Classifications

• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B82—NANOTECHNOLOGY
  • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
  • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K6/00—Preparations for dentistry
  • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
  • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
  • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K6/00—Preparations for dentistry
  • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
  • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
  • A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • A61K6/893—Polyurethanes

Definitions

• the present invention relates to a light-polymerizable dental composition comprising a specific inhibitor. Moreover, the present invention also relates to the use of specific fullerene compounds in a dental composition.
• Light-polymerizable dental compositions comprise a polymerizable monomer, a light-sensitive polymerization initiator, and optionally further components such as an organic or inorganic filler or an organic or inorganic pigment. It is known to use a stabilizer for preventing a composition containing polymerizable acrylates and/or methacrylates from spontaneous polymerization. 2,6-Di-tert-butyl-4-cresol (BHT), hydroquinone or hydroquinonemonomethylether (HQME) are known as free radical savengers for dental compositions.
• BHT 2,6-Di-tert-butyl-4-cresol
• HQME hydroquinone or hydroquinonemonomethylether
• Light curing polymerisable dental compositions are usually applied in the presence of substantial irradiation of the environment particularily radiation generated by operating lamps.
• international standards require that a dental dental composite remains stable under an illumination of 10.000 lux for 60 seconds (ISO 4049).
• Dental pit and fissure sealants are required to remain stable under an illumination of 8000 lux for 25 seconds (ISO 6874) and light activated water- based cements are required to remain stable under an illumination of 8000 lux for 30 seconds (ISO 99917-2).
• TEMPO 2,2,6,6-tetramethylpiperidinyl-1 -oxide
• galvinoxyl radicals, hydroxy-TEMPO and 2,2-diphenyl-1-picrylhydrazyl radicals as anaerobic polymerization inhibitors (US 5,468,789).
• TEMPO as polymerization inhibitor in polymerizable dental compositions and its influence on the depth of curing is known for light curing restorative materials from W.D. Cook, P.M. Standish, Austr. Dent. J., 28 (1983) 307.
• US 5,847,025 discloses the use of TEMPO and other stable radiclas such as 2,2-Diphenyl- -picrylhydrazyl radicals, galvinoxyl radicals and triphenylmethyl radicals for reducing the light sensitivity of a dental light-curing composite material.
• the dental composition of the present invention comprises an inhibitor which is a substituted fullerene compound.
• the inhibitor may contain one or more substituted fullerene compounds.
• the substituted fullerene compoundd is preferably soluble in the composition, in particular in the polymerisable monomer.
• the inhibitor is selected from the group of substituted C 60 , C 70 , C 72 , C 76 , C 78 , or C 84 fullerenes.
• a substituted fullerene compound according to the invention is derived from an unsubstituted fullerene compound by addition or insertion of substituents to the fullerene cage.
• the substituents added or inserted to the fulleren cage may be further modified in order to provide the desired substituted fullerene compound used in the dental compositions of the invention.
• the substituents are preferably able to render the fullerene compound soluble in the composition, in particular in the polymerisable monomer.
• the substituents preferably contribute to the electronic properties of the inhibitor as a radical scavenger.
• the substituents preferably are able to modify the fullerene cage such that any chromophores absorbing in the range of visible light are destroyed.
• substituents may be present on the fullerene cage whereby it is preferred that at least two substituents are present. In case at least two substituents are present on the fullerene cage , the substituents may be the same or different.
• the substituents of the substituted fullerenes are preferably selected from the group of substituted or unsubstituted C ⁇ o-alkyl groups, C ⁇ -alkoxy groups, C 1 . 2 o-alkyl-C 1 . 20 -alkoxy groups, C,. 20 -alkylthio groups, C ⁇ o-alkylthio-C ⁇ o-alkyl groups, C ⁇ oalkylamino groups, C ⁇ o - groups or groups.
• substituents of the fullerene cage may be selected form the group of substituents given as substituents for the fullerene cage. Moreover, such substituents may be selected from the group consisting of hydroxyl groups, amino groups, thiol groups. In a specific embodiment, one or more substituents of the fullerene cage are substitued with a polymerizable group.
• the polymerizable group may be selected from acryloyl, C 1 . 20 -alkylacryloyl, or C 1 . 20 -alkenyl groups.
• the substituted fullerenes are added to the dental composition in an amount ranging from 0.001 to 3.0% by weight, preferably in an amount of from 0.01 to 1.0% by weight and most preferably in an amount of from 0.01 to 0.2% by weight.
• the dental composition of the present invention comprises a light-polymerizable monomer component.
• the light-polymerizable monomer component contains one or more monomer compounds. In case the monomer component contains two or more monomer compounds, the monomer compounds may differ with regard to the molecular weight and/or the number of polymerizable moieties.
• a macromonomer and a reactive diluent are used in the polymerizable monomer component.
• the monomer compound to be used in the monomer component of the dental composition of the present invention preferably has at least one polymerizable group and is a mono- or polyfunctional (meth)acrylate or a macromonomer.
• Preferable monomers are 2,2-Bis-[p-(2-hydroxy-3-methacryloyloxypropoxy)-phenyl]-propane, 7, 7,9-trimethyl-4, 13-dioxo-3, 14-dioxa-5, 12-diazahexadecan-1 , 16-diol methacrylate, dipentaerthrytrolpentamethacrylate monophosphate, ⁇ , ⁇ -methacryloyl terminated epoxide-amine macromonomers, ⁇ , ⁇ -methacryloyl terminated epoxidecarboxylic acid macromonomers, ⁇ , ⁇ -methacryloyl terminated epoxide-phenol macromonomers.
• U the macromonomers disclosed in U.
• Reactive diluents are mono(meth) acrylates and polyfunctional (meth) acrylates, such as polyalkylenoxide di-(meth)acrylates or poly(meth)acrylates, urethane di(meth) acrylates or poly(meth)acrylates, vinyl-, vinylen- or vinyliden-, acrylate- or methacrylate substituted spiroorthoesters, spiroorthocarbonates or bicycloorthoesters.
• mono(meth) acrylates and polyfunctional (meth) acrylates such as polyalkylenoxide di-(meth)acrylates or poly(meth)acrylates, urethane di(meth) acrylates or poly(meth)acrylates, vinyl-, vinylen- or vinyliden-, acrylate- or methacrylate substituted spiroorthoesters, spiroorthocarbonates or bicycloorthoesters.
• Preferred reactive diluents are diethyleneglycol dimethacrylate, triethyleneglycol dimethacrylate, 3,(4),8,(9)dimethacryloyloxymethyltricyclodecane, dioxolan bismethacrylate, glycerol trimethacrylate, and furfuryl methacrylate.
• the polymerizable monomer component may be present in the dental composition of the present invention in an amount of from 1 to 99 percent by weight, preferably in an amount of from 10 to 60 percent by weight.
• the dental composition of the present invention comprises a light-sensitive polymerization initiator.
• Suitable initiators are benzophenone, benzoin or derivatives therof.
• Preferred initiators are ⁇ -diketones such as 9,10-phenanthrene quinone, diacetyl, furyl, anisyl, 4,4'-dichlorobenzil and 4,4'-dialkoxybenzil. Particularily preferred is camphorquinone.
• the initiators may be used in combination with an amine as activator. Examples for such activators are N.N-dimethyl-p-toluidine, N,N- dihydroxyethyl-p-toluidine, and N-(2-cyanoethyl)-N-methylaniline.
• the initiator may be present in the dental composition of the present invention in an amount of 0.001 to 2 percent by weight, preferably in an amount of from 0.5 to 1 percent by weight.
• the dental composition of the present invention optionally comprises a filler.
• the filler may be an inorganic fillers such as La 2 O 3 , ZrO 2 , BiPO 4 , CaWO 4 , BaWO 4 , SrF 2 , Bi 2 O 3 , glasses.
• the filler may also be or an organic fillers, such as a polymer granulate.
• the filler may be a combination of organic and inorganic fillers.
• the filler may be present in the dental composition of the present invention in an amount of 20 to 85 percent by weight.
• the filler is present in an amount of from 50 to 85 percent by weight, and in case of a sealer the filler is preferably present in an amount of from 20 to 50 percent by weight.
• the dental composition of the present invention optionally comprises a pigment.
• pigments which may be incorporated into a composition of the present invention are titanium oxides and iron oxides.
• the dental composition of the present invention optionally comprises a solvent. Suitable solvents for use in a dental composition according to the invention are acetone, methylethyl ketone, and ethanol.
• a preferred dental composition according to the invention is a composite comprising from
• a preferred dental composition according to the invention is a sealer comprising from
• an inhibitor optionally 20 to 50 percent by weight of a filler and/or pigment, and optionally 0 to 10 percent by weight of a solvent.
• the dental composition according to the present invention may be prepared by mixing the components of the composition.

Landscapes

• Health & Medical Sciences (AREA)
• Oral & Maxillofacial Surgery (AREA)
• Engineering & Computer Science (AREA)
• Chemical & Material Sciences (AREA)
• Veterinary Medicine (AREA)
• Plastic & Reconstructive Surgery (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Life Sciences & Earth Sciences (AREA)
• Nanotechnology (AREA)
• Epidemiology (AREA)
• Animal Behavior & Ethology (AREA)
• Composite Materials (AREA)
• Condensed Matter Physics & Semiconductors (AREA)
• General Physics & Mathematics (AREA)
• Materials Engineering (AREA)
• Crystallography & Structural Chemistry (AREA)
• Physics & Mathematics (AREA)
• Dental Preparations (AREA)

Applications Claiming Priority (3)

Publications (1)

Family

ID=7682388

Family Applications (1)

Country Status (4)

Families Citing this family (28)

Family Cites Families (2)

• 2001
  • 2001-04-23 DE DE10119831A patent/DE10119831A1/de not_active Withdrawn
• 2002
  • 2002-04-16 WO PCT/US2002/011978 patent/WO2002085974A1/en not_active Application Discontinuation
  • 2002-04-16 EP EP02739151A patent/EP1381646A1/de not_active Withdrawn
  • 2002-04-16 CA CA002425953A patent/CA2425953A1/en not_active Abandoned

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events