JPWO2015152220A1 - 歯科材料用重合性モノマー組成物 - Google Patents
歯科材料用重合性モノマー組成物 Download PDFInfo
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- JPWO2015152220A1 JPWO2015152220A1 JP2016511922A JP2016511922A JPWO2015152220A1 JP WO2015152220 A1 JPWO2015152220 A1 JP WO2015152220A1 JP 2016511922 A JP2016511922 A JP 2016511922A JP 2016511922 A JP2016511922 A JP 2016511922A JP WO2015152220 A1 JPWO2015152220 A1 JP WO2015152220A1
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- polymerizable monomer
- monomer composition
- dental
- carbon atoms
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- 239000000203 mixture Substances 0.000 title claims abstract description 212
- 239000005548 dental material Substances 0.000 title claims abstract description 165
- 239000000178 monomer Substances 0.000 title claims abstract description 152
- -1 urethane acrylate compound Chemical class 0.000 claims abstract description 123
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 85
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 79
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 23
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 71
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 43
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 29
- 239000000945 filler Substances 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 10
- 239000000047 product Substances 0.000 description 61
- 238000006243 chemical reaction Methods 0.000 description 55
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 40
- 239000001301 oxygen Substances 0.000 description 40
- 229910052760 oxygen Inorganic materials 0.000 description 40
- 238000006116 polymerization reaction Methods 0.000 description 31
- 239000000805 composite resin Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 24
- 238000000034 method Methods 0.000 description 20
- 125000000962 organic group Chemical group 0.000 description 18
- 238000005452 bending Methods 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 9
- 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 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000011256 inorganic filler Substances 0.000 description 8
- 229910003475 inorganic filler Inorganic materials 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 150000001451 organic peroxides Chemical class 0.000 description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
- 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 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 4
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- 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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 0 COC(N*NC(O[Rh]OC(C(*)=C)=O)=O)=O Chemical compound COC(N*NC(O[Rh]OC(C(*)=C)=O)=O)=O 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 239000003479 dental cement Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical group OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 3
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical class CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000002245 particle 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
- 239000000049 pigment Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-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
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 2
- NJRHMGPRPPEGQL-UHFFFAOYSA-N 2-hydroxybutyl prop-2-enoate Chemical compound CCC(O)COC(=O)C=C NJRHMGPRPPEGQL-UHFFFAOYSA-N 0.000 description 2
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- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 2
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-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
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
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- 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
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
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- 239000006087 Silane Coupling Agent Substances 0.000 description 2
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- GWUIMLVRUIQFRX-UHFFFAOYSA-N [2,9-dicarbamoyloxy-5,7,7-trimethyl-10-(2-methylprop-2-enoyloxy)decyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(OC(N)=O)CCC(C)CC(C)(C)CC(COC(=O)C(C)=C)OC(N)=O GWUIMLVRUIQFRX-UHFFFAOYSA-N 0.000 description 2
- KAOQCJIKVJCWDU-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCC(CO)CC1 KAOQCJIKVJCWDU-UHFFFAOYSA-N 0.000 description 2
- URLYGBGJPQYXBN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methyl prop-2-enoate Chemical compound OCC1CCC(COC(=O)C=C)CC1 URLYGBGJPQYXBN-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 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 2
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- 238000001816 cooling Methods 0.000 description 2
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
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- 229950000688 phenothiazine Drugs 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 2
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- 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
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Abstract
Description
(I)該ウレタンアクリレート化合物(A)が下記一般式(1)で表されるヒドロキシアクリレート(a1)と、2つのイソシアネート基が炭化水素基で置換されていてもよいメチレン基を介して二価の炭素数6〜9の芳香族炭化水素基または二価の炭素数6〜9の橋かけ環式炭化水素基と結合しているジイソシアネート(a2)とを反応して得られる。
(II)前記重合性モノマー組成物中のメタクリロイル基およびアクリロイル基の合計数に対して、該ウレタンアクリレート化合物(A)に含有されるアクリロイル基の数が10%以上90%未満の割合である。
[2]前記重合性モノマー組成物中のメタクリロイル基およびアクリロイル基の合計数に対して、該ウレタンアクリレート化合物(A)に含有されるアクリロイル基の数が40%以上90%未満の割合である[1]に記載の歯科材料用重合性モノマー組成物。
[6]前記ジイソシアネート(a2)が、下記一般式(3)〜(5)で示される化合物より選択される少なくとも1つであることを特徴とする[5]に記載の歯科材料用重合性モノマー組成物。
[ウレタンアクリレート(A)]
本発明における歯科材料用重合性モノマー組成物には、下記一般式(1)で表される適度な柔軟性を有するヒドロキシアクリレート(a1)と、適度な剛性を有するジイソシアネート(a2)として、二価の芳香族炭化水素基または二価の橋かけ環式炭化水素基が、水素原子が炭化水素基で置換されていてもよいメチレン基を介して2つのイソシアネート基と結合したジイソシアネート(a2)とを反応させることにより得られるウレタンアクリレート(A)が含有されている。
また一般式(3’)の化合物の場合、メチレン基の結合位置が異なる位置異性体の混合物であってもよいし、単離された1種の位置異性体であってもよい。中でも、一般式(3)で示される化合物がより好ましい。
本発明における歯科材料用重合性モノマー組成物は、上述したウレタンアクリレート(A)に加えて、さらにメタクリロイル基およびアクリロイル基から選ばれる少なくとも1つの重合性基を含有する重合性化合物(B)(ただし、ウレタンアクリレート(A)を除く)を含有する。
本発明の歯科材料用重合性モノマー組成物は、本発明の歯科材料用組成物の成分として好適に使用でき、歯科材料用組成物は、上述した歯科材料用モノマー組成物、重合開始剤、及びフィラーを含有する。かかる歯科材料用組成物は、常温重合性、熱重合性、または光重合性を有し、例えば歯科修復材料として好ましく使用することができる。
TEGDMA:トリエチレングリコールジメタクリレート
DEGDMA:ジエチレングリコールジメタクリレート
TEGDA:トリエチレングリコールジアクリレート
EBADMA(4.0):エトキシ化ビスフェノールAジメタクリレート(4.0EO変成)
UDMA:2,2,4−トリメチルヘキサメチレンビス(2−カルバモイルオキシエチル)ジメタクリレート
HEA:2−ヒドロキシエチルアクリレート
TMXDI:1,3−テトラメチルキシリレンジイソシアネート
DBTDL:ジブチルスズジラウレート
BHT:ジブチルヒドロキシトルエン
CQ:カンファーキノン
DMAB2−BE:4−(ジメチルアミノ)安息香酸2−ブトキシエチル
[曲げ試験の方法]
本発明の実施例及び比較例における曲げ試験の方法を、以下に示す。
実施例及び比較例の歯科材料用重合性モノマー組成物100重量部に対して、CQ0.5重量部、DMAB2−BE0.5重量部を添加し、均一になるまで室温で撹拌して、光重合性モノマー溶液を得た。該光重合性モノマー溶液を、2x2x25mmのステンレス製型に入れ、可視光照射装置(松風社製 ソリディライトV)を用いて、片面3分間ずつ両面合わせて6分間ずつ光照射した。さらに型より取りだした試験片を、オーブン中において110℃、15分間の条件で熱処理した。オーブンより取り出した試験片を室温まで冷却したのち、密閉できるサンプル瓶中に試験片を蒸留水に浸漬して、37℃で24時間保持したものを試験片として使用した。
実施例及び比較例の歯科材料用重合性モノマー組成物100重量部、CQ0.5重量部、DMAB2−BE0.5重量部からなる光重合性モノマー溶液にシリカガラス(Fuselex−X(株式会社 龍森))300重量部を配合し、乳鉢を用いて均一になるまで撹拌したのち、脱泡を行うことで歯科用重合組成物を調製した。得られた歯科用重合組成物を、2x2x25mmのステンレス製型に入れ、可視光照射装置(松風社製 ソリディライトV)を用いて、片面3分間ずつ両面合わせて6分間ずつ光照射した。さらに型より取りだした試験片を、オーブン中において110℃、15分間の条件で熱処理した。オーブンより取り出した試験片を室温まで冷却したのち、密閉できるサンプル瓶中に試験片を蒸留水に浸漬して、37℃で24時間保持したものを試験片として使用した。
上記方法で作成した試験片を、試験機(島津製作所製 オートグラフEZ−S)を使用して、支点間距離20mm、クロスヘッドスピード1mm/分で三点曲げ試験を行った。なお、表2中の破断強度と破断エネルギー結果の括弧内の値は、比較例1の測定値と比べた場合の増減値を%で表したものである。
本発明の実施例及び比較例における粘度は、E型粘度計(東機産業製TVE−22H)を用い測定した。温度は循環式恒温水槽を用いて、25℃にコントロールした。
十分に乾燥させた攪拌羽根、及び温度計を備えた1リットル4ツ口フラスコ内に、HEA270.0g(2.325モル)、DBTDL0.55g(ヒドロキシエチルアクリレートとTMXDIの合計重量に対して0.1重量%)、及びBHT0.28g(HEAとTMXDIの合計重量に対して0.05重量%)を添加し、均一になるまで撹拌した後、60℃に昇温した。続いて、TMXDI284.0g(1.163モル)を1時間かけて滴下した。滴下中に反応熱により内温が上昇したので、80℃以下となるように滴下量をコントロールした。全量滴下後反応温度を80℃に保って、10時間反応を行った。この際、HPLC分析で反応の進行を追跡して、反応の終点を確認した。反応器から生成物を排出することにより、下記式で表わされるウレタンアクリレート530gを得た。65℃における粘度は1670mPa・sであった。
表1に示すヒドロキシアクリレートとジイソシアネートとを用いて、製造例1と同様の合成操作を行うことによりウレタンアクリレートを得た。
製造例1で得られたウレタンアクリレート10.0g(21.3ミリモル)と、TEGDMA4.53g(15.8ミリモル)とを容器に入れ、均一になるまで50℃で撹拌して、歯科材料用重合性モノマー組成物を得た。このとき、製造例1で得られたウレタンアクリレートはアクリロイル基を2個有し、TEGDMAはメタクリロイル基を2個有しているので、ウレタンアクリレート(A)である製造例1で得られたウレタンアクリレート含有のアクリロイル基数が該歯科材料用重合性モノマー組成物の全重合性基数に占める割合は57%であり、該組成物中のアクリロイル基とメタクリロイル基の比率は、57:43となる。
表2に示すウレタンアクリレートとその他の重合性モノマーを用いて、実施例1と同様の操作で、歯科材料用重合性モノマー組成物を得た。さらに、実施例1と同様の操作を行い、曲げ試験の結果を得た。結果を表2に示す。
実施例1で得られた歯科材料用重合性モノマー組成物100重量部に対して、フィラー(Fuselex−X)300重量部、CQ 0.5重量部、DMAB2−BE 0.5重量部を添加し、混合し、均一なペーストの歯科材料用組成物を得た。該歯科材料用組成物の硬化物の曲げ試験の結果は表3に示す。
実施例1で得られた歯科材料用重合性モノマー組成物の代わりに、それぞれ実施例2、3、5、6で得られた歯科材料用重合性モノマー組成物を用いた以外は、同様の操作で歯科材料用組成物を得た。該歯科材料用組成物の硬化物の曲げ試験の結果は表3に示す。
製造例1で得られたウレタンアクリレートを等モルのUDMAに変更した以外は、実施例1の操作に従い、歯科材料用重合性モノマー組成物を得た。さらに、実施例1と同様の操作を行い、曲げ試験の結果を得た。結果を表2に示す。なお比較例1の組成物は、ウレタンアクリレート(A)を含有していないが、表2中、「ウレタンアクリレート(A)」の項の括弧書きで示されるモル%、および「ウレタンアクリレート(A)含有のアクリロイル基数が、全重合性基数に占める割合」の項に括弧書きで示される%は、それぞれ、組成物中に含まれるUDMAのモル%、UDMA含有のメタクリロイル基が全重合性基数に占める割合を示したものである。
製造例1で得られたウレタンアクリレートを等モルの製造例8で得られたウレタンメタクリレートに変更した以外は、実施例1の操作に従い、歯科材料用重合性モノマー組成物を得た。さらに、実施例1と同様の操作を行い、曲げ試験の結果を得た。結果を表2に示す。なお比較例2の組成物は、ウレタンアクリレート(A)を含有していないが、表2中、「ウレタンアクリレート(A)」の項の括弧書きで示されるモル%、および「ウレタンアクリレート(A)含有のアクリロイル基数が、全重合性基数に占める割合」の項に括弧書きで示される%は、それぞれ、組成物中に含まれる製造例8で得られたウレタンメタクリレートのモル%、製造例8で得られたメタクリレート含有のメタクリロイル基が全重合性基数に占める割合を示したものである。
TEGDMAのみを歯科材料用重合性モノマー組成物として使用した以外は、実施例1と同様の操作を行い、曲げ試験の結果を得た。結果を表2に示す。
TEGDAのみを歯科材料用重合性モノマー組成物として使用した以外は、実施例1と同様の操作を行い、曲げ試験の結果を得た。結果を表2に示す。
比較例1で得られた歯科材料用重合性モノマー組成物を用いた以外は実施例18と同様の操作を行い、均一なペーストの歯科材料用組成物を得た。該歯科材料用組成物の硬化物の曲げ試験の結果は表3に示す。
比較例2で得られた歯科材料用重合性モノマー組成物を用いた以外は実施例18と同様の操作を行い、均一なペーストの歯科材料用組成物を得た。該歯科材料用組成物の硬化物の曲げ試験の結果は表3に示す。
Claims (12)
- ウレタンアクリレート化合物(A)と、メタクリロイル基およびアクリロイル基から選ばれる少なくとも1つの重合性基を含有する重合性化合物(B)とを含有し、かつ、以下の(I)および(II)を満たす歯科材料用重合性モノマー組成物。
(I)該ウレタンアクリレート化合物(A)が下記一般式(1)で表されるヒドロキシアクリレート(a1)と、2つのイソシアネート基が炭化水素基で置換されていてもよいメチレン基を介して二価の炭素数6〜9の芳香族炭化水素基または二価の炭素数6〜9の橋かけ環式炭化水素基と結合しているジイソシアネート(a2)とを反応して得られる。
(II)前記重合性モノマー組成物中のメタクリロイル基およびアクリロイル基の合計数に対して、該ウレタンアクリレート化合物(A)に含有されるアクリロイル基の数が10%以上90%未満の割合である。
- 前記重合性モノマー組成物中のメタクリロイル基およびアクリロイル基の合計数に対して、該ウレタンアクリレート化合物(A)に含有されるアクリロイル基の数が40%以上90%未満の割合である請求項1に記載の歯科材料用重合性モノマー組成物。
- 該歯科材料用重合性モノマー組成物に含有されるアクリロイル基とメタクリロイル基との比率が、10:90〜90:10の範囲にある、請求項1に記載の歯科材料用重合性モノマー組成物。
- 該歯科材料用重合性モノマー組成物に含有されるアクリロイル基とメタクリロイル基との比率が、40:60〜90:10の範囲にある、請求項1から3のいずれか1項に記載の歯科材料用重合性モノマー組成物。
- 前記一般式(1)中のRaが、それぞれ独立に、水素原子が炭素数1〜3のアルキル基で置換されてもよい炭素数2〜6の直鎖アルキレン基、または炭素数2〜6の直鎖オキシアルキレン基である請求項1に記載の歯科材料用重合性モノマー組成物。
- 前記一般式(6)中のRgおよびRhが、それぞれ独立に、水素原子が炭素数1〜3のアルキル基で置換されてもよい炭素数2〜6の直鎖アルキレン基、または炭素数2〜6の直鎖オキシアルキレン基であり、Rjが水素原子である請求項7に記載の歯科材料用重合性モノマー組成物。
- 25℃における粘度が1〜100,000mPa・sであることを特徴とする請求項1〜9のいずれか1項に記載の歯科材料用重合性モノマー組成物。
- 請求項1〜10のいずれか1項に記載の歯科材料用重合性モノマー組成物、重合開始剤、及びフィラーを含有する歯科材料用組成物。
- 請求項11に記載の歯科材料用組成物を硬化させてなる歯科材料。
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EP3719043A4 (en) * | 2017-11-28 | 2021-08-25 | Mitsui Chemicals, Inc. | (METH) ACRYLATE, MONOMER COMPOSITION, DENTAL MATERIAL CONSISTING OF THE SAID COMPOSITION, AND CORRESPONDING PRODUCTION PROCESS |
EP3871650A4 (en) * | 2018-12-12 | 2022-07-13 | Mitsui Chemicals, Inc. | MONOMER COMPOSITION, METHOD OF MANUFACTURE THEREOF, RAW MATERIAL COMPOSITION, CURABLE COMPOSITION AND MOLDING ARTICLE |
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US11718744B2 (en) | 2021-03-26 | 2023-08-08 | Dentca, Inc. | Photo-curable resin compositions containing impact modifier for three dimensional printing and cured dental product made of the same |
DE102021108477A1 (de) | 2021-04-02 | 2022-10-06 | Kulzer Gmbh | Selbstadhäsiver Fissurenversiegler |
DE102021108476A1 (de) | 2021-04-02 | 2022-10-06 | Kulzer Gmbh | Selbstadhäsives Dentalmaterial |
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CN106132383B (zh) | 2021-09-07 |
WO2015152221A1 (ja) | 2015-10-08 |
JP6514686B2 (ja) | 2019-05-15 |
US10130564B2 (en) | 2018-11-20 |
CN106132383A (zh) | 2016-11-16 |
WO2015152220A1 (ja) | 2015-10-08 |
US20170181932A1 (en) | 2017-06-29 |
US20170174621A1 (en) | 2017-06-22 |
US10130563B2 (en) | 2018-11-20 |
EP3135270A1 (en) | 2017-03-01 |
EP3135270B1 (en) | 2020-05-13 |
JPWO2015152221A1 (ja) | 2017-04-13 |
EP3135270A4 (en) | 2017-12-27 |
EP3135271A1 (en) | 2017-03-01 |
JP6426712B2 (ja) | 2018-11-21 |
EP3135271A4 (en) | 2017-12-27 |
EP3135271B1 (en) | 2019-05-08 |
CN106132382A (zh) | 2016-11-16 |
CN110464657A (zh) | 2019-11-19 |
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