JP2021059515A - 歯科用接着性組成物 - Google Patents
歯科用接着性組成物 Download PDFInfo
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- JP2021059515A JP2021059515A JP2019185498A JP2019185498A JP2021059515A JP 2021059515 A JP2021059515 A JP 2021059515A JP 2019185498 A JP2019185498 A JP 2019185498A JP 2019185498 A JP2019185498 A JP 2019185498A JP 2021059515 A JP2021059515 A JP 2021059515A
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- JP
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- Prior art keywords
- polymerizable monomer
- meth
- adhesive composition
- group
- dental adhesive
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000003479 dental cement Substances 0.000 title claims abstract description 74
- 239000000178 monomer Substances 0.000 claims abstract description 144
- 239000000853 adhesive Substances 0.000 claims abstract description 54
- 230000001070 adhesive effect Effects 0.000 claims abstract description 53
- 230000002378 acidificating effect Effects 0.000 claims abstract description 43
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims description 27
- 230000002209 hydrophobic effect Effects 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229940023487 dental product Drugs 0.000 claims 1
- 210000004268 dentin Anatomy 0.000 abstract description 45
- 230000001747 exhibiting effect Effects 0.000 abstract description 5
- -1 difluoromethylene group Chemical group 0.000 description 70
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 239000002245 particle Substances 0.000 description 29
- 239000000945 filler Substances 0.000 description 26
- 239000001294 propane Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 9
- 238000011049 filling Methods 0.000 description 9
- 239000011256 inorganic filler Substances 0.000 description 9
- 229910003475 inorganic filler Inorganic materials 0.000 description 9
- 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 8
- 230000001588 bifunctional effect Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 7
- 239000000805 composite resin Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005530 etching Methods 0.000 description 6
- 230000000149 penetrating effect Effects 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 235000011180 diphosphates Nutrition 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 4
- SXNICUVVDOTUPD-UHFFFAOYSA-N CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C1=CC=CC=C1 SXNICUVVDOTUPD-UHFFFAOYSA-N 0.000 description 4
- 102100021758 E3 ubiquitin-protein transferase MAEA Human genes 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 101000616009 Homo sapiens E3 ubiquitin-protein transferase MAEA Proteins 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000007561 laser diffraction method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
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- 150000001451 organic peroxides Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000000790 scattering method Methods 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- 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
- CJSXYPVHJPHCCG-UHFFFAOYSA-N 2-(prop-2-enoylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(=O)C=C CJSXYPVHJPHCCG-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- ZKFOEDSYSPDTEB-UHFFFAOYSA-N 2-prop-2-enoyloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C=C ZKFOEDSYSPDTEB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-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
- 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
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 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 2
- OTFAQGCBYAXPCR-UHFFFAOYSA-N CC1=C(C(=O)COP(C2=CC=CC=C2)=O)C(=CC(=C1)C)C Chemical compound CC1=C(C(=O)COP(C2=CC=CC=C2)=O)C(=CC(=C1)C)C OTFAQGCBYAXPCR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 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 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000006353 oxyethylene group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 239000012756 surface treatment agent Substances 0.000 description 2
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- BWTMTZBMAGYMOD-UHFFFAOYSA-N (2,2,3,3,4,4,5,5-octafluoro-6-prop-2-enoyloxyhexyl) prop-2-enoate Chemical compound C=CC(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C=C BWTMTZBMAGYMOD-UHFFFAOYSA-N 0.000 description 1
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- JLLAWIKMLAQZCZ-UHFFFAOYSA-N (2,6-dichlorophenyl)-diphenylphosphorylmethanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 JLLAWIKMLAQZCZ-UHFFFAOYSA-N 0.000 description 1
- SUEDCWGEKSLKOM-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-diphenylphosphorylmethanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SUEDCWGEKSLKOM-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- XFHQGYBXSCRMNT-JTQLQIEISA-N (2s)-3-phenyl-2-(prop-2-enoylamino)propanoic acid Chemical compound C=CC(=O)N[C@H](C(=O)O)CC1=CC=CC=C1 XFHQGYBXSCRMNT-JTQLQIEISA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
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- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
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- ZESGLEJYMHVEKI-UHFFFAOYSA-N 10-prop-2-enoyloxydecylazanium chloride Chemical compound [Cl-].C(C=C)(=O)OCCCCCCCCCC[NH3+] ZESGLEJYMHVEKI-UHFFFAOYSA-N 0.000 description 1
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- IVBBKDXIZQKTOK-UHFFFAOYSA-N 16-phosphonooxyhexadecyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCCCCCCCCCCCOC(=O)C=C IVBBKDXIZQKTOK-UHFFFAOYSA-N 0.000 description 1
- GLCVQJJSGABYQF-UHFFFAOYSA-M 16-pyridin-1-ium-1-ylhexadecyl prop-2-enoate chloride Chemical compound [Cl-].C(C=C)(=O)OCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 GLCVQJJSGABYQF-UHFFFAOYSA-M 0.000 description 1
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- JPOUDZAPLMMUES-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)octane Chemical compound CCCCCCC(C)(OOC(C)(C)C)OOC(C)(C)C JPOUDZAPLMMUES-UHFFFAOYSA-N 0.000 description 1
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- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HKZXVRSDEWSULK-UHFFFAOYSA-N 2-[hydroxy(6-prop-2-enoyloxyhexoxy)phosphoryl]acetic acid Chemical compound C=CC(=O)OCCCCCCOP(=O)(CC(=O)O)O HKZXVRSDEWSULK-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
[1]フルオロカーボン基、2つ以上のオレフィン性二重結合、及び1つ以上のエーテル結合を有する重合性単量体(A)、酸性基含有重合性単量体(B)、並びに重合開始剤(C)を含有する、歯科用接着性組成物。
[2]前記重合性単量体(A)が下記一般式(1)又は(2)で表される前記重合性単量体を含有する、[1]に記載の歯科用接着性組成物。
[3]前記重合性単量体(A)が一般式(1)で表される重合性単量体であり、Xが一般式(3)で表される基である、[2]に記載の歯科用接着性組成物。
[4]R3がHである、[2]又は[3]に記載の歯科用接着性組成物。
[5]Yにおける−CF2−の数が2〜9である、[2]〜[4]のいずれかに記載の歯科用接着性組成物。
[6]Yにおける−O−の数が2〜9である、[2]〜[5]のいずれかに記載の歯科用接着性組成物。
[7]Yが−CF2−CF2−を含む、[2]〜[6]のいずれかに記載の歯科用接着性組成物。
[8]前記重合性単量体(A)が有するエーテル結合の数が1〜10である、[1]〜[7]のいずれかに記載の歯科用接着性組成物。
[9]前記重合性単量体(A)が有するフッ素原子の数が2〜20である、[1]〜[8]のいずれかに記載の歯科用接着性組成物。
[10]酸性基を有しない親水性重合性単量体(D)をさらに含む、[1]〜[9]のいずれかに記載の歯科用接着性組成物。
[11]酸性基を有しない疎水性重合性単量体(E)(ただし、重合性単量体(A)に該当するものを除く)をさらに含む、[1]〜[10]のいずれかに記載の歯科用接着性組成物。
[12]前記重合開始剤(C)が、光重合開始剤(C−1)である、[1]〜[11]のいずれかに記載の歯科用接着性組成物。
[13]前記酸性基含有重合性単量体(B)が、リン酸基含有重合性単量体である、[1]〜[12]のいずれかに記載の歯科用接着性組成物。
[14]前記重合性単量体(A)の含有量が、重合性単量体の全量100質量部において、0.5〜40質量部である、[1]〜[13]のいずれかに記載の歯科用接着性組成物。
[15][1]〜[14]のいずれかに記載の歯科用接着性組成物からなる、歯科用ボンディング材。
本発明の歯科用接着性組成物は、フルオロカーボン基、2つ以上のオレフィン性二重結合、及び1つ以上のエーテル結合を有する重合性単量体(A)(以下、単に「重合性単量体(A)」と記載することもある)を含む。本発明では重合性単量体(A)を用いることを技術の核とし、このような重合性単量体(A)を他の成分と組み合わせることで、歯科用接着性組成物の象牙質に対する高い接着性(初期接着力及び接着耐久性)、及び高い象牙質凝集破壊率を達成することができる。重合性単量体(A)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。
酸性基含有重合性単量体(B)は、酸エッチング効果及びプライマー処理効果を有しており、脱灰作用及び浸透作用を与える成分である。また、酸性基含有重合性単量体(B)は、重合可能であり、硬化作用も付与する。酸性基含有重合性単量体(B)を含有することにより、歯質に対する接着性と接着耐久性が向上する。
本発明に用いられる重合開始剤(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る重合開始剤が好ましく用いられる。重合開始剤(C)は、特に、光重合開始剤(C−1)及び化学重合開始剤(C−2)からなる群から選ばれる少なくとも1種を使用できる。
酸性基を有しない親水性重合性単量体(D)としては、酸性基を有さず、重合性基を有するラジカルモノマーが好ましく、ラジカル重合が容易である観点から、重合性基は(メタ)アクリル基及び/又は(メタ)アクリルアミド基が好ましい。酸性基を有しない親水性重合性単量体(D)とは、25℃における水に対する溶解度が10質量%以上のものを意味し、該溶解度が30質量%以上のものが好ましく、25℃において任意の割合で水に溶解可能なものがより好ましい。酸性基を有しない親水性重合性単量体(D)は、歯科用接着性組成物の成分の歯質への浸透を促進するとともに、自らも歯質に浸透して歯質中の有機成分(コラーゲン)に接着する。酸性基を有しない親水性重合性単量体(D)としては、水酸基、オキシメチレン基、オキシエチレン基、オキシプロプレン基、アミド基などの親水性基を有するものが好ましく、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、ポリエチレングリコールジ(メタ)アクリレート(オキシエチレン基の数が9以上のもの)などの親水性の単官能性(メタ)アクリレート系重合性単量体;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)アクリルアミド及び下記一般式(5)で表される単官能(メタ)アクリルアミド系単量体などの親水性の単官能性(メタ)アクリルアミド系重合性単量体などが挙げられる。
酸性基を有しない疎水性重合性単量体(E)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)アクリル基及び/又は(メタ)アクリルアミド基が好ましい。酸性基を有しない疎水性重合性単量体(E)とは、25℃における水に対する溶解度が10質量%未満のものを意味し、例えば、芳香族化合物系の二官能性単量体、脂肪族化合物系の二官能性単量体、三官能性以上の単量体などの架橋性の単量体が例示される(ただし、重合性単量体(A)に該当するものを除く)。酸性基を有しない疎水性重合性単量体(E)は、歯科用接着性組成物の硬化物の機械的強度、取り扱い性などを向上させる。
MDP:10−メタクリロイルオキシデシルジヒドロジェンホスフェート
CQ:カンファーキノン
BAPO:ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキシド
HEMA:2−ヒドロキシエチルメタクリレート
Bis−GMA:2,2−ビス〔4−(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)フェニル〕プロパン
DABE:4−(N,N−ジメチルアミノ)安息香酸エチル(重合促進剤)
DEPT:N,N−ジ(2−ヒドロキシエチル)−p−トルイジン(重合促進剤)
BHT:2,6−ジ−t−ブチル−4−メチルフェノール(安定剤(重合禁止剤))
水:精製水
EtOH:エタノール
R972:日本アエロジル株式会社製、微粒子シリカ「AEROSIL(商標登録) R 972」、平均粒子径:16nm
8FMA:オクタフルオロペンチルメタクリレート
ウシ下顎前歯の唇面を流水下にて#80シリコンカーバイド紙(日本研紙株式会社製)で研磨して、象牙質の平坦面を露出させたサンプルを得た。得られたサンプルを流水下にて#1000のシリコンカーバイド紙(日本研紙株式会社製)でさらに研磨した。研磨終了後、表面の水をエアブローすることで乾燥した。乾燥後の平滑面に、直径3mmの丸穴を有する厚さ約150μmの粘着テープを貼着し、接着面積を規定した。
上記初期接着力及び接着耐久性に関して引張り接着強さの測定を行った接着試験供試サンプルのそれぞれについて、該試験後の破断面を目視で観察し、全サンプル中、象牙質側が破壊しているサンプルの数の割合(%)を象牙質凝集破壊率とした。象牙質凝集破壊率が高ければ、樹脂含浸層内部への歯科用接着性組成物の浸透性が高く、それによって樹脂含浸層内部の硬化性に寄与でき、結果的に接着界面及び樹脂含浸層内部の硬化性が高くなり、接着界面の接合状態が良好であることを意味する。
調製した実施例及び比較例の歯科用接着性組成物に圧縮空気を吹き付けて揮発性有機溶媒を揮発させた。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、該硬化物を金型から取り出した後、37℃の蒸留水中に24時間保管した。保管後の硬化物を試験供試サンプルとして、万能試験機(商品名:AG−I 100N、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/分の条件下で曲げ強さを測定し、各サンプルの測定値の平均値を算出し、曲げ強さとした。
Claims (15)
- フルオロカーボン基、2つ以上のオレフィン性二重結合、及び1つ以上のエーテル結合を有する重合性単量体(A)、酸性基含有重合性単量体(B)、並びに重合開始剤(C)を含有する、歯科用接着性組成物。
- 前記重合性単量体(A)が一般式(1)で表される重合性単量体であり、Xが一般式(3)で表される基である、請求項2に記載の歯科用接着性組成物。
- R3がHである、請求項2又は3に記載の歯科用接着性組成物。
- Yにおける−CF2−の数が2〜9である、請求項2〜4のいずれか1項に記載の歯科用接着性組成物。
- Yにおける−O−の数が2〜9である、請求項2〜5のいずれか1項に記載の歯科用接着性組成物。
- Yが−CF2−CF2−を含む、請求項2〜6のいずれか1項に記載の歯科用接着性組成物。
- 前記重合性単量体(A)が有するエーテル結合の数が1〜10である、請求項1〜7のいずれか1項に記載の歯科用接着性組成物。
- 前記重合性単量体(A)が有するフッ素原子の数が2〜20である、請求項1〜8のいずれか1項に記載の歯科用接着性組成物。
- 酸性基を有しない親水性重合性単量体(D)をさらに含む、請求項1〜9のいずれか1項に記載の歯科用接着性組成物。
- 酸性基を有しない疎水性重合性単量体(E)(ただし、重合性単量体(A)に該当するものを除く)をさらに含む、請求項1〜10のいずれか1項に記載の歯科用接着性組成物。
- 前記重合開始剤(C)が、光重合開始剤(C−1)である、請求項1〜11のいずれか1項に記載の歯科用接着性組成物。
- 前記酸性基含有重合性単量体(B)が、リン酸基含有重合性単量体である、請求項1〜12のいずれか1項に記載の歯科用接着性組成物。
- 前記重合性単量体(A)の含有量が、重合性単量体の全量100質量部において、0.5〜40質量部である、請求項1〜13のいずれか1項に記載の歯科用接着性組成物。
- 請求項1〜14のいずれか1項に記載の歯科用接着性組成物からなる、歯科用ボンディング材。
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