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WO2002015848A2 - Compositions dentaires restauratrices et leur procedes d'utilisation - Google Patents

Compositions dentaires restauratrices et leur procedes d'utilisation Download PDF

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Publication number
WO2002015848A2
WO2002015848A2 PCT/US2001/041815 US0141815W WO0215848A2 WO 2002015848 A2 WO2002015848 A2 WO 2002015848A2 US 0141815 W US0141815 W US 0141815W WO 0215848 A2 WO0215848 A2 WO 0215848A2
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composition
cement
component
weight
weight percent
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PCT/US2001/041815
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English (en)
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WO2002015848A3 (fr
Inventor
Larry A. Lopez
Weitao Jia
Shuhua Jin
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Jeneric/Pentron Incorporated
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Application filed by Jeneric/Pentron Incorporated filed Critical Jeneric/Pentron Incorporated
Priority to AU2001287198A priority Critical patent/AU2001287198A1/en
Publication of WO2002015848A2 publication Critical patent/WO2002015848A2/fr
Publication of WO2002015848A3 publication Critical patent/WO2002015848A3/fr

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    • 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
    • A61K6/849—Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
    • 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

  • This invention relates to compositions for restorative dentistry, and more particularly to curable compositions usable as restoring materials suitable for dental fillings, crowns and bridges, and especially for root canal sealing and pulp capping. These compositions have improved physical and mechanical properties, as well as improved setting time.
  • materials used for dental restorations have comprised principally cured acrylate or methacrylate monomers or oligomers.
  • Typical cured acrylate resinous materials are disclosed in U.S. Patents No. 3,066,112 to Bowen, No. 3,179,623 to Bowen, No. 3,194,784 to Bowen, No. 3,751,399 to Lee et al. and No. 3,926,906 to Lee et al.
  • An especially important curable methacrylate monomer is the condensation product of bisphenol A and glycidyl methacrylate, 2,2'-bis [4-(3-methacryloxy-2-hydroxy propoxy)-phenyl] -propane (hereinafter abbreviated "Bis-GMA").
  • Bis-GMA 2,2'-bis [4-(3-methacryloxy-2-hydroxy propoxy)-phenyl] -propane
  • glass ionomers typically referred to as glass ionomer cements, wherein a poly(carboxylic acid) (such as a homo- or co-polymer of acrylic acid) is reacted with a fluoride ion leachable species (such as a fluoroaluminosilicate glass) in the presence of water to yield a crosshnked network structure.
  • a poly(carboxylic acid) such as a homo- or co-polymer of acrylic acid
  • a fluoride ion leachable species such as a fluoroaluminosilicate glass
  • cementitious materials for dental restorations.
  • Portland cements in particular are disclosed to have use as filling and sealing materials for tooth cavities in U.S. Patent No. 5,415,547 and U.S. Patent No. 5,769,638.
  • current cement-based materials may be of some utility as sealing materials, there accordingly remains a need in the art for cementitious materials with improved physical properties.
  • a curable dental composition comprising a polymerizable, ethylenically unsaturated component, a calcium silicate cement component, and at least one non-water curing component.
  • the curable dental composition can be self-curing and/or light curing, in conjunction with water curing.
  • Such curable dental compositions are useful for a variety of dental treatments and restorative functions including crown and bridge materials (including temporary crown and bridge materials), sealants, fixing cements, inlays, onlays, veneer shells, and filling materials.
  • a curable dental restorative composition comprises a curable, ethylenically unsaturated component, preferably a hydrophilic, methacrylate-containing monomer or oligomer component, a calcium silicate cement component, and a non-water curing component.
  • curable monomers or oligomers as part of the hardening agent for the cement component results in improved setting time and physical properties in the cured product.
  • the composition also comprises one or more fillers, for example barium glasses, calcium phosphates, and other fillers. These fillers promote the linkage between the polymerized component and the cement and therefore improve the mechanical strength of the composition.
  • the curable, ethylenically unsaturated component is preferably a monomer or oligomer containing at least two acrylate or methacrylate groups, and generally comprises viscous acrylate or methacrylate monomers such as those disclosed in U.S. Patent No. 3,066,112 to Bowen No. 3,179,623 to Bowen, No. 3,194,784 to Bowen, No. 3,751,399 to Lee et al., No. 3,926,906 to Lee et al., and commonly assigned U.S. Patents No. 5,276,068 and No. 5,444,104 to Waknine, all of which are incorporated herein by reference.
  • urethane dimethacrylate UDMA
  • DMDMA diurethane dimethacrylate
  • PPDMA polyurethane dimethacrylate
  • PEGDMA polyethylene glycol dimethacrylate
  • PCDMA polycarbonate dimethacrylate
  • the polymerizable component may comprise one of the so-called "diluent" acrylate or methacrylate monomers.
  • Suitable diluent monomers include those known in the art such as hydroxy alkyl methacrylates, for example 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate; ethylene glycol methacrylates, including ethylene glycol methacrylate, diethylene glycol methacrylate, tri(ethylene glycol) dimethacrylate and tetra(ethylene glycol) dimethacrylate; and diol dimethacrylates such as butanedimethacrylate, dodecanedimethacryalte, or 1,6-hexanedioldimethacrylate. Tri(ethylene glycol) dimethacrylate (TEGDMA) is particularly preferred.
  • the polymerizable component is a hydrophilic, ethylenically unsaturated monomer, or comprises such a monomer.
  • Suitable hydrophilic, ethylenically unsaturated monomers may have carboxyl, phosphoryl, sulfonyl, and/or hydroxyl functional groups, together with at least one ethylidenyl, acrylate, or methacrylate group.
  • hydrophilic monomers having at least one carboxyl group include but are not limited to methacrylic acid, maleic acid, p- vinylbenzoic acid, ll-methacryloyloxy-l,l-undecanedicarboxylic acid, 1,4- dimethacryloyloxyethylpyromellitic acid, 6-methacryloyloxyethylnaphthalene- 1,2,6- tricarboxylic acid, 4-methacryloyloxymethyltrimellitic acid and the anhydride thereof, 4-methacryloyloxyethyltrimellitic acid (“4-MET”) and an anhydride thereof (“4- META”), 4-(2-hydroxy-3-methacryloyloxy)butyltrimellitic acid and an anhydride thereof, 2,3-bis(3,4-dicarboxybenzoyloxy)propyl methacrylate, methacryloyloxytyrosine, N-methacryloyloxyphenylalan
  • hydrophilic monomers include BPDM, the reaction product of an aromatic dianhydride with an excess of 2-HEMA (2-hydroxyethyl methacrylate), as disclosed in U.S. Patent No. 5,348,988, which is incorporated by reference herein.
  • Other presently preferred hydrophilic monomers include EDMT, the reaction product of 2-hydroxyethyl methacrylate ("2-HEMA") with ethylene glycol bistrimellitate dianhydride; DSDM, the reaction product of 3,3',4,4'- diphenylsulfone tetracarboxylic dianhydride and 2-HEMA; PMDM; and PMGDM, the adduct of pyromellitic dianhydride with glycerol dimethacrylate.
  • 2-HEMA 2-hydroxyethyl methacrylate
  • Another type of preferred hydrophilic, ethylenically unsaturated species includes the degradable macromonomers having terminal acrylate or methacrylate groups disclosed in DENTAL COMPOSITIONS COMPRISING DEGRADABLE POLYMERS AND METHODS OF MANUFACTURE THEREOF, filed August 10, 2000, and claiming priority to U.S. provisional application Ser. No. 60/148,887, filed August 13, 1999, and incorporated by reference herein in its entirety.
  • Degradable macromonomers are manufactured by the polymerization of cyclic lactide, glycolide, or caprolactone in the presence of a compound having at least one active hydrogen and at least one acrylate or methacrylate functionality.
  • Preferred active hydrogen containing acrylate or methacrylate compounds comprise 2-hydroxyethyl methacrylate, hydroxypolyethyl methacrylate, phenoxy-2-hydroxypropyl methacrylate, and the like.
  • Preferred co-polymerizable acrylate or methacrylate monomers include diluent monomers such as 1,6-hexanediol dimethacrylate, triethylene glycol trimethacrylate, and 2-hydroxyethyl methacrylate.
  • Degradable macromonomers can also be manufactured by the esterification of hydroxyl-group(s) terminated macromonomers of the above-mentioned hydroxy acids with acrylic acid, methacrylic acid, and their derivatives.
  • the polymerizable component is used in amounts of about 5 to about 90 weight percent, preferably about 20 to about 70, and more preferably about 30 to about 60 weight percent based on the total weight of the polymerizable component, cement component, and curing component.
  • cement component is a dry cement settable in an aqueous environment.
  • the preferred cement component is a calcium silicate cement commonly known as Portland cement.
  • the process of making Portland cement is well known, and it can be purchased from any number of manufacturers under various trade names.
  • the basic raw materials for Portland cement are lime (CaO), silica (SiO 2 ), alumina (Al 2 O 3 ), and iron oxide (Fe O 3 ), appropriately proportioned to produce various types of Portland cement.
  • the selected raw materials are crushed, ground, and then blended in the desired proportions.
  • the mixture is then fed into a rotary kiln where it is heated to temperatures of up to 1400° to 1650°C, cooled, and subsequently pulverized.
  • a small amount of gypsum (CaSO »2H O) may be added to the cement to control the setting time.
  • the resulting cement consists principally of tricalcium silicate (3CaO»SiO ), dicalcium silicate (2CaO»SiO 2 ), tricalcium aluminate (3CaO»Al O ), and tetracalcium aluminoferrite (4CaO»Al 2 O 3 »Fe 2 O ). It is common, however, to report Portland cement compositions on the basis of the corresponding oxides.
  • the principal component of Portland cement by weight is calcium, which is present in amount of about 50 to about 75 weight percent, preferably about 65 weight percent of the total cement composition, calculated as calcium oxide (CaO). Silicon is present in an amount of about 15 to about 25 weight percent, preferably about 21 weight percent of the total cement composition, calculated on the basis of silicon dioxide (SiO 2 ). The combination of calcium and silicon components is present in an amount of about 70 to about 95 weight percent, preferably about 86 weight percent of the total cement composition, based on the corresponding oxides.
  • CaO calcium oxide
  • Silicon is present in an amount of about 15 to about 25 weight percent, preferably about 21 weight percent of the total cement composition, calculated on the basis of silicon dioxide (SiO 2 ).
  • the combination of calcium and silicon components is present in an amount of about 70 to about 95 weight percent, preferably about 86 weight percent of the total cement composition, based on the corresponding oxides.
  • the suitability of a particular cement component for a given purpose is typically determined by a combination of its chemical component and its physical attributes, i.e. the manner and degree to which the cement is ground (granulation) and the resulting particle size.
  • the fineness of a cement is indicated by the Blaine number, which represents the ratio of the particle surface area to its weight (square centimeters of surface per gram).
  • Portland cements generally have a Blaine number in the range of 3,200 to 5,500 cm 2 /g or greater.
  • Faster setting cements like that preferably utilized in the present invention, have a Blaine number in the range of 4,000-5,500 cm 2 /g.
  • the most preferable cement utilized in the present invention has a Blaine number in the range of 4,500-4,600 cm 2 /g.
  • Type I is called normal Portland cement and is a general purpose cement suitable for all uses when the special properties of the other types are not required.
  • Type I Portland cement is more generally available than are the other types of cement, and in its normal applications, is used where the heat generated by the hydration of the cement will not cause an objectionable rise in temperature. Such conditions are typical of the mouth, which would normally not necessitate the use of ASTM Types II through V.
  • the preferred embodiment accordingly utilizes a Type I Portland cement having the following approximate composition by weight (calculated on the basis of the corresponding oxides): 21% SiO 2 , 4% Al 2 O 3 , 5% Fe 2 O 3 , 65% CaO, 2% MgO, 2.5% SO 3 , and 0.5% of alkalis such as Na 2 O and/or K O.
  • This Portland cement is commercially available as the Colton Fast-Set brand of the California Portland Cement Company.
  • Type I Portland cement Although the preferred embodiment thus comprises an ASTM Type I Portland cement, other types of hydraulic (water-settable) cements, particularly calcium silicate cements, may be suitable for the purposes described herein.
  • Type III Portland cement is used when early strength is desired, which may be suitable for certain applications where early strength may be advantageous.
  • Type IV is a low heat of hydration cement useful when the heat of hydration is critical. It would typically not be required in anatomical structures, but it may be useful, for example, if an additive were used that may be adversely affected by a higher heat of hydration.
  • the cement component is generally present in an amount from about 10 to about 95 percent by weight, preferably in an amount from about 20 to about 60 percent by weight, and even more preferably in an amount from about 30 to about 50 percent by weight of the polymerizable component, cement component, and curing component.
  • various amounts of water from 0 to
  • the dental restorative composition 50 % by weight of the dry cement component may be utilized in the dental restorative composition. Enough water is added to the cement to give it a putty consistency, which then solidifies to a rock-like hardness.
  • the water content is in the range of 10 to 40 weight percent, and most preferably three parts cement are used with one part water, or 25 weight percent of the dry cement component is water.
  • Use of water as a reactant in the hardening reaction offers significant advantages in dental restorative compositions.
  • Calcium silicate cements harden upon reaction with water. The hardening reactions are complex, but principally involve the hydration of tricalcium silicate (3CaO»SiO 2 ) and dicalcium silicate (2CaO»SiO 2 ).
  • the principal early reaction product is tricalcium silicate hydrate, a colloidal gel of extremely small particles (less than about one micron) that is most responsible for the early strength of Portland cement.
  • the dicalcium silicate has a slower hydration reaction and is mainly responsible for strength increases beyond one week.
  • Tricalcium aluminate which plays a lesser role in the hardening process, hydrates rapidly also and contributes to early strength of development.
  • the curable dental restorative composition further includes a non-water curing component such as a light-curing and/or self-curing system.
  • the light-cure system is selected from known light-activated polymerization initiators, including but not being limited to benzil, benzoin, benzoin methyl ether, DL-camphorquinone (CQ), and benzil diketones. Either UV-activated cure or visible light-activated cure (approx. 230 to 750 nm) is acceptable.
  • the amount of photoinitiator is selected according to the curing rate desired. A minimally catalytically effective amount is generally about 0.01 percent by weight of the polymerizable components, and will lead to a slower cure.
  • UV absorber in amounts ranging from about 0.01 to about 1.0 weight percent.
  • Such UV absorbers are particularly desirable in the visible light curable components in order to avoid discoloration of the resin from any incident ultraviolet light.
  • Suitable UV absorbers are the various benzophenones, particularly UV-5411 available from American Cyanamid Company. Light-cure systems are generally proved to the practitioner as one-part systems.
  • the dental restorative composition may be formulated with a self-curing system.
  • Self-curing components will generally contain free radical polymerization initiators such as, for example, a peroxide in amounts of about 0.01 to about 3.0 weight percent.
  • free radical initiators are lauryl peroxide, tributyl hydroperoxide and, more particularly benzoyl peroxide (BPO).
  • Self-cure systems may further comprise an accelerator such as a tertiary amine, generally tertiary aromatic amines such as ethyl 4-(dimethylamino)benzoate (commonly known as AEDMAB”), 2-[4-(dimethylamino)phenyl] ethanol, N, N- dimethyl-p-toluidine (DMPT), bis(hydroxyethyl)-p-toluidine (DHEPT), and triethanolamine.
  • AEDMAB ethyl 4-(dimethylamino)benzoate
  • 2-[4-(dimethylamino)phenyl] ethanol N, N- dimethyl-p-toluidine (DMPT), bis(hydroxyethyl)-p-toluidine (DHEPT), and triethanolamine.
  • AEDMAB ethyl 4-(dimethylamino)benzoate
  • DMPT N- dimethyl-p-toluidine
  • DHEPT bis
  • Self-cure systems are generally provided to the practitioner as two-part systems, one part comprising the liquid components (e.g., monomer, oligomer, macromonomer and water) and a second part comprising the dry components (e.g., dry cement, initiators, and optional filler).
  • liquid components e.g., monomer, oligomer, macromonomer and water
  • dry components e.g., dry cement, initiators, and optional filler
  • the curable dental restorative compositions may furthermore optionally comprise a filler component selected from those known in the art of dental restorative materials.
  • suitable filling materials include but are not limited to, silica, quartz, strontium silicate, strontium borosilicate, lithium silicate, lithium alumina silicate, amorphous silica, ammoniated or deamnioniated calcium phosphate, alumina, zirconia, chopped glass fibers, tin oxide, and titania.
  • Particularly suitable fillers are those having a particle size in the range from about 0.1-5.0 ⁇ m, mixed with a silicate colloid of 0.001 to about 0.07 microns.
  • Calcium phosphates preferred in the present invention are, for example, calcium phosphates and tricalcium phosphate.
  • radiopaque/high refractive index materials such as apatites
  • Suitable high refractive index filler materials include, but are not limited to, high refractive index silica glass fillers, calcium silicate based fillers such as apatites, hydroxyapatites or modified hydroxyapatite components.
  • inert, non-toxic radiopaque materials such as bismuth oxide (Bi 2 O 3 ), barium sulfate, and bismuth subcarbonate may be used.
  • Certain fillers, such as glass fillers may be silanized to improve the bond between filler and resin.
  • the filler is generally present in amounts of about 0 to about 80 percent by weight, preferably about 10 to about 70 percent by weight, and most preferably about 20 to about 60 percent by weight of filler based on the total dental curable composition (i.e., polymerizable component, cement component, curing component, and filler).
  • the amount of filler is readily determined by those of ordinary skill in the art, depending on the intended application and identity of the components.
  • the dental restorative compositions may further comprise handling agents to aid in dispersion and long-term suspension of the components, particularly the cement.
  • Suitable handling agents may be, for example, viscous materials such as polyethylene glycol (PEG) or polypropylene glycol (PPG), each having a molecular weight of about 400 or greater.
  • Effective quantities of handling agent may be readily determined by one of ordinary skill in the art, depending on the characteristics of the composition and the agent, and may comprise, for example, about 1 to about 50 percent by weight of the total composition, preferably about 10 to about 40 percent by weight of the total composition.
  • the dental restorative composition may further comprise other additives, for example anti-oxidants, such as BHT (2,6-di-tert-butyl-4-methylphenol) or hydroquinone methyl ether, in amounts in the range from about 0.1 to about 0.3% by weight of the polymerizable components; ultraviolet stabilizers to prevent discoloration, for example benzophenones such as 2-hydroxy-4- methoxybenzophenone, benzotriazoles such as 2-(2'-hydroxy-5'-methylphenyl) benzotriazole, 2-(2-hydroxy-5-tert-octylphenyl) benzotriazole (available under the trade name UV-54 from American Cyanamid Company) and other derivatives thereof; fluorescent whitening agents such as 2,5-bis(5-tert-butyl-2-benzoxazole) thiophene (available under the trade name UV-OB); trace amounts of FDA and FDC approved dyes, for example carbon black, yellow No.
  • anti-oxidants such as BHT (2,6-d
  • additives known in the art such as fluoride, fluoride-releasing agents, polycarboxyhc acids useful in the formation of glass ionomer cements such as the homo- and copolymers of acrylic acid and/or itaconic acid, and various medicaments, such as Novocain (procaine hydrochloride), Benzocaine (ethyl aminobenzoate), ascorbic acid, butacaine sulfate, dibucaine hydrochloride, phenobarbital, pentabarbital sodium, butabarbital, diethyl stilbestrol, xylocaine and various known antibiotics.
  • Novocain procaine hydrochloride
  • Benzocaine ethyl aminobenzoate
  • ascorbic acid butacaine sulfate
  • dibucaine hydrochloride dibucaine hydrochloride
  • phenobarbital pentabarbital sodium, butabarbital, diethyl stilbestrol, x
  • antibiotics are particularly preferred, as an antibiotic can provide sterilization (which is particularly important in sealants and pulp capping materials) and/or caries prevention (which is particularly important for filling materials).
  • Useful antibiotics include, but are not limited to, one or more of salicylic acid, salicylic acid esters, sulfanilamide, chlorhexidine, erythromycin, bacitracin, hexachloraphene, lincomycin hydrochloride, p-amino salicylic acid, sulfadiazine, procaine penicillin, Aureomycin, streptomycin, tetramycin, chloramphenicol, penicillin, neomycin sulfate, succinoyl-sulfathiazole, cetyl pyridinium chloride, trimethyl benzyl ammonium chloride, triethyl dodecyl ammonium bromide, sulfathiazole, sulfanilamide, and tetracycline
  • Preferred antibiotics include but are not limited to metronidazole, ciprofloxacin, and minocycline.
  • Other useful antibiotics include amoxicillin, cefroxadine, cefaclor, fosfomycin, or rokitamycin, each of which may be used individually or to replace minocycline.
  • the antibiotic can be co-polymerized with the dental restorative composition, as disclosed in U.S. Patent 5,408,022 and 5,733,949 to Imazato et al., which teaches anti-microbial polymerizable components comprising an ethylenically unsaturated monomer, at least one mono-, di-, or tri-functional ethylenically unsaturated monomer having anti-microbial activity, and a polymerization initiator.
  • the dental restorative materials can be formulated so as to leach the antibiotics to the site to be restored at a controlled rate.
  • therapeutically effective quantities of antibiotics are readily determined by those of ordinary skill in the art, depending on exemplary factors such as the particular restorative material and use, the strength of the antibiotic, the rate of release from the dental restorative material, cost, and the like. In general, however, therapeutically effective quantities that do not interfere with the advantageous properties of the dental restorative components are between about 0.05 to about 5.0% wt. % of the total composition.
  • Another preferred embodiment is a method of making a dental restorative comprising preparing a site to be restored in a tooth; and applying the above-describe curable dental restorative composition to the tooth.
  • the restoration is an endodontically prepared tooth, i.e., a tooth that has been prepared for an endodontic restoration.
  • ProRoot MTA is a commercial root canal repair material containing Portland cement, sold by Dentsply Tulsa Dental, Tulsa, Oklahoma, and prepared according to the distributor's instructions. It is believed that there is no polymerizable component or non-water curing component in the system. As may be seen by reference to Table 3, the inventive compositions have far greater flexural strength than the comparative material, and much shorter setting times.

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  • 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)
  • Inorganic Chemistry (AREA)
  • Dental Preparations (AREA)

Abstract

L'invention porte sur une comprenant: un composant durcissable non saturé en éthylène, de préférence un monomère ou oligomère contenant du méthacrylate; un composant de ciment de silicate de calcium, et un durcisseur autre que l'eau, et facultativement de l'eau et/ou des charges. Le recours à des monomères ou oligomères durcissables parmi les agents durcisseurs du ciment améliore le temps de prise et les propriétés physiques du produit durci.
PCT/US2001/041815 2000-08-22 2001-08-22 Compositions dentaires restauratrices et leur procedes d'utilisation WO2002015848A2 (fr)

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AU2001287198A AU2001287198A1 (en) 2000-08-22 2001-08-22 Dental restorative compositions and method of use thereof

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US22711100P 2000-08-22 2000-08-22
US60/227,111 2000-08-22
US23250200P 2000-09-13 2000-09-13
US60/232,502 2000-09-13

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WO2008103712A3 (fr) * 2007-02-20 2008-10-09 Bisco Inc Matériau de cicatrisation, de coiffage, et de recouvrement de pulpe dentaire polymérisable et son procédé d'utilisation
WO2009131415A3 (fr) * 2008-04-24 2010-01-14 Jang Sung Wook Type auto-neutralisant de préparation d'hydroxyde de calcium destinée à être utilisée en dentisterie
JP2012020983A (ja) * 2010-07-16 2012-02-02 Sun Medical Co Ltd 歯科用組成物
WO2013013275A1 (fr) * 2011-07-27 2013-01-31 B Athanassiadis Dental Pty Ltd Compositions alcalines et leur utilisation dentaire et médicale
JP2015074624A (ja) * 2013-10-08 2015-04-20 サンメディカル株式会社 複合充填材及び歯科用組成物
US9084802B2 (en) 2010-05-12 2015-07-21 Rempex Pharmaceuticals, Inc. Tetracycline compositions
WO2018038227A1 (fr) * 2016-08-26 2018-03-01 国立大学法人北海道大学 Ciment dentaire
CN109453037A (zh) * 2018-11-27 2019-03-12 吉林省登泰克牙科材料有限公司 一种用于牙科正畸粘结的非调和型组合物、其制备方法和应用
RU2699371C1 (ru) * 2018-12-06 2019-09-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный медицинский университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО КубГМУ Минздрава России) Стоматологическая паста для временного пломбирования каналов корней зубов при лечении хронического деструктивного периодонтита

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JP2007524635A (ja) * 2003-07-02 2007-08-30 エーディーエー ファウンデーション 再石灰化作用のある歯科用セメント
US7619016B2 (en) 2003-07-02 2009-11-17 Ada Foundation Remineralizing dental cements
WO2005002531A1 (fr) * 2003-07-02 2005-01-13 Ada Foundation Ciments dentaires de remineralisation
WO2008103712A3 (fr) * 2007-02-20 2008-10-09 Bisco Inc Matériau de cicatrisation, de coiffage, et de recouvrement de pulpe dentaire polymérisable et son procédé d'utilisation
US8801846B2 (en) 2008-04-24 2014-08-12 Sung Wook Jang Self-neutralising type of calcium hydroxide preparation for use in dentistry
WO2009131415A3 (fr) * 2008-04-24 2010-01-14 Jang Sung Wook Type auto-neutralisant de préparation d'hydroxyde de calcium destinée à être utilisée en dentisterie
CN102065822A (zh) * 2008-04-24 2011-05-18 张星旭 用于牙科学的自中和型氢氧化钙制剂
US9084802B2 (en) 2010-05-12 2015-07-21 Rempex Pharmaceuticals, Inc. Tetracycline compositions
US11944634B2 (en) 2010-05-12 2024-04-02 Melinta Subsidiary Corp. Tetracycline compositions
US9278105B2 (en) 2010-05-12 2016-03-08 Rempex Pharmaceuticals, Inc. Tetracycline compositions
US9744179B2 (en) 2010-05-12 2017-08-29 Rempex Pharmaceuticals, Inc. Tetracycline compositions
US12161656B2 (en) 2010-05-12 2024-12-10 Melinta Subsidiary Corp. Tetracycline compositions
JP2012020983A (ja) * 2010-07-16 2012-02-02 Sun Medical Co Ltd 歯科用組成物
AU2012286596B2 (en) * 2011-07-27 2015-08-20 B Athanassiadis Dental Pty Ltd Alkaline compositions and their dental and medical use
WO2013013275A1 (fr) * 2011-07-27 2013-01-31 B Athanassiadis Dental Pty Ltd Compositions alcalines et leur utilisation dentaire et médicale
JP2015074624A (ja) * 2013-10-08 2015-04-20 サンメディカル株式会社 複合充填材及び歯科用組成物
WO2018038227A1 (fr) * 2016-08-26 2018-03-01 国立大学法人北海道大学 Ciment dentaire
JPWO2018038227A1 (ja) * 2016-08-26 2019-06-24 国立大学法人北海道大学 歯科用セメント
CN109453037B (zh) * 2018-11-27 2022-01-28 吉林省登泰克牙科材料有限公司 一种用于牙科正畸粘结的非调和型组合物、其制备方法和应用
CN109453037A (zh) * 2018-11-27 2019-03-12 吉林省登泰克牙科材料有限公司 一种用于牙科正畸粘结的非调和型组合物、其制备方法和应用
RU2699371C1 (ru) * 2018-12-06 2019-09-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кубанский государственный медицинский университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО КубГМУ Минздрава России) Стоматологическая паста для временного пломбирования каналов корней зубов при лечении хронического деструктивного периодонтита

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