WO2017110582A1 - Composition for oral cavity - Google Patents

Composition for oral cavity Download PDF

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Publication number
WO2017110582A1
WO2017110582A1 PCT/JP2016/087054 JP2016087054W WO2017110582A1 WO 2017110582 A1 WO2017110582 A1 WO 2017110582A1 JP 2016087054 W JP2016087054 W JP 2016087054W WO 2017110582 A1 WO2017110582 A1 WO 2017110582A1
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Prior art keywords
composition
salt
oral
component
ascorbic acid
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PCT/JP2016/087054
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French (fr)
Japanese (ja)
Inventor
祐輔 吉田
更 石動
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ライオン株式会社
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Priority to JP2017557896A priority Critical patent/JPWO2017110582A1/en
Publication of WO2017110582A1 publication Critical patent/WO2017110582A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/335Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365Lactones
    • A61K31/375Ascorbic acid, i.e. vitamin C; Salts thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/20Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention relates to a composition for oral cavity with improved retention and absorption of ascorbic acid phosphate ester or a salt thereof in the oral mucosa.
  • Ascorbic acid plays an important role in the expression of enzyme activity in the body and is known to have a variety of physiological activities. In particular, it acts as a coenzyme for prolyl and lysyl hydroxylase and is essential for collagen synthesis. ing. For this reason, it is useful for the prevention and treatment of gingivitis and periodontitis associated with collagen destruction, and various ascorbic acid derivatives have been developed in the past, especially ascorbic acid esters and salts thereof have been used in oral compositions. It has been.
  • Patent Documents 1 to 7 propose techniques for oral compositions containing ascorbic acid esters and salts thereof.
  • the oral cavity is different from the skin in that saliva is always supplied and wet, and it is often rinsed with water after applying the formulation, so that water-soluble components stay on the wet gingival surface or inside the gingiva. Or in an environment where absorption is difficult. For this reason, in the composition for oral cavity, there existed a problem that the retentivity to the gingival surface of the ascorbic acid ester and its salt, and the absorptivity to the inside of gingiva were not enough.
  • the present invention has been made in view of the above circumstances, and an object of the present invention is to provide an oral composition that is excellent in retention and absorbability of ascorbic acid phosphate ester or a salt thereof in the oral mucosa.
  • the present inventors have (B) acyl taurine salt and / or acyl glutamic acid in (A) an oral composition containing ascorbic acid phosphate or a salt thereof. It has been found that when salt is added, the retention and absorbability of the component (A) in the oral mucosa are improved, and a remarkable effect is obtained with respect to the above problems, and the present invention has been made.
  • the retention and absorbability of ascorbic acid ester or a salt thereof in the oral mucosa is not sufficient, and the conventional technique could not satisfactorily improve the retention and absorbability.
  • the retention and absorption of the component (A) in the oral mucosa are remarkably improved, and thereby, an anionic interface generally blended in the oral composition.
  • the water-soluble (A) ascorbic acid phosphate ester or a salt thereof is particularly difficult to stay and absorb in the oral mucosa, which is mostly wet with saliva or water
  • the retention / absorption rate is improved by 20% or more in the test using mouse skin as shown in the experimental examples described later, as compared to the case of the component (A) alone. It is possible to impart exceptionally excellent retention and absorbency.
  • (C) a polyoxyethylene alkyl ether having an alkyl group having 12 to 22 carbon atoms and an average added mole number of ethylene oxide of 10 to 50 is combined.
  • the retention and absorption of the component (A) in the oral mucosa are further improved, and oral irritation can be sufficiently suppressed.
  • the present invention provides the following oral compositions and methods for improving the retention and absorbability of ascorbic acid phosphates or salts thereof in the oral mucosa in the oral compositions described below.
  • A Ascorbic acid phosphate ester or salt thereof 0.1 to 5% by mass
  • B Acyl taurate and / or acyl glutamate 0.1-4% by mass
  • a composition for oral cavity comprising: [2] The oral composition according to [1], wherein the component (B) is an acyl taurine salt and / or an acyl glutamate whose acyl group has 10 to 20 carbon atoms.
  • component (B) is sodium lauroylmethyl taurate and / or sodium lauroyl glutamate.
  • (C) 0.1 to 4% by mass of a polyoxyethylene alkyl ether having an alkyl group having 12 to 22 carbon atoms and an average addition mole number of ethylene oxide of 10 to 50 is contained [I] to [4 ]
  • [6] The composition for oral cavity according to [5], wherein (B) / (C) is 0.1 to 12 as a mass ratio.
  • (A) 0.1B to 4% by mass of (B) acyl taurine salt and / or acyl glutamate is added to the oral composition containing 0.1 to 5% by mass of ascorbic acid phosphate or a salt thereof.
  • (B) / (A) is 0.1 to 15 in terms of mass ratio, and (A) ascorbic acid phosphate or salt thereof in the oral mucosa and absorbability in the oral composition according to [9] How to improve.
  • (C) polyoxyethylene alkyl ether having an alkyl group with 12 to 22 carbon atoms and an average added mole number of ethylene oxide of 10 to 50 is blended.
  • (B) / (C) is 0.1 to 12 in terms of mass ratio, and (A) ascorbic acid phosphate or salt thereof in the oral mucosa and absorbability in the oral composition according to [11] How to improve.
  • (A) Ascorbic acid phosphate containing (B) acyl taurine salt and / or acyl glutamate for blending oral composition containing 0.1-5% by mass of ascorbic acid phosphate or salt thereof An agent for improving retention and absorption of an ester or a salt thereof in the oral mucosa, and blended in the oral composition so that the amount of the component (B) is 0.1 to 4% by mass of the whole composition.
  • (A) The ascorbic acid phosphate ester or a salt thereof in the oral mucosa and the absorbability improver.
  • [14] The retention and absorbency improver according to [13], wherein (B) / (A) is blended in the oral composition so that the mass ratio is 0.1 to 15.
  • (C) polyoxyethylene alkyl ether having 12 to 22 carbon atoms in the alkyl group and an average addition mole number of ethylene oxide of 10 to 50, and (C) the amount of the component is 0.1% of the total composition.
  • an oral composition having excellent retention and absorption of ascorbic acid phosphate or a salt thereof in the oral mucosa. Furthermore, in this invention, the improvement of the prevention or improvement effect of a periodontal disease can also be anticipated by the retention and absorption property to the oral mucosa of ascorbic acid phosphate ester or its salt.
  • composition for oral cavity of the present invention contains (A) an ascorbic acid phosphate or a salt thereof, (B) an acyl taurine salt and / or an acyl glutamate.
  • Ascorbic acid phosphate or a salt thereof ascorbic acid, one, or two or more of the hydroxyl groups at the 2nd, 3rd, 5th and 6th positions are converted to phosphates, for example, L-ascorbic acid-2-phosphate ester, L-ascorbic acid-3-phosphate ester, L-ascorbic acid-6-phosphate ester, etc., and salts thereof include sodium salt, potassium salt, A calcium salt, a magnesium salt, etc. are mentioned.
  • One kind selected from these ascorbic acid phosphates and salts thereof can be used alone or in combination of two or more.
  • a derivative in which the hydroxyl group at the 2-position or 3-position of ascorbic acid is converted to a phosphate ester is preferable, and a magnesium salt or sodium salt of ascorbic acid-2-phosphate is more preferable.
  • the blending amount of the ascorbic acid phosphate ester or salt thereof as component (A) is 0.1 to 5% (mass%, the same applies hereinafter) of the entire composition, preferably 0.2 to 2%. As the blending amount increases, the effect of preventing and improving the periodontal disease of the component (A) is sufficiently exerted, but when it exceeds 5%, the feeling of use (astringency, bitterness, tastelessness) becomes worse.
  • the acyl taurine salt and / or acyl glutamate is a retention and absorption improver for the component (A), and an acyl taurine salt and an acyl glutamate whose acyl group has 10 to 20 carbon atoms can be used.
  • alkali metal salts such as sodium and potassium are suitable.
  • acyl taurine salts are preferred in terms of effect expression.
  • acyl taurine salts include cocoyl methyl taurine sodium, cocoyl methyl taurine potassium, lauroyl methyl taurine sodium, stearoyl methyl taurine sodium, myristoyl methyl taurine sodium, oleoyl methyl taurine sodium, palmitoyl methyl taurine sodium, cocoyl taurine sodium.
  • acyl glutamate examples include sodium cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, and sodium stearoyl glutamate.
  • the component (B) one or two or more selected from these can be used.
  • sodium lauroylmethyl taurate, sodium lauroyl glutamate, and particularly sodium lauroylmethyl taurate are preferred from the viewpoint of effect expression.
  • the blending amount of the acyl taurine salt and / or acyl glutamate as the component (B) is 0.1 to 4% of the whole composition, and preferably 0.2 to 3%.
  • the blending amount is less than 0.1%, the retention and absorbability of the component (A) are inferior.
  • it exceeds 4% the retention and absorbability of the component (A) are lowered.
  • (B) / (A) indicating the blending ratio of the component (A) and the component (B) can be 0.02 to 40 as the mass ratio, preferably 0.1 to 15, Preferably it is 0.3 to 14, more preferably 0.5 to 10. Within this range, the retention and absorbability of the component (A) are more excellent.
  • (C) the polyoxyethylene alkyl ether in which the number of carbon atoms of the alkyl group and the average number of added moles of ethylene oxide are in a specific range, respectively.
  • the polyoxyethylene alkyl ether of component (C) has 12 to 22 carbon atoms in the alkyl group, and the average added mole number of ethylene oxide is 10 to 50, preferably 15 to 50, more preferably Is twenty.
  • Specific examples include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, and polyoxyethylene behenyl ether, in which the average added mole number of ethylene oxide is within the above range. 1 type, or 2 or more types selected from these can be used.
  • polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, and polyoxyethylene stearyl ether are preferable, and polyoxyethylene lauryl ether is more preferable from the viewpoint of no irritation in the oral cavity.
  • the blending amount is preferably 0.1 to 4%, more preferably 0.2 to 3% of the entire composition.
  • 0.1% or more is blended, oral irritation is sufficiently suppressed, and when it exceeds 4%, oral irritation may occur.
  • blend (B) and (C) component by a specific ratio, (B) / (C) which shows the mixture ratio of (B) component and (C) component is preferably as mass ratio. It is 0.1 to 12, more preferably 0.4 to 6. Within this range, the retention and absorption of component (A) and the absence of oral irritation are more excellent.
  • the dosage form and shape of the oral composition of the present invention are not particularly limited.
  • liquid solution, emulsion, suspension, etc.
  • semi-solid gel, cream, paste, etc.
  • solid tablet, particulate agent
  • Capsules films, kneaded materials, molten solids, waxy solids, elastic solids, etc.
  • dentifrices teethpaste, liquid toothpaste, liquid toothpaste, powder toothpaste, etc.
  • mouthwash can be used as products of various dosage forms such as agents, coating agents, patches, mouth fresheners, foods (for example, chewing gum, tablet candy, candy, gummi, film, troche etc.).
  • dentifrices teethpastes, liquid dentifrices, liquid dentifrices
  • mouthwashes are suitable, and dentifrices are more preferred.
  • the oral composition of the present invention can be blended with known additive components depending on the shape, dosage form, etc. that can be used for the oral composition within a range not impairing the effects of the present invention. .
  • abrasives, binders, surfactants other than components (B) and (C) surfactants other than components (B) and (C)
  • pH adjustment Agents can be added.
  • silica-based abrasives such as silica gel, precipitated silica, aluminosilicate, zirconosilicate, calcium pyrophosphate, calcium carbonate, aluminum hydroxide, alumina, magnesium carbonate, tribasic magnesium phosphate, zeolite, zirconium silicate, Examples thereof include hydroxyapatite and synthetic resin-based abrasives (the amount is usually 2 to 40%, particularly 10 to 25% of the total composition).
  • organic binders such as sodium carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxymethylethylcellulose, methylcellulose, cationized cellulose and other cellulosic binders, xanthan gum, carrageenan, guar gum, alginic acid
  • examples thereof include sodium, montmorillonite, gelatin, sodium polyacrylate, and the like
  • examples of the inorganic binder include gelling silica, gelling aluminum silica, bee gum, and laponite. 1-10%, especially 0.5-5%).
  • Anionic surfactant Alkyl sulfate such as sodium lauryl sulfate and sodium myristyl sulfate, sodium dodecylbenzenesulfonate, hydrogenated coconut fatty acid monoglyceride sodium monosulfate, sodium lauryl sulfoacetate, sodium ⁇ -olefin sulfonate, etc.
  • Nonionic surfactant such as distearylmethylammonium chloride, stearyldimethylbenzylammonium chloride: sugar alcohol fatty acid esters such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, glycerin fatty acid ester, polyglycerin Polyhydric alcohol fatty acid ester such as fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyethylene glycol fatty acid ester Terionic, polyoxyethylene polyoxypropylene copolymers, polyoxyethylene alkylphenyl ethers, ether type activators such as polyoxyethylene hydrogenated castor oil, and zwitterionic surfactants such as fatty acid alkanolamides such as lauric acid diethanolamide N-alkyldiaminoethylglycine, such as 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine,
  • an anionic surfactant such as an alkyl sulfate (such as sodium lauryl sulfate) may not be added, and the amount added may be a composition. It may be 0.8% or less of the whole, preferably 0.6% or less.
  • sugar alcohol such as sorbit, xylitol, erythritol, propylene glycol, pentylene glycol, hexylene glycol, octylene glycol, polyethylene glycol having an average molecular weight of 200 to 6000, ethylene glycol, 1,3 -Examples include sugar alcohols such as butylene glycol and glycerin, and polyhydric alcohols (the amount is usually 5 to 50%, particularly 20 to 45% of the total composition).
  • Examples of the pigment include legal pigments such as Blue No. 1, Yellow No. 4, and Green No. 3, natural pigments such as caramel, and titanium oxide.
  • fragrances As fragrances, menthol, anethole, carvone, eugenol, limonene, n-decyl alcohol, citronellol, ⁇ -terpineol, citronellyl acetate, cineol, linalool, ethyl linalool, crocodile, thymol, spearmint oil, peppermint oil, lemon oil, orange Oil, sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon leaf oil, perilla oil, winter green oil, clove oil, eucalyptus oil and the like.
  • the blending amount of the fragrance is preferably 0.000001 to 2% of the entire composition.
  • Sweetening agents include saccharin sodium, aspartame, stevioside, stevia extract, paramethoxycinnamic aldehyde, neohesperidyl dihydrochalcone, perilartin and the like.
  • a nonionic fungicide such as isopropylmethylphenol, a cationic fungicide such as cetylpyridinium chloride, a fluorine-containing compound such as sodium fluoride, sodium monofluorophosphate, and the like as long as the effects of the present invention are not impaired.
  • examples include anti-inflammatory agents such as tranexamic acid and allantoin, enzymes such as dextranase, vitamins other than component (A), plant extracts, and the like.
  • the said active ingredient can be mix
  • the pH (25 ° C.) of the composition of the present invention is preferably 6.5 to 9, more preferably 6.8 to 8.8, and particularly preferably 7.0 to 8.6.
  • the pH may be adjusted using a pH adjuster, and examples of the pH adjuster include organic acids such as citric acid, lactic acid and malic acid and salts thereof, hydrochloric acid, sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, Examples include inorganic compounds such as sodium dihydrogen phosphate.
  • (I) Containing (B) component for composition for oral cavity containing said (A) component More preferably, it contains (C) component.
  • Agent (II) Component (B) for producing a preparation for improving retention and absorption of the component (A) in the oral mucosa in the oral composition containing the component (A), preferably (B)
  • component (C) (III) component (B) for retention in the oral mucosa of component (A) in the oral composition containing component (A) and use as an absorbency improver Preferably, components (B) and (C) are provided.
  • a suitable component, the compounding quantity of each component, a compounding ratio, etc. are the same as that of the said composition for oral cavity.
  • Oral compositions having the compositions shown in Tables 1 to 3 were prepared by a conventional method and evaluated by the following methods. The results are shown in the table.
  • ⁇ Detector UV absorption photometer (measurement wavelength: 210 nm)
  • Eluent 0.2% phosphate buffer solution / 5% methanol aqueous solution mixture
  • composition for oral cavity which is the same composition except not containing (C) component and also (C) component (For example, in the case of the Example whose compounding quantity of (A) component is 0.3% of the comparative example 1)
  • the retention / absorption rate of each example when the retention / absorption rate of ascorbic acid phosphate ester or a salt thereof was taken as 100% was calculated, and the retention / absorption property was determined according to the following criteria. From this result, the retention and absorbability of ascorbic acid phosphate or its salt in the oral mucosa were evaluated.
  • the oral composition of the prescription example was excellent in the retention and absorption of ascorbic acid phosphate or a salt thereof. Moreover, intraoral irritation was suppressed.

Abstract

A composition for the oral cavity that shows excellent retention and absorption properties of an ascorbic acid phosphate ester or a salt thereof in the mucous membranes in the oral cavity, said composition containing (A) 0.1-5 mass% of an ascorbic acid phosphate ester or a salt thereof, and (B) 0.1-4 mass% of an acyltaurine salt and/or an acylglutamic acid salt, preferably together with (C) a specific polyoxyethylene alkyl ether. A method for improving, in a composition for the oral cavity containing component (A), the retention and absorption properties of component (A) in the mucous membranes in the oral cavity, said method comprising adding, to the composition for the oral cavity, component (B) preferably together with component (C). An agent for improving the retention and absorption properties of component (A) in the mucous membranes in the oral cavity, said agent being to be added to a composition for the oral cavity containing component (A) and containing component (B) preferably together with component (C). Use of component (B) preferably together with component (C) in a composition for the oral cavity containing component (A).

Description

口腔用組成物Oral composition
 本発明は、アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性が向上した口腔用組成物に関する。 The present invention relates to a composition for oral cavity with improved retention and absorption of ascorbic acid phosphate ester or a salt thereof in the oral mucosa.
 アスコルビン酸は、生体中で酵素活性発現に重要な役割を演じ、多様な生理活性を持つことが知られ、特に、プロリル及びリジルヒドロキシラーゼの補酵素として作用し、コラーゲン合成に必須であるとされている。このため、コラーゲンの破壊に伴う歯肉炎、歯周炎の予防、治療に有用であり、従来からアスコルビン酸誘導体が種々開発され、特にアスコルビン酸エステル及びその塩が注目され、口腔用組成物に用いられている。 Ascorbic acid plays an important role in the expression of enzyme activity in the body and is known to have a variety of physiological activities. In particular, it acts as a coenzyme for prolyl and lysyl hydroxylase and is essential for collagen synthesis. ing. For this reason, it is useful for the prevention and treatment of gingivitis and periodontitis associated with collagen destruction, and various ascorbic acid derivatives have been developed in the past, especially ascorbic acid esters and salts thereof have been used in oral compositions. It has been.
 アスコルビン酸エステル及びその塩を配合した口腔用組成物の技術は、特許文献1~7に提案されている。 Patent Documents 1 to 7 propose techniques for oral compositions containing ascorbic acid esters and salts thereof.
特開2009-149537号公報JP 2009-149537 A 特開2014-5212号公報JP 2014-5212 A 特開2004-323488号公報JP 2004-323488 A 特開2011-6351号公報JP 2011-6351 A 国際公開第2010/143589号International Publication No. 2010/143589 特開2013-129601号公報JP 2013-129601 A 特開2005-239655号公報JP 2005-239655 A
 しかしながら、口腔内は、常に唾液が供給され濡れた状態である点で皮膚とは異なり、また、製剤適用後に水で漱ぐ場合が多く、濡れた歯肉表面や歯肉内部への水溶性成分の滞留や吸収が困難な環境にある。このため、口腔用組成物において、アスコルビン酸エステル及びその塩の歯肉表面への滞留性や歯肉内部への吸収性が十分でないという問題があった。 However, the oral cavity is different from the skin in that saliva is always supplied and wet, and it is often rinsed with water after applying the formulation, so that water-soluble components stay on the wet gingival surface or inside the gingiva. Or in an environment where absorption is difficult. For this reason, in the composition for oral cavity, there existed a problem that the retentivity to the gingival surface of the ascorbic acid ester and its salt, and the absorptivity to the inside of gingiva were not enough.
 本発明は、上記事情に鑑みなされたもので、アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性が優れる口腔用組成物を提供することを目的とする。 The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an oral composition that is excellent in retention and absorbability of ascorbic acid phosphate ester or a salt thereof in the oral mucosa.
 本発明者らは、上記目的を達成するため鋭意検討を行った結果、(A)アスコルビン酸リン酸エステル又はその塩を含有する口腔用組成物に、(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を配合すると、(A)成分の口腔粘膜への滞留及び吸収性が向上し、上記課題に対して顕著な効果が得られることを知見し、本発明をなすに至った。 As a result of intensive studies to achieve the above object, the present inventors have (B) acyl taurine salt and / or acyl glutamic acid in (A) an oral composition containing ascorbic acid phosphate or a salt thereof. It has been found that when salt is added, the retention and absorbability of the component (A) in the oral mucosa are improved, and a remarkable effect is obtained with respect to the above problems, and the present invention has been made.
 即ち、口腔用組成物において、アスコルビン酸エステル又はその塩の口腔粘膜への滞留及び吸収性は十分ではなく、従来の技術では滞留及び吸収性を満足に改善することはできなかったが、本発明では、(B)成分を特定量配合することによって、(A)成分の口腔粘膜への滞留及び吸収性が顕著に向上し、これにより、口腔用組成物に一般的に配合されるアニオン性界面活性剤のラウリル硫酸ナトリウム又はラウロイルサルコシンナトリウムの単なる配合で、しかも(B)成分が無配合の場合には達成し得ない、特異的かつ格別な作用効果を与える。この場合、水溶性である(A)アスコルビン酸リン酸エステル又はその塩は、特に、唾液や水で濡れた状態にあることがほとんどである口腔粘膜には滞留及び吸収し難いにもかかわらず、(A)成分に(B)成分を組み合わせると、後述の実験例に示すようにマウス皮膚を使用した試験において、(A)成分単独の場合に比較して滞留・吸収率が20%以上向上するという、格段に優れた滞留及び吸収性を付与できる。
 更に、本発明では、(B)成分に加えて、(C)アルキル基の炭素数が12~22、エチレンオキサイドの平均付加モル数が10以上50以下であるポリオキシエチレンアルキルエーテルを組み合わせて配合すると、前記(A)成分の口腔粘膜への滞留及び吸収性が更に向上し、口腔内刺激を十分に抑制することも可能となる。
That is, in the composition for oral cavity, the retention and absorbability of ascorbic acid ester or a salt thereof in the oral mucosa is not sufficient, and the conventional technique could not satisfactorily improve the retention and absorbability. Then, by blending a specific amount of the component (B), the retention and absorption of the component (A) in the oral mucosa are remarkably improved, and thereby, an anionic interface generally blended in the oral composition. It is a simple formulation of the active agent sodium lauryl sulfate or sodium lauroyl sarcosine, and provides a specific and exceptional effect that cannot be achieved when the component (B) is not added. In this case, the water-soluble (A) ascorbic acid phosphate ester or a salt thereof is particularly difficult to stay and absorb in the oral mucosa, which is mostly wet with saliva or water, When the component (A) is combined with the component (B), the retention / absorption rate is improved by 20% or more in the test using mouse skin as shown in the experimental examples described later, as compared to the case of the component (A) alone. It is possible to impart exceptionally excellent retention and absorbency.
Furthermore, in the present invention, in addition to the component (B), (C) a polyoxyethylene alkyl ether having an alkyl group having 12 to 22 carbon atoms and an average added mole number of ethylene oxide of 10 to 50 is combined. As a result, the retention and absorption of the component (A) in the oral mucosa are further improved, and oral irritation can be sufficiently suppressed.
 従って、本発明は、下記の口腔用組成物及び口腔用組成物におけるアスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法等を提供する。
〔1〕
 (A)アスコルビン酸リン酸エステル又はその塩  0.1~5質量%、
(B)アシルタウリン塩及び/又はアシルグルタミン酸塩
                         0.1~4質量%
を含有してなることを特徴とする口腔用組成物。
〔2〕
 (B)成分が、アシル基の炭素数が10~20であるアシルタウリン塩及び/又はアシルグルタミン酸塩である〔1〕記載の口腔用組成物。
〔3〕
 (B)成分が、ラウロイルメチルタウリンナトリウム及び/又はラウロイルグルタミン酸ナトリウムである〔2〕記載の口腔用組成物。
〔4〕
 (B)/(A)が質量比として0.1~15である〔1〕~〔3〕のいずれかに記載の口腔用組成物。
〔5〕
 更に、(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを0.1~4質量%含有する〔I〕~〔4〕のいずれかに記載の口腔用組成物。
〔6〕
 (B)/(C)が質量比として0.1~12である〔5〕記載の口腔用組成物。
〔7〕
 歯磨剤である〔1〕~〔6〕のいずれかに記載の口腔用組成物。
〔8〕
 洗口剤である〔1〕~〔6〕のいずれかに記載の口腔用組成物。
〔9〕
 (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%配合した口腔用組成物に、(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を0.1~4質量%配合することを特徴とする、前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。
〔10〕
 (B)/(A)が質量比として0.1~15である、〔9〕記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。
〔11〕
 前記(B)成分と共に、更に、(C)アルキル基の炭素数が12~22、エチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを0.1~4質量%配合する、〔9〕又は〔10〕記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。
〔12〕
 (B)/(C)が質量比として0.1~12である、〔11〕記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。

〔13〕
 (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%含有する口腔用組成物配合用の(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を含む、(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性向上剤であって、(B)成分量が組成物全体の0.1~4質量%となるように前記口腔用組成物に配合されることを特徴とする、前記(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性向上剤。
〔14〕
 (B)/(A)が質量比として0.1~15となるよう前記口腔用組成物に配合される、〔13〕記載の滞留及び吸収性向上剤。
〔15〕
 更に、(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを含み、(C)成分量が組成物全体の0.1~4質量%となるように前記口腔用組成物に配合される、〔13〕又は〔14〕記載の滞留及び吸収性向上剤。
〔16〕
 (B)/(C)が質量比として0.1~12となるよう前記口腔用組成物に配合される、〔15〕記載の滞留及び吸収性向上剤。
〔17〕
 (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%含有する口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性を向上するための製剤製造のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩の使用であって、前記(B)成分の使用量が組成物全体の0.1~4質量%であることを特徴とする、前記(B)アシルタウリン塩及び/又はアシルグルタミン酸塩の使用。
〔18〕
 (B)/(A)が質量比として0.1~15である、〔17〕記載の使用。
〔19〕
 前記(B)成分及び(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルの使用であって、(C)成分の使用量が組成物全体の0.1~4質量%である、〔17〕又は〔18〕記載の使用。
〔20〕
 (B)/(C)が質量比として0.1~12である、〔19〕記載の使用。
〔21〕
 (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%含有する口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性向上剤としての使用のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩であって、(B)成分の使用量が組成物全体の0.1~4質量%であることを特徴とする、前記使用のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩。
〔22〕
 (B)/(A)が質量比として0.1~15である、〔21〕記載の使用のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩。
〔23〕
 前記使用のための前記(B)成分及び(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルであって、(C)成分の使用量が組成物全体の0.1~4質量%である、〔21〕又は〔22〕記載の使用のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩並びに(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテル。
〔23〕
 (B)/(C)が質量比として0.1~12である、〔23〕記載の使用のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩並びに(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテル。
Accordingly, the present invention provides the following oral compositions and methods for improving the retention and absorbability of ascorbic acid phosphates or salts thereof in the oral mucosa in the oral compositions described below.
[1]
(A) Ascorbic acid phosphate ester or salt thereof 0.1 to 5% by mass,
(B) Acyl taurate and / or acyl glutamate 0.1-4% by mass
A composition for oral cavity, comprising:
[2]
The oral composition according to [1], wherein the component (B) is an acyl taurine salt and / or an acyl glutamate whose acyl group has 10 to 20 carbon atoms.
[3]
The composition for oral cavity according to [2], wherein the component (B) is sodium lauroylmethyl taurate and / or sodium lauroyl glutamate.
[4]
The composition for oral cavity according to any one of [1] to [3], wherein (B) / (A) is 0.1 to 15 in terms of mass ratio.
[5]
Further, (C) 0.1 to 4% by mass of a polyoxyethylene alkyl ether having an alkyl group having 12 to 22 carbon atoms and an average addition mole number of ethylene oxide of 10 to 50 is contained [I] to [4 ] The composition for oral cavity in any one of.
[6]
The composition for oral cavity according to [5], wherein (B) / (C) is 0.1 to 12 as a mass ratio.
[7]
The oral composition according to any one of [1] to [6], which is a dentifrice.
[8]
The composition for oral cavity according to any one of [1] to [6], which is a mouthwash.
[9]
(A) 0.1B to 4% by mass of (B) acyl taurine salt and / or acyl glutamate is added to the oral composition containing 0.1 to 5% by mass of ascorbic acid phosphate or a salt thereof. A method for improving retention and absorbability of (A) an ascorbic acid phosphate ester or a salt thereof in the oral cavity composition in the oral cavity composition.
[10]
(B) / (A) is 0.1 to 15 in terms of mass ratio, and (A) ascorbic acid phosphate or salt thereof in the oral mucosa and absorbability in the oral composition according to [9] How to improve.
[11]
In addition to the component (B), 0.1 to 4% by mass of (C) polyoxyethylene alkyl ether having an alkyl group with 12 to 22 carbon atoms and an average added mole number of ethylene oxide of 10 to 50 is blended. [9] A method for improving retention and absorbability of (A) ascorbic acid phosphate ester or a salt thereof in the oral composition of [9] or [10].
[12]
(B) / (C) is 0.1 to 12 in terms of mass ratio, and (A) ascorbic acid phosphate or salt thereof in the oral mucosa and absorbability in the oral composition according to [11] How to improve.

[13]
(A) Ascorbic acid phosphate containing (B) acyl taurine salt and / or acyl glutamate for blending oral composition containing 0.1-5% by mass of ascorbic acid phosphate or salt thereof An agent for improving retention and absorption of an ester or a salt thereof in the oral mucosa, and blended in the oral composition so that the amount of the component (B) is 0.1 to 4% by mass of the whole composition. (A) The ascorbic acid phosphate ester or a salt thereof in the oral mucosa and the absorbability improver.
[14]
The retention and absorbency improver according to [13], wherein (B) / (A) is blended in the oral composition so that the mass ratio is 0.1 to 15.
[15]
And (C) polyoxyethylene alkyl ether having 12 to 22 carbon atoms in the alkyl group and an average addition mole number of ethylene oxide of 10 to 50, and (C) the amount of the component is 0.1% of the total composition. The retention and absorbency improver according to [13] or [14], which is added to the composition for oral cavity so as to be 4% by mass.
[16]
The retention and absorbency improver according to [15], wherein (B) / (C) is blended in the oral composition so that the mass ratio is 0.1 to 12.
[17]
(A) In order to improve the retention and absorbability of (A) ascorbic acid phosphate or a salt thereof in the oral mucosa in an oral composition containing 0.1 to 5% by mass of ascorbic acid phosphate or a salt thereof. (B) acyl taurine salt and / or acyl glutamate for the preparation of the preparation, wherein the amount of the component (B) used is 0.1 to 4% by mass of the total composition (B) Use of acyl taurine salt and / or acyl glutamate.
[18]
The use according to [17], wherein (B) / (A) is 0.1 to 15 in terms of mass ratio.
[19]
Use of the polyoxyethylene alkyl ether in which the component (B) and the (C) alkyl group have 12 to 22 carbon atoms and the average added mole number of ethylene oxide is 10 to 50, and the use of the component (C) Use according to [17] or [18], wherein the amount is from 0.1 to 4% by weight of the total composition.
[20]
The use according to [19], wherein (B) / (C) is 0.1 to 12 as a mass ratio.
[21]
(A) In the composition for oral cavity containing 0.1 to 5% by mass of ascorbic acid phosphate ester or salt thereof (A) Ascorbic acid phosphate ester or salt thereof in the oral mucosa as an agent for improving retention and absorption (B) acyl taurine salt and / or acyl glutamate for use, wherein the amount of component (B) used is 0.1 to 4% by mass of the total composition (B) Acyl taurate and / or acyl glutamate for
[22]
(B) Acyl taurine salt and / or acyl glutamate for use according to [21], wherein (B) / (A) is 0.1 to 15 in terms of mass ratio.
[23]
A polyoxyethylene alkyl ether in which the component (B) and (C) the alkyl group have 12 to 22 carbon atoms and the average added mole number of ethylene oxide is 10 to 50 for the use, (B) acyl taurine salt and / or acyl glutamate salt and (C) alkyl group for use according to [21] or [22], wherein the amount of the component used is 0.1 to 4% by mass of the total composition Polyoxyethylene alkyl ether having 12 to 22 carbon atoms and an average addition mole number of ethylene oxide of 10 to 50.
[23]
(B) acyl taurine salt and / or acyl glutamate for use according to [23], wherein (B) / (C) is 0.1 to 12 in terms of mass ratio, and (C) the carbon number of the alkyl group is Polyoxyethylene alkyl ether having 12 to 22 and an average addition mole number of ethylene oxide of 10 to 50.
 本発明によれば、アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性が優れる口腔用組成物を提供できる。更に、本発明では、アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性が向上することで、歯周疾患の予防又は改善効果の向上を期待することもできる。 According to the present invention, it is possible to provide an oral composition having excellent retention and absorption of ascorbic acid phosphate or a salt thereof in the oral mucosa. Furthermore, in this invention, the improvement of the prevention or improvement effect of a periodontal disease can also be anticipated by the retention and absorption property to the oral mucosa of ascorbic acid phosphate ester or its salt.
 以下、本発明につき更に詳述する。本発明の口腔用組成物は、(A)アスコルビン酸リン酸エステル又はその塩、(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を含有する。 Hereinafter, the present invention will be described in further detail. The composition for oral cavity of the present invention contains (A) an ascorbic acid phosphate or a salt thereof, (B) an acyl taurine salt and / or an acyl glutamate.
 (A)アスコルビン酸リン酸エステル又はその塩としては、アスコルビン酸の2位、3位、5位、6位の水酸基のいずれか1つ又は2つ以上がリン酸エステルになったもの、例えば、L-アスコルビン酸-2-リン酸エステル、L-アスコルビン酸-3-リン酸エステル、L-アスコルビン酸-6-リン酸エステル等が挙げられ、また、その塩類としては、ナトリウム塩、カリウム塩、カルシウム塩、マグネシウム塩等が挙げられる。これらアスコルビン酸リン酸エステル及びその塩から選ばれる1種を単独で又は2種以上を組み合わせて使用できる。中でも、組成の安定性の点から、アスコルビン酸の2位又は3位の水酸基がリン酸エステル化された誘導体が好ましく、より好ましくはアスコルビン酸-2-リン酸エステルのマグネシウム塩やナトリウム塩である。 (A) Ascorbic acid phosphate or a salt thereof, ascorbic acid, one, or two or more of the hydroxyl groups at the 2nd, 3rd, 5th and 6th positions are converted to phosphates, for example, L-ascorbic acid-2-phosphate ester, L-ascorbic acid-3-phosphate ester, L-ascorbic acid-6-phosphate ester, etc., and salts thereof include sodium salt, potassium salt, A calcium salt, a magnesium salt, etc. are mentioned. One kind selected from these ascorbic acid phosphates and salts thereof can be used alone or in combination of two or more. Among them, from the viewpoint of the stability of the composition, a derivative in which the hydroxyl group at the 2-position or 3-position of ascorbic acid is converted to a phosphate ester is preferable, and a magnesium salt or sodium salt of ascorbic acid-2-phosphate is more preferable. .
 (A)成分のアスコルビン酸リン酸エステル又はその塩の配合量は、組成物全体の0.1~5%(質量%、以下同様。)であり、好ましくは0.2~2%である。配合量が多いほど、(A)成分が有する歯周疾患の予防・改善効果が十分に発揮されるが、5%を超えると使用感(渋味・苦味・異味のなさ)が悪くなる。 The blending amount of the ascorbic acid phosphate ester or salt thereof as component (A) is 0.1 to 5% (mass%, the same applies hereinafter) of the entire composition, preferably 0.2 to 2%. As the blending amount increases, the effect of preventing and improving the periodontal disease of the component (A) is sufficiently exerted, but when it exceeds 5%, the feeling of use (astringency, bitterness, tastelessness) becomes worse.
 (B)アシルタウリン塩及び/又はアシルグルタミン酸塩は、(A)成分の滞留及び吸収性向上剤であり、アシル基の炭素数が10~20であるアシルタウリン塩及びアシルグルタミン酸塩を使用できる。これらの塩としてはナトリウム、カリウム等のアルカリ金属塩が好適である。中でも、効果発現の点からアシルタウリン塩が好ましい。 (B) The acyl taurine salt and / or acyl glutamate is a retention and absorption improver for the component (A), and an acyl taurine salt and an acyl glutamate whose acyl group has 10 to 20 carbon atoms can be used. As these salts, alkali metal salts such as sodium and potassium are suitable. Of these, acyl taurine salts are preferred in terms of effect expression.
 具体的に、アシルタウリン塩としては、ココイルメチルタウリンナトリウム、ココイルメチルタウリンカリウム、ラウロイルメチルタウリンナトリウム、ステアロイルメチルタウリンナトリウム、ミリストイルメチルタウリンナトリウム、オレオイルメチルタウリンナトリウム、パルミトイルメチルタウリンナトリウム、ココイルタウリンナトリウムが挙げられる。アシルグルタミン酸塩としては、ココイルグルタミン酸ナトリウム、ラウロイルグルタミン酸ナトリウム、ミリストイルグルタミン酸ナトリウム、ステアロイルグルタミン酸ナトリウムが挙げられる。
 (B)成分としては、これらから選ばれる1種又は2種以上を使用し得るが、特に、効果発現の点から、ラウロイルメチルタウリンナトリウム、ラウロイルグルタミン酸ナトリウム、とりわけラウロイルメチルタウリンナトリウムが好適である。
Specifically, acyl taurine salts include cocoyl methyl taurine sodium, cocoyl methyl taurine potassium, lauroyl methyl taurine sodium, stearoyl methyl taurine sodium, myristoyl methyl taurine sodium, oleoyl methyl taurine sodium, palmitoyl methyl taurine sodium, cocoyl taurine sodium. Can be mentioned. Examples of the acyl glutamate include sodium cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, and sodium stearoyl glutamate.
As the component (B), one or two or more selected from these can be used. In particular, sodium lauroylmethyl taurate, sodium lauroyl glutamate, and particularly sodium lauroylmethyl taurate are preferred from the viewpoint of effect expression.
 (B)成分のアシルタウリン塩及び/又はアシルグルタミン酸塩の配合量は、組成物全体の0.1~4%であり、特に0.2~3%が好ましい。配合量が0.1%未満であると、(A)成分の滞留及び吸収性が劣る。4%を超えると(A)成分の滞留及び吸収性が低下する。 The blending amount of the acyl taurine salt and / or acyl glutamate as the component (B) is 0.1 to 4% of the whole composition, and preferably 0.2 to 3%. When the blending amount is less than 0.1%, the retention and absorbability of the component (A) are inferior. When it exceeds 4%, the retention and absorbability of the component (A) are lowered.
 (A)成分と(B)成分との配合割合を示す(B)/(A)は、質量比として0.02~40とすることができるが、好ましくは0.1~15であり、より好ましくは0.3~14、更に好ましくは0.5~10である。この範囲内であると、(A)成分の滞留及び吸収性がより優れる。 (B) / (A) indicating the blending ratio of the component (A) and the component (B) can be 0.02 to 40 as the mass ratio, preferably 0.1 to 15, Preferably it is 0.3 to 14, more preferably 0.5 to 10. Within this range, the retention and absorbability of the component (A) are more excellent.
 本発明では、更に、(C)アルキル基の炭素数とエチレンオキサイドの平均付加モル数とがそれぞれ特定範囲であるポリオキシエチレンアルキルエーテルを含有することが好ましい。(B)成分に(C)成分を組み合わせると、(A)成分の口腔粘膜への滞留及び吸収性がより向上し、また、口腔内刺激を抑制することもできる。 In the present invention, it is preferable that (C) the polyoxyethylene alkyl ether in which the number of carbon atoms of the alkyl group and the average number of added moles of ethylene oxide are in a specific range, respectively. When the component (C) is combined with the component (B), the retention and absorption of the component (A) in the oral mucosa are further improved, and oral irritation can be suppressed.
 (C)成分のポリオキシエチレンアルキルエーテルは、アルキル基の炭素数が12~22であり、また、エチレンオキサイドの平均付加モル数が10以上50以下であり、好ましくは15以上50以下、より好ましくは20のものである。
 具体的には、エチレンオキサイドの平均付加モル数が上記範囲内である、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンベヘニルエーテルが挙げられ、これらから選ばれる1種又は2種以上を使用し得る。これらの中でも、口腔内刺激のなさの点からポリオキシエチレンラウリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンステアリルエーテルが好ましく、より好ましくはポリオキシエチレンラウリルエーテルである。
The polyoxyethylene alkyl ether of component (C) has 12 to 22 carbon atoms in the alkyl group, and the average added mole number of ethylene oxide is 10 to 50, preferably 15 to 50, more preferably Is twenty.
Specific examples include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, and polyoxyethylene behenyl ether, in which the average added mole number of ethylene oxide is within the above range. 1 type, or 2 or more types selected from these can be used. Among these, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, and polyoxyethylene stearyl ether are preferable, and polyoxyethylene lauryl ether is more preferable from the viewpoint of no irritation in the oral cavity.
 (C)成分のポリオキシエチレンアルキルエーテルを配合する場合、その配合量は、組成物全体の0.1~4%が好ましく、より好ましくは0.2~3%である。0.1%以上配合すると、口腔内刺激が十分に抑制され、4%を超えると、口腔内刺激が発生する場合がある。 When the polyoxyethylene alkyl ether (C) is blended, the blending amount is preferably 0.1 to 4%, more preferably 0.2 to 3% of the entire composition. When 0.1% or more is blended, oral irritation is sufficiently suppressed, and when it exceeds 4%, oral irritation may occur.
 また、(B)、(C)成分は特定割合で配合することがより好ましく、(B)成分と(C)成分との配合割合を示す(B)/(C)は、質量比として好ましくは0.1~12、より好ましくは0.4~6である。この範囲内であると、(A)成分の滞留及び吸収性と口腔内刺激のなさとがより優れる。 Moreover, it is more preferable to mix | blend (B) and (C) component by a specific ratio, (B) / (C) which shows the mixture ratio of (B) component and (C) component is preferably as mass ratio. It is 0.1 to 12, more preferably 0.4 to 6. Within this range, the retention and absorption of component (A) and the absence of oral irritation are more excellent.
 本発明の口腔用組成物の剤型・形状は特に限定されず、例えば、液体(溶液、乳液、懸濁液等)、半固体(ゲル、クリーム、ペースト等)、固体(錠剤、粒子状剤、カプセル剤、フィルム剤、混練物、溶融固体、ロウ状固体、弾性固体等)等の任意の形状に調製でき、例えば歯磨剤(練歯磨、液体歯磨、液状歯磨、粉歯磨等)、洗口剤、塗布剤、貼付剤、口中清涼剤、食品(例えば、チューインガム、錠菓、キャンディ、グミ、フィルム、トローチ等)等の各種剤型の製品として利用できる。特に、歯磨剤(練歯磨剤、液状歯磨剤、液体歯磨剤)、洗口剤が好適であり、歯磨剤がより好ましい。 The dosage form and shape of the oral composition of the present invention are not particularly limited. For example, liquid (solution, emulsion, suspension, etc.), semi-solid (gel, cream, paste, etc.), solid (tablet, particulate agent) , Capsules, films, kneaded materials, molten solids, waxy solids, elastic solids, etc.), such as dentifrices (toothpaste, liquid toothpaste, liquid toothpaste, powder toothpaste, etc.), mouthwash It can be used as products of various dosage forms such as agents, coating agents, patches, mouth fresheners, foods (for example, chewing gum, tablet candy, candy, gummi, film, troche etc.). In particular, dentifrices (toothpastes, liquid dentifrices, liquid dentifrices) and mouthwashes are suitable, and dentifrices are more preferred.
 本発明の口腔用組成物には、上記各成分に加えて、本発明の効果を損なわない範囲において、口腔用組成物に使用し得る形状、剤型等に応じた公知の添加成分を配合できる。具体的に歯磨剤には、研磨剤、粘結剤、(B)、(C)成分以外の界面活性剤、湿潤剤、色素、香料、甘味剤、(A)成分以外の有効成分、pH調整剤等を配合できる。 In addition to the above-mentioned components, the oral composition of the present invention can be blended with known additive components depending on the shape, dosage form, etc. that can be used for the oral composition within a range not impairing the effects of the present invention. . Specifically for dentifrices, abrasives, binders, surfactants other than components (B) and (C), wetting agents, pigments, fragrances, sweeteners, active ingredients other than component (A), pH adjustment Agents can be added.
 研磨剤としては、シリカゲル、沈降シリカ、アルミノシリケート、ジルコノシリケート等のシリカ系研磨剤、ピロリン酸カルシウム、炭酸カルシウム、水酸化アルミニウム、アルミナ、炭酸マグネシウム、第3リン酸マグネシウム、ゼオライト、ケイ酸ジルコニウム、ハイドロキシアパタイト、合成樹脂系研磨剤等が挙げられる(配合量は通常、組成物全体の2~40%、特に10~25%)。 As abrasives, silica-based abrasives such as silica gel, precipitated silica, aluminosilicate, zirconosilicate, calcium pyrophosphate, calcium carbonate, aluminum hydroxide, alumina, magnesium carbonate, tribasic magnesium phosphate, zeolite, zirconium silicate, Examples thereof include hydroxyapatite and synthetic resin-based abrasives (the amount is usually 2 to 40%, particularly 10 to 25% of the total composition).
 粘結剤としては、有機粘結剤として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、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、ヒドロキシメチルエチルセルロース、メチルセルロース、カチオン化セルロースなどのセルロース系粘結剤、キサンタンガム、カラギーナン、グアガム、アルギン酸ナトリウム、モンモリロナイト、ゼラチン、ポリアクリル酸ナトリウム等が挙げられ、無機粘結剤としてゲル化性シリカ、ゲル化性アルミニウムシリカ、ビーガム、ラポナイト等が挙げられる(配合量は通常、組成物全体の0.1~10%、特に0.5~5%)。 As binders, organic binders such as sodium carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydroxymethylethylcellulose, methylcellulose, cationized cellulose and other cellulosic binders, xanthan gum, carrageenan, guar gum, alginic acid Examples thereof include sodium, montmorillonite, gelatin, sodium polyacrylate, and the like, and examples of the inorganic binder include gelling silica, gelling aluminum silica, bee gum, and laponite. 1-10%, especially 0.5-5%).
 界面活性剤としては、具体的に下記に示すものが挙げられる。
アニオン性界面活性剤: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塩、ドデシルベンゼンスルホン酸ナトリウム、水素添加ココナッツ脂肪酸モノグリセリドモノ硫酸ナトリウム、ラウリルスルホ酢酸ナトリウム、α-オレフィンスルホン酸ナトリウム等
カチオン性界面活性剤:塩化ジステアリルメチルアンモニウム、塩化ステアリルジメチルベンジルアンモニウム等
非イオン性界面活性剤:ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ショ糖脂肪酸エステルなどの糖アルコール脂肪酸エステル類、グリセリン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリエチレングリコール脂肪酸エステルなどの多価アルコール脂肪酸エステル、ポリオキシエチレンポリオキシプロピレン共重合体、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレン硬化ヒマシ油などのエーテル型の活性剤、ラウリン酸ジエタノールアミドなどの脂肪酸アルカノールアミド類等
両イオン性界面活性剤:2-アルキル-N-カルボキシメチル-N-ヒドロキシエチルイミダゾリウムベタイン、N-ラウリルジアミノエチルグリシン、N-ミリスチルジアミノエチルグリシンなどのN-アルキルジアミノエチルグリシン、N-アルキル-1-ヒドロキシエチルイミダゾリンベタインナトリウム等
 これら界面活性剤を配合する場合、その配合量は、組成物全体の0.2~15%、とりわけ0.5~10%が好ましい。なお、(A)成分の口腔粘膜への滞留及び吸収性の点からは、特にアルキル硫酸塩(ラウリル硫酸ナトリウムなど)等のアニオン性界面活性剤は配合しなくてもよく、配合量が組成物全体の0.8%以下、好ましくは0.6%以下であってもよい。
Specific examples of the surfactant include those shown below.
Anionic surfactant: Alkyl sulfate such as sodium lauryl sulfate and sodium myristyl sulfate, sodium dodecylbenzenesulfonate, hydrogenated coconut fatty acid monoglyceride sodium monosulfate, sodium lauryl sulfoacetate, sodium α-olefin sulfonate, etc. Agent: Nonionic surfactant such as distearylmethylammonium chloride, stearyldimethylbenzylammonium chloride: sugar alcohol fatty acid esters such as sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, glycerin fatty acid ester, polyglycerin Polyhydric alcohol fatty acid ester such as fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyethylene glycol fatty acid ester Terionic, polyoxyethylene polyoxypropylene copolymers, polyoxyethylene alkylphenyl ethers, ether type activators such as polyoxyethylene hydrogenated castor oil, and zwitterionic surfactants such as fatty acid alkanolamides such as lauric acid diethanolamide N-alkyldiaminoethylglycine, such as 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolium betaine, N-lauryldiaminoethylglycine, N-myristyldiaminoethylglycine, N-alkyl-1-hydroxyethylimidazoline betaine When these surfactants and the like are blended, the blending amount is preferably 0.2 to 15%, particularly 0.5 to 10% of the whole composition. In addition, from the viewpoint of retention and absorption of the component (A) in the oral mucosa, an anionic surfactant such as an alkyl sulfate (such as sodium lauryl sulfate) may not be added, and the amount added may be a composition. It may be 0.8% or less of the whole, preferably 0.6% or less.
 湿潤剤としては、還元でんぷん糖化物、ソルビット、キシリトール、エリスリトール等の糖アルコール、プロピレングリコール、ペンチレングリコール、ヘキシレングリコール、オクチレングリコール、平均分子量200~6000のポリエチレングリコール、エチレングリコール、1,3-ブチレングリコール、グリセリン等の糖アルコール、多価アルコールが挙げられる(配合量は通常、組成物全体の5~50%、特に20~45%)。 As the wetting agent, reduced starch saccharified product, sugar alcohol such as sorbit, xylitol, erythritol, propylene glycol, pentylene glycol, hexylene glycol, octylene glycol, polyethylene glycol having an average molecular weight of 200 to 6000, ethylene glycol, 1,3 -Examples include sugar alcohols such as butylene glycol and glycerin, and polyhydric alcohols (the amount is usually 5 to 50%, particularly 20 to 45% of the total composition).
 色素としては、青色1号、黄色4号、緑色3号等の法定色素、カラメル等の天然色素及び酸化チタンが挙げられる。 Examples of the pigment include legal pigments such as Blue No. 1, Yellow No. 4, and Green No. 3, natural pigments such as caramel, and titanium oxide.
 香料としては、メントール、アネトール、カルボン、オイゲノール、リモネン、n-デシルアルコール、シトロネロール、α-テレピネオール、シトロネリルアセテート、シネオール、リナロール、エチルリナロール、ワニリン、チモール、スペアミント油、ペパーミント油、レモン油、オレンジ油、セージ油、ローズマリー油、桂皮油、ピメント油、桂葉油、シソ油、冬緑油、丁字油、ユーカリ油等が挙げられる。
 香料の配合量は、組成物全体の0.000001~2%が好ましい。
As fragrances, menthol, anethole, carvone, eugenol, limonene, n-decyl alcohol, citronellol, α-terpineol, citronellyl acetate, cineol, linalool, ethyl linalool, crocodile, thymol, spearmint oil, peppermint oil, lemon oil, orange Oil, sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon leaf oil, perilla oil, winter green oil, clove oil, eucalyptus oil and the like.
The blending amount of the fragrance is preferably 0.000001 to 2% of the entire composition.
 甘味剤としては、サッカリンナトリウム、アスパラテーム、ステビオサイド、ステビアエキス、パラメトキシシンナミックアルデヒド、ネオヘスペリジルジヒドロカルコン、ペリラルチン等が挙げられる。 Sweetening agents include saccharin sodium, aspartame, stevioside, stevia extract, paramethoxycinnamic aldehyde, neohesperidyl dihydrochalcone, perilartin and the like.
 有効成分としては、本発明の効果を妨げない範囲でイソプロピルメチルフェノール等の非イオン性殺菌剤、塩化セチルピリジニウム等のカチオン性殺菌剤、フッ化ナトリウム、モノフルオロリン酸ナトリウム等のフッ素含有化合物、トラネキサム酸、アラントイン等の抗炎症剤、デキストラナーゼ等の酵素、(A)成分以外のビタミン類、植物抽出物などが挙げられる。なお、上記有効成分は、本発明の効果を妨げない範囲で有効量配合することができる。 As an active ingredient, a nonionic fungicide such as isopropylmethylphenol, a cationic fungicide such as cetylpyridinium chloride, a fluorine-containing compound such as sodium fluoride, sodium monofluorophosphate, and the like as long as the effects of the present invention are not impaired. Examples include anti-inflammatory agents such as tranexamic acid and allantoin, enzymes such as dextranase, vitamins other than component (A), plant extracts, and the like. In addition, the said active ingredient can be mix | blended in an effective amount in the range which does not prevent the effect of this invention.
 本発明組成物のpH(25℃)は好ましくは6.5~9、より好ましくは6.8~8.8、特に好ましくは7.0~8.6である。pH調整剤を用いてpH調整してもよく、pH調整剤としては、クエン酸、乳酸、リンゴ酸などの有機酸及びその塩類、塩酸、水酸化ナトリウム、水酸化カリウム、リン酸水素二ナトリウム、リン酸二水素ナトリウム等の無機化合物が挙げられる。 The pH (25 ° C.) of the composition of the present invention is preferably 6.5 to 9, more preferably 6.8 to 8.8, and particularly preferably 7.0 to 8.6. The pH may be adjusted using a pH adjuster, and examples of the pH adjuster include organic acids such as citric acid, lactic acid and malic acid and salts thereof, hydrochloric acid, sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, Examples include inorganic compounds such as sodium dihydrogen phosphate.
 本発明は上記特徴を有するため、更に、
(I)上記の(A)成分を含有する口腔用組成物配合用の(B)成分を含み、更に好ましくは(C)成分を含む、(A)成分の口腔粘膜への滞留及び吸収性向上剤、
(II)上記の(A)成分を含有する口腔用組成物における(A)成分の口腔粘膜への滞留及び吸収性を向上するための製剤製造のための(B)成分、好ましくは(B)及び(C)成分の使用
(III)上記の(A)成分を含有する口腔用組成物における(A)成分の口腔粘膜への滞留及び吸収性向上剤としての使用のための(B)成分、好ましくは(B)及び(C)成分
等を提供する。なお、好適な成分、各成分の配合量や配合割合等は上記口腔用組成物と同様である。
Since the present invention has the above characteristics,
(I) Containing (B) component for composition for oral cavity containing said (A) component, More preferably, it contains (C) component. Agent,
(II) Component (B) for producing a preparation for improving retention and absorption of the component (A) in the oral mucosa in the oral composition containing the component (A), preferably (B) And the use of component (C) (III) component (B) for retention in the oral mucosa of component (A) in the oral composition containing component (A) and use as an absorbency improver, Preferably, components (B) and (C) are provided. In addition, a suitable component, the compounding quantity of each component, a compounding ratio, etc. are the same as that of the said composition for oral cavity.
 以下、実施例及び比較例、処方例を示し、本発明を具体的に説明するが、本発明は下記の実施例に制限されるものではない。なお、下記の例において%は特に断らない限りいずれも質量%を示す。 Hereinafter, although an Example, a comparative example, and a formulation example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to the following Example. In the following examples, “%” means “% by mass” unless otherwise specified.
 [実施例、比較例]
 表1~3に示す組成の口腔用組成物(練歯磨剤)を常法によって調製し、下記方法で評価した。結果を表に併記した。
[Examples and Comparative Examples]
Oral compositions (toothpastes) having the compositions shown in Tables 1 to 3 were prepared by a conventional method and evaluated by the following methods. The results are shown in the table.
(1)アスコルビン酸リン酸エステル又はその塩の滞留・吸収性の評価方法
 1.5cm四方にカットした7週齢雄性ヘアレスマウスの皮膚(日本エスエルシー(株);ラボスキン)を6ウェルプレートに置き、人工唾液を5mL加え、2時間静置した。透過面積(約0.8cm2)が一定になるように、ガラス枠を当該皮膚の上に載せ、表に示す実施例又は比較例の口腔用組成物を人工唾液で3倍希釈した液を300μLずつ注入し、5分間静置した。その後、当該希釈液を捨て、5mLの水を加えて振とう機を用いて160rpmで1分間洗浄した。前記洗浄を繰り返し、計2回行った。
 洗浄液を捨て皮膚をチューブに回収し、1mLのエタノール(90%)を加えてボルテックスミキサーで5分間抽出操作を行った。抽出液を回収し、精製水で等倍希釈後、下記試験条件でHPLC(高速液体クロマトグラフィー)によってアスコルビン酸リン酸エステル又はその塩を定量した。
(1) Method for evaluating retention / absorbability of ascorbic acid phosphate or salt thereof Place the skin of 7-week-old male hairless mouse (Japan SLC Co., Ltd .; Lab Skin) cut into a 1.5 cm square on a 6-well plate. Then, 5 mL of artificial saliva was added and allowed to stand for 2 hours. A glass frame is placed on the skin so that the permeation area (approximately 0.8 cm 2 ) is constant, and 300 μL of a solution obtained by diluting the oral composition of Examples or Comparative Examples shown in the table with artificial saliva three times. Each was injected and allowed to stand for 5 minutes. Thereafter, the diluted solution was discarded, and 5 mL of water was added, followed by washing at 160 rpm for 1 minute using a shaker. The washing was repeated for a total of 2 times.
The washing solution was discarded, the skin was collected in a tube, 1 mL of ethanol (90%) was added, and extraction was performed with a vortex mixer for 5 minutes. The extract was collected, diluted 1-fold with purified water, and then ascorbic acid phosphate or a salt thereof was quantified by HPLC (high performance liquid chromatography) under the following test conditions.
(使用機器)
・ポンプ:日本分光(株)製、PU-980
・試料導入部:協和精密(株)製、KSP-100X
・検出器:日本分光(株)製、UV-970
・カラム恒温槽:(株)センシュー科学製、SCC-2100
・溶離液流量:1mL/min
(試験条件)
 アスコルビン酸リン酸エステル又はその塩を定量するためのHPLC条件は以下のとおりである。
・検出器:紫外吸光光度計(測定波長:210nm)
・カラム:CAPCELL PAK C18 MG-II S-3
・カラム温度:40℃
・溶離液:0.2%リン酸緩衝溶液/5%メタノール水溶液混液
(Used equipment)
Pump: JASCO Corporation, PU-980
・ Sample introduction part: KSP-100X, manufactured by Kyowa Precision Co., Ltd.
Detector: JASCO Corporation, UV-970
-Column thermostat: SCC-2100, manufactured by Senshu Kagaku Co., Ltd.
・ Eluent flow rate: 1 mL / min
(Test conditions)
The HPLC conditions for quantifying ascorbic acid phosphate ester or a salt thereof are as follows.
・ Detector: UV absorption photometer (measurement wavelength: 210 nm)
Column: CAPCELL PAK C18 MG-II S-3
-Column temperature: 40 ° C
Eluent: 0.2% phosphate buffer solution / 5% methanol aqueous solution mixture
 (B)成分、更には(C)成分を含まない以外は同組成である口腔用組成物(例えば(A)成分の配合量が0.3%である実施例の場合は比較例1)のアスコルビン酸リン酸エステル又はその塩の滞留・吸収率を100%とした際の各例の滞留・吸収率を算出し、下記基準に従って滞留・吸収性を判定した。この結果からアスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性を評価した。
 評価基準
  ◎:150%以上
  ○:120%以上150%未満
  △:110%以上120%未満
  ×:110%未満
(B) The composition for oral cavity which is the same composition except not containing (C) component and also (C) component (For example, in the case of the Example whose compounding quantity of (A) component is 0.3% of the comparative example 1) The retention / absorption rate of each example when the retention / absorption rate of ascorbic acid phosphate ester or a salt thereof was taken as 100% was calculated, and the retention / absorption property was determined according to the following criteria. From this result, the retention and absorbability of ascorbic acid phosphate or its salt in the oral mucosa were evaluated.
Evaluation criteria ◎: 150% or more ○: 120% or more and less than 150% △: 110% or more and less than 120% ×: Less than 110%
 また、表2に示す口腔用組成物(歯磨剤)の口腔内刺激のなさについて、下記方法で評価した。結果を表に併記した。 Moreover, the following method evaluated the absence of intraoral irritation of the composition for oral cavity (dentifrice) shown in Table 2. The results are shown in the table.
(2)口腔内刺激のなさの評価方法
 評価者として専門家パネラー10人を用いた官能試験を実施した。口腔用組成物約0.5gを市販品の歯ブラシにのせて3分間ブラッシングを行い、使用中に感じた口腔内刺激性を評価した。下記の4段階の評点に従って官能評価し、10名の評価結果の平均値を求め、以下の基準で口腔内刺激のなさを評価した。○以上のものを口腔内刺激性が低く合格であると判定した。
 評点基準:
  4点:刺激がまったくない。
  3点:刺激がほとんどない。
  2点:刺激がややある。
  1点:刺激がかなりある。
 評価基準:
  ◎:3.5点以上4.0点以下
  ○:3.0点以上3.5点未満
  △:2.0点以上3.0点未満
  ×:2.0点未満
(2) Evaluation method of absence of intraoral irritation A sensory test was conducted using 10 expert panelists as evaluators. About 0.5 g of the oral composition was placed on a commercially available toothbrush and brushed for 3 minutes to evaluate the oral irritation felt during use. Sensory evaluation was performed according to the following four grades, the average value of the evaluation results of 10 persons was determined, and the absence of oral irritation was evaluated according to the following criteria. ○ The above were judged to be acceptable because of low oral irritation.
Score criteria:
4 points: No irritation.
3 points: There is almost no irritation.
2 points: There is some irritation.
1 point: There is considerable stimulation.
Evaluation criteria:
◎: 3.5 points or more and 4.0 points or less ○: 3.0 points or more and less than 3.5 points △: 2.0 points or more and less than 3.0 points ×: Less than 2.0 points
 使用原料の詳細を下記に示す。なお、ポリオキシエチレンアルキルエーテルの( )内の数字はエチレンオキサイドの平均付加モル数である(以下同様。)。
(A)リン酸L-アスコルビルマグネシウム:和光純薬工業(株)製、生化学用
(B)ラウロイルメチルタウリンナトリウム:
 日光ケミカルズ(株)製、商品名 LMT-P
(B)ラウロイルグルタミン酸ナトリウム:
 旭化成ケミカルズ(株)製、商品名 ALMS-P1
(C)ポリオキシエチレン(20)ラウリルエーテル:
 日本エマルジョン(株)製、商品名 EMALEX720
ラウリル硫酸ナトリウム(比較品):
 BASF(株)製、商品名 Texapon OC-P
Details of the raw materials used are shown below. In addition, the number in () of polyoxyethylene alkyl ether is the average added mole number of ethylene oxide (the same applies hereinafter).
(A) L-ascorbyl magnesium phosphate: manufactured by Wako Pure Chemical Industries, Ltd. for biochemistry (B) sodium lauroylmethyl taurate:
Product name LMT-P, manufactured by Nikko Chemicals
(B) Sodium lauroyl glutamate:
Product name ALMS-P1 manufactured by Asahi Kasei Chemicals Corporation
(C) Polyoxyethylene (20) lauryl ether:
Product name EMALEX720, manufactured by Nippon Emulsion Co., Ltd.
Sodium lauryl sulfate (comparative product):
BASF Corporation, trade name Texapon OC-P
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
 以下、処方例を示す。下記組成の口腔用組成物を上記と同様に調製し、評価したところ、処方例の口腔用組成物は、アスコルビン酸リン酸エステル又はその塩の滞留・吸収性が優れた。また、口腔内刺激が抑制されていた。 The following are examples of prescriptions. When an oral composition having the following composition was prepared and evaluated in the same manner as described above, the oral composition of the prescription example was excellent in the retention and absorption of ascorbic acid phosphate or a salt thereof. Moreover, intraoral irritation was suppressed.
[処方例1]練歯磨剤
(A)リン酸L-アスコルビルマグネシウム         0.3%
(B)ラウロイルメチルタウリンナトリウム         1.2
(C)ポリオキシエチレン(20)ラウリルエーテル     1.5
無水ケイ酸                       12
ソルビット液(70%)                 40
サッカリンナトリウム                   0.2
増粘性シリカ                       6
酸化チタン                        0.5
プロピレングリコール                   3
キサンタンガム                      0.7
ポリアクリル酸ナトリウム                 0.4
クエン酸                         0.1
水酸化ナトリウム                     0.1
香料                           0.8
精製水                         バランス 
 合計                        100.0%
 (B)/(A)=4
 (B)/(C)=0.8
[Prescription Example 1] Toothpaste (A) L-ascorbyl magnesium phosphate 0.3%
(B) Lauroylmethyl taurine sodium 1.2
(C) Polyoxyethylene (20) lauryl ether 1.5
Silicic anhydride 12
Sorbit liquid (70%) 40
Saccharin sodium 0.2
Thickening silica 6
Titanium oxide 0.5
Propylene glycol 3
Xanthan gum 0.7
Sodium polyacrylate 0.4
Citric acid 0.1
Sodium hydroxide 0.1
Fragrance 0.8
Purified water balance
Total 100.0%
(B) / (A) = 4
(B) / (C) = 0.8
[処方例2]練歯磨剤
(A)リン酸L-アスコルビルマグネシウム         0.2%
(B)ラウロイルメチルタウリンナトリウム         1.2
(C)ポリオキシエチレン(20)ラウリルエーテル     2.0
無水ケイ酸                       12
ソルビット液(70%)                 40
サッカリンナトリウム                   0.2
増粘性シリカ                       6
酸化チタン                        0.5
プロピレングリコール                   3
キサンタンガム                      0.7
ポリアクリル酸ナトリウム                 0.4
クエン酸                         0.1
水酸化ナトリウム                     0.1
香料                           0.8
精製水                         バランス 
 合計                        100.0%
 (B)/(A)=6
 (B)/(C)=0.6
[Prescription Example 2] Toothpaste (A) L-ascorbyl magnesium phosphate 0.2%
(B) Lauroylmethyl taurine sodium 1.2
(C) Polyoxyethylene (20) lauryl ether 2.0
Silicic anhydride 12
Sorbit liquid (70%) 40
Saccharin sodium 0.2
Thickening silica 6
Titanium oxide 0.5
Propylene glycol 3
Xanthan gum 0.7
Sodium polyacrylate 0.4
Citric acid 0.1
Sodium hydroxide 0.1
Fragrance 0.8
Purified water balance
Total 100.0%
(B) / (A) = 6
(B) / (C) = 0.6
[処方例3]練歯磨剤
(A)リン酸L-アスコルビルマグネシウム         2.0%
(B)ラウロイルメチルタウリンナトリウム         1.2
(C)ポリオキシエチレン(20)ラウリルエーテル     1.5
無水ケイ酸                       12
ソルビット液(70%)                 40
サッカリンナトリウム                   0.2
増粘性シリカ                       6
酸化チタン                        0.5
プロピレングリコール                   3
キサンタンガム                      0.7
ポリアクリル酸ナトリウム                 0.4
クエン酸                         0.1
水酸化ナトリウム                     0.1
香料                           0.8
精製水                         バランス 
 合計                        100.0%
 (B)/(A)=0.6
 (B)/(C)=0.8
[Prescription Example 3] Toothpaste (A) L-ascorbyl magnesium phosphate 2.0%
(B) Lauroylmethyl taurine sodium 1.2
(C) Polyoxyethylene (20) lauryl ether 1.5
Silicic anhydride 12
Sorbit liquid (70%) 40
Saccharin sodium 0.2
Thickening silica 6
Titanium oxide 0.5
Propylene glycol 3
Xanthan gum 0.7
Sodium polyacrylate 0.4
Citric acid 0.1
Sodium hydroxide 0.1
Fragrance 0.8
Purified water balance
Total 100.0%
(B) / (A) = 0.6
(B) / (C) = 0.8
[処方例4]洗口剤
(A)リン酸L-アスコルビルマグネシウム         0.3%
(B)ラウロイルメチルタウリンナトリウム         0.2
(C)ポリオキシエチレン(20)ラウリルエーテル     0.5
プロピレングリコール                   3
グリセリン                        4.5
キシリトール                       3
エタノール                        2
クエン酸                         0.015
クエン酸ナトリウム                    0.12
リン酸一水素二ナトリウム                 0.1
香料                           0.2
精製水                         バランス 
 合計                        100.0%
 (B)/(A)=0.67
 (B)/(C)=0.4
[Prescription Example 4] Mouthwash (A) L-ascorbyl magnesium phosphate 0.3%
(B) Lauroylmethyl taurine sodium 0.2
(C) Polyoxyethylene (20) lauryl ether 0.5
Propylene glycol 3
Glycerin 4.5
Xylitol 3
Ethanol 2
Citric acid 0.015
Sodium citrate 0.12
Disodium monohydrogen phosphate 0.1
Fragrance 0.2
Purified water balance
Total 100.0%
(B) / (A) = 0.67
(B) / (C) = 0.4

Claims (20)

  1.  (A)アスコルビン酸リン酸エステル又はその塩
                          0.1~5質量%、
    (B)アシルタウリン塩及び/又はアシルグルタミン酸塩
                          0.1~4質量%
    を含有してなることを特徴とする口腔用組成物。
    (A) Ascorbic acid phosphate ester or salt thereof 0.1 to 5% by mass,
    (B) Acyl taurate and / or acyl glutamate 0.1-4% by mass
    A composition for oral cavity, comprising:
  2.  (B)成分が、アシル基の炭素数が10~20であるアシルタウリン塩及び/又はアシルグルタミン酸塩である請求項1記載の口腔用組成物。 The oral composition according to claim 1, wherein the component (B) is an acyl taurine salt and / or an acyl glutamate having an acyl group having 10 to 20 carbon atoms.
  3.  (B)成分が、ラウロイルメチルタウリンナトリウム及び/又はラウロイルグルタミン酸ナトリウムである請求項2記載の口腔用組成物。 The composition for oral cavity according to claim 2, wherein the component (B) is sodium lauroylmethyl taurate and / or sodium lauroyl glutamate.
  4.  (B)/(A)が質量比として0.1~15である請求項1~3のいずれか1項記載の口腔用組成物。 The composition for oral cavity according to any one of claims 1 to 3, wherein (B) / (A) is 0.1 to 15 in terms of mass ratio.
  5.  更に、(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを0.1~4質量%含有する請求項1~4のいずれか1項記載の口腔用組成物。 Further, (C) 0.1 to 4% by mass of a polyoxyethylene alkyl ether having 12 to 22 carbon atoms of an alkyl group and an average addition mole number of ethylene oxide of 10 to 50 is contained. The composition for oral cavity of any one of Claims.
  6.  (B)/(C)が質量比として0.1~12である請求項5記載の口腔用組成物。 The composition for oral cavity according to claim 5, wherein (B) / (C) is 0.1 to 12 as a mass ratio.
  7.  歯磨剤である請求項1~6のいずれか1項記載の口腔用組成物。 The oral composition according to any one of claims 1 to 6, which is a dentifrice.
  8.  洗口剤である請求項1~6のいずれか1項記載の口腔用組成物。 The oral composition according to any one of claims 1 to 6, which is a mouthwash.
  9.  (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%配合した口腔用組成物に、(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を0.1~4質量%配合することを特徴とする、前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。 (A) 0.1B to 4% by mass of (B) acyl taurine salt and / or acyl glutamate is added to the oral composition containing 0.1 to 5% by mass of ascorbic acid phosphate or a salt thereof. A method for improving retention and absorbability of (A) an ascorbic acid phosphate ester or a salt thereof in the oral cavity composition in the oral cavity composition.
  10.  (B)/(A)が質量比として0.1~15である、請求項9記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。 The retention and absorption of (A) ascorbic acid phosphate or a salt thereof in the oral mucosa in the oral composition according to claim 9, wherein (B) / (A) is 0.1 to 15 in terms of mass ratio. How to improve.
  11.  前記(B)成分と共に、更に、(C)アルキル基の炭素数が12~22、エチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを0.1~4質量%配合する、請求項9又は10記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。 In addition to the component (B), 0.1 to 4% by mass of (C) polyoxyethylene alkyl ether having an alkyl group with 12 to 22 carbon atoms and an average added mole number of ethylene oxide of 10 to 50 is blended. A method for improving retention and absorbability of (A) ascorbic acid phosphate or a salt thereof in the oral composition according to claim 9 or 10.
  12.  (B)/(C)が質量比として0.1~12である、請求項11記載の前記口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性の向上方法。 The retention and absorbability of (A) ascorbic acid phosphate or a salt thereof in the oral mucosa in the composition for oral cavity according to claim 11, wherein (B) / (C) is 0.1 to 12 as a mass ratio. How to improve.
  13.  (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%含有する口腔用組成物配合用の(B)アシルタウリン塩及び/又はアシルグルタミン酸塩を含む、(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性向上剤であって、(B)成分量が組成物全体の0.1~4質量%となるように前記口腔用組成物に配合されることを特徴とする、前記(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性向上剤。 (A) Ascorbic acid phosphate containing (B) acyl taurine salt and / or acyl glutamate for blending oral composition containing 0.1-5% by mass of ascorbic acid phosphate or salt thereof An agent for improving retention and absorption of an ester or a salt thereof in the oral mucosa, and blended in the oral composition so that the amount of the component (B) is 0.1 to 4% by mass of the whole composition. (A) The ascorbic acid phosphate ester or a salt thereof in the oral mucosa and the absorbability improver.
  14.  (B)/(A)が質量比として0.1~15となるよう前記口腔用組成物に配合される、請求項13記載の滞留及び吸収性向上剤。 The retention and absorbency improver according to claim 13, wherein (B) / (A) is blended in the oral composition so that the mass ratio is 0.1 to 15.
  15.  更に、(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルを含み、(C)成分量が組成物全体の0.1~4質量%となるように前記口腔用組成物に配合される、請求項13又は14記載の滞留及び吸収性向上剤。 And (C) polyoxyethylene alkyl ether having 12 to 22 carbon atoms in the alkyl group and an average addition mole number of ethylene oxide of 10 to 50, and (C) the amount of the component is 0.1% of the total composition. The retention and absorbency improver according to claim 13 or 14, which is added to the composition for oral cavity so as to be -4% by mass.
  16.  (B)/(C)が質量比として0.1~12となるよう前記口腔用組成物に配合される、請求項15記載の滞留及び吸収性向上剤。 The retention and absorbency improver according to claim 15, wherein (B) / (C) is added to the oral composition so that the mass ratio is 0.1 to 12.
  17.  (A)アスコルビン酸リン酸エステル又はその塩を0.1~5質量%含有する口腔用組成物における(A)アスコルビン酸リン酸エステル又はその塩の口腔粘膜への滞留及び吸収性を向上するための製剤製造のための(B)アシルタウリン塩及び/又はアシルグルタミン酸塩の使用であって、前記(B)成分の使用量が組成物全体の0.1~4質量%であることを特徴とする、前記(B)アシルタウリン塩及び/又はアシルグルタミン酸塩の使用。 (A) In order to improve the retention and absorbability of (A) ascorbic acid phosphate or a salt thereof in the oral mucosa in an oral composition containing 0.1 to 5% by mass of ascorbic acid phosphate or a salt thereof. (B) acyl taurine salt and / or acyl glutamate for the preparation of the preparation, wherein the amount of the component (B) used is 0.1 to 4% by mass of the total composition (B) Use of acyl taurine salt and / or acyl glutamate.
  18.  (B)/(A)が質量比として0.1~15である、請求項17記載の使用。 The use according to claim 17, wherein (B) / (A) is 0.1 to 15 in terms of mass ratio.
  19.  前記(B)成分及び(C)アルキル基の炭素数が12~22、かつエチレンオキサイドの平均付加モル数が10~50であるポリオキシエチレンアルキルエーテルの使用であって、(C)成分の使用量が組成物全体の0.1~4質量%である、請求項17又は18記載の使用。 Use of the polyoxyethylene alkyl ether in which the component (B) and the (C) alkyl group have 12 to 22 carbon atoms and the average added mole number of ethylene oxide is 10 to 50, and the use of the component (C) Use according to claim 17 or 18, wherein the amount is from 0.1 to 4% by weight of the total composition.
  20.  (B)/(C)が質量比として0.1~12である、請求項19記載の使用。 The use according to claim 19, wherein (B) / (C) is 0.1 to 12 as a mass ratio.
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Publication number Priority date Publication date Assignee Title
WO2019049988A1 (en) * 2017-09-11 2019-03-14 ライオン株式会社 Oral biofilm removing agent and composition for oral cavity containing same
JP2019048802A (en) * 2017-09-11 2019-03-28 ライオン株式会社 Oral biofilm removing agent and composition for oral cavity containing the same
JP2019048801A (en) * 2017-09-11 2019-03-28 ライオン株式会社 Liquid composition for oral cavity

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