WO2022168894A1

WO2022168894A1 - Cloth or paper anti-pollution material

Info

Publication number: WO2022168894A1
Application number: PCT/JP2022/004140
Authority: WO
Inventors: 瑞希坂田
Original assignee: 日産化学株式会社
Priority date: 2021-02-05
Filing date: 2022-02-02
Publication date: 2022-08-11
Also published as: JP2024042716A; TW202246447A

Abstract

[Problem] To provide a new material that prevents adhesion of pollutants by forming a film on a cloth or paper surface, and that prevents the cloth and paper surfaces from being polluted by the pollutants. [Solution] An anti-pollution material capable of forming an anti-pollution film on the surface of cloth or paper, the anti-pollution material being characterized by containing a lipid-peptide compound in which a peptide moiety formed by repetition of at least two amino acids that are the same or different is bonded to a lipid moiety composed of a C10-24 aliphatic group.

Description

Cloth or paper contamination prevention material

The present invention relates to an anti-contamination material, and more particularly to a material that prevents adhesion of dust, pollen, particulate matter, etc. by forming a film on the surface of cloth or paper.

In recent years, interest in harmful substances such as allergens such as pollen and fine particulate matter such as PM2.5 has increased, and various products including masks have been developed to prevent these substances from being taken into the human body. there is
As one of such products, there has been proposed a product designed to prevent harmful substances from adhering to the body, clothes, etc. by spraying or the like. For example, a pollen adsorption inhibitor containing a polymer containing a monomer unit having a specific amphoteric ion group or an anion group as a structural unit (Patent Document 1), a harmful substance adhesion inhibitor containing hydroxyalkyl chitosan (Patent Document 2), etc. I have a suggestion.

Japanese Patent No. 4562585 Japanese Patent No. 6198799

So far, there has been no report on a material that prevents adhesion of dust, pollen, particulate matter, etc. to the surface of cloth or paper by using a gel-like substance using a polypeptide.
SUMMARY OF THE INVENTION An object of the present invention is to provide a new material that prevents the adhesion of contaminants by forming a film on the surface of cloth or paper and prevents the surface of cloth or paper from being contaminated by the substance.

The present inventors have found that a material containing at least one lipid peptide compound prevents the adhesion of contaminants by forming a film on the surface of cloth or paper, and completed the present invention.

That is, the present invention provides, as a first aspect, a lipid peptide in which a peptide portion formed by repeating at least two identical or different amino acids is bound to a lipid portion comprising an aliphatic group having 10 to 24 carbon atoms. An antifouling material that prevents substances from adhering to the surface of cloth or paper, characterized by containing a mold compound.
As a second aspect, the anti-pollution material according to the first aspect, wherein the substance is dust, pollen, particulate matter, mites (including corpses), gaseous substances, or odorants.
As a third aspect, the lipid peptide compound is composed of at least one compound represented by the following formulas (1) to (3) or a pharmaceutically usable salt thereof. The antifouling material according to the first aspect or the second aspect.

(In the formula, R ¹ represents an aliphatic group having 9 to 23 carbon atoms, R ² represents a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms which may have a branched chain having 1 or 2 carbon atoms. , R ³ represents a —(CH ₂ ) _n —X group, n represents a number from 1 to 4, X is an amino group, a guanidino group, a —CONH ₂ group, or has 1 to 3 nitrogen atoms represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)

(In the formula, R ⁴ represents an aliphatic group having 9 to 23 carbon atoms, R ⁵ to R ⁷ each independently represents a hydrogen atom, or a branched chain having 1 or 2 carbon atoms. 1 to 4 alkyl groups or —(CH ₂ ) _n —X groups, where n is a number of 1 to 4, and X is an amino group, a guanidino group, a —CONH ₂ group, or 1 to 3 nitrogen atoms; represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)

(In the formula, R ⁸ represents an aliphatic group having 9 to 23 carbon atoms, R ⁹ to R ¹² each independently represent a hydrogen atom, or a branched chain having 1 or 2 carbon atoms. 1 to 4 alkyl groups or —(CH ₂ ) _n —X groups, where n is a number of 1 to 4, and X is an amino group, a guanidino group, a —CONH ₂ group, or 1 to 3 nitrogen atoms; represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)
As a fourth aspect, the pollution control material according to any one of the first aspect to the third aspect, further containing alcohol.
As a fifth aspect, the antifouling material according to any one of the first aspect to the fourth aspect, which prevents adhesion of substances by forming a film on the surface of cloth or paper.
As a sixth aspect, the anti-contamination material according to the fifth aspect, wherein the film surface has roughness and the average surface roughness is 3 nm to 500 nm.
As a seventh aspect, the surface of cloth or paper, comprising a film forming step of forming a film made of the antifouling material according to any one of the first to sixth aspects on the surface of cloth or paper. How to prevent surface contamination.
As an eighth aspect, the method according to the seventh aspect, including the step of volatilizing the alcohol when the antifouling material contains alcohol.
As a ninth aspect, the surface of cloth or paper, comprising a film forming step of forming a film made of the antifouling material according to any one of the first to sixth aspects on the surface of cloth or paper. A method for preventing the deposition of surface contaminants.
As a tenth aspect, the method according to the ninth aspect, comprising the step of volatilizing the alcohol when the antifouling material contains alcohol.

According to the present invention, by forming a film on the surface of cloth or paper with an anti-fouling material containing a specific lipid peptide compound, adhesion of dust, pollen, particulate matter, etc. is prevented, and these substances are It is possible to prevent contamination of cloth or paper by
In addition, according to the present invention, since the anti-pollution substance can prevent adhesion of dust, pollen, particulate matter, etc., skin irritation that can be caused by these substances can be suppressed, and troubles such as inflammation, oxidation, and skin aging can be avoided. .
Furthermore, according to the present invention, since it is possible to prevent the adhesion of fine particulate matter such as pollen and PM2.5, it is possible to bring contaminants into the house, etc., which may be caused by moving these while adhering to cloth or paper. In addition, it is possible to prevent the inhalation of these substances, and it is expected that the occurrence of allergic symptoms due to these substances can be suppressed.
According to the present invention, it is possible to prevent unpleasant odors such as cigarette smoke and odorous substances from adhering to the surfaces of cloth and paper.
In addition, the lipid peptide type compound used in the pollution control material of the present invention is a highly safe artificial low-molecular-weight compound composed only of lipid and peptide. Therefore, the material of the present invention has high biosafety and is very useful in the above applications from the viewpoint of high safety required for pharmaceutical and cosmetic applications. In addition, compared with conventionally proposed products that prevent the adsorption and adhesion of pollen, etc., the present invention uses a membrane composed of a low-molecular-weight lipid peptide compound. When doing so, the feeling of use can be improved.
Further, according to the present invention, high quick-drying properties can be obtained by blending alcohol into the antifouling material using the lipid peptide compound.

FIG. 1 is a diagram showing observation results of a PM2.5 particle adhesion test on a surgical mask. FIG. 2 is a diagram showing the results of observation by scanning microscope (SEM) of a film containing a lipid peptide-type compound and formed by applying an antifouling material. FIG. 3 is a diagram showing the results of measurement of roughness when a film was formed on the surface of a silicon wafer using an atomic force microscope (AFM).

The present invention relates to antifouling materials containing specific lipid peptide type compounds.
The anti-contamination material of the present invention can form a film on the surface of cloth or paper, thereby preventing the adhesion of contaminants such as dust to the surface of cloth and paper, It has an effect (anti-pollution effect) that can prevent contamination by these substances.
Substances to be prevented from adhering to and contaminating the surface of cloth and paper include dust, pollen, air pollutants such as exhaust gas and factory smoke, and particulate matter that can be contained in cigarette smoke, etc. PM10, yellow sand), suspended particulate matter (SPM), PM2.5 (microparticulate matter, etc.), gaseous matter (SOx, CO, etc.), odorants, house dust, allergens such as fungi, dust mites (corpses) including), viruses such as influenza virus, and bacteria.
Each component will be described below.

At least 2 or more of the same or different amino acids are repeated in the lipid portion composed of an aliphatic group having 10 to 24 carbon atoms (10 to 24 carbon atoms in the entire lipid portion) used in the pollution control material of the present invention. Examples of the lipid peptide-type compound to which a peptide portion formed by and a peptide portion that is a hydrophilic portion) can be used.

In the above formula (1), R ¹ represents an aliphatic group having 9 to 23 carbon atoms, preferably R ¹ is a straight chain having 11 to 23 carbon atoms which may have 0 to 2 unsaturated bonds Desirably, it is an aliphatic group.
Specific examples of the lipid moiety (acyl group) composed of R ¹ and an adjacent carbonyl group include lauroyl group, dodecylcarbonyl group, myristoyl group, tetradecylcarbonyl group, palmitoyl group, margaroyl group, oleoyl group, and elaidoyl group. , a linoleoyl group, a stearoyl group, a vaxenoyl group, an octadecylcarbonyl group, an arachidoyl group, an eicosylcarbonyl group, a behenoyl group, an erucanoyl group, a docosylcarbonyl group, a lignoceyl group, a nervonoyl group, and the like. Examples include lauroyl, myristoyl, palmitoyl, margaroyl, stearoyl, oleoyl, elaidoyl and behenoyl groups.

In formula (1) above, R ² contained in the peptide portion represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms which may have a branched chain having 1 or 2 carbon atoms.
The above alkyl group having 1 to 4 carbon atoms and possibly having a branched chain having 1 or 2 carbon atoms means that the main chain has 1 to 4 carbon atoms and has a branched chain having 1 or 2 carbon atoms. means an alkyl group that may have, specific examples thereof include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group or tert-butyl group etc.
R ² above is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms which may have a branched chain of 1 carbon atom, more preferably a hydrogen atom.
An alkyl group having 1 to 3 carbon atoms and possibly having a branched chain having 1 carbon atom is an alkyl group having a main chain having 1 to 3 carbon atoms and possibly having a branched chain having 1 carbon atom. Specific examples thereof include methyl group, ethyl group, n-propyl group, i-propyl group, i-butyl group and sec-butyl group, preferably methyl group, i-propyl group, i-butyl group or sec-butyl group.

In formula (1) above, R ³ represents a —(CH ₂ )nX group. In the —(CH ₂ )nX group, n represents a number of 1 to 4, and X is an amino group, a guanidino group, a —CONH ₂ group, or a 5-membered ring group which may have 1 to 3 nitrogen atoms. Alternatively, it represents a 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.
In the —(CH ₂ )nX group representing R ³ above, X is preferably an amino group, a guanidino group, a carbamoyl group (—CONH ₂ group), a pyrrole group, an imidazole group, a pyrazole group or an indole group, and more An imidazole group is preferred. In the —(CH ₂ )nX group, n is preferably 1 or 2, more preferably 1.
Therefore, the —(CH ₂ )nX group is preferably an aminomethyl group, a 2-aminoethyl group, a 3-aminopropyl group, a 4-aminobutyl group, a carbamoylmethyl group, a 2-carbamoylethyl group, a 3- represents a carbamoylbutyl group, a 2-guanidinoethyl group, a 3-guanidinobutyl group, a pyrrolemethyl group, a 4-imidazolemethyl group, a pyrazolemethyl group, or a 3-indolemethyl group, more preferably a 4-aminobutyl group and a carbamoylmethyl group; 2-carbamoylethyl group, 3-guanidinobutyl group, 4-imidazolemethyl group or 3-indolemethyl group, more preferably 4-imidazolemethyl group.

A particularly suitable lipid peptide in the compound represented by the above formula (1) as a lipid peptide type compound is a compound formed from the following lipid portion and peptide portion (amino acid assembly portion). Amino acid abbreviations include alanine (Ala), asparagine (Asn), glutamine (Gln), glycine (Gly), histidine (His), isolesine (Ile), leucine (Leu), lysine (Lys), tryptophan (Trp ), representing valine (Val). : Lauroyl-Gly-His, Lauroyl-Gly-Gln, Lauroyl-Gly-Asn, Lauroyl-Gly-Trp, Lauroyl-Gly-Lys, Lauroyl-Ala-His, Lauroyl-Ala-Gln, Lauroyl-Ala-Asn, Lauroyl -Ala-Trp, Lauroyl-Ala-Lys; Myristoyl-Gly-His, Myristoyl-Gly-Gln, Myristoyl-Gly-Asn, Myristoyl-Gly-Trp, Myristoyl-Gly-Lys, Myristoyl-Ala-His, Myristoyl-Ala -Gln, Myristoyl-Ala-Asn, Myristoyl-Ala-Trp, Myristoyl-Ala-Lys; Palmitoyl-Gly-His, Palmitoyl-Gly-Gln, Palmitoyl-Gly-Asn, Palmitoyl-Gly-Trp, Palmitoyl-Gly-Lys , Palmitoyl-Ala-His, Palmitoyl-Ala-Gln, Palmitoyl-Ala-Asn, Palmitoyl-Ala-Trp, Palmitoyl-Ala-Lys; Stearoyl-Gly-His, Stearoyl-Gly-Gln, Stearoyl-Gly-Asn, Stearoyl -Gly-Trp, Stearoyl-Gly-Lys, Stearoyl-Ala-His, Stearoyl-Ala-Gln, Stearoyl-Ala-Asn, Stearoyl-Ala-Trp, Stearoyl-Ala-Lys.

Most preferred are Lauroyl-Gly-His, Lauroyl-Ala-His, Myristoyl-Gly-His, Myristoyl-Ala-His, Palmitoyl-Gly-His (Pal-GH), Palmitoyl-Ala-His, Stearoyl-Gly- His, Stearoyl-Ala-His.

In formula (2) above, R ⁴ represents an aliphatic group having 9 to 23 carbon atoms, and preferred specific examples include the same groups as defined for R ¹ above.
In the above formula (2), R ⁵ to R ⁷ are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a branched chain having 1 or 2 carbon atoms, or -( CH ₂ )nX group, preferably at least one or more of R ⁵ to R ⁷ represent —(CH ₂ )nX group. n represents a number from 1 to 4, X is an amino group, a guanidino group, a —CONH ₂ group, or a 5- or 6-membered ring group which may have 1 to 3 nitrogen atoms, or a 5-membered ring and 6 represents a condensed heterocyclic group composed of membered rings. Preferred specific examples of R ⁵ to R ⁷ are the same groups as defined for R ² and R ³ above.

In the compound represented by the above formula (2), a suitable lipid peptide is a compound formed from the following lipid portion and peptide portion (amino acid assembly portion). Lauroyl-Gly-Gly-His, Myristoyl-Gly-Gly-His, Myristoyl-Gly-Gly-Gln, Myristoyl-Gly-Gly-Asn, Myristoyl-Gly-Gly-Trp, Myristoyl-Gly-Gly-Lys, Myristoyl- Gly-Ala-His, Myristoyl-Gly-Ala-Gln, Myristoyl-Gly-Ala-Asn, Myristoyl-Gly-Ala-Trp, Myristoyl-Gly-Ala-Lys, Myristoyl-Ala-Gly-His, Myristoyl-Ala- Gly-Gln, Myristoyl-Ala-Gly-Asn, Myristoyl-Ala-Gly-Trp, Myristoyl-Ala-Gly-Lys, Myristoyl-Gly-His-Gly, Myristoyl-His-Gly-Gly, Palmitoyl-Gly-Gly- His, palmitoyl-Gly-Gly-Gln, palmitoyl-Gly-Gly-Asn, palmitoyl-Gly-Gly-Trp, palmitoyl-Gly-Gly-Lys, palmitoyl-Gly-Ala-His, palmitoyl-Gly-Ala-Gln, Palmitoyl-Gly-Ala-Asn, Palmitoyl-Gly-Ala-Trp, Palmitoyl-Gly-Ala-Lys, Palmitoyl-Ala-Gly-His, Palmitoyl-Ala-Gly-Gln, Palmitoyl-Ala-Gly-Asn, Palmitoyl- Ala-Gly-Trp, Palmitoyl-Ala-Gly-Lys, Palmitoyl-Gly-His-Gly, Palmitoyl-His-Gly-Gly. Stearoyl-Gly-Gly-His.

Among these, the most preferred are lauroyl-Gly-Gly-His, myristoyl-Gly-Gly-His, palmitoyl-Gly-Gly-His, palmitoyl-Gly-His-Gly, palmitoyl-His-Gly-Gly, stearoyl -Gly-Gly-His.

In formula (3) above, R ⁸ represents an aliphatic group having 9 to 23 carbon atoms, and preferred specific examples thereof include the same groups as defined for R ¹ above.
In the above formula (3), R ⁹ to R ¹² are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a branched chain having 1 or 2 carbon atoms, or -( CH ₂ )nX group, preferably at least one or more of R ⁹ to R ¹² represents a —(CH ₂ )nX group. n represents a number from 1 to 4, X is an amino group, a guanidino group, a —CONH ₂ group, or a 5- or 6-membered ring group which may have 1 to 3 nitrogen atoms, or a 5-membered ring and 6 represents a condensed heterocyclic group composed of membered rings. Preferable specific examples of R ⁹ to R ¹² include the same groups as defined for R ² and R ³ above.

Therefore, in the compound represented by the above formula (3), preferred lipid peptide compounds, particularly preferred lipid peptides, include lauroyl-Gly-Gly-Gly-His, myristoyl-Gly-Gly-Gly-His, palmitoyl -Gly-Gly-Gly-His, palmitoyl-Gly-Gly-His-Gly, palmitoyl-Gly-His-Gly-Gly, palmitoyl-His-Gly-Gly-Gly, stearoyl-Gly-Gly-Gly-His, etc. mentioned.

In the present invention, the amount of the lipid peptide compound is, for example, 0.0001 to 30% by mass, preferably 0.001 to 20% by mass, more preferably 0.001 to 10% by mass, relative to the total mass of the antifouling material. % by mass, more preferably 0.01 to 5% by mass.
The lipid peptide-type compound used in the present invention consists of at least one compound (lipid peptide) represented by the above formulas (1) to (3) or a pharmaceutically usable salt thereof, and these compounds can be used singly or in combination of two or more.

The alcohol used in the antifouling material of the present invention is a monohydric alcohol, such as an alcohol having 1 to 6 carbon atoms that dissolves in water at any ratio, specifically methanol, ethanol, 2-propanol. and i-butanol, and higher alcohols, specifically oleyl alcohol and phenoxy alcohol. Ethanol is preferred.

In the present invention, when alcohol is included, its content is, for example, 1% to 50% by mass, preferably 1% to 20% by mass, more preferably 1% to 50% by mass, relative to the total mass of the antifouling material. It can be 10%.
In addition, in this invention, when alcohol is included, alcohol can be used individually by 1 type or in combination of 2 or more types.

The fabrics used in the present invention include natural fibers such as cotton, wool, hemp, silk and cellulose; synthetic fibers such as polyester, nylon and acrylic; semi-synthetic fibers such as acetate; regenerated fibers such as rayon, tencel and polynosic; Fiber blended products, mixed woven products, mixed knitted products, etc., include those formed as woven fabrics and nonwoven fabrics. Papers include cardboard, fine paper, Kent paper, kraft paper, cardboard, Japanese paper, filter paper, etc. include.

The cloth or paper in the present invention is not limited to its use, but clothing such as clothes, skin pads, socks, shoes, hats, mufflers, stoles, scarves, gloves; pillowcases, sheets, beds, Bedding such as pillows, futons, and mattresses; Furniture and miscellaneous goods such as sofas, curtains, and cushions; Hygiene products such as masks, bandages, gauze, plasters, supporters, pads, and tapes; Interior materials such as carpets and cloths; Protective sheets and covers for furniture and miscellaneous goods; Filters for masks, air purifiers, air conditioners, vacuum cleaners, ventilation fans, etc.; Paper products such as tissues, toilet paper, wrapping paper, drawing paper, notebooks, memos, etc.

The antifouling material of the present invention can contain water, polyhydric alcohol, or a mixed solution thereof, in addition to the lipid peptide compound and alcohol.

Examples of the water include purified water, purified water, hard water, soft water, natural water, deep sea water, electrolytic alkaline ionized water, electrolytic acidic ionized water, ionized water, and cluster water.

The polyhydric alcohol is an alcohol having a valence of 2 or more, and examples thereof include propylene glycol, 1,3-butanediol, 2-ethyl-1,3-hexanediol, glycerin, isopentyldiol, ethylhexanediol, and erythrulose. , ozonated glycerin, caprylyl glycol, glycol, (C15-18) glycol, (C20-30) glycol, diethylene glycol, diglycerin, dithiaoctanediol, DPG, thioglycerin, 1,10-decanediol, decylene glycol , triethylene glycol, chilimethylgidroxymethylcyclohexanol, phytantriol, phenoxypropanediol, 1,2-butanediol, 2,3-butanediol, butylethylpropanediol, 1,2-hexanediol, hexylene glycol , pentylene glycol, methylpropanediol, menthanediol, lauryl glycol and polypropylene glycol. Preferred are 1,2-hexanediol and 1,3-butanediol.

In the present invention, when a polyhydric alcohol is included, the content thereof is, for example, 0.001% by mass to 60% by mass, preferably 0.001% by mass to 30% by mass, based on the total mass of the antifouling material. More preferably, it can be 0.01% by mass to 30% by mass.
In addition, in this invention, when a polyhydric alcohol is included, a polyhydric alcohol can be used individually by 1 type or in combination of 2 or more types.

Preferred surfactants include anionic surfactants, nonionic surfactants, cationic surfactants, amphoteric surfactants, polymeric surfactants, and the like. Examples of preferred surfactants include anionic surfactants such as fatty acid salts such as potassium laurate and potassium myristate; alkyl sulfate salts such as sodium lauryl sulfate, triethanolamine lauryl sulfate and ammonium lauryl sulfate; Polyoxyethylene alkyl sulfates such as sodium laureth sulfate and triethanolamine laureth sulfate; sodium cocoyl methyl taurate, potassium cocoyl methyl taurate, sodium lauroyl methyl taurate, sodium myristoyl methyl taurate, sodium lauroyl methyl alanine, sodium lauroyl sarcosinate, lauroyl sarcosyntriate Ethanolamine, acyl N-methyl amino acid salts such as sodium methylalanine lauroyl glutamate; sodium cocoyl glutamate, triethanolamine cocoyl glutamate, sodium lauroyl glutamate, sodium myristoyl glutamate, sodium stearoyl glutamate, ditriethanolamine palmitoyl aspartate, cocoyl alanine triethanol Acyl amino acid salts such as amines; Polyoxyethylene alkyl ether acetates such as sodium laureth acetate; Succinic acid ester salts such as sodium lauroyl monoethanolamide succinate; Fatty acid alkanolamide ether carboxylates; Amine sulfates; fatty acid alkanolamide sulfates; fatty acid glyceride sulfates such as hydrogenated coconut oil fatty acid sodium glycerol sulfate; alkylbenzene polyoxyethylene sulfates; olefin sulfonates such as sodium α-olefin sulfonate; alkyl sulfosuccinates such as dioctyl sodium sulfosuccinate;
Alkyl ether sulfosuccinates such as disodium laureth sulfosuccinate, monolauroyl monoethanolamide sodium polyoxyethylene sulfosuccinate, sodium lauryl polypropylene glycol sulfosuccinate; alkylbenzenes such as sodium tetradecylbenzene sulfonate, triethanolamine tetradecylbenzene sulfonate sulfonate; alkylnaphthalenesulfonate; alkanesulfonate; α-sulfo fatty acid methyl ester salt; acyl isethionate; alkylglycidyl ether sulfonate; Alkyl ether phosphates such as sodium acid and sodium monooleth phosphate; Alkyl phosphates such as potassium lauryl phosphate; Sodium caseinate; Alkyl aryl ether phosphates; Fatty acid amide ether phosphates;
Phospholipids such as phosphatidylglycerol, phosphatidylinositol, and phosphatidic acid; silicone-based anionic surfactants such as carboxylic acid-modified silicone, phosphoric acid-modified silicone, and sulfuric acid-modified silicone; nonionic surfactants include laureth ( polyoxyethylene lauryl ether), ceteth (polyoxyethylene cetyl ether), steareth (polyoxyethylene stearyl ether), beheneth (polyoxyethylene behenyl ether), isosteareth (polyoxyethylene isostearyl ether), octyldodeceth Polyoxyethylene alkyl ethers with various polyoxyethylene addition numbers such as (polyoxyethylene octyldodecyl ether); polyoxyethylene alkylphenyl ethers; polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil and hydrogenated castor oil derivatives such as castor oil monoisostearate, polyoxyethylene hydrogenated castor oil triisostearate, polyoxyethylene hydrogenated castor oil monopyroglutamic acid monoisostearate diester, polyoxyethylene hydrogenated castor oil maleic acid; Polyoxyethylene phytosterol; Polyoxyethylene cholesterol; Polyoxyethylene cholestanol; Polyoxyethylene lanolin; Polyoxyethylene reduced lanolin; , polyoxyethylene/polyoxypropylene monobutyl ether, polyoxyethylene/polyoxypropylene hydrogenated lanolin, polyoxyethylene/polyoxypropylene alkyl ether such as polyoxyethylene/polyoxypropylene glycerin ether; polyoxyethylene/polyoxypropylene Glycol; (poly)glycerol polyoxypropylene glycol such as PPG-9 diglyceryl; glyceryl stearate, glyceryl isostearate, glyceryl palmitate, glyceryl myristate, glyceryl oleate, glyceryl coconut oil, monocottonseed glycerin, monoerucic acid glycerin fatty acid partial esters such as glycerin, glycerin sesquioleate, α,α'-pyroglutamic acid glyceryl oleate, glyceryl monostearate malic acid;
Polyglyceryl-2 stearate, 3, 4, 5, 6, 8, 10, polyglyceryl-6, 10 distearate, polyglyceryl-2 tristearate, polyglyceryl-10 destearate, polyglyceryl isostearate -2, 3, 4, 5, 6, 8, 10, polyglyceryl-2 diisostearate (diglyceryl diisostearate), 3, 10, polyglyceryl-2 triisostearate, polyglyceryl tetraisostearate -2, polyglyceryl-10 decaisostearate, polyglyceryl-2 oleate, 3, 4, 5, 6, 8, 10, polyglyceryl-6 dioleate, polyglyceryl-2 trioleate, polyglyceryl decaoleate polyglycerin fatty acid esters such as -10; ethylene glycol mono fatty acid esters such as ethylene glycol monostearate; propylene glycol mono fatty acid esters such as propylene glycol monostearate; pentaerythritol partial fatty acid esters; sorbitol partial fatty acid esters; ester;
Maltitol ether; sorbitan monooleate, sorbitan monoisostearate, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan sesquioleate, sorbitan trioleate, diglycerol sorbitan penta-2-ethylhexylate, tetra -Sorbitan fatty acid esters such as 2-ethylhexyl diglycerol sorbitan; sucrose caprate, sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, sucrose oleate, sucrose esters such as sucrose arachidate and sucrose behenate; sugar derivative partial esters such as methyl glucoside fatty acid esters and trehalose undecylenate; alkyl glucosides such as caprylyl glucoside; alkyl polyglycosides; lanolin alcohol; Polyoxyethylene fatty acid mono- and diesters such as polyoxyethylene distearate, polyethylene glycol diisostearate, polyoxyethylene monooleate, polyoxyethylene dioleate; polyoxyethylene/propylene glycol fatty acid esters; polyoxyethylene Polyoxyethylene glycerin fatty acid esters such as polyoxyethylene monooleates such as glycerin monostearate, polyoxyethylene glycerin monoisostearate, polyoxyethylene glycerin triisostearate;
Polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan tetraoleate; polyoxyethylene sorbitol monolaurate, polyoxyethylene Polyoxyethylene sorbitol fatty acid esters such as sorbitol monooleate, polyoxyethylene sorbitol pentaoleate, polyoxyethylene sorbitol monostearate; polyoxyethylene methyl glucoside fatty acid esters; polyoxyethylene alkyl ether fatty acid esters; polyoxyethylene sorbitol beeswax Polyoxyethylene animal and vegetable oils and fats such as;
Alkyl glyceryl ethers such as isostearyl glyceryl ether, chimyl alcohol, selachyl alcohol, and batyl alcohol; polyhydric alcohol alkyl ethers; polyoxyethylene alkylamines; tetrapolyoxyethylene/tetrapolyoxypropylene-ethylenediamine condensates; , natural surfactants such as sophorolipid; polyoxyethylene fatty acid amides; coconut oil fatty acid monoethanolamide (cocamide MEA), coconut oil fatty acid diethanolamide (cocamide DEA), lauric acid monoethanolamide (lauramide MEA), lauric acid diethanolamide fatty acid alkanolamides such as de (Lauramide DEA), lauric acid monoisopropanolamide (Lauramide MIPA), palmitic acid monoethanolamide (Partamide MEA), palmitic acid diethanolamide (Partamide DEA), coconut oil fatty acid methylethanolamide (Cocamide methyl MEA) Alkyldimethylamine oxides such as lauramine oxide, cocamine oxide, stearamine oxide, and behenamine oxide; Alkyldimethylamine oxides; Polyoxyethylene alkylmercaptans; Silicone-based nonionic surfactants such as oxyalkylene copolymers, polyglycerin-modified silicones, and sugar-modified silicones;
Cationic surfactants include alkyltrimethylammonium chlorides such as behentrimonium chloride, steartrimonium chloride, cetrimonium chloride and lauryltrimonium chloride; alkyltrimethylammonium bromides such as stearyltrimonium bromide; and distearyldimonium chloride. , Dialkyldimethylammonium chloride such as dicocodimonium chloride; Fatty acid amide amines such as stearamidopropyldimethylamine, stearamidoethyldiethylamine and salts thereof; Alkyl ether amines such as stearoxypropyldimethylamine and salts or quaternary salts thereof; Ethyl sulfate Long-chain branched fatty acid (12-31) fatty acid amide type quaternary ammonium salts such as aminopropylethyldimethylammonium, ethyl sulfate lanolin fatty acid aminopropylethyldimethylammonium; polyoxyethylene alkylamines and their salts or quaternary salts; alkylamine salts fatty acid amide guanidinium salts; alkyl ether amine monium salts; alkyltrialkylene glycol ammonium salts; benzalkonium salts; benzethonium salts; pyridinium salts such as cetylpyridinium chloride; morphonium salts; polyamine fatty acid derivatives; silicone cationic surfactants such as amino-modified silicones such as aminopropyl dimethicone and amodimethicone, cation-modified silicones, cation-modified and polyether-modified silicones, amino-modified and polyether-modified silicones etc;
Amphoteric surfactants include N-alkyl-N,N-dimethyl amino acid betaines such as lauryl betaine (betaine lauryldimethylaminoacetate); fatty acid amide alkyl-N,N-dimethyl such as cocamidopropyl betaine and lauramidopropyl betaine Amino acid betaines; imidazoline-type betaines such as sodium cocoamphoacetate and sodium lauroamphoacetate; alkylsulfobetaines such as alkyldimethyltaurine and laurylhydroxysulfobetaine; sulfate-type betaines such as alkyldimethylaminoethanol sulfate; phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, sphingophospholipids such as sphingomyelin, lysolecithin, hydrogenated soybean phospholipids, partially hydrogenated soybean phospholipids, hydrogenated egg yolk phospholipids, partially hydrogenated egg yolk phospholipids , Phospholipids such as hydroxylated lecithin; Silicone-based amphoteric surfactants, etc.;
Preferred polymer surfactants include polyvinyl alcohol, sodium alginate, starch derivatives, tragacanth gum, acrylic acid/methacrylate alkyl copolymers, and various silicone surfactants. Most preferred are sucrose esters, polyoxyethylene alkyl ethers, alkylsulfobetaines, alkylglucosides.

In the present invention, when a surfactant is included, its content is, for example, 0.001% by mass to 50% by mass, preferably about 0.01% by mass to 20% by mass, relative to the total mass of the antifouling material. can do.

The fatty acid is preferably at least one selected from the group consisting of saturated fatty acids and unsaturated fatty acids having 10 to 20 carbon atoms and salts of these fatty acids. Examples of fatty acids include capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid. More preferred are capric acid, lauric acid, myristic acid, palmitic acid and stearic acid. Stearic acid is most preferred.

In the present invention, when fatty acid is included, the content thereof is preferably 0.01 to 1% by mass, more preferably 0.01 to 0.5% by mass, still more preferably 0.01 to 0.5% by mass, based on the total mass of the pollution control material. It can be 0.025 to 0.1% by mass.
In addition, the fatty acid used in the present invention is at least one selected from the above fatty acid group, and these fatty acids can be used alone or in combination of two or more.

The antifouling material of the present invention can contain additives that can be generally used as additives for cosmetics, additives for quasi-drugs, and additives for pharmaceuticals, if necessary. Examples of additive components such as physiologically active substances and functional substances that are blended in external skin preparations such as cosmetics, quasi-drugs, and pharmaceuticals include pigments, oily bases, moisturizers, texture improvers, and surfactants other than the above. agent, polymer/thickener/gelling agent, solvent, antioxidant, reducing agent, oxidizing agent, preservative, antibacterial agent, bactericide, chelating agent, pH adjuster, acid, alkali, powder, inorganic salt , UV absorbers, whitening agents, vitamins and their derivatives, hair growth agents, blood circulation promoters, stimulants, hormones, anti-wrinkle agents, anti-aging agents, tightening agents, cooling agents, warming agents, wound healing stimulant, stimulant, analgesic, cell activator, plant/animal/microorganism extract, antipruritic, exfoliating/dissolving agent, antiperspirant, cooling agent, astringent, enzyme, nucleic acid, fragrance, pigment, colorant , dyes, anti-inflammatory agents, anti-inflammatory agents, anti-asthmatic agents, anti-chronic obstructive pulmonary disease agents, anti-allergic agents, immunomodulators, anti-infective agents and anti-fungal agents. The content of these other additives may vary depending on the type, but is, for example, about 0.001% to 20% by mass, or about 0.01% to 10% by mass, relative to the total mass of the antifouling material. can be

The antifouling material of the present invention may be of any formulation as long as it can form a film (layer) on the surface of cloth or paper.
For example, emulsion type such as oil-in-water (O/W) type, water-in-oil (W/O) type, W/O/W type, O/W/O type, oily type, solid type, liquid type, dough type, stick type , volatile oil type, powder type, jelly type, gel, paste type, emulsified polymer type, sheet type, mist type, spray type, etc., but not limited to these. Moreover, the product form is also arbitrary, and it can be used as a dispersion, milky lotion, cream, pack, spray, gel, and the like.
Various components known to those skilled in the art can be blended into the antifouling material according to the dosage form/product form in order to realize the dosage form/product form.

[Manufacturing method of antifouling material]
The antifouling material of the present invention can be produced, for example, by mixing and stirring at least one lipid peptide compound, water, and optionally other components while heating, and then allowing the mixture to stand and cool to about room temperature.
The heating/stirring temperature is not particularly limited as long as each component can be uniformly mixed. can be appropriately selected, for example, from 5 minutes to 3 hours.

The present invention also relates to a method for preventing contamination of the surface of cloth or paper, comprising a film-forming step of forming a film of a contamination-preventing material containing the lipid peptide compound on the surface of cloth or paper. .
Furthermore, the present invention provides a method for removing dust, pollen, and particles from the surface of cloth or paper, comprising a film-forming step of forming a film of the antifouling material containing the lipid peptide compound on the surface of cloth or paper. The present invention relates to a method for preventing adherence of odorous substances, gaseous substances, odorous substances, viruses or bacteria.
Used in the method for preventing contamination of the surface of cloth or paper and the method for preventing adhesion of dust, pollen, particulate matter, gaseous substances, odorous substances, viruses or bacteria to the surface of cloth or paper Contamination-preventing materials can be those detailed above.

The antifouling material of the present invention exhibits its effects by forming moderate roughness (hereinafter also referred to as roughness) on the surface of cloth or paper. Roughness is represented by the width between the maximum and minimum heights in the vertical direction with respect to the surface of cloth or paper.

The roughness formed by the anti-contamination material in the present invention is, for example, an average surface roughness of 3 nm to 500 nm, more preferably 10 nm to 300 nm.

The anti-contamination material in the present invention is formed by a fiber structure, and preferably has an average diameter of 10 nm to 100 nm. The average diameter of the fibers can be calculated from the image of the surface of the anti-contamination material, which is obtained by detecting secondary electrons using a scanning microscope.

Hereinafter, the present invention will be described in detail with examples and test examples, but the present invention is not limited to these examples.

[Synthesis Example 1: Synthesis of lipid peptide (N-palmitoyl-Gly-His)]
The lipid peptide-type compound used in this example was synthesized by the method shown below. 14.2 g (91.6 mmol) of histidine, 30.0 g (91.6 mmol) of N-palmitoyl-Gly-methyl, and 300 g of toluene were added to a 500 mL four-necked flask, and a 28% methanol solution of sodium methoxide as a base was added. 35.3 g (183.2 mmol) was added, heated to 60° C. in an oil bath, and stirred for 1 hour. After that, the oil bath was removed and the solution was allowed to cool to 25° C., and the solution was reprecipitated with 600 g of acetone and collected by filtration. The solid obtained here was dissolved in a mixed solution of 600 g of water and 750 g of methanol, and neutralized by adding 30.5 ml (183.2 mmol) of 6N hydrochloric acid to precipitate a solid, followed by filtration. Next, the obtained solid was dissolved in a mixed liquid of 120 g of tetrahydrofuran and 30 g of water at 60°C, 150 g of ethyl acetate was added, and the solution was cooled from 60°C to 30°C. After that, the precipitated solid was filtered. Further obtained solid was dissolved in a solvent of 120 g of tetrahydrofuran and 60 g of acetonitrile, heated to 60° C., stirred for 1 hour, cooled and filtered. The solid obtained here was washed with 120 g of water, filtered and then dried under reduced pressure. %) was obtained.

[Comparative Example 1, Examples 1 to 6]
-Preparation of specimen According to Table 1 below, each raw material heated to 75°C was stirred in a 200 mL beaker (manufactured by HARIO Co., Ltd.), and heated and stirred at 75°C for 30 minutes. After 30 minutes, the mixture was stirred and cooled to 40°C. In the above steps, stirring was performed at 200 rpm.

Ethanol: manufactured by Junsei Chemical Co., Ltd. Phenoxyethanol: manufactured by Tokyo Chemical Industry Co., Ltd. 1,2-Hexanediol: manufactured by Kankosha Co., Ltd. [Product name: KMO-6]
1,3-butylene glycol: manufactured by Daicel Co., Ltd. Polyoxyethylene lauryl ether: manufactured by Nikko Chemicals Co., Ltd. [trade name: BL-4.2]
Lauryl hydroxysulfobetaine: manufactured by Kao Corporation [trade name: Amphithor 20HD]
Sucrose laurate (L-1695): manufactured by Mitsubishi Chemical Foods Co., Ltd. [trade name: Ryoto Sugar Ester L-1695]
Sucrose laurate (L-595): manufactured by Mitsubishi Chemical Foods Co., Ltd. [trade name: Ryoto Sugar Ester L-595]
Myristyl alcohol: manufactured by Kao Corporation [trade name: Calcol 4098]
Cetanol: manufactured by Kao Corporation [trade name: Calcol 6098]
Stearic acid: manufactured by Kao Corporation [trade name: Lunax S-98]

・ Suppression of adhesion of PM2.5 particles on the mask A surgical mask (manufactured by Tokunaga Electric Co., Ltd.) was cut into a size of 2 cm × 2 cm, and 1.0 mL each of the solutions of Comparative Example 1 and Examples 1 to 6 was applied. , and dried in a constant temperature bath at 32°C for 1 hour. Put 1.5 g of PM2.5 particles (NIES-CRM No. city air dust) in a 4 cm × 4 cm weighing dish, bring each sample prepared above into contact with PM2.5 particles, press them 10 times with tweezers, and pull them up. After that, the PM2.5 particles adhering excessively were removed by shaking for 10 seconds. The adhesion amount of 5 particles was evaluated. The results are shown in FIG. The masks coated with Comparative Examples 1 to 6 suppressed adhesion of PM2.5 particles compared to Comparative Example 1, indicating that they had an anti-pollution effect.

・ Field emission scanning electron microscope measurement of the film formed on the mask surface. It was applied and dried in a constant temperature bath at 32°C for 1 hour. After that, the film formed on the mask surface was peeled off by sticking a carbon tape on the mask surface, and the result of observing the film with a field emission scanning electron microscope JSM-7400F (manufactured by JEOL Ltd.) is shown in FIG. .

Measurement of Roughness of Formed Film A silicon substrate was cut into a size of 2 cm×2 cm, 1.0 mL of each of the solutions of Examples 1 to 6 was applied, and dried in a constant temperature bath at 32° C. for 1 hour. FIG. 3 shows the result of measuring the roughness of the film formed on the surface of the silicon substrate with an AFM atomic force microscope Dimension Icon (manufactured by Bruker AXS). The average roughness of the surface of the silicon substrate coated with Examples 1 to 6 was about 20 nm to 80 nm.

・ Measurement of drying time of the applied solution 100 μL each of the solutions of Comparative Example 1 and Examples 1 to 6 are applied to a 26 mm × 76 mm microslide glass (manufactured by Matsunami Glass Industry Co., Ltd.) using a micropipetter. did. Then, it was placed on a digital hot plate stirrer PC-620D (manufactured by Corning Incorporated) set at 50° C., and the time required for complete drying was measured. Table 2 shows the results of recording the measurement time with a stopwatch.

Claims

Characterized by containing a lipid peptide type compound in which a peptide portion formed by repeating at least two or more of the same or different amino acids is bound to a lipid portion consisting of an aliphatic group having 10 to 24 carbon atoms. , an anti-fouling material that prevents substances from adhering to the surface of cloth or paper.
2. The anti-pollution material of claim 1, wherein the substance is dust, pollen, particulate matter, mites (including corpses), gaseous substances, or odorants.
1 or 2, wherein the lipid peptide compound comprises at least one compound represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof: 2. The antifouling material according to 2.

(In the formula, R 1 represents an aliphatic group having 9 to 23 carbon atoms, R 2 represents a hydrogen atom, or an alkyl group having 1 to 4 carbon atoms which may have a branched chain having 1 or 2 carbon atoms. , R 3 represents a —(CH 2 ) n —X group, n represents a number from 1 to 4, X is an amino group, a guanidino group, a —CONH 2 group, or has 1 to 3 nitrogen atoms represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)

(In the formula, R 4 represents an aliphatic group having 9 to 23 carbon atoms, R 5 to R 7 each independently represents a hydrogen atom, or a branched chain having 1 or 2 carbon atoms. 1 to 4 alkyl groups or —(CH 2 ) n —X groups, where n is a number of 1 to 4, and X is an amino group, a guanidino group, a —CONH 2 group, or 1 to 3 nitrogen atoms; represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)

(In the formula, R 8 represents an aliphatic group having 9 to 23 carbon atoms, R 9 to R 12 each independently represent a hydrogen atom, or a branched chain having 1 or 2 carbon atoms. 1 to 4 alkyl groups or —(CH 2 ) n —X groups, where n is a number of 1 to 4, and X is an amino group, a guanidino group, a —CONH 2 group, or 1 to 3 nitrogen atoms; represents a 5-membered ring group or 6-membered ring group, or a condensed heterocyclic group composed of a 5-membered ring and a 6-membered ring.)
4. A pollution control material according to any one of claims 1 to 3, further comprising alcohol.
5. The antifouling material according to any one of claims 1 to 4, which prevents adhesion of substances by forming a film on the surface of cloth or paper.
6. The anti-pollution material according to claim 5, which has roughness on the film surface and has an average surface roughness of 3 nm to 500 nm.
Preventing contamination of the surface of cloth or paper, comprising a film forming step of forming a film made of the anti-contamination material according to any one of claims 1 to 6 on the surface of cloth or paper how to.
8. The method of claim 7, comprising volatilizing the alcohol if the antifouling material contains alcohol.
A film forming step of forming a film made of the anti-contamination material according to any one of claims 1 to 6 on the surface of the cloth or paper, removing contaminants on the surface of the cloth or paper. How to prevent sticking.
10. The method of claim 9, comprising volatilizing the alcohol if the antifouling material contains alcohol.