JP4832129B2 - Dental composition - Google Patents
Dental composition Download PDFInfo
- Publication number
- JP4832129B2 JP4832129B2 JP2006077325A JP2006077325A JP4832129B2 JP 4832129 B2 JP4832129 B2 JP 4832129B2 JP 2006077325 A JP2006077325 A JP 2006077325A JP 2006077325 A JP2006077325 A JP 2006077325A JP 4832129 B2 JP4832129 B2 JP 4832129B2
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acid
- component
- dental composition
- water
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 239000002245 particle Substances 0.000 claims abstract description 58
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 229920000642 polymer Polymers 0.000 claims abstract description 39
- 239000000178 monomer Substances 0.000 claims abstract description 34
- 210000005239 tubule Anatomy 0.000 claims abstract description 30
- 230000002378 acidificating effect Effects 0.000 claims abstract description 14
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000002612 dispersion medium Substances 0.000 claims abstract description 6
- 150000007513 acids Chemical class 0.000 claims abstract description 5
- -1 acryloxyethyl trimellitic acid Chemical compound 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 239000000839 emulsion Substances 0.000 claims description 47
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 27
- 229910019142 PO4 Inorganic materials 0.000 claims description 17
- 239000010452 phosphate Substances 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 16
- 206010020751 Hypersensitivity Diseases 0.000 claims description 14
- 208000026935 allergic disease Diseases 0.000 claims description 14
- 230000009610 hypersensitivity Effects 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 235000006408 oxalic acid Nutrition 0.000 claims description 11
- 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 claims description 10
- 235000002639 sodium chloride Nutrition 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 229940043430 calcium compound Drugs 0.000 claims description 5
- 150000001674 calcium compounds Chemical class 0.000 claims description 5
- 239000011164 primary particle Substances 0.000 claims description 4
- ASEUXRQULQEGGL-UHFFFAOYSA-N 2-decyl-2-prop-2-enoyloxypropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)(C(O)=O)OC(=O)C=C ASEUXRQULQEGGL-UHFFFAOYSA-N 0.000 claims description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 230000000873 masking effect Effects 0.000 claims description 2
- 230000001629 suppression Effects 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 229920003169 water-soluble polymer Polymers 0.000 claims description 2
- 210000004268 dentin Anatomy 0.000 abstract description 23
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 3
- 239000004615 ingredient Substances 0.000 abstract description 2
- 238000012216 screening Methods 0.000 abstract description 2
- 208000035154 Hyperesthesia Diseases 0.000 abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 45
- 230000000694 effects Effects 0.000 description 15
- 239000008213 purified water Substances 0.000 description 11
- 238000007789 sealing Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 210000003298 dental enamel Anatomy 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004220 aggregation Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 238000004061 bleaching Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 159000000007 calcium salts Chemical class 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005520 cutting process Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 230000001699 photocatalysis Effects 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- DYXRKIIWXQASHJ-JTQLQIEISA-N (2s)-3-(4-hydroxyphenyl)-2-(prop-2-enoyloxyamino)propanoic acid Chemical compound C=CC(=O)ON[C@H](C(=O)O)CC1=CC=C(O)C=C1 DYXRKIIWXQASHJ-JTQLQIEISA-N 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical class C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 235000011148 calcium chloride Nutrition 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- JFZKSSFKEXIEHY-JTQLQIEISA-N (2S)-3-phenyl-2-(prop-2-enoyloxyamino)propanoic acid Chemical compound C(C=C)(=O)ON[C@@H](CC1=CC=CC=C1)C(=O)O JFZKSSFKEXIEHY-JTQLQIEISA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004908 Emulsion polymer Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 239000000551 dentifrice Substances 0.000 description 2
- 201000002170 dentin sensitivity Diseases 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 229960000414 sodium fluoride Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000811 xylitol Substances 0.000 description 2
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- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 2
- 235000010447 xylitol Nutrition 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- DTOUUUZOYKYHEP-UHFFFAOYSA-N 1,3-bis(2-ethylhexyl)-5-methyl-1,3-diazinan-5-amine Chemical compound CCCCC(CC)CN1CN(CC(CC)CCCC)CC(C)(N)C1 DTOUUUZOYKYHEP-UHFFFAOYSA-N 0.000 description 1
- BWAYIRSPWAVMDG-UHFFFAOYSA-N 1-(1,3-dihydroxypropan-2-yl)imidazolidine-2,4-dione Chemical compound OCC(CO)N1CC(=O)NC1=O BWAYIRSPWAVMDG-UHFFFAOYSA-N 0.000 description 1
- SIQZJFKTROUNPI-UHFFFAOYSA-N 1-(hydroxymethyl)-5,5-dimethylhydantoin Chemical compound CC1(C)N(CO)C(=O)NC1=O SIQZJFKTROUNPI-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- GGIDUULRWQOXLR-UHFFFAOYSA-N 2,3,4,5-tetrabromo-6-methylphenol Chemical compound CC1=C(O)C(Br)=C(Br)C(Br)=C1Br GGIDUULRWQOXLR-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- IYOLBFFHPZOQGW-UHFFFAOYSA-N 2,4-dichloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=C(Cl)C(C)=C1Cl IYOLBFFHPZOQGW-UHFFFAOYSA-N 0.000 description 1
- DBHODFSFBXJZNY-UHFFFAOYSA-N 2,4-dichlorobenzyl alcohol Chemical compound OCC1=CC=C(Cl)C=C1Cl DBHODFSFBXJZNY-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
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- DYPOHVRBXIPFIK-UHFFFAOYSA-N 2-(2-methylanilino)acetic acid Chemical compound CC1=CC=CC=C1NCC(O)=O DYPOHVRBXIPFIK-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- HTYFFCPFVMJTKM-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(Cl)C=C1 HTYFFCPFVMJTKM-UHFFFAOYSA-N 0.000 description 1
- WWCLLFXXGLYNKI-UHFFFAOYSA-N 2-(prop-2-enoylamino)oxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1ONC(=O)C=C WWCLLFXXGLYNKI-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- NALMPLUMOWIVJC-UHFFFAOYSA-N n,n,4-trimethylbenzeneamine oxide Chemical compound CC1=CC=C([N+](C)(C)[O-])C=C1 NALMPLUMOWIVJC-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002917 oxazolidines Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- URKBBEIOEBOBIY-UHFFFAOYSA-N pentane-1,1,1,2-tetrol Chemical compound CCCC(O)C(O)(O)O URKBBEIOEBOBIY-UHFFFAOYSA-N 0.000 description 1
- FVGBHSIHHXTYTH-UHFFFAOYSA-N pentane-1,1,1-triol Chemical compound CCCCC(O)(O)O FVGBHSIHHXTYTH-UHFFFAOYSA-N 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- BFDWBSRJQZPEEB-UHFFFAOYSA-L sodium fluorophosphate Chemical compound [Na+].[Na+].[O-]P([O-])(F)=O BFDWBSRJQZPEEB-UHFFFAOYSA-L 0.000 description 1
- 239000011697 sodium iodate Substances 0.000 description 1
- 235000015281 sodium iodate Nutrition 0.000 description 1
- 229940032753 sodium iodate Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- WHWMOMRHHQLBQQ-UHFFFAOYSA-N tert-butyl 4-hydroxybenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(O)C=C1 WHWMOMRHHQLBQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical compound [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Dental Preparations (AREA)
Abstract
Description
本発明は、変色などの不具合の生じた歯の被覆、とくに知覚過敏の症状を有する歯牙などの被覆に有用な歯科用組成物に関する。 The present invention relates to a dental composition useful for coating a tooth having a defect such as discoloration, particularly a tooth having a sensation of hypersensitivity.
歯牙の着色改善は、大きく分類して、漂白によるか、あるいは歯牙色の遮蔽効果を持つ粒子を含んだ硬化性組成物の接着により、行われることが多い。
このうち、漂白はその多くが過酸化水素水を用いることにより行われている。過酸化水素による漂白は、表面に沈着した汚染物を分解するとともに、エナメル質表面を脱灰することにより、歯牙表面の光散乱性を上昇させることによって、見かけ上の歯牙色を白くみせる方法である。この場合、象牙質を被覆するエナメル質が脱灰され、象牙質が露出することにより、特にエナメル質厚の小さい歯頸部において知覚過敏が発生しやすいことが問題点としてあげられる。
Tooth coloring improvement is often roughly classified and performed by bleaching or by adhesion of a curable composition containing particles having a tooth-color shielding effect.
Of these, most bleaching is performed by using hydrogen peroxide. Bleaching with hydrogen peroxide is a method that makes the apparent tooth color whiter by decomposing contaminants deposited on the surface and decalcifying the enamel surface to increase the light scattering property of the tooth surface. is there. In this case, the problem is that the enamel covering the dentin is decalcified and the dentin is exposed, and thus hypersensitivity is likely to occur particularly in the tooth neck portion having a small enamel thickness.
また、歯牙色を遮蔽する効果を持つ粒子を含んだ硬化性組成物を塗布する際の治療方法としては、印象採取し、エナメル質を切削し、印象から得た硬化体の切削表面をエッチングし、その後に、歯科用セメント等を用いて切削表面に接着する方法がとられている。しかしながらこの場合、最初の切削時に、エナメル質に限局した切削が比較的困難であり、局所的に象牙質が露出する可能性があり、硬化体の接着までには硬化体作製の時間を要することから、この期間、重篤な知覚過敏の症状が発生しやすいことが問題点としてあげられる。
さらに、エナメル質の人為的な脱灰により、象牙質が露出した状況においては、象牙質の石灰化度がエナメル質のそれと比較して、格段に低いため、う蝕罹患の危険度（カリエスリスク）が上昇してしまうことが、問題となる。
Also, as a treatment method when applying a curable composition containing particles having an effect of shielding the tooth color, an impression is taken, the enamel is cut, and the cut surface of the cured body obtained from the impression is etched. Thereafter, a method of adhering to the cutting surface using dental cement or the like is employed. In this case, however, cutting limited to enamel is relatively difficult at the time of the first cutting, and the dentin may be locally exposed, and it takes time to make a cured body before bonding the cured body. Therefore, the problem is that during this period, symptoms of severe hypersensitivity are likely to occur.
Furthermore, in the situation where dentin is exposed due to artificial decalcification of enamel, the degree of calcification of dentin is much lower than that of enamel, so the risk of caries (caries risk) ) Is a problem.
象牙質知覚過敏においては、特許文献１に（メタ）アクリル酸エステルから誘導される繰返し単位、および官能基−ＳＯ３Ｒ（Ｒは水素、アルカリ金属またはアンモニウムイオン）を有するビニル化合物から誘導される繰返し単位からなる乳化重合体のエマルジョンから誘導された接着性フィルムによる歯牙の被覆が提案されている。また、さらに、象牙細管を封鎖する技術としては、特許文献２において、カルシウム化合物と反応し、象牙細管径よりも大きな凝集体を形成する水性エマルジョンよりなる抗象牙質知覚過敏症組成物が提案されている。しかしながら、両者とも露出した象牙細管の封鎖に関してのみの記述であり、う蝕病原菌に対する抗菌性も述べられてはいない。さらにこれら組成物を用いると、着色改善のための治療ステップには、知覚過敏を抑制する作業が発生してしまうために、煩雑となる。
本発明の目的は、歯牙色の改善時に必要となる知覚過敏の抑制を効果的に行うために、象牙質の露出した歯質において、象牙細管の開口による知覚過敏を抑制するとともに、露出象牙質近傍の抗菌性を上昇させることができる歯科用組成物を提供することにある。 The object of the present invention is to suppress the hypersensitivity caused by the opening of the dentinal tubules in the exposed dentin in order to effectively suppress the hypersensitivity required when the tooth color is improved. It is providing the dental composition which can raise the antimicrobial property of the vicinity.
発明者らが鋭意検討した結果、本発明の上記目的は、
下記（Ａ）、（Ｂ）、（Ｃ）および（Ｄ）成分からなりそして歯牙色遮蔽および／または知覚過敏抑制に用いられることを特徴とする歯科用組成物。
（Ａ）分子内に酸性基を少なくとも１つ有する重合性単量体（Ｍａ）の少なくとも１種に由来する単量体単位を有する重合体、
（Ｂ）アナターゼ型二酸化チタン粒子、
（Ｃ）溶媒および／または分散媒および
（Ｄ）水溶性酸性化合物。
によって、達成しうることを見いだし、本発明を完成させるに至った。
As a result of intensive studies by the inventors, the object of the present invention is as follows.
A dental composition comprising the following components (A), (B), (C) and (D) and used for tooth color masking and / or suppression of hypersensitivity.
(A) a polymer having a monomer unit derived from at least one polymerizable monomer (Ma) having at least one acidic group in the molecule;
(B) anatase-type titanium dioxide particles,
(C) A solvent and / or a dispersion medium and (D) a water-soluble acidic compound.
As a result, the inventors have found out what can be achieved and have completed the present invention.
歯牙色遮蔽作用と知覚過敏抑制作用とを有する本発明の歯科用組成物を用いることにより、漂白前の知覚過敏を抑制できるだけでなく、その後に行う漂白操作の代替となるか、あるいは漂白効果を向上できる可能性も見い出された。さらに、本発明の歯科用組成物を歯牙表面に塗布することにより、露出象牙質近傍の抗菌性を上昇させうることも見い出した。 By using the dental composition of the present invention having a tooth color shielding action and a hypersensitivity suppressing action, not only can the hypersensitivity before bleaching be suppressed, but also an alternative to the subsequent bleaching operation or the bleaching effect. The possibility of improvement was also found. Furthermore, it has also been found that the antibacterial properties near the exposed dentin can be increased by applying the dental composition of the present invention to the tooth surface.
以下、本発明を詳述する。以下、特別の断りのない限り「部」あるいは「％」は重量基準を示す。又、各パラメータ数値範囲において、「XX〜YY」(XX、YYは数値)というような標記は、原則として「XX以上および／またはYY以下」を意味するものとする。 The present invention is described in detail below. Hereinafter, unless otherwise specified, “part” or “%” indicates a weight basis. In addition, in each parameter numerical value range, a notation such as “XX to YY” (XX and YY are numerical values) basically means “XX or more and / or YY or less”.
本発明における（Ａ）成分は分子内に酸性基を少なくとも１つ有する重合性単量体（Ｍａ）の少なくとも１種に由来する単量体単位を有する重合体である。（Ａ）成分は（Ｍａ）に由来する単量体単位として含んでいれば、特に限定されるものではなく、１種の重合体であっても、２種類以上の重合体の混合物でもかまわない。（Ａ）成分は（Ｍａ）のみに由来する単量体単位のみを単量体単位として含んでいても、後述するような他の単量体（Ｍｂ）に由来する単量体単位をさらに含む共重合体であってもかまわない。
（Ｍａ）は分子内に酸性基を少なくとも１つ有する重合性単量体である。重合性基としては、ラジカル重合性基が好ましく、例えばビニル基、シアン化ビニル基、アクリロイル基、メタアクリロイル基、アクリルアミド基、メタアクリルアミド基などを挙げることができる。また、酸性基としては、例えばカルボキシル基、およびその酸無水基、リン酸基、チオリン酸基、スルホン酸基、スルフィン酸基などを例示することができる。あるいはカルボキシル基の酸無水基のように、実用条件において容易に分解して前記酸性基になるなど、実質上酸性基として機能するものも、酸性基と見なされる。
The component (A) in the present invention is a polymer having a monomer unit derived from at least one polymerizable monomer (Ma) having at least one acidic group in the molecule. The component (A) is not particularly limited as long as it is contained as a monomer unit derived from (Ma), and may be one kind of polymer or a mixture of two or more kinds of polymers. . The component (A) further includes a monomer unit derived from another monomer (Mb) as described later, even if the monomer unit includes only the monomer unit derived from (Ma) alone. It may be a copolymer.
(Ma) is a polymerizable monomer having at least one acidic group in the molecule. The polymerizable group is preferably a radical polymerizable group, and examples thereof include a vinyl group, a vinyl cyanide group, an acryloyl group, a methacryloyl group, an acrylamide group, and a methacrylamide group. Examples of the acidic group include a carboxyl group and its acid anhydride group, phosphoric acid group, thiophosphoric acid group, sulfonic acid group, and sulfinic acid group. Alternatively, a substance that substantially functions as an acidic group, such as an acid anhydride group of a carboxyl group, which easily decomposes under practical conditions to become the acidic group is also regarded as an acidic group.
具体的な（Ｍａ）として、分子中にカルボキシル基を有する重合性化合物としては、（メタ）アクリル酸（以下、アクリル酸とメタアクリル酸の総称として、「（メタ）アクリル酸」と記載する。）、マレイン酸等のα−不飽和カルボン酸；
４−ビニル安息香酸等のビニル芳香環化合物；
１１−（メタ）アクリロイルオキシ−１，１−ウンデカンジカルボン酸（以下、アクリロイルとメタアクリロイルの総称として「（メタ）アクリロイル」と記載する。）等の（メタ）アクリロイルオキシ基とカルボン酸基の間に直鎖炭化水素基が存在するカルボン酸化合物；
６−（メタ）アクリロイルオキシエチルナフタレン−１，２，６−トリカルボン酸等の（メタ）アクリロイルオキシアルキルナフタレン（ポリ）カルボン酸；
４−（メタ）アクリロイルオキシアルキルトリメリット酸（４−（メタ）アクリロイルオキシメチルトリメリット酸、４−（メタ）アクリロイルオキシエチルトリメリット酸、４−（メタ）アクリロイルオキシブチルトリメリット酸）等といった（メタ）アクリロイルオキシアルキルトリメリット酸；
４−［２−ヒドロキシ−３−（メタ）アクリロイルオキシ］ブチルトリメリット酸等のさらに水酸基を含有する化合物；
２，３−ビス（３，４−ジカルボキシベンゾイルオキシ）プロピル（メタ）アクリレ−ト（以下、アクリレートとメタアクリレートの総称として「（メタ）アクリレート」のように記載する。）等のカルボキシベンゾイルオキシを有する化合物；
Ｎ，Ｏ−ジ（メタ）アクリロイルオキシチロシン、Ｏ−（メタ）アクリロイルオキシチロシン、Ｎ−（メタ）アクリロイルオキシチロシン、Ｎ−（メタ）アクリロイルオキシフェニルアラニン、Ｏ−（メタ）アクリロイルオキシフェニルアラニン、Ｎ，Ｏ−ビス（（メタ）アクリロイルオキシ）フェニルアラニン等のＮ−および／またはＯ−モノまたはＮ，Ｏ−ジ（メタ）アクリロイルオキシアミノ酸；
Ｎ−（メタ）アクリロイル−４−アミノ安息香酸、Ｎ−（メタ）アクリロイル−５−アミノ安息香酸、２−または３−または４−（メタ）アクリロイルオキシ安息香酸、４−または５−（メタ）アクリロイルアミノサリチル酸等のＮ−および／またはＯ−モノまたはジ（メタ）アクリロイル（アミノまたはオキシ）安息香酸系化合物；
２−ヒドロキシエチル（メタ）アクリレートとピロメリット酸二無水物の付加生成物、２−ヒドロキシエチル（メタ）アクリレ−トと無水マレイン酸または３，３’，４，４’−ベンゾフェノンテトラカルボン酸二無水物または３，３’，４，４’−ビフェニルテトラカルボン酸二無水物の付加反応物等のヒドロキシアルキル（メタ）アクリレートと不飽和ポリカルボン酸無水物の付加反応物；
２−（３，４−ジカルボキシベンゾイルオキシ）−１，３−ジ（メタ）アクリロイルオキシプロパン等）などのポリカルボキシベンゾイルオキシと（メタ）アクリロイルオキシを有する化合物；
Ｎ−フェニルグリシンまたはＮ−トリルグリシンとグリシジル（メタ）アクリレ−トとの付加物；
４−［Ｎ−（２−ヒドロキシ−３−（メタ）アクリロイルオキシプロピル）アミノ］フタル酸、３または４−［Ｎ−メチル−Ｎ−（２−ヒドロキシ−３−（メタ）アクリロイルオキシプロピル）アミノ］フタル酸などのＮ−アルキル−Ｎ−（ヒドロキシ（メタ）アクリロイルオキシアルキル）アミノフタル酸化合物
などを挙げることができる。これらのうち、１１−（メタ）アクリロイルオキシ−１，１−ウンデカンジカルボン酸および４−（メタ）アクリロイルオキシエチルトリメリット酸が好ましく用いられる。
As specific (Ma), as the polymerizable compound having a carboxyl group in the molecule, (meth) acrylic acid (hereinafter referred to as “(meth) acrylic acid” is a generic term for acrylic acid and methacrylic acid). ), Α-unsaturated carboxylic acids such as maleic acid;
Vinyl aromatic ring compounds such as 4-vinylbenzoic acid;
Between a (meth) acryloyloxy group and a carboxylic acid group such as 11- (meth) acryloyloxy-1,1-undecanedicarboxylic acid (hereinafter referred to as “(meth) acryloyl” as a generic term for acryloyl and methacryloyl). A carboxylic acid compound in which a linear hydrocarbon group is present;
(Meth) acryloyloxyalkylnaphthalene (poly) carboxylic acids such as 6- (meth) acryloyloxyethylnaphthalene-1,2,6-tricarboxylic acid;
4- (meth) acryloyloxyalkyl trimellitic acid (4- (meth) acryloyloxymethyl trimellitic acid, 4- (meth) acryloyloxyethyl trimellitic acid, 4- (meth) acryloyloxybutyl trimellitic acid), etc. (Meth) acryloyloxyalkyl trimellitic acid;
A compound further containing a hydroxyl group such as 4- [2-hydroxy-3- (meth) acryloyloxy] butyl trimellitic acid;
Carboxybenzoyloxy such as 2,3-bis (3,4-dicarboxybenzoyloxy) propyl (meth) acrylate (hereinafter referred to as “(meth) acrylate” as a generic term for acrylate and methacrylate). A compound having:
N, O-di (meth) acryloyloxytyrosine, O- (meth) acryloyloxytyrosine, N- (meth) acryloyloxytyrosine, N- (meth) acryloyloxyphenylalanine, O- (meth) acryloyloxyphenylalanine, N, N- and / or O-mono or N, O-di (meth) acryloyloxyamino acids such as O-bis ((meth) acryloyloxy) phenylalanine;
N- (meth) acryloyl-4-aminobenzoic acid, N- (meth) acryloyl-5-aminobenzoic acid, 2- or 3- or 4- (meth) acryloyloxybenzoic acid, 4- or 5- (meth) N- and / or O-mono or di (meth) acryloyl (amino or oxy) benzoic acid compounds such as acryloylaminosalicylic acid;
Addition product of 2-hydroxyethyl (meth) acrylate and pyromellitic dianhydride, 2-hydroxyethyl (meth) acrylate and maleic anhydride or 2,3 ', 4,4'-benzophenone tetracarboxylic acid An addition reaction product of a hydroxyalkyl (meth) acrylate and an unsaturated polycarboxylic acid anhydride, such as an addition reaction product of an anhydride or 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride;
Compounds having polycarboxybenzoyloxy and (meth) acryloyloxy such as 2- (3,4-dicarboxybenzoyloxy) -1,3-di (meth) acryloyloxypropane);
An adduct of N-phenylglycine or N-tolylglycine and glycidyl (meth) acrylate;
4- [N- (2-hydroxy-3- (meth) acryloyloxypropyl) amino] phthalic acid, 3 or 4- [N-methyl-N- (2-hydroxy-3- (meth) acryloyloxypropyl) amino And N-alkyl-N- (hydroxy (meth) acryloyloxyalkyl) aminophthalic acid compounds such as phthalic acid. Of these, 11- (meth) acryloyloxy-1,1-undecanedicarboxylic acid and 4- (meth) acryloyloxyethyl trimellitic acid are preferably used.
少なくとも１個の水酸基がリン原子に結合している基および水中で容易に該基に変換し得る官能基として、例えばリン酸エステル基で水酸基を１個または２個を有する基を好ましく例示することができる。このような基を有する重合性単量体としては、例えば２−（メタ）アクリロイルオキシエチルアシドホスフェート、２−および／または３−（メタ）アクリロイルオキシプロピルアシドホスフェート、４−（メタ）アクリロイルオキシブチルアシドホスフェート、６−（メタ）アクリロイルオキシヘキシルアシドホスフェート、８−（メタ）アクリロイルオキシオクチルアシドホスフェート、１０−（メタ）アクリロイルオキシデシルアシドホスフェート、１２−（メタ）アクリロイルオキシドデシルアシドホスフェート等の（メタ）アクリロイルオキシアルキルアシドホスフェート；
ビス［２−（メタ）アクリロイルオキシエチル］アシドホスフェート、ビス［２−または３−（メタ）アクリロイルオキシプロピル］アシドホスフェート等の２つ以上の（メタ）アクリロイルオキシアルキル基を有するアシドホスフェート；
２−（メタ）アクリロイルオキシエチルフェニルアシドホスフェート、２−（メタ）アクリロイルオキシエチル−ｐ−メトキシフェニルアシドホスフェート等の（メタ）アクリロイルオキシアルキル基とフェニレン基などの芳香環やさらには酸素原子などのヘテロ原子を介して有するアシドホスフェート
などを挙げることができる。これらの化合物におけるリン酸基を、チオリン酸基に置き換えた化合物も例示することができる。これらのうち、２−（メタ）アクリロイルオキシエチルアシドホスフェートを好ましく使用することができる。
Preferred examples of the group having at least one hydroxyl group bonded to the phosphorus atom and the functional group that can be easily converted to the group in water include, for example, a phosphate ester group having one or two hydroxyl groups. Can do. Examples of the polymerizable monomer having such a group include 2- (meth) acryloyloxyethyl acid phosphate, 2- and / or 3- (meth) acryloyloxypropyl acid phosphate, 4- (meth) acryloyloxybutyl. (Meta) such as acid phosphate, 6- (meth) acryloyloxyhexyl acid phosphate, 8- (meth) acryloyloxyoctyl acid phosphate, 10- (meth) acryloyloxydecyl acid phosphate, 12- (meth) acryloyl oxide decyl acid phosphate ) Acryloyloxyalkyl acid phosphate;
An acid phosphate having two or more (meth) acryloyloxyalkyl groups such as bis [2- (meth) acryloyloxyethyl] acid phosphate, bis [2- or 3- (meth) acryloyloxypropyl] acid phosphate;
Aromatic rings such as 2- (meth) acryloyloxyethylphenyl acid phosphate, 2- (meth) acryloyloxyethyl-p-methoxyphenyl acid phosphate, (meth) acryloyloxyalkyl groups and phenylene groups, and oxygen atoms The acid phosphate etc. which have via a hetero atom can be mentioned. The compound which substituted the phosphate group in these compounds by the thiophosphate group can also be illustrated. Of these, 2- (meth) acryloyloxyethyl acid phosphate can be preferably used.
スルホン酸基あるいはスルホン酸基に容易に水中で変換し得る官能基を有する重合性単量体として、例えば２−スルホエチル（メタ）アクリレート、２−または１−スルホ−１−または２−プロピル（メタ）アクリレート、１−または３−スルホ−２−ブチル（メタ）アクリレート等のスルホアルキル（メタ）アクリレート；
３−ブロモ−２−スルホ−２−プロピル（メタ）アクリレート、３−メトキシ−１−スルホ−２−プロピル（メタ）アクリレート等の前記のアルキル部にハロゲンや酸素などのヘテロ原子を含む原子団を有する化合物；
１，１−ジメチル−２−スルホエチル（メタ）アクリルアミド、２−メチル−２−（メタ）アクリルアミドプロパンスルホン酸等の前記アクリレートに換えてアクリルアミドである化合物など；
さらには４−スチレンスルホン酸、４−（プロプ−１−エン−２−イル）ベンゼンスルホン酸などのビニルアリールスルホン酸
などを挙げることができる。これらのうち、４−スチレンスルホン酸を好ましく使用することができる。これら化合物は単独であるいは２種以上組み合わせて使用することができる。
Examples of the polymerizable monomer having a sulfonic acid group or a functional group that can be easily converted into a sulfonic acid group in water include 2-sulfoethyl (meth) acrylate, 2- or 1-sulfo-1- or 2-propyl (meta ) Sulfoalkyl (meth) acrylates such as acrylate, 1- or 3-sulfo-2-butyl (meth) acrylate;
An atomic group containing a hetero atom such as halogen or oxygen in the alkyl part such as 3-bromo-2-sulfo-2-propyl (meth) acrylate and 3-methoxy-1-sulfo-2-propyl (meth) acrylate Having a compound;
A compound that is acrylamide instead of the acrylate such as 1,1-dimethyl-2-sulfoethyl (meth) acrylamide, 2-methyl-2- (meth) acrylamidepropanesulfonic acid, and the like;
Furthermore, vinyl aryl sulfonic acid, such as 4-styrene sulfonic acid and 4- (prop-1-en-2-yl) benzene sulfonic acid, etc. can be mentioned. Of these, 4-styrenesulfonic acid can be preferably used. These compounds can be used alone or in combination of two or more.
また、重合体（Ａ）を構成しえる（Ｍａ）以外の他の単量体単位である酸性基を含まない単量体（Ｍｂ）としては、（Ｍａ）と共重合しうるラジカル重合性基を有する単量体を好ましく使用することができる。具体的な化合物名としては、
例えばブタジエン，イソプレンなどの共役ジエン単量体；
スチレン，α−メチルスチレン，クロルスチレンなどの芳香族ビニル単量体；
塩化ビニル，臭化ビニル，塩化ビニリデン，臭化ビニリデンなどのハロゲン化ビニルおよびハロゲン化ビニリデン；
酢酸ビニル，プロピオン酸ビニルなどのビニルエステル；
メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート等のアルキル（メタ）アクリレート；
エチレングリコールモノメチルエーテル（メタ）アクリレート、
２−ハイドロキシエチル（メタ）アクリレート、３−ハイドロキシプロピル（メタ）アクリレートなどのハイドロキシアルキル（メタ）アクリレート；
エチレングリコールモノメチルエーテル（メタ）アクリレート、エチレングリコールモノエチルエーテル（メタ）アクリレート、ジエチレングリコールモノメチルエーテル（メタ）アクリレート、ジエチレングリコールモノエチルエーテル（メタ）アクリレート等のポリエチレングリコールモノアルキルエーテル（メタ）アクリレート；
アセトアセトキシエチル（メタ）アクリレート；
シクロブチル（メタ）アクリレート、シクロヘキシル（メタ）アクリレートなどのシクロアルキル（メタ）アクリレート；
（テトラハイドロフラン−２−イル）（メタ）アクリレートなどのヘテロ原子を含む環状アルキル（メタ）アクリレート；
パーフルオロオクチル（メタ）アクリレートおよびヘキサフルオロ（メタ）アクリレートなどの（メタ）アクリル酸のフルオロアルキルエステル；
３−（トリメトキシシリル）プロピル（メタ）アクリレートなどの （メタ）アクリロキシアルキル基を有するシラン化合物
あるいは、
エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレートなどのポリ（オキシアルキレン）ジ（メタ）アクリレート；
グリセロールジ（メタ）アクリレート；
トリメチロールプロパンなどのブタントリオールのジ（メタ）アクリレート；
メソ−エリスリトールなどのブタンテトラオールのジ（メタ）アクリレートまたはトリ（メタ）アクリレート、ペンタントリオールのジ（メタ）アクリレート；
テトラメチロールメタンなどのペンタンテトラオールのジ（メタ）アクリレートまたはトリ（メタ）アクリレート；
キシリトール及びその異性体の水酸基を１〜２個有する多官能（メタ）アクリレート；
ヘキサントリオールのジ（メタ）アクリレート；
ヘキサンテトラオールのジ（メタ）アクリレートまたはトリ（メタ）アクリレート；
ヘキサンペンタオールの水酸基を１〜２個有する多官能（メタ）アクリレート；
ヘキサンヘキサオールの水酸基を１〜２個有する多官能（メタ）アクリレート；
あるいは下記式（１）
Moreover, as a monomer (Mb) which does not contain the acidic group which is other monomer units other than (Ma) which can comprise a polymer (A), it is a radically polymerizable group which can be copolymerized with (Ma). The monomer which has can be used preferably. Specific compound names include
For example, conjugated diene monomers such as butadiene and isoprene;
Aromatic vinyl monomers such as styrene, α-methylstyrene, chlorostyrene;
Vinyl halides and vinylidene halides such as vinyl chloride, vinyl bromide, vinylidene chloride, vinylidene bromide;
Vinyl esters such as vinyl acetate and vinyl propionate;
Alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate;
Ethylene glycol monomethyl ether (meth) acrylate,
Hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 3-hydroxypropyl (meth) acrylate;
Polyethylene glycol monoalkyl ether (meth) acrylates such as ethylene glycol monomethyl ether (meth) acrylate, ethylene glycol monoethyl ether (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate;
Acetoacetoxyethyl (meth) acrylate;
Cycloalkyl (meth) acrylates such as cyclobutyl (meth) acrylate and cyclohexyl (meth) acrylate;
Cyclic alkyl (meth) acrylates containing heteroatoms such as (tetrahydrofuran-2-yl) (meth) acrylate;
Fluoroalkyl esters of (meth) acrylic acid such as perfluorooctyl (meth) acrylate and hexafluoro (meth) acrylate;
Silane compounds having a (meth) acryloxyalkyl group such as 3- (trimethoxysilyl) propyl (meth) acrylate, or
Poly (oxyalkylene) di (meth) acrylates such as ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate;
Glycerol di (meth) acrylate;
Di (meth) acrylates of butanetriol, such as trimethylolpropane;
Di (meth) acrylate or tri (meth) acrylate of butanetetraol such as meso-erythritol, di (meth) acrylate of pentanetriol;
Di (meth) acrylate or tri (meth) acrylate of pentanetetraol such as tetramethylolmethane;
Polyfunctional (meth) acrylate having 1-2 hydroxyl groups of xylitol and its isomers;
Di (meth) acrylate of hexanetriol;
Di (meth) acrylate or tri (meth) acrylate of hexanetetraol;
Polyfunctional (meth) acrylate having 1 to 2 hydroxyl groups of hexanepentaol;
Polyfunctional (meth) acrylate having 1 to 2 hydroxyl groups of hexanehexaol;
Or following formula (1)
〔式中、Ｒ１は少なくとも１個の芳香族環を有しかつ分子中に酸素原子または硫黄原子を有していてもよい２価の芳香族残基あるいはシクロアルキル残基、好ましくは下記式（２） [In the formula, R 1 is a divalent aromatic residue or cycloalkyl residue which has at least one aromatic ring and may have an oxygen atom or a sulfur atom in the molecule, preferably the following formula (2)
から選択されるいずれかを示し、Ｒ２およびＲ３は互いに独立して水素原子またはメチル基を示し、ｎおよびｍは正の整数を示す〕で示される多官能（メタ）アクリレートなどを挙げることができる。
これらは単独で、あるいは２種類以上を組み合わせて使用することができる。
R 2 and R 3 each independently represent a hydrogen atom or a methyl group, and n and m each represent a positive integer.] Can do.
These can be used alone or in combination of two or more.
（Ａ）成分は構成物全量を基準に、好ましくは０．１〜３０％、より好ましくは０．２〜１５％、さらに好ましくは０．５〜１０％の範囲で用いられる。この範囲を下回ると、知覚過敏の抑制効果が発現され難く、上回ると、保存中の構成成分の凝集等が懸念され、ともに好ましくない。
また、単量体（Ｍａ）に由来する単量体単位の含有量は重合体（Ａ）を構成する単量体単位の全量に対して、好ましくは０．１〜３０モル％、より好ましくは０．１〜２モル％、さらに好ましくは０．５〜１０モル％の範囲である。この範囲を下回ると、知覚過敏抑制効果が発現され難く、上回ると、配合する（Ｂ）成分との凝集が懸念され、ともに好ましくない。
The component (A) is preferably used in the range of 0.1 to 30%, more preferably 0.2 to 15%, and still more preferably 0.5 to 10% based on the total amount of the component. Below this range, it is difficult for the effect of suppressing hypersensitivity to be expressed, and when it exceeds this range, there is a concern about aggregation of constituent components during storage, and both are not preferable.
Further, the content of the monomer unit derived from the monomer (Ma) is preferably 0.1 to 30 mol%, more preferably based on the total amount of the monomer unit constituting the polymer (A). It is 0.1-2 mol%, More preferably, it is the range of 0.5-10 mol%. If it is below this range, the hypersensitivity suppressing effect is hardly expressed, and if it exceeds, there is a concern about aggregation with the component (B) to be blended, which is not preferable.
さらに、（Ａ）成分は水性エマルジョンあるいは水溶性の性状を有していることが好ましい。なお、（Ａ）成分の存在形態としては、水性エマルジョンあるいは水溶された状態だけでなく、溶媒が実質上除去された状態であるが溶媒を加えれば容易に水性エマルジョンあるいは水溶状態になりえる乾燥状態（粉末など）のものも包含するものである。ここで言う水性エマルジョンとは、水を含む分散媒中に、微細な粒子状の重合体が分散した状態を言う。また特に、水溶性である場合には、（Ａ）の水に対する溶解度が３０％以上であることが好ましい。
（Ａ）成分が水性エマルジョンの性状を有している場合、象牙質細管を封鎖するのに十分な深さにまで水性エマルジョンを侵入させるために、水性エマルジョン中の（Ａ）成分の粒径は象牙質細管の直径よりも小さいことが必要である。象牙細管の直径は、位置や深さ、また個体差があるものの通常１〜３μｍの範囲にある。従って、水性エマルジョンである（Ａ）成分の粒子の平均粒径は３μｍ以下であることが好ましく、より好ましくは１μｍ以下である。
Furthermore, the component (A) preferably has an aqueous emulsion or water-soluble properties. The presence form of the component (A) is not only an aqueous emulsion or a water-soluble state, but is a state in which the solvent is substantially removed, but if the solvent is added, it can easily become an aqueous emulsion or a water-soluble state. (Powder etc.) is also included. The aqueous emulsion here refers to a state in which a fine particle polymer is dispersed in a dispersion medium containing water. In particular, when it is water-soluble, the solubility of (A) in water is preferably 30% or more.
When the component (A) has the properties of an aqueous emulsion, the particle size of the component (A) in the aqueous emulsion is determined in order to penetrate the aqueous emulsion to a depth sufficient to seal the dentinal tubules. It must be smaller than the diameter of the dentinal tubule. The diameter of the dentinal tubule is usually in the range of 1 to 3 μm, although there are positions, depths, and individual differences. Therefore, the average particle diameter of the particles of the component (A) which is an aqueous emulsion is preferably 3 μm or less, more preferably 1 μm or less.
なお、象牙質細管の直径は、通常、抜去した歯牙のエナメル質を削り取って露出した象牙質表面を歯磨剤と歯ブラシを使って１分以上ブラッシングを行った後、水中で超音波洗浄を施し、走査型電子顕微鏡（ＳＥＭ）にて観察することによって計測できる。
また、水性エマルジョンの性状を持つ（Ａ）成分の粒径には分布があり、すべてのエマルジョン粒子の粒径が象牙細管径よりも小さい必要はない。（Ａ）成分の水性エマルジョン粒子のうち、粒径が３μｍ未満のものが５０％以上占めることが好ましく、９０％以上のエマルジョン粒子の粒径が３μｍ未満であることがより好ましい。上記の条件に加えて、（Ａ）成分の水性エマルジョン粒子のうち、粒径が１μｍ以下のものが６５％以上占めることが特に好ましく、７５％以上占めることがとりわけ好ましい。エマルジョン粒子が上記のような粒径分布を有することにより本発明の目的が優れて達成される。
The diameter of the dentinal tubule is usually determined by scraping the enamel of the extracted tooth and brushing the exposed dentin surface with a dentifrice and a toothbrush for at least 1 minute, followed by ultrasonic cleaning in water. It can be measured by observing with a scanning electron microscope (SEM).
Further, the particle size of the component (A) having the properties of an aqueous emulsion is distributed, and it is not necessary that the particle size of all the emulsion particles is smaller than the dentinal tubule diameter. Of the aqueous emulsion particles (A), those having a particle size of less than 3 μm preferably account for 50% or more, and more preferably 90% or more of the emulsion particles have a particle size of less than 3 μm. In addition to the above conditions, among the aqueous emulsion particles of component (A), those having a particle size of 1 μm or less preferably occupy 65% or more, and particularly preferably 75% or more. The object of the present invention is excellently achieved when the emulsion particles have the particle size distribution as described above.
さらに好ましい（Ａ）成分として、例えば重合体のエマルジョン粒子を高速ミキサーやホモジナイザーなどの分散・粉砕器で、好ましくは直径３μｍ以下、より好ましくは直径１μｍ以下、最も好ましくは直径０．５μｍ以下のエマルジョン粒子となし、このエマルジョン粒子が（Ａ）成分の中に０．５％以上存在するように調製して分散安定性を向上させたものを使用することができる。また、粒径が１．０μｍ以下の（Ａ）のエマルジョン粒子が、エマルジョン粒子全体の５０％以上、特には７５％以上占めることが好ましく、そしてエマルジョン粒子の全体を占めることが最も好ましい。 As a more preferred component (A), for example, a polymer emulsion particle is dispersed in a high-speed mixer, homogenizer, or the like, and is preferably an emulsion having a diameter of 3 μm or less, more preferably 1 μm or less, and most preferably 0.5 μm or less. It is possible to use particles which are prepared so that the emulsion particles are present in an amount of 0.5% or more in the component (A) and the dispersion stability is improved. The emulsion particles (A) having a particle size of 1.0 μm or less preferably occupy 50% or more, particularly 75% or more, and most preferably occupy the entire emulsion particles.
（Ａ）成分に含まれる象牙質細管径よりも小さい粒子径を有する（Ａ）成分の水性エマルジョン粒子は、カルシウム化合物、例えば塩化カルシウムを（Ａ）成分中に添加したときに、該カルシウム化合物と反応して象牙質細管径よりも大きな径を有する凝集体を形成し得る。
通常、該凝集体の径は３μｍを超え、好ましくは１０μｍ以上、より好ましくは５０〜数千μｍに達する。
上記カルシウム化合物の添加量は、エマルジョン中の不揮発性成分１００重量部に対して、好ましくは１０〜１００重量部の範囲である。
The aqueous emulsion particles of the component (A) having a particle size smaller than the diameter of the dentin tubule contained in the component (A) are obtained when the calcium compound, for example, calcium chloride is added to the component (A). Can form an aggregate having a diameter larger than the diameter of the dentinal tubule.
Usually, the diameter of the aggregate exceeds 3 μm, preferably 10 μm or more, and more preferably 50 to several thousand μm.
The amount of the calcium compound added is preferably in the range of 10 to 100 parts by weight with respect to 100 parts by weight of the nonvolatile component in the emulsion.
このような性質を有する成分（Ａ）を本発明の組成物に用いることにより、象牙質細管に侵入した小さい径の（Ａ）成分のエマルジョン粒子は、主に象牙質細管を形成する管周象牙質中に存在するハイドロキシアパタイトから溶出したカルシウムイオンや象牙質中に含まれる髄液中のカルシウムイオンと反応して、大きな凝集体を多数形成する。
この形成された多数の大凝集体は、象牙質細管内の長さ方向に連続的に充填された状態（被膜）となる。このような状態が形成されることにより、該細管は封鎖される。該細管が封鎖された状態は、後述する（Ｄ）成分を使用することにより速かに形成される。またこの状態は、凝集体と象牙質の密着性が長く維持されるので、長期間保持される。
なお、上記酸性基あるいは当該官能基に水中で容易に変換し得る官能基は、エマルジョン中乃至は親水性溶媒溶液中に、好ましくは０．００００１〜０．０１モル／ｇ、より好ましくは０．００００２〜０．００５モル／ｇで存在する。
By using the component (A) having such properties in the composition of the present invention, the emulsion particles of the component (A) having a small diameter that have invaded into the dentinal tubules mainly form the dentinal tubules. It reacts with calcium ions eluted from hydroxyapatite present in the material and calcium ions contained in the cerebrospinal fluid contained in the dentin to form many large aggregates.
A large number of the formed large aggregates are continuously filled in the length direction in the dentinal tubule (film). By forming such a state, the capillaries are blocked. The state where the narrow tube is sealed is quickly formed by using the component (D) described later. Further, this state is maintained for a long time because the adhesion between the aggregate and the dentin is maintained for a long time.
The acidic group or the functional group that can be easily converted into the functional group in water is preferably 0.00001 to 0.01 mol / g, more preferably 0.001 in an emulsion or a hydrophilic solvent solution. Present at 00002 to 0.005 mol / g.
（Ａ）成分に含まれる重合体の数平均分子量Ｍｎは、ＧＰＣ法で測定した値として、好ましくは３，０００以上であり、より好ましくは７，０００以上、さらに好ましくは１０，０００以上である。数平均分子量の上限は通常５００万である。（Ａ）成分はエマルジョン粒子としての高分子重合体を、好ましくは０．１〜６０重量％、より好ましくは０．５〜４０重量％、さらに好ましくは１〜２０重量％の範囲で含有することができる。
（Ａ）成分としての好ましい水溶性を有する重合体（Ａｗ）としては、重合体の分子中に、Ｍａに由来する単量体単位として、（メタ）アクリルアマイドアルカンスルホン酸（Ｈ２Ｃ＝Ｃ（Ｒ４）−ＣＯ−ＮＨ−Ｒ５−ＳＯ３Ｈ， Ｒ４：Ｈ又はＣＨ３， Ｒ５：２価の炭化水素基）に由来する単量体単位あるいは重合体の分子中に、水酸基を1つ以上有する炭素数４〜８の（ポリ）ハイドロキシアルキル（メタ）アクリルアマイド（Ｈ２Ｃ＝Ｃ（Ｒ６）−ＣＯ−ＮＨ−Ｒ７（ＯＨ）ｎ，） Ｒ６：Ｈ又はＣＨ３， Ｒ７：炭化水素基、ｎ：１以上の整数）に由来する単量体単位を水酸基モル比（前記単位中の水酸基モル数／重合体中の単量体単位の総モル数）にて、好ましくは０．７〜１１．０、より好ましくは０．７５〜１０．５、更に好ましくは０．８〜１０．０［モル／モル］で有するもを挙げることができる。
The number average molecular weight Mn of the polymer contained in the component (A) is preferably 3,000 or more, more preferably 7,000 or more, and further preferably 10,000 or more as a value measured by the GPC method. . The upper limit of the number average molecular weight is usually 5 million. The component (A) contains a polymer as emulsion particles, preferably in the range of 0.1 to 60% by weight, more preferably 0.5 to 40% by weight, still more preferably 1 to 20% by weight. Can do.
As the polymer (Aw) having a preferable water solubility as the component (A), (meth) acrylamide alkanesulfonic acid (H 2 C═C) is used as a monomer unit derived from Ma in the polymer molecule. In the monomer unit or polymer molecule derived from (R 4 ) —CO—NH—R 5 —SO 3 H, R 4 : H or CH 3 , R 5 : a divalent hydrocarbon group, (Poly) hydroxyalkyl (meth) acrylamide (H 2 C═C (R 6 ) —CO—NH—R 7 (OH) n ,) R 6 : H or CH 3 , R 7 : hydrocarbon group, n: an integer of 1 or more) in a hydroxyl group molar ratio (number of hydroxyl groups in the unit / total number of monomer units in the polymer) And preferably 0.7-11.0, more preferably 0.75-1 .5, more preferably can be exemplified also has at 0.8 to 10.0 [mol / mol].
前記（メタ）アクリルアマイドアルカンスルホン酸単位と（ポリ）ハイドロキシアルキル（メタ）アクリルアマイド単位を有する共重合体(ここでは、以下、ＡＳ−ＨＡ重合体という)以外の共重合体(ここでは、以下、ＡＳ−ＨＡ相当重合体という)では、ＡＳ−ＨＡ相当重合体の重量に対するＡＳ−ＨＡ相当重合体に含まれる酸性基（スルホン酸等）や水酸基のモル数の比率であるモル重量比［モル／ｇ］の数値範囲が、ＡＳ−ＨＡ重合体の場合におけるモル比［モル／モル］の数値範囲に対応するモル重量比（但し、ＡＳ−ＨＡ重合体は２，３−ジハイドロキシプロピルメタクリルアマイドと２−アクリルアマイド−２−メチルプロパンスルホン酸よりなり、必要に応じてアクリル酸メチルを有する共重合体として比を計算)の範囲にあることが好ましい。 Copolymers other than the copolymer having the (meth) acrylamide alkanesulfonic acid unit and the (poly) hydroxyalkyl (meth) acrylamide unit (hereinafter referred to as AS-HA polymer) (herein , AS-HA equivalent polymer) is a molar weight ratio [mole that is a ratio of the number of moles of acidic groups (sulfonic acid, etc.) and hydroxyl groups contained in the AS-HA equivalent polymer to the weight of the AS-HA equivalent polymer. / G] is a molar weight ratio corresponding to the numerical range of the molar ratio [mol / mol] in the case of AS-HA polymer (where AS-HA polymer is 2,3-dihydroxypropyl methacrylate). And 2-acrylamido-2-methylpropane sulfonic acid, and if necessary, the ratio is calculated as a copolymer having methyl acrylate). It is preferred.
（Ａ）成分として好ましい水性エマルジョン形態を有する重合体（Ａｓ）は、Ｍａに由来する単量体単位としてスチレンスルホン酸単位を有するものである。更に、重合体の分子中に、炭素数４〜８の（メタ）アクリル酸アルキルエステル単位をモル比（前記単位のモル数／重合体中の重合単位の総モル数）にて、好ましくは７０〜９９．９、より好ましくは９０〜９９．９、更に好ましくは９８〜９９．５［モル／モル］有する共重合体をエマルジョン粒子として含有するエマルジョンである。
（Ａ）成分の製造方法は、特に限定されるものではなく、従来公知の方法を用いて製造することができる。
具体的には、（Ａ）成分が水溶性を有する場合には、水あるいは水溶性有機溶媒等の溶媒、重合開始剤、単量体を撹拌しながら加温し、重合の後、再沈殿などにより精製し得る方法を挙げることができる。
The polymer (As) having a preferred aqueous emulsion form as the component (A) has a styrene sulfonic acid unit as a monomer unit derived from Ma. Further, in the polymer molecule, the (meth) acrylic acid alkyl ester unit having 4 to 8 carbon atoms is preferably in a molar ratio (number of moles of the unit / total number of moles of polymerized units in the polymer). It is an emulsion containing a copolymer having -99.9, more preferably 90-99.9, and still more preferably 98-99.5 [mol / mol] as emulsion particles.
(A) The manufacturing method of a component is not specifically limited, It can manufacture using a conventionally well-known method.
Specifically, when the component (A) is water-soluble, a solvent such as water or a water-soluble organic solvent, a polymerization initiator, and a monomer are heated with stirring, and after polymerization, reprecipitation, etc. The method which can be refine | purified by can be mentioned.
（Ａ）成分が水性エマルジョンの場合においては重合開始剤を含んだ分散媒を加温し、高速回転の下、単量体を滴下して重合させ、濃縮あるいは噴霧乾燥等により（Ａ）成分を得る方法、あるいは単量体、重合開始剤、溶媒を撹拌しながら加熱して、（Ａ）成分を得る方法などを挙げることができる。
重合温度は、好ましくは４０〜２００℃の範囲である。
In the case where the component (A) is an aqueous emulsion, the dispersion medium containing a polymerization initiator is heated, the monomer is dropped and polymerized under high speed rotation, and the component (A) is obtained by concentration or spray drying. Examples thereof include a method for obtaining a component (A) by heating a monomer, a polymerization initiator and a solvent while stirring.
The polymerization temperature is preferably in the range of 40 to 200 ° C.
本発明における（Ｂ）成分はアナターゼ型二酸化チタン粒子である。変色した歯の色を遮蔽して目立たないようにする効果と、光触媒効果で細菌を無活性化する効果とを示す。
二酸化チタンの結晶形は、アナターゼ型である。アナターゼ型二酸化チタンは、光触媒性を有するので形状、性状に限定されない。さらに、二酸化チタンに白金を担持させることによって光触媒活性を向上させたもの、あるいは二酸化チタンにプラズマ処理等を行うことによって、可視光領域の光に応答して光触媒作用を示すものも用いることができる。二酸化チタンは、粉末状態のものでも水などの媒体に分散したゾル状態のものであってもよい。二酸化チタンの１次粒子の平均粒径は好ましくは１〜５００ｎｍであり、より好ましくは５〜２００ｎｍである。また、この１次粒子の幾つかは粒子同士で凝集していてもよい。凝集後の粒子径は好ましくは５ｎｍ〜５０μｍの範囲であり、より好ましくは１０ｎｍ〜３０μｍの範囲である。もっとも好ましくは、アナターゼ型［要件（ｄ１）］であり、平均粒径が前記条件（１次粒子の平均粒径が１〜５００ｎｍ等）［要件（ｄ２）］である二酸化チタン粒子である。これは、一つ一つの粒子が（ｄ１）と（ｄ２）を同時に満たすということであり、これと比べて、（ｄ１）かつ非（ｄ２）の粒子と非（ｄ１）かつ（ｄ２）の粒子の混合物では、余り効果が期待できない。
The component (B) in the present invention is anatase type titanium dioxide particles. It shows the effect of blocking the discolored tooth color to make it inconspicuous and the effect of deactivating bacteria by the photocatalytic effect.
Crystalline form of titanium dioxide, Ru anatase der. Anatase titanium dioxide, so that having a photocatalytic shape, but are not limited to property. In addition, it is possible to use a photocatalytic activity improved by supporting platinum on titanium dioxide, or a photocatalytic action in response to light in the visible light region by performing plasma treatment or the like on titanium dioxide. . The titanium dioxide may be in a powder state or in a sol state dispersed in a medium such as water. The average particle diameter of the primary particles of titanium dioxide is preferably 1 to 500 nm, more preferably 5 to 200 nm. Some of the primary particles may be aggregated with each other. The particle diameter after aggregation is preferably in the range of 5 nm to 50 μm, more preferably in the range of 10 nm to 30 μm. Most preferably, it is an anatase type [requirement (d1)] and the average particle size is titanium dioxide particles having the above-mentioned conditions (the average particle size of primary particles is 1 to 500 nm, etc.) [requirement (d2)]. This means that each particle satisfies (d1) and (d2) simultaneously. Compared with this, (d1) and non- (d2) particles and non- (d1) and (d2) particles In the case of this mixture, the effect is not expected.
本発明における（Ｂ）成分は構成物の全量に対して、好ましくは０．０１〜２４％、より好ましくは０．１〜１２％、さらに好ましくは０．１〜８％の範囲で配合することができる。この範囲を下回る０．０１％未満においては所望の歯牙色遮蔽効果が発揮できず、この範囲を上回ると、保管中に（Ｂ）成分および（Ａ）成分と反応し、著しい凝集を引き起こし、ともに好ましくない。 Component (B) in the present invention is preferably blended in the range of 0.01 to 24%, more preferably 0.1 to 12%, and still more preferably 0.1 to 8% with respect to the total amount of the constituents. Can do. If it is less than 0.01% below this range, the desired tooth color shielding effect cannot be exhibited, and if it exceeds this range, it reacts with component (B) and component (A) during storage, causing significant aggregation, It is not preferable.
本発明における（Ｃ）成分は溶媒および／または分散媒である。生体への為害性を考慮して使用すべきであり、エタノール、アセトン、水を好ましく使用することができ、特に水の使用が好ましい。水の種類については特に限定するものではないが、日本薬局方精製水に準じた水の使用が好ましい。 The component (C) in the present invention is a solvent and / or a dispersion medium. It should be used in consideration of harm to the living body, and ethanol, acetone, and water can be preferably used, and the use of water is particularly preferable. Although it does not specifically limit about the kind of water, Use of the water according to Japanese Pharmacopoeia purified water is preferable.
本発明における（Ｄ）成分は水溶性酸性化合物である。該水溶性酸性化合物のカルシウム塩は、水不溶性あるいは難溶性塩である。水不溶性または難溶性は、（Ｄ）成分を含む溶液とカルシウムイオンを含む溶液を混合した際の沈殿生成の有無で判別される。沈澱生成の有無は、一般的に溶解度積とイオン積の関係で知ることができる。すなわち、（Ｄ）成分のカルシウム塩のイオン積が溶解度積と等しい場合、もしくはイオン積が溶解度積よりも大きい場合に水難溶性および水不溶性とすることができる。簡便な沈澱生成の目安として、水溶性有機酸またはその水溶性塩成分の１〜５％の濃度範囲の水溶液と同濃度範囲の塩化カルシウム水溶液を混合した場合に肉眼的に沈澱の生成を確認する方法がある。 The component (D) in the present invention is a water-soluble acidic compound. The calcium salt of the water-soluble acidic compound is a water-insoluble or hardly soluble salt. Water insolubility or poor solubility is determined by the presence or absence of precipitation when a solution containing component (D) and a solution containing calcium ions are mixed. Presence or absence of precipitation can generally be known from the relationship between solubility product and ionic product. That is, when the ionic product of the calcium salt of the component (D) is equal to the solubility product, or when the ionic product is larger than the solubility product, it can be made hardly soluble in water and insoluble in water. As a guideline for simple precipitation, when a water-soluble organic acid or its water-soluble salt component is mixed with an aqueous solution with a concentration range of 1 to 5% and an aqueous calcium chloride solution with the same concentration range, the formation of the precipitate is visually confirmed There is a way.
本発明において（Ｄ）成分は水中において酸性の性状を有していれば、特に限定されるものではないが、（Ａ）よりも有意に低分子量例えば、分子量２００以下の水溶性弱酸および／またはその塩が好ましく、該酸のカルシウム塩は水不溶性あるいは難溶性である。ここで塩は金属塩、アンモニウム塩、アミン塩である。水溶性の目安は、２５℃における水への溶解度が０．５ｇ／１００ｇ以上である。具体的には、シュウ酸、クエン酸、酒石酸，プロピオン酸および／またはその塩を好ましく使用することができる。又、（Ｄ）成分としては、エチレン性二重結合を有しないものが好適に用いられる。 In the present invention, the component (D) is not particularly limited as long as it has acidic properties in water. However, the water-soluble weak acid having a molecular weight significantly lower than that of (A), for example, a molecular weight of 200 or less, and / or The salt is preferable, and the calcium salt of the acid is insoluble or hardly soluble in water. Here, the salt is a metal salt, an ammonium salt, or an amine salt. As a measure of water solubility, the solubility in water at 25 ° C. is 0.5 g / 100 g or more. Specifically, oxalic acid, citric acid, tartaric acid, propionic acid and / or a salt thereof can be preferably used. Moreover, as (D) component, what does not have an ethylenic double bond is used suitably.
本発明において、（Ｄ）成分の配合量は組成物の全量に対し、好ましくは０．０１〜５０％、より好ましくは０．０２〜３０％、さらに好ましくは０．１〜１０％である。上記の濃度範囲から外れた低い濃度では管周象牙質、あるいは歯牙表面からのカルシウム析出量が少なかったり、得られる該酸のカルシウム塩の結晶サイズが小さ過ぎたりするため、期待される効果が十分に発揮されないことがあり、上記の範囲から外れた高い濃度では、飽和濃度に達して溶液から析出したり、保管中の著しい凝集が起こる可能性がある。 In this invention, the compounding quantity of (D) component becomes like this. Preferably it is 0.01 to 50% with respect to the whole quantity of a composition, More preferably, it is 0.02 to 30%, More preferably, it is 0.1 to 10%. At low concentrations outside the above concentration range, the amount of precipitated calcium from the ductal dentine or tooth surface is small, or the crystal size of the resulting calcium salt of the acid is too small, so the expected effect is sufficient In a high concentration outside the above range, a saturated concentration may be reached and precipitate from the solution, or significant aggregation during storage may occur.
本発明の歯科用組成物には、所望により防腐剤および／または抗菌剤を使用することができる。本発明において好適に使用しうる防腐剤および／または抗菌剤（Ｄ）成分として，歯科用予防剤として知られている塩酸クロルヘキシジン，塩化セチルピリジニウム，キシリトール，グルコン酸クロルヘキシジン，グリチルリチン酸ジカリウムなどが挙げられるが，さらには，エタノール，プロパノール，イソプロパノ−ルなどの脂肪族アルコール；
クロロブタノールや２−ブロモ−２−ニトロ−プロパノル−１，３−ジオールなどのハロゲン化脂肪族アルコール；
２，４−ジクロロベンジルアルコール，２−フェノキシエタノール，フェノキシイロプロパノール，フェニルエチルアルコール，３−（４−クロロフェノキシ）−１，２−プロパンジオールなどの芳香族アルコール；
５−ブロモ−５−ニトロ−１，３−ジオキサン，ホルムアルデヒド，パラホルムアルデヒド，グルタルアルデヒドなどのアルデヒドおよびヘキサメチレンテトラミン，モノメチロールジメチルヒダントイン，ジメチロールメチルヒダントインなどの酸性条件下でアルデヒドを生成させうるアルデヒド徐放剤；
クロロアセトアマイドなどのアマイド；
Ｎ，Ｎ’−メチレン−ビス（Ｎ’−（１−（ヒドロキシメチル）−２，５−ジオキソ−４−イミダゾリジニル）ウレア，Ｎ−（ヒドロキシメチル）−Ｎ−（１，３−ジヒドロキシメチル−２，５−ジオキソ−４−イミダゾリジニル）−Ｎ’ −（ヒドロオキシメチル）ウレアなどのウレア；
亜硫酸ナトリウム，亜硫酸カリウム，重亜硫酸ナトリウム，重亜硫酸カリウム，ピロ亜硫酸ナトリウム，ピロ亜硫酸カリウムなどの無機亜硫酸塩，重亜硫酸塩およびピロ亜硫酸塩；ホウ酸などの無機酸；
ギ酸，プロピオン酸，１０−ウンデセン酸，ソルビン酸，安息香酸，サリチル酸，２−アセチル−５−ヒドロキシ−３−オキソ−４−ヘキサン酸−β−ラクトンなどの有機酸化合物；
２，６−ジアセチル−７，９−ジヒドロキシ−８，９ｂ−ジメチル−１．３−（２Ｈ，９ｂＨ）−ジベンゾフランジオンなどの抗生物質；
ｐ−ヒドロキシ安息香酸メチル、ｐ−ヒドロキシ安息香酸エチル、ｐ−ヒドロキシ安息香酸ｎ−プロピルならびにイソプロピル、ｐ−ヒドロキシ安息香酸ｎ−ブチルまたはイソブチルまたはｔ−ブチル、ｐ−ヒドロキシ安息香酸ベンジルなどのｐ−ヒドロキシ安息香酸エステル化合物；
４−クロル−３−メチルフェノール、４−クロル−３，５−キシレノール、３，４，５，６−テトラブロモ−ｏ−クレゾ−ル、２，４−ジクロロ−３，５−キシレノール、２−ベンジル−４−クロロフェノール、２，２’−メチレンビス（４−クロロフェノール）、３，３’−ジブロモ−５，５’ −ジクロロ−２，２’−ジヒドロキシ−ジフェニルメタン、２，２’−メチレンビス（３，４，６−トリクロロフェノール）などのハロゲン化フェノール化合物;
３，４，４’−トリクロロカルバニリド、４，４’−ジクロロ−３−（３−フルオロメチル）カルバニリドなどのカルバニリド化合物；４，４’−ジアミジノ−α，ω−ジフェノキシプロパンイセチオネート、４，４’−（トリメチレンジオキサン）−ビス−（３−プロモベンザミジン）ジイセチオネート、１，６−ジ（４−アミジノフェノキシ）−ｎ−ヘキサンなどのベンザミジン化合物;
If desired, an antiseptic and / or an antibacterial agent can be used in the dental composition of the present invention. Examples of the preservative and / or antibacterial agent (D) component that can be suitably used in the present invention include chlorhexidine hydrochloride, cetylpyridinium chloride, xylitol, chlorhexidine gluconate, and dipotassium glycyrrhizinate which are known as dental preventive agents. But also aliphatic alcohols such as ethanol, propanol and isopropanol;
Halogenated aliphatic alcohols such as chlorobutanol and 2-bromo-2-nitro-propanol-1,3-diol;
Aromatic alcohols such as 2,4-dichlorobenzyl alcohol, 2-phenoxyethanol, phenoxyiropropanol, phenylethyl alcohol, 3- (4-chlorophenoxy) -1,2-propanediol;
Aldehydes such as 5-bromo-5-nitro-1,3-dioxane, formaldehyde, paraformaldehyde, glutaraldehyde, and aldehydes capable of generating aldehydes under acidic conditions such as hexamethylenetetramine, monomethyloldimethylhydantoin, dimethylolmethylhydantoin Sustained release agent;
Amides such as chloroacetamide;
N, N′-methylene-bis (N ′-(1- (hydroxymethyl) -2,5-dioxo-4-imidazolidinyl) urea, N- (hydroxymethyl) -N- (1,3-dihydroxymethyl-2) , 5-dioxo-4-imidazolidinyl) -N ′-(hydroxymethyl) urea;
Inorganic sulfites, bisulfites and pyrosulfites such as sodium sulfite, potassium sulfite, sodium bisulfite, potassium bisulfite, sodium pyrosulfite, potassium pyrosulfite; inorganic acids such as boric acid;
Organic acid compounds such as formic acid, propionic acid, 10-undecenoic acid, sorbic acid, benzoic acid, salicylic acid, 2-acetyl-5-hydroxy-3-oxo-4-hexanoic acid-β-lactone;
Antibiotics such as 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1.3- (2H, 9bH) -dibenzofurandion;
p-hydroxy, such as methyl p-hydroxybenzoate, ethyl p-hydroxybenzoate, n-propyl p-hydroxybenzoate and isopropyl, n-butyl or isobutyl or t-butyl p-hydroxybenzoate, benzyl p-hydroxybenzoate Hydroxybenzoic acid ester compounds;
4-chloro-3-methylphenol, 4-chloro-3,5-xylenol, 3,4,5,6-tetrabromo-o-cresol, 2,4-dichloro-3,5-xylenol, 2-benzyl -4-chlorophenol, 2,2'-methylenebis (4-chlorophenol), 3,3'-dibromo-5,5'-dichloro-2,2'-dihydroxy-diphenylmethane, 2,2'-methylenebis (3 , 4,6-trichlorophenol) and the like;
Carbanilide compounds such as 3,4,4′-trichlorocarbanilide, 4,4′-dichloro-3- (3-fluoromethyl) carbanilide; 4,4′-diamidino-α, ω-diphenoxypropane isethionate Benzamidine compounds such as 4,4 ′-(trimethylenedioxane) -bis- (3-promobenzamidine) diisethionate, 1,6-di (4-amidinophenoxy) -n-hexane;
ピリジン−１−オキサイド−２−チオール−ナトリウム塩、ジンクビス−（２−ピリジンチオ−ル−１−オキサイド）ビス−（２−ピリジルチオ）ジンク−１，１’−ジオキサイド（ジンクピリジオン）などの環状チオヒドロキサム酸またはその塩；
５−アミノ−１，３−ビス（２−エチルヘキシル）−５−メチルヘキサヒドロピリミジン、トリス−ヒドロキシエチルヘキサヒドロトリアジンなどのＮ−アセタール化合物；Ｎ−（トリクロロメチルチオ）−４−シクロヘキサン−１，２−ジカルボキシミドなどのフタルイミド誘導体；
６−アセトキシ−２，４−ジメチル−ｍ−ジオキサンなどのｏ−アセタール化合物；
４，４−ジメチル−１，３−オキサゾリジンなどのオキサゾリジン化合物；
８−ヒドロキシキノリンなどのキノリン化合物；
ビス（ｐ−クロロフェニルジグアナイド）ヘキサン、ポリヘキサメチレンビグアナイド塩酸塩などの陽イオン性物質；
アルキルトリメチルアンモニウムブロマイド、Ｎ−ドデシル−Ｎ，Ｎ−ジメチルベンジルアンモニウム、Ｎ，Ｎ−ジメチル−Ｎ−（２−（２−（４−（１，１，３，４−テトラメチルブチル）フェノキシ）エトキシ）エチル）ベンゼンメタンアンモニウムクロライドなどの４級塩化合物；
エチルマーキュリーチオサリシレート、酢酸フェニル水銀などの有機水銀化合物；
よう素酸ナトリウムなどのよう素化合物；
グリセリルモノラウレート；
１−ヒドロキシ−４−メチル−６−（２，４，４−トリメチルペンチル）−２−（１Ｈ）−ピリドンエタノールアミン塩などのピリドン誘導体
などを挙げることができる。これらの防腐剤は使用する（Ａ）成分の著しい凝集を引き起こさないものを選択使用することが好ましい。
防腐剤成分（Ｅ）は，通常、０．０１〜５０％，より好ましくは０．０２〜３０％，さらに好ましくは０．０５〜１０％の範囲で使用できる。
Cyclic such as pyridine-1-oxide-2-thiol-sodium salt, zinc bis- (2-pyridinethiol-1-oxide) bis- (2-pyridylthio) zinc-1,1′-dioxide (zinc pyridione) Thiohydroxamic acid or a salt thereof;
N-acetal compounds such as 5-amino-1,3-bis (2-ethylhexyl) -5-methylhexahydropyrimidine and tris-hydroxyethylhexahydrotriazine; N- (trichloromethylthio) -4-cyclohexane-1,2 Phthalimide derivatives such as dicarboximide;
O-acetal compounds such as 6-acetoxy-2,4-dimethyl-m-dioxane;
Oxazolidine compounds such as 4,4-dimethyl-1,3-oxazolidine;
Quinoline compounds such as 8-hydroxyquinoline;
Cationic substances such as bis (p-chlorophenyldiguanide) hexane, polyhexamethylenebiguanide hydrochloride;
Alkyltrimethylammonium bromide, N-dodecyl-N, N-dimethylbenzylammonium, N, N-dimethyl-N- (2- (2- (4- (1,1,3,4-tetramethylbutyl) phenoxy) ethoxy ) Ethyl) quaternary salt compounds such as benzenemethane ammonium chloride;
Organic mercury compounds such as ethyl mercury thiosalicylate and phenylmercuric acetate;
Iodine compounds such as sodium iodate;
Glyceryl monolaurate;
Examples include pyridone derivatives such as 1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2- (1H) -pyridone ethanolamine salt. These preservatives are preferably selected and used without causing significant aggregation of the component (A) used.
The preservative component (E) can be used generally in the range of 0.01 to 50%, more preferably 0.02 to 30%, and still more preferably 0.05 to 10%.
歯牙色遮蔽効果と知覚過敏抑制作用を有する本発明の組成物には、所望により、水中においてフッ化物イオンを放出する化合物（Ｆ）を含有させることができる。かかる化合物としては、可溶性の有効フッ素イオンを組成物中に放出するものであれば、いずれのものも使用しうる。例えば、フルオロリン酸二ナトリウム、フッ化スズ、フッ化ナトリウム、フッ化カリウム、フッ化ケイ素ナトリウム、フルオロアルミノシリケ−トガラス、フッ化アンモニウム等を使用しうる。中でもフッ化ナトリウム、フッ化カルシウム、モノフルオロリン酸ナトリウム、フッ化第一スズの使用が特に好ましい。その配合量は、本発明の歯牙色遮蔽効果を有する知覚過敏抑制材の使用量と適用頻度、ならびに耐酸性や再石灰化の有効性と人体への影響を考慮して適宜設定される。（Ｆ）成分の存在により、歯質自体の耐酸性の向上効果が期待できる。本発明において、（Ｆ）成分は、組成物中のフッ素イオン濃度として好ましくは０．０００１〜５％、より好ましくは０．００１〜２％、特に好ましくは０．０１〜１％の範囲である。０．０００１％未満では、所望の歯質の耐酸性効果や再石灰化効果が十分に表れず、５％を超えると、生体への為害性が懸念される。 If desired, the composition of the present invention having a tooth color shielding effect and a hypersensitivity suppressing effect can contain a compound (F) that releases fluoride ions in water. Any compound can be used as long as it releases soluble effective fluorine ions into the composition. For example, disodium fluorophosphate, tin fluoride, sodium fluoride, potassium fluoride, sodium silicon fluoride, fluoroaluminosilicate glass, ammonium fluoride and the like can be used. Among these, use of sodium fluoride, calcium fluoride, sodium monofluorophosphate, and stannous fluoride is particularly preferable. The blending amount is appropriately set in consideration of the usage amount and application frequency of the hypersensitivity suppressing material having the tooth color shielding effect of the present invention, the acid resistance, the effectiveness of remineralization and the influence on the human body. The presence of the component (F) can be expected to improve the acid resistance of the tooth itself. In the present invention, the component (F) is preferably in the range of 0.0001 to 5%, more preferably 0.001 to 2%, particularly preferably 0.01 to 1% as the fluorine ion concentration in the composition. . If it is less than 0.0001%, the acid resistance effect and remineralization effect of the desired tooth substance do not sufficiently appear, and if it exceeds 5%, there is a concern about harm to the living body.
また、本発明の組成物には、所望により、発明の効果を損なわない範囲において、例えば塩化カルシウム、水酸化カルシウム、炭酸水素カルシウム、炭酸カルシウム、酸化カルシウム、リン酸水素カルシウム、リン酸カルシウム、ハイドロキシアパタイトなどの無機カルシウム塩や有機酸カルシウム塩などを使用することができる。
又、本発明の組成物には、エチレン性二重結合を有する低分子量、例えば４００以下、好ましくは２００以下の単量体乃至はトリマー以下のオリゴマーが少量含まれていても良い。その配合量は組成物の全量を基準に、好ましくは５％以下、より好ましくは２％以下、更に好ましくは１％以下、特に好ましくは０．５％以下、特段に好ましくは０．２％以下、もっとも好ましくは０．１％以下である。
In addition, the composition of the present invention can be applied to the composition of the present invention, as desired, within a range not impairing the effects of the invention, for example, calcium chloride, calcium hydroxide, calcium hydrogen carbonate, calcium carbonate, calcium oxide, calcium hydrogen phosphate, calcium phosphate, hydroxyapatite, etc. Inorganic calcium salts and organic acid calcium salts can be used.
Further, the composition of the present invention may contain a small amount of a low molecular weight monomer having an ethylenic double bond, for example, a monomer of 400 or less, preferably 200 or less, or an oligomer of trimer or less. The blending amount is preferably 5% or less, more preferably 2% or less, still more preferably 1% or less, particularly preferably 0.5% or less, particularly preferably 0.2% or less, based on the total amount of the composition. Most preferably, it is 0.1% or less.
本発明の組成物の使用の形態としては、好ましくは、次に挙げる様式が選択される。
（１）（Ａ）成分、（Ｂ）成分、（Ｃ）成分と（Ｄ）成分とを一緒に含む組成物を混合して容器に保存し、筆やスポンジ等を用いて直接患部に塗布し、被膜を形成して使用する方法、
（２）（Ａ）成分、（Ｂ）成分と（Ｃ）成分とを含む組成物の入った容器Ｉと（Ｂ）成分を含む組成物の入った容器ＩＩによって保存して、それぞれの組成物を任意の順で逐次的に塗布または使用直前に混合し、筆やスポンジ等を用いて直接患部に塗布し、被膜を形成して使用する方法、
（３）（Ａ）成分と（Ｃ）成分とを含む組成物の入った容器ＩＩＩと（Ｂ）成分と（Ｄ）成分とを含む組成物の入った容器ＩＶによって保存し、それぞれの組成物を任意の順で逐次的に塗布または使用直前に混合し、筆やスポンジ等を用いて直接患部に塗布し、被膜を形成して使用する方法、
（４）（Ａ）成分と（Ｃ）成分とを含む組成物の入った容器Ｖ、（Ｂ）成分と（Ｃ）成分とを含む組成物の入った容器ＶＩ、（Ｃ）成分と（Ｄ）成分とを含む組成物の入った容器ＶＩＩによって保存し、それぞれの組成物を任意の順で逐次的に塗布または使用直前に混合し、筆やスポンジ等を用いて直接患部に塗布し、被膜を形成して使用する方法、
などを例示することができる。
As the form of use of the composition of the present invention, the following modes are preferably selected.
(1) Components (A), (B), (C) and (D) are mixed together, stored in a container, and applied directly to the affected area using a brush or sponge. , A method of forming and using a film,
(2) Each of the compositions stored in a container I containing a composition containing the components (A), (B) and (C) and a container II containing the composition containing the component (B). Are applied in order in any order or mixed immediately before use, applied directly to the affected area using a brush or sponge, etc., used to form a film,
(3) Preserved in a container III containing a composition containing the components (A) and (C) and a container IV containing a composition containing the components (B) and (D). Are applied in order in any order or mixed immediately before use, applied directly to the affected area using a brush or sponge, etc., used to form a film,
(4) Container V containing a composition containing (A) component and (C) component, Container VI containing a composition containing (B) component and (C) component, (C) component and (D ) Store in a container VII containing the composition containing the ingredients, apply each composition sequentially in any order or mix immediately before use, and apply directly to the affected area using a brush or sponge, etc. How to form and use,
Etc. can be illustrated.
以下、実施例により本発明をさらに詳述するが、本発明は実施例により何ら限定されるものではない。 EXAMPLES Hereinafter, although an Example further demonstrates this invention in detail, this invention is not limited at all by an Example.
＜象牙質モデルの作製＞
新鮮なウシ下顎前歯を抜去し、水中で凍結し保存したものを歯質サンプルとして使用した。解凍したウシ歯を低速回転式ダイヤモンドカッター（ＩＳＯＭＥＴ、ＢＵＥＨＬＥＲ）にて注水下で約１０×１０×２ｍｍの象牙質板を切り出した。耐水研磨紙（＃６００）で切削面を研磨し平滑にした後、象牙質表面の片面を歯磨剤（ホワイトアンドホワイト、ライオン）のついた歯ブラシ（ガム、バトラー）で注水下２０〜３０ｇ／ｃｍ２の力で３分間ブラッシングした。精製水で洗浄の後、さらに精製水中で３５分超音波をかけることによって洗浄し、ブラッシングした表面を象牙質モデルとした。
<Production of dentin model>
Fresh bovine mandibular anterior teeth were removed, frozen and stored in water, and used as a tooth sample. About 10 × 10 × 2 mm dentin plate was cut out from the thawed bovine teeth under water injection with a low-speed rotating diamond cutter (ISOMET, BUEHLER). After polishing and smoothing the cutting surface with water-resistant abrasive paper (# 600), one side of the dentin surface is poured with a toothbrush (gum, butler) with dentifrice (white and white, lion) under water injection at 20-30 g / cm Brushed with a force of 2 for 3 minutes. After washing with purified water, it was further washed by applying ultrasonic waves in purified water for 35 minutes, and the brushed surface was used as a dentin model.
＜象牙細管封鎖の評価方法＞
水中から取り出した象牙質モデル表面からエアブローによって見かけ上の水分を取り除き乾燥した。実施例で示す組成物を充分に浸したフェルトチップ（ＭＳコート付属フェルトチップ、サンメディカル）を用いて象牙質モデル表面に塗布して２０秒間静置、さらに液が飛散しないようにエアブローによって乾燥することによって象牙細管封鎖のための被膜を形成した。被膜形成した象牙質モデルは、条件（ｉ）水中において超音波をかける処理を行った後に、あるいは条件（ｉｉ）歯ブラシを用いて注水下１００ｇの荷重で１，０００回ブラッシングし水洗する処理を行った後に、象牙細管の封鎖状況を１，０００倍に拡大した走査型電子顕微鏡（ＳＥＭ、ＪＳＭ−５６１０、日本電子）写真にて観察した。象牙細管の封鎖状況は、次式の象牙細管の封鎖率によって評価した。
<Evaluation method of ivory tubule blockage>
Apparent moisture was removed from the surface of the dentin model taken out of water by air blow and dried. Using a felt tip sufficiently soaked with the composition shown in the examples (Felt tip attached to MS coat, Sun Medical), it is applied to the surface of the dentin model and left to stand for 20 seconds, and further dried by air blow so that the liquid does not scatter. This formed a film for sealing the dentinal tubules. The coated dentin model is subjected to condition (i) treatment with ultrasonic waves in water, or condition (ii) using a toothbrush and brushing 1,000 times under water injection with a load of 100 g. Thereafter, the occlusion state of the dentinal tubule was observed with a scanning electron microscope (SEM, JSM-5610, JEOL) photograph magnified 1,000 times. The blocking condition of the dentinal tubule was evaluated by the blocking rate of the dentinal tubule of the following formula.
上記評価を行うに当たり、条件（ｉ）を行うことによって表面の被膜に吸着した異物を除去して被膜による象牙細管の封鎖状態のみを評価することができる。条件（ｉｉ）によって被膜の歯ブラシ摩耗耐久性と封鎖耐久性を評価することができ、実際の口腔内における耐久性を評価することができる。 In performing the above evaluation, by performing the condition (i), the foreign matter adsorbed on the surface film can be removed, and only the sealed state of the dentinal tubule by the film can be evaluated. According to the condition (ii), the toothbrush wear durability and the sealing durability of the coating can be evaluated, and the durability in the actual oral cavity can be evaluated.
＜歯牙色の遮蔽性試験＞
水中から取り出した象牙質モデル表面からエアブローによって見かけ上の水分を取り除き乾燥した。実施例で示す組成物を充分に浸したフェルトチップ（ＭＳコート付属フェルトチップ、サンメディカル）を用いて象牙質モデル表面に塗布して２０秒間静置、さらに液が飛散しないようにエアブローによって乾燥することによって象牙細管封鎖のための被膜を形成した。その後、組成物塗布面を肉眼で確認し、遮蔽性を以下の区分で評価した。
×明確に見える（遮蔽性なし）、
△不明確だが見える（弱い遮蔽性あり）、
○見えない（遮蔽性あり）
<Tooth color screening test>
Apparent moisture was removed from the surface of the dentin model taken out of water by air blow and dried. Using a felt tip sufficiently soaked with the composition shown in the examples (Felt tip attached to MS coat, Sun Medical), it is applied to the surface of the dentin model and left to stand for 20 seconds, and further dried by air blow so that the liquid does not scatter. This formed a film for sealing the dentinal tubules. Then, the composition application surface was confirmed with the naked eye, and the shielding properties were evaluated in the following categories.
× Clearly visible (no shielding)
△ unclear but visible (with weak shielding),
○ Invisible (with shielding)
＜水性エマルジョンの製造例＞
撹拌装置、滴下ロート、温度計、窒素導入口を備えたガラス製反応容器に、日本薬局方精製水５０ｇを６０℃に昇温し、窒素ガスを１時間バブリングした。窒素雰囲気下、メチルメタクリレート２．０ｇ、スチレンスルホン酸ナトリウム０．５４ｇ、過硫酸カリウム３０ｍｇ、亜硫酸水素ナトリウム１０ｍｇを添加し、２．５時間６０℃で激しく攪拌した。さらに、メチルメタアクリレート１．０ｇ、過硫酸カリウム１５ｍｇ、亜硫酸水素ナトリウム７ｍｇを３０分間隔で４回添加した後、さらに１９．５時間激しく攪拌した。室温に冷却後、濃塩酸０．１９ｍｌを加えて２時間攪拌し、透析チュ−ブに入れて蒸留水を５日間毎日交換しながら透析を繰り返した。このチュ−ブを常温、常圧下、乾燥して、固形分１０．９％のエマルジョンを得た。元素分析からこの重合体のメチルメタアクリレートユニットの含量は９６．９ｍｏｌ％であった。得られた重合体を分子量既知のポリメタクリル酸メチルを標準試料としてゲル除外クロマトグラフィを用いて分析したところ数平均分子量（Ｍｎ）は１．０×１０６であった。透過型顕微鏡観察より、この乳化重合体エマルジョン粒子は直径０．１〜０．５μｍの範囲にあり、レーザ回折／散乱式粒度分布測定装置（ＬＡ−９１０、堀場製作所）により全ての重合体のエマルジョン粒子の直径が１μｍ以下であることが確認された。以下、このエマルジョンをＭＳＥと略記する。
<Examples of aqueous emulsion production>
In a glass reaction vessel equipped with a stirrer, a dropping funnel, a thermometer, and a nitrogen inlet, 50 g of Japanese Pharmacopoeia purified water was heated to 60 ° C., and nitrogen gas was bubbled for 1 hour. Under a nitrogen atmosphere, 2.0 g of methyl methacrylate, 0.54 g of sodium styrenesulfonate, 30 mg of potassium persulfate, and 10 mg of sodium bisulfite were added, and the mixture was vigorously stirred at 60 ° C. for 2.5 hours. Further, 1.0 g of methyl methacrylate, 15 mg of potassium persulfate, and 7 mg of sodium bisulfite were added four times at 30-minute intervals, and the mixture was further vigorously stirred for 19.5 hours. After cooling to room temperature, 0.19 ml of concentrated hydrochloric acid was added and stirred for 2 hours. The mixture was placed in a dialysis tube and dialyzed repeatedly while exchanging distilled water every day for 5 days. The tube was dried at room temperature and normal pressure to obtain an emulsion having a solid content of 10.9%. From the elemental analysis, the content of methyl methacrylate units in this polymer was 96.9 mol%. When the obtained polymer was analyzed using gel exclusion chromatography with polymethyl methacrylate having a known molecular weight as a standard sample, the number average molecular weight (Mn) was 1.0 × 10 6 . From observation under a transmission microscope, the emulsion polymer emulsion particles are in the range of 0.1 to 0.5 μm in diameter, and all the polymer emulsions are measured by a laser diffraction / scattering type particle size distribution analyzer (LA-910, Horiba Seisakusho). It was confirmed that the diameter of the particles was 1 μm or less. Hereinafter, this emulsion is abbreviated as MSE.
上記エマルジョンＭＳＥを蒸留水で希釈して、不揮発性成分５重量％とし、これとカルシウム化合物としての塩化カルシウムを１重量％溶解する水溶液を等重量添加し、攪拌した後、粒度分布測定装置ＬＡ−９１０にて同様に粒径を測定した。エマルジョンＭＳＥに存在していた重合体エマルジョン粒子は、凝集しており、その粒径は０．１〜７００μｍの広範囲に分布し、約０．３および約４０μｍにピークを有していた。なお、重合体に対する４００以下の低分子量体乃至はトリマー以下のオリゴマーの比率は０．２％以下であった。 The emulsion MSE is diluted with distilled water to make 5% by weight of a non-volatile component, and an equal weight of an aqueous solution in which 1% by weight of calcium chloride as a calcium compound is dissolved is added and stirred. Similarly, the particle size was measured at 910. The polymer emulsion particles present in the emulsion MSE were agglomerated, and the particle size was distributed over a wide range of 0.1 to 700 μm and had peaks at about 0.3 and about 40 μm. The ratio of the low molecular weight compound of 400 or less to the polymer or the oligomer of trimer or less was 0.2% or less.
＜水溶性ポリマーの製造例＞
撹拌装置、冷却管、温度計、窒素導入口、滴下ロートを取り付けた反応装置に蒸留水２００ｇ、２，３−ジハイドロキシプロピルメタクリルアマイド３１．８ｇ（０．２ｍｏｌ）、２−アクリルアマイド−２−メチルプロパンスルホン酸１０．４ｇ（０．０５ｍｏｌ）、過硫酸アンモニウム１．１ｇ、亜硫酸ナトリウム０．６ｇを装入、１５分間窒素バブリングし、撹拌しながら内温を７０℃に昇温し、２時間重合を行った後、室温に冷却した。反応マスをアセトン／メタノールで再沈殿精製し、乾燥、無色のポリマー３０ｇを得た。得られたポリマーの分子量は９８０，０００であった。以下、このポリマーをＭＣＰと略記する。なお、重合体に対する４００以下の低分子量体乃至はトリマー以下のオリゴマーの比率は０．２％以下であった。
<Example of water-soluble polymer production>
A reactor equipped with a stirrer, a condenser, a thermometer, a nitrogen inlet, and a dropping funnel, 200 g of distilled water, 31.8 g (0.2 mol) of 2,3-dihydroxypropyl methacrylamide, 2-acrylamide-2- Charged 10.4 g (0.05 mol) of methylpropanesulfonic acid, 1.1 g of ammonium persulfate and 0.6 g of sodium sulfite, bubbled with nitrogen for 15 minutes, raised the internal temperature to 70 ° C. with stirring, and polymerized for 2 hours And then cooled to room temperature. The reaction mass was purified by reprecipitation with acetone / methanol to obtain 30 g of a dried and colorless polymer. The molecular weight of the obtained polymer was 980,000. Hereinafter, this polymer is abbreviated as MCP. The ratio of the low molecular weight compound of 400 or less to the polymer or the oligomer of trimer or less was 0.2% or less.
実施例１
上記エマルジョンＭＳＥを４．５８ｇ、アナターゼ型酸化チタン（スーパーチタニア、昭和電工、平均粒径６ｎｍ、凝集後の粒子はＳＥＭ１５，０００倍で、０．１〜２μｍの粒子が確認できた。）４．８ｍｇ、日本薬局方精製水５．４２ｇを激しく混合し、最終濃度がエマルジョンの固形分５％、二酸化チタン０．０４８％となる組成物Ａ１を調製した。一方、シュウ酸０．３ｇを脱イオン蒸留水９．７ｇに完全に溶解させ、組成物Ｂを得た。組成物Ａ１およびＢよりそれぞれ０．０５ｇずつ取り出し、使用直前に混合し、液の混合から１分以内に上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Example 1
4.58 g of the above emulsion MSE, anatase type titanium oxide (Super Titania, Showa Denko, average particle size of 6 nm, aggregated particles were SEM 15,000 times and particles of 0.1 to 2 μm were confirmed). 8 mg and 5.42 g of Japanese Pharmacopoeia purified water were vigorously mixed to prepare a composition A1 having a final concentration of 5% solid content of emulsion and 0.048% titanium dioxide. On the other hand, 0.3 g of oxalic acid was completely dissolved in 9.7 g of deionized distilled water to obtain a composition B. 0.05 g each was taken out from each of the compositions A1 and B, mixed immediately before use, and within 1 minute of mixing the liquid, the sealing performance of the dentinal tubule and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
実施例２
上記エマルジョンＭＳＥを４．５８ｇ、アナターゼ型酸化チタン（スーパーチタニア、昭和電工、平均粒径６ｎｍ、凝集後の粒子はＳＥＭ１５，０００倍で、０．１〜２μｍの粒子が確認できた）４．８ｍｇ、シュウ酸０．３ｇ、日本薬局方精製水５．１１ｇを激しく混合し、最終濃度がエマルジョンの固形分５％、二酸化チタン０．０４８％、シュウ酸１．５％となる組成物Ｃを調製した。組成物Ｃより０．１ｇ取り出し、上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Example 2
4.58 g of the above emulsion MSE, anatase type titanium oxide (Super titania, Showa Denko, average particle size 6 nm, aggregated particles were SEM 15,000 times, and 0.1 to 2 μm particles could be confirmed) 4.8 mg , 0.3 g of oxalic acid and 5.11 g of Japanese Pharmacopoeia purified water were vigorously mixed to prepare a composition C having a final concentration of 5% solids of emulsion, 0.048% titanium dioxide, and 1.5% oxalic acid. did. 0.1 g was taken out from the composition C, and the sealing performance of the dentinal tubule and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
実施例３
上記ポリマーＭＣＰを０．５ｇ、アナターゼ型酸化チタン（スーパーチタニア、昭和電工、平均粒径６ｎｍ、凝集後の粒子はＳＥＭ１５，０００倍で、０．１〜２μｍの粒子が確認できた。）４．８ｍｇ、日本薬局方精製水９．５ｇを激しく混合し、最終濃度が重合体５％、二酸化チタン０．０４８％となる組成物Ａ２を調製した。一方、シュウ酸０．３ｇを脱イオン蒸留水９．７ｇに完全に溶解させ、組成物Ｂを得た。組成物Ａ２およびＢよりそれぞれ０．０５ｇずつ取り出し、使用直前に混合し、液の混合から１分以内に上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Example 3
3. 0.5 g of the above polymer MCP, anatase type titanium oxide (Super titania, Showa Denko, average particle size 6 nm, aggregated particles were SEM 15,000 times, and 0.1 to 2 μm particles could be confirmed). 8 mg and 9.5 g of Japanese Pharmacopoeia purified water were vigorously mixed to prepare a composition A2 having a final concentration of 5% polymer and 0.048% titanium dioxide. On the other hand, 0.3 g of oxalic acid was completely dissolved in 9.7 g of deionized distilled water to obtain a composition B. 0.05 g each was taken out from each of the compositions A2 and B, mixed immediately before use, and within 1 minute from the mixing of the liquids, the sealing performance of the dentinal tubule and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
実施例４
上記ポリマーＭＣＰを０．５ｇ、アナターゼ型酸化チタン（スーパーチタニア、昭和電工、平均粒径６ｎｍ、凝集後の粒子はＳＥＭ１５，０００倍で、０．１〜２μｍの粒子が確認できた。）４．８ｍｇ、シュウ酸０．１５ｇ、日本薬局方精製水９．３５ｇを激しく混合し、最終濃度が重合体５％、二酸化チタン０．０４８％、シュウ酸１．５％となる組成物Ｄを調製した。組成物Ｄより０．１ｇ取り出し、上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Example 4
3. 0.5 g of the above polymer MCP, anatase type titanium oxide (Super titania, Showa Denko, average particle size 6 nm, aggregated particles were SEM 15,000 times, and 0.1 to 2 μm particles could be confirmed). 8 mg, oxalic acid 0.15 g, and Japanese Pharmacopoeia purified water 9.35 g were vigorously mixed to prepare a composition D having a final concentration of 5% polymer, titanium dioxide 0.048%, and oxalic acid 1.5%. . 0.1 g was taken out from the composition D, and the sealing performance of the dentinal tubule and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
比較例１
実施例１において、組成物Ａ１およびＢに代えて、どちらも脱イオン精製水を使用した以外は同様に操作した。結果を表１に記す。
Comparative Example 1
In Example 1, it replaced with composition A1 and B, and it operated similarly except having used deionized purified water for both. The results are shown in Table 1.
比較例２
上記エマルジョンＭＳＥを４．５８ｇ、日本薬局方精製水５．４２ｇを激しく混合し、最終濃度がエマルジョンの固形分５％となる組成物Ｅを調製した。一方、シュウ酸０．３ｇを脱イオン蒸留水９．７ｇに完全に溶解させ、組成物Ｂを得た。組成物ＥおよびＢよりそれぞれ０．０５ｇずつ取り出し、使用直前に混合し、液の混合から１分以内に上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Comparative Example 2
4.58 g of the above emulsion MSE and 5.42 g of Japanese Pharmacopoeia purified water were vigorously mixed to prepare a composition E having a final concentration of 5% solid content of the emulsion. On the other hand, 0.3 g of oxalic acid was completely dissolved in 9.7 g of deionized distilled water to obtain a composition B. 0.05 g each was taken out from each of the compositions E and B, mixed immediately before use, and within 1 minute from the mixing of the liquids, the sealing performance of the dentinal tubules and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
比較例３
上記エマルジョンＭＳＥを４．５８ｇ、シュウ酸０．３ｇ、日本薬局方精製水５．１１ｇを激しく混合し、最終濃度がエマルジョンの固形分５％、シュウ酸１．５％となる組成物Ｆを調製した。組成物Ｆより０．１ｇ取り出し、上記象牙細管の封鎖性評価、歯牙色遮蔽性評価を行った。結果を表１に記す。
Comparative Example 3
4.58 g of the above emulsion MSE, 0.3 g of oxalic acid and 5.11 g of Japanese Pharmacopoeia purified water are vigorously mixed to prepare a composition F having a final concentration of 5% solid content of emulsion and 1.5% oxalic acid. did. 0.1 g was taken out from the composition F, and the sealing performance of the dentinal tubule and the evaluation of the tooth color shielding were performed. The results are shown in Table 1.
Claims (7)
（Ａ）分子内に酸性基を少なくとも１つ有する重合性単量体（Ｍａ）の少なくとも１種に由来する単量体単位を有する重合体、
（Ｂ）アナターゼ型二酸化チタン粒子、
（Ｃ）溶媒および／または分散媒および
（Ｄ）水溶性酸性化合物。 A dental composition comprising the following components (A), (B), (C) and (D) and used for tooth color masking and / or suppression of hypersensitivity.
(A) a polymer having a monomer unit derived from at least one polymerizable monomer (Ma) having at least one acidic group in the molecule;
(B) anatase-type titanium dioxide particles,
(C) A solvent and / or a dispersion medium and (D) a water-soluble acidic compound.
象牙細管径よりも小さい粒子径を有する水性エマルジョン形態を有する重合体（Ａｓ）および／または水溶性重合体（Ａｗ）
でありそしてカルシウム化合物と反応して象牙細管径よりも大きな凝集体を形成する請求項１に記載の歯科用組成物。 (A) component is
Polymer (As) and / or water-soluble polymer (Aw) having an aqueous emulsion form having a particle diameter smaller than the dentinal tubule diameter
The dental composition of claim 1, wherein the dental composition reacts with a calcium compound to form an aggregate larger than the dentinal tubule diameter.
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