JP2006143710A - Liquid composition for oral cavity - Google Patents
Liquid composition for oral cavity Download PDFInfo
- Publication number
- JP2006143710A JP2006143710A JP2005304313A JP2005304313A JP2006143710A JP 2006143710 A JP2006143710 A JP 2006143710A JP 2005304313 A JP2005304313 A JP 2005304313A JP 2005304313 A JP2005304313 A JP 2005304313A JP 2006143710 A JP2006143710 A JP 2006143710A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- acid ester
- oil
- oral cavity
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 239000007788 liquid Substances 0.000 title claims abstract description 26
- 210000000214 mouth Anatomy 0.000 title claims abstract description 15
- -1 fatty acid ester Chemical class 0.000 claims abstract description 57
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 41
- 239000000194 fatty acid Substances 0.000 claims abstract description 41
- 229930195729 fatty acid Natural products 0.000 claims abstract description 41
- 125000002091 cationic group Chemical group 0.000 claims abstract description 19
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 11
- 239000004359 castor oil Substances 0.000 claims abstract description 10
- 235000019438 castor oil Nutrition 0.000 claims abstract description 10
- 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 claims abstract description 10
- 239000002304 perfume Substances 0.000 claims abstract description 4
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 3
- 239000000417 fungicide Substances 0.000 claims description 14
- 230000000855 fungicidal effect Effects 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004386 Erythritol Substances 0.000 claims description 5
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 5
- 235000019414 erythritol Nutrition 0.000 claims description 5
- 229940009714 erythritol Drugs 0.000 claims description 5
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 5
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 4
- 239000000811 xylitol Substances 0.000 claims description 4
- 235000010447 xylitol Nutrition 0.000 claims description 4
- 229960002675 xylitol Drugs 0.000 claims description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 4
- SERLAGPUMNYUCK-DCUALPFSSA-N 1-O-alpha-D-glucopyranosyl-D-mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SERLAGPUMNYUCK-DCUALPFSSA-N 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 abstract description 17
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 16
- 238000001179 sorption measurement Methods 0.000 abstract description 9
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000003205 fragrance Substances 0.000 description 17
- 235000019640 taste Nutrition 0.000 description 10
- 239000002324 mouth wash Substances 0.000 description 9
- 229940051866 mouthwash Drugs 0.000 description 8
- 210000002200 mouth mucosa Anatomy 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 235000019658 bitter taste Nutrition 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000005846 sugar alcohols Chemical class 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 229940041616 menthol Drugs 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229930007050 cineol Natural products 0.000 description 3
- 229960005233 cineole Drugs 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
- 239000000796 flavoring agent Substances 0.000 description 3
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 235000019477 peppermint oil Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- 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
- 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
- 241000894006 Bacteria Species 0.000 description 2
- 206010006326 Breath odour Diseases 0.000 description 2
- 239000005973 Carvone Substances 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
- 235000021360 Myristic acid Nutrition 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 235000009421 Myristica fragrans Nutrition 0.000 description 2
- 240000009023 Myrrhis odorata Species 0.000 description 2
- 235000007265 Myrrhis odorata Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 2
- 229960001950 benzethonium chloride Drugs 0.000 description 2
- 150000004283 biguanides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 2
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 239000000551 dentifrice Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 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 2
- 229940087305 limonene Drugs 0.000 description 2
- 235000001510 limonene Nutrition 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000001683 mentha spicata herb oil Substances 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
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- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
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Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、殺菌剤の歯や口腔粘膜への吸着性に優れ、異味が少なく、安定性の良好な液体口腔用組成物に関する。 The present invention relates to a liquid oral composition having excellent adsorbability of a bactericidal agent to teeth and oral mucosa, little taste, and good stability.
塩化ベンゼトニウムや塩化セチルピリジニウム等のカチオン性殺菌剤は、口腔細菌に対する殺菌活性が高く、かつ歯牙や口腔粘膜などの口腔組織表面へ吸着しやすい性質を有し、歯垢や舌苔などのバイオフィルムの形成を防ぐことから、多くの口腔用組成物に配合されている。 Cationic fungicides such as benzethonium chloride and cetylpyridinium chloride have a high bactericidal activity against oral bacteria and are easily adsorbed on the surface of oral tissues such as teeth and oral mucosa, and are used in biofilms such as plaque and tongue coating. In order to prevent formation, it is blended in many oral compositions.
一方、カチオン性殺菌剤は一般的に苦味等の異味が強いことから、これをマスキングし使用感を高めるために油溶性香料が併用されている。油溶性香料を配合する場合には、可溶化剤としてアニオン系やノニオン系界面活性剤が必須成分として配合されているが、界面活性剤や油溶性香料はカチオン性殺菌剤の殺菌活性や歯牙や口腔粘膜などの口腔組織表面へ吸着性を低下させることが多い。そこで、このような不都合を解消する方法として油溶性香料や界面活性剤を配合しない技術(特許文献1)の報告があるが、この技術は、香料として水溶性香料を使用するため清涼感に欠けるとともに、香味タイプの自由度が少ないなどの問題点があった。また、油溶性香料を少量の界面活性剤で可溶化する技術(特許文献2)が提案されているが、この場合ポリオキシエチレン付加ノニオン系界面活性剤を使用しているため、カチオン性殺菌剤の歯牙や口腔粘膜などの口腔組織表面へ吸着は必ずしも充分とはいえない。さらに、ノニオン界面活性剤であるポリオキシエチレンポリオキシプロピレングリコールを配合することで殺菌剤の効果を発揮させるための技術(特許文献3)が提案されているが、当該界面活性剤の可溶化力の問題から、透明でかつ安定な液体組成物を得るために必要な界面活性剤の含有量では、油溶性香料の清涼感を損ねるという問題点があった。
本発明の目的は、カチオン性殺菌剤を含有し、当該殺菌剤の歯牙や口腔粘膜などの口腔組織表面への吸着性に優れ、かつ長期間の安定性の良好な液体口腔用組成物を提供することにある。 An object of the present invention is to provide a liquid oral composition containing a cationic bactericidal agent, having excellent adsorbability of the bactericidal agent on the surface of oral tissues such as teeth and oral mucosa, and good long-term stability. There is to do.
そこで本発明者は、カチオン性殺菌剤の異味をマスキングすべく油溶性香料を配合した口腔用組成物において、当該組成物を用いた場合のカチオン性殺菌剤の歯牙等への吸着性について種々検討した結果、通常ノニオン界面活性剤は殺菌剤の吸着性を低下させると考えられていたにもかかわらず、糖脂肪酸エステルとポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油及びソルビタン脂肪酸エステルからなる群より選ばれる1種又は2種以上とを組み合せて配合すれば、カチオン性殺菌剤の歯牙等への吸着性が飛躍的に向上し、苦味等が少なく、かつ安定性の良好な液体口腔用組成物が得られることを見出した。 Therefore, the present inventor conducted various studies on the adsorptivity of the cationic fungicide to the teeth and the like when the composition is used in an oral composition containing an oil-soluble fragrance to mask the taste of the cationic fungicide. As a result, in spite of the fact that nonionic surfactants were generally thought to reduce the adsorptivity of bactericides, sugar fatty acid esters and polyglycerin fatty acid esters, polyoxyethylene hydrogenated castor oil and sorbitan fatty acid esters When combined with one or two or more selected ones, the liquid composition for oral cavity can be improved in the adsorptivity of the cationic bactericidal agent to teeth, less bitterness, etc., and stable. It was found that can be obtained.
すなわち、本発明は、次の成分(A)、(B)、(C)及び(D)、
(A)油溶性香料
(B)カチオン性殺菌剤
(C)糖脂肪酸エステル
(D)ポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油及びソルビタン脂肪酸エステルからなる群より選ばれる1種又は2種以上
を含有する液体口腔用組成物を提供するものである。
That is, the present invention includes the following components (A), (B), (C) and (D),
(A) Oil-soluble perfume (B) Cationic fungicide (C) Sugar fatty acid ester (D) Polyglycerol fatty acid ester, polyoxyethylene hydrogenated castor oil and sorbitan fatty acid ester The composition for liquid oral cavity to contain is provided.
本発明の液体口腔用組成物を用いれば、カチオン性殺菌剤が歯牙や口腔粘膜等の口腔組織表面に多量に吸着するため強い殺菌力が得られることから、歯垢や舌苔などのバイオフィルムの形成を強く抑制でき、結果的にむし歯、歯周病、口臭などの口腔トラブル予防効果に優れている。また、苦味などの異味が少ないので継続使用でき、さらに長期安定性も良好である。 When the liquid oral composition of the present invention is used, a strong bactericidal power is obtained because a large amount of the cationic bactericidal agent is adsorbed on the surface of oral tissues such as teeth and oral mucosa. Formation can be strongly suppressed, and as a result, it is excellent in preventing oral troubles such as caries, periodontal disease, and bad breath. Moreover, since there are few unpleasant tastes, such as bitterness, it can be used continuously and also long-term stability is also favorable.
本発明の液体口腔用組成物に用いられる(A)油溶性香料は、カチオン性殺菌剤の苦味などの異味をマスキングするものであり、ClogPが−0.5〜6の香料、好ましくはClogPが0.2〜5の香料である。ClogP値とは、有機化合物の水と1-オクタノールに対する親和性を示す係数であり、1-オクタノール/水の分配係数Pは、1-オクタノールと水の2液相の溶媒に微量の化合物が溶質として溶け込んだときの分配平衡で、それぞれの溶媒中における化合物の平衡濃度の比であり、底10に対するそれらの対数logPの形で示すのが一般的である。多くの化合物のlogP値が報告されており、Daylight Chemical Information Systems, Inc.(Daylight CIS)などから入手しうるプログラム“CLOGP”で計算できる。またDaylight CISのデータベースには多くの値が掲載されている。 The (A) oil-soluble fragrance used in the liquid oral cavity composition of the present invention masks off-flavors such as the bitter taste of a cationic bactericidal agent, and a fragrance having a ClogP of -0.5 to 6, preferably ClogP. It is a fragrance of 0.2-5. The ClogP value is a coefficient indicating the affinity of an organic compound for water and 1-octanol, and the 1-octanol / water partition coefficient P is a small amount of a solute in a two-phase solvent of 1-octanol and water. Partition equilibrium when dissolved as, is the ratio of the equilibrium concentration of the compounds in each solvent and is generally shown in the form of their log P against the base 10. The logP values of many compounds have been reported and can be calculated with the program “CLOGP” available from Daylight Chemical Information Systems, Inc. (Daylight CIS). The Daylight CIS database also contains many values.
“CLOGP”は、Hansch Leoのフラグメントアプローチにより算出される計算logP(ClogP)の値を使用したものである。ここでフラグメントアプローチは、化合物の化学構造に基づいており、原子の数及び化学結合のタイプを考慮している(cf. A. Leo Comprehensive Medicinal Chemistry, Vol.4C. Hansch, P. G. Sammens, J. B Taylor and C. A. Ramsden, Eds., P.295, Pergamon Press, 1990)。 “CLOGP” uses the calculated logP (ClogP) value calculated by Hansch Leo's fragment approach. The fragment approach here is based on the chemical structure of the compound and takes into account the number of atoms and the type of chemical bond (cf. A. Leo Comprehensive Medicinal Chemistry, Vol. 4C. Hansch, PG Sammens, J. B. Taylor and CA Ramsden, Eds., P.295, Pergamon Press, 1990).
このClogP値は現在最も汎用的で信頼できる推定値であるので、化合物の選択に際して実測のlogP値の代わりに用いることができる。本発明では、logPの実測値があればそれを、無い場合にはプログラムCLOGP v4.01により計算したClogP値を用いる。 Since this ClogP value is currently the most general and reliable estimate, it can be used in place of the measured logP value when selecting a compound. In the present invention, if there is an actual measured value of logP, the ClogP value calculated by the program CLOGP v4.01 is used when there is no measured value.
当該成分(A)としては、メントール、カルボン、アネトール、オイゲノール、シネオール、チモール、サリチル酸メチル、プレゴン、メントン、ピネン、リモネン、メンチルアセテート等の合成香料の他に、ペパーミント油、スペアミント油、ハッカ油等のミント油、レモン、オレンジ、グレープフルーツ、ライムなどの柑橘油、ユーカリ、セージ、ローズマリー、タイム、ローレル、バジル、シソ、ベイ、エストラゴン、パセリ、セロリ、コリアンダー等のハーブ油、シナモン、ペッパー、ナツメグ、メース、クローブ、ジンジャー、カルダモン、アニスなどのスパイス油などのような天然精油、アップル、バナナ、メロン、グレープ、ピーチ、ストロベリー、ブルーベリー、ラズベリー、ブラックカラント、ライチ、スターフルーツ、パッションフルーツ、プラム、パイナップル、マスカットなどのフルーツフレーバーなどを用いることができる。これら油溶性香料の中でも、口腔内へ清涼感やさわやかさを付与するという点からメントール、カルボン、ペパーミント油、スペアミント油、ハッカ油、サリチル酸メチル、シネオール、リモネン、ピネンが特に好ましい。これらの油溶性香料は1種又は2種以上を組み合せて用いられる。 In addition to synthetic fragrances such as menthol, carvone, anethole, eugenol, cineol, thymol, methyl salicylate, pregon, menthone, pinene, limonene, menthyl acetate, peppermint oil, spearmint oil, mint oil, etc. Mint oil, citrus oil such as lemon, orange, grapefruit, lime, eucalyptus, sage, rosemary, thyme, laurel, basil, perilla, bay, estragon, parsley, celery, coriander and other herbal oils, cinnamon, pepper, nutmeg Natural essential oils, such as spice oil such as mace, clove, ginger, cardamom, anise, apple, banana, melon, grape, peach, strawberry, blueberry, raspberry, blackcurrant, lychee, star fruit, Tsu Deployment fruit, can be used plum, pineapple, and fruit flavors, such as Muscat. Among these oil-soluble fragrances, menthol, carvone, peppermint oil, spearmint oil, peppermint oil, methyl salicylate, cineol, limonene, and pinene are particularly preferable from the viewpoint of imparting a refreshing feeling and refreshingness to the oral cavity. These oil-soluble fragrances are used alone or in combination of two or more.
成分(A)は、カチオン性殺菌剤の異味のマスキング効果を得る点から、本発明液体口腔用組成物中に0.1〜2質量%、さらに0.2〜1質量%、特に0.3〜0.7質量%含有するのが好ましい。 Component (A) is 0.1 to 2% by mass, more preferably 0.2 to 1% by mass, especially 0.3 to 0.3% by mass in the liquid oral cavity composition of the present invention, from the viewpoint of obtaining the masking effect of the cationic fungicide. It is preferable to contain -0.7 mass%.
(B)カチオン性殺菌剤は、口腔組織表面、例えば歯牙表面、口腔粘膜(歯ぐきを含む)等に吸着し、むし歯、歯周病、口臭等の原因となる菌に対して殺菌作用を有するものであり、第四級アンモニウム化合物、ビグアニド系化合物等が挙げられる。第四級アンモニウム化合物に属する殺菌剤としては、例えば塩化セチルピリジニウム、塩化デカリニウム、塩化ベンゼトニウム、塩化ベンザルコニウム、塩化アルキルジメチルアンモニウム、塩化アルキルトリメチルアンモニウム、塩化メチルベンゼトニウム、塩化ラウロイルコラミノホルミルメチルピリジニウム等が挙げられる。また、ビグアニド系化合物に属する殺菌剤としては、例えばクロルヘキシジンおよびその塩を挙げることができ、好ましくはグルコン酸クロルヘキシジンおよび塩酸クロルヘキシジンである。成分(B)として、上記殺菌剤を1種又は2種以上組み合わせて用いることができるが、殺菌作用及び味の点から、本発明液体口腔用組成物中に0.001〜0.5質量%、さらに0.005〜0.2質量%含有するのが好ましい。 (B) Cationic fungicides adsorb on oral tissue surfaces such as tooth surfaces, oral mucosa (including gums), etc., and have a bactericidal action against bacteria that cause caries, periodontal disease, bad breath, etc. And quaternary ammonium compounds, biguanide compounds and the like. Examples of the bactericides belonging to the quaternary ammonium compounds include cetylpyridinium chloride, decalinium chloride, benzethonium chloride, benzalkonium chloride, alkyldimethylammonium chloride, alkyltrimethylammonium chloride, methylbenzethonium chloride, lauroylcoraminoformylmethylpyridinium chloride, and the like. Is mentioned. Examples of the bactericides belonging to the biguanide compounds include chlorhexidine and salts thereof, preferably chlorhexidine gluconate and chlorhexidine hydrochloride. As the component (B), one or more of the above bactericides can be used in combination, but from the viewpoint of bactericidal action and taste, 0.001 to 0.5% by mass in the liquid oral composition of the present invention. Furthermore, it is preferable to contain 0.005-0.2 mass%.
(C)糖脂肪酸エステルとは、糖の炭素数が6〜18の糖脂肪酸エステル、好ましくは糖の炭素数が10〜14の糖脂肪酸エステル、さらに好ましくは糖の炭素数が12の糖脂肪酸エステルであり、ショ糖脂肪酸エステル、マルトース脂肪酸エステル、ラクトース脂肪酸エステル等を挙げることができる。これらの糖脂肪酸エステルは、カチオン性殺菌剤の歯牙等への吸着量を飛躍的に向上させる作用を有する。当該糖脂肪酸エステルの脂肪酸部分としては、炭素数6〜24の飽和又は不飽和脂肪酸が挙げられ、具体的にはラウリン酸、ミリスチン酸、パルミチン酸、オレイン酸、ステアリン酸等が挙げられる。成分(C)は、前記吸着力向上効果、安定性及び味の点から、本発明液体口腔用組成物中に0.01〜2質量%、さらに0.05〜1質量%、特に0.1〜0.8質量%含有するのが好ましい。 (C) The sugar fatty acid ester is a sugar fatty acid ester having 6 to 18 sugar carbon atoms, preferably a sugar fatty acid ester having 10 to 14 carbon atoms, more preferably a sugar fatty acid ester having 12 sugar carbon atoms. And sucrose fatty acid ester, maltose fatty acid ester, lactose fatty acid ester and the like. These sugar fatty acid esters have the effect of dramatically improving the amount of adsorption of the cationic fungicide on the teeth and the like. Examples of the fatty acid portion of the sugar fatty acid ester include saturated or unsaturated fatty acids having 6 to 24 carbon atoms, and specific examples include lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, and the like. Component (C) is 0.01 to 2% by mass, more preferably 0.05 to 1% by mass, and particularly 0.1 to 0.1% by mass in the composition for liquid oral cavity of the present invention from the viewpoint of the above-mentioned effect of improving the adsorptive power, stability and taste. It is preferable to contain -0.8 mass%.
前記成分(C)と組み合せて使用したときに、(D)ポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油及び/又はソルビタン脂肪酸エステルは味及び安定性を向上させる作用を有する。特にポリグリセリン脂肪酸エステルは、カチオン性殺菌剤の歯牙等への吸着量向上の点から好ましい。ここで、ポリグリセリン脂肪酸エステルのグリセリンの縮合度は2〜20、さらに5〜12が好ましい。また、脂肪酸部分としては、炭素数6〜24の飽和又は不飽和脂肪酸が挙げられ、安定性の点からラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸の脂肪酸が好ましい。ポリオキシエチレン硬化ヒマシ油のポリオキシエチレンの重合度は、5〜120、さらに10〜100が好ましい。ソルビタン脂肪酸エステルの脂肪酸部分としては、炭素数6〜24の飽和又は不飽和脂肪酸が挙げられ、安定性の点からラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸の脂肪酸が好ましい。これらのポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油、ソルビタン脂肪酸エステルは単独で配合してもよいし、併用して配合してもよい。成分(D)は、味及び安定性、特に安定性の点から本発明液体口腔用組成物中に0.001〜2質量%、さらに0.005〜1質量%、特に0.01〜0.8質量%含有するのが好ましい。安定性、カチオン性殺菌剤の歯牙等への吸着量向上の点から成分(C)と成分(D)の含有量は、質量比で30:1〜1:10、さらには10:1〜1:5であることが好ましい。 When used in combination with the component (C), the (D) polyglycerin fatty acid ester, polyoxyethylene hydrogenated castor oil and / or sorbitan fatty acid ester has an effect of improving taste and stability. In particular, polyglycerin fatty acid esters are preferable from the viewpoint of improving the amount of adsorption of the cationic fungicide on the teeth and the like. Here, the glycerin condensation degree of the polyglycerin fatty acid ester is preferably 2 to 20, and more preferably 5 to 12. Moreover, as a fatty-acid part, a C6-C24 saturated or unsaturated fatty acid is mentioned, The fatty acid of a lauric acid, myristic acid, a palmitic acid, and a stearic acid is preferable from a stability point. The degree of polymerization of polyoxyethylene in the polyoxyethylene hydrogenated castor oil is preferably 5 to 120, more preferably 10 to 100. Examples of the fatty acid portion of the sorbitan fatty acid ester include saturated or unsaturated fatty acids having 6 to 24 carbon atoms, and fatty acids such as lauric acid, myristic acid, palmitic acid, and stearic acid are preferable from the viewpoint of stability. These polyglycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, and sorbitan fatty acid esters may be blended alone or in combination. Component (D) is 0.001 to 2% by mass, more preferably 0.005 to 1% by mass, particularly 0.01 to 0.00% in the liquid oral composition of the present invention in terms of taste and stability, particularly stability. It is preferable to contain 8 mass%. The content of component (C) and component (D) is from 30: 1 to 1:10, more preferably from 10: 1 to 1 in terms of stability and the amount of adsorption of cationic bactericides to teeth, etc. : 5 is preferable.
本発明の液体口腔用組成物には、さらに殺菌効果、清涼感を向上させる点から、エタノールを配合するのが好ましい。エタノールの含有量は、液体口腔用組成物中に0.5〜30質量%、さらに1〜20質量%、特に4〜15質量%が好ましい。 It is preferable to mix | blend ethanol with the liquid oral cavity composition of this invention from the point which improves a bactericidal effect and a refreshing feeling further. The content of ethanol is preferably 0.5 to 30% by mass, more preferably 1 to 20% by mass, and particularly preferably 4 to 15% by mass in the liquid oral composition.
さらに本発明の液体口腔用組成物中は、アニオン界面活性剤、成分(C)及び(D)以外のノニオン界面活性剤、糖アルコール、粘結剤、多価アルコール、緩衝剤、その他の薬効剤、甘味剤、水等を含有することができる。 Further, in the liquid oral cavity composition of the present invention, anionic surfactants, nonionic surfactants other than components (C) and (D), sugar alcohols, binders, polyhydric alcohols, buffers, and other medicinal agents , Sweeteners, water and the like.
アニオン界面活性剤としては、ラウリル硫酸ナトリウム、ミリスチル硫酸ナトリウム等のアルキル硫酸エステル塩;ラウロイルサルコシンナトリウム等のN−アシルアミノ酸塩;ラウロイルメチルタウリンナトリウム等のアシルタウリン塩;ヤシ油脂肪酸エチルエステルスルホン酸ナトリウム塩等の脂肪酸エステルスルホン酸塩等が挙げられる。 Examples of the anionic surfactant include alkyl sulfate salts such as sodium lauryl sulfate and sodium myristyl sulfate; N-acyl amino acid salts such as sodium lauroyl sarcosine; acyl taurine salts such as sodium lauroylmethyl taurine; sodium coconut oil fatty acid ethyl ester sulfonate And fatty acid ester sulfonates such as salts.
これらのアニオン界面活性剤の含有量は、刺激及びカチオン性殺菌剤の歯牙等への吸着の点から、液体口腔用組成物中に0.01質量%以下(0〜0.01質量%)が好ましい。 The content of these anionic surfactants is 0.01% by mass or less (0 to 0.01% by mass) in the liquid oral composition from the viewpoint of stimulation and adsorption of the cationic bactericidal agent to the teeth and the like. preferable.
本発明に用いられる糖アルコールとしては、エリスリトール、キシリトール、リビトール、アラビトール、ガラクチトール、ソルビトール、マンニトール、マルチトール、パラチニット、ラクチトール、マルトトリイトール、イソマルトトリイトール、マルトテトライトール、イソマルトテトライトール、還元水あめ類等が挙げられるが、このうちバイオフィルム形成抑制の点でエリスリトール、キシリトール、パラチニットが好ましい。糖アルコール中のエリスリトール、キシリトール及びパラチニットの含有量の合計(質量比)は、1/2以上となることが好ましく、さらに好ましくは2/3以上である。 Examples of the sugar alcohol used in the present invention include erythritol, xylitol, ribitol, arabitol, galactitol, sorbitol, mannitol, maltitol, palatinit, lactitol, maltotriitol, isomaltoteitol, maltotetriitol, isomaltotetriol. Among them, erythritol, xylitol, and paratinite are preferable from the viewpoint of suppressing biofilm formation. The total content (mass ratio) of erythritol, xylitol, and palatinit in the sugar alcohol is preferably 1/2 or more, and more preferably 2/3 or more.
これらの糖アルコールは、良好な清涼感、異味・異臭防止作用を得る点から、本発明液体口腔用組成物中に4〜50質量%、さらに5〜35質量%、特に6〜20質量%含有するのが好ましい。 These sugar alcohols are contained in the liquid oral composition of the present invention in an amount of 4 to 50% by mass, more preferably 5 to 35% by mass, particularly 6 to 20% by mass, from the viewpoint of obtaining a good refreshing feeling and a taste and odor prevention effect. It is preferable to do this.
粘結剤としては、カルボキシメチルセルロースナトリウム、ヒドロキシエチルセルロース等のセルロース誘導体、アルギン酸ナトリウム、アルギン酸プロピレングリコール等のアルギン酸誘導体、カラギーナン、キサンタンガム、ジュランガム、トラガントガム、カラヤガム等のガム類、ポリビニルアルコール、ポリアクリル酸ナトリウム、カルボキシビニルポリマー等の合成粘結剤、シリカゲル、ビーガム、ラポナイト等の無機粘結剤、デキストリン、還元デキストリン等の澱粉分解物等が挙げられる。これらは1種又は2種以上を混合して用いることができる。 As a binder, cellulose derivatives such as sodium carboxymethylcellulose and hydroxyethylcellulose, alginic acid derivatives such as sodium alginate and propylene glycol alginate, gums such as carrageenan, xanthan gum, duran gum, tragacanth gum and karaya gum, polyvinyl alcohol, sodium polyacrylate, Examples thereof include synthetic binders such as carboxyvinyl polymer, inorganic binders such as silica gel, bee gum and laponite, and starch degradation products such as dextrin and reduced dextrin. These may be used alone or in combination of two or more.
多価アルコールとしては、プロピレングリコール、グリセリン、ポリエチレングリコール等が挙げられる。緩衝剤としては、クエン酸及びその塩、リンゴ酸及びその塩、リン酸及びその塩等が挙げられる。甘味剤としては、サッカリンナトリウム、アセスルファームカリウム、ステビオサイド、ネオヘスペリジルジヒドロカルコン、グリチルリチン、ペリラルチン、ソウマチン、アスパラチルフェニルアラニルメチルエステル、スクラロース等が挙げられる。その他の薬効剤としてはトラネキサム酸、イプシロンアミノカプロン酸等の抗プラスミン剤、アスコルビン酸、トコフェロールエステル等のビタミン類、グリチルリチン塩類、アラントイン類、オウバク、オウゴン、カミツレ、ラタニア、ミルラ等の植物抽出物、デキストラナーゼ、ムタナーゼ、塩化リゾチーム等の酵素、モノフルオロリン酸ナトリウム等のアルカリ金属モノフルオロフォスフェート、フッ化ナトリウム、フッ化第1錫等のフッ化物、塩化ナトリウム、硝酸カリウム、炭酸塩、重炭酸塩、セスキ炭酸塩等の塩類、銅クロロフィリンナトリウム、グルコン酸銅、塩化亜鉛、ゼオライト、水溶性無機リン酸化合物、乳酸アルミニウム等の1種又は2種以上が挙げられる。 Examples of the polyhydric alcohol include propylene glycol, glycerin, and polyethylene glycol. Examples of the buffer include citric acid and its salt, malic acid and its salt, phosphoric acid and its salt, and the like. Examples of the sweetener include saccharin sodium, acesulfame potassium, stevioside, neohesperidyl dihydrochalcone, glycyrrhizin, perilartine, saumatine, asparatylphenylalanyl methyl ester, sucralose and the like. Other medicinal agents include anti-plasmin agents such as tranexamic acid and epsilon aminocaproic acid, vitamins such as ascorbic acid and tocopherol esters, glycyrrhizin salts, allantoins, plant extracts such as buckwheat, ogon, chamomile, latania, myrrh, Enzymes such as stranase, mutanase, lysozyme chloride, alkali metal monofluorophosphates such as sodium monofluorophosphate, fluorides such as sodium fluoride, stannous fluoride, sodium chloride, potassium nitrate, carbonate, bicarbonate , Salts such as sesquicarbonate, copper chlorophyllin sodium, copper gluconate, zinc chloride, zeolite, water-soluble inorganic phosphate compound, aluminum lactate, etc.
本発明の液体口腔用組成物は、液体歯磨、水歯磨、洗口液、マウススプレー、うがい薬等として適用できる。 The liquid oral composition of the present invention can be applied as liquid dentifrice, water dentifrice, mouthwash, mouth spray, mouthwash, and the like.
表1および表2に示す洗口液を調製し、下記の方法で安定性試験、香味試験および殺菌剤の歯牙への吸着試験を行った。なお、いずれの洗口液もメントール等の香料を界面活性剤を含有する水に溶解した後、エリスリトール水溶液と混合して製造した。 Mouthwashes shown in Table 1 and Table 2 were prepared, and a stability test, a flavor test, and a fungicide adsorption test on teeth were performed by the following methods. Each mouthwash was prepared by dissolving a fragrance such as menthol in water containing a surfactant and then mixing it with an erythritol aqueous solution.
[安定性試験]
洗口液を調整後、50℃にて2週間放置したときの、液の性状を下記に示す判定基準にて評価した。
判定基準
◎:透明
○:やや透明
△:透明ではないが分離なし
×:分離
[Stability test]
After adjusting the mouthwash, the properties of the liquid when allowed to stand at 50 ° C. for 2 weeks were evaluated according to the following criteria.
Criteria ◎: Transparent ○: Slightly transparent △: Not transparent but no separation ×: Separation
[苦味試験]
洗口液10mLで30秒間含嗽し吐き出したときに口の中に残る苦味を下記に示す判定基準にて判定した。
判定基準
◎:苦くない
○:わずかに苦い
△:やや苦い
×:かなり苦い
[Bitter taste test]
The bitterness remaining in the mouth when the mouthwash was sprinkled with 10 mL of mouthwash for 30 seconds was determined according to the following criteria.
Judgment criteria ◎: not bitter ○: slightly bitter △: slightly bitter ×: quite bitter
[殺菌剤の吸着試験]
歯牙のモデルとしてエナメル質の主成分であるハイドロキシアパタイト(HA)粉末(太平化学産業;以下、HAと略す)を用いた。10mgのHAを表1および表2に示す各洗口液1mLに30秒間浸漬後、イオン交換水2mLにて洗浄し、HAに吸着した殺菌剤を65%アセトニトリル溶液で抽出したものを高速液体クロマトグラフィ(ODSカラム:Superspher100(関東化学製)、流速:1mL/min、測定波長:210nm)にて定量し、吸着量を算出した。
[Bactericide adsorption test]
Hydroxyapatite (HA) powder (Taihei Chemical Industry; hereinafter abbreviated as HA), which is the main component of enamel, was used as a tooth model. 10 mg of HA is immersed in 1 mL of each mouthwash shown in Tables 1 and 2 for 30 seconds, then washed with 2 mL of ion-exchanged water, and the bactericide adsorbed on HA is extracted with a 65% acetonitrile solution. (ODS column: Superspher100 (manufactured by Kanto Chemical), flow rate: 1 mL / min, measurement wavelength: 210 nm) was quantified, and the amount of adsorption was calculated.
ポリオキシエチレン硬化ヒマシ油:ポリオキシエチレン(60)硬化ヒマシ油
糖脂肪酸エステル:ショ糖ミリスチン酸エステル
ポリグリセリン脂肪酸エステル:ポリグリセリンミリスチン酸エステル(縮合度10)
ソルビタン脂肪酸エステル:ソルビタンステアリン酸エステル
香料:メントール+シネオール+スパイス油
Polyoxyethylene hydrogenated castor oil: Polyoxyethylene (60) hydrogenated castor oil Sugar fatty acid ester: Sucrose myristic acid ester Polyglycerin fatty acid ester: Polyglyceryl myristic acid ester (condensation degree 10)
Sorbitan fatty acid ester: Sorbitan stearate Perfume: Menthol + Cineol + Spice oil
表1及び表2の結果より、カチオン性殺菌剤と油溶性香料を含有した系に、糖脂肪酸エステルを配合すると、殺菌剤の吸着性が飛躍的に向上することがわかる。このような吸着性向上効果は、糖脂肪酸エステルに特異的である。そして、その系にポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油又はソルビタン脂肪酸エステルを配合すると殺菌剤の吸着性、組成物の味、安定性に優れた洗口液を得ることができる。 From the results of Tables 1 and 2, it can be seen that when a sugar fatty acid ester is added to a system containing a cationic fungicide and an oil-soluble fragrance, the adsorptivity of the fungicide is dramatically improved. Such an adsorbability improving effect is specific to sugar fatty acid esters. When a polyglycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, or sorbitan fatty acid ester is added to the system, a mouthwash with excellent disinfectant adsorbability, composition taste, and stability can be obtained.
Claims (4)
(A)油溶性香料
(B)カチオン性殺菌剤
(C)糖脂肪酸エステル
(D)ポリグリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油及びソルビタン脂肪酸エステルからなる群より選ばれる1種又は2種以上
を含有する液体口腔用組成物。 The following components (A), (B), (C) and (D),
(A) Oil-soluble perfume (B) Cationic fungicide (C) Sugar fatty acid ester (D) Polyglycerol fatty acid ester, polyoxyethylene hydrogenated castor oil and sorbitan fatty acid ester Liquid oral composition to contain.
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JP2009001511A (en) * | 2007-06-20 | 2009-01-08 | Kao Corp | Liquid oral composition |
JP2009096724A (en) * | 2007-10-12 | 2009-05-07 | Kao Corp | Liquid composition for oral cavity |
JP2013067570A (en) * | 2011-09-21 | 2013-04-18 | Sunstar Inc | Composition for oral cavity |
JP2013075858A (en) * | 2011-09-30 | 2013-04-25 | Kobayashi Pharmaceutical Co Ltd | Composition for oral cavity |
JP2014118373A (en) * | 2012-12-14 | 2014-06-30 | Kao Corp | Liquid oral composition |
JP2021506741A (en) * | 2017-12-20 | 2021-02-22 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | Oral care composition |
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JP7268012B2 (en) | 2017-12-20 | 2023-05-02 | フイルメニツヒ ソシエテ アノニム | oral care composition |
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