EP2180871A2 - Matériau de remplissage de canal radiculaire - Google Patents

Matériau de remplissage de canal radiculaire

Info

Publication number
EP2180871A2
EP2180871A2 EP08773702A EP08773702A EP2180871A2 EP 2180871 A2 EP2180871 A2 EP 2180871A2 EP 08773702 A EP08773702 A EP 08773702A EP 08773702 A EP08773702 A EP 08773702A EP 2180871 A2 EP2180871 A2 EP 2180871A2
Authority
EP
European Patent Office
Prior art keywords
composition according
polymerizable composition
meth
molecular weight
acrylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08773702A
Other languages
German (de)
English (en)
Inventor
Jürgen Engelbrecht
Gunther Groeger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
S&C Polymer Silicon und Composite Spezialitaeten GmbH
Original Assignee
S&C Polymer Silicon und Composite Spezialitaeten GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by S&C Polymer Silicon und Composite Spezialitaeten GmbH filed Critical S&C Polymer Silicon und Composite Spezialitaeten GmbH
Publication of EP2180871A2 publication Critical patent/EP2180871A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
    • A61L24/001—Use of materials characterised by their function or physical properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/50—Preparations specially adapted for dental root treatment
    • A61K6/54—Filling; Sealing
    • 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

Definitions

  • the invention describes polymerizable compositions containing higher molecular weight di (meth) acrylates, curing agents and X-ray opacifying additives, resulting in cured, easily removable materials and being particularly suitable for filling and sealing root canals.
  • Root canal filling materials are used to fill in the prepared root canal. Preparations for these fillings are usually done "blindly”. This means that the result of preparatory measures and the filling itself are not directly visually assessable.
  • a disadvantage of most filling materials for root canal fillings is that they shrink when hardened in the root canal. This, in turn, can lead to shrinkage-induced gaps occurring. For example, secretions can penetrate into the tooth cavity from the apex of the root through these gaps, thereby creating a breeding ground for bacteria.
  • a root canal treatment the pulp tissue is first removed. Subsequently, the root canal lumen is treated with standardized instruments. Often the root canal is not filled immediately, but filled with an antimicrobial calcium hydroxide paste for a few days to weeks.
  • BESTATIGUNGSKOPIE The prepared root canal is fitted with a standardized gutta-percha point (conforming to the last instrument size of the reprocessing).
  • the seat of this pen (Masterpoint) is often checked by X-ray inspection.
  • the pin and / or the channel wall are coated with a root canal filling material and the pin is again introduced into the root canal.
  • any remaining gaps can be reduced by the subsequent insertion of needle-like condensation instruments.
  • the deformed pin and the filling material of the channel wall are adapted. Additional pins can be added to fill the often irregular channel wall. This procedure is very cumbersome.
  • a root canal filling sealant currently widely used is a material containing zinc oxide and eugenol as main components.
  • the zinc oxide / eugenol sealant composition for root canal filling can fill the space between the root canal wall and gutta-percha point, it does not have the adhesive properties for both root canal wall and gutta-percha point. Consequently, this is associated with the defect that the seals ability for the root canal is not sufficient from a clinical perspective.
  • eugenol has a harmful effect on living things and thus poses a security problem.
  • the glass ionomer cement When the glass ionomer cement is used as a sealant, not only are its adhesive properties for the gutta-percha stent and dentin high, but also its strength is high (the compressive strength is about 110 MPa). Consequently, when complications occur, it is difficult to remove the gutta-percha point and the glass ionomer cement when excising with a reamer or a file, because removal of the root canal filling with a bur can not be re-established without risk of canal wall penetration and its negative consequences. Therefore, there is often the case where tooth extraction becomes inevitable.
  • the root canal has a complicated shape and three to four root canals may be present depending on the type of tooth.
  • the shape includes various variations depending on the particular teeth, such as a flat shape, a cylinder shape or a curved shape.
  • Root filling materials are often introduced through a needle into the root canal. Due to the dimension of the needle (and the root canal), it is necessary that the material used be sufficiently low viscosity. Alternatively, root canal filling materials may be introduced with a Lentulo or gutta percha tip. Accordingly, the viscosity must be low enough that a film can form. In addition, there must be the possibility that the material can penetrate into the dentinal canals of the root canal.
  • WO 2002/13767 describes root canal filling materials which are constructed as a paste / paste system of addition-polymerizing equivalent amounts of low molecular weight diamines and low molecular weight diacrylates.
  • a reactive diluent is used here to regulate the viscosity.
  • Root canal filling materials based on primary monoamines and / or secondary diamines and diepoxides are distinguished by advantages such as a long processing time, a high radioopacity Endod. J. 2003, Jan. 36 (1): 54-63; Int. Endod. J. 1999 Sep. 32 (5): 415-418; Aust. Endod. J. 2001 Apr. 27 (1): 33-5; J. Endod. 1999 Mar. 25 (3): 172-7)].
  • Polyaminoesters as described in WO 2002/13767, are highly viscous and require the use of a not inconsiderable amount of a reactive diluent to lower the viscosity.
  • Such reactive diluents can not be polymerized by addition polymerization and require the presence of a polymerization initiator.
  • US 2002/0143108 discloses macromonomers obtained in a two-step reaction in the reaction of diepoxides with secondary diamines.
  • the intermediate prepolymer reacts in a second step with a 2,3-epoxypropyl (meth) acrylate and was not isolated. No further information has been published, which indicated that the prepolymer would be capable of providing an amino terminal prepolymer having a viscosity of ⁇ 100 Pas at 23 0 C.
  • the object of the present invention was to find root canal filling materials with sufficiently low viscosity, sufficiently long processing time and sufficient radiopacity for the controlled introduction into the root canal,
  • the composition fulfilling the object of the invention is very well suited as a root canal filling material and according to the invention is characterized in particular in that it one or more higher molecular weight di (meth) acrylates, one or more curing agents and one or more X-ray opacifying additives.
  • the composition is sufficiently thin-flowing prior to the polymerization and, after the polymerization, leads to well-sealable, easily spreadable moldings.
  • the root canal filling material according to the invention has the great advantage that an improved edge sealing of the root canal filling can be achieved by the lower polymerization shrinkage and the balanced hydrophilicity of the higher molecular weight monomers.
  • the volume behavior of the root canal filling material according to the invention is markedly improved.
  • acrylates which can be used as monomers according to the invention have e.g. the general formula (I) on:
  • R is a (meth) acrylic-free organic radical, a dimer, an oligomer or a polymer composed of up to 1000 monomeric units
  • R ' is a hydrogen, halogen, alkyl radical , preferably Cx-Cs-alkyl, substituted alkyl, preferably substituted Ci-C 6 -alkyl, or cyano radical
  • n is an integer from 1 to 6.
  • n 1
  • a lower polymerization rate can be achieved and thus a less solid material can be obtained, if desired.
  • R is an organic radical such as e.g. Alkyl, aryl, cycloalkyl or polyether, polyurethane, polyester, glycol, polyglycol, which may be substituted with carboxylic acid, phosphoric acid or other acids and their salts.
  • organic radical such as e.g. Alkyl, aryl, cycloalkyl or polyether, polyurethane, polyester, glycol, polyglycol, which may be substituted with carboxylic acid, phosphoric acid or other acids and their salts.
  • n 2, ie a diacrylate having the general formula (II):
  • R 1 and R 2 may independently be a hydrogen atom, a halogen atom, an optionally substituted alkyl group or a cyano group.
  • R1 and R2 are the same.
  • R 1 and / or R 2 are preferably a hydrogen atom or a C 3 -C 6 -alkyl group which may be optionally substituted by a hydroxyl group, a C 1 -C 6 -alkoxy group, an amino group or a halogen atom.
  • R 1 and / or R 2 are a hydrogen atom or a methyl group; most preferably R 1 and R 2 are a hydrogen atom or a methyl group, ie a di (meth) acrylate.
  • R is preferably an organic radical having an average molecular weight of at least 400.
  • R is preferably alkyl, alkoxyl, aryl, alkylaryl, alkoxylaryl, polyalkoxyl and polyalkoxyaryl, each of which may be substituted by one or more groups selected from alkyl, alkoxyl, polyalkoxyl, carboxyl and phosphate.
  • R particularly preferably has one or more polyalkoxy groups of the formula
  • x is an integer from 1 to 6, preferably 2, ie R contains one or more polyethylene groups, and y is an integer from 1 to 1000, preferably 1 to 200, more preferably 2 to 50, even more preferably 5 to 40, most preferably 10 to 30.
  • the root canal filling material of the invention may e.g. additionally dimeric and / or oligomeric and / or prepolymeric polyester and / or polyether (meth) acrylates, urethane (meth) acry- late and polyglycol (meth) acrylates and unsaturated polyesters.
  • Preferred polymerizable di (meth) acrylates according to the invention include e.g. Polyethylene glycol dimethacrylate with 10 to 30 ethylene oxide repeat units and / or ethoxylated bisphenol dimethacrylate with 10 to 30 ethylene oxide repeat units.
  • polyethyleneglycol 600 dimethacrylate (MW 754), polyethylene glycol 600 diacrylate (MW 770) from Cray Valley, polyalkylene glycol dimethacrylate EP100 DMA (MW 1114) from Bisomer, ethoxylated bisphenol A dimethacrylate E (IO) BADMA (MW 804) from bisomer, ethoxylated Bisphenol A dimethacrylate E (30) BADMiA (MVJ 1673), longer-chain aliphatic urethanedi acrylates, longer chain aliphatic urethane dimethacrylates, aliphatic polyester urethane diacrylates, aliphatic polyester urethane dimethacrylates, polybutadiene dimethacrylate, polymethylpolysiloxane dimethacrylate, or mixtures of these.
  • the mixtures according to the invention are formulated sufficiently thin for the application.
  • higher molecular weight di (meth) acrylates comprise at least 10, preferably 20 and more preferably 30 hydrophilic units.
  • the higher molecular weight di (meth) acrylates used should preferably have an average molecular weight of more than 600, preferably of at least 750. Preferably, they are contained in amounts of 2-90 weight percent, more preferably in amounts of 10-50 weight percent, most preferably in amounts of 15-30 weight percent in the polymerizable composition. Preference is given to di (meth) acrylates having hydrophilic units, for example -CH 2 -O- or -CH 2 -CH 2 -O- and / or OH-, NH 2 -, groups. Particularly preferred are -CH 2 -CH 2 -O- units.
  • di (meth) acrylates having a plurality of hydrophilic units are used. Preference is given to compounds having 10 hydrophilic units, more preferably having 20 hydrophilic units, very particularly preferably having 30 hydrophilic units.
  • the polymerizable composition according to the invention contains at least two different relatively high molecular weight di (meth) acrylates.
  • the (average) molecular weight of the present compounds is given as the weight-average molecular weight.
  • the polymerizable (meth) acrylates according to the invention may contain low-viscosity and / or high-viscosity, higher molecular weight di (meth) acrylates.
  • one or more lower molecular weight di (meth) acrylates may also be present in the compositions according to the invention in addition to the higher molecular weight di (meth) acrylates.
  • the lower molecular weight di (meth) acrylates have a molecular weight of less than 600, more preferably less than 400, and even more preferably less than 300.
  • composition (s) for adjusting the viscosity and / or the hydrophilicity according to the invention preferably have a viscosity of up to 100 mPas, preferably from 6 to 50 mPas.
  • the composition according to the invention can both be diluted and its necessary flexibility can be achieved.
  • Preferred lower molecular weight di (meth) acrylates are, for.
  • They are preferably present at less than 30 percent by weight, more preferably at less than 18 percent by weight in the composition.
  • the root filling material can be cold and / or polymerized by light.
  • one or more radical-providing systems such as e.g. Dibenzoyl peroxide or Bisdichlorbenzoylperoxid together with activators such.
  • Malonylsulfamide, as described in EP 00 59 451, or autoxidatively acting CH active compounds such as.
  • malonyl derivatives described in "Macromolecular Chemistry" 99 (1966) 96-102, dibenzoyl peroxide and / or malonyl derivatives are preferably used.
  • the curing agent (catalyst) for the photopolymerization there can be used, for example, benzophenone and its derivatives, as well as benzoin and its derivatives, or mixtures thereof. More preferred photosensitizers are diketones such as 9,10-phenanthrenequinone, diacetyl, furil, anisil, 4,4'-dichlorobenzil and 4,4'-dialkoxybenzil, camphorquinone, or mixtures thereof.
  • Camphorquinone is particularly preferably used Photosensitizers together with a reducing agent are preferred
  • reducing agents are amines such as cyanoethylmethylaniline, N, N-dimethyl-sym-xylidine and N, N-3, 5-tetramethylaniline and 4-dimethylaminobenzoic acid ester or mixtures thereof.
  • the root filling materials contain dual-curing curing systems, that is, they are cold-curing and additionally contain catalysts for light curing.
  • the amount of the polymerization catalysts in the dental material is usually from 0.001 to 5 weight percent, preferably from 0.1 to 3 weight percent.
  • the root filling material is preferably prepared as a two-component material, which cures cold after mixing and is additionally polymerizable by light.
  • the catalysts of the initiator systems described above are incorporated in separate pastes. By mixing both pastes, a composition is obtained which gives a sufficiently long working time and then cures slowly. The surface can be prematurely polymerized with light, so that above the filling with other materials such. B. can continue to work with methacrylate composites for butt structures or with conventional filling composites.
  • formulations are also suitable as one-component paste.
  • compositions of the invention contain X-ray opacifying additives, eg. Example as microfine metallic powders from the group zinc, ytterbium, yttrium, gadolinium, zirconium, titanium, strontium, tungsten, tantalum, niobium, barium, bismuth, molybdenum and tantalum or alloys thereof, and / or as their oxides, fluorides, sulfates , Phosphates, silicates, carbonates, tungstates and carbides and / or as mixtures or as described, for example, in US Pat. No. 3,925,895.
  • the X-ray opacifying additive or additives according to the invention are present in the range from 10 to 70% by weight, preferably from 30 to 50% by weight.
  • the surfaces of the X-ray opacifying additives and other auxiliaries should not be treated with a coupling agent (crosslinking agent), which inhibits the bond between the filler and the polymerizable resin increased.
  • a coupling agent crosslinking agent
  • the surfaces of the X-ray opacifying additives are not treated with a silanizing agent.
  • the surfaces of the X-ray opacifying additives according to the invention are not treated with, for example, trimethylsilane, methacryloxypropyltrimethoxysilane.
  • the root filling material according to the invention may also contain customary auxiliaries, such as, in particular, inert fillers such as dental glasses, quartz or aluminum oxide and / or ion-donating inorganic fillers and / or thixotropic filler additives, preferably silicic acid.
  • these fillers are not silanized for the purpose of the desired weaker mechanics of the root canal filling material.
  • non-(meth) acrylate-containing liquid, solid or waxy additives such as silicone oil, paraffin oil, vaseline, waxes, all-lyl tendency-containing compounds, saturated or unsaturated esters of di- or polybasic acids may also be included, if all these are sufficiently insoluble in the reacted or unreacted state.
  • the filler can also consist of prepolymerized filled and / or unfilled resins according to the invention.
  • the root canal filling material is prepolymerized and ground and then used as a filler in the root canal filling material.
  • disinfecting additives such as benzalkonium chloride, chlorhexidine, nanosilver or nano copper or devaluating additives.
  • ion-donating filler fillers As calcium, strontium or zinc glasses or oxides and / or carbonate, fluoride or phosphate-containing additives may be present. Examples of ion-donating glasses are, for. As glass powder as used in glass ionomer cements. Calcium-containing additives are z. As calcium carbonate, tricalcium phosphate and tetracalcium phosphate, calcium hydroxyapatite, Ca / Sr-Apatite, fluoroapatite or apatites as described in DE 102004025030 Al. Zinc oxide may preferably be used as the zinc-containing additive.
  • compositions according to the invention may contain at least one bioactive or remineralizing additive such as calcium hydroxide, calcium oxide, calcium fluoride, hydroxyapatite, fluorapatite or one or more other apatites.
  • bioactive or remineralizing additive such as calcium hydroxide, calcium oxide, calcium fluoride, hydroxyapatite, fluorapatite or one or more other apatites.
  • the surfaces of the ion-donating filler fillers are not silanized.
  • polymerizable or non-polymerizable acids may additionally be present, as in dental adhesives, dental compomers or dental resin-modified cements are common such.
  • These additives can improve adhesion to the root canal wall and / or the migration of ions.
  • amorphous silicon dioxide modifications are advantageous.
  • fumed and precipitated silicas and kieselguhr are particularly suitable.
  • agglomerated pyrogenic silicas or sintered silica gel as described in EP 0040232 and EP 0113926 (for example methyl silanized fumed silica).
  • These fillers have little tendency to thicken and have the characteristic that their thixotropic behavior is uniform and hardly depends on how quickly the processing takes place.
  • the root canal filling materials according to the invention are new and extremely advantageous. They can, for example, be filled into application capsules, mixed in commercial capsule mixers and applied directly into the root canal with a suitable attached application cannula. But they can also be filled in double cartridges or double syringes and mixed with attached mixing cannula and added directly into the root canal. They can be adjusted in sufficiently low viscosity and sufficiently long working time. Sufficient radiopacity allows accurate placement of the optionally introduced gutta-percha and root filling material. After curing, the strength is sufficient to withstand the required loads from the optional stump post or chewing loads.
  • the root fillings are hardly swelled or just a few percent by volume and, thanks to their high seal quality, are totally bacteria-proof. Thus, the occurring polymerization shrinkage can be compensated.
  • the water absorption is determined in accordance with standard ISO 4049.
  • compositions of the invention show a significantly lower compressive strength, which is determined according to the standard ISO 9917-1, of less than 50 MPa, more preferably less than 25 MPa, and thus significantly less than normal Fülungscomposit preparations (usually with clear over 200 MPa); Furthermore, in contrast to these, they show high ductility and cuttability.
  • the compositions according to the invention, used as root filling materials can easily be removed at any time with a root canal cutter and without piercing the root canal walls in the case of apical problems at the root tip. This is advantageous because tooth roots are often heavily bent. After eliminating the problem, the root canal can be closed without problems again with new material according to the invention.
  • the present invention relates in particular to a polymerizable composition
  • a polymerizable composition comprising a) from 10 to 50% by weight, particularly preferably from 15 to 30% by weight, of at least one relatively high molecular weight di (meth) acrylate, b) at least one curing agent, and b) 10 to 70 wt .-%, preferably 30 to 50 wt .-% of at least one X-ray opacifying additive.
  • the surfaces of the x-ray opacifying additives are not treated with a coupling agent (crosslinking agent) which increases the bond between the filler and the polymerizable resin.
  • the surfaces of the X-ray opacifying additives are not silanized.
  • compositions according to the invention show a very low solubility and are very well tolerated.
  • the compositions of the invention may remain as a root filling material temporarily (e.g., a few days), semipermanently (for months) or permanently in the root canal.
  • compositions of the invention are also excellent for use as a temporary cement for fixing crowns and bridges as well as for use as a material for provisional fillings of cavities.
  • the materials seal off bacteria and can be removed easily and without damaging the prepared tooth structure.
  • Both pastes are well flowable. After mixing, they cure with a working time of 8 minutes and a hardening time of 20 minutes. After 24 h, the following properties are measured:
  • the compressive strength is calculated according to the ISO standard 9917-1, the bending strength and the modulus of elasticity are determined according to ISO 4049.
  • the hardened material is very hard and can not be removed with a file or a hand instrument from a root canal. If mechanical drilling out is required, there can not be enough between the filling and the root canal wall. to be divorced.
  • the radiopacity with corresponding 1.9 mm aluminum is not sufficient for a clear diagnosis in the root canal. After several weeks of storage in water, marginal gaps between the filling and root canal wall are visible. A bacteria tightness can not be guaranteed.
  • Tetraethylene glycol dimethacrylate (short chain) 21 Ethoxylated bisphenol A dimethacrylate (2-4) BADMA (short chain) 21 Dimethyl p-toluidine 0.3
  • Tetraethylene glycol dimethacrylate (short chain) 21 Ethoxylated bisphenol A dimethacrylate (2-4) BADMA (short chain) 21 Dibenzoyl peroxide 0.5
  • the cured material is solid, but can be easily removed with a file or a hand instrument from a cavity. If necessary, a mechanical drilling out can be easily distinguished between filling and root canal wall.
  • the radiopacity with 5.5 mm aluminum is excellent for a diagnosis in the root canal. After several weeks of storage in water, there are no marginal gaps between the filling and the root canal wall. A bacteria tightness can be guaranteed.
  • composition of the present invention and the resulting polymerization product have the following advantageous properties: the composition is thin-flowing the non-surface-treated fillers result in a weaker mechanism (eg compressive strength of ⁇ 50 MPa) a very high radiopacity of> 400% Al is achieved easy fragility with a root canal file, the product is manually removable cuttability

Landscapes

  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Surgery (AREA)
  • Dental Preparations (AREA)
  • Sealing Material Composition (AREA)

Abstract

L'invention concerne des compositions polymérisables contenant des di(méth)acrylates de poids moléculaire élevé, des agents durcissants et des additifs opacifiants radiographiques. Lesdites compositions forment des matériaux durcis pouvant être retirés aisément, et sont particulièrement adaptées à l'obturation de canaux radiculaires.
EP08773702A 2007-06-26 2008-06-26 Matériau de remplissage de canal radiculaire Withdrawn EP2180871A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007029640A DE102007029640A1 (de) 2007-06-26 2007-06-26 Wurzelkanalfüllmaterial
PCT/EP2008/005227 WO2009000537A2 (fr) 2007-06-26 2008-06-26 Matériau de remplissage de canal radiculaire

Publications (1)

Publication Number Publication Date
EP2180871A2 true EP2180871A2 (fr) 2010-05-05

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP08773702A Withdrawn EP2180871A2 (fr) 2007-06-26 2008-06-26 Matériau de remplissage de canal radiculaire

Country Status (4)

Country Link
US (1) US20110053117A1 (fr)
EP (1) EP2180871A2 (fr)
DE (1) DE102007029640A1 (fr)
WO (1) WO2009000537A2 (fr)

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US20110053117A1 (en) 2011-03-03
WO2009000537A3 (fr) 2009-12-30
DE102007029640A1 (de) 2009-01-02

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