JP6474963B2 - Cleaning composition - Google Patents

Description

  The present invention relates to a cleaning composition for pharmaceuticals, quasi-drugs or cosmetics, which contains miconazole and / or a salt thereof stably and / or has an effect of suppressing unpleasant odor such as body odor.

Miconazole is widely used as an imidazole antifungal agent. An antibacterial effect against Pityrosporum ovale, one of the resident fungi of the head skin, is also recognized, and an antidandruff agent containing this as an active ingredient is known (see Patent Document 1). Moreover, the antifungal activity with respect to the genus Malassezia including the antifungal activity with respect to Candida albicans and Malassezia furfur (refer patent document 2) of the cleaning composition containing miconazole has also been confirmed.
Scalp shampoos (quasi-drugs) containing miconazole as an anti-dandruff ingredient are already on the market.

JP-A-8-3042 JP 2007-277227 A

Regarding the cleaning composition containing miconazole as an active ingredient (antifungal agent) as described above, the stability over time was examined. In some cases, the content of the active ingredient (quantitative value) decreased after storage for a predetermined period. I got the knowledge that there is. Specifically, it was recognized that the content of the active ingredient after storage for a predetermined period may be reduced depending on the lot of co-cleaning agent (surfactant). For this reason, although some influence by surfactant is estimated, it is difficult to clarify the causal relationship.
In addition, with the recent increase in cleanliness, it is desired to provide a cleaning composition that can effectively suppress body odor by preventing the generation of body odor and / or deodorizing the generated body odor.
It is an object of the present invention to provide a cleaning composition that improves at least one of these properties.

Based on the above knowledge, the present invention provides a cleaning composition that can be maintained in a predetermined amount containing the active ingredient miconazole without depending on coexisting components such as a surfactant even after the preparation of the cleaning composition. The purpose is to do. As a result of examining these problems, it is possible to suppress a decrease in the content of the active ingredient by adding a specific compound to the cleaning composition containing miconazole and / or a salt thereof as an active ingredient of the antifungal agent. I found. The compound specified in the present application is a compound that is generally classified as an antioxidant, but in the present application, compared to the case where sodium sulfite or the like that has been conventionally used as an antioxidant in a cleaning composition is added. The compound to be identified shows a special inhibitory effect on the decrease in miconazole content.
Moreover, it was confirmed by the inventors' examination that it has the unpleasant odor suppression effect irrespective of the kind of unpleasant odor by adding a specific compound in the cleaning composition containing miconazole.
Therefore, the present application relates to a compound as an active ingredient stabilizing agent (inhibition of content reduction) in a cleaning composition containing miconazole and / or a salt thereof as an active ingredient of an antifungal agent, and an active ingredient containing the compound is stabilized. The present invention as described below relating to the cleaned composition is provided.
In addition, the present invention as described below relating to a cleaning composition containing miconazole and / or a salt thereof as an active ingredient of an antifungal agent and excellent in an unpleasant odor suppressing effect is provided.

The first aspect of the present invention is:
(A) miconazole and / or a salt thereof,
(B) at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry-distilled extract and tea extract, and (C) a pharmaceutical or quasi-drug containing a surfactant Or it is a cleaning composition for cosmetics.
Another aspect of the present invention is:
(A) miconazole and / or a salt thereof,
(B) A cleaning composition for pharmaceuticals, quasi-drugs, or cosmetics containing cachytannin and / or medicinal charcoal and (C) a surfactant.

  The said cleaning composition of the aspect whose (C) surfactant is at least 1 sort (s) chosen from the group which consists of an anionic surfactant, an amphoteric surfactant, and a nonionic surfactant.

  The cleaning composition according to an embodiment containing two or more (B) antioxidants.

Usually, with respect to the total amount of the composition,
(A) 0.1 to 2.0% by mass of miconazole and / or a salt thereof,
(B) 0.001 to 5.0% by mass of an antioxidant, and (C) 5.0 to 50% by mass of a surfactant, preferably the remaining water,
Any one of the said cleaning compositions contained.
The cleaning composition of the present invention may be provided as a concentrate or dilution within the above composition range, and this case is also included in the composition of the present invention.

  The said cleaning composition of the aspect which is shampoo (hair shampoo, dry shampoo, rinse-in shampoo etc.) or soap (solid soap, liquid soap, foam soap, body soap, hand soap, facial soap, etc.).

The second aspect of the present invention is:
(A) for incorporation into a cleaning composition containing miconazole and / or a salt thereof, and (C) a surfactant,
(B) The above-mentioned (A) miconazole and / or its salt stabilizer comprising at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract is there.

The third aspect of the present invention is:
(A) miconazole and / or a salt thereof;
(B) green tea dry distillation extract;
(C) A cleaning composition for pharmaceuticals, quasi drugs or cosmetics containing a surfactant.

The fourth aspect of the present invention is:
(A) miconazole and / or a salt thereof;
(B) at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract;
(C) It is a body odor inhibitor or a composition for body odor suppression containing surfactant.

  The body odor suppressor or body odor control composition is selected from nonenal, i-valeric acid, methyl mercaptan, ammonia, 2-ethylhexanal, 6-methyl-5-pepten-2-one, hexanoic acid, and acetic acid. The said body odor inhibitor or the composition for body odor suppression which suppresses at least 1 sort of unpleasant odor.

The present invention also relates to a cleaning composition containing (A) miconazole and / or a salt thereof, and (C) a surfactant.
(B) By using together with at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract, (A) miconazole and / or a salt thereof can be stabilized. A method of converting can also be provided. In the present invention, the term “combination” includes simultaneous application, separate application, divided application before and after in combination, and a combination as two agents.

The present invention also relates to a cleaning composition containing (A) miconazole and / or a salt thereof, and (C) a surfactant.
(B) The method of suppressing body odor can also be provided by using together green tea dry distillation extract.

  ADVANTAGE OF THE INVENTION According to this invention, the composition for washing | cleaning which can maintain the active ingredient by the predetermined amount mix | blended without suppressing the time-dependent content fall of the active ingredient miconazole regardless of coexisting ingredients, such as surfactant, is provided can do. Moreover, the composition for washing | cleaning which suppresses unpleasant odors, such as a body odor, effectively can be provided.

The cleaning composition according to the present invention contains (A) miconazole and / or a salt thereof as an active ingredient of the antifungal agent.
Miconazole is a known compound with the chemical name 1-[(2RS) -2- (2,4-dichlorobenzyloxy) -2- (2,4-dichlorophenyl) ethyl] -1H-imidazole. The antifungal spectrum of miconazole is known, and for example, as described above, the antibacterial effect against Candida albicans and Malassezia fungi has been confirmed.
Examples of the salt include nitrate and hydrochloride. Miconazole and its salt are commercially available. Of the miconazole and its salts, miconazole nitrate is preferable from the viewpoint of ease of blending.
The blending amount is not particularly limited, but in the case of miconazole nitrate, it is usually 0.1 to 2.0% by mass, preferably 0.1 to 1.0% by mass, based on the total amount of the composition. Preferably it is 0.5-1.0 mass%.

The cleaning composition according to the present invention contains at least one (B) antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract.
Sodium pyrosulfite is a compound represented by Na ₂ S ₂ O ₅ and is also called disodium disulfite or sodium metabisulfite.
Tocopherols are various (α, β, γ, δ) methylated derivatives of tocol, either synthetically produced or naturally derived by extraction from plants, etc. Two or more kinds may be combined. Specific examples of the tocopherol include dl-α-tocopherol, dl-α-tocopherol acetate, d-α-tocopherol, d-β-tocopherol, d-γ-tocopherol, d-δ-tocopherol, preferably Dl-α-tocopherol, d-δ-tocopherol.
Natural vitamin E is obtained by extraction from plants such as soybeans, and is a mixture of d-α-tocopherol, d-β-tocopherol, d-γ-tocopherol, and d-δ-tocopherol.
Green tea dry distillation extract is a liquid obtained by dry distillation of green tea under reduced pressure, and is an extract containing ethanol or propylene glycol. As a commercial item, there are Fresh E, FS-1000, FS-500G, etc. of Shiraimatsu Shinyaku Co., Ltd.
The tea extract is an extract obtained by extracting green tea with water, ethanol, an ethanol solution, a propylene glycol solution, or a glycerin solution. Commercially available products include green tea extract LA from Maruzen Pharmaceutical Co., Ltd., tea extract S from Koei Kogyo Co., Ltd., and green tea liquid from Ichimaru Falcos Co., Ltd.
All of these substances are available as commercial products.
(B) Two or more of the above substances can be used in combination as an antioxidant.
The blending amount of the (B) antioxidant varies depending on the substance to be used, but the total amount of the (B) antioxidant is usually 0.001 to 5.0% by mass with respect to the total amount of the composition, preferably It is 0.1-2.0 mass%.

In the case of (B) green tea dry-distilled extract, it is 0.001-5.0 mass% normally with the whole quantity of (B) antioxidant with respect to the whole composition, Preferably it is 0.1-2.0 mass%. More preferably, it is 0.2-2.0 mass%, More preferably, it is 0.75-1.5 mass%.
In addition, the mixing ratio of (A) miconazole and / or salt thereof and green tea dry distillation extract is preferably 1: 0.5 to 5, more preferably 1: 1 to 3, more preferably 1: 1 to 2 in terms of mass ratio. It is.

The antioxidant (B) specified above has an effect of suppressing a decrease in storage content of an active ingredient in a cleaning composition containing (A) miconazole and / or a salt thereof as an active ingredient of an antifungal agent. . That is, in the accelerated test of the cleaning composition containing (A) miconazole and / or a salt thereof, a decrease in the content of (A) miconazole and / or a salt thereof in the composition may be observed. By blending a specific antioxidant, the decrease in content is suppressed.
The decrease in content refers to an accelerated test relating to the stability of the composition relative to the content of the active ingredient immediately after production of the cleaning composition, for example, for 2 months under conditions of 40 ° C. and 75% humidity. In a test, it represents that the content of an active ingredient falls. The degree of suppression of the decrease in the content is preferably a state in which the content of the active ingredient is maintained at 95% or more before the start of the test in the test for 2 months under the conditions of 40 ° C. and 75% humidity. Examples of the method for measuring the content of the active ingredient in the cleaning composition include measurement by liquid chromatography.

  (B) In the case of using a green tea dry distillation extract as an antioxidant, (A) In a cleaning composition containing miconazole and / or a salt thereof as an active ingredient of an antifungal agent, the effect of suppressing an unpleasant odor such as body odor is exerted. Particularly preferred. That is, a preferred embodiment of the present invention is a cleaning composition for pharmaceuticals, quasi-drugs or cosmetics comprising (A) miconazole and / or a salt thereof, (B) a green tea dry distillation extract, and (C) a surfactant. It is. Another preferred embodiment of the present invention is a body odor suppressor or body odor control composition containing (A) miconazole and / or a salt thereof, (B) a green tea dry distillation extract, and (C) a surfactant. The unpleasant odor is not particularly limited, and examples thereof include odors that humans feel unpleasant, bad odors, and body odors of animals including humans. Substances causing body odor include nonenal, i-valeric acid, methyl mercaptan, ammonia, 2-ethylhexanal, 6-methyl-5-pepten-2-one, hexanoic acid, and acetic acid, and at least two of these As described above, it is sufficient that the substance has an inhibitory effect on three or more substances, more preferably four or more substances. In particular, at least two, preferably three, and more preferably all four selected from nonenal, i-valeric acid, methyl mercaptan, and ammonia may be more effective.

The unpleasant odor suppressing effect is not particularly limited as long as humans feel that the odor can be suppressed. For example, when the above-described cleaning composition is used, one or more of the substances causing unpleasant odor may be a cleaning composition. 50%, preferably 60%, more preferably 80% or more should be removed, assuming that the detection amount when no is used is 100%. Such a removal rate can be evaluated by a known method. For example, it can be evaluated using Test Example 2 described later. Moreover, since the presence or absence of an unpleasant odor depends on human subjectivity, it may be evaluated by a sensory test. In the case of the sensory test, the odor score is evaluated, for example, in 3 to 10 stages, and the rating may be improved by using the cleaning composition of the present invention.
The removal rate of unpleasant odors in human tests and in vitro tests such as Test Example 2 described below, after use of the cleaning composition, in a sealed environment or an open environment, assuming a room temperature or summer temperature (for example, At 30 ° C. or 40 ° C.), for example, evaluation can be performed after 30 minutes, 1 hour, 3 hours, 6 hours, 12 hours, and 24 hours. When an accelerated test is performed, for example, the evaluation can be performed after 30 minutes under the conditions of 40 ° C. and 75% humidity.

In this invention, you may mix | blend another antioxidant in addition to the said (B) antioxidant. Other antioxidants can be added without particular limitation as long as safety to the human body has been confirmed. For example, sodium sulfite, piroctone olamine, dibutylhydroxytoluene (BHT), butylhydroxy Anisole (BHA), propyl gallate, ascorbic acid and its salt, erythorbic acid and its salt, tocotrienol, ferulic acid and the like can be used. These can be arbitrarily blended in an amount usually used separately from the above-mentioned (B) antioxidant.
In the present invention, oyster tannin and / or medicinal charcoal may be blended in place of the antioxidant (B). The blending amount can be arbitrarily selected within the same range as the antioxidant.

In the present invention, the (C) surfactant as the cleaning component is at least one selected from the group consisting of an anionic surfactant, an amphoteric surfactant and a nonionic surfactant.
Specifically, examples of the anionic surfactant include fatty acid salt, alkyl sulfate ester salt, monoalkyl phosphate ester salt, alkyl ether sulfate ester salt, polyoxyethylene alkyl ether sulfate ester, polyoxyethylene alkyl ether phosphate ester Salt, polyoxyethylene alkyl ether acetate, higher fatty acid alkanolamide sulfate, acyl isethionate, alkyl sulfosuccinate, α-olefin sulfonate, alkyl ether carboxylate, acyl lactate, N-acyl sarcosine salt, N-acyl glutamate, N-acyl methyl alanine salt, N-acyl methyl taurate, N-acyl aspartate, sodium laureth sulfate and the like can be mentioned.

  Examples of amphoteric surfactants include sulfobetaine type amphoteric surfactants, aminopropion type amphoteric surfactants, aminoacetic acid betaine type amphoteric surfactants (such as amidopropyl betaine laurate), glycine type amphoteric surfactants, and imidazoline. Type amphoteric surfactants and the like.

Nonionic surfactants include fatty acid alkanolamides, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkyl ethers (such as polyoxyethylene lauryl ether), alkyl glycosides, polyoxyethylene sorbitan fatty acid esters, and the like.
All the above surfactants are commercially available. Two or more surfactants can be used in appropriate combination.
Examples of combinations of surfactants include an embodiment containing three kinds of sodium lauroylmethyl-β-alanine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, and coconut oil fatty acid diethanolamide, and lauroylmethyl- An embodiment containing at least four kinds selected from β-alanine sodium, coconut oil fatty acid sodium methyltaurine, lauryldimethylaminoacetic acid betaine, coconut oil fatty acid amidopropyl betaine and coconut oil fatty acid diethanolamide is preferable.

The surfactant is preferably low-irritating from the viewpoint of irritation to the skin and feeling of use.
Among the above, hypoallergenic anionic surfactants include N-acyl glutamate such as sodium coconut oil fatty acid acyl glutamate, N-acyl methyl such as sodium lauroylmethyl-β-alanine and sodium coconut oil fatty acid methylalanine. N-acyl asparagine such as alanine salt, coconut oil fatty acid methyl taurine sodium, N-acyl methyl taurine salt such as lauroyl methyl taurine sodium, lauroyl sarcosine sodium, coconut oil fatty acid sodium sarcosine sodium, and lauroyl aspartate sodium Acid salts, sodium laureth sulfate and the like.

  Examples of hypoallergenic amphoteric surfactants include aminoacetic acid betaine amphoteric surfactants such as lauryldimethylaminoacetic acid betaine and coconut oil fatty acid amidopropyl betaine (such as lauric acid amidopropyl betaine), 2-alkyl-N-carboxymethyl. Examples include imidazoline type amphoteric surfactants such as -N-hydroxyethyl imidazolinium betaine.

  Examples of the non-irritating nonionic surfactant include fatty acid alkanolamides such as coconut oil fatty acid monoethanolamide, coconut oil fatty acid diethanolamide, coconut oil fatty acid N-methylethanolamide, and polyoxyethylene sorbitan monooleate. Examples include oxyethylene sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil, and polyoxyethylene lauryl ether.

  The surfactant may be commercially available after being diluted with water or the like. In this specification, the blending amount as the surfactant (C) is the total amount of the cleaning composition of the surfactant itself unless otherwise specified. It is shown as mass% with respect to. (C) Surfactant is 5-50 mass% normally, Preferably it is 5-30 mass%, More preferably, it is 10-30 mass%, More preferably, it is 15-25 mass%.

  (A) In the cleaning composition containing miconazole or a salt thereof, (C) the surfactant is preferably a combination of the above-mentioned hypoallergenic anionic surfactant and hypoallergenic amphoteric surfactant. The mixing ratio is not particularly limited. For example, anionic surfactant: amphoteric surfactant = 1: 0.1 to 5, preferably 1: 0.3 to 4, more preferably 1: 0.5 to 2, Especially preferably, it can be set to 1: 0.5-1.

  (A) When miconazole or a salt thereof having low solubility is completely dissolved or uniformly dispersed, the preferable surfactant combination described above is a cleaning composition in which the active ingredient of the antifungal agent is completely dissolved. Can be obtained.

In addition to the above (A) to (C), the cleaning composition according to the present invention can contain other components as long as the effects of the present invention are not impaired.
As other components, for example, (A) at least one alkanediol having 3 to 8 carbon atoms can be blended in order to suppress precipitation of miconazole or a salt thereof. Examples of the alkanediol having 3 to 8 carbon atoms include butanediol, propanediol (1,3-propanediol, 1,2-propanediol), pentanediol, hexanediol, and octanediol. Preferred are alkanediols having 3 to 5 carbon atoms, and particularly preferred are 1,3-butanediol (1,3-butylene glycol) and 1,2-propanediol (propylene glycol).
Although the compounding quantity of the said alkanediol is not specifically limited, 0.1-15 mass% is preferable with respect to the composition whole quantity, and 1.0-10 mass% is more preferable.

  Other ingredients include triclosan, isopropylmethylphenol, trichlorocarbanilide, trichlorohydroxydiphenyl ether, benzalkonium chloride, resorcinol, alkylisoquinolinium bromide and other antibacterial agents, zinc pyrithione, selenium disulfide, sulfur, and salicylic acid. Other active ingredients such as anti-dandruff agents such as dandruff glycyrrhizinate, stearyl glycyrrhetinate, allantoin, and other anti-dandruff agents such as and salts thereof, piroctone olamine, and the like can also be appropriately blended.

  Furthermore, the cleaning composition according to the present invention has, as other components, viscosities of components generally used in cleaning compositions such as coloring agents such as pigments and pigments, cellulose derivatives, polyethylene glycol, and carboxyvinyl polymers. Adjusting agents, higher alcohols such as behenyl alcohol and stearyl alcohol, pearlescent agents such as glycol distearate and ethylene glycol distearate, pH adjustment of citric acid, sodium citrate, sodium benzoate, monosodium succinate, potassium hydroxide, etc. Agents, salts such as sodium chloride, plant extracts, vegetable oils, fresheners, preservatives such as methyl paraoxybenzoate and propyl paraoxybenzoate, vitamins, fragrances, UV absorbers such as oxybenzone, wetting agents such as amino acids and sugars Glycerin, Moisturizing agents such as glycerin and sorbitol, chelating agents such as edetate, cationic polymers (polyquaternium-10, guar hydroxypropyltrimonium chloride), conditioning components such as silicone oil (dimethicone), ethanol, water, etc. are added as appropriate. be able to.

In the present invention, the cleaning composition is a composition intended to remove stains on the application site and / or to exert an antifungal action, and is mixed with a cleaning agent component and washed away with running water after use. It may be used in any form such as wiping.
The cleaning composition according to the present invention is a cleaning composition for pharmaceuticals, quasi-drugs, or cosmetics. Examples of dosage forms include ointments, creams, emulsions, lotions, solutions, and aerosols. The specific form is not particularly limited. For example, soap (solid soap, liquid soap, foam soap, body soap (also called body shampoo), hand soap, etc.), cleansing agent (makeup remover), shampoo ( Hair shampoo, dry shampoo, rinse-in shampoo, etc.), rinse (hair rinse, hair conditioner, etc.) and the like.
Among these, soap and shampoo are preferable, and shampoo is particularly preferable.
In addition, the cleaning composition according to the present invention can be soaked into clean cotton and used for wiping.
The cleaning composition of the present invention can be applied not only to human bodies such as cleaning of skin such as limbs and hair, but also to various animals such as cleaning of the whole body of pets. It can also be used for cleaning dishes, medical instruments, and the like.

As a preferred embodiment of the cleaning composition of the present invention, for example, (A) 0.1% to 1.0% by mass of miconazole nitrate,
(B) 0.1 to 2.0% by mass of at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract,
(C) 10-20% by mass of sodium lauroylmethyl-β-alanine,
5 to 15% by mass of 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine,
1.0-10% by mass of propylene glycol,
0.2 to 1.0% by mass of the cationic polymer, and an appropriate amount of the pH adjusting agent, preservative and water, respectively, or the balance of the above mass%,
The cleaning composition containing is mentioned.

Also,
(A) 0.1 to 1.0% by mass of miconazole nitrate,
(B) 0.1 to 2.0% by mass of at least one antioxidant selected from the group consisting of sodium pyrosulfite, tocopherol, natural vitamin E, green tea dry distillation extract and tea extract,
(C) 5 to 15% by mass, preferably 6 to 12% by mass of sodium lauroylmethyl-β-alanine and / or coconut oil fatty acid methyl taurine sodium,
(D) 1 to 10% by weight, preferably 2.9 to 9% by weight of 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine and / or coconut oil fatty acid amidopropyl betaine,
Propylene glycol in an amount of 1.0 to 10% by mass, and a pH adjuster, an antiseptic and water in an appropriate amount, or the balance of the above mass%,
The cleaning composition containing is mentioned.

Also,
(A) 0.1 to 1.0% by mass of miconazole nitrate,
(B) 0.1 to 2.0 mass% of green tea dry distillation extract,
(C) 5 to 15% by mass, preferably 6 to 12% by mass of sodium lauroylmethyl-β-alanine and / or coconut oil fatty acid methyl taurine sodium,
(D) 1 to 10% by weight, preferably 2.9 to 9% by weight of 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine and / or coconut oil fatty acid amidopropyl betaine,
Propylene glycol in an amount of 1.0 to 10% by mass, and a pH adjuster, an antiseptic and water in an appropriate amount, or the balance of the above mass%,
The cleaning composition containing is mentioned.

Examples of the present invention are shown below, but these examples are for specifically explaining the present invention, and do not limit the scope of the present invention.
(Examples 1-20 and Comparative Examples 1-2)
Each component shown in Table 1 that was 100% by mass in total was mixed, dissolved by heating to 80 ° C., cooled to 35 ° C. with stirring, and the cleaning compositions having the compositions shown in Tables 1 and 2 were prepared.

(Test Example 1)
About each composition of Examples 1-9 obtained above and Comparative Examples 1-2, the following acceleration test is performed, the content before and behind the test of an active ingredient is quantified, and after the test with respect to the content quantitative value before a test The stability was examined by determining the ratio (%) of the quantitative content value. The results are shown in Table 3.
Accelerated test method: The prepared composition was placed in a container free of miconazole nitrate adsorption and moisture evaporation, and stored in a constant temperature and humidity chamber at a temperature of 40 ° C. and a humidity of 75%, and sampling was performed after 2 months.
Content measurement method: quantified by high performance liquid chromatography under the following conditions.
Detector: UV absorptiometer (measurement wavelength: 230 nm)
Column: Octadecylsilylated silica gel column Column temperature: Constant temperature around 40 ° C. Mobile phase: Methanol / 0.05 mol / L ammonium dihydrogen phosphate solution mixture (4: 1)

  As shown in the table, in the composition of the comparative example, a clear decrease in the content of the active ingredient miconazole nitrate was observed in the test period of 2 months, whereas the content was determined by the blending of the antioxidant (B) specified in the present invention. The effect of suppressing the decrease was observed.

(Examples 2-1 to 2-2, Comparative examples 2-1 to 2-3)
A cleaning composition having the composition shown in Table 4 was prepared according to the method of Example 1 and the like.

(Test Example 2) Confirmation of unpleasant odor suppression effect using pork skin <Test method>
Pork skin (Yucatan micropig skin set Nippon Charles River Co., Ltd.) was pretreated to remove subcutaneous fat and made 5 × 5 cm.
The pretreated pork skin was immersed in physiological saline for 1 hour or more, then drained lightly with a wiper, and one of the following unpleasant odor sources was dropped on the surface. It was folded in two so that the source of unpleasant odor was inside, and left undisturbed for 1 minute so as to soak up the unpleasant odor.
Cleaning compositions of Examples 2-1 to 2-2, Comparative Examples 2-1 to 2-2, or Compositions of Comparative Example 2-3 (Comparative Example 2-3 is a general medicinal cleaning containing triclosan. 30 g (which is an agent and does not contain miconazole) was placed in a 90 mm petri dish, and pork skin was immersed in it for 1 minute. After rinsing with 3 L of water for 30 seconds, it was drained lightly and placed in a 350 mL glass sealed container. The subject used water instead of 30 g of the cleaning composition, and the subsequent treatment was the same.
<Evaluation method>
After heating a 350 mL sealed container containing pork skin at 40 ° C. for 30 minutes, the unpleasant odor concentration in the head space in the container was measured by the following quantitative method. The removal rate of the unpleasant odor by each composition was calculated | required by the following formula. The results are shown in Tables 5-6.
Removal rate (%) = (control gas concentration (ppm) −gas concentration (ppm) when using the composition) / (control gas concentration (ppm)))
<Measurement method>
The gas concentration was determined for each of the four types of unpleasant odor sources by the following method.
Nonenal Gas chromatography method Gas chromatograph: GC-2014 (Shimadzu Corporation)
Detector: FID (Shimadzu Corporation)
Column: Thermon-3000 5% Shincarbon A 60/80 3 mm × 2.1 m (Shinwa Chemical Co., Ltd.)
Column temperature: constant temperature around 130 ° C. INJ. T / DET.T: 180 ° C / 180 ° C
Injection volume: 1 mL
i-Valeric acid gas detector tube method (8L)
Methyl mercaptan gas detector tube method (7L)
Ammonia gas detector tube method (3M, 3L)

In the table, “◯” indicates that the component is included in the formulation.

  As shown in Table 5, when the unpleasant odor source is Nonenal, Comparative Example 2-3 which is a general medicinal detergent has a low removal rate of 12.2%, whereas Comparative Example 2-1 containing miconazole has 55 It can be seen that the removal rate was significantly improved to 0.7%, and that the removal rate was further improved to 66.4% in Example 2-1 containing the green tea dry distillation extract. Further, it can be seen that the same tendency is observed in Comparative Example 2-2 and Example 2-2 having a large content of main components, and in particular, Example 2-2 shows a removal rate as high as 92.3%.

In the table, “◯” indicates that the component is included in the formulation.

  Table 6 shows the results for i-valeric acid, methyl mercaptan and ammonia unpleasant odor sources. In Table 6, as in Table 5, it can be seen that Examples 2-1 and 2-2 containing the green tea dry-distilled extract show a higher removal rate than Comparative Examples 2-1 and 2-2, respectively.

(Test Example 3) Confirmation of the effect of suppressing unpleasant odors by humans The unpleasant odor source is placed at an arbitrary location of 3 cm × 3 cm such as a human arm, for example, so as to have an odor corresponding to an odor intensity of 5 in a 6-step odor intensity display method Apply. The cleaning composition of Examples 2-1 to 2-2 and the composition of Comparative Examples 2-1 to 2-3 are washed with 1 mL, and the odor after drying is sensory evaluated.

  Although it changes with unpleasant odor sources, it turns out that the composition of Comparative Example 2-1 and 2-2 has an unpleasant odor suppression effect compared with a control | contrast. Furthermore, in Example 2-1 and 2-2 containing a green tea dry-distilled extract, it turns out that there is a high unpleasant odor suppression effect regardless of a source of unpleasant odor. From this, by adding the green tea dry-distilled extract to the composition, a high effect of suppressing unpleasant odor can be expected regardless of the unpleasant odor source.

(Test Example 4) Anti-malassezia effect test <Medium medium preparation>
An agar dilution method was used.
Each component of miconazole nitrate, green tea dry distillation extract, or a mixture thereof was diluted with DMSO and stirred to prepare a stock solution for cleaning composition. The prepared composition is shown in Table 7. This was serially diluted with Sabouraud dextrose agar medium (SDA) to prepare a 2-fold dilution series.

<Preculture and preparation of bacterial solution>
A test bacterium (Malassezia furfur) was inoculated into SDA supplemented with olive oil and cultured at 30 ± 2 ° C. for 72 hours. The bacterial solution after the culture was diluted with sterilized physiological saline, and prepared so that the number of bacteria became 10 ⁶ cells / mL.
<Measurement method>
The prepared medium was inoculated into the prepared medium, and olive oil was added, followed by culturing at 30 ± 2 ° C. After 72 hours, the presence or absence of the growth of the test bacteria was observed with the naked eye, and the growth of the bacteria in the culture medium was observed and judged in three stages. A sample in which the growth of the bacteria was observed in the whole medium was designated as “+”, a growth in which the growth of the bacteria was less than 1/3 of the culture medium was designated as “±”, and a growth in which the growth of the bacteria was not observed in the medium was designated as “−”. The results are shown in Table 8.

  Comparative Example 3-1 is a formulation of miconazole nitrate, and Table 8 shows that the minimum growth inhibitory concentration (MIC) of the test bacteria is 125 ppm. Comparative Example 3-2 is a prescription of green tea dry distillation extract, but as is clear from the results in Table 8, it can be seen that the green tea dry distillation extract itself has no effect of suppressing the growth of bacteria. In Comparative Example 3-2, the growth of the fungus was confirmed even at a cleaning composition component concentration of 2000 ppm. On the other hand, in Example 3-1, including both miconazole nitrate and green tea dry distillation extract, the MIC was 62.5 ppm, which was lower than that of Comparative Example 3-1. Since the green tea dry distillation extract itself does not have the effect of inhibiting the growth of fungi, it is considered that the green tea dry distillation extract enhanced the fungal growth inhibitory effect of miconazole nitrate.

Claims (17)

(A) miconazole and / or a salt thereof,
(B) at least one antioxidant selected from the group consisting of green tea dry distillation extract and tea extract, and contains (C) a surfactant, pharmaceuticals, met quasi drugs or cleaning composition for cosmetics And
The content of at least one antioxidant selected from the group consisting of (B) green tea dry-distilled extract and tea extract is 1.0 to 2.0% by mass (provided that the total mass of the cleaning composition is 1.0 to 2.0% by mass). , Except 1.0% by mass). The cleaning composition according to claim 1, further comprising at least one selected from the group consisting of sodium pyrosulfite, tocopherol, and natural vitamin E. The cleaning composition according to claim 1 or 2 , wherein the (C) surfactant is at least one selected from the group consisting of an anionic surfactant, an amphoteric surfactant, and a nonionic surfactant. The surfactant (C) is
N-acylglutamate, N-acylmethylalanine, N-acylmethyltaurine, N-acylsarcosine, N-acylaspartate, aminoacetic acid betaine-type amphoteric surfactant, imidazoline-type amphoteric surfactant, fatty acid The cleaning composition according to any one of claims 1 to 3 , which is at least one selected from the group consisting of alkanolamides, polyoxyethylene sorbitan fatty acid esters, and polyoxyethylene hydrogenated castor oil. The cleaning composition according to any one of claims 1 to 4 , comprising two types of the antioxidant (B). (B) the antioxidant comprises a green tea dry distillation extract, cleaning composition according to any one of claims 1-5. For the total amount of the composition,
(A) 0.1 to 2.0% by mass of miconazole and / or a salt thereof,
(B) 1.0 to 2.0% by mass of an antioxidant (excluding 1.0% by mass) , and (C) 5.0 to 50% by mass of a surfactant.
Containing, cleaning composition according to any one of claims 1-6. The cleaning composition according to any one of claims 1 to 7 , further comprising 0.1 to 15% by mass of at least one alkanediol having 3 to 8 carbon atoms. The cleaning composition according to claim 8 , wherein the at least one alkanediol having 3 to 8 carbon atoms is 1,3-butanediol or 1,2-propanediol. Further, containing Pirokutooramin, cleaning composition according to any one of claims 1-9. It said cleaning composition is a shampoo or soap, cleaning composition according to any one of claims 1-10. For the total amount of the composition,
(A) 0.1 to 1.0% by mass of miconazole nitrate,
(B) 1.0 to 2.0% by mass (excluding 1.0% by mass) of at least one antioxidant selected from the group consisting of green tea dry distillation extract and tea extract, and (C) N- At least one anionic surfactant selected from the group consisting of acylglutamate, N-acylmethylalanine, N-acylmethyltaurate, N-acylsarcosine and N-acylaspartate, and / or aminoacetic acid 10-30% by mass of a betaine-type amphoteric surfactant and / or an imidazoline-type amphoteric surfactant,
Containing, cleaning composition according to any one of claims 1 to 1 1. The anionic surfactant is sodium palm fatty acid acyl glutamate, sodium lauroylmethyl-β-alanine, sodium palm oil fatty acid methylalanine, palm oil fatty acid methyl taurine sodium, lauroyl methyl taurine sodium, lauroyl sarcosine sodium, palm oil fatty acid sarcosine sodium And at least one selected from the group consisting of sodium lauroyl aspartate, and
The amphoteric surfactant is at least one selected from the group consisting of lauryldimethylaminoacetic acid betaine, coconut oil fatty acid amidopropyl betaine, and 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine. cleaning composition according to claim 1 2. (A) 0.1 to 1.0% by mass of miconazole nitrate,
(B) 1.0 to 2.0% by mass (excluding 1.0% by mass ) of green tea dry-distilled extract,
(C) 5-15% by mass of sodium lauroylmethyl-β-alanine and / or coconut oil fatty acid methyl taurine sodium
(D) optionally 1 to 10% by weight of 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine and / or coconut fatty acid amidopropyl betaine,
A cleaning composition, which is a shampoo or soap containing 1.0 to 10% by weight of propylene glycol and a pH adjuster, preservative and water. (A) miconazole and / or a salt thereof;
(B) green tea dry distillation extract;
(C) a body odor inhibitor containing a surfactant ,
The body odor inhibitor whose content of the said (B) green tea dry distillation extract is 1.0-2.0 mass% (however, except 1.0 mass%) with respect to the total mass of the said body odor inhibitor. (A) 0.1 to 1.0% by mass of miconazole nitrate,
(B) 1.0 to 2.0% by mass (excluding 1.0% by mass ) of green tea dry-distilled extract,
(C) 5-15% by mass of sodium lauroylmethyl-β-alanine and / or coconut oil fatty acid methyl taurine sodium
(D) optionally 1 to 10% by weight of 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine and / or coconut fatty acid amidopropyl betaine,
A composition for suppressing body odor, which is a shampoo or soap containing 1.0 to 10% by mass of propylene glycol, and a pH adjuster, an antiseptic and water. (A) miconazole and / or a salt thereof,
(B) A cleaning composition for pharmaceuticals, quasi-drugs or cosmetics, comprising at least one antioxidant selected from the group consisting of green tea dry-distilled extract and tea extract, and (C) a surfactant. Because
The content of at least one antioxidant selected from the group consisting of (B) green tea dry-distilled extract and tea extract is 1.0 to 2.0% by mass (provided that the total mass of the cleaning composition is 1.0 to 2.0% by mass). , Except 1.0% by mass).