WO2023106419A1 - 歯科用硬化性組成物 - Google Patents
歯科用硬化性組成物 Download PDFInfo
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- WO2023106419A1 WO2023106419A1 PCT/JP2022/045570 JP2022045570W WO2023106419A1 WO 2023106419 A1 WO2023106419 A1 WO 2023106419A1 JP 2022045570 W JP2022045570 W JP 2022045570W WO 2023106419 A1 WO2023106419 A1 WO 2023106419A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 166
- 239000000945 filler Substances 0.000 claims abstract description 231
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- -1 thiourea compound Chemical class 0.000 claims description 101
- 239000000126 substance Substances 0.000 claims description 50
- 238000006116 polymerization reaction Methods 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 25
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- 239000007822 coupling agent Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
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- 150000003863 ammonium salts Chemical class 0.000 description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- UMIVUKFKISBKQB-UHFFFAOYSA-N praseodymium(3+);propan-2-olate Chemical compound [Pr+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] UMIVUKFKISBKQB-UHFFFAOYSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- QZGHTLPTQXPXDG-UHFFFAOYSA-N propan-2-ol scandium Chemical compound [Sc].CC(C)O.CC(C)O.CC(C)O QZGHTLPTQXPXDG-UHFFFAOYSA-N 0.000 description 1
- NREVZTYRXVBFAQ-UHFFFAOYSA-N propan-2-ol;yttrium Chemical compound [Y].CC(C)O.CC(C)O.CC(C)O NREVZTYRXVBFAQ-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- LJAHYMASTZZGNH-UHFFFAOYSA-N propan-2-olate thulium(3+) Chemical compound [Tm+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] LJAHYMASTZZGNH-UHFFFAOYSA-N 0.000 description 1
- HJCRVWSKQNDSPZ-UHFFFAOYSA-N propan-2-olate;samarium(3+) Chemical compound [Sm+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] HJCRVWSKQNDSPZ-UHFFFAOYSA-N 0.000 description 1
- RAKJHSBPOPJWKI-UHFFFAOYSA-N propan-2-olate;ytterbium(3+) Chemical compound [Yb+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] RAKJHSBPOPJWKI-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- HCOKJWUULRTBRS-UHFFFAOYSA-N propan-2-yloxysilane Chemical compound CC(C)O[SiH3] HCOKJWUULRTBRS-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 159000000005 rubidium salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 159000000008 strontium salts Chemical class 0.000 description 1
- YTBRWVXQNMQQTK-UHFFFAOYSA-N strontium;ethanolate Chemical compound CCO[Sr]OCC YTBRWVXQNMQQTK-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JKNHZOAONLKYQL-UHFFFAOYSA-K tribromoindigane Chemical compound Br[In](Br)Br JKNHZOAONLKYQL-UHFFFAOYSA-K 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- STDMRMREKPZQFJ-UHFFFAOYSA-H tricopper;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[Cu+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O STDMRMREKPZQFJ-UHFFFAOYSA-H 0.000 description 1
- MCXZOLDSEPCWRB-UHFFFAOYSA-N triethoxyindigane Chemical compound [In+3].CC[O-].CC[O-].CC[O-] MCXZOLDSEPCWRB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BYMUNNMMXKDFEZ-UHFFFAOYSA-K trifluorolanthanum Chemical compound F[La](F)F BYMUNNMMXKDFEZ-UHFFFAOYSA-K 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- QNWOFLWXQGHSRH-UHFFFAOYSA-N trimethyl-[methyl(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[SiH](C)O[Si](C)(C)C QNWOFLWXQGHSRH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229940041260 vanadyl sulfate Drugs 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/50—Preparations specially adapted for dental root treatment
- A61K6/54—Filling; Sealing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
-
- 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
- A61K6/80—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 a dental curable composition.
- a dental curable composition is a mixture of a polymerizable monomer, a filler, and a polymerization initiator, and is currently the most widely used material for filling and repairing tooth defects or tooth decay. It's becoming The composition is classified into several types according to its application. The characteristics required for each application are different, and for example, a dental hardening composition used for dental cement requires high fluidity.
- a dental curable composition used as a dental abutment building material is particularly required to have high formability, ie, shape retention, and high mechanical strength. By using specific compounding components in the composition or by adjusting the ratio of compounding components, etc., it is possible to exhibit properties preferable for each application.
- Patent Document 1 by combining a spherical filler and an irregular filler, it is possible to achieve both excellent fluidity of the paste and physical properties such as mechanical strength of the cured product, which have been difficult to achieve in the past.
- a curable composition is disclosed.
- the dental curable composition of Patent Document 2 uses a filler treated with a surfactant and a hydrophobizing agent to obtain particles having a particle size of less than 0.05 ⁇ m, which is widely used as a thixotropic modifier. It is described that it is possible to improve moldability while maintaining high paste fluidity and physical properties such as mechanical strength of cured products without using fine particle fillers.
- Patent Literature 1 does not describe the shapeability of the paste when building the abutment, and only explains that a filler with a particle size of less than 0.05 ⁇ m can be used as a thixotropy modifier.
- a filler with a particle size of less than 0.05 ⁇ m can be used as a thixotropy modifier.
- Patent Document 1 directly describes this. no.
- the curable dental composition described in Patent Document 1 contains a filler having an average particle size of less than 0.05 ⁇ m as a thixotropic property modifier, and is used as a dental abutment building material. It was found that when the paste was made to have important sculpting properties, the flowability was compromised.
- the dental curable composition of Patent Document 2 uses a filler treated with a surfactant and a hydrophobic treatment agent to Although the formability of the paste can be improved to some extent, the formability is not at a sufficient level as a dental abutment building material, and the flow of the paste decreases as the filling amount of the filler is increased to further improve the formability. sexuality is severely impaired. Therefore, it has been found that the dental curable composition of Patent Document 2 cannot achieve both sufficient formability as a dental abutment construction material and paste fluidity at a high level. .
- the composition of the dental hardening composition is changed so as to have the desired fluidity, and the dental abutment that requires the moldability of the paste.
- Applications such as building materials can be accommodated by changing the composition of the dental hardenable composition so as to have the desired formability. Therefore, the problem of providing a dental curable composition that has both the properties of compatibility between paste fluidity and paste formability, which are contradictory, has been hardly studied due to its difficulty. It was adapted for each application.
- an object of the present invention is to provide a dental curable composition that has excellent mechanical strength in a cured product and that has paste properties such as high fluidity and sufficient formability.
- the present inventors have made intensive studies to solve the above problems, and found that, in addition to combining a spherical filler and an amorphous filler in a specific ratio, a hydrophilic polymerizable monomer in the polymerizable monomer By reducing the content of the paste to a certain level or less, it was found that the paste has high formability when left standing, but exhibits high fluidity when an external force is applied. We have succeeded in obtaining a dental curable composition that has paste properties, which were conventionally thought to be contradictory. Based on these findings, the inventors have made further studies and completed the present invention.
- the present invention includes the following inventions.
- the polymerizable monomer (A) is, in a total of 100 parts by mass of the polymerizable monomer (A), 0 parts by mass or more and less than 15 parts by mass of a hydrophilic polymerizable monomer having no acidic group (A-1a), and 55 parts by mass or more of a hydrophobic polymerizable monomer having no acidic group (A-1b) including The solubility of the hydrophilic polymerizable monomer (A-1a) having no acidic group in water at 25° C.
- the filler (B) is, in a total of 100 parts by mass of the filler (B), 1 to 60 parts by mass of a spherical filler (B-1) having an average particle diameter of 0.01 to 1 ⁇ m; 40 to 99 parts by mass of an irregularly shaped filler (B-2) having an average particle diameter of 0.5 to 6.0 ⁇ m, and 0 to 10 parts by mass of an irregularly shaped fine particle filler having an average particle diameter of less than 0.5 ⁇ m (including B-3), Spherical filler (B-1) is hydrophobized with a hydrophobizing agent (x-1), A dental curable composition, wherein the polymerization initiator (C) contains a photopolymerization initiator (C-1).
- the filler (B) is, in a total of 100 parts by mass of the filler (B), 10 to 30 parts by mass of the spherical filler (B-1),
- the hydrophobizing agent (x-1) is at least one selected from the group consisting of silane coupling agents, titanate coupling agents, aluminate coupling agents, and zirco-aluminate coupling agents.
- the hydrophobizing agent (x-2) is a silane coupling agent having a polymerizable group represented by the following general formula (1).
- Y-SiR n X (3-n) (1)
- Y represents a polymerizable group or a monovalent organic group having a polymerizable group
- R represents a group selected from the group consisting of an alkyl group, an aryl group and an aralkyl group
- X represents a hydroxyl group or hydrolysis
- n represents an integer of 0, 1 or 2.
- multiple R's may be the same or different
- multiple X's may be the same or different.
- Y is a group in which a (meth)acryloyl group and an organic group are bonded via a divalent group containing an oxygen atom, wherein the (meth)acryloyl group is bonded via the divalent group containing an oxygen atom
- the first agent contains a polymerizable monomer (A), a filler (B), and a chemical polymerization accelerator (D-2),
- a dental abutment building material comprising the dental curable composition according to any one of [1] to [11].
- a dental resin cement comprising the dental curable composition according to any one of [1] to [11].
- a dental curable composition that has both excellent mechanical strength in a cured product and paste properties of high fluidity and sufficient formability.
- the property of the paste of the curable dental composition changes such that it is excellent in formability when it is left still and becomes highly fluid when an external force (for example, pressure contact) is applied. Because it has both the contradictory properties of excellent fluidity and moldability, it has a single composition without changing the composition, such as dental cement that requires fluidity and dental cement that requires moldability. It is possible to provide a dental curable composition that can be used for any application such as abutment building materials.
- the dental curable composition of the present invention comprises a polymerizable monomer (A), a filler (B), and a polymerization initiator (C), wherein the polymerizable monomer (A) is the polymerizable monomer Of the total 100 parts by mass of the monomer (A), 0 parts by mass or more and less than 15 parts by mass of a hydrophilic polymerizable monomer (A-1a) that does not have an acidic group, and 55 parts by mass or more that does not have an acidic group.
- the solubility of the hydrophilic polymerizable monomer (A-1a) containing the hydrophobic polymerizable monomer (A-1b) and having no acidic group in water at 25° C.
- Spherical filler (B-1) in which the filler (B) has an average particle diameter of 0.01 to 1 ⁇ m in 1 to 60 parts by mass of the total 100 parts by mass of the filler (B), and 40 to 99 parts by mass of the average particle Including irregularly shaped filler (B-2) having a diameter of 0.5 to 6.0 ⁇ m and 0 to 10 parts by mass of irregularly shaped fine particle filler (B-3) having an average particle diameter of less than 0.5 ⁇ m, spherical
- the filler (B-1) is hydrophobized with a hydrophobizing agent (x-1), and the polymerization initiator (C) contains a photopolymerization initiator (C-1).
- a hydrophilic interaction between a polymerizable monomer and a filler is generally known as a factor that increases the viscosity of the paste. Therefore, for the purpose of suppressing the viscosity increase of the paste, from the viewpoint of weakening the hydrophilic interaction, it is conceivable to use a relatively low hydrophilic polymerizable monomer and a filler whose surface has been subjected to a hydrophobic treatment. be done. The interaction that occurs between the polymerizable monomer having relatively low hydrophilicity and the filler whose surface has been subjected to hydrophobic treatment is extremely weak.
- the dental curable composition of the present invention has sufficient shapeability and contains a certain amount of spherical filler in the filler, so that the sliding effect of the spherical filler generated when an external force is applied , the interference between fillers can be reduced, so that the fluidity of the paste is not impaired when an external force is applied.
- the dental curable composition of the present invention has high formability when left standing, and has the property of changing that the paste exhibits high fluidity when an external force is applied.
- a radically polymerizable monomer is preferably used as the polymerizable monomer (A) used in the dental curable composition of the present invention.
- the radical polymerizable monomer in the polymerizable monomer (A) include (meth)acrylate polymerizable monomers, (meth)acrylamide polymerizable monomers, ⁇ -cyanoacrylic acid, (meth)acryl acid, ⁇ -halogenated acrylic acid, crotonic acid, cinnamic acid, sorbic acid, maleic acid, esters such as itaconic acid, vinyl esters, vinyl ethers, mono-N-vinyl derivatives, styrene derivatives and the like.
- the polymerizable monomer (A) is roughly classified into a polymerizable monomer (A-1) having no acidic group and a polymerizable monomer (A-2) having an acidic group.
- the term (meth)acryl is a generic term for methacryl and acryl.
- a hydrophilic polymerizable monomer having no acidic group and having a solubility in water at 25° C. of 4.5 g/L or more A-1a: divided into hydrophobic polymerizable monomers (A-1b) having no acidic group, which have a solubility in water at 25° C. of less than 4.5 g/L.
- the polymerizable monomer (A) is a hydrophilic polymerizable monomer (A-1a) having no acidic group (hereinafter simply referred to as "hydrophilic polymerizable monomer ( A-1a)”) in an amount of less than 15 parts by mass based on the total 100 parts by mass of the polymerizable monomer (A).
- the hydrophilic polymerizable monomer (A-1a) means a monomer having no acidic group and having a solubility in water at 25° C. of 4.5 g/L or more.
- the hydrophilic polymerizable monomer (A-1a) which is defined by the amount dissolved in water, is contained from the viewpoint of compatibility between paste fluidity and formability.
- the amount is less than 15 parts by weight in total 100 parts by weight of the polymerizable monomer (A).
- the content of the hydrophilic polymerizable monomer (A-1a) in the dental curable composition of the present invention is 15 parts by mass or more based on the total 100 parts by mass of the polymerizable monomer (A) reduces the fluidity of the paste and becomes incompatible with formability. Therefore, the content of the hydrophilic polymerizable monomer (A-1a) in the dental curable composition of the present invention is 10 parts by mass or less based on the total of 100 parts by mass of the polymerizable monomer (A). Preferably, 5 parts by mass or less is more preferable. Also, the content of the hydrophilic polymerizable monomer (A-1a) may be 0 parts by mass in the total 100 parts by mass of the polymerizable monomer (A).
- the hydrophilic polymerizable monomer (A-1a) improves the wettability of the curable dental composition to tooth substance.
- the hydrophilic polymerizable monomer (A-1a) is preferably a radically polymerizable monomer having a polymerizable group without an acidic group, and from the viewpoint of facilitating radical polymerization, the polymerizable group is (meth ) acryloyloxy groups and/or (meth)acrylamide groups are preferred.
- hydrophilic polymerizable monomer (A-1a) examples include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 1,3-dihydroxypropyl Hydrophilic (meth)acrylate monofunctionals such as (meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, 2-((meth)acryloyloxy)ethyltrimethylammonium chloride, tetrahydrofurfuryl (meth)acrylate, etc.
- Polymerizable monomer triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, nonaethylene glycol di(meth)acrylate, 1,3-bis(methacryloyloxy)-2-propanol, 1,2 - hydrophilic (meth)acrylate-based polyfunctional polymerizable monomers such as bis(3-methacryloyloxy-2-hydroxypropoxy)ethane; N-methylol (meth)acrylamide, N-hydroxyethyl (meth)acrylamide, N,N-bis(2-hydroxyethyl) (meth)acrylamide, N-methoxymethyl (meth)acrylamide, N-ethoxymethyl (meth)acrylamide, diacetone (meth)acrylamide, 4-(meth)acryloylmorpholine, N- hydrophilic (meth)acrylamide-based polymerizable monomers such as trihydroxymethyl-N-methyl(meth)acrylamide, N,N-dimethylacrylamide, N,
- hydrophilic polymerizable monomers (A-1a) it is preferable to use (meth)acrylate polyfunctional polymerizable monomers from the viewpoint of curability.
- (meth)acrylate polyfunctional polymerizable monomers from the viewpoint of curability.
- triethylene glycol dimethacrylate commonly known as "3G”
- 1,3-bis(methacryloyloxy)-2-propanol 1,2-bis(3-methacryloyloxy-2-hydroxypropoxy)ethane
- #801 is even more preferred.
- the above hydrophilic polymerizable monomer (A-1a) may be used alone or in combination of two or more.
- the polymerizable monomer (A) is a hydrophobic polymerizable monomer (A-1b) having no acidic group (hereinafter simply referred to as "hydrophobic polymerizable monomer ( A-1b)”).
- the hydrophobic polymerizable monomer (A-1b) means a monomer having no acidic group and having a solubility in water at 25° C. of less than 4.5 g/L.
- the hydrophobic polymerizable monomer (A-1b) when combined with the filler (B) containing the hydrophobized spherical filler (B-1), the polymerizable monomer and between the filler weakens the hydrophilic interaction, and can improve the fluidity of the paste.
- the hydrophobic polymerizable monomer (A-1b) can suppress the stringiness (ease of stringiness) of the dental curable composition and improve the mechanical strength of the cured product. .
- the hydrophobic polymerizable monomer (A-1b) is preferably a radically polymerizable monomer having a polymerizable group without an acidic group, and from the viewpoint of facilitating radical polymerization, the polymerizable group is (meth ) acryloyloxy groups and/or (meth)acrylamide groups are preferred.
- the hydrophobic polymerizable monomer (A-1b) include, in addition to a hydrophobic monofunctional polymerizable monomer, a hydrophobic aromatic compound-based bifunctional polymerizable monomer, a hydrophobic Crosslinkable polymerizable monomers such as aliphatic compound-based bifunctional polymerizable monomers and hydrophobic trifunctional or higher polymerizable monomers are exemplified.
- hydrophobic monofunctional polymerizable monomers examples include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, p-cumyl- phenoxyethylene glycol (meth)acrylate, 2-phenoxybenzyl (meth)acrylate, stearyl (meth)acrylate, dicyclopentanyl (meth)acrylate, butoxydiethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, etc. .
- benzyl methacrylate, isobornyl methacrylate, and p-cumyl-phenoxyethylene glycol methacrylate are preferred.
- Hydrophobic aromatic compound-based bifunctional polymerizable monomers include, for example, 2,2-bis((meth)acryloyloxyphenyl)propane, 2,2-bis[4-(2-hydroxy-3- (meth)acryloyloxypropoxy)phenyl]propane, 2,2-bis(4-(meth)acryloyloxyethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypolyethoxyphenyl)propane, 2, 2-bis(4-(meth)acryloyloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxytriethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxytetra ethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxypentaethoxyphenyl)propane, 2,2-bis(4-(meth)acryloyloxyd
- Bis-GMA 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane
- Bis-GMA 2,2-bis(4-methacryloyloxyethoxyphenyl)propane
- 2,2-bis(4-methacryloyloxypolyethoxyphenyl)propane average number of added moles of ethoxy groups: 2.6, commonly known as "D-2.6E”
- D-2.6E 2,2-bis(4-methacryloyloxydiethoxy phenyl)propane
- D-2.6E 2,2-bis(4-methacryloyloxytriethoxyphenyl)propane
- Bis-methacryloyloxytetraethoxyphenyl)propane 2,2-bis(4-methacryloyloxypentaethoxyphenyl) Propane
- Bis-GMA, D-2.6E are more preferred.
- aliphatic compound-based bifunctional polymerizable monomers include monoethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, butylene glycol di(meth)acrylate, neo Pentyl glycol di(meth)acrylate, 1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, 2,2,4- and trimethylhexamethylenebis(2-carbamoyloxyethyl)di(meth)acrylate.
- NPG neopentyl glycol dimethacrylate
- UDMA 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl) dimethacrylate
- DD 1,10-decanediol dimethacrylate
- trifunctional or higher polymerizable monomers examples include trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, trimethylolmethane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, N,N-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetra( meth)acrylate, 1,7-diacryloyloxy-2,2,6,6-tetra(meth)acryloyloxymethyl-4-oxaheptane and the like.
- N,N-(2,2,4-trimethylhexamethylene)bis[2-(aminocarboxy)propane-1,3-diol]tetramethacrylate is
- hydrophobic polymerizable monomers (A-1b) from the viewpoint of handling properties and mechanical strength of cured products, aromatic compound-based bifunctional polymerizable monomers and aliphatic compound-based bifunctional polypolymerizable monomers are preferred.
- the above hydrophobic polymerizable monomer (A-1b) may be blended singly or in combination of two or more.
- the content of the hydrophobic polymerizable monomer (A-1b) in the dental curable composition of the present invention is excessive, the wettability of the dental curable composition to tooth substance is lowered. If the content is too small, the hydrophilic interaction between the polymerizable monomer and the filler is strong, and the fluidity of the paste may become insufficient. The mechanical strength of the object may become insufficient. Therefore, the content of the hydrophobic polymerizable monomer (A-1b) in the dental curable composition of the present invention is 55 parts by mass or more based on the total 100 parts by mass of the polymerizable monomer (A).
- the content of the hydrophobic polymerizable monomer (A-1b) is 55 parts by mass or more and 100 parts by mass or less based on the total 100 parts by mass of the polymerizable monomer (A). is a dental curable composition.
- the dental curable composition of the present invention contains a hydrophilic polymerizable monomer (A-1a)
- the total amount of the polymerizable monomer (A) is 100 In the parts by mass, the content of the hydrophilic polymerizable monomer (A-1a) is more than 0 parts by mass and less than 15 parts by mass, and the content of the hydrophobic polymerizable monomer (A-1b) is 85 parts by mass.
- a dental curable composition containing at least 100 parts by mass and less than 100 parts by mass may be mentioned.
- the dental curable composition of the present invention contains a polymerizable monomer (A-2) having an acidic group
- the content of the polymerizable monomer (A-2) having an acidic group is more than 0 parts by mass and 30 parts by mass or less
- the hydrophobic polymerizable monomer (A-1b) content is 55 parts by mass or more and less than 100 parts by mass.
- the content of each monomer can be appropriately changed based on the description of this specification.
- the dental curable composition of the present invention may contain a polymerizable monomer (A-2) having an acidic group.
- a polymerizable monomer (A-2) having an acidic group used in the present invention a radically polymerizable monomer having at least one or more acidic group and polymerizable group is preferred.
- the acidic group possessed by the polymerizable monomer (A-2) having an acidic group includes a phosphoric acid group, a pyrophosphate group, a thiophosphoric acid group, a phosphonic acid group, a carboxylic acid group, Acidic groups such as sulfonic acid groups are preferred.
- the polymerizable group possessed by the polymerizable monomer (A-2) having an acidic group is preferably a (meth)acryloyloxy group and/or a (meth)acrylamide group.
- Polymerizable monomers having a phosphoric acid group include 2-(meth)acryloyloxyethyl dihydrogen phosphate, 3-(meth)acryloyloxypropyl dihydrogen phosphate, 4-(meth)acryloyloxybutyl dihydrogen Phosphate, 5-(meth)acryloyloxypentyl dihydrogen phosphate, 6-(meth) acryloyloxyhexyl dihydrogen phosphate, 7-(meth) acryloyloxyheptyl dihydrogen phosphate, 8-(meth) acryloyloxyoctyl dihydrogen phosphate hydrogen phosphate, 9-(meth)acryloyloxynonyl dihydrogen phosphate, 10-(meth)acryloyloxydecyldihydrogenphosphate, 11-(meth)acryloyloxyundecyldihydrogenphosphate, 12-(meth)acryloyl oxidodecyl
- Examples of the polymerizable monomer having a pyrophosphate group include bis[2-(meth)acryloyloxyethyl] pyrophosphate, bis[4-(meth)acryloyloxybutyl] pyrophosphate, bis[6-(meth)pyrophosphate acryloyloxyhexyl], bis[8-(meth)acryloyloxyoctyl] pyrophosphate, bis[10-(meth)acryloyloxydecyl] pyrophosphate, and acid chlorides, alkali metal salts and amine salts thereof.
- Polymerizable monomers having a thiophosphoric acid group include 2-(meth)acryloyloxyethyl dihydrogenthiophosphate, 3-(meth)acryloyloxypropyl dihydrogenthiophosphate, 4-(meth)acryloyloxybutyl dihydrogenthiophosphate, hydrogenthiophosphate, 5-(meth)acryloyloxypentyl dihydrogenthiophosphate, 6-(meth)acryloyloxyhexyldihydrogenthiophosphate, 7-(meth)acryloyloxyheptyldihydrogenthiophosphate, 8-( meth)acryloyloxyoctyl dihydrogenthiophosphate, 9-(meth)acryloyloxynonyl dihydrogenthiophosphate, 10-(meth)acryloyloxydecyldihydrogenthiophosphate, 11-(meth)acryloyloxyundecyldihydro Genthiophosphate, 12-(
- Polymerizable monomers having a phosphonic acid group include 2-(meth)acryloyloxyethylphenylphosphonate, 5-(meth)acryloyloxypentyl-3-phosphonopropionate, 6-(meth)acryloyloxyhexyl- 3-phosphonopropionate, 10-(meth)acryloyloxydecyl-3-phosphonopropionate, 6-(meth)acryloyloxyhexylphosphonoacetate, 10-(meth)acryloyloxydecylphosphonoacetate and these acid chlorides, alkali metal salts and ammonium salts of
- polymerizable monomer having a carboxylic acid group a monofunctional (meth)acrylic acid ester having one carboxyl group or its acid anhydride group in the molecule, a plurality of carboxyl groups in the molecule or its acid anhydride group monofunctional (meth)acrylic acid esters having a monofunctional group and acid chlorides, alkali metal salts and ammonium salts thereof.
- Monofunctional polymerizable monomers having one carboxyl group or an acid anhydride group thereof in the molecule include (meth)acrylic acid, N-(meth)acryloylglycine, N-(meth)acryloylaspartic acid, 2-(meth) acryloyloxyethyl hydrogen succinate, 2-(meth) acryloyloxyethyl hydrogen phthalate, 2-(meth) acryloyloxyethyl hydrogen malate, O-(meth) acryloyl tyrosine, N-(meth) Acryloyltyrosine, N-(meth)acryloylphenylalanine, N-(meth)acryloyl-p-aminobenzoic acid, N-(meth)acryloyl-o-aminobenzoic acid, 2-(meth)acryloyloxybenzoic acid, 3-( meth)acryloyloxybenzoic acid, 4-(meth)acryloyloxybenz
- Monofunctional polymerizable monomers having multiple carboxyl groups or acid anhydride groups thereof in the molecule include 6-(meth)acryloyloxyhexane-1,1-dicarboxylic acid, 9-(meth)acryloyloxynonane -1,1-dicarboxylic acid, 10-(meth)acryloyloxydecane-1,1-dicarboxylic acid, 11-(meth)acryloyloxyundecane-1,1-dicarboxylic acid, 12-(meth)acryloyloxydecane-1 ,1-dicarboxylic acid, 13-(meth)acryloyloxytridecane-1,1-dicarboxylic acid, 4-(meth)acryloyloxyethyl trimellitate, 4-(meth)acryloyloxyethyl trimellitate anhydride, 4 -(meth) acryloyloxybutyl trimellitate, 4-(meth) acryloyloxyhexyl trim
- Polymerizable monomers having a sulfonic acid group include 2-sulfoethyl (meth)acrylate and their acid chlorides, alkali metal salts and ammonium salts.
- a phosphoric acid group-containing polymerizable monomer Or polymerizable monomers having a carboxylic acid group are preferred, such as 2-(meth)acryloyloxyethyl dihydrogenphosphate, 3-(meth)acryloyloxypropyl dihydrogenphosphate, 4-(meth)acryloyloxybutyl dihydrogen phosphate, gen phosphate, 5-(meth) acryloyloxypentyl dihydrogen phosphate, 6-(meth) acryloyloxyhexyl dihydrogen phosphate, 7-(meth) acryloyloxyheptyl dihydrogen phosphate, 8-(meth) acryloyloxy octyl Dihydrogen Phosphate, 9-(Meth) Acryloyloxy Nonyl Dihydrogen Phosphate, 10-(
- the above-mentioned polymerizable monomer (A-2) having an acidic group may be blended singly or in combination of two or more.
- the content of the polymerizable monomer (A-2) having an acidic group in the dental curable composition of the present invention should be set to It is preferably from 0 to 30 parts by mass, more preferably from 0 to 20 parts by mass, and even more preferably from 0 to 15 parts by mass, based on the total of 100 parts by mass.
- the dental hardenable composition of the present invention must contain a filler (B) in order to adjust the fluidity and formability of the paste and to increase the mechanical strength of the hardened product.
- a filler B
- examples of such fillers include inorganic fillers, organic fillers, and organic-inorganic composite fillers.
- various glasses mainly composed of silica, and containing oxides of heavy metals, boron, aluminum, etc., if necessary.
- glass powder of general composition such as fused silica, quartz, soda lime silica glass, E glass, C glass, borosilicate glass (Pyrex (registered trademark) glass); barium glass (GM27884, 8235, manufactured by SCHOTT, E-2000, E-3000, manufactured by ESSTECH), strontium borosilicate glass (E-4000, manufactured by ESSTECH), lanthanum glass ceramics (GM31684, manufactured by SCHOTT), fluoroaluminosilicate glass (GM35429, G018-091, G018-117, manufactured by SCHOTT), etc.], various ceramics, composite oxides such as silica-titania, silica-zirconia, diatomaceous earth, kaolin, clay minerals (montmorillonite, etc.), activated clay, synthetic zeo
- various glasses composite oxides such as silica-titania and silica-zirconia, silica-coated core-shell calcium fluoride, and silica-coated core-shell structure ytterbium fluoride, core-shell yttrium fluoride surface-coated with silica, core-shell calcium phosphate surface-coated with silica, core-shell barium sulfate surface-coated with silica, silica-coated surface Zirconium dioxide having a core-shell structure, titanium dioxide having a core-shell structure having a surface coated with silica, and hydroxyapatite having a core-shell structure having a surface coated with silica are preferable.
- organic filler components include polymethyl methacrylate, polyethyl methacrylate, methyl methacrylate-ethyl methacrylate copolymer, crosslinked polymethyl methacrylate, crosslinked polyethyl methacrylate, polyamide, polyvinyl chloride, and polystyrene. , chloroprene rubber, nitrile rubber, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, acrylonitrile-styrene copolymer, acrylonitrile-styrene-butadiene copolymer and the like.
- the organic-inorganic composite filler is obtained by previously adding a polymerizable monomer to the above inorganic filler, making it into a paste, polymerizing it, and pulverizing it.
- a polymerizable monomer for example, TMPT filler (trimethylolpropane methacrylate and silica filler are mixed, polymerized and pulverized) can be used.
- the shape of the filler (B) includes spherical and irregular shapes.
- the spherical filler (B-1) and the amorphous filler (B-2) are used as the filler (B) from the viewpoint of achieving both paste fluidity and formability. must be used together.
- the spherical filler (B-1) is obtained by taking a photograph of the filler with an electron microscope and observing round particles in the unit field of view. It is a filler having an average degree of uniformity of 0.6 or more.
- the spherical filler (B-1) in the dental curable composition of the present invention preferably has an average degree of uniformity of 0.7 or more, more preferably 0.8 or more, from the viewpoint of excellent slipping effect. .
- the material of the filler is not particularly limited because the spherical filler exhibits a slipping effect and can reduce interference between fillers.
- One embodiment includes a dental curable composition in which the spherical filler (B-1) is an inorganic filler.
- the spherical filler (B-1) used in the present invention has an average particle size of 0.01 to 1 ⁇ m, preferably 0.02 to 0.5 ⁇ m, more preferably 0.05 to 0.1 ⁇ m. If the average particle size is less than 0.01 ⁇ m, the specific surface area increases and the paste is thickened, so that a sufficient amount of filler cannot be added and the mechanical strength is lowered. On the other hand, if the average particle size exceeds 1 ⁇ m, the surface area of the spherical filler is reduced, and a hardened product of the dental hardenable composition having high formability cannot be obtained.
- the average particle size of the filler (B) means the average particle size before the surface treatment.
- the spherical filler (B-1) does not necessarily have to be produced or obtained as a single particle. It may be obtained by mixing one or more fillers.
- the spherical filler (B-1) used in the present invention must be a spherical filler hydrophobized with a hydrophobizing agent (x-1).
- a hydrophobizing agent (x-1) By including a certain amount of the hydrophobically treated spherical filler (B-1), in addition to the sliding effect that occurs when an external force is applied, the hydrophilic interaction that occurs between the polymerizable monomer and the filler is suppressed. It is possible to improve the fluidity of the paste without impairing the fluidity of the paste when it is weakened and an external force is applied.
- the hydrophobizing agent (x-1) will be described later.
- the average particle size of the amorphous filler (B-2) used in the present invention is 0.5 to 6.0 ⁇ m, preferably 1.0 to 5.0 ⁇ m from the viewpoint of mechanical strength and film thickness. 5 to 3.0 ⁇ m is more preferable.
- the average particle size is less than 0.5 ⁇ m, the specific surface area of the irregular filler increases, and the fluidity of the paste decreases.
- the average particle size exceeds 6.0 ⁇ m, the dispersibility of the amorphous filler in the dental curable composition deteriorates, making it impossible to prepare a uniform paste.
- the amorphous filler (B-2) does not necessarily have to be produced or obtained as a single particle, and if the average particle size of each is within the above range, the average particle size or the components are different. It may be obtained by mixing two or more fillers.
- the cured product has excellent mechanical strength and the paste shapeability is excellent.
- the amorphous filler (B-2) By including a predetermined amount of the amorphous filler (B-2) in the total of 100 parts by mass of the filler (B), the cured product has excellent mechanical strength and the paste shapeability is excellent.
- the amorphous filler (B-2) By combining the amorphous filler (B-2) with the spherical filler (B-1), excellent fluidity of the paste of the dental curable composition of the present invention can be obtained.
- the irregularly shaped fine particle filler (B-3) acts as a thixotropy modifier, so fine adjustment of fluidity and the like can be performed.
- the amorphous fine particle filler (B-3) does not necessarily have to be produced or obtained as a single particle. It may be obtained by mixing one or more fillers.
- the dental curable composition of the present invention contains 1 to 60 parts by mass of the spherical filler (B-1) and 40 to 99 parts by mass of the amorphous filler (B-2) in the total of 100 parts by mass of the filler (B). , and 0 to 10 parts by mass of the amorphous fine particle filler (B-3). Outside this range, it becomes impossible to achieve both excellent fluidity and formability.
- the filler (B) contains 3 to 55 parts by mass of the spherical filler (B-1), 54.9 to 96.9 parts by mass of the irregular filler (B-2), and the irregular fine particle filler (B-3).
- the content of the filler (B) in the dental curable composition of the present invention is the sum of the polymerizable monomers (A) With respect to 100 parts by mass, it is preferably 50 to 2000 parts by mass, more preferably 100 to 1500 parts by mass, and even more preferably 150 to 1000 parts by mass from the viewpoint of superior effects.
- the content of the filler (B) in the dental curable composition of the present invention is , preferably 45 to 95 parts by mass, more preferably 55 to 92 parts by mass, even more preferably 60 to 90 parts by mass.
- the average particle size of the filler can be obtained by a laser diffraction scattering method or electron microscope observation of the particles.
- the laser diffraction scattering method is convenient for measuring the particle size of 0.1 ⁇ m or more
- the electron microscope observation is convenient for measuring the particle size of ultrafine particles of less than 0.1 ⁇ m.
- 0.1 ⁇ m is a value measured by a laser diffraction scattering method.
- the laser diffraction scattering method is measured on a volume basis using a 0.2% sodium hexametaphosphate aqueous solution as a dispersion medium using a laser diffraction particle size distribution analyzer (SALD-2300: manufactured by Shimadzu Corporation). be able to.
- SALD-2300 manufactured by Shimadzu Corporation
- electron microscopic observation is performed by taking a photograph of particles with an electron microscope (manufactured by Hitachi, Ltd., S-4000 type), and measuring the particle diameter of the particles (200 or more) observed in the unit field of view of the photograph. , image analysis type particle size distribution measurement software (Mac-View (manufactured by Mountec Co., Ltd.)). At this time, the particle diameter is obtained as an arithmetic mean value of the longest length and the shortest length of the particles, and the average primary particle diameter is calculated from the number of particles and their particle diameters.
- the dental curable composition of the present invention it is necessary to use two or more fillers having different materials, particle size distributions and morphologies by mixing or combining them.
- the fillers are densely packed and the number of interaction points between the fillers and the polymerizable monomer or between the fillers increases.
- Different types of fillers may be included in each particle size filler.
- particles other than the filler may be unintentionally contained as impurities within a range that does not impair the effects of the present invention.
- the filler (B) in the present invention preferably has its surface treated with a hydrophobizing agent for the purpose of improving dispersibility in the polymerizable monomer, and in particular the spherical filler (B-1) is It must be hydrophobized with a hydrophobizing agent (x-1). Further, the amorphous filler (B-2) is hydrophobized with a hydrophobizing agent (x-2) from the viewpoint of excellent dispersibility in polymerizable monomers, mechanical strength, etc. is preferred.
- a hydrophobizing agent is not particularly limited, because a hydrophobizing-treated filler (especially spherical filler (B-1)) can weaken the hydrophilic interaction with the polymerizable monomer.
- a hydrophobizing-treated filler especially spherical filler (B-1)
- Any known surface treatment agent capable of imparting hydrophobicity is employed without limitation.
- the hydrophobic treatment agents (x-1) and (x-2) may be the same or different.
- the surface treatment agent used for surface treatment may not contain a surfactant.
- One embodiment is a curable dental composition in which spherical fillers (B-1) are hydrophobized only with a hydrophobizing agent (x-1).
- Other embodiments include dental hardenable compositions in which the spherical filler (B-1) is not treated with a surfactant.
- Yet another embodiment includes dental hardenable compositions wherein all fillers (B) are not treated with surfactants.
- Another embodiment includes a dental curable composition containing a polymerizable monomer (A), a filler (B), and a polymerization initiator (C) and containing no surfactant.
- Examples of typical hydrophobizing agents (x-1) include silane coupling agents, titanate coupling agents, aluminate coupling agents, and zirco-aluminate coupling agents. Among these, treatment with a silane coupling agent is particularly preferable because the effect of the present invention is high.
- the hydrophobizing agent (x-1) may be used alone or in combination of two or more.
- the surface treatment layer using them may be a surface treatment layer of a mixture of two or more surface treatment agents, or a plurality of surface treatment layers. It may be a surface treatment layer having a multi-layer structure in which is laminated.
- As the surface treatment method a known method can be used without any particular limitation.
- the silane coupling agent is not particularly limited as long as it can impart hydrophobicity, and known silane coupling agents can be used.
- a silane coupling agent having a functional group is preferably used.
- a silane coupling agent having a polymerizable group represented by the following general formula (1) the dispersibility of the filler is improved and the fluidity of the paste is improved. Polymerization with the polymer improves the mechanical strength of the cured product.
- Y-SiR n X (3-n) (1)
- Y represents a polymerizable group or a monovalent organic group having a polymerizable group
- R represents a group selected from the group consisting of an alkyl group, an aryl group and an aralkyl group
- X represents a hydroxyl group or hydrolysis
- n represents an integer of 0, 1 or 2.
- multiple R's may be the same or different, and multiple X's may be the same or different. is also good.
- Y has there are no particular restrictions on the type of polymerizable group that Y has, and examples include (meth)acryloyl groups, vinyl groups, mercapto groups, (meth)allyl groups, and epoxy groups. Among these, a (meth)acryloyl group is preferred, and a methacryloyl group is more preferred, from the viewpoint of mechanical strength and the like.
- Y is a monovalent organic group having a polymerizable group
- the polymerizable group when the polymerizable group is bonded to the organic group, the polymerizable group may be directly bonded to the organic group, an oxygen atom, a nitrogen atom may be bonded through a divalent group containing a heteroatom such as
- Y when the polymerizable group of Y is a (meth)acryloyl group, Y may form a (meth)acryloyloxy group or a (meth)acrylamide group.
- the number of polymerizable groups that Y has is not particularly limited, but is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1. When Y has a plurality of polymerizable groups, they may be the same or different.
- Y may be only the above polymerizable group, or may be a monovalent organic group having a polymerizable group.
- the functional group and the organic group are bonded directly or indirectly via a divalent group containing a heteroatom such as an oxygen atom or a nitrogen atom. It may be a group formed by The organic group is not particularly limited, and examples thereof include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 18 carbon atoms, and aralkyl groups having 7 to 26 carbon atoms.
- alkyl group having 1 to 20 carbon atoms is preferable, an alkyl group having 3 to 11 carbon atoms is more preferable, and an alkyl group having 5 carbon atoms is more preferable because the adhesiveness to both the dental restorative material and the dentin is further improved.
- Alkyl groups of -11 are more preferred.
- alkyl groups having 5 to 11 carbon atoms include n-pentyl group, n-hexyl group, n-octyl group and n-undecyl group, with n-octyl group and n-undecyl group being preferred.
- Examples of Y include (meth)acryloyloxymethyl group, (meth)acryloyloxyethyl group, ⁇ -(meth)acryloyloxypropyl group, ⁇ -(meth)acryloyloxyoctyl group, ⁇ -(meth)acryloyloxyun Decyl group, ⁇ -(meth)acrylamidopropyl group, vinyl group, (meth)allyl group, ⁇ -glycidoxypropyl group and the like, (meth)acryloyloxymethyl group, (meth)acryloyloxyethyl group, ⁇ -(meth)acryloyloxypropyl group, ⁇ -(meth)acryloyloxyoctyl group, ⁇ -(meth)acryloyloxyundecyl group is preferable, ⁇ -(meth)acryloyloxyoctyl group, ⁇ -(meth)acryloyloxyundecyl group A dec
- the type of alkyl group represented by R is not particularly limited, and examples thereof include alkyl groups having 1 to 5 carbon atoms, and more specific examples include methyl group, ethyl group, n-propyl group and isopropyl group. , n-butyl group, n-pentyl group and the like.
- the type of aryl group represented by R is not particularly limited, and examples include aryl groups having 6 to 10 carbon atoms, and more specific examples include phenyl groups and naphthyl groups.
- aralkyl group represented by R is not particularly limited, and examples thereof include aralkyl groups having 7 to 12 carbon atoms, more specifically, benzyl group and the like.
- R is preferably an alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms, and even more preferably a methyl group.
- the hydrolyzable group represented by X can be a group capable of forming a silanol group with the silicon atom to which it is attached by hydrolysis, such as alkoxy groups, acyloxy groups, siloxy groups, halogen atoms etc.
- the type of the alkoxy group is not particularly limited, and examples thereof include alkoxy groups having 1 to 5 carbon atoms. More specific examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n -butoxy group, n-pentyloxy group and the like.
- the type of the acyloxy group is not particularly limited, and examples thereof include acyloxy groups having 1 to 5 carbon atoms. roxy group, n-butanoyloxy group, n-pentanoyloxy group and the like.
- the type of the siloxy group is not particularly limited, and examples thereof include a trimethylsiloxy group.
- halogen atom examples include a chlorine atom and a bromine atom.
- X is preferably an alkoxy group, more preferably an alkoxy group having 1 to 5 carbon atoms, and further preferably a methoxy group or an ethoxy group.
- n represents an integer of 0 to 2, and n is preferably 0 or 1 from the viewpoint of the mechanical strength of the cured product of the curable dental composition.
- n is 0 or 1
- multiple X may be the same or different
- multiple R may be the same or different.
- Silane coupling agents include, for example, (meth)acryloyloxymethyltrimethoxysilane, 2-(meth)acryloyloxyethyltrimethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 4-(meth)acryloyloxy Butyltrimethoxysilane, 5-(meth)acryloyloxypentyltrimethoxysilane, 6-(meth)acryloyloxyhexyltrimethoxysilane, 7-(meth)acryloyloxyheptyltrimethoxysilane, 8-(meth)acryloyloxyoctyltri Methoxysilane, 9-(meth)acryloyloxynonyltrimethoxysilane, 10-(meth)acryloyloxydecyltrimethoxysilane, 11-(meth)acryloyloxyundecyltrimethoxysilane, 11-
- Hydrophobizing agent (x-1) used for surface treatment of spherical filler (B-1) is preferably used in combination of two or more hydrophobizing agents (x-1) from the viewpoint of surface treatment layer density.
- silane coupling agent having a polymerizable group represented by the general formula (1) and a silane coupling agent having no polymerizable group 3-methacryloyloxypropyltrimethoxysilane, 8 -(meth)acryloyloxyoctyltrimethoxysilane, 11-(meth)acryloyloxyundecyltrimethoxysilane, and a silane coupling agent having at least one polymerizable group selected from the group consisting of hydrolysates thereof , 1,1,1,3,3,3-hexamethyldisilazane is more preferably used in combination.
- the hydrolyzate can maintain the polymerization activity of the polymerizable group.
- two or more hydrophobizing agents (x-1) are used in combination, in particular, a silane coupling agent having a polymerizable group represented by the general formula (1) and a silane coupling agent having no polymerizable group
- treatment agents with different molecular bulkiness together such as using a ring agent together, the surface treatment layer formed on the surface of the filler is formed more densely, and the effect of the present invention can be further enhanced. .
- the hydrophobizing agent (x-2) used for the surface treatment of the irregular filler (B-2) is exemplified by the same hydrophobizing agent (x-1) used for the surface treatment of the spherical filler (B-1). be done.
- the hydrophobizing agent (x-2) may be used alone or in combination of two or more.
- Hydrophobic treatment agent (x-2) from the viewpoint of mechanical strength of the cured product, dispersibility of filler, etc., 3-methacryloyloxypropyltrimethoxysilane, 8-(meth)acryloyloxyoctyltrimethoxysilane, 11- A silane coupling agent having at least one polymerizable group selected from the group consisting of (meth)acryloyloxyundecyltrimethoxysilane and hydrolysates thereof is preferred, and 8-(meth)acryloyloxyoctyltrimethoxysilane , 11-(meth)acryloyloxyundecyltrimethoxysilane and silane coupling agents having at least one polymerizable group selected from the group consisting of hydrolysates thereof are more preferred, and 8-(meth)acryloyloxy Octyltrimethoxysilane and its hydrolysates are more preferred.
- the polymerization initiator (C) is classified into a photopolymerization initiator (C-1) and a chemical polymerization initiator (C-2).
- a photopolymerization initiator (C-1) As the polymerization initiator (C), and the photopolymerization initiator (C-1) alone may be used,
- the photopolymerization initiator (C-1) and the chemical polymerization initiator (C-2) may be used together.
- photopolymerization initiator (C-1) The type of photopolymerization initiator (C-1) is not particularly limited, and conventionally known photopolymerization initiators can be used without any limitation. Conventionally known photopolymerization initiators include ⁇ -diketones, ketals, thioxanthones, (bis)acylphosphine oxides, ⁇ -aminoacetophenones and the like.
- ⁇ -diketones include camphorquinone (commonly known as "CQ”), benzyl, and 2,3-pentanedione.
- Ketals include benzyl dimethyl ketal and benzyl diethyl ketal.
- Thioxanthones include 2-chlorothioxanthone and 2,4-diethylthioxanthone.
- (Bis)acylphosphine oxides include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, dibenzoylphenylphosphine oxide, bis(2,6-dimethoxy benzoyl)phenylphosphine oxide, tris(2,4-dimethylbenzoyl)phosphine oxide, tris(2-methoxybenzoyl)phosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2, 3,5,6-tetramethylbenzoyldiphenylphosphine oxide, benzoyl-bis(2,6-dimethylphenyl)phosphine oxide, 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide and those disclosed in JP-B-3-57916. Water-soluble
- ⁇ -Aminoacetophenones include 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 2-benzyl-2-diethylamino-1-(4-morpholinophenyl)-1-butanone , 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-propanone, 2-benzyl-2-diethylamino-1-(4-morpholinophenyl)-1-propanone, 2-benzyl-2- Dimethylamino-1-(4-morpholinophenyl)-1-pentanone, 2-benzyl-2-diethylamino-1-(4-morpholinophenyl)-1-pentanone.
- the photopolymerization initiator (C-1) is preferably ⁇ -diketones and acylphosphine oxides, more preferably ⁇ -diketones, and camphorquinone, from the viewpoint of curability and the like. is more preferred.
- the photopolymerization initiator (C-1) may be used alone or in combination of two or more. Further, from the viewpoint of curability and storage stability, the content of the photopolymerization initiator (C-1) is 0.01 to 10 parts by weight with respect to the total 100 parts by weight of the polymerizable monomer (A). is preferred, 0.05 to 5 parts by weight is more preferred, and 0.1 to 3 parts by weight is even more preferred.
- C-2) ⁇ Chemical polymerization initiator (C-2)>
- the type of chemical polymerization initiator (C-2) is not particularly limited, and conventionally known chemical polymerization initiators can be used without any limitation.
- the mechanical strength of the resulting cured product can be further improved.
- the chemical polymerization initiator (C-2) preferably contains an organic peroxide and/or an inorganic peroxide.
- organic peroxides examples include hydroperoxides, peroxyesters, ketone peroxides, peroxyketals, dialkyl peroxides, diacyl peroxides, and peroxydicarbonates. Among these, hydroperoxides and peroxyesters are preferred.
- hydroperoxide examples include cumene hydroperoxide, t-butyl hydroperoxide, t-hexyl hydroperoxide, p-menthane hydroperoxide, diisopropylbenzene hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide and the like.
- peroxyester known peroxyesters having an acyl group on one side of the peroxy group and a hydrocarbon group or a similar group on the other side can be used without any limitation.
- specific examples include ⁇ , ⁇ -bis(neodecanoylperoxy)diisopropylbenzene, cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1- methyl ethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, 1,1,3,3-tetramethyl Butyl peroxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane
- t-butylperoxymaleic acid t-butylperoxy-3,5,5-trimethylhexanoate
- t-butylperoxybenzoate t-butylperoxyisopropyl Monocarbonate
- t-butylperoxy-2-ethylhexylmonocarbonate t-butylperoxyacetate
- t-butylperoxybenzoate is more preferred.
- ketone peroxide examples include methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, and acetylacetone peroxide.
- peroxyketal examples include 1,1-bis(t-hexylperoxy) 3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, and 1,1-bis(t-butylperoxy).
- dialkyl peroxide examples include ⁇ , ⁇ -bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, t-butylcumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)3-hexyne and the like.
- diacyl peroxide examples include isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearyl peroxide, succinic acid peroxide, and m-toluoyl benzoyl. Peroxide, benzoyl peroxides and the like.
- peroxydicarbonate examples include di-n-propylperoxydicarbonate, diisopropylperoxydicarbonate, bis(4-t-butylcyclohexyl)peroxydicarbonate, di(2-ethoxyethyl)peroxydicarbonate, and di(2-ethylhexyl).
- peroxydicarbonate di(2-methoxybutyl)peroxydicarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate and the like.
- inorganic peroxides examples include peroxodisulfates and peroxodiphosphates, and among these, peroxodisulfates are preferred in terms of reactivity.
- the peroxodisulfate includes sodium peroxodisulfate, potassium peroxodisulfate, aluminum peroxodisulfate and ammonium peroxodisulfate, among which sodium peroxodisulfate, potassium peroxodisulfate and ammonium peroxodisulfate are preferred.
- the chemical polymerization initiator (C-2) may be blended singly or in combination of two or more.
- the content of the chemical polymerization initiator (C-2) is 0 with respect to a total of 100 parts by mass of the polymerizable monomer (A) from the viewpoint of adhesive strength with the adherend and operation margin time. 0.001 to 20 parts by weight is preferred, 0.005 to 10 parts by weight is more preferred, and 0.025 to 5 parts by weight is even more preferred. If the content is 0.001 parts by mass or more, appropriate adhesiveness is likely to be obtained, and if it is 20 parts by mass or less, it is easy to maintain the operating margin time.
- the dental curable composition of the present invention may contain a polymerization accelerator (D).
- the polymerization accelerator (D) is a compound that promotes the reaction in combination with the polymerization initiator (C) described above, and is classified into a photopolymerization accelerator (D-1) and a chemical polymerization accelerator (D-2). be.
- These polymerization accelerators (D) may contain either the photopolymerization accelerator (D-1) or the chemical polymerization accelerator (D-2), and the photopolymerization accelerator (D-1 ) and the chemical polymerization accelerator (D-2) may be included.
- photopolymerization accelerator (D-1) The type of photopolymerization accelerator (D-1) is not particularly limited, and conventionally known photopolymerization accelerators can be used without any limitation.
- Examples of the photopolymerization accelerator (D-1) used in the dental curable composition of the present invention include aldehydes, thiol compounds, aminobenzoic acid ester compounds, and amine-based reducing agents.
- Aldehydes include terephthalaldehyde and benzaldehyde derivatives.
- Benzaldehyde derivatives include dimethylaminobenzaldehyde, p-methoxybenzaldehyde, p-ethoxybenzaldehyde, pn-octyloxybenzaldehyde and the like.
- Thiol compounds include 2-mercaptobenzoxazole, decanethiol, 3-mercaptopropyltrimethoxysilane, and thiobenzoic acid.
- aminobenzoic acid ester compounds include 4-(N,N-dimethylamino)ethyl benzoate, 4-(N,N-dimethylamino)methyl benzoate, 4-N,N-(dimethylamino)benzoate n- Butoxyethyl, 4-(N,N-dimethylamino)benzoic acid 2-[(meth)acryloyloxy]ethyl, 4-(N,N-dimethylamino)benzophenone, 4-(N,N-dimethylamino)benzoic acid and n-butyl.
- Amine-based reducing agents are roughly classified into aromatic amines and aliphatic amines, and in the present invention, either aromatic amines or aliphatic amines may be used.
- Aromatic secondary amines or aromatic tertiary amines include N,N-bis(2-hydroxyethyl)-3,5-dimethylaniline, N,N-di(2-hydroxyethyl)-p-toluidine , N,N-bis(2-hydroxyethyl)-3,4-dimethylaniline, N,N-bis(2-hydroxyethyl)-4-ethylaniline, N,N-bis(2-hydroxyethyl)-4 - isopropylaniline, N,N-bis(2-hydroxyethyl)-4-t-butylaniline, N,N-bis(2-hydroxyethyl)-3,5-di-isopropylaniline, N,N-bis( 2-hydroxyethyl)-3,5-di-t-butylaniline, N,N-dimethylaniline, N,N-d
- the aliphatic amines include aliphatic primary amines such as n-butylamine, n-hexylamine and n-octylamine; aliphatic secondary amines such as diisopropylamine, dibutylamine and N-methylethanolamine; Methyldiethanolamine, N-ethyldiethanolamine, Nn-butyldiethanolamine, N-lauryldiethanolamine, 2-(dimethylamino)ethyl (meth)acrylate, N-methyldiethanolamine di(meth)acrylate, N-ethyldiethanolamine di(meth) Aliphatic tertiary amines such as acrylates, triethanolamine tri(meth)acrylate, triethanolamine, trimethylamine, triethylamine and tributylamine.
- aliphatic primary amines such as n-butylamine, n-hexylamine and n-octyl
- aminobenzoic acid ester compounds and aliphatic tertiary amines are preferred, 4-(N,N-dimethylamino) ethyl benzoate, N- Methyldiethanolamine and triethanolamine are more preferred.
- the photopolymerization accelerator (D-1) described above may be blended alone or in combination of two or more. Further, the content of the photopolymerization accelerator (D-1) is 0.01 to 10 parts by weight with respect to the total 100 parts by weight of the polymerizable monomer (A) from the viewpoint of curability and storage stability. is preferred, 0.05 to 5 parts by weight is more preferred, and 0.1 to 3 parts by weight is even more preferred. When the content is 0.01 parts by mass or more, appropriate adhesiveness is likely to be obtained, and when the content is 10 parts by mass or less, it is easy to secure an operation margin time.
- the polymerizable monomer (A) contains a polymerizable monomer (A-2) having an acidic group.
- the chemical polymerization accelerator (D-2) is a chemical polymerization accelerator (D -2a) or only one of the chemical polymerization accelerator (D-2b) that is preferably used when the polymerizable monomer (A) contains a polymerizable monomer (A-2) having an acidic group may be included or both may be included.
- the polymerizable monomer (A) contains a polymerizable monomer (A-2) having an acidic group and a polymerizable monomer (A-2) having an acidic group. Since it is suitably used both with and without it, both are exemplified.
- the chemical polymerization accelerator (D-2a) in the dental curable composition includes an aromatic amine having no electron-withdrawing group in the aromatic ring, a 4th period transition metal compound, a transition metal compound other than the 4th period transition metal compound, Examples include thiourea compounds, and specific examples include the following compounds.
- aromatic amines having no electron-withdrawing group in the aromatic ring include N,N-bis(2-hydroxyethyl)-3,5-dimethylaniline, N,N-bis(2-hydroxyethyl)-p- toluidine, N,N-bis(2-hydroxyethyl)-3,4-dimethylaniline, N,N-bis(2-hydroxyethyl)-4-ethylaniline, N,N-bis(2-hydroxyethyl)- 4-isopropylaniline, N,N-bis(2-hydroxyethyl)-4-t-butylaniline, N,N-bis(2-hydroxyethyl)-3,5-di-isopropylaniline, N,N-bis (2-hydroxyethyl)-3,5-di-t-butylaniline, N,N-dimethylaniline, N,N-dimethyl-p-toluidine, N,N-dimethyl-m-toluidine, N,N-
- the 4th period transition metal compound is a vanadium compound, a copper compound, or a 4th period transition metal compound other than vanadium and copper (hereinafter simply referred to as "another 4th period transition metal compound”).
- the chemical polymerization accelerator (D-2a) in the present invention is preferably a vanadium compound or a copper compound from the viewpoint of the polymerization acceleration effect.
- vanadium compounds include vanadium acetylacetonate, vanadyl acetylacetonate, vanadyl stearate, vanadium naphthenate, vanadium benzoylacetonate, vanadyl oxalate, bis(maltrate)oxovanadium(IV), oxobis(1-phenyl- 1,3-butanedionate) vanadium (IV), vanadium (V) oxytriisopropoxide, ammonium metavanadate (V), sodium metavanadate (V), vanadium pentoxide (V), divanadium tetroxide (IV) ) and vanadyl sulfate (IV).
- vanadium acetylacetonate, vanadyl acetylacetonate, and bis(maltolate)oxovanadium (IV) are preferable from the viewpoint of solubility in solvents, and vanadyl acetylacetonate and bis(maltolate)oxovanadium (IV) are more preferable. preferable.
- copper compound is a compound soluble in the radically polymerizable monomer.
- Copper compounds include copper (II) carboxylate, copper (II) ⁇ -diketone, copper (II) ⁇ -ketoester, copper alkoxide, copper dithiocarbamate, salt of copper and inorganic acid, copper procetonate, copper complexes and the like.
- the copper (II) carboxylates include copper (II) acetate, copper (II) benzoate, copper (II) isobutyrate, copper (II) gluconate, copper (II) citrate, copper (II) phthalate, Copper (II) tartrate, Copper (II) oleate, Copper (II) octylate, Copper (II) octenoate, Copper (II) naphthenate, Copper (II) methacrylate, Copper (II) acrylate, 4- Copper cyclohexylbutyrate and the like can be mentioned.
- ⁇ -diketone copper includes acetylacetone copper (II), trifluoroacetylacetone copper (II), hexafluoroacetylacetone copper (II), 2,2,6,6-tetramethyl-3,5-heptanedionato copper ( II), benzoylacetone copper (II), and the like.
- the ⁇ -ketoester copper (II) includes ethyl copper (II) acetoacetate and the like.
- Copper alkoxides include copper (II) methoxide, copper (II) ethoxide, copper (II) isopropoxide, copper (II) 2-(2-butoxyethoxy) ethoxide, copper (II) 2-(2-methoxyethoxy ) ethoxide and the like.
- copper dithiocarbamate examples include copper (II) dimethyldithiocarbamate. Salts of copper and inorganic acids include copper nitrate and copper chloride.
- carboxylic acid copper (II), ⁇ -diketone copper (II), and ⁇ -ketoester copper (II) are preferable from the viewpoint of solubility and reactivity with respect to radically polymerizable monomers, and copper acetate (II ), more preferably copper(II) acetylacetone.
- Examples of other fourth period transition metal compounds include scandium isopropoxide, iron(III) ethoxide, titanium methoxide, titanium ethoxide, titanium isopropoxide, titanium butoxide, titanium hydroxide, titanium fluoride, and the like. mentioned.
- vanadyl acetylacetonate (IV) and bis(maltrate) oxovanadium (IV) are preferable from the viewpoint of high polymerization promoting effect, and vanadyl acetylacetonate (IV) is preferable. more preferred.
- non-fourth period transition metal compounds include strontium carbonate, strontium hydroxide, strontium ethoxide, tin(II) methoxide, indium ethoxide, actinium ethoxide, yttrium isopropoxide, lanthanum methoxide, lanthanum Ethoxide, lanthanum isopropoxide, lanthanum butoxide, lanthanum hydroxide, lanthanum carbonate, lanthanum fluoride, cerium isopropoxide, praseodymium isopropoxide, promethium isopropoxide, neodymium isopropoxide, samarium isopropoxide, europi um isopropoxide, gadolinium isopropoxide, terbium ethoxide, terbium methoxide, dysprosium isopropoxide, holmium isopropoxide, erbium isopropoxide,
- thiourea compounds include thiourea, methylthiourea, ethylthiourea, ethylenethiourea, N,N'-dimethylthiourea, N,N'-diethylthiourea, N,N'-di-n-propylthiourea, N, N'-dicyclohexylthiourea, trimethylthiourea, triethylthiourea, tri-n-propylthiourea, tricyclohexylthiourea, tetramethylthiourea, tetraethylthiourea, tetra-n-propylthiourea, tetracyclohexylthiourea, 1-( 2-pyridyl)-2-thiourea, (6-methyl-pyridin-2-yl)thiourea, 4,4-dimethylethylenethiourea and the like.
- 1-(2-pyridyl)-2-thiourea (6-methyl-pyridin-2-yl)thiourea, 4,4-dimethylethylenethiourea Urea is preferred.
- the chemical polymerization accelerator (D-2a) described above may be blended alone or in combination of two or more.
- the content of the chemical polymerization accelerator (D-2a) is 0.001 to 20 parts by weight with respect to the total 100 parts by weight of the polymerizable monomer (A) from the viewpoint of curability and storage stability. is preferred, 0.005 to 10 parts by weight is more preferred, and 0.025 to 5 parts by weight is even more preferred.
- ⁇ Chemical polymerization accelerator (D-2b) Chemical polymerization accelerators (D-2b) in the dental curable composition include copper compounds, aromatic sulfinic acids and salts thereof, benzotriazole compounds, benzimidazole compounds, bromides, reducing inorganic compounds containing sulfur, and the like. Specific examples include the following.
- Copper compounds include copper (II) carboxylate, copper (II) ⁇ -diketone, copper (II) ⁇ -ketoester, copper alkoxide, copper dithiocarbamate, salt of copper and inorganic acid, copper procetonate, copper complexes and the like.
- Specific examples of copper (II) carboxylate, copper (II) ⁇ -diketone, copper (II) ⁇ -ketoester, copper alkoxide, copper dithiocarbamate, and salt of copper and inorganic acid are those exemplified in (D-2a). can be used as well.
- carboxylic acid copper (II), ⁇ -diketone copper (II), ⁇ -ketoester copper (II) are preferable from the viewpoint of solubility and reactivity with respect to the polymerizable monomer, and copper (II) acetate , acetylacetone copper(II) are more preferred.
- Aromatic sulfinic acids and salts thereof include benzenesulfinic acid, p-toluenesulfinic acid, o-toluenesulfinic acid, ethylbenzenesulfinic acid, decylbenzenesulfinic acid, dodecylbenzenesulfinic acid, and 2,4,6-trimethylbenzenesulfinic acid.
- 2,4,6-triisopropylbenzenesulfinic acid chlorobenzenesulfinic acid, naphthalenesulfinic acid and their lithium salts, sodium salts, potassium salts, rubidium salts, cesium salts, magnesium salts, calcium salts, strontium salts, iron salts , zinc salt, ammonium salt, tetramethylammonium salt, tetraethylammonium salt.
- lithium salts, sodium salts, potassium salts, and magnesium salts of 2,4,6-trimethylbenzenesulfinic acid and 2,4,6-triisopropylbenzenesulfinic acid are used in terms of the polymerizability and storage stability of the composition. Salts and calcium salts are preferred, and lithium, sodium, potassium, magnesium and calcium salts of 2,4,6-triisopropylbenzenesulfinic acid are more preferred.
- At least part of the aromatic sulfinic acid and its salt is preferably dispersed in the composition in the form of powder.
- the curable dental composition of the present invention can easily secure a longer operating time, and when applied to a wet body such as dentin.
- the aromatic sulfinic acid and its salt dissolve in the water on the surface of the wet body, the polymerizability of the adhesive interface and the interior of the resin-impregnated layer can be further enhanced.
- the aromatic sulfinic acid and its salt When the aromatic sulfinic acid and its salt are dispersed in powder form, the aromatic sulfinic acid and its salt preferably have a solubility in water of 1 mg/100 mL or more at room temperature (25° C.).
- the solubility is 1 mg/100 mL or more, so that when the curable dental composition of the present invention is applied to a wet body, the aromatic sulfinic acid and its salt are sufficiently dissolved in the water of the wet body at the adhesion interface. As a result, the effect of dispersing with powder becomes easy to manifest.
- the aromatic sulfinic acid and its salt are less likely to settle, so the average particle size is preferably 500 ⁇ m or less, more preferably 100 ⁇ m or less, and even more preferably 50 ⁇ m or less.
- the average particle size is preferably 0.01 ⁇ m or more from the viewpoint of preventing the specific surface area of the powder from becoming excessively large and making it easier to maintain good handleability of the curable dental composition. That is, when dispersed as powder, the average particle size is preferably in the range of 0.01 to 500 ⁇ m, more preferably in the range of 0.01 to 100 ⁇ m, and even more preferably in the range of 0.01 to 50 ⁇ m.
- the average particle size can be measured in the same manner as the average particle size of the filler (B).
- Aromatic sulfinates can be made into fine powder by conventionally known methods such as pulverization and freeze-drying.
- the content of the aromatic sulfinic acid and its salt is 0.1, based on a total of 100 parts by mass of the polymerizable monomer (A) in the adhesive composition of the present invention, from the viewpoint of operation margin time and adhesiveness. 5 parts by mass is preferable, 0.2 to 4 parts by mass is more preferable, and 0.5 to 3 parts by mass is even more preferable. If the content is less than 0.1 parts by mass, the adhesiveness may be lowered, and if it exceeds 5 parts by mass, the operation margin time may be shortened.
- the benzotriazole compound and the benzimidazole compound are represented by the following general formulas (2) and (3), respectively.
- R 1 to R 8 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group, an aryl group, an alkoxy group, an alkenyl group, an aralkyl group, or a halogen atom.
- the alkyl groups represented by R 1 to R 8 may be linear, branched or cyclic, and preferably have 1 to 10 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl , neopentyl group, tert-pentyl group, cyclopentyl group, n-hexyl group, isohexyl group, cyclohexyl group, n-heptyl group, cycloheptanyl group, n-octyl group, 2-ethylhexyl group, cyclooctyl group, n-nonyl group, cyclononyl group, n-decyl group and the like. Among these, a
- the aryl groups represented by R 1 to R 8 preferably have 6 to 10 carbon atoms. Examples include phenyl groups, naphthyl groups, anthryl groups, and the like.
- the alkoxy groups represented by R 1 to R 8 may be linear, branched or cyclic, and preferably have 1 to 8 carbon atoms. Examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-hexyloxy, cyclohexyloxy, n-octyloxy, 2-ethylhexyloxy etc.
- the alkenyl groups represented by R 1 to R 8 may be linear, branched or cyclic, and preferably have 1 to 6 carbon atoms. Examples include vinyl, allyl, methylvinyl, propenyl, butenyl, pentenyl, hexenyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like.
- the aralkyl group represented by R 1 to R 8 is preferably an alkyl group (especially an alkyl group having 1 to 10 carbon atoms) substituted with an aryl group (especially an aryl group having 6 to 10 carbon atoms). Examples include benzyl group and the like.
- Halogen atoms represented by R 1 to R 8 include fluorine, chlorine, bromine and iodine atoms.
- R 1 to R 8 are preferably hydrogen atoms or methyl groups.
- the benzotriazole compound and the benzimidazole compound may be used singly or in combination.
- Benzotriazole compounds and benzimidazole compounds include 1H-benzotriazole, 5-methyl-1H-benzotriazole, 5,6-dimethyl-1H-benzotriazole, benzimidazole, 5-methylbenzimidazole, 5,6-dimethylbenzo imidazole and the like.
- 1H-benzotriazole and 5-methyl-1H-benzotriazole are preferred from the viewpoint of operation margin time.
- Bromides include zinc bromide, potassium bromide, sodium bromide, calcium bromide, indium bromide, ammonium bromide, and tetrabutylammonium bromide. Among these, zinc bromide, ammonium bromide, and tetrabutylammonium bromide are particularly preferred.
- Examples of reducing inorganic compounds containing sulfur include sulfites, bisulfites, pyrosulfites, thiosulfates, thionates, dithionites, etc. Among these, sulfites and bisulfites are preferred. . Specific examples include sodium sulfite, potassium sulfite, calcium sulfite, ammonium sulfite, sodium hydrogen sulfite and potassium hydrogen sulfite.
- At least a portion of the sulfur-containing reducing inorganic compound is preferably dispersed in the composition in powder form.
- the dental curable composition of the present invention can ensure a longer operating time, and when applied to dentin, Since the sulfur-containing reducing inorganic compound dissolves in the water on the surface of the dentin, it is possible to further increase the polymerizability in the adhesive interface and inside the resin-impregnated layer.
- the sulfur-containing reducing inorganic compound preferably has a solubility in water of 1 mg/100 mL or more at room temperature (25° C.).
- the solubility is 1 mg/100 mL or more
- the reducing inorganic compound containing sulfur at the adhesion interface is sufficiently dissolved in the water of dentin. It is easy to dissolve, and as a result, the effect of dispersing in powder is easy to manifest.
- the reducing inorganic compound containing sulfur preferably has an average particle size of 500 ⁇ m or less, more preferably 100 ⁇ m or less, and even more preferably 50 ⁇ m or less, from the viewpoint of making it difficult to settle.
- the average particle size is preferably 0.01 ⁇ m or more from the viewpoint of preventing the specific surface area of the powder from becoming excessively large and making it easier to maintain good handleability of the curable dental composition. That is, when dispersed as powder, the average particle size is preferably in the range of 0.01 to 500 ⁇ m, more preferably in the range of 0.01 to 100 ⁇ m, and even more preferably in the range of 0.01 to 50 ⁇ m.
- the average particle size can be measured in the same manner as the average particle size of the filler (B).
- a reducing inorganic compound containing sulfur can be made into a fine powder by a conventionally known method such as a pulverization method or a freeze-drying method.
- the chemical polymerization accelerator (D-2b) described above may be blended alone or in combination of two or more.
- the content of the chemical polymerization accelerator (D-2b) is 0.001 to 40 parts by mass with respect to the total 100 parts by mass of the polymerizable monomer (A) from the viewpoint of curability and storage stability. is preferred, 0.005 to 20 parts by weight is more preferred, and 0.025 to 10 parts by weight is even more preferred.
- the dental curable composition of the present invention contains various known additives such as viscosity modifiers, thickeners, polymerization inhibitors, polymerization modifiers, ultraviolet absorbers, water, organic solvents, dyes, pigments, antibacterial agents, Agents, acid multipliers, base multipliers, inorganic or organic acids, hydrophobizing agents and the like can be appropriately combined depending on the purpose.
- additives such as viscosity modifiers, thickeners, polymerization inhibitors, polymerization modifiers, ultraviolet absorbers, water, organic solvents, dyes, pigments, antibacterial agents, Agents, acid multipliers, base multipliers, inorganic or organic acids, hydrophobizing agents and the like can be appropriately combined depending on the purpose.
- polymerization inhibitors examples include hydroquinone, hydroquinone monomethyl ether, dibutylhydroquinone, dibutylhydroquinone monomethyl ether, t-butylcatechol, 2-t-butyl-4,6-dimethylphenol, 2,6-di-t-butylphenol, 2,6-di-t-butyl-4-methylphenol and the like.
- the dental curable composition of the present invention contains a chemical polymerization initiator (C-2) and a chemical polymerization accelerator (D-2), when it is made into a product form, from the viewpoint of storage stability It is preferable to divide the composition into 2 or 3 or more agents so that each component of the composition does not react before use.
- the chemical polymerization initiator (C-2) is preferably blended with an agent different from the thiourea compound or the aromatic sulfinic acid and its salt.
- the polymerizable monomer (A) and the filler (B) are blended in both the first component and the second component in order to form a two-paste composition. is preferred.
- the dental curable composition in which the second agent contains a polymerizable monomer (A), a filler (B), and a chemical polymerization initiator (C-2).
- each component of the filler (B) is not particularly limited as long as the desired content is achieved by mixing at the time of use and the effect of the present invention can be obtained.
- the first agent contains a spherical filler (B-1) and an irregular filler (B-2), and the second agent contains a spherical filler (B-1) and an irregular filler (B -2), including a dental curable composition.
- the first agent contains an irregular filler (B-2), and the second agent contains a spherical filler (B-1) and an irregular filler (B-2).
- Curable compositions are included.
- the first agent contains a spherical filler (B-1) and an amorphous filler (B-2), and the second agent contains an amorphous filler (B-2).
- Dental curable compositions are included.
- the first agent and/or the second agent may contain the amorphous fine particle filler (B-3).
- the dental curable composition of the present invention achieves both paste fluidity and formability at a high level.
- the dental curable composition of the present invention can be used, for example, in dental cements, self-adhesive dental cements, dental abutment building materials, pit and fissure filling materials, loose tooth fixation materials, and orthodontic bonding materials.
- it is preferably used as a dental cement, a self-adhesive dental cement, or a dental abutment building material. Specific embodiments of application of the dental curable composition are shown below.
- dental curable composition of the present invention is dental cement.
- Suitable dental cements include dental resin cement, dental glass ionomer cement, dental resin-reinforced glass ionomer cement, and the like.
- a self-etching primer or the like may be used as a pretreatment material for the dental cement.
- the dental curable composition of the present invention contains a polymerizable monomer (A), a filler (B), a polymerization initiator (C) and a polymerization accelerator (D), and a polymerization initiator As (C), a photopolymerization initiator (C-1) and a chemical polymerization initiator (C-2) are preferably used in combination.
- each component in the dental cement is less than 15 parts by mass of the hydrophilic polymerizable monomer (A-1a) in a total of 100 parts by mass of the polymerizable monomer (A) in the curable dental composition, It preferably contains 85 to 100 parts by mass of a hydrophobic polymerizable monomer (A-1b) and 0 to 15 parts by mass of a polymerizable monomer (A-2) having an acidic group, and a hydrophilic polymerizable monomer.
- A-1a 1 to 10 parts by mass
- hydrophobic polymerizable monomer (A-1b) 90 to 99 parts by mass
- polymerizable monomer having an acidic group (A-2) 0 to 10 parts by mass
- a hydrophobic polymerizable monomer (A-1b) 95 to 98 parts by mass
- a polymerizable monomer having an acidic group (A-2) It is more preferable to contain 0 to 3 parts by mass.
- the dental curable composition used as dental cement may not contain the hydrophilic polymerizable monomer (A-1a), and when used as a type of dental cement that uses a pretreatment material in combination, it contains an acidic group. may not contain the polymerizable monomer (A-2).
- One preferred embodiment of the curable dental composition of the present invention is a self-adhesive dental cement that does not use a pretreatment material such as a primer among the above dental cements.
- the dental curable composition of the present invention contains a polymerizable monomer (A), a filler (B), a polymerization initiator (C) and a polymerization accelerator (D),
- the polymerizable monomer (A) is a hydrophilic polymerizable monomer (A-1a), a hydrophobic polymerizable monomer (A-1b), and a polymerizable monomer (A-2) having an acidic group. is preferably included.
- a photopolymerization initiator (C-1) and a chemical polymerization initiator (C-2) together as the polymerization initiator (C).
- a pretreatment material may be used. You don't have to.
- the content of each component in the self-adhesive dental cement is 15 parts by mass of the hydrophilic polymerizable monomer (A-1a) in a total of 100 parts by mass of the polymerizable monomer (A) in the curable dental composition.
- the hydrophobic polymerizable monomer (A-1b) 84 to 99 parts by weight, the polymerizable monomer having an acidic group (A-2) preferably contains 1 to 16 parts by weight, hydrophilic polymerizable Monomer (A-1a) 1 to 10 parts by mass, hydrophobic polymerizable monomer (A-1b) 89 to 98 parts by mass, polymerizable monomer having an acidic group (A-2) 1 to 10 parts by mass part, the hydrophilic polymerizable monomer (A-1a) 2 to 5 parts by mass, the hydrophobic polymerizable monomer (A-1b) 94 to 97 parts by mass, the polymerizable having an acidic group More preferably, it contains 1 to 4 parts by mass of the monomer (A-2).
- a dental curable composition used as a self-adhesive dental cement may not contain the hydrophilic polymerizable monomer (A-1a).
- the dental curable composition of the present invention is a dental abutment building material.
- a self-etching primer or the like may be used as a pretreatment material for the dental abutment building material.
- the dental curable composition of the present invention contains a polymerizable monomer (A), a filler (B), a polymerization initiator (C) and a polymerization accelerator ( Spherical filler (B-1) having an average particle size of 0.01 ⁇ m to 1 ⁇ m in which the filler (B) is treated with a hydrophobizing agent (x-1), and an average particle size of 0.5 to 6.0 ⁇ m.
- It preferably contains an irregularly shaped filler (B-2) of 0 ⁇ m and an irregularly shaped fine particle filler (B-3) having an average particle diameter of less than 0.05 ⁇ m.
- each component in the dental abutment building material is 15 parts by mass of the hydrophilic polymerizable monomer (A-1a) in a total of 100 parts by mass of the polymerizable monomer (A) in the dental curable composition. part or less, the hydrophobic polymerizable monomer (A-1b) 85 to 100 parts by weight, the polymerizable monomer having an acidic group (A-2) preferably contains 0 to 15 parts by weight, hydrophilic polymerizable Monomer (A-1a) 1 to 10 parts by mass, hydrophobic polymerizable monomer (A-1b) 90 to 99 parts by mass, polymerizable monomer having an acidic group (A-2) 0 to 9 parts by mass part, the hydrophilic polymerizable monomer (A-1a) 2 to 5 parts by mass, the hydrophobic polymerizable monomer (A-1b) 95 to 98 parts by mass, the polymerizable having an acidic group It is more preferable to contain 0 to 3 parts by mass of the monomer (A-1
- the filler (B-1) 1.0 to 900 parts by weight, the filler (B-2) 40 to 1485 parts by weight, and the filler (B- 3) preferably contains 0.1 to 150 parts by mass, filler (B-1) 7.5 to 500 parts by mass, filler (B-2) 74.85 to 949 parts by mass, and filler (B-3) It is more preferable to contain 0.15 to 80 parts by mass, including filler (B-1) 20 to 150 parts by mass, filler (B-2) 138 to 445 parts by mass, and filler (B-3) 2 to 25 parts by mass. is more preferred.
- 0.001 to 20 parts by mass of a polymerization initiator (C) and 0.001 to 40 parts by mass of a polymerization accelerator (D) are contained with respect to a total of 100 parts by mass of the polymerizable monomer (A). is preferable, and it is more preferable to contain 0.05 to 10 parts by mass of a polymerization initiator (C) and 0.05 to 20 parts by mass of a polymerization accelerator (D).
- the dental curable composition used as a dental abutment building material may not contain the hydrophilic polymerizable monomer (A-1a), and in the case of a type using a pretreatment material, a polymerizable composition having an acidic group.
- the monomer (A-2) may not be included.
- any of the preferred embodiments of the above-described dental cement, self-adhesive dental cement, and dental abutment building material the content of each component can be changed as appropriate based on the description in the above specification. , any component can be changed such as addition or deletion.
- the present invention includes embodiments in which the above configurations are combined in various ways within the technical scope of the present invention as long as the effects of the present invention are exhibited.
- Examples 3-1 to 3-13 and Comparative Examples 3-1 to 3-8 (Preparation of dental curable composition) First agent and second agent, in the same manner as in Examples 1-1 to 1-24, 2-1 to 2-11 and Comparative Examples 1-1 to 1-9, 2-1 to 2-8, Table 6
- a paste-like curable dental composition by mixing and kneading the raw materials shown in Table 7 at normal temperature (25 ° C.) in a dark place, equal amounts of the first agent and the second agent were taken and kneaded for 10 seconds.
- the properties of the samples were examined according to the methods of Test Examples 1 to 3 below. The results are shown in Tables 6 and 7.
- Test Example 1 Consistency
- Consistency indicates that the higher the consistency, the softer the paste, and is an index generally used as a method for evaluating the fluidity of a curable dental composition.
- a consistency of 20 mm to 40 mm is suitable for the dental hardenable composition of the present invention, a consistency of 20 mm to 35 mm is more suitable, and a consistency of 20 mm to 30 mm is even more suitable.
- the strength of the dental curable composition of the present invention is preferably 100 MPa or more, more preferably 110 MPa or more, and even more preferably 120 MPa or more.
- the dental curable composition of the present invention those having a formability evaluation of "3" to "5" are suitable from the viewpoint of the level of formability required as a dental abutment building material. , those having a shapeability evaluation of "4" or "5" are more suitable.
- FIG. 1 shows the paste at the start of weighing
- FIG. 2 shows the paste after 10 minutes at 37° C.
- the paste (after settling) is shown.
- FIG. 2 since the shape can be maintained even after 10 minutes have passed, there is no problem that the shape cannot be maintained due to dripping of the paste or the like in constructing the abutment for dental treatment.
- FIG. 3 shows the paste at the time of weighing (at the start of evaluation), and FIG. The paste is shown after 10 minutes at 37°C (after standing).
- FIG. 3 shows the shape of the paste collapses from the start of weighing, and there is a risk that the shape formed by build-up cannot be maintained in building the abutment.
- FIG. 4 shows the shape of the paste changes after a certain period of time, and even when the paste is built up in the construction of the abutment for dental treatment, the formed shape cannot be maintained.
- the dental curable compositions of the examples are excellent in mechanical strength, have a consistency in the range of 20 to 40 mm, and have high paste fluidity. It can be seen that it also has a good shapeability.
- the dental curable composition according to the present invention is suitably used as a dental cement, a self-adhesive dental cement, a dental abutment building material, etc. in the field of dentistry.
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Abstract
Description
支台築造においては、築盛されたペーストの形状を支台歯の形状となるように整える必要があるため、ペーストの賦形性が重要となるが、特許文献1にはこれに関する直接的な記載はない。
本発明者らが検討した結果、特許文献1に記載された歯科用硬化性組成物において、チキソトロピー性調整剤として平均粒子径が0.05μm未満のフィラーを配合し、歯科用支台築造材料として重要な賦形性を有するようにペーストを作製した場合、流動性が損なわれることが判明した。
[1]重合性単量体(A)、フィラー(B)、及び重合開始剤(C)を含み、
前記重合性単量体(A)が、重合性単量体(A)の合計100質量部中、
0質量部以上15質量部未満の酸性基を有しない親水性重合性単量体(A-1a)、及び
55質量部以上の酸性基を有しない疎水性重合性単量体(A-1b)を含み、
酸性基を有しない親水性重合性単量体(A-1a)の25℃の水に対する溶解量が4.5g/L以上であり、
前記フィラー(B)が、フィラー(B)の合計100質量部中、
1~60質量部の平均粒子径が0.01~1μmである球状フィラー(B-1)、
40~99質量部の平均粒子径が0.5~6.0μmである不定形フィラー(B-2)、及び
0~10質量部の平均粒子径が0.5μm未満である不定形微粒子フィラー(B-3)を含み、
球状フィラー(B-1)が、疎水化処理剤(x-1)で疎水化処理されてなり、
前記重合開始剤(C)が光重合開始剤(C-1)を含む、歯科用硬化性組成物。
[2]前記不定形微粒子フィラー(B-3)の平均粒子径が0.05μm未満である、[1]に記載の歯科用硬化性組成物。
[3]前記フィラー(B)が、フィラー(B)の合計100質量部中、
球状フィラー(B-1)を10~30質量部、
不定形フィラー(B-2)を69~89質量部、及び
不定形微粒子フィラー(B-3)を1~5質量部含む、[1]又は[2]に記載の歯科用硬化性組成物。
[4]前記疎水化処理剤(x-1)が、シランカップリング剤、チタネート系カップリング剤、アルミネート系カップリング剤、及びジルコ-アルミネート系カップリング剤からなる群から選ばれる少なくとも1種を含む、[1]~[3]のいずれかに記載の歯科用硬化性組成物。
[5]前記不定形フィラー(B-2)が、疎水化処理剤(x-2)で疎水化処理されてなる、[1]~[4]のいずれかに記載の歯科用硬化性組成物。
[6]前記疎水化処理剤(x-2)が、下記一般式(1)で表される重合性基を有するシランカップリング剤である、[5]に記載の歯科用硬化性組成物。
Y-SiRnX(3-n) (1)
(式中、Yは重合性基、又は重合性基を有する1価の有機基を表し、Rはアルキル基、アリール基及びアラルキル基からなる群より選ばれる基を表し、Xは水酸基又は加水分解性基を表し、nは0、1又は2の整数を表す。ただし、複数存在するRは互いに同一であっても異なっていてもよく、複数存在するXは互いに同一であっても異なっていてもよい。)
[7]Yが、(メタ)アクリロイル基と有機基とが酸素原子を含む2価基を介して結合した基であって、酸素原子を含む2価基を介して(メタ)アクリロイル基と結合する有機基が炭素数5~11のアルキル基である、[6]に記載の歯科用硬化性組成物。
[8]前記重合性単量体(A)が酸性基を有する重合性単量体(A-2)をさらに含む、[1]~[7]のいずれかに記載の歯科用硬化性組成物。
[9]前記重合開始剤(C)が化学重合開始剤(C-2)をさらに含む、[1]~[8]のいずれかに記載の歯科用硬化性組成物。
[10]第一剤と、第二剤とからなり、
第一剤が、重合性単量体(A)、フィラー(B)、及び化学重合促進剤(D-2)を含み、
第二剤が、重合性単量体(A)、フィラー(B)、及び化学重合開始剤(C-2)を含む、[9]に記載の歯科用硬化性組成物。
[11]前記化学重合促進剤(D-2)がチオ尿素化合物及び/又は芳香族スルフィン酸塩を含む、[10]に記載の歯科用硬化性組成物。
[12][1]~[11]のいずれかに記載の歯科用硬化性組成物からなる、歯科用支台築造材料。
[13][1]~[11]のいずれかに記載の歯科用硬化性組成物からなる、歯科用レジンセメント。
一般的にペーストの粘度を上昇させる要因として重合性単量体とフィラー間の親水性相互作用が知られている。そのため、ペーストの粘度上昇の抑制を目的として、前記親水性相互作用を弱める観点から、比較的親水性の低い重合性単量体と、表面に疎水化処理を施したフィラーとを用いることが考えられる。比較的親水性の低い重合性単量体と、表面に疎水化処理を施したフィラーの間では、発生する相互作用は極めて弱いものとなる。これによって、ペーストの粘度上昇を抑制でき、流動性が得られるものの、このままでは、賦形性に劣る組成物になってしまう。
ここで、比較的親水性の低い重合性単量体と、表面に疎水化処理を施したフィラーを含む組成物において、フィラーを多量に配合することで、重合性単量体とフィラー間の接触面積が増加し、これらの間に生じる相互作用が弱い状態でも十分な賦形性を得ることが可能となる。このとき、これらの相互作用は、前記親水性相互作用に比べて弱い相互作用であるため、わずかな力で簡単に解消される。
本発明の歯科用硬化性組成物に用いられる重合性単量体(A)には、ラジカル重合性単量体が好適に用いられる。
重合性単量体(A)におけるラジカル重合性単量体としては、(メタ)アクリレート系重合性単量体、(メタ)アクリルアミド系重合性単量体、α-シアノアクリル酸、(メタ)アクリル酸、α-ハロゲン化アクリル酸、クロトン酸、桂皮酸、ソルビン酸、マレイン酸、イタコン酸等のエステル類、ビニルエステル類、ビニルエーテル類、モノ-N-ビニル誘導体、スチレン誘導体などが挙げられる。これらの中でも、硬化性の観点から(メタ)アクリレート系重合性単量体、(メタ)アクリルアミド系重合性単量体が好ましい。
前記重合性単量体(A)は、酸性基を有しない重合性単量体(A-1)、酸性基を有する重合性単量体(A-2)に大別される。
なお、本明細書中において、(メタ)アクリルなる記載はメタクリルとアクリルとの総称である。
本発明における酸性基を有しない重合性単量体(A-1)としては、25℃の水に対する溶解量が4.5g/L以上である酸性基を有しない親水性重合性単量体(A-1a);25℃の水に対する溶解量が4.5g/L未満である酸性基を有しない疎水性重合性単量体(A-1b)に分けられる。
本発明の歯科用硬化性組成物において、重合性単量体(A)は酸性基を有しない親水性重合性単量体(A-1a)(以下、単に「親水性重合性単量体(A-1a)」と称することがある)を重合性単量体(A)の合計100質量部中、15質量部未満含む。
親水性重合性単量体(A-1a)とは、酸性基を有さずかつ25℃の水に対する溶解量が4.5g/L以上の単量体を意味する。
本発明の歯科用硬化性組成物において、ペーストの流動性と、賦形性との両立の点から、前記水に対する溶解量で規定された親水性重合性単量体(A-1a)の含有量は重合性単量体(A)の合計100質量部中、15質量部未満である。
親水性重合性単量体(A-1a)としては、酸性基を有さず重合性基を有するラジカル重合性単量体が好ましく、ラジカル重合が容易である観点から、重合性基は(メタ)アクリロイルオキシ基及び/又は(メタ)アクリルアミド基が好ましい。
親水性重合性単量体(A-1a)としては、例えば、2-ヒドロキシエチル(メタ)アクリレート、3-ヒドロキシプロピル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、1,3-ジヒドロキシプロピル(メタ)アクリレート、2,3-ジヒドロキシプロピル(メタ)アクリレート、2-((メタ)アクリロイルオキシ)エチルトリメチルアンモニウムクロライド、テトラヒドロフルフリル(メタ)アクリレートなどの親水性の(メタ)アクリレート系単官能性重合性単量体;トリエチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ノナエチレングリコールジ(メタ)アクリレート、1,3-ビス(メタクリロイルオキシ)-2-プロパノール、1,2-ビス(3-メタクリロイルオキシ-2-ヒドロキシプロポキシ)エタンなどの親水性の(メタ)アクリレート系多官能性重合性単量体;N-メチロール(メタ)アクリルアミド、N-ヒドロキシエチル(メタ)アクリルアミド、N,N-ビス(2-ヒドロキシエチル)(メタ)アクリルアミド、N-メトキシメチル(メタ)アクリルアミド、N-エトキシメチル(メタ)アクリルアミド、ジアセトン(メタ)アクリルアミド、4-(メタ)アクリロイルモルホリン、N-トリヒドロキシメチル-N-メチル(メタ)アクリルアミド、N,N-ジメチルアクリルアミド、N,N-ジエチルアクリルアミド、N-メタクリロイルオキシエチルアクリルアミドなどの親水性の(メタ)アクリルアミド系重合性単量体などが挙げられる。
上述の親水性重合性単量体(A-1a)は、1種を単独で用いてもよく、2種以上を併用してもよい。
本発明の歯科用硬化性組成物において、重合性単量体(A)は酸性基を有しない疎水性重合性単量体(A-1b)(以下、単に「疎水性重合性単量体(A-1b)」と称することがある)を含む。
ここで、疎水性重合性単量体(A-1b)とは、酸性基を有さずかつ25℃の水に対する溶解量が4.5g/L未満の単量体を意味する。
疎水性重合性単量体(A-1b)を用いることで、疎水化処理された球状フィラー(B-1)を含むフィラー(B)と組み合わせた際に、重合性単量体と、フィラー間の親水性相互作用が弱まり、ペーストの流動性を向上させることができる。
また、疎水性重合性単量体(A-1b)は、歯科用硬化性組成物の曵糸性(糸引きのしやすさ)を抑え、硬化物の機械的強度などを向上させることができる。
疎水性重合性単量体(A-1b)としては、例えば、疎水性の単官能性重合性単量体に加え、疎水性の芳香族化合物系二官能性重合性単量体、疎水性の脂肪族化合物系二官能性重合性単量体、疎水性の三官能性以上の重合性単量体などの架橋性の重合性単量体などが例示される。
そこで、本発明の歯科用硬化性組成物中における疎水性重合性単量体(A-1b)の含有量は、重合性単量体(A)の合計100質量部中、55質量部以上であり、55質量部以上であることが好ましく、70質量部以上であることがより好ましく、85質量部以上であることがさらに好ましく、90質量部以上であることが特に好ましく、100質量部であってもよい。
ある好適な実施形態としては、例えば、疎水性重合性単量体(A-1b)の含有量が、重合性単量体(A)の合計100質量部中、55質量部以上100質量部以下である、歯科用硬化性組成物が挙げられる。
別のある好適な実施形態としては、例えば、本発明の歯科用硬化性組成物が、親水性重合性単量体(A-1a)を含む場合、重合性単量体(A)の合計100質量部中、親水性重合性単量体(A-1a)の含有量が、0質量部超15質量部未満であり、疎水性重合性単量体(A-1b)の含有量が、85質量部以上100質量部未満である、歯科用硬化性組成物が挙げられる。
別の他のある好適な実施形態としては、例えば、本発明の歯科用硬化性組成物が、酸性基を有する重合性単量体(A-2)を含む場合、重合性単量体(A)の合計100質量部中、酸性基を有する重合性単量体(A-2)の含有量が、0質量部超30質量部以下であり、疎水性重合性単量体(A-1b)の含有量が、55質量部以上100質量部未満である、歯科用硬化性組成物が挙げられる。
前記したいずれの実施形態において、各単量体の含有量は、本明細書の記載に基づいて、含有量を適宜変更できる。
本発明の歯科用硬化性組成物は、酸性基を有する重合性単量体(A-2)を含んでいてもよい。
本発明に用いられる酸性基を有する重合性単量体(A-2)としては、少なくとも一つ以上の酸性基と重合性基を有するラジカル重合性単量体が好ましい。酸性基を有する重合性単量体(A-2)が有する酸性基としては、接着性の観点から、酸性基はリン酸基、ピロリン酸基、チオリン酸基、ホスホン酸基、カルボン酸基、スルホン酸基等の酸性基が好ましい。
また、ラジカル重合が容易である観点から、酸性基を有する重合性単量体(A-2)が有する重合性基は(メタ)アクリロイルオキシ基及び/又は(メタ)アクリルアミド基が好ましい。
また、本発明の歯科用硬化性組成物中における酸性基を有する重合性単量体(A-2)の含有量は、歯質に対する接着性の観点から、重合性単量体(A)の合計100質量部中、0~30質量部であることが好ましく、0~20質量部であることがより好ましく、0~15質量部であることがさらに好ましい。
本発明の歯科用硬化性組成物は、ペーストの流動性及び賦形性を調整するために、また硬化物の機械的強度を高めるために、フィラー(B)を含むことが必要である。このようなフィラーとして、無機フィラー、有機フィラー、及び有機-無機複合フィラーなどが挙げられる。
これらの中でも、強度等の観点から、各種ガラス類、シリカ-チタニア、シリカ-ジルコニア等の複合酸化物、シリカで表面をコートされたコアシェル構造のフッ化カルシウム、シリカで表面をコートされたコアシェル構造のフッ化イッテルビウム、シリカで表面をコートされたコアシェル構造のフッ化イットリウム、シリカで表面をコートされたコアシェル構造のリン酸カルシウム、シリカで表面をコートされたコアシェル構造の硫酸バリウム、シリカで表面をコートされたコアシェル構造の二酸化ジルコニウム、シリカで表面をコートされたコアシェル構造の二酸化チタン、シリカで表面をコートされたコアシェル構造のヒドロキシアパタイトが好ましい。
球状フィラー(B-1)とは、電子顕微鏡でフィラーの写真を撮り、その単位視野内に観察される粒子が丸みをおびており、その最大径に直交する方向の粒子径をその最大径で割った平均均斉度が0.6以上であるフィラーである。本発明の歯科用硬化性組成物における球状フィラー(B-1)は、滑り効果により優れる点から、平均均斉度が0.7以上であることが好ましく、0.8以上であることがより好ましい。
疎水化処理された球状フィラー(B-1)を一定量含むことで、外力を加えた際に生じる滑り効果に加えて、重合性単量体と、フィラーとの間に生じる親水性相互作用を弱め、外力を加えた際にペーストの流動性を損なうことがなく、ペーストの流動性を向上させることができる。疎水化処理剤(x-1)については、後述する。
本発明に用いられる不定形フィラー(B-2)の平均粒子径は0.5~6.0μmであり、機械的強度及び被膜厚さの観点から1.0~5.0μmが好ましく、1.5~3.0μmがより好ましい。平均粒子径が0.5μm未満の場合、前記不定形フィラーの比表面積が増大し、ペーストの流動性が低くなる。一方、平均粒子径が6.0μmを超える場合、歯科用硬化性組成物中の不定形フィラーの分散性が悪化し、均一なペーストを作製できない。
また、不定形フィラー(B-2)を球状フィラー(B-1)と組み合わせることで、本発明の歯科用硬化性組成物のペーストの優れた流動性も得られる。
さらに本発明の歯科用硬化性組成物には、上述のフィラー(B)が球状フィラー(B-1)及び不定形フィラー(B-2)に加えて、平均粒子径0.5μm未満の不定形微粒子フィラー(B-3)を0~10質量部含む。不定形微粒子フィラー(B-3)は、チキソトロピー性調整剤として作用するため流動性等の微調整を行うことが可能である。
フィラー(B)は、球状フィラー(B-1)を3~55質量部、不定形フィラー(B-2)を54.9~96.9質量部、及び不定形微粒子フィラー(B-3)を0.1~8質量部含むことが好ましく、球状フィラー(B-1)を5~50質量部、不定形フィラー(B-2)を49.9~94.9質量部、及び不定形微粒子フィラー(B-3)を0.1~8質量部含むことがより好ましく、球状フィラー(B-1)を10~30質量部、不定形フィラー(B-2)を69~89質量部、及び不定形微粒子フィラー(B-3)を1~5質量部含むことがさらに好ましい。
また、優れた流動性と賦形性との両立しやすい点から、不定形フィラー(B-2)の含有量が、球状フィラー(B-1)の含有量より多いことが好ましい。
また、フィラーの種類により、剪断力の有無によるペーストの流動性をコントロール可能となる。各粒子径のフィラーに異なる種類のフィラーが含まれていてもよい。
また、本発明の効果を損なわない範囲内で、意図せずに、フィラー以外の粒子が不純物として含まれていてもよい。
また、不定形フィラー(B-2)は、重合性単量体への分散性、機械的強度等により優れる点から、疎水化処理剤(x-2)で疎水化処理されてなるものであることが好ましい。
また、疎水化処理剤(x-1)及び(x-2)は、同一の疎水化処理剤を用いてもよく、それぞれ異なるものを用いてもよい。
また、本発明の歯科用硬化性組成物が疎水化処理された球状フィラー(B-1)を含む限り、疎水化処理による所望の効果を奏するため、球状フィラー(B-1)の材質は特に限定されない。
本発明において、表面処理に用いる表面処理剤は、界面活性剤は含まなくてもよい。ある実施形態としては、球状フィラー(B-1)が、疎水化処理剤(x-1)のみで疎水化処理されてなる、歯科用硬化性組成物が挙げられる。
他の実施形態としては、球状フィラー(B-1)が界面活性剤では処理されていない、歯科用硬化性組成物が挙げられる。
別の他の実施形態としては、すべてのフィラー(B)が界面活性剤では処理されていない、歯科用硬化性組成物が挙げられる。
また、他の実施形態としては、重合性単量体(A)、フィラー(B)、及び重合開始剤(C)を含み、界面活性剤を含有しない、歯科用硬化性組成物が挙げられる。
Y-SiRnX(3-n) (1)
(式中、Yは重合性基、又は重合性基を有する1価の有機基を表し、Rはアルキル基、アリール基及びアラルキル基からなる群より選ばれる基を表し、Xは水酸基又は加水分解性基を表し、nは0、1又は2の整数を表す。ただし、複数存在するRは互いに同一であっても異なっていてもよく、複数存在するXは互いに同一であっても異なっていてもよい。)
球状フィラー(B-1)の表面処理に用いる疎水化処理剤(x-1)は、表面処理層密度の観点から、2種以上の疎水化処理剤(x-1)を併用することが好ましく、上記一般式(1)で表される重合性基を有するシランカップリング剤と、重合性基を有しないシランカップリング剤を併用することがより好ましく、3-メタクリロイルオキシプロピルトリメトキシシラン、8-(メタ)アクリロイルオキシオクチルトリメトキシシラン、11-(メタ)アクリロイルオキシウンデシルトリメトキシシラン及び、これらの加水分解物からなる群から選ばれる少なくとも1種の重合性基を有するシランカップリング剤と、1,1,1,3,3,3-ヘキサメチルジシラザンを併用することがさらに好ましい。前記加水分解物は、加水分解性基が加水分解されるため、重合性基の重合活性を維持することができる。2種以上の疎水化処理剤(x-1)を併用する場合において、特に、上記一般式(1)で表される重合性基を有するシランカップリング剤と、重合性基を有しないシランカップリング剤とを併用する等、分子のかさ高さの異なる処理剤を併用することによって、フィラーの表面に形成される表面処理層がより密に形成され、本発明の効果をより高めることができる。
不定形フィラー(B-2)の表面処理に用いる疎水化処理剤(x-2)は、球状フィラー(B-1)の表面処理に用いる疎水化処理剤(x-1)と同じものが例示される。疎水化処理剤(x-2)は、1種を単独で用いてもよく、2種以上を併用してもよい。疎水化処理剤(x-2)は、硬化物の機械的強度、フィラーの分散性などの観点から、3-メタクリロイルオキシプロピルトリメトキシシラン、8-(メタ)アクリロイルオキシオクチルトリメトキシシラン、11-(メタ)アクリロイルオキシウンデシルトリメトキシシラン及び、これらの加水分解物からなる群から選ばれる少なくとも1種の重合性基を有するシランカップリング剤が好ましく、8-(メタ)アクリロイルオキシオクチルトリメトキシシラン、11-(メタ)アクリロイルオキシウンデシルトリメトキシシラン及び、これらの加水分解物からなる群から選ばれる少なくとも1種の重合性基を有するシランカップリング剤がより好ましく、8-(メタ)アクリロイルオキシオクチルトリメトキシシラン、及びその加水分解物がさらに好ましい。
重合開始剤(C)は光重合開始剤(C-1)と化学重合開始剤(C-2)に分類される。本発明の歯科用硬化性組成物においては、重合開始剤(C)として光重合開始剤(C-1)を含む必要があり、光重合開始剤(C-1)のみを用いてもよく、光重合開始剤(C-1)と化学重合開始剤(C-2)とを併用してもよい。
光重合開始剤(C-1)の種類に特に制限はなく、従来公知の光重合開始剤をなんら制限なく使用することができる。従来公知の光重合開始剤としては、α-ジケトン類、ケタール類、チオキサントン類、(ビス)アシルホスフィンオキシド類、α-アミノアセトフェノン類などが挙げられる。
化学重合開始剤(C-2)の種類に特に制限はなく、従来公知の化学重合開始剤をなんら制限なく使用することができる。
本発明の歯科用硬化性組成物が、化学重合開始剤(C-2)を含有する場合、得られる硬化物の機械的強度をより向上させることができる。
化学重合開始剤(C-2)は、有機過酸化物及び/又は無機過酸化物を含むことが好ましい。
化学重合開始剤(C-2)は、1種を単独で配合してもよく、2種以上を併用してもよい。また、化学重合開始剤(C-2)の含有量は、被着体との接着強さ、操作余裕時間の観点から、重合性単量体(A)の合計100質量部に対して、0.001~20質量部が好ましく、0.005~10質量部がより好ましく、0.025~5質量部がさらに好ましい。同含有量が0.001質量部以上であれば適切な接着性が得られやすく、20質量部以下であれば、操作余裕時間を維持しやすい。
本発明の歯科用硬化性組成物は、重合促進剤(D)を含んでいてもよい。重合促進剤(D)は、上述の重合開始剤(C)と組み合わせて反応を促進させる化合物であり、光重合促進剤(D-1)と化学重合促進剤(D-2)とに分類される。
これらの重合促進剤(D)は、光重合促進剤(D-1)或いは化学重合促進剤(D-2)のどちらか一方のみが含まれていてもよく、光重合促進剤(D-1)と化学重合促進剤(D-2)のどちらも含まれていてもよい。
光重合促進剤(D-1)の種類に特に制限はなく、従来公知の光重合促進剤をなんら制限なく使用することができる。
本発明の歯科用硬化性組成物で用いられる光重合促進剤(D-1)としては、例えば、アルデヒド類、チオール化合物、アミノ安息香酸エステル化合物、アミン系還元剤などが挙げられる。
また、光重合促進剤(D-1)の含有量は、硬化性及び保存安定性の観点から、重合性単量体(A)の合計100質量部に対して、0.01~10質量部が好ましく、0.05~5質量部がより好ましく、0.1~3質量部がさらに好ましい。同含有量が0.01質量部以上であれば、適切な接着性が得られやすく、10質量部以下であれば操作余裕時間を確保しやすい。
本発明の歯科用硬化性組成物で用いられる化学重合促進剤(D-2)としては、前記重合性単量体(A)が、酸性基を有する重合性単量体(A-2)を含まない場合に好適に用いられる化学重合促進剤(D-2a)と、重合性単量体(A)が、酸性基を有する重合性単量体(A-2)を含む場合に好適に用いられる化学重合促進剤(D-2b)とに大別される。
なお、銅化合物は重合性単量体(A)が、酸性基を有する重合性単量体(A-2)を含む場合と、酸性基を有する重合性単量体(A-2)を含まない場合とのどちらでも好適に用いられるため、双方に例示される。
歯科用硬化性組成物中の化学重合促進剤(D-2a)としては、芳香環に電子吸引基を有しない芳香族アミン、第4周期の遷移金属化合物、第4周期以外の遷移金属化合物、チオ尿素化合物などが挙げられ、具体的には下記の化合物が挙げられる。
その中でも溶媒への溶解性などの観点から、バナジウムアセチルアセトネート、バナジルアセチルアセトネート、ビス(マルトラート)オキソバナジウム(IV)が好ましく、バナジルアセチルアセトネート及びビス(マルトラート)オキソバナジウム(IV)がより好ましい。
銅化合物としては、カルボン酸銅(II)、β-ジケトン銅(II)、β-ケトエステル銅(II)、銅アルコキシド、ジチオカルバミン酸銅、銅と無機酸の塩、銅プロセトネート(copper procetonate)、銅錯体等が挙げられる。
カルボン酸銅(II)としては、酢酸銅(II)、安息香酸銅(II)、イソ酪酸銅(II)、グルコン酸銅(II)、クエン酸銅(II)、フタル酸銅(II)、酒石酸銅(II)、オレイン酸銅(II)、オクチル酸銅(II)、オクテン酸銅(II)、ナフテン酸銅(II)、メタクリル酸銅(II)、アクリル酸銅(II)、4-シクロヘキシル酪酸銅等が挙げられる。
β-ジケトン銅(II)としては、アセチルアセトン銅(II)、トリフルオロアセチルアセトン銅(II)、ヘキサフルオロアセチルアセトン銅(II)、2,2,6,6-テトラメチル-3,5-ヘプタンジオナト銅(II)、ベンゾイルアセトン銅(II)等が挙げられる。
β-ケトエステル銅(II)としては、アセト酢酸エチル銅(II)等が挙げられる。
銅アルコキシドとしては、銅(II)メトキシド、銅(II)エトキシド、銅(II)イソプロポキシド、銅(II)2-(2-ブトキシエトキシ)エトキシド、銅(II)2-(2-メトキシエトキシ)エトキシド等が挙げられる。
ジチオカルバミン酸銅としては、ジメチルジチオカルバミン酸銅(II)等が挙げられる。
銅と無機酸の塩としては、硝酸銅、及び塩化銅が挙げられる。
これらの内でも、ラジカル重合性単量体に対する溶解性と反応性の観点から、カルボン酸銅(II)、β-ジケトン銅(II)、β-ケトエステル銅(II)が好ましく、酢酸銅(II)、アセチルアセトン銅(II)がより好ましい。
歯科用硬化性組成物中の化学重合促進剤(D-2b)としては、銅化合物、芳香族スルフィン酸及びその塩、ベンゾトリアゾール化合物、ベンゾイミダゾール化合物、臭化物、硫黄を有する還元性無機化合物などが挙げられ、具体的には下記のものが挙げられる。
銅化合物としては、カルボン酸銅(II)、β-ジケトン銅(II)、β-ケトエステル銅(II)、銅アルコキシド、ジチオカルバミン酸銅、銅と無機酸の塩、銅プロセトネート(copper procetonate)、銅錯体等が挙げられる。
カルボン酸銅(II)、β-ジケトン銅(II)、β-ケトエステル銅(II)、銅アルコキシド、ジチオカルバミン酸銅、銅と無機酸の塩の具体例は、(D-2a)で例示したものが同様に使用できる。
これらの内でも、重合性単量体に対する溶解性と反応性の観点から、カルボン酸銅(II)、β-ジケトン銅(II)、β-ケトエステル銅(II)が好ましく、酢酸銅(II)、アセチルアセトン銅(II)がより好ましい。
これらの中でも、組成物の重合性及び保存安定性の点で、2,4,6-トリメチルベンゼンスルフィン酸及び2,4,6-トリイソプロピルベンゼンスルフィン酸のリチウム塩、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩が好ましく、2,4,6-トリイソプロピルベンゼンスルフィン酸のリチウム塩、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩がより好ましい。
また、芳香族スルフィン酸及びその塩は、沈降し難くなるため、平均粒子径は500μm以下が好ましく、100μm以下がより好ましく、50μm以下がさらに好ましい。また、粉末の比表面積が過大にならず歯科用硬化性組成物の取り扱い性を良好に保ちやすくする観点から、平均粒子径は0.01μm以上が好ましい。すなわち、粉末で分散する場合の平均粒子径は0.01~500μmの範囲が好ましく、0.01~100μmの範囲がより好ましく、0.01~50μmの範囲がさらに好ましい。なお平均粒子径は、前記のフィラー(B)の平均粒子径と同様にして測定することができる。
硫黄を含有する還元性無機化合物を粉末状の形態で分散させることにより、本発明の歯科用硬化性組成物は、より長い操作余裕時間を確保することができ、また歯質に適用した場合に、硫黄を含有する還元性無機化合物が歯質表面の水に溶解するため、接着界面部及び樹脂含浸層内部における重合性をさらに高めることができる。
硫黄を含有する還元性無機化合物を粉末状の形態で分散させる場合、硫黄を含有する還元性無機化合物は、その常温(25℃)における水に対する溶解度が1mg/100mL以上のものが好ましい。同溶解度が1mg/100mL以上であることによって、本発明の歯科用硬化性組成物を歯質に適用した場合に、接着界面部において硫黄を含有する還元性無機化合物が歯質の水に十分に溶解しやすく、その結果、粉末で分散する効果が発現し易くなる。また、硫黄を含有する還元性無機化合物は、沈降し難くする観点から、平均粒子径は500μm以下が好ましく、100μm以下がより好ましく、50μm以下がさらに好ましい。
また、粉末の比表面積が過大にならず歯科用硬化性組成物の取り扱い性を良好に保ちやすくする観点から、平均粒子径は0.01μm以上が好ましい。すなわち、粉末で分散する場合の平均粒子径は0.01~500μmの範囲が好ましく、0.01~100μmの範囲がより好ましく、0.01~50μm以下がさらに好ましい。
なお、平均粒子径は、前記のフィラー(B)の平均粒子径と同様にして測定することができる。
また、化学重合促進剤(D-2b)の含有量は、硬化性及び保存安定性の観点から、重合性単量体(A)の合計100質量部に対して、0.001~40質量部が好ましく、0.005~20質量部がより好ましく、0.025~10質量部がさらに好ましい。
前記第一剤と、第二剤とからなる歯科用硬化性組成物において、フィラー(B)の各成分(球状フィラー(B-1)、不定形フィラー(B-2)、及び不定形微粒子フィラー(B-3))の配合の組み合わせは、使用時に混合して、所望の含有量となり本発明の効果が得られる限り、特に限定されない。
ある実施形態としては、第一剤が、球状フィラー(B-1)、及び不定形フィラー(B-2)を含み、第二剤が、球状フィラー(B-1)、及び不定形フィラー(B-2)を含む、歯科用硬化性組成物が挙げられる。
他の実施形態としては、第一剤が、不定形フィラー(B-2)を含み、第二剤が、球状フィラー(B-1)、及び不定形フィラー(B-2)を含む、歯科用硬化性組成物が挙げられる。
別の他の実施形態としては、第一剤が、球状フィラー(B-1)、及び不定形フィラー(B-2)を含み、第二剤が、不定形フィラー(B-2)を含む、歯科用硬化性組成物が挙げられる。
前記したいずれの実施形態においても、第一剤及び/又は第二剤が、不定形微粒子フィラー(B-3)を含んでいてもよい。
本発明の歯科用硬化性組成物の好適な実施形態の一つとして、歯科用セメントが挙げられる。歯科用セメントとしては、歯科用レジンセメント、歯科用グラスアイオノマーセメント、歯科用レジン強化型グラスアイオノマーセメントなどが好適なものとして例示される。歯科用セメントは、セルフエッチングプライマーなどを前処理材として用いてもよい。
本発明の歯科用硬化性組成物を歯科用セメントとして用いる場合、重合性単量体(A)、フィラー(B)、重合開始剤(C)及び重合促進剤(D)を含み、重合開始剤(C)として光重合開始剤(C-1)と化学重合開始剤(C-2)を併用することが好ましい。
本発明の歯科用硬化性組成物の好適な実施形態の一つとして、前記歯科用セメントの中でもプライマー等の前処理材を使用しない態様である自己接着性歯科用セメントが挙げられる。本発明の歯科用硬化性組成物を自己接着性歯科用セメントとして用いる場合、重合性単量体(A)、フィラー(B)、重合開始剤(C)及び重合促進剤(D)を含み、重合性単量体(A)が親水性重合性単量体(A-1a)、疎水性重合性単量体(A-1b)、及び酸性基を有する重合性単量体(A-2)を含むことが好ましい。また、重合開始剤(C)として光重合開始剤(C-1)と化学重合開始剤(C-2)を併用することが好ましい。本発明の歯科用硬化性組成物を自己接着性歯科用セメントとして用いる場合、前処理材を使用してもよいが、自己接着性を有するため前処理材は必須ではなく、前処理材を使用しなくてもよい。
本発明の歯科用硬化性組成物の好適な実施形態の一つとして、歯科用支台築造材料が挙げられる。歯科用支台築造材料は、セルフエッチングプライマーなどを前処理材として用いてもよい。
本発明の歯科用硬化性組成物を歯科用セメントとして用いる場合、歯科用硬化性組成物は、重合性単量体(A)、フィラー(B)、重合開始剤(C)及び重合促進剤(D)を含み、フィラー(B)が疎水化処理剤(x-1)で処理された平均粒子径0.01μm~1μmの球状フィラー(B-1)、及び平均粒子径0.5~6.0μmの不定形フィラー(B-2)、及び平均粒子径0.05μm未満の不定形微粒子フィラー(B-3)を含むことが好ましい。
#801:1,2-ビス(3-メタクリロイルオキシ-2-ヒドロキシプロポキシ)エタン
3G:トリエチレングリコールジメタクリレート
Bis-GMA:2,2-ビス〔4-(2-ヒドロキシ-3-メタクリロイルオキシプロポキシ)フェニル〕プロパン
NPG:ネオペンチルグリコールジメタクリレート
D-2.6E:2,2-ビス(4-メタクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数:2.6)
MDP:10-メタクリロイルオキシデシルジハイドロジェンホスフェート
フィラー1:下記の製造例1-1で製造したものを用いた。
フィラー2:下記の製造例1-2で製造したものを用いた。
フィラー3:下記の製造例2-1で製造したものを用いた。
フィラー4:下記の製造例2-2で製造したものを用いた。
フィラー5:下記の製造例3-1で製造したものを用いた。
・フィラー1の製造
シリカ粒子(日産化学工業株式会社製、商品名「スノーテックス(登録商標)OL」、コロイダルシリカ、固形分濃度20質量%の水分散体、平均粒子径:50nm、平均均斉度0.8以上)100質量部にイソプロパノール60質量部を加え、室温(約25℃)で混合することで分散液を得た。この分散液に3-メタクリロイルオキシプロピルトリメトキシシラン(信越化学工業株式会社製、商品名「KBM-503」)0.48質量部及び重合禁止剤(関東化学株式会社製の2,6-ジ-t-ブチル-4-メチルフェノール(BHT))0.01質量部を加え、40℃で72時間混合した。次いで、この混合物に1,1,1,3,3,3-ヘキサメチルジシラザン(信越化学工業株式会社製、商品名「HMDS-1」)0.78質量部を加え、40℃で72時間放置した。当該工程においてシリカ粒子の表面処理が進行し、疎水性になったシリカ粒子が水及びイソプロパノール中で安定に存在できなくなり、凝集及び沈殿した。表面処理後に得られた混合物全量に対して35%塩酸水溶液2.6質量部を加え、シリカ粒子を沈殿させた。沈殿物を濾紙(株式会社アドバンテック製、定量濾紙「No.5A」)で濾過した。濾過残渣(固形分)を純水で洗浄した後に100℃で真空乾燥して、フィラー1を得た。
・フィラー2の製造
シリカ粒子(日産化学工業株式会社製、商品名「スノーテックス(登録商標)OS」、コロイダルシリカ、固形分濃度20質量%の水分散体、平均粒子径:10nm、平均均斉度0.8以上)100質量部にイソプロパノール200質量部を加え、室温(約25℃)で混合することで分散液を得た。この分散液に3-メタクリロイルオキシプロピルトリメトキシシラン(信越化学工業株式会社製、商品名「KBM-503」)2.4質量部及び重合禁止剤(関東化学株式会社製の2,6-ジ-t-ブチル-4-メチルフェノール(BHT))0.01質量部を加え、40℃で72時間混合した。次いで、この混合物に1,1,1,3,3,3-ヘキサメチルジシラザン(信越化学工業株式会社製、商品名「HMDS-1」)3.9質量部を加え、40℃で72時間放置した。当該工程においてシリカ粒子の表面処理が進行し、疎水性になったシリカ粒子が水及びイソプロパノール中で安定に存在できなくなり、凝集・沈殿した。表面処理後に得られた混合物全量に対して35%塩酸水溶液7.8質量部を加え、シリカ粒子を沈殿させた。沈殿物を濾紙(株式会社アドバンテック製、定量濾紙「No.5A」)で濾過した。濾過残渣(固形分)を純水で洗浄した後に100℃で真空乾燥して、フィラー2を得た。
・フィラー3の製造
GM27884 UF2.0グレード(SCHOTT社製バリウムガラス、平均粒子径:2.0μm)100質量部に、蒸留水80質量部を加え、室温(約25℃)で混合することで分散液を得た。この分散液に3-メタクリロイルオキシトリメトキシシラン(信越化学工業株式会社製、商品名「KBM-503」)3.0質量部及び0.3質量%酢酸水溶液200質量部を三口フラスコに入れ、1時間、室温下で撹拌した。凍結乾燥により水を除去した後、90℃で3時間加熱処理を行い、フィラー3を得た。
・フィラー4の製造
GM27884 UF2.0グレード(SCHOTT社製バリウムガラス、平均粒子径:2.0μm)100質量部に、イソプロパノール250質量部を加え、室温(約25℃)で混合することで分散液を得た。この分散液に8-メタクリロイルオキシオクチルトリメトキシシラン(信越化学工業株式会社製、商品名「KBM-5803」)1.4質量部、0.3質量%酢酸水溶液5質量部、及びイソプロパノール50質量部を三口フラスコに入れ、1時間、室温下で撹拌した。真空乾燥により溶媒を除去した後、90℃で3時間加熱処理を行い、フィラー4を得た。
・フィラー5の製造
ヒュームドシリカ(日本アエロジル株式会社製、商品名「アエロジル(登録商標)130」、平均粒子径:0.016μm)を、このヒュームドシリカ100質量部に対して、通法により3質量部の3-メタクリロイルオキシプロピルトリメトキシシランで表面処理を行い、フィラー5を得た。
CQ:カンファーキノン
THP:1,1,3,3-テトラメチルブチルハイドロペルオキシド
PDE:4-(N,N-ジメチルアミノ)安息香酸エチル
DMETU: 4,4-ジメチルエチレンチオ尿素
VOAA:バナジルアセチルアセトナート(IV)
BHT:2,6-ジ-t-ブチル-4-メチルフェノール
表1~表5に示す原料を常温(25℃)暗所で混合、及び混練してペースト状の歯科用硬化性組成物を調製し、以下の試験例1~3の方法に従って特性を調べた。結果を表1~表5に示す。
第一剤及び第二剤を、実施例1-1~1-24、2-1~2-11及び比較例1-1~1-9、2-1~2-8と同様に、表6~表7に示す原料を常温(25℃)暗所で混合、及び混練してペースト状の歯科用硬化性組成物を調製し、第一剤及び第二剤を等量採取し10秒間練和したものについて、以下の試験例1~3の方法に従って特性を調べた。結果を表6~表7に示す。
調製した各実施例及び比較例の歯科用硬化性組成物を25℃の恒温室(湿度50%)に1日間静置した後、ガラス板上に該歯科用硬化性組成物を0.5mL計量した。その上に40gのガラス板(5cm×5cm)を載せ、120秒経過後のサンプルの長径と短径をガラス板越しに測定し、その両者の算術平均を算出し、これを稠度(mm)とした(n=3)。
サンプルの径が50mmを超え、ガラス板からはみ出した場合は、稠度50mm以上として記録した。
稠度は、稠度が大きいほどペーストが柔らかいことを示し、歯科用硬化性組成物の流動性の評価方法として一般的に用いられる指標である。
本発明の歯科用硬化性組成物には、稠度20mmから40mmのものが適しており、稠度20mmから35mmのものがより適しており、稠度20mmから30mmのものがさらに適している。
ISO 4049:2009に準拠して曲げ試験により曲げ強さを評価した。具体的には以下のとおりである。作製したペースト(歯科用硬化性組成物)をSUS製の金型(縦2mm×横25mm×厚さ2mm)に充填し、ペーストの上下(2mm×25mmの面)をスライドガラスで圧接した。次いで、歯科用可視光照射器「ペンキュアー2000」(株式会社モリタ製)で、スライドガラス越しに10秒間ずつ片面5箇所でペーストの裏表に光照射してペーストを硬化させた。
得られた硬化物について、万能試験機(オートグラフAG-I 100kN、株式会社島津製作所製)を用いて、支点間距離20mm、クロスヘッドスピード1mm/minで曲げ試験を実施し、3点曲げ強さを測定し(n=5)、平均値を算出した。
本発明の歯科用硬化性組成物の強度としては、100MPa以上のものが適しており、110MPa以上のものがより適しており、120MPa以上のものがさらに適している。
30mm×30mmの正方形のガラス板上に、予め直径3mmの円を描いておき、その円内にペースト0.03gを計量し、ガラス板を37℃の恒温器内で水平におき、その状態で60秒間静置してペーストの形状を目視で観察し、下記の評価基準に従って、ペーストの形状(賦形性)を評価した(n=3で測定し、最も低い評価を採用した。)。
〔賦形性の評価基準〕
5:横から見た場合に半球状を形成せず、計量時の形状を維持する
4:横から見た場合に半球状を形成しつつも、計量時の形状を一部維持する
3:横から見た場合に半球を形成するが、上から見た場合にペーストの直径は計量時と変わらない
2:横から見た場合に半球を形成し、上から見た場合にペーストの直径が計量時よりも大きくなる
1:計量時からペーストが高さを維持できずにつぶれる
図2に示されるように、10分経過しても形状を維持できるため、歯科治療の支台築造において、ペーストが垂れる等により、形状を維持できないという問題が生じない。
さらに、図4に示されるように、ペーストの形状が所定時間経過後に変化し、歯科治療の支台築造において、ペーストが築盛された場合においても、形成された形状を維持できない。
Claims (13)
- 重合性単量体(A)、フィラー(B)、及び重合開始剤(C)を含み、
前記重合性単量体(A)が、重合性単量体(A)の合計100質量部中、
0質量部以上15質量部未満の酸性基を有しない親水性重合性単量体(A-1a)、及び
55質量部以上の酸性基を有しない疎水性重合性単量体(A-1b)を含み、
酸性基を有しない親水性重合性単量体(A-1a)の25℃の水に対する溶解量が4.5g/L以上であり、
前記フィラー(B)が、フィラー(B)の合計100質量部中、
1~60質量部の平均粒子径が0.01~1μmである球状フィラー(B-1)、
40~99質量部の平均粒子径が0.5~6.0μmである不定形フィラー(B-2)、及び
0~10質量部の平均粒子径が0.5μm未満である不定形微粒子フィラー(B-3)を含み、
球状フィラー(B-1)が、疎水化処理剤(x-1)で疎水化処理されてなり、
前記重合開始剤(C)が光重合開始剤(C-1)を含む、歯科用硬化性組成物。 - 前記不定形微粒子フィラー(B-3)の平均粒子径が0.05μm未満である、請求項1に記載の歯科用硬化性組成物。
- 前記フィラー(B)が、フィラー(B)の合計100質量部中、
球状フィラー(B-1)を10~30質量部、
不定形フィラー(B-2)を69~89質量部、及び
不定形微粒子フィラー(B-3)を1~5質量部含む、請求項1又は2に記載の歯科用硬化性組成物。 - 前記疎水化処理剤(x-1)が、シランカップリング剤、チタネート系カップリング剤、アルミネート系カップリング剤、及びジルコ-アルミネート系カップリング剤からなる群から選ばれる少なくとも1種を含む、請求項1~3のいずれか1項に記載の歯科用硬化性組成物。
- 前記不定形フィラー(B-2)が、疎水化処理剤(x-2)で疎水化処理されてなる、請求項1~4のいずれか1項に記載の歯科用硬化性組成物。
- 前記疎水化処理剤(x-2)が、下記一般式(1)で表される重合性基を有するシランカップリング剤である、請求項5に記載の歯科用硬化性組成物。
Y-SiRnX(3-n) (1)
(式中、Yは重合性基、又は重合性基を有する1価の有機基を表し、Rはアルキル基、アリール基及びアラルキル基からなる群より選ばれる基を表し、Xは水酸基又は加水分解性基を表し、nは0、1又は2の整数を表す。ただし、複数存在するRは互いに同一であっても異なっていてもよく、複数存在するXは互いに同一であっても異なっていてもよい。) - Yが、(メタ)アクリロイル基と有機基とが酸素原子を含む2価基を介して結合した基であって、酸素原子を含む2価基を介して(メタ)アクリロイル基と結合する有機基が炭素数5~11のアルキル基である、請求項6に記載の歯科用硬化性組成物。
- 前記重合性単量体(A)が酸性基を有する重合性単量体(A-2)をさらに含む、請求項1~7のいずれか1項に記載の歯科用硬化性組成物。
- 前記重合開始剤(C)が化学重合開始剤(C-2)をさらに含む、請求項1~8のいずれか1項に記載の歯科用硬化性組成物。
- 第一剤と、第二剤とからなり、
第一剤が、重合性単量体(A)、フィラー(B)、及び化学重合促進剤(D-2)を含み、
第二剤が、重合性単量体(A)、フィラー(B)、及び化学重合開始剤(C-2)を含む、請求項9に記載の歯科用硬化性組成物。 - 前記化学重合促進剤(D-2)がチオ尿素化合物及び/又は芳香族スルフィン酸塩を含む、請求項10に記載の歯科用硬化性組成物。
- 請求項1~11のいずれか1項に記載の歯科用硬化性組成物からなる、歯科用支台築造材料。
- 請求項1~11のいずれか1項に記載の歯科用硬化性組成物からなる、歯科用レジンセメント。
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JPH0357916B2 (ja) | 1981-04-09 | 1991-09-03 | Basf Ag | |
JP2005170813A (ja) | 2003-12-09 | 2005-06-30 | Tokuyama Corp | 歯科用硬化性組成物 |
JP2020040937A (ja) | 2018-09-05 | 2020-03-19 | 株式会社トクヤマデンタル | 歯科用重合硬化性組成物 |
WO2020179852A1 (ja) * | 2019-03-05 | 2020-09-10 | クラレノリタケデンタル株式会社 | 非溶媒系歯科用接着性組成物 |
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JPH0357916B2 (ja) | 1981-04-09 | 1991-09-03 | Basf Ag | |
JP2005170813A (ja) | 2003-12-09 | 2005-06-30 | Tokuyama Corp | 歯科用硬化性組成物 |
JP2020040937A (ja) | 2018-09-05 | 2020-03-19 | 株式会社トクヤマデンタル | 歯科用重合硬化性組成物 |
WO2020179852A1 (ja) * | 2019-03-05 | 2020-09-10 | クラレノリタケデンタル株式会社 | 非溶媒系歯科用接着性組成物 |
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