WO1999051190A1 - Produit d'obturation composite organique, procede de production associe, et composition dentaire de produit d'obturation polymerisable renfermant ledit produit - Google Patents

Produit d'obturation composite organique, procede de production associe, et composition dentaire de produit d'obturation polymerisable renfermant ledit produit Download PDF

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Publication number
WO1999051190A1
WO1999051190A1 PCT/JP1999/001687 JP9901687W WO9951190A1 WO 1999051190 A1 WO1999051190 A1 WO 1999051190A1 JP 9901687 W JP9901687 W JP 9901687W WO 9951190 A1 WO9951190 A1 WO 9951190A1
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Prior art keywords
meth
organic composite
composite filler
acrylate
weight
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PCT/JP1999/001687
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English (en)
Japanese (ja)
Inventor
Tatsuya Ori
Narimichi Honda
Yasukazu Saimi
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Sun Medical Co., Ltd.
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Application filed by Sun Medical Co., Ltd. filed Critical Sun Medical Co., Ltd.
Publication of WO1999051190A1 publication Critical patent/WO1999051190A1/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
    • A61K6/884—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 present invention relates to an organic composite filler, a method for producing the same, and a polymerizable dental filling composition containing the same. More specifically, the organic composite filler, its production method and its high content in the organic polymerizable monomer, have excellent mechanical properties due to polymerization, especially high flexural strength, and also have abrasion resistance and water resistance.
  • the present invention relates to a polymerizable dental filling composition that gives a cured product having good properties.
  • dental filling compositions containing an organic polymerizable monomer and an inorganic filler and a polymerization initiator can be used for prosthetic restoration and restoration of tooth defects, as well as for artificial teeth. It has been used for crowns and the like. Therefore, the cured product imparts mechanical strength, abrasion resistance, water resistance, and adhesiveness, and has an aesthetic property that takes into account not only transparency but also abrasiveness in order to approximate natural teeth. It is important to combine them.
  • dental filling compositions containing a glass filler having a particle diameter of l to 100 ⁇ m as an inorganic filler have been known, but cured products of this composition have excellent mechanical properties, However, since the elasticity and hardness of the organic resin were smaller than those of the filler in the cured product, the abrasion and abrasion resistance were poor. In addition, fillers protrude from the hardened material surface worn in the human oral cavity, causing damage to opposing teeth.
  • the silane coupling agent T-methacryloxypropyltrimethoxysilane MP-MPTS
  • MP-MPTS silane coupling agent T-methacryloxypropyltrimethoxysilane
  • Japanese Patent Application Laid-Open No. 56-20666 discloses a method for producing a filler obtained by coating an inorganic filler with a polymerizable monomer, that is, an organic composite filler.
  • the organic composite filler produced by this method uses a polyfunctional (meth) acrylate having three or more polymerizable double bonds in the (meth) acrylic acid-based monomer. Therefore, all of them do not completely polymerize, and some of them remain. Therefore, the obtained organic composite filler has a high reactivity with the organic polymerizable monomer, and by chemically bonding, the mechanical properties of the cured material obtained by blending the compound are obtained. It is proposed to be effective in improving the quality. However, since the mechanical properties, particularly the bending strength, of the organic composite filler and the cured product obtained by blending the same are not sufficient, improvement of the organic composite filler has been desired.
  • Japanese Patent Publication No. Hei 7-80773 Japanese Patent Publication No. Hei 7-80773
  • each X Q is independently 0, S, or NH
  • each Y Q is independently selected from the group consisting of alkylene, oxyalkylene, cycloalkylene, arylene, and aralkylene groups.
  • Each RQ is independently an organic group, provided that at least two polymerizable ethylenically unsaturated groups are present in the RQ group as a whole). Having poly (ethylenically unsaturated) dynamite Disclosed are restoratives, prostheses and polymerizable compositions for use in treating teeth, which are characterized by containing isocyanurate.
  • This composition is intended to be used as a dental filling composition per se, rather than as a dental filler.
  • Japanese Patent Application Laid-Open No. 5-246819 discloses an organic composite filler obtained by polymerizing a specific carboxylic acid-based monomer and a specific vinyl monomer in an inorganic compound dispersion system. It is disclosed for use in compositions. However, the organic composite filler of the present invention is not described. Disclosure of the invention
  • An object of the present invention is to provide a polymerizable dental filling composition which is excellent in mechanical properties, especially bending strength, and which gives a cured product having good abrasion resistance and water resistance.
  • Another object of the present invention is to provide an organic composite filler suitably used in the polymerizable dental filling composition.
  • Still another object of the present invention is to provide a method for producing the organic composite filler of the present invention.
  • the polymerization initiator (D) is heated to a temperature of 60 to 200 ° C. under a pressure of 1 to 200 kg / cm 2 to cause the mixture to be hardened.
  • a method for producing an organic composite filler as a pulverized material is provided.
  • a polymerizable dental filling composition comprising an organic polymerizable monomer (E), a polymerization initiator (D) and the above-mentioned organic composite filler of the present invention. It is.
  • n is an integer of 1 to 15, and X 1 and X 2 each independently represent H or a methyl group).
  • the compound represented by is preferred.
  • examples of such a compound include a hexafunctional urethane (meta) having, for example, a methylene group, an ethylene group, a propylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group or the like as — (CH 2 ) n ) in the formula ( ⁇ ).
  • metal a hexafunctional urethane
  • R is-(CH 2 ).
  • Such compounds include, for example, ethyl isocyanurate (meth) acrylate, propyl tri (meth) acrylate, isocyanuric acid butyl tri (meth) acrylate, pentyl tri (meth) acrylate isocyanurate, hexyl tri (meth) acrylate, isocyanurate (meth) acrylate, Socyanuric acid (hexyl keto) ethyltri (meth) acrylate and the like.
  • isocyanurate (A) having an ethylenically unsaturated group a hexafunctional isocyanurate-based urethane methacrylate in which n in the formula ( ⁇ ) is 3 to 10 is preferably used. More preferably.
  • difunctional or higher functional (meth) acrylate monomer (B) used in the present invention conventionally known ones can be used.
  • Poly (alkylene glycol) di (meth) acrylates such as di (meth) acrylate and neopentyl alcohol di (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (
  • inorganic filler (C) used in the present invention those commonly used as inorganic fillers of rubber or organic polymerizable monomers are generally used.
  • silicon dioxide, glass powder, quartz powder, barium sulfate, aluminum oxide, titanium oxide, barium salt, glass beads, glass fiber, and barium fluoride include glass fillers containing lithium, lead salts and talc, colloidal silica, silica gel, zirconium oxide, tin oxide, carbon fiber, and other ceramic powders. These can be used after the surface is hydrophobically treated.
  • fine-particle silica obtained by subjecting a silica surface, which is a high-purity silicon dioxide aerosol, to a surface treatment for imparting hydrophobicity with dimethyldichlorosilane is preferable.
  • the shape of the inorganic filler is not limited, and may be spherical or amorphous, and is appropriately selected along with the particle diameter.
  • the particle size of the inorganic filler is usually appropriately selected and used from 01 to 50 m.
  • the particle size of the finely divided silica is preferably in the range of 0.001 to 1 m, more preferably 0.001 to 0.1 ⁇ 1, and still more preferably 0.005 to 0.07 m.
  • the mixing ratio of the inorganic filler (C) to the component (A) and the component (B) is selected in consideration of the shape and particle size of the inorganic filler, the viscosity of the monomer, and the like.
  • Component (A) is 5 to 400 parts by weight
  • component (B) is 5 to 400 parts by weight
  • component (B) is 10 to 150 parts by weight based on 100 parts by weight of the inorganic filler. It is in the range of parts by weight.
  • the compounding amounts of the isocyanurate having an ethylenically unsaturated group (A) and the bifunctional or higher (meth) acrylate monomer (B) are determined based on the total weight of these components. Is preferably 30 to 95% by weight, more preferably 50 to 95% by weight, and particularly preferably 70 to 95% by weight. Within the range of the above weight ratios, the viscosity of the mixture obtained by mixing them is preferably in the range of 500 to 20000 cps (at 25), more preferably 1000 to 10000 cps (at 25 ° C.). Ratios are advantageously used.
  • the polymerization initiator (D) a light, chemical or thermal polymerization initiator is used.
  • the chemical and thermal polymerization initiators organic peroxides and diazo compounds can be preferably used.
  • a compound having a decomposition half-life at 80 ° C of 10 hours or less include, for example, organic peroxides such as acetyl peroxide, isobutyl peroxide, decanol peroxide, benzoyl peroxide, and peroxy succinate.
  • Tert-carbonate such as diisopropyl peroxide; diisopropylperoxydicarbonate, di-2-ethylhexylperoxydicarbonate, diarylperoxydicarbonate, etc .; tert — Peroxyesters such as butylhydroxyisobutyrate, tert-butylneodecanate, and cuproxyneodecanate; and peroxysulfonates such as acetylcyclohexylsulfonyl peroxide.
  • diazo compound examples include, for example, 2,2, -azobisisobutyronitrile, 4,4, -azobis (4-cyanovaleric acid), 2,2'-azobis (4-methoxy-2,4-dimethoxy) Valeronitrile), 2,2'-azobis (2-cyclopropylpropionitrile) and the like.
  • benzoyl peroxide and 2,2'-azobisisobutyronitrile are more preferred.
  • a reducing agent such as amine can be used in combination.
  • a photosensitizer alone or a combination of a photosensitizer and a photopolymerization accelerator can be used.
  • the photosensitizer include visible light such as benzyl, camphorquinone, ⁇ -naphthyl, ⁇ , ⁇ '-dimethoxybenzyl, pentadione, 1,4-phenanthrenequinone, naphthoquinone, and trimethylbenzoyldiphenylphosphine oxide.
  • Known ketone compounds that are excited by light or ultraviolet light irradiation and start polymerization are preferably used. These can be used alone or in combination of two or more.
  • camphorquinone is preferably used.
  • Examples of the photopolymerization accelerator include ⁇ , ⁇ -dimethylaniline, ⁇ , ⁇ -ethylylaniline, ⁇ , ⁇ -dibenzylylarealine, ⁇ , ⁇ -dimethyl- ⁇ -toluidine, ⁇ - ⁇ , ⁇ -dimethylaminobenzo.
  • nitrogen atoms were directly bonded to aromatics such as p-N, N-dimethylaminobenzoic acid, ⁇ - ⁇ , ⁇ ⁇ ⁇ ⁇ -dimethylaminobenzoic acid 2- ⁇ -butoxyshethyl, and ⁇ , ⁇ -dimethylaminoethyl methacrylate.
  • aromatics such as p-N, N-dimethylaminobenzoic acid, ⁇ - ⁇ , ⁇ ⁇ ⁇ ⁇ -dimethylaminobenzoic acid 2- ⁇ -butoxyshethyl, and ⁇ , ⁇ -dimethylaminoethyl methacrylate.
  • Tertiary aromatic amines or aliphatic tertiary amines having a polymerizable group are preferably used.
  • a combination of a photosensitizer and a photopolymerization accelerator is preferable for quickly terminating curing, and camphorquinone and ⁇ - ⁇ , ⁇ -dimethylaminobenzoate, ⁇ - ⁇ , ⁇ -dimethylaminobenzoate are preferred.
  • camphorquinone and ⁇ - ⁇ , ⁇ -dimethylaminobenzoate, ⁇ - ⁇ , ⁇ -dimethylaminobenzoate are preferred.
  • a combination of an ester compound of a tertiary aromatic amine in which a nitrogen atom is directly bonded to an aromatic such as 2- ⁇ -butoxyshethyl is preferably used.
  • the polymerization initiator (D) for producing the organic composite filler a chemical or thermal polymerization initiator is preferably used.
  • the polymerization initiator (D) is used in an amount of preferably from 0.01 to 5 parts by weight, more preferably from 0.1 to 100 parts by weight of the mixture of the components ( ⁇ ), ( ⁇ ) and (C). It is blended in up to 1 part by weight.
  • the organic composite filler of the present invention comprises a mixture of the component ( ⁇ ⁇ ), the component ( ⁇ ), the component (C), and the component (D) under a pressure of 1 to 200 kg at a pressure of 60 to 200 °. It can be manufactured by heating to C and curing, and then pulverizing the obtained cured product.
  • a mixture composed of these components is placed in a mold, and a pressure range of 1 to 200 kg / cm2, preferably 10 to 200 kgZcm2, and a temperature range of 6 is applied by a heat compression molding machine. 0 to 200, more preferably 100 to 150, for several minutes to several hours, more preferably for 5 minutes to 1 hour, and the obtained cured product is pulverized. You.
  • the pulverization is performed using, for example, a dry pulverizer such as a pole mill or a jet mill or a wet pulverizer.
  • the particle shape may be spherical or amorphous, and the process is carried out until a desired particle size is obtained.
  • a polymerization initiator may be used. May be heated and polymerized as it is to produce an organic composite filler.
  • the average particle size of the organic composite filler in the present invention is preferably 1 to 30 zm, particularly preferably 3 to 30 zm, in view of the viscosity of the composition obtained by blending the same and the mechanical strength of the cured product. It is in the range of ⁇ 15 ⁇ m. In the organic composite filler of the present invention, it is preferable that the polymerizable double bond remains partially unreacted.
  • the polymerizable dental filling composition of the present invention is similarly provided using the organic composite filler of the present invention.
  • the compounding amounts of the organic polymerizable monomer (E), the polymerization initiator (D) and the organic composite filler are determined according to the amount of the organic composite filler used in the filler. Is appropriately selected according to the particle size of the compound and the purpose of use.
  • the polymerization initiator (D) is 0.01 to 10 parts by weight based on 100 parts by weight of the organic polymerizable monomer (E)
  • the organic composite filler of the present invention is 40 to 400 parts by weight. Parts are blended. In consideration of operability, it is more preferable to replace one part of 40 to 400 parts by weight of the organic composite filler with 10 to 300 parts by weight of hydrophobic silica.
  • the organic polymerizable monomer (E) is not particularly limited as long as it is a known one used in a dental filling composition, and various ones can be used.
  • the following polymerizable monofunctional (meth) acrylates or the same as the bifunctional or higher-functional (meth) acrylate-based monomer (B) used in producing the organic composite filler described above Can be used and is appropriately selected according to the purpose of use.
  • Monomer for example, di (meth) acrylates such as propanediol, butanediol, hexanediol, octanediol, nonanediol, decanediol, eicosanediol;
  • Urethane-based polymerizable monomers used to form hydroxyl groups such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 3-hydroxypropyl (meth) acrylate.
  • bi- or higher functional organic polymerizable monomers for example, triethylene glycol acrylate, trimethylolpropane monoacrylate dimethacrylate, pen erythri 1 ⁇ -l-diacrylate dimethacrylate And compounds having both methacrylate and acrylate groups in one molecule.
  • the organic polymerizable monomer (E) may be used alone or in combination of two or more, if necessary. If a monofunctional polymerizable monomer is used alone, the polymerizability may be inferior or the strength of the polymer may be reduced. It is preferably used as a body.
  • polymerization initiator (D) a light, chemical or thermal polymerization initiator is used as in the case of the above-mentioned polymerization initiator (D) for producing the organic composite filler of the present invention.
  • Polymerization initiator (D) a light, chemical or thermal polymerization initiator is used as in the case of the above-mentioned polymerization initiator (D) for producing the organic composite filler of the present invention.
  • Examples of the compound (D) include the same compounds as those described above.
  • a photopolymerization initiator is preferably used for a dental filling composition.
  • hydroquinone compounds such as hydroquinone and dibutylhydroquinone; hydroquinone monomethyl ether, 2,6-di-tert-butylphenol, 2,6 It is preferable to mix one or more phenols such as —di-6 rt-butyl; p-cresol and the like as a polymerization inhibitor.
  • phenols such as —di-6 rt-butyl
  • p-cresol p-cresol and the like
  • a combination of hydroquinone monomethyl ether and 2,6-di-tert-butyl-p-cresol is preferably used.
  • the amount is not particularly limited, but is generally preferably 0.01 to 2 parts by weight, more preferably 0.02 parts by weight, based on 100 parts by weight of the organic polymerizable monomer (E). It is 2 to 1 parts by weight.
  • the polymerizable dental filling composition of the present invention may optionally contain a colorant, an ultraviolet absorber, an X-ray contrast agent, a pigment, a dye, and the like.
  • TAG DMA dimer acrylate
  • R972 hydrophobic fine-particle silica having an average particle diameter of 16 nm
  • the average particle size shown in the examples is a value measured by LA-910 unless otherwise specified.
  • Residual double bond content of the powder surface of the organic composite filler (%) is the Fourier transform infrared component photometer by (PERKIN ELMER Co.), the double bond of the peak height at 1640 c ⁇ 1 (baseline method ) was calculated as 100% before curing.
  • ⁇ -Light manufactured by Moriyasu
  • a 3mmx3mmx30mm prismatic cured product obtained by the same method is polished with water-resistant abrasive paper No. 600, immersed in water (37 ° C) for 24 hours, and then Autograph AG-500B (manufactured by Shimadzu Corporation) It was measured in a three-point bending strength test at a distance between supports of 20 mm.
  • a cylindrical cured product 5 mm in diameter and 3 mm in thickness obtained by the same method is immersed in water (3 ⁇ ° for 24 hours, and then subjected to a maximum load of 1000 kg using an Autograph AGS-1000D (Shimadzu).
  • the crosshead speed was measured under the condition of 2.0 mm / in.
  • a cylindrical cured product of 4 mm in diameter and 3 mm in thickness obtained by the same method is immersed in water (37 ° C) for 24 hours. The measurement was performed under the conditions of a hard sphere diameter of 1.5 mm, a load time of 30 seconds and a load of 25 kg.
  • a disk-shaped cured product having a diameter of 15 mm and a thickness of 0.5 mm obtained by the same method was polished with a water-resistant abrasive paper No. 220 and dried overnight in a desiccator to obtain a constant weight. Next, it was immersed in water (37 ° C) for one week, saturated with water absorption, weighed, and dried again in a desiccator overnight to obtain a constant weight. The amount of water absorption and the amount of dissolution were calculated according to the following equations.
  • V Volume of test piece (mm 3 )
  • the center line average roughness (m) and the maximum roughness (m) were measured according to JIS surface roughness (B0601).
  • UDMA Trimethylhexamethylene diurethane
  • TEGDMA Trimethylhexamethylene diurethane
  • P-N N-dimethylaminobenzoic acid 2
  • N-butoxyshethyl 0.3% by weight
  • hydroquinone monomethyl ether 0.06% by weight
  • an organic composite filler was prepared using hexa (methacryloxyethylenedioxy) cyclotriphosphazene (PPZ; manufactured by Kyoeisha Chemical Co., Ltd.).
  • PPZ hexa (methacryloxyethylenedioxy) cyclotriphosphazene
  • 6.12 g of an organic composite filler having an average particle diameter of 27 m and a RM-50 of 4.08 g through an 280 mesh sieve were mixed with 4.80 g of the photopolymerizable composition of Example 1 to prepare a photopolymerizable dental filler.
  • the cured product was evaluated as a composition.
  • the cured product containing the organic composite filler prepared using U-6HZTEGDMA of Example 1 has excellent mechanical properties compared to Comparative Examples 1 and 2, and also wear resistance was good, composite dental filling regard waterproof Toresin JIST 6514 (1993) standard value according (water absorption; 50 g / mm 3 or less, the dissolved amount; 7. below) good cured product satisfying the Is given. In particular, it can be seen that the bending strength is excellent.
  • the average composite particle diameter through a 500-mesh sieve was 15 m.
  • the organic composite filler was 6.12 g and RM-5. 0: 4.08 g was filled into 4.80 g of the photopolymerizable composition of Example 1 to obtain a photopolymerizable dental filling composition.
  • the bending strength of the cured product of this composition was measured, and the results in Table 2 were obtained.
  • Organic composite filler 6.1 m and RM— 50: 4.08 g was filled into 4.80 g of the photopolymerizable composition of Example 1 to obtain a photopolymerizable dental filling composition.
  • the same measurement as in Example 2 was performed on the cured product of this composition. The results in Table 2 were obtained.
  • the organic composite filler having an average particle diameter of 150; m, which passes through the 500-mesh sieve of Example 2 is an organic composite filler of 6.1 m and RM. —50: 4.08 g was charged into 4.80 g of the photopolymerizable composition of Example 1 to obtain a photopolymerizable dental filling composition. The same applies to the cured product of this composition. Measurements were made. The results in Table 2 were obtained.
  • the organic composite filler of Example 1 was prepared by setting the weight percentage ratio of U-6H / TEGDMA to 550% by weight.
  • Organic composite filler 6.12 g and RM-50: 4.08 g were added to the photopolymerizable composition of Example 1 4.80 g. to obtain a photopolymerizable dental filling composition.
  • Physical properties of a cured product of this composition were evaluated in the same manner as in Example 1.
  • An organic composite filler was produced in the same manner as in Example 1, except that the weight percentage ratio of U-6HZTE GDMA was 30/70 weight%. Average of 2 80 mesh sieve passage 6.12 g of the organic composite filler having a particle diameter of 21 xm and RM-50: 4.08 g were mixed with 4.80 g of the photopolymerizable composition of Example 1 to obtain a photopolymerizable dental filling composition. Physical properties of the cured product of this composition were evaluated in the same manner as in Example 1.
  • TMPT trimethylolpropane trimethacrylate
  • TEGDMA trimethylolpropane trimethacrylate
  • the weight percentage ratio of U-6HZTMPT was 70/30 weight%, and an organic composite filler was produced in the same manner as in Example 1.
  • Organic composite filler 6.12 g and RM-50: 4.08 g were mixed with 4.80 g of the photopolymerizable composition of Example 1 to form a photopolymerizable dental filling composition. It was decided. Physical properties of the cured product of this composition were evaluated in the same manner as in Example 1.
  • Example 7 an organic composite filler was prepared in the same manner as in Example 1, except that TEGDMA was used instead of TEGDMA, and the weight ratio of U-6H / TMPT was 30/70% by weight.
  • the average particle size of 12 im organic composite filler passing through a 280 mesh sieve, 6.12 g, and RM—50: 4.08 g were mixed with 4.80 g of the photopolymerizable composition of Example 1 to form a photopolymerizable dental filling composition. And Physical properties of this composition were evaluated in the same manner as in Example 1.
  • Example 1 In the preparation of the organic composite filler of Example 1 according to the present invention, 1,3-butyleneglycol dimethyl acrylate (BG; manufactured by Shin-Nakamura Chemical Co., Ltd.) was used instead of TEGDMA.
  • the weight percent ratio of U-6HZBG was set to 70Z30% by weight, and an organic composite filler was produced in the same manner as in Example 1.
  • Organic composite filler 6.12 g and RM-50: 4.08 g were mixed with 4.80 g of the photopolymerizable composition of Example 1 to fill photopolymerizable dental filler. The composition was used. Physical properties of the cured product of this composition were evaluated in the same manner as in Example 1.
  • the polymerizable dental filling composition of the present invention not only has excellent mechanical strength, particularly bending strength, but also has good abrasion resistance and water resistance.
  • a composition having more excellent bending strength can be obtained.
  • excellent effects can be exhibited not only when used as a dental restoration material such as a hard resin or a composite inlay, but also as a dental restoration material such as a composite resin.

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

Abstract

L'invention concerne une composition dentaire de produit d'obturation polymérisable présentant une excellente résistance mécanique, notamment une résistance à la flexion, une résistance satisfaisante à l'usure et à l'eau, et permettant d'obtenir un matériau durci présentant une excellente résistance à la flexion. Cette composition renferme un monomère organique polymérisable (E), un initiateur de polymérisation, et une charge composite organique. Le produit d'obturation comprend une poudre d'un matériau durci obtenu par polymérisation d'un mélange constitué (A) d'un isocyanurate ayant un groupe éthyléniquement insaturé, (B) d'un monomère (méth)acrylate de fonctionnalité égale ou supérieure à 2, (C) d'une charge organique, et (D) d'un initiateur de polymérisation.
PCT/JP1999/001687 1998-04-01 1999-03-31 Produit d'obturation composite organique, procede de production associe, et composition dentaire de produit d'obturation polymerisable renfermant ledit produit WO1999051190A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP8873798 1998-04-01
JP10/88737 1998-04-01

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WO1999051190A1 true WO1999051190A1 (fr) 1999-10-14

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6136204A (ja) * 1984-07-27 1986-02-20 Mitsui Petrochem Ind Ltd 歯牙用硬化性樹脂組成物
JPS6270304A (ja) * 1985-07-19 1987-03-31 ミネソタ　マイニング　アンド　マニュファクチュアリング　コンパニ− ポリエチレン性不飽和カルバモイルイソシアヌレ−トを含む組成物
JPH02174842A (ja) * 1988-12-28 1990-07-06 Jishi Toushi Kogyo Kk 人工歯とその製造方法
JPH05246819A (ja) * 1992-03-06 1993-09-24 Mitsubishi Rayon Co Ltd 光重合性歯科用組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6136204A (ja) * 1984-07-27 1986-02-20 Mitsui Petrochem Ind Ltd 歯牙用硬化性樹脂組成物
JPS6270304A (ja) * 1985-07-19 1987-03-31 ミネソタ　マイニング　アンド　マニュファクチュアリング　コンパニ− ポリエチレン性不飽和カルバモイルイソシアヌレ−トを含む組成物
JPH02174842A (ja) * 1988-12-28 1990-07-06 Jishi Toushi Kogyo Kk 人工歯とその製造方法
JPH05246819A (ja) * 1992-03-06 1993-09-24 Mitsubishi Rayon Co Ltd 光重合性歯科用組成物

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