EP4312947A1 - Matériau de scellement de sillons autoadhésif - Google Patents

Matériau de scellement de sillons autoadhésif

Info

Publication number
EP4312947A1
EP4312947A1 EP22720599.4A EP22720599A EP4312947A1 EP 4312947 A1 EP4312947 A1 EP 4312947A1 EP 22720599 A EP22720599 A EP 22720599A EP 4312947 A1 EP4312947 A1 EP 4312947A1
Authority
EP
European Patent Office
Prior art keywords
meth
acrylate
weight
acid
urethane
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.)
Pending
Application number
EP22720599.4A
Other languages
German (de)
English (en)
Inventor
Maria Lechmann-Dorn
Michael Gerlach
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.)
Kulzer GmbH
Original Assignee
Kulzer GmbH
Kulzer and Co 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
Priority claimed from DE102021108477.6A external-priority patent/DE102021108477A1/de
Priority claimed from DE102021108476.8A external-priority patent/DE102021108476A1/de
Application filed by Kulzer GmbH, Kulzer and Co GmbH filed Critical Kulzer GmbH
Publication of EP4312947A1 publication Critical patent/EP4312947A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K6/50—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
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/62—Photochemical radical initiators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/76—Fillers comprising silicon-containing compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/71—Fillers
    • A61K6/77—Glass
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/70—Preparations for dentistry comprising inorganic additives
    • A61K6/78—Pigments

Definitions

  • Self-adhesive, radiation-curable fissure sealant comprising A) a monomer component with a) at least one difunctional urethane (meth)acrylate, b) at least one hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinkers, c) a mixture of acidic monomers of an olefinic carboxylic acid and/or an olefinic carboxylic acid anhydride in combination with an olefinic, acidic monoester of a phosphoric acid and/oran olefinic, acidic monoester of a thiophosphoric acid and d) an initiator and/or an initiator system each with an absorption maximum of 420 to 550 nm optionally with a co-initiator and B) a filler component comprising at least one dental glass, wherein A) the monomer component and B) the filler component are present in the fissure sealant in a mass ratio of 60:40 to 100:0, and
  • Fissure sealants are preventative products to minimize the risk of caries in deep fissures or in susceptible patients. Fissure sealants are polymerizable compositions that adhere to enamel.
  • the standard procedure for fissure sealing involves acid etching of the enamel followed by sealing with a low-viscosity flow material or glass ionomer cement - without the prior use of a bonding agent. Alternatively, suitable flow materials can be used in combination with an adhesive.
  • W00025729A1 fillers of a special shape are recommended for dental material and similar material.
  • the material can also contain customary glass fillers, pigments and X-ray opaque additives.
  • EP363095A2 describes fluoride-releasing materials suggested as an underfill material, among other things.
  • Example 9 describes an enamel sealant comprising 0.77% by weight PO2.
  • a similar fluoride donating material is described in GB2257433A.
  • DIN-ISO 6874 - 2015 regulates a curing depth of 1.5 mm polymerization depth for fissure sealants. Since a fissure sealant usually penetrates into fissures of freshly erupted molars or premolars and is intended to bring about chemical anchoring there, it is desirable for the depth of hardening and the chemical connection to the enamel to be further improved. Another challenge is that a self-adhesive fissure sealant should penetrate and chemically bond to untreated fissures in enamel. Untreated fissures are defined as fissures that have been cleaned but not previously etched. The object of the invention was to provide a dental, self-adhesive fissure sealant which binds adhesively to enamel with high adhesive strength.
  • the fissure sealant to be developed should preferably be usable without prior chemical treatment of the enamel or fissures, preferably without prior etching of the enamel or fissure surface. Furthermore, the fissure sealant should be applied to enamel without prior application of an adhesive. Another object was to provide a fissure sealant that further improves the hardening depth of the fissure sealant by means of radiation curing. The fissure sealant should also adhere to aprismatic enamel. This morphology is present in the enamel of deciduous teeth and deep pits of teeth. Furthermore, there was the task of developing a self-adhesive, opaque fissure sealant with reduced water absorption (g/mm 3 ) and/or reduced solubility (g/mm 3 ). In addition, there was the task of developing a Bis-GMA and HEMA-free fissure sealant, since an allergenic and mutagenic potential is ascribed to these monomers.
  • a fissure sealant according to the invention shows a shear bond strength on aprismatic enamel of 14.6 MPa, while the aforementioned products with a previous etching step exhibit shear bond strengths of 0.7 to 13.9 MPa under otherwise identical conditions (Helioseal F (13.6 MPA), Clinpro (10 .1 MPa), Grandio Seal (13.9 MPa), Ultra Seal XT Hydro (0.7 MPa)).
  • improved shear adhesion could be achieved through a specific combination of polymerizable acidic monomers in the fissure sealant directly with the application of the fissure sealant. Furthermore, by combining an increased content of initiator or initiator system in combination with a specific selection of reactive diluents, it has been possible to adjust the viscosity and at the same time the reactivity of the fissure sealant for optimal flow of the fissure sealant with improved curing or polymerisation at the same time. At the same time, the chemical connection to the enamel surface could be improved.
  • a self-adhesive fissure sealant offers the advantage of using the sealant on the tooth surface comprising enamel and optionally dentine without prior use of an adhesive system and etchant.
  • the fissure sealant according to the invention has a high level of adhesion due to the synergistic effect of the particularly coordinated monomers in the formulation and optionally in combination with the initiator system. Due to its self-etching properties, the fissure sealant intrinsically develops a very high adhesive strength on enamel. The achieved adhesive values are significantly higher than the values achieved by the competitor on the market. On untreated enamel, even after artificial aging, the fissure sealant shows a higher adhesion than the products of market competitors that provide for a prior etching step.
  • the shear bond strength of the fissure sealant according to the invention could be increased from the very good value of 16.3 [MPa] without an etching step to 21.1 [MPa] with an etching step, each measured after artificial aging (TWL, 5000 cycles).
  • the invention relates to a self-adhesive, radiation-curable, dental fissure sealant, in particular a fissure sealant that can be cured or polymerized with visible light, comprising A) a monomer component comprising a) at least one at least difunctional urethane (meth)acrylate, b) at least one hydrophilic alkylene oxide-based difunctional ( Meth)acrylate-based
  • Crosslinker which i) contains no urethane (meth)acrylate and/or ii) no aromatic residues, or a mixture of at least two of these crosslinkers, and/or c) acidic monomers, in particular a mixture of acidic monomers, comprising i) at least one olefinic Carboxylic acid and/or at least one olefinic carboxylic anhydride, in particular at least one carboxylic acid-functionalized and/or carboxylic anhydride-functionalized (meth)acrylate monomer, and ii) at least one olefinic, acidic ester of a phosphoric acid, in particular a monoester of a phosphoric acid and/or at least one olefinic, acidic ester of a thiophosphoric acid, in particular a monoester of a thiophosphoric acid at least one monoester of a phosphoric acid with a mono-, di-, tri- or tetra-(meth)acrylate
  • A) and B) are preferably present as a mixture in the fissure sealant.
  • the fissure sealant is preferably in the form of a flowable fissure sealing material which is readily visible as such and which can be distinguished from the hard tooth substance and hardens with visible light.
  • the aforementioned urethane (meth)acrylates also include urethane methacrylate and/or urethane acrylate as a (meth)acrylate component.
  • carboxylic anhydride-functionalized (meth)acrylate monomers also include the respective carboxylic anhydride-functionalized methacrylate and/or carboxylic anhydride-functionalized acrylate monomers.
  • the fissure sealant can comprise at least one white pigment, which is preferably present from 0.1 to 1.0% by weight in relation to the total composition.
  • the fissure sealant e) can contain at least one white pigment and optionally at least one dye, photochromic compound and/or a compound that changes color in the presence of free-radical compounds, which bleaches again over time.
  • a white pigment or synonymous white pigment are particularly suitable oxides with a high refractive index, such as titanium dioxide, Al 2 O 3 , ZrO 2 or ZnO. Titanium dioxide is preferred.
  • the white pigment is advantageously contained in the fissure sealant at 0.3-1.0% by weight.
  • fissure sealant is described here as a fissure sealant comprising a monomer component A) and a filler component B), these two components are present in the fissure sealant as a mixture.
  • This type of disclosure is known to the person skilled in the art in the dental field, since it only serves to characterize the two initially prepared components A) and B) before they are mixed to form the fissure sealant.
  • the fissure sealant is available as a ready-to-use mixture.
  • the monomer component A) and filler component B) can be mixed to produce the fissure sealant in a ratio of 60:40 to 100:0, in particular 60:40 to 80:20 or 90:10 to 100:0, preferably 90:10 to 99: 1, particularly preferred are 95:5 to 100:0.
  • filler-free fissure sealants are particularly preferred.
  • the initiator system preferably comprises an initiator such as a diketone and a co-initiator.
  • At least one initiator and/or one initiator system with an absorption maximum of 420 to 550 nm, each comprising at least one cycloaliphatic diketone and, as a co-initiator, an aromatic tert-amine.
  • the fissure sealant preferably comprises d) at least one initiator and/or an initiator system comprising i) diketone and ii) co-initiator which is selected from a tert-amine, which has a molar ratio of ii): i) of greater than or equal to 1.15 are present, and in particular wherein i) the diketone is present in an amount greater than or equal to 0.5% by weight, preferably greater than 0.4% by weight, in the overall composition of the dental material of 100% by weight.
  • the diketone is present in the fissure sealant in an amount of greater than or equal to 0.15% by weight, preferably greater than 0.2% by weight, particularly preferably greater than or equal to 0.3% by weight.
  • the fissure sealant in A) monomer component d) comprises 0.3 to 2.5% by weight of at least one diketone, in particular 1,7,7-trimethylbicyclo[2.2.1]hepta-2 ,3-dione (champhorquinone), and 0.6 to 2.5% by weight of at least one tert-amine, in particular 2-n-butoxyethyl 4-(dimethylamino)benzoate, based on the total composition of 100% by weight the A) monomer component.
  • the fissure sealant preferably comprises from 0.3 to 2.5% by weight of at least one diketone selected from 1,7,7-trimethylbicyclo[2.2.1]hepta-2,3-dione (champhorquinone), phenylpropanedione, and 0.6 to 2.5% by weight of at least one co-initiator selected from 2-n-butoxyethyl 4-(dimethylamino)benzoate and/or piperonyl alcohol, the mass ratio of diketone to co-initiator being from 1:1 .5 to 1:3, preferably 1:2 with +/- 0.15.
  • diketone selected from 1,7,7-trimethylbicyclo[2.2.1]hepta-2,3-dione (champhorquinone), phenylpropanedione
  • co-initiator selected from 2-n-butoxyethyl 4-(dimethylamino)benzoate and/or piperonyl alcohol
  • a fissure sealant is included with a
  • A) Monomer component comprising a) 40 to 80% by weight, in particular 50 to 80% by weight, of at least one at least difunctional urethane (meth)acrylate, b) 10 to 35% by weight, in particular 15 to 35% by weight , preferably 20% by weight with +/- 5% by weight, in particular with +/- 3% by weight, of at least one hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinker which i) does not contain any urethane (meth) acrylate and/or ii) no aromatic radicals, or a mixture of at least two of these crosslinkers, c) 5 to 30% by weight, in particular 10 to 20% by weight, of a mixture of acidic monomers as disclosed, d) 0.3 up to 5% by weight, in particular 0.3 to 3% by weight, of at least one initiator and/or an initiator system each having an absorption maximum of 420 to 550 nm, the content of the at least one diketone being 0.
  • a filler component comprising a) 90 to 100% by weight of at least one dental glass or a mixture of dental glasses, b) 0 to 10% by weight, in particular 5 to 10% by weight, of inorganic fluoride, preferably ytterbium fluoride, metal oxide, such as S1O2, ZrÜ2, and mixed oxides, in particular mixed oxides of S1O2 and ZrÜ2, b) 0 to 1.0% by weight, in particular 0.1 to 0.5% by weight, at least one pigment selected from titanium dioxide, and optionally a dye , UV and/or Vis stabilizer, and wherein A) the monomer component and B) the filler component are present in the fissure sealant in a mass ratio of 60:40 to 100:0, and the total composition of the fissure sealant is 100% by weight. It is preferred here if the content of at least one white pigment is from 0 to 1.0% by weight, preferably from 0.1 to 1.0% by weight, based on the
  • component b) of the hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinker can be present in the monomer component as a mixture of at least two hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinkers.
  • Ethers and esters of di- to polyols with (meth)acrylic acids are generally considered to be alkylene oxide-based difunctional (meth)acrylate-based crosslinkers, i.e. as alkylene oxide-based difunctional methacrylate-based crosslinkers or alkylene oxide-based difunctional acrylate-based crosslinkers.
  • (Meth)acrylate is also understood here to mean methacrylate or acrylate monomers.
  • PEGDA polyethylene glycol diacrylate
  • PPGDA polyprop
  • difunctional urethane (meth)acrylate preferably
  • fissure sealants comprise the monomer component A) or a mixture of monomer component A) and filler component B), the fissure sealant comprising a) 25 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, in particular 30 to 75% by weight. %, b) 8 to 20 wt two of these crosslinkers, c) 3 to 20 wt.
  • filler component comprising at least one dental glass or a mixture of dental glasses, in particular a dental glass content of up to 40% by weight, the overall composition of the fissure sealant being 100% by weight.
  • the weight ratio of the acidic monomers i) to ii) is preferably from 1:1 to 2:1, more preferably from 5:4 to 5:2, particularly preferably from 5:4 to 5:3.
  • the weight ratio of dental glasses with particle sizes from 0.8 to 2.5 microns and particle sizes from 0.1 to 0.8 microns is preferably from 4:1 to 1:1, preferably from 3:1 to 1.5:1.
  • the content of acidic monomers can preferably include c) 8 to 20% by weight of a mixture of acidic monomers comprising i) at least one olefinic carboxylic acid and/or at least one olefinic carboxylic acid anhydride, in particular 1.5 to 8% by weight, in combination with ii) at least one olefinic, acidic ester of a phosphoric acid and/or at least one olefinic, acidic ester of a thiophosphoric acid, in particular 6.5 to 12% by weight.
  • a fissure sealant comprising the monomer component A) or a mixture of monomer component A) and filler component B), the fissure sealant comprising a) 30 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) 8 to 16 Wt up to 15 wt , acid ester of a thiophosphoric acid, in particular at least one monoester of phosphoric acid of the formula I and/or II, or a mixture of i) and ii), d) 0.8 to 3 wt % at least one initiator system each having an absorption maximum of 420 to 550 nm and comprising a diketone and at least one co-initiator selected from a tert-amine and a 1,2-methylenedioxybenzene, and optionally
  • filler component comprising at least one dental glass or a mixture of dental glasses, the total composition of the fissure sealant being 100% by weight.
  • Pentapropylene Glycol Diacrylate Hexapropylene Glycol Dimethacrylate, Hexapropylene Glycol Diacrylate, Hepta(propylene Glycol) Dimethacrylate, Hepta(propylene Glycol) Diacrylate, Octapropylene Glycol Dimethacrylate, Octapropylene Glycol Diacrylate, Nonapropylene Glycol Dimethacrylate,
  • PPGDA polypropylene glycol diacrylate
  • PEGDMA polyethylene glycol dimethacrylate
  • a) at least one at least difunctional urethane (meth)acrylate is preferably selected from difunctional urethane (meth)acrylate with a divalent alkylene group, including difunctional urethane (meth)acrylates with a linear or branched divalent alkylene group with 3 up to 20 carbon atoms, urethane dimethacrylate functionalized ether with linear or branched bivalent alkylene group with 3 to 20 carbon atoms, urethane dimethacrylate functionalized polyether with linear or branched bivalent alkylene group with 3 to 20 carbon atoms, urethane diacrylate Oligomer, preference is given to bis(methacryloxy-2-ethoxycarbonylamino)-alkylene and/or bis(methacryloxy-2-ethoxycarbonylamino)-substituted alkylene ethers, particular preference being given to 1,6-bis(methacryloxy-2-ethoxycarbonylamino)-2,
  • the difunctional urethane (meth)acrylate with a divalent alkylene group is preferably selected from linear or branched urethane dimethacrylates functionalized with a divalent alkylene group, urethane dimethacrylate-functionalized ethers or polyethers with alkylene group(s), such as bis(methacryloxy-2-ethoxycarbonylamino) - Alkylene, bis (methacryloxy-2-ethoxycarbonylamino) substituted polyalkylene ether, preferably 1, 6-bis (methacryloxy-2-ethoxycarbonylamino) -2,4,4-trimethylhexane.
  • alkylene group(s) such as bis(methacryloxy-2-ethoxycarbonylamino) - Alkylene, bis (methacryloxy-2-ethoxycarbonylamino) substituted polyalkylene ether, preferably 1, 6-bis (methacryloxy-2-ethoxycarbonylamino) -2,4,4-trimethyl
  • a bis(methacryloxy-2-ethoxycarbonylamino)-alkylene is preferred, where alkylene comprises linear or branched C3 to C20, preferably C3 to C6, such as particularly preferably an alkylene substituted with methyl groups, such as HEMA-TMDI.
  • the divalent alkylene preferably includes 2,2,4-trimethylhexamethylene and/or 2,4,4-trimethylhexamethylene.
  • UDMA (1,6-bis(methacryloxy-2-ethoxycarbonylamino)-2,4,4-trimethylhexane), especially HEMA-TDMI.
  • the subject of the invention is also a fissure sealant, which preferably comprises: b) at least two hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinkers, each selected from the combinations i) and ii) or i) and iii) or i) , ii) and iii), b) at least one mono-, di-, tri-, tetra-, polyfunctional alkylene oxide-based difunctional (meth)acrylate-based crosslinker is particularly preferred, i) 1,2-ethanediol dimethacrylate, diethylene glycol dimethacrylate ( DEGMA), triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate, propylene glycol dimethacrylate, 1,2- ethanediol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, tetraethylene glycol diacrylate, propylene glycol diacrylate,
  • the fissure sealant can include: b) at least one tri-, tetra-, penta- and/or hexa-functional (meth)acrylate-based crosslinker that is not a urethane (meth)acrylate and is selected from (i) with three (meth) -) acrylate groups from trimethylolpropane trimethacrylate, ethoxylated (15)-trimethylolpropane triacrylate, ethoxylated 5-pentaerythritol triacrylate, propoxylated (5.5)-glyceryl triacrylate, trimethylolpropane trimethacrylate, and/or (ii) with four ( Meth)acrylate groups from di-trimethylolpropane tetraacrylate, ethoxylated-(4)-pentaerythritol tetraacrylate, pentaerythritol tetraacrylate, di-trimethylolpropanetetrame
  • the c) mixture of the acidic monomers preferably comprises i) at least one olefinic carboxylic acid and/or at least one olefinic carboxylic acid anhydride, comprising, in particular selected from, maleic acid, p-vinylbenzoic acid, 11-(meth)acryloyloxy-1,1-undecanedicarboxylic acid (MAC- 10), 1,4-di(meth)acryloyloxyethyl pyromellitic acid, 6-(meth)acryloyloxyethylnaphthalene-1,2,6-tricarboxylic acid, 4-(meth)acryloyloxymethyl trimellitic acid and anhydrides thereof, 4-(meth)acryloyloxyethyl trimellitic acid and its anhydride, 4-(meth)acryloyloxybutyltrimellitic acid and its anhydride, 4-[2-hydroxy-3-(meth)acryloyloxy]butyltrimellitic acid and its an
  • a particularly preferred fissure sealant contains c) acidic monomers, especially a mixture of acidic monomers, including, especially selected from i) 4-methacryloyloxyethyl trimellitic acid (4-MET) and/or its anhydride (4-META), and ii) acidic(s).
  • Monoester(s) of at least one phosphoric acid comprising at least two urethane (meth)acrylate groups, in particular where at least two urethane (meth)acrylate groups are bonded by means of a group containing at least one trivalent carbon atom and optionally O atoms, in particular -0H 2 CC( -0-)-CH 2 0 ⁇ group covalently bonded to an O-atom of phosphoric acid and forming the monoester of phosphoric acid, wherein the urethane (meth)acrylate groups are independently selected from urethane methyl acrylate and urethane acrylate groups, 2- Methacryloyloxyethylphenyl acid phosphate, 10-
  • Methacryloyloxydecyl acid phosphate 2-acryloyloxyethylphenyl acid phosphate and/or 10-acryloyloxydecyl acid phosphate and mixtures comprising at least two of the aforementioned monoesters.
  • At least two urethane (meth)acrylate groups are covalently bonded via an O atom each to a group comprising a quaternary C atom and at least one monoester of a phosphoric acid.
  • the group comprising a trivalent or quaternary carbon atom preferably comprises 3 to 6 carbon atoms, in particular the respective urethane (meth)acrylate group and the monoester of phosphoric acid can be covalently bonded to the group independently via a polyalkylene oxide group.
  • Polyalkylene oxide includes polyethylene oxide, polypropylene oxide, polyalkylene oxide groups comprising propylene oxide and ethylene oxide groups, blocks of polypropylene oxide and polyethylene oxide.
  • the remaining groups can be selected from at least two formulas from IV, V, VIA and/or VIla.
  • one radical preferably corresponds to the radicals R 1 , R 2 and R 3 of the formula III and the remaining radicals each correspond to a group of the formula IV, V, VIA or VI la, preferably the remaining radicals are selected accordingly R 1 , R 2 and R 3 are identical groups of the formulas IV, V, Via or VI la. More preferably, R 2 corresponds to the formula III and the remaining are identical groups selected from the formulas IV, V, VIA, VI la, IV is preferred.
  • a preferred monoester corresponds to the formula I with R 2 the same as formula III and R 1 and R 2 equal to formula IV or VIIa.
  • R 1 , R 2 and R 3 correspond to a group of the formula III, IIIb and/or IIIa and the or the remaining radicals of R 1 , R 2 and R 3 are selected from at least one group of the formulas IV, V, Via, VIb, VIIa, VI Ib, Villa and/or VIIlb, where R 4 and R 5 are each independently in the groups of the formulas IV, V, Via , VIlb, VIIa, VIIb, Villa and VIIlb are selected from H, methyl and ethyl, in particular the remaining groups are selected from at least two formulas from IV, V, Via, VIIb, VIIa, VIIb, Villa and/or VIIlb, and
  • R 6 is independently selected from H and methyl in the groups of the formulas Ia, Ib, IIIa, IIIb, Villa and VIIIb,
  • m 0 or 1 to 100 in formulas VIIIa and/or VIIIb, in particular 1 to 20, with R 6 being selected from H and methyl.
  • n is preferably 1 to 10, particularly preferably 1
  • MAC-10 11-(meth)acryloyloxy-1,1-undecanedioic acid
  • Meth acrylates particular preference being given to the monoesters of phosphoric acids of the formulas I and II, 2-(meth)acryloyloxyethylphenyl acid phosphate and/or 10-(meth)acryloyloxydecyl acid phosphate.
  • the content of the acidic monomers MDP and 4-META and/or 4-MET in the monomer component can be very low and very good adhesion values are nevertheless achieved with the fissure sealant according to the invention.
  • the MDP content can be about 4 to 5% by weight and the 4-META and/or 4-MET content can be about 2% by weight in the monomer component, with adhesion to dentine (cattle tooth) preferably being ensured in the range from 16 to 21 MPa and on enamel (cattle tooth) in the range from 4 to 21 MPa (DIN:ISO 29022).
  • the fissure sealant which is colored bright white, since such a material is only used in a thin layer. Because if such a demarcation material had the same opacity as a conventional flow composite, it would not be visible on the hard tooth substance, or only insufficiently so, despite its white color.
  • the setting of a correspondingly high opacity is technically not a problem in principle, the subsequent light-curing of the material becomes problematic with increasing opacity. The more opaque a light-curing material is, the smaller the layer thickness that can be polymerized in one polymerization cycle.
  • the fissure sealant in the A) monomer component can comprise at least one monofunctional (meth)acrylate-based monomer, with the exception of 2-hydroxyethyl methyl acrylate (HEMA).
  • HEMA 2-hydroxyethyl methyl acrylate
  • suitable monofunctional (meth)acrylate-based monomers include aromatic vinyl compounds such as styrene and divinylbenzene, vinyl esters such as vinyl acetate, aliphatic esters of (meth)acrylic acid such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate.
  • filler component preferably at least one a) dental glass or a mixture of dental glasses, and b) optionally comprising at least one inorganic fluoride and/or amorphous metal oxide, mixed oxide, crystalline metal oxide, silicate, are used in the fissure sealant, with a) comprising at least one dental glass Aluminosilicate glasses or fluoroaluminosilicate glasses, barium aluminum silicate, barium aluminum borofluorosilicate, strontium silicate, strontium borosilicate, lithium silicate and/or lithium aluminum silicate, dental glasses containing ytterbium fluoride and mixtures of at least two of the aforementioned dental glasses, and b) includes ytterbium fluoride, amorphous spherical fillers based on oxide or mixed oxides, such as amorphous S1O2, ZrÜ2 or also mixed oxides of S1O2 and ZrÜ2, quartz, feldspar, pyrogenic or precipitated silica,
  • the fillers can all preferably be silanized.
  • Common silanizing agents include (meth)acryloyloxypropyltrimethoxysilane and (meth)acryloyloxypropyltriethoxysilane or (meth)acryloyloxymethyltrimethoxysilane and (meth)acryloyloxymethyltriethoxysilane.
  • the dental fissure sealant comprises at least one dental glass and/or mixtures thereof, in particular a radiopaque dental glass or mixtures thereof, with an average particle size dso of 0.2 to 5.0 mhi, preferably with dso of 0.2 to 2.0 mGh, preferably with an average particle size of 0.2 to 1.75 mhi, in particular with dso of 1.0 mhi, optionally plus/minus 0.6 mhi.
  • a particularly preferred dental glass comprises barium aluminum borosilicate glass, in particular barium aluminum borosilicate.
  • a barium aluminum silicate glass with a refractive index of n 1.52 to 1.55, preferably 1.53.
  • the invention also relates to a dental fissure sealant comprising a filler component comprising at least one dental glass or a mixture of dental glasses comprising barium aluminum borosilicate glass, barium aluminum borofluorosilicate glass, in particular silanized, preferably functionalized with methacryloxypropyl groups and optionally at least one non-agglomerated amorphous metal oxide with a primary particle size of 2 to 45 nm , wherein the amorphous metal oxide comprises precipitated silicon dioxide, zirconium oxide, mixed oxides or mixtures of these, in particular the metal oxides are silanized.
  • the diketone is preferably a 1,7,7-trimethylbicyclo[2.2.1]hepta-2,3-dione (champhorquinone), phenylpropanedione, benzoyltrimethylgermane (BTMGe) and/or dibenzoyldiethylgermane (DBDEGe ), and the co-initiator preferably comprises 2-n-butoxyethyl-4-(dimethylamino)benzoate and/or as 1,2-methylenedioxybenzene piperonyl alcohol (1,2-methylenedioxybenzene-4-methanol).
  • tert-amines may include 2-(ethylhexyl)-4-(N,N-dimethylamino)benzoate, dimethylaminobenzoic acid ester, triethanolamine, N,N-3,5-,N,N-3,5-tetramethylaniline, 4 - (dimethylamino)phenylethyl alcohol, dimethylaminobenzoic acid ester, 4-(N,N-
  • the fissure sealant contains from 0.2 to
  • At least one further pigment, a dye, and in particular at least one UV and/or Vis stabilizer comprising 2-hydroxy-4-methoxybenzophenone can be present both in the monomer component and/or in the filler component.
  • the pigment is assigned to the filler component with its content.
  • the c) acidic monomers in particular the mixture of acidic monomers, preferably comprises i) at least one olefinic carboxylic acid and/or the at least one olefinic carboxylic anhydride, preferably at least one carboxylic acid-functionalized and/or carboxylic anhydride-functionalized (meth)acrylate monomer, and ii ) at least one olefinic, acidic ester of phosphoric acid, in particular a monoester of phosphoric acid, and/or at least one olefinic, acidic ester of thiophosphoric acid, in particular a monoester of thiophosphoric acid, preferably at least one monoester of phosphoric acid and a (meth)acrylate, monoester of phosphoric acid and a urethane (meth)acrylate, in particular at least one monoester of phosphoric acid of the formula I and/or II, and/or at least one monoester of a Thiophosphoric acid and a (me
  • a fissure sealant preferably comprises c) a mixture of acidic monomers comprising i) at least one olefinic carboxylic acid and/or at least one olefinic carboxylic acid anhydride, in combination with ii) at least one olefinic, acidic ester of a phosphoric acid, in particular of the formula I and/or II, and/ or at least one olefinic, acidic ester of a thiophosphoric acid, i) and ii) being present in a weight ratio of from 1:1 to 2:1, in particular from 7:6 to 5:2, preferably from 5:4 to 5:2.
  • the fissure sealant in the A) monomer component in c) as i) comprises 2 to 10% by weight, in particular 3.75 to 10% by weight, of at least one olefinic carboxylic acid and/or the at least one olefinic carboxylic acid anhydride, preferably at least one carboxylic acid-functionalized and/or carboxylic anhydride-functionalized (meth)acrylate monomer, and as ii) 4 to 20% by weight, in particular 9.5 to 20% by weight, of at least one olefinic, acidic ester of a phosphoric acid and /or at least one olefinic, acidic ester of a thiophosphoric acid, preferably at least one monoester of a phosphoric acid and a (meth)acrylate, monoester of a phosphoric acid and at least one urethane (meth)acrylate, in particular monoester of phosphoric acid of the formula I and/or II, and/or at least one mono
  • a fissure sealant contains A) the monomer component optionally mixed with B) the filler component, the fissure sealant comprising a) 30 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) 8 to 20% by weight % at least one hydrophilic alkylene oxide-based difunctional (meth)acrylate-based crosslinker which i) does not include any urethane (meth)acrylate and/or ii) does not contain any aromatic radicals, or a mixture of at least two of these crosslinkers, c) i) 2 to 10% by weight of at least one olefinic carboxylic acid and/or at least one olefinic carboxylic anhydride, in particular at least one carboxylic acid-functionalized and/or carboxylic anhydride-functionalized (meth)acrylate monomer, and ii) 4 to 20 wt )acrylate and/or at least one monoester of a thi
  • At least one co-initiator selected from tert-amine and 1,2-methylenedioxybenzene particularly selected from 2-n-butoxyethyl 4-(dimethylamino)benzoate and/or piperonyl alcohol, wherein the mass ratio of diketone to co-initiator selected from tert-amine or 1,2-methylenedioxybenzene is from 1:1.5 to 1:3, e) 0 to 1% by weight of at least one pigment comprising titanium dioxide, and 0 to 2 % by weight dye, UV and/or Vis stabilizer, and f) 0 to 30% by weight of at least one dental glass, in particular a content of up to 30% by weight, g) 0 to 10% by weight inorganic Fluoride, such as ytterbium fluoride, metal oxide, mixed oxides and/or silicates, h) 0 to 1% by weight, in particular 0.1 to 0.5% by weight, of at least one pigment comprising titanium dioxide, and 0
  • a fissure sealant which comprises as A) monomer component comprising a) 50 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) 10 to 35% by weight, in particular 15 to 25% by weight , at least one hydrophilic alkylene oxide-based difunctional (meth) acrylate-based crosslinker, which i) no urethane (meth) acrylate and / or ii) comprises no aromatic radicals, or a mixture of at least two of these crosslinkers, and / or
  • a filler component comprising a) 90 to 100% by weight of at least one dental glass or a mixture of dental glasses, b) 0 to 10% by weight, in particular 5 to 10% by weight, of inorganic fluoride, such as ytterbium fluoride, metal oxide, such as S1O2, mixed oxides, silicates, quartz, feldspar and/or mixtures thereof, c) 0 to 1% by weight, in particular 0.1 to 0.5% by weight, of at least one pigment comprising titanium dioxide, and optionally 0 to 2 Wt
  • the fissure sealant is present in a mass ratio of from 60:40 to 100:0, and the total composition of the fissure sealant is 100% by weight.
  • the invention also relates to a fissure sealant with an A) monomer component which comprises a) 50 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) 10 to 35% by weight, in particular 15 to 25 wt preferably at least one di- to poly-alkylene oxide-based difunctional (meth)acrylate-based crosslinker, c) i) 2 to 10% by weight, in particular 3.75 to 10% by weight, of 4-(methacryloyloxyethyl) - trimellitic anhydride (4-META) and/or 4-methacryloyloxyethyl trimellitic acid (4-MET) and ii) 4 to 20% by weight, in particular 9.5 to 20% by weight, of monoesters of phosphoric acid of formula I and/or II , 2-(meth)acryloyloxyethylphenyl acid phosphate and/or 10-(meth)acryloylo xylec
  • B) a filler component comprising a) 90 to 100% by weight of at least one dental glass, b) 0 to 10% by weight, in particular 5 to 10% by weight, of inorganic fluoride, such as ytterbium fluoride, metal oxide, such as S1O2, mixed oxides, silicate, c) 0 to 0.5% by weight of at least one pigment comprising titanium dioxide and 0 to 2% by weight of dye, UV and/or Vis stabilizer, and/or
  • inorganic fluoride such as ytterbium fluoride, metal oxide, such as S1O2, mixed oxides, silicate
  • Another particularly preferred fissure sealant comprises as A) a monomer component which comprises a) 50 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) at least one hydrophilic alkylene oxide-based difunctional (meth)acrylate Crosslinker selected from i) and ii) or i) and iii) or i), ii) and iii), with i) 5 to 15% by weight of 1,2-ethanediol dimethacrylate, diethylene glycol dimethacrylate
  • DEGMA triethylene glycol dimethacrylate
  • TEGDMA triethylene glycol dimethacrylate
  • tetraethylene glycol dimethacrylate propylene glycol dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate dipropylene glycol diacrylate
  • B) comprising a filler component a) 90 to 100% by weight of at least one dental glass or a mixture of dental glasses, b) 0 to 10% by weight, in particular 5 to 10% by weight, of inorganic fluoride such as ytterbium fluoride, metal oxide such as S1O2, mixed oxides, crystalline metal oxide, silicate, c) 0 to 0.5% by weight of at least one pigment comprising titanium dioxide, and 0 to 2% by weight of dye, UV and/or Vis stabilizer, and/or mixtures of at least two fillers, and wherein the total composition of the filler components is 100% by weight, and/or a mixture of at least two of the fillers, and wherein the total composition of the filler component is 100% by weight, and wherein A) the monomer component and B) the filler component in the mass ratio from 60:40 to 100:0 are present in the fissure sealant and wherein the total composition of the fissure sealant is 100% by weight.
  • inorganic fluoride such as yt
  • a fissure sealant in particular comprising A) the monomer component optionally in a mixture with B) the filler component, the fissure sealant comprising a) 30 to 80% by weight of at least one at least difunctional urethane (meth)acrylate, b) 8 to 20 Wt ) 2 to 10% by weight of at least one olefinic carboxylic acid and/or at least one olefinic carboxylic anhydride, in particular at least one carboxylic acid-functionalized and/or carboxylic anhydride-functionalized (meth)acrylate monomer, and ii) 4 to 20% by weight at least an olefinic, acidic ester of a phosphoric acid and/or at least one olefinic, acidic ester of a thiophosphoric acid, in particular at least one monoester r phosphoric acid and a (meth)acrylate, monoester of a phosphoric acid and a urethane (meth)acrylate and
  • At least one co-initiator selected from tert-amine and 1,2-methylenedioxybenzene particularly selected from 2-n-butoxyethyl 4-(dimethylamino)benzoate and/or piperonyl alcohol, wherein the mass ratio of diketone to co-initiator selected from tert-amine or 1,2-methylenedioxybenzene is from 1:1.5 to 1:3, e) 0 to 1% by weight of at least one pigment comprising titanium dioxide, and 0 to 2 % by weight of dye, UV and/or Vis stabilizer, and f) 0 to 30% by weight of at least one dental glass, in particular 1 to 30% by weight, preferably 10 to 30% by weight, g) 0 to 10% by weight of inorganic fluoride, such as ytterbium fluoride, in particular ytterbium(III ) fluoride, metal oxide, mixed oxides and/or silicates, h) 0 to 1% by weight, inorganic fluoride, such as
  • compositions specified in which the contents of the components are mentioned, the contents which are mentioned behind in particular are to be understood as belonging together; the same applies in subgroups for the contents mentioned there as preferred.
  • the disclosure is also to be understood in connection with the non-exhaustive examples and is aimed at the chemist or materials scientist.
  • the invention also relates to a polymerised, dental fissure sealant obtainable by polymerisation, in particular by polymerisation by means of visible light, of a fissure sealant, in particular the polymerised fissure sealant has a shear bond strength to untreated bovine tooth enamel and to ground bovine tooth enamel of greater than or equal to 11 MPa, in particular greater than or equal to 13 MPa, preferably greater than or equal to 15 MPa, particularly preferably greater than or equal to 17 MPa, further preferably greater than or equal to 19 MPa, preferably greater than or equal to 22 MPa, particularly preferably greater than or equal to 23 MPa.
  • the fissure sealant comprising A) 80 to 100% by weight monomer component and B) 0 to 20% by weight filler component with a total composition of 100% by weight has a shear bond strength of greater than or equal to 15 MPa, preferably greater equal to 17 MPa, particularly preferably greater than or equal to 18 MPa, in particular on unpolished bovine tooth enamel after thermocycling and preferably without a separate etching step having a composition deviating from the fissure sealant being applied to the unpolished enamel before the application of the fissure sealant, i.e. not on pre-etched ox tooth enamel.
  • the subject matter of the invention is also the use of a hardenable or polymerizable dental fissure sealant for radiation-hardening, self-adhesive adhesion to dentin and/or enamel of teeth, in particular human or veterinary teeth.
  • Radiation curing preferably takes place by means of visible light (Vis radiation), preferably in the wavelength range from 420 to 500 nm, preferably at 485 nm. Suitable light sources are LED lamps.
  • the invention also relates to a self-adhesive, radiation-curable, dental fissure sealant or self-adhesive, polymerized, in particular radiation-cured, fissure sealant for use in sealing fissures in enamel and/or dentin with very fine fissures and/or horn, such as hooves, or for use for radiation-curing, self-adhesive adhesion to substrates comprising inorganic glass, PMMA, ceramics, hybrid ceramics, metals and/or alloys, etc., to dentine and/or enamel of teeth, in particular human or veterinary teeth, and/or as a base material.
  • the shear bond strength is measured according to DIN EN:ISO 29022 (2013).
  • Bovine tooth enamel and/or dentin surfaces were prepared on 120-320 grit SiC paper. In the case of the "uncut" surfaces, mechanically cleaned bovine tooth enamel surfaces are used as the adhesive surface (Sof-Lex discs from 3M).
  • the fissure sealant is massaged onto the tooth substrate and exposed to light for 10 s with a Tranzlux Wave (Kulzer GmbH, spectrum: 440 to 480 nm, power density 1200 milliwatts/cm 2 ). The material is then filled into cylindrical plastic molds (Ultradent equipment) and cured for 20 s.
  • TWC thermal cycle, thermal change bath
  • RZS / RZD are the 24-hour measurements.
  • RZD bovine dentine
  • the flexural strength and the flexural modulus of elasticity are determined according to DIN ISO standard 4049 (polymer-based filling, restoration and fixing materials, measurements at room temperature, 2019).
  • the water absorption/solubility is determined according to DIN-ISO 4049 Section 7.12 to 4 to 8 test specimens with a diameter of 15 mm and a width of 1 mm are hardened, dried, stored in H2O at 37 °C for 7 days and dried again.
  • the film thickness of the fissure sealant is determined according to DIN-ISO 4049 7.5. The material is loaded between 2 glass plates with 150 N for 180 s, hardened and the difference is measured with an outside micrometer.
  • the hardness is determined as follows: Harden the 10 mm Delrin mold/Teflon mold test specimen for 20 s on the upper side (OS). Mark underside (US). Store in H2O for 24 h at 37 °C, grind flat and determine the penetration force (N/mm 2 )/penetration depth of the top/bottom with Zwick universal hardness using a diamond.
  • alkylene oxide-based difunctional methacrylates used in the following examples such as TEGDMA, PEGDMA or DDDMA (dodecanediol dimethacrylate), particularly in preferred alternatives due to the combination of these and/or due to the content in the non-polymerized state of the fissure sealant, cause good flow the enamel and penetration into fissures and thus the high adhesive strength after radiation curing. Adhesion to the enamel occurs without prior etching of the enamel.
  • the concentration of the initiator system in the fissure sealant is also crucial, since a high conversion of crosslinking during polymerisation also results in good adhesion to the substrate, in this case enamel.
  • the content of the combination of camphorquinone (CQ)/tertiary amine (2-n-butoxyethyl)-4-(dimethylamino)benzoate, BEDB) should be greater than 0.3%/greater than 0.6% by weight as the initiator system in the monomer component, preferably in the overall composition of the fissure sealant.
  • Table 1 shows the shear bond strength values achieved on ground cattle tooth enamel (RZS), unpolished enamel (RZS-unpolished/RZS-uncut) after a thermal change bath (TWL) in otherwise qualitatively and quantitatively identical fissure sealants with a filler content of 40 wt. -% shown (measurement according to ISO 29022 in MPa).
  • RZS ground cattle tooth enamel
  • RZS-unpolished/RZS-uncut after a thermal change bath
  • Particle sizes of the fillers The particle sizes are determined using laser diffraction.
  • the particle size is usually determined by means of laser diffraction with the Cilas device or alternatively Horiba LA-950 (Retsch) or DT1200 (Dispersion Technology). Unsilanized fillers are measured in (distilled) water and silanized fillers are measured in isopropanol.
  • the accuracy with particle sizes of 1.5 microns or D50 1.5 microns is also at least in this range. List of abbreviations:
  • the shear bond strength on enamel is 9.0 MPa in the first case and after TWL 17.1 MPa and in the second case with even lower concentration only 6.3 MPa (24h) and 7.8 MPa after TWL.
  • 4-META (4-methacryloyloxyethytrimellitic acid anhydride) in combination with a phosphoric acid-containing monomer such as MDP (10-methacryloyloxydecyl dihydrogen phosphate) significantly increases enamel adhesion.
  • High shear bond strengths can also be achieved with fissure sealants containing a combination of acidic monomers of carboxylic acids or carboxylic acid anhydrides with acidic esters of phosphoric acid and two different alkylene oxide-based difunctional methacrylates including TEGDMA and PEGDMA (polyethylene glycol dimethyl acrylate), TEGDMA and polyethylene glycol diacrylate, or TEGDMA and DDDA be achieved.
  • TEGDMA and PEGDMA polyethylene glycol dimethyl acrylate
  • TEGDMA and DDDA polyethylene glycol diacrylate
  • the propylene glycol diacrylate-based fissure sealants also show reduced water absorption with simultaneously increased shear adhesion with and without TWL.
  • Table 2 Fissure sealant with A) monomer component with 0.6% by weight CQ and 1.2% by weight BEDB, which is 100% by weight of the total composition.
  • fissure sealants with a monomer component with a content of 60% by weight and with a proportion of filler component of 40% by weight in the overall composition of 100% by weight were also produced as fissure sealants.
  • the adhesive performance of the fissure sealant according to the invention stands out clearly from the competitor Constic (15 MPa enamel adhesion 24h and 12 MPa enamel adhesion according to TWL) and Vertise Flow (16.4 MPa enamel adhesion 24h and 2.1 MPa enamel adhesion according to TWL). These are not special fissure sealants, but self-adhesive flows that are approved as fissure sealants, but can be used in the same way as the present invention (without a prior etching step).
  • Table 3 Fissure sealant with A) monomer component, which is 100% by weight of the total composition.
  • aprismatic enamel (MZS aprismatic human enamel) consists of unprepared enamel that does not have any enamel prisms. Aprismatic enamel does not produce a retentive etching pattern.
  • Table 4b Fissure sealant on aprismatic enamel after thermal cycling (thermal cycling).
  • the fissure sealants Helioseal F and Clinpro have a lower or comparable shear bond strength than those according to the invention without a previous etching step.
  • Unpolished means the enamel was not previously sanded, but only cleaned, as would be done with fissure sealing without an etching step. Consequently, the retentive anchoring possibility is further minimized. The liability is thus formed via a chemical bond.
  • a curing depth of 1.5 mm polymerization depth for fissure sealants regulates a curing depth of 1.5 mm polymerization depth for fissure sealants.
  • a curing depth of 3.4 mm Translux wave, LED, 440-480 nm, power density greater than 1200 mmW/cm 2 ) can be achieved with the formulations according to the invention.

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  • Health & Medical Sciences (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Biophysics (AREA)
  • Plastic & Reconstructive Surgery (AREA)
  • Dental Preparations (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Matériau de scellement de sillons autoadhésif radiodurcissable comprenant un pigment blanc et A) un composant monomère comprenant a) au moins un (méth)acrylate d'uréthane difonctionnel, b) au moins un agent de réticulation à base de (méth)acrylate difonctionnel à base d'oxyde d'alkylène hydrophile, c) un mélange de monomères acides d'un acide carboxylique oléfinique et/ou d'un anhydride d'acide carboxylique oléfinique en combinaison avec un monoester acide oléfinique d'un acide phosphorique et/ou un monoester acide oléfinique d'un acide thiophosphorique et d) un initiateur et/ou un système initiateur présentant respectivement un maximum d'absorption compris entre 420 et 550 nm, éventuellement avec un co-initiateur, et B) un composant de charge comprenant au moins un verre dentaire, A) le composant monomère et B) le composant de charge étant présents avec un rapport massique compris entre 60 : 40 et 100 : 0 dans le matériau de scellement de sillons et la composition totale du matériau de scellement de sillons étant égale à 100 % en poids.
EP22720599.4A 2021-04-02 2022-03-31 Matériau de scellement de sillons autoadhésif Pending EP4312947A1 (fr)

Applications Claiming Priority (3)

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DE102021108477.6A DE102021108477A1 (de) 2021-04-02 2021-04-02 Selbstadhäsiver Fissurenversiegler
DE102021108476.8A DE102021108476A1 (de) 2021-04-02 2021-04-02 Selbstadhäsives Dentalmaterial
PCT/EP2022/058711 WO2022207879A1 (fr) 2021-04-02 2022-03-31 Matériau de scellement de sillons autoadhésif

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EP22720373.4A Pending EP4312945A1 (fr) 2021-04-02 2022-03-31 Matériau dentaire autoadhésif

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4871786A (en) 1988-10-03 1989-10-03 Minnesota Mining And Manufacturing Company Organic fluoride sources
GB2257433A (en) 1991-07-12 1993-01-13 Bipin Chandra Muljibhai Patel Dental material usable as e.g. fissure sealant
DE69937960T2 (de) 1998-11-03 2008-12-24 New Age Biomaterials, Inc., Halifax Verbesserte füllstoffe für dentalverbundmaterialien
CA2574296C (fr) * 2004-07-27 2013-02-05 Dentsply Detrey Gmbh Composition dentaire adhesive en un seul emballage comprenant du t-butanol en tant que solvant
JP2010184997A (ja) * 2009-02-12 2010-08-26 Gc Corp 二成分系開始剤及びそれを利用した重合性組成物
DE102010003881A1 (de) * 2010-04-12 2011-10-13 Voco Gmbh Dentale Abdeckmasse
EP3603606A4 (fr) * 2017-03-31 2020-10-28 Mitsui Chemicals, Inc. Monomère adhésif pour matériau dentaire
JP7121809B2 (ja) * 2018-12-28 2022-08-18 三井化学株式会社 歯科材料用モノマー組成物、歯科材料用組成物及び歯科材料

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JP2024512756A (ja) 2024-03-19
US20240216229A1 (en) 2024-07-04
WO2022207877A1 (fr) 2022-10-06
US20240197577A1 (en) 2024-06-20
EP4312945A1 (fr) 2024-02-07
JP2024512755A (ja) 2024-03-19

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