WO2013094504A1 - Composition orale - Google Patents

Composition orale Download PDF

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Publication number
WO2013094504A1
WO2013094504A1 PCT/JP2012/082298 JP2012082298W WO2013094504A1 WO 2013094504 A1 WO2013094504 A1 WO 2013094504A1 JP 2012082298 W JP2012082298 W JP 2012082298W WO 2013094504 A1 WO2013094504 A1 WO 2013094504A1
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WO
WIPO (PCT)
Prior art keywords
component
composition
sodium
salt
mass
Prior art date
Application number
PCT/JP2012/082298
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English (en)
Japanese (ja)
Inventor
亜紀子 二階堂
尚子 川口
Original Assignee
ライオン株式会社
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Publication date
Application filed by ライオン株式会社 filed Critical ライオン株式会社
Publication of WO2013094504A1 publication Critical patent/WO2013094504A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention relates to an oral composition particularly suitable as a liquid preparation, in which the irritant feeling of glycerophosphoric acid or a salt thereof is suppressed and the astringency and taste are improved, giving a good feeling of use.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 2005-47855 proposes that glycerophosphoric acid and its salt are effective in suppressing oral biofilms.
  • calcium glycerophosphate is considered to increase calcium and phosphate concentrations in dental plaque to promote remineralization, prevent a marked decrease in plaque pH, and inhibit mutans bacteria metabolism.
  • glycerophosphoric acid and salts thereof have a sense of irritation, astringency and taste, and for this reason, oral compositions containing glycerophosphoric acid or salts thereof, particularly liquid oral compositions such as mouthwashes, There was a problem that the aftertaste was bad and the feeling of use was impaired.
  • Patent Document 2 Japanese Patent Laid-Open No. 2009-149560 contains glycero by adding raffinose and / or melibiose to calcium glycerophosphate and sodium monofluorophosphate. Although it has been proposed that the astringency and bitterness derived from calcium phosphate and sodium monofluorophosphate are suppressed, there is no indication regarding the irritation and its relaxation.
  • Patent Document 3 Japanese Patent Laid-Open No. 2010-215568 proposes a technique for reducing astringency, bitterness, and irritation by adding lactone and propylene glycol alginate to calcium glycerophosphate.
  • this technique has a problem that the propylene glycol alginate becomes sticky, and there is room for improvement in the feeling of use.
  • the kind of flavor which can be used was limited.
  • the present invention has been made in order to solve the above-mentioned problems, and provides an oral composition that gives a good feeling of use, with the irritant feeling of glycerophosphoric acid or a salt thereof being suppressed and the astringency and taste being improved.
  • the purpose is to do.
  • the present invention provides the following oral composition. [1] It contains (A) glycerophosphoric acid or a salt thereof and (B) glycyrrhizic acid or a salt thereof, and the component (B) / component (A) is 0.15 to 20 as a mass ratio. A composition for oral cavity. [2] The oral composition according to [1], further comprising (C) one or more components selected from vanilla absolute, vanillin, ethyl vanillin and nutmeg oil.
  • an oral composition that suppresses the irritation of glycerophosphoric acid or a salt thereof, improves astringency and taste, and gives a good feeling of use.
  • composition for oral cavity of this invention contains (A) glycerophosphoric acid or its salt, and (B) glycyrrhizic acid or its salt.
  • glycerophosphoric acid or salt thereof as component (A) examples include glycerophosphoric acid, alkali metal salts such as sodium salt and potassium salt thereof, and alkaline earth metal salts such as calcium salt. Two or more kinds can be mixed and blended. Among these, calcium glycerophosphate is more preferable from the viewpoint of effect expression.
  • Component (A) can be either a natural product or a synthetic product.
  • calcium glycerophosphate can be used from a natural product or a synthetic product.
  • a commercially available product such as a trade name “Calcium glycerophosphate” manufactured by Iwaki Pharmaceutical Co., Ltd. can be used.
  • the blending amount of component (A) is preferably 0.005 to 1% (mass%, hereinafter the same) of the total composition, more preferably 0.01 to 0.2%.
  • the blending effect improves as the blending amount increases. However, when the blending amount exceeds 1%, the feeling of irritation, astringency and off-taste derived from the component (A) may become too strong and the usability may be impaired.
  • the component (B) glycyrrhizic acid or a salt thereof is a stimulant, astringent or unpleasant mitigating / suppressing agent derived from the component (A).
  • Examples of the component (B) glycyrrhizic acid or a salt thereof include glycyrrhizic acid, dipotassium glycyrrhizinate, tripotassium glycyrrhizinate, disodium glycyrrhizinate, trisodium glycyrrhizinate, monoammonium glycyrrhizinate, and diammonium glycyrrhizinate.
  • dipotassium glycyrrhizinate is particularly preferable from the viewpoint of solubility in water and taste.
  • a plant containing glycyrrhizic acid or a salt thereof for example, herbal medicine such as licorice or licorice extract can be blended.
  • the amount of glycyrrhizic acid or its salt is preferably 0.001 to 0.25%, more preferably 0.01 to 0.2% of the total composition. The greater the amount, the less the irritation and the better the astringency / taste. .
  • the component (B) / component (A) indicating the blending ratio of the components (A) and (B) is 0.15 to 20, and preferably 0.2 to 10, as a mass ratio.
  • the ratio is less than 0.15, the effect of suppressing the irritation of component (A) and improving the feeling of use (astringency and taste) are not sufficiently obtained. If it exceeds 20, the astringency, nasty taste, etc. of the component (B) itself become strong and the feeling of use is inferior.
  • composition of the present invention preferably further contains (C) a component selected from vanilla absolute, vanillin, ethyl vanillin, and nutmeg oil.
  • a component (C) is mix
  • vanillin and ethyl vanillin for example, commercially available products such as “Wanilin” manufactured by Toyoda Fragrance Co., Ltd., and “Ethyl Vanillin” manufactured by Kamata Fragrance Co., Ltd. can be used.
  • Vanilla absolute can be obtained, for example, by solvent extraction of vanilla beans by the following method.
  • Commercial products can also be used.
  • Vanilla beans are extracted with an organic solvent (benzene, acetone, hexane, petroleum ether, etc.), and the solvent is distilled off (reduced pressure) to obtain vanilla oleoresin.
  • This is extracted with a solvent (ethanol), cooled, the insoluble matter is filtered, and then the solvent is distilled off (reduced pressure) to obtain vanilla absolute.
  • a solution diluted with a solvent such as ethanol, jojoba oil, or medium chain fatty acid ester can also be used.
  • the brand name "Vanilla absolute (50% ethanol dilution product)" by the Kamata perfume company can be used, for example.
  • Nutmeg oil can be obtained by steam distillation of nutmeg seeds (Nutmeg, Nutaceae, scientific name: Myristica fragrance Hout.).
  • a commercial item can also be used, for example, "Nutmeg Oil” manufactured by We Mann Fis Fragrance Co., Ltd. can be used.
  • Component (C) can be used alone or in combination of two or more of the above compounds.
  • vanilla absolute alone or a combination of vanilla absolute and one or more selected from vanillin, ethyl vanillin, and nutmeg oil is preferable in terms of effect.
  • the combined use of vanilla absolute and nutmeg oil is particularly preferable.
  • the blending amount is preferably 0.0000001 to 0.004%, more preferably 0.0000004 to 0.00075% of the entire composition. If it is less than 0.0000001%, the effect of alleviating irritation and improving the feeling of use may not be satisfactorily improved. If it exceeds 0.004%, the feeling of use may be impaired by the flavor of itself.
  • Component (C) / component (A) has a mass ratio of preferably 0.0000002 to 0.6, more preferably 0.000004 to 0.3, and still more preferably 0.000008 to 0.05. If it is less than 0.0000002, the usability improvement effect may not be sufficiently improved. When it exceeds 0.6, the flavor characteristic of component (C) itself may become strong and may be inferior to a feeling of use.
  • composition of the present invention can further contain a cationic fungicide.
  • a cationic fungicide one or more of cetylpyridinium chloride, benzethonium chloride, benzalkonium chloride and the like can be used, and cetylpyridinium chloride and benzethonium chloride are particularly preferable, and chloride is particularly preferable in terms of usability. More preferred is cetylpyridinium.
  • the blending amount is preferably 0.005 to 0.1%, more preferably 0.01 to 0.08% of the entire composition. If it is less than 0.005%, the blending effect may not be recognized. If it exceeds 0.1%, astringent taste and off-taste derived from the cationic fungicide may occur, and the feeling in use may be impaired. Further, the blending amount of cetylpyridinium chloride is preferably 0.01 to 0.1%, more preferably 0.02 to 0.08% of the total composition. The blending amount of benzethonium chloride is preferably 0.005 to 0.1%, more preferably 0.008 to 0.05% of the total composition.
  • the composition of the present invention is particularly suitably prepared as a liquid oral composition in which the blending components are solubilized.
  • the composition of the present invention is also effective in paste-form preparations such as dentifrices.
  • liquid preparations such as mouthwashes and liquid dentifrices are particularly irritating and astringent. -Although a nasty taste is strongly expressed, according to this invention, an irritation feeling can be relieved with such a liquid formulation, and astringency and taste can be suppressed.
  • a mouthwash of the type that is used as it is a freshener in the mouth
  • a mouthwash that is diluted at the time of use in a concentrated type a mouthwash that is diluted at the time of use in a concentrated type
  • a liquid dentifrice that is used by brushing with a toothbrush.
  • a mouthwash is particularly suitable as a mouthwash.
  • the liquid oral composition contains a wetting agent, a surfactant, a solvent, and if necessary, a sweetener, a coloring agent, a fragrance, an active ingredient, and the like.
  • solid components which do not solubilize such as an abrasive
  • wetting agent examples include sugar alcohols such as sorbitol, malt, and lactit, and polyhydric alcohols such as glycerin, ethylene glycol, and polyethylene glycol.
  • sugar alcohols such as sorbitol, malt, and lactit
  • polyhydric alcohols such as glycerin, ethylene glycol, and polyethylene glycol.
  • the blending amount of these wetting agents is preferably 2 to 20% of the total composition.
  • surfactant known anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants can be blended, and it is particularly preferable to blend nonionic surfactants.
  • anionic surfactants include sodium alkyl sulfates such as sodium lauryl sulfate and sodium myristyl sulfate, sodium N-acyl sarcosine such as sodium N-lauroyl sarcosine, sodium N-myristoyl sarcosine, sodium dodecylbenzenesulfonate, hydrogenated coconut fatty acid Sodium monoglyceride, sodium lauryl sulfoacetate, N-acyl glutamate such as sodium N-palmitoyl glutamate, sodium N-methyl-N-acyl taurate, sodium N-methyl-N-acylalanine, sodium ⁇ -olefin sulfonate, etc. Is mentioned.
  • Nonionic surfactants include, for example, sugar alcohol fatty acid esters such as sucrose fatty acid ester, maltose fatty acid ester, maltitol fatty acid ester, lactol fatty acid ester, polyoxyethylene fatty acid ester such as polyoxyethylene hydrogenated castor oil, alkylol amide, Examples include polyoxyethylene sorbitan fatty acid ester, polyglycerin fatty acid ester, hexaglyceryl monocetylate, fatty acid diethanolamide, sorbitan fatty acid ester, polyoxyethylene higher alcohol ether, and the like.
  • sugar alcohol fatty acid esters such as sucrose fatty acid ester, maltose fatty acid ester, maltitol fatty acid ester, lactol fatty acid ester
  • polyoxyethylene fatty acid ester such as polyoxyethylene hydrogenated castor oil, alkylol amide
  • examples include polyoxyethylene sorbitan fatty acid ester, polyglycerin fatty acid
  • Nonionic surfactants include, in particular, polyoxyethylene hydrogenated castor oil having an average addition mole number of ethylene oxide of 40 to 100 moles, an average addition mole of ethylene oxide having an alkyl group having 16 (cetyl) to 18 (stearyl) carbon atoms.
  • polyoxyethylene hydrogenated castor oil is preferable in terms of sufficiently exerting the adhesion inhibitory effect of dental plaque on the tooth surface and appearance stability (no orientation), and in particular, the average added mole number of ethylene oxide is Those having 40 to 100 mol, particularly 60 to 100 mol are preferred. When the average added mole number of ethylene oxide is less than 40 moles, orientation is generated particularly in liquid preparations and stored at 50 ° C., and appearance stability (no orientation) may be impaired. Those exceeding 100 mol are generally not commercially available.
  • polyoxyethylene hydrogenated castor oil commercially available products such as NIKKOL HCO system manufactured by Nikko Chemicals, Emarex HC system manufactured by Nihon Emulsion Co., Ltd., UNIOX HC system manufactured by NOF Corporation, and the like can be used.
  • polyoxyethylene alkyl ether commercially available products such as Emarex 100 series and Emarex 600 series manufactured by Nikko Chemicals can be used.
  • decaglycerin monofatty acid ester commercially available products such as NIKKOL Decagln series manufactured by Nikko Chemicals, Ryoto (registered trademark) polyglycerester D series manufactured by Mitsubishi Chemical Foods, Inc. can be used.
  • Examples of the cationic surfactant include alkyl ammonium and alkyl benzyl ammonium salts.
  • Amphoteric surfactants include betaine acetate-type amphoteric surfactants such as alkyldimethylaminoacetic acid betaines and fatty acid amidopropyldimethylaminoacetic acid betaines, and imidazoline types such as N-fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine salts. Examples include amphoteric surfactants. The blending amount of these surfactants is preferably 0.05 to 5% of the entire composition.
  • xylitol xylitol, maltitol, saccharin, saccharin sodium, stevioside, aspartame and the like can be blended.
  • a colorant a highly safe water-soluble pigment such as Blue No. 1, Green No. 3, Yellow No. 4, Red No. 105, and the like can be added.
  • natural essential oils such as peppermint oil, spearmint oil, eucalyptus oil, winter green oil, clove oil, thyme oil, sage oil, cardamom oil, rosemary oil, marjoram oil, lemon oil, lavender oil and paracres oil, And l-menthol, l-carvone, orange oil, anethole, 1,8-cineole, methyl salicylate, eugenol, thymol, linalool, limonene, menthone, eugenol, menthyl acetate, citral, camphor, borneol, pinene, spirantol, etc.
  • natural essential oils such as peppermint oil, spearmint oil, eucalyptus oil, winter green oil, clove oil, thyme oil, sage oil, cardamom oil, rosemary oil, marjoram oil, lemon oil, lavender oil and paracres oil, And l-menthol, l-carvone, orange oil,
  • Perfume ingredients contained in natural essential oils ethyl acetate, ethyl butyrate, isoamyl acetate, hexanal, hexenal, methyl anthranilate, ethyl methyl phenyl glycidate, benzalde Perfume ingredients such as flavonol, furaneol, maltol, ethyl maltol, gamma / delta decalactone, gamma / deltown decalactone, N-ethyl-p-menthane-3-carboxamide, menthyl lactate, ethylene glycol-l-menthyl carbonate, etc. Is a combination of several fragrance ingredients and natural essential oils.
  • species or 2 or more types can be added in the range which does not prevent the effect of this invention.
  • the addition amount is usually 0.00001 to 3% in the composition.
  • Active ingredients include, for example, bactericides such as isopropyl methyl cellulose, enzymes such as dextranase and mutanase, fluorides such as sodium fluoride and sodium monofluorophosphate, aluminum chlorohydroxy allantoin, allantoin, azulene, lysozyme chloride, ascorbic acid
  • bactericides such as isopropyl methyl cellulose
  • enzymes such as dextranase and mutanase
  • fluorides such as sodium fluoride and sodium monofluorophosphate
  • aluminum chlorohydroxy allantoin, allantoin, azulene lysozyme chloride
  • ascorbic acid Such as vitamin C, dihydrocholesterol, glycyrrhetin salts, hydrocholesterol, chlorophyll, copper chlorophyllin sodium, thyme, ogon, clove, hamamelis, plant extracts, copper gluconate, caropeptide
  • the solvent water is usually used, and the water content is preferably 60% or more of the total composition.
  • a lower monohydric alcohol such as ethanol may be blended within a range not impeding the effects of the present invention, but when added, it is preferably 10% or less of the entire composition.
  • Liquid oral compositions having the compositions shown in Tables 1 to 3 were prepared by conventional methods and evaluated by the following methods. The results are shown in Tables 1 to 3.
  • the sample (liquid oral composition) contains about 10 ml in the mouth, rinsed for 30 seconds, and then evaluated for lack of irritation after mouthwash in the following 5 levels. Are indicated by ⁇ , ⁇ , ⁇ , ⁇ , ⁇ in accordance with the following criteria. Evaluation criteria for lack of irritation: 5 points: There was no irritation. 4 points: There was no irritation. 3 points: There was a slight irritation. 2 points: There was some irritation. 1 point: There was considerable irritation.
  • Criteria for lack of irritation ⁇ : Average point 4.5 points or more and 5.0 points or less ⁇ : Average point 4.0 points or more and less than 4.5 points ⁇ : Average point 3.0 points or more and less than 4.0 points ⁇ : Average point 2.0 points More than less than 3.0 points x: Average point less than 2.0 points
  • a prescription example is shown below.
  • the oral compositions of these prescription examples all had a good feeling of use because the irritation of glycerophosphoric acid and its salts was suppressed, and the astringency and taste were improved.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention porte sur une composition orale, la sensation d'irritation provoquée par l'acide glycérophosphorique ou un sel de celui-ci étant éliminée, l'astringence et le goût spécial étant améliorés et une bonne sensation à l'application étant assurée. La composition orale comprend (A) de l'acide glycérophosphorique ou un sel de celui-ci et (B) de l'acide glycyrrhizique ou un sel de celui-ci, ladite composition orale étant caractérisée en ce que le rapport (composant (B))/(composant (A)) est de 0,15 à 20 en masse. La composition orale peut de plus contenir (C) au moins un composant choisi parmi l'essence absolue de vanille, la vanilline, l'éthylvanilline et l'essence de muscade.
PCT/JP2012/082298 2011-12-21 2012-12-13 Composition orale WO2013094504A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-279170 2011-12-21
JP2011279170A JP5874383B2 (ja) 2011-12-21 2011-12-21 口腔用組成物

Publications (1)

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WO2013094504A1 true WO2013094504A1 (fr) 2013-06-27

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016124808A (ja) * 2014-12-26 2016-07-11 アース製薬株式会社 口腔用組成物
WO2017012764A1 (fr) * 2015-07-21 2017-01-26 Henkel Ag & Co. Kgaa Crème dentifrice à inactivation réduite du fluorure
JP2017100965A (ja) * 2015-11-30 2017-06-08 ライオン株式会社 口腔用組成物
CN109771340A (zh) * 2019-03-29 2019-05-21 上海涵博生物科技有限公司 一种口气清新喷雾
WO2019194068A1 (fr) * 2018-04-06 2019-10-10 ライオン株式会社 COMPOSITION DESTINÉE À ÊTRE UTILISÉE DANS LA BOUCHE ET AGENT D'ATTÉNUATION DE L'AMERTUME POUR SULFONATES D'α–OLÉFINE
JP2020172467A (ja) * 2019-04-10 2020-10-22 花王株式会社 口腔用組成物

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101636430B1 (ko) * 2014-07-10 2016-07-05 동아제약 주식회사 항염 및 살균력이 증진된 치주질환 예방 또는 개선용 조성물
JP6471667B2 (ja) * 2015-09-28 2019-02-20 ライオン株式会社 液体口腔用組成物
JP6861010B2 (ja) * 2015-11-30 2021-04-21 花王株式会社 練歯磨組成物
WO2020174914A1 (fr) * 2019-02-28 2020-09-03 花王株式会社 Composition pour cavité buccale
JP6960434B2 (ja) * 2019-06-27 2021-11-05 花王株式会社 口腔用組成物

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JPH09241140A (ja) * 1996-03-04 1997-09-16 Sunstar Inc 口腔用組成物
JP2005336078A (ja) * 2004-05-25 2005-12-08 Nippon Paper Chemicals Co Ltd マスキング剤
JP2008266251A (ja) * 2007-04-24 2008-11-06 Lion Corp 歯磨組成物
JP2009062339A (ja) * 2007-09-07 2009-03-26 Humic Kenkyusho:Kk 口腔用組成物
JP2009517384A (ja) * 2005-11-23 2009-04-30 ザ・コカ−コーラ・カンパニー 高効能甘味料を用いた歯科用組成物
JP2011140454A (ja) * 2010-01-06 2011-07-21 Sunstar Inc 口腔用組成物

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JPH09241140A (ja) * 1996-03-04 1997-09-16 Sunstar Inc 口腔用組成物
JP2005336078A (ja) * 2004-05-25 2005-12-08 Nippon Paper Chemicals Co Ltd マスキング剤
JP2009517384A (ja) * 2005-11-23 2009-04-30 ザ・コカ−コーラ・カンパニー 高効能甘味料を用いた歯科用組成物
JP2008266251A (ja) * 2007-04-24 2008-11-06 Lion Corp 歯磨組成物
JP2009062339A (ja) * 2007-09-07 2009-03-26 Humic Kenkyusho:Kk 口腔用組成物
JP2011140454A (ja) * 2010-01-06 2011-07-21 Sunstar Inc 口腔用組成物

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016124808A (ja) * 2014-12-26 2016-07-11 アース製薬株式会社 口腔用組成物
WO2017012764A1 (fr) * 2015-07-21 2017-01-26 Henkel Ag & Co. Kgaa Crème dentifrice à inactivation réduite du fluorure
JP2017100965A (ja) * 2015-11-30 2017-06-08 ライオン株式会社 口腔用組成物
WO2019194068A1 (fr) * 2018-04-06 2019-10-10 ライオン株式会社 COMPOSITION DESTINÉE À ÊTRE UTILISÉE DANS LA BOUCHE ET AGENT D'ATTÉNUATION DE L'AMERTUME POUR SULFONATES D'α–OLÉFINE
CN111902125A (zh) * 2018-04-06 2020-11-06 狮王株式会社 口腔用组合物及α-烯烃磺酸盐的苦味改进剂
JPWO2019194068A1 (ja) * 2018-04-06 2021-04-08 ライオン株式会社 口腔用組成物及びα−オレフィンスルホン酸塩の苦味改善剤
JP7255587B2 (ja) 2018-04-06 2023-04-11 ライオン株式会社 口腔用組成物及びα－オレフィンスルホン酸塩の苦味改善剤
CN111902125B (zh) * 2018-04-06 2023-10-20 狮王株式会社 口腔用组合物及α-烯烃磺酸盐的苦味改进剂
CN109771340A (zh) * 2019-03-29 2019-05-21 上海涵博生物科技有限公司 一种口气清新喷雾
JP2020172467A (ja) * 2019-04-10 2020-10-22 花王株式会社 口腔用組成物
JP6994478B2 (ja) 2019-04-10 2022-01-14 花王株式会社 口腔用組成物

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JP5874383B2 (ja) 2016-03-02

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