JP2003155206A - Bactericide and antiseptic - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a bactericide and an antiseptic having excellent antimicrobial activity and high chemical stability, a composition for application to the skin, a cleaning composition and an antimicrobial fiber assembly using the antiseptic and/or the bactericide and to provide a method for sterilizing microorganisms and a method for controlling propagation of microorganisms. SOLUTION: This bactericide comprises at least an amide group-containing guanidine derivative represented by general formula (I) (R<1> and R<2> are each a hydrogen atom, a 1-4C straight-chain or branched-chain alkyl group or alkenyl group and may be the same or different; R<3> is a 1-22C straight-chain or branched-chain alkyl group or alkenyl group; A is a 1-10C straight-chain or branched-chain alkylene group or alkenylene group) or its salt. This antiseptic comprises the amide group-containing guanidine derivative or its salt.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a preservative or bactericidal agent using an amide group-containing guanidine derivative or a salt thereof, and a composition for skin application and a cleaning composition using the preservative and / or bactericidal agent. Object, antibacterial fiber assembly,
The present invention relates to a method for sterilizing microorganisms and a method for suppressing the growth of microorganisms.

[0002]

2. Description of the Related Art Conventionally, products such as lotions, emulsions, ointments, lotions, lotions, creams, cosmetics such as external skin preparations, wet tissues, oral compositions, etc. containing water have been manufactured. Bacteria at the time of use and
Various preservatives or bactericides have been used to prevent deterioration due to contamination of microorganisms such as mold and to sterilize bacteria and microorganisms in the oral cavity, skin and hair.

Examples of preservatives and bactericides used in these products include isopropylmethylphenol, paraoxybenzoic acid ester, phenoxyethanol, hinokitiol and other phenols, benzoic acid and its salts, salicylic acid and its salts, dehydroacetic acid and Acids such as salts thereof, sorbic acid and salts thereof, quaternary ammoniums such as benzalkonium chloride, benzethonium chloride, alkyltrimethylammonium chloride, etc., amphoteric surfactants such as alkylaminoethylglycine hydrochloride, sodium stearylhydroxyethylbetaine chloride, etc. , Photosensitizer, zinc undecylenate, behidene, iodine and the like.

However, the preservatives or bactericides described above have practically effective antibacterial activities because their amounts are regulated from the viewpoint of safety in the Japanese Pharmacopoeia, the standard for cosmetic raw materials, and the official standard for food additives. In many cases, the amount cannot be blended.

[0005] In recent years, a variety of amino acid derivatives have been studied under the growing social concern about safety and natural orientation. N- which is a natural amino acid derivative and is a cationic activator like quaternary ammonium salts.
A long-chain acyl basic amino acid derivative and its acid addition salt have been known as antiseptic detergents for a long time (Japanese Patent Publication No. 51-5413), and for example, one of them, N-cocoyl-L-arginine ethyl. Ester-DL-
Pyrrolidonecarboxylate is commercially available under the trade name of "CAE", exhibits excellent safety, and has good antiseptic or bactericidal properties.

However, the N-long-chain acyl basic amino acid derivative is usually used in the form of a salt, and since it is water-soluble, the ester salt in the molecule of the derivative acid salt may be hydrolyzed. .

On the other hand, an amino group-containing guanidine derivative having a structure in which an ester group which is a hydrolysis site is removed from an N-long chain acyl basic amino acid derivative or a salt thereof is
JP-A-2-243614, JP-A-4-49221
As described in JP-A-4-49222 and JP-A-4-49222, it has excellent adsorptivity to hair, and imparts flexibility and moisturizing property to hair and a good feeling of finishing, and therefore is widely used. It is used as an excellent surfactant as compared with the quaternary ammonium salt. In addition, JP-A-6-3217
As disclosed in Japanese Patent Publication No. 27, when an amino group-containing guanidine derivative or a salt thereof is used as a skin external preparation, it has an excellent moisturizing effect, spreads well at the time of use, and gives a smooth and non-greasy feeling. Was known.

However, although the amino group-containing guanidine derivative or its salt is known to be used as a texture improving agent in hair cosmetics and external preparations for skin as described above, it is used and studied as a preservative or bactericide. The present situation is that no amino acid-containing guanidine derivative or a salt thereof is used in wet tissues or oral compositions at all. In addition, in this specification, a "bactericidal agent" means the chemical | medical agent which kills microorganisms, and a "preservative" means the chemical | medical agent which suppresses the growth of microorganisms.

[0009]

DISCLOSURE OF THE INVENTION The present invention provides a preservative and a bactericidal agent having excellent antibacterial activity and high chemical stability, and a composition for skin application using the preservative and / or the bactericidal agent. An object of the present invention is to provide a product, a cleaning composition, an antibacterial fiber assembly, a method for sterilizing microorganisms, and a method for suppressing the growth of microorganisms.

[0010]

As a result of intensive studies in view of the above objects, the present inventors have found that a specific amide group-containing guanidine derivative or a salt thereof has excellent antibacterial activity and high chemical stability. The present invention was conceived and the present invention was conceived.

That is, the present invention is as follows.

(1) At least the following general formula (I)

[Chemical 7] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A bactericidal agent comprising an amide group-containing guanidine derivative represented by the formula (4) or a salt thereof.

(2) At least the following general formula (I)

[Chemical 8] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) An amide group-containing guanidine derivative represented by (4) or a salt thereof is contained.

(3) A composition for skin application, which comprises the bactericide described in (1) above and / or the preservative described in (2) above.

(4) A cleaning composition containing the bactericide described in (1) above and / or the preservative described in (2) above.

(5) The following general formula (I) is added to the fiber assembly.

[Chemical 9] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A composition containing an amide group-containing guanidine derivative represented by the formula (4) or a salt thereof is impregnated with the composition, and the antibacterial fiber assembly is characterized.

(6) The following general formula (I) is applied to the fiber surface.

[Chemical 10] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) An amide group-containing guanidine derivative represented by the formula (1) or a salt thereof is carried on the antibacterial fiber assembly.

(7) The following general formula (I)

[Chemical 11] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A method of sterilizing a microorganism by using an amide group-containing guanidine derivative represented by the above) or a salt thereof.

(8) The following general formula (I)

[Chemical 12] (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A method for suppressing the growth of microorganisms using an amide group-containing guanidine derivative represented by the above) or a salt thereof.

[0020]

BEST MODE FOR CARRYING OUT THE INVENTION The fungicide and preservative of the present invention are:
An amide group-containing guanidine derivative is used as an active ingredient. Moreover, the composition for skin application, the composition for cleaning, and the antibacterial fiber assembly of the present invention utilize the fungicide and / or preservative of the present invention. Hereinafter, the present invention will be described in detail in the following order. [I] Amide Group-Containing Guanidine Derivatives [II] Bactericides and Preservatives Containing Amide Group-Containing Guanidine Derivatives [III] Skin Application Compositions [IV] Cleaning Compositions [V] Antibacterial Fiber Aggregates

[I] Amide Group-Containing Guanidine Derivative The amide group-containing guanidine derivative used in the present invention is represented by the following general formula (I).

[0022]

[Chemical 13]

In the above general formula (I), R ¹ and R ² are
It represents a hydrogen atom or a linear or branched alkyl group or alkenyl group having 1 to 4 carbon atoms. R ¹ and R ² may be the same or different. Most preferred as R ¹ and R ² are hydrogen atoms.

In the general formula (I), an acyl group (R ³ C
Examples of O) include a straight chain or branched chain saturated or unsaturated acyl group having 1 to 22 carbon atoms. Specific examples of the acyl group (R ³ CO) include acetic acid, propionic acid,
From capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linoleic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acid, beef tallow fatty acid, hardened beef tallow fatty acid, etc. Mention may be made of derived acyl groups.
Preferred acyl groups include a caproyl group, a lauroyl group, a myristyl group, a palmitoyl group, a stearoyl group,
Examples thereof include behenoyl group, cocoyl group, hydrogenated tallow oil fatty acid acyl group, and the like, and more preferable examples include lauroyl group, myristyl group, palmitoyl group, and stearoyl group.

In the general formula (I), A has 1 to 1 carbon atoms.
10, preferably 2 to 6 branched or linear alkylene or alkenylene groups. Specific examples of A include ethylene group, propylene group, butylene group, pentylene group and hexylene group.

The amino group-containing guanidine derivative is usually
Compounded in the form of a salt, specifically, inorganic acid salts such as hydrochloride, sulfate, phosphate, etc., glycolate, acetate, citrate, acidic amino acid salt, pyrrolidone carboxylate, fatty acid salt, acyl It can be used as an organic acid salt such as an amino acid salt. Further, the inorganic acid or organic acid used may be a single acid or a mixture of two or more kinds of acids.

The amide group-containing guanidine derivative or its salt used in the present invention is described in, for example, JP-A-6-312972.
As disclosed in Japanese Patent Publication No. JP-A-2003-96242, monoamidoamine derived from diamine is heated under reduced pressure, heated under nitrogen bubbling, or stored under a carbon dioxide-free atmosphere, then guanidylated with cyanamide, S-methylisothiourea, etc., Further, it can be obtained by removing the mixed impurities by means such as crystallization.

It can also be produced by reacting an amino group-containing guanidine derivative represented by the following general formula (II) with a fatty acid halide or a fatty acid ester.

[0029]

[Chemical 14] (In the general formula (II), R ¹ and R ^{2 each} represent a hydrogen atom or a carbon number of 1 to 1.
4 are linear or branched alkyl groups or alkenyl groups, which may be the same or different. A has 1 carbon
10 is a linear or branched alkylene group or alkenylene group. )

[II] Fungicides and preservatives containing amide group-containing guanidine derivatives The amide group-containing guanidine derivatives represented by the general formula (I) and salts thereof have excellent bactericidal action and antiseptic action against various microorganisms. Having Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Caries fungus, Acne bacterium, Candida, Aspergillus niger, athlete's foot fungus, dandruff fungus, water mold, methicillin-resistant Staphylococcus aureus against any of Have. The active ingredient content and application rate of the amide group-containing guanidine derivative can be varied over a wide range depending on the dosage form, the type of microorganisms to be applied, and the conditions such as the expected timing and duration of their occurrence. .

Usually, when the amide group-containing guanidine derivative represented by the general formula (I) is applied as a bactericide or preservative, the concentration is 0.001 to 10% by weight. However, in special cases, it is possible to exceed or fall below these ranges. For example, when the mixture is applied with other fungicides and preservatives and a synergistic effect is observed, it can be used in a lower dose.

[III] Skin Application Composition The skin application composition of the present invention contains the amide group-containing guanidine derivative represented by the general formula (I) as a bactericide and a preservative. The composition for skin application of the present invention includes lotions, emulsions, creams, makeup products (eye shadow, white powder, cream, lipstick), fragrances, perfumes, colognes, fragrances, deodorants, deodorants, masking. Agents, antiperspirants, bath agents, insecticides, and other skin cosmetics; hair tonics, hair conditioners, hair makeup, hair creams, pomades, hair restorers, other hair cosmetics; insect repellents, ointments, etc. Examples thereof include agents and the like, and an amide group-containing guanidine derivative can be added thereto in an appropriate amount to impart antiseptic properties or bactericidal properties to enhance commercial value.

In the composition for skin application of the present invention, the blending amount of the amide group-containing guanidine derivative is appropriately determined depending on the intended product and is not particularly limited, but it is preferably 0.001 to 10% by weight, Particularly preferably, it is 0.01 to 5% by weight. If it is less than 0.001% by weight, the effect of the present invention may not be sufficiently exhibited.

In the composition for skin application of the present invention, in addition to the amide group-containing guanidine derivative or a salt thereof, various additives usually used in the composition for skin application are included within a range not impairing the effects of the present invention. It can be added as an optional component. Examples include surfactants, wetting agents, silicone compounds, polymer substances (polymer compounds), alcohols, UV absorbers, dyes, pigments, vitamins, antioxidants, sequestering agents, anti-inflammatory agents, pH. Examples include standard ingredients for cosmetics such as regulators, pearlizing agents, nucleic acids, enzymes, natural extracts, standard for blending ingredients by cosmetic variety, standard for raw materials of the Pharmaceutical Department, Japanese Pharmacopoeia, and raw materials described in the official compendial for food additives. Further, an antiseptic and a bactericide other than the amide group-containing guanidine derivative represented by the general formula (I) may be added.

Examples of surfactants are: Anionic surfactant alkyl sulfate, alkyl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene alkyl carboxylate, alkylphenyl ether sulfonate, alkylsulfosuccinic acid and the like Derivative salt, N
-Acyl sarcosine and its derivative salts, N-acyl-N-methyl-β-alanine salt, polyoxyethylene coconut oil fatty acid mono-ethanolamide sulfate, polyoxyethylene alkyl ether phosphate, higher fatty acid salt, N
-Acylglycine salt, N-acylalanine salt, etc. Amphoteric surfactant Carbobetaine-type amphoteric surfactant, Sulfobetaine-type amphoteric surfactant, Hydroxysulfobetaine-type amphoteric surfactant, Amidosulfobetaine-type amphoteric surfactant, Phosphobetaine-type amphoteric surfactant, Imidazoline-type amphoteric surfactant Activator, lecithin derivative, etc. 3. Nonionic surfactant Propylene glycol fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester,
Polyoxyethylene alkylphenyl formaldehyde condensate, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, polyoxyethylene sterol and its derivatives, polyethylene glycol fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene alkyl ether, Polyoxyethylene alkyl phenyl ether, polyoxyethylene lanolin and its derivatives, polyoxyethylene beeswax derivatives, polyoxyethylene alkylamines, polyoxyethylene fatty acid amides, alkanolamides, sugar esters, polyoxyethylene hydrogenated castor oil pyroglutamic acid ester, Polyoxyethylene glyceryl pyroglutamate, etc. 4. Cationic surfactant quaternary ammonium Umushio, amidoamines, N- acyl arginine ester salts, N- [3- alkyloxy-2-hydroxypropyl] -L- arginine salts, and the like. Examples of the salt of the anionic surfactant include sodium salt, magnesium salt, potassium salt, ammonium salt, diethanolamine salt, triethanolamine salt, arginine salt, lysine salt, etc., and these various surfactants should be added. You can

Examples of wetting agents are: 1. Polyhydric alcohol glycerin, propylene glycol, 1,3-butylene glycol, isoprene glycol, polyethylene glycol, diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, decaglycerin, sorbitol, ethylene glycol, erythritol, etc. Natural Moisturizing Factor (NMF) Proline, Glycine, Alanine, Serine, Threonine,
2. Amino acids such as arginine, glutamic acid, aspartic acid, leucine, isoleucine, valine, pyrrolidonecarboxylic acid or pyrrolidonecarboxylate, lactic acid or lactate, urea, glucosamine, creatine, citrate, etc. 3. Sugars, polysaccharides and polysaccharide derivatives sucrose, lactose, trehalose, natural oligosaccharides, hyaluronic acid and sodium salts, chondroitin sulfate, etc. Examples include polyamino acids such as polyamino acids polyglutamic acid and polyaspartic acid, and salts thereof, as well as amino acid derivatives, soybean protein degradation products, deoxyribonucleic acid, glycine betaine, chitin, chitosan, and deacetylated chitin.

Examples of silicone compounds are: Ether-modified silicone methyl polysiloxane, highly polymerized methyl polysiloxane,
Polyoxyethylene / methylpolysiloxane copolymer,
1. Polyoxypropylene / methylpolysiloxane copolymer and poly (oxyethylene, oxypropylene) / methylpolysiloxane copolymer, etc. Amino-modified silicone stearoxymethylpolysiloxane, stearoxytrimethylsilane, methylhydrogenpolysiloxane,
Cyclic silicones such as octamethylpolysiloxane, decamethylpolysiloxane, decamethylcyclopentasiloxane, octamethylcyclotetrasiloxane, tetrahydrotetramethylcyclotetrasiloxane, methylcyclopolysiloxane and dodecamethylcyclohexasiloxane; methylphenylpolysiloxane, trimethyl 2. Siloxysilicic acid, aminoethylaminopropylsiloxane / dimethylsiloxane copolymer, etc. Other examples include silanol-modified polysiloxane, alkoxy-modified polysiloxane, fatty acid-modified polysiloxane, fluorine-modified polysiloxane, epoxy-modified polysiloxane, alkoxy-modified polysiloxane perfluoropolyether, polyvinyl acetate dimethylpolysiloxane, and the like. In addition, a silicone emulsion obtained by emulsifying one or more of these may also be used.

Examples of polymer substances (polymer compounds) are: 1. Plant type polysaccharide polymer guar gum, locust bingham, quince seed, carrageenan, galactan, gum arabic, tragacanth gum, pectin, mannan, starch, pullulan, etc. 2. Microorganism-derived polysaccharide polymer xanthan gum, dextran, succinoglucan, curdlan, hyaluronic acid, etc. 3. Animal-based proteins gelatin, casein, albumin, collagen, etc., 4. 4. Cellulose derivatives methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose and salts thereof, methyl hydroxypropyl cellulose, etc. 6. Starch derivative soluble starch, carboxyl starch, methyl starch, etc. 6. Alginic acid derivative, propylene glycol alginate, alginate, etc., 7. Vinyl derivative polyvinyl alcohol, polyvinyl butyral, vinyl acetate / vinyl pyrrolidone copolymer, vinyl acetate / crotonic acid copolymer, vinyl methyl ether / ethyl maleate copolymer, vinyl methyl ether / butyl maleate copolymer, croton Acid / vinyl acetate / vinyl neodecanoate copolymer, methoxyethylene maleic anhydride copolymer, isobutylene / sodium maleate copolymer, N
-Methylpyrrolidone, vinylpyrrolidone / N, N-dimethylaminoethylmethacrylic acid copolymer diethyl sulfate, vinylimidazolium methochloride / vinylpyrrolidone copolymer, polyvinylpyrrolidone, vinylpyrrolidone / styrene copolymer, vinylpyrrolidone / hexadecene Copolymer, styrene-vinylpyrrolidone copolymer,
7. Eicosene / vinylpyrrolidone copolymer, carboxyvinyl polymer, etc. (Meth) acrylic acid derivative alkyl acrylate copolymer, polyacrylic acid and its salts (sodium, potassium, ammonium, triethanolamine, arginine, lysine, etc.), alkyl polyacrylate, alkyl acrylate copolymer, acrylic Acid amide / styrene copolymer, alkyl acrylate / styrene copolymer, acrylic acid octylamide / acrylic acid ester copolymer and its salt, acrylic acid octylamide / hydroxypropyl acrylate / butylaminoethyl methacrylate copolymer , Acrylic resin alkanolamine, hydroxyethyl acrylate / methoxyethyl acrylate copolymer, acrylic acid alkyl ester / methacrylic acid alkyl ester / diacetone / acetone acrylamide / methacrylic acid copolymer, chloride Methacryloylethyl dimethyl betaine / methacryloyl ethyl trimethyl ammonium chloride / methoxy polyethylene glycol methacrylate copolymer, such as methyl diallyl ammonium / acrylamide copolymer, methacryloyl ethyl dimethyl betaine / methacryloyl ethyl trimethyl ammonium chloride / 2-hydroxyethyl methacrylate copolymer , 9. Cationized cellulose O- [2-hydroxy-3- (trimethylammonio) propyl] hydroxyethyl cellulose chloride, O-chloride
[2-hydroxy-3- (lauryldimethylammonio) propyl] hydroxyethyl cellulose and the like, 10. Cationized guar gum O- [2-hydroxy-3- (trimethylammonio) propyl] guar gum, etc. 11. Others carboxymethyl dextran and its salts, epoxy resin isostearic acid ester, polyamide epichlorohydrin resin, bisphenol epoxy resin fatty acid ester, polyethylene Glycol epichlorohydrone
Examples thereof include coconut oil alkylamine / dipropylenetriamine condensate, perfluoropolyether and the like.

Examples of alcohols include higher alcohols such as cetyl alcohol, stearyl alcohol, behenyl alcohol, isostearyl alcohol, octyldodecanol, oleyl alcohol and myristyl alcohol, and lower alcohols such as ethanol and isopropyl alcohol.

Examples of ultraviolet absorbers are benzophenone derivatives, para-aminobenzoic acid derivatives, methoxycinnamic acid derivatives, salicylic acid derivatives, urocanic acid and its derivatives, 4-tert-butyl-4'-methoxydibenzoylmethane, 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, methyl anthranilate, etc. are mentioned.

Examples of dyes are Red No. 201 and Red 2.
02, red 204, red 205, red 220,
Red 226, Red 228, Red 405, Orange 20
No. 3, Orange No. 204, Yellow No. 205, Yellow No. 401, Blue No. 404, Red No. 3, Red No. 104, Red No. 106,
Red 227, Red 230, Red 401, Red 50
No. 5, Orange No. 205, Yellow No. 4, Yellow No. 5, Yellow 202
No. 203, yellow No. 203, green No. 3, blue No. 1, and the like.

Examples of pigments include natural pigments such as β-carotene, calsamine, and cochineal, mica, talc, kaolin, calcium carbonate, magnesium carbonate, silicic anhydride, aluminum oxide, barium sulfate, red iron oxide, iron oxide yellow, and black. Iron oxide, chromium oxide, ultramarine, navy blue, carbon black, titanium oxide, zinc oxide, titanium mica, fish scale foil,
Examples include inorganic pigments such as bismuth oxychloride, boron nitride, photochromic pigments, synthetic fluorophlogopite, iron-containing synthetic fluorophlogopite, and fine particle composite powder.

Examples of vitamins include vitamin A, B1, B2, B6 and its derivatives used as nutritional supplements, vitamin C and its derivatives also used as whitening agents, vitamin E and its derivatives used as vasodilators, etc. Is mentioned.

Examples of antioxidants include tocophenols, dibutylhydroxytoluene (BHT), butylhydroxyanisole (BHA) and the like.

Examples of the sequestering agent include ethylenediaminetetraacetic acid (EDTA) sodium salt, phosphoric acid, citric acid, succinic acid, gluconic acid, polyphosphoric acid, sodium metaphosphate and the like.

Examples of preservatives and fungicides other than the amide group-containing guanidine derivative represented by the general formula (I) are benzoic acid, sodium benzoate, isopropylmethylphenol, zinc undecylenate, undecylene monoethanolamide, and chloride. Zinc, benzalkonium chloride, alkyltrimethylammonium chloride, cetylpyridinium chloride, benzalkonium chloride, alkyldiaminoethylglycine hydrochloride, chlorhexidine hydrochloride, O-phenylphenol, photosensitive element 101, photosensitive element 201, chlorhexidine gluconate, cresol , Chloramine T, chlorxylenol, chlorcresol, chlorphenesin,
Chlorobutanol, salicylic acid, sodium salicylate, alkylisoquinolinium bromide, domiphen bromide,
Examples include sorbic acid and salts, thymol, tiram, dehydroacetic acid and sodium, trichlorocarbanilide, p-oxybenzoic acid ester, chlorophenol, halocarbane, phenol, hexachlorophene, resorcin, triclosan, benzethonium chloride and the like.

Examples of anti-inflammatory agents include β-glycyrrhetinic acid, glycyrrhizic acid derivatives, allantoin, azulene, ε-aminocaproic acid, hydrocortisone, hinokitiol and the like.

In addition, arbutin, kojic acid as a whitening agent, cembranthin as a hair-growth agent, cepharanthin, γ-oryzanol, capsicum tincture, ginger tincture, nicotinic acid benzyl ester, female hormone agents estradiol, ethinyl estradiol, hair root Examples of the activator include pantothenic acid and its derivatives, placenta extract, allantoin, and photosensitive element 301.

Further, as a skin roughness preventing agent, zinc oxide, zinc sulfate, allantoin hydroxyaluminum,
Aluminum chloride, aluminum sulfate, zinc sulfocarbonate, tannic acid, menthol, camphor and the like as a cooling agent.

Further, anti-histamines include diphenhydramine hydrochloride, chlorferamine maleate, and keratin exfoliating / dissolving agents such as sulfur, salicylic acid, and resorcin.

Naturally-derived agents include purified oils such as hamamelis, odricho grass, birch, rhubarb, licorice, yellow cypress, shikon, sawtooth grass, aloe, chamomile, eucalyptus oil, carrot extract, aloe, shikon, lily, loofah , Horse chestnut, psyllium, safflower and the like.

In addition, hydrolyzed protein collagen, hydrolyzed protein such as hydrolyzed silk, blood-sucking insects (mosquitoes, lice,
Fleas, mites, etc.), dimethyl phthalate, 2-ethyl-1,3-hexanediol, bisbutylene tetrahydrofurfural, N, N-diethyl-m
-Toluamide and the like.

The composition for skin application is not particularly limited in its dosage form, and may be emulsified system, solution system, solubilized system,
Any formulation such as powder dispersion system, water-oil two-layer system, water-oil-powder three-layer system, etc. may be used.

[IV] Cleaning Composition Next, the cleaning composition of the present invention will be described in detail. The cleaning composition of the present invention contains the amide group-containing guanidine derivative represented by the general formula (I) as a bactericide and a preservative. Examples of the cleaning composition of the present invention include powder toothpaste, toothpaste, mouthwash (liquid toothpaste, mouthwash, rinse), other oral cleaning agents; shampoo, rinse, other hair cleaning agents; body Soap, facial cleanser, cosmetic detergent, soap, and other skin cleansing agents; dish washing detergent, laundry detergent, softener, disinfecting detergent, deodorant detergent, furnichia care, bleach, etc. can be exemplified. An appropriate amount of the amide group-containing guanidine derivative can be added to these to impart antiseptic or bactericidal properties, and the commercial value can be increased. In particular, in the composition for oral cavity, some efficacy in the oral cavity, often commercialized with some effect, one of its typical efficacy, the bactericidal action against oral bacteria, General formula (I)
The amide group-containing guanidine derivative represented by can be used as a preservative or bactericide against oral bacteria.

In the cleaning composition of the present invention, the blending amount of the amide group-containing guanidine derivative represented by the general formula (I) is appropriately determined depending on the intended product and is not particularly limited, but preferably 0.001. 10 to 10% by weight, particularly preferably 0.01 to 5% by weight. 0.0
If it is less than 01% by weight, the effect of the present invention may not be sufficiently exhibited.

The cleaning composition of the present invention has the general formula (I)
In addition to the amide group-containing guanidine derivative represented by or the salt thereof, various additives usually used in cleaning compositions can be added as optional components within a range that does not impair the effects of the present invention. Examples include fungicides or preservatives other than the amide group-containing guanidine derivative represented by the general formula (I), chelating agents, surfactants, fragrances, sweeteners, binders, wetting agents, abrasives, and pH adjusters. Agents and other medicinal components can be blended.

Examples of fungicides or preservatives other than the amide group-containing guanidine derivative represented by the general formula (I) are:
Paraoxybenzoic acid and paraoxybenzoic acid ester (eg, methyl paraoxybenzoate, ethyl paraoxybenzoate); cetylpyridinium chloride, benzalkonium chloride, etc .; methyl sodium paraoxybenzoate, benzyl paraoxybenzoate, paraphenolsulfonic acid and the like Salt (eg sodium paraphenolsulfonate), phenol, parachlorophenol, parachlorometacresol, parachlorometaxylenol, dichloroxylenol; isopropylmethylphenol, resorcin, resorcinol monoacetate, orthophenylphenol; thiobischlorophenol, ortho Sodium phenol, sodium phenoxide, chlorophenesin, phenoxyethanol, thymol, chlorothymol; pyrogallol, cre Phenols such as oleic acid, hinokitiol and hydroxybenzosathiol; benzoic acid and its salts, salicylic acid and its salts, dehydroacetic acid and its salts, sorbic acid and its salts, acids such as boric acid; hexachlorophenone, 2,4,4 '-
Halogenated bisphenols such as trichloro-2'-hydroxydiphenyl ether, 3,4,4'-trichlorocarbanilide, 3-trifluoromethyl-4,4 '
Amides such as dichlorocarbanilide, undecylenic acid monoethanolamide, chloroacetamide; domiphen bromide, alkylisoquinolinium bromide, alkyltrimethylammonium bromide; cetyltrimethylammonium saccharin, methylbenzethonium chloride, laurylpyridinium chloride, Laurylcholaminoformulmethylpyridinium chloride, decanium chloride, stearyldimethylbenzylammonium chloride; quaternary ammonium compounds such as benzethonium chloride and alkyltrimethylammonium chloride; lauryldi (aminoethyl) glycine, laurylaminoethylglycine, alkyldiaminoethylglycine hydrochloride, etc. Zwitterionic compounds; chlorohexidine, dibromopropamidine diisethionate; chlorohexidine gluconate; phenyl Ethyl alcohol, benzyl alcohol, dichlorobenzyl alcohol, glutardialdehyde, chloramine T, zinc pyrithione, sodium pyrithione, furfural, platolin, pionine, luminex, paradimethylaminostyrylheptylmethylthiazonium iodide; 5-bromo-5-nitro- 1,3-dioxane; tetramethylthiuram disulfide, 1-
Hydroxypyridine-2-thione, imidazoylurea compound, N-trichloromethyl mercapto-4-cyclohexene-1,2-dicarboximide, lysodium chloride, chlorobutanol, 2-bromo-2-nitro-
1,3-propanediol, 6-acetoxy-2,4-
Examples thereof include dimethyl-m-dioxane, diethyl pyrocarbonate, ethylene oxide and β-propiolactone, and these can be used alone or in combination of two or more.

Examples of the chelating agent include hydroxyethylethylenediamine triacetate, disodium edetate, glucono delta lactone, gluconic acid, sodium polyphosphate, alanine and sodium citrate.

As the surfactant, the same surfactants as those exemplified in the composition [III] for skin application can be used.

Further, as the fragrance, for example, menthol, carvone, anethole, eugenol, methyl salicylate, limonene, ocimene, n-decyl alcohol,
Citronell, α-terpineol, methyl acetate, citronenyl acetate, methyl eugenol, cineole, linalool, ethyl linalool, vanillin,
Thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil,
Perilla oil, winter green oil, clove oil, eucalyptus oil, etc.
These can be used alone or in combination of two or more.

Examples of sweeteners include saccharin sodium, acesulfame potassium, stevioside, neohesperidyl dihydrochalcone, glycyrrhizin, perillartin, thaumatin, asparatyl phenylalanyl methyl ester, p-methoxycinnamic aldehyde and the like. These can be used alone or in combination of two or more.

Examples of the binder include carrageenan, cellulose derivatives such as carboxymethyl cellulose, alkali metal alginates such as sodium alginate,
Gums such as xanthan gum, tragacanth gum, gum arabic, polyvinyl alcohol, synthetic binders such as sodium polyacrylate, silica gel, aluminum silica gel, inorganic binders such as bee gum, and the like,
These can be used alone or in combination of two or more.

Examples of the wetting agent include sorbit, glycerin, ethylene glycol, propylene glycol, 1,3-butylene glycol, polyethylene glycol, polypropylene glycol, xylit, maltite and lactit, which may be used alone or in combination of two or more. Can be combined and compounded.

As the abrasive, for example, dibasic calcium phosphate dihydrate and anhydrous, monobasic calcium phosphate,
Examples include tricalcium phosphate, calcium carbonate, calcium pyrophosphate, aluminum hydroxide, alumina, insoluble sodium metaphosphate, magnesium triphosphate, magnesium carbonate, calcium sulfate, polymethylmethacrylate, and synthetic resins, which may be used alone or in combination with 2 It is possible to mix and combine one or more species.

Further, when used as an oral composition,
As a medicinal component, vitamin Es such as dl-α-tocopherol acetate, tocopherol succinate, or tocopherol nicotinate, nonionic fungicides such as triclosan, amphoteric fungicides such as dodecyldiaminoethylglycine, dextranase, amylase, Enzymes such as protease, mutanase, lysozyme, lytic enzyme (Litech Enzyme), alkali metal monofluorophosphates such as sodium monofluorophosphate, potassium monofluorophosphate, fluorides such as sodium fluoride, stannous fluoride, tranexam Acid, epsilon aminocaproic acid, aluminum chlorohydroxy allantoin,
Dihydrocholesterol, glycyrrhizin salts, glycyrrhetinic acid, glycerophosphate, chlorophyll, sodium chloride, caropeptide, water-soluble inorganic phosphate compounds and the like can be blended alone or in combination of two or more.

There are no particular restrictions on the dosage form of the cleaning composition, and emulsion compositions, solution systems, solubilization systems, powder dispersion systems, water-oil two-layer systems, and water-oil-powder compositions are available. Any formulation such as a layer system may be used.

[V] Antibacterial Fiber Assembly Next, the antibacterial fiber assembly of the present invention will be described. The antibacterial fiber assembly of the present invention is a wet type of the fiber assembly impregnated with a chemical solution containing an amide group-containing guanidine derivative represented by the general formula (I) or a salt thereof,
It can be roughly classified into a dry type in which an amide group-containing guanidine derivative represented by the general formula (I) or a salt thereof is supported on the fiber surface. Hereinafter, (i) a wet type antibacterial fiber aggregate and (ii) a dry type antibacterial fiber aggregate will be described separately.

(I) Wet type antibacterial fiber assembly A wet type antibacterial fiber assembly is prepared by impregnating a chemical solution containing an amide group-containing guanidine derivative represented by the general formula (I) or a salt thereof. Examples include wet tissues which are wrapped in a plastic film and hermetically sealed, or stored in a container and taken out at the time of use to wipe hands and the like. Since wet tissues are stored in a wet state and bacteria are easily proliferated, generally, preservatives and bactericides are added to prevent bacterial growth.

The fiber aggregate used for wet tissues is a fiber woven fabric or a nonwoven fabric in which the fibers are aggregated to form a predetermined shape. Specific examples include rayon, paper which is a non-woven fabric of cellulose fibers, cotton cotton which is an aggregate of cotton fibers, paper made of pulp, and silk aggregate made of silk yarn.

The amount of the amide group-containing guanidine derivative in the liquid medicine used for the wet type antibacterial fiber assembly of the present invention is not particularly limited, but preferably 0.00
It is 1 to 10% by weight, and particularly preferably 0.01 to 5% by weight. If it is less than 0.001% by weight, the effect of the present invention may not be sufficiently exhibited.

In addition to the amide group-containing guanidine derivative or its salt, the chemicals used for the wet type antibacterial fiber assembly of the present invention are usually used for wet tissues and the like as long as the effects of the present invention are not impaired. Various additives can be added as optional components. For example, in addition to a surfactant, a wetting agent, alcohols, an antiseptic and a bactericide other than the amide group-containing guanidine derivative represented by the general formula (I) may be added. As specific examples of these other additives, the same as those exemplified in [III] Composition for skin application can be used. Besides these, anti-inflammatory agents,
Fragrances, deodorants and the like can be added.

(Ii) Dry-type antibacterial fiber assembly A dry-type antibacterial fiber assembly is a fiber assembly in which an amide group-containing guanidine derivative represented by the general formula (I) or a salt thereof is carried on the fiber surface. For example, a fiber aggregate is impregnated with a chemical solution containing an amide group-containing guanidine derivative represented by the general formula (I) or a salt thereof and then dried, or a powdery amide group-containing guanidine derivative. And the like, and the powder of the amide group-containing guanidine derivative is fixed to the fiber surface by heating and pressurizing. Such a dry type antibacterial fiber assembly can be used for, for example, an air filter of an air conditioner, and can suppress / prevent bacterial growth on the air filter.

The amount of the amide group-containing guanidine derivative supported on the dry type antibacterial fiber assembly of the present invention is not particularly limited, but is 0.1 to 100 g / 1 m ² .

As the fiber assembly used for the dry type antibacterial fiber assembly, the same fiber assembly as described for the wet type antibacterial fiber assembly can be used.

[0075]

EXAMPLES The present invention will be described in more detail with reference to Comparative Examples and Examples.

Example 1, Comparative Example 1 (1) Synthesis of amide group-containing guanidine derivative 4-aminobutylguanidine sulfate 52.7 g (0.23 mol) in water 1
80 g and 110 g of 2-propanol were added, and the pH of the system was adjusted to 11.0 and the temperature was adjusted to 10 ° C. with a 27% sodium hydroxide aqueous solution. 50.3 g (0.23 mol) of lauroyl chloride was added dropwise to the system over 35 minutes. At this time, the system temperature was maintained at 8 to 12 ° C and the pH was maintained at 10.9 to 11.0 with 27% aqueous sodium hydroxide solution. After the dropping was completed, the reaction was aged for 35 minutes. After the reaction was completed, the reaction system was adjusted to 50 ° C., the resulting oil layer was adjusted to pH 14.0 by adding 27% aqueous sodium hydroxide solution, and then cooled to room temperature. The precipitated solid was collected by filtration, washed with water, and dried. From the results of identification of the reaction product by ¹ H-NMR, ESI-Mass, high performance liquid chromatography, and ion chromatography, it was confirmed that the product was 4-guanidinobutyldodecane amide.

Light yellow solid, 65.8 g (yield 92%) ¹ H-NMR (CD3OD): σ = 0.90 (3H, t), 1.28-1.38 (18H,
m), 1.57 (6H, m), 2.17 (2H, t), 3.19 (4H, m) ESI-Mass: 313 (MH +) High Performance Liquid Chromatography (Column: YMC-Pack ODS-
AM AM-312, S-5um, 120A, 150 * 6.0mm, Column temperature: 40
C, eluent: 30 mM phosphate buffer (pH 3.0) / methanol = 25/75, flow rate: 1.0 ml / min, detection: UV210nm). Ion chromatography (column: Ion
pac AS-11 HC 2mm (Dionex), Guard column: Ion pac
AG-11 HC 2mm (Dionex), column temperature: room temperature, eluent: N
aOH aqueous solution 1.5 mM (0 min) → 30 mM (20 min), flow rate: 0.38
ml / min, regenerant solution: 5 mM H ₂ SO ₄ approx. 3 mL / min, detection: conductivity)
The residual sulfuric acid amount of 0.1% was confirmed by.

The amide group-containing guanidine derivatives having other acyl chain lengths used in the examples were also prepared by the same method.

(2) Evaluation of antibacterial activity 4-guanidinobutyldodecane amide hydrochloride (LAG.HCL) which is a salt of an amide group-containing guanidine derivative and N-cocoyl-L-arginine which is an N-long chain acyl basic amino acid derivative. The inhibitory concentration (MIC) at which the growth of the test strain of ethyl ester-DL-pyrrolidone carboxylate was completely inhibited was measured.

As a test bacterium, Escherichia coli
i ATCC 8739), Pseudomonas aeruginosa
ATCC 9027), Staphylococcus
aureus ATCC 6538), dental caries (Streptococcus mut
ans ATCC35275), acne bacteria (Propionibacteriu
macnes ATCC 6919), Candida albican
s ATCC10231), Black Aspergillus (Aspergillus ni
ger ATCC16404), athlete's foot fungus (Trichophyton menta
grophytes ATCC11480), dandruff fungus (Malassezia f
urfur ATCC14521) was used.

The test bacterial solution was prepared by using E. coli, P. aeruginos
For a, S. aureus, and S. mutans, precultured in a sensitive broth medium at 35 ° C. for 20 hours was used as a test bacterial solution. For P. acnes, GAM agar at 35 ° C,
After anaerobically culturing for 20 hours, it was scraped off with a platinum loop and suspended in sterile physiological saline to prepare about 10 ⁸ cells / ml, which was used as a test bacterial solution. For C. albicans, after culturing in potato dextrose agar at 25 ° C for 48 hours,
Scratch with a platinum loop and suspend in sterile physiological saline, about 10
^The test bacterial solution was prepared at ⁶ cells / ml. A. niger
For potato dextrose agar at 25 ° C,
After culturing for 7 days, scrape with platinum loop and suspend in sterile physiological saline water, pass through sterile gauze, and pass through 10 ⁶ cells / ml.
The test bacterial solution was prepared as described above. T. mentagrophytes
After culturing in Sabouraud agar for 7 days at 25 ° C, the spores and hyphae were scraped off with a platinum loop, suspended in sterile physiological saline, and crushed with a homogenizer 1 to about 10 ⁶
What was adjusted to the number of cells / ml was used as the test bacterial solution. M. furfur
For, the test strain that had been pre-cultured on YMO agar medium at 25 ° C for 7 days was suspended in sterile phosphate-buffered saline, and
Those adjusted to 0 ⁶ cells / ml was tested bacterial solution.

As the antibacterial activity test sample, 4-guanidinobutyldodecaneamide hydrochloride (LAG.HCL) was dissolved in ethylene glycol to prepare a 2% solution as a mother liquor, and then diluted with water. N-cocoyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate was dissolved in water to prepare a test substance. The minimum inhibitory concentration (μg / ml) at which the microorganism did not grow was determined.

The agar medium described below was used according to each test bacterium. The agar medium (19 ml) was once dissolved and then kept at 50 ° C., and 1 ml of the diluent was added to the agar medium so that the desired concentration was obtained, and the mixture was mixed well and solidified on a plate.

After that, the test bacterial solution is collected with a platinum loop and streaked on an agar plate containing an antibacterial agent with a length of about 1 cm. Each of them was cultured below at a predetermined temperature and time.

[Table 1]

The minimum inhibitory concentration (μg / ml) of 4-guanidinobutyldodecaneamide hydrochloride (LAG.HCL) and N-cocoyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate (CAE) is shown below. .

[0086]

[Table 2]

As shown in Table 2 above, 4-guanidinobutyldodecane amide hydrochloride (LAG.HCl) and N-
It was confirmed that both cocoyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate (CAE) had good antibacterial activity against all test bacteria.

As described above, it is understood that the amide group-containing guanidine derivative has an excellent antibacterial activity almost equal to that of N-cocoyl-L-arginine ethyl ester-DL-pyrrolidone carboxylate (CAE).

(3) Evaluation of chemical stability 4-guanidinobutyl dodecane amide hydrochloride (LAG.
HCl) to evaluate the chemical stability of 4-guanidinobutyldodecane amide hydrochloride (LAG.HCl).
After dissolving 0497 g in 50 ml of water, it was stored at 50 ° C. for 2 weeks. After storage for 2 weeks, the sample was analyzed by HPLC, and when compared with the HPLC data of the sample before storage, no new peak was observed after storage and no change was observed in the peak area. It was found that guanidinobutyl dodecane amide hydrochloride (LAG.HCl) exhibits high stability in aqueous solution.

This is because 4-guanidinobutyldodecane amide hydrochloride (LAG.HCl) was converted to N-like CAE.
This is probably because, unlike the long-chain acyl basic amino acid derivative, it does not have an ester group that may undergo hydrolysis in the molecule.

Examples 2 to 5 4-guanidinobutyl decanamide acetic acid salt (DAG.AcOH), 4-guanidinobutyldodecane amide acetic acid salt (LAG.AcOH), 4-guanidinobutyl, which is a salt of an amide group-containing guanidine derivative. The inhibitory concentration (MIC) of myristylamide acetate (MAG · AcOH) and 4-guanidinobutylpalmitylamide acetate (PAG · AcOH) at which the growth of the test bacteria was completely inhibited was measured.

As a test bacterium, Escherichia col
i ATCC 8739), Pseudomonas aeruginosa
ATCC 9027), Staphylococcus a
ureus ATCC6538), dental caries (Streptococcus mutan
s ATCC35275), acne bacteria (Propionibacterium
acnes ATCC6919), Candida albica
ns ATCC10231), Black Aspergillus (Aspergillus)
niger ATCC16404), athlete's foot fungus (Trichophyton me
ntagrophytes ATCC11480), dandruff fungus (Malassez
ia furfur ATCC14521), mesicillin-resistant Staphylococcus aureus (MRSA), water mold (Cladosporium cladosporioi)
des IFO 6348) was used.

The test bacterial solution was prepared by Escherichia coli, Ps
eudomonas aeruginosa, Staphylococcus aureus, Strep
tococcus mutans, Propionibacterium acnes, Candida
albicans, Aspergillus niger, Trichophyton mentagro
The phytes and Malassezia furfur were prepared as described in Example 1.

MRSA was precultured in a sensitive broth medium at 35 ° C. for 48 hours and used as a test bacterial solution. Cladosporium cla
For dosporioides, after culturing in potato dextrose agar medium at 25 ° C for 5 days, scrape with platinum loops and suspend in sterile physiological saline, and pass through a sterile gauze for about 1 day.
Those prepared 0 ⁶ cells / ml was tested bacterial solution.

As a test sample for antibacterial activity, a water dilution series was prepared for each of the samples, and the minimum inhibitory concentration (μg / ml) at which the microorganism did not grow was determined.

MRSA, Cladosporium cladosporioid
For es, the agar medium described below was used. For the other cells, the agar medium as described above was used. The agar medium (19 ml) was once dissolved and then kept at 50 ° C., and 1 ml of a diluting solution was added to the agar medium to give a desired concentration, and the mixture was mixed well and solidified into a plate. After that, the test bacterial solution was collected with a platinum loop,
A streak of about 1 cm was streaked on an antibacterial-added agar plate. Each of them was cultured below at a predetermined temperature and time.

[Table 3]

The following are 4-guanidinobutyl decanamide acetate (DAG.AcOH), 4-guanidinobutyl dodecaneamide acetate (LAG.AcOH), 4-guanidinobutyramide acetic acid salt.
The minimum inhibitory concentration (ug / ml) is shown for (MAG · AcOH) and 4-guanidinobutyl palmitylamide acetate (PAG · AcOH).

[Table 4]

As shown in the above table, 4-guanidinobutyl decanamide acetic acid salt (DAG.AcOH), 4-guanidinobutyl dodecane amide acetic acid salt (LAG.AcOH), 4-guanidinobutyl myristyl amide acetic acid salt (MAG.AcOH) , 4-guanidinobutylpalmitylamide acetate (PAG · AcOH) were confirmed to have good antibacterial activity against the test bacteria. Especially 4-guanidinobutyl dodecane amide acetate (LAG
・ AcOH) was confirmed to have the best antibacterial activity.

Examples 6 and 7 Compositions shown in Table 5 below (composition pure weight% display, total amount 100%)
Of antibacterial lotion was prepared. When the obtained antibacterial lotion was used, a good feeling of use was obtained.

[0100]

[Table 5]

Examples 8 to 10 Compositions in Table 6 below (composition pure weight% display, total amount 100%)
Was prepared. When the obtained antibacterial emulsion was used, a good feeling of use was obtained.

[0102]

[Table 6]

Examples 11 and 12 Compositions shown in Table 7 below (composition pure weight% display, total amount 100%)
Of antibacterial cream was prepared. When the obtained antibacterial cream was used, a good feeling of use was obtained.

[0104]

[Table 7]

Examples 13 to 15 Compositions shown in Table 8 below (composition pure weight% display, total amount 100%)
Of antibacterial rinse was prepared. When the obtained antibacterial rinse was used, a good feeling of use was obtained.

[0106]

[Table 8]

Examples 16 to 20 Compositions shown in Table 9 below (composition pure weight% display, total amount 100%)
A wet tissue was prepared by impregnating the above-mentioned chemical solution into a cellulose fiber nonwoven fabric. When the obtained wet tissue was used, a good feeling of use was obtained.

[0108]

[Table 9]

Examples 21 and 22 Compositions shown in Table 10 below (composition pure weight% display, total amount 100
%) Chemical solution was impregnated into a rayon nonwoven fabric to prepare a wet sheet. When the obtained wet sheet was used, a good feeling of use was obtained.

[0110]

[Table 10]

Examples 23 to 25 Compositions shown in the following Table 11 (composition pure weight% display, total amount 100)
%) Chemical solution was impregnated into a rayon nonwoven fabric to prepare a wet tissue. When the obtained wet tissue was used, a good feeling of use was obtained.

[0112]

[Table 11]

Examples 26 and 27 Compositions shown in Table 12 below (composition pure weight% display, total amount 100
%) Chemical solution was impregnated into a cellulose fiber nonwoven fabric to prepare a wet tissue. When the obtained wet tissue was used, a good feeling of use was obtained.

[0114]

[Table 12]

Examples 28 to 31 Compositions shown in Table 13 below (composition pure weight% display, total amount 100
%) Toothpaste was adjusted. When the obtained toothpaste was used, a good feeling of use was obtained.

[0116]

[Table 13]

Examples 32-35 Compositions shown in Table 14 below (composition pure weight% display, total amount 100
%) Transparent type toothpaste was prepared. When the obtained toothpaste was used, a good feeling of use was obtained.

[0118]

[Table 14]

Examples 36 to 39 Compositions shown in Table 15 below (composition pure weight% display, total amount 100
%) Liquid toothpaste. When the obtained liquid toothpaste was used, a good feeling of use was obtained.

[0120]

[Table 15]

Examples 40-42 Compositions shown in Table 16 below (composition pure weight% display, total amount 100
%) Liquid toothpaste. When the obtained liquid toothpaste was used, a good feeling of use was obtained.

[0122]

[Table 16]

Examples 43 to 45 Compositions shown in Table 17 below (composition pure weight% display, total amount 100
%) Stock solution type mouthwash. When the obtained mouthwash was used as an undiluted solution, a good feeling of use was obtained.

[0124]

[Table 17]

Examples 46, 47 Compositions shown in Table 18 below (composition pure weight% display, total amount 100
%) Concentrated type mouthwash. When the obtained mouthwash was diluted and used, a good feeling of use was obtained.

[0126]

[Table 18]

Examples 48 and 49 Compositions shown in Table 19 below (expressed as composition weight% by weight, total amount 100)
%) Liquid type mouth freshener was prepared. When the obtained mouth cooling agent was used, a good feeling of use was obtained.

[0128]

[Table 19]

Examples 50 to 54 Compositions shown in Table 20 below (composition pure weight% display, total amount 100
%) Mouthwash was adjusted. When the obtained mouthwash was used, a good feeling of use was obtained.

[0130]

[Table 20]

[0131]

EFFECT OF THE INVENTION The amide group-containing guanidine derivative or its salt used in the present invention has excellent antibacterial activity against various microorganisms and has high chemical stability. Therefore, it is a composition for skin application and a composition for cleaning. , It is extremely useful as a bactericide and antiseptic for antibacterial fiber aggregates.

Front page continuation (51) Int.Cl. ⁷ identification code FI theme code (reference) A61K 7/40 A61K 7/40 7/50 7/50 D06M 13/432 D06M 13/432 // C11D 1/50 C11D 1 / 50 (72) Inventor Hiroshi Yokota 1-1 Suzuki Term, Kawasaki-ku, Kawasaki-shi, Kanagawa Ajinomoto Co., Inc. F-term (reference) 4C083 AA082 AA122 AB172 AB292 AB332 AC012 AC022 AC072 AC102 AC122 AC132 AC172 AC182 AC242 AC272 AC312 AC402 AC422 AC432 AC442 AC472 AC482 AC582 AC612 AC662 AC682 AC692 AC741 AC742 AC782 AC812 AC862 AD042 AD052 AD092 AD152 AD272 AD322 AD352 AD512 AD532 AD552 AD572 AD662 BB48 CC04 CC05 CC24 CC39 CC41 DD01 DD12 DD22 DD23 DD27 DD31 EE01 EE03 EE15 FA16 FA02 FA03 FA02 FA03 FA02 FA03 FA02 AA03 BA01 BA05 BA06 BB05 BB11 BB18 BC01 BC03 BC04 BC06 BC07 BC08 BC09 BC18 BC19 BC22 DA07 DA13 DA16 DA17 DC10 DH03 DH07 DH10 DH13 4L033 AA02 AB07 AC10 AC15 BA81

Claims (8)

[Claims] 1. At least the following general formula (I): (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A bactericidal agent comprising an amide group-containing guanidine derivative represented by the formula (4) or a salt thereof. 2. At least the following general formula (I): (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) An amide group-containing guanidine derivative represented by (4) or a salt thereof is contained. 3. A composition for skin application, comprising the bactericidal agent according to claim 1 and / or the preservative according to claim 2. 4. A cleaning composition comprising the bactericidal agent according to claim 1 and / or the antiseptic agent according to claim 2. 5. A fiber assembly having the following general formula (I): (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A composition containing an amide group-containing guanidine derivative represented by the formula (4) or a salt thereof is impregnated with the composition, and the antibacterial fiber assembly is characterized. 6. The following general formula (I) on the surface of the fiber: (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) An amide group-containing guanidine derivative represented by the formula (1) or a salt thereof is carried on the antibacterial fiber assembly. 7. The following general formula (I): (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A method of sterilizing a microorganism by using an amide group-containing guanidine derivative represented by the above) or a salt thereof. 8. The following general formula (I): (In the general formula (I), R ¹ and R ² are each a hydrogen atom or a carbon number 1 to
4 straight or branched chain alkyl or alkenyl groups, which may be the same or different. R ³ is a linear or branched alkyl group or alkenyl group having 1 to 22 carbon atoms. A is a linear or branched alkylene group having 1 to 10 carbon atoms or an alkenylene group. ) A method for suppressing the growth of microorganisms using an amide group-containing guanidine derivative represented by the above) or a salt thereof.