JP6458034B2 - 歯科用組成物 - Google Patents
歯科用組成物 Download PDFInfo
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- JP6458034B2 JP6458034B2 JP2016536885A JP2016536885A JP6458034B2 JP 6458034 B2 JP6458034 B2 JP 6458034B2 JP 2016536885 A JP2016536885 A JP 2016536885A JP 2016536885 A JP2016536885 A JP 2016536885A JP 6458034 B2 JP6458034 B2 JP 6458034B2
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- Prior art keywords
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- dental composite
- formula
- compound
- polymerizable
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 66
- 239000011350 dental composite resin Substances 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 46
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 25
- 239000000945 filler Substances 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000000068 pit and fissure sealant Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- -1 bis-GMA Chemical compound 0.000 description 26
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 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 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 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 12
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 12
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 10
- 239000002105 nanoparticle Substances 0.000 description 10
- 239000003505 polymerization initiator Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 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 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- NEPKLUNSRVEBIX-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,4-dicarboxylate Chemical compound C=1C=C(C(=O)OCC2OC2)C=CC=1C(=O)OCC1CO1 NEPKLUNSRVEBIX-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000003444 phase transfer catalyst Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 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 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000002723 alicyclic 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
- 150000001412 amines Chemical class 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-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
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 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 class 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
- 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
- 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 1
- 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
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- VKZNKGOTADCMCL-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl N-[6-(1,3-dihydroxypropan-2-yloxycarbonylamino)-2,2,4-trimethylhexyl]carbamate 2-methylprop-2-enoic acid Chemical compound C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.CC(CNC(=O)OC(CO)CO)(CC(CCNC(=O)OC(CO)CO)C)C VKZNKGOTADCMCL-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- ZNVJYOSWOAZKSM-UHFFFAOYSA-N 1-(2-hydroxypropoxy)ethyl prop-2-enoate Chemical compound C(C=C)(=O)OC(C)OCC(C)O ZNVJYOSWOAZKSM-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- ZESGLEJYMHVEKI-UHFFFAOYSA-N 10-prop-2-enoyloxydecylazanium chloride Chemical compound [Cl-].C(C=C)(=O)OCCCCCCCCCC[NH3+] ZESGLEJYMHVEKI-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
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- 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
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FTVAVVASDKWQLQ-UHFFFAOYSA-N 2-[2-hydroxyethyl(methyl)amino]ethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCCN(C)CCO FTVAVVASDKWQLQ-UHFFFAOYSA-N 0.000 description 1
- NKANYVMWDXJHLE-UHFFFAOYSA-N 2-[[2-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1OCC1CO1 NKANYVMWDXJHLE-UHFFFAOYSA-N 0.000 description 1
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 1
- MUBQKSBEWRYKES-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO MUBQKSBEWRYKES-UHFFFAOYSA-N 0.000 description 1
- FSYPIGPPWAJCJG-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1OCC1CO1 FSYPIGPPWAJCJG-UHFFFAOYSA-N 0.000 description 1
- DEWPRFSWNWKLHF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCCN(CCO)CCO DEWPRFSWNWKLHF-UHFFFAOYSA-N 0.000 description 1
- NKFNBVMJTSYZDV-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCCCCCCCCCN(CCO)CCO NKFNBVMJTSYZDV-UHFFFAOYSA-N 0.000 description 1
- BHICZSRCJVGOGG-UHFFFAOYSA-N 2-[ethyl-[2-(2-methylprop-2-enoyloxy)ethyl]amino]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN(CC)CCOC(=O)C(C)=C BHICZSRCJVGOGG-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [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
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 229940105963 yttrium fluoride Drugs 0.000 description 1
- RBORBHYCVONNJH-UHFFFAOYSA-K yttrium(iii) fluoride Chemical compound F[Y](F)F RBORBHYCVONNJH-UHFFFAOYSA-K 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
L’は、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を主鎖中に含有していてもよく、かつ1つ又は複数のヒドロキシル基、又は−COOL’’基(式中、L’’は重合性部分である)で置換されてもよい(l+1)価の炭化水素基であり、
lは1〜3の整数である)のx当量の1つ又は複数の化合物と、
(b)下記式(IIa)、(IIb)及び/又は(IIc):
nは1〜3の整数であり、
Yは、存在しても存在していなくてもよく、存在する場合、カルボニル基を表し、
Y’は独立して、存在しても存在していなくてもよく、カルボニル基を表し、
Rmは、同じであっても異なっていてもよく、ハロゲン原子、アルキル基及びアルコキシ基から選択される1つ〜3つの置換基を表すか、又は、2つのRmが、それらが結合する環の炭素原子とともに、縮環芳香族環を形成する)のy当量の1つ又は複数の化合物と、
(c)下記式(III):
R1は、水素原子又はアルキル基であり、
kは1〜3の整数であり、ここで、
kが1、2又は3である場合、Lは、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を含有し得る(k+1)価の炭化水素基であり、Xは、Lの芳香族環形成部位に結合するカルボン酸基又はヒドロキシル基であるか、又は、
kが1である場合、Lは単結合を表し、Xは水素原子である)のz当量の1つ又は複数の化合物と、
を含み、
0.05≦x/y≦0.66であり、かつ、
x、y及びzが、成分(a)、(b)及び(c)のモル当量であり、かつ、
混合物を反応させること、及び
任意に、前記混合物の反応生成物のL’上のヒドロキシル基を、重合性二重結合を有する化合物と反応させることと、
によって得られる、重合性組成物と、
(ii)粒状フィラーと、
を含む、歯科用コンポジットを提供する。
L’は、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を主鎖中に含有していてもよく、かつ1つ又は複数のヒドロキシル基、又は−COOL’’基(式中、L’’は重合性部分である)で置換されてもよい(l+1)価の炭化水素基であり、
lは1〜3の整数である)のx当量の1つ又は複数の化合物と、
(b)下記式(IIa)、(IIb)及び/又は(IIc):
nは1〜3の整数であり、
Yは、存在しても存在していなくてもよく、存在する場合、カルボニル基を表し、
Y’は独立して、存在しても存在していなくてもよく、カルボニル基を表し、
Rmは、同じであっても異なっていてもよく、ハロゲン原子、アルキル基及びアルコキシ基から選択される1つ〜3つの置換基を表すか、又は、2つのRmが、それらが結合する環の炭素原子とともに、縮環芳香族環を形成する)のy当量の1つ又は複数の化合物と、
(c)下記式(III):
R1は、水素原子又はアルキル基であり、
kは1〜3の整数であり、ここで、
kが1、2又は3である場合、Lは、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を含有し得る(k+1)価の炭化水素基であり、Xは、Lの芳香族環形成部位に結合するカルボン酸基又はヒドロキシル基であるか、又は、
kが1である場合、Lは単結合を表し、Xは水素原子である)のz当量の1つ又は複数の化合物と、
を含み、
0.05≦x/y≦0.66であり、かつ、
x、y及びzが、成分(a)、(b)及び(c)のモル当量であり、かつ、
混合物を反応させること、及び
任意に、前記混合物の反応生成物のL’上のヒドロキシル基を、重合性二重結合を有する化合物と反応させること、
を含む、歯科用組成物を製造する方法を提供する。
100.000g(0.450mol)のレゾルシノールジグリシジルエーテル、17.712g(0.15mol)のコハク酸、51.650g(0.60mol)のメタクリル酸、0.847gのトリエチルベンジルアンモニウムクロリド、及び0.169gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で6.5時間反応させた。
η=41.7±0.4Pa*s、
15.000g(0.539mol)のテレフタル酸ジグリシジルエステル、1.273g(0.108mol)のコハク酸、7.425g(0.315mol)のメタクリル酸、0.118gのトリエチルベンジルアンモニウムクロリド、及び0.024gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で6.5時間反応させた。
15.000g(0.539mol)のテレフタル酸ジグリシジルエステル、1.403g(0.108mol)のイタコン酸、7.425g(0.315mol)のメタクリル酸、0.118gのトリエチルベンジルアンモニウムクロリド、及び0.024gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で6.5時間反応させた。
5.480g(0.025mol)のレゾルシノールジグリシジルエーテル、2.048g(0.012mol)のイソフタル酸、2.123g(0.025mol)のメタクリル酸、0.056gのトリエチルベンジルアンモニウムクロリド、及び0.003gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で3時間反応させた。その後、この混合物に、2.740g(0.012mol)のレゾルシノールジグリシジルエーテル及び2.123g(0.025mol)のメタクリル酸を更に添加し、90℃で3時間反応させた。
4.00g(0.018mol)のレゾルシノールジグリシジルエーテル、3.60g(0.009mol)のブタン−1,2,3,4−テトラカルボン酸ジ−2−ヒドロキシエチルメタクリレート(TCBレジン)、1.55g(0.018mol)のメタクリル酸、0.150gのトリエチルベンジルアンモニウムクロリド、及び0.003gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で4時間反応させた。
[比較例1](AG18−144−1)
6.808g(0.020mol)のビスフェノールAジグリシジルエーテル、1.462g(0.010mol)のアジピン酸、1.722g(0.020mol)のメタクリル酸、0.091gのトリエチルベンジルアンモニウムクロリド、及び0.009gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃で4時間反応させた。得られたメタクリレート末端マクロマー(式2中、n=0.5)は、クロロホルム、DMF及びTHF等の有機溶媒に可溶性のものである。IRスペクトルでは、915cm−1〜3050cm−1におけるエポキシド基の吸収が観測されなかった。エステル基の新たな吸収が1720cm−1に見られた。
200.000g(0.900mol)のレゾルシノールジグリシジルエーテル、53.136g(0.450mol)のコハク酸、77.475g(0.900mol)のメタクリル酸、1.653gのトリエチルベンジルアンモニウムクロリド、及び0.331gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃まで加熱しながら均質混合し、90℃で6時間反応させた。得られたメタクリレート末端マクロマー(n=1)は、クロロホルム、DMF及びTHF等の有機溶媒に可溶性のものである。IRスペクトルでは、915cm−1〜3050cm−1におけるエポキシド基の吸収が観測されなかった。エステル基の新たな吸収が1720cm−1に見られた。
10.000g(0.036mol)の1,2−ジグリシジルフタレート、2.122g(0.018mol)のコハク酸、3.094g(0.036mol)のメタクリル酸、0.334gのトリエチルベンジルアンモニウムクロリド、及び0.069gの2,6−ジ−tert−ブチル−p−クレゾールを、90℃で6時間反応させた。得られたメタクリレート末端マクロマー(n=1)は、クロロホルム、DMF及びTHF等の有機溶媒に可溶性のものである。IRスペクトルでは、915cm−1〜3050cm−1におけるエポキシド基の吸収が観測されなかった。エステル基の新たな吸収が1720cm−1に見られた。
Claims (13)
- 歯科用コンポジットであって、
(i)(a)下記式(I):
L’は、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を主鎖中に含有していてもよく、かつ1つ又は複数のヒドロキシル基、又は−COOL’’基(式中、L’’は重合性部分である)で置換されてもよい(l+1)価の炭化水素基であり、
lは1〜3の整数である)のx当量の1つ又は複数の化合物と、
(b)下記式(IIa)、(IIb)及び/又は(IIc):
nは1〜3の整数であり、
Yは、存在しても存在していなくてもよく、存在する場合、カルボニル基を表し、
Y’は独立して、存在しても存在していなくてもよく、カルボニル基を表し、
Rmは、同じであっても異なっていてもよく、ハロゲン原子、アルキル基及びアルコキシ基から選択される1つ〜3つの置換基を表すか、又は、2つのRmが、それらが結合する環の炭素原子とともに、縮環芳香族環を形成する)のy当量の1つ又は複数の化合物と、
(c)下記式(III):
R1は、水素原子又はアルキル基であり、
kは1〜3の整数であり、ここで、
kが1、2又は3である場合、Lは、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を含有し得る(k+1)価の炭化水素基であり、Xは、Lの芳香族環形成部位に結合するカルボン酸基又はヒドロキシル基であるか、又は、kが1である場合、Lは単結合を表し、Xは水素原子である)のz当量の1つ又は複数の化合物と、
を含み、
0.05≦x/y≦0.66であり、かつ、
x、y及びzが、成分(a)、(b)及び(c)のモル当量であり、かつ、
混合物を反応させること、及び
任意に、前記混合物の反応生成物のL’上のヒドロキシル基及び/又はカルボン酸基を、重合性二重結合を有する化合物と反応させること、
によって得られる、重合性組成物と、
(ii)粒状フィラーと、
を含む、歯科用コンポジット。 - 前記混合物が式(IIa)の化合物を含有する、請求項1に記載の歯科用コンポジット。
- nが1である、請求項1又は2に記載の歯科用コンポジット。
- 式(III)の化合物中、kが1であり、Lが単結合を表し、Xが水素原子である、請求項1〜3のいずれか一項に記載の歯科用コンポジット。
- 式(I)の化合物中、lが1である、請求項1〜4のいずれか一項に記載の歯科用コンポジット。
- 前記重合性組成物が、前記混合物の前記反応生成物のL’上の前記ヒドロキシル基を、重合性二重結合を有する化合物と反応させることによって得られる、請求項1〜5のいずれか一項に記載の歯科用コンポジット。
- 重合性二重結合を有する前記化合物が、ヒドロキシアルキル(メタ)アクリレートである、請求項6に記載の歯科用コンポジット。
- 前記重合性組成物(i)が、23℃で1Pas〜30Pa・sの動粘度を有する、請求項1〜7のいずれか一項に記載の歯科用コンポジット。
- 前記重合性組成物(i)が、1.500〜1.540の屈折率を有する、請求項1〜8のいずれか一項に記載の歯科用コンポジット。
- 有機溶媒から選択される希釈剤を含有しない、請求項1〜9のいずれか一項に記載の歯科用コンポジット。
- 歯科用コンポジットに使用される重合性組成物を製造する方法であって、
(a)下記式(I):
L’は、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を主鎖中に含有していてもよく、かつ1つ又は複数のヒドロキシル基、又は−COOL’’基(式中、L’’は重合性部分である)で置換されてもよい(l+1)価の炭化水素基であり、lは1〜3の整数である)
のx当量の1つ又は複数の化合物と、
(b)下記式(IIa)、(IIb)及び/又は(IIc):
nは1〜3の整数であり、
Yは、存在しても存在していなくてもよく、存在する場合、カルボニル基を表し、
Y’は独立して、存在しても存在していなくてもよく、カルボニル基を表し、
Rmは、同じであっても異なっていてもよく、ハロゲン原子、アルキル基及びアルコキシ基から選択される1つ〜3つの置換基を表すか、又は、2つのRmが、それらが結合する環の炭素原子とともに、縮環芳香族環を形成する)のy当量の1つ又は複数の化合物と、
(c)下記式(III):
R1は、水素原子又はアルキル基であり、
kは1〜3の整数であり、ここで、
kが1、2又は3である場合、Lは、酸素原子及び硫黄原子から選択される1個〜3個のヘテロ原子を含有し得る(k+1)価の炭化水素基であり、Xは、Lの芳香族環形成部位に結合するカルボン酸基又はヒドロキシル基であるか、又は、
kが1である場合、Lは単結合を表し、Xは水素原子である)のz当量の1つ又は複数の化合物と、
を含み、
0.05≦x/y≦0.66であり、かつ、
x、y及びzが、成分(a)、(b)及び(c)のモル当量であり、かつ、
混合物を反応させること、及び
任意に、前記混合物の反応生成物のL’上のヒドロキシル基を、重合性二重結合を有する化合物と反応させること、
を含む、方法。 - 下記式(IVa)、(IVb)及び/又は(IVc):
- 流動性歯科用コンポジット、汎用性歯科用コンポジット、充填性歯科用コンポジット、又は小窩裂溝封鎖材である、請求項12に記載の歯科用コンポジット。
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CA2929438A1 (en) | 2015-06-11 |
EP2881103B1 (en) | 2016-02-24 |
JP2017500300A (ja) | 2017-01-05 |
EP2881103A1 (en) | 2015-06-10 |
WO2015082642A1 (en) | 2015-06-11 |
CA2929438C (en) | 2023-01-24 |
US10188587B2 (en) | 2019-01-29 |
US20160256363A1 (en) | 2016-09-08 |
CN105792794A (zh) | 2016-07-20 |
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