JPH0368842B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a stable skin cosmetic that suppresses oxidation during product storage. In general, raw materials for cosmetics include relatively many natural substances, some of which have stability problems. Many of these stability problems arise from the fact that the substance has multiple bonds such as double bonds in its molecules. That is, chemical substances are susceptible to oxidation reactions at multiple bond sites, and such oxidation reactions not only change the original properties of the raw material components, but also cause discoloration and generation of off-odor. Conventionally, two methods have been used to prevent the oxidation of raw materials for cosmetics.
One of them is to add an antioxidant to the raw material components. BHT, BHA, etc. are widely used as antioxidants. However, since these antioxidants have drawbacks in terms of safety, an alternative antioxidant is desired. The second method uses 2 of the raw material components.
This method eliminates heavy bonds through hydrogenation to make it less susceptible to oxidation. However, with this method,
Hydrogenation has the disadvantage that, for example, a liquid raw material component changes to a solid state, making it impossible for the raw material component to maintain its original properties and state. The present invention was made under these circumstances, and is a method for suppressing oxidation during the storage period of a product.
Our objective is to provide stable skin cosmetics. That is, the skin cosmetic of the present invention contains one or two components selected from the group consisting of fats and oils, oily components, and surfactants, each of which has at least one multiple bond greater than or equal to a double bond in its molecule. The present invention is characterized in that 1-hydroxy-2-pyridone or a salt thereof represented by the following general formula is blended into a cosmetic containing the following. [In the formula, R ₁ is an alkyl group having 1 to 17 carbon atoms, an alkenyl group having 2 to 17 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, or a cycloalkyl group having 7 to 9 carbon atoms. a bicycloalkyl group having atoms, a cycloalkyl-alkyl group in which alkyl has 1 to 4 carbon atoms, even if the cycloalkyl residue is substituted by an alkyl group having 1 to 4 carbon atoms. good), aryl group,
Aralkyl group where alkyl has 1 to 4 carbon atoms, arylalkenyl group where alkenyl has 2 to 4 carbon atoms, alkyl group has 1 to 4 carbon atoms, respectively
Aryloxyalkyl or arylmercaptoalkyl groups with 4 carbon atoms, benzhydryl groups, phenylsulfonylalkyl groups where alkyl has 1 to 4 carbon atoms, furyl or furyl where alkenyl has 2 to 4 carbon atoms represents an alkenyl group, and the aryl radicals mentioned above represent an alkyl group having 1 to 4 carbon atoms, 1 to 4 carbon atoms;
an alkoxy group having 5 carbon atoms, a nitro group,
Each may be substituted with a cyano group or a halogen. R ₂ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, an alkenyl or alkynyl group each having 2 to 4 carbon atoms,
Represents halogen, phenyl group, cyclohexyl group or benzyl group. ] Hereinafter, the skin cosmetic of the present invention will be explained in detail. The oils and fats used in the skin cosmetics of the present invention are:
Substances that contain unsaturated fatty acids in their molecules include, for example, olive oil, almond oil, peanut oil, avocado oil, castor oil, cocoa oil, coconut oil, cottonseed oil, lard, palm oil, and palm kernel oil. , sesame oil, turtle oil, wood wax, jojoba oil, etc. In addition to these fats and oils, it is also possible to simultaneously use fats and oils that do not contain unsaturated fatty acids. Oily components used in the skin cosmetics of the present invention include waxes such as spermaceti, beeswax, carnauba wax, and lanolin, hydrocarbons such as squalene, unsaturated fatty acids such as oleic acid and linoleic acid, and unsaturated fatty acids such as oleyl alcohol. Examples include esters containing unsaturated chain portions such as saturated higher alcohols, ethyl linoleate, and oleyl oleate. In addition to these oily components, it is also possible to simultaneously use an oily component that does not contain unsaturated chains. These fats and oils and oily components can be used alone or as a mixture of two or more in a range of 0.1 to 70% by weight depending on the type of cosmetic. The surfactant used in the skin cosmetic of the present invention contains an unsaturated chain in its molecule, and examples of such surfactants include polyoxyethylene fatty acid ester, polyoxyethylene higher alcohol ether, Ethylene glycol difatty acid ester, diethylene glycol difatty acid ester, polyethylene glycol difatty acid ester,
Examples include propylene glycol mono- or difatty acid ester, polyoxyethylene sorbitatol fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glyceryl trifatty acid ester, glycerin fatty acid ester, sorbitan fatty acid ester, and the like. Furthermore, in addition to these surfactants, it is also possible to use a surfactant that does not contain an unsaturated chain moiety. These surfactants range from 0.1 to 30% by weight,
It can be used alone or as a mixture of two or more. The following compounds or salts thereof are examples of the no-hydroxy-2-pyridones that are added to skin cosmetics containing the above-mentioned various ingredients for the purpose of preventing oxidation. 1-hydroxy-6-methyl-2-pyridone,
1-hydroxy-4,6-dimethyl-2-pyridone, 1-hydroxy-4-methyl-6-heptyl-2-pyridone, 1-hydroxy-4-methyl-
6-(1-ethylpentyl)-2-pyridone, 1-
Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone, 1-hydroxy-4-methyl-6-undecyl-2-pyridone, 1-hydroxy-4-methyl-6-propenyl -2-pyridone, 1-hydroxy-4-methyl-6-octenyl-2-pyridone, 1-hydroxy-4-methyl-6-(2,2-diptyl-vinyl)-2-pyridone, 1-hydroxy-4 -Methyl-6-(cyclohexenylidene-methyl)-2-
Pyridone, 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone, 1-hydroxy-
4-Methyl-6-(methyl-cyclohexyl)-2
-pyridone, 1-hydroxy-4-methyl-6-
(2-bicyclo[2,2,1]heptyl)-2-pyridone, 1-hydroxy-4-methyl-6-[2
-(dimethylcyclohexyl)-propyl]-2-
Pyridone, 1-hydroxy-4-methyl-6-
(4-Methyl-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(3-methyl-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-tert-butyl -phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(3
-methyl-4-chloro-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(3,5
-dichloro-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(3-prom-4-
Chlor-phenyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-methoxystyryl)
-2-pyridone, 1-hydroxy-4-methyl-
6-[1-4-nitrophenoxy)-butyl]-2
-pyridone, 1-hydroxy-4-methyl-6-
(4-cyanophenoxymethyl)-2-pyridone,
1-hydroxy-4-methyl-6-(phenylsulfonylmethyl)-2-pyridone, 1-hydroxy-4-methyl-6-[1-(4-chlorophenylsulfonyl)-butyl]-2-pyridone, 1-hydroxy-4-methyl-6-benzyl-2-pyridone, 1-hydroxy-4-methyl-6-(2,4
-dimethylbenzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(tert-butyl-benzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(2-chloro-benzyl)-2 -pyridone, 1-hydroxy-4-methyl-6-(4-chlorobenzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(2,5-dichlorobenzyl)-2-pyridone, 1- Hydroxy-4-methyl-6-(4-prom-benzyl)-2-pyridone, 1-hydroxy-4-methyl-6-(phenoxymethyl)-2-pyridone, 1-hydroxy-
4-Methyl-6-(3-methylphenoxy-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-sec-butylphenoxy-methyl)-
2-pyridone, 1-hydroxy-4-methyl-6
-(2,4,5-trichlorophenoxy-methyl)
-2-pyridone, 1-hydroxy-4-methyl-
6-(4-bromphenoxy-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-
Chlorphenylmercapto-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(4-
methylphenylmercapto-methyl)-2-pyridone, 1-hydroxy-4-methyl-6-(2-
naphthyl)-2-pyridone, 1-hydroxy-4
-methyl-6-benzhydryl-2-pyridone,
1-hydroxy-4-methyl-6-furyl-2-
Pyridone, 1-hydroxy-4-methyl-6-
(furylvinyl)-2-pyridone, 1-hydroxy-4-methyl-6-styryl-2-pyridone, 1
-Hydroxy-4-methyl-6-(phenylbutadienyl)-2-pyridone, 1-hydroxy-4
-phenyl-6-methyl-2-pyridone, 1-hydroxy-4,6-diphenyl-2-pyridone. Moreover, as the salt of the above compound, an organic amine salt is preferable. The organic amines include ethanolamine, diethanolamine, N-ethylethanolamine, N-methyl-diethanolamine,
Triethanolamine, diethylaminoethanol, 2-amino-2-methyl-n-propanol, dimethylaminopropanol, 2-amino-
2-methyl-propanediol, tri-isopropanolamine, ethylenediamine, hexamenediamine, morpholine, piperidine, cyclohexylamine, triptylamine, dodecylamine, N,N-dimethyl-dodecylamine, stearylamine, oleylamine, benzylamine,
dibenzylamine, N-ethylbenzylamine,
Examples include dimethylstearylamine, N-methyl-morpholine, N-methylpiperazine, 4-methylcyclohexylamine, and N-hydroxyethyl-morpholine. In addition to organic amine salts, alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as magnesium salts and calcium salts, and ammonium salts can also be used. The amount of 1-hydroxy-2-pyridone or its salt explained above is based on oils and fats that undergo oxidative deterioration,
Although it varies depending on the type and amount of oily components and surfactants, generally 0.05 to 10% by weight,
Preferably it is 0.1 to 5% by weight. The skin cosmetics of the present invention may include other optional ingredients such as lotions, liquid alcohol-based skin care products such as aftershave lotions, emulsified products such as creams and emulsions, and cosmetic products such as stick-like products. Known ingredients can be blended depending on the type of material. Such ingredients include, for example, polyhydric alcohols such as glycerin and propylene glycol, preservatives, polymeric thickeners, fragrances, extracts of plants, etc., disinfectants, medicinal agents, vitamins, ultraviolet absorbers, caustic soda, and triglycerides. Examples include ethanolamine, edetate, and ethanol. EXAMPLES Below, Examples and Comparative Examples of the present invention will be shown to explain the effects of the present invention. The storage stability of the composition of each example was determined mainly by sensory evaluation of slope. That is, after the samples were stored at 45° C. for one month, they were evaluated according to the following criteria by five testers who are experienced in the field of grading. No change in slope: ○ Slight change in slope: Δ Occurrence of off-flavor: × Examples 1 to 5 Ten types of cosmetic compositions with the compositions shown in Table 1 were prepared. and tested their storage stability (slope). The results are shown in the same table. Note that all amounts are expressed in weight percent. As is clear from the same table, it can be seen that all of the compositions of the present invention (Examples 1 to 5) containing 1-hydroxy-2-pyridone or a salt thereof exhibit excellent storage stability.

【table】

[Table] Example 6 A milky lotion having the following composition was prepared and its storage stability was tested. This emulsion exhibited no discoloration or odor during an accelerated storage test at 45°C for one month. Squalene 5% by weight Vaseline 2 Beeswax 0.5 Sorbitan sesquioleate 0.8 Polyoxyethylene (2OEO) oleyl ether 1.2 Propylene glycol 5 Carboxy vinyl polymer 20 (1% aqueous solution) Triethanolamine 0.1 1-Hydroxy-2-pyridone salt*10 0.5 Fragrance 0.5 Methyl paraoxybenzoate 0.2 Butyl paraoxybenzoate 0.1 Purified water Balance Example 7 An aftershave lotion having the following composition was prepared and its storage stability was tested. This aftershave lotion showed no discoloration or generation of off-odor in an accelerated storage test at 45°C for one month. Oleyl alcohol 5% by weight Propylene glycol 4 Acetylated lanolin alcohol 3 Ethanol 63 1-Hydroxy-2-pyridone salt *11 0.3 Fragrance Appropriate amount Menthol Appropriate amount Purified water Balance Example 8 Lipsticks having the following composition were prepared and their storage stability was tested. This lipstick showed no discoloration or generation of off-odor in an accelerated test of storage at 45°C for 1 month. Castor oil 40% by weight Beeswax 18 Lanolin 3 Isopropyl myristate 2 Parafine wax 5 Carnauba wax 4 Candelilla wax 7 Propylene glycol 5 Glyceryl monostearate 3 Pigment 2 Fragrance 2 Lake 8 1-Hydroxy-2-pyridone salt *12 1 *12 is * Example 9 Same compound as 11 In Example 1, 1-hydroxy-2-
1-Hydroxy-4-methyl- as pyridone salt
A similar evaluation was conducted using diethanolamine salt of 6-(3-bromo-4-chlorophenyl)-2-pyridone, but no discoloration or generation of off-odor was observed. Example 10 Similar evaluations were conducted using 1-hydroxy-4,6-diphenyl-2-pyridone sodium as the 1-hydroxy-2-pyridone salt in Example 1, but discoloration and generation of off-odor were observed. was not recognized. Example 11 In Example 2, 1-hydroxy-4-bromo-6- was used as 1-hydroxy-2-pyridone.
A similar evaluation was conducted using (methylcyclohexyl)-2-pyridone, but no discoloration or generation of off-odor was observed. Example 12 In Example 2, 1-hydroxy-4-benzyl-6 was used as 1-hydroxy-2-pyridone.
A similar test was conducted using -(methoxyphenyl)-2-pyridone, but no discoloration or generation of off-odor was observed. Example 13 In Example 6, 1-hydroxy-4-chloro-6 was used as the 1-hydroxy-2-pyridone salt.
A similar evaluation was conducted using sodium -(4-chlorophenyl)-2-pyridone, but no discoloration or generation of off-odor was observed.

Claims (1)

[Claims] 1. Contains one or more components selected from the group consisting of fats and oils, oily components, and surfactants, each of which has at least one multiple bond of double bond or more in its molecule. A skin cosmetic comprising 1-hydroxy-2-pyridone or a salt thereof represented by the following general formula. In the formula, R ₁ is an alkyl group having 1 to 17 carbon atoms, a cycloalkyl-alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms or halogen. Therefore, it represents an aryl group which may be substituted, and R ₂ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen, a phenyl group, a cycloalkyl group, or a benzyl group.