JP7464615B2 - 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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- JP7464615B2 JP7464615B2 JP2021546992A JP2021546992A JP7464615B2 JP 7464615 B2 JP7464615 B2 JP 7464615B2 JP 2021546992 A JP2021546992 A JP 2021546992A JP 2021546992 A JP2021546992 A JP 2021546992A JP 7464615 B2 JP7464615 B2 JP 7464615B2
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- meth
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- 239000000203 mixture Substances 0.000 title claims description 128
- 239000000178 monomer Substances 0.000 claims description 133
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000002245 particle Substances 0.000 claims description 52
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- 238000006116 polymerization reaction Methods 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 21
- 239000003505 polymerization initiator Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
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- 125000001931 aliphatic group Chemical group 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 8
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- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
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- 125000004122 cyclic group Chemical group 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- 241000283690 Bos taurus Species 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 150000003926 acrylamides Chemical class 0.000 description 5
- 150000001642 boronic acid derivatives Chemical class 0.000 description 5
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- 159000000000 sodium salts Chemical class 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 4
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- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
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- 229920000570 polyether Polymers 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
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- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- KCWWCWMGJOWTMY-UHFFFAOYSA-N 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)NC(=O)N1CC1=CC=CC=C1 KCWWCWMGJOWTMY-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical class [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 208000004188 Tooth Wear Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
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- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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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 3
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- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical class CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 2
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- BXBOUPUNKULVKB-UHFFFAOYSA-N 10-trimethoxysilyldecyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCCCOC(=O)C(C)=C BXBOUPUNKULVKB-UHFFFAOYSA-N 0.000 description 2
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- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 2
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- HAZQZUFYRLFOLC-UHFFFAOYSA-N 2-phenyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=CC=CC=2)=N1 HAZQZUFYRLFOLC-UHFFFAOYSA-N 0.000 description 2
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- SANIRTQDABNCHF-UHFFFAOYSA-N 7-(diethylamino)-3-[7-(diethylamino)-2-oxochromene-3-carbonyl]chromen-2-one Chemical compound C1=C(N(CC)CC)C=C2OC(=O)C(C(=O)C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=CC2=C1 SANIRTQDABNCHF-UHFFFAOYSA-N 0.000 description 2
- GAYWTJPBIQKDRC-UHFFFAOYSA-N 8-trimethoxysilyloctyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCOC(=O)C(C)=C GAYWTJPBIQKDRC-UHFFFAOYSA-N 0.000 description 2
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
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- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
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- AFJXJDKUWZPRQX-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boron Chemical compound [B]C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AFJXJDKUWZPRQX-UHFFFAOYSA-N 0.000 description 2
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
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- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
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- HPWMVNFJSFHJIW-UHFFFAOYSA-M potassium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [K+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 HPWMVNFJSFHJIW-UHFFFAOYSA-M 0.000 description 1
- NLZLDWFYQXFPSZ-UHFFFAOYSA-M potassium;2,4,6-triethylbenzenesulfinate Chemical compound [K+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 NLZLDWFYQXFPSZ-UHFFFAOYSA-M 0.000 description 1
- SCRWQCKSJIHKKV-UHFFFAOYSA-M potassium;2,4,6-trimethylbenzenesulfinate Chemical compound [K+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 SCRWQCKSJIHKKV-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
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- 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
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- SLUHLANJIVXTRQ-UHFFFAOYSA-N pyridin-2-ylthiourea Chemical compound NC(=S)NC1=CC=CC=N1 SLUHLANJIVXTRQ-UHFFFAOYSA-N 0.000 description 1
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- VMMZJFAHOAKUQM-UHFFFAOYSA-N sodium;1,3,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound [Na].CC1C(=O)N(C)C(=O)N(C)C1=O VMMZJFAHOAKUQM-UHFFFAOYSA-N 0.000 description 1
- VFTILSBBLXWMQK-UHFFFAOYSA-M sodium;1-cyclohexyl-5-ethyl-4,6-dioxopyrimidin-2-olate Chemical compound [Na+].O=C1C(CC)C(=O)[N-]C(=O)N1C1CCCCC1 VFTILSBBLXWMQK-UHFFFAOYSA-M 0.000 description 1
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- 238000010557 suspension polymerization reaction Methods 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
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-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
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-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
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical class O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 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
- 230000000007 visual effect Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 229940105963 yttrium fluoride Drugs 0.000 description 1
- RBORBHYCVONNJH-UHFFFAOYSA-K yttrium(iii) fluoride Chemical compound F[Y](F)F RBORBHYCVONNJH-UHFFFAOYSA-K 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
- A61K6/17—Particle size
Description
[1]重合性単量体(A)、充填材(B)、及び重合開始剤(C)を含む歯科用硬化性組成物であって、前記重合性単量体(A)が、炭素数1~15のアルコキシレン繰返し単位からなる部位(X)を有し芳香環を有さない多官能(メタ)アクリル系単量体(A-1)と、芳香環を有し水酸基を有さない多官能(メタ)アクリル系単量体(A-2)とを含み、前記部位(X)に含まれる炭素原子の総数と酸素原子の総数の比C/Oが2.5~10であり、前記部位(X)の主鎖を構成する炭素原子の総数と酸素原子の総数の合計が25~60であり、且つ重合性単量体(A)100質量部において前記多官能(メタ)アクリル系単量体(A-1)を3~60質量部を含む、歯科用硬化性組成物。
[2]前記重合性単量体(A)の30℃における粘度が10~2500cPである、[1]に記載の歯科用硬化性組成物。
[3]前記多官能(メタ)アクリル系単量体(A-2)の含有量が、前記重合性単量体(A)100質量部において、10~97質量部である、[1]又は[2]に記載の歯科用硬化性組成物。
[4]前記多官能(メタ)アクリル系単量体(A-1)が下記一般式(1)で表されるジ(メタ)アクリル酸エステルである、[1]~[3]のいずれかに記載の歯科用硬化性組成物。
[5]前記X1を構成するアルコキシレン繰返し単位の炭素数が3~5である、[4]に記載の歯科用硬化性組成物。
[6]前記多官能(メタ)アクリル系単量体(A-1)が下記一般式(4)で表されるポリブチレングリコールジメタクリレート(ブチレングリコール基の平均付加モル数:5~11)である、[1]~[5]のいずれかに記載の歯科用硬化性組成物。
[8]前記充填材(B)の平均粒子径が0.01~50μmである、[1]~[7]のいずれかに記載の歯科用硬化性組成物。
[9]硬化物の曲げ弾性率が8GPa以下である、[1]~[8]のいずれかに記載の歯科用硬化性組成物。
[10]重合収縮応力が12.0MPa以下である、[1]~[9]のいずれかに記載の歯科用硬化性組成物。
[11][1]~[10]のいずれかに記載の歯科用硬化性組成物を用いてなる、歯科用コンポジットレジン。
上記の構成とすることにより、重合収縮応力が小さいとともに、硬化物の機械的強度に優れ、吸水性が低く、対合歯の摩耗量が少なく、さらに、窩洞に充填しやすい稠度である、歯科用コンポジットレジンなどとして好適な歯科用硬化性組成物となる。また、本明細書において、「稠度」とは歯科用硬化性組成物のペースト一定荷重で押しつぶした際のペーストの広がりを意味し、稠度が高い値ほど歯科用硬化性組成物のペーストが柔らかいことを意味し、低い値ほど歯科用硬化性組成物のペーストが硬いことを意味する。
本発明の歯科用硬化性組成物における重合性単量体(A)は、炭素数1~15のアルコキシレン繰返し単位からなる部位(X)を有し芳香環を有さない多官能(メタ)アクリル系単量体(A-1)と、芳香環を有し水酸基を有さない多官能(メタ)アクリル系単量体(A-2)とを含む。
本発明における多官能(メタ)アクリル系単量体(A-1)は、炭素数1~15のアルコキシレン繰返し単位からなる部位(X)を有し、芳香環を有さず、前記部位(X)に含まれる炭素原子の総数と酸素原子の総数の比C/Oが2.5~10であり、前記部位(X)の主鎖を構成する炭素原子の総数と酸素原子の総数の合計が25~60である。
本発明における多官能(メタ)アクリル系単量体(A-2)は、芳香環を有し水酸基を有さない。前記芳香環としては、ベンゼン環や、ナフタレン環等、縮合環を含む芳香族性環などが挙げられる。
例えば、メチル(メタ)アクリレート、イソブチル(メタ)アクリレート、ベンジル(メタ)アクリレート、ドデシル(メタ)アクリレート、2-(N,N-ジメチルアミノ)エチル(メタ)アクリレート、2,3-ジブロモプロピル(メタ)アクリレート、3-(メタ)アクリロイルオキシプロピ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、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、4-ヒドロキシブチル(メタ)アクリレート、6-ヒドロキシヘキシル(メタ)アクリレート、10-ヒドロキシデシル(メタ)アクリレート、プロピレングリコールモノ(メタ)アクリレート、グリセリンモノ(メタ)アクリレート、エリスリトールモノ(メタ)アクリレート、フェノキシエチレングリコール(メタ)アクリレート、イソボルニル(メタ)アクリレート、3-フェノキシベンジル(メタ)アクリレート、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(ヒドロキシエチル)(メタ)アクリルアミド、N,N-ジメチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N,N-ジ-n-プロピル(メタ)アクリルアミド、N-エチル-N-メチル(メタ)アクリルアミド、(メタ)アクリロイルモルホリン、(メタ)アクリロイルオキシドデシルピリジニウムブロミド、(メタ)アクリロイルオキシドデシルピリジニウムクロリド、(メタ)アクリロイルオキシヘキサデシルピリジニウムブロミド、(メタ)アクリロイルオキシヘキサデシルピリジニウムクロリドなどが挙げられる。
例えば、芳香族系の二官能性の(メタ)アクリル酸エステル(前記多官能(メタ)アクリル系単量体(A-2)に相当するものを除く)、脂肪族系の二官能性の(メタ)アクリル酸エステルなどが挙げられる。
例えば、トリメチロールプロパントリ(メタ)アクリレート、トリメチロールエタントリ(メタ)アクリレート、トリメチロールメタントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、N,N’-(2,2,4-トリメチルヘキサメチレン)ビス〔2-(アミノカルボキシ)プロパン-1,3-ジオール〕テトラ(メタ)アクリレート、1,7-ジ(メタ)アクリロイルオキシ-2,2,6,6-テトラ(メタ)アクリロイルオキシメチル-4-オキサヘプタンなどが挙げられる。
本発明の歯科用硬化性組成物は充填材(B)を含む。充填材(B)は1種を単独で使用してもよく、2種以上を併用してもよい。
H2C=CR6-CO-R7-(CH2)z-SiR8 yR9 (3-y) (3)
(式中、R6は水素原子又はメチル基であり、R7は酸素原子、硫黄原子、又は-NR10-であり、ここでR10は水素原子又は炭素数1~8の脂肪族基(直鎖状でも分岐鎖状でも環状でもよい)であり、R8は加水分解可能な基であり、R9は炭素数1~6の炭化水素基であり、yは1~3の整数であり、zは1~13の整数であり、複数存在するR8及びR9は、それぞれ、互いに同一であっても異なっていてもよい。)
本発明の歯科用硬化性組成物は重合開始剤(C)を含む。重合開始剤(C)としては、一般工業界で使用されている重合開始剤から選択して使用でき、中でも歯科用途に用いられている重合開始剤が好ましく用いられる。特に、光重合開始剤及び化学重合開始剤が好ましく用いられる。重合開始剤(C)は、1種を単独で用いてもよく、2種以上を適宜組み合わせて使用してもよい。
本発明の歯科用硬化性組成物は、重合促進剤(D)をさらに含んでいてもよい。重合促進剤としては、アミン類、スルフィン酸及びその塩、バルビツール酸誘導体、ボレート化合物、トリアジン化合物、銅化合物、錫化合物、バナジウム化合物、ハロゲン化合物、アルデヒド類、チオール化合物、亜硫酸塩、亜硫酸水素塩、チオ尿素化合物などが挙げられる。重合促進剤(D)は、1種を単独で使用してもよく、2種以上を併用してもよい。ある好適な実施形態では、重合開始剤(C)が光重合開始剤を含み、さらに重合促進剤(D)を含み、前記重合促進剤(D)が第3級アミンである、歯科用硬化性組成物が挙げられる。前記第3級アミンとしては、第3級芳香族アミンが好ましい。
本発明の歯科用硬化性組成物は、上記した重合性単量体(A)、充填材(B)、重合開始剤(C)、及び重合促進剤(D)以外にも、必要に応じて、重合禁止剤、紫外線吸収剤、酸化防止剤、抗菌剤、分散剤、pH調整剤、蛍光剤、着色剤(顔料、染料)等の添加剤(E)をさらに含んでいてもよい。添加剤(E)は、1種を単独で使用してもよく、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の調製方法に特に制限はなく、各成分を所定の配合量で配合することにより得ることができる。この際の配合順序に特に制限はなく、各成分を一括して配合してもよいし、2回以上に分けて配合してもよい。また、必要に応じて混合ないし練合したり、あるいは、真空脱泡処理等の脱泡処理を施したりしてもよい。得られた歯科用硬化性組成物は、単一の容器(シリンジ等)に充填するなどして、1材型(1ペースト型)の歯科用硬化性組成物とすることができる。
本発明の歯科用硬化性組成物の用途に特に制限はなく、各種歯科材料として用いることができ、具体的には、歯科用コンポジットレジン(例えば、齲蝕窩洞充填用コンポジットレジン、支台築造用コンポジットレジン、歯冠用コンポジットレジン等)、義歯床用レジン、義歯床用裏装材、印象材、合着用材料(例えば、レジンセメント、レジン添加型グラスアイオノマーセメント等)、歯科用接着材(例えば、歯科矯正用接着材、窩洞塗布用接着材等)、歯牙裂溝封鎖材、CAD/CAM用レジンブロック、テンポラリークラウン、人工歯材料などとして好ましく用いることができる。これらの中でも、本発明の歯科用硬化性組成物は、操作性に優れるとともに硬化物の機械的強度及び研磨性に優れ、しかも、窩洞に充填しやすい稠度であり、重合収縮応力も小さいことなどから、歯科用コンポジットレジンとして用いることが特に好ましい。
(充填材の平均粒子径)
下記の充填材について、エタノールを分散媒とし、レーザー回折式粒度分布測定装置(株式会社島津製作所製「SALD-2300」)を用いて0.2%ヘキサメタリン酸ナトリウム水溶液を分散媒に用いて体積基準で平均粒子径を測定した。
表1に記載の重合性単量体(A)の合計100質量部について粘度計(東機産業株式会社製、TV-30E型粘度計、JIS K-7117-2:1999に適合、コーン・プレートタイプ)を用いて、0.8°×R24のコーンロータで、サンプル量0.6mL、30℃にて測定した。1分間のプレヒートを行った後、測定を開始し、5分後の測定値をその粘度とした。
各実施例及び比較例で得られた歯科用硬化性組成物を真空脱泡後、ステンレス製の金型(寸法2mm×2mm×25mm)に充填し、上下をスライドガラスで圧接し、歯科重合用LED光照射器(株式会社モリタ製、商品名「ペンキュアー2000」)で1点10秒、片面を5点ずつ、スライドガラスの両面に光を照射して硬化させて硬化物の試験片を得た。各実施例及び比較例について、硬化物を5本ずつ作製し、硬化物は、金型から取り出した後、37℃の蒸留水中に24時間保管した。各試験片について、JIS T 6514:2015及びISO4049:2009に従って、精密万能試験機(株式会社島津製作所製、商品名「オートグラフAG-I 100kN」)を用いて、支点間距離20mm、クロスヘッドスピード1mm/分の条件下で3点曲げ試験を実施し、曲げ強さ及び曲げ弾性率を測定した(N=5)。各試験片の測定値の平均値を算出し、曲げ強さ及び曲げ弾性率とした。曲げ強さは80MPa以上であることが好ましく、90MPa以上であることがより好ましく、100MPa以上であることがさらに好ましく、120MPa以上であることが特に好ましい。曲げ強さの上限に特に制限はなく、例えば、200MPa以下、さらには150MPa以下であってもよい。曲げ弾性率は、重合収縮応力及び対合歯の摩耗を抑制することができる点から、8GPa以下が好ましく、2~7.5GPaがより好ましく、4~7GPaがさらに好ましい。
厚さ4.0mmのガラス板上に設置したリング状の金型(ステンレス製、内径5.5mm×厚さ0.8mm)内に、各実施例及び比較例で作製した歯科用硬化性組成物を充填した。前記ガラス板は、粒子径が50μmのアルミナパウダーでサンドブラスト処理したものを使用した。充填した歯科用硬化性組成物上に、万能試験機(株式会社島津製作所製、商品名「オートグラフAG-I 100kN」)と連結したステンレス製治具(φ5mm)を設置した。次いで、歯科重合用LED光照射器(株式会社モリタ製、商品名「ペンキュアー2000」)を用いて、ガラス板越しに20秒間歯科用硬化性組成物に光照射して歯科用硬化性組成物を硬化させた。この際、かかる光照射によって進行する歯科用硬化性組成物の重合反応による硬化に伴う重合収縮応力を、上記万能試験機で測定した(N=5)。各試験片の測定値を用いて算出した平均値を表1に示す。重合収縮応力が小さいほどコントラクションギャップが生じにくく好ましい。また、重合収縮応力が小さいと、一度により多くの歯科用硬化性組成物を充填することができるようになり、作業の面からも好ましい。重合収縮応力は、12.0MPa以下であることが好ましく、10.0MPa以下であることがより好ましく、9.0MPa以下であることがさらに好ましい。
各実施例及び比較例で得られた歯科用硬化性組成物のペースト0.25ccを測りとり、その上にガラス板を静置し、ガラス板を介して1kgの荷重を30秒間かけ、ペーストを押しつぶした。展延された円板状のペーストの最大直径及び最小直径の2点を測定し、2点の平均値(mm)を稠度とした(N=3)。各試験片の測定値を用いて算出した平均値を表1に示す。稠度が大きいほどペーストが柔らかいことを示し、ペーストの操作性の観点から11.0mm以上が好ましく、13.0mm以上がより好ましく、14.0mm以上がさらに好ましく、15.0mm以上が特に好ましい。また、100mm以下が好ましく、80mm以下がより好ましい。
各実施例及び比較例で得られた歯科用硬化性組成物の吸水量は、JIS T 6514:2015及びISO4049:2009に従って測定した(N=5)。各試験片の測定値を用いて算出した平均値を表1に示す。歯科用硬化性組成物の硬化には歯科重合用LED光照射器(株式会社モリタ製、商品名「ペンキュアー2000」)を用いた。吸水量は、35μg/mm3以下が好ましく、25μg/mm3以下がより好ましく、20μg/mm3以下がさらに好ましい。
牛歯エナメル質表面の準備:牛歯表面を耐水研磨紙(♯80、#1000、#3000;日本研紙株式会社製)で順次研磨し、エナメル質平滑鏡面を有する試験片を作製し、そのエナメル質表面(φ5mm以上)が出るように即時重合レジン(株式会社ジーシー製、商品名「ユニファストII」)にて試験片を金属モールドに包埋した。
歯科用硬化性組成物の準備:半球状のプラスチック製の型(φ11mm)に各実施例及び比較例で得られた歯科用硬化性組成物を充填した。充填した歯科用硬化性組成物を円柱状のプラスチック製のバーに立てて、LED重合器(株式会社モリタ製、商品名「αライトV」)にて3分間光照射した。光照射後、得られた硬化物の表面を耐水研磨紙(♯1000、♯2000、♯3000;日本研紙株式会社製)で順次研磨した。
上記で準備した牛歯エナメル質表面と歯科用硬化性組成物の硬化物をラインフェルダー式摩耗試験機(ナビック株式会社製)へセットした。次いで、牛歯を蒸留水に浸して室温下、硬化物を試験荷重7.9kgにて牛歯エナメル質表面に圧接して最大荷重時に30°回転させ、荷重が除かれるとともに回転も元に戻した(0°)。これを1回の操作として、この操作を40万回繰り返した。試験後、削れたエナメル質表面の体積をレーザー顕微鏡(株式会社キーエンス製、商品名「VR-3200」)により測定し、対合歯摩耗体積とした(N=6)。各試験片の測定値を用いて算出した平均値を表1に示す。対合歯摩耗体積は、0.3mm3以下が好ましく、0.25mm3以下がより好ましく、0.2mm3以下がさらに好ましい。
(多官能(メタ)アクリル系単量体(A-1))
9BG:ポリブチレングリコールジメタクリレート(下記式(4)、ブチレングリコール基の平均付加モル数:9)(C/O:4、主鎖を構成する炭素原子の総数と酸素原子の総数の合計:45)
D2.6E: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(エチレンオキシ基の平均付加モル数:2.6)
D7E: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(エチレンオキシ基の平均付加モル数:7)
(その他の重合性単量体(A-3))
3G:トリエチレングリコールジメタクリレート(C/O:2、主鎖を構成する炭素原子の総数と酸素原子の総数の合計:9)
9G:ポリエチレングリコールジメタクリレート(エチレングリコール基の平均付加モル数:9)(C/O:2、主鎖を構成する炭素原子の総数と酸素原子の総数の合計:27)
14G:ポリエチレングリコールジメタクリレート(エチレングリコール基の平均付加モル数:14)(C/O:2、主鎖を構成する炭素原子の総数と酸素原子の総数の合計:42)
3PG:トリプロピレングリコールジメタクリレート(下記式(5)、(C/O:3、主鎖を構成する炭素原子の総数と酸素原子の総数の合計:9))
充填材としては、下記の製造例で得られたものを用いた。
・NF180の製造
市販のバリウムガラス(ショット社製「GM27884 NanoFine180」)100質量部、3-メタクリロイルオキシプロピルトリメトキシシラン7質量部、及びトルエン173質量部を三口フラスコに入れ、2時間、室温下で撹拌した。トルエンを減圧下で留去した後、40℃で16時間真空乾燥を行い、さらに90℃で3時間加熱し、表面処理層が設けられた無機充填材(NF180)を得た。得られた無機充填材(NF180)の平均粒子径は0.2μmであった。
・UF2.0の製造
市販のバリウムガラス(ショット社製「UltraFine UF2.0」)100質量部、3-メタクリロイルオキシプロピルトリメトキシシラン5質量部、及びトルエン173質量部を三口フラスコに入れ、2時間、室温下で撹拌した。トルエンを減圧下で留去した後、40℃で16時間真空乾燥を行い、さらに90℃で3時間加熱し、表面処理層が設けられた無機充填材(UF2.0)を得た。得られた無機充填材(UF2.0)の平均粒子径は2.0μmであった。
・NF-CFの製造
予め重合開始剤としてアゾビスイソブチロニトリル(AIBN)を1質量%溶解した、Bis-GMAと3Gの重合性単量体混合物(質量比1:1)100質量部に対して、無機充填材として上記で製造したNF180を100質量部添加、混合しペースト化した。これを100℃、減圧雰囲気下で5時間加熱重合した。得られた硬化物を、振動ボールミルを用いて、平均粒子径が5μmとなるまで粉砕した。得られた粉末100gに対して、γ-メタクリロイルオキシプロピルトリメトキシシラン2質量%含有エタノール溶液200mL中、90℃で5時間還流することで表面処理を行ない、平均粒子径が5μmである有機無機複合充填材(NF-CF)を得た。
CQ:カンファーキノン
PDE:4-(N,N-ジメチルアミノ)安息香酸エチル
TN326:「チヌビン326」(BASFジャパン株式会社製)(紫外線吸収剤)
BHT:3,5-ジ-t-ブチル-4-ヒドロキシトルエン(重合禁止剤)
表1に記載された材料及び割合にて、これらを常温(23℃)及び暗所で混合することにより、歯科用硬化性組成物を調製した。これらの歯科用硬化性組成物について、上記した方法で各試験を行った。結果を表1に示した。
Claims (11)
- 重合性単量体(A)、充填材(B)、及び重合開始剤(C)を含む歯科用硬化性組成物であって、前記重合性単量体(A)が、炭素数1~15のアルコキシレン繰返し単位からなる部位(X)を有し芳香環を有さない多官能(メタ)アクリル系単量体(A-1)と、芳香環を有し水酸基を有さない多官能(メタ)アクリル系単量体(A-2)とを含み、前記部位(X)に含まれる炭素原子の総数と酸素原子の総数の比C/Oが2.5~10であり、前記部位(X)の主鎖を構成する炭素原子の総数と酸素原子の総数の合計が25~60であり、且つ重合性単量体(A)100質量部において前記多官能(メタ)アクリル系単量体(A-1)を3~60質量部を含む、歯科用硬化性組成物。
- 前記重合性単量体(A)の30℃における粘度が10~2500cPである、請求項1に記載の歯科用硬化性組成物。
- 前記多官能(メタ)アクリル系単量体(A-2)の含有量が、前記重合性単量体(A)100質量部において、10~97質量部である、請求項1又は2に記載の歯科用硬化性組成物。
- 前記X1を構成するアルコキシレン繰返し単位の炭素数が3~5である、請求項4に記載の歯科用硬化性組成物。
- 前記充填材(B)の平均粒子径が0.01~50μmである、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。
- 硬化物の曲げ弾性率が8GPa以下である、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。
- 重合収縮応力が12.0MPa以下である、請求項1~9のいずれか1項に記載の歯科用硬化性組成物。
- 請求項1~10のいずれか1項に記載の歯科用硬化性組成物を用いてなる、歯科用コンポジットレジン。
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