JP4824517B2 - Composition for external use - Google Patents

Description

The present invention relates to an external composition, and more particularly to an external composition containing a fatty acid ester of an oxyalkylene derivative of 1,2-diol.

For external preparations such as cosmetics and hair treatment agents, oily bases are widely used for the purpose of imparting moisture transpiration suppression, smoothness and gloss from the skin and hair. Since the oily base used for the external preparation is the skin or hair of the human body, it is particularly important that there is no irritation or toxicity to the skin or the like from the viewpoint of safety. As an oily base, from the viewpoint of safety, attempts have been made to use ceramide and the like contained in a large amount of human stratum corneum (Patent Documents 1 and 2), but ceramide generally has a very high melting point. Its use is very limited due to its high crystallinity and high cost due to its difficulty in obtaining.
In addition, the use of 1,2-alkanediol in a composition for external use or the like means that an oil-in-water emulsion composition used as a mild emulsifier for action on the skin in combination with an alkali metal salt of N-long chain acylglutamic acid (Patent Document- 3) and a surfactant composition (Patent Document 4) that alleviates skin irritation of an anionic surfactant, and a fatty acid ester of 1,2-alkanediol has been proposed as an external preparation. (Patent Literature-5). Furthermore, it is also known that an alkylene oxide adduct of 1,2-alkanediol is useful as a surfactant (Patent Document 6).
However, 1,2-alkanediol has a problem of strong skin irritation, and fatty acid esters of 1,2-alkanediol and alkylene oxide adducts of 1,2-alkanediol are used in other preparations for external use. When mixed with the components, there is a problem that stability at low temperatures (for example, 0 ° C. or lower) is poor and separation often occurs.
Japanese Patent Publication No. 6-57651 Japanese Patent Publication No. 6-37429 Japanese Patent Publication No. 61-28367 Japanese Patent Publication No. 7-59716 JP 2001-10921 A JP 2002-114844 A

The present invention provides an external composition that is excellent in safety, imparts wettability to the skin, is easy to wash out, imparts flexibility and wettability to the hair, has good stability at low temperatures and does not cause separation. The purpose is to provide.

The inventors of the present invention have arrived at the present invention as a result of intensive studies to solve the above-mentioned object.
That is, this invention is a composition for external use which contains the component (A) which consists of 1 type, or 2 or more types of the compound shown by General formula (1) as an essential component.

In the formula, R ¹ is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms; X and Y are a hydrogen atom or an acyl group represented by —CO—R ² , and R ² is 1 to 30 carbon atoms. An aliphatic or alicyclic hydrocarbon group in which at least one of X and Y is an acyl group; AO is an alkyleneoxy group having 2 to 6 carbon atoms; m and n are 0 or 1 to 60 An integer, at least one of which is not zero.

The external composition of the present invention is an external composition that is excellent in safety, imparts wettability to the skin, is easy to wash away, provides flexibility and wettability to the hair, and does not cause separation even at low temperatures. .

The composition for external use of this invention contains the component (A) which consists of 1 or more types of the compound shown by General formula (1), Preferably 2 or more types, More preferably, 3-30 types as an essential component.

In the general formula (1), R ¹ preferably has 8 to 20 carbon atoms, more preferably 8 to 16, and if R ¹ is less than 6 carbon atoms, the external preparation containing component (A) is sufficiently stable at low temperature. However, even if the number of carbons exceeds 30, sufficient low-temperature stability cannot be obtained.
Examples of the aliphatic hydrocarbon group in R ¹ include linear or branched alkyl groups (n-hexyl group, n-heptyl group, n-octyl, n-decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, docosyl). , 3,5,7-trimethyloctyl group, etc.) and linear or branched alkenyl groups (1-hexenyl, 1-decenyl, 6-dodecenyl, oleyl group, etc.).
Examples of the alicyclic hydrocarbon group in R ¹ include a cycloalkyl group (such as cyclohexyl), an alkylcyclohexyl group (such as propylcyclohexyl group and octylcyclohexyl group), and a cycloalkylalkyl group (such as cyclohexylbutyl group and cyclohexyloctyl group). And a cycloalkenyl group (2-cyclohexenyl group) and the like.
Among R ¹ , an aliphatic hydrocarbon group is preferable, and two or more of them having different carbon numbers may be used in combination.

In the general formula (1), X and Y is an acyl group represented by hydrogen or -CO-R ^2, at least one of X and Y is an acyl group represented by -CO-R ^2, X Both of Y and Y may be an acyl group. Preferred is a combination of a compound in which both are acyl groups, or both are acyl groups, and a compound in which one is an acyl group.
R ² in -CO-R ² is an aliphatic or alicyclic hydrocarbon group having 1 to 30 carbon atoms, the other groups listed above for R ^1, the number of carbon atoms as aliphatic hydrocarbon groups 1 to 5 linear or branched alkyl groups (methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, etc.) and linear or branched alkenyl groups (vinyl group, propenyl group, An allyl group).
R ² is preferably an aliphatic hydrocarbon group from the viewpoint of low temperature stability of the external preparation.
When both X and Y are acyl groups, the two R2s may be the same or different, but are preferably the same group from the viewpoint of ease of production.

Examples of the alkyleneoxy group having 2 to 6 carbon atoms represented by AO in the general formula (1) include an ethyleneoxy group, a 1,2-propyleneoxy group, a 1,3-propyleneoxy group, a 1,2-butyleneoxy group, Examples include 1,4-butyleneoxy group and 1,6-hexyleneoxy group. Among AOs, ethyleneoxy groups, 1,2-propyleneoxy groups, and combinations thereof are preferable from the viewpoint of low-temperature stability and skin irritation of an external preparation containing the component (A).

In the general formula (1), m and n are 0 or an integer of 1 to 60, preferably 0 or an integer of 1 to 30, and at least one of m and n is not 0, and m + n is 1 to 120, preferably Is an integer from 1 to 60.
The compound in which both m and n are 0 includes conventionally known esterified products of 1,2-alkanediol. However, the esterified product of 1,2-alkanediol alone has skin irritation and external use. When used as a component of the agent, the low temperature stability is insufficient.

The component (A) in the present invention contains at least one alkylene ether group (—O— (AO) —) as represented by the general formula (1). The alkylene ether group is a hydrophilic group, and the presence thereof reduces the skin irritation and is presumed to be favorable for the low temperature stability of the external preparation containing the component (A).

Moreover, it is preferable that the component (A) in this invention contains 2 or more types of compounds shown by General formula (1). When two or more types are included, there may be two or more types with different R ¹ , two or more types with different A, two or more types with different X and Y, and two or more types with different m + n. Among these, 2 or more types with different R ¹ and 2 or more types with different m + n are preferable, 2 or more types with different m + n are more preferable, 3 or more types with particularly different m + n, and especially 3 to 30 different types It is preferable to have. By having two or more different m + n types, a synergistic effect is exhibited, low-temperature stability is improved, and skin irritation tends to be reduced.

When component (A) in the present invention contains two or more compounds having different m + n of the compound represented by the general formula (1), the alkylene oxide is usually added to the 1,2-diol represented by the general formula (2). Is a carboxylic acid ester of an alkylene oxide adduct obtained by addition reaction.

In the formula, R ¹ is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms.

In general, an alkylene oxide adduct is a mixture of two or more kinds of compounds having a distribution of the number of added moles of alkylene oxide and different numbers of added moles.
In the present invention, the average addition mole number of alkylene oxide per molecule of 1,2-diol is preferably 0.5 to 50, more preferably 0.5 to 40, and particularly preferably 0.5 to 30. When the average added mole number is 0.5 or more, the low-temperature stability of the external preparation containing the component (A) is easily exhibited, and the skin irritation is reduced. Further, when the average added mole number is 60 or less, particularly 40 or less, the low temperature stability is easily exhibited sufficiently. Moreover, the added mole number of alkylene oxide in each compound constituting the mixture is preferably 1 to 120, more preferably 1 to 60.

In addition, in the alkylene oxide adduct, a compound having 0 addition moles, that is, a smaller amount of unreacted 1,2-diol is preferred, but when 1,2 diol is subjected to addition reaction with a relatively small number of moles of alkylene oxide. In addition, unreacted 1,2-diol tends to remain. The content of unreacted 1,2-diol is preferably less than 50% by weight, more preferably 40% by weight or less, particularly preferably based on the weight (100% by weight) of the obtained alkylene oxide adduct. 30% by weight or less. If it is less than 50% by weight, the effects of the present invention are easily exerted, the odor is small, and it is preferable from the viewpoint of low-temperature stability and skin irritation of an external preparation containing the component (A) that is the carboxylic acid ester. Even if less than 50% by weight of unreacted 1,2-diol remains, if the alkylene oxide adduct is present, the low-temperature stability of the carboxylic acid ester exhibits the effect of the alkylene oxide adduct. There is a tendency. Similarly, regarding the skin irritation, even if unreacted 1,2-diol is contained, the effect of the carboxylic acid ester on the skin irritation tends to be canceled by the alkylene oxide adduct.

The alkylene oxide adduct of 1,2-diol can be produced by a usual alkylene oxide addition reaction.

For example, 1,2 diol represented by the general formula (2) may be added to an alkaline catalyst (alkali metal hydroxide, alkaline earth metal hydroxide, alkaline earth metal oxide, etc.) or acid catalyst (sulfuric acid, hydrochloric acid, etc.). Inorganic acids, Lewis acids such as BF ₃ ), and the like, and a reaction is performed while injecting a predetermined amount of alkylene oxide at a temperature of 90 to 180 ° C. and a pressure of 0.3 MPa or less. Further, a specific catalyst in the production method described in JP-A No. 2002-114844 (an acid having an acid strength H ₀ by Hammett acidity function H ₀ of −30.0 to −11.0 or a metal salt thereof, and Schrodinger's wave equation Or a strong acid salt of a metal having the lowest empty orbit in -10 to -3).

The distribution of the number of added moles of alkylene oxide can be measured under the following conditions by liquid chromatography after reacting a sample with an excess of phenyl isocyanate (special reagent grade) to label hydroxyl groups.
Model: LC-10ADVP manufactured by Shimadzu Corporation
Column: μ-Porasil (Waters)
Mobile phase: 2% isopropyl alcohol / butyl chloride
Gradient detector up to 32% isopropyl alcohol / butyl chloride; UV (240 nm)
Temperature: 40 ° C
From the ratio of the value obtained by dividing the peak area of each added mole number by the molecular weight of the corresponding added mole number compound, the weight ratio of each added mole number can be known, and the weight% can be calculated based on the ratio. .

The esterified product of the alkylene oxide adduct in the present invention can be produced by an esterification reaction between the above alkylene oxide adduct and a carboxylic acid represented by the following general formula (3) or an ester-forming derivative thereof.
R ² —COOH (3)
R ² in the formula includes the same groups as those mentioned for R ² above.
Examples of ester-forming derivatives include carboxylic acid halides (such as carboxylic acid chlorides and carboxylic acid bromides), carboxylic acid anhydrides, and carboxylic acid lower alkyl (alkyl groups having 1 to 4 carbon atoms) esters.
The esterification reaction is carried out at 80 to 150 ° C. using an inorganic acid (sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, etc.) or an organic acid (p-toluenesulfonic acid, etc.) as a catalyst when esterifying with a carboxylic acid. It is possible to proceed while removing water from the system by heating and stirring. Moreover, when esterifying with a carboxylic acid halide or a carboxylic acid anhydride, it is possible to proceed by heating and stirring at 80 to 150 ° C. using a catalyst such as a non-catalyst or pyridine.
After completion of the esterification reaction, purification may be carried out by removing the catalyst, deoxidation and decolorization as necessary.

The component (A) in the present invention is a mixture of two compounds of a compound represented by the general formula (1) wherein m is 1 and n is 0 and a compound where m is 0 and n is 1. In general, low molecular weight diols (2 to 6 carbon diols such as ethylene glycol, propylene glycol and butylene glycol) and long chain aliphatic 1,2-epoxy compounds (for example, 1,2-epoxydodecane, etc.) The adduct is a carboxylic acid ester obtained by the reaction with A, and can be produced, for example, by the method described in JP-A No. 2003-96435.

The component (A) in the present invention is usually in a solid or liquid state at 25 ° C., and is preferably in a liquid state from the viewpoint of ease of handling.

The composition for external use of the present invention is a composition for external use containing the above component (A) as an essential component, and is used as a composition for skin such as cosmetics, quasi-drugs, and pharmaceuticals, and a composition for hair. Is. Examples of cosmetics include lotions, emulsions, creams (cleansing creams, etc.), packs, facial cleansers, foundations, lipsticks, bathing agents, and the like. Examples of the hair composition include shampoo, rinse, hair treatment, hair conditioner, hair cream and the like.

As components other than the component (A) contained in the composition for external use of the present invention, components usually blended in cosmetics, quasi drugs, pharmaceuticals and the like can be used.
For example, anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, oils, polyhydric alcohols, sugars, vitamins, plant extracts, moisturizers, silicones, chelating agents, perfumes, antiseptics Any additive such as an agent, ultraviolet absorber, colorant and filler can be used.

Examples of the anionic surfactant include sodium lauryl sulfate, polyoxyethylene (polymerization degree = 1 to 100), sodium lauryl sulfate, polyoxyethylene (polymerization degree = 1 to 100), lauryl sulfate triethanolamine, and polyoxyethylene (polymerization degree = 1-100) Sodium lauryl ether acetate, polyoxyethylene (degree of polymerization = 1-100) Coconut oil fatty acid sodium monoethanolamide sulfate, polyoxyethylene (degree of polymerization = 1-100) disodium lauryl sulfosuccinate, polyoxysulfosuccinate Ethylene (degree of polymerization = 1-100) Lauroylethanolamide disodium, coconut oil fatty acid methyl taurine sodium, coconut oil fatty acid sarcosine sodium, coconut oil fatty acid sarcosine triethanolamine, N-coconut oil fatty acid acyl-L-g Glutamic acid triethanolamine, N- cocoyl -L- glutamate sodium lauroyl methyl -β- sodium alanine, and sodium lauryl phosphate and the like.

Nonionic surfactants include 1: 1 coconut oil fatty acid diethanolamide, lauryl dimethylamine oxide, glyceryl monostearate, ethylene glycol monostearate, polyethylene glycol monostearate (polymerization degree = 1-100), distearic acid. Polyethylene glycol (degree of polymerization = 1 to 100), polyoxyethylene (degree of polymerization = 1 to 100) higher alcohol (carbon number 8 to 32) ether, sorbitan monolaurate, polyoxyethylene monolaurate (degree of polymerization = 1 to 100) Examples include sorbitan, polyoxyethylene (polymerization degree = 1 to 100) dioleic acid methyl glucoside, polyoxyethylene (polymerization degree = 1 to 100) beef tallow alkyl hydroxymyristyl ether, and ethylene glycol monostearate.

Examples of cationic surfactants include cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride, distearyldimethylammonium chloride, ethyl lanolin sulfate fatty acid aminopropylethyldimethylammonium, and lactate of diethylaminoethylamide stearate. .

Amphoteric surfactants include coconut oil fatty acid amidopropiyldimethylaminoacetic acid betaine, lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, laurylhydroxysulfobetaine, lauroylamidoethyl Examples thereof include sodium hydroxyethylcarboxymethylbetaine hydroxypropyl phosphate, sodium β-laurylaminopropionate and the like.

Oils include hydrocarbons (liquid paraffin, squalane, etc.), higher alcohols (coconut oil alcohol, cetyl alcohol, isostearyl alcohol, etc.), higher fatty acids (coconut oil fatty acid and isostearic acid, etc.), synthetic ester oils (isopropyl myristate, 2-octyldodecyl myristate, octyl palmitate and cetyl 2-ethylhexanoate, silicone oil (such as methylpolysiloxane and methylphenylpolysiloxane) and vegetable oil (safflower oil, sunflower oil, rosemary oil, jojoba oil, Macadamia nut oil, olive oil, camellia oil and castor oil).

Examples of the humectant include polyhydric alcohols such as glycerin, 1,3-butylene glycol, 1,3-butanediol, and propylene glycol. Examples of silicone include dimethylpolysiloxane, modified silicon in which various organic groups are introduced into part of the methyl group of dimethylpolysiloxane, and cyclic dimethylsiloxane. Examples of the chelating agent include sodium ethylenediaminetetraacetate and sodium 1-hydroxyethane-1,1-diphosphonate. Examples of the preservative include benzoic acids, sorbic acids, and tribromosaran. Examples of the ultraviolet absorber include benzophenone derivatives, p-aminobenzoic acid derivatives, salicylic acid derivatives, and the like. Colorants include inorganic pigments (titanium oxide, lithopone, lead white, zinc white, cobalt compounds, etc.) and organic pigments (azo lakes, monoazos, disazos, chelate azos, etc., benzimidazolones, phthalocyanines Quinacridone, dioxazine, isoindolinone, thioindigo, perylene, quinophthalone, and anthraquinone pigments). Examples of the filler include inorganic powders (talc, mica, kaolin, calcium carbonate, aluminum oxide, magnesium silicate, etc.) and organic powders (protein powder, nylon powder, acrylic powder, urethane powder, etc.).

The external preparation composition of the present invention may further contain water and a hydrophilic solvent. Examples of the hydrophilic solvent include lower alcohols (alcohols having 1 to 4 carbon atoms such as methanol, ethanol, and propanol).

In the external preparation composition of the present invention, when the components other than water and the hydrophilic solvent are defined as “solid content”, the concentration of the solid content is usually 1 to 100%, preferably 3 to 95%. The content of the component (A) in the solid content is 10 to 100% of the solid content of 100%, preferably 20 to 100%, and the content of the other components is 0 to 90%, preferably 0 to 0%. 80%. Each content of other components in the solid content is anionic surfactant, nonionic surfactant, cationic surfactant, amphoteric surfactant, fats and oils, polyhydric alcohols, saccharides, humectant, coloring The amount of the material and the filler is 50% or less, preferably 40% or less, respectively, and the vitamins, plant extract, silicone, chelating agent, fragrance, preservative and ultraviolet absorber are each 20% or less, preferably 10% or less. is there.

[Example]
EXAMPLES Hereinafter, the present invention will be further described with reference to examples, but the present invention is not limited thereto. The part in an Example shows a weight part and% shows weight%.

Production Example 1
To a glass autoclave with stirring and temperature control functions, 202 parts (1, 1 part by mole) of 1,2-n-dodecanediol and 0.2 part of potassium hydroxide were added, and the inside of the mixed system was replaced with nitrogen. Dehydration was performed at 120 ° C. for 1 hour under reduced pressure (about 20 mmHg). Subsequently, 55 parts (1.25 mol parts) of EO was introduced at 150 ° C. so that the gauge pressure was 1 to 3 kgf / cm ² . After 8 hours, 257 parts of 1,2-n-dodecanediol EO adduct (A ₀ -1) in which a predetermined amount of EO was introduced was obtained. The added mole number distribution of EO is shown in Table 1.
257 parts (1 mole part) of the above (A ₀ -1), 440 parts (2.2 mole parts) of lauric acid, 700 parts of toluene and p-toluenesulfonic acid in a glass Kolben with stirring and temperature control functions 5 parts were charged and the esterification reaction was carried out at 115 ° C. for 8 hours while removing water under reflux. After completion of the reaction, the mixture was cooled to 20 ° C., 200 parts of a 5% aqueous sodium hydroxide solution was added with stirring, allowed to stand for 3 hours, and then the lower layer was separated and the upper layer was distilled at 80 ° C. under reduced pressure. And filtered at 50 ° C. to obtain an esterified product (A-1).

Production Example 2
Into a glass autoclave with stirring and temperature control functions, 174 parts (1, mol part) of 1,2-dihydroxy-n-decane and 0.2 part of aluminum perchlorate 9 hydrate were added, and the inside of the mixed system was nitrogen. Then, dehydration was performed at 120 ° C. for 1 hour under reduced pressure (about 20 mmHg). Next, 110 parts (2.5 mole parts) of EO was introduced at 95 ° C. so that the gauge pressure was 1 to ² kgf / cm ² . After 8 hours, 284 parts of 1,2-n-decanediol EO adduct (A ₀ -2) into which a predetermined amount of EO was introduced were obtained. The added mole number distribution of EO is shown in Table 1.
In a glass Kolben with stirring and temperature control functions, 284 parts (1 mole part) of the above (A ₀ -2), 316.8 parts (2.2 mole parts) of n-octanoic acid, 500 parts of toluene and p -5 parts of toluenesulfonic acid was charged, and the esterification reaction was carried out at 115 ° C for 8 hours while removing water under reflux. After completion of the reaction, the mixture was cooled to 20 ° C., 200 parts of a 5% aqueous sodium hydroxide solution was added with stirring, allowed to stand for 3 hours, and then the lower layer was separated and the upper layer was distilled at 80 ° C. under reduced pressure. And filtered at 50 ° C. to obtain an esterified product (A-2).

Production Examples 3-5
Manufacture except that the type and amount of raw material 1,2-diol, the amount of potassium hydroxide as a catalyst, the type and amount of alkylene oxide, and the type and amount of carboxylic acid were changed as shown in Table 1. In the same manner as in Example 1, esterified products (A-3) to (A-6) of 1,2-diol alkylene oxide adducts of Production Examples 3 to 5 were obtained. These added mole number distributions are shown in Table 1.

Comparative production example 1
In a glass Kolben with stirring and temperature control function, 202 parts (1 mol part) of 1,2-n-dodecanediol, 440 parts (2.2 mol parts) of n-lauric acid, 600 parts of toluene and p-toluene 5 parts of sulfonic acid was charged, and the esterification reaction was carried out at 115 ° C. for 8 hours while removing water under reflux. After completion of the reaction, the mixture was cooled to 20 ° C., 200 parts of a 5% aqueous sodium hydroxide solution was added with stirring, allowed to stand for 3 hours, and then the lower layer was separated and the upper layer was distilled at 80 ° C. under reduced pressure. And filtered at 50 ° C. to obtain an esterified product (X-1).

Abbreviations in Table 1 are as follows.
8D: 1,2-n-octanediol 10D: 1,2-n-decanediol 12D: 1,2-n-dodecanediol 16D: 1,2-n-hexadecanediol 24D: 1,2-n-tetraeico Sundiol EO: ethylene oxide PO: 1,2-propylene oxide

Examples 1-5, Comparative Examples 1-3
<Production of oil-based cleansing composition>
(A-1) to (A-5) obtained in the above production examples, and comparative products (A ₀ -1), (A ₀ -2) and (X-1) are shown in Table 2. In addition, liquid paraffin and octyl palmitate as liquid oil were blended in the number of parts shown in Table 2 to prepare an oil-based cleansing composition.
(1) Evaluation of low temperature stability About each oil-based cleansing composition, it left still at 25 degreeC and 0 degreeC for 24 hours, and -5 degreeC for 6 months, and the change of the external appearance was observed visually. The results are shown in Table 2.
Evaluation criteria ○; Clear liquid △; Slightly turbid / Slightly separable ×; Slightly turbid / Separated (2) Evaluation of skin irritation Each oil-based cleansing composition was prepared and a human patch test (five men and women) (Closed, 48 hours, inner side of upper arm) was evaluated according to the following criteria and expressed as the total score.
Evaluation criteria No reaction (erythema); 3 points Very mild erythema; 2 points Clear erythema; 1 point Intense erythema; 0 points

(3) Ease of washing, evaluation of freshness after washing and moisturizing 20 panelists applied the foundation to the entire face and allowed to dry for about 30 minutes, then took 3 mL of each cleansing composition and used their fingers Then stretched over the entire face and blended well with the foundation, and then washed off with hot water of about 35 ° C. Ease of washing at this time, a refreshing feeling after washing, and a moist feeling (wetability) were expressed by the following scoring standards and evaluated by an average score of 20 people.
Scoring criteria Very good; 5 points Good; 4 points Normal; 3 points Bad; 2 points Very bad; 1 point

(4) Evaluation of emulsifiability with water 1 g of each cleansing composition and 19 g of water were placed in a 50 mL screw tube, shaken and mixed for 30 seconds, and the appearance after standing for 1 hour was observed with the naked eye. It was evaluated with.
Evaluation criteria ○; Uniformly milky white (good emulsification)
Δ: Uniform but lightly cloudy (slightly emulsified)
×: Not uniform, oil droplets are separated (emulsified)

(5) Evaluation of Detergency Makeup (lip color red, 50 mg / 4 cm ² ) was uniformly applied to the forearm and dried at room temperature for 5 minutes. Then, 1.0 g of each cleansing composition was applied to the entire application part for about 30 seconds using a finger in the same manner as a normal makeup remover, and then rinsed off without rubping with 35 ° C. tap water, and the makeup after drying. The residual rate was determined and the cleaning power was evaluated according to the following criteria. The makeup remaining rate was determined by measuring the color before and after the lip color application and after using the cleansing composition using a spectrocolorimeter (Spectro Photometer SD5000, manufactured by Nippon Denshoku), and obtaining the cleaning power from the following formula.
Detergency (%) = 100 − [(E2−E0) / (E1−E0)} × 100
E0; Color before applying lip color E1; Color after applying lip color E2; Color after using cleansing material

  As can be seen from Table 2, excellent evaluation results were obtained in Examples 1 to 5 which are the compositions of the present invention.

Examples 6-10, Comparative Examples 4-6
<Manufacture of hair conditioners>
(A-1) to (A-5) obtained in the above production examples and comparative products (A ₀ -1), (A ₀ -2), (X-1) In addition, a hair conditioner (100 parts) was prepared using the following ingredients as other ingredients.

Any one of (A-1) to (A-5), comparative product (A ₀ -1), (A ₀ -2), and (X-1)
2.0 parts polyoxyethylene (average 10 moles) cetyl ether 1.0 part stearyltrimethylammonium chloride 2.0 parts cetyl alcohol 5.0 parts glycerin 5.0 parts methyl paraoxybenzoate 0.1 part purified water remainder

(1) Evaluation of low-temperature stability About each hair conditioner, it left still at 25 degreeC and 0 degreeC for 24 hours, and -5 degreeC for 6 months, and the change of the external appearance was observed visually. The results are shown in Table 3.
Evaluation criteria ○; Clear liquid △; Slightly turbid / slightly separable ×; Remarkably turbid / separated (2) Evaluation of hair flexibility and moisturizing For each hair conditioner, 20 female panelists per day The hair was soft (softness) and moisturized (wetability) using the following scoring standards and evaluated by the average score of 20 people.
Scoring criteria Very good; 5 points Good; 4 points Normal; 3 points Bad; 2 points Very bad; 1 point

As can be seen from Table 3, excellent evaluation results were obtained for Examples 6 to 10 which are the compositions of the present invention.

The external composition of the present invention can be used as a cosmetic composition, a quasi-drug, a dermatological composition such as a pharmaceutical, and a hair composition. Examples of the cosmetics include lotions, emulsions, creams, packs, facial cleansers, foundations, lipsticks, bathing agents and the like.
Examples of the hair composition include shampoo, rinse, hair treatment, hair conditioner, hair cream and the like.

Claims (6)

A composition for external use comprising, as an essential component, a component (A) composed of one or more of the compounds represented by the general formula (1).
(In the formula, R ¹ is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms; X and Y is an acyl group represented by hydrogen or -CO-R ^2, R ² is 1 to the number of carbon atoms 30 aliphatic or alicyclic hydrocarbon groups, wherein at least one of X and Y is an acyl group; AO is an alkyleneoxy group having 2 to 6 carbon atoms; m and n are 0 or 1 to 60 (At least one is not 0.) Component (A) is an esterified product of an alkylene oxide adduct obtained by addition reaction of alkylene oxide with 1,2-diol represented by general formula (2) and a carboxylic acid or an ester-forming derivative thereof. Item 1. A composition for external use according to Item 1.
(In the formula, R ¹ is an aliphatic or alicyclic hydrocarbon group having 6 to 30 carbon atoms.) The composition for external use according to claim 2, wherein the alkylene oxide adduct is an adduct obtained by adding alkylene oxide to 1,2-diol at an average addition mole number of 0.5 to 50. The composition for external use according to claim 2 or 3, wherein the content of unreacted 1,2-diol in the alkylene oxide adduct is less than 50% by weight based on the weight of the alkylene oxide adduct. The external composition according to any one of claims 1 to 4, wherein the external composition is a cosmetic. The composition for external use according to any one of claims 1 to 4, wherein the composition for external use is for hair.