JP2017061418A - Oral composition - Google Patents
Oral composition Download PDFInfo
- Publication number
- JP2017061418A JP2017061418A JP2015186783A JP2015186783A JP2017061418A JP 2017061418 A JP2017061418 A JP 2017061418A JP 2015186783 A JP2015186783 A JP 2015186783A JP 2015186783 A JP2015186783 A JP 2015186783A JP 2017061418 A JP2017061418 A JP 2017061418A
- Authority
- JP
- Japan
- Prior art keywords
- group
- composition
- oil
- phosphorylcholine
- meth
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- NJNWCIAPVGRBHO-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-[(oxo-$l^{5}-phosphanylidyne)methyl]azanium Chemical group OCC[N+](C)(C)C#P=O NJNWCIAPVGRBHO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003899 bactericide agent Substances 0.000 claims abstract description 6
- 210000000214 mouth Anatomy 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- LWLHCZLCSDUDEL-UHFFFAOYSA-O C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C Chemical compound C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C LWLHCZLCSDUDEL-UHFFFAOYSA-O 0.000 claims description 5
- 230000007505 plaque formation Effects 0.000 abstract description 14
- 230000003405 preventing effect Effects 0.000 abstract description 10
- 244000005700 microbiome Species 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000008021 deposition Effects 0.000 abstract 1
- -1 acryl Chemical group 0.000 description 35
- 238000000034 method Methods 0.000 description 31
- 230000000694 effects Effects 0.000 description 18
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000796 flavoring agent Substances 0.000 description 11
- 235000019634 flavors Nutrition 0.000 description 11
- 239000008363 phosphate buffer Substances 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
- 239000007943 implant Substances 0.000 description 5
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 238000012423 maintenance Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 241000194019 Streptococcus mutans Species 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 208000002925 dental caries Diseases 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 2
- XHXUANMFYXWVNG-ADEWGFFLSA-N (-)-Menthyl acetate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 description 2
- ZSZRUEAFVQITHH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(=C)C(=O)OCCOP([O-])(=O)OCC[N+](C)(C)C ZSZRUEAFVQITHH-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 206010006326 Breath odour Diseases 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 235000011203 Origanum Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000008312 Tooth Loss Diseases 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000002272 anti-calculus Effects 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940030225 antihemorrhagics Drugs 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 239000007621 bhi medium Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000002874 hemostatic agent Substances 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- DFENKTCEEGOWLB-UHFFFAOYSA-N n,n-bis(methylamino)-2-methylidenepentanamide Chemical compound CCCC(=C)C(=O)N(NC)NC DFENKTCEEGOWLB-UHFFFAOYSA-N 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 235000019477 peppermint oil Nutrition 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 201000001245 periodontitis Diseases 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 2
- IAEGWXHKWJGQAZ-UHFFFAOYSA-N trimethylpyrazine Chemical compound CC1=CN=C(C)C(C)=N1 IAEGWXHKWJGQAZ-UHFFFAOYSA-N 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 description 1
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- 239000001605 (5-methyl-2-propan-2-ylcyclohexyl) acetate Substances 0.000 description 1
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JHEPBQHNVNUAFL-AATRIKPKSA-N (e)-hex-1-en-1-ol Chemical compound CCCC\C=C\O JHEPBQHNVNUAFL-AATRIKPKSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- MVOSYKNQRRHGKX-UHFFFAOYSA-N 11-Undecanolactone Chemical compound O=C1CCCCCCCCCCO1 MVOSYKNQRRHGKX-UHFFFAOYSA-N 0.000 description 1
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 description 1
- CFAKWWQIUFSQFU-UHFFFAOYSA-N 2-hydroxy-3-methylcyclopent-2-en-1-one Chemical compound CC1=C(O)C(=O)CC1 CFAKWWQIUFSQFU-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 1
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- TWXUTZNBHUWMKJ-UHFFFAOYSA-N Allyl cyclohexylpropionate Chemical compound C=CCOC(=O)CCC1CCCCC1 TWXUTZNBHUWMKJ-UHFFFAOYSA-N 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229940093158 polyhexanide Drugs 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- GEYJUFBPCGDENK-UHFFFAOYSA-M sodium;3,8-dimethyl-5-propan-2-ylazulene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC=C(C)C2=C(S([O-])(=O)=O)C=C(C)C2=C1 GEYJUFBPCGDENK-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、ホスホリルコリン基含有重合体を含有する口腔用組成物に関する。より詳しくは、歯科補綴物使用者に好適に使用できる口腔用組成物に関する。 The present invention relates to an oral composition containing a phosphorylcholine group-containing polymer. More specifically, the present invention relates to an oral composition that can be suitably used for a dental prosthesis user.
歯科補綴物とは、歯の欠損や喪失があった時に歯の状態を元に戻すために補われる人工物である。歯の欠損および喪失原因には、破折、う蝕、歯周病等が挙げられる。欠損歯や喪失歯の増加は、食事や会話の不満につながり、ひいては体調悪化や病臥する原因にもなりうる。そのため、歯科補綴物は治療に不可欠である。
一方、補綴物を使用する際は、そのメンテナンスが重要となる。例えば、義歯は隙間ができやすいことから義歯床下にプラークが生成されやすいことが知られている（非特許文献１）。プラークとは、微生物とその代謝物の複合体で、歯や歯肉、歯科補綴物等に微生物が付着し、増殖することで形成される。また、インプラント使用者は、インプラント歯根部にプラークが形成されると天然歯と比較し、歯周炎を引き起こすリスクが高まることも知られている（非特許文献２）。補綴物に形成されたプラークは、容易に周囲の健康歯にも伝播する。そのため、補綴物のメンテナンスを怠ると健康歯の喪失を促す原因になりうる。
A dental prosthesis is an artificial object that is supplemented to restore the state of a tooth when a tooth is lost or lost. Causes of tooth loss and loss include fracture, caries, periodontal disease and the like. An increase in missing or lost teeth can lead to dissatisfaction with food and conversation, which can lead to poor physical condition and illness. Therefore, dental prostheses are essential for treatment.
On the other hand, when using a prosthesis, its maintenance is important. For example, it is known that plaque tends to be generated under the denture base because a denture easily forms a gap (Non-patent Document 1). Plaque is a complex of microorganisms and their metabolites, and is formed when microorganisms adhere to and grow on teeth, gums, dental prostheses and the like. In addition, it is also known that an implant user has a higher risk of causing periodontitis than a natural tooth when plaque is formed in an implant root (Non-Patent Document 2). Plaques formed on the prosthesis easily propagate to surrounding healthy teeth. Therefore, neglecting maintenance of the prosthesis can cause loss of healthy teeth.
義歯の場合は、日々取り外して専用の洗浄剤を用いて付着したプラークを除去するメンテナンス方法が取れるため、比較的清潔に保つことができる。しかしながら、クラウンやインプラント等の埋没型の補綴物の場合、使用者が取り外すことはできないために、義歯のようなメンテナンスができない。
そこで、補綴物へのプラーク付着を防止するコーティング剤に関する技術が公開されている。例えば、フッ素含有ポリマーからなるコーティング組成物（特許文献１、２）や、２−メタクリロイルオキシエチルホスホリルコリンと（メタ）アクリル酸エステルの共重合体からなるコーティング組成物が公開されている（特許文献３）。しかし、これらはレジン系材料に対してのみ有効性を確認しているが、歯科補綴物には金属製の義歯床やブリッジ等も存在し、また、インプラント歯周炎は、金属製の人工歯根部にプラークが形成されることで発症する疾患である。このことから、プラーク形成を抑制する歯科補綴物コーティング剤に対しては、レジン系材料のみならず金属材料に対してもプラーク形成防止効果を有することが求められている。
In the case of a denture, it can be kept relatively clean because it can be removed daily and a maintenance method can be used to remove the adhering plaque using a special cleaning agent. However, in the case of an embedded type prosthesis such as a crown or an implant, maintenance cannot be performed like a denture because the user cannot remove it.
Then, the technique regarding the coating agent which prevents the plaque adhesion to a prosthesis is published. For example, a coating composition made of a fluorine-containing polymer (Patent Documents 1 and 2) and a coating composition made of a copolymer of 2-methacryloyloxyethyl phosphorylcholine and (meth) acrylic acid ester are disclosed (Patent Document 3). ). However, these have been confirmed to be effective only for resin-based materials, but there are metal denture bases and bridges in dental prostheses, and implant periodontitis is a metal artificial root. It is a disease that develops due to the formation of plaque. For this reason, dental prosthesis coating agents that suppress plaque formation are required to have an effect of preventing plaque formation not only on resin materials but also on metal materials.
上記の通り、本発明の課題は、歯科補綴物への微生物付着防止効果およびプラーク形成防止効果に優れた歯科補綴物使用者向け口腔用組成物を提供することである。 As above-mentioned, the subject of this invention is providing the composition for oral cavity for dental prosthesis users excellent in the microorganisms adhesion prevention effect and plaque formation prevention effect to a dental prosthesis.
本発明者らは、上記課題を解決するために鋭意検討を行った結果、特定の重量平均分子量を有するホスホリルコリン基含有重合体を特定量、殺菌剤と組合せて含有する口腔用組成物が上記の課題を解決することの知見を見出し、本発明を完成するに至った。
すなわち、本発明は次の〔１〕である。
As a result of intensive investigations to solve the above problems, the present inventors have found that an oral composition containing a specific amount of a phosphorylcholine group-containing polymer having a specific weight average molecular weight in combination with a bactericidal agent is described above. The present inventors have found the knowledge of solving the problems and have completed the present invention.
That is, the present invention is the following [1].
〔１〕２−（メタ）アクリロイルオキシエチルホスホリルコリンに基づく構成単位（Ａ）１０〜９０モル％と、アルキル基含有（メタ）アクリル系単量体に基づく構成単位（Ｂ１）および／または（メタ）アクリルアミド系単量体に基づく構成単位（Ｂ２）１０〜９０モル％とを含有し、重量平均分子量５１０，０００〜５，０００，０００であるホスホリルコリン基含有重合体（Ｐ）０．００１重量％〜１０重量％と、
殺菌剤（Ｃ）と、を含有する口腔用組成物。
[1] Structural unit (A) based on 2- (meth) acryloyloxyethyl phosphorylcholine (A) 10 to 90 mol%, and structural unit (B1) and / or (meth) based on alkyl group-containing (meth) acrylic monomer A phosphorylcholine group-containing polymer (P) having a weight average molecular weight of 510,000 to 5,000,000 containing 0.001% by weight to a structural unit (B2) based on an acrylamide monomer and 10 to 90% by mole 10% by weight,
An oral composition containing a bactericidal agent (C).
〔２〕歯科補綴物用口腔用組成物である前項１に記載の口腔用組成物。
[2] The composition for oral cavity according to 1 above, which is a composition for oral cavity for dental prosthesis.
本発明によって、歯科補綴物への微生物付着防止効果およびプラーク形成防止効果に優れた歯科補綴物使用者向け口腔用組成物を提供することが可能となる。 ADVANTAGE OF THE INVENTION By this invention, it becomes possible to provide the composition for oral cavity for dental prosthesis users excellent in the microorganisms adhesion prevention effect and plaque formation prevention effect to a dental prosthesis.
以下、本発明をさらに詳細に説明する。
本発明の口腔用組成物は、下記のホスホリルコリン基含有重合体（Ｐ）と殺菌剤（Ｃ）とを含有する。
Hereinafter, the present invention will be described in more detail.
The composition for oral cavity of the present invention contains the following phosphorylcholine group-containing polymer (P) and a bactericidal agent (C).
＜ホスホリルコリン基含有重合体（Ｐ）＞
本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、２−（メタ）アクリロイルオキシエチルホスホリルコリンに基づく構成単位（Ａ）１０〜９０モル％と、アルキル基含有（メタ）アクリル系単量体に基づく構成単位（Ｂ１）および／または（メタ）アクリルアミド系単量体に基づく構成単位（Ｂ２）１０〜９０モル％とを含有し、重量平均分子量５１０，０００〜５，０００，０００である。
<Phosphorylcholine group-containing polymer (P)>
The phosphorylcholine group-containing polymer (P) used in the present invention is based on a structural unit (A) of 10 to 90 mol% based on 2- (meth) acryloyloxyethyl phosphorylcholine and an alkyl group-containing (meth) acrylic monomer. It contains 10 to 90 mol% of the structural unit (B1) and / or the structural unit (B2) based on the (meth) acrylamide monomer, and has a weight average molecular weight of 510,000 to 5,000,000.
＜２−（メタ）アクリロイルオキシエチルホスホリルコリンに基づく構成単位（Ａ）＞
２−（メタ）アクリロイルオキシエチルホスホリルコリンに基づく構成単位（Ａ）は、より具体的には下記の式（Ａ）で表され、式（Ａ'）で表される単量体の重合によって得られる。
なお、本発明において「（メタ）アクリル」は、アクリルまたはメタアクリル（メタクリル）を意味し、「（メタ）アクリロイル」は、アクリロイルまたはメタアクリロイル（メタクリロイル）を意味し、「（メタ）アクリレート」は、アクリレートまたはメタアクリレート（メタクリレート）を意味し、「（メタ）アクリルアミド」は、アクリルアミドまたはメタアクリルアミド（メタクリルアミド）を意味する。
<Structural Unit (A) Based on 2- (Meth) acryloyloxyethyl phosphorylcholine>
The structural unit (A) based on 2- (meth) acryloyloxyethyl phosphorylcholine is more specifically represented by the following formula (A), and is obtained by polymerization of a monomer represented by the formula (A ′). .
In the present invention, “(meth) acryl” means acryl or methacryl (methacryl), “(meth) acryloyl” means acryloyl or methacryloyl (methacryloyl), and “(meth) acrylate” , Acrylate or methacrylate (methacrylate), and “(meth) acrylamide” means acrylamide or methacrylamide (methacrylamide).
式（Ａ）および（Ａ'）において、Ｒ１は水素原子もしくはメチル基のいずれでも良いが、好ましくはメチル基である。
本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、分子鎖中に構成単位（Ａ）を有することによって、歯科補綴物表面におけるプラーク形成防止効果を発現することができる。本発明に用いるホスホリルコリン基含有重合体（Ｐ）中の構成単位（Ａ）の組成比は、１０〜９０モル％であり、好ましくは２０〜９０モル％であり、より好ましくは３０〜９０モル％である。組成比が低すぎるとプラーク形成防止効果が低くなり、高すぎるとそれ自身が超親水性のために水中に流れ出てしまうために効果が低くなる。
In the formulas (A) and (A ′), R 1 may be either a hydrogen atom or a methyl group, but is preferably a methyl group.
The phosphorylcholine group-containing polymer (P) used in the present invention can exhibit the effect of preventing plaque formation on the dental prosthesis surface by having the structural unit (A) in the molecular chain. The composition ratio of the structural unit (A) in the phosphorylcholine group-containing polymer (P) used in the present invention is 10 to 90 mol%, preferably 20 to 90 mol%, more preferably 30 to 90 mol%. It is. If the composition ratio is too low, the effect of preventing plaque formation will be low, and if it is too high, the effect will be low because it will flow out into water due to its super hydrophilicity.
＜アルキル基含有（メタ）アクリル系単量体に基づく構成単位（Ｂ１）＞
アルキル基含有（メタ）アクリル系単量体に基づく構成単位（Ｂ１）は、より具体的には下記の式（Ｂ１）で表され、式（Ｂ１'）で表される単量体の重合によって得られる。本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、分子鎖中に構成単位（Ｂ１）を有することによって、ホスホリルコリン基含有重合体（Ｐ）の歯面への吸着性をより高めることが出来る。
<Constitutional unit (B1) based on alkyl group-containing (meth) acrylic monomer>
The structural unit (B1) based on the alkyl group-containing (meth) acrylic monomer is more specifically represented by the following formula (B1), and by polymerization of the monomer represented by the formula (B1 ′). can get. The phosphorylcholine group-containing polymer (P) used in the present invention can further enhance the adsorptivity of the phosphorylcholine group-containing polymer (P) to the tooth surface by having the structural unit (B1) in the molecular chain.
式（Ｂ１）および式（Ｂ１'）において、Ｒ２は水素原子もしくはメチル基のいずれでも良いが、好ましくはメチル基である。Ｒ３は炭素数４〜１８の直鎖状または分岐状のアルキル基のいずれでも良い。 In Formula (B1) and Formula (B1 ′), R 2 may be either a hydrogen atom or a methyl group, but is preferably a methyl group. R 3 may be a linear or branched alkyl group having 4 to 18 carbon atoms.
炭素数４〜１８の直鎖状アルキル基としては、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−へプチル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−ドデシル基、ｎ−トリデシル基、ｎ−テトラデシル基、ｎ−ペンタデシル基、ｎ−ヘキサデシル基、ｎ−ヘプタデシル基、ｎ−オクタデシル基が挙げられる。炭素数４〜１８の分岐状アルキル基としては、ｔ−ブチル基、イソブチル基、イソペンチル基、ｔ−ペンチル基、ネオペンチル基、イソヘキシル基、イソへプチル基、イソオクチル基、イソノニル基、イソデシル基、イソウンデシル基、イソドデシル基、イソトリデシル基、イソテトラデシル基、イソペンタデシル基、イソヘキサデシル基、イソヘプタデシル基、イソオクタデシル基などが挙げられる。
Ｒ３は、好ましくはｎ−ブチル基であるが、ホスホリルコリン基含有重合体（Ｐ）中に式（Ｂ２）を含有する場合はこの限りでない。
アルキル基含有（メタ）アクリル系単量体の好適な例として、ブチルメタクリレート、ステアリルメタクリレート等が挙げられる。
Examples of the linear alkyl group having 4 to 18 carbon atoms include n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, Examples include n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group and n-octadecyl group. Examples of the branched alkyl group having 4 to 18 carbon atoms include t-butyl group, isobutyl group, isopentyl group, t-pentyl group, neopentyl group, isohexyl group, isoheptyl group, isooctyl group, isononyl group, isodecyl group, and isoundecyl. Group, isododecyl group, isotridecyl group, isotetradecyl group, isopentadecyl group, isohexadecyl group, isoheptadecyl group, isooctadecyl group and the like.
R 3 is preferably an n-butyl group, but this is not the case when the phosphorylcholine group-containing polymer (P) contains the formula (B2).
Preferable examples of the alkyl group-containing (meth) acrylic monomer include butyl methacrylate and stearyl methacrylate.
＜（メタ）アクリルアミド系単量体に基づく構成単位（Ｂ２）＞
（メタ）アクリルアミド系単量体に基づく構成単位（Ｂ２）は、より具体的には下記の式（Ｂ２）で表され、式（Ｂ２'）で表される単量体の重合によって得られる。本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、分子鎖中に構成単位（Ｂ２）を有することによって、ホスホリルコリン基含有重合体（Ｐ）を高分子量化し、ホスホリルコリン基含有重合体（Ｐ）の歯面への密着性をより高めることが出来る。
<Structural Unit (B2) Based on (Meth) acrylamide Monomer>
More specifically, the structural unit (B2) based on the (meth) acrylamide monomer is represented by the following formula (B2), and is obtained by polymerization of the monomer represented by the formula (B2 ′). The phosphorylcholine group-containing polymer (P) used in the present invention has a structural unit (B2) in the molecular chain, thereby increasing the molecular weight of the phosphorylcholine group-containing polymer (P). The adhesion to the tooth surface can be further increased.
式（Ｂ２）および式（Ｂ２'）において、Ｒ４は水素原子もしくはメチル基のいずれでも良いが、好ましくは水素原子である。Ｒ５およびＲ６はそれぞれ独立に水素原子または炭素数１〜６のアルキル基を示し、アルキル基は直鎖状、分岐状および環状のいずれであっても良い。具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基、イソペンチル基、ｎ−ヘキシル基、イソヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などが挙げられる。
Ｒ５およびＲ６として好ましくは、水素原子、メチル基、エチル基、プロピル基もしくはイソプロピル基であり、より好ましくはメチル基である。
（メタ）アクリルアミド系単量体の好適な例としては、Ｎ，Ｎ−ジメチルアミノプロピルアクリルアミド等を挙げることができる。
In formula (B2) and formula (B2 ′), R 4 may be either a hydrogen atom or a methyl group, but is preferably a hydrogen atom. R 5 and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear, branched or cyclic. Specifically, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group , Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
R 5 and R 6 are preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, or an isopropyl group, and more preferably a methyl group.
Preferable examples of the (meth) acrylamide monomer include N, N-dimethylaminopropylacrylamide.
本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、分子鎖中に構成単位（Ｂ１）および／または（Ｂ２）を有することによって、歯科補綴物へ吸着することができる。本発明に用いるホスホリルコリン基含有重合体（Ｐ）中の構成単位（Ｂ１）および（Ｂ２）の組成比（（Ｂ１）および（Ｂ２）のうちいずれか１つの構成単位のみ有する場合は当該構成単位の組成比、（Ｂ１）および（Ｂ２）を両方有する場合は、それらの構成単位の合計組成比）は、１０〜９０モル％であり、好ましくは１０〜８０モル％であり、より好ましくは１０〜７０モル％である。組成比が低すぎるとホスホリルコリン基含有重合体（Ｐ）の親水性が高いために口腔内において本発明の組成物の歯科補綴物へのコーティング力が弱くなり、高すぎるとプラーク形成防止効果が低くなる。 The phosphorylcholine group-containing polymer (P) used in the present invention can be adsorbed to a dental prosthesis by having the structural units (B1) and / or (B2) in the molecular chain. The composition ratio of the structural units (B1) and (B2) in the phosphorylcholine group-containing polymer (P) used in the present invention (when only one of the structural units (B1) and (B2) is present) In the case of having both (B1) and (B2), the composition ratio is 10 to 90 mol%, preferably 10 to 80 mol%, more preferably 10 to 90 mol%. 70 mol%. If the composition ratio is too low, the phosphorylcholine group-containing polymer (P) has high hydrophilicity, so that the coating power of the composition of the present invention on the dental prosthesis is weak in the oral cavity, and if it is too high, the effect of preventing plaque formation is low. Become.
本発明に用いるホスホリルコリン基含有重合体（Ｐ）の分子鎖中に含まれる、構成単位（Ａ）と構成単位（Ｂ１）および／または（Ｂ２）の組み合わせの好適な例は、以下の通りである。便宜上、単量体の名称で組み合わせを記載する。
２−メタクリロイルオキシエチルホスホリルコリン（以下、ＭＰＣ）およびブチルメタクリレート（以下、ＢＭＡ）；ならびに
ＭＰＣ、Ｎ，Ｎ−ジメチルアミノプロピルアクリルアミド（以下、ＤＭＡＰＡＡ）およびＳＭＡ。
Preferred examples of the combination of the structural unit (A) and the structural units (B1) and / or (B2) contained in the molecular chain of the phosphorylcholine group-containing polymer (P) used in the present invention are as follows. . For convenience, the combination is described by the name of the monomer.
2-methacryloyloxyethyl phosphorylcholine (hereinafter referred to as MPC) and butyl methacrylate (hereinafter referred to as BMA); and MPC, N, N-dimethylaminopropylacrylamide (hereinafter referred to as DMAPAA) and SMA.
本発明に用いるホスホリルコリン基含有重合体（Ｐ）は、構成単位（Ａ）および構成単位（Ｂ１）、（Ｂ２）以外の構成単位を有してもよいが、好ましくは、構成単位（Ａ）および構成単位（Ｂ１）、（Ｂ２）を９０モル％以上含む。
本発明に用いられるホスホリルコリン基含有重合体（Ｐ）は、好ましくは、ラジカル重合によって製造する。例えば、公開公報特開平１１−０３５６０５の方法や公開公報特開２０１３−０１８７４９の方法に準ずる重合方法を用いることができる。
The phosphorylcholine group-containing polymer (P) used in the present invention may have a structural unit other than the structural unit (A) and the structural units (B1) and (B2), but preferably the structural unit (A) and 90 mol% or more of structural units (B1) and (B2) are included.
The phosphorylcholine group-containing polymer (P) used in the present invention is preferably produced by radical polymerization. For example, a polymerization method according to the method disclosed in Japanese Patent Laid-Open No. 11-035605 or the method disclosed in Japanese Patent Laid-Open No. 2013-018749 can be used.
本発明に用いるホスホリルコリン基含有重合体（Ｐ）の重量平均分子量は５１０，０００〜５，０００，０００であり、好ましくは、５１０，０００〜１，０００，０００である。重量平均分子量が５１０，０００未満であると口腔内に装着状態の歯科補綴物に対してプラーク形成防止効果を十分に得られず、重量平均分子量が５，０００，０００より大きいと粘度が急激に上昇し、口腔用組成物を製することが困難となる恐れがある。 The weight average molecular weight of the phosphorylcholine group-containing polymer (P) used in the present invention is 510,000 to 5,000,000, preferably 510,000 to 1,000,000. If the weight average molecular weight is less than 510,000, the effect of preventing plaque formation cannot be sufficiently obtained for a dental prosthesis mounted in the oral cavity. It may rise and it may be difficult to produce an oral composition.
＜口腔用組成物＞
本発明の口腔用組成物に含有するホスホリルコリン基含有重合体（Ｐ）の配合量は、ホスホリルコリン基含有重合体（Ｐ）を組成物全体に対して、０．００１〜１０重量％である。配合量が０．００１重量％未満であると、歯科補綴物へのプラークの付着防止効果が得られない恐れがあり、配合量が１０重量％以上であっても、添加量に見合った効果が得られない。
<Oral composition>
The compounding quantity of the phosphorylcholine group containing polymer (P) contained in the composition for oral cavity of this invention is 0.001 to 10 weight% with respect to the whole composition of a phosphorylcholine group containing polymer (P). If the blending amount is less than 0.001% by weight, the effect of preventing the adhesion of plaque to the dental prosthesis may not be obtained. Even if the blending amount is 10% by weight or more, the effect corresponding to the addition amount is obtained. I can't get it.
本発明の口腔用組成物に配合される殺菌剤（Ｃ）は、口腔用に薬事的に配合することが可能な量を含有することができる。この殺菌剤としては、例えば、イソプロピルメチルフェノール、塩化セチルピリジニウム、塩化デカリニウム、塩化ベンザルコニウム、塩化ベンゼトニウム、塩酸アルキルジアミノエチルグリシン、塩酸クロルヘキシジン、グルコン酸クロルヘキシジン、トリクロサン、ラウロイルサルコシンナトリウム、ヒノキチオール、塩酸ポリヘキサニド、塩化スズ、フッ化スズ等が挙げられるが、特に限定はされない。 The disinfectant (C) blended in the oral composition of the present invention can contain an amount that can be formulated pharmacologically for the oral cavity. Examples of the disinfectant include isopropylmethylphenol, cetylpyridinium chloride, decalinium chloride, benzalkonium chloride, benzethonium chloride, alkyldiaminoethylglycine hydrochloride, chlorhexidine hydrochloride, chlorhexidine gluconate, triclosan, sodium lauroyl sarcosine, hinokitiol, polyhexanide hydrochloride , Tin chloride, tin fluoride and the like, but are not particularly limited.
本発明は、洗口液、含嗽剤、歯磨剤、口中清涼剤、チュアブル剤などの口腔用組成物に応用・適用することができ、その形態も液状、粘性液体、ジェル状など特に限定されない。
さらに、本発明の口腔用組成物は、ホスホリルコリン基含有重合体および殺菌剤以外に必要に応じて一般に口腔用組成物に使用でき、例えば、ｐＨ調節剤、湿潤剤、溶解補助剤、粘稠化剤、溶剤、消炎剤、止血剤、知覚過敏緩和剤、う蝕予防剤、歯石沈着防止剤、口臭除去剤、収斂剤、歯垢除去剤、ビタミン剤、洗浄助剤、甘味剤、着色剤、防腐剤、香料等を配合することができる。
The present invention can be applied to and applied to oral compositions such as mouthwashes, mouthwashes, dentifrices, mouth fresheners, chewable agents and the like, and the form thereof is not particularly limited, such as liquid, viscous liquid, and gel.
Furthermore, the oral composition of the present invention can be generally used in oral compositions as needed in addition to the phosphorylcholine group-containing polymer and the bactericidal agent. For example, a pH adjuster, a wetting agent, a solubilizing agent, and a thickening agent. Agent, solvent, anti-inflammatory agent, hemostatic agent, hypersensitivity relieving agent, caries preventive agent, anticalculus agent, halitosis remover, astringent, plaque remover, vitamin agent, cleaning aid, sweetener, colorant, An antiseptic | preservative, a fragrance | flavor, etc. can be mix | blended.
ｐＨ調節剤としては、クエン酸、リン酸、リンゴ酸、グルコン酸およびこれらの塩が挙げられるが、特に限定はされない。
湿潤剤としては、グリセリン、プロピレングリコール、ブチレングリコール、ペンチレングリコール、ジプロピレングリコール、ポリエチレングリコール、キシリトール、マンニトール、エリスリトールが挙げられるが、特に限定はされない。
溶解補助剤としては、ポリオキシエチレン硬化ヒマシ油、ポリオキシエチレン硬化ヒマシ油６０、ソルビタン脂肪酸エチレン付加物、ポリグリセリン脂肪酸エステル、アシルアミノ酸塩、脂肪酸アミノプロピルベタイン、脂肪酸アミドベタインなどが挙げられるが、特に限定はされない。
Examples of the pH adjuster include citric acid, phosphoric acid, malic acid, gluconic acid, and salts thereof, but are not particularly limited.
Examples of the wetting agent include glycerin, propylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, polyethylene glycol, xylitol, mannitol, and erythritol, but are not particularly limited.
Examples of the solubilizer include polyoxyethylene hydrogenated castor oil, polyoxyethylene hydrogenated castor oil 60, sorbitan fatty acid ethylene adduct, polyglycerin fatty acid ester, acylamino acid salt, fatty acid aminopropyl betaine, fatty acid amide betaine, There is no particular limitation.
粘稠化剤としては、例えばメチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロース等のセルロース系粘稠化剤、ヒアルロン酸およびその塩、コンドロイチン硫酸およびその塩、アルギン酸およびその塩、ジュランガム、キサンタンガム等の多糖類系粘稠化剤が挙げられるが、特に限定はされない。
溶剤としては、口腔に対する安全性が確認されているものであれば特に限定はされないが、例えば水、エタノール、プロピレングリコールが挙げられる。
Examples of the thickening agent include cellulose-based thickening agents such as methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, hyaluronic acid and its salt, chondroitin sulfate and its salt, alginic acid and its salt, dulan gum And polysaccharide thickeners such as xanthan gum, but not particularly limited.
The solvent is not particularly limited as long as safety for the oral cavity has been confirmed, and examples thereof include water, ethanol, and propylene glycol.
消炎剤としては特に限定はされないが、アズレンスルホン酸ナトリウム、アラントイン、アラントインクロルヒドロキシアルミニウム、アラントインジヒドロキシアルミニウム、エピジヒドロキシコレステリン、ジヒドロコレステロール、グリチルリチン酸およびその塩、β−グリチルレチン酸、塩化リゾチーム、サリチル酸メチル等が挙げられる。
止血剤としては特に限定はされないが、ε−アミノカプロン酸、トラネキサム酸等が挙げられる。
The anti-inflammatory agent is not particularly limited, but sodium azulenesulfonate, allantoin, allantochlorohydroxyaluminum, allantoindihydroxyaluminum, epidihydroxycholesterin, dihydrocholesterol, glycyrrhizic acid and its salt, β-glycyrrhetinic acid, lysozyme chloride, methyl salicylate Etc.
Although it does not specifically limit as a hemostatic agent, (epsilon) -aminocaproic acid, tranexamic acid, etc. are mentioned.
ビタミン剤としては特に限定はされないが、アスコルビン酸およびその塩、塩酸ピリドキシン、酢酸ｄｌ−α−トコフェロール、ニコチン酸ｄｌ−α−トコフェロール等が挙げられる。
知覚過敏緩和剤としては特に限定はされないが、硝酸カリウム、乳酸アルミニウム等が挙げられる。
う蝕予防剤としては特に限定はされないが、フッ化ナトリウム、モノフルオロリン酸ナトリウム等が挙げられる。
歯石沈着防止剤としては特に限定はされないが、ピロリン酸二水素二ナトリウム、ピロリン酸ナトリウム、塩化亜鉛等が挙げられる。
Although it does not specifically limit as a vitamin agent, Ascorbic acid and its salt, a pyridoxine hydrochloride, dl- (alpha) -tocopherol acetate, nicotinic acid dl- (alpha) -tocopherol, etc. are mentioned.
Although it does not specifically limit as a hypersensitivity alleviating agent, Potassium nitrate, aluminum lactate, etc. are mentioned.
Although it does not specifically limit as a caries preventive agent, Sodium fluoride, sodium monofluorophosphate, etc. are mentioned.
The anticalculus agent is not particularly limited, and examples thereof include disodium dihydrogen pyrophosphate, sodium pyrophosphate, zinc chloride and the like.
口臭除去剤としては特に限定はされないが、銅クロロフィリンナトリウム等が挙げられる。
収斂剤としては特に限定はされないが、塩化ナトリウム、ｌ−メントール等が挙げられる。
歯垢除去剤としては特に限定はされないが、ポリエチレングリコール、ポリビニルピロリドン等が挙げられる。
洗浄助剤としては、特に限定されないが、ゼオライト、リン酸１水素ナトリウム、リン酸三ナトリウム、ポリリン酸ナトリウムなどが挙げられる。
甘味剤としては、例えばサッカリン、ステビア、スクラロース、アスパルテーム、カンゾウエキスが挙げられるが、特に限定はされない。
防腐剤としては、例えばメチルパラベン、エチルパラベン、プロピルパラベン、ブチルパラベン、安息香酸ナトリウムが挙げられるが、特に限定はされない。
Although it does not specifically limit as a bad breath removal agent, Copper chlorophyllin sodium etc. are mentioned.
Although it does not specifically limit as an astringent, Sodium chloride, 1-menthol, etc. are mentioned.
Although it does not specifically limit as a plaque removal agent, Polyethylene glycol, polyvinyl pyrrolidone, etc. are mentioned.
The cleaning aid is not particularly limited, and examples thereof include zeolite, sodium monohydrogen phosphate, trisodium phosphate, and sodium polyphosphate.
Examples of the sweetener include saccharin, stevia, sucralose, aspartame, and licorice extract, but are not particularly limited.
Examples of the preservative include methyl paraben, ethyl paraben, propyl paraben, butyl paraben, and sodium benzoate, but are not particularly limited.
香料としては、ペパーミント油、スペアミント油、アニス油、ユーカリ油、ウィンターグリーン油、カシア油、クローブ油、タイム油、セージ油、レモン油、オレンジ油、ハッカ油、カルダモン油、コリアンダー油、マンダリン油、ライム油、ラベンダー油、ローズマリー油、ローレル油、カモミル油、キャラウェイ油、マジョラム油、ベイ油、レモングラス油、オリガナム油、パインニードル油、ネロリ油、ローズ油、ジャスミン油、グレープフルーツ油、スウィーティー油、柚油、イリスコンクリート、アブソリュートペパーミント、アブソリュートローズ、オレンジフラワー等の天然香料、およびこれら天然香料の加工処理（前溜部カット、後溜部カット、分留、液液抽出、エッセンス化、粉末香料化等）した香料、ｌ−メントール、カルボン、アネトール、シネオール、サリチル酸メチル、シンナミックアルデヒド、オイゲノール、３−ｌ−メントキシプロパン−１、２−ジオール、チモール、リナロール、リナリールアセテート、リモネン、メントン、メンチルアセテート、Ｎ−置換−ｐ−メンタン−３−カルボキサミド、ピネン、オクチルアルデヒド、シトラール、プレゴン、カルビールアセテート、アニスアルデヒド、エチルアセテート、エチルブチレート、アリルシクロヘキサンプロピオネート、メチルアンスラニレート、エチルメチルフェニルグリシデート、バニリン、ウンデカラクトン、ヘキサナール、ブタノール、イソアミルアルコール、ヘキセノール、ジメチルサルファイド、シクロテン、フルフラール、トリメチルピラジン、エチルラクテート、エチルチオアセテート等の単品香料、さらに、ストロベリーフレーバー、アップルフレーバー、バナナフレーバー、パイナップルフレーバー、グレープフレーバー、マンゴーフレーバー、バターフレーバー、ミルクフレーバー、フルーツミックスフレーバー、トロピカルフルーツフレーバー等の調合香料などが挙げられるが、特に限定はされない。 Perfumes include peppermint oil, spearmint oil, anise oil, eucalyptus oil, winter green oil, cassia oil, clove oil, thyme oil, sage oil, lemon oil, orange oil, peppermint oil, cardamom oil, coriander oil, mandarin oil, Lime oil, lavender oil, rosemary oil, laurel oil, camomil oil, caraway oil, marjoram oil, bay oil, lemongrass oil, origanum oil, pine needle oil, neroli oil, rose oil, jasmine oil, grapefruit oil, sweetie Natural fragrances such as oil, coconut oil, Iris concrete, absolute peppermint, absolute rose, orange flower, and processing of these natural fragrances (front reservoir cut, rear reservoir cut, fractional distillation, liquid-liquid extraction, essence, powder Perfume, l-menthol, etc. Rubon, Anethole, Cineol, Methyl salicylate, Synamic aldehyde, Eugenol, 3-l-Mentoxypropane-1, 2-diol, Thymol, Linalool, Linarel acetate, Limonene, Menthone, Menthyl acetate, N-substituted-p- Menthane-3-carboxamide, pinene, octylaldehyde, citral, pulegone, carbyl acetate, anisaldehyde, ethyl acetate, ethyl butyrate, allylcyclohexane propionate, methyl anthranilate, ethyl methyl phenyl glycidate, vanillin, undeca Lactone, hexanal, butanol, isoamyl alcohol, hexenol, dimethyl sulfide, cycloten, furfural, trimethylpyrazine, ethyl lactate, ethyl Single flavors such as o-acetate, and fragrances such as strawberry flavor, apple flavor, banana flavor, pineapple flavor, grape flavor, mango flavor, butter flavor, milk flavor, fruit mix flavor, tropical fruit flavor, etc. There is no particular limitation.
以上からなる本発明の組成物は、レジンやチタン含有金属への適合性のみならず歯および口腔粘膜への適合性があることから、歯科補綴物使用者向け口腔用組成物として用いることができる。好適に用いられる歯科補綴物とは具体的に、インレー、アンレー、クラウン、ブリッジ、全部床義歯、部分床義歯、インプラントが挙げられるが、これらに限定はされない。 The composition of the present invention composed of the above can be used as an oral composition for dental prosthesis users because it is compatible not only with resins and titanium-containing metals but also with teeth and oral mucosa. . Specific examples of suitably used dental prostheses include, but are not limited to, inlays, onlays, crowns, bridges, full dentures, partial dentures, and implants.
本発明の組成物は、金属性（チタン、金、銀、パラジウム、プラチナ、コバルトクロム、ステンレス）の歯科補綴物用口腔用組成物だけでなく、プラスチック、セラミックス、樹脂（例えば、硬質レジン）の歯科補綴物用口腔用組成物にも適用可能である。
加えて、下記の実施例の結果から明らかなように、歯科補綴物使用者は、歯科補綴物を装着したままでも本発明の組成物を使用できる。
The composition of the present invention is not only a metallic (titanium, gold, silver, palladium, platinum, cobalt chrome, stainless steel) oral composition for dental prosthesis, but also plastic, ceramic, resin (for example, hard resin). It is applicable also to the composition for oral cavity for dental prostheses.
In addition, as is apparent from the results of the following examples, the dental prosthesis user can use the composition of the present invention while wearing the dental prosthesis.
以下、本発明について実施例および比較例により、本発明およびその効果を具体的に説明するが、本発明はこれらの実施例によって限定されるものではない。 EXAMPLES Hereinafter, although an Example and a comparative example demonstrate this invention and its effect concretely, this invention is not limited by these Examples.
＜ホスホリルコリン基含有重合体（Ｐ）の重量平均分子量の測定＞
ホスホリルコリン基含有重合体（Ｐ）の重量平均分子量は、ポリエチレンオキシドを標準サンプルとしてゲルパーミエーションクロマトグラフィー（ＧＰＣ）により測定した値である。すなわち、得られたホスホリルコリン基含有重合体（Ｐ）を０．５重量％になるように精製水で希釈し、この溶液を孔径０．４５μｍのセルロースアセテートメンブレンフィルターでろ過し、試験溶液とした。なお、ＧＰＣの測定条件は次の通りである。
<Measurement of weight average molecular weight of phosphorylcholine group-containing polymer (P)>
The weight average molecular weight of the phosphorylcholine group-containing polymer (P) is a value measured by gel permeation chromatography (GPC) using polyethylene oxide as a standard sample. That is, the obtained phosphorylcholine group-containing polymer (P) was diluted with purified water so as to be 0.5% by weight, and this solution was filtered through a cellulose acetate membrane filter having a pore size of 0.45 μm to obtain a test solution. The measurement conditions for GPC are as follows.
＜ＧＰＣの測定条件＞
溶離液：２０ｍｍｏｌ／Ｌリン酸緩衝水溶液、検出器：示差屈折計ＲＩ−８０２０（東ソー（株）製）、ＧＰＣ分析１次カラム：ＳＢ−８０２．５ ＨＱ（昭和電工（株）製）、ＧＰＣ分析２次カラム：ＳＢ−８０６Ｍ ＨＱ（昭和電工（株）製）、ガードカラム：ＳＢ−Ｇ（昭和電工（株）製）、カラム温度：４５℃。
<GPC measurement conditions>
Eluent: 20 mmol / L phosphate buffer aqueous solution, detector: differential refractometer RI-8020 (manufactured by Tosoh Corporation), GPC analysis primary column: SB-802.5 HQ (manufactured by Showa Denko KK), GPC Analysis secondary column: SB-806M HQ (manufactured by Showa Denko KK), guard column: SB-G (manufactured by Showa Denko KK), column temperature: 45 ° C.
表１に実施例および比較例に示すポリマーの組成比と重量平均分子量を示す。 Table 1 shows the composition ratios and weight average molecular weights of the polymers shown in Examples and Comparative Examples.
［実施例１〜５６および比較例１〜４２］
表２〜１１に示す組成の口腔用組成物は、常法に従って調製した。
[Examples 1 to 56 and Comparative Examples 1 to 42]
The composition for oral cavity of the composition shown to Tables 2-11 was prepared in accordance with the conventional method.
＜試験１：酸化チタン板への微生物付着防止性の評価＞
リン酸緩衝生理食塩水を対照として、実施例１〜５６および比較例１〜４２を用いて以下の試験を実施した。
<Test 1: Evaluation of antimicrobial adhesion to titanium oxide plate>
The following tests were conducted using Examples 1-56 and Comparative Examples 1-42 using phosphate buffered saline as a control.
（手順１）Ｓｔｒｅｐｔｏｃｏｃｃｕｓ ｍｕｔａｎｓ ＮＢＲＣ１３９５５（以下、Ｓ．ｍｕｔａｎｓ）をＢｒａｉｎ Ｈｅａｒｔ Ｉｎｆｕｓｉｏｎ培地（ベクトン・ディッキンソン社製、以下、ＢＨＩ培地）に植菌し、一晩培養した。
（手順２）培養したＳ．ｍｕｔａｎｓ液を遠心分離し、リン酸緩衝液で洗浄した。
（手順３）Ｓ．ｍｕｔａｎｓ液の光学濃度（６６０ｎｍ）が１．０になるようにリン酸緩衝液で調製した。
（手順４）２４ウェルマイクロプレートに対照、実施例１〜５６および比較例１〜４２の組成物を１ｍＬずつ添加し、それぞれに酸化チタン板を入れ、１分間静置した。
（手順５）各組成物を取り除き、酸化チタン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順６）酸化チタン板の入った２４ウェルマイクロプレートに手順３で調製したＳ．ｍｕｔａｎｓ液を０．５ｍＬずつ加え、５時間培養し、酸化チタン板にＳ．ｍｕｔａｎｓを付着させた。
（手順７）Ｓ．ｍｕｔａｎｓ液を取り除き、酸化チタン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順８）酸化チタン板の入った２４ウェルマイクロプレートにビクトリアブルー液を０．５ｍＬずつ加え、１０分間静置し、Ｓ．ｍｕｔａｎｓを染色した。
（手順９）ビクトリアブルー液を取り除き、酸化チタン板を０．５ｍＬの脱色液で２回洗浄した。
（手順１０）酸化チタン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順１１）酸化チタン板の入った２４ウェルマイクロプレートにエタノール０．５ｍＬを加え、Ｓ．ｍｕｔａｎｓに取り込まれたビクトリアブルー液を抽出した。
（手順１２）抽出したビクトリアブルー液を０．１ｍＬ量り取り、マイクロプレートリーダー（型式：ＳｐｅｃｔｒａＭａｘ Ｍ３、モレキュラーデバイスジャパン社製）を用いて、５９５ｎｍにおける吸光度を測定した。微生物由来の堆積物の付着防止効果を対照処理時の吸光度と組成物処理時の吸光度から式（１）を用いて、Ｓ．ｍｕｔａｎｓの付着量減少率から評価した。評価結果は、表２〜１１に示した。
(Procedure 1) Streptococcus mutans NBRC13955 (hereinafter referred to as S. mutans) was inoculated in Brain Heart Infusion medium (Becton Dickinson, hereinafter referred to as BHI medium) and cultured overnight.
(Procedure 2) Cultured S. cerevisiae The mutans solution was centrifuged and washed with phosphate buffer.
(Procedure 3) The mutans solution was prepared with a phosphate buffer so that the optical density (660 nm) was 1.0.
(Procedure 4) 1 mL each of the compositions of Control, Examples 1 to 56 and Comparative Examples 1 to 42 was added to a 24-well microplate, and a titanium oxide plate was added to each, and allowed to stand for 1 minute.
(Procedure 5) Each composition was removed, and the titanium oxide plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 6) S. cerevisiae prepared in Procedure 3 on a 24-well microplate containing a titanium oxide plate. Add 0.5 mL of mutans solution at a time, and incubate for 5 hours. Mutans were attached.
(Procedure 7) The mutans solution was removed, and the titanium oxide plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 8) Victoria Blue liquid was added 0.5 mL at a time to a 24-well microplate containing a titanium oxide plate and allowed to stand for 10 minutes. Mutans was stained.
(Procedure 9) The Victoria blue liquid was removed, and the titanium oxide plate was washed twice with 0.5 mL of a decolorizing liquid.
(Procedure 10) The titanium oxide plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 11) 0.5 mL of ethanol was added to a 24-well microplate containing a titanium oxide plate. The Victoria blue liquid taken in by mutans was extracted.
(Procedure 12) 0.1 mL of the extracted Victoria Blue liquid was weighed and the absorbance at 595 nm was measured using a microplate reader (Model: SpectraMax M3, manufactured by Molecular Device Japan). The anti-adhesion effect of deposits derived from microorganisms was determined using the equation (1) from the absorbance during the control treatment and the absorbance during the composition treatment. It evaluated from the adhesion amount decreasing rate of mutans. The evaluation results are shown in Tables 2-11.
Ｓ．ｍｕｔａｎｓ付着量減少率（％）＝（１−組成物処理時の吸光度／対照処理時の吸光度）×１００・・・式（１） S. Mutans adhesion reduction rate (%) = (1-absorbance during composition treatment / absorbance during control treatment) × 100 (1)
＜試験２：レジン板への微生物付着防止性の評価＞
リン酸緩衝生理食塩水を対照として、実施例１〜５６および比較例１〜４２を用いて以下の試験を実施した。
<Test 2: Evaluation of antimicrobial adhesion to resin plate>
The following tests were conducted using Examples 1-56 and Comparative Examples 1-42 using phosphate buffered saline as a control.
（手順１）Ｓ．ｍｕｔａｎｓをＢＨＩ培地に植菌し、一晩培養した。
（手順２）培養したＳ．ｍｕｔａｎｓ液を遠心分離し、リン酸緩衝液で洗浄した。
（手順３）Ｓ．ｍｕｔａｎｓ液の光学濃度（６６０ｎｍ）が１．０になるようにリン酸緩衝液で調製した。
（手順４）２４ウェルマイクロプレートに対照、実施例１〜５６および比較例１〜４２の組成物を１ｍＬずつ添加し、それぞれにレジン板を入れ、１分間静置した。
（手順５）各組成物を取り除き、レジン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順６）レジン板の入った２４ウェルマイクロプレートに手順３で調製したＳ．ｍｕｔａｎｓ液を０．５ｍＬずつ加え、５時間培養し、レジン板にＳ．ｍｕｔａｎｓを付着させた。
（手順７）Ｓ．ｍｕｔａｎｓ液を取り除き、レジン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順８）レジン板の入った２４ウェルマイクロプレートにビクトリアブルー液を０．５ｍＬずつ加え、１０分間静置し、Ｓ．ｍｕｔａｎｓを染色した。
（手順９）ビクトリアブルー液を取り除き、レジン板を０．５ｍＬの脱色液で２回洗浄した。
（手順１０）レジン板を１ｍＬのリン酸緩衝液で３回洗浄した。
（手順１１）レジン板の入った２４ウェルマイクロプレートにエタノール０．５ｍＬを加え、Ｓ．ｍｕｔａｎｓに取り込まれたビクトリアブルー液を抽出した。
（手順１２）抽出したビクトリアブルー液を０．１ｍＬ量り取り、マイクロプレートリーダー（型式：ＳｐｅｃｔｒａＭａｘ Ｍ３、モレキュラーデバイスジャパン社製）を用いて、５９５ｎｍにおける吸光度を測定した。微生物由来の堆積物の付着防止効果を対照処理時の吸光度と組成物処理時の吸光度から上記式（１）を用いて、Ｓ．ｍｕｔａｎｓの付着量減少率から評価した。評価結果は、表２〜１１に示した。
(Procedure 1) Mutans was inoculated into BHI medium and cultured overnight.
(Procedure 2) Cultured S. cerevisiae The mutans solution was centrifuged and washed with phosphate buffer.
(Procedure 3) The mutans solution was prepared with a phosphate buffer so that the optical density (660 nm) was 1.0.
(Procedure 4) 1 mL each of the compositions of Control, Examples 1 to 56 and Comparative Examples 1 to 42 was added to a 24-well microplate, and a resin plate was added to each of them and allowed to stand for 1 minute.
(Procedure 5) Each composition was removed, and the resin plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 6) S. cerevisiae prepared in Procedure 3 on a 24-well microplate containing a resin plate. 0.5 ml of mutans solution was added and cultured for 5 hours. Mutans were attached.
(Procedure 7) The mutans solution was removed, and the resin plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 8) 0.5 mL of Victoria Blue solution was added to a 24-well microplate containing a resin plate, and allowed to stand for 10 minutes. Mutans was stained.
(Procedure 9) The Victoria blue solution was removed, and the resin plate was washed twice with 0.5 mL of a decolorizing solution.
(Procedure 10) The resin plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 11) 0.5 mL of ethanol was added to a 24-well microplate containing a resin plate. The Victoria blue liquid taken in by mutans was extracted.
(Procedure 12) 0.1 mL of the extracted Victoria Blue liquid was weighed and the absorbance at 595 nm was measured using a microplate reader (Model: SpectraMax M3, manufactured by Molecular Device Japan). The anti-adhesion effect of the microorganism-derived deposits was determined using the above formula (1) from the absorbance during the control treatment and the absorbance during the composition treatment. It evaluated from the adhesion amount decreasing rate of mutans. The evaluation results are shown in Tables 2-11.
上記の結果より、実施例１〜５６のポリマー１あるいはポリマー２を０．００１〜１０％含有する口腔用組成物で処理した酸化チタン板およびレジン板は、殺菌剤の種類に関わらずＳ．ｍｕｔａｎｓ付着量を５０〜７４％減少させた。すなわち、本発明によって、プラーク形成の初期段階に主に存在するＳ．ｍｕｔａｎｓの歯科補綴物材料への付着量が非常に少ない口腔用組成物が提供されることが明らかとなった。 From the above results, the titanium oxide plate and the resin plate treated with the composition for oral cavity containing 0.001 to 10% of the polymer 1 or the polymer 2 of Examples 1 to 56 are S.P. Mutans adhesion was reduced by 50-74%. That is, according to the present invention, S. cerevisiae, which exists mainly in the initial stage of plaque formation. It has been found that oral compositions with very little mutans adherence to dental prosthetic materials are provided.
これに対して、比較例１〜２８においては、ホスホリルコリン基含有重合体の配合量が本発明要件の配合量範囲の下限を下回っているため、Ｓ．ｍｕｔａｎｓ付着減少量は１９〜３４％と顕著な付着防止効果は見られなかった。また、比較例２９〜４２においては、Ｓ．ｍｕｔａｎｓ付着減少量が１１〜１９％となり、顕著な付着防止効果は見られなかった。これは、重合体中に構成成分（Ｂ１）および（Ｂ２）を含んでいないことにより、補綴物材料に対して付着しなかったためである。また、ホスホリルコリン基含有重合体の重量平均分子量が本発明要件の下限である５１０，０００未満であることにより、（Ｃ）成分がポリマー中に保持されなかったことが、Ｓ．ｍｕｔａｎｓ付着減少量が小さい原因である。 On the other hand, in Comparative Examples 1-28, since the compounding quantity of a phosphorylcholine group containing polymer is less than the minimum of the compounding quantity range of this invention requirement, S.I. The mutans adhesion reduction amount was 19 to 34%, and no remarkable adhesion preventing effect was observed. In Comparative Examples 29 to 42, S.E. Mutans adhesion reduction amount became 11-19%, and the remarkable adhesion prevention effect was not seen. This is because the polymer did not adhere to the prosthetic material because it did not contain the constituent components (B1) and (B2). In addition, since the weight average molecular weight of the phosphorylcholine group-containing polymer is less than 510,000 which is the lower limit of the requirements of the present invention, it was confirmed that the component (C) was not retained in the polymer. This is a cause of a small amount of mutans adhesion reduction.
以上に詳述した通り、本発明に係る歯科補綴物使用者向け口腔用組成物を使用することで、歯科補綴物を装着したままの状態で、補綴物の素材であるチタンおよびレジン等へのプラーク形成の原因となるＳ．ｍｕｔａｎｓの付着を防止し、プラークの形成を防止することを可能にする。 As described in detail above, by using the oral composition for a dental prosthesis user according to the present invention, the dental prosthesis can be attached to titanium, resin, etc., while the dental prosthesis is still worn. S. is responsible for plaque formation. Mutans adherence can be prevented and plaque formation can be prevented.
歯科補綴物への微生物付着防止効果およびプラーク形成防止効果に優れた歯科補綴物使用者向け口腔用組成物を提供することができる。 It is possible to provide a composition for oral cavity for dental prosthesis users that is excellent in the effect of preventing microbial adhesion to a dental prosthesis and the effect of preventing plaque formation.
Claims (2)
殺菌剤（Ｃ）と、を含有する口腔用組成物。
Structural unit (A1) based on 2- (meth) acryloyloxyethyl phosphorylcholine and structural unit (B1) based on alkyl group-containing (meth) acrylic monomer and / or (meth) acrylamide based monomer 0.001 wt% to 10 wt% of a phosphorylcholine group-containing polymer containing 10 to 90 mol% of the structural unit (B2) based on the body and having a weight average molecular weight of 510,000 to 5,000,000,
An oral composition containing a bactericidal agent (C).
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|---|---|---|---|
| JP2015186783A JP6672665B2 (en) | 2015-09-24 | 2015-09-24 | Oral composition |
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| JP2015186783A JP6672665B2 (en) | 2015-09-24 | 2015-09-24 | Oral composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017186333A (en) * | 2016-03-31 | 2017-10-12 | 小林製薬株式会社 | Oral composition |
| CN108929403A (en) * | 2017-05-25 | 2018-12-04 | 日油株式会社 | Binder resin, conductive paste composition, ceramic binder resin and ceramic composition |
| JP2018197323A (en) * | 2017-05-25 | 2018-12-13 | 日油株式会社 | Ceramic binder resin and ceramic composition |
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| JP2003327778A (en) * | 2002-05-10 | 2003-11-19 | Nof Corp | Formulated composition and method for alleviating cytotoxicity |
| JP2004194874A (en) * | 2002-12-18 | 2004-07-15 | Gc Corp | Coating material composition for dental prosthesis |
| JP2011153101A (en) * | 2010-01-28 | 2011-08-11 | Nof Corp | Microbial adhesion prevention agent for oral cavity |
| JP2015000853A (en) * | 2013-06-14 | 2015-01-05 | 日油株式会社 | Preventive agent for gingivitis |
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| JP2003327778A (en) * | 2002-05-10 | 2003-11-19 | Nof Corp | Formulated composition and method for alleviating cytotoxicity |
| JP2004194874A (en) * | 2002-12-18 | 2004-07-15 | Gc Corp | Coating material composition for dental prosthesis |
| JP2011153101A (en) * | 2010-01-28 | 2011-08-11 | Nof Corp | Microbial adhesion prevention agent for oral cavity |
| JP2015000853A (en) * | 2013-06-14 | 2015-01-05 | 日油株式会社 | Preventive agent for gingivitis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017186333A (en) * | 2016-03-31 | 2017-10-12 | 小林製薬株式会社 | Oral composition |
| JP6998123B2 (en) | 2016-03-31 | 2022-01-18 | 小林製薬株式会社 | Oral composition |
| CN108929403A (en) * | 2017-05-25 | 2018-12-04 | 日油株式会社 | Binder resin, conductive paste composition, ceramic binder resin and ceramic composition |
| JP2018197323A (en) * | 2017-05-25 | 2018-12-13 | 日油株式会社 | Ceramic binder resin and ceramic composition |
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