JP2006225371A - Pharmaceutical preparation for protecting skin - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pharmaceutical preparation for protecting the skin and effectively relieving stimulation on the skin caused by a stimulating substance, to provide a method for protecting the skin by applying the pharmaceutical preparation before or after applying the stimulus substance on the skin. <P>SOLUTION: The pharmaceutical preparation for protecting the skin is obtained by containing one or more acyl compounds having two or more acyl groups and two or more hydrophilic groups in a molecule. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a preparation for protecting the skin comprising an acyl compound having a specific structure, and a method for protecting the skin, wherein the preparation for protecting the skin is applied before and / or after applying an irritant substance to the skin. About.

Conventionally, surfactants have been important constituents in cosmetic compositions and detergent compositions as detergents such as shampoos and dishwashing agents, and as emulsifiers and solubilizers in cosmetics such as emulsions and creams. It is often used. However, on the other hand, the surfactant has a strong skin irritation and has a protein denaturing action, and is known to cause rough skin when used for a long time or when a person with weak skin is used. In addition, since general-purpose surfactants have strong irritation to mucous membranes and the like, they have not been used for drug applications that come into contact with skin or mucosal tissues such as drugs for external use.
In recent years, the number of allergic patients and people with sensitive skin has increased, and the number of people who feel irritation with cosmetics and the like has increased, and there is a demand for products with lower irritation. For example, as disclosed in Patent Document 1, an amino acid base material is used. Development of products using low-irritant surfactants has been underway, but this is not sufficient. Therefore, development of a preparation that protects the skin having a function of mitigating irritation to an irritating substance without affecting the function of a surfactant or the like has been eagerly desired.

Japanese Patent Laid-Open No. 10-182367

  The present invention relates to a preparation for protecting the skin that can alleviate the protein denaturing action by a stimulating substance such as a surfactant, and to protect the skin to which the preparation is applied before and / or after applying the stimulating substance to the skin. The purpose of this is to provide a method.

As a result of intensive studies to solve the above problems, the present inventors have paid attention to a compound having two or more acyl groups and hydrophilic groups in the molecule (acyl compound), which is used as a surfactant or the like. It has been found that by applying a substance having strong irritation to the skin before and / or after application to the skin, protein denaturation is alleviated and irritation is alleviated, and the present invention has been completed.
That is, the present invention is as follows.
1. A preparation for protecting the skin comprising one or more acyl compounds each having two or more acyl groups and hydrophilic groups in the molecule.
2. At least one acyl compound has an amino acid residue in the molecule. A preparation for protecting the skin according to 1.
3. The preparation for protecting skin according to either 1. or 2. wherein at least one of the acyl compounds is a compound represented by the following general formula (1).

(In the above general formula (1), X is a linear, branched, cyclic or aromatic hydrocarbon chain having a molecular weight of 1,000,000 or less, which may have m functional groups and other substituents. N (m ≧ n) Qs bonded to X are substituents represented by the following general formula (2), which may be the same as or different from each other. In Formula (2), Z is a bond derived from a functional group of X, R ¹ CO represents a long-chain acyl group derived from a saturated or unsaturated fatty acid having 2 to 20 carbon atoms, R ² represents hydrogen, or a lower alkyl group having 1 to 3 carbon atoms which may be substituted with a hydroxyl group or a carboxyl group, and Y represents a carboxyl group, a sulfonic acid group, a sulfate group, or a phosphate group. Or show their salts j, k is any of independently 0,1,2, and j, k is an integer of .n 2 to 20 do not represent 0 at the same time.)

4.1. ~ 3. A paper or fiber containing the preparation for protecting the skin according to any one of the above, or a sheet-like material comprising the same.
5. 1. applying irritant to skin before and / or after application to skin ~ 3. The formulation which protects the skin in any one of.
6). 5. The paper, fiber or sheet-like material comprising the same according to 4, wherein the irritating substance is applied to the skin before and / or after being applied to the skin.
7). A method for protecting skin, comprising applying the preparation for protecting skin according to any one of 1 to 4 before and / or after applying an irritating substance to the skin.
8). 3. before and / or after applying the irritant to the skin; A method for protecting the skin, which comprises applying the paper, fiber, or a sheet-like material comprising them to the skin.

  The present invention provides a preparation that protects the skin against irritation such as a surfactant and protects the skin by applying the preparation before and / or after applying the irritating substance to the skin. A method can also be provided.

Hereinafter, the present invention will be specifically described focusing on its preferred form.
The preparation for protecting the skin of the present invention is structurally a composition comprising at least one acyl compound having two or more acyl groups and hydrophilic groups in the molecule. A compound known so far may be used.
The acyl groups are each independently, that is, each may be different or the same, and those derived from a saturated or unsaturated fatty acid having 2 to 20 carbon atoms are preferable, and may be linear, branched or cyclic. Absent.

For example, acetic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid , Linear fatty acids such as nonadecanoic acid, arachidic acid;
2-butyl-5-methylpentanoic acid, 2-isobutyl-5-methylpentanoic acid, dimethyloctanoic acid, dimethylnonanoic acid, 2-butyl-5-methylhexanoic acid, methylundecanoic acid, dimethyldecanoic acid, 2-ethyl- 3-methylnonanoic acid, 2,2-dimethyl-4-ethyloctanoic acid, methyldocosanoic acid, 2-propyl-3-methylnonanoic acid, methyltridecanoic acid, dimethyldodecanoic acid, 2-butyl-3-methylnonanoic acid, methyltetradecanoic acid , Ethyltridecanoic acid, propyldodecanoic acid, butylundecanoic acid, pentyldecanoic acid, hexylnonanoic acid, 2- (3-methylbutyl) -3-methylnonanoic acid, 2- (2-methylbutyl) -3-methylnonanoic acid, butylethylnonane Acid, methylpentadecanoic acid, ethyltetradecanoic acid, propyltri Canic acid, butyldodecanoic acid, pentylundecanoic acid, hexyldecanoic acid, heptylnonanoic acid, dimethyltetradecanoic acid, butylpentylheptanoic acid, trimethyltridecanoic acid, methylhexadecanoic acid, ethylpentadecanoic acid, propyltetradecanoic acid, butyltridecanoic acid, pentyldodecane Acid, hexylundecanoic acid, heptyldecanoic acid, methylheptylnonanoic acid, dipentylheptanoic acid, methylheptadecanoic acid, ethylhexadecanoic acid, ethylhexadecanoic acid, propylpentadecanoic acid, butyltetradecanoic acid, pentyltridecanoic acid, hexyldodecanoic acid, heptyl Undecanoic acid, octyldecanoic acid, dimethylhexadecanoic acid, methyloctylnonanoic acid, methyloctadecanoic acid, ethylheptadecanoic acid, dimethylheptadecanoic acid, Octyl decanoic acid, Mechirunonadekan acid, Mechirunonadekan acid, dimethyl octadecanoic acid, branched fatty acids such as butyl heptyl nonanoic acid;

Octenoic acid, nonenoic acid, decenoic acid, caproleic acid, undecylenic acid, Lindellic acid, touric acid, lauroleic acid, tridecenoic acid, tuzuic acid, myristoleic acid, pentadecenoic acid, hexedenoic acid, palmitoleic acid, heptadecenoic acid, octadecenoic acid, Linear monoenoic acids such as oleic acid, nonadecenoic acid, gondoic acid;
Such as methylheptenoic acid, methylnonenoic acid, methylundecenoic acid, dimethyldecenoic acid, methyldodecenoic acid, methyltridecenoic acid, dimethyldodecenoic acid, dimethyltridecenoic acid, methyloctadecenoic acid, dimethylheptadecenoic acid, ethyloctadecenoic acid Branched monoenoic acid;

Di- or trienoic acids such as linoleic acid, linoleic acid, eleostearic acid, linolenic acid, linolenic elaidic acid, pseudoeleostearic acid, parinaric acid, arachidonic acid;
Acetylene acids such as octinoic acid, nonic acid, decinic acid, undecinic acid, dodecinic acid, tridecinic acid, tetradecinic acid, pentadecinic acid, heptadesinic acid, octadecinic acid, nonadesinic acid, dimethyloctadesinic acid;
Of methyleneoctadecenoic acid, methyleneoctadecanoic acid, aleprolic acid, alepresinic acid, allepuric acid, alepuric acid, hydnocarpic acid, shoulmuccinic acid, gorulic acid, α-cyclopentylic acid, α-cyclohexylic acid, α-cyclopentylethylic acid And acyl groups derived from such cyclic acids.

  Moreover, the acyl group derived from the fatty acid obtained from natural fats and oils may be sufficient, and the acyl group derived from the mixed fatty acid containing 80% or more of the saturated or unsaturated fatty acid having 2 to 20 carbon atoms is preferable. For example, acyl groups derived from palm oil fatty acid, palm oil fatty acid, linseed oil fatty acid, sunflower oil fatty acid, soybean oil fatty acid, sesame oil fatty acid, castor oil fatty acid, olive oil fatty acid, camellia oil fatty acid, rapeseed oil fatty acid, palm kernel oil fatty acid, etc. Etc. Two or more of these acyl compounds may be used in combination. The acyl group preferably has 8 to 20 carbon atoms.

  In the preparation for protecting the skin of the present invention, the acyl compound and the hydrophilic group are each independently a carboxyl group, a sulfonic acid group, a sulfuric acid residue, a phosphoric acid residue or a salt thereof, or an oxyalkylene group, polyethylene It has a glycol group or the like, or an amino group, a quaternary ammonium group, a pyridinium group, a sulfonium group or a salt thereof. The hydrophilic group of the acyl compound is preferably each independently a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group or a salt thereof.

  When the acyl compound is used as a salt, examples thereof include alkali metal salts, alkaline earth metal salts, ammonium salts, organic amine salts, basic amino acid salts, and the like. Specifically, alkalis such as sodium, potassium, and lithium are used. Arbitrary metals such as metals, alkaline earth metals such as calcium and magnesium, metals such as aluminum and zinc, organic amines such as ammonia, monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, and basic amino acids such as arginine and lysine It is a salt with 1 type, or 2 or more types chosen by these. Among these, sodium salts, potassium salts, organic amine salts, and basic amino acid salts are particularly preferable.

In the present invention, it is preferable that at least one of the acyl compounds contained in the preparation for protecting the skin is an acyl compound represented by the above general formulas (1) and (2).
The acyl compound here is structurally a structure in which a compound having at least one acyl group and a hydrophilic group in the molecule is connected by an appropriate spacer as shown in the general formulas (1) and (2). belongs to.
In the above general formula (2), the acyl groups represented by R ¹ CO are independent, that is, they may be different or the same, and are derived from a saturated or unsaturated fatty acid having 2 to 20 carbon atoms as described above. Any of straight-chain, branched, and cyclic structures can be used.
In the general formula (2), the acyl group represented by R ¹ CO is preferably derived from a saturated or unsaturated fatty acid having 8 to 20 carbon atoms.

In the general formula (2), R ² is hydrogen, or the number of carbon atoms that may be substituted by a hydroxyl group or a carboxyl group, a sulfonic acid group, a sulfate ester group, a phosphate ester group, or a salt thereof. 1 to 3 lower alkyl groups, for example, methyl group, ethyl group, propyl group, isopropyl group, hydroxymethyl group, hydroxyethyl group, hydroxy (iso) propyl group, dihydroxy (iso) propyl group, carboxymethyl group, A carboxyethyl group, a carboxypropyl group, a sulfoethyl group, etc. are mentioned.
In the general formula (1), n substituents Q bonded to X (the above general formula (2)) may be different from each other or the same. Moreover, the said General formula (2) shows what the so-called acidic amino acid was N-acylated, and it does not ask | require whether they are optical isomers, for example, D-form, L-form, and a racemate.

The acidic amino acid is a monoaminodicarboxylic acid having 2 and 1 carboxyl groups and 1 amino group, respectively, in the molecule, and the amino group may be an N-methyl group or an N-ethyl group. It does not matter whether it is an optical isomer, for example, a D-form, an L-form, or a racemate. Examples of acidic amino acids include glutamic acid, aspartic acid, lanthionine, β-methyllanthionine, cystathionine, diencholic acid, ferrinin, aminomalonic acid, β-oxyaspartic acid, α-amino-α-methylsuccinic acid, β-oxyglutamic acid. , Γ-oxyglutamic acid, γ-methylglutamic acid, γ-methyleneglutamic acid, γ-methyl-γ-oxyglutamic acid, α-aminoadipic acid, α-amino-γ-oxyadipic acid, α-aminopimelic acid, α-amino- Examples thereof include γ-oxypimelic acid, β-aminopimelic acid, α-aminosuberic acid, α-aminosebacic acid, pantothenic acid and the like.
The n substituents (the above general formula (2)) attached to X are preferable because the acidic amino acid is an L-acidic amino acid molecule because it is excellent in biodegradability.

In the above general formula (2), Z represents a bonding portion (-) derived from m functional groups (hydroxyl group, amino group, thiol group) substituted with X (m ≧ n and an integer of 2 to 20). ^{O -, - NR 3 -,} - it is S-). Here, R ³ is hydrogen, or an alkyl group, alkenyl group, aryl group or alkylaryl group having 1 to 10 carbon atoms.
In the general formula (1), X is a linear, branched or cyclic chain having a molecular weight of 1 million or less and having m functional groups consisting of one or more selected from a hydroxyl group, an amino group and a thiol group. Or it is a spacer which is an aromatic hydrocarbon chain | strand, and X may have substituents other than the said hydroxyl group, an amino group, and a thiol group.
In the general formula (1), X is preferably a residue of an m-valent compound having a molecular weight of 1 million or less and having m functional groups of one kind or two or more kinds selected from a hydroxyl group, an amino group and a thiol group. And a compound residue that may have a substituent other than a hydroxyl group, an amino group, and a thiol group. Here, the m-valent compound means that a bond derived from m functional groups can be formed. It does not matter whether they are optical isomers such as D-form, L-form, and racemate.

Examples of such m-valent compounds include amino acids such as serine, threonine, cysteine, cystine, cystine disulfoxide, cystathionine, methionine, arginine, lysine, tyrosine, histidine, tryptophan, and oxyproline;
Aminoethanol, aminopropanol, aminobutanol, aminopentanol, aminohexanol, aminopropanediol, aminoethylethanolamine, aminoethylaminoethanol, aminocresol, aminonaphthol, aminonaphtholsulfonic acid, aminohydroxybenzoic acid, aminohydroxybutanoic acid Compounds having an amino group and a hydroxyl group in the molecule such as aminophenol, aminophenethyl alcohol, glucosamine;

Compounds having a thiol group and a hydroxyl group in the molecule such as mercaptoethanol, mercaptophenol, mercaptopropanediol, glucothiose;
Compounds having a thiol group and an amino group in the molecule such as aminothiophenol and aminotriazole thiol;
Is mentioned. Further, proteins, peptides, etc., or those obtained by hydrolyzing them may be used.

In the general formula (1), X is preferably an m-valent (m ≧ n) polyhydroxyl compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than a hydroxyl group. Here, the m-valent polyhydroxyl compound means that m ester bonds can be formed. It does not matter whether they are optical isomers such as D-form, L-form, and racemate.
Examples of such m-valent polyhydroxyl compounds include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, and 1,4-butanediol. , Pentanediol, 1,6-hexanediol, cyclohexanediol, dimethylolcyclohexane, neopentyl glycol, 1,8-octanediol,

2,2,4-trimethyl-1,3-pentanediol, isoprene glycol, 3-methyl-1,5-pentanediol, sorbite, catechol, resorcin, hydroquinone, bisphenol A, bisphenol F, hydrogenated bisphenol A, hydrogenated Bisphenol F,
Dimerdiol, dimethylolpropionic acid, dimethylolbutanoic acid, tartaric acid, dihydroxytartaric acid, mevalonic acid, 3,4-dihydroxycinnamic acid, 3,4-dihydroxyhydrocinnamic acid, hydroxybenzoic acid, dihydroxystearic acid, dihydroxyphenylalanine And divalent hydroxyl compounds such as each of these isomers;

Glycerin, trioxyisobutane, 1,2,3-butanetriol, 1,2,3-pentanetriol, 2-methyl-1,2,3-propanetriol, 2-methyl-2,3,4-butanetriol, 2-ethyl-1,2,3-butanetriol, 2,3,4-pentanetriol,
2,3,4-hexanetriol, 4-propyl-3,4,5-heptanetriol, 2,4-dimethyl-2,3,4-pentanetriol, 1,2,4-butanetriol, 1,2, Trivalent polyhydroxyl compounds such as 4-pentanetriol, trimethylolethane, trimethylolpropane, diethanolamine, triethanolamine, trihydroxystearic acid;

Pentaerythritol, erythritol, 1,2,3,4-pentanetetrol, 2,3,4,5-hexanetetrol, 1,2,4,5-pentanetetrol, 1,3,4,5-hexane Tetravalent polyhydroxyl compounds such as tetrol, diglycerin and sorbitan;
Pentavalent polyhydroxyl compounds such as adonitol, arabitol, xylitol, triglycerin;
Hexavalent polyhydroxyl compounds such as dipentaerythritol, sorbitol, mannitol, iditol, inositol, dulcitol, talose, allose;
Or these dehydration condensates, polyglycerol, etc. are mentioned.

Sugars such as tetroses such as erythrose, sreose, erythrulose;
Pentose such as ribose, arabinose, xylose, lyxose, xylulose, ribulose; monosaccharides such as hexose such as allose, altrose, glucose, mannose, guylose, idose, galactose, talose, fructose, sorbose, psicose, tagatose;
Examples thereof include oligosaccharides such as maltose, isomaltose, cellobiose, gentiobiose, melibiose, lactose, tulanose, trehalose, saccharose, mannitolose, cellotriose, gentianose, raffinose, meletitose, cellotetorose, stachyose and the like.

In addition, other saccharides such as heptose, deoxy sugar, amino sugar, thio sugar, seleno sugar, aldone sugar, uronic acid, sugar acid, ketoaldonic acid, anhydro sugar, unsaturated sugar, sugar ester, sugar ether, glycoside, etc. It may be a group, and may be a polysaccharide such as starch, glycogen, cellulose, chitin, chitosan or the like, or a hydrolyzed product thereof.
In the general formula (1), X is preferably an m-valent polyamino compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than an amino group. Here, the m-valent polyamino compound means that m acid amide bonds can be formed. It does not matter whether they are optical isomers such as D-form, L-form, and racemate.

Examples of such m-valent polyamino compounds include N, N′-dimethylhydrazine, ethylenediamine, N, N′-dimethylethylenediamine, diaminopropane, diaminobutane, diaminopentane, diaminohexane, diaminoheptane, diaminooctane, diaminononane, Aliphatic diamines such as diaminodecane, diaminododecane, diaminoadipic acid, diaminopropanoic acid, diaminobutanoic acid and their isomers;
Diethylenetriamine, triaminohexane, triaminododecane, 1,8-diamino-4-aminomethyl-octane, 2,6-diaminocapric acid-2-aminoethyl ester, 1,3,6-triaminohexane, 1,6 , 11-triaminoundecane, aliphatic triamines such as di (aminoethyl) amine and isomers thereof;

Alicyclic polyamines such as diaminocyclobutane, diaminocyclohexane, 3-aminomethyl-3,5,5-trimethylcyclohexylamine, triaminocyclohexane;
Aromatic polyamines such as diaminobenzene, diaminotoluene, diaminobenzoic acid, diaminoanthraquinone, diaminobenzenesulfonic acid, diaminobenzoic acid, and their respective isomers;
Diaminoxylene, di (aminomethyl) benzene, di (aminomethyl) pyridine, di (
Araliphatic polyamines such as aminomethyl) naphthalene and isomers thereof;
And polyamines substituted with hydroxyl groups such as diaminohydroxypropane and isomers thereof.

In the general formula (1), X is preferably an m-valent polythiol compound residue having a molecular weight of 1,000,000 or less, which may have a substituent other than a thiol group. Here, the m-valent polythiol compound means that m thioester bonds can be formed. It does not matter whether they are optical isomers such as D-form, L-form, and racemate.
Examples of such m-valent polythiol compounds include dithiol compounds such as dithioethylene glycol, dithioerythritol, and dithiothreitol.
X is preferably a group having 1 to 40 carbon atoms among the residues of the compounds listed above, and more preferably X has 1 to 20 carbon atoms. X is preferably a naturally occurring type from the viewpoint of excellent biodegradability.

In the general formula (2), a carboxyl group represented by Y, a sulfonic acid group, a sulfuric ester group, a phosphoric ester group, and a carboxyl group, a sulfonic acid group, a sulfuric ester group, a phosphoric ester group, etc. that can be contained in X Can form salts with various basic substances.
Examples of such salts include alkali metal salts, alkaline earth metal salts, ammonium salts, organic amine salts, basic amino acid salts, polyvalent metal salts, and the like, specifically, alkalis such as sodium, potassium, and lithium. Metals, alkaline earth metals such as calcium and magnesium, metals such as aluminum, zinc, iron, cobalt, titanium and zirconium, organic amines such as ammonia, monoethanolamine, diethanolamine, triethanolamine and triisopropanolamine, arginine and lysine Or a salt with one or more kinds selected arbitrarily from basic amino acids and the like.

  The method for producing the acyl compound represented by the general formula (1) is selected from an N-acyl acidic amino acid anhydride represented by the following general formula (3) and a hydroxyl group, an amino group, and a thiol group in the molecule. By reacting the compound having one or more kinds of m functional groups in water and / or a mixed solvent of water and an organic solvent, or tetrahydrofuran, benzene, toluene, xylene, carbon tetrachloride It can be obtained by reacting using an inert solvent such as chloroform, acetone or the like, or mixing at a temperature not lower than -5 ° C to 200 ° C at any melting point or higher without solvent.

Alternatively, the acyl compound represented by the general formula (1) includes an N-acyl acidic amino acid mono-lower ester (for example, methyl ester, ethyl ester) and a polyhydroxyl compound, a polyamino compound, or a polythiol compound, or a hydroxyl group, amino group in the molecule. A compound having any two or three of a group and a thiol group is dissolved in a suitable solvent such as dimethylformamide, a catalyst such as potassium carbonate is added, and the reaction is heated at -5 ° C to 250 ° C under reduced pressure. It can be obtained by removing the reaction solvent. Alternatively, the acyl compound can be obtained by melting with heating without a solvent, adding a catalyst such as sodium hydroxide, and performing a transesterification reaction at room temperature to 250 ° C.

The thus-obtained preparation for protecting the skin of the present invention can be used in various forms depending on the purpose such as liquid, solid, gel, paste, slurry, mist and the like. However, it is not limited to this form.
The amount of the acyl compound in the preparation for protecting the skin of the present invention is not particularly limited. For example, in a product such as a cosmetic composition, a detergent composition or an external medicine composition, the acyl compound content is 0.001 to 0.001. It is preferably 50% by weight, and can be adjusted according to the purpose. More preferably, it is 0.01 to 30% by weight in the composition.

Further, the acyl compound in the preparation for protecting the skin of the present invention can be used in a wide pH range of preferably 3 to 12 by adjusting the neutralization rate with a basic substance, more preferably the composition. PH 4.5-11. More preferably, it can be used at pH 5-8.
Since the preparation for protecting the skin of the present invention is excellent in the effect of alleviating the irritation of an irritating substance such as a surfactant, a solvent, and other hydroxy acids, for example, an anionic, cationic, nonionic or amphoteric surfactant It can be applied as a soothing agent for all compositions containing irritating substances such as, and can be used for applications that may come into contact with the skin, mucous membranes, and the like.

For example, preparations for protecting the skin include detergent compositions (for clothing, kitchen, residential, hard surface, tableware, body, hair, food, industrial, etc.), cosmetics Compositions, contact lens preparations (cleaning solution, preservative solution, etc.) and external drugs (eye drops, eye ointments, nasal drops, ear drops, suppositories, poultices, oral preparations, vaginal cleaning agents, skin preparations, etc. It can be widely applied before and / or after the application of a composition that contacts humans.
The preparation for protecting the skin of the present invention can be used in various forms depending on the purpose such as liquid, solid, gel, paste, slurry, mist, liquid crystal, powder, aerosol and the like. However, it is not limited to this form.

The cosmetic product in the present invention is a generic name for quasi-drugs and cosmetics referred to in the Pharmaceutical Affairs Law. Specifically, quasi-drugs include mouth fresheners, odor control agents, tempered powders, hair nourishing agents, List hair removal agents, hair dyes, permanent wave agents, bath agents, medicated cosmetics, medicated toothpastes, etc.
Cosmetics include cosmetic soap, face wash (cream / paste, liquid / gel, granule / powder, aerosol, etc.), shampoo, rinse, etc.
Hair dyes, hair treatments (including cream, mist, oil, gel and other forms and split hair coats), hair set (hair oil, set lotion, curler lotion, pomade, tics, bottles Cosmetics for hair, such as oiling, hair spray, hair mist, hair liquid, hair foam, hair gel, water grease);

General cream, milky lotion (cleansing cream, cold cream, burnishing cream, hand cream, etc.), shaving cream (after shaving cream, shaving cream, etc.), lotion (hand lotion, general lotion, etc.), cologne, shaving Basic cosmetics such as lotions (after shaving lotions, shaving lotions, etc.), cosmetic oils, packs;
Oshiroi (Cream Occasion, Solid Oroze, Powder Ooiro, Talcum Powder, Kneading Oro, Baby Powder, Body Powder, Water Osoiro, etc.), Powder, Foundation (Cream, Liquid, Solid etc.), Blusher, Eyebrows, Eye Cream, Eye Makeup cosmetics such as shadow mascara;

Perfumes such as general perfume, kneaded perfume, powdered perfume; fragrance, deodorant, deodorant such as gel type, liquid type, ceramic type;
Sunscreen / sunscreen cosmetics such as sunscreen / sunscreen cream, sunscreen / sunscreen lotion, sunscreen / sunscreen oil;
Nail cosmetics such as nail cream, enamel, enamel remover;
Eyeliner cosmetics;
Lip cosmetics such as lipstick and lip balm;
Oral cosmetics such as toothpaste;
Listed are bath cosmetics such as bath salt, bath oil, and bubble bath.

Moreover, in the formulation which protects the skin of this invention, unless the objective of this invention is impaired, it can use together with various base materials according to a use and the objective.
Specifically, natural rubbers such as gum arabic and tragacanth, glucosides such as saponin, cellulose derivatives such as methylcellulose, carboxycellulose, and hydroxymethylcellulose, natural polymers such as lignin sulfonate and shellac, polyacrylates, Styrene-acrylic acid copolymer salt, vinyl naphthalene-maleic acid copolymer salt, β-naphthalene sulfonic acid formalin condensate sodium salt, anionic polymer such as phosphate, polyvinyl alcohol, polyvinyl pyrrolidone, Dispersants such as nonionic polymers such as polyethylene glycol;

Higher fatty acid salt (soap); salt of higher fatty acid having 8 to 20 carbon atoms in the hydrophobic base,
N-acyl amino acid type anionic surfactant; examples of the acyl group include those having 8 to 20 carbon atoms as described above, and examples of the constituent amino acids include the above-mentioned acidic amino acids such as glutamic acid and aspartic acid, or Glycine, alanine, valine, leucine, isoleucine, proline, methionine, cysteine, tryptophan, tyrosine, phenylalanine, asparagine, glutamine, serine, threonine, oxyproline, β-aminopropionic acid, γ-aminobutyric acid, anthranilic acid, m-amino Amino acids such as benzoic acid, p-aminobenzoic acid, etc .; alkyl ether carboxylates, amide ether carboxylates, etc., alkyl sulfate esters (AS), polyoxyethylene alkyl ether sulfates (AES), alkyl ether sulfates Acid salt, sulfate of higher fatty acid ester, sulfate of higher fatty acid alkylolamide, sulfated oil, polyoxyethylene styrenated phenyl ether sulfate, alpha-olefin sulfonate (AOS), alkylbenzene sulfonate, alkylnaphthalene Sulfonates, alkyl sulfonates (SAS), dialkyl sulfosuccinates, alpha-sulfonated fatty acid salts, alkane sulfonates, sulfonates of higher fatty acid esters, alpha-sulfonated fatty acid salts, sulfonates of higher fatty acid amides, N-acyl-N-alkyl taurate, N-acyl-N-methyl taurate, alkyl phosphate, alkyl ether phosphate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, Naphtha Anionic surfactants such as Nsurufon formalin condensate;

Amphoteric surfactants such as alkylbetaines, alkylamidobetaines, alkylsulfobetaines, imidazolinium betaines, lecithins;
Polyoxyethylene alkyl ether (AE), polyoxyethylene alkyl phenyl ether, polyoxyethylene polystyryl phenyl ether, polyoxyethylene polyoxypropylene glycol, polyoxyethylene polyoxypropylene alkyl ether, polyoxyalkylene fatty acid ester, polyoxyalkylene Sorbitan fatty acid ester, polyoxyalkylene fatty acid alkanolamide, polyoxyalkylene alkyl glucoside, polyoxyalkylene hydrogenated castor oil, polyoxyalkylene alkyl amine, polyoxyalkylene alkyl phenyl ether, and other ethylene oxide condensation types,

  Polyhydric alcohol fatty acid partial ester, polyoxyethylene polyhydric alcohol fatty acid partial ester, polyoxyethylene fatty acid ester, (poly) glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkylamine, triethanolamine fatty acid partial ester, alkyl Nonion such as polyglucoside, propylene glycol fatty acid ester, sorbitan fatty acid ester, fatty acid ester such as sho, fatty acid alkanolamide, sugar amine acylated product, triethanolamine fatty acid partial ester, fatty acid alkylolamide, alkylamine oxide, etc. Surfactants;

Primary to tertiary fatty amine salts, alkylammonium chloride salts, tetraalkylammonium salts, trialkylbenzylammonium salts, alkylpyridinium salts, alkylhydroxyethylimidazolinium salts, dialkylmorpholinium salts, alkylisoquinolium salts, Cationic surfactants such as benzethonium salts and benzalkonium salts;
Polymeric surfactants such as sodium alginate, starch derivatives, tragacanth gum;
Natural surfactants such as phospholipids, lecithin, lanolin, cholesterol, saponins;

  Avocado oil, turtle oil, corn oil, almond oil, olive oil, cacao oil, sesame oil, safflower oil, soy oil, camellia oil, persic oil, castor oil, grape seed oil, macadamia nut oil, mink oil, cottonseed oil, molasses, palm oil Egg yolk oil, palm oil, palm kernel oil, glyceryl triisooctanoate, glyceryl tri-2-ethylhexanoate, wheat germ oil, sasanqua oil, linseed oil, evening primrose oil, eno oil, peanut oil, tea seed oil, Kaya oil, rice bran oil, cinnagyl oil, Japanese kiri oil, jojoba oil, germ oil, trioctanoic acid glycerin, triisopalmitic acid glycerin, horse oil, hardened palm oil, beef tallow, beef leg fat, sheep fat, hardened beef tallow, pork Fats and oils such as beef fat, beef bone oil, owl kernel oil, hydrogenated oil, owl, hydrogenated castor oil;

Hydrocarbons such as liquid paraffin, petrolatum, ceresin, microcrystalline wax, isoparaffin, ozokerite, squalene, pristane, squalane;
Beeswax, whale wax, lanolin, carnauba wax, candelilla wax, cotton wax, bayberry wax, ibotarou, montan wax, nukarou, lanolin, cabbage wax, lanolin acetate, liquid lanolin, sugar cane wax, lanolin fatty acid isopropyl, lauryl hexyl, reduced lanolin, jojoba wax Waxes such as hard lanolin, shellac wax, polyoxyethylene lanolin alcohol ether, polyoxyethylene lanolin alcohol acetate, lanolin fatty acid polyethylene glycol, polyoxyethylene hydrogenated lanolin alcohol ether and derivatives thereof;

Lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, behenic acid, undecylenic acid, lanolin fatty acid, hard lanolin fatty acid, soft lanolin fatty acid, linoleic acid, linolenic acid, eicosapentaenoic acid, 12-hydroxystearic acid Higher fatty acids such as;
Higher alcohols such as lauryl alcohol, cetanol, cetostearyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, lanolin alcohol, hydrogenated lanolin alcohol, hexyldecanol, octyldodecanol;

Sterols such as cholesterol and phytosterol;
Isopropyl myristate, butyl stearate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, hexyl laurate, myristyl myristate, decyl oleate, hexyl decyl dimethyloctanoate, cetyl lactate, myristyl lactate, lanolin acetate, stearic acid Isocetyl, isocetyl isostearate, cholesteryl 12-hydroxystearylate, ethylene glycol di-2-ethylhexylate, dipentaerythritol fatty acid ester, monoisostearate N-alkyl glycol, neopentyl glycol dicaprate, diisostearyl malate, di- 2-glyceryl 2-heptylundecanoate, trimethylolpropane tri-2-ethylhexylate, trimethylolpropane triisostearate Bread, pentaerythritol tetra-2-ethylhexylate, glycerol tri-2-ethylhexylate, trimethylolpropane triisostearate, cetyl-2-ethylhexanoate, 2-ethylhexyl palmitate, glyceryl trimyristate, tri-2- Heptylundecanoic acid glyceride, castor oil fatty acid methyl ester, oleic oil, cetostearyl alcohol, acetoglyceride, palmitic acid-2-heptylundecyl, adipic acid diisopropyl, N-lauroyl-L-glutamic acid-2-octyldodecyl ester, adipine Di-2-heptyl undecyl acid, ethyl laurate, di-2-ethylhexyl sepatate, 2-hexyl decyl myristate, 2-hexyl decyl palmitate, adipine 2-hexyl decyl, Sebachiru acid diisopropyl succinate 2-ethylhexyl, ethyl acetate, butyl acetate, amyl acetate, ester oils such as triethyl citrate;

Silicone such as metal soap, dimethylpolysiloxane, polyether-modified silicone, alcohol-modified silicone, methylphenylpolysiloxane, epoxy-modified silicone, fluorine-modified silicone, alkyl-modified silicone, alkoxy-modified silicone, amino-modified silicone, volatile silicone, and cyclic silicone Volatile and non-volatile oils such as
Polyols such as glycerin, diglycerin, polyglycerin, 1,3-butanediol, propanediol, polyethylene glycol;
N-methylglycine, N, N-dimethylglycine, N, N, N-trimethylglycine, N-ethylglycine, alkylglycines such as glycylbetaine, sorbitol, raffinose, pyrrolidonecarboxylates, lactates, hyaluronates , Ceramides, trehalose, xylobiose, maltose, sucrose, glucose, (poly) saccharides and derivatives thereof such as plant mucous polysaccharides, glycosaminoglycans such as water-soluble chitin, chitosan, pectin, chondroitin sulfate and salts thereof, and Its salts, amino acids such as glycine, serine, threonine, alanine, aspartic acid, tyrosine, valine, leucine, arginine, glutamine, prophosphoric acid, etc., sugar amino acid compounds such as aminocarbonyl reaction products, plants such as aloe, maronier Extract, urea Uric acid, ammonia, glucosamine, creatinine, DNA, humectants, such as nucleic acid-related substance such as RNA;

Hydroxyethylcellulose, carboxymethylcellulose, hydroxyethylcellulose hydroxypropyltrimethylammonium chloride ether, methylcellulose, ethylcellulose, hydroxypropylcellulose, methylhydroxypropylcellulose, soluble starch, carboxymethylstarch, methylstarch,
Propylene glycol alginate, polyvinyl alcohol, polyvinyl pyrrolidone, polyvinyl methyl ether, carboxyvinyl polymer, polyacrylate, guar gum, locust bin gum, quince seed, carrageenan, galactan, gum arabic, pectin, mannan, starch, xanthan gum, dextran, sac Sinoglucan, curdlan, hyaluronic acid, gelatin, casein, albumin, collagen, methoxyethylene maleic anhydride copolymer, amphoteric methacrylate copolymer, polydimethylmethylenepiperidinium chloride, polyacrylate copolymer, Water-soluble and oil-soluble polymers such as polyvinyl acetate, nitrocellulose, silicone resin;

Cationized cellulose derivative, cationic starch, cationized guar gum derivative, diallyl quaternary ammonium salt / acrylamide copolymer, quaternized polyvinylpyrrolidone derivative, quaternized vinylpyrrolidone / vinylimidazole polymer, polyglycol / amine condensate, Quaternized collagen polypeptide, polyethyleneimine, cationic silicone polymer, adipic acid / dimethylaminohydroxypropyldiethylenetriamine copolymer,
Cationic polymers such as polyaminopolyamides, cationic chitin derivatives and quaternized polymers;
Thickening and foam increasing components such as polyethylene glycol fatty acid ester, polyoxyethylene fatty acid ester methyl glycoside, tetradecene sulfonate;
Oil gelling agents such as dextrin fatty acid ester, glycerin fatty acid ester, hydroxystearic acid;

Sequestering agents such as ethylenediaminetetraacetic acid and its salts, hydroxyethylenediaminetriacetic acid and its salts, phosphoric acid, ascorbic acid, succinic acid, gluconic acid, polyphosphates, metaphosphates, hinokitiles;
P-hydroxybenzoates, benzoic acid and its salts, phenoxyethanol, hinokitile, salicylic acid and its salts, sorbic acid and its salts, dehydroacetic acid and its salts, parachlormetacresol, hexachlorophene, boric acid, resorcin, tribromosaran, Orthophenylphenol, thiram, photosensitizer 201, halocarban, trichlorocarbanide, tocopherol acetate, zinc pyrithione, phenol, isopropylmethylphenol, 2,4,4-trichloro-2-hydroxyphenol, hexachlorophene, chlorhexidine, benzethonium chloride, Benzalkonium chloride, cetylpyridinium chloride, decalinium chloride, stearyldimethylammonium chloride, stearyltrimethylammonium chloride, chloride Tilt trimethyl ammonium, chloride methyl benzethonium, lauryl trimethyl ammonium chloride, lauroyl Kola amino formyl methyl pyridinium, triclosan, preservative and antibacterial agents such as Biozoru;

PH adjusters such as citric acid, malic acid, adipic acid, glutamic acid, aspartic acid;
Other anti-dandruff and itching agents such as trichlorocarbanilide, salicylic acid, zinc pyrithione, isopropylmethylphenol;
Benzophenone derivatives, paraaminobenzoic acid derivatives, paramethoxycinnamic acid derivatives, salicylic acid derivatives and other UV absorbers;
Ascorbic acid and its salts (sodium salt, potassium salt, magnesium salt, alkali metal salt such as calcium salt, alkaline earth metal salt, ammonium salt, amino acid salt, etc.), ascorbic acid derivative (L-ascorbic acid alkyl ester) L-ascorbic acid phosphate and salts thereof, L-ascorbic acid-2-sulfate and salts thereof, L-ascorbic acid glucoside and the like, alkoxysalicylic acid and salts thereof (alkoxy groups include, for example, methoxy group and ethoxy group) , Propoxy group, isopropoxy group, butoxy group, isobutoxy group, etc.), hydroquinone glycosides and derivatives thereof (arbutin, etc.), kojic acid and its derivatives, ellagic acid, chamomile extract, altea extract, licorice extract, sucha akuhi extract, raspberry extract Apple flavonoid, bran extract, vitamin E and its derivatives, hinokitiol, placenta extract, lucinol, chamomile ET, glutathione, clove extract, tea extract, astaxanthin, cow placenta extract, tranexamic acid and its derivatives, derivatives of resorcin, azulene, γ- Whitening agents such as hydroxybutyric acid;

Blood circulation promoters such as assembly extract, cephalanthin, vitamin E and its derivatives, gamma oryzanol;
Local stimulants such as pepper tincture, ginger tincture, cantharis tincture, nicotinic acid benzyl ester;
Nutrients such as various vitamins and amino acids;
Female hormone agent;
Hair root activator;
Anti-inflammatory agents such as glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, aminocaproic acid, hydrocortisone;
Astringents such as zinc oxide, zinc sulfate, allantoin hydroxyaluminum, aluminum chloride, aluminum sulfate, zinc sulfocolate, tannic acid, citric acid, lactic acid;

Refreshing agents such as menthol and camphor;
Antihistamines such as diphenhydramine hydrochloride, chlorpheniramine maleate, glycyrrhizic acid derivatives;
Silicone materials such as high molecular silicones and cyclic silicones;
Antioxidants such as tocopherols, BHA, BHT, gallic acid, NDGA;
Sebum inhibitors such as estradiol, estrone, ethinyl estradiol;
Exfoliating / dissolving agents such as sulfur, salicylic acid, resorcin;
Α-hydroxy acids such as glycolic acid, lactic acid, malic acid, tartaric acid, citric acid;
Β-hydroxylic acid such as salicylic acid;

  Talc, kaolin, sericite, calcium carbonate, zinc oxide, aluminum oxide, magnesium oxide, zirconium oxide, magnesium carbonate, calcium carbonate, barium sulfate, chromium oxide, chromium hydroxide, tar dyes, mica, (synthetic) sericite , Silicon carbide, boron nitride, titanium dioxide, black titanium oxide, conger, red iron oxide, black iron oxide, yellow iron oxide, ultramarine, titanium coated mica, bismuth oxychloride, bengara, caking pigment, gunjo pink, gunjo Violet, chromium hydroxide, mica titanium, chromium oxide, aluminum cobalt oxide, carbon black, silicic anhydride, magnesium silicate, bentonite, (synthetic) mica, zirconium oxide, magnesium (meth) silicate aluminate, aluminate silicate Calcium, polye Len powder, nylon powder, polymethyl methacrylate, polyethylene terephthalate-polymethyl methacrylate laminated powder, acrylonitrile-methacrylic acid copolymer powder, vinylidene chloride-methacrylic acid copolymer powder, wool powder, silk powder, crystalline cellulose, N-acyl lysine, poly Methyl silsesquioxane powder, plant fruit or skin powder, bismuth oxychloride, mica titanium, iron oxide coated mica, iron oxide mica titanium, organic pigment treated mica titanium, aluminum powder, fine titanium oxide, fine particles Zinc oxide, fine particle titanium oxide coated mica titanium, fine particle zinc oxide coated mica titanium, barium sulfate coated mica titanium, carmine, β-carotene, chlorophyll, sunset yellow FCF, Ponceau SX, eosin YS, tetrab Lomofluorescein, rhodamine B, quinoline yellow SS, quinoline yellow WS, alizanin cyanine green, quinizarin green, resolbin BCA, resolbin BCA, permaton red, herringdon pink CN, phthalocyanine blue, β-apo-8-carotenal, Capsanthin, lilopine, bixin, crocin, canthaxanthin, shisonin, raphanin, ninocyanin, calsamine, safrole yellow, rutin, quercetin, cacao pigment, lipoflavin, lacainate, carminic acid, kermesic acid, alizanine, shikonin, alkanine, niquinochrome, hemoglobin, Cosmetic colorants such as curcumin and betanin:

Purified water, others, oyster extract, N-methyl-L-serine, whey, nicotinamide, diisopropylamine dichloroacetic acid, mevalonic acid, γ-aminobutyric acid (including γ-amino-β-hydroxybutyric acid), altea extract, Aloe extract, apricot kernel extract, turmeric extract, oolong tea extract, dried sea water, hydrolyzed wheat powder, hydrolyzed silk, carrot extract, cucumber extract, gentian extract, yeast extract, rice germ oil, comfrey extract, savonso extract, Giant extract, lion extract, birch extract, Atlantic mint extract, assembly extract, bisabolol, propolis, loofah extract, bodaiju extract, hop extract, marronnier extract, muroji extract, melissa extract, eucalyptus extract, yukinoshita extract, rosemary Can kiss, Roman chamomile extract, royal jelly extract, seaweed, rice bran, licorice, citrus unshiu peel, angelica, pulverized Momonoha, sphingolipids, guaiazulene, may contain vitamin C, and the like.
In particular, combined use with fatty acid diethanolamide, polyoxyethylene dioleic acid methyl glucoside, polyethylene glycol distearate, tetradecene sulfonate, myristic acid salts, myristyl dimethylamine is useful in terms of increasing viscosity and foaming power. In addition, the combined use with each zwitterionic surfactant is extremely useful in that the irritation is further reduced.

The method of using the preparation for protecting the skin of the present invention is not particularly limited, and various methods can be used. For example, it can be used by mixing with a composition containing an irritating substance, and it can be reduced by applying to the skin and mucous membrane before and / or after applying the composition containing the irritating substance. It can be used as a composition.
In addition, after washing with a cleaning composition, such as clothing such as contact lenses and underwear, there is an application in which it is used in contact with the skin and mucous membrane on the body. It is possible that components such as a surfactant in the cleaning composition remain on the surface. The preparation for protecting the skin of the present invention can be used as an irritation-reducing composition by applying before and / or after applying an object to be used in contact with the skin or mucous membrane.

In addition, it can be used as a stimulus-reducing agent for other irritating substances by containing it in paper or fiber, or a sheet made of them, and applying it to the skin or mucous membrane. In addition, the irritation to the skin and mucous membrane of the paper or fiber, or the sheet itself made of them can be reduced.
Examples of the paper or fiber to which the preparation for protecting the skin of the present invention is applied, or a sheet-like material comprising them, include the following.
As the paper product, for example, tissue paper, toilet paper, paper towel, paper diaper, paper napkin, sanitary paper, dust paper, Kyoto flower paper, wiper, etc. can be applied.

The fiber product is not particularly limited as long as it is, for example, animal hair such as wool or rayon, synthetic fiber such as cotton, acrylic, polyester, nylon or the like, or a blended fiber itself, and a fiber product made of those fibers. The form can also be used for clothes such as coats, sweaters, shirts, mufflers, shawls, kimonos, various linings, futons, blankets, stuffed animals, carpets and the like. Among them, application to cellulose fibers such as cotton / hemp and pulp, regenerated cellulose fibers such as rayon / cupra / polynosic, and protein fibers such as wool and silk is more preferable.
As the sheet-like material, for example, woven fabric, knitted fabric, non-woven fabric, felt, quilted cotton sanded with non-woven fabric or the like, and cotton processed into a sheet shape can be applied.

The amount of the preparation for protecting the skin of the present invention applied to paper or fiber, or a sheet made of them is not particularly limited, but generally paper or fiber or a sheet made of them as a solid content. However, the applied amount can be appropriately determined according to the purpose, use, and material.
As a method for incorporating the preparation for protecting the skin of the present invention into paper or fiber, or a sheet-like material comprising them, impregnation with an impregnation machine (bath), spraying with a sprayer, or application with a coating machine. It can also be used by a method of attaching with a roll or the like. Alternatively, it can be kneaded and spun into a molten polymer, used in a method in which it is dissolved or dispersed in a spinning bath and adhered at the time of spinning, or used as a fiber finishing oil after spinning, Furthermore, the method of heat-processing after attaching a processing agent and drying can also be used.

In particular, in fibers obtained by wet spinning, such as regenerated cellulose fibers such as cupra and rayon, the treatment agent is mixed with the spinning dope, dissolved or dispersed in the spinning bath, and the fiber after spinning is dissolved in the treatment agent. It is also possible to take a method of immersing in a treatment bath.
Hereinafter, the present invention will be described more specifically using examples and the like, but the present invention is not limited to these examples and the like.

The evaluation means used in the examples of the present invention are as follows.
(Irritation relaxation test)
A panel of 5 healthy boys was exposed to 1 cm ² of forearm flexion skin with 0.1 g of sodium lauryl sulfate aqueous solution adjusted to the concentration shown in Table 1 (5% by mass) for 3 days to check for skin irritation. In the test to evaluate, 10 minutes before or 10 minutes after applying the sodium lauryl sulfate aqueous solution, 0.1 g of the aqueous solution of Production Example 1 or 2 prepared at the concentration (1 to 5% by mass) shown in Table 1 was applied. Evaluation was performed. The determination result is shown as an average of the following evaluation points.
Judgment criteria and score Erythema, edema, blisters (4 points)
Erythema, edema (3 points)
Erythema (2 points)
Minor erythema (1 point)
No erythema, no edema (0 points)

(Irritation relaxation test using non-woven fabric)
The treated non-woven fabric was closed and pasted for 48 hours on 1 cm ² of forearm flexion skin of 5 panelists with allergic dermatitis, and the presence or absence of skin irritation was evaluated. The evaluation criteria are described below.
When the number of people showing erythema is 1 or less ○
When 2 to 3 people show erythema △
If more than 4 people show erythema ×

(Production Example 1 of acyl compound)
9.1 g (0.05 mol) of L-lysine hydrochloride was mixed with 57 g of water. While this solution was adjusted to a pH range of 10 to 11 with a 25% aqueous sodium hydroxide solution and the reaction temperature was maintained at 5 ° C., 31.1 g of N-lauroyl-L-glutamic anhydride (0. 1 mol) was added over 2 hours to carry out the reaction. After stirring for another 30 minutes, tertiary butanol was added to a concentration of 20% by weight in the liquid, 75% sulfuric acid was added dropwise to bring the pH value of the liquid to 2, and the liquid temperature to 65 ° C. It was adjusted. After completion of the dropwise addition, stirring was stopped and the mixture was allowed to stand at 65 ° C. for 20 minutes, so that the organic layer and the aqueous layer were separated, and the organic layer was separated therefrom. Tertiary butanol and water were added to the separated organic layer, the temperature was raised to 65 ° C., and the mixture was stirred for 20 minutes. After the stirring was stopped, the mixture was allowed to stand to separate into an organic layer and an aqueous layer. After repeating the same water washing operation on the obtained organic layer, the solvent was removed from the obtained organic layer, and neutralized with sodium hydroxide to an aqueous solution having a solid content of 30% by weight and a pH of 6.5 (25 ° C.). After the preparation, it was dried to obtain a composition containing an acyl compound represented by the following formula (4) (wherein X is independently H or Na).

(Production Example 2 of acyl compound)
In Production Example 1, 31.1 g of N-lauroyl-L-glutamic anhydride was changed to 31.1 g (0.1 mol) of N-cocoyl-L-glutamic anhydride, solid content 30% by weight, pH 6.0 (25 ° C.) Except for having been prepared in the same manner as in Production Example 1, a composition containing an acyl compound was obtained.
[Examples 1 to 4, Comparative Example 1]
An aqueous solution having the composition shown in Table 1 was prepared, and a skin irritation relaxation test was performed. The results are shown in Table 1.
As shown in Table 1, it is clear that irritation is alleviated by the preparation for protecting the skin of the present invention.

[Examples 5 to 6, Comparative Example 2]
Using a regenerated cellulose nonwoven fabric made of continuous filaments of copper ammonia rayon (trade name “Benlyse”, Asahi Kasei Fibers Co., Ltd.), the amount of trimethylcetylammonium chloride deposited on the nonwoven fabric is 0.25% by mass with respect to the nonwoven fabric. The adhered nonwoven fabric was used as a raw material nonwoven fabric, and the composition of Production Example 1 or 2 was applied to the nonwoven fabric in the form of an aqueous solution. At this time, the adhesion amount of the composition of Production Example 1 or 2 with respect to the nonwoven fabric weight was set to 0.25% by weight. Thereafter, the nonwoven fabric was dried and hot-pressed at 80 ° C. for 5 seconds to obtain a treated nonwoven fabric. Table 2 shows the evaluation results of the stimulus relaxation test using this.
As shown in Table 2, it is clear that the use of the preparation for protecting the skin of the present invention reduces the irritation even when a nonwoven fabric is used.

The present invention provides a preparation that protects the skin against irritation such as a surfactant, and protects the skin by applying the preparation to the skin before or after applying the irritating substance to the skin. Since the method can also be provided, it can be suitably used in the fields of cosmetic compositions such as cosmetics and quasi-drugs, external pharmaceutical compositions, and detergent compositions.

Claims (8)

  A preparation for protecting the skin comprising one or more acyl compounds each having two or more acyl groups and hydrophilic groups in the molecule.   The preparation for protecting the skin according to claim 1, wherein at least one of the acyl compounds has an amino acid residue in the molecule. The preparation for protecting skin according to claim 1 or 2, wherein at least one of the acyl compounds is a compound represented by the following general formula (1).

(In the above general formula (1), X is a linear, branched, cyclic or aromatic hydrocarbon chain having a molecular weight of 1,000,000 or less, which may have m functional groups and other substituents. N (m ≧ n) Qs bonded to X are substituents represented by the following general formula (2), which may be the same as or different from each other. In Formula (2), Z is a bond derived from a functional group of X, R ¹ CO represents a long-chain acyl group derived from a saturated or unsaturated fatty acid having 2 to 20 carbon atoms, R ² represents hydrogen, or a lower alkyl group having 1 to 3 carbon atoms which may be substituted with a hydroxyl group or a carboxyl group, and Y represents a carboxyl group, a sulfonic acid group, a sulfate group, or a phosphate group. Or show their salts j, k is any of independently 0,1,2, and j, k is an integer of .n 2 to 20 do not represent 0 at the same time.)

Paper or fiber containing the preparation for protecting the skin according to any one of claims 1 to 3, or a sheet-like material comprising the same.   The preparation for protecting the skin according to any one of claims 1 to 3, which is applied to the skin before and / or after the irritating substance is applied to the skin.   The paper, the fiber, or the sheet-like material comprising them according to claim 4, wherein the stimulant is applied to the skin before and / or after the application.   A method for protecting skin, comprising applying the preparation for protecting skin according to any one of claims 1 to 4 to the skin before and / or after applying the irritating substance to the skin. A method for protecting the skin, characterized by applying the paper, fiber, or sheet comprising the same according to claim 4 to the skin before and / or after applying the irritating substance to the skin.