CA2285317C - Ternary photoinitiator system for curing of epoxy/polyol resin compositions - Google Patents
Ternary photoinitiator system for curing of epoxy/polyol resin compositions Download PDFInfo
- Publication number
- CA2285317C CA2285317C CA002285317A CA2285317A CA2285317C CA 2285317 C CA2285317 C CA 2285317C CA 002285317 A CA002285317 A CA 002285317A CA 2285317 A CA2285317 A CA 2285317A CA 2285317 C CA2285317 C CA 2285317C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- composition
- aryl
- groups
- photoinitiator system
- 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.)
- Expired - Fee Related
Links
- 239000004593 Epoxy Substances 0.000 title description 47
- 229920005862 polyol Polymers 0.000 title description 27
- 150000003077 polyols Chemical class 0.000 title description 25
- 239000011342 resin composition Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 161
- -1 diphenyl iodonium hexafluoroantimonate Chemical compound 0.000 claims abstract description 101
- 239000000463 material Substances 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 53
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 44
- 239000003822 epoxy resin Substances 0.000 claims abstract description 41
- 229930006711 bornane-2,3-dione Natural products 0.000 claims abstract description 36
- 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 claims abstract description 35
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012086 standard solution Substances 0.000 claims abstract description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003479 dental cement Substances 0.000 claims abstract 3
- 239000011350 dental composite resin Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 239000000499 gel Substances 0.000 claims description 38
- 239000002131 composite material Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 13
- 150000002118 epoxides Chemical class 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000012955 diaryliodonium Substances 0.000 claims description 10
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 claims description 4
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 229910006069 SO3H Inorganic materials 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- SOLBSNQBVLAREX-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-2-hydroxy-2-phenylethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C(O)C1=CC=CC=C1 SOLBSNQBVLAREX-UHFFFAOYSA-N 0.000 claims description 3
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 3
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical compound C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000003384 imaging method Methods 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 claims description 2
- OAKFFVBGTSPYEG-UHFFFAOYSA-N (4-prop-2-enoyloxycyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1CCC(OC(=O)C=C)CC1 OAKFFVBGTSPYEG-UHFFFAOYSA-N 0.000 claims description 2
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HTWRFCRQSLVESJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCOC(=O)C(C)=C HTWRFCRQSLVESJ-UHFFFAOYSA-N 0.000 claims description 2
- GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- JYMNQRQQBJIMCV-UHFFFAOYSA-N 4-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C=C1 JYMNQRQQBJIMCV-UHFFFAOYSA-N 0.000 claims description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003082 abrasive agent Substances 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 229920002120 photoresistant polymer Polymers 0.000 claims description 2
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910000679 solder Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- GGRBZHPJKWFAFZ-UHFFFAOYSA-N 3,4-bis(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(OC(=O)C(C)=C)COC(=O)C(C)=C GGRBZHPJKWFAFZ-UHFFFAOYSA-N 0.000 claims 1
- 229940106691 bisphenol a Drugs 0.000 claims 1
- 238000001429 visible spectrum Methods 0.000 abstract description 2
- 239000000386 donor Substances 0.000 description 53
- 229920005989 resin Polymers 0.000 description 41
- 239000011347 resin Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- 239000000945 filler Substances 0.000 description 38
- 238000001723 curing Methods 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000003999 initiator Substances 0.000 description 17
- 239000005548 dental material Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000003607 modifier Substances 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000004809 Teflon Substances 0.000 description 10
- 229920006362 Teflon® Polymers 0.000 description 10
- 229940048053 acrylate Drugs 0.000 description 10
- 125000002091 cationic group Chemical group 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- 229920002799 BoPET Polymers 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 229920000909 polytetrahydrofuran Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000010453 quartz Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- LBCCPKFTHIBIKU-UHFFFAOYSA-N 3,4-Heptanedione Chemical compound CCCC(=O)C(=O)CC LBCCPKFTHIBIKU-UHFFFAOYSA-N 0.000 description 4
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XYZAPOXYXNIBEU-UHFFFAOYSA-N octane-4,5-dione Chemical compound CCCC(=O)C(=O)CCC XYZAPOXYXNIBEU-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- UDLBSRQHKWDKQA-UHFFFAOYSA-N acetyl acetate;sulfuric acid Chemical compound OS(O)(=O)=O.CC(=O)OC(C)=O UDLBSRQHKWDKQA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000000805 composite resin Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- BCQKUSCWNFMCKI-UHFFFAOYSA-M diphenyliodanium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 BCQKUSCWNFMCKI-UHFFFAOYSA-M 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 3
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 2
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-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
- 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 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 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
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 description 2
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000001018 xanthene dye Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-LDWIPMOCSA-N (+/-)-Camphorquinone Chemical compound C1C[C@@]2(C)C(=O)C(=O)[C@@H]1C2(C)C VNQXSTWCDUXYEZ-LDWIPMOCSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- FMYXOBBPXQZKKY-UHFFFAOYSA-N 1,2-bis(4-hydroxyphenyl)ethane-1,2-dione Chemical compound C1=CC(O)=CC=C1C(=O)C(=O)C1=CC=C(O)C=C1 FMYXOBBPXQZKKY-UHFFFAOYSA-N 0.000 description 1
- BWSIKJKXQWLTLS-UHFFFAOYSA-N 1,2-dimethoxyanthracene Chemical compound C1=CC=CC2=CC3=C(OC)C(OC)=CC=C3C=C21 BWSIKJKXQWLTLS-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- ZKSVYBRJSMBDMV-UHFFFAOYSA-N 1,3-diphenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C=CC=CC=2)O1 ZKSVYBRJSMBDMV-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- JBCVRTMLHPWTJI-UHFFFAOYSA-N 1-(10-acetylanthracen-9-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(C=CC=C3)C3=C(C(C)=O)C2=C1 JBCVRTMLHPWTJI-UHFFFAOYSA-N 0.000 description 1
- LVQFKRXRTXCQCZ-UHFFFAOYSA-N 1-(2-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1C(C)=O LVQFKRXRTXCQCZ-UHFFFAOYSA-N 0.000 description 1
- LKENZCXDBCULOT-UHFFFAOYSA-N 1-(2-hydroxyphenyl)-2-phenylethane-1,2-dione Chemical compound OC1=CC=CC=C1C(=O)C(=O)C1=CC=CC=C1 LKENZCXDBCULOT-UHFFFAOYSA-N 0.000 description 1
- CWILMKDSVMROHT-UHFFFAOYSA-N 1-(2-phenanthrenyl)ethanone Chemical compound C1=CC=C2C3=CC=C(C(=O)C)C=C3C=CC2=C1 CWILMKDSVMROHT-UHFFFAOYSA-N 0.000 description 1
- VCHOFVSNWYPAEF-UHFFFAOYSA-N 1-(3-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C(C)=O)=C1 VCHOFVSNWYPAEF-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- FQORHEMAUBKTGC-UHFFFAOYSA-N 1-(8-acetylnaphthalen-1-yl)ethanone Chemical compound C1=CC(C(C)=O)=C2C(C(=O)C)=CC=CC2=C1 FQORHEMAUBKTGC-UHFFFAOYSA-N 0.000 description 1
- NXXNVJDXUHMAHU-UHFFFAOYSA-N 1-anthracen-9-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=C(C=CC=C3)C3=CC2=C1 NXXNVJDXUHMAHU-UHFFFAOYSA-N 0.000 description 1
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
- JKVNPRNAHRHQDD-UHFFFAOYSA-N 1-phenanthren-3-ylethanone Chemical compound C1=CC=C2C3=CC(C(=O)C)=CC=C3C=CC2=C1 JKVNPRNAHRHQDD-UHFFFAOYSA-N 0.000 description 1
- UIFAWZBYTTXSOG-UHFFFAOYSA-N 1-phenanthren-9-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC3=CC=CC=C3C2=C1 UIFAWZBYTTXSOG-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical compound CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 1
- AJKXDPSHWRTFOZ-UHFFFAOYSA-N 2-ethylhexane-1,6-diol Chemical compound CCC(CO)CCCCO AJKXDPSHWRTFOZ-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- CNCFLCLXJBPMIR-UHFFFAOYSA-N 2-fluorofluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC(F)=CC=C3C2=C1 CNCFLCLXJBPMIR-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- OFUVUDZHGRTQMW-UHFFFAOYSA-N 3,3,8,8-tetramethylcyclooctane-1,2-dione Chemical compound CC1(C)CCCCC(C)(C)C(=O)C1=O OFUVUDZHGRTQMW-UHFFFAOYSA-N 0.000 description 1
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 1
- CSPIFKKOBWYOEX-UHFFFAOYSA-N 3-acetylcoumarin Chemical compound C1=CC=C2OC(=O)C(C(=O)C)=CC2=C1 CSPIFKKOBWYOEX-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- ZDTNHRWWURISAA-UHFFFAOYSA-N 4',5'-dibromo-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C(Br)=C1OC1=C(Br)C(O)=CC=C21 ZDTNHRWWURISAA-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-M 4-(dimethylamino)benzoate Chemical compound CN(C)C1=CC=C(C([O-])=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-M 0.000 description 1
- UTHHKUBZIBBOIT-UHFFFAOYSA-N 4-methyl-2-[(4-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl]-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic acid Chemical compound CC1CC2OC2C(CC2CC3OC3CC2C)=C1C(O)=O UTHHKUBZIBBOIT-UHFFFAOYSA-N 0.000 description 1
- UXQFGCIAJSWBTO-UHFFFAOYSA-N 5-methyl-4-[(5-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl]-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1CC2OC2C(C)C1(C(O)=O)CC1CCC2OC2C1C UXQFGCIAJSWBTO-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- PTEZHEBXZIBKNA-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane;2-tetradecyloxirane Chemical compound C1CCCC2OC21C=C.CCCCCCCCCCCCCCC1CO1 PTEZHEBXZIBKNA-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- ALJHHTHBYJROOG-UHFFFAOYSA-N 7-(dimethylamino)phenothiazin-3-one Chemical compound C1=CC(=O)C=C2SC3=CC(N(C)C)=CC=C3N=C21 ALJHHTHBYJROOG-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- AOYQDLJWKKUFEG-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]hept-4-ene-4-carboxylate Chemical compound C=1C2OC2CCC=1C(=O)OCC1CC2OC2CC1 AOYQDLJWKKUFEG-UHFFFAOYSA-N 0.000 description 1
- FKDIWXZNKAZCBY-UHFFFAOYSA-N 9,10-dichloroanthracene Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=C(Cl)C2=C1 FKDIWXZNKAZCBY-UHFFFAOYSA-N 0.000 description 1
- GJNKQJAJXSUJBO-UHFFFAOYSA-N 9,10-diethoxyanthracene Chemical compound C1=CC=C2C(OCC)=C(C=CC=C3)C3=C(OCC)C2=C1 GJNKQJAJXSUJBO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OHNVYUFGHVIYEF-UHFFFAOYSA-N 9,9-bis[4-(oxiran-2-ylmethoxy)phenyl]-2h-fluoren-1-one Chemical compound O=C1CC=CC(C2=CC=CC=C22)=C1C2(C=1C=CC(OCC2OC2)=CC=1)C(C=C1)=CC=C1OCC1CO1 OHNVYUFGHVIYEF-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 229910002020 Aerosil® OX 50 Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910001312 Amalgam (dentistry) Inorganic materials 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- FYYIUODUDSPAJQ-XVBQNVSMSA-N [(1S,6R)-7-oxabicyclo[4.1.0]heptan-3-yl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CC[C@H]2O[C@H]2C1 FYYIUODUDSPAJQ-XVBQNVSMSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 239000000999 acridine dye Substances 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229940000489 arsenate Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- PIPBVABVQJZSAB-UHFFFAOYSA-N bis(ethenyl) benzene-1,2-dicarboxylate Chemical compound C=COC(=O)C1=CC=CC=C1C(=O)OC=C PIPBVABVQJZSAB-UHFFFAOYSA-N 0.000 description 1
- AJCHRUXIDGEWDK-UHFFFAOYSA-N bis(ethenyl) butanedioate Chemical compound C=COC(=O)CCC(=O)OC=C AJCHRUXIDGEWDK-UHFFFAOYSA-N 0.000 description 1
- JZQAAQZDDMEFGZ-UHFFFAOYSA-N bis(ethenyl) hexanedioate Chemical compound C=COC(=O)CCCCC(=O)OC=C JZQAAQZDDMEFGZ-UHFFFAOYSA-N 0.000 description 1
- HMKCSFHWMJHMTG-UHFFFAOYSA-N bis(furan-2-yl)methanone Chemical compound C=1C=COC=1C(=O)C1=CC=CO1 HMKCSFHWMJHMTG-UHFFFAOYSA-N 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229940075894 denatured ethanol Drugs 0.000 description 1
- 239000000448 dental amalgam Substances 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 210000004513 dentition Anatomy 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- QPOWUYJWCJRLEE-UHFFFAOYSA-N dipyridin-2-ylmethanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=N1 QPOWUYJWCJRLEE-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical compound C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UKZQEOHHLOYJLY-UHFFFAOYSA-M ethyl eosin Chemical compound [K+].CCOC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 UKZQEOHHLOYJLY-UHFFFAOYSA-M 0.000 description 1
- LSGWSXRILNPXKJ-UHFFFAOYSA-N ethyl oxirane-2-carboxylate Chemical compound CCOC(=O)C1CO1 LSGWSXRILNPXKJ-UHFFFAOYSA-N 0.000 description 1
- ZTFPVUVWTIJYHK-UHFFFAOYSA-N ethyl prop-2-enoate;methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C=C.COC(=O)C(C)=C.CC(=C)C(=O)OCC1CO1 ZTFPVUVWTIJYHK-UHFFFAOYSA-N 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- PWVDFPINYKVAFM-UHFFFAOYSA-N fluoren-4-one Chemical compound C1=CC=CC2=C3C(=O)C=CC=C3C=C21 PWVDFPINYKVAFM-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000001021 fluorone dye Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000003052 fractional factorial design Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- FBTOLGZVPDIVPS-UHFFFAOYSA-N iodo prop-2-enoate Chemical compound IOC(=O)C=C FBTOLGZVPDIVPS-UHFFFAOYSA-N 0.000 description 1
- JLUCVDLESNBWQK-UHFFFAOYSA-N iodyl hydrogen sulfate Chemical compound I(=O)(=O)OS(O)(=O)=O JLUCVDLESNBWQK-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- KOARAHKGQSHYGJ-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl prop-2-enoate Chemical compound COC(=O)C(C)=C.C=CC(=O)OCC1CO1 KOARAHKGQSHYGJ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- LOTWRKOXHCMWDB-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)benzamide Chemical compound OCCN(CCO)C(=O)C1=CC=CC=C1 LOTWRKOXHCMWDB-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- LUUFSCNUZAYHAT-UHFFFAOYSA-N octadecane-1,18-diol Chemical compound OCCCCCCCCCCCCCCCCCCO LUUFSCNUZAYHAT-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- YPNZYYWORCABPU-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C(=O)OCC1CO1 YPNZYYWORCABPU-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 239000001415 potassium malate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical group C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 239000011043 treated quartz Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0037—Production of three-dimensional images
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/908—Dental utility
Landscapes
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/840,093 US5998495A (en) | 1997-04-11 | 1997-04-11 | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US08/840093 | 1997-04-11 | ||
| PCT/US1998/004458 WO1998047047A1 (en) | 1997-04-11 | 1998-03-06 | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2285317A1 CA2285317A1 (en) | 1998-10-22 |
| CA2285317C true CA2285317C (en) | 2009-09-08 |
Family
ID=25281434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002285317A Expired - Fee Related CA2285317C (en) | 1997-04-11 | 1998-03-06 | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5998495A (enExample) |
| EP (1) | EP0974078B1 (enExample) |
| JP (1) | JP4009754B2 (enExample) |
| KR (1) | KR20010006281A (enExample) |
| CN (1) | CN1252137A (enExample) |
| AU (1) | AU744316B2 (enExample) |
| BR (1) | BR9807971A (enExample) |
| CA (1) | CA2285317C (enExample) |
| DE (1) | DE69815520T2 (enExample) |
| NO (1) | NO314041B1 (enExample) |
| WO (1) | WO1998047047A1 (enExample) |
Families Citing this family (156)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5998495A (en) * | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US5980253A (en) * | 1998-01-12 | 1999-11-09 | 3M Innovative Properties Company | Process for treating hard tissues |
| US6306926B1 (en) * | 1998-10-07 | 2001-10-23 | 3M Innovative Properties Company | Radiopaque cationically polymerizable compositions comprising a radiopacifying filler, and method for polymerizing same |
| WO2000026973A1 (en) | 1998-11-02 | 2000-05-11 | Presstek, Inc. | Transparent conductive oxides for plastic flat panel displays |
| WO2000040206A1 (en) * | 1999-01-08 | 2000-07-13 | 3M Innovative Properties Company | Dental mill blanks |
| US6458865B2 (en) * | 1999-01-15 | 2002-10-01 | Curators Of The University Of Missouri | Photopolymerizable vinyl ether based monomeric formulations and polymerizable compositions which may include certain novel spiroorthocarbonates |
| EP1029880A1 (de) * | 1999-02-17 | 2000-08-23 | LSP Dental Chemistry AG | Epoxidverbindungen enthaltende Zusammensetzung für zahnmedizinische und/oder zahntechnische Anwendungen |
| EP1182985A1 (en) | 1999-06-04 | 2002-03-06 | Denfotex Ltd. | Method and apparatus for filling a dental root canal |
| DE19937091A1 (de) | 1999-08-06 | 2001-02-22 | Espe Dental Ag | Adhäsivsysteme II |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| DE19961355A1 (de) * | 1999-12-17 | 2001-06-21 | S & C Polymer Silicon & Compos | Photoinitiatorsystem mit Titanocen-Initiatoren |
| US6439698B1 (en) * | 2000-01-14 | 2002-08-27 | Lexmark International, Inc | Dual curable encapsulating material |
| US6444725B1 (en) | 2000-01-21 | 2002-09-03 | 3M Innovative Properties Company | Color-changing dental compositions |
| US6610759B1 (en) | 2000-03-06 | 2003-08-26 | Curators Of The University Of Missouri | Cationically polymerizable adhesive composition containing an acidic component and methods and materials employing same |
| DE60021710T2 (de) * | 2000-06-07 | 2006-06-01 | Sicpa Holding S.A. | Durch UV-Strahlung härtbare Zusammensetzung |
| WO2001096915A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Microfabrication of organic optical elements |
| US7381516B2 (en) * | 2002-10-02 | 2008-06-03 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| US6852766B1 (en) * | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| US7005229B2 (en) * | 2002-10-02 | 2006-02-28 | 3M Innovative Properties Company | Multiphoton photosensitization method |
| AU2001268465A1 (en) | 2000-06-15 | 2001-12-24 | 3M Innovative Properties Company | Multiphoton curing to provide encapsulated optical elements |
| US7118845B2 (en) * | 2000-06-15 | 2006-10-10 | 3M Innovative Properties Company | Multiphoton photochemical process and articles preparable thereby |
| US7060419B2 (en) * | 2000-06-15 | 2006-06-13 | 3M Innovative Properties Company | Process for producing microfluidic articles |
| US7265161B2 (en) * | 2002-10-02 | 2007-09-04 | 3M Innovative Properties Company | Multi-photon reactive compositions with inorganic particles and method for fabricating structures |
| US7790353B2 (en) | 2000-06-15 | 2010-09-07 | 3M Innovative Properties Company | Multidirectional photoreactive absorption method |
| DE60139620D1 (de) | 2000-06-15 | 2009-10-01 | 3M Innovative Properties Co | Methode und gerät zur erzielung wiederholter multiphotonabsorption |
| WO2001096952A2 (en) * | 2000-06-15 | 2001-12-20 | 3M Innovative Properties Company | Multicolor imaging using multiphoton photochemical processes |
| GB0019251D0 (en) * | 2000-08-04 | 2000-09-27 | Lintfield Limited | Photoinitiated reactions |
| US6528555B1 (en) * | 2000-10-12 | 2003-03-04 | 3M Innovative Properties Company | Adhesive for use in the oral environment having color-changing capabilities |
| US7101942B2 (en) | 2001-01-19 | 2006-09-05 | Ivoclar Vivadent Ag | Dental materials based on metal oxide clusters |
| DE10107985C1 (de) | 2001-02-19 | 2002-04-18 | 3M Espe Ag | Polymerisierbare Zubereitungen auf der Basis von Siliziumverbindungen mit aliphatischen und cycloaliphatischen Epoxidgruppen und deren Verwendung |
| US7241856B2 (en) * | 2003-06-02 | 2007-07-10 | Pentron Clinical Technologies Llc | Dental resins, dental composite materials, and method of manufacture thereof |
| US7470728B2 (en) * | 2001-05-01 | 2008-12-30 | Pentron Clinical Technologies Llc | Dental glazes and method of manufacture and use thereof |
| US7589132B2 (en) * | 2001-05-01 | 2009-09-15 | Pentron Clinical Technologies, Llc | Dental resins, dental composite materials, and method of manufacture thereof |
| US7160941B2 (en) * | 2001-05-01 | 2007-01-09 | Pentron Clinical Technologies, Llc | Dental composite materials and method of manufacture thereof |
| US20040012872A1 (en) * | 2001-06-14 | 2004-01-22 | Fleming Patrick R | Multiphoton absorption method using patterned light |
| US6750266B2 (en) * | 2001-12-28 | 2004-06-15 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| US6765036B2 (en) * | 2002-01-15 | 2004-07-20 | 3M Innovative Properties Company | Ternary photoinitiator system for cationically polymerizable resins |
| JP4748938B2 (ja) | 2002-01-31 | 2011-08-17 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科ペースト、歯科物品、および方法 |
| US20050164118A1 (en) * | 2002-01-31 | 2005-07-28 | Claus Barholm -Hansen | Method of joining a workpiece and a microstructure light exposure |
| EP1483310A1 (en) * | 2002-03-08 | 2004-12-08 | Rensselaer Polytechnic Institute | Accelerators for cationic photopolymerization |
| US7008229B2 (en) * | 2002-04-12 | 2006-03-07 | 3M Innovative Properties Company | Stainless steel dental crowns with a polyester/epoxy coating |
| JP4276407B2 (ja) | 2002-05-08 | 2009-06-10 | ヘンケル コーポレイション | 光カチオン硬化型エポキシ樹脂組成物 |
| JP4485117B2 (ja) * | 2002-06-27 | 2010-06-16 | 日東電工株式会社 | 保護剥離用フィルム |
| US7134875B2 (en) * | 2002-06-28 | 2006-11-14 | 3M Innovative Properties Company | Processes for forming dental materials and device |
| US6773261B2 (en) * | 2002-06-28 | 2004-08-10 | 3M Innovative Properties Company | Processes for forming dental materials |
| US7232650B2 (en) * | 2002-10-02 | 2007-06-19 | 3M Innovative Properties Company | Planar inorganic device |
| US20030155667A1 (en) * | 2002-12-12 | 2003-08-21 | Devoe Robert J | Method for making or adding structures to an article |
| DE10261241A1 (de) * | 2002-12-20 | 2004-07-15 | 3M Espe Ag | Dentalmaterial mit bakteriostatischen und/oder bakteriziden Substanzen |
| US20040120901A1 (en) * | 2002-12-20 | 2004-06-24 | Dong Wu | Dental compositions including enzymes and methods |
| US20040122126A1 (en) * | 2002-12-20 | 2004-06-24 | Dong Wu | Free-radical initiator systems containing enzymes, compositions, and methods |
| US20040206932A1 (en) * | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
| TWI236374B (en) * | 2003-02-13 | 2005-07-21 | Univ Nat Taiwan | Light curable epoxy nano composite for dental restorative material |
| US6986662B2 (en) | 2003-04-09 | 2006-01-17 | Ultradent Products, Inc. | Adhesive endodontic cones and related methods |
| US20040219303A1 (en) * | 2003-04-30 | 2004-11-04 | Klaus Wissing | Process for multi-layer coating of substrates |
| EP1498098B1 (en) * | 2003-07-14 | 2006-05-03 | 3M Espe Ag | Adhesive composition with decreased polarity upon polymerization |
| AU2004266623B8 (en) * | 2003-08-12 | 2011-10-27 | 3M Deutschland Gmbh | Self-etching dental compositions and methods |
| US7250452B2 (en) * | 2003-09-26 | 2007-07-31 | 3M Innovative Properties Company | Dental compositions and methods with arylsulfinate salts |
| US7030169B2 (en) * | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US7064152B2 (en) * | 2003-09-26 | 2006-06-20 | 3M Innovative Properties Company | Arylsulfinate salts in photoinitiator systems for polymerization reactions |
| US7026367B2 (en) * | 2003-09-26 | 2006-04-11 | 3M Innovative Properties Company | Photoiniators having triarylsulfonium and arylsulfinate ions |
| JP4581401B2 (ja) * | 2003-12-26 | 2010-11-17 | コニカミノルタエムジー株式会社 | 活性光線硬化型インクジェットインク組成物、活性光線硬化型インクジェットインクセットと、それを用いた画像形成方法及びインクジェット記録装置 |
| AU2003304694A1 (en) * | 2003-12-05 | 2005-08-12 | 3M Innovative Properties Company | Process for producing photonic crystals and controlled defects therein |
| US20050124712A1 (en) * | 2003-12-05 | 2005-06-09 | 3M Innovative Properties Company | Process for producing photonic crystals |
| US7166008B2 (en) * | 2003-12-22 | 2007-01-23 | 3M Innovative Properties Company | Method of curing using an electroluminescent light |
| JP5214242B2 (ja) * | 2004-07-08 | 2013-06-19 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用の方法、組成物、および酸感受性色素を含むキット |
| US20080085494A1 (en) * | 2004-07-14 | 2008-04-10 | Mader Roger M | Dental Compositions Containing Oxirane Monomers |
| AU2004321435A1 (en) | 2004-07-14 | 2006-01-19 | 3M Espe Ag | Dental composition containing an epoxy functional carbosilane compound |
| CN101018536A (zh) * | 2004-07-14 | 2007-08-15 | 3M埃斯佩股份公司 | 含环氧官能可聚合化合物的牙科组合物 |
| ATE424179T1 (de) | 2004-07-14 | 2009-03-15 | 3M Espe Ag | Dentalzusammensetzung mit ungesättigten halogenierten arylalkylether-bestandteilen |
| US8722760B2 (en) * | 2004-08-11 | 2014-05-13 | 3M Innovative Properties Company | Self-adhesive compositions including a plurality of acidic compounds |
| ATE439116T1 (de) * | 2004-09-24 | 2009-08-15 | 3M Espe Ag | Dentalklebstoffzusammensetzung |
| EP1811942B1 (en) | 2004-11-16 | 2011-10-05 | 3M Innovative Properties Company | Dental compositions with calcium phosphorus releasing glass |
| ATE480214T1 (de) | 2004-11-16 | 2010-09-15 | 3M Innovative Properties Co | Dentalfüllstoffe, verfahren, zusammensetzungen mit einem caseinat |
| US20060205838A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Hardenable antimicrobial dental compositions and methods |
| US20060204452A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Antimicrobial film-forming dental compositions and methods |
| US7571979B2 (en) * | 2005-09-30 | 2009-08-11 | Lexmark International, Inc. | Thick film layers and methods relating thereto |
| EP1787627A1 (en) * | 2005-11-17 | 2007-05-23 | 3M Innovative Properties Company | Anti-microbial dental impression material |
| US20070142498A1 (en) * | 2005-12-20 | 2007-06-21 | Brennan Joan V | Dental compositions including thermally responsive additives, and the use thereof |
| US7776940B2 (en) * | 2005-12-20 | 2010-08-17 | 3M Innovative Properties Company | Methods for reducing bond strengths, dental compositions, and the use thereof |
| US7896650B2 (en) * | 2005-12-20 | 2011-03-01 | 3M Innovative Properties Company | Dental compositions including radiation-to-heat converters, and the use thereof |
| US8026296B2 (en) | 2005-12-20 | 2011-09-27 | 3M Innovative Properties Company | Dental compositions including a thermally labile component, and the use thereof |
| JP4880701B2 (ja) * | 2005-12-21 | 2012-02-22 | スリーエム イノベイティブ プロパティズ カンパニー | 多光子硬化反応性組成物を処理するための方法及び装置 |
| US7583444B1 (en) * | 2005-12-21 | 2009-09-01 | 3M Innovative Properties Company | Process for making microlens arrays and masterforms |
| US9993393B2 (en) | 2005-12-29 | 2018-06-12 | 3M Innovative Properties Company | Dental compositions and initiator systems with polycyclic aromatic component |
| EP1968528B1 (en) * | 2005-12-29 | 2016-02-17 | 3M Innovative Properties Company | Dental compositions with surface-treated filler for shelf stability |
| CN101351183A (zh) * | 2005-12-29 | 2009-01-21 | 3M创新有限公司 | 包含水清除剂的牙科用组合物 |
| US8858807B2 (en) * | 2006-03-24 | 2014-10-14 | 3M Innovative Properties Company | Process for making microneedles, microneedle arrays, masters, and replication tools |
| EP1849449A1 (en) * | 2006-04-26 | 2007-10-31 | 3M Innovative Properties Company | Filler containing composition and process for production and use thereof |
| CN101448632B (zh) * | 2006-05-18 | 2012-12-12 | 3M创新有限公司 | 用于制备具有提取结构的光导的方法以及由此方法生产的光导 |
| EP2377507B1 (en) | 2006-09-13 | 2013-04-24 | 3M Innovative Properties Company | Dental compositions including organogelators, products, and methods |
| JP5168860B2 (ja) | 2006-09-14 | 2013-03-27 | 株式会社スリーボンド | 光重合性組成物 |
| CN100584301C (zh) * | 2006-10-04 | 2010-01-27 | 中国科学院长春应用化学研究所 | 一种可见光固化纳米复合树脂牙体修复材料及制备方法 |
| US9539065B2 (en) | 2006-10-23 | 2017-01-10 | 3M Innovative Properties Company | Assemblies, methods, and kits including a compressible material |
| US20080096150A1 (en) | 2006-10-23 | 2008-04-24 | 3M Innovative Properties Company | Dental articles, methods, and kits including a compressible material |
| WO2008053552A1 (fr) * | 2006-11-01 | 2008-05-08 | Fujitsu Limited | Appareil de communication sans fil et procédé de communication sans fil |
| JP5507256B2 (ja) | 2006-12-13 | 2014-05-28 | スリーエム イノベイティブ プロパティズ カンパニー | 酸性成分及び光退色性染料を有する歯科用組成物の使用方法 |
| CN101209228B (zh) * | 2006-12-27 | 2010-11-10 | 华东理工大学 | 抗菌牙科修复材料及其制备方法 |
| US8647426B2 (en) | 2006-12-28 | 2014-02-11 | 3M Innovative Properties Company | Dental filler and methods |
| WO2008083067A2 (en) * | 2006-12-28 | 2008-07-10 | 3M Innovative Properties Company | Dental compositions with natural tooth fluorescence |
| US20100021869A1 (en) * | 2006-12-28 | 2010-01-28 | Abuelyaman Ahmed S | (meth)acryloyl-containing materials, compositions, and methods |
| KR20100080785A (ko) | 2007-09-06 | 2010-07-12 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 광 출력의 영역 제어를 제공하는 광 추출 구조물을 갖는 도광체 |
| US9102083B2 (en) | 2007-09-06 | 2015-08-11 | 3M Innovative Properties Company | Methods of forming molds and methods of forming articles using said molds |
| EP2203144A2 (en) | 2007-10-01 | 2010-07-07 | 3M Innovative Properties Company | Orthodontic composition with polymeric fillers |
| WO2009048808A1 (en) * | 2007-10-11 | 2009-04-16 | 3M Innovative Properties Company | Chromatic confocal sensor |
| CN102112097B (zh) * | 2007-11-01 | 2013-08-07 | 3M创新有限公司 | 牙科组合物以及具有颜色稳定的胺电子供体的引发剂系统 |
| JP5524856B2 (ja) * | 2007-12-12 | 2014-06-18 | スリーエム イノベイティブ プロパティズ カンパニー | エッジ明瞭性が向上した構造の製造方法 |
| EP2229130A2 (en) * | 2007-12-13 | 2010-09-22 | 3M Innovative Properties Company | Remineralizing compositions and methods |
| JP5801558B2 (ja) * | 2008-02-26 | 2015-10-28 | スリーエム イノベイティブ プロパティズ カンパニー | 多光子露光システム |
| EP2133063A1 (en) | 2008-06-10 | 2009-12-16 | 3M Innovative Properties Company | Initiator system with biphenylene derivates, method of production and use thereof |
| EP2133064A1 (en) | 2008-06-10 | 2009-12-16 | 3M Innovative Properties Company | Initiator system containing a diarylalkylamine derivate, hardenable composition and use thereof |
| US8883948B2 (en) * | 2008-07-01 | 2014-11-11 | The Regents Of The University Of Colorado | Methods for extensive dark curing based on visible-light initiated, controlled radical polymerization |
| WO2010002725A2 (en) * | 2008-07-03 | 2010-01-07 | 3M Innovative Properties Company | Fixed abrasive particles and articles made therefrom |
| WO2010027676A2 (en) * | 2008-09-04 | 2010-03-11 | 3M Innovative Properties Company | Dental composition comprising biphenyl di(meth)acrylate monomer |
| EP2341885A2 (en) * | 2008-09-30 | 2011-07-13 | 3M Innovative Properties Company | Orthodontic composition with heat modified minerals |
| WO2010048067A2 (en) * | 2008-10-22 | 2010-04-29 | 3M Innovative Properties Company | Dental composition comprising biphenyl di(meth)acrylate monomer comprising urethane moieties |
| CN102301277B (zh) | 2008-12-05 | 2013-07-17 | 3M创新有限公司 | 使用非线性热聚合的三维制品 |
| US8790707B2 (en) * | 2008-12-11 | 2014-07-29 | 3M Innovative Properties Company | Surface-treated calcium phosphate particles suitable for oral care and dental compositions |
| EP2419243A1 (en) * | 2009-04-17 | 2012-02-22 | 3M Innovative Properties Company | Metal particle transfer article, metal modified substrate, and method of making and using the same |
| US8492454B2 (en) | 2009-10-05 | 2013-07-23 | Creative Nail Design, Inc. | Removable color layer for artificial nail coatings and methods therefore |
| US8541482B2 (en) | 2009-10-05 | 2013-09-24 | Creative Nail Design, Inc. | Removable multilayer nail coating system and methods therefore |
| US8263677B2 (en) | 2009-09-08 | 2012-09-11 | Creative Nail Design, Inc. | Removable color gel basecoat for artificial nail coatings and methods therefore |
| GB2476976A (en) | 2010-01-18 | 2011-07-20 | Lintfield Ltd | Protected aryl ketones and their use as photoinitiators |
| EP2412361A1 (en) | 2010-07-29 | 2012-02-01 | 3M Innovative Properties Company | Kit of parts, method of producing and use thereof |
| CN103281986B (zh) | 2010-12-30 | 2016-08-17 | 3M创新有限公司 | 包括可压缩材料的可粘合牙科用组件和方法 |
| KR101971745B1 (ko) | 2011-02-02 | 2019-04-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 노즐 및 그 제조 방법 |
| EP2683350A4 (en) | 2011-03-07 | 2015-08-05 | Creative Nail Design Inc | UV CURABLE NAILS COSMETIC COATING COMPOSITIONS AND RELATED METHODS |
| US20140017637A1 (en) | 2011-03-24 | 2014-01-16 | 3M Iinnovative Properties Company | Dental adhesive comprising a coated polymeric component |
| WO2012170204A1 (en) | 2011-06-08 | 2012-12-13 | 3M Innovative Properties Company | Photoresists containing polymer-tethered nanoparticles |
| KR101377840B1 (ko) * | 2011-10-18 | 2014-03-26 | (주)엘지하우시스 | 입자 프리징이 없는 전자종이용 접착 필름 형성용 조성물 및 이에 의해 제조된 접착 필름 |
| WO2015050751A1 (en) | 2013-10-02 | 2015-04-09 | 3M Innovative Properties Company | Articles and methods comprising polyacrylate primer with nitrogen-containing polymer |
| CN105593323B (zh) | 2013-10-02 | 2018-11-09 | 3M创新有限公司 | 包含聚丙烯酸酯压敏底漆以及含聚丙烯酸酯组分的粘合剂的制品 |
| KR102267204B1 (ko) | 2013-10-02 | 2021-06-22 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 제1 미세구조화 층 및 코팅을 포함하는 미세구조화 확산기, 광학 적층체, 및 방법 |
| EP2923689B1 (en) * | 2014-03-27 | 2020-03-18 | DENTSPLY DETREY GmbH | Dental composition |
| KR20170024114A (ko) | 2014-07-10 | 2017-03-06 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 2성분 자가-접착성 치과용 조성물, 이의 제조 방법 및 용도 |
| EP3386462B1 (en) | 2015-12-08 | 2024-10-23 | Solventum Intellectual Properties Company | Two-component self-adhesive dental composition, storage stable initiator system, and use thereof |
| JP2019532165A (ja) | 2016-09-14 | 2019-11-07 | スリーエム イノベイティブ プロパティズ カンパニー | 速硬化性光学接着剤 |
| US11160733B2 (en) | 2017-05-15 | 2021-11-02 | 3M Innovative Properties Company | Dental adhesive composition, preparation and use thereof |
| EP3706708B1 (en) | 2017-11-08 | 2022-01-12 | 3M Innovative Properties Company | Radiopaque dental composition |
| EP3501837A1 (en) * | 2017-12-21 | 2019-06-26 | Université de Haute Alsace | Thermal amplification of free radical polymerization induced by red to near-infrared irradiation |
| CN108403443A (zh) * | 2018-02-27 | 2018-08-17 | 苏州凌科特新材料有限公司 | 一种牙科粘合剂及其制备方法 |
| CN112638606A (zh) | 2018-08-31 | 2021-04-09 | 3M创新有限公司 | 用于制备非氧化物陶瓷制品以及气凝胶、干凝胶和多孔陶瓷制品的叠层制造方法 |
| EP3628697A1 (en) * | 2018-09-27 | 2020-04-01 | Université de Haute Alsace | Ultrafast cyclic ether-amine photopolyaddition and uses thereof |
| WO2020100041A1 (en) | 2018-11-14 | 2020-05-22 | 3M Innovative Properties Company | Storage stable two-component dual cure dental composition |
| US20220380260A1 (en) | 2019-08-06 | 2022-12-01 | 3M Innovative Properties Company | Continuous Additive Manufacturing Method for Making Ceramic Articles, and Ceramic Articles |
| WO2021124114A1 (en) | 2019-12-18 | 2021-06-24 | 3M Innovative Properties Company | Composition including unsaturated polyester resin, epoxy resin, and photoinitiator and method of using the same |
| EP4106710A1 (en) | 2020-02-19 | 2022-12-28 | 3M Innovative Properties Company | Ascorbic acid component for use in a method of treating the surface of a prepared tooth |
| JP7473996B2 (ja) * | 2020-08-07 | 2024-04-24 | 株式会社トクヤマデンタル | 歯科用硬化性組成物 |
| WO2022136969A1 (en) | 2020-12-23 | 2022-06-30 | 3M Innovative Properties Company | Methods of making articles including inkjet printing sols containing metal oxide nanoparticles |
| EP4288489B1 (en) * | 2021-02-03 | 2025-11-05 | Arkema, Inc. | Crosslinkable acrylic-modified epoxy coating composition |
| US12311037B2 (en) | 2022-04-26 | 2025-05-27 | Solventum Intellectual Properties Company | Dental composition containing a resorcinol or catechol moiety containing component and use thereof |
| PL441956A1 (pl) * | 2022-08-07 | 2024-02-12 | Politechnika Krakowska im.Tadeusza Kościuszki | Nowe sole jodoniowe, sposób wytwarzania nowych soli jodoniowych, zastosowania nowych soli jodoniowych, nowe kompozyty fotoutwardzalne przeznaczone na wypełnienia stomatologiczne, sposób wytwarzania nowych kompozytów fotoutwardzalnych przeznaczonych na wypełnienia stomatologiczne, nowe dwuskładnikowe systemy fotoinicjujące, nowe pochodne benzenu i zastosowanie pochodnych benzenu |
| PL441957A1 (pl) * | 2022-08-07 | 2024-02-12 | Politechnika Krakowska im.Tadeusza Kościuszki | Nowe sole jodoniowe, sposób wytwarzania nowych soli jodoniowych, zastosowania nowych soli jodoniowych, nowe kompozyty fotoutwardzalne przeznaczone na wypełnienia stomatologiczne, sposób wytwarzania nowych kompozytów fotoutwardzalnych przeznaczonych na wypełnienia stomatologiczne, nowe dwuskładnikowe systemy fotoinicjujące, nowe pochodne bifenylu i zastosowanie pochodnych bifenylu |
| EP4629958A1 (en) | 2022-12-06 | 2025-10-15 | Solventum Intellectual Properties Company | Surface-treated filler, dental composition containing such a filler, process of production and use thereof |
| CN115894888A (zh) * | 2022-12-06 | 2023-04-04 | 万华化学（烟台）容威聚氨酯有限公司 | 一种含氟苯胺基聚醚多元醇及其制备方法和聚氨酯硬质泡沫 |
| CN120857914A (zh) | 2023-03-01 | 2025-10-28 | 舒万诺知识产权公司 | 陶瓷贴面和用于制作陶瓷贴面的连续增材制造方法 |
| WO2025114114A1 (en) | 2023-11-27 | 2025-06-05 | Elantas Pdg, Inc. | Continuous process for producing poly(esterimide) polymer |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018262A (en) * | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
| NL298323A (enExample) * | 1959-12-24 | |||
| US3808006A (en) * | 1971-12-06 | 1974-04-30 | Minnesota Mining & Mfg | Photosensitive material containing a diaryliodium compound, a sensitizer and a color former |
| US3729313A (en) * | 1971-12-06 | 1973-04-24 | Minnesota Mining & Mfg | Novel photosensitive systems comprising diaryliodonium compounds and their use |
| US3741769A (en) * | 1972-10-24 | 1973-06-26 | Minnesota Mining & Mfg | Novel photosensitive polymerizable systems and their use |
| AU497960B2 (en) * | 1974-04-11 | 1979-01-25 | Minnesota Mining And Manufacturing Company | Photopolymerizable compositions |
| US4256828A (en) * | 1975-09-02 | 1981-03-17 | Minnesota Mining And Manufacturing Company | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| US4250053A (en) * | 1979-05-21 | 1981-02-10 | Minnesota Mining And Manufacturing Company | Sensitized aromatic iodonium or aromatic sulfonium salt photoinitiator systems |
| US4695251A (en) * | 1980-04-07 | 1987-09-22 | Minnesota Mining And Manufacturing Company | Orthodontic bracket adhesive and abrasive for removal thereof |
| JPS6072918A (ja) * | 1983-09-30 | 1985-04-25 | Toshiba Corp | 光重合性エポキシ樹脂組成物 |
| US4503169A (en) * | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| US4642126A (en) * | 1985-02-11 | 1987-02-10 | Norton Company | Coated abrasives with rapidly curable adhesives and controllable curvature |
| US4652274A (en) * | 1985-08-07 | 1987-03-24 | Minnesota Mining And Manufacturing Company | Coated abrasive product having radiation curable binder |
| CA1323949C (en) * | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
| US5639802A (en) * | 1991-05-20 | 1997-06-17 | Spectra Group Limited, Inc. | Cationic polymerization |
| DE69520222T2 (de) * | 1994-10-31 | 2001-08-23 | Minnesota Mining And Mfg. Co., Saint Paul | Mit sichtbarem licht härtbares epoxysystem mit verbesserter härtungstiefe |
| US5808108A (en) * | 1997-01-15 | 1998-09-15 | Chappelow; Cecil C. | Polymeric compositions and composites prepared from spiroorthocarbonates and epoxy monomers |
| US5998495A (en) * | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US6025406A (en) * | 1997-04-11 | 2000-02-15 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy resins |
-
1997
- 1997-04-11 US US08/840,093 patent/US5998495A/en not_active Expired - Lifetime
-
1998
- 1998-03-06 AU AU66903/98A patent/AU744316B2/en not_active Ceased
- 1998-03-06 WO PCT/US1998/004458 patent/WO1998047047A1/en not_active Ceased
- 1998-03-06 KR KR1019997009365A patent/KR20010006281A/ko not_active Withdrawn
- 1998-03-06 EP EP98909015A patent/EP0974078B1/en not_active Expired - Lifetime
- 1998-03-06 CA CA002285317A patent/CA2285317C/en not_active Expired - Fee Related
- 1998-03-06 JP JP54388598A patent/JP4009754B2/ja not_active Expired - Fee Related
- 1998-03-06 CN CN98804068A patent/CN1252137A/zh active Pending
- 1998-03-06 DE DE69815520T patent/DE69815520T2/de not_active Expired - Lifetime
- 1998-03-06 BR BR9807971-9A patent/BR9807971A/pt not_active IP Right Cessation
-
1999
- 1999-07-28 US US09/362,621 patent/US6187833B1/en not_active Expired - Lifetime
- 1999-10-11 NO NO19994955A patent/NO314041B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2285317A1 (en) | 1998-10-22 |
| JP4009754B2 (ja) | 2007-11-21 |
| AU6690398A (en) | 1998-11-11 |
| NO994955L (no) | 1999-10-11 |
| EP0974078A1 (en) | 2000-01-26 |
| KR20010006281A (ko) | 2001-01-26 |
| AU744316B2 (en) | 2002-02-21 |
| DE69815520T2 (de) | 2004-04-29 |
| EP0974078B1 (en) | 2003-06-11 |
| US6187833B1 (en) | 2001-02-13 |
| BR9807971A (pt) | 2000-03-08 |
| DE69815520D1 (de) | 2003-07-17 |
| CN1252137A (zh) | 2000-05-03 |
| NO994955D0 (no) | 1999-10-11 |
| US5998495A (en) | 1999-12-07 |
| JP2001520759A (ja) | 2001-10-30 |
| WO1998047047A1 (en) | 1998-10-22 |
| NO314041B1 (no) | 2003-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2285317C (en) | Ternary photoinitiator system for curing of epoxy/polyol resin compositions | |
| EP0968459B1 (en) | Ternary photoinitiator system for curing of epoxy resins | |
| US6765036B2 (en) | Ternary photoinitiator system for cationically polymerizable resins | |
| EP1083859B1 (en) | Photopolymerizable dental compositions | |
| JP3321173B2 (ja) | 増強された硬化深さを有する可視光硬化性エポキシ系 | |
| EP2285339B1 (en) | Initiator system containing a diarylakylamine derivative, hardenable composition and use thereof | |
| EP1684693A1 (en) | Photoinitiator systems with anthracene-based electron donors for curing cationically polymerizable resins | |
| CN102112095A (zh) | 具有连邻亚苯衍生物的引发剂体系、其制备方法和用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |