JPH0331210A - Composition for oral cavity - Google Patents
Composition for oral cavityInfo
- Publication number
- JPH0331210A JPH0331210A JP16630889A JP16630889A JPH0331210A JP H0331210 A JPH0331210 A JP H0331210A JP 16630889 A JP16630889 A JP 16630889A JP 16630889 A JP16630889 A JP 16630889A JP H0331210 A JPH0331210 A JP H0331210A
- Authority
- JP
- Japan
- Prior art keywords
- polysaccharide
- oral cavity
- lentinan
- composition
- amount
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 210000000214 mouth Anatomy 0.000 title abstract description 6
- 150000004676 glycans Chemical class 0.000 claims abstract description 18
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 18
- 239000005017 polysaccharide Substances 0.000 claims abstract description 18
- 230000002519 immonomodulatory effect Effects 0.000 claims abstract description 7
- 229920001491 Lentinan Polymers 0.000 abstract description 11
- 229940115286 lentinan Drugs 0.000 abstract description 11
- 208000002925 dental caries Diseases 0.000 abstract description 10
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 abstract description 5
- 108010001062 polysaccharide-K Proteins 0.000 abstract description 5
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 abstract description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 abstract description 4
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 abstract description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 abstract description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 abstract description 4
- 229940034610 toothpaste Drugs 0.000 abstract description 4
- 239000000606 toothpaste Substances 0.000 abstract description 4
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 abstract description 2
- 229930091371 Fructose Natural products 0.000 abstract description 2
- 239000005715 Fructose Substances 0.000 abstract description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract description 2
- PNNNRSAQSRJVSB-SLPGGIOYSA-N Fucose Natural products C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-SLPGGIOYSA-N 0.000 abstract description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 2
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 abstract description 2
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 abstract description 2
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 abstract description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 abstract description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 abstract description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract description 2
- 229940112822 chewing gum Drugs 0.000 abstract description 2
- 235000015218 chewing gum Nutrition 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract description 2
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- 229930182830 galactose Natural products 0.000 abstract description 2
- 239000008103 glucose Substances 0.000 abstract description 2
- 229940097043 glucuronic acid Drugs 0.000 abstract description 2
- 208000010266 Aggressive Periodontitis Diseases 0.000 abstract 1
- AVGPOAXYRRIZMM-UHFFFAOYSA-N D-Apiose Natural products OCC(O)(CO)C(O)C=O AVGPOAXYRRIZMM-UHFFFAOYSA-N 0.000 abstract 1
- ASNHGEVAWNWCRQ-LJJLCWGRSA-N D-apiofuranose Chemical compound OC[C@@]1(O)COC(O)[C@@H]1O ASNHGEVAWNWCRQ-LJJLCWGRSA-N 0.000 abstract 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N D-apiofuranose Natural products OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 abstract 1
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 abstract 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 abstract 1
- 229920000519 Sizofiran Polymers 0.000 abstract 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 201000006727 periodontosis Diseases 0.000 abstract 1
- 229950001403 sizofiran Drugs 0.000 abstract 1
- -1 abiose Chemical compound 0.000 description 6
- 210000000416 exudates and transudate Anatomy 0.000 description 6
- 208000028169 periodontal disease Diseases 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 5
- 229920002305 Schizophyllan Polymers 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000001768 carboxy methyl cellulose Substances 0.000 description 5
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 5
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 5
- 229940105329 carboxymethylcellulose Drugs 0.000 description 5
- 201000001245 periodontitis Diseases 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- 241001465754 Metazoa Species 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
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000000987 immune system Anatomy 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000002324 mouth wash Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 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
- 230000000740 bleeding effect Effects 0.000 description 2
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-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
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 210000004195 gingiva Anatomy 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 210000003296 saliva Anatomy 0.000 description 2
- 239000005720 sucrose Substances 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
- 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
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- FEBUJFMRSBAMES-UHFFFAOYSA-N 2-[(2-{[3,5-dihydroxy-2-(hydroxymethyl)-6-phosphanyloxan-4-yl]oxy}-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-4-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl phosphinite Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(OC2C(C(OP)C(O)C(CO)O2)O)C(O)C(OC2C(C(CO)OC(P)C2O)O)O1 FEBUJFMRSBAMES-UHFFFAOYSA-N 0.000 description 1
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
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- 210000003850 cellular structure Anatomy 0.000 description 1
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 1
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 229910000393 dicalcium diphosphate Inorganic materials 0.000 description 1
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 1
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 1
- 229960003720 enoxolone Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- AXCXHFKZHDEKTP-UHFFFAOYSA-N para-methoxycinnamaldehyde Natural products COC1=CC=C(C=CC=O)C=C1 AXCXHFKZHDEKTP-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-UHFFFAOYSA-N para-methoxyphenyl Natural products COC1=CC=C(C=CC)C=C1 RUVINXPYWBROJD-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 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
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 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
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AQMNWCRSESPIJM-UHFFFAOYSA-M sodium metaphosphate Chemical compound [Na+].[O-]P(=O)=O AQMNWCRSESPIJM-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 229940013618 stevioside Drugs 0.000 description 1
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
- 235000019202 steviosides Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001519 tissue Anatomy 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
- 230000000007 visual effect Effects 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000009538 yokuinin Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は口腔用組成物に関し、更に詳細にはう蝕及び歯
周病の予防、治療に有効な口腔用組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an oral composition, and more particularly to an oral composition effective for preventing and treating caries and periodontal disease.
う蝕と歯周病は口腔の二人疾病であり、これらの予防、
治療については、古くから多大な努力が払われてきた。Caries and periodontal disease are two diseases of the oral cavity, and their prevention,
Great efforts have been made since ancient times regarding treatment.
しかしながら、これらは医学の進歩のめざましい今日に
あっても人類が未だ完全に克服することのできない疾病
の一つであり、これを克服するために底知れぬ努力がは
られれ、これまで数多くの治療法が実施されてきた。特
に近年、新しい試みとして免疫系を介したう蝕の予防に
関する検討が行われている。例えば、う蝕の原因菌であ
るストレプトコッカス・ミュータンス、バタテロイデス
・ジンジバリス若しくは口腔内混合菌の菌体または菌体
成分を抗原とした抗体を用いてう蝕を予防しようとする
報告がある(特開昭60−38327号、特開昭60−
38329号、特開昭60−142915号、特開昭6
1−112028号、特開昭61−112029号、特
開昭61−112030号、特開昭61−277632
号、特開昭61289024号、特開昭61−417号
)。また、免疫系を介したう蝕の予防に関して、フェニ
ルアラニン等も検討されている(特開昭63−1471
3号)。However, even in today's world of remarkable medical advances, these are among the diseases that humanity has not been able to completely overcome, and endless efforts have been made to overcome them. The law has been implemented. Particularly in recent years, new attempts have been made to investigate the prevention of caries via the immune system. For example, there are reports of attempts to prevent dental caries using antibodies that are antigenic to the cells or cell components of Streptococcus mutans, Batateroides gingivalis, or oral mixed bacteria that cause caries (Unexamined Japanese Patent Publication No. No. 60-38327, JP-A-60-
No. 38329, JP-A-60-142915, JP-A-6
1-112028, JP 61-112029, JP 61-112030, JP 61-277632
No., JP-A-61289024, JP-A-61-417). In addition, phenylalanine and the like are being investigated for the prevention of dental caries via the immune system (Japanese Patent Application Laid-Open No. 1471-1471).
No. 3).
一方、歯周病に関しても免疫系を介した予防及び治療法
が提案されており、有効成分としてクマリン(特開昭6
2−39516号)、グリチルレチン酸(特開昭61−
152622号、特開昭59−227812号)、キチ
ン、キトサン(特開昭59−101416号)を用いた
ものがすでに開示されている。On the other hand, prevention and treatment methods for periodontal disease via the immune system have been proposed, and coumarin (Japanese Patent Laid-open No. 6
No. 2-39516), glycyrrhetinic acid (Japanese Patent Application Laid-open No. 1983-
152622, JP-A No. 59-227812), and those using chitin and chitosan (JP-A-59-101416) have already been disclosed.
以上のように免疫を介したう蝕及び歯周病の予防、治療
に関しては幾つかの試みはある。しかしながら、未だ、
真に有効な方法は見出されていないのが実情である。As mentioned above, there have been several attempts to prevent and treat caries and periodontal disease through immunity. However, still
The reality is that no truly effective method has been found.
本発明者は上記実情に鑑み、う蝕及び歯周病の予防、治
療に有効な口腔用組成物を得るべく鋭意研究を行った結
果、免疫調節作用を有する多糖類が、これらの疾病の予
防、治療に有効であることを見出し本発明を完成した。In view of the above circumstances, the present inventor conducted intensive research to obtain an oral composition effective in preventing and treating dental caries and periodontal disease. As a result, the present inventor found that polysaccharides with immunomodulatory effects are effective in preventing and treating these diseases. They found that it is effective for treatment and completed the present invention.
すなわち、本発明は免疫調節作用を有する多糖類を含有
することを特徴とする口腔用組成物を提供するものであ
る。That is, the present invention provides an oral composition characterized by containing a polysaccharide having an immunomodulatory effect.
本発明の有効成分である多糖類はグルコース、ガラクト
ース、マンノース、アラビノース、キシロース、フラク
トース、フコース、ラムノース、アビオース、グルクロ
ン酸、ガラクチュロン酸のうち少なくとも1種類を構成
糖とし、かつ免疫調節作用を有するものである。具体的
には、例えばレンチナン、U−パヒマン、ヒドロキシエ
チルパヒマン、シゾフィラン、スクレログルカン、直鎖
レンチナン、バヒマラン、ブスチュラン、クレスチン、
トウキアラビノガラククン、ソウヨウ酸性へテロ多糖、
ヨクイニン酸性へテロ多糖、シコニン中性多糖等が挙げ
られる。就中、レンチナン、シゾフィラン、クレスチン
等が特に好ましい。これらの多糖類は、1種類で用いる
こともできるが、複数の多糖類を混合して用いてもよい
。これら多糖類の有効濃度は多糖類の種類によって異な
り一概に言えないが、例えば、レンチナンまたはシゾフ
ィランでは0.001〜1重量%(以下、単に「%」と
いう)、好ましくは0.O1〜0.5%、クレスチンで
は0.05〜5%、好ましくは0.05−2.5%であ
る。従って、本発明口腔用組成物には、これら多糖類が
口腔内でその濃度に達するような量を配合すればよい。The polysaccharide that is the active ingredient of the present invention has at least one constituent sugar among glucose, galactose, mannose, arabinose, xylose, fructose, fucose, rhamnose, abiose, glucuronic acid, and galacturonic acid, and has an immunomodulatory effect. It is. Specifically, for example, lentinan, U-pahiman, hydroxyethylpahiman, schizophyllan, scleroglucan, linear lentinan, bahimaran, busturan, krestin,
Tokiarabinogalakukun, Souyou acidic heteropolysaccharide,
Examples include yokuinin acidic heteropolysaccharide and shikonin neutral polysaccharide. Among these, lentinan, schizophyllan, krestin, etc. are particularly preferred. Although these polysaccharides can be used alone, a plurality of polysaccharides may be used as a mixture. The effective concentration of these polysaccharides differs depending on the type of polysaccharide and cannot be generalized, but for example, for lentinan or schizophyllan, the effective concentration is 0.001 to 1% by weight (hereinafter simply referred to as "%"), preferably 0.001% to 1% by weight (hereinafter simply referred to as "%"). O1-0.5%, Krestin 0.05-5%, preferably 0.05-2.5%. Therefore, the oral composition of the present invention may contain these polysaccharides in an amount that will reach the concentration in the oral cavity.
なお、本発明の口腔用組成物の他の成分としては、使用
目的及び使用態様に応じ、適宜従来の口腔用組成物に使
用されていた成分が使用可能である。例えば練り歯磨き
の場合であれば、第ニリン酸カルシウム、炭酸カルシウ
ム、ピロリン酸カルシウム、不溶性メタリン酸ナトリウ
ム、非晶質シリカ、アルミノシリケート、酸化アルミニ
ウム、水酸化アルミニウム、レジン等の研磨剤;カルボ
キシメチルセルロース、ヒドロキシエチルセルロース、
アルギン酸塩、カラゲチン、アラビアゴム、ポリビニル
アルコール等の粘結剤ニラウリル硫酸ナトリウム、ドデ
シルベンゼンスルホン酸ナトリウム、N−ラウロイルザ
ルコシン酸ナトリウム、N−アシルグルタミン酸塩、蔗
糖脂肪酸エステル等の発泡剤;ペパーミント、スペアミ
ント等の精油;l−メントール、カルボン、オイゲノー
ル、アネトール等の香料;サッカリンナトリウム、ステ
ビオサイド、ネオヘスベリジルジヒドロカルコン、グリ
チルリチン、ベルラリチン、p−メトキシシンナミック
アルデヒド等の甘味剤;防腐剤等の成分を水と混和し、
常法に従って製造する。また、マウスウォッシュ等の口
腔用洗浄剤その他においても、製品の性状に応じた成分
が適宜配合、される。In addition, as other components of the oral composition of the present invention, components used in conventional oral compositions can be used as appropriate depending on the purpose and mode of use. For example, in the case of toothpaste, abrasives such as calcium diphosphate, calcium carbonate, calcium pyrophosphate, insoluble sodium metaphosphate, amorphous silica, aluminosilicate, aluminum oxide, aluminum hydroxide, and resin; carboxymethyl cellulose, hydroxyethyl cellulose ,
Binder such as alginate, caragetin, gum arabic, polyvinyl alcohol; Foaming agent such as sodium nilauryl sulfate, sodium dodecylbenzenesulfonate, sodium N-lauroyl sarcosinate, N-acylglutamate, sucrose fatty acid ester; peppermint, spearmint essential oils such as; fragrances such as l-menthol, carvone, eugenol, anethole; sweeteners such as saccharin sodium, stevioside, neohesberidyl dihydrochalcone, glycyrrhizin, verlaritin, p-methoxycinnamic aldehyde; ingredients such as preservatives with water. mix,
Manufactured according to conventional methods. In addition, in mouthwashes and other oral cleansing agents, ingredients are appropriately blended according to the properties of the product.
なお、本発明口腔用組成物には、前記免疫調節作用を有
する多糖類以外の有効成分として、塩化ナトリウム、ビ
タミンC1ビタミンE2ニコチン酸エステル、アラント
インクロルヒドロキシアルミニウム、アズレン、水溶性
第一または第ニリン酸塩、第四級アンモニウム化合物、
フッ化化合物、塩化リゾチーム、ヒノキチオール、ゼオ
ライト、プロテアーゼ、生薬抽出物を更に配合すること
もできる。In addition, the oral composition of the present invention contains sodium chloride, vitamin C1 vitamin E2 nicotinic acid ester, allantoin chlorhydroxyaluminum, azulene, and water-soluble primary or dilinic acid as active ingredients other than the polysaccharide having an immunomodulating effect. acid salts, quaternary ammonium compounds,
Fluorinated compounds, lysozyme chloride, hinokitiol, zeolite, protease, and crude drug extracts can also be further blended.
本発明に用いる多糖類は、液剤またはクリームとして患
部に直接塗布したり、練り歯磨き、マウスウォッシュ、
トローチ、チュウインガム等に含有せ(、めたり、口腔
粘膜張付型製剤としても使用することが出来る。The polysaccharide used in the present invention can be applied directly to the affected area as a liquid or cream, or can be applied to toothpaste, mouthwash, etc.
It can be included in troches, chewing gum, etc., and can also be used as a preparation that sticks to the oral mucosa.
本発明口腔用組成物は、現存の口腔用組成物に比べう蝕
及び歯周病の予防、治療に極めて有効である。The oral composition of the present invention is extremely effective in preventing and treating caries and periodontal disease compared to existing oral compositions.
次に、実施例及び試験例を挙げて本発明を更に詳細に説
明するが、本発明はこれらに限定されるものではない。Next, the present invention will be explained in more detail with reference to Examples and Test Examples, but the present invention is not limited thereto.
実施例1 歯周炎動物モデルでの゛効果:歯周炎モデル
動物を用いて本発明口腔用組成物に用いる多糖類の歯周
炎に対する効果を調べた。Example 1 Effect on periodontitis animal model: The effect of the polysaccharide used in the oral composition of the present invention on periodontitis was investigated using a periodontitis model animal.
モデル動物として、歯周炎の自然発生した体重約14k
g、4歳、雌のピーグル犬3頭を用い、臼歯部を各上下
左右4部位に分け、その1つに0.1%レンチナンを含
む2.0%カルボキシメチルセルロース水溶液、他の1
つに0.1%シゾフィランを含む2.0%カルボキシメ
チルセルロース水溶液を、さらに他の1つにコントロー
ルとして2.0%カルボキシメチルセルロースのみを塗
布し10分間作用させた。塗布は麻酔後、臼歯部歯肉の
唾液を抜き取った後に行った。As a model animal, naturally occurring periodontitis weighs approximately 14 kg.
g. Using three 4-year-old female pegle dogs, the molars were divided into four parts, top, bottom, left, and right, and one part was treated with a 2.0% carboxymethylcellulose aqueous solution containing 0.1% lentinan, and the other part was treated with a 2.0% carboxymethylcellulose aqueous solution containing 0.1% lentinan.
A 2.0% carboxymethylcellulose aqueous solution containing 0.1% schizophyllan was applied to one of the two, and 2.0% carboxymethylcellulose alone was applied to the other as a control for 10 minutes. The application was performed after anesthesia and after removing saliva from the molar gingiva.
このような薬剤処理を1日1回ずつ8日間行い、0日目
、3日目、8日目1こジンジバルインデックス、歯肉間
溝滲出液量及び細菌数を測定し、夫々の時点においての
3頭のデータの平均を求め測定値とした。Such drug treatment was performed once a day for 8 days, and the gingival index, the amount of intergingival sulcus exudate, and the number of bacteria were measured on the 0th, 3rd, and 8th days. The average of the data from the three animals was determined and used as the measured value.
ジンジバルインデックス(シOeら; J、 ofP
eriodontolo、 38.610−616.1
967)の測定は細かく差を見るために以下の様な評価
を設け、2人による肉眼観察により測定した。Gingival index (Shi Oe et al.; J, ofP
eriodontolo, 38.610-616.1
967) was measured by visual observation by two people using the following evaluation to see the difference in detail.
スコア 0.5 1.0 1.5 2.0 3.0 歯肉炎の進行程度 臨床的正常歯肉。Score 0.5 1.0 1.5 2.0 3.0 Progression level of gingivitis Clinically normal gingiva.
はぼ正常であるが歯肉に若干の発赤が見られる。Her face is normal, but there is some redness on her gums.
歯肉に軽度の炎症。ポケットを探針で触れても出血なし
。Mild inflammation of the gums. There was no bleeding when I touched the pocket with the probe.
ポケットを探針で触れても出血しないが、してもおかし
くない状態。When I touch my pocket with a probe, it doesn't bleed, but it's still normal.
歯肉に中程度の炎症。ポケットを探針で触れると出血。Moderate inflammation of the gums. When I touch my pocket with a probe, it bleeds.
歯肉に強度の炎症。自然に出血。Severe inflammation of the gums. spontaneous bleeding.
歯肉間溝滲出液量は唾液の混入を防止するため、まずサ
ンプリング部位をティッシュペーパーで拭い、ペリオペ
−パー(Interstate Drug Excha
nge社製、商品名)を歯肉溝に10秒間挿入してサン
プリングし、1度目は捨て、同部位で2度目、3度目の
ものを測定し、この平均を測定値とした。To measure the amount of intergingival sulcus exudate, first wipe the sampling site with a tissue paper and wipe it with period paper (Interstate Drug Excha) to prevent saliva from getting mixed in.
nge (trade name) was inserted into the gingival sulcus for 10 seconds, the first sample was discarded, and the second and third measurements were taken at the same site, and the average was taken as the measured value.
なお、測定は、ペリオドロン()IARCO社製、商品
名)を用いて行い、測定値は計器の読みそのものを採用
した。The measurement was performed using Periodron (manufactured by IARCO, trade name), and the readings of the meter were used as the measured values.
細菌数はペーパーポイント(ジョンソン・アンド・ジョ
ンソン社製)を用いて歯肉間溝滲出液を採取し、5%羊
血入りBHI培地に接種し、5日間嫌気培養し形成した
コロニー数を数えることにより測定した。The number of bacteria was determined by collecting intergingival sulcus exudate using a paper point (manufactured by Johnson & Johnson), inoculating it into BHI medium containing 5% sheep blood, culturing it anaerobically for 5 days, and counting the number of colonies formed. It was measured.
ジンジバルインデックスの経時変化を第1図に、歯肉間
溝滲出液量の経時変化を第2図に、細菌数の経時変化を
第3図にそれぞれ示す。Figure 1 shows the change in the gingival index over time, Figure 2 shows the change in the amount of intergingival sulcus exudate over time, and Figure 3 shows the change in the number of bacteria over time.
この結果から、レンチナンまたはシフフィランを塗布し
たものはジンジバルインデックス、歯肉間溝滲出液量及
び細菌数の明らかな低下が認められた。The results showed that the gingival index, amount of intergingival sulcus exudate, and bacterial count were clearly reduced in those treated with lentinan or schiffilan.
実施例2 ペースト状歯磨剤:
レンチナン 0.10(%)歯
磨用リン酸カルシウム 30.00無水ケイ
酸 2.00カルボキシメチル
セルロース
ラウリル硫酸ナトリウム
グリセリン
70%ソルビット液
香料
精製水
合計
実施例3 クリーム状歯肉塗布剤ニ
ジシフイラン
モノエタノールアミン
流動パラフィン
ポリビニルアルコール
脂肪酸モノグリセライド
グリセリン
香料
粉末蔗糖
合計
実施例4 トローチニ
レンチナン
クエン酸
2.00
0.10
10、00
15.00
0.80
適量
100.00
0.50(%〉
0.10
7.00
5.00
3.00
15、00
0、lO
適量
100、00
0.50(%)
0.10
アスパルテーム
デキストリン
アラビアゴム
香料
乳糖
7.00
5.00
3.00
微蛍
適量
合計 100.D。Example 2 Paste dentifrice: Lentinan 0.10 (%) Calcium phosphate for toothpaste 30.00 Silicic anhydride 2.00 Carboxymethyl cellulose Sodium lauryl sulfate Glycerin 70% Sorbitol liquid Flavor Purified water Total Example 3 Creamy gum liniment Niji Sifiran Monoethanolamine Liquid Paraffin Polyvinyl Alcohol Fatty Acid Monoglyceride Glycerin Flavor Powder Sucrose Total Example 4 Trotinylentinane Citric Acid 2.00 0.10 10,00 15.00 0.80 Appropriate Amount 100.00 0.50 (%> 0 .10 7.00 5.00 3.00 15,00 0, 1O Appropriate amount 100,00 0.50 (%) 0.10 Aspartame dextrin Gum arabic flavoring Lactose 7.00 5.00 3.00 Microfluorescence Appropriate amount total 100 .D.
実施例5 マウスウォッシ5ニ
ジシフイラン 0.50(%)
エタノール 10. DOモノ
エタノールアミン 0.10グルコン酸
クロルヘキシジン 0.10プルロニツク型1’
108 0.50香料 0
.20
精製水 適量合計
100.D。Example 5 Mouthwash 5 Nijishifiran 0.50 (%)
Ethanol 10. DO monoethanolamine 0.10 Chlorhexidine gluconate 0.10 Pluronic type 1'
108 0.50 Fragrance 0
.. 20 Purified water appropriate amount total
100. D.
第1図はジンジバルインデックスの経時変化を、第2図
は歯肉間溝滲出液量の経時変化を示し、第3図は、細菌
数の経時変化を示す図面である。
なお、第1図から第3図中、Δ−△はレンチナン水溶液
、ローロはシフフィラン水溶液、○−○はコントロール
を示す。FIG. 1 shows the change over time in the gingival index, FIG. 2 shows the change over time in the amount of intergingival sulcus exudate, and FIG. 3 shows the change over time in the number of bacteria. In addition, in FIGS. 1 to 3, Δ-Δ indicates a lentinan aqueous solution, Rolo indicates a Schifffilan aqueous solution, and ○-○ indicates a control.
Claims (1)
とする口腔用組成物。1. An oral composition characterized by containing a polysaccharide having an immunomodulatory effect.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16630889A JPH0331210A (en) | 1989-06-28 | 1989-06-28 | Composition for oral cavity |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16630889A JPH0331210A (en) | 1989-06-28 | 1989-06-28 | Composition for oral cavity |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0331210A true JPH0331210A (en) | 1991-02-12 |
Family
ID=15828934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16630889A Pending JPH0331210A (en) | 1989-06-28 | 1989-06-28 | Composition for oral cavity |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0331210A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996034608A1 (en) * | 1995-05-01 | 1996-11-07 | Colgate-Palmolive Company | Oral lubricating composition comprising a beta-glucan |
JP2002539145A (en) * | 1999-03-12 | 2002-11-19 | バイオテク エイエスエイ | Use of surfactant mixtures |
CN102430124A (en) * | 2011-11-24 | 2012-05-02 | 清华大学 | Pill coating with ultralow friction coefficient and preparation method thereof |
-
1989
- 1989-06-28 JP JP16630889A patent/JPH0331210A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996034608A1 (en) * | 1995-05-01 | 1996-11-07 | Colgate-Palmolive Company | Oral lubricating composition comprising a beta-glucan |
US6159459A (en) * | 1995-05-01 | 2000-12-12 | Colgate Palmolive Company | Oral lubricating composition |
JP2002539145A (en) * | 1999-03-12 | 2002-11-19 | バイオテク エイエスエイ | Use of surfactant mixtures |
JP4643014B2 (en) * | 1999-03-12 | 2011-03-02 | バイオテク エイエスエイ | Use of surfactant mixtures |
CN102430124A (en) * | 2011-11-24 | 2012-05-02 | 清华大学 | Pill coating with ultralow friction coefficient and preparation method thereof |
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