters and Amides

Zeuner, Frank; Quint, S.; Geipel, Franz; Moszner, Norbert

doi:10.1081/scc-120028349

Cited by 7 publications

(7 citation statements)

References 13 publications

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“…Therefore, we synthesised the phosphonic acid monomer AEPA-4, which was completely stable under aqueous conditions at 42 8C during 4 months of investigation. [11][12][13][14] The improved hydrolytic stability of AEPA-4 in comparison to AEPA-1 is caused by the steric hindrance of hydrolysis regarding the methyl groups in the 2-and 6-position of the phenyl group. However, the bulky mesityl group also affects the reactivity of AEPA-4 in the free-radical polymerisation and AEPA-4 was therefore less reactive in the free-radical Figure 3.…”

Section: New Phosphorous-containing Adhesive Monomers With Improved Hmentioning

confidence: 99%

“…In addition, we found [118] that polycondensates, for example, of silane DMATES-1 can be used in mixtures with conventional dental dimethacrylates as UDMA (Figure 12) resulting in cured networks with reduced residual unsaturation and increased monomer conversion. Moreover, the mechanical properties of organicinorganic hybrids based on polycondensates of silane DMATES-2 or DMATES-4 could be improved by the methacrylate-substituted cluster Zr 4 O 2 (methacrylate) 12 . [120] Recently, we demonstrated [121] by size exclusion chromatography and matrix-assisted laser desorption/ionisation time-of-flight mass spectroscopy (MALDI-TOF MS) that the structure of the methacrylate based polycondensates was composed of different cyclic polyhedral oligomers, depending both on the kind of catalyst used for the hydrolytic condensation and the bulkiness of the organic substituent at the silicon atom.…”

Section: Organic-inorganic Components For Dental Restorative Materialsmentioning

confidence: 99%

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Recent Developments of New Components for Dental Adhesives and Composites

Moszner¹,

Salz²

2007

Macro Materials & Eng

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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%

Section: Organic-inorganic Components For Dental Restorative Materialsmentioning

confidence: 99%

Recent Developments of New Components for Dental Adhesives and Composites

Moszner¹,

Salz²

2007

Macro Materials & Eng

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203

110

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“…2,4,6-Trimethylphenyl 2-[4-(dimethoxyphosphoryl)-2-oxa-butyl]acrylate was synthesized as described recently. [5] Monomers 2 and 3 (Scheme 2) were prepared as previously described. [1,3] Methyl methacrylate (MMA) was washed with a 5.0 wt.-% NaOH solution, dried over anhydrous sodium sulfate, and distilled from calcium hydride under argon.…”

Section: Experimental Partmentioning

confidence: 99%

“…Recently, we were able to synthesize new steric hindered a-methylsubstituted acrylate -containing dimethyl phosphonate groups. [5] In this paper, the synthesis, characterization, and homopolymerization of the exceptionally hydrolytically stable monomer 1 (Scheme 1), are described. Furthermore, the copolymerization of 1 with MMA, the polymerizable phosphonic acid 2 and the hydrolytically stable crosslinking bis(acrylamide) 3 were investigated.…”

Section: Introductionmentioning

confidence: 99%

Monomers for Adhesive Polymers, 5

Pavlineč

Zeuner

Angermann

et al. 2005

Macro Chemistry & Physics

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Summary: 2,4,6‐Trimethylphenyl 2‐[4‐(dihydroxyphosphoryl)‐2‐oxa‐butyl]acrylate (1) was synthesized by silylation of 2,4,6‐trimethylphenyl 2‐[4‐(dimethoxyphosphoryl)‐2‐oxa‐butyl]acrylate with trimethylsilyl bromide (TMSBr) and the hydrolysis of the silyl ester resulted in the formation of polymerizable phosphonic acid 1. The structure of this new monomer was characterized by IR, 1H, 13C and 31P NMR spectroscopy. The monomer dissolves well in ethyl acetate, ethanol or water and shows a high hydrolytic stability. 1 was homopolymerized with 2,2′‐azobisisobutyronitrile (AIBN), 2,2′‐azobis‐(2‐methylpropionamidine) dihydrochloride (AMPAHC) or dibenzoyl peroxide (DBPO) as the initiators. In a tetrahydrofuran (THF) solution, the deviations from the standard reaction kinetics were comparable with those of polymerizations of the other water soluble acrylate monomers. The unusual polymerization rate‐monomer concentration dependence with monomer intensity exponent less than 1 (m = 0.5) observed in THF solutions was even more declined from 1 in the polar medium EtOH‐H2O. The DBPO was a more effective polymerization initiator than AIBN. However, the overall activation energy of 81 kJ · mol−1 showed a usual temperature‐rate dependence observed in methacrylate ester polymerizations. In addition, monomer 1 was copolymerized with methyl methacrylate (MMA), ethyl 2‐[4‐(dihydroxyphosphoryl)‐2‐oxa‐butyl]acrylate (2), and N,N′‐diethyl‐1,3‐bis(acrylamido)propane (3), respectively, using THF as the solvent and AIBN as the initiator. The copolymerization curves revealed only slight deviations from the ideal copolymer‐feed composition. The estimated copolymerization parameters indicate a ready incorporation of comonomer units into polymer chains, preferably by alteration rather than at random.

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“…One of the major problems encountered with the dental composites is the lack of bonding to the tooth material. To address that problem, novel monomers with binding ability have been designed 3–15. In general, this binding ability is provided by acid functional groups such as carboxylic, phosphonic, and phosphoric acids, which form chelates with the calcium ions in the tooth surface.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photopolymerizations of new phosphonated methacrylates from alkyl α‐hydroxymethacrylates and glycidyl methacrylate

Sahin

Avcı

Karahan

et al. 2009

J of Applied Polymer Sci

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Novel aromatic mono-and di(phosphonate) or phosphonic acid monomers for use in dental composites were synthesized. Synthesis of monomer 1a involved three steps: (i) reaction of t-butyl a-bromomethacrylate (tBuBMA) and Bisphenol A, (ii) conversion to diacid chloride derivative using thionyl chloride, (iii) reaction of diacid chloride with diethyl (2-hydroxyphenyl) phosphonate. Monomer 2a was synthesized from the reaction of 2-chloromethacryloyl chloride and diethyl (2-hydroxyphenyl) phosphonate. Synthesis of monomer 3a involved reaction of glycidyl methacrylate (GMA) with diethyl (2-hydroxyphenyl) phosphonate. Hydrolysis of the phosphonate groups of monomers 1a and 2a with trimethylsilyl bromide (TMSBr) gave monomers 1b and 2b with phosphonic acid functionality, which is intended to improve binding ability of dental composites. The homopolymerization and copolymerization behaviors of the synthesized monomers with (Bis-GMA) were investigated using photodifferential scanning calorimetry at 40 C with 2,2 0 -dimethoxy-2-phenyl acetophenone as photoinitiator. The interaction of the monomer 1b with hydroxyapatite (HAP) was investigated using Fourier transform infrared technique.

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A Simple Method for the Preparation of Functionalized Steric Hindered Methacrylic Acid Esters and Amides

Cited by 7 publications

References 13 publications

Recent Developments of New Components for Dental Adhesives and Composites

Recent Developments of New Components for Dental Adhesives and Composites

Monomers for Adhesive Polymers, 5

Synthesis and photopolymerizations of new phosphonated methacrylates from alkyl α‐hydroxymethacrylates and glycidyl methacrylate

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