JP7022749B2 - 2ペースト型歯科用硬化性組成物 - Google Patents
2ペースト型歯科用硬化性組成物 Download PDFInfo
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- JP7022749B2 JP7022749B2 JP2019527040A JP2019527040A JP7022749B2 JP 7022749 B2 JP7022749 B2 JP 7022749B2 JP 2019527040 A JP2019527040 A JP 2019527040A JP 2019527040 A JP2019527040 A JP 2019527040A JP 7022749 B2 JP7022749 B2 JP 7022749B2
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- 239000000203 mixture Substances 0.000 title claims description 105
- -1 acryloxy group Chemical group 0.000 claims description 164
- 239000000178 monomer Substances 0.000 claims description 91
- 125000004432 carbon atom Chemical group C* 0.000 claims description 89
- 239000000945 filler Substances 0.000 claims description 62
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001931 aliphatic group Chemical group 0.000 claims description 49
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 40
- 230000002378 acidificating effect Effects 0.000 claims description 35
- 239000011521 glass Substances 0.000 claims description 34
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 229910052788 barium Inorganic materials 0.000 claims description 11
- 239000003505 polymerization initiator Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 229910052726 zirconium Inorganic materials 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
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- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
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- 239000000853 adhesive Substances 0.000 description 71
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
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- 238000012360 testing method Methods 0.000 description 16
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- 210000004268 dentin Anatomy 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
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- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 8
- WVMPCBWWBLZKPD-UHFFFAOYSA-N dilithium oxido-[oxido(oxo)silyl]oxy-oxosilane Chemical compound [Li+].[Li+].[O-][Si](=O)O[Si]([O-])=O WVMPCBWWBLZKPD-UHFFFAOYSA-N 0.000 description 8
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- 229910001220 stainless steel Inorganic materials 0.000 description 8
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 7
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- 230000000052 comparative effect Effects 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
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- 229910000077 silane Inorganic materials 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical group [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 6
- 125000005370 alkoxysilyl group Chemical group 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000003479 dental cement Substances 0.000 description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000000542 sulfonic acid group Chemical group 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000012766 organic filler Substances 0.000 description 5
- 150000001451 organic peroxides Chemical class 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 239000012756 surface treatment agent Substances 0.000 description 5
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 4
- 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 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
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 235000011180 diphosphates Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000006112 glass ceramic composition Substances 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000000790 scattering method Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- 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 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 3
- BVSXRCDUVXEDNL-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfinic acid Chemical compound CC(C)C1=CC(C(C)C)=C(S(O)=O)C(C(C)C)=C1 BVSXRCDUVXEDNL-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 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
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 125000005385 peroxodisulfate group Chemical group 0.000 description 3
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- YYJNCOSWWOMZHX-UHFFFAOYSA-N triethoxy-(4-triethoxysilylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C([Si](OCC)(OCC)OCC)C=C1 YYJNCOSWWOMZHX-UHFFFAOYSA-N 0.000 description 3
- 125000004953 trihalomethyl group Chemical group 0.000 description 3
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- GXMBHQRROXQUJS-UHFFFAOYSA-N (2-hept-2-ynylsulfanylphenyl) acetate Chemical compound CCCCC#CCSC1=CC=CC=C1OC(C)=O GXMBHQRROXQUJS-UHFFFAOYSA-N 0.000 description 2
- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 2
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
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- KAJICSGLHKRDLN-UHFFFAOYSA-N 1,3-dicyclohexylthiourea Chemical compound C1CCCCC1NC(=S)NC1CCCCC1 KAJICSGLHKRDLN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- CGRMGOGJWHPCFJ-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfinic acid Chemical compound CC1=CC(C)=C(S(O)=O)C(C)=C1 CGRMGOGJWHPCFJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 2
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 2
- ASEUXRQULQEGGL-UHFFFAOYSA-N 2-decyl-2-prop-2-enoyloxypropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)(C(O)=O)OC(=O)C=C ASEUXRQULQEGGL-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- AUZRCMMVHXRSGT-UHFFFAOYSA-N 2-methylpropane-1-sulfonic acid;prop-2-enamide Chemical compound NC(=O)C=C.CC(C)CS(O)(=O)=O AUZRCMMVHXRSGT-UHFFFAOYSA-N 0.000 description 2
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 2
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 description 2
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 description 2
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 2
- SKKXTPQPJYBUEF-UHFFFAOYSA-N 3-phosphonooxypropyl prop-2-enoate Chemical compound OP(O)(=O)OCCCOC(=O)C=C SKKXTPQPJYBUEF-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- LKNDYQNNDRTHFP-UHFFFAOYSA-N n,n,3,4-tetramethylaniline Chemical compound CN(C)C1=CC=C(C)C(C)=C1 LKNDYQNNDRTHFP-UHFFFAOYSA-N 0.000 description 1
- NBFRQCOZERNGEX-UHFFFAOYSA-N n,n,3,5-tetramethylaniline Chemical compound CN(C)C1=CC(C)=CC(C)=C1 NBFRQCOZERNGEX-UHFFFAOYSA-N 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- MJRUTYCVCLZWSR-UHFFFAOYSA-N n,n-dimethyl-4-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(N(C)C)C=C1 MJRUTYCVCLZWSR-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- BFYJDHRWCNNYJQ-UHFFFAOYSA-N oxo-(3-oxo-3-phenylpropoxy)-(2,4,6-trimethylphenyl)phosphanium Chemical compound CC1=CC(C)=CC(C)=C1[P+](=O)OCCC(=O)C1=CC=CC=C1 BFYJDHRWCNNYJQ-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NPUSTSBKXOLJIC-UHFFFAOYSA-N phenyl(2-prop-2-enoyloxyethoxy)phosphinic acid Chemical compound C=CC(=O)OCCOP(=O)(C1=CC=CC=C1)O NPUSTSBKXOLJIC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-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
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 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
- 150000003297 rubidium Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 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
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 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
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- WWYACYKHLMCNBG-UHFFFAOYSA-M sodium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 WWYACYKHLMCNBG-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
- 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
- 125000000101 thioether group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine group Chemical class C(CCC)N(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
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- OSAJVUUALHWJEM-UHFFFAOYSA-N triethoxy(8-triethoxysilyloctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCC[Si](OCC)(OCC)OCC OSAJVUUALHWJEM-UHFFFAOYSA-N 0.000 description 1
- WCTSVVHHSWBVAX-UHFFFAOYSA-N triethoxy-[2-[4-(2-triethoxysilylethyl)phenyl]ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=C(CC[Si](OCC)(OCC)OCC)C=C1 WCTSVVHHSWBVAX-UHFFFAOYSA-N 0.000 description 1
- KENDGHJJHKCUNB-UHFFFAOYSA-N triethoxy-[4-(4-triethoxysilylphenyl)phenyl]silane Chemical group C1=CC([Si](OCC)(OCC)OCC)=CC=C1C1=CC=C([Si](OCC)(OCC)OCC)C=C1 KENDGHJJHKCUNB-UHFFFAOYSA-N 0.000 description 1
- GNBPMOQUHWCSGK-UHFFFAOYSA-N trimethoxy(1-trimethoxysilyldecan-2-yl)silane Chemical compound CCCCCCCCC([Si](OC)(OC)OC)C[Si](OC)(OC)OC GNBPMOQUHWCSGK-UHFFFAOYSA-N 0.000 description 1
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 description 1
- JEPXSTGVAHHRBD-UHFFFAOYSA-N trimethoxy(nonyl)silane Chemical compound CCCCCCCCC[Si](OC)(OC)OC JEPXSTGVAHHRBD-UHFFFAOYSA-N 0.000 description 1
- MAFQBSQRZKWGGE-UHFFFAOYSA-N trimethoxy-[2-[4-(2-trimethoxysilylethyl)phenyl]ethyl]silane Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CC[Si](OC)(OC)OC)C=C1 MAFQBSQRZKWGGE-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
- GKMJIVDFRBQRTH-UHFFFAOYSA-N trimethoxy-[[4-(trimethoxysilylmethyl)phenyl]methyl]silane Chemical compound CO[Si](OC)(OC)CC1=CC=C(C[Si](OC)(OC)OC)C=C1 GKMJIVDFRBQRTH-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/77—Glass
-
- 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
- A61K6/849—Preparations for artificial teeth, for filling teeth or for capping teeth comprising inorganic cements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
- C08F222/1025—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate of aromatic dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/40—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
Description
[1]酸性基を有する重合性単量体(a)、酸性基を有しない重合性単量体(b)、重合開始剤(c)、及びフィラー(d)を含む第1剤と、
酸性基を有しない重合性単量体(b)、塩基性ガラスフィラー及びアルミナからなる群より選ばれる少なくとも1種のフィラー(e)、重合促進剤(f)、及び下記一般式〔I〕
で表されるシランカップリング剤(g)を含む第2剤とから構成される2ペースト型歯科用硬化性組成物。
M(R22)n 〔VII〕
(式中、MはTi、Zr又はAlを表し、R22は脂肪族基を表し、nは1~4の整数を表し、R22が複数存在する場合、R22は互いに同一であってもよいし異なっていてもよい。)
で表される芳香族ジ(メタ)アクリレートなどが挙げられる。芳香族化合物系の二官能性重合性単量体の具体例としては、2,2-ビス((メタ)アクリロイルオキシフェニル)プロパン、2,2-ビス〔4-(3-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-(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(以下、「Bis-GMA」と略称することがある)、2,2-ビス(4-(メタ)アクリロイルオキシエトキシフェニル)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ト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-(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)アクリロイルオ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)ア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)ア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)アクリロイルオ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イソプロポキシフェニル)プロパン、1,4-ビス(2-(メタ)アクリロイルオキシエチル)ピロメリテートなどが挙げられる。これらの中でも、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、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)(以下、「D2.6E」と略称することがある)が好ましい。
で表されるシランカップリング剤(g)を含む。
M(R22)n 〔VII〕
(式中、MはTi、Zr又はAlを表し、R22は脂肪族基を表し、nは1~4の整数を表し、R22が複数存在する場合、R22は互いに同一であってもよいし異なっていてもよい。)
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
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
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(エトキシ基の平均付加モル数:2.6)
酢酸銅(II)
VOAA:バナジルアセチルアセトネート
BPB:t-ブチルペルオキシベンゾエート
BPO:ベンゾイルペルオキシド
KPS:過硫酸カリウム
THP:1,1,3,3-テトラメチルブチルヒドロペルオキシド
F1:シラン処理石英粉:
石英(MARUWA QUARTZ社製)をボールミルで粉砕し、平均粒子径が約4.5μmの石英粉を得た。この石英粉100質量部に対して、通法により3質量部のγ-メタクリロキシプロピルトリメトキシシランで表面処理を行い、シラン処理石英粉を得た。
R972:日本アエロジル株式会社製微粒子シリカ「アエロジル(登録商標)R972」、平均粒子径:16nm
F2:シラン処理バリウムガラス粉:
バリウムガラス(エステック社製、商品コード「Raysorb E-3000」)をボールミルで粉砕し、平均粒子径が約2.4μmのバリウムガラス粉を得た。このバリウムガラス粉100質量部に対して、通法により3質量部のγ-メタクリロキシプロピルトリメトキシシランで表面処理を行い、シラン処理バリウムガラス粉を得た。
アルミナ:日本アエロジル株式会社製、商品名「AEROXIDE Alu C」、平均粒子径:13nm、pH:4.5~5.5
TPBSS:2,4,6-トリイソプロピルベンゼンスルフィン酸ナトリウム
DEPT:N,N-ビス(2-ヒドロキシエチル)-p-トルイジン
BTA:1H-ベンゾトリアゾール
DMETU:4,4-ジメチルエチレンチオ尿素
8-MOS:8-メタクリロキシオクチルトリメトキシシラン
11-MUS:11-メタクリロキシウンデシルトリメトキシシラン
11-MUES:11-メタクリロキシウンデシルトリエトキシシラン
APhS:アクリロキシメチルフェネチルトリメトキシシラン
〔他のシランカップリング剤〕
γ-MPS:γ-メタクリロキシプロピルトリメトキシシラン
γ-MPES:γ-メタクリロキシプロピルトリエトキシシラン
〔架橋剤(h)〕
TSPI:トリス(トリメトキシシリルプロピル)イソシアヌレート
BSB:1,4-ビス(トリエトキシシリル)ベンゼン
BSE:1,2-ビス(トリエトキシシリル)エタン
BSH:1,6-ビス(トリエトキシシリル)ヘキサン
BSO:1,8-ビス(トリメトキシシリル)オクタン
Ti(OBu)4 :チタン(IV)テトラブトキシド
Ti(C3H7O)2(AcAc)2 :チタン(IV)ビス(アセチルアセトナート)ジイソプロポキシド(75%イソプロパノール溶液)
Ti(C3H7O)2(C6H9O3)2:チタン(IV)ビス(エチルアセトアセテート)ジイソプロポキシド(95%イソプロパノール溶液)
Ti(C8H17O)2(C8H17O2)2:チタン(IV)ビス(エチルヘキソキシ)ビス(2-エチル-3-ヒドロキシヘキソキシド)
Zr(C5H7O2)4:ジルコニウム(IV)テトラアセチルアセトナート
CQ:dl-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(光重合開始剤の重合促進剤)
BHT:2,6-ジ-t-ブチル-4-メチルフェノール(安定剤)
表1及び表2に示す組成の第1剤及び第2剤を調製した。第1剤は、粉末状成分(フィラー)以外の成分を調合後、撹拌して均一な溶液とした後、粉末状成分を練り込み脱泡して作製した。第1剤中の粉末状成分は、粉末状態で分散した状態であった。また、第2剤は、粉末状成分(フィラー及びTPBSS)以外の成分を調合後、撹拌して均一な溶液とした後、粉末状成分を練り込み脱泡して作製した。第2剤中の粉末状成分は、粉末状に分散した状態であった。2剤をダブルシリンジ(Mixpac社製;5mLダブルシリンジ)にそれぞれ充填し、プランジャーをセットした。ダブルシリンジの先端にミキシングチップ(Mixpac社製)を装着し、2剤を質量比1:1で自動混和し、その混和物を歯科用硬化性組成物として評価に用いた。下記に示す方法により、陶材及び二ケイ酸リチウムガラスへの引張接着強さについて試験した。結果を表1及び表2に示す。
歯科用陶材(長石系セラミックス、VITA Zahnfabrik H.Rauter GmbH & Co.KG社製「ビタブロック マークII」)を流水下にて#1000のシリコンカーバイド紙にて研磨した。研磨後、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5mmの丸穴を有する厚さ約150μmの粘着テープを貼着し、接着面積を規制した。各実施例、比較例において第1剤と第2剤を混和して得られた歯科用硬化性組成物を、ステンレス製円柱棒(直径7mm、長さ2.5cm)の一方の端面(円形断面)に築盛した。次いで、上記の丸穴の中心と上記のステンレス製円柱棒の中心とが略一致するように、該歯科用硬化性組成物を築盛した側の端面を丸穴内の平滑面(被着面)に載置し、その平滑面に対して垂直にステンレス製の円柱棒を押し付けて接着して、供試サンプルを作製した。供試サンプルは、10個作製した。押し付けた際にステンレス製の円柱棒の周囲からはみ出た余剰の該歯科用硬化性組成物を除去した後、供試サンプルを、30分間室温で静置し、蒸留水に浸漬した。蒸留水に浸漬した供試サンプルを、37℃に保持した恒温器内に24時間静置した。10個の供試サンプルのうち、5個については、37℃で24時間静置した後の引張接着強さを調べた。この引張接着強さは初期の引張接着強さを示す。また、残りの5個の供試サンプルについては、さらに70℃に保持した恒温器内に10日間静置した後、引張接着強さを調べた。この引張接着強さは、接着耐久性を表す。引張接着強さは、万能試験機(株式会社島津製作所製)にてクロスヘッドスピードを2mm/分に設定して測定した。表中の引張接着強さは、37℃、24時間後、及び70℃、10日後いずれもそれぞれ5個の供試サンプルについての測定値の平均値である。
歯科用二ケイ酸リチウムガラスセラミックス(Ivoclar Vivadent社製「IPS e.max CAD」)を、製品パンフレットに記載の焼成プログラムの条件に従い焼成し、流水下にて#1000のシリコンカーバイド紙にて研磨した。研磨後、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5mm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。各実施例、比較例において第1剤と第2剤を混和して得られた歯科用硬化性組成物を、ステンレス製円柱棒(直径7mm、長さ2.5cm)の一方の端面(円形断面)に築盛し、上記の丸穴の中心と上記のステンレス製円柱棒の中心とが略一致するように、該歯科用硬化性組成物を築盛した側の端面を丸穴内の平滑面(被着面)に載置し、その平滑面に対して垂直にステンレス製の円柱棒を押し付けて接着して、供試サンプルを作製した。供試サンプルは、10個作製した。押し付けた際にステンレス製の円柱棒の周囲からはみ出た余剰の該歯科用硬化性組成物を除去した後、供試サンプルを、30分間室温で静置し、蒸留水に浸漬した。蒸留水に浸漬した供試サンプルを、37℃に保持した恒温器内に24時間静置した。10個の供試サンプルのうち、5個については、37℃で24時間静置した後の引張接着強さを調べた。この引張接着強さは初期の引張接着強さを示す。また、残りの5個の供試サンプルについては、さらに70℃に保持した恒温器内に3日間静置した後、引張接着強さを調べた。この引張接着強さは、接着耐久性を表す。引張接着強さは、万能試験機(株式会社島津製作所製)にてクロスヘッドスピードを2mm/分に設定して測定した。表中の引張接着強さは、37℃、24時間後、及び70℃、3日後いずれもそれぞれ5個の供試サンプルについての測定値の平均値である。
Claims (16)
- 酸性基を有する重合性単量体(a)、酸性基を有しない重合性単量体(b)、重合開始剤(c)、及びフィラー(d)を含む第1剤と、
酸性基を有しない重合性単量体(b)、ランタンガラス、バリウムガラス、ストロンチウムガラス、ソーダガラス、亜鉛ガラス、フルオロアルミノシリケートガラス及びアルミナからなる群より選ばれる少なくとも1種のフィラー(e)、重合促進剤(f)、及び下記一般式〔I〕
で表されるシランカップリング剤(g)を含む第2剤とから構成される2ペースト型歯科用硬化性組成物。 - R1が、二価基を有していてもよい炭素鎖長が7以上20以下の直鎖を有する二価の脂肪族基、又は二価基を有していてもよい炭素数7以上20以下の二価の芳香族基である、請求項1に記載の2ペースト型歯科用硬化性組成物。
- R2、R3、及びR4が、それぞれ独立して、水酸基、炭素数1~3のアルキル基又は炭素数1~3のアルコキシ基であり、R2、R3、及びR4の少なくとも1つが炭素数1~3のアルコキシ基である、請求項1又は2に記載の2ペースト型歯科用硬化性組成物。
- R2、R3、及びR4が、それぞれ独立して、水酸基、メチル基又はメトキシ基であり、R2、R3、及びR4の少なくとも1つがメトキシ基である、請求項1~3のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- R2、R3、及びR4がメトキシ基である、請求項1~4のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- R1が、二価基を有していてもよい炭素鎖長が8以上20以下の直鎖を有する二価の脂肪族基である、請求項1~5のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- R1が、二価基を有していてもよい炭素数8以上20以下の二価の芳香族基である、請求項1~5のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- シランカップリング剤(g)が、5-(メタ)アクリロキシペンチルトリメトキシシラン、6-(メタ)アクリロキシヘキシルトリメトキシシラン、7-(メタ)アクリロキシへプチルトリメトキシシラン、8-(メタ)アクリロキシオクチルトリメトキシシラン、9-(メタ)アクリロキシノニルトリメトキシシラン、10-(メタ)アクリロキシデシルトリメトキシシラン、11-(メタ)アクリロキシウンデシルトリメトキシシラン、8-(メタ)アクリロキシオクチルメチルジメトキシシラン、10-(メタ)アクリロキシデシルメチルジメトキシシラン、11-(メタ)アクリロキシウンデシルメチルジメトキシシラン、及び(メタ)アクリロキシメチルフェネチルトリメトキシシランからなる群より選ばれる少なくとも1種である、請求項1~7のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- シランカップリング剤(g)が、8-(メタ)アクリロキシオクチルトリメトキシシラン、9-(メタ)アクリロキシノニルトリメトキシシラン、10-(メタ)アクリロキシデシルトリメトキシシラン、11-(メタ)アクリロキシウンデシルトリメトキシシラン、及び(メタ)アクリロキシメチルフェネチルトリメトキシシランからなる群より選ばれる少なくとも1種である、請求項1~7のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- R8が二価基を有していてもよい炭素数6以上の二価の芳香族基であり、R15が二価基を有していてもよい炭素数6以上の三価の芳香族基である、請求項10に記載の2ペースト型歯科用硬化性組成物。
- 架橋剤(h)が一般式〔V〕で表される化合物であり、R8が二価基を有していてもよい炭素鎖長が1以上である二価の脂肪族基である、請求項10に記載の2ペースト型歯科用硬化性組成物。
- さらに第1剤に下記一般式〔VII〕で表されるシラノール縮合触媒(i)を含む、請求項1~12のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
M(R22)n 〔VII〕
(式中、MはTi、Zr又はAlを表し、R22は脂肪族基を表し、nは1~4の整数を表し、R22が複数存在する場合、R22は互いに同一であってもよいし異なっていてもよい。) - R22が、炭素数1~9のアルコキシ基、炭素数2~9のアシロキシ基、炭素数3~9のアルケニルオキシ基、炭素数5~15のβ-ジケトナート基、又は炭素数1~9のアシル基を有するジアシルメチル基である、請求項13に記載の2ペースト型歯科用硬化性組成物。
- さらに第1剤と第2剤の少なくとも一方に光重合開始剤(j)を含む、請求項1~14のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
- フィラー(e)がバリウムガラス及び/又はアルミナである、請求項1~15のいずれか1項に記載の2ペースト型歯科用硬化性組成物。
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CN110785159B (zh) | 2023-06-09 |
AU2018291349B2 (en) | 2021-11-18 |
EP3646847A1 (en) | 2020-05-06 |
US20200155421A1 (en) | 2020-05-21 |
WO2019004391A1 (ja) | 2019-01-03 |
US11400030B2 (en) | 2022-08-02 |
CA3067786A1 (en) | 2019-01-03 |
CA3067786C (en) | 2021-12-28 |
CN110785159A (zh) | 2020-02-11 |
EP3646847A4 (en) | 2021-01-13 |
AU2018291349A1 (en) | 2020-01-30 |
JPWO2019004391A1 (ja) | 2020-04-16 |
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