JP6548661B2 - 歯科用材料を調製するためのモノマー混合物 - Google Patents
歯科用材料を調製するためのモノマー混合物 Download PDFInfo
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- JP6548661B2 JP6548661B2 JP2016557608A JP2016557608A JP6548661B2 JP 6548661 B2 JP6548661 B2 JP 6548661B2 JP 2016557608 A JP2016557608 A JP 2016557608A JP 2016557608 A JP2016557608 A JP 2016557608A JP 6548661 B2 JP6548661 B2 JP 6548661B2
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- monomer mixture
- mixture according
- hydroperoxide
- bis
- methacrylate
- Prior art date
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- 239000000178 monomer Substances 0.000 title claims description 83
- 239000000203 mixture Substances 0.000 title claims description 79
- 239000005548 dental material Substances 0.000 title description 32
- 239000000463 material Substances 0.000 claims description 33
- 239000000945 filler Substances 0.000 claims description 27
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 21
- 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 17
- 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 16
- 239000003999 initiator Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- -1 nonanoylthiourea Chemical compound 0.000 claims description 14
- 150000003585 thioureas Chemical class 0.000 claims description 12
- 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 11
- 238000010526 radical polymerization reaction Methods 0.000 claims description 11
- 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 claims description 9
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 claims description 6
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- VCUNKEUDSCZBQQ-UHFFFAOYSA-N 2-[[3,3,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCC(C)CC(C)(C)CCNC(=O)OCCOC(=O)C(C)=C VCUNKEUDSCZBQQ-UHFFFAOYSA-N 0.000 claims description 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 4
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- 239000003479 dental cement Substances 0.000 claims description 4
- 150000002432 hydroperoxides Chemical class 0.000 claims description 4
- YNRXRRMQCMANTF-UHFFFAOYSA-N n-carbamothioylhexanamide Chemical compound CCCCCC(=O)NC(N)=S YNRXRRMQCMANTF-UHFFFAOYSA-N 0.000 claims description 4
- JAEZSIYNWDWMMN-UHFFFAOYSA-N 1,1,3-trimethylthiourea Chemical compound CNC(=S)N(C)C JAEZSIYNWDWMMN-UHFFFAOYSA-N 0.000 claims description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 3
- DZZWKUMHMSNBSG-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)thiourea Chemical compound C=CCNC(=S)NCC=C DZZWKUMHMSNBSG-UHFFFAOYSA-N 0.000 claims description 3
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 claims description 3
- LIZVXGBYTGTTTI-UHFFFAOYSA-N 2-[(4-methylphenyl)sulfonylamino]-2-phenylacetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C(O)=O)C1=CC=CC=C1 LIZVXGBYTGTTTI-UHFFFAOYSA-N 0.000 claims description 3
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 claims description 3
- LIEMOMJIUYRBNE-UHFFFAOYSA-N 2-methylprop-2-enoic acid;1-[4-(2-phenylpropan-2-yl)phenoxy]ethane-1,2-diol Chemical compound CC(=C)C(O)=O.C=1C=C(OC(O)CO)C=CC=1C(C)(C)C1=CC=CC=C1 LIEMOMJIUYRBNE-UHFFFAOYSA-N 0.000 claims description 3
- 102100026735 Coagulation factor VIII Human genes 0.000 claims description 3
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 claims description 3
- AHMICEFOMAGZRP-UHFFFAOYSA-N N-carbamothioyldecanamide Chemical compound CCCCCCCCCC(=O)NC(S)=N AHMICEFOMAGZRP-UHFFFAOYSA-N 0.000 claims description 3
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 claims description 3
- VWXMPPDQGVOCCW-UHFFFAOYSA-N [(4-methoxybenzoyl)-dimethylgermyl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)[Ge](C)(C)C(=O)C1=CC=C(OC)C=C1 VWXMPPDQGVOCCW-UHFFFAOYSA-N 0.000 claims description 3
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 claims description 3
- 229960001748 allylthiourea Drugs 0.000 claims description 3
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 3
- LMYQWQCDUHNQLF-UHFFFAOYSA-N hexylthiourea Chemical compound CCCCCCNC(N)=S LMYQWQCDUHNQLF-UHFFFAOYSA-N 0.000 claims description 3
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 claims description 3
- JHPAWUKVLIURBU-UHFFFAOYSA-N n-carbamothioylbutanamide Chemical compound CCCC(=O)NC(N)=S JHPAWUKVLIURBU-UHFFFAOYSA-N 0.000 claims description 3
- HQQSVTFPFYOGPS-UHFFFAOYSA-N n-carbamothioylheptanamide Chemical compound CCCCCCC(=O)NC(N)=S HQQSVTFPFYOGPS-UHFFFAOYSA-N 0.000 claims description 3
- DXZVIWFRNGADRH-UHFFFAOYSA-N n-carbamothioyloctanamide Chemical compound CCCCCCCC(=O)NC(N)=S DXZVIWFRNGADRH-UHFFFAOYSA-N 0.000 claims description 3
- PKENCYBXCVFWSR-UHFFFAOYSA-N n-carbamothioylpentanamide Chemical compound CCCCC(=O)NC(N)=S PKENCYBXCVFWSR-UHFFFAOYSA-N 0.000 claims description 3
- VVWCJSVUWOIXAD-UHFFFAOYSA-N n-carbamothioylpropanamide Chemical compound CCC(=O)NC(N)=S VVWCJSVUWOIXAD-UHFFFAOYSA-N 0.000 claims description 3
- QAKUNEDFMJPMGO-UHFFFAOYSA-N octylthiourea Chemical compound CCCCCCCCNC(N)=S QAKUNEDFMJPMGO-UHFFFAOYSA-N 0.000 claims description 3
- SLUHLANJIVXTRQ-UHFFFAOYSA-N pyridin-2-ylthiourea Chemical compound NC(=S)NC1=CC=CC=N1 SLUHLANJIVXTRQ-UHFFFAOYSA-N 0.000 claims description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims description 2
- 230000009977 dual effect Effects 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 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 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 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
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- 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
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N anhydrous trimellitic acid Natural products OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 239000005368 silicate glass Substances 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 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
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 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
- ILIMOFAFBPEQAT-UHFFFAOYSA-N 1,5,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)NC(=O)C(C)(C)C1=O ILIMOFAFBPEQAT-UHFFFAOYSA-N 0.000 description 1
- 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 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
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-UHFFFAOYSA-N 0.000 description 1
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-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
- XNRWLWYNGROTLU-UHFFFAOYSA-N 2-(2-ethoxycarbonylprop-2-enoxy)ethylphosphonic acid Chemical compound CCOC(=O)C(=C)COCCP(O)(O)=O XNRWLWYNGROTLU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 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
- OKKJMXCNNZVCPO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethylphosphonic acid Chemical compound CC(=C)C(=O)OCCP(O)(O)=O OKKJMXCNNZVCPO-UHFFFAOYSA-N 0.000 description 1
- XXEYEDZRUQKMLI-UHFFFAOYSA-N 2-(2-phosphonoethoxymethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)COCCP(O)(O)=O XXEYEDZRUQKMLI-UHFFFAOYSA-N 0.000 description 1
- RNQMRGKIIJATHS-UHFFFAOYSA-N 2-(3-prop-2-enoyloxypropoxy)ethylphosphonic acid Chemical compound OP(O)(=O)CCOCCCOC(=O)C=C RNQMRGKIIJATHS-UHFFFAOYSA-N 0.000 description 1
- AAMTXHVZOHPPQR-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enoic acid Chemical compound OCC(=C)C(O)=O AAMTXHVZOHPPQR-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JDKSTARXLKKYPS-UHFFFAOYSA-N 2-[10-(2-methylprop-2-enoyloxy)decyl]propanedioic acid Chemical compound CC(=C)C(=O)OCCCCCCCCCCC(C(O)=O)C(O)=O JDKSTARXLKKYPS-UHFFFAOYSA-N 0.000 description 1
- XQLIXIMAPOYOBV-UHFFFAOYSA-N 2-[2-(2,4,6-trimethylphenoxy)carbonylprop-2-enoxy]ethylphosphonic acid Chemical compound CC1=CC(C)=C(OC(=O)C(=C)COCCP(O)(O)=O)C(C)=C1 XQLIXIMAPOYOBV-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LMWVCJZYRYMGSL-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane Chemical compound CCC.CC(=C)C(O)=O.CC(=C)C(O)=O LMWVCJZYRYMGSL-UHFFFAOYSA-N 0.000 description 1
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 description 1
- LRQCBMGUUWENBW-UHFFFAOYSA-N 3-(2-methylprop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)NCCCS(O)(=O)=O LRQCBMGUUWENBW-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- LDUNNUKQPKEIJR-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C.C1CC2(C)C(=O)C(=O)C1C2(C)C LDUNNUKQPKEIJR-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-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
- 229920002799 BoPET Polymers 0.000 description 1
- HNAQKNFJWVDFMD-UHFFFAOYSA-N CC[Ge](CC)C(=O)c1ccc(OC)cc1 Chemical compound CC[Ge](CC)C(=O)c1ccc(OC)cc1 HNAQKNFJWVDFMD-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 244000137852 Petrea volubilis Species 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 240000007591 Tilia tomentosa Species 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- AMUNHMVMESMYQL-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]phenyl]propan-2-yl]phenyl]propyl] 2-methylprop-2-enoate Chemical compound C1=CC(CC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(CC(O)COC(=O)C(C)=C)C=C1 AMUNHMVMESMYQL-UHFFFAOYSA-N 0.000 description 1
- KJBLLFKNQIHZFC-UHFFFAOYSA-N [4-methyl-4-(2-methylprop-2-enoylamino)pentyl]phosphonic acid Chemical compound CC(=C)C(=O)NC(C)(C)CCCP(O)(O)=O KJBLLFKNQIHZFC-UHFFFAOYSA-N 0.000 description 1
- COHCXWLRUISKOO-UHFFFAOYSA-N [AlH3].[Ba] Chemical compound [AlH3].[Ba] COHCXWLRUISKOO-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- FWGZLZNGAVBRPW-UHFFFAOYSA-N alumane;strontium Chemical compound [AlH3].[Sr] FWGZLZNGAVBRPW-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012568 clinical material Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 239000011350 dental composite resin Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 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 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001698 pyrogenic effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical group NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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 compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- FIXNOXLJNSSSLJ-UHFFFAOYSA-N ytterbium(III) oxide Inorganic materials O=[Yb]O[Yb]=O FIXNOXLJNSSSLJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C13/00—Dental prostheses; Making same
- A61C13/225—Fastening prostheses in the mouth
- A61C13/26—Dentures without palates; Partial dentures, e.g. bridges
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C5/00—Filling or capping teeth
- A61C5/70—Tooth crowns; Making thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
- A61K6/17—Particle size
-
- 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
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/22—Esters containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
- Dental Prosthetics (AREA)
Description
2〜50wt%、特に好ましくは5〜45wt%、かなり特に好ましくは10〜30wt%の少なくとも1種の低揮発性モノメタクリレート;
5〜65wt%、特に好ましくは8〜60wt%、かなり特に好ましくは25〜50wt%の少なくとも1種の高粘度多官能性メタクリレート、好ましくは二官能性メタクリレート;および
5〜55wt%、特に好ましくは10〜50wt%、かなり特に好ましくは20〜45wt%の低粘度多官能性メタクリレート、好ましくは二官能性メタクリレート
を含有する。
(a)12.0〜75wt%、特に好ましくは19〜56wt%の本発明によるモノマー混合物、
(b)20〜85wt%、特に好ましくは40〜80wt%の充填剤(複数可)、
(c)ラジカル重合のための0.05〜4wt%、好ましくは0.1〜2.0wt%の開始剤、および任意選択で
(d)0.1〜5.0wt%、特に好ましくは0.1〜2.0wt%の添加剤(複数可)。
本発明によるモノマー混合物に基づく光硬化複合体
本発明の実施形態は、例えば、以下のものを含む。
(項目1)
少なくとも1種の低揮発性モノメタクリレート、少なくとも1種の高粘度多官能性メタクリレート、および少なくとも1種の低粘度多官能性メタクリレートを含有する、歯科用材料を調製するためのモノマー混合物。
(項目2)
前記低揮発性モノマー(複数可)が、標準圧力で150℃超の沸点を有し、前記高粘度モノマー(複数可)が、5Pa・s超の粘度(25℃で毛細管粘度計を使用して測定される)を有し、前記低粘度モノマー(複数可)が、300mPa・s未満の粘度(25℃で回転粘度計を使用して測定される)を有する、項目1に記載のモノマー混合物。
(項目3)
2〜50wt%、好ましくは5〜45wt%、特に好ましくは10〜30wt%の少なくとも1種の低揮発性モノメタクリレート;
5〜65wt%、好ましくは8〜60wt%、特に好ましくは25〜50wt%の少なくとも1種の高粘度多官能性メタクリレート、好ましくは二官能性メタクリレート;および
5〜55wt%、好ましくは10〜50wt%、特に好ましくは20〜45wt%の低粘度多官能性メタクリレート、好ましくは二官能性メタクリレート
を含有する、項目1または2に記載のモノマー混合物。
(項目4)
高粘度ジメタクリレートとして、TMX−UDMA(HEMAおよびヒドロキシプロピルメタクリレート(HPMA)とα,α,α’,α’−テトラメチル−m−キシリレンジイソシアネート(TMXDI)との付加生成物)、および/または1,6−ビス−[2−メタクリロイルオキシエトキシカルボニルアミノ]−2,4,4−トリメチルヘキサン(UDMA)、低粘度ジメタクリレートとして、ビスメタクリロイルオキシメチルトリシクロ[5.2.1.]デカン(TCDMA)、グリセロールジメタクリレート(GDMA)、および/またはデカンジオール−1,10−ジメタクリレート(D 3 MA)、ならびに低揮発性モノメタクリレートとして、p−クミルフェノキシエチレングリコールメタクリレート(CMP−1E)を含有する、項目1から3の一項に記載のモノマー混合物。
(項目5)
20wt%のCMP−1E、20wt%のGDMA、20wt%のTMX−UDMA、25wt%のUDMA、および15wt%のD 3 MAを含有する、項目4に記載のモノマー混合物。
(項目6)
いずれのTEGDMAも含有せず、好ましくはまた、いずれのビス−GMAも含有しない、項目1から5の一項に記載のモノマー混合物。
(項目7)
ラジカル重合のための開始剤、好ましくはチオ尿素誘導体およびビスアシルジアルキルゲルマニウム化合物の組合せをさらに含有する、項目1から6の一項に記載のモノマー混合物。
(項目8)
チオ尿素誘導体として、メチルチオ尿素、エチルチオ尿素、アリルチオ尿素、ブチルチオ尿素、ヘキシルチオ尿素、オクチルチオ尿素、ベンジルチオ尿素、1,1,3−トリメチルチオ尿素、1,1−ジアリルチオ尿素、1,3−ジアリルチオ尿素、1−(2−ピリジル)−2−チオ尿素、アセチルチオ尿素、プロパノイルチオ尿素、ブタノイルチオ尿素、ペンタノイルチオ尿素、ヘキサノイルチオ尿素、ヘプタノイルチオ尿素、オクタノイルチオ尿素、ノナノイルチオ尿素、デカノイルチオ尿素、ベンゾイルチオ尿素、またはこれらの混合物を含有する、項目7に記載のモノマー混合物。
(項目9)
ビスアシルジアルキルゲルマニウム化合物として、ビスベンゾイルジエチルゲルマニウム、ビスベンゾイルジメチルゲルマニウム、ビスベンゾイルジブチルゲルマニウム、ビス(4−メトキシベンゾイル)ジメチルゲルマニウム、ビス(4−メトキシベンゾイル)ジエチルゲルマニウム、またはこれらの混合物を含有する、項目7または8に記載のモノマー混合物。
(項目10)
過酸化物、または好ましくはヒドロペルオキシドをさらに含有する、項目7から9の一項に記載のモノマー混合物。
(項目11)
ヒドロペルオキシドとして、1,1,3,3−テトラメチルブチルヒドロペルオキシド、t−ブチルヒドロペルオキシド、クメンヒドロペルオキシド、ピナンヒドロペルオキシド、p−メンタンヒドロペルオキシド、ジイソプロピルベンゼンヒドロペルオキシド、t−アミルヒドロペルオキシド、またはこれらの混合物を含有する、項目10に記載のモノマー混合物。
(項目12)
有機粒子状充填剤または無機粒子状充填剤をさらに含有する、項目1から11の一項に記載のモノマー混合物。
(項目13)
600nm未満の最大粒径を有する充填剤のみを含有する、項目12に記載のモノマー混合物。
(項目14)
(a)12〜75wt%、特に好ましくは19〜56wt%の本発明によるモノマー混合物、
(b)20〜85wt%、特に好ましくは40〜80wt%の充填剤(複数可)、
(c)0.05〜4wt%、好ましくは0.1〜2.0wt%のラジカル重合のための開始剤、および任意選択で
(d)0.1〜5.0wt%、特に好ましくは0.1〜2.0wt%の添加剤(複数可)
を含有する、項目1から13の一項に記載のモノマー混合物。
(項目15)
歯科用セメント、充填複合体、コーティング材料、ベニアリング材料としての、インレー、アンレー、クラウン、またはブリッジを調製するための材料としての、項目1から14の一項に記載のモノマー混合物の使用。
Claims (16)
- 2〜50wt%のp−クミルフェノキシエチレングリコールメタクリレート(CMP−1E)である低揮発性モノメタクリレート、
5〜65wt%の、TMX−UDMA(HEMAおよびヒドロキシプロピルメタクリレート(HPMA)とα,α,α’,α’−テトラメチル−m−キシリレンジイソシアネート(TMXDI)との付加生成物)、および/または1,6−ビス−[2−メタクリロイルオキシエトキシ−カルボニルアミノ]−2,4,4−トリメチルヘキサン(UDMA)から選択される少なくとも1種の高粘度多官能性メタクリレート、および
5〜55wt%の、ビスメタクリロイルオキシメチルトリシクロ[5.2.1.]デカン(TCDMA)、グリセロールジメタクリレート(GDMA)、および/またはデカンジオール−1,10−ジメタクリレート(D3MA)から選択される少なくとも1種の低粘度多官能性メタクリレート
を含有する、歯科用材料を調製するためのモノマー混合物。 - 5〜45wt%の低揮発性モノメタクリレート;
8〜60wt%の少なくとも1種の高粘度多官能性メタクリレート;および
10〜50wt%の低粘度多官能性メタクリレートを含有する、請求項1に記載のモノマー混合物。 - 10〜30wt%の低揮発性モノメタクリレート;
25〜50wt%の少なくとも1種の高粘度多官能性メタクリレート;および
20〜45wt%の低粘度多官能性メタクリレートを含有する、請求項1に記載のモノマー混合物。 - 20wt%のCMP−1E、20wt%のGDMA、20wt%のTMX−UDMA、25wt%のUDMA、および15wt%のD3MAを含有する、請求項2に記載のモノマー混合物。
- いずれのTEGDMAも含有せず、いずれのビス−GMAも含有しない、請求項1から4の一項に記載のモノマー混合物。
- ラジカル重合のための開始剤をさらに含有する、請求項1から5の一項に記載のモノマー混合物。
- ラジカル重合のための開始剤として、チオ尿素誘導体およびビスアシルジアルキルゲルマニウム化合物の組合せを含有する、請求項6に記載のモノマー混合物。
- チオ尿素誘導体として、メチルチオ尿素、エチルチオ尿素、アリルチオ尿素、ブチルチオ尿素、ヘキシルチオ尿素、オクチルチオ尿素、ベンジルチオ尿素、1,1,3−トリメチルチオ尿素、1,1−ジアリルチオ尿素、1,3−ジアリルチオ尿素、1−(2−ピリジル)−2−チオ尿素、アセチルチオ尿素、プロパノイルチオ尿素、ブタノイルチオ尿素、ペンタノイルチオ尿素、ヘキサノイルチオ尿素、ヘプタノイルチオ尿素、オクタノイルチオ尿素、ノナノイルチオ尿素、デカノイルチオ尿素、ベンゾイルチオ尿素、またはこれらの混合物を含有する、請求項7に記載のモノマー混合物。
- ビスアシルジアルキルゲルマニウム化合物として、ビスベンゾイルジエチルゲルマニウム、ビスベンゾイルジメチルゲルマニウム、ビスベンゾイルジブチルゲルマニウム、ビス(4−メトキシベンゾイル)ジメチルゲルマニウム、ビス(4−メトキシベンゾイル)ジエチルゲルマニウム、またはこれらの混合物を含有する、請求項7または8に記載のモノマー混合物。
- 過酸化物、またはヒドロペルオキシドをさらに含有する、請求項6から9の一項に記載のモノマー混合物。
- ヒドロペルオキシドとして、1,1,3,3−テトラメチルブチルヒドロペルオキシド、t−ブチルヒドロペルオキシド、クメンヒドロペルオキシド、ピナンヒドロペルオキシド、p−メンタンヒドロペルオキシド、ジイソプロピルベンゼンヒドロペルオキシド、t−アミルヒドロペルオキシド、またはこれらの混合物を含有する、請求項10に記載のモノマー混合物。
- 有機粒子状充填剤または無機粒子状充填剤をさらに含有する、請求項1から11の一項に記載のモノマー混合物。
- 600nm未満の最大粒径を有する充填剤のみを含有する、請求項12に記載のモノマー混合物。
- (a)12〜75wt%の請求項1から5のいずれか一項に記載のモノマー混合物、
(b)20〜85wt%の1種または複数の充填剤、
(c)0.05〜4wt%のラジカル重合のための開始剤、および
(d)0.1〜5.0wt%の1種または複数の添加剤
を含有する、請求項1から13の一項に記載のモノマー混合物。 - (a)19〜56wt%の請求項1から5のいずれか一項に記載のモノマー混合物、
(b)40〜80wt%の1種または複数の充填剤、
(c)0.1〜2.0wt%のラジカル重合のための開始剤、および
(d)0.1〜2.0wt%の1種または複数の添加剤
を含有する、請求項14に記載のモノマー混合物。 - 歯科用セメント、充填複合体、コーティング材料、ベニアリング材料としての、インレー、アンレー、クラウン、またはブリッジを調製するための材料としての、請求項1から15の一項に記載のモノマー混合物の使用。
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EP14160841.4A EP2921156B1 (de) | 2014-03-20 | 2014-03-20 | Monomermischung zur Herstellung von Dentalwerkstoffen |
EP14160841.4 | 2014-03-20 | ||
PCT/EP2015/000449 WO2015139811A1 (de) | 2014-03-20 | 2015-02-26 | Monomermischung zur herstellung von dentalwerkstoffen |
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US3991008A (en) | 1974-08-12 | 1976-11-09 | The Kendall Company | Dental compositions having improved color stability |
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