WO2024075641A1 - Matériau polymère destiné à être utilisé en dentisterie - Google Patents
Matériau polymère destiné à être utilisé en dentisterie Download PDFInfo
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- WO2024075641A1 WO2024075641A1 PCT/JP2023/035577 JP2023035577W WO2024075641A1 WO 2024075641 A1 WO2024075641 A1 WO 2024075641A1 JP 2023035577 W JP2023035577 W JP 2023035577W WO 2024075641 A1 WO2024075641 A1 WO 2024075641A1
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- mass
- compounds
- dental
- transition metal
- acid
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- 239000002861 polymer material Substances 0.000 title abstract description 5
- 239000000178 monomer Substances 0.000 claims abstract description 52
- 230000002378 acidificating effect Effects 0.000 claims abstract description 43
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 38
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 17
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 113
- 239000000945 filler Substances 0.000 claims description 16
- 239000003504 photosensitizing agent Substances 0.000 claims description 13
- 150000003624 transition metals Chemical group 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 7
- 239000005749 Copper compound Substances 0.000 claims description 6
- 150000001880 copper compounds Chemical class 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 150000001869 cobalt compounds Chemical class 0.000 claims description 5
- 150000002506 iron compounds Chemical class 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 150000003682 vanadium compounds Chemical class 0.000 claims description 5
- 150000001845 chromium compounds Chemical class 0.000 claims description 4
- 150000002697 manganese compounds Chemical class 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- -1 amine compound Chemical class 0.000 description 66
- 238000006116 polymerization reaction Methods 0.000 description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 229910001428 transition metal ion Inorganic materials 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- JEHKKBHWRAXMCH-UHFFFAOYSA-M benzenesulfinate Chemical compound [O-]S(=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-M 0.000 description 10
- 239000010949 copper Substances 0.000 description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- JJLJMEJHUUYSSY-UHFFFAOYSA-L copper(II) hydroxide Inorganic materials [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 5
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 5
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 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 4
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 4
- VLUWLNIMIAFOSY-UHFFFAOYSA-N 2-methylbenzenesulfinic acid Chemical compound CC1=CC=CC=C1S(O)=O VLUWLNIMIAFOSY-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 229930006711 bornane-2,3-dione Natural products 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- AEJIMXVJZFYIHN-UHFFFAOYSA-N copper;dihydrate Chemical compound O.O.[Cu] AEJIMXVJZFYIHN-UHFFFAOYSA-N 0.000 description 3
- 125000005520 diaryliodonium group Chemical group 0.000 description 3
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 150000004992 toluidines Chemical class 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 3
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical class O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 2
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 2
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 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
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 2
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000010376 calcium ascorbate Nutrition 0.000 description 2
- 229940047036 calcium ascorbate Drugs 0.000 description 2
- 239000011692 calcium ascorbate Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
- 239000000805 composite resin Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical compound CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 description 2
- UPWOEMHINGJHOB-UHFFFAOYSA-N oxo(oxocobaltiooxy)cobalt Chemical compound O=[Co]O[Co]=O UPWOEMHINGJHOB-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- YEMGQZDWLLBIEY-UHFFFAOYSA-M sodium;2-anilinoacetate Chemical compound [Na+].[O-]C(=O)CNC1=CC=CC=C1 YEMGQZDWLLBIEY-UHFFFAOYSA-M 0.000 description 2
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- DSJDHQOKMCDBEW-UHFFFAOYSA-O (4,7-dihydroxynaphthalen-1-yl)-dimethylsulfanium Chemical compound C1=C(O)C=C2C([S+](C)C)=CC=C(O)C2=C1 DSJDHQOKMCDBEW-UHFFFAOYSA-O 0.000 description 1
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- GCQNBIQDEIUKOD-UHFFFAOYSA-M benzyl(trimethyl)azanium;naphthalene-2-sulfinate Chemical compound C[N+](C)(C)CC1=CC=CC=C1.C1=CC=CC2=CC(S(=O)[O-])=CC=C21 GCQNBIQDEIUKOD-UHFFFAOYSA-M 0.000 description 1
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- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 1
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- UIFVGWNLHVCKCX-UHFFFAOYSA-N butan-1-amine 4-chlorobenzenesulfinic acid Chemical compound CCCCN.OS(=O)c1ccc(Cl)cc1 UIFVGWNLHVCKCX-UHFFFAOYSA-N 0.000 description 1
- XUPCLXDANQVGBJ-UHFFFAOYSA-N butan-1-amine 4-methylbenzenesulfinic acid Chemical compound C1(=CC=C(C=C1)S(=O)[O-])C.C(CCC)[NH3+] XUPCLXDANQVGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
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- JPLNMWITWCOINR-UHFFFAOYSA-L calcium;4-methylbenzenesulfinate Chemical compound [Ca+2].CC1=CC=C(S([O-])=O)C=C1.CC1=CC=C(S([O-])=O)C=C1 JPLNMWITWCOINR-UHFFFAOYSA-L 0.000 description 1
- CQTBCRGSMDMCKL-UHFFFAOYSA-L calcium;benzenesulfinate Chemical compound [Ca+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 CQTBCRGSMDMCKL-UHFFFAOYSA-L 0.000 description 1
- FAYYUXPSKDFLEC-UHFFFAOYSA-L calcium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Ca+2].[O-]S([O-])(=O)=S FAYYUXPSKDFLEC-UHFFFAOYSA-L 0.000 description 1
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- 150000001768 cations Chemical class 0.000 description 1
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- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
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- OBWXQDHWLMJOOD-UHFFFAOYSA-H cobalt(2+);dicarbonate;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Co+2].[Co+2].[Co+2].[O-]C([O-])=O.[O-]C([O-])=O OBWXQDHWLMJOOD-UHFFFAOYSA-H 0.000 description 1
- IUYLTEAJCNAMJK-UHFFFAOYSA-N cobalt(2+);oxygen(2-) Chemical compound [O-2].[Co+2] IUYLTEAJCNAMJK-UHFFFAOYSA-N 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(II) oxide Inorganic materials [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 229910000335 cobalt(II) sulfate Inorganic materials 0.000 description 1
- UBEWDCMIDFGDOO-UHFFFAOYSA-N cobalt(II,III) oxide Inorganic materials [O-2].[O-2].[O-2].[O-2].[Co+2].[Co+3].[Co+3] UBEWDCMIDFGDOO-UHFFFAOYSA-N 0.000 description 1
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- PKSIZOUDEUREFF-UHFFFAOYSA-N cobalt;dihydrate Chemical compound O.O.[Co] PKSIZOUDEUREFF-UHFFFAOYSA-N 0.000 description 1
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 description 1
- 238000012669 compression test Methods 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
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- 229910000009 copper(II) carbonate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- ZKXWKVVCCTZOLD-FDGPNNRMSA-N copper;(z)-4-hydroxypent-3-en-2-one Chemical compound [Cu].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O ZKXWKVVCCTZOLD-FDGPNNRMSA-N 0.000 description 1
- SVOAENZIOKPANY-CVBJKYQLSA-L copper;(z)-octadec-9-enoate Chemical compound [Cu+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O SVOAENZIOKPANY-CVBJKYQLSA-L 0.000 description 1
- VURZAXVELVEAAN-UHFFFAOYSA-L copper;1,3-benzothiazole-2-thiolate Chemical compound [Cu+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 VURZAXVELVEAAN-UHFFFAOYSA-L 0.000 description 1
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 1
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- XPLSDXJBKRIVFZ-UHFFFAOYSA-L copper;prop-2-enoate Chemical compound [Cu+2].[O-]C(=O)C=C.[O-]C(=O)C=C XPLSDXJBKRIVFZ-UHFFFAOYSA-L 0.000 description 1
- KLMIJCPYCOMSQF-UHFFFAOYSA-N copper;propane-1,3-diamine Chemical compound [Cu].NCCCN KLMIJCPYCOMSQF-UHFFFAOYSA-N 0.000 description 1
- LROWILPKXRHMNL-UHFFFAOYSA-N copper;thiourea Chemical compound [Cu].NC(N)=S LROWILPKXRHMNL-UHFFFAOYSA-N 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 235000019854 cupric carbonate Nutrition 0.000 description 1
- 239000011646 cupric carbonate Substances 0.000 description 1
- 235000019856 cupric gluconate Nutrition 0.000 description 1
- 239000011642 cupric gluconate Substances 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- NVJBFARDFTXOTO-UHFFFAOYSA-N diethyl sulfite Chemical compound CCOS(=O)OCC NVJBFARDFTXOTO-UHFFFAOYSA-N 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- BBLSYMNDKUHQAG-UHFFFAOYSA-L dilithium;sulfite Chemical compound [Li+].[Li+].[O-]S([O-])=O BBLSYMNDKUHQAG-UHFFFAOYSA-L 0.000 description 1
- JTNDNBUJMQNEGL-UHFFFAOYSA-N dimethyl(phenacyl)sulfanium Chemical compound C[S+](C)CC(=O)C1=CC=CC=C1 JTNDNBUJMQNEGL-UHFFFAOYSA-N 0.000 description 1
- HUDDJECNGKLELJ-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;chloride Chemical compound [Cl-].C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 HUDDJECNGKLELJ-UHFFFAOYSA-M 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 description 1
- IIKLEMKAKOISSP-UHFFFAOYSA-N dipropan-2-yl sulfite Chemical compound CC(C)OS(=O)OC(C)C IIKLEMKAKOISSP-UHFFFAOYSA-N 0.000 description 1
- MAIQPVFXODAAIG-UHFFFAOYSA-N dipropyl sulfite Chemical compound CCCOS(=O)OCCC MAIQPVFXODAAIG-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
- 235000019268 ferrous carbonate Nutrition 0.000 description 1
- 239000004222 ferrous gluconate Substances 0.000 description 1
- 235000013924 ferrous gluconate Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 1
- 229910000015 iron(II) carbonate Inorganic materials 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
- 229910021519 iron(III) oxide-hydroxide Inorganic materials 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NGBOPQGPOHMAGY-UHFFFAOYSA-M lithium;2-methylbenzenesulfinate Chemical compound [Li+].CC1=CC=CC=C1S([O-])=O NGBOPQGPOHMAGY-UHFFFAOYSA-M 0.000 description 1
- MSUZXYWQEDRGFN-UHFFFAOYSA-M lithium;4-methylbenzenesulfinate Chemical compound [Li+].CC1=CC=C(S([O-])=O)C=C1 MSUZXYWQEDRGFN-UHFFFAOYSA-M 0.000 description 1
- NVSKMOMNGUJKCL-UHFFFAOYSA-M lithium;benzenesulfinate Chemical compound [Li+].[O-]S(=O)C1=CC=CC=C1 NVSKMOMNGUJKCL-UHFFFAOYSA-M 0.000 description 1
- 229940062135 magnesium thiosulfate Drugs 0.000 description 1
- MUZDAAUUCSJIRK-UHFFFAOYSA-L magnesium;benzenesulfinate Chemical compound [Mg+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 MUZDAAUUCSJIRK-UHFFFAOYSA-L 0.000 description 1
- TZKHCTCLSRVZEY-UHFFFAOYSA-L magnesium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [Mg+2].[O-]S([O-])(=O)=S TZKHCTCLSRVZEY-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 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
- BGAPSUYNXVVTHA-UHFFFAOYSA-N n,n-diethylethanamine;naphthalene-2-sulfinic acid Chemical compound CCN(CC)CC.C1=CC=CC2=CC(S(=O)O)=CC=C21 BGAPSUYNXVVTHA-UHFFFAOYSA-N 0.000 description 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
- IQBYDPCDBRUPCU-UHFFFAOYSA-N n-methylaniline;4-methylbenzenesulfinic acid Chemical compound CNC1=CC=CC=C1.CC1=CC=C(S(O)=O)C=C1 IQBYDPCDBRUPCU-UHFFFAOYSA-N 0.000 description 1
- ICYDASAGOZFWIC-UHFFFAOYSA-N naphthalene-1-sulfinic acid Chemical compound C1=CC=C2C(S(=O)O)=CC=CC2=C1 ICYDASAGOZFWIC-UHFFFAOYSA-N 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- SJDXYUDKQYOEES-UHFFFAOYSA-L oxalate;oxovanadium(2+) Chemical compound [V+2]=O.[O-]C(=O)C([O-])=O SJDXYUDKQYOEES-UHFFFAOYSA-L 0.000 description 1
- KFAFTZQGYMGWLU-UHFFFAOYSA-N oxo(oxovanadiooxy)vanadium Chemical compound O=[V]O[V]=O KFAFTZQGYMGWLU-UHFFFAOYSA-N 0.000 description 1
- DYYSJNQVLWANCC-UHFFFAOYSA-N oxolan-2-ylmethylthiourea Chemical compound NC(=S)NCC1CCCO1 DYYSJNQVLWANCC-UHFFFAOYSA-N 0.000 description 1
- RBFRVUKIVGOWND-UHFFFAOYSA-L oxygen(2-);vanadium(4+);sulfate Chemical compound [O-2].[V+4].[O-]S([O-])(=O)=O RBFRVUKIVGOWND-UHFFFAOYSA-L 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019275 potassium ascorbate Nutrition 0.000 description 1
- 229940017794 potassium ascorbate Drugs 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
- CONVKSGEGAVTMB-RXSVEWSESA-M potassium-L-ascorbate Chemical compound [K+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RXSVEWSESA-M 0.000 description 1
- MQXBJGDCPQIMPM-UHFFFAOYSA-M potassium;2-methylbenzenesulfinate Chemical compound [K+].CC1=CC=CC=C1S([O-])=O MQXBJGDCPQIMPM-UHFFFAOYSA-M 0.000 description 1
- KQZLTJGDWZAZPQ-UHFFFAOYSA-M potassium;4-chlorobenzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=C(Cl)C=C1 KQZLTJGDWZAZPQ-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SLUHLANJIVXTRQ-UHFFFAOYSA-N pyridin-2-ylthiourea Chemical compound NC(=S)NC1=CC=CC=N1 SLUHLANJIVXTRQ-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 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
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- KHDBMTLGTSGEEG-UHFFFAOYSA-M sodium;2-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=CC=C1S([O-])=O KHDBMTLGTSGEEG-UHFFFAOYSA-M 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- JGGFVSGYTHUAOQ-UHFFFAOYSA-M sodium;naphthalene-2-sulfinate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)[O-])=CC=C21 JGGFVSGYTHUAOQ-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YDOSLMFOLKFQBA-UHFFFAOYSA-L strontium naphthalene-2-sulfinate Chemical compound [Sr+2].C1=CC=CC2=CC(S(=O)[O-])=CC=C21.C1=CC=CC2=CC(S(=O)[O-])=CC=C21 YDOSLMFOLKFQBA-UHFFFAOYSA-L 0.000 description 1
- JBROWOKLRZQSRX-UHFFFAOYSA-L strontium;benzenesulfinate Chemical compound [Sr+2].[O-]S(=O)C1=CC=CC=C1.[O-]S(=O)C1=CC=CC=C1 JBROWOKLRZQSRX-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- STDMRMREKPZQFJ-UHFFFAOYSA-H tricopper;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Cu+2].[Cu+2].[Cu+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O STDMRMREKPZQFJ-UHFFFAOYSA-H 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 description 1
- ZOYIPGHJSALYPY-UHFFFAOYSA-K vanadium(iii) bromide Chemical compound [V+3].[Br-].[Br-].[Br-] ZOYIPGHJSALYPY-UHFFFAOYSA-K 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/64—Thermal radical initiators
-
- 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
Definitions
- the present invention relates to a dental polymeric material.
- dental polymerization materials containing a polymerizable monomer and a radical polymerization initiator are known for use in prosthetic treatment of missing teeth, etc.
- a dental polymerization material using a photopolymerization initiator as the radical polymerization initiator has been proposed (see, for example, Patent Document 1).
- the dental polymerization material of Patent Document 1 contains a radical polymerization monomer, an ⁇ -diketone compound, an amine compound, and an aryl iodonium salt.
- dental polymer materials require a high hardening depth to accommodate treatment at deep sites.
- the dental polymerized material of Patent Document 1 has the disadvantage that it does not cure sufficiently in deep areas where light does not reach, resulting in a low curing depth. Furthermore, because dental polymerized materials are continuously subjected to forces such as occlusal force, there is a demand for improved mechanical strength.
- the present invention aims to provide a dental polymeric material that has a high hardening depth and excellent mechanical strength.
- the present invention [1] is a dental polymerizable material for polymerizing a non-acidic monomer having no acidic group and an ethylenically unsaturated group in dental treatment, the dental polymerizable material containing a photoacid generator, a transition metal compound, and a reducing agent, the transition metal compound being solid in the dental polymerizable material, and being soluble in the acid generated by decomposition of the photoacid generator.
- the present invention [2] includes the dental polymeric material described in [1] above, which contains the non-acidic monomer and does not contain an acidic monomer.
- the present invention [3] includes the dental polymeric material described in [1] or [2] above, in which the transition metal compound contains a transition metal atom belonging to the fourth period of the periodic table.
- the present invention [4] includes a dental polymeric material according to any one of [1] to [3] above, in which the transition metal compound is at least one selected from the group consisting of copper compounds, iron compounds, cobalt compounds, chromium compounds, zinc compounds, manganese compounds, and vanadium compounds.
- the present invention [5] includes a dental polymerizable material according to any one of [1] to [4] above, in which the photoacid generator is soluble in the non-acidic monomer.
- the present invention [6] further includes a dental polymeric material according to any one of [1] to [5] above, which contains a filler.
- the present invention [7] further includes a dental polymeric material according to any one of [1] to [6] above, which contains a photosensitizer.
- the present invention [8] further includes a dental polymerizable material according to any one of [1] to [7] above, which contains a photopolymerization initiator.
- the present invention [9] includes a dental polymeric material described in any one of [1] to [8] above, which is a one-component type.
- the photoacid generator decomposes upon irradiation with light, generating radicals and acid.
- the radicals generated from the photoacid generator photopolymerize the nonacidic monomer.
- the acid generated from the photoacid generator dissolves the transition metal compound, generating transition metal ions.
- the generated transition metal ions react chemically with a reducing agent to generate radicals.
- the radicals generated by the chemical reaction chemically polymerize the nonacidic monomer. Since photopolymerization and chemical polymerization occur simultaneously, the degree of polymerization increases and the mechanical strength improves.
- the heat of polymerization generated by photopolymerization and chemical polymerization causes decomposition into the photoacid generator, and polymerization proceeds (frontal polymerization) even in deep areas where light does not directly reach, resulting in a high cure depth.
- the dental polymerization material may be, for example, a one-component dental polymerization material.
- one-component dental polymerization materials do not require mixing before use. If the one-component dental polymerization material has self-adhesive properties, it can be used by applying it directly to tooth structure. On the other hand, if the one-component dental polymerization material does not have self-adhesive properties, it can be used in combination with a pretreatment material.
- Self-adhesive means that the material has sufficient adhesion to tooth structure even without applying a pretreatment material to the tooth structure.
- pretreatment materials are used in dental treatment, for example, to improve the adhesion between one-component dental polymerizable materials and at least one of a prosthesis and tooth structure.
- Examples of one-component dental polymerizable materials include one-component polymerizable composite resins and one-component polymerizable cements.
- One-component polymerizable composite resins are used in dental treatment to fill missing teeth.
- One-component polymerizable cements are used to attach prosthetic devices to missing teeth.
- the one-component dental polymerizable material of the present invention contains a photoacid generator, a transition metal compound, and a reducing agent as essential components for polymerizing a non-acidic monomer that does not have an acidic group but has an ethylenically unsaturated group.
- the one-component dental polymeric material preferably contains a non-acidic monomer and does not contain an acidic monomer.
- the one-component dental polymerization material may not contain non-acidic monomers and may not contain acidic monomers. In this case, the one-component dental polymerization material is used to polymerize the monomers.
- Non-acidic monomers do not have an acidic group and have an ethylenically unsaturated group.
- ethylenically unsaturated groups examples include acryloyl groups, methacryloyl groups, and vinyl groups.
- Non-acidic monomers are monomers that do not have an acidic group and are classified into non-acidic monomers that have a hydroxyl group, non-acidic monomers that have a urethane bond, and non-acidic monomers that do not have a hydroxyl group or a urethane bond.
- non-acidic monomers having a hydroxyl group examples include mono(meth)acrylates and di(meth)acrylates.
- Examples of mono(meth)acrylates having a hydroxyl group include 2-hydroxyethyl(meth)acrylate, 3-hydroxypropyl(meth)acrylate, 6-hydroxyhexyl(meth)acrylate, and dihydroxypropyl mono(meth)acrylate.
- a preferred example of a mono(meth)acrylate having a hydroxyl group is 2-hydroxyethyl(meth)acrylate.
- An example of a di(meth)acrylate having a hydroxyl group is a bisphenol A derivative.
- An example of a bisphenol A derivative having a hydroxyl group is 2,2-bis[4-(3-(meth)acryloyloxy-2-hydroxypropoxy)phenyl]propane (Bis-GMA).
- UDMA UDMA
- Examples of mono(meth)acrylates that do not have a hydroxyl group or a urethane bond include alkyl(meth)acrylates.
- Examples of alkyl(meth)acrylates include methyl(meth)acrylate, ethyl(meth)acrylate, and butyl(meth)acrylate.
- di(meth)acrylates that do not have hydroxyl groups or urethane bonds include alkanediol di(meth)acrylates, polyoxyalkylene group-containing di(meth)acrylates, and bisphenol A derivatives.
- alkanediol di(meth)acrylates examples include ethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate.
- polyoxyalkylene group-containing di(meth)acrylate is a polyoxyethylene group-containing di(meth)acrylate.
- polyoxyethylene group-containing di(meth)acrylates examples include triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, and nonaethylene glycol di(meth)acrylate, and preferably triethylene glycol di(meth)acrylate (TEGDMA).
- TEGDMA triethylene glycol di(meth)acrylate
- An example of a bisphenol A derivative that does not have a hydroxyl group or a urethane bond is ethylene oxide-modified bisphenol A di(meth)acrylate.
- Non-acidic monomers can be used alone or in combination of two or more types. It is preferable to use two or more types of non-acidic monomers in combination.
- Non-acidic monomer is the combination of UDMA and TEGDMA.
- the proportion of non-acidic monomer in the one-component dental polymeric material is, for example, 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, particularly preferably 25% by mass or more, and, for example, 95% by mass or less, preferably 80% by mass or less, more preferably 65% by mass or less, even more preferably 50% by mass or less, particularly preferably 40% by mass or less.
- the content of the non-acidic monomer is, for example, 500 parts by mass or more, preferably 1000 parts by mass or more, more preferably 1500 parts by mass or more, and for example, 5000 parts by mass or less, preferably 4000 parts by mass or less, more preferably 3000 parts by mass or less, per 100 parts by mass of the photoacid generator.
- a photoacid generator is a compound that decomposes when exposed to light such as visible light and/or ultraviolet light, generating radicals and acid.
- the radicals generated from the photoacid generator photopolymerize non-acidic monomers.
- the acid generated from the photoacid generator dissolves transition metal compounds and generates transition metal ions.
- the generated transition metal ions react chemically with a reducing agent to generate radicals.
- the radicals generated by the chemical reaction chemically polymerize the non-acidic monomers.
- the photoacid generator is preferably soluble in the non-acidic monomers described above.
- photoacid generators examples include ionic photoacid generators and nonionic photoacid generators.
- Ionic photoacid generators include, for example, iodonium salt compounds and sulfonium salt compounds.
- iodonium salt compounds include diaryliodonium compounds.
- the diaryliodonium salt compound is a compound represented by the following general formula (1).
- R1 to R4 each represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkenyl group, an alkoxy group, an aryloxy group, or a nitro group, and X represents an anion.
- R1 to R4 are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkenyl group, an alkoxy group, an aryloxy group, or a nitro group, and X represents an anion.
- Halogen atoms include, for example, fluoro, chloro, bromo, and iodine groups.
- alkyl groups include hydrocarbon groups having 1 to 20 carbon atoms. Specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, pentyl, isopentyl, and hexyl groups.
- Aryl groups include, for example, hydrocarbon groups having 6 to 14 carbon atoms. Specific examples include phenyl groups, p-methylphenyl groups, p-chlorophenyl groups, and naphthyl groups.
- alkenyl groups include hydrocarbon groups having 1 to 6 carbon atoms. Specific examples include vinyl groups, allyl groups, isopropenyl groups, butenyl groups, 2-phenylethenyl groups, and 2-(substituted phenyl)ethenyl groups.
- alkoxy groups include alkoxy groups having 1 to 6 carbon atoms. Specific examples include methoxy, ethoxy, propoxy, and butoxy groups.
- Aryloxy groups include, for example, aryloxy groups having 6 to 14 carbon atoms. Specific examples include phenoxy, p-methoxyphenyl, and p-octyloxyphenyl.
- R1 to R4 are preferably hydrogen atoms or alkyl groups.
- diaryliodonium salt compounds include diaryliodonium salt compounds consisting of cations of diphenyliodonium, bis(p-chlorophenyl)iodonium, ditolyliodonium, bis(p-tert-butylphenyl)iodonium, p-isopropylphenyl-p-methylphenyliodonium, bis(m-nitrophenyl)iodonium, p-tert-butylphenylphenyliodonium, p-methoxyphenylphenyliodonium, bis(p-methoxyphenyl)iodonium, and p-octyloxyphenylphenyliodonium, and anions of chloride, bromide, p-toluenesulfonate, trifluoromethanesulfonate, trifluorotris(pentafluoroethyl)phosphate, tetrafluorobo
- a preferred diaryliodonium salt compound is a diaryliodonium salt compound consisting of a p-isopropylphenyl-p-methylphenyliodonium cation and a trifluorotris(pentafluoroethyl)phosphate anion.
- Sulfonium salt compounds include, for example, dimethylphenacylsulfonium, dimethylbenzylsulfonium, dimethyl-4-hydroxyphenylsulfonium, dimethyl-4-hydroxynaphthylsulfonium, dimethyl-4,7-dihydroxynaphthylsulfonium, dimethyl-4,8-dihydroxynaphthylsulfonium, triphenylsulfonium, p-tolyldiphenylsulfonium, p-tert-butylphenyldiphenylsulfonium, and diphenyl-4-phenylthiophenylsulfonium chloride, bromide, p-toluenesulfonate, trifluoromethanesulfonate, tetrafluoroborate, tetrakispentafluorophenylborate, tetrakispentafluorophenylgal
- Ionic photoacid generators are preferably iodonium salt compounds.
- Nonionic photoacid generators include, for example, s-triazine compounds having a trihalomethyl group as a substituent, diazomethane compounds, sulfone compounds, sulfonate compounds, and arylsulfonate compounds.
- Examples of s-triazine compounds having a trihalomethyl group as a substituent include 2,4,6-tris(trichloromethyl)-s-triazine, 2,4,6-tris(tribromomethyl)-s-triazine, 2-methyl-4,6-bis(trichloromethyl)-s-triazine, 2-methyl-4,6-bis(tribromomethyl)-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methylthiophenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-chlorophenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(2,4-dichlorophenyl)-4,6-bis(trichloromethyl)-s
- Diazomethane compounds include, for example, bis(cyclohexylsulfonyl)diazomethane, bis(tert-butylsulfonyl)diazomethane, and bis(4-methylphenylsulfonyl)diazomethane.
- sulfone compound 2-methyl-2-([4-methylphenyl]sulfonyl)-1-(4-[methylthio]phenyl)-1-propanone.
- sulfonic acid ester compounds and arylsulfonic acid ester compounds include benzoin tosylate, ⁇ -methylolbenzoin tosylate, o-nitrobenzyl p-toluenesulfonate, and p-nitrobenzyl-9,10-diethoxyanthracene-2-sulfonate.
- Photoacid generators can be used alone or in combination of two or more types.
- the proportion of the photoacid generator in the one-component dental polymerizable material is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and even more preferably 1.5% by mass or more, and is, for example, 10% by mass or less, preferably 5% by mass or less, and more preferably 3% by mass or less.
- the content of the photoacid generator is, for example, 1 part by mass or more, preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and for example, 30 parts by mass or less, preferably 20 parts by mass or less, more preferably 10 parts by mass or less, per 100 parts by mass of the non-acidic monomer.
- Transition metal compounds At least a part of the transition metal compound is soluble in acid. Preferably, the entire transition metal compound is soluble in acid.
- the transition metal compound is soluble in acid generated by decomposition of a photoacid generator in a one-component dental polymerizable material. By dissolving in acid, transition metal ions are generated. The transition metal ions react chemically with a reducing agent to generate radicals. The generated radicals polymerize non-acidic monomers.
- the transition metal compound contains a transition metal atom that belongs to the fourth period of the periodic table.
- the periodic table is the IUPAC Periodic Table of the Elements (version date 1 December 2018).
- transition metal atoms include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), zinc (Zn), and gallium (Ga).
- Preferred examples of transition metal atoms include vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), copper (Cu), and zinc (Zn), and more preferably copper (Cu).
- transition metal compounds include oxides, hydroxides, halides, carboxylates, sulfates, nitrates, carbonates, and complexes of transition metals.
- halides include chlorides and bromides.
- carboxylates include formates, acetates, oleates, acrylates, gluconates, phthalates, and citrates.
- Transition metal complexes have a transition metal atom as the central metal and ligands that coordinate to the transition metal atom.
- Examples of the ligands include diketone-based ligands, amine-based ligands, thiol-based ligands, urea-based ligands, and thiourea-based ligands.
- Examples of the diketone-based ligands include acetylacetonate.
- Examples of the amine-based ligands include alkanediamines, benzimidazole, and benzothiazole.
- Examples of the thiol-based ligands include mercaptoethanol, mercaptotriazole, mercaptobenzothiazole, and mercaptobenzimidazole.
- Examples of the urea-based ligands include urea and ethyleneurea.
- Examples of the thiourea-based ligands include thiourea, acetylthiourea, pyridylthiourea, and ethylenethiourea.
- transition metal compounds include copper compounds, iron compounds, cobalt compounds, chromium compounds, zinc compounds, manganese compounds, and vanadium compounds.
- the transition metal compound is at least one selected from the group consisting of copper compounds, iron compounds, cobalt compounds, chromium compounds, zinc compounds, manganese compounds, and vanadium compounds.
- copper compounds include copper(II) hydroxide, copper(I) chloride, copper(II) chloride, copper(I) bromide, copper(II) bromide, copper(II) formate, copper(I) acetate, copper(II) acetate, copper(II) sulfate, copper(II) nitrate, copper(II) iodide, basic copper(II) carbonate, copper(I) oxide, copper(II) oxide, metallic copper, copper(II) oleate, copper(II) acrylate, copper(II) gluconate, copper(II) phthalate, copper(II) citrate, copper(II) acetylacetonate, copper mercaptobenzothiazole, copper 1,3-propanediamine, copper benzimidazole, copper benzothiazole, and copper thiourea.
- copper(II) hydroxide is used.
- iron compounds include iron(II) hydroxide, iron(III) oxide hydroxide, iron(II) chloride, iron(III) chloride, iron(I) bromide, iron(II) bromide, iron(II) acetate, iron(III) acetate, iron(II) carbonate, iron(II) oxide, iron(III) oxide, iron(II,III) oxide, metallic iron, iron(II) sulfate, iron(III) sulfate, iron(III) acetylacetonate, iron(III) citrate, and iron(II) gluconate.
- cobalt compounds include cobalt(II) hydroxide, cobalt(II) chloride, cobalt(II) acetate, cobalt(II) bromide, basic cobalt carbonate, cobalt(II) sulfate, cobalt(II) oxide, cobalt(III) oxide, cobalt(II,III) oxide, metallic cobalt, cobalt(II) nitrate, and cobalt(III) acetylacetonate.
- vanadium compounds include vanadium(III) chloride, vanadium(III) bromide, metallic vanadium, vanadium(II) oxide, vanadium(III) oxide, vanadium(V) oxide, vanadium(IV) oxyacetylacetonate, vanadium(III) acetylacetonate, oxovanadium(IV) oxalate, vanadium(IV) stearate, vanadium(IV) oxide sulfate, ammonium vanadate(V), and sodium orthovanadate(V).
- a transition metal compound As a transition metal compound, a copper compound is preferably used.
- the transition metal compound is solid in the one-component dental polymerizable material. That is, the one-component dental polymerizable material contains the components in the one-component dental polymerizable material and a powder of a transition metal compound that is insoluble in water and may be obtained by moisture absorption during storage. At 20°C and 1 atm, the transition metal compound is solid. The amount of the transition metal compound dissolved in 100 g of water at 20°C and 1 atm is, for example, 5 g or less, preferably 4 g or less, and more preferably 3 g or less. That is, in the one-component dental polymerizable material, the transition metal compound being solid means that at least a part of the transition metal compound is solid, and may be partially dissolved.
- the average particle size of the powder is not limited, but if it is too large, it is likely to settle, and if it is too small, the specific surface area becomes too large and the amount that can be dispersed decreases. Therefore, the average particle size is, for example, 0.01 ⁇ m or more, preferably 0.1 ⁇ m or more, more preferably 1 ⁇ m or more, and, for example, 500 ⁇ m or less, preferably 100 ⁇ m or less, and more preferably 50 ⁇ m or less.
- Transition metal compounds can be used alone or in combination of two or more types.
- the blending ratio of the transition metal compound in the one-component dental polymeric material is, for example, 0.0001 mass% or more, preferably 0.0005 mass% or more, more preferably 0.001 mass% or more, even more preferably 0.01 mass% or more, and, for example, 1 mass% or less, preferably 0.5 mass% or less, more preferably 0.1 mass% or less, even more preferably 0.05 mass% or less.
- the content of the transition metal compound is, for example, 0.01 parts by mass or more, preferably 0.03 parts by mass or more, more preferably 0.05 parts by mass or more, and for example, 3 parts by mass or less, preferably 1 part by mass or less, more preferably 0.5 parts by mass or less, per 100 parts by mass of the non-acidic monomer.
- the content of the transition metal compound is, for example, 0.5 parts by mass or more, preferably 1.0 parts by mass or more, more preferably 1.5 parts by mass or more, and for example, 8 parts by mass or less, preferably 5 parts by mass or less, more preferably 3 parts by mass or less, per 100 parts by mass of the photoacid generator.
- the reducing agent reduces the transition metal ions.
- the reducing agent is oxidized by the transition metal ions.
- the reducing agent is oxidized by the transition metal ions to generate radicals.
- the reducing agent may be any agent that reduces the above-mentioned transition metal ions, without any particular limitations.
- reducing agents include aromatic amine compounds, sulfinic acid compounds or their salts, thiourea compounds, thiosulfate compounds, phosphorous acid compounds, sulfurous acid compounds, (thio)barbituric acid compounds or their salts, ascorbic acid compounds or their salts, and ascorbic acid ester compounds or their salts.
- aromatic amine compounds include aromatic tertiary amines and aromatic amino acids.
- aromatic tertiary amines examples include N,N-dialkyltoluidine, N,N-bis(hydroxyalkyl)toluidine, N,N-dialkylaniline, and dialkylaminobenzoic acid esters.
- N,N-dialkyl toluidines examples include N,N-dimethyl-p-toluidine (DMPT) and N,N-diethyl-p-toluidine.
- N,N-bis(hydroxyalkyl)toluidine examples include N,N-bis(2-hydroxyethyl)-p-toluidine and N,N-bis(2-hydroxypropyl)-p-toluidine.
- N,N-dialkylanilines examples include N,N-dimethylaniline and N,N-diethylaniline.
- dialkylaminobenzoate esters examples include methyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate (EDAB), 2-butoxyethyl 4-(dimethylamino)benzoate, and isoamyl 4-(dimethylamino)benzoate.
- Aromatic amino acids include, for example, N-phenylglycine acid, sodium N-phenylglycine (SPG), and potassium N-phenylglycine.
- Sulfinic acid compounds and their salts include, for example, aromatic sulfinic acids and their salts.
- Aromatic sulfinic acids include, for example, benzenesulfinic acid, o-toluenesulfinic acid, p-toluenesulfinic acid, ethylbenzenesulfinic acid, decylbenzenesulfinic acid, dodecylbenzenesulfinic acid, chlorobenzenesulfinic acid, fluorobenzenesulfinic acid, and naphthalenesulfinic acid.
- Salts of aromatic sulfinic acid compounds include, for example, lithium benzenesulfinate, sodium benzenesulfinate, potassium benzenesulfinate, magnesium benzenesulfinate, calcium benzenesulfinate, strontium benzenesulfinate, barium benzenesulfinate, butylamine salt of benzenesulfinate, aniline salt of benzenesulfinate, toluidine salt of benzenesulfinate, phenylenediamine salt of benzenesulfinate, diethylamine salt of benzenesulfinate, diphenylamine salt of benzenesulfinate, triethylamine salt of benzenesulfinate, tributylamine salt of benzenesulfinate, ammonium salt of benzenesulfinate, tetraethylamine salt of benzenesulfinate, tetra
- Thiourea compounds include, for example, thiourea, methylthiourea, ethylthiourea, n-propylthiourea, isopropylthiourea, cyclohexylthiourea, benzylthiourea, phenylthiourea, acetylthiourea, benzoylthiourea, adamantylthiourea, (2-pyridyl)thiourea (PTU), 1-(2-tetrahydrofurfuryl)-2-thiourea, N,N'-dimethylthiourea, N,N'-diethylthiourea, N,N'-di-n-propylthiourea, and N,N'-di -isopropylthiourea, N,N'-dicyclohexylthiourea, N,N'-diphenylthiourea, trimethylthiourea (TM
- thiosulfate compounds include sodium thiosulfate, calcium thiosulfate, potassium thiosulfate, and magnesium thiosulfate.
- Examples of phosphorous compounds include inorganic phosphorous compounds and organic phosphorous compounds.
- inorganic phosphite compounds include calcium hypophosphite and sodium phosphite.
- organic phosphite compounds include diethyl phosphite, dibutyl phosphite, diisopropyl phosphite, di-n-propyl phosphite, triphenyl phosphite, triallyl phosphite, diethyl phosphite, dibutyl phosphite, diisopropyl phosphite, di-n-propyl phosphite, triphenyl phosphite, and triallyl phosphite.
- sulfite compounds include inorganic sulfite compounds and organic sulfite compounds.
- inorganic sulfite compounds include lithium sulfite, sodium sulfite, potassium sulfite, calcium sulfite, and sodium hydrogen sulfite.
- organic sulfite compounds include diethyl sulfite, di-n-propyl sulfite, diisopropyl sulfite, glycol sulfite, 1,3-propylene sulfite, and diallyl sulfite.
- (Thio)barbituric acid compounds and their salts include, for example, barbituric acid, 1,3-dimethylbarbituric acid, 1,3-diphenylbarbituric acid, 1,5-dimethylbarbituric acid, 5-butylbarbituric acid, 5-ethylbarbituric acid, 5-isopropylbarbituric acid, 5-cyclohexylbarbituric acid, 1,3,5-trimethylbarbituric acid, 1,3-dimethyl-5-ethylbarbituric acid, 1,3-dimethyl-n-butylbarbituric acid, 1,3-dimethyl-5-isobutylbarbituric acid, 1,3-dimethyl-5-cyclohexylbarbituric acid, 1,3-dimethyl-5-phenylbarbituric acid, 1-cyclohexyl-5-ethylbarbituric acid, thiobarbituric acid, and alkali metal or alkaline earth metal salts thereof
- ascorbic acid compounds and salts thereof include sodium ascorbate, calcium ascorbate, and potassium ascorbate.
- Ascorbate salts calcium ascorbate is preferred.
- ascorbic acid ester compounds and their salts include ascorbic acid palmitate, sodium salt of ascorbic acid palmitate, calcium salt of ascorbic acid palmitate, and potassium salt of ascorbic acid palmitate.
- a preferred example of the salt of an ascorbic acid ester is potassium salt of ascorbic acid palmitate.
- Reducing agents can be used alone or in combination of two or more types.
- the reducing agent is preferably a salt of an ascorbic acid compound.
- the mixing ratio of the reducing agent in the one-component dental polymerizable material is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1.0% by mass or more, and, for example, 30% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less.
- the content of the reducing agent is, for example, 1 part by mass or more, preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and for example, 10 parts by mass or less, preferably 7 parts by mass or less, more preferably 5 parts by mass or less, per 100 parts by mass of the non-acidic monomer.
- the content of the reducing agent is, for example, 10 parts by mass or more, preferably 30 parts by mass or more, more preferably 50 parts by mass or more, and for example, 100 parts by mass or less, preferably 85 parts by mass or less, more preferably 70 parts by mass or less, relative to 100 parts by mass of the photoacid generator.
- the one-component dental polymerizable material may contain a filler, if necessary.
- the filler may be any of the conventionally known fillers that can be used in dental materials.
- Specific examples of the filler include silica, silica alumina, alumina, alumina quartz, glass, titania, zirconia, and ytterbium fluoride.
- Examples of silica include fumed silica.
- the filler may be surface-treated with a silane coupling agent or the like to be made hydrophobic or hydrophilic.
- Fillers can be used alone or in combination of two or more types.
- a filler As a filler, a combination of silica and ytterbium fluoride is preferred.
- the filler content in the one-component dental polymeric material is, for example, 0.5% by mass or more, preferably 5% by mass or more, more preferably 15% by mass or more, even more preferably 30% by mass or more, and particularly preferably 50% by mass or more, and is, for example, 95% by mass or less, preferably 80% by mass or less, more preferably 65% by mass or less, and even more preferably 60% by mass or less.
- the content of the filler is, for example, 30 parts by mass or more, preferably 50 parts by mass or more, more preferably 100 parts by mass or more, and for example, 500 parts by mass or less, preferably 300 parts by mass or less, more preferably 200 parts by mass or less, per 100 parts by mass of the non-acidic monomer.
- the content of the filler is, for example, 1,000 parts by mass or more, preferably 2,000 parts by mass or more, more preferably 2,500 parts by mass or more, and for example, 7,000 parts by mass or less, preferably 4,000 parts by mass or less, more preferably 3,500 parts by mass or less, per 100 parts by mass of the photoacid generator.
- the one-component dental polymerizable material may contain a photosensitizer, if necessary.
- the photosensitizer transmits the energy it obtains by absorbing light to the photoacid generator, accelerating the decomposition of the photoacid generator.
- photosensitizers include ketone compounds, anthracene compounds, naphthalene compounds, thioxanthone compounds, and coumarin compounds.
- Ketone compounds include, for example, ⁇ -diketone compounds.
- ⁇ -diketone compounds include camphorquinone, benzil, diacetyl, acetylbenzoyl, 2,3-pentadione, 2,3-octadione, 4,4'-dimethoxybenzyl, 4,4'-oxybenzyl, 9,10-phenanthrenequinone, and acenaphthenequinone.
- anthracene compounds include 9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dimethoxyanthracene.
- Naphthalene compounds include, for example, 1,4-dimethoxynaphthalene and 1,4-diethoxynaphthalene.
- Photosensitizers can be used alone or in combination of two or more types.
- the photosensitizer is an anthracene compound.
- the proportion of the photosensitizer in the one-component dental polymeric material is, for example, 0.001% by mass or more, preferably 0.005% by mass or more, more preferably 0.01% by mass or more, and, for example, 10% by mass or less, preferably 5% by mass or less, more preferably 1% by mass or less.
- the content of the photosensitizer is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, more preferably 0.1 parts by mass or more, and for example, 5 parts by mass or less, preferably 3 parts by mass or less, more preferably 1 part by mass or less, per 100 parts by mass of the non-acidic monomer.
- the content of the photosensitizer is, for example, 1 part by mass or more, preferably 1.5 parts by mass or more, more preferably 2 parts by mass or more, and for example, 20 parts by mass or less, preferably 10 parts by mass or less, more preferably 5 parts by mass or less, per 100 parts by mass of the photoacid generator.
- the one-component dental polymerizable material may contain, as necessary, a polymerization inhibitor, a photopolymerization initiator, an acid amplifier, a thickener, a silane coupling agent, an ultraviolet absorbing agent, a fluorescent agent, a pigment, and a solvent.
- a photopolymerization initiator is a compound that is excited and starts polymerization when exposed to light such as visible light and/or ultraviolet light. Photopolymerization initiators do not include photoacid generators.
- photopolymerization initiators examples include ketone compounds and acylphosphine oxide compounds, with ketone compounds being preferred.
- Ketone compounds include, for example, ⁇ -diketone compounds.
- ⁇ -diketone compounds include camphorquinone, benzil, diacetyl, acetylbenzoyl, 2,3-pentadione, 2,3-octadione, 4,4'-dimethoxybenzyl, 4,4'-oxybenzyl, 9,10-phenanthrenequinone, and acenaphthenequinone, and preferably camphorquinone.
- polymerization inhibitors examples include dibutylhydroxytoluene (BHT) and 4-methoxyphenol (MeHQ), and preferably dibutylhydroxytoluene.
- the proportion of the polymerization inhibitor in the one-component dental polymerization material is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and, for example, 10% by mass or less, preferably 5% by mass or less, more preferably 1% by mass or less.
- the content of the polymerization inhibitor is, for example, 0.1 parts by mass or more, preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, and for example, 5 parts by mass or less, preferably 3 parts by mass or less, more preferably 2 parts by mass or less, per 100 parts by mass of the non-acidic monomer.
- the content of the polymerization inhibitor is, for example, 0.1 parts by mass or more, preferably 1 part by mass or more, more preferably 5 parts by mass or more, and for example, 70 parts by mass or less, preferably 50 parts by mass or less, more preferably 30 parts by mass or less, per 100 parts by mass of the photoacid generator.
- One-component dental polymeric materials can be applied to tooth structure alone or in combination with a pretreatment material.
- the photoacid generator decomposes, generating radicals and acid.
- the radicals generated from the photoacid generator photopolymerize nonacidic monomers.
- the acid generated from the photoacid generator dissolves transition metal compounds and generates transition metal ions.
- the generated transition metal ions react chemically with a reducing agent to generate radicals.
- the radicals generated by the chemical reaction polymerize the nonacidic monomers.
- the heat of polymerization generated by photopolymerization and chemical polymerization also causes decomposition of the photoacid generator, and polymerization progresses (frontal polymerization), even in deep areas where light does not directly reach.
- dental polymerizable materials polymerize nonacidic monomers during dental treatment.
- frontal polymerization occurs, allowing for a high cure depth.
- the transition metal compound is a solid in the one-component dental polymerizable material. Therefore, the reaction between the transition metal compound and the reducing agent in the one-component dental polymerizable material can be suppressed.
- the dental polymerizable material is a one-component dental polymerizable material.
- the dental polymerization material may be a multi-component dental polymerization material.
- multi-component dental polymerization materials include two-component dental polymerization materials.
- Two-component dental polymerization materials have, for example, component A and component B.
- Two-component dental polymerization materials are used, for example, by mixing components A and B.
- Two-component dental polymerization materials are also used, for example, by applying component A and then component B. If a two-component dental polymerization material has self-adhesive properties, it can be used by applying it directly to tooth structure.
- a two-component dental polymerization material does not have self-adhesive properties, it can be used in combination with a pretreatment material.
- At least one of components A and B contains a photoacid generator, a transition metal compound, and a reducing agent, and optionally contains a non-acidic monomer, a filler, a photosensitizer, and other additives.
- component B located on the surface that is irradiated with light contains a photoacid generator, and at least one of components A and B contains a transition metal compound and a reducing agent, and optionally a non-acidic monomer, a filler, a photosensitizer, and other additives.
- component A may contain a photoacid generator.
- the dental polymerizable material may contain no non-acidic monomers and no acidic monomers. In this case, the dental polymerizable material is used to polymerize the monomers.
- the dental polymeric material may not contain a filler.
- the dental polymeric material can be used as a dental coating material.
- UDMA [2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)]dimethacrylate
- TEGDMA triethylene glycol di(meth)acrylate
- IK-1 Photoacid generator (iodonium salt) manufactured by San-Apro Co., Ltd.
- DBA 9,10-dibutoxyanthracene
- CQ camphorquinone
- Cu(OH) 2 copper(II) hydroxide
- CaAA calcium ascorbate dihydrate
- BHT dibutylhydroxytoluene
- R812 fumed silica manufactured by Aerosil YbF 3 : ytterbium fluoride
- Example 1 the transition metal compound (Cu(OH) 2 ) was a solid in the one-part dental polymerizable material.
- the dental polymeric material of the present invention is suitable for use in dental treatment to fill missing teeth and to adhere prosthetic devices to missing teeth.
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- Dental Preparations (AREA)
Abstract
Ce matériau polymère destiné à être utilisé en dentisterie est utilisé, dans des traitements dentaires, pour polymériser un monomère non acide qui n'a pas de groupes acides mais qui a des groupes éthyléniquement insaturés. Le matériau polymère destiné à être utilisé en dentisterie contient un générateur de photoacide, un composé de métal de transition et un agent réducteur. Le composé de métal de transition est un solide dans le matériau polymère destiné à être utilisé en dentisterie et peut être dissous par l'acide généré lorsque le générateur de photoacide se décompose.
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WO2021251023A1 (fr) * | 2020-06-12 | 2021-12-16 | 株式会社トクヤマデンタル | Composition dentaire durcissable |
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JP2001158804A (ja) * | 1999-09-24 | 2001-06-12 | Tokuyama Corp | 重合触媒 |
JP2009102640A (ja) * | 2007-10-22 | 2009-05-14 | Heraeus Medical Gmbh | 自己硬化性プラスチックのための開始剤系、その使用および該開始剤系を含有する骨セメント組成物 |
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JP2021116346A (ja) * | 2020-01-24 | 2021-08-10 | 三井化学株式会社 | 重合開始剤、硬化性組成物調製用キット、硬化性組成物、硬化物及び歯科材料 |
JP2021128259A (ja) * | 2020-02-14 | 2021-09-02 | サンアプロ株式会社 | 感光性組成物 |
WO2021251023A1 (fr) * | 2020-06-12 | 2021-12-16 | 株式会社トクヤマデンタル | Composition dentaire durcissable |
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