Hair or fiber treatment composition containing an alkylketene compound

Abstract

The present invention relates to a hair or fiber treatment composition comprising an alkylketene compound that can covalently bond with protein residues on the surface of hair or fibers, and the alkylketene compound can form a covalent bond with the hair or fiber to provide beneficial effects such as long-lasting conditioning.

Description

[Technical Field]

[0001] The present invention relates to hair or fiber treatment compositions containing alkylketene compounds. [Background technology]

[0002] Generally, hair cosmetics are intended to be painted, sprinkled, and otherwise similarly applied to hair to beautify, enhance attractiveness, alter appearance, or invigorate the hair by imparting beneficial properties such as smoothness, softness, ease of brushing, volume, neatness, and styling.

[0003] Hair conditioning must be a continuous process. Hair is essentially a mass of dead cells derived from a small number of living cells present deep within the skin's surface. Therefore, hair conditioning ingredients have no effect on the growth of actual cells and cannot affect the fundamental repair of cells. Therefore, hair conditioning only temporarily improves the properties of damaged hair, and must be applied again once the conditioning is removed.

[0004] Damage to hair caused by physical and chemical treatments induces changes in the physical structure of hair. Although conditioning ingredients cannot fundamentally heal hair, they can temporarily enhance the cosmetic value and functionality of hair before it is cleansed and removed with a cleanser. Therefore, it is very important for conditioning ingredients to remain on hair for a long time without being removed even when a cleanser is used, thereby maintaining their effect.

[0005] Most hair damage occurs due to hair care practices such as cosmetic shampooing, drying, brushing, styling, conditioning, perming, exposure to chemicals, and environmental factors such as sunlight, air pollution, wind, salt water, and chlorinated swimming pools. Conditioners can improve the cosmetic value of weathered hair through various mechanisms such as reducing static, improving hair strength, protecting against UV radiation, and increasing shine.

[0006] In the present invention, hair treatments include reducing hair breakage and porosity, increasing strength and luster, and alleviating, preventing, or repairing hair damage caused by a variety of damaging factors, such as heat, dyeing, perms, washing, and UV rays. Conditioners using cationic surfactant or cationic polymer components contain highly efficient conditioning ingredients that directly participate in the electrical interaction between the surfactant or polymer and the opposite charge on the hair surface, resulting in affinity. Conditioners generally remain on the surface of hair strands, reducing friction and hair flutter upon brushing and making hair feel soft and flexible. In some other systems, conditioners impart volume enhancement, curl retention, fullness, ease of care, etc., and these properties are also included in the hair treatments of the present invention.

[0007] In addition, recent conditioners are designed to provide one or more of the following functions: making hair easy to brush in wet and dry states; providing softness by filling in and rearranging damaged areas of the hair; minimizing porosity; imparting shine and a silky feel to the hair; providing protection against thermal and mechanical damage; moisturizing; imparting volume and a thick feel; and eliminating static electricity; and the provision of such properties is also included in the hair treatment of the present invention.

[0008] Generally, the human hair cuticle is composed of flat, overlapping cells (scales). Cuticle cells are attached from the base to the tip of the hair fiber like roof tiles. Each cuticle layer is approximately 0.3 to 0.5 μm thick, and the visible cuticle portion is approximately 5 to 10 μm. The human hair cuticle generally has 5 to 10 layers. Each cuticle cell in the hair is composed of various sublamellar layers, such as the epicuticle, A-layer, exocuticle, endocuticle, and inner layer, as well as a cell membrane complex. The outermost epicuticle layer is covered with covalently bonded lipids (fatty acids), the most abundant of which is 18-methyl eicosanoic acid (18-MEA). This layer constitutes the outer β-layer of the cuticle cell membrane complex and plays a role in lubrication, friction reduction, and hydrophobic surface formation.

[0009] The part of the hair that protrudes from the scalp is called the hair shaft, and this part changes depending on the lifespan and length of the hair. It also changes depending on environmental stresses such as cutting, shampooing, using a hair dryer, brushing, permanent waving, and hair coloring, as well as dryness, ultraviolet rays, seawater, and limescale in swimming pools. In particular, the cuticle, which surrounds the outside of the hair shaft, is damaged when these stresses accumulate in complex ways, even if they are not directly affected. Damaged hair has elongated or partially peeled cuticle ends, and is more prone to falling out. Such hair diffuses light, losing its luster and becoming dull. As hair damage progresses, the cuticle layer falls off completely, exposing the inner cortex, eventually making the hair more prone to splitting or breaking.

[0010] In order to improve the damaged hair surface caused by the loss of 18-MEA, various treatments have been attempted. In particular, products that provide conditioning effects to hair, such as hair manicures and hair essences that use silicone to coat the hair surface, are sold or applied at beauty salons. However, when such conditioning ingredients are used on hair, they only provide a temporary and short-term effect until the next wash after treatment, and there is always the inconvenience of having to re-treat after washing.

[0011] Patent Document 1 relates to a non-aqueous personal care product for skin or hair, and lists functional groups capable of covalently bonding with protein residues on the surface of hair or skin, such as carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, and hydroxysuccinimidyl ester. The present invention discloses a conditioning ingredient having one or more selected from the group consisting of alkyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, and a functional group represented by RX (wherein R is any one selected from the group consisting of alkyl, aryl, aralkyl, a ring, and an unsaturated ring, and X is I, Br, or Cl). The invention also discloses a personal care product for hair or skin that contains the conditioning ingredient and is separated into a non-aqueous part and an aqueous part, which are mixed together immediately before use. The various functional groups listed above are either harmful to the human body or react with lysine (1.9-3.1% in hair, 3.1-6.9% in skin keratin) or cysteine ​​(16.6-18% in hair, 2.3-3.8% in skin keratin), which are found in low concentrations among the amino acids that make up hair or skin, resulting in low reaction efficiency and the need to synthesize each substance separately.

[0012] In the present invention, the functions of the fiber treatment agent mean functions such as imparting a softening effect to fibers, preventing damage due to light, suppressing wrinkle formation in fibers, easily removing wrinkles that have formed, making the original color of fibers vivid, maintaining the original color for a long period of time, easily removing surface stains, imparting fragrance, removing odors, having antibacterial properties and insect repellent properties, preventing damage due to washing, and preventing penetration of rainwater and the like.

[0013] In the present invention, the textile treatment composition may include compositions for cleaning, conditioning, pointing, etc., for general textile care, as well as compositions for textile beneficial functions such as dyeing, bleaching, softening, disinfecting, UV protection, fragrance, and the like.

[0014] Examples of products formulated with such compositions include detergents, fabric softeners, fabric rinses, treatments, and partial treatment agents.

[0015] Typical raw materials used to constitute such fabric care compositions include oily raw materials such as fats and oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, ester oils and silicone oils, anionic, cationic, amphoteric and nonionic surfactants, polymeric compounds used as moisturizers, thickeners and film formers, ultraviolet light absorbers and screeners, antioxidants, sequestering agents, ion exchange agents, builders, bleaching agents, enzymes, foam regulators, optical brighteners, dye transfer inhibitors, colorants including dyes and pigments, fragrances and preservatives.

[0016] In addition, as a fabric care ingredient for providing special performance, ingredients may be included that impart a softening effect to fabrics, prevent damage by light, inhibit wrinkle formation in fabrics, make formed wrinkles easily removable, brighten the original color of fabrics, maintain the original color for a long time, make surface contamination easily removable, impart a fragrance, remove odors, have antibacterial or pest repellent properties, prevent damage due to washing, or prevent penetration of rainwater, etc., and specific examples thereof include soap, alkyl benzene sulfonate, alkane sulfonate, alpha olefin sulfonate, alpha sulfo fatty acid ester, alkyl sulfate, alkyl ether sulfate, alcohol ethoxylate, alkylphenol ethoxylate, fatty acid alkanolamide, alkylamine oxide, methyl glucamide, alkyl polyglucoside, distearyl dimethyl ammonium chloride, imidazolinium derivative, alkyl dimethyl benzene ammonium chloride, ester quat, amino ester salt, alkyl betaine, alkyl sulfobetaine, sodium carbonate, calcium carbonate, ketone ... The surfactants may include sodium carbonate, sodium triphosphate, nitrilotriacetic acid, polycarboxylates, zeolites, sodium polycarboxylates, sodium polyacrylates, sodium hydroxyethane diphosphate, sodium perborate, sodium percarbonate, peroxide, hypochlorite, tetraacetylethylenediamine, sodium paranonanoyloxybenzenesulfonate, sodium percarbonate, sodium perborate, proteolytic enzymes, lipolytic enzymes, amylolytic enzymes, pectinolytic enzymes, cellulolytic enzymes, carboxymethylcellulose, carboxymethyl starch, cellulose ethers, polyethylene terephthalic acid / polyoxyethylene terephthalic acid copolymers, fatty acid amides, fatty acid alkanolamides, amine oxides, stilbenes, coumarins, bisbenzazoles, distyryl biphenyl, polyvinylpyrrolidone, polyvinylpyridine oxide, fragrances, cyclodextrins, sodium sulfate, silicones and derivatives, alkylamines, fatty alcohols, fatty acids, polyethylene, magnesium chloride, calcium chloride, sodium chloride, and sodium acetate.

[0017] However, when such fabric care ingredients are used on fabrics, there is always the inconvenience that after treatment they only provide a temporary effect until the next wash, and they must be reapplied after washing.

[0018] Patent Document 2 discloses a cosmetic treatment method for long-lasting cosmetic properties on hair, which has similar components to wool fibers. This technique requires a hair activation process to occur before the cosmetic treatment, using physical methods such as heat, electromagnetic waves, electric fields, sound waves, and plasma, or chemical methods (excluding reduction methods) to alter the hair surface. However, this hair activation process requires the application of high energy such as heat, electromagnetic waves, electric fields, sound waves, and plasma to the hair, and oxidizing agents such as hydrogen peroxide and bromate, which are used as chemical deactivators (excluding reduction methods), can cause severe damage to the hair. While activation is possible with other polyamine and polysaccharide polymers, these polymers are not covalently bonded to the hair and are therefore easily removed by washing.

[0019] In addition, Patent Document 3 proposes a method of microencapsulating and adding a fragrance using chitosan, an antibacterial ingredient, to impart antibacterial properties to fabrics, while also providing fabric softening effects and excellent fragrance durability. Microencapsulating a fragrance in this way offers the advantage of excellent fragrance durability in fabrics, as the capsules protect the fragrance of the core material from the external environment and improve storage stability. However, these fragrance capsules are mostly washed away during the washing process, rather than remaining on the fabric surface. This limits the effectiveness of the capsule components remaining on the fabric, and also poses an economical problem: used capsules perform little function and are washed away in the wash water. [Prior art documents] [Patent documents]

[0020] [Patent Document 1] Korean Patent Publication No. 2008-0064467 [Patent Document 2] Japanese Patent Publication No. 2004-182731 [Patent Document 3] Korean Patent Publication No. 2002-0068427 Summary of the Invention [Problem to be solved by the invention]

[0021] An object of the present invention is to provide a hair or fiber treatment composition that can provide beneficial effects such as conditioning for a long period of time without damaging the hair or fiber.

[0022] Another object of the present invention is to provide a hair or fiber treatment composition that can maintain a lingering fragrance on hair or fibers and enhance softness, softness, hydrophobicity, and / or shrinkage prevention. [Means for solving the problem]

[0023] As a means for solving the above problems, the present invention provides a hair or fiber treatment composition containing an alkylketene compound represented by the following chemical formula 1:

[0024] [ka]

[0025] In the above chemical formula 1, R1 and R2 are each independently a saturated or unsaturated alkyl group having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid group having 1 to 40 carbon atoms.

[0026] The present invention also provides a method for conditioning hair or fibers, which comprises applying the above-described hair or fiber treatment composition to hair or fibers. The method may further comprise a heat treatment step.

[0027] The present invention also provides a hair or fiber treatment product for preventing or improving heat damage, which comprises the above-mentioned hair or fiber treatment composition.

[0028] The present invention also provides use of a composition containing the alkylketene compound represented by the aforementioned Chemical Formula 1 for producing a hair or fiber treatment product. [Effects of the Invention]

[0029] The hair or fiber treatment composition according to the present invention contains an alkylketene compound capable of forming a covalent bond with protein residues in hair or fibers. The alkylketene compound forms a covalent bond with the protein residues without damaging the hair or fibers, and can provide beneficial effects such as long-lasting conditioning by imparting permanent hydrophobicity to the hair or fibers.

[0030] Furthermore, the hair or fiber treatment composition according to the present invention can prevent and / or improve damage to hair or fibers caused by heat.

[0031] Furthermore, the hair or fiber treatment composition according to the present invention can leave a lingering fragrance on the hair or fiber, and can enhance flexibility, softness, hydrophobicity, or shrinkage prevention. BEST MODE FOR CARRYING OUT THE INVENTION

[0032] The present invention relates to a hair or fiber treatment composition containing an alkylketene compound represented by the following chemical formula 1:

[0033] The present invention also relates to the use of a composition comprising an alkylketene compound represented by the following Chemical Formula 1 for producing a hair or fiber treatment product.

[0034] [ka]

[0035] The configuration of the present invention will be specifically described below.

[0036] The hair or fiber treatment composition according to the present invention contains the alkyl ketene compound, which forms a covalent bond with hair or fiber to maximize the conditioning effect and maintain the effect for a long time. Furthermore, the alkyl ketene compound can prevent damage to hair or fiber caused by heat. That is, the hair or fiber treatment composition according to the present invention can be used as a hair or fiber conditioning composition.

[0037] In the present invention, the "conditioning" effect refers to the application, spraying, or other similar methods to the body (hair) or fibers to impart beneficial properties such as ease of brushing, smoothness, softness, neatness, shine, and volume to hair or fibers, thereby beautifying and increasing their attractiveness, changing their appearance, and invigorating them. Examples of conditioning effects include imparting luster and shine and reducing static electricity. Furthermore, by making the surface of hair or fibers hydrophobic, it prevents moisture from penetrating the hair from the external environment and also prevents moisture from escaping from within the hair or fibers, thereby helping to maintain moisture in the hair or fibers. It can also prevent damage to hair and protein-based fibers (such as wool and silk) that can lead to the elution of protein components from within the hair or fibers during washing. Therefore, it can not only alleviate or restore the symptoms of damaged hair or fibers, but also ultimately prevent damage to hair or fibers.

[0038] In the present invention, a conditioning composition means a composition used for conditioning the hair or fibers.

[0039] The alkylketene compound used in the present invention can be represented by the following chemical formula 1.

[0040] [ka]

[0041] In the above chemical formula 1, R1 and R2 may each independently be a saturated or unsaturated alkyl group having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid group having 1 to 40 carbon atoms.

[0042] As used herein, unless otherwise specified, "alkyl" refers to a straight, branched, or cyclic hydrocarbon having the specified number of carbon atoms.

[0043] In the present invention, unless otherwise specified, the term "fatty acid" refers to a carboxylic acid having a specified number of carbon atoms, which may have a linear or branched chain structure.

[0044] In one specific example, R1 and R2 may each independently be a linear or branched, saturated or unsaturated alkyl group having 8 to 22 carbon atoms or a linear or branched, saturated or unsaturated fatty acid having 8 to 22 carbon atoms. Preferably, it is selected from the group consisting of a linear, saturated or unsaturated alkyl group having 16 to 18 carbon atoms and 18-methyleicosanoic acid (18-MEA), and most preferably 18-MEA.

[0045] In addition to the alkyl group or fatty acid, R1 and / or R2 may contain a nucleophilic group such as a terminal alcohol of 2-oxetanone dimer, and the alkyl group of such an alcohol may contain a functional group such as an ester or ether. It may also contain an ethoxylate (EO / PO addition) or hydrogenated product of the alcohol.

[0046] In one embodiment, the alkyl ketene compound is, for example, alkyl (R1, R2; C12-16) ketene, hydrogenated tallow fatty acid (R1, R2; C12-16) diketene (R1, R2; fatty acids, tallow, hydrogenated, dimers, diketene derivatives), alkyl (R1, R2; C14-16) ketene, alkyl (R1, R2; C16-18) ketene, alkyl (R1, R2; C20-22) ketene, alkyl (R1, R2; C14) ketene, alkyl (R1, R2; C16) ketene, alkyl (R1, R2; C18) ketene, alkyl (R1, R2; C22) ketene, alkyl (R1; C14, R2; C16) ketene, alkyl (R1; C16, R2; C14) ketene, alkyl (R1; C16, R2; C18) ketene, alkyl (R1; C18, R2; C16) ketene, alkyl A variety of alkylketene compounds can be used, including, but not limited to, one or more selected from the group consisting of alkyl(R1, R2; C18-MEA) ketene, alkyl(R1; C16, R2; C18-MEA) ketene, alkyl(R1; C18, R2; C18-MEA) ketene, alkyl(R1; C22, R2; C18-MEA) ketene, alkyl(R1; C18-MEA, R2; C16) ketene, alkyl(R1; C18-MEA, R2; C18) ketene, and alkyl(R1; C18-MEA, R2; C22) ketene. For example, "C12" means a saturated or unsaturated alkyl group having 12 carbon atoms, "C12-16" means a mixture of saturated or unsaturated alkyl groups having 12 to 16 carbon atoms, and "C18-MEA" means 18-methyleicosanoic acid (18-MEA). Furthermore, "alkyl(R1; C18, R2; C16) ketene" means that in the compound of Chemical Formula 1, R1 is a saturated or unsaturated alkyl group having 18 carbon atoms, and R2 is a saturated or unsaturated alkyl group having 16 carbon atoms, and "alkyl(R1, R2; C14) ketene" means that in the compound of Chemical Formula 1, R1 and R2 are each a saturated or unsaturated alkyl group having 14 carbon atoms.

[0047] In one embodiment, the content of the alkyl ketene compound is not particularly limited and may be 0.0001 to 10 parts by weight, 0.01 to 7 parts by weight, or 0.1 to 5 parts by weight, based on 100 parts by weight of the total composition. If the content is less than 0.0001 part by weight, it is difficult to achieve a lasting conditioning effect, and if it exceeds 10 parts by weight, the compound may be present in excess of the reaction sites present on the hair or fibers, resulting in a problem of loss of the remaining alkyl ketene compound that has reacted with the hair or fibers.

[0048] Such alkylketene compounds can be applied to hair or fibers to form covalent bonds with protein residues in the hair or fibers, thereby maximizing the conditioning effect on the hair or fibers.

[0049] In the present invention, the alkylketene compound represented by Chemical Formula 1 may be contained in the hair or fiber treatment composition in a pre-dispersed, pre-emulsified or pre-encapsulated form.

[0050] When used in a dispersed and emulsified form, the composition may contain a dispersant and an emulsifier, and conventional dispersants and emulsifiers can be used. For example, anionic surfactants such as sodium lauryl sulfate, palmitic acid, stearic acid, and other fatty acid soaps; nonionic surfactants such as ethoxylated fatty alcohols, glyceryl esters, and sorbitan esters of fatty acids; cationic surfactants such as quaternary ammonium salts; and cationic polymers such as cationic starch and cationic cellulose can be used. Specifically, the nonionic surfactant (emulsifier) ​​can be one or more selected from the group consisting of glycerin fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and polyoxyethylene alkylphenyl ethers, but is not limited thereto.

[0051] When used in an encapsulated form, the alkylketene compound can be diluted with a liquid hydrocarbon, ester oil, silicone oil, etc., and encapsulated with gelatin, carrageenan, agar, silica, etc. The encapsulation technique is not limited to the examples listed above, and formulation techniques commonly used in cosmetics can be applied.

[0052] The composition according to the present invention may further comprise one or more selected from the group consisting of cationic surfactants and anionic surfactants. By including such components, the conditioning effect can be further improved.

[0053] The composition according to the present invention can use, without any limitation, cationic surfactants that can be used in conventional hair or fiber treatment compositions. For example, one or more selected from the group consisting of alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, ester quats, alkylpyridinium salts, alkylimidazolinium salts, alkylamine salts, and fatty acid amidoamine salts can be used. Preferably, dialkyldimethylammonium salts, alkylimidazolinium salts, and ester quats can be used, and more preferably, ester quats can be used.

[0054] In the present invention, the use of a combination of an alkylketene compound and a cationic surfactant can help the alkylketene compound to more easily act on a substrate due to the interaction between the hydrophobic moieties of the alkylketene compound and the cationic surfactant, which is expected to result in better effects than when each compound is formulated and used alone, but the present invention is not limited to this theory.

[0055] Furthermore, the composition of the present invention can use, without limitation, any anionic surfactant typically used in hair or fiber treatment compositions, such as one or more selected from the group consisting of soap, alkyl sulfate, alkyl ether sulfate, alkyl benzene sulfonate, alkane sulfonate, alpha olefin sulfonate, alpha sulfo fatty acid ester salt, alkyl sulfoacetate, alkyl sulfosuccinate, alkyl ether sulfosuccinate, alkyl phosphate, alkyl ether phosphate, alkyl ether carboxylate, acyl lactate, acyl taurate, acyl glutamate, acyl alaninate, acyl isethionate, and acyl succosinate. Preferably, soap, alkyl ether sulfate, or alkyl benzene sulfonate can be used, and more preferably, alkyl benzene sulfonate can be used.

[0056] In the present invention, by using an alkylketene compound and an anionic surfactant in combination, the anionic surfactant can remove lipids from the substrate, helping the alkylketene compound to more easily act on the substrate. This is expected to produce better effects than when each compound is formulated and used alone, but the present invention is not limited to this theory.

[0057] In one embodiment, the content of the cationic surfactant and / or anionic surfactant is not particularly limited, and may be 0.01 to 50 parts by weight, 1 to 30 parts by weight, or 10 to 20 parts by weight per 100 parts by weight of the total composition. Within this content range, better conditioning effects can be achieved.

[0058] The compositions according to the invention may further comprise water-soluble cellulose derivatives such as hydroxyethyl-, hydroxypropyl-, carboxymethylcellulose, and dispersion and emulsion stabilizers such as starch, xanthan gum, polyvinyl alcohol, acrylate polymers and carboxyvinyl polymers.

[0059] The composition according to the present invention may further comprise a fragrance. The type of fragrance is not particularly limited as long as it is one that can be used in ordinary hair or fabric treatment compositions, and fragrances having a log P value of -1.0 to 4.5 can be used.

[0060] The P is a partition coefficient and indicates the solubility of a compound in two solvents. For example, P can be the ratio of the solubility of a compound in octanol to the solubility of the compound in water. If the compound is lipophilic, the P value can be very large and can be expressed as a log P value. Preferably, the log P value of the fragrance is 0.5 to 4.5, 0.7 to 4.5, 1.0 to 4.4, or 2.0 to 4.4.

[0061] In one embodiment, the fragrance may be, for example, (2-tert-butylcyclohexyl)acetate, (3-oxo-2-pentylcyclopentyl)acetic acid, acid), (E)-4-decanal, 1-(1,2,3,4,5,6,7,8-Octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)ethanone, 1-(2,6,6-trimethyl-1-cyclohex-3-enyl)but-2-en1-one one), 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)penten-3-one, 1,2-dichloroethane, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, 1,4-dioxane, 1,6 hexanediol diglycidyl ether, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acetateacetate, 10-undecenal, 17a-hydroxyprogesterone, 1-bromoethane, 1-bromopentane, 1-butanol, 1-butene, 1-chlorohexane, 1-fluorooctane, 1-heptanol, 1-heptene, 1-hexanol, 1-hexene, 1-iodobutane, 1-methoxy-2-propanol an-2-ol, 1-naphthol, 1-nonanol, 1-octanol, 1-octyne, 1-pentanol (1.56), 1-pentene (2.80), 1-propanol (0.25), 2-(2-butoxyethoxy)ethanol (0.65), 2-(dimethylamino)-5,6-dimethylpyrimidin-4-ol (1.63), 2-(ethoxycarbonyl)benzoic acid (1.65 ... acid) (1.80), 2,2,2-trichloro-1-phenylethanol, 2,3-butanediol, 2,4,6-trichlorophenol, 2,4-dichlorophenol, 2,4-dichlorophenoxyacetic acid, 2,4-dihydroxy-3,6-dimethylbenzoic acidacid, 2,4-dimethylcyclohex-3-ene-1-carbaldehyde, 2,6-dimethyl-2-heptanol, 2-butanol, 2-butanone, 2-butoxyethanol, 2-butyne, 2-chlorophenol, 2-cresol, 2-decanone, 2-ethoxyethanol ethanol, 2-ethyl-1-hexanol, 2-ethylhexene, 2-heptanone, 2-hexanol, 2-hexanone, 2-hexen-1-ol, 2-hydroxybenzoic acid acid, 2-iodobutane, 2-isopropoxyethanol, 2-isopropoxyphenol, 2-MeTHF, 2-methoxy-4-(2-propenyl)-phenol, 2-methoxy-4-propylphenol, 2-methoxy-4-vinylphenol, 2-methoxyethanol, 2-methoxyethanol, 2-methoxyethyl acetateacetate, 2-methyl-1-butanol, 2-methyl-1-propanal, 2-methyl-2-butanol, 2-methyl-2-pentanol, 2-methyl-2-propanol, 2-methylbutyl acetate, 2-methylbutyric acid, 2-methylpropane, 2-methylpropionic acid acid, 2-naphthol, 2-naphthylamine, 2-nitro-4-phenylenediamine, 2-nonanone, 2-octanone, 2-octyne, 2-pentanone, 2-phenoxyethanol, 2-phenyl-1-ethanol, 2-phenylphenol, 2-propanol, 2-undecanone, 3(4)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde,4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, 3-(4-tert-butylphenyl)-2-methylpropanal (Lilial), 3,4-xylenol, 3,7-dimethyloct-6-en-1-ol, 3,7-dimethyl-2,6-octadiol 3,7-dimethylocta-2,6-dienal, 3,7-dimethyl-3-octanol, 3-cresol, 3-hexanol, 3-hexanone, 3-methyl-1-butanol, 3-methyl-3-pentanol, 3-methylbutyl acetate acetate, 3-methylbutyric acid, 3-nitrophenol, 3-phenyl butanal, 3-phenyl-1-propanol, 4-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-butene-2-one, 4-(methylthio)-3,5-xylenol, 4-acetamidophenol, 4-amino-2-nitrophenol, 4-aminobenzoic acidacid, 4-aminophenol, 4-bromophenol, 4-chloro-3-xylenol, 4-chlorocresol, 4-chlorophenol, 4-cresol, 4-cyanophenol, 4-ethoxy-4-oxobut-2-enoic acid, 4-ethylphenol, 4-heptyloxyphenol, 4-iodophenol, 4-methoxyacetophenone, 4-methoxybenzyl alcohol, 4-methylpentanoic acid acid, 4-nitroaniline, 4-nitrophenol, 4-pentyloxyphenol, 5-fluorouracil, 5-hexyloxolan-2-one, acetaldehyde, acetic acid, acetone, acetonitrile, acetophenone, acetyl cedrene, acetylcysteine, acetylsalicylic acid, allyl alcohol, allylheptanoate, alpha terpineol, amobarbital, amyl alcohol alcohol), amyl salicylate, androstenedione, anethole USPUSP, Aniline, α-terpineol, Atrazine, Atropine, Azodrin, Barbital, Benzaldehyde, Benzene zene, benzocaine, benzoic acid, benzoic acid, 2-amino-, dihydrochloride, benzophenone, benzyl acetate, benzyl alcohol, benzyl benzoate, benzyl nicotinate, benzyl salicylate, beta-terpineol, beta-estradiol, boric acid, butachlor, butobarbital, butyl 4-hydroxybenzoate, butyl acetate, butyl alcohol, butyl nicotinate nicotinate, butyraldehyde, butyric acid, caffeine, carbamic acid, dimethyl-, ethyl ester, carbaryl, carvone, catechol, chloramphenicol, chlorocresol, chloroform, chloroxylenol, chlorpheniramine, cinnamic acid, cinnamic aldehyde, cinnamic alcohol, cinnamyl alcohol, cinnamyl anthranilate anthranilate, cis-1,3-dichloropropene, cis-3-hexenyl acetateacetate, cis-6-nonenal, cis-jasmone, codeine, cortexone, coumarin, cumene, cyclododecanone, cyclohexane, cyclohexanone, cyclopentanone, cycloundecanone, decanal, decanoic acid, deoxycorticosterone, diisopropyl fluorophosphate (DFP), dehydroepiandrosterone phosphate (DHEA), diazinon, dichloromethane, diclofenac, diethyl ether, diethyl maleate maleate, diethyl malonate, diethyl phthalate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylether, dihydro linalool, dihydromyrcenol, dihydro-α-terpineol, dimethoate, dimethyl benzyl carbinyl acetate, dimethyl carbonateCarbonate, Dimethylcyclohexanol, Dimethylethylamine, Dimethylformamide, Dimethylnitrosamine, Dinitrochlorobenzene, Diphenyl ether, Dipropylene glycol methyl ether, dl-Citronellol, d-Limonene, Dimethylphthalate (DMP), E-2-Butenal, E-2-Hexenal, E-2-Octene, Ethylene Glycol glycol), ephedrine, estradiol, estragole, estriol, estrone, ethane, ethanol, ethyl acetate, ethyl benzene, ethyl ether, ethyl hydrogen malonate, ethyl nicotinate, ethyl vanillin, ethylbenzene, ethylene glycol methyl ether, ethynylbenzene, eucalyptol, eugenol, eugenyl methyl ether, floracetate acetate), Flutamide, Geraniol, Geranyl nitrile, Glycerol FormalFormal, Hedione, Heptanal, Heptane, Heptanoic acid, Heptanol, Hexanal, Hexanoic acid, Hexanol, Hippuric acid, Hydrochloric acid, Hydroxycitronellal, Ibuprofen, Indole, Iodomethane, Isoeugenol, Isobutyl isobutyrate, Isobutyl salicylate, Isoeugenol, Isopentyl isovalerate isovalerate, isoquinoline, koavone, lactic acid, LIFFAROME, linalool, lindane, malathion, maleic acid, malonic acid, 4,4'-methylenebis(2-chloroaniline) (MbOCA), m-cresol, MDA, meperidine, mesitylene, methanol, methiocarb, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, methyl 2-nonynoate, methyl acetate acetate), methyl anthranilate, methyl atrarate, methyl benzoate, methyl beta naphthyl ketone, methyl dihydrojasmonatedihydrojasmonate, methyl isobutyl ketone, methyl N methylanthranilate, methyl nicotinate, methyl propionate, methyl salicylate, methyl tert-butyl ether, methyl-4-hydroxy benzoate, methyl-4-OH benzoate, methyl-parathion, methylsalicylate, morphine, musk ketone ketone, m-xylene, N,N-Diethyl-m-toluamide, naproxen, n-butane, n-butanol, n-decanol, nerol, n-heptane, n-heptanol, n-hexane, n-hexanol, N-hexyl nicotinate, nicotinamide, nicotine, nicotinic acid, nitrobenzene, nitroglycerin, N-methylpyrrolidone pyrrolidone, N-methylcarbamate, n-nonanol, n-octanol, nonalactone, nonanoic acidacid, n-pentane, n-pentanol, N-phenyl-2-naphthylamine, n-propanol, n-propoxyethanol, o-chlorotoluene, o-cresol, o-cresyl glycidyl ether, octanal, octanoic acid, octanol, orange flower ether phenyl ethyl acetate, o-toluidine, o-xylene, paraoxon, parathion, p-cresol , Pentanoic acid, Pentanol, Phenethyl alcohol, Phenobarbital, Phenol, Phenoxanol, Phenoxyethyl isobutyrate, Phenylethysmethanol, Phenylethysmethanol, Phenylethysmethanol, Phosmet, Phoxim, Phthalic acid, Pirimicarb, Pregnenolone, Progesterone, 2-Prophenylheptanoate heptanoate, propane, propenal, propene, propionaldehyde, propionic acid, propoxur, propranolol, propyl acetate, propyl butyrate, propyl formate, propylene carbonate, propylene glycol, pt-butyl-α-methylhydrocinnamic aldehyde, p-xylene, pyridine, resorcinol, safrole, salicylic acidacid, scopolamine, styrene, terpinen-4-ol, tert-butanol, testosterone, tetrahydrofuran, tetrahydrolinalool, theophylline, thymol, toluene, triacetin, trichloromethane, trichloromethyl phenyl carbinyl acetate, triclopyr, tricyclododecenyl acetate, triethanolamine, trifluoroacetic acid, trimethylamine, undecanoic acid, valeric acid The composition may contain one or more compounds selected from the group consisting of α-methyl-1,3-benzodioxole-5-propionaldehyde, vanillin, and α-methyl-1,3-benzodioxole-5-propionaldehyde.

[0062] In one embodiment, the content of the fragrance is not particularly limited and may be 0.0001 to 30 parts by weight based on 100 parts by weight of the total composition.

[0063] The composition according to the present invention may further contain fatty acids, fatty alcohols, cationic starches, cationic celluloses, cationic guar, cationic acrylates and acrylamides, cationic polymers such as polyvinylpyrrolidone, silicones, etc., to concomitantly enhance stabilization and conditioning effects. Furthermore, for formulation purposes, the composition may further contain formulation ingredients such as solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, sequestering agents, pearlizing agents, appearance improvers, pigments, and powder particles.

[0064] When the composition according to the present invention is used as a hair treatment composition, i.e., a hair conditioning cosmetic composition, the formulation is not particularly limited and may include all formulations such as shampoo, rinse, treatment, hair pack, hair essence, wax, gel, and spray.

[0065] Furthermore, when the composition of the present invention is used as a fiber treatment composition, it may generally contain components that impart functions such as cleaning, tidying, and spot treatment for fiber care, as well as components that impart beneficial functions to fibers such as dyeing, bleaching, softening, sterilization, UV protection, fragrance, and the like. The formulation of the fiber treatment composition is not particularly limited, and examples of its application include products such as detergents, fabric softeners, fiber rinses, treatments, and spot treatment agents.

[0066] Each of the above-mentioned ingredients contained in the composition of the present invention may be included in the composition of the present invention within the range of the maximum use amount specified in the standards prescribed by the government of each country. For example, when providing a pharmaceutical composition, it may be included in the present invention within the range of the manufacturing method, properties, use amount, etc. specified in the Pharmacopoeia or Formulary of Korea, the United States, Europe, Germany, Japan, China, etc. Furthermore, when providing a cosmetic composition, it may be included in the cosmetic composition of the present invention within the range of the maximum use amount specified in the Cosmetic Safety Law prescribed by the government of each country or the Cosmetic Safety Technical Specifications prescribed by the Chinese government.

[0067] The present invention also relates to a conditioning method in which the aforementioned hair or fiber treatment composition is applied to hair or fibers.

[0068] In the present invention, the treatment can be carried out by painting, spraying, or other similar methods.

[0069] When the hair or fiber treatment composition according to the present invention is applied to hair or fibers, the alkylketene compound represented by Chemical Formula 1 forms a covalent bond with the protein residues of the hair or fibers, thereby imparting permanent hydrophobicity to the hair or fibers and providing a long-lasting conditioning effect.

[0070] The activated group (lactone ring) of the alkylketene compound can be bonded to hair or fibers in the form of a fixed covalent bond through an esterification reaction with a hydroxyl group in the hair or fibers. Specifically, the alkylketene compound can form a covalent bond with the hydroxyl group to impart hydrophobicity to the surface, increasing rigidity without inhibiting flexibility.

[0071] In the present invention, the treatment temperature, i.e., the temperature at which the hair or fiber treatment composition according to the present invention is applied to hair or fibers, is not particularly limited, and treatment can be performed at 20 to 250° C., preferably 30 to 230° C., and more preferably 80 to 120° C. Within this temperature range, the efficiency of permanent bonding between the compound and the hair or fiber can be increased, thereby providing a long-lasting conditioning effect.

[0072] As an example, the compositions of the present invention can prevent and / or ameliorate damage to hair or fibers caused by heat.

[0073] Also, by way of example, the compositions of the present invention may leave hair or fabric with a lingering fragrance and may also enhance the flexibility, softness, hydrophobicity and / or shrink resistance of hair or fabric. DETAILED DESCRIPTION OF THE INVENTION

[0074] The present invention will be described in detail below with reference to examples. The following examples are merely illustrative of the present invention, and the scope of the present invention is not limited to the following examples. The examples are provided to fully disclose the present invention and to fully inform those skilled in the art of the scope of the invention, and the present invention is defined only by the scope of the claims.

[0075] The materials used in the following examples and comparative examples were purchased from common raw material suppliers. [Example]

[0076] Production Example 1. Production of hair treatment compositions (Examples 1 to 8 and Comparative Examples 1 to 6) Hair treatment compositions (Examples 1 to 8 and Comparative Examples 1 to 6) were prepared containing the ingredients shown in Tables 1 and 2. In Table 2 below, the alkylketene compound is a compound having the structure of Chemical Formula 1, with R1 and R2 shown.

[0077] First, a fatty acid or alkylketene compound, a nonionic emulsifier, and a thickener were added to purified water, heated to 70°C, thoroughly stirred, and then cooled to room temperature (25°C) to prepare a composition.

[0078] [Table 1]

[0079] [Table 2] TIFF0007791122000006.tif21168

[0080] Experimental Example 1. Comparison of conditioning effects of hair treatment compositions (1) Method 1 g of each of the prepared hair treatment compositions of Examples 1 to 8 and Comparative Examples 1 to 6 was evenly applied to approximately 4 g of hair tress, left at room temperature for 30 minutes to induce a reaction, and then first washed with running water and shampoo, and the initial conditioning effect (satisfaction level of hair smoothness immediately after use_satisfaction level 1) was compared.

[0081] Thereafter, the subjects were shampooed once a day, and after 10 days, the hair conditioning effect (satisfaction with hair smoothness after 10 shampoos_satisfaction 2) was compared.

[0082] The conditioning effects were compared by sensory evaluation using a 5-point scale (5: excellent, 4: slightly excellent, 3: no difference, 2: no effect, 1: very no effect).

[0083] (2) Results The results of the evaluation of the degree of satisfaction are shown in Table 3 below.

[0084] As shown in Table 3, it can be seen that Examples 1 to 8, which used an alkylketene compound, exhibited better conditioning effects and sustained conditioning effects than Comparative Examples 1 to 6, which did not contain an alkylketene compound.

[0085] [Table 3]

[0086] Experimental Example 2: Comparison of conditioning effects of hair treatment compositions depending on treatment temperature (1) Method Using the compositions of Examples 1 to 8, 1 g of each composition was evenly applied to approximately 4 g of hair tresses, and the hair was dried for 5 minutes using a hair dryer at a temperature of 80 to 100°C.

[0087] After treatment, the subjects were first washed with running water and shampoo, and the initial conditioning effect (satisfaction with hair smoothness immediately after use_satisfaction 1) was compared.

[0088] Thereafter, the subjects were shampooed once a day, and after 10 days, the hair conditioning effect (satisfaction with hair smoothness after 10 shampoos_satisfaction 2) was compared.

[0089] The conditioning effects were compared by sensory evaluation using a 5-point scale (5: excellent, 4: slightly excellent, 3: no difference, 2: no effect, 1: very no effect).

[0090] (2) Results The results of the evaluation of the degree of satisfaction are shown in Table 4 below.

[0091] As shown in Table 4, it can be seen that the hair tresses containing the alkyl ketene compounds of the Examples and treated with a hair dryer at 80-100°C for 5 minutes have better conditioning effects and durability than the hair tresses treated with the same composition and dried at room temperature.

[0092] This confirms that when heat treatment conditions are added, the efficiency of covalent bond formation between the alkylketene compound and hair is even greater, resulting in better conditioning effects and lasting effects. That is, when using the composition according to the present invention, the surprising effect of preventing hair from being damaged by heat and further improving conditioning effects was obtained.

[0093] [Table 4]

[0094] Production Example 2: Production of fiber treatment composition (Examples 9 to 16 and Comparative Examples 7 to 12) Fiber treatment compositions (Examples 9 to 16 and Comparative Examples 7 to 12) were prepared containing the components shown in Tables 5 and 6. In Table 6 below, the alkylketene compound is a compound having the structure of Chemical Formula 1, with R1 and R2 shown.

[0095] First, a fatty acid or alkylketene compound, a nonionic emulsifier, and ethanol were added to purified water, heated to 70°C, thoroughly stirred, and then cooled to room temperature (25°C) to prepare a composition.

[0096] [Table 5] TIFF0007791122000010.tif47168

[0097] [Table 6] TIFF0007791122000012.tif67168

[0098] Experimental Example 3: Comparison of conditioning effects of fiber treatment compositions (1) Method 1 g of each of the prepared fiber treatment compositions of Examples 8 to 16 and Comparative Examples 7 to 12 was uniformly applied to a standard wool cloth measuring 20 cm x 20 cm, left at room temperature for 30 minutes to induce a reaction, first washed with running water and detergent, and then dried, and the initial fiber softening effect (satisfaction level of fiber softening power immediately after use_satisfaction level 1) was compared.

[0099] The garments were then washed three times using laundry detergent, dried, and the fabric softening effect (satisfaction with fabric softening power after three washes_satisfaction 2) was compared.

[0100] The fabric softening effect was compared by sensory evaluation using a 5-point scale (5: very good, 4: slightly good, 3: no difference, 2: no effect, 1: very bad effect).

[0101] (2) Results The results of the evaluation of the degree of satisfaction are shown in Table 7 below.

[0102] As shown in Table 7, it can be seen that Examples 9 to 16, which used alkyl ketene compounds, exhibited better fabric softening effects and sustained fabric softening effects than Comparative Examples 7 to 12, which did not contain alkyl ketene compounds.

[0103] [Table 7]

[0104] Experimental Example 4. Comparison of conditioning effects of fiber treatment compositions depending on treatment temperature (1) Method Using the compositions of Examples 9 to 16, 1 g of each was uniformly applied to a standard wool cloth measuring 20 cm x 20 cm, and the cloth was ironed for 1 minute at a temperature of approximately 150 to 170°C to induce a thermal reaction.

[0105] After that, they were first washed with running water, shampoo, and detergent, then dried, and the initial fabric softening effect (satisfaction with fabric softening power immediately after use_satisfaction 1) was compared.

[0106] The garments were then washed three times using laundry detergent, dried, and the fabric softening effect (satisfaction with fabric softening power after three washes_satisfaction 2) was compared.

[0107] The fabric softening effect was compared by sensory evaluation using a 5-point scale (5: very good, 4: slightly good, 3: no difference, 2: no effect, 1: very bad effect).

[0108] (2) Results The results of the evaluation of the degree of satisfaction are shown in Table 8 below.

[0109] As shown in Table 8, wool fabric containing an alkylketene compound and treated with an iron at 150 to 170°C for 1 minute was evaluated to have superior fabric softening effect and durability compared to the same composition dried at room temperature.

[0110] This confirms that when heat treatment conditions are added, the efficiency of covalent bond formation between the alkylketene compound and wool fibers is superior, resulting in superior fiber softening and lasting effects. That is, when the composition according to the present invention is used, the fibers are not damaged by heat, and the conditioning effect is further improved, which is a surprising effect.

[0111] [Table 8]

[0112] Furthermore, the compositions according to the examples also had similar effects when subjected to heat treatment using a clothes dryer (LG Electronics-RH16VS).

[0113] Production Example 3: Production of fiber treatment composition (Examples 17 to 23 and Comparative Examples 13 to 18) Fiber treatment compositions (Examples 17 to 23 and Comparative Examples 13 to 18) containing the components shown in Tables 9 and 10 below were prepared.

[0114] Alkyl ether sulfates, alkyl benzene sulfonates, and soaps are anionic surfactants, dialkyldimethylammonium salts, alkyl imidazolinium salts, and ester quats are cationic surfactants, and polyoxyethylene sorbitan fatty acid esters are nonionic surfactants.

[0115] In addition, a C12-16 alkyl ketene dimer was used as the alkyl ketene compound.

[0116] First, an anionic surfactant or cationic surfactant, a nonionic surfactant, and an alkylketene compound were added to purified water, heated to 70°C, and thoroughly stirred. Then, the temperature was lowered to 40°C, the fragrance was added, thoroughly stirred, and cooled to room temperature (25°C) to prepare the composition.

[0117] [Table 9]

[0118] [Table 10]

[0119] Experimental Example 5: Evaluation of the fiber property improvement effect of the combination of alkylketene compounds and surfactants The compositions of Examples 17 to 23 were evaluated for sensory evaluation (lingering fragrance strength, flexibility), stiffness, friction coefficient, contact angle, and shrinkage rate.

[0120] Sample processing was carried out as follows.

[0121] First, the fiber treatment composition was diluted 10 times.

[0122] A standard cotton cloth (E-211, Center For Test Materials BV, Netherlands) measuring 8 cm x 8 cm was immersed in the diluted fiber treatment composition and stirred with a magnetic bar at 400 rpm and 35°C for 1 hour. The cotton cloth was then removed and washed with running tap water for 3 minutes, after which the surface was wiped dry with a kitchen towel and placed in a dry oven at 60°C for 2 hours to dry. After storing for 24 hours at 25°C and 50% RH, tests for each evaluation item were performed.

[0123] (1) Sensory evaluation (1) Method (A) After the sample treatment, the strength of the fragrance remaining on the cotton fabric and the degree of softness were evaluated by sensory evaluation and given a score from 1 to 5. The evaluation was conducted by experienced panelists, and the average score was calculated from 10 repeated evaluations. (B) Cotton fabric was treated with a 15% SLES solution three times in the same manner as in the sample treatment, and after washing and drying were repeated three times, a sensory evaluation was carried out in the same manner as in (A). - Scent strength: 1: Almost no scent, 2: Weak scent, 3: Moderate scent, 4: Strong scent, 5: Very strong scent -Flexibility: 1: Very hard, 2: Slightly hard, 3: Normal, 4: Slightly soft, 5: Very soft

[0124] (2) Results The results of the sensory evaluation are shown in Tables 11 and 12 below.

[0125] As can be seen from the table, Example 23, which used an alkyl ketene compound alone, and Examples 17 to 22, which used an alkyl ketene compound together with a surfactant, were rated higher in lingering fragrance strength and flexibility scores than the comparative examples. In particular, it can be seen that when an alkyl ketene compound is used together with a surfactant, better lingering fragrance strength and flexibility are achieved.

[0126] This trend continued even after washing.

[0127] [Table 11]

[0128] [Table 12]

[0129] (2) Stiffness evaluation (1) Method (A) After sample treatment, the two opposing edges of the cotton fabric were spread flat and fixed on two axes of the device (Pure Bending Tester (KES-FB2-S, Kato Tech, Japan)). One axis was fixed while the other axis was rotated. The moment M (gf cm / cm) applied when the cotton fabric was bent was calculated as the curvature K (cm -1 ) recorded (Rotation range: K = ±2.5 cm -1 , rotation speed: 0.5cm -1 / sec). (B) Curvature K=0~2.5cm -1The gradient value of 1 was obtained through linear fitting for the interval where the moment change was constant within the range. (C) The cotton fabric was rotated 90 degrees and processes (A) and (B) were repeated, resulting in a gradient value of 2. (D) Stiffness (gf cm) calculated by taking the geometric mean of gradient values ​​1 and 2 2 / cm) (average of 10 repetitions). (E) In addition, cotton fabric was treated with a 15% SLES solution three times in the same manner as in the sample treatment method described above, and after washing and drying were repeated three times, stiffness was evaluated in the same manner as in (A) to (D) (average of 10 repetitions). The experiment was carried out at 25°C and 50% RH.

[0130] (2) Results The evaluation results of the stiffness are shown in Tables 13 and 14 below.

[0131] As shown in the table, Example 23, in which an alkylketene compound was used alone, and Examples 17 to 22, in which an alkylketene compound was used in combination with a surfactant, were found to have lower stiffness and greater flexibility compared to the comparative examples. In particular, it was found that the effect was even better when an alkylketene compound was used in combination with a surfactant.

[0132] This tendency continued even after washing. The results are similar to the results of the softness sensory evaluation described above.

[0133] [Table 13]

[0134] [Table 14]

[0135] (3) Evaluation of the friction coefficient (1) Method (A) A dedicated rubber probe and a weight that applies a normal force of 200 g were attached to a friction tester (MTT175, Dia-stron, UK). The sample-treated cotton fabric was spread flat and fixed to the moving plate of the device. The rubber probe was placed in contact with one edge of the cotton fabric, and the moving plate was moved at a speed of 200 mm / min. The friction force generated between the rubber probe and the cotton fabric was recorded according to the position on the cotton fabric. The coefficient of friction was calculated from the average friction force and normal force in a specific area of ​​the cotton fabric (average of 10 repeats). (B) Cotton fabric was treated with a 15% SLES solution three times in the same manner as in the sample treatment method described above, and after washing and drying were repeated three times, the coefficient of friction was evaluated in the same manner as in (A) (average value of 10 repetitions). The experiment was carried out at 25°C and 50% RH.

[0136] (2) Results The evaluation results of the friction coefficient are shown in Tables 15 and 16 below.

[0137] As shown in the table, Example 23, in which an alkyl ketene compound was used alone, and Examples 17 to 22, in which an alkyl ketene compound was used in combination with a surfactant, had lower friction coefficients than the comparative examples, and therefore, the fiber surface was less damaged and softer. In particular, it was confirmed that the effect was even better when an alkyl ketene compound was used in combination with a surfactant.

[0138] This trend continued even after washing.

[0139] [Table 15]

[0140] [Table 16]

[0141] (4) Contact angle (1) Method (A) After sample treatment, the cotton fabric was spread flat and placed on a parallel plate. 10 μL of distilled water was dropped onto five randomly selected locations. Images of the droplets were captured using a Drop Shape Analyzer (DSA100, Kruss, Germany), and the contact angles were measured (average of 10 replicates). (B) Cotton fabric was treated with a 15% SLES solution three times in the same manner as in the sample treatment described above, and after washing and drying were repeated three times, the contact angle was evaluated in the same manner as in (A) (average of 10 repetitions). The experiment was carried out at 25°C and 50% RH.

[0142] (2) Results The evaluation results of the contact angles are shown in Table 17 below.

[0143] In Comparative Examples 13 to 18, which were treated with only a surfactant, the droplets were completely absorbed by the cotton fabric, making it impossible to measure the contact angle.

[0144] However, Example 23, which used an alkylketene compound alone, and Examples 17 to 22, which used an alkylketene compound and a surfactant together, showed contact angles of 30° or more, which confirmed that the fiber surfaces were hydrophobicized, and that the surface hydrophobicity was maintained to some extent even after washing.

[0145] In particular, Examples 17 to 22, which used both an alkylketene compound and a surfactant, exhibited contact angles close to 90° and maintained a high contact angle even after washing, thereby imparting the hydrophobicity desired by the present invention and providing a long-lasting conditioning effect.

[0146] [Table 17]

[0147] (5) Shrinkage rate (1) Method (A) The fiber treatment compositions prepared in Examples 17 to 23 and Comparative Examples 13 to 18 were applied to a standard wool fabric (537, Testfabrics, Inc., USA). The treatment method was the same as that described above in Experimental Example 5. (B) The woolen cloth was unfolded and one end was held and hung by a gripper inside the device (Volume Tester (Bolero Lite, BOSSA NOVA VISION, USA)). A photograph was then taken with a camera, and the area of ​​the woolen cloth was measured. The degree of shrinkage relative to the original area (8 cm x 8 cm) was expressed as a shrinkage rate (%) (average of 10 repeats). (C) In addition, wool fabric was treated with a 15% SLES solution three times in the same manner as in the sample treatment method described above, and then washed and dried three times. The shrinkage rate was evaluated in the same manner as in (B) (average of 10 repetitions).

[0148] (2) Results The evaluation results of the shrinkage rates are shown in Tables 18 and 19 below.

[0149] As shown in the table, Example 23, which used an alkyl ketene compound alone, and Examples 17 to 22, which used an alkyl ketene compound together with a surfactant, had lower shrinkage rates and thus higher fiber shrinkage prevention capabilities than the comparative examples. In particular, it was confirmed that the effect was even better when an alkyl ketene compound was used together with a surfactant.

[0150] This trend continued even after washing.

[0151] [Table 18]

[0152] [Table 19] [Industrial Applicability]

[0153] The hair or fiber treatment composition according to the present invention contains an alkylketene compound capable of forming a covalent bond with protein residues in hair or fibers. The alkylketene compound forms a covalent bond with the protein residues without damaging the hair or fibers, and can provide beneficial effects such as long-lasting conditioning by imparting permanent hydrophobicity to the hair or fibers.

[0154] Furthermore, the hair or fiber treatment composition according to the present invention can prevent and / or improve damage to hair or fibers caused by heat.

[0155] Furthermore, the hair or fiber treatment composition according to the present invention can leave a lingering fragrance on the hair or fiber, and can enhance flexibility, softness, hydrophobicity, or shrinkage prevention.

Claims

1. an alkylketene compound represented by the following chemical formula 1; One or more selected from the group consisting of cationic surfactants and anionic surfactants A hair treatment composition comprising: 【Chemistry 1】 In the above chemical formula 1, R １ and R ２ are each independently a saturated or unsaturated alkyl group having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid group having 1 to 40 carbon atoms.

2. R １ and R ２ and each independently represent a linear or branched, saturated or unsaturated alkyl group having 8 to 22 carbon atoms or a linear or branched, saturated or unsaturated fatty acid having 8 to 22 carbon atoms.

3. R １ and R ２ and each independently represent a linear saturated or unsaturated alkyl group having 16 to 18 carbon atoms or 18-methyl eicosanoic acid (18-MEA).

4. 2. The hair treatment composition according to claim 1, wherein the alkylketene compound is contained in an amount of 0.1 to 5 parts by weight based on the total weight of the hair treatment composition.

5. 2. The hair treatment composition of claim 1, wherein the alkylketene compound is applied to the hair to form a covalent bond with the hair.

6. A method for conditioning hair, comprising treating hair with the hair treatment composition of claim 1.

7. 7. The method for conditioning hair according to claim 6, wherein the alkylketene compound in the hair treatment composition forms a covalent bond with the hair.

8. 7. The method for conditioning hair according to claim 6, wherein the treatment on the hair is carried out at 20 to 250°C.

9. A hair treatment product for preventing or improving heat damage, comprising the hair treatment composition according to claim 1.

10. Use of a composition comprising an alkylketene compound represented by the following chemical formula 1 and one or more selected from the group consisting of cationic surfactants and anionic surfactants, for producing a hair treatment product: 【Chemistry 2】 In the above chemical formula 1, R １ and R ２ are each independently a saturated or unsaturated alkyl group having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid group having 1 to 40 carbon atoms.

11. R １ and R ２ and each independently represent a linear or branched, saturated or unsaturated alkyl group having 8 to 22 carbon atoms or a linear or branched, saturated or unsaturated fatty acid group having 8 to 22 carbon atoms.

12. R １ and R ２ and each independently represent a linear saturated or unsaturated alkyl group having 16 to 18 carbon atoms or 18-methyl eicosanoic acid (18-MEA).

13. The use according to claim 10, wherein the alkylketene compound is contained in an amount of 0.1 to 5 parts by weight relative to the total weight of the composition.

14. The use according to claim 10, wherein the alkylketene compound is applied to the hair to form a covalent bond with said hair.

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