JP2005076022A - 光重合開始剤 - Google Patents
光重合開始剤 Download PDFInfo
- Publication number
- JP2005076022A JP2005076022A JP2003312279A JP2003312279A JP2005076022A JP 2005076022 A JP2005076022 A JP 2005076022A JP 2003312279 A JP2003312279 A JP 2003312279A JP 2003312279 A JP2003312279 A JP 2003312279A JP 2005076022 A JP2005076022 A JP 2005076022A
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- JP
- Japan
- Prior art keywords
- group
- light
- photopolymerization initiator
- compound
- dental
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003999 initiator Substances 0.000 title claims abstract description 47
- -1 aromatic amine compound Chemical class 0.000 claims abstract description 87
- 125000000962 organic group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 28
- 239000011350 dental composite resin Substances 0.000 claims description 16
- 239000011256 inorganic filler Substances 0.000 claims description 16
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical group 0.000 abstract description 21
- 238000006116 polymerization reaction Methods 0.000 abstract description 17
- 239000000805 composite resin Substances 0.000 abstract description 16
- 125000004953 trihalomethyl group Chemical group 0.000 abstract description 8
- 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 abstract description 6
- 229930006711 bornane-2,3-dione Natural products 0.000 abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- YYBBCEVUANFEQR-UHFFFAOYSA-N 2,6-bis(trichloromethyl)-1h-1,3,5-triazin-4-one Chemical compound ClC(Cl)(Cl)C1=NC(=O)N=C(C(Cl)(Cl)Cl)N1 YYBBCEVUANFEQR-UHFFFAOYSA-N 0.000 abstract description 3
- 208000002925 dental caries Diseases 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000005286 illumination Methods 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- 230000037048 polymerization activity Effects 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000945 filler Substances 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000005548 dental material Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000005452 bending Methods 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000003479 dental cement Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000001678 irradiating effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001634 bornane-2,3-dione derivatives Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 210000000214 mouth Anatomy 0.000 description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PWCBSPFFLHCDKT-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-(2,4,4-trimethylpentylphosphonoyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)CC(C)CC(C)(C)C PWCBSPFFLHCDKT-UHFFFAOYSA-N 0.000 description 1
- IIJKHYBWZHCZFS-UHFFFAOYSA-N (4-fluorophenyl)boron;sodium Chemical compound [Na].[B]C1=CC=C(F)C=C1 IIJKHYBWZHCZFS-UHFFFAOYSA-N 0.000 description 1
- BSPJSKYURNZWFE-UHFFFAOYSA-N (4-methyl-3-oxopent-4-enyl) N-(2,2,3-trimethyloxan-3-yl)carbamate Chemical compound C(=O)(C(=C)C)CCOC(=O)NC1(C(OCCC1)(C)C)C BSPJSKYURNZWFE-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- FKMRHLPAQLOPPF-UHFFFAOYSA-N 1,2-diethoxythioxanthen-9-one Chemical compound C(C)OC1=C(C=2C(C3=CC=CC=C3SC2C=C1)=O)OCC FKMRHLPAQLOPPF-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- MFGSQXUNSUJWPZ-UHFFFAOYSA-N 1,7,7-trimethyl-2,3-dioxobicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2(C(O)=O)C(=O)C(=O)C1(C)C2(C)C MFGSQXUNSUJWPZ-UHFFFAOYSA-N 0.000 description 1
- QUDNWFSGYBTWLF-UHFFFAOYSA-N 1,7,7-trimethyl-2,3-dioxobicyclo[2.2.1]heptane-4-sulfonic acid Chemical compound C1CC2(S(O)(=O)=O)C(=O)C(=O)C1(C)C2(C)C QUDNWFSGYBTWLF-UHFFFAOYSA-N 0.000 description 1
- TYQQQRVWMDKQSV-UHFFFAOYSA-N 1-ethenyl-6-(trichloromethyl)-1,3,5-triazin-2-one Chemical compound ClC(Cl)(Cl)C1=NC=NC(=O)N1C=C TYQQQRVWMDKQSV-UHFFFAOYSA-N 0.000 description 1
- QZKVUSSYPPWURQ-UHFFFAOYSA-N 1-methylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C QZKVUSSYPPWURQ-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
- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-UHFFFAOYSA-N 0.000 description 1
- WNZVRDLNCMFQRZ-UHFFFAOYSA-N 2,6-bis(tribromomethyl)-1h-1,3,5-triazin-4-one Chemical compound BrC(Br)(Br)C1=NC(=O)N=C(C(Br)(Br)Br)N1 WNZVRDLNCMFQRZ-UHFFFAOYSA-N 0.000 description 1
- OXTDANZUTWFVHC-UHFFFAOYSA-N 2-(2-phenylethenyl)-6-(tribromomethyl)-1h-1,3,5-triazin-4-one Chemical compound N1C(C(Br)(Br)Br)=NC(=O)N=C1C=CC1=CC=CC=C1 OXTDANZUTWFVHC-UHFFFAOYSA-N 0.000 description 1
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 1
- ZAHQQNZWWAHDFC-UHFFFAOYSA-N 2-(3-methoxyphenyl)-6-(trichloromethyl)-1h-1,3,5-triazin-4-one Chemical compound COC1=CC=CC(C=2NC(=NC(=O)N=2)C(Cl)(Cl)Cl)=C1 ZAHQQNZWWAHDFC-UHFFFAOYSA-N 0.000 description 1
- VSDISEOTCDTPJW-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(trichloromethyl)-1h-1,3,5-triazin-4-one Chemical compound C1=CC(Cl)=CC=C1C1=NC(=O)N=C(C(Cl)(Cl)Cl)N1 VSDISEOTCDTPJW-UHFFFAOYSA-N 0.000 description 1
- LKGHREOIVDZMKI-UHFFFAOYSA-N 2-(4-methoxyphenyl)-6-(trichloromethyl)-1h-1,3,5-triazin-4-one Chemical compound C1=CC(OC)=CC=C1C1=NC(=O)N=C(C(Cl)(Cl)Cl)N1 LKGHREOIVDZMKI-UHFFFAOYSA-N 0.000 description 1
- UYFKZTUOHBNRCQ-UHFFFAOYSA-N 2-(4-phenylphenyl)-6-(trichloromethyl)-1h-1,3,5-triazin-4-one Chemical compound N1C(C(Cl)(Cl)Cl)=NC(=O)N=C1C1=CC=C(C=2C=CC=CC=2)C=C1 UYFKZTUOHBNRCQ-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-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
- XUPKQJGWOGGTQN-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;boron Chemical compound [B].OCCN(CCO)CCO XUPKQJGWOGGTQN-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
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
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- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
Abstract
【解決手段】 (A)下記一般式(1)
【化1】
(式中、R1は水素原子、水酸基又は炭素数1〜15の有機基であり、Xはハロゲン原子である。)で示される4、6−ビス(トリクロロメチル)−1,3,5−トリアジン−2(1H)−オン等のトリハロメチル基により置換されたトリアジン−2(1H)−オン化合物、(B)カンファーキノン等のα−ジケトン、(C)N,N−ジメチル安息香酸エチル等の芳香族アミン化合物からなる光重合開始剤。
【選択図】 なし
Description
上記置換基を有していてもよいアルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、n−ヘキシル基等の非置換のアルキル基;クロロメチル基、2−クロロエチル基等のハロゲンにより置換されたアルキル基;2−ヒドロキシエチル基等の水酸基により置換されたアルキル基等の炭素数1〜6のものが挙げられる。置換基を有していてもよいアリール基としては、フェニル基、p−メトキシフェニル、p−メチルチオフェニル基、p−クロロフェニル基、4−ビフェニリル基等の炭素数6〜12のものが例示され、置換基を有していてもよいアルケニル基としては、ビニル基、アリル基、2−フェニルエテニル基等の炭素数2〜12のものが、置換基を有していてもよいアルコキシ基としては、メトキシ基、エトキシ基、ブトキシ基等の炭素数1〜10のもの等が例示され、置換基を有していても良いアルキルオキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、ブトキシカルボニル基、アミルオキシカルボニル基、イソアミルオキシカルボニル基等のアルキルオキシ基部分の炭素数が1〜10のものが例示される。
(i)芳香族化合物系のもの
2,2−ビス(メタクリロイルオキシフェニル)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と略記する)、2,2−ビス(4−メタクリロイルオキシフェニル)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(以下、D−2.6Eと略記する)、2,2−ビス(4−メタ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−メタクリロイルオキシジエトキシフェニル)−2(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2(4−メタクリロイルオキシジプロポキシフェニル)−2−(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシプロポキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシイソプロポキシフェニル)プロパン及びこれらのメタクリレートに対応するアクリレート;2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレートあるいはこれらメタクリレートに対応するアクリレートのような−OH基を有するビニルモノマーと、ジイソシアネートメチルベンゼン、4,4‘−ジフェニルメタンジイソシアネートのような芳香族基を有するジイソシアネート化合物との付加から得られるジアダクト等。
エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート(以下、3Gと略記する)、テトラエチレングリコールジメタクリレート、ネオペンチルグリコールジメタクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレートおよびこれらのメタクリレートに対応するアクリレート;2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレートあるいはこれらのメタクリレートに対応するアクリレートのような−OH基を有するビニルモノマーと、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)のようなジイソシアネート化合物との付加体から得られるジアダクト;1,2−ビス(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)エチル等。
トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールメタントリメタクリレート等のメタクリレート及びこれらのメタクリレートに対応するアクリレート等。
ペンタエリスリトールテトラメタクリレート、ペンタエリスリトールテトラアクリレート及びジイソシアネートメチルベンゼン、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)、4,4−ジフェニルメタンジイソシアネート、トリレン−2,4−ジイソシアネートのようなジイソシアネート化合物とグリシドールジメタクリレートとの付加体から得られるジアダクト等。
(A)トリハロメチル基により置換された1,3,5−トリアジン−2(1H)−オン化合物
・4,6−ビス(トリクロロメチル)−1,3,5−トリアジン−2(1H)−オン(BTTO)
・4−フェニル−6−トリクロロメチル−1,3,5−トリアジン−2(1H)−オン(PTTO)
(B)α―ジケトン
・カンファーキノン(CQ)
(C)芳香族アミン化合物
・N,N−ジメチルp−安息香酸エチル(DMBE)
・N,N−ジメチルp−安息香酸イソアミル(DMBI)
・N,N−ジメチルp−トルイジン(DMPT)
(D)重合性単量体
・2,2−ビス[(3−メタクリロイルオキシ−2−ヒドロキシプロピルオキシ)フェニル]プロパン(bis−GMA)
・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(D2.6E)
・トリエチレングリコールジメタクリレート(3G)
・1,6−ビス(メタクリルエチルオキシカルボニルアミノ)トリメチルオキサン(UDMA)
(E)無機充填材
・球状シリカ−ジルコニア、γ−メタクリロイルオキシトリメトキシシラン表面処理物;平均粒径;0.5μm(E−1)
・球状シリカ−チタニア、γ−メタクリロイルオキシトリメトキシシラン表面処理物;平均粒径;0.08μm(E−2)
(F)その他の成分
・2,4,6−トリス(トリクロロメチル)−s−トリアジン(TCT)
・トリエタノールアミン(TEOA)
・ハイドロキノンモノメチルエーテル(HQME)
また、光硬化性コンポジットレジンの調製方法、硬化特性(環境光安定性、硬化時間)及び硬化体の機械的強度の測定は以下の方法を用いた。
重合性単量体に対し所定量の光重合開始剤と無機充填材を加え、赤色光下にて均一に攪拌、脱泡して調製した。
被照射面における光強度(mW/cm2)は、ウシオ電機株式会社製UIT−101を用い、360〜500nmの波長で測定して得た値を用いた。
6mmφ×1.0mmの孔を有するポリテトラフルオロエチレン製のモールドに、調製したコンポジットレジンのペーストを充填してポリプロピレンフィルムで圧接し、歯科用光照射器(トクソーパワーライト、トクヤマデンタル社;光出力密度700mW/cm2)をポリプロピレンフィルムに密着して5秒、10秒、15秒と5秒間隔で照射し、それぞれの照射時間での硬化体の硬さを手で触って以下の基準で評価した。このときの照射面における光強度は640〜650mW/cm2であった。
6mmφ×1.0mmの孔を有するポリテトラフルオロエチレン製のモールドにペーストを充填してポリプロピレンフィルムで圧接し、歯科用光照射器(LUX・O・MAX、アケダデンタル社;光出力密度137mW/cm2)をポリプロピレンフィルムに密着して10秒照射し、硬化体を調製した。得られた硬化体を微小硬度計(松沢精機製MHT−1型)にてヴィッカース圧子を用いて、荷重100gf、荷重保持時間30秒で試験片にできたくぼみの対角線長さにより求めた。このときの照射面における光強度は640〜650mW/cm2であった。
調製した光硬化性コンポジットレジンを50℃に設定したインキュベーター内に遮光下保管し、一定期間毎に(3)と同様な方法でヴィッカース硬度を測定し、得られたヴィッカース硬度値の経時変化から保存安定性を評価した。
ペースト状の硬化性組成物試料の表面が10000ルックスになるように光源と試料との距離を設定した。光源には15W蛍光灯(松下電器製、商品名パルック)を用い、照度計(デジタルルックスメーターFLX−1330、東京硝子器械製。400〜700nmに感度を有する。)にて測定される照度が上記照度になるよう、試料と蛍光灯の距離を設定した。この照射面における光強度は0.4mW/cm2であった。作製した光硬化性コンポジットレジンのペーストをポリプロピレンフィルムに0.03g量り採り、上記蛍光灯の光を所定時間時間照射した後、試料を押しつぶし、試料内部が固まり始めた時間を計測した。なお、照射時間は5秒間隔とした。この時間が長いほど環境光安定性に優れ、良好な操作余裕時間を得ることができる。
ステンレス製型枠に硬化性組成物を充填し、ポリプロピレンで圧接した状態で、一方の面から10秒×3回、全体に光が当たるように場所を変えてトクソーパワーライトにてポリプロピレンに密着させて光照射を行なった。ついで、反対の面からも同様にポリプロピレンに密着させて10秒×3回光照射を行ない硬化体を得た。#800の耐水研磨紙にて、硬化体を2×2×25mmの角柱状に整え、この試料片を試験機(島津製作所製、オートグラフAG5000D)に装着し、支点間距離20mm、クロスヘッドスピード1mm/分で3点曲げ破壊強度を測定した。
bisGMA(60重量部)、3G(40重量部)からなる重合性単量体100重量部、無機充填材E−1を140重量部、E−2を60重量部、重合禁止剤としてHQMEを0.15重量部、及び表1に示す光重合開始剤からなる光硬化型コンポジットレジンを暗所下、メノウ乳鉢を用いて攪拌混合してペースト状の組成物を調製した。上記ペーストの環境光安定性ならびに硬化速度、硬化体のヴィッカース硬度ならびに曲げ強度を測定した。また、保存安定性に関しても評価を行なった。結果を表1に示す。
実施例1〜5と同様に、表1に示す組成からなるペースト状の光硬化型コンポジットレジンを調製し、環境光安定性、硬化速度、曲げ強度及びヴィッカース硬度による保存安定性を評価した。なお、ヴィッカース硬度の測定は光照射の所定時間を10秒として得られた硬化体で行なった。
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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