JP4904015B2 - 未反応モノマーを軽減した医科歯科用材料 - Google Patents
未反応モノマーを軽減した医科歯科用材料 Download PDFInfo
- Publication number
- JP4904015B2 JP4904015B2 JP2005114020A JP2005114020A JP4904015B2 JP 4904015 B2 JP4904015 B2 JP 4904015B2 JP 2005114020 A JP2005114020 A JP 2005114020A JP 2005114020 A JP2005114020 A JP 2005114020A JP 4904015 B2 JP4904015 B2 JP 4904015B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mass
- meth
- acrylate
- medical
- 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.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims description 34
- 239000005548 dental material Substances 0.000 title description 2
- 239000012567 medical material Substances 0.000 title description 2
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 239000003178 glass ionomer cement Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000005518 polymer electrolyte Substances 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 238000000108 ultra-filtration Methods 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- -1 5-hydroxypentyl Chemical group 0.000 description 18
- 239000002253 acid Substances 0.000 description 14
- 239000011344 liquid material Substances 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 239000004568 cement Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920000867 polyelectrolyte Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000007656 barbituric acids Chemical class 0.000 description 4
- 238000003795 desorption Methods 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical class OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 3
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- QJCPEOFEBREKQB-UHFFFAOYSA-N benzenesulfinamide Chemical compound NS(=O)C1=CC=CC=C1 QJCPEOFEBREKQB-UHFFFAOYSA-N 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 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
- 238000009835 boiling Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 2
- NPZOFLLFFNIYON-UHFFFAOYSA-N n,n,4-trimethylbenzenesulfinamide Chemical compound CN(C)S(=O)C1=CC=C(C)C=C1 NPZOFLLFFNIYON-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PZGVVCOOWYSSGB-KWZUVTIDSA-L (z)-but-2-enedioate;dioctyltin(2+) Chemical class [O-]C(=O)\C=C/C([O-])=O.CCCCCCCC[Sn+2]CCCCCCCC PZGVVCOOWYSSGB-KWZUVTIDSA-L 0.000 description 1
- OZOSSJWZNHBBDV-UHFFFAOYSA-N 1,3,5-trimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CC1C(=O)N(C)C(=S)N(C)C1=O OZOSSJWZNHBBDV-UHFFFAOYSA-N 0.000 description 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 1
- NFQAQKVFBFWVKQ-UHFFFAOYSA-N 1,3-dimethyl-5-(2-methylpropyl)-1,3-diazinane-2,4,6-trione Chemical compound CC(C)CC1C(=O)N(C)C(=O)N(C)C1=O NFQAQKVFBFWVKQ-UHFFFAOYSA-N 0.000 description 1
- UGFMJBRXTRUGJC-UHFFFAOYSA-N 1,3-dimethyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1C1=CC=CC=C1 UGFMJBRXTRUGJC-UHFFFAOYSA-N 0.000 description 1
- FBQJKKPQBMSWEP-UHFFFAOYSA-N 1,3-diphenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 FBQJKKPQBMSWEP-UHFFFAOYSA-N 0.000 description 1
- DABBHRQKJNIVFT-UHFFFAOYSA-N 1,5-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CC1C(=O)NC(=O)N(C)C1=O DABBHRQKJNIVFT-UHFFFAOYSA-N 0.000 description 1
- KCWWCWMGJOWTMY-UHFFFAOYSA-N 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)NC(=O)N1CC1=CC=CC=C1 KCWWCWMGJOWTMY-UHFFFAOYSA-N 0.000 description 1
- DCGGMHIZEAHUJL-UHFFFAOYSA-N 1-methyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)NC1=O DCGGMHIZEAHUJL-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- GPLACOONWGSIIP-UHFFFAOYSA-N 2-(n-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]anilino)acetic acid Chemical compound CC(=C)C(=O)OCC(O)CN(CC(O)=O)C1=CC=CC=C1 GPLACOONWGSIIP-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
- JZXVADSBLRIAIB-UHFFFAOYSA-N 2-pyrrolidin-2-ylethanol Chemical compound OCCC1CCCN1 JZXVADSBLRIAIB-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- CDZKKWTUOUWMAN-UHFFFAOYSA-N 4-(4-methylphenyl)sulfinylmorpholine Chemical compound C1=CC(C)=CC=C1S(=O)N1CCOCC1 CDZKKWTUOUWMAN-UHFFFAOYSA-N 0.000 description 1
- HTKIZIQFMHVTRJ-UHFFFAOYSA-N 5-butyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC1C(=O)NC(=O)NC1=O HTKIZIQFMHVTRJ-UHFFFAOYSA-N 0.000 description 1
- PAAOBODHLHVLMN-UHFFFAOYSA-N 5-butyl-1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC1C(=O)N(C)C(=O)N(C)C1=O PAAOBODHLHVLMN-UHFFFAOYSA-N 0.000 description 1
- IRSXYVMZLDSECN-UHFFFAOYSA-N 5-butyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CCCCC1C(=O)NC(=S)NC1=O IRSXYVMZLDSECN-UHFFFAOYSA-N 0.000 description 1
- ANBKBYQJFJUEBR-UHFFFAOYSA-N 5-cyclohexyl-1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1C1CCCCC1 ANBKBYQJFJUEBR-UHFFFAOYSA-N 0.000 description 1
- WTUYGYIHVPSHQF-UHFFFAOYSA-N 5-cyclopentyl-1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1C1CCCC1 WTUYGYIHVPSHQF-UHFFFAOYSA-N 0.000 description 1
- FMTLDVACNZDTQL-UHFFFAOYSA-N 5-ethyl-1,3-diazinane-2,4,6-trione Chemical compound CCC1C(=O)NC(=O)NC1=O FMTLDVACNZDTQL-UHFFFAOYSA-N 0.000 description 1
- QBCQXNDNMOHQIU-UHFFFAOYSA-N 5-ethyl-1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CCC1C(=O)N(C)C(=O)N(C)C1=O QBCQXNDNMOHQIU-UHFFFAOYSA-N 0.000 description 1
- GFPIGNBQTXNNAG-UHFFFAOYSA-N 5-propan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound CC(C)C1C(=O)NC(=O)NC1=O GFPIGNBQTXNNAG-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
- 229960001748 allylthiourea Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-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
- VIJYFGMFEVJQHU-UHFFFAOYSA-N aluminum oxosilicon(2+) oxygen(2-) Chemical compound [O-2].[Al+3].[Si+2]=O VIJYFGMFEVJQHU-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- PZGVVCOOWYSSGB-UHFFFAOYSA-L but-2-enedioate;dioctyltin(2+) Chemical compound CCCCCCCC[Sn]1(CCCCCCCC)OC(=O)C=CC(=O)O1 PZGVVCOOWYSSGB-UHFFFAOYSA-L 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000013043 cell viability test Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000006059 cover glass Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000013022 formulation composition Substances 0.000 description 1
- 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 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 238000004898 kneading Methods 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- WKOLGNXVNMSYKY-UHFFFAOYSA-N n-(1,3-dihydroxypropyl)prop-2-enamide Chemical compound OCCC(O)NC(=O)C=C WKOLGNXVNMSYKY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 231100000820 toxicity test Toxicity 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 239000002672 zinc phosphate cement Substances 0.000 description 1
Landscapes
- Dental Preparations (AREA)
Description
酸反応性フィラーとしては酸化アルミニウム−酸化ケイ素を基本骨格とし、修飾イオンンとしてカルシウム及び/またはストロンチウムを含むフルオロアルミノシリケート粉末が好適である。また該酸反応性フィラーは液材とのなじみ性や寿命性を共存させる目的でシランカップリング剤にて表面処理を施してもよい。
1.酸性高分子電解質の調整
株式会社松風製グラスアイオノマーCX-Plusの液材100mlに蒸留水900mlを加水し、ベーンポンプにて日本ミリポア製限外濾過膜(バイオマックス 分画分子量 濾過面積0.1m2)にて最終体積が100mlになるまで限外濾過を行った。その後、さらに蒸留水を400ml加え予備凍結し東京理科器械製フリーズドライヤーを使用し、凍結乾燥した。得られたポリアルケン酸粉末を蒸留水にて固形分濃度が45wt%になるように溶液調整した。この酸性高分子電解質溶液をリン酸緩衝液にて希釈しGPC測定を行ったが、未重合モノマーは認められなかった。この45wt%溶液を標準液1(実施例用液1)とする。
標準液1にアクリル酸モノマーを表1に示した濃度になるように添加した。
実施例用液又は比較例用液を用いて粉液型レジンモディファイドグラスアイオノマーセメントの液材を表2の調合組成で調整した。また粉材は表3の調合組成にて調整した。なお表3に記載した過硫酸カリウムおよびアスコルビン酸は市販薬品の結晶をアルミナ乳鉢にて50μm以下に微粉砕し株式会社松風製CX-PLUS粉材に均一混合した。
2-HEMA:2−ヒドロキシエチルメタクリレート
医科・歯科用硬化性組成物の実施例用液材又は比較例用液材から揮発するアクリル酸モノマーの定量分析を以下の分析方法にて行った。
試料50mgを石英製試料皿に秤量し、加熱炉に設置した加熱管(室温25℃)中央部に導入した。窒素ガスを50ml/minの流速で流し、追い出される揮発性成分を吸着管(Carbotrap400)に捕集した。捕集時間は20分とした。(気体採取量1L)
捕集した吸着管を熱脱離GC/MS分析システムのチャンバー部にセットした。チャンバー部(吸着管)を急速加熱して有機成分を離脱させ、GC/MSに導入し測定した。得られたトータルイオンクロマトグラム(TIC)で試料間の比較を行い、検出された成分のスペクトル同定を行った。なお、GC/MS測定条件は以下のとうりである。
(熱離脱条件)
装置 :スペルコ社製 熱離脱装置(TDU)
離脱条件 :300℃まで急速昇温し5分間保持
(GC/MS測定条件)
GC/MS :HP6890/HP5973
分離カラム:SPB-1(sulfur)30m×0.32mmI.D 4.0μm Film
GC温度 :‐30℃→300℃ 昇温10℃/min
GC注入口:TDU使用
キャリアー:ヘリウム 3ml/min
検出器 :質量分析計(MS)230℃
測定質量範囲:m/Z=33~600
上述した分析の結果を表4に記載する。
東洋紡績株式会社製三次元培養皮膚モデル「テストスキン」を用いて以下に記載した方法にて抽出した溶液を該細胞に10時間原液のまま作用させた後に細胞生存率を算出した。なお実験操作は「テストスキン」使用方法に従い行った。
実施例用液材1〜3は刺激臭をほとんど感じず、比較例用液材1,2は刺激臭が認められた。
Claims (1)
- レジンモディファイドグラスアイオノマーセメントにおいて、フルオロアルミノシリケートガラス粉末、重合開始材、重合促進材を含む粉成分と、液成分として未反応モノマー0.00001〜1質量%を含む酸性高分子電解質、精製水、ヒドロキシカルボン酸およびラジカル重合性単量体からなり、前記未反応モノマーは、限外濾過膜分離によって、前記0.00001〜1質量%の濃度まで除去されたものであるレジンモディファイドグラスアイオノマーセメント。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005114020A JP4904015B2 (ja) | 2005-04-11 | 2005-04-11 | 未反応モノマーを軽減した医科歯科用材料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005114020A JP4904015B2 (ja) | 2005-04-11 | 2005-04-11 | 未反応モノマーを軽減した医科歯科用材料 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006290803A JP2006290803A (ja) | 2006-10-26 |
JP4904015B2 true JP4904015B2 (ja) | 2012-03-28 |
Family
ID=37411762
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005114020A Active JP4904015B2 (ja) | 2005-04-11 | 2005-04-11 | 未反応モノマーを軽減した医科歯科用材料 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP4904015B2 (ja) |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU618772B2 (en) * | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
JP2894856B2 (ja) * | 1991-03-25 | 1999-05-24 | 三井化学株式会社 | 歯質表面処理用アクリル系共重合体およびその用途 |
JP2922036B2 (ja) * | 1991-10-31 | 1999-07-19 | 日東電工株式会社 | 耐熱性にすぐれた感圧性接着剤およびその接着シート類の製造方法 |
JP3040032B2 (ja) * | 1992-03-27 | 2000-05-08 | 日東電工株式会社 | 耐熱性にすぐれた感圧性接着剤およびその接着シ―ト類とこれらの製造方法 |
JP3450059B2 (ja) * | 1994-09-28 | 2003-09-22 | 大日本塗料株式会社 | 歯科セメント用ガラス粉末 |
JPH0948702A (ja) * | 1995-08-03 | 1997-02-18 | Dainippon Toryo Co Ltd | 歯科用セメント組成物 |
JP4759782B2 (ja) * | 2000-02-16 | 2011-08-31 | ダイキン工業株式会社 | フッ素系アイオノマーの精製・濃縮方法 |
-
2005
- 2005-04-11 JP JP2005114020A patent/JP4904015B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2006290803A (ja) | 2006-10-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU618772B2 (en) | Photocurable ionomer cement systems | |
Wilson | Resin-modified glass-ionomer cements. | |
CN107406723B (zh) | 加成-断裂低聚物 | |
EP2394628B1 (en) | Dental filling repair kit | |
US9682018B2 (en) | Denture tooth and material | |
EP0684033B1 (en) | Adhesive composition for dental treatment | |
EP2163234A1 (en) | Dental filling/restoration kit | |
US20090258966A1 (en) | Dental Composition | |
Nie et al. | Synthesis and photopolymerization of N, N′-dimethyl,-N, N′-di (methacryloxy ethyl)-1, 6-hexanediamine as a polymerizable amine coinitiator for dental restorations | |
JPH09255515A (ja) | 歯科用セメント組成物 | |
JP5765896B2 (ja) | 歯科用組成物 | |
WO2005067866A1 (ja) | 歯科用または外科用接着剤およびそのための重合開始剤組成物 | |
Cadenaro et al. | The effect of curing mode on extent of polymerization and microhardness of dual-cured, self-adhesive resin cements. | |
US3635889A (en) | Adhesion promoting dental materials | |
KR19980032737A (ko) | 치과용 또는 외과용 접착성 조성물 | |
JP2937808B2 (ja) | 歯科用接着性組成物 | |
JP2024500564A (ja) | 硬組織補修用接着性組成物 | |
JP4904015B2 (ja) | 未反応モノマーを軽減した医科歯科用材料 | |
JP2007031339A (ja) | pH調整接着剤組成物 | |
JPH09110913A (ja) | 歯科用または外科用接着剤およびそのための重合開始剤組成物 | |
JP2011173867A (ja) | タンパク質含有レジン系組成物 | |
JP4932210B2 (ja) | 歯科用組成物 | |
KR101868873B1 (ko) | 폴리아크릴산계 공중합체를 포함하는 치과용 시멘트 조성물 | |
WO2018181710A1 (ja) | 歯科材料用多官能モノマーおよび歯科材料用水酸基含有モノマー | |
WO2005090281A1 (ja) | (メタ)アクリル化合物及びその用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080128 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110627 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110912 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111110 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20111110 |
|
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: 20111213 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120106 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 4904015 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150113 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |