JP2022024778A - 重合性組成物の製造方法及び重合性組成物 - Google Patents
重合性組成物の製造方法及び重合性組成物 Download PDFInfo
- Publication number
- JP2022024778A JP2022024778A JP2020127566A JP2020127566A JP2022024778A JP 2022024778 A JP2022024778 A JP 2022024778A JP 2020127566 A JP2020127566 A JP 2020127566A JP 2020127566 A JP2020127566 A JP 2020127566A JP 2022024778 A JP2022024778 A JP 2022024778A
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable monomer
- polymerizable
- solution
- polymerizable composition
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 160
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 239000007787 solid Substances 0.000 claims abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000011350 dental composite resin Substances 0.000 description 18
- 239000006185 dispersion Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 13
- 239000011521 glass Substances 0.000 description 10
- 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 7
- 239000004570 mortar (masonry) Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- VIYWVRIBDZTTMH-UHFFFAOYSA-N 2-[4-[2-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOC(=O)C(C)=C)C=C1 VIYWVRIBDZTTMH-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- -1 acryloyloxy groups Chemical group 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BTLXPCBPYBNQNR-UHFFFAOYSA-N 1-hydroxyanthraquinone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2O BTLXPCBPYBNQNR-UHFFFAOYSA-N 0.000 description 2
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- LWMFAFLIWMPZSX-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene Chemical compound N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LWMFAFLIWMPZSX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 2
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 2
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- DRIRMYPZOAOUPR-UHFFFAOYSA-N 10,10-dioxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)(=O)C2=C1 DRIRMYPZOAOUPR-UHFFFAOYSA-N 0.000 description 1
- YEZOVIIHKKPUOS-UHFFFAOYSA-N 10-oxothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3S(=O)C2=C1 YEZOVIIHKKPUOS-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 1
- SQOUGRMFFXWSRY-UHFFFAOYSA-N 2-chloro-7-(trifluoromethyl)thioxanthen-9-one Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(C(F)(F)F)=CC=C3SC2=C1 SQOUGRMFFXWSRY-UHFFFAOYSA-N 0.000 description 1
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ZWVCZSFSZUTSCR-UHFFFAOYSA-N 2-methylprop-2-enoic acid;1-phenoxyethane-1,2-diol Chemical compound CC(=C)C(O)=O.OCC(O)OC1=CC=CC=C1 ZWVCZSFSZUTSCR-UHFFFAOYSA-N 0.000 description 1
- UPTHZKIDNHJFKQ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane-1,2,3-triol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(O)CO UPTHZKIDNHJFKQ-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- DYRJLHNVMSBZLR-UHFFFAOYSA-N 2-nitrothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3SC2=C1 DYRJLHNVMSBZLR-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- NMZSJIQGMAGSSO-UHFFFAOYSA-N 3-[[1-amino-2-[[1-amino-1-(2-carboxyethylimino)-2-methylpropan-2-yl]diazenyl]-2-methylpropylidene]amino]propanoic acid Chemical compound OC(=O)CCNC(=N)C(C)(C)N=NC(C)(C)C(=N)NCCC(O)=O NMZSJIQGMAGSSO-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 description 1
- GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZMXAGBLXFWEIHG-UHFFFAOYSA-N C(C1=CC=CC=C1)Cl.C(C=C)(=O)OCCN Chemical compound C(C1=CC=CC=C1)Cl.C(C=C)(=O)OCCN ZMXAGBLXFWEIHG-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 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
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- WQHCGPGATAYRLN-UHFFFAOYSA-N chloromethane;2-(dimethylamino)ethyl prop-2-enoate Chemical group ClC.CN(C)CCOC(=O)C=C WQHCGPGATAYRLN-UHFFFAOYSA-N 0.000 description 1
- RYHUWOIBTVWXFZ-UHFFFAOYSA-N chloromethane;5-(dimethylamino)-2-methylidenepentanamide Chemical compound ClC.CN(C)CCCC(=C)C(N)=O RYHUWOIBTVWXFZ-UHFFFAOYSA-N 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 239000004851 dental resin Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 1
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- JZBZLRKFJWQZHU-UHFFFAOYSA-N n,n,2,4,6-pentamethylaniline Chemical compound CN(C)C1=C(C)C=C(C)C=C1C JZBZLRKFJWQZHU-UHFFFAOYSA-N 0.000 description 1
- DZXAIYQRCQALGE-UHFFFAOYSA-N n,n,2,4-tetramethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1C DZXAIYQRCQALGE-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- IRRRAJMWQGSBKY-UHFFFAOYSA-N n,n-diethyl-2,4,6-trimethylaniline Chemical compound CCN(CC)C1=C(C)C=C(C)C=C1C IRRRAJMWQGSBKY-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- KSOMQZOHPWJPMM-UHFFFAOYSA-N propyl 4-(diethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(CC)CC)C=C1 KSOMQZOHPWJPMM-UHFFFAOYSA-N 0.000 description 1
- SCNYCWQULCHALD-UHFFFAOYSA-N propyl 4-(dimethylamino)benzoate Chemical compound CCCOC(=O)C1=CC=C(N(C)C)C=C1 SCNYCWQULCHALD-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- A61K6/80—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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
- C08F2/08—Organic solvent with the aid of dispersing agents for the polymer
-
- 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
- C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08F222/00—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
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/56—Non-aqueous solutions or dispersions
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本実施形態の重合性組成物の製造方法は、第1の重合性単量体の中に、第2の重合性単量体及び/又は第2の重合性単量体の重合体が分散している重合性組成物を製造する方法である。
第1の重合性単量体は、(メタ)アクリレートであることが好ましく、(メタ)アクリロイルオキシ基を2個以上有する多官能(メタ)アクリレートであることがさらに好ましい。
第2の重合性単量体は、第1の重合性単量体に不溶である。
溶媒としては、第1の重合性単量体及び第2の重合性単量体を溶解させることが可能であれば、特に限定されないが、例えば、エタノール、アセトン、ヘキサン、クロロホルム等の有機溶媒等が挙げられ、二種以上を併用してもよい。
光重合開始剤としては、例えば、カンファーキノン、フェニルビス(2,4,6-トリメチルベンゾイル)ホスフィンオキシド、2,4,6-トリメチルベンゾイルジフェニルホスフィンオキサイド、ベンジルケタール、ジアセチルケタール、ベンジルジメチルケタール、ベンジルジエチルケタール、ベンジルビス(2-メトキシエチル)ケタール、4,4'-ジメチル(ベンジルジメチルケタール)、アントラキノン、1-クロロアントラキノン、2-クロロアントラキノン、1,2-ベンズアントラキノン、1-ヒドロキシアントラキノン、1-メチルアントラキノン、2-エチルアントラキノン、1-ブロモアントラキノン、チオキサントン、2-イソプロピルチオキサントン、2-ニトロチオキサントン、2-メチルチオキサントン、2,4-ジメチルチオキサントン、2,4-ジエチルチオキサントン、2,4-ジイソプロピルチオキサントン、2-クロロ-7-トリフルオロメチルチオキサントン、チオキサントン-10,10-ジオキシド、チオキサントン-10-オキシド、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル、ベンゾフェノン、ビス(4-ジメチルアミノフェニル)ケトン、4,4'-ビス(ジエチルアミノ)ベンゾフェノン等が挙げられ、二種以上を併用してもよい。
第3級アミンは、第3級脂肪族アミン及び第3級芳香族アミンのいずれであってもよいが、第3級芳香族アミンであることが好ましく、p-ジアルキルアミノ安息香酸アルキルであることが特に好ましい。
重合禁止剤としては、例えば、ジブチルヒドロキシトルエン(2,6-ジ-tert-ブチル-p-クレゾール)、6-tert-ブチル-2,4-キシレノール等が挙げられ、二種以上を併用してもよい。
フィラーとしては、例えば、無水ケイ酸粉末、ヒュームドシリカ、アルミナ粉末、ガラス粉末(例えば、バリウムガラス粉末、フルオロアルミノシリケートガラス粉末)等が挙げられ、二種以上を併用してもよい。
熱重合開始剤としては、2,2'-アゾビス(2-メチルプロピオン酸)ジメチル、2,2'-アゾビス(イソブチロニトリル)、2,2'-アゾビス(2,4-ジメチルバレロニトリル)、2,2'-アゾビス(2-メチルブチロニトリル)、1,1'-アゾビス(シクロヘキサンカルボニトリル)、2,2'-アゾビス(4-メトキシ-2,4-ジメチルバレロニトリル)、4,4'-アゾビス(4-シアノ吉草酸)、2,2'-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド]、2,2'-アゾビス[N-(2-カルボキシエチル)-2-メチルプロピオンアミジン]n水和物、2,2'-アゾビス(2-メチルプロピオンアミジン)二塩酸塩、2,2'-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]、2,2'-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]二塩酸塩等が挙げられ、二種以上を併用してもよい。
本実施形態の重合性組成物は、第1の重合性単量体の中に、第2の重合性単量体及び/又は第2の重合性単量体の重合体が分散している。ここで、第1の重合性単量体は、液体であり、第2の重合性単量体は、固体である。
第1の重合性単量体としての、エトキシ化ビスフェノールAジメタクリレート(以下、BisMEPPという)3.5g及びネオペンチルグリコールジメタクリレート(以下、NPGという)7.2g、(±)-カンファーキノン0.01g、p-ジメチルアミノ安息香酸エチル0.03gを混合し、液状組成物(1)を得た。
第1の重合性単量体としての、BisMEPP3.3g及びNPG6.5g、第2の重合性単量体としての、2-(メタクリロイルオキシ)エチルトリメチルアンモニウムクロライド(以下、MTMACという)2.5g、(±)-カンファーキノン0.01g、p-ジメチルアミノ安息香酸エチル0.04gを、エタノール100mLに溶解させ、第1の溶液を得た。
BisMEPP4.7g、NPG9.5g、MTMAC2.5g、(±)-カンファーキノン0.01g、p-ジメチルアミノ安息香酸エチル0.04gを、エタノール100mLに溶解させ、第1の溶液を得た。
BisMEPP12.0g、NPG24.5g、MTMAC2.5g、(±)-カンファーキノン0.01g、p-ジメチルアミノ安息香酸エチル0.04gを、エタノール100mLに溶解させ、第1の溶液を得た。
第2の重合性単量体として、3-(アクリルアミドプロピル)トリメチルアンモニウムクロライド(以下、AATMACという)を用いた以外は、実施例1-1と同様にして、歯科用コンポジットレジンを得た。
第2の重合性単量体として、(2-(アクリロイルオキシ)エチル)トリメチルアンモニウムクロライド(以下ATMACという)を用いた以外は、実施例1-1と同様にして、歯科用コンポジットレジンを得た。
BisMEPP1.5g、NPG3.0g、MTMAC9.0g、(±)-カンファーキノン0.02g、p-ジメチルアミノ安息香酸エチル0.04gを、エタノール100mLに溶解させ、第1の溶液を得た。
第1の重合性単量体としての、NPG20g、第2の重合性単量体としての、MTMAC20gを、エタノール1Lに溶解させ、第1の溶液を得た。次に、第1の溶液を70℃で15時間撹拌した後、室温まで流水冷却し、第2の溶液を得た。次に、第2の溶液90g、液状組成物(2)5.5gを撹拌し、第3の溶液を得た。
NPG20g、MTMAC20g、2,2'-アゾビス(2-メチルプロピオン酸)ジメチル0.05gを、エタノール1Lに溶解させ、第1の溶液を得た。次に、第1の溶液を55℃で15時間撹拌し、NPGとMTMACを共重合した後、室温まで流水冷却し、第2の溶液を得た。次に、第2の溶液90g、液状組成物(2)5.5gを撹拌し、第3の溶液を得た。
MTMAC0.3g、メジアン径0.4μmの3-グリシジルオキシトリメトキシシランにより表面処理されているフルオロアルミノシリケートガラス粉末3.3g、液状組成物(1)2.4gを自動乳鉢で混錬し、歯科用コンポジットレジンを得た。
凍結粉砕器に、MTMAC2g、液体窒素10mLを投入した後、5分間粉砕した。しかしながら、MTMACの粉砕物は、取り出した直後から吸湿が始まり、潮解したため、粉末として得られず、歯科用コンポジットレジンが得られなかった。
直径1cm、厚さ5mmのシリコーンモールドに歯科用コンポジットレジンを流し込んだ後、歯科用光照射器を用いて、歯科用コンポジットレジンを硬化させた。得られた硬化体の表面を耐水研磨紙#4000で注水研磨し、試験片を得た。
試験片の表面を目視で観察し、硬化体の外観を評価した。
不可:試験片の表面が不均一である場合
<硬化体の抗菌効果>
試験片の表面をSEMで観察し、硬化体の抗菌効果を評価した。
不可:試験片の表面にMTMACの重合体の粒子が存在していない場合
なお、硬化体の抗菌効果は、一般に、抗菌性基を有する重合体の粒子が硬化体の表面に存在している場合に優れる。
Claims (7)
- 第1の重合性単量体の中に、第2の重合性単量体及び/又は第2の重合性単量体の重合体が分散している重合性組成物を製造する方法であって、
前記第1の重合性単量体と、前記第2の重合性単量体及び/又は前記第2の重合性単量体の重合体とが、溶媒に溶解している溶液を得る第1の工程と、
前記溶液から前記溶媒を留去する第2の工程を含み、
前記第1の重合性単量体は、液体であり、
前記第2の重合性単量体は、固体である、重合性組成物の製造方法。 - 前記第1の重合性単量体及び/又は前記第2の重合性単量体は、(メタ)アクリレートである、請求項1に記載の重合性組成物の製造方法。
- 前記第2の重合性単量体は、抗菌性基を有する、請求項1又は2に記載の重合性組成物の製造方法。
- 前記第1の工程は、前記第1の重合性単量体の少なくとも一部と、前記第2の重合性単量体を、前記溶媒に溶解させて第1の溶液を得る工程を含む、請求項1~3の何れか1項に記載の重合性組成物の製造方法。
- 前記第1の工程は、前記第1の重合性単量体の一部と、前記第2の重合性単量体を、前記溶媒に溶解させて第1の溶液を得る工程と、前記第1の溶液を加熱し、前記第1の重合性単量体の一部と、前記第2の重合性単量体を共重合して第2の溶液を得る工程と、前記第2の溶液と、前記第1の重合性単量体の残部の少なくとも一部を混合して第3の溶液を得る工程を含む、請求項1~3の何れか1項に記載の重合性組成物の製造方法。
- 第1の重合性単量体の中に、第2の重合性単量体及び/又は第2の重合性単量体の重合体が分散しており、
前記第1の重合性単量体は、液体であり、
前記第2の重合性単量体は、固体である、重合性組成物。 - 前記第2の重合性単量体は、抗菌性基を有する、請求項6に記載の重合性組成物。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020127566A JP7453083B2 (ja) | 2020-07-28 | 2020-07-28 | 重合性組成物の製造方法及び重合性組成物 |
US17/443,357 US20220033533A1 (en) | 2020-07-28 | 2021-07-26 | Method of producing polymerizable composition and polymerizable composition |
EP21187673.5A EP3944851A1 (en) | 2020-07-28 | 2021-07-26 | Method of producing polymerizable composition and polymerizable composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020127566A JP7453083B2 (ja) | 2020-07-28 | 2020-07-28 | 重合性組成物の製造方法及び重合性組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2022024778A true JP2022024778A (ja) | 2022-02-09 |
JP7453083B2 JP7453083B2 (ja) | 2024-03-19 |
Family
ID=77050910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020127566A Active JP7453083B2 (ja) | 2020-07-28 | 2020-07-28 | 重合性組成物の製造方法及び重合性組成物 |
Country Status (3)
Country | Link |
---|---|
US (1) | US20220033533A1 (ja) |
EP (1) | EP3944851A1 (ja) |
JP (1) | JP7453083B2 (ja) |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3357094B2 (ja) | 1991-10-18 | 2002-12-16 | 株式会社クラレ | 抗菌性重合性組成物、それより得られるポリマーおよび用品 |
JP4198237B2 (ja) | 1998-08-20 | 2008-12-17 | 株式会社クラレ | 抗菌性歯科用接着剤システム |
CA2379626C (en) * | 2000-05-22 | 2010-04-13 | Kuraray Co., Ltd. | Antibacterial composition |
JP4822609B2 (ja) | 2000-05-22 | 2011-11-24 | クラレメディカル株式会社 | 抗菌性組成物 |
DE60314433T2 (de) * | 2002-09-20 | 2008-02-14 | Nisshinbo Industries, Inc. | Zusammensetzung für polyelektrolyte,polyelektrolyte,elektrische doppelschichtkondensatoren und sekundärzellen mit wasserfreiem elektrolyt |
US20110256510A1 (en) * | 2009-01-10 | 2011-10-20 | David Henry Pashley | Use of Quaternary Ammonium Compounds to Inhibit Endogenous MMPs in Tooth Dentin |
US9199203B2 (en) * | 2012-04-19 | 2015-12-01 | Saltworks Technologies, Inc. | Resilient ion exchange membranes prepared by polymerizing ionic surfactant monomers |
US20160266286A1 (en) | 2013-09-16 | 2016-09-15 | Coelux S.R.L. | Composite system comprising a polymer matrix and core-shell nanoparticles, process for preparing it and use thereof |
CN106749878B (zh) * | 2016-12-30 | 2019-05-31 | 中科院广州化学有限公司南雄材料生产基地 | 一种季铵盐阳离子型水性含氟聚丙烯酸酯和乳液及该乳液的制备 |
JP7104488B2 (ja) | 2018-03-30 | 2022-07-21 | 株式会社松風 | ウレタン結合を有するラジカル重合性シランカップリング化合物およびそれらを含有する医科歯科用硬化性組成物 |
JP7053433B2 (ja) | 2018-11-15 | 2022-04-12 | クラレノリタケデンタル株式会社 | 硬化性組成物 |
JP2021187833A (ja) | 2020-05-29 | 2021-12-13 | 株式会社ジーシー | 重合性組成物の製造方法、重合性組成物、及び硬化物 |
-
2020
- 2020-07-28 JP JP2020127566A patent/JP7453083B2/ja active Active
-
2021
- 2021-07-26 EP EP21187673.5A patent/EP3944851A1/en active Pending
- 2021-07-26 US US17/443,357 patent/US20220033533A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
US20220033533A1 (en) | 2022-02-03 |
EP3944851A1 (en) | 2022-02-02 |
JP7453083B2 (ja) | 2024-03-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Moszner et al. | A partially aromatic urethane dimethacrylate as a new substitute for Bis-GMA in restorative composites | |
JP4986437B2 (ja) | 歯科用硬化性組成物 | |
ES2601057T3 (es) | Composición curable para fines dentales | |
WO2001095862A1 (en) | Low shrinking polymerizable dental material | |
EP1393705A1 (en) | Dental restorative compounds | |
WO2017098724A1 (ja) | 歯科用接着材 | |
WO2019044815A1 (ja) | 非溶媒系歯科用接着性組成物 | |
JP2021187833A (ja) | 重合性組成物の製造方法、重合性組成物、及び硬化物 | |
JPH08245329A (ja) | 義歯床用裏装材 | |
JP5634298B2 (ja) | 分包型の歯科用重合性支台築造材料 | |
JP7453083B2 (ja) | 重合性組成物の製造方法及び重合性組成物 | |
JP2937808B2 (ja) | 歯科用接着性組成物 | |
US11697694B2 (en) | Method of manufacturing polymerizable composition, polymerizable composition, and cured product | |
JP5894100B2 (ja) | 歯科用重合性組成物 | |
JP6035073B2 (ja) | 歯科用硬化性組成物 | |
WO2022030643A1 (ja) | 光硬化性歯科矯正具用樹脂組成物 | |
JP3468901B2 (ja) | 義歯床用硬化性組成物 | |
Howard et al. | Preparation and evaluation of a novel star-shaped polyacid-constructed dental glass–ionomer system | |
JP5342907B2 (ja) | 重合性アダマンタン誘導体及び歯科用組成物 | |
JP4926440B2 (ja) | 歯科用グラスアイオノマーセメント液 | |
WO2022209203A1 (ja) | 歯科用組成物の製造方法、及び歯科用組成物 | |
JP7074842B2 (ja) | 歯科用充填材及び歯科用重合性組成物 | |
JP6821165B2 (ja) | 義歯床、マウスピース及びそれらの製造方法 | |
JP4644459B2 (ja) | 歯科用硬化性組成物 | |
WO2022138972A1 (ja) | 歯科用組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20230329 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20231018 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231024 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20231220 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240305 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20240307 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 7453083 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |