JP5359546B2 - Liquid oral composition - Google Patents

Description

  The present invention exerts a high penetrating and bactericidal effect on periodontopathic biofilms, suppresses degradation of isopropylmethylphenol, which is an active ingredient, by ultraviolet rays, has an excellent penetrating bactericidal effect over time, and has an appearance stability. Also relates to a liquid oral composition containing good isopropylmethylphenol.

  Conventionally, the causes of caries, periodontal disease, bad breath, etc. are thought to be due to various bacteria in plaque, and sterilization of plaque bacteria is important for the prevention of oral diseases as an effective means for prevention and improvement of oral diseases. For this reason, nonionic and cationic fungicides have been incorporated into oral care products. In particular, non-ionic disinfectants such as isopropylmethylphenol among disinfectants blended in oral care products have characteristics that tend to have a broad antibacterial spectrum compared to cationic disinfectants. It is blended and marketed in oral compositions.

  Isopropylmethylphenol is a nonionic fungicide that is attracting attention as a fungicide with a high penetration bactericidal effect on periodontopathic biofilms. So far, oral compositions (see Patent Documents 1 and 2) that exhibit a high penetrating and bactericidal effect on periodontopathic biofilms by blending isopropylmethylphenol with liquid oral compositions have been proposed. Has been.

  However, isopropylmethylphenol degrades over time due to UV exposure, resulting in a decrease in penetrating bactericidal power to periodontal pathogenic biofilms and a deterioration in the appearance stability (ori, nigori, discoloration) of the preparation. There was a problem.

  As a method for preventing decomposition of isopropylmethylphenol due to exposure to ultraviolet rays, a method in which an ultraviolet absorber, a pigment, or the like is blended in a preparation or a resin that forms a container such as a bottle can be considered. However, in the case of the first method to be blended in the preparation, general UV absorbers are mostly water-insoluble substances such as rutin and inferior in storage stability at low temperatures. It may cause. Furthermore, since the light stability of the ultraviolet absorber itself is not so good, the discoloration of the preparation easily proceeds even if the ultraviolet absorber is added. Therefore, it is difficult for the first method to satisfactorily improve the appearance stability of the preparation over time by preventing the decomposition of isopropylmethylphenol by UV exposure.

  On the other hand, in the case of the second method in which an ultraviolet absorber or pigment is blended in a resin that forms a container such as a bottle, the container includes an opaque bottle and a transparent bottle. Is usually about 0 to 10%, and although it can suppress the degradation of isopropylmethylphenol due to exposure to ultraviolet rays and the resulting deterioration in appearance stability (ori, digori, discoloration) to some extent, its effect is still insufficient. is there. A transparent bottle is desirable as a container from the viewpoint of making the container colorless and transparent in recent years. However, the ultraviolet transmittance of the transparent bottle is usually about 30 to 100%, and the effect of suppressing the decomposition of isopropylmethylphenol by ultraviolet absorption is effective. Therefore, from the viewpoint of flexibility such as the design of the bottle, the oral composition containing isopropylmethylphenol is currently in the form of an opaque bottle and marketed.

  Like isopropylmethylphenol, triclosan, which is a nonionic fungicide, has a broad antibacterial spectrum and is blended in various oral compositions. However, triclosan is not decomposed by exposure to ultraviolet rays and has a high bactericidal power against airborne bacteria, but the penetrating bactericidal power of periodontopathic biofilms is insufficient. Moreover, the technique (refer patent documents 3-8) which improves an osmotic | sterilization bactericidal power by using together non-ionic bactericides, such as a triclosan, and isopropyl methylphenol until now, In this case, By irradiating with ultraviolet rays, isopropylmethylphenol is decomposed and the sterilizing power of penetrating into the biofilm is lowered, and the appearance stability (orientation, stain, discoloration) is also deteriorated.

  Therefore, in oral compositions containing isopropylmethylphenol, the degradation of isopropylmethylphenol over time due to UV exposure is effectively suppressed, and the penetration and bactericidal power of periodontopathic biofilm over time and the appearance of the preparation Development of technology that can improve stability (origin, stain, discoloration) is desired.

JP 2006-0669909 A JP 2006-182663 A JP 11-12141 A Japanese Patent Laid-Open No. 11-12142 JP 2000-281545 A JP 2000-319153 A JP 2002-12536 A JP 2004-26658 A

  The present invention has been made in view of the above circumstances, exhibits a high osmotic bactericidal effect on periodontopathic biofilms, and suppresses degradation of isopropylmethylphenol over time even when exposed to sunlight, and its penetration An object of the present invention is to provide a liquid oral composition containing isopropylmethylphenol, which exhibits a bactericidal effect over a long period of time and has good appearance stability.

  As a result of intensive investigations to achieve the above object, the present inventors have obtained a liquid oral composition containing isopropylmethylphenol, a rutin glycoside such as α-glucosylrutin, an anionic surfactant and / or When combined with a nonionic surfactant, degradation of isopropylmethylphenol by ultraviolet rays over time is suppressed, a high penetrating and bactericidal effect on periodontopathic biofilms is demonstrated over a long period of time, and exposure to sunlight It was found that the appearance stability was good even when stored underneath.

  That is, in the present invention, as is clear from the examples described later, isopropylmethylphenol can be used in combination with natural flavonoid component rutin, which is a known natural antioxidant (photodegradation inhibitor), in combination with isopropylmethylphenol. The penetrating and bactericidal effect on periodontopathic biofilms derived from methylphenol is not satisfactorily demonstrated, and the appearance stability is inferior due to the occurrence of orientation and scratches and discoloration. By compounding a saccharide with an anionic surfactant and / or a nonionic surfactant, isopropylmethylphenol can be prevented from being decomposed by ultraviolet rays over time. For example, a resin containing no UV absorber Even if it is stored in a container with an ultraviolet transmittance of 30% or more, such as a transparent container formed, and stored under exposure to ultraviolet light, periodontal pathogenic bio Excellent osmotic and sterilizing effect on film, and no oligo, stains or discoloration in liquid preparations. Therefore, high osmotic and sterilizing effect on periodontopathic biofilm derived from isopropylmethylphenol is demonstrated over a long period of time. In addition, a liquid preparation having good appearance stability can be obtained. Such an effect of the present invention cannot be achieved when any component is lacking.

Accordingly, the present invention provides the following liquid oral composition.
[Claim 1]
A liquid oral composition comprising (A) isopropylmethylphenol, (B) a rutin glycoside, and (C) an anionic surfactant and / or a nonionic surfactant.
[Claim 2]
The composition for liquid oral cavity according to claim 1 or 2, wherein the mixing ratio of the component (A) and the component (C) is (C) / (A) in the mass ratio of 1.8 to 60. .
[Claim 3]
The liquid oral composition according to claim 1 or 2, wherein the component (C) is an anionic surfactant, and (C) / (A) is 2 to 20 in terms of mass ratio.
[Claim 4]
The liquid oral composition according to claim 1 or 2, wherein the component (C) is a nonionic surfactant, and (C) / (A) is 2 to 60 in mass ratio.
[Claim 5]
The liquid oral composition according to claim 1, 2 or 3, wherein the anionic surfactant is sodium alkyl sulfate and / or N-acyl sarcosine sodium.
[Claim 6]
The liquid oral composition according to claim 1, 2 or 4, wherein the nonionic surfactant is polyoxyethylene hydrogenated castor oil having an average addition mole number of ethylene oxide of 60 to 100 moles.
[Claim 7]
The composition for liquid oral cavity according to any one of claims 1 to 6, which is contained in a container having an ultraviolet transmittance of 30 to 100%.

  The composition for liquid oral cavity of the present invention can suppress degradation of isopropylmethylphenol over time even when it is stored in a transparent bottle containing no UV absorber and left exposed to sunlight. A high penetrating and sterilizing effect is exhibited over a long period of time, and the appearance stability over time is good.

Hereinafter, the present invention will be described in more detail.
The composition for liquid oral cavity of the present invention contains (A) isopropylmethylphenol, and (B) a rutin glycoside, and (C) an anionic surfactant and / or a nonionic surfactant. .

A commercially available thing can be used as isopropyl methyl phenol of a component (A), For example, the isopropyl methyl phenol etc. by Osaka Kasei Co., Ltd. can be used.
The blending amount of isopropylmethylphenol is 0.01 to 0.1% (mass%, the same shall apply hereinafter) of the whole composition in terms of exerting an osmotic and bactericidal effect on periodontopathic biofilm and in terms of appearance stability. In particular, 0.02 to 0.08% is preferable. If it is less than 0.01%, the penetrating bactericidal power to periodontal pathogenic biofilms may not be sufficiently exerted, and if it exceeds 0.1%, the preparation may be stored during storage under sunlight exposure or at 5 ° C. Turbidity and appearance stability may be impaired.

The rutin glycoside of component (B) is a water-soluble flavonol glycoside, and is an enzyme-treated rutin obtained by a known enzyme treatment method in which sugar is added to natural rutin, such as α-glucosyl rutin or enzyme-treated isoquer. Citrine (manufactured by San-Eigen Co., Ltd.)
As the rutin glycoside, α-glucosylrutin is suitable, and specifically, commercially available products such as α-glucosylrutin (trade name αG-rutin) manufactured by Toyo Seika Co., Ltd. can be used, and the molecular weight is 772-1258. .

The compounding amount of rutin glycoside is preferably 0.05% or more, particularly 0.1% or more of the whole composition, and the upper limit is preferably 25% or less, particularly 1% or less. If it is less than 0.05%, the effect of inhibiting the decomposition of isopropylmethylphenol by UV exposure may not be obtained satisfactorily, and the osmotic sterilization effect may not be obtained satisfactorily. The appearance stability may be impaired.
In addition, the rutin glycoside of the component (B) is in a mass ratio with respect to the blending amount of the isopropylmethylphenol of the component (A) in terms of the effect of suppressing decomposition of isopropylmethylphenol by exposure to ultraviolet rays and the appearance stability. (B) / (A) is preferably blended in the range of 1 to 500, particularly 1.25 to 20.

  Component (C) is blended as a solubilizing component. As the anionic surfactant of component (C), an alkyl sulfate (for example, sodium lauryl sulfate, potassium lauryl sulfate, sodium myristyl sulfate, potassium myristyl sulfate, etc.) Salt), alkali metal salt of N-acyl amino acid having 12 to 16 carbon atoms in acyl group, lauroylmethyl taurine, acyl amino acid salt, sodium dodecylbenzenesulfonate, α-sulfo fatty acid alkyl ester / sodium, alkyl phosphate ester salt 1 type can be used individually or in combination of 2 or more types. Among them, sodium alkyl sulfate and sodium N-acyl sarcosine are preferable, and sodium lauryl sulfate and sodium lauroyl sarcosine are more preferable from the viewpoints of penetrating bactericidal ability to periodontal pathogenic biofilms and appearance stability.

  The compounding amount of the anionic surfactant is preferably 0.1 to 1.0%, particularly preferably 0.1 to 0.5% of the entire composition. If it is less than 0.1%, isopropylmethylphenol is not solubilized satisfactorily and becomes cloudy, and there are cases where it is inferior in penetrating bactericidal power and appearance stability to periodontopathic biofilms. During storage, the anionic surfactant itself may precipitate over time, and the appearance stability (orientation, scratch) may be impaired.

  Nonionic surfactants include polyoxyethylene hydrogenated castor oil, polyglycerin fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene sterol, polyoxyethylene lanolin having an average addition mole number of ethylene oxide of 60 to 100 mol. Etc., and one or more of these are used. Especially, the polyoxyethylene hydrogenated castor oil whose average added mole number of ethylene oxide is 60-100 mol is preferable at the point of the osmotic | sterilization power with respect to periodontal pathogenic biofilm, and isopropyl methylphenol solubilization. If the average added mole number of ethylene oxide in the polyoxyethylene hydrogenated castor oil is less than 60 moles, isopropylmethylphenol may be precipitated during low-temperature storage, and those exceeding 100 moles are generally not commercially available.

  The blending amount of the nonionic surfactant is preferably 0.1 to 1.0%, more preferably 0.2 to 0.7%. If it is less than 0.1%, it may be difficult to maintain the appearance stability (Ori, Nigori), and if it exceeds 1.0%, it may be inferior in penetrating sterilization power to periodontopathic biofilms.

  As the component (C), an anionic surfactant or a nonionic surfactant may be blended, or an anionic surfactant and a nonionic surfactant may be blended. When an anionic surfactant and a nonionic surfactant are used in combination, the solubilizing power is increased by a synergistic effect, so that there is an advantage that the blending amount can be reduced. The total amount of the anionic surfactant and / or the nonionic surfactant is 0.1% of the total composition in order to achieve both penetration and bactericidal power to periodontal pathogenic biofilms and appearance stability (Ori, Nigori). -1.0%, especially 0.2-0.8% is preferable, and if it is less than 0.1%, isopropylmethylphenol cannot be solubilized, and it is inferior in penetrating bactericidal power and appearance stability to periodontopathic biofilms. If it exceeds 1.0%, the penetrating and bactericidal power to the periodontopathic biofilm and the appearance stability may be inferior.

The component (C) anionic surfactant and / or nonionic surfactant has a mass ratio of (C) / (A) of 1.8 to 60, particularly 3.75 to the blending amount of isopropylmethylphenol. It is preferable to mix | blend in the ratio of 30.
Furthermore, when component (C) is an anionic surfactant, (C) / (A) is preferably 2 to 20, particularly 8 to 12 in terms of mass ratio with respect to the amount of isopropylmethylphenol. When component (C) is a nonionic surfactant, (C) / (A) is preferably 2 to 60, particularly preferably 3.75 to 30. When component (C) is an anionic surfactant and a nonionic surfactant, (C) / (A) is 1.8-60 in terms of mass ratio with respect to the amount of isopropylmethylphenol. It is preferable to mix | blend especially in the ratio of 4-16. If the ratio of (C) / (A) is less than the lower limit value, the penetrating bactericidal power and periodontal pathogenic biofilm are inferior, and if the ratio exceeds the upper limit, penetrating bactericidal power to the periodontal pathogenic biofilm. And appearance stability may be inferior.

  The liquid oral composition of the present invention can be prepared and applied as a dosage form such as a mouthwash, liquid toothpaste, dentifrice gel, mouth freshener, concentrated mouthwash, etc. In addition to the above, appropriate known components according to the dosage form can be blended as necessary. For example, a solvent, a wetting agent, a thickener, a pH adjuster, an antiseptic, a sweetener, a fragrance, a surfactant, an active ingredient, a colorant, and the like can be contained.

  As the solvent, purified water is generally blended, but alcohols such as lower monohydric alcohols having 2 to 4 carbon atoms such as ethanol can also be blended. The blending amount of purified water is 20% or more of the total amount of the composition, and more preferably 80% or more from the viewpoint of feeling of use. The upper limit of the amount of purified water is preferably such that the total of the lower limit amounts of the components (A) to (C) is 100% or less, that is, 99.84%. The blending amount of alcohols such as lower alcohols is 0 to 30%.

Examples of the wetting agent include polyhydric alcohols such as glycerin, sorbitol, ethylene glycol, and polyethylene glycol, and sugar alcohols such as xylit, maltite, and lactit.
Examples of the thickener include xanthan gum, sodium alginate, polyvinyl alcohol and the like.

  Examples of pH adjusters include phthalic acid, phosphoric acid, citric acid, succinic acid, acetic acid, fumaric acid, malic acid, carbonic acid and salts thereof such as potassium salt, sodium salt, ammonium salt, ribonucleic acid and salts thereof, hydroxylation One or more of sodium and the like can be used, and a combination of phosphoric acid and its sodium salt, or citric acid and its sodium salt is particularly preferable. In particular, the liquid oral composition of the present invention preferably adjusts the pH at 25 ° C. to 5.5 to 7.5, and sodium dihydrogen phosphate and sodium monohydrogen phosphate as pH adjusters in the vicinity thereof, or It is preferable to use a combination of citric acid and sodium citrate.

  Preservatives include: sodium benzoate, paraparabenzoic acid esters such as methylparaben, ethylparaben, propylparaben, butylparaben, benzoic acid such as sodium benzoate or salts thereof, cetylpyridinium hydrochloride, alkyldiaminoethylglycine hydrochloride, potassium sorbate Etc.

  Examples of sweetening agents include saccharin sodium, steviosite, sucralose, reduced palatinose, and erythritol.

  Natural flavors such as peppermint oil, spearmint oil, eucalyptus oil, wintergreen oil, clove oil, thyme oil, sage oil, cardamom oil, rosemary oil, marjoram oil, lemon oil, nutmeg oil, lavender oil, paracres oil, etc. Essential oils and flavor components contained in the above natural essential oils such as l-carvone, 1,8-cineole, methyl salicylate, eugenol, thymol, linalool, limonene, menthone, menthyl acetate, citral, camphor, borneol, pinene, spirantol Also, ethyl acetate, ethyl butyrate, isoamyl acetate, hexanal, hexenal, methyl anthranilate, ethyl methyl phenyl glycidate, benzaldehyde, vanillin, ethyl vanillin, furaneol, malto , Perfume ingredients such as ethyl maltol, gamma / delta decalactone, gamma / deltown decalactone, N-ethyl-p-menthane-3-carboxamide, menthyl lactate, ethylene glycol-l-menthyl carbonate, A combination of fragrance ingredients and natural essential oils (preferably not containing ethanol), apple, banana, strawberry, blueberry, melon, peach, pineapple, grape, muscat, wine, cherry, squash, coffee, brandy, yogurt, etc. For example. These fragrance | flavors can mix | blend 0.00001-3% in the composition in the range which does not prevent the effect of this invention 1 type, or 2 or more types.

  As the surfactant, in addition to the surfactant of component (C), other surfactants, specifically, betaine acetate type amphoteric surfactants such as alkyldimethylaminoacetic acid betaine and fatty acid amidopropyldimethylaminoacetic acid betaine. Amphoteric surfactants such as imidazoline type amphoteric surfactants such as N-fatty acid acyl-N-carboxymethyl-N-hydroxyethylethylenediamine salt and amino acid type amphoteric surfactants such as N-fatty acid acyl-L-alginate salt You may mix | blend. When a surfactant other than the component (C) is blended, the blending amount is preferably 0.01 to 2% of the total composition within a range not impeding the effects of the present invention.

  As the active ingredient, in addition to isopropylmethylphenol, other known active ingredients such as antibacterial agents other than isopropylmethylphenol such as triclosan and cetylpyridinium chloride, anti-inflammatory agents such as tranexamic acid and epsilon-aminocaproic acid, dextran Enzymes such as ase, amylase, protease, mutanase, lysozyme, lytic enzyme, lytechenzyme, fluorides such as sodium fluoride, sodium monofluorophosphate, stannous fluoride, aluminum chlorohydroxy allantoin, allantoin, azulene, lysozyme chloride , Vitamin C such as ascorbic acid and its derivatives, dihydrocholesterol, glycyrrhetin salts, glycyrrhetinic acids, hydrocholesterol, chlorophyll, copper chlorophyllin sodium, thyme, o Add plant extracts such as citrus, clove, hamamelis, copper gluconate, caropeptide, sodium polyphosphate, water-soluble inorganic phosphate compound, polyethylene glycol, polyvinylpyrrolidone, anticalculus, anti-plaque, potassium nitrate, aluminum lactate, etc. can do. In addition, when mix | blending active ingredients other than these isopropylmethylphenol, the compounding quantity can be made into an effective quantity in the range which does not inhibit the effect of this invention.

  As a colorant, a highly safe water-soluble pigment such as Blue No. 1, Green No. 3, Yellow No. 4, Red No. 105, or the like can be added.

As the container for the composition of the present invention, a container made of PET (polyethylene terephthalate), glass, polypropylene, polyethylene or the like can be used. From the viewpoint of suppressing adsorption of nonionic disinfectant and fragrance, the container of PET or glass is used. Use is preferred. The container can be either a transparent container or an opaque container, but the composition of the present invention does not contain an ultraviolet absorber in a material such as a resin that forms a non-light-shielding container, for example, a container. Alternatively, the surface of the material such as glass can be suitably accommodated in a container that is not subjected to a coating treatment for shielding ultraviolet rays.
In this case, as the container, an opaque container has an ultraviolet transmittance of 0 to 10%, and when a transparent container is used, a container having an ultraviolet transmittance of 30% or more can be used, and the upper limit is 100% or less. Even if the composition of the present invention is stored in a container having an ultraviolet transmittance of 30% or more, such as a transparent container formed of a resin containing no ultraviolet absorber, and stored under exposure to ultraviolet light, the periodontal pathogen of isopropylmethylphenol The high penetration sterilization effect on the biofilm is satisfactorily exhibited over time, and the appearance stability is also good.
In addition, the said ultraviolet transmittance uses Shimadzu ultraviolet visible spectrophotometer UV-160A (SHIMADZU), the flat section (length / width / thickness = 40/10 / 1.2mm) of a container is usually the mass which puts a cell. And the ultraviolet transmittance was measured (hereinafter the same).

  EXAMPLES Hereinafter, although this invention is demonstrated in detail based on an Example and a comparative example, this invention is not restrict | limited by these Examples.

  For the preparation of the liquid oral composition in each case, isopropylmethylphenol (Osaka Kasei Co., Ltd.), α-glucosyl rutin (Toyo Seika Co., Ltd.), rutin (Tokyo Kasei Kogyo Co., Ltd.), sodium lauryl sulfate (Toho Chemical Co., Ltd.) ), Lauroyl sarcosine sodium (manufactured by Kawaken Fine Chemical Co., Ltd.), polyoxyethylene (60) hydrogenated castor oil (manufactured by Nikko Chemicals), polyoxyethylene (80) hydrogenated castor oil (manufactured by Nikko Chemicals), cetylpyridinium chloride ( Wako Pure Chemical Industries, Ltd.) was used. In the table, POE represents polyoxyethylene, and the percentages shown below mean mass% unless otherwise specified. In the following examples, all samples after storage were returned to room temperature and used.

Examples and comparative examples
Liquid oral compositions having the compositions shown in Tables 1 to 3 were prepared by conventional methods, and each evaluation was performed by the following methods. The results are shown in Tables 1-3.

<Experiment 1>
(1) Appearance stability evaluation The liquid oral cavity composition (sample) shown in Tables 1 to 3 is a 80 mL colorless and transparent PET container (polyethylene terephthalate container, manufactured by Yoshino Kogyo, no UV absorber for resin materials) Filled with 80 mL of the container (83% UV transmittance), and in August, exposed to sunlight, or not exposed to sunlight (in the refrigerator) at 5 ° C, the total UV irradiation of the sun-exposed product was 350 Langley. After storage in the storage period until it was, appearance stability (progress of discoloration) was visually determined according to the following criteria.
The degree of progression of discoloration was evaluated for sun-exposed products using a 5 ° C.-stored product as non-exposed to control. Appearance stability (Ori, Nigori) is determined by exposing the sun-exposed product to room temperature until 1 month from the first storage after exposure to sun, and then exposing the product to sunlight and non-sun-exposed product at 5 ° C. Was absolutely evaluated.

Discoloration progress criteria:
(Double-circle): Discoloration has not progressed at all compared with the control product.
○: Compared with the control product, discoloration is proceeding slightly, but there is no problem.
Δ: Discoloration is progressing compared to the control product.
X: Remarkably discolored without comparison with the control product.
ORI and NIGORI judgment criteria;
(Double-circle): There is no orientation and no negation, and it is transparent.
○: Although very small orientation is observed when shaken, it is at a satisfactory level and is transparent.
(Triangle | delta): Slight orientation or tingling is recognized.
X: Remarkable orientation or scratch is recognized.

<Experiment 2>
(1) Method for producing model periodontopathic biofilm 4 hours with human unstimulated saliva obtained by filtering a hydroxyapatite (HA) plate (manufactured by Asahi Optical Co., Ltd.) having a diameter of 7 mm and a thickness of 3.5 mm with a 0.45 μm filter. The treated solution is used as a model biofilm carrier, and the culture solution is 30 mg of trypticase soy broth (Difco) dissolved in 1 L of purified water, 5 mg of hemin (Sigma), menadione (Sigma) (Product) 0.5 mg added was used. In order to produce a model biofilm, Streptococcus gordonii ATC51656 strain and Actinomyces naesrandi ATCC51655 strain were used as oral resident bacteria, and Porphyromonas gingivalis ATCC33277 strain was used as a pathogenic bacterium. These three bacterial species were inoculated into the above-mentioned culture solution so as to be 2 × 10 ⁷ cfu / mL (cfu: colony forming units), respectively, and the saliva-treated HA carrier at 37 ° C. under anaerobic conditions (5% carbon dioxide gas). , 95 volume% nitrogen) for 2 weeks (the replacement rate of the culture medium was set to 10 volume%) to form a model biofilm mixed with three bacterial species on the HA surface.

(2) Osmotic and bactericidal effect on model biofilm The formed model biofilm was stored in a liquid oral composition shown in Tables 1 to 3 (contained in the same container as in Experiment 1 above and stored under exposure to sunlight under the same conditions) 1) It was immersed in 2 mL for 3 minutes and washed 6 times with 1 mL of sterile physiological saline. Thereafter, the model biofilm was dispersed by sonication (200 μA, 10 seconds) with 4 mL of sterilized physiological saline, a 10% cotton defibrinated blood-containing trypticase soy agar plate (manufactured by Difco) and kanamycin sulfate (200 mg / L: 50 μL was spread on a tripty case soy blood agar plate containing Sigma) and cultured under anaerobic conditions. The grown colonies were counted, and the number of remaining Porphyromonas gingivalis bacteria (cfu) was determined and determined according to the following criteria.

Judgment standard ◎: Viable count is less than 10 ⁶ ○: Viable count is 10 ⁶ or more and less than 10 ⁷ △: Viable count is 10 ⁷ or more and less than 10 ⁸ ×: Viable count is 10 ⁸ or more

<Experiment 3>
(1) Residual ratio of isopropylmethylphenol The liquid oral composition shown in Tables 1 to 3 is contained in the same container as in Experiment 1 and stored under the same conditions. After adding 1 mL of a solution prepared by dissolving 0.3 g of isoamyl paraoxybenzoate (manufactured by Tokyo Chemical Industry Co., Ltd.) in 200 mL of 60% ethanol (99.5) (manufactured by Kanto Chemical Co., Ltd.), liquid chromatography (sample injection amount) 20 μL), and the amount of isopropylmethylphenol was quantified.

In addition, the mobile phase of liquid chromatography uses methanol / purified water / phosphoric acid mixture (volume ratio 1300: 700: 1), pump: JASCO PU-980, sample introduction part: JASCO AS -950, detector: JASCO Corporation UV-970 (set to a measurement wavelength of 280 nm), recording device: System Instruments Co., Ltd. Chromatocoder 21J, column hot bath: JASCO Corporation CO-966 (at 50 ° C) Setting), column: Mightysil RP-18 GP (5 μm) manufactured by Kanto Chemical Co., Inc. was used. Moreover, as an initial value for comparison of the remaining ratio, a sample after storage at 5 ° C. was prepared by the same method as in Experiment 1 described above, and quantified by liquid chromatography, which was used as the initial value.
a formula:
From the peak area ratio of isopropylmethylphenol / internal standard substance, the residual ratio of isopropylmethylphenol in the sample was calculated using the following formula, and the residual ratio of isopropylmethylphenol was evaluated based on the following criteria.

a formula:
Isopropylmethylphenol residual rate (%) = (A / B) × (C / D) × 100
A: Peak area of isopropyl methyl phenol in the sample exposed to sunlight / peak area of internal standard substance B: Peak area of isopropyl methyl phenol in the sample stored at 5 ° C. without exposure to sunlight / Peak area of internal standard substance C: Storage after exposure to sunlight Amount of sample collected (g)
D: Amount of sample stored at 5 ° C. without exposure to sunlight (g)

Criteria for residual rate of isopropylmethylphenol;
◎: Residual rate of isopropylmethylphenol is 95% or more ○: Residual rate of isopropylmethylphenol is 90% or more and less than 95% △: Residual rate of isopropylmethylphenol is 85% or more and less than 90% ×: Residual rate of isopropylmethylphenol Is less than 85%

Claims (7)

  A liquid oral composition comprising (A) isopropylmethylphenol, (B) a rutin glycoside, and (C) an anionic surfactant and / or a nonionic surfactant.   The composition for liquid oral cavity according to claim 1 or 2, wherein the mixing ratio of the component (A) and the component (C) is (C) / (A) in the mass ratio of 1.8 to 60. .   The liquid oral composition according to claim 1 or 2, wherein the component (C) is an anionic surfactant, and (C) / (A) is 2 to 20 in terms of mass ratio.   The liquid oral composition according to claim 1 or 2, wherein the component (C) is a nonionic surfactant, and (C) / (A) is 2 to 60 in mass ratio.   The liquid oral composition according to claim 1, 2 or 3, wherein the anionic surfactant is sodium alkyl sulfate and / or N-acyl sarcosine sodium.   The liquid oral composition according to claim 1, 2 or 4, wherein the nonionic surfactant is polyoxyethylene hydrogenated castor oil having an average addition mole number of ethylene oxide of 60 to 100 moles.   The composition for liquid oral cavity according to any one of claims 1 to 6, which is contained in a container having an ultraviolet transmittance of 30 to 100%.