JP2017523161A - 制御されたネットワーク構造を有する複合物 - Google Patents
制御されたネットワーク構造を有する複合物 Download PDFInfo
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- JP2017523161A JP2017523161A JP2017501017A JP2017501017A JP2017523161A JP 2017523161 A JP2017523161 A JP 2017523161A JP 2017501017 A JP2017501017 A JP 2017501017A JP 2017501017 A JP2017501017 A JP 2017501017A JP 2017523161 A JP2017523161 A JP 2017523161A
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- 239000002131 composite material Substances 0.000 title claims description 32
- 239000005548 dental material Substances 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000000945 filler Substances 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 26
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 26
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 50
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 42
- -1 acryloyloxy Chemical group 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 238000011049 filling Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003944 tolyl group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004568 cement Substances 0.000 claims description 5
- 230000008439 repair process Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 210000000214 mouth Anatomy 0.000 claims description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003464 sulfur compounds Chemical class 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 18
- 230000003111 delayed effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- 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 11
- 238000004440 column chromatography Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000499 gel Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- MTJCQDWBFAUXLD-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylmethyl]prop-2-enoic acid Chemical compound CC1=CC=C(S(=O)(=O)CC(=C)C(O)=O)C=C1 MTJCQDWBFAUXLD-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- BDSPQZRKYYVTIC-UHFFFAOYSA-N 2-[2-[2-[2-[2-[(4-methylphenyl)sulfonylmethyl]prop-2-enoyloxy]ethoxy]ethoxy]ethoxy]ethyl 2-[(4-methylphenyl)sulfonylmethyl]prop-2-enoate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)CC(C(=O)OCCOCCOCCOCCOC(C(=C)CS(=O)(=O)C1=CC=C(C=C1)C)=O)=C)C BDSPQZRKYYVTIC-UHFFFAOYSA-N 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 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 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- JSBSJTYIHUWPGS-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)CC(=C)C(=O)OCCCOC(=O)C(=C)CS(=O)(=O)C2=CC=C(C=C2)C Chemical compound CC1=CC=C(C=C1)S(=O)(=O)CC(=C)C(=O)OCCCOC(=O)C(=C)CS(=O)(=O)C2=CC=C(C=C2)C JSBSJTYIHUWPGS-UHFFFAOYSA-N 0.000 description 5
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 5
- 229930006711 bornane-2,3-dione Natural products 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- SDMHKNRXCMIZSA-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylmethyl]prop-2-enenitrile Chemical compound CC1=CC=C(S(=O)(=O)CC(=C)C#N)C=C1 SDMHKNRXCMIZSA-UHFFFAOYSA-N 0.000 description 4
- YDZYREHHCRHTRZ-UHFFFAOYSA-N 4-methylbenzenesulfonyl iodide Chemical compound CC1=CC=C(S(I)(=O)=O)C=C1 YDZYREHHCRHTRZ-UHFFFAOYSA-N 0.000 description 4
- QKVSFUUWDCPAFZ-UHFFFAOYSA-N N-methyl-2-[(4-methylphenyl)sulfonylmethyl]-N-propylprop-2-enamide Chemical compound CN(C(C(=C)CS(=O)(=O)C1=CC=C(C)C=C1)=O)CCC QKVSFUUWDCPAFZ-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- KIMKGBGMXUPKJT-UHFFFAOYSA-N [diethyl-(4-methoxybenzoyl)germyl]-(4-methoxyphenyl)methanone Chemical compound C=1C=C(OC)C=CC=1C(=O)[Ge](CC)(CC)C(=O)C1=CC=C(OC)C=C1 KIMKGBGMXUPKJT-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- PJIRIBQEWWBGCM-UHFFFAOYSA-N dodecyl 2-[(4-methylphenyl)sulfonylmethyl]prop-2-enoate Chemical compound C(CCCCCCCCCCC)OC(C(=C)CS(=O)(=O)C1=CC=C(C=C1)C)=O PJIRIBQEWWBGCM-UHFFFAOYSA-N 0.000 description 4
- MTCMFVTVXAOHNQ-UHFFFAOYSA-N ethyl 2-(bromomethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CBr MTCMFVTVXAOHNQ-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003479 dental cement Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 3
- PANYXKXCQVQOTD-UHFFFAOYSA-N ethyl 2-(methylsulfonylmethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CS(C)(=O)=O PANYXKXCQVQOTD-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ARSJPNMEXCCUFJ-UHFFFAOYSA-N methyl 2-methylidene-3-(4-methylphenyl)sulfonylbutanoate Chemical compound COC(C(C(C)S(=O)(=O)C1=CC=C(C=C1)C)=C)=O ARSJPNMEXCCUFJ-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- YENKRZXDJWBUIY-UHFFFAOYSA-N 1-phosphonooxypropan-2-yl 2-methylprop-2-enoate Chemical compound OP(=O)(O)OCC(C)OC(=O)C(C)=C YENKRZXDJWBUIY-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 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 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 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
- 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 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011350 dental composite resin Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009863 impact test Methods 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- UZLYXNNZYFBAQO-UHFFFAOYSA-N oxygen(2-);ytterbium(3+) Chemical compound [O-2].[O-2].[O-2].[Yb+3].[Yb+3] UZLYXNNZYFBAQO-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- ZZCNGCMJBJERQI-UHFFFAOYSA-N (1-prop-2-enoylpiperidin-4-yl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCN(C(=O)C=C)CC1 ZZCNGCMJBJERQI-UHFFFAOYSA-N 0.000 description 1
- IJAOUFAMBRPHSJ-UHFFFAOYSA-N (4-ethenylphenyl)methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=C(C=C)C=C1 IJAOUFAMBRPHSJ-UHFFFAOYSA-N 0.000 description 1
- CJBYXOUKKQTXPF-UHFFFAOYSA-N (4-ethenylphenyl)phosphonic acid Chemical compound OP(O)(=O)C1=CC=C(C=C)C=C1 CJBYXOUKKQTXPF-UHFFFAOYSA-N 0.000 description 1
- HGFPNCCIFWOGHW-UHFFFAOYSA-N 1,3-bis[prop-2-enoyl(propyl)amino]propan-2-yl dihydrogen phosphate Chemical compound CCCN(C(=O)C=C)CC(OP(O)(O)=O)CN(CCC)C(=O)C=C HGFPNCCIFWOGHW-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- CFKBCVIYTWDYRP-UHFFFAOYSA-N 10-phosphonooxydecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCOP(O)(O)=O CFKBCVIYTWDYRP-UHFFFAOYSA-N 0.000 description 1
- NTMDDSQESSRCTM-UHFFFAOYSA-N 10-phosphonooxydecyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCCCCCOC(=O)C=C NTMDDSQESSRCTM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
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- UHWLJHBFRWUMNP-UHFFFAOYSA-N 2-(2-methylprop-2-enoylamino)ethylphosphonic acid Chemical compound CC(=C)C(=O)NCCP(O)(O)=O UHWLJHBFRWUMNP-UHFFFAOYSA-N 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical group OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910003454 ytterbium oxide Inorganic materials 0.000 description 1
- 229940075624 ytterbium oxide Drugs 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
Images
Classifications
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
Aは、H;−CN;CH3、C2H5、OH、OCH3、O−COCH3、重合性ビニル、(メタ)アクリロイルオキシまたは(メタ)アクリルアミド基などの置換基の1つまたは1つより多くを保持し得るフェニル残基;あるいは1,4−フェニレン基、ウレタン基、OまたはSの1つまたは1つより多くに介在され得、かつ末端位置に重合性ビニル、(メタ)アクリロイルオキシまたは(メタ)アクリルアミド基を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり;
R1は、H、脂肪族直鎖状または分枝状C1〜C9アルキル残基、トリルまたはフェニルであり;
Lは、SR2、CO−フェニル、SO2R3、PO(R4R5)、PO(OR6)(R7)、PO(OR8)(OR9)またはハロゲンであり、式中、
R2〜9は、各場合にて互いに独立して、CH3、C2H5、OH、OCH3、−O−COCH3、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13などの置換基の1つまたは1つより多くを保持し得るフェニル残基であるか;あるいはOまたはSに介在され得、かつ末端位置に、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11〜13は、各場合にて互いに独立して、直鎖状または分枝状C1〜6残基であり;
Xは、−COO−、−CON(R10)−または存在せず、Aへの結合は、OまたはNを介して起こり、式中、
R10は、H、あるいはOまたはSの1つまたは1つより多くに介在され得、かつ末端位置に、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11〜13は、各場合にて互いに独立して、直鎖状または分枝状C1〜6ラジカルであり;
nは、1〜6の整数である。
Aは、H、−CN、フェニル残基、脂肪族直鎖状または分枝状C1〜C15アルキル残基であって、1,4−フェニレン基、ウレタン基、またはOの1つまたは1つより多くに介在され得、かつ末端位置に、重合性(メタ)アクリロイルオキシ基を保持し得る脂肪族直鎖状または分枝状C1〜C15アルキル残基であり;
R1は、H、フェニル、トリル、脂肪族直鎖状C1〜C3アルキル残基であり;
Lは、SR2またはSO2R3であり、式中、
R2〜3は、各場合にて互いに独立して、Oに介在され得、かつ末端位置に、重合性(メタ)アクリロイルオキシ基または−C(=CH2)−COOR11を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11は、直鎖状または分枝状C1〜3残基;あるいは置換基、好ましくは、CH3、C2H5、OCH3、および/またはO−COCH3の1つまたは1つより多くを保持し得るフェニル残基であり;
Xは、−COO−または−CON(R10)−であり、式中、R10は、メチルであるかまたは存在せず;
nは、1または2である。
Aは、1〜12個の炭素原子を有し、1,4−フェニレン基、ウレタン基またはOの1つまたは1つより多くに介在され得、かつメタクリロイルオキシ基を保持し得る、飽和直鎖状脂肪族炭化水素残基であり;
Xは、−COO−または−CON(R10)−であり、式中、R10は、メチルであるかまたは存在せず;
R1は、Hであり;
Lは、−SO2R3であり、式中、R3は、CH3またはトリルであり;
nは、1または2である。
Aは、6〜12個の炭素原子を有し、1〜3個のO原子に介在され得る、飽和直鎖状脂肪族炭化水素残基であり;
Xは、−COO−であり;
R1は、Hであり;
Lは、SO2R3であり、式中、R3は、CH3またはトリルであり;
nは、1または2である。
(a)5〜80重量%、好ましくは10〜70重量%、特に好ましくは10〜60重量%の多官能性(メタ)アクリレート(単数または複数)、
(b)0.01〜5.0重量%、好ましくは0.1〜5.0重量%、特に好ましくは0.1〜3.0重量%の開始剤(単数または複数)、
(c)0.5〜60重量%、好ましくは1.0〜50重量%、特に好ましくは1.0〜40重量%の少なくとも1つの一般式Iの化合物、
(d)0〜50重量%、好ましくは0〜40重量%、特に好ましくは0〜30重量%の単官能性(メタ)アクリレート(単数または複数)、
(e)0〜90重量%、好ましくは5〜90重量%、特に好ましくは5〜80重量%の充填材(単数または複数)、ならびに
(f)0〜5重量%、好ましくは0〜3重量%、特に好ましくは0.2〜3重量%の添加剤(単数または複数)。
1H-NMR (200 MHz, CDCl3, δ):7.71 (d, J = 8.2 Hz, 2H; Ar-H), 7.30 (d, J = 8.2Hz, 2H; Ar-H), 6.47 (s, 1H; =CH2), 5.89 (s, 1H; =CH2), 4.12 (s, 2H; -SO2-CH2-), 3.94 (t, 2H; -O-CH 2 -CH2-), 2.42 (s, 3H; Ar-CH3), 1.52 (m, 2H; -O-CH2-CH 2 -), 1.25 (s, 18H; -O-CH2-CH2-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH3); 0.86 (m, 3H; -CH2-CH 3 );
13C-NMR (50 MHz, CDCl3, δ):164.9 (C=O), 144.8 (C4), 135.5 (C4), 133.1 (C2), 129.6 (C3), 129.2 (C4), 128.8 (C3), 65.6 (C2), 57.5 (C2), 31.9 (C2), 29.6 (C2, C2, C2), 29.5 (C2), 29.3 (C2), 29.2 (C2), 28.4 (C2), 25.8 (C2), 22.7 (C2), 21.6 (C1), 14.1 (C1).
1H-NMR (200 MHz, CDCl3, δ): 7.73 (d, J = 8.2Hz, 4H; Ar-H), 7.32 (d, J = 8.2Hz, 4H; Ar-H), 6.52 (s, 2H; =CH2), 5.89 (s, 2H; =CH2), 4.14 (m, 8H; OOC-CH2-, SO2-CH2-), 3.62 (m, 12H; -CH2-O-CH2-CH2-), 2.43 (s, 6H; Ar-CH3).
13C-NMR (50 MHz, CDCl3, δ): 164.9 (C=O), 144.9 (C4), 135.4 (C4), 133.6 (C2), 129.7 (C3), 128.9 (C4), 128.8 (C4), 70.7 (C2), 68.8 (C2), 64.5 (C2), 57.5 (C2), 21.6 (C1).
1H-NMR (200 MHz, CDCl3, δ):7.73 (d, J = 8.2Hz, 4H; Ar-H), 7.32 (d, J = 8.2Hz, 4H; Ar-H), 6.52 (s, 2H; =CH2), 5.89 (s, 2H; =CH2), 4.14 (m, 8H; OOC-CH2-, SO2-CH2-), 3.62 (m, 12H; -CH2-O-CH2-CH2-), 2.43 (s, 6H; Ar-CH3);
13C-NMR (50 MHz, CDCl3, δ):164.9 (C=O), 144.9 (C4), 135.4 (C4), 133.6 (C2), 129.7 (C3), 128.9 (C4), 128.8 (C4), 70.7 (C2), 68.8 (C2), 64.5 (C2), 57.5 (C2), 21.6 (C1);
実施例1由来の移動試薬1を含む複合物の調製
実施例2由来の移動試薬2を含む複合物の調製
実施例3由来の移動試薬3を含む充填用複合物の調製
衝撃強度の測定(ダインスタット衝撃試験)
1H-NMR (200 MHz, CDCl3, δ):0.92-1.34 (9.1 H, m,3x -CH2-CH3), 2.77 (1 H, d, J=0.78 Hz, =C(COOEt)-CH2-PO(OEt)2), 2.87 (1 H, d, J=0.78 Hz, =C(COOEt)-CH2-PO(OEt)2), 3.87-4.18 (6.1 H, m,3x -O-CH2-CH3), 5.73 (1 H, dd, J=5.46 Hz, J=0.78 Hz, H2C=C(COOEt)-), 6.22 (1 H, dd, J=5.66 Hz, J=0.58 Hz, H2C=C(COOEt)-).
1H-NMR (200 MHz, CDCl3, δ):0.85 (3.5 H, t, J=6.46 Hz, -C10H20-CH 3), 1.10-1.65 (27.1 H, m, -CH2-C10 H 20-CH3 and -O-CH2-CH 3), 2.42 (2.1 H, t, J=7.24 Hz, -S-CH 2-C11H23), 3.35 (2 H, s, =C(COOC2H5)-CH 2-S-), 4.21 (2.2 H, q, J=7.11 Hz, -O-CH 2-CH3), 5.61 (1H, d, J=1.17 Hz, H 2C=C(COOC2H5)-), 6.17 (1 H, d, J=1.98 Hz, H 2C=C(COOC2H5)-).
1H-NMR (200 MHz, CDCl3, δ):1.18 (6.1 H, t, J=7.13 Hz, 2x -CH2-CH 3), 3.20 (3.8 H, d, J=0.58 Hz, 2x =C(COOC2H5)-CH 2-S-), 4.10 (4.1 H, q, J=7.11 Hz, -O-CH 2-CH3), 5.55 (2 H, d, J=0.98 Hz, 2x H 2C=C(COOC2H5)-), 6.09 (2 H, d, J=0.98 Hz, 2x H 2C=C(COOC2H5)-).
1H-NMR (200 MHz, CDCl3, δ):1.24 (6.4 H, t, J=7.14 Hz, 2x -CH2-CH 3), 4.03 (4.1 H, s, 2x =C(COOC2H5)-CH 2-S-), 4.18 (4.1 H, q, J=7.17 Hz, -O-CH 2-CH3), 6.08 (2 H, s, 2x H 2C=C(COOC2H5)-), 6.53 (2 H, s, 2x H 2C=C(COOC2H5)-).
1H-NMR (200 MHz, CDCl3) δ= 7.73 (d, 8.45 Hz, 2 H; Ar-H), 7.33 (d, J= 8.45 Hz, 2 H; Ar-H), 6.15 (s, 1 H; C=H2), 5.94 (s, 1 H; C=H2), 3.84 (s, 2 H; -SO2-CH2-), 2.41 (s, 3 H; Ar-CH3) ppm.
1H-NMR (200 MHz, CDCl3) δ= 7.59 (d, J= 7.64 Hz, 2 H; Ar-H), 7.5-6.9 (m, 7 H; Ar-H), 5.51 (s, 1 H; C=H2), 5.14 (s, 1 H; C=H2), 4.18 (s, 2 H; -SO2-CH2-), 2.32 (s, 3 H; Ar-CH3) ppm.
1H-NMR (200 MHz, CDCl3) δ= 8.81 (bs, 1H), 7.67 (d, J= 8.6 Hz, 2 H; Ar-H), 7.27 (d, J= 8.6 Hz, 2 H; Ar-H), 6.55 (s, 1 H; C=H2), 5.94 (s, 1 H; C=H2), 4.04 (s, 2 H; -SO2-CH2-), 2.36 (s, 3 H; Ar-CH3) ppm.
1H-NMR (200 MHz, CDCl3) δ= 7.78 (d, J= 8.1 Hz, 2 H; Ar-H), 7.34 (d, J= 8.1 Hz, 2 H; Ar-H), 5.51 (bs, 1 H; C=H2), 5.41 (s, 1 H; C=H2), 4.09 (s, 2 H; -SO2-CH2-), 3.5-2.7 (m, 5 H; N-CH 3 , N-CH 2 -CH2-CH3), 2.38 (s, 3 H; Ar-CH3), 1.7-1.3 (m, 2H; N-CH2-CH 2 -CH3), 0.85 (t, J= 7.5 Hz, 3 H; N-CH2-CH2-CH 3 ) ppm.
1H-NMR (200 MHz, CDCl3, δ): 7.70 (d, J = 8.2Hz, 2H; Ar-H), 7.31 (d, J = 8.2Hz, 2H; Ar-H), 6.49 (s, 1H; =CH2), 6.10 (m, 1H; =CH2), 5.86 (s, 1H; =CH2), 5.50 (m, 1H; =CH2), 4.27 (m, 2H; -OOC-CH2-), 4.12 (m, 4H; -OOC-CH2-, -SO2-CH2-), 3.71 (m, 2H; OOC-CH2-CH 2 -), 3.63 (m, 10H; -CH2-O-CH2-CH2-O-CH2-CH2-), 2.41 (s, 6H; Ar-CH3) 1.92 (m, 3H; -CO-C-CH3).
13C-NMR (50 MHz, CDCl3, δ): 164.9 (C=O), 145.0 (C4), 136.2 (C4) 135.5 (C4), 133.7 (C2), 129.8 (C3), 129.0 (C4), 128.9 (C3), 125.9 (C2), 70.7 (C2), 69.2 (C2), 68.9 (C2), 64.6 (C2), 64.0 (C2), 57.7 (C2), 21.8 (C1), 18.4 (C1).
1H-NMR (200 MHz, CDCl3, δ):6.64 (s, 1H; =CH2), 6.15 (s, 1H; =CH2), 4.28 (q, J = 7.1Hz, 2H; -COO-CH 2 -CH3), 4.06 (s, 2H; -SO2-CH 2 -C-), 2.90 (s, 3H; -SO2-CH3), 1.33 (t, J = 7.1Hz, 3H; -COO-CH2-CH 3 ).
13C-NMR (50 MHz, CDCl3, δ):165.3 (C=O), 133.9 (C2), 129.1 (C4), 61.9 (C2), 56.4 (C2), 40.5 (C1), 14.1 (C1).
1H-NMR (200 MHz, CDCl3, δ):7.69 (d, J = 8.2 Hz, 2H; Ar-H), 7.30 (d, J = 8.2Hz, 2H; Ar-H), 6.53 (s, 1H; =CH2), 5.98 (s, 1H; =CH2), 4.58 (q, J = 7.2 Hz, 1H; -SO2-CH-), 3.60 (s, 3H; -COO-CH3), 2.42 (s, 3H; Ar-CH3), 1.54 (d, J = 7.2 Hz, 3H; -SO2-CH-CH 3 ).
ジメタクリレートおよび移動試薬を含むポリマーの調製および特徴付け
Claims (16)
- 少なくとも1つの式Iの化合物:
Aは、H;−CN;CH3、C2H5、OH、OCH3、O−COCH3、重合性ビニル、(メタ)アクリロイルオキシまたは(メタ)アクリルアミド基などの置換基の1つまたは1つより多くを保持し得るフェニル残基;あるいは1,4−フェニレン基、ウレタン基、OまたはSの1つまたは1つより多くに介在され得、かつ末端位置に重合性ビニル、(メタ)アクリロイルオキシまたは(メタ)アクリルアミド基を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり;
R1は、H、脂肪族直鎖状または分枝状C1〜C9アルキルラジカル、トリルまたはフェニルであり;
Lは、SR2、CO−フェニル、SO2R3、PO(R4R5)、PO(OR6)(R7)、PO(OR8)(OR9)またはハロゲンであり、式中、
R2〜9は、各場合にて互いに独立して、CH3、C2H5、OH、OCH3、−O−COCH3、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13などの置換基の1つまたは1つより多くを保持し得るフェニル残基であるか;あるいはOまたはSに介在され得、かつ末端位置に、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11〜13は、各場合にて互いに独立して、直鎖状または分枝状C1〜6ラジカルであり;
Xは、−COO−、−CON(R10)−または存在せず、Aへの結合は、OまたはNを介して起こり、式中、
R10は、H;あるいはOまたはSの1つまたは1つより多くに介在され得、かつ末端位置に、重合性ビニル、(メタ)アクリロイルオキシ、(メタ)アクリルアミド基、−C(=CH2)−COOR11または−C(=CH2)−CO−NR12R13を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11〜13は、各場合にて互いに独立して、直鎖状または分枝状C1〜6ラジカルであり;
nは、1〜6の整数である)
を含む、ラジカル重合性歯科用材料。 - 少なくとも1つのラジカル重合性モノマー、好ましくは前記ラジカル重合用の少なくとも1つの開始剤をさらに含む、請求項1に記載の歯科用材料。
- 前記式Iの変数が、以下の意味を有する、請求項1または2に記載の歯科用材料:
Aは、H、−CN、フェニル残基、脂肪族直鎖状または分枝状C1〜C15アルキル残基であって、1,4−フェニレン基、ウレタン基、またはOの1つまたは1つより多くに介在され得、かつ末端位置に、重合性(メタ)アクリロイルオキシ基を保持し得る脂肪族直鎖状または分枝状C1〜C15アルキル残基であり;
R1は、H、フェニル、トリル、脂肪族直鎖状C1〜C3アルキル残基であり;
Lは、SR2またはSO2R3であり、式中、
R2〜3は、各場合にて互いに独立して、Oに介在され得、かつ末端位置に、重合性(メタ)アクリロイルオキシ基または−C(=CH2)−COOR11を保持し得る脂肪族直鎖状または分枝状C1〜C20アルキレン残基であり、式中、R11は、直鎖状または分枝状C1〜3ラジカル;あるいは置換基、好ましくは、CH3、C2H5、OCH3、および/またはO−COCH3の1つまたは1つより多くを保持し得るフェニルラジカルであり;
Xは、−COO−または−CON(R10)−であり、式中、R10は、メチルであるかまたは存在せず;
nは、1または2である。 - 前記式Iの変数が、以下の意味を有する、請求項3に記載の歯科用材料:
Aは、1〜12個の炭素原子を有し、1,4−フェニレン基、ウレタン基またはOの1つまたは1つより多くに介在され得、かつメタクリロイルオキシ基を保持し得る、飽和直鎖状脂肪族炭化水素残基であり;
Xは、−COO−または−CON(R10)−であり、式中、R10は、メチルであるかまたは存在せず;
R1は、Hであり;
Lは、−SO2R3であり、式中、R3は、CH3またはトリルであり;
nは、1または2である。 - 前記式Iの変数が、以下の意味を有する、請求項4に記載の歯科用材料:
Aは、6〜12個の炭素原子を有し、1〜3個のO原子に介在され得る、飽和直鎖状脂肪族炭化水素ラジカルであり;
Xは、−COO−であり;
R1は、Hであり;
Lは、SO2R3であり、式中、R3は、CH3またはトリルであり;
nは、1または2である。 - 少なくとも1つの多官能性(メタ)アクリレートまたは単官能性(メタ)アクリレートおよび多官能性(メタ)アクリレートの混合物を含む、請求項1〜5の1項に記載の歯科用材料。
- 少なくとも1つの充填材を含む、請求項1〜6の1項に記載の歯科用材料。
- 前記ラジカル重合用の少なくとも1つの開始剤をさらに含む、請求項1〜7の1項に記載の歯科用材料。
- 以下を含む、請求項1〜8の1項に記載の歯科用材料:
各場合にて前記歯科用材料の合計質量に対して、
0.5〜60重量%、好ましくは1.0〜50重量%、特に好ましくは1.0〜40重量%の少なくとも1つの一般式Iの化合物、
0.01〜5.0重量%、好ましくは0.1〜5.0重量%、特に好ましくは0.1〜3.0重量%の前記ラジカル重合用の開始剤(単数または複数)、および任意選択で、
5〜80重量%、好ましくは10〜70重量%、特に好ましくは10〜60重量%の多官能性(メタ)アクリレート(単数または複数)。 - 以下の組成を有する、請求項9に記載の歯科用材料:
各場合にて前記歯科用材料の合計質量に対して、
(a)5〜80重量%、好ましくは10〜70重量%、特に好ましくは10〜60重量%の多官能性(メタ)アクリレート(単数または複数)、
(b)0.01〜5.0重量%、好ましくは0.1〜5.0重量%、特に好ましくは0.1〜3.0重量%の開始剤(単数または複数)、
(c)0.5〜60重量%、好ましくは1.0〜50重量%、特に好ましくは1.0〜40重量%の少なくとも1つの一般式Iの化合物、
(d)0〜50重量%、好ましくは0〜40重量%、特に好ましくは0〜30重量%の単官能性(メタ)アクリレート(単数または複数)、
(e)0〜90重量%、好ましくは5〜90重量%、特に好ましくは0〜80重量%の充填材(単数または複数)、
(f)0〜5重量%、好ましくは0〜3重量%、特に好ましくは0.2〜3重量%の添加剤(単数または複数)。 - 揮発性メルカプタンを含まず、好ましくはいずれのメルカプタンも全く含まず、また好ましくはその他の硫黄化合物も含まない、請求項1〜10の1項に記載の歯科用材料。
- 損傷した歯を修復するために口腔内で使用するための、請求項1〜11の1項に記載の歯科用材料。
- セメント、充填用複合物またはベニア材料として使用するための、請求項12に記載の歯科用材料。
- 口外での歯科用修復物の製造または修繕のための材料としての、請求項1〜11の1項に記載の歯科用材料の使用。
- インレー、アンレー、クラウンまたはブリッジの製造のための、請求項14に記載の使用。
- 前記歯科用材料の重合収縮応力を低減するために、前記変数が、請求項1または請求項3〜5の1項で定められる通りである、式(I)の化合物の使用。
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EP14176729.3A EP2965741A1 (de) | 2014-07-11 | 2014-07-11 | Komposite mit gesteuerter Netzwerkstruktur |
EP14176729.3 | 2014-07-11 | ||
PCT/EP2015/065771 WO2016005534A1 (de) | 2014-07-11 | 2015-07-09 | Komposite mit gesteuerter netzwerkstruktur |
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EP (2) | EP2965741A1 (ja) |
JP (1) | JP6700247B2 (ja) |
CN (1) | CN106535862B (ja) |
ES (1) | ES2711757T3 (ja) |
WO (1) | WO2016005534A1 (ja) |
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JP2019014887A (ja) * | 2017-07-06 | 2019-01-31 | イフォクレール ヴィヴァデント アクチェンゲゼルシャフトIvoclar Vivadent AG | シランベースの移動試薬を含むポリマー材料 |
JP2020083891A (ja) * | 2018-11-28 | 2020-06-04 | イフォクレール ヴィヴァデント アクチェンゲゼルシャフトIvoclar Vivadent AG | 急速硬化および低収縮応力を有する光重合性歯科用コンポジット |
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ES2695237T3 (es) * | 2015-09-29 | 2019-01-02 | Ivoclar Vivadent Ag | Fotoiniciadores de acilgermanio y procedimiento para su preparación |
EP3622942B1 (de) * | 2018-09-17 | 2024-01-17 | Ivoclar Vivadent AG | Polymerwerkstoffe mit ungesättigten übertragungsreagenzien |
DE102019122174A1 (de) | 2019-08-19 | 2021-02-25 | Voco Gmbh | Dentale polymerisierbare Zusammensetzung auf der Basis kondensierter Silane |
EP3854374A1 (de) | 2020-01-24 | 2021-07-28 | Ivoclar Vivadent AG | Ästhetisches dentales füllungsmaterial mit hoher durchhärtungstiefe |
EP3932383B1 (de) * | 2020-07-03 | 2022-08-24 | Ivoclar Vivadent AG | Komposite mit verringerter polymerisationsschrumpfungsspannung |
EP4124331A1 (de) | 2021-07-27 | 2023-02-01 | Ivoclar Vivadent AG | Ästhetisches dentales füllungsmaterial mit hoher durchhärtungstiefe |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US2856390A (en) * | 1953-09-30 | 1958-10-14 | Eastman Kodak Co | Organophosphorus compounds derived from alkyl methacrylates |
US5932675A (en) | 1989-06-05 | 1999-08-03 | Commonwealth Scientific And Industrial Research Organisation | Free-radical chain transfer polymerization process |
US6316519B1 (en) | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
US8455565B2 (en) | 2011-05-18 | 2013-06-04 | 3M Innovative Properties Company | Disulfide monomers comprising ethylenically unsaturated groups suitable for dental compositions |
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US20120016052A1 (en) * | 2005-02-10 | 2012-01-19 | The Regents Of The University Of Colorado, A Body Corporate | Stress Relaxation in Crosslinked Polymers |
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JP2019014887A (ja) * | 2017-07-06 | 2019-01-31 | イフォクレール ヴィヴァデント アクチェンゲゼルシャフトIvoclar Vivadent AG | シランベースの移動試薬を含むポリマー材料 |
JP7094165B2 (ja) | 2017-07-06 | 2022-07-01 | イフォクレール ヴィヴァデント アクチェンゲゼルシャフト | シランベースの移動試薬を含むポリマー材料 |
JP2020083891A (ja) * | 2018-11-28 | 2020-06-04 | イフォクレール ヴィヴァデント アクチェンゲゼルシャフトIvoclar Vivadent AG | 急速硬化および低収縮応力を有する光重合性歯科用コンポジット |
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ES2711757T3 (es) | 2019-05-07 |
EP3166569B1 (de) | 2018-11-28 |
US20170172855A1 (en) | 2017-06-22 |
CN106535862B (zh) | 2021-04-13 |
JP6700247B2 (ja) | 2020-05-27 |
WO2016005534A1 (de) | 2016-01-14 |
US10342744B2 (en) | 2019-07-09 |
CN106535862A (zh) | 2017-03-22 |
EP3166569A1 (de) | 2017-05-17 |
EP2965741A1 (de) | 2016-01-13 |
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