JP5802960B2 - 歯質用接着材 - Google Patents
歯質用接着材 Download PDFInfo
- Publication number
- JP5802960B2 JP5802960B2 JP2011113601A JP2011113601A JP5802960B2 JP 5802960 B2 JP5802960 B2 JP 5802960B2 JP 2011113601 A JP2011113601 A JP 2011113601A JP 2011113601 A JP2011113601 A JP 2011113601A JP 5802960 B2 JP5802960 B2 JP 5802960B2
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- Japan
- Prior art keywords
- polymerizable monomer
- acidic group
- group
- adhesive
- silica
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003479 dental cement Substances 0.000 title claims description 36
- 239000000178 monomer Substances 0.000 claims description 117
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 112
- 230000002378 acidificating effect Effects 0.000 claims description 104
- 239000000853 adhesive Substances 0.000 claims description 73
- 230000001070 adhesive effect Effects 0.000 claims description 71
- 239000000377 silicon dioxide Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 229910021645 metal ion Inorganic materials 0.000 claims description 31
- 239000002245 particle Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 22
- 210000004268 dentin Anatomy 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 14
- 229910021485 fumed silica Inorganic materials 0.000 claims description 11
- 239000003505 polymerization initiator Substances 0.000 claims description 11
- -1 methacryloyl group Chemical group 0.000 description 43
- 125000005372 silanol group Chemical group 0.000 description 32
- 238000000034 method Methods 0.000 description 26
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 16
- 210000003298 dental enamel Anatomy 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 238000003860 storage Methods 0.000 description 14
- 150000007513 acids Chemical class 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 150000002736 metal compounds Chemical class 0.000 description 12
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 12
- 239000001294 propane Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000011164 primary particle Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 6
- 239000000805 composite resin Substances 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 239000011775 sodium fluoride Substances 0.000 description 6
- 235000013024 sodium fluoride Nutrition 0.000 description 6
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 229910001512 metal fluoride Inorganic materials 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 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 4
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 4
- 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 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 229930006711 bornane-2,3-dione Natural products 0.000 description 4
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000004819 silanols Chemical class 0.000 description 4
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 4
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JDKSTARXLKKYPS-UHFFFAOYSA-N 2-[10-(2-methylprop-2-enoyloxy)decyl]propanedioic acid Chemical compound CC(=C)C(=O)OCCCCCCCCCCC(C(O)=O)C(O)=O JDKSTARXLKKYPS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- 102100026735 Coagulation factor VIII Human genes 0.000 description 3
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 208000002925 dental caries Diseases 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 150000002432 hydroperoxides Chemical class 0.000 description 3
- SORGMJIXNUWMMR-UHFFFAOYSA-N lanthanum(3+);propan-2-olate Chemical compound [La+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SORGMJIXNUWMMR-UHFFFAOYSA-N 0.000 description 3
- YXEUGTSPQFTXTR-UHFFFAOYSA-K lanthanum(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[La+3] YXEUGTSPQFTXTR-UHFFFAOYSA-K 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000011163 secondary particle Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- BYMUNNMMXKDFEZ-UHFFFAOYSA-K trifluorolanthanum Chemical compound F[La](F)F BYMUNNMMXKDFEZ-UHFFFAOYSA-K 0.000 description 3
- 150000003682 vanadium compounds Chemical class 0.000 description 3
- YGGMQWSJXSNGDT-UHFFFAOYSA-N (4-fluorophenyl)boron Chemical compound [B]C1=CC=C(F)C=C1 YGGMQWSJXSNGDT-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 229910017569 La2(CO3)3 Inorganic materials 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052771 Terbium Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- XKGMHABTFTUWDV-UHFFFAOYSA-N [W+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] Chemical compound [W+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] XKGMHABTFTUWDV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- NYPANIKZEAZXAE-UHFFFAOYSA-N butan-1-olate;lanthanum(3+) Chemical compound [La+3].CCCC[O-].CCCC[O-].CCCC[O-] NYPANIKZEAZXAE-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000005115 demineralization Methods 0.000 description 2
- 230000002328 demineralizing effect Effects 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- ZFSQRSOTOXERMJ-UHFFFAOYSA-N ethanol;iron Chemical compound [Fe].CCO.CCO.CCO ZFSQRSOTOXERMJ-UHFFFAOYSA-N 0.000 description 2
- NPAJGHOZGYPSTK-UHFFFAOYSA-N ethanolate;lanthanum(3+) Chemical compound [La+3].CC[O-].CC[O-].CC[O-] NPAJGHOZGYPSTK-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000010335 hydrothermal treatment Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- NZPIUJUFIFZSPW-UHFFFAOYSA-H lanthanum carbonate Chemical compound [La+3].[La+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O NZPIUJUFIFZSPW-UHFFFAOYSA-H 0.000 description 2
- 229960001633 lanthanum carbonate Drugs 0.000 description 2
- RCFZUDZONKPRJX-UHFFFAOYSA-N lanthanum(3+) methanolate Chemical compound [La+3].[O-]C.[O-]C.[O-]C RCFZUDZONKPRJX-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 2
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 2
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 2
- YFGRPIXHCIXTLM-UHFFFAOYSA-N tungsten(4+) Chemical compound [W+4] YFGRPIXHCIXTLM-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
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- 235000003270 potassium fluoride Nutrition 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
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-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
- SLACPSWSQQIQTG-UHFFFAOYSA-N propan-2-olate;scandium(3+) Chemical compound [Sc+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SLACPSWSQQIQTG-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- SOFSSZFBVOGIKD-UHFFFAOYSA-N pyrimidine-2,4,5-trione Chemical class O=C1NC(=O)C(=O)C=N1 SOFSSZFBVOGIKD-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 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
- 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
- 125000005504 styryl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- USLHPQORLCHMOC-UHFFFAOYSA-N triethoxygallane Chemical compound CCO[Ga](OCC)OCC USLHPQORLCHMOC-UHFFFAOYSA-N 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical group OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- SPDOFQMJCKDTKZ-UHFFFAOYSA-N zinc;ethoxymethanolate Chemical compound [Zn+2].CCOC[O-].CCOC[O-] SPDOFQMJCKDTKZ-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical compound F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Dental Preparations (AREA)
Description
(A)酸性基を有する重合性単量体を少なくとも一部として含んでなる重合性単量体成分、及び
(B)シリカ系粒子としてフュームドシリカ
を含有する歯質用接着材であって、
前記シリカ系粒子が、比表面積が50〜500m2/gであり、表面にシラノール基を少なくとも3.5個/nm2含むシリカ系粒子であり、且つ水を含まない1液の歯質用接着材が提供される。
(A)重合性単量体成分
本発明において重合性単量体は、分子中に少なくとも1つの重合性不飽和基を含有し、重合反応によって高分子を形成し得る化合物が制限なく使用できる。ここで、重合性不飽和基を例示すれば、アクリロイル基、メタクリロイル基、アクリルアミド基、メタクリルアミド基、ビニル基、アリル基、エチニル基、スチリル基などを挙げることができる。特に、硬化速度の速さから、アクリロイル基、メタクリロイル基、アクリルアミド基、メタクリルアミド基等が好ましく、アクリロイル基、メタクリロイル基が最も好ましい。
本発明において、(A1)酸性基含有重合性単量体は、上記重合性単量体において、分子中に少なくとも1つの酸性基を有するものであり、該酸性基としては、pKa(25℃)が5より小さく、活性プロトンを解離可能な官能基を言う。好適には、次に示すような基を挙げることができる。
また、これら化合物以外にも、ビニル基に直接ホスホン酸基が結合したビニルホスホン酸類や、アクリル酸、メタクリル酸、ビニルスルホン酸等を使用することができる。
非酸性基含有重合性単量体は、少なくとも一つの重合性不飽和基を有する重合性単量体の内、酸性基を有しない公知のものが制限無く使用できる。複数の重合性不飽和基を有する多官能重合性単量体は、硬化速度、硬化体の機械的物性、耐水性、および耐着色性等を良好にする観点から好適に用いられる。また、(メタ)アクリレート系重合性単量体が好適に使用される。多官能性の(メタ)アクリレート系重合性単量体の代表例としては、下記(1)〜(3)に示されるものが挙げられる。
(1−1)芳香族化合物系のもの
2,2’−ビス{4−[3−(メタ)アクリロイルオキシ−2−ヒドロキシプロポキシ]フェニル}プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシポリエトキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシジエトキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシテトラエトキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシペンタエトキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシジプロポキシフェニル]プロパン、2,2’−ビス[4−(メタ)アクリロイルオキシエトキシエトキシフェニル]プロパン、2[4−(メタ)アクリロイルオキシジエトキシフェニル]−2[4−(メタ)クリロイルオキシトリエトキシフェニル]プロパン、2[4−(メタ)アクリロイルオキシジプロポキシフェニル]−2−[4−(メタ)クリロイルオキシトリエトキシフェニル]プロパン、2,2−ビス[4−(メタ)クリロイルオキシプロポキシフェニル]プロパン;上記の各種メタクリレートに対応するアクリレート;及びOH基含有ビニルモノマーと、脂肪族ジイソシアネート化合物との付加から得られるジアダクト等。
(上記OH基含有ビニルモノマーとしては、2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレート、あるいはこれらメタクリレートに対応するアクリレートを例示できる。また、上記ジイソシアネートとしては、ジイソシアネートメチルベンゼン、4,4’−ジフェニルメタンジイソシアネートを例示できる。)
(1−2)脂肪族化合物系のもの
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、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、テトラエチレングリコールジメタクリレート、ネオペンチルグリコールジメタクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレート及びこれらのメタクリレートに対応するアクリレート;およびOH基含有ビニルモノマーと、脂肪族ジイソシアネート化合物との付加から得られるジアダクト等。
(上記のOH基含有ビニルモノマーとしては、先に例示したものと同様のものを挙げることができ、脂肪族ジイソシアネート化合物としては、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)等を挙げることができる。)
(2)三官能重合性単量体
トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールメタントリメタクリレート等のメタクリレート;及びこれらのメタクリレートに対応するアクリレート等。
ペンタエリスリトールテトラメタクリレート、ペンタエリスリトールテトラアクリレート;及びジイソシアネート化合物とグリシドールジメタクリレートとの付加体から得られるジアダクト等;
(上記のジイソシアネート化合物としては、ジイソシアネートメチルベンゼン、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)、4,4−ジフェニルメタンジイソシアネート、トリレン−2,4−ジイソシアネート等を挙げることができる。
(B)シリカ系粒子
本発明において(B)シリカ系粒子は、比表面積が50〜500m2/gであり、表面にシラノール基を少なくとも3.5個/nm2含むものが使用される。歯科用接着材にシリカ系粒子をフィラー等として配合することは公知であるが、その場合に用いられるものは上記比表面積を満足しないものも多く、また、満足しているものについても、表面のシラノール基量は上記範囲を大きく下回るのが普通である。例えば、特許文献7には、酸性基含有重合性単量体を含有する歯科用接着材に対して、フュームドシリカを配合することが開示されているが、このヒュームドシリカは、係る表面のシラノール基量は0.1個/nm2以上であり、上限は2個/nm2になっている。
シリカ1g当たりのシラノールの数(個/g)=水分量(質量%)×0.01×水分子1個を生成するシラノールの数(=2)×アボガドロ定数/水の分子量
=水分量(質量%)×0.01×2×6.02×1023/18.0
=水分量(質量%)×6.689×1020
次いで、得られたシリカ1g当たりのシラノールの数(個/g)から下記式により、単位非表面積当たりのシラノール基数(個/nm2;表面シラノール基量)を求める。
表面シラノール基量(個/nm2)=水分量(質量%)×6.689×1020/(非表面積(m2/g)×1018)
=668.9×水分量(wt%)×非表面積(m2/g)
本発明において使用するシリカ系粒子の平均粒子径は特に限定されないが、前記比表面積の範囲の要件を満足させるためには、平均1次粒子径が1〜100nm、平均二次粒子径が0.01μm〜100μmのものが好ましい。さらに、平均二次粒子径は、0.02〜10μmのものが最も好ましい。こうしたシリカの平均一次粒子径は、走査電子顕微鏡にて撮影した画像を画像解析して求めたものである。具体的には、倍率10万倍において、走査電子顕微鏡にて視野を変えて50の画像を撮影し、これを用いて2500個の原体シリカ微粒子について平均一次粒子径を画像解析し、個数平均を求めた値である。また、平均二次粒子径は、遠心沈降式光透過法の粒度分布計(例えば、ブルックヘブン社製「BI−DCP」)を用いて求めた体積平均粒子径である。
本発明の歯質用接着材において、(A1)酸性基含有重合性単量体は、その一部を多価金属塩として含有させても良い。特に、多価金属塩を形成する(C)多価金属イオンが、酸性基含有重合性単量体が有する酸性基の酸の価数よりも大きいイオン価の金属イオンである場合には、一個の多価金属イオンに対して、複数の酸性基含有重合性単量体がイオン結合するものになるため、硬化体では酸性基と多価金属イオンとの架橋構造が形成される。しかも、本発明においては(B)シリカ系粒子が配合されているため、該シリカ系粒子の隙間を、係るイオン架橋した重合体が絡むことになる。そして、多価金属イオンは、このシリカ系粒子上のシラノール基とも結合し、これらからより強固で密度の高い架橋ネットワークが形成されると考えられる。これらから、得られる硬化体の耐水性は大きく向上し、歯質に対する接着強度も著しく高くでき好ましい。
本発明の歯質用接着材には、有効量の重合開始剤を配合させるのが好適である。このような重合開始剤としては、光重合型、化学重合型、加熱重合型、いずれも使用できるが、任意のタイミングで重合効果させることができ、必ずしも混合の必要性がないことから、光重合型の重合開始剤が好ましい。
(その他の成分)
本発明の歯質用接着材には、さらに揮発性有機溶媒を配合しても良い。揮発性有機溶媒は、室温で揮発性を有し水溶性を示すものを好適に使用することができる。ここで言う揮発性とは、760mmHgでの沸点が100℃以下であり、且つ20℃における蒸気圧が1.0KPa以上であることを言う。また、水溶性とは、20℃での水への溶解度が20g/100ml以上であり、好ましくは該20℃において水と任意の割合で相溶することを言う。このような揮発性の水溶性有機溶媒としては、メタノール、エタノール、n−プロパノール、イソプロピルアルコール、ターシャリーブタノール、アセトン、メチルエチルケトン等を挙げることができる。これら有機溶媒は必要に応じ複数を混合して用いることも可能である。生体に対する毒性を考慮すると、エタノール、イソプロピルアルコール及びアセトンが好ましい。
略称及び略号
[(A)酸性基を有する重合性単量体を少なくとも一部として含んでなる重合性単量体]
(A1)酸性基含有重合性単量体
SPM:2−メタクリロイルオキシエチルジハイドロジェンフォスフェートとビス(2−メタクリロイルオキシエチル)ハイドロジェンフォスフェートの混合物
MAC−10:11−メタクリロイルオキシ−1,1−ウンデカンジカルボン酸
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
(A2)非酸性基含有重合性単量体
BisGMA:2,2−ビス(4−(2−ヒドロキシ−3−メタクリルオキシプロポキシ)フェニル)プロパン
3G:トリエチレングリコールジメタクリレート
HEMA:2−ヒドロキシエチルメタクリレート
[(B)シリカ]
FS1:フュームドシリカ、平均1次粒子径18nm、比表面積220m2/g、表面シラノール基量5.0個/nm2
FS2:フュームドシリカ、平均1次粒子径7nm、比表面積230m2/g、表面シラノール基量1.2個/nm2、ジメチルジクロロシラン処理
SS:ゾルゲルシリカ、平均1次粒子径60nm、比表面積70m2/g、表面シラノール基量3.0個/nm2、3−メタクリルオキシプロピルトリメトキシシラン処理
PS:沈降シリカ、平均1次粒子径30nm、比表面積180m2/g、表面シラノール基量6.0個/nm2、3−メタクリルオキシプロピルトリメトキシシラン処理
MS:溶融シリカ、平均1次粒子径0.4μm、比表面積8m2/g、表面シラノール基量2個/nm2、3−メタクリルオキシプロピルトリメトキシシラン処理
なお、シリカの表面シラノール基量は、次のような手法で測定した。すなわち、シリカ試料を25℃、相対湿度80%の雰囲気中に45日放置した後、120℃で12時間乾燥した。次いで、このシリカ試料を、メタノール溶媒中に分散し、カールフィッシャー水分計(例えば、京都電子工業社製「MKS-210型」)により、滴定試薬として、「HYDRANAL COMPOSITE 5K」(Riedel−deHaen社製)を用いて水分量を滴定した。測定された水分量から、下記式により表面シラノール基量を計算して求めた。
[(C)多価金属イオンの供給源]
Ti(O−nBu)4:チタニウムテトラブトキシド
Ti(O−iPr)4:チタニウムテトライソプロポキシド
TiF4 :フッ化チタニウム
TiO2 :酸化チタン
W(O−iPr)4 :タングステン(IV)テトライソプロポキシド
ZrO2 :酸化ジルコニウム
Al(O−iPr)3:アルミニウムトリイソプロポキシド
AlF3 :フッ化アルミニウム
La(O−iPr)3:ランタントリイソプロポキシド
La(OH)3 :ランタンヒドロキシド
Sc(O−iPr)3:スカンジウムトリイソプロポキシド
Yb(O−iPr)3:イッテルビウムトリイソプロポキシド
Fe(O−Et)3 :鉄(III)エトキシド
Ca(OH)2 :カルシウムヒドロキシド
[(D)重合開始剤]
CQ:カンファーキノン
DMBE:p−N,N−ジメチルアミノ安息香酸エチル
TPO:2,4,6−トリメチルベンゾイルジフェニルフォスフィンオキシド
[その他成分]
[フッ化物イオン源]
NaF:フッ化ナトリウム
[重合禁止剤]
BHT:2,6−ジ−t−ブチル−p−クレゾール
HQME:ハイドロキノンモノメチルエーテル
[揮発性の水溶性有機溶媒]
IPA:イソプロピルアルコール
アセトン
また、以下の実施例及び比較例において、得られた歯科用接着材の物性の測定は以下の方法により実施した。
(1)初期接着強度の試験方法
屠殺後24時間以内に牛前歯を抜去し、注水下、#600のエメリーペーパーで唇面に平行になるようにエナメル質及び象牙質平面を削りだした。次に、これらの面に圧縮空気を約10秒間吹き付けて乾燥した後、エナメル質及び象牙質のいずれかの平面に直径3mmの孔の開いた両面テープを固定し、次いで、厚さ0.5mm直径8mmの孔の開いたパラフィンワックスを上記円孔上に同一中心となるように固定して模擬窩洞を形成した。この模擬窩洞内に歯質用接着材を塗布し、10秒間放置後、圧縮空気を約10秒間吹き付けて乾燥し、歯科用可視光照射器(トクソーパワーライト、トクヤマ社製)にて10秒間光照射した。さらにその上に歯科用コンポジットレジン(エステライトΣクリック、トクヤマデンタル社製)を充填し、可視光照射器により10秒間光照射して、接着試験片を作製した。
(2)保存安定性の試験方法
歯科用接着材を、調製後50℃のインキュベーター内で2ヶ月間保存した。この接着材を用いて、上記初期接着強度測定方法と同様の方法により接着強度を測定し、保存前の初期接着強度と比較した。
重合性単量体として25.0gのSPM、30gのBisGMA、20gの3G及び25gのHEMAと、シリカとして20gのFS1と、重合開始剤として1.25gのカンファーキノン、1.25gのDMBE、1.0gのTPOと、及びその他成分としてIPAを85g、NaFを0.84g、BHTを0.63g、HQMEを0.1g用い、これらを均一になるまで攪拌混合して本発明の歯質用接着材を調製した。
実施例1の方法に準じ、表1に示した、組成の異なる接着材を各調製した。得られた歯質用接着材について、エナメル質、象牙質に対する初期接着強度を各測定した。また、こられの接着材について、50℃のインキュベーター内で2ヶ月間保存し、保存安定性を評価した。接着材組成を表1に、評価結果を表2にそれぞれ示した。
酸性基含有重合性単量体として25.0gのSPMと多価金属イオン源として5.2gのチタニウムテトラブトキシドを均一になるまで撹拌混合した後、30gのBisGMA、20gの3G及び25gのHEMAと、シリカとして20gのFS1と、重合開始剤として1.25gのカンファーキノン、1.25gのDMBE、1.0gのTPOと、及びその他成分としてIPAを85g、NaFを0.84g、BHTを0.63g、HQMEを0.1g用い、これらを均一になるまで攪拌混合して本発明の歯質用接着材を調製した。
実施例6の方法に準じ、表3及び表5に示した、組成の異なる接着材を各調製した。得られた歯質用接着材について、エナメル質、象牙質に対する初期接着強度を各測定した。また、こられの接着材について、50℃のインキュベーター内で2ヶ月間保存し、保存安定性を評価した。接着材組成を表3及び表5に、評価結果を表4及び表6にそれぞれ示した。
Claims (5)
- (A)酸性基を有する重合性単量体を少なくとも一部として含んでなる重合性単量体成分、及び
(B)シリカ系粒子としてフュームドシリカ
を含有する歯質用接着材であって、
前記フュームドシリカが、比表面積が50〜500m2/gであり、表面にシラノール基を少なくとも3.5個/nm2含むフュームドシリカであり、
且つ水を含まないことを特徴とする1液の歯質用接着材。 - 前記(A)重合性単量体100質量部としたとき、(B)フュームドシリカの含有量が10〜100質量部である請求項1に記載の歯質用接着材。
- さらに、酸性基を有する重合性単量体の一部が、多価金属塩を形成している請求項1または請求項2に記載の歯質用接着材。
- 多価金属塩を形成する(C)多価金属イオンが、酸性基を有する重合性単量体が有する酸性基の酸の価数よりも大きいイオン価の金属イオンである請求項3に記載の歯質用接着材。
- さらに、(D)重合開始剤を含む請求項1〜4のいずれか一項に記載の歯質用接着材。
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