RU2573997C2 - Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации - Google Patents
Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации Download PDFInfo
- Publication number
- RU2573997C2 RU2573997C2 RU2013136505/15A RU2013136505A RU2573997C2 RU 2573997 C2 RU2573997 C2 RU 2573997C2 RU 2013136505/15 A RU2013136505/15 A RU 2013136505/15A RU 2013136505 A RU2013136505 A RU 2013136505A RU 2573997 C2 RU2573997 C2 RU 2573997C2
- Authority
- RU
- Russia
- Prior art keywords
- dental composition
- meth
- monomer
- dental
- group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 230
- 238000013467 fragmentation Methods 0.000 title claims abstract description 44
- 238000006062 fragmentation reaction Methods 0.000 title claims abstract description 44
- 239000000178 monomer Substances 0.000 claims abstract description 117
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052809 inorganic oxide Inorganic materials 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 56
- 239000000945 filler Substances 0.000 claims description 52
- -1 vinyloxy Chemical group 0.000 claims description 45
- 125000005647 linker group Chemical group 0.000 claims description 31
- 239000002105 nanoparticle Substances 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 10
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 claims description 10
- 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 7
- 239000012634 fragment Substances 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 claims description 5
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 claims description 4
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- MKVYSRNJLWTVIK-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O MKVYSRNJLWTVIK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002265 redox agent Substances 0.000 claims description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
- ZQRXOCGXVFDJPG-UHFFFAOYSA-N n-(2-phenylethenyl)prop-2-enamide Chemical compound C=CC(=O)NC=CC1=CC=CC=C1 ZQRXOCGXVFDJPG-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 20
- 239000000546 pharmaceutical excipient Substances 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000008602 contraction Effects 0.000 abstract 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
- 238000001723 curing Methods 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 39
- 239000002253 acid Substances 0.000 description 36
- 239000011347 resin Substances 0.000 description 32
- 229920005989 resin Polymers 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 30
- 239000002245 particle Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 28
- 238000012360 testing method Methods 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000011521 glass Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 18
- 125000000524 functional group Chemical group 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000006116 polymerization reaction Methods 0.000 description 16
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 15
- 239000002131 composite material Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 12
- 210000000214 mouth Anatomy 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 11
- 239000003999 initiator Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 10
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000007800 oxidant agent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000010998 test method Methods 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000004568 cement Substances 0.000 description 9
- 229940023487 dental product Drugs 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- HIPPBUJQSIICJN-UHFFFAOYSA-N 3385-61-3 Chemical compound C12CC=CC2C2CC(O)C1C2 HIPPBUJQSIICJN-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 125000004404 heteroalkyl group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 241000183024 Populus tremula Species 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 239000003479 dental cement Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 210000003298 dental enamel Anatomy 0.000 description 6
- 210000004268 dentin Anatomy 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000003607 modifier Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 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 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011164 primary particle Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000007970 thio esters Chemical class 0.000 description 4
- 239000011345 viscous material Substances 0.000 description 4
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000008119 colloidal silica Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000011350 dental composite resin Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 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 3
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- LBNDGEZENJUBCO-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethyl]butanedioic acid Chemical compound CC(=C)C(=O)OCCC(C(O)=O)CC(O)=O LBNDGEZENJUBCO-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- DWTKNKBWDQHROK-UHFFFAOYSA-N 3-[2-(2-methylprop-2-enoyloxy)ethyl]phthalic acid Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C(O)=O)=C1C(O)=O DWTKNKBWDQHROK-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- SXMUXFDPJBTNRM-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propoxy]phenyl]propan-2-yl]phenoxy]propyl] 2-methylprop-2-enoate;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.C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 SXMUXFDPJBTNRM-UHFFFAOYSA-N 0.000 description 2
- XQAXGZLFSSPBMK-UHFFFAOYSA-M [7-(dimethylamino)phenothiazin-3-ylidene]-dimethylazanium;chloride;trihydrate Chemical compound O.O.O.[Cl-].C1=CC(=[N+](C)C)C=C2SC3=CC(N(C)C)=CC=C3N=C21 XQAXGZLFSSPBMK-UHFFFAOYSA-M 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000004053 dental implant Substances 0.000 description 2
- 239000005548 dental material Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000977 initiatory effect Effects 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
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- 229960000907 methylthioninium chloride Drugs 0.000 description 2
- 239000011859 microparticle Substances 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000011236 particulate material Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920000193 polymethacrylate Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- KXUAJVWQWIQAKA-QMMMGPOBSA-N (2s)-4-methyl-2-[2-(2-methylprop-2-enoyl)hydrazinyl]pentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NNC(=O)C(C)=C KXUAJVWQWIQAKA-QMMMGPOBSA-N 0.000 description 1
- JHVQWALHXJPODC-ALCCZGGFSA-N (z)-2-[2-(2-methylprop-2-enoyloxy)ethyl]but-2-enedioic acid Chemical compound CC(=C)C(=O)OCC\C(C(O)=O)=C\C(O)=O JHVQWALHXJPODC-ALCCZGGFSA-N 0.000 description 1
- 0 *C(C(O**N(C(N(*)C(N1**OC(C(*)=C)=O)=O)=O)C1=O)=O)=C Chemical compound *C(C(O**N(C(N(*)C(N1**OC(C(*)=C)=O)=O)=O)C1=O)=O)=C 0.000 description 1
- ZSPQVOFATJEJMT-UHFFFAOYSA-N 1,1,3,3-tetraethylthiourea Chemical compound CCN(CC)C(=S)N(CC)CC ZSPQVOFATJEJMT-UHFFFAOYSA-N 0.000 description 1
- OVRQXQSDQWOJIL-UHFFFAOYSA-N 1,1-dibutylthiourea Chemical compound CCCCN(C(N)=S)CCCC OVRQXQSDQWOJIL-UHFFFAOYSA-N 0.000 description 1
- LKGZXHMACFZOBP-UHFFFAOYSA-N 1-diethoxyphosphoryl-4-methylsulfanylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=C(SC)C=C1 LKGZXHMACFZOBP-UHFFFAOYSA-N 0.000 description 1
- KCHNMIKAMRQBHD-UHFFFAOYSA-N 1-hydroperoxypentane Chemical compound CCCCCOO KCHNMIKAMRQBHD-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GHWOVMXVQKOPHC-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyl)hydrazinyl]acetic acid Chemical compound CC(=C)C(=O)NNCC(O)=O GHWOVMXVQKOPHC-UHFFFAOYSA-N 0.000 description 1
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 1
- TYMZWBMKPLVKSI-UHFFFAOYSA-N 2-[[ethoxy(phenyl)phosphoryl]methyl]-1,3,5-trimethylbenzene Chemical compound C=1C=CC=CC=1P(=O)(OCC)CC1=C(C)C=C(C)C=C1C TYMZWBMKPLVKSI-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OZJJSQVLXHKGHV-UHFFFAOYSA-N 2-isocyanoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC[N+]#[C-] OZJJSQVLXHKGHV-UHFFFAOYSA-N 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- VALXVSHDOMUUIC-UHFFFAOYSA-N 2-methylprop-2-enoic acid;phosphoric acid Chemical compound OP(O)(O)=O.CC(=C)C(O)=O VALXVSHDOMUUIC-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DVUWFIWQOSNKQJ-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one;sodium Chemical compound [Na].[Na].O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 DVUWFIWQOSNKQJ-UHFFFAOYSA-N 0.000 description 1
- DTLUXZSCFRVBER-UHFFFAOYSA-N 3,3,6,6-tetramethylcyclohexane-1,2-dione Chemical compound CC1(C)CCC(C)(C)C(=O)C1=O DTLUXZSCFRVBER-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- NCAVPEPBIJTYSO-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.OCCCCOC(=O)C=C NCAVPEPBIJTYSO-UHFFFAOYSA-N 0.000 description 1
- SJDILFZCXQHCRB-UHFFFAOYSA-N 4-tert-butyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C(C)(C)C)C=C1 SJDILFZCXQHCRB-UHFFFAOYSA-N 0.000 description 1
- UNLGHUTUQNFLSO-UHFFFAOYSA-N 6-phosphonooxyhexyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCOC(=O)C=C UNLGHUTUQNFLSO-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
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UUEYEUDSRFNIQJ-UHFFFAOYSA-N CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O Chemical compound CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O UUEYEUDSRFNIQJ-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 229910021581 Cobalt(III) chloride Inorganic materials 0.000 description 1
- 235000013175 Crataegus laevigata Nutrition 0.000 description 1
- 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 description 1
- 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 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229910021577 Iron(II) chloride Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 229910009520 YbF3 Inorganic materials 0.000 description 1
- ASFHYIAIHXYBEN-UHFFFAOYSA-N [2-(2-methylprop-2-enoyloxy)-3-phosphonooxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(COP(O)(O)=O)OC(=O)C(C)=C ASFHYIAIHXYBEN-UHFFFAOYSA-N 0.000 description 1
- LGVWZIPWNLYURF-UHFFFAOYSA-N [decoxy(hydroxy)phosphoryl] prop-2-eneperoxoate Chemical compound C(C=C)(=O)OOP(OCCCCCCCCCC)(O)=O LGVWZIPWNLYURF-UHFFFAOYSA-N 0.000 description 1
- DTJQVBJWTFJZPE-UHFFFAOYSA-N [hydroxy(octoxy)phosphoryl] prop-2-eneperoxoate Chemical compound P(=O)(OOC(C=C)=O)(OCCCCCCCC)O DTJQVBJWTFJZPE-UHFFFAOYSA-N 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 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
- 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
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000005385 borate glass Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000008376 breath freshener Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004075 cariostatic agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000012936 correction and preventive action Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 201000002170 dentin sensitivity Diseases 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- INPXKEACWBDDSB-UHFFFAOYSA-L disodium;2-(4,5-diiodo-3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=CC(=O)C(I)=C2OC2=C(I)C([O-])=CC=C21 INPXKEACWBDDSB-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical class [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 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
- ZBQZBWKNGDEDOA-UHFFFAOYSA-N eosin B Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC([N+]([O-])=O)=C(O)C(Br)=C1OC1=C2C=C([N+]([O-])=O)C(O)=C1Br ZBQZBWKNGDEDOA-UHFFFAOYSA-N 0.000 description 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
- QGAYMQGSQUXCQO-UHFFFAOYSA-L eosin b Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC([N+]([O-])=O)=C([O-])C(Br)=C1OC1=C2C=C([N+]([O-])=O)C([O-])=C1Br QGAYMQGSQUXCQO-UHFFFAOYSA-L 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 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
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000009969 flowable effect Effects 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 238000007496 glass forming Methods 0.000 description 1
- 239000003178 glass ionomer cement Substances 0.000 description 1
- 238000005816 glass manufacturing process Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000005027 hydroxyaryl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005365 phosphate glass Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 230000036347 tooth sensitivity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 1
- ZFZDWMXUMXACHS-IACGZSPGSA-N tricyclo[5.2.1.02,6]decane-4,8-dimethanol Chemical compound C([C@H]1C2)C(CO)[C@H]2C2C1CC(CO)C2 ZFZDWMXUMXACHS-IACGZSPGSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/61—Cationic, anionic or redox initiators
-
- 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
- A61K6/40—Primers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161443218P | 2011-02-15 | 2011-02-15 | |
| US61/443,218 | 2011-02-15 | ||
| US201161521134P | 2011-08-08 | 2011-08-08 | |
| US61/521,134 | 2011-08-08 | ||
| PCT/US2012/024222 WO2012112350A2 (en) | 2011-02-15 | 2012-02-08 | Dental compositions comprising ethylenically unsaturated addition-fragmentation agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2013136505A RU2013136505A (ru) | 2015-03-27 |
| RU2573997C2 true RU2573997C2 (ru) | 2016-01-27 |
Family
ID=45688265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2013136505/15A RU2573997C2 (ru) | 2011-02-15 | 2012-02-08 | Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9056043B2 (enExample) |
| EP (2) | EP2965742B1 (enExample) |
| JP (1) | JP6077463B2 (enExample) |
| CN (1) | CN103370041B (enExample) |
| BR (1) | BR112013019702B1 (enExample) |
| RU (1) | RU2573997C2 (enExample) |
| WO (1) | WO2012112350A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2765824C1 (ru) * | 2018-08-13 | 2022-02-03 | Стик Тек Ой | Стоматологическая композиция |
| EP4048708A1 (de) * | 2019-10-31 | 2022-08-31 | Kulzer GmbH | Polymerisierbare zusammensetzung |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120208965A1 (en) * | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
| EP2675421A2 (en) | 2011-02-15 | 2013-12-25 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| US10370322B2 (en) * | 2011-02-15 | 2019-08-06 | 3M Innovative Properties Company | Addition-fragmentation agents |
| US8980969B2 (en) | 2011-08-23 | 2015-03-17 | 3M Innovative Properties Company | Addition-fragmentation agents |
| CN103732203B (zh) | 2011-08-23 | 2017-05-03 | 3M创新有限公司 | 包含加成‑断裂剂的牙科组合物 |
| US9410030B2 (en) | 2012-11-12 | 2016-08-09 | 3M Innovative Properties Company | Addition-fragmentation agents |
| US9414996B2 (en) | 2012-11-12 | 2016-08-16 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
| US9463146B2 (en) | 2012-12-17 | 2016-10-11 | 3M Innovative Properties Company | Addition-fragmentation oligomers |
| WO2014116461A1 (en) | 2013-01-24 | 2014-07-31 | 3M Innovative Properties Company | Photoinitiated oligomerization of methacrylate esters |
| CN105051007B (zh) * | 2013-03-20 | 2020-03-13 | 3M创新有限公司 | 高折射率加成-断裂剂 |
| KR102226633B1 (ko) * | 2013-09-20 | 2021-03-10 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 트라이티오카르보네이트-함유 부가-단편화제 |
| US9758478B2 (en) | 2013-10-16 | 2017-09-12 | 3M Innovative Properties Company | Allyl disulfide-containing addition-fragmentation oligomers |
| EP3107975B1 (en) * | 2014-02-18 | 2020-01-15 | 3M Innovative Properties Company | Addition-fragmentation oligomers having high refractive index groups |
| US10159548B2 (en) | 2014-09-17 | 2018-12-25 | Garrison Dental Solutions, L.L.C. | Dental curing light |
| US10350297B2 (en) | 2014-10-31 | 2019-07-16 | 3M Innovative Properties Company | Dental materials and methods |
| EP3212153A1 (en) | 2014-10-31 | 2017-09-06 | 3M Innovative Properties Company | Dental materials and methods |
| TWI515255B (zh) * | 2014-12-31 | 2016-01-01 | 財團法人工業技術研究院 | 可固化樹脂及應用其之可固化組成物 |
| WO2016133668A1 (en) * | 2015-02-20 | 2016-08-25 | 3M Innovative Properties Company | Addition-fragmentation oligomers |
| EP3124009A1 (en) * | 2015-07-27 | 2017-02-01 | DENTSPLY DETREY GmbH | Dental adhesive |
| CN105107025B (zh) * | 2015-09-11 | 2018-06-15 | 上海沪亮生物医药科技有限公司 | 一种有机/无机复合材料及其制备方法和在义齿制作中的用途 |
| RU2018128362A (ru) | 2016-02-05 | 2020-03-05 | 3М Инновейтив Пропертиз Компани | Стоматологические композиции, содержащие наночастицы, обеспечивающие разницу между показателями преломления полимеризуемой смолы и наполнителя |
| USD810293S1 (en) | 2017-01-20 | 2018-02-13 | Garrison Dental Solutions, Llc | Dental instrument |
| KR101929652B1 (ko) | 2017-03-20 | 2018-12-17 | 주식회사 케이씨씨 | 경화성 조성물 |
| JP7238785B2 (ja) * | 2017-12-05 | 2023-03-14 | Jnc株式会社 | 重合性極性化合物、液晶組成物、および液晶表示素子 |
| JP7238786B2 (ja) * | 2017-12-06 | 2023-03-14 | Jnc株式会社 | 化合物、液晶組成物、および液晶表示素子 |
| EP4501303A3 (en) | 2017-12-21 | 2025-04-30 | Solventum Intellectual Properties Company | Inorganic dental fillers including a silane treated surface |
| WO2019211724A2 (en) | 2018-05-02 | 2019-11-07 | 3M Innovative Properties Company | One-part dental adhesive composition for fixing dental composite materials |
| CN112367959A (zh) * | 2018-06-29 | 2021-02-12 | 3M创新有限公司 | 包含在水性环境中具有改善的强度的固化的可自由基聚合组合物的正畸制品 |
| EP3622942B1 (de) | 2018-09-17 | 2024-01-17 | Ivoclar Vivadent AG | Polymerwerkstoffe mit ungesättigten übertragungsreagenzien |
| US12138325B2 (en) | 2018-11-27 | 2024-11-12 | Kuraray Noritake Dental Inc. | Dental composition |
| DE102019122174A1 (de) | 2019-08-19 | 2021-02-25 | Voco Gmbh | Dentale polymerisierbare Zusammensetzung auf der Basis kondensierter Silane |
| WO2021205326A1 (en) * | 2020-04-08 | 2021-10-14 | 3M Innovative Properties Company | Curable compositions and methods of using the same |
| JP7515361B2 (ja) * | 2020-09-30 | 2024-07-12 | 株式会社松風 | 医科歯科用低重合収縮性モノマーの合成・製造方法 |
| WO2022096973A1 (en) | 2020-11-05 | 2022-05-12 | 3M Innovative Properties Company | Imide addition-fragmentation agents |
| US20220153918A1 (en) * | 2020-11-17 | 2022-05-19 | Divergent Technologies, Inc. | Isocyanurate resin compositions |
| US11992539B2 (en) | 2020-11-25 | 2024-05-28 | Solventum Intellectual Properties Company | Curable dental compositions and uses thereof |
| EP4308571A1 (en) | 2021-03-17 | 2024-01-24 | 3M Innovative Properties Company | Polymerizable 4,4'-spirobi[chromane]-2,2'-diones and curable compositions including the same |
| EP4444809A1 (en) | 2021-12-06 | 2024-10-16 | 3M Innovative Properties Company | Adhesives comprising cyclic imide addition-fragmentation and adhesion agents |
| US12329833B2 (en) * | 2021-12-06 | 2025-06-17 | Solventum Intellectual Properties Company | Dental compositions |
| US20230210731A1 (en) * | 2022-01-04 | 2023-07-06 | Cao Group, Inc. | Reduction resistant hydrogel thickeners |
| WO2023209463A1 (en) | 2022-04-26 | 2023-11-02 | 3M Innovative Properties Company | Dental composition containing a resorcinol or catechol moiety containing component and use thereof |
| CN120456887A (zh) | 2022-12-06 | 2025-08-08 | 舒万诺知识产权公司 | 经表面处理的填料、含有这种填料的牙科组合物、其生产方法和用途 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318845A (en) * | 1940-03-23 | 1943-05-11 | Austenal Lab Inc | Dental resin |
| US6316519B1 (en) * | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| US6900280B2 (en) * | 2001-03-01 | 2005-05-31 | Ciba Specialty Chemicals Corp. | Acid macromonomers and their method of preparation |
| RU2275183C2 (ru) * | 2000-08-26 | 2006-04-27 | Дегусса Аг | Стоматологический материал с гибридными наполнителями и способ его получения |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547323A (en) | 1984-03-21 | 1985-10-15 | Scm Corporation | Synthesis of 2,2-dimethyl-4-methyleneglutaric acid and derivatives |
| US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| US4886861A (en) * | 1985-04-23 | 1989-12-12 | E. I. Dupont De Nemours And Company | Molecular weight control in free radical polymerizations |
| US5324879A (en) * | 1985-12-03 | 1994-06-28 | Commonwealth Scientific And Industrial Research Organisation | Oligomerization process |
| CA1323949C (en) | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
| AU618772B2 (en) | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
| US5444118A (en) * | 1989-06-30 | 1995-08-22 | Japan Synthetic Rubber Co., Ltd. | Process for producing copolymer latex and paper coating composition, carpet backing composition or adhesive composition comprising said latex |
| US5154762A (en) | 1991-05-31 | 1992-10-13 | Minnesota Mining And Manufacturing Company | Universal water-based medical and dental cement |
| US5264530A (en) * | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| US5501727A (en) | 1994-02-28 | 1996-03-26 | Minnesota Mining And Manufacturing Company | Color stability of dental compositions containing metal complexed ascorbic acid |
| US6126922A (en) | 1995-11-17 | 2000-10-03 | 3M Innovative Properties Company | Fluorid-releasing compositions and compositions with improved rheology |
| US5770646A (en) * | 1996-10-29 | 1998-06-23 | E. I. Du Pont De Nemours And Company | Aqueous branched polymer dispersant for hydrophobic materials |
| US6001897A (en) | 1997-01-13 | 1999-12-14 | American Dental Association Health Foundation | Polymerizable conditioners for adhesive bonding to dentin and enamel |
| JP4083257B2 (ja) | 1997-03-19 | 2008-04-30 | 株式会社ジーシー | 歯科充填用レジン組成物 |
| US6096903A (en) | 1997-03-25 | 2000-08-01 | Ivoclar Ag | Hydrolysable and polymerizable oxetane silanes |
| US6506816B1 (en) | 1997-07-17 | 2003-01-14 | 3M Innovative Properties Company | Dental resin cements having improved handling properties |
| US6174953B1 (en) * | 1998-02-19 | 2001-01-16 | E. I. Du Pont De Nemours And Company | Low molecular weight (meth) acrylate copolymer emulsions |
| US6030606A (en) | 1998-06-22 | 2000-02-29 | 3M Innovative Properties Company | Dental restoratives comprising Bis-EMA6 |
| CA2336960A1 (en) * | 1998-07-10 | 2000-01-20 | E.I. Du Pont De Nemours And Company | Microgels and process for their preparation |
| DE19943712C1 (de) | 1999-09-08 | 2001-05-17 | Ivoclar Ag Schaan | Hydrolysierbare und polymerisierbare Silane auf der Basis von Methylendithiepan |
| US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
| DE60042038D1 (de) | 1999-10-28 | 2009-05-28 | 3M Innovative Properties Co | Siliziumdioxid-Nanoteilchen in Form eines trockenen Pulvers |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| US6572693B1 (en) | 1999-10-28 | 2003-06-03 | 3M Innovative Properties Company | Aesthetic dental materials |
| US20060009574A1 (en) * | 2001-01-26 | 2006-01-12 | Aert Huub V | Method of emulsion polymerization |
| DE10106372A1 (de) | 2001-02-12 | 2002-08-29 | Ivoclar Vivadent Ag | Thermochromer Dentalwerkstoff |
| EP2272485A3 (en) | 2001-08-15 | 2014-07-16 | 3M Innovative Properties Co. | Hardenable self-supporting structures and methods |
| CN1319507C (zh) | 2002-01-31 | 2007-06-06 | 3M创新有限公司 | 牙科糊剂、牙科制品和方法 |
| US7649029B2 (en) | 2004-05-17 | 2010-01-19 | 3M Innovative Properties Company | Dental compositions containing nanozirconia fillers |
| US7090721B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Use of nanoparticles to adjust refractive index of dental compositions |
| US7156911B2 (en) | 2004-05-17 | 2007-01-02 | 3M Innovative Properties Company | Dental compositions containing nanofillers and related methods |
| US7090722B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Acid-reactive dental fillers, compositions, and methods |
| WO2006020760A1 (en) | 2004-08-11 | 2006-02-23 | 3M Innovative Properties Company | Self-adhesive compositions including a plurality of acidic compounds |
| US7241437B2 (en) | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| EP2803677B1 (en) * | 2005-02-10 | 2016-06-08 | The Regents of the University of Colorado, a Body Corporate | Stress relaxation in crosslinked polymers |
| CN102512329A (zh) | 2005-05-09 | 2012-06-27 | 3M创新有限公司 | 含有杂化单体的牙科组合物 |
| CA2655070C (en) | 2006-06-09 | 2014-12-30 | Dentsply International Inc. | Flowable dental resin compositions with low polymerization stress |
| EP2114350A1 (en) | 2006-12-28 | 2009-11-11 | 3M Innovative Properties Company | (meth)acryloyl-containing materials, compositions, and methods |
| EP2231714B1 (en) | 2008-01-15 | 2012-08-29 | DENTSPLY International Inc. | Functional resin composition for regulated polymerization stress |
| US8545222B2 (en) * | 2008-10-21 | 2013-10-01 | Chan Qian Wang | Method of dental implant restoration |
| EP2552380B1 (en) | 2010-03-31 | 2019-04-24 | 3M Innovative Properties Company | Polymerizable isocyanurate monomers and dental compositions |
| EP2401998A1 (en) | 2010-07-02 | 2012-01-04 | 3M Innovative Properties Company | Dental composition, kit of parts and use thereof |
| US20120208965A1 (en) | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
-
2012
- 2012-02-08 EP EP15175714.3A patent/EP2965742B1/en active Active
- 2012-02-08 JP JP2013553505A patent/JP6077463B2/ja active Active
- 2012-02-08 RU RU2013136505/15A patent/RU2573997C2/ru not_active IP Right Cessation
- 2012-02-08 WO PCT/US2012/024222 patent/WO2012112350A2/en not_active Ceased
- 2012-02-08 CN CN201280008646.3A patent/CN103370041B/zh active Active
- 2012-02-08 BR BR112013019702-1A patent/BR112013019702B1/pt active IP Right Grant
- 2012-02-08 US US13/978,557 patent/US9056043B2/en active Active
- 2012-02-08 EP EP12704603.5A patent/EP2675422B1/en active Active
-
2015
- 2015-05-08 US US14/707,096 patent/US9320685B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318845A (en) * | 1940-03-23 | 1943-05-11 | Austenal Lab Inc | Dental resin |
| US6316519B1 (en) * | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| RU2275183C2 (ru) * | 2000-08-26 | 2006-04-27 | Дегусса Аг | Стоматологический материал с гибридными наполнителями и способ его получения |
| US6900280B2 (en) * | 2001-03-01 | 2005-05-31 | Ciba Specialty Chemicals Corp. | Acid macromonomers and their method of preparation |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2765824C1 (ru) * | 2018-08-13 | 2022-02-03 | Стик Тек Ой | Стоматологическая композиция |
| US12268762B2 (en) | 2018-08-13 | 2025-04-08 | Stick Tech Oy | Dental composition |
| EP4048708A1 (de) * | 2019-10-31 | 2022-08-31 | Kulzer GmbH | Polymerisierbare zusammensetzung |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013019702A2 (pt) | 2017-10-24 |
| US20150238389A1 (en) | 2015-08-27 |
| EP2965742A1 (en) | 2016-01-13 |
| RU2013136505A (ru) | 2015-03-27 |
| CN103370041A (zh) | 2013-10-23 |
| EP2965742B1 (en) | 2020-09-09 |
| BR112013019702B1 (pt) | 2018-05-22 |
| US20130316307A1 (en) | 2013-11-28 |
| EP2675422B1 (en) | 2020-09-30 |
| WO2012112350A3 (en) | 2012-12-27 |
| JP6077463B2 (ja) | 2017-02-08 |
| WO2012112350A2 (en) | 2012-08-23 |
| CN103370041B (zh) | 2016-06-15 |
| US9056043B2 (en) | 2015-06-16 |
| JP2014505105A (ja) | 2014-02-27 |
| US9320685B2 (en) | 2016-04-26 |
| EP2675422A2 (en) | 2013-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2573997C2 (ru) | Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации | |
| US9012531B2 (en) | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer | |
| US9168206B2 (en) | Curable dental compositions and articles comprising polymerizable ionic liquids | |
| RU2586743C2 (ru) | Стоматологические композиции, содержащие агенты присоединения-фрагментации | |
| EP2552380B1 (en) | Polymerizable isocyanurate monomers and dental compositions | |
| US10022306B2 (en) | Dental compositions comprising a fatty mono(meth)acrylate | |
| KR102174015B1 (ko) | 부가-단편화제를 포함하는 치과용 조성물 | |
| US9675529B2 (en) | Dental composition containing high refractive index monomers | |
| US8455565B2 (en) | Disulfide monomers comprising ethylenically unsaturated groups suitable for dental compositions | |
| US20110171609A1 (en) | Dental Composition Comprising Biphenyl Di(meth)acrylate Monomer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20210209 |