KR102502512B1 - Cosmetics compositions for antioxidant - Google Patents

Abstract

The present invention relates to an antioxidant cosmetic composition.
The antioxidant cosmetic composition according to the present invention contains an antioxidant component having a specific functional group capable of covalently bonding with a protein residue on the skin surface, and forms a covalent bond without damaging the skin to provide a desired antioxidant effect semi-permanently.

Description

Antioxidant cosmetic composition {Cosmetics compositions for antioxidant}

The present invention relates to a reactive antioxidant component and an antioxidant cosmetic composition to which a protein-binding functional group is bound.

In general, antioxidants in cosmetics have the ability to significantly reduce or prevent the destruction and exhaustion of skin functions and structures damaged by oxidation, and to restore damaged skin due to exposure to ultraviolet rays.

In addition, a quasi-drug is defined as having a minor effect even if it has an effect on the human body, not being used for the treatment or prevention of disease, and not having a purpose of use such as influencing the structure and function of the body.

Antioxidant cosmetics are generally basic antioxidant cosmetics for skin conditioning and protection, base, point, makeup antioxidant cosmetics for nails and body antioxidant cosmetics such as cleaning, sun care, suntanning, and pre-shampoo compositions, shampoo, It may include all cosmetic preparations that can be used for hair, such as rinse, treatment, wax, spray, mousse, hair lotion, essence, hair cream, permanent hair dye, temporary hair dye, and perm. However, when these antioxidant cosmetic raw materials and pharmaceutical ingredients are used for skin and hair, only temporary effects are provided until the next washing after treatment, and there is always a hassle of reprocessing after washing.

Patent Document 1 relates to a non-aqueous personal care product for skin or hair, in which the non-aqueous part contains carbonate, aldehyde, propionaldehyde, Butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide ), hydroxysuccinimidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic ester, disulfide, ketone, and functional groups represented by RX ( R is any one selected from the group consisting of alkyl, aryl, aralkyl, ring and unsaturated ring, and X is I, Br or Cl), including a conditioning component having at least one selected from the group consisting of a non-aqueous part and Disclosed is a personal care product for hair or skin, which is separated into water-based parts and is characterized in that it is mixed and used immediately before use. Among them, target lysine containing a small amount of hair (1.9-3.1%) and skin keratin (3.1-6.9%), or when it is about hair (16.6-18%) and skin keratin (2.3-3.8%). Since the stain is targeted and reacted, there is a problem in that the reaction efficiency is lowered and each material must be synthesized separately.

Korean Patent Publication No. 2008-0064467

An object of the present invention is to provide an antioxidant cosmetic composition that can continuously impart a semi-permanent antioxidant effect without damaging the skin.

As a means for solving the above problems, the present invention is a dihydroquinoline-based compound; And it provides an antioxidant cosmetic composition containing an antioxidant component.

As another means for solving the above problems, the present invention provides an antioxidant cosmetic composition further comprising a peptide bond formation promoting additive to the composition.

The antioxidant cosmetic composition according to the present invention contains a reactive antioxidant ingredient and/or a dihydroquinoline-based compound that introduces a specific functional group capable of covalent bonding with protein residues in the skin, so it forms a covalent bond without damaging the skin, resulting in a semi-permanent antioxidant effect. provides In addition, it provides an effective antioxidant effect by including a peptide bond formation promoting additive.

The present invention relates to an antioxidant cosmetic composition comprising a dihydroquinoline-based compound and an antioxidant component.

The antioxidant cosmetic composition according to the present invention, for example, reacts a dihydroquinoline-based compound with a previously known antioxidant component to form a covalent bond with a skin protein through a hydroquinoline-coupled reactive antioxidant component, thereby maximizing the antioxidant effect. can

The dihydroquinoline-based compound may be used in an amount of 0.001 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 cosmetic composition. If the content is less than 0.001 parts by weight, it is difficult to show a continuous skin antioxidant effect, and if it exceeds 10 parts by weight, the dihydroquinoline-based compound present in excess beyond the reactive site in the skin is effective in a state where it does not react with the skin. By reacting with the material, there is a problem that it does not help to improve sustainability and can act as a component that is lost.

In the present invention, the term 'antioxidant effect' refers to the reduction of cells by highly reactive free radicals or reactive oxygen species (ROS) according to intracellular metabolism or oxidative stress caused by the influence of ultraviolet rays. It refers to inhibiting oxidation, and by removing free radicals or reactive oxygen species, it can reduce cell damage and exhibit an anti-aging effect on the skin.

The antioxidant component used in the present invention is aminoethane sulfonic acid, acetamidocaproic acid, acetyl benzoyloxy prasterone, acetyl cysteine, 2-acetylhydroquinone (2- acetylhydroquinone), adamantanylcarboxamido hydroxylbenzamide, aminoethanesulfinic acid, aminopropyl ascorbyl phosphate, angoroside C, anserine ( anserine), apigenin, arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, butylhydroxyanisol (BHA), Butylated Hydroxy Toluene (BHT), bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane, bis-(tetramethyl hydroxypiperidinyl) sebacate , butylated xylenol, t-butylbenzamido hydroxylbenzamide, 4-butylresorcinol, caffeic acid, ascor Calcium ascorbate, carnosic acid, carotenoids, chitosan ascorbate, chlorogenic acid, cobalt DNA lt DNA), copper ATP (copper adenosine triphosphate), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine hydrochloride (cysteine HCl), decapeptide-6 -6), decapeptide-7, decursinol, decyl mercaptomethylimidazole, diamylhydroquinone, di-t-butylhydroquinone -t-butylhydroquinone), dicetyl thiodipropionate, dicyclopentadiene/t-butylcresol copolymer, digalloyl trioleate, diisooctyl sebacate, dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide, dimethoxy di-p-cresol cresol), dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, diosmine, diretinyl ether (diretinyl ether), disodium ascorbyl sulfate, distearyl thiodipropionate, ditridecyl thiodipropionate, dodecyl gal late), Dunaliella bardawil powder, ellagic acid, epigallocatechin gallate, ergothioneine, eriobotrya japonica leaf protoplasts , erythorbic acid, ethylbisiminomethylguaiacol manganese chloride, ethyl ferulate, ethylhexyl ferulate, ferulic acid, ferrule feruloyl soy glycerides, furfuryl palmitate, genistein glucoside, ginkgo leaf terpenoids, glucosylrutin, glyceryl chromonyl glyceryl chromonyl ether, glyceryl diferulate, hesperetin, hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin ( hydrolyzed proanthocyanidin, hydroquinone, p-hydroxyanisole, hydroxydecyl ubiquinone, hydroxylamine hydrochloride (hydroxylamine HCl), hydroxylamine sulfate , hydroxyphenyl dihydroxybenzamide, inositol hexaniacinate hexaascorb ate), isooctyl caprylate/caprate, isooctyl thioglycolate, isoquercitrin, kaempferol, kojic acid, kojyl glucoside glucoside, kojyl methylenedioxycinnamate, kou-cha ekisu, lycopene, madecassoside, magnesium ascorbate, magnolol, manganese Naise ATP (manganese adenosine triphosphate), matrine, melatonin, methoxy PEG-7 ascorbic acid, methoxytrimethylphenyl dihydroxyphenyl propanol, Methyl di-t-butyl hydroxyhydrocinnamate, methylene di-t-butylcresol, methyl-methacrylate/trimethoxysilylpropyl methyl methacrylate/trimethoxysilylpropyl methacrylate crosspolymer, methyl myristic acid, niacinamide hydroxybenzoate, nictoflorin, nordihydroguaiaret acid (nordihydroguaiaretic acid), octanicotinoyl epigallocatechin gallate, octapeptide-4 (octapeptide-4), oligopeptide-28 (oligo peptide-28), paeonol, palmatine, PEG/PPG-2/5 tocopheryl ether, perillyl alcohol, phenethyl carb Phenethyl caffeate, phenylethyl resorcinol, phenylthioglycolic acid, phloretin, phloroglucinol, piceatannol, pipelonguminin (piperlonguminine), porphyridium polysaccharide, potassium ascorbyl tocopheryl phosphate, potassium sulfite, PPG-2 tocophereth-5 , propyl gallate, protocatechuicaldehyde, puerarin, pyridoxine hydroxybenzoate, pyridyloxide t-butylnitrone, que quercetin, resacetophenone, resorcinol, resveratrol, retinyl formyl aspartamate, rosmarinic acid, rutin, rutin rutinyl succinate, green tea extract (ryoku-cha ekisu), salnacedin, sodium ascorbate, sodium sulfite, sodium tocopheryl phosphate, Sodium escortate (sodium erythorbate), sodium phosphono-pyridoxylidenerhodanine, sodium thioglycolate, sodium zinc histidine dithiooctanamide, sorbityl furfural, stearyl gallate, succinoyl ascorbate pentapeptide-6, tangeritin, tert-butylhydroquinone (TBHQ), tetrabutyl ethylidine bisphenol ethylidinebisphenol), tetrahydrodemethoxydiferuloylmethane, tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetra Methylchromanol glucoside, thioctic acid, thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, thymol trimethoxy thymol trimethoxycinnamate, tococysteamide, tocophereth-5, tocopherol, tocophersolan, tocopheryl acetate, tocoquinone ( tocoquinone, toluene, o-tolyl biguanide, totol arool), tripropylene glycol, tris-BHT mesitylene, tris(nonylphenyl)phosphate, trisodium ascorbyl isopalmitate phosphate), tyrosyl histidine hydrochloride (tyrosyl histidine HCl), ubiquinol, ubiquinone, ulva lactuca powder, oolong tea extract (uuron-cha ekisu), xylyl dibutyl Benzofuranone (xylyl dibutylbenzofuranone), zinc adenosine triphosphate (ATP), zinc dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-phosphate phosphate) and derivatives thereof, but is not limited thereto.

The antioxidant component is preferably used in an amount of 0.001 to 50 parts by weight, 0.001 to 30 parts by weight, 0.01 to 10 parts by weight, or 0.1 to 5 parts by weight based on 100 parts by weight of the total cosmetic composition. If the content is less than 0.001, the effect is insignificant and there is a limit, and if it exceeds 50 parts by weight, there are problems in formulation and stabilization.

In particular, the antioxidant component in the present invention can increase the reaction efficiency with the dihydroquinoline-based compound by including a carboxyl group or an amine group in the molecule.

In addition, in the present invention, the antioxidant component may have a functional group capable of covalently bonding with a protein residue on the skin surface.

Functional groups covalently bonded to the protein include carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butyraldehydes, nitrophenyl carbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, hydroxysuccinimidyl esters , imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides, ketones, carboxylic acids, and phosphates. There can be more than one, but is no longer limited.

In addition, the protein may include a reactive residue such as thiol, hydroxyl, carboxyl, or amine.

The dihydroquinoline-based compound may be a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

R ₁ represents a water-soluble nonionic polymer, a polymer resin in the form of beads or resins, or silica beads,

R ₂ and R ₃ are the same or different, respectively, and represent any one selected from the group consisting of straight-chain or branched saturated or unsaturated alkyl having 1 to 10 carbon atoms and saturated or unsaturated alkoxy having 1 to 10 carbon atoms.

The water-soluble nonionic polymer preferably has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da, and when the molecular weight is 300,000 Da or more, the ratio of dihydroxyquitoline-based compounds that induce covalent bonds is too small to show efficacy.

The water-soluble nonionic polymer is specifically polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivative, starch derivative, dextran and guar gum It may be one or more polymers selected from the group consisting of.

It is preferable that the weight average molecular weight of the polymer in the form of beads or resin is 1,000 Da or more and less than 300,000 Da, and when the molecular weight is 300,000 Da or more, the ratio of dihydroxyquinoline-based compounds inducing covalent bonds is too small to show efficacy.

The bead-type or resin-type polymer resin is specifically styrene, ethylene, butadiene, acrylonitrile, methyl styrene, terephthalate, ethylene chloride, ether ketone, ether imide, ether sulfone, phthalamide, phenylene ether, phenylene oxide , It may be a copolymer polymerized with a monomer selected from the group consisting of phenylene sulfide, sulfone, urethane, vinylidene fluoride and tetrafluoroethylene.

The polymer beads have an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 μm, more preferably 1 μm to 100 μm, and most preferably 1 μm to 70 μm. can be included If the diameter of the polymer bead is less than 100 nm, it may cause safety problems on the skin surface, and if the diameter of the polymer bead is greater than 1 mm, there is a problem in formulation and stabilization.

The silica beads have an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 μm, more preferably 1 μm to 100 μm, and most preferably 1 μm to 70 μm. can be included When the diameter of the silica bead is smaller than 100 nm, it may cause safety problems on the skin surface, and when the diameter of the silica bead is larger than 1 mm, there is a problem in formulation and stabilization.

In a preferred embodiment of the antioxidant cosmetic composition according to the present invention, the antioxidant component having a carboxyl group is made in the form of a reactive ester antioxidant component having direct bioreactivity, or an amino acid present in excess in skin keratin (15.5 to 23.5%) (ex, Aspartic acid, glutamic acid) can be reactively esterified to form a form that can be targeted by an antioxidant component containing an amine group, thereby increasing the reaction efficiency, thereby significantly increasing the effect. As a more preferred embodiment, a reactive ester is formed by first reacting the polymeric dihydroquinoline-based compound of Formula 1 on the surface of an antioxidant component molecule having a carboxyl group or skin protein, and the formed reactive ester functional group has an amine in the molecule again. An excellent antioxidant effect can be obtained by reacting antioxidant components or reacting with amines on the skin surface.

In Reaction Scheme 1 below, an antioxidant component molecule having a carboxyl group first reacts with a dihydroquinoline-based compound to form a reactive ester, and subsequently reacts with an amino acid in a living body having an amine residue to form a covalent bond.

[Scheme 1]

As shown in Scheme 2 below, aspartic acid and glutamic acid, biogenic amino acids having a carboxyl group on the surface of skin proteins, react first with a dihydroquinoline-based compound to form a reactive ester, and then react with an antioxidant component having an amine residue to form a covalent bond. A schematic diagram of the reaction is shown.

In the following Reaction Scheme 2, aspartic acid and glutamic acid, which are biogenic amino acids having carboxyl groups on the surface of skin proteins, react with dihydroquinoline-based compounds to form reactive esters and subsequently react with antioxidant components having amine residues to form covalent bonds. A schematic diagram was shown.

[Scheme 2]

Antioxidant components attached to skin proteins and peptide bonds using dihydroquinoline-based compounds can remain attached to the skin semi-permanently without being removed from the skin by washing methods such as soaps and cleansers.

Dihydroquinoline-based compounds increase the reaction efficiency of skin proteins and antioxidants, so the reactive antioxidants bonded to the skin do not come off easily during general washing with soap, etc., and can remain attached to the skin almost permanently. there is.

The present invention also relates to antioxidant components such as carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butyraldehydes, nitrophenyl carbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, hydroxysuccinimidyl esters , imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides, ketones, carboxylic acids, and phosphates. It may include a reactive antioxidant component to which a functional group covalently bonded to one or more proteins is bound.

For example, as shown in Reaction Scheme 1, the dihydroquinoline-based compound produced by first reacting the dihydroquinoline-based compound may include an antioxidant component coupled thereto. In addition, the present invention may include an antioxidant cosmetic composition containing the reactive antioxidant component.

In the antioxidant cosmetic composition according to the present invention, hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, hydroxy At least one peptide bond formation reaction promoting additive selected from the group consisting of oxybenzotriazine and oxyma may be included. The peptide bond formation reaction promoting additive may be used in an amount of 0.0001 to 10 parts by weight based on 100 parts by weight of the total composition. Preferably it is 0.001 to 1 part by weight, more preferably 0.001 to 0.1 part by weight. Even if 10 parts by weight or more is used, the rate of chemical reaction is saturated, so the product is not economically viable, and it is not helpful for product stability. When used below 0.0001, it provides little or no benefit to reactivity.

In addition, in order to additionally increase the effect in the antioxidant cosmetic composition according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, linear and branched long-chain alkyl quaternary ammonium salts, etc. Preparation can be facilitated when mixed with cationized surfactants, cationized cellulose, cationized guar, cationized polymers such as cationized polyvinylpyrrolidone, silicone, and the like. In addition, for formulation into cosmetic formulations, solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, metal ion sequestering agents, pearlescent agents, appearance improvers, emollients, pigments, powder particles, etc. Ingredients may be included incidentally. Components for the formulation may be used in an amount of 40 to 99 parts by weight, 60 parts by weight or 98 parts by weight, or 80 parts by weight or 95 parts by weight based on 100 parts by weight of the total composition.

The antioxidant cosmetic composition according to the present invention may be used in the prescription of an antioxidant cosmetic composition including an antioxidant functional component having a functional group. Examples of application of hair products include pre-shampoo compositions, shampoos, rinses, treatments, waxes, gels, sprays, mousses, hair lotions, hair packs, hair essences, hair creams, research hair dyes, temporary hair dyes, perms, It may include both non-woven fabrics and sheets, and examples of application of skin products generally include basic cosmetics (toilet, serum, essence, lotion, cream, etc.) for skin care and protection, color cosmetics (make-up base, foundation, powder, Eye shadow, lip gloss, lipstick, lip balm, etc.), makeup for hands and toenails (manicure, nutrients, strengthening agent, top coat, etc.), cosmetics for cleansing (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, Masks, soaps, cleansing tissues, etc.), sun care cosmetics, and body cosmetics (body lotion, shower gel, body cream, body oil, etc.) can all be included.

More preferably, the antioxidant cosmetic composition according to the present invention includes a dihydroquinoline-based compound and at the same time contains an antioxidant component having a reactive functional group. It is easier to maintain, and the reaction can be caused by mixing with a buffer to adjust the pH immediately before use or by contact with water in the cleaning process. Examples of non-aqueous formulations include liquid form, sheet form, powder form, tablet form, oil, wax, ampoule, gel, etc., which are used as conventional non-aqueous cosmetic preparations. In addition, the dihydroquinoline-based compound and the antioxidant component may be formulated as a single agent in encapsulated form or in two separate forms. In addition, a method of blocking moisture from a derivative in which a functional group having a reactive function and a component having an antioxidant function are combined through encapsulation may also be used.

In order to increase the antioxidant effect having a functional group in the antioxidant cosmetic composition according to the present invention, 2-base acid ester oil such as dioctyl succinate, dioctyl adipate, diethyl sebacate, etc., polyol, polyethylene glycol, propylene glycol, hexylene Glycol, butanediol and their isomers, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof can be used. The above-mentioned solvent increases skin permeability and is used as a solvent for poorly soluble substances. More preferably, the solvent used to increase the effect of maintaining the activity of the antioxidant component having a functional group includes diethyl sebacate, ethoxy glycol, bis-ethoxy glycol cyclohexane 1,4-dicarboxylate, and the like.

Hereinafter, the present invention will be described in detail by the following examples. However, the following examples are only to illustrate the present invention, and the content of the present invention is not limited to the following examples.

Example 1 and comparative example 1: cream ( 100 grams ) formulation preparation

According to the composition and content of Table 1 below, a creamy antioxidant cosmetic composition was prepared and tested.

After heating the water phase raw materials 3 to 13 to 70 ° C., they were uniformly mixed for 5 minutes at 1500 rpm using a homomixer. Oil phase components 15 to 24 previously dissolved by heating to 70 ° C were added to the mixed aqueous phase and mixed uniformly for 5 minutes at 3500 rpm using a homo mixer. After that, the temperature was lowered to 50 ° C and a neutralizing agent, PS-IIDQ (Polystyrene supported 1-isobutoxycarbonyl-2-isobutoxy-1,2-dihydroquinoline) 1, a dihydroxyquinoline-based compound, and NHS (N-hydroxysuccinimide) 2, an additive for promoting peptide bond formation, were added. and fragrance 14 were added and uniformly mixed for 3 minutes with a homo mixer, followed by degassing, filtration, and cooling.

In the PS-IIDQ, R ₁ in Formula 1 is represented by the following Formula 2 (m + n + x + y: z = 99: 1 mole ratio), and is a resin-type polymer resin having a weight average molecular weight of 200,000 Da ; R ₂ and R ₃ are isobutyl. The z is a crosslinker that randomly connects between polymers without being attached to a specific position, Tetrahedron Letters 41 (2000) 2463-2466 and / or Chem. Rev. 2011, 111, 6557-6602 was synthesized by reference.

[Formula 2]

No ingredient Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 One PS-IIDQ - - - 0.1 0.1 0.1 2 NHS - - - 0.01 0.01 0.01 3 acetyl cysteine 2.0 - - 2.0 - 2.0 caffeic acid - 2.0 - - 2.0 - aminoethane sulfonic acid - - 2.0 - - 2.0 4 glycerin 6.0 6.0 6.0 6.0 6.0 6.0 5 DPG 3.0 3.0 3.0 3.0 3.0 3.0 6 1,3-butylene glycol 2.0 2.0 2.0 2.0 2.0 2.0 7 Urea/HEPES 0.8 0.8 0.8 0.8 0.8 0.8 8 antiseptic 1.0 1.0 1.0 1.0 1.0 1.0 9 anti-inflammatory 2.0 2.0 2.0 2.0 2.0 2.0 10 carbomer 0.2 0.2 0.2 0.2 0.2 0.2 11 xanthan gum 0.05 0.05 0.05 0.05 0.05 0.05 12 corrector 0.28 0.28 0.28 0.28 0.28 0.28 13 Purified water To 100 To 100 To 100 To 100 To 100 To 100 14 spices 0.1 0.1 0.1 0.1 0.1 0.1 15 Cetearyl alcohol 2.5 2.5 2.5 2.5 2.5 2.5 16 Glyceryl stearate 1.2 1.2 1.2 1.2 1.2 1.2 17 PEG-100 stearate 0.3 0.3 0.3 0.3 0.3 0.3 18 PEG-40 stearate 0.5 0.5 0.5 0.5 0.5 0.5 19 Stearic acid 0.3 0.3 0.3 0.3 0.3 0.3 20 Cyclohexasiloxane 6.0 6.0 6.0 6.0 6.0 6.0 21 Petaerythrityl tetraethylhexanoate 3.0 3.0 3.0 3.0 3.0 3.0 22 Dimethicone 5.0 5.0 5.0 5.0 5.0 5.0 23 macadamia oil 2.0 2.0 2.0 2.0 2.0 2.0 24 Hydrogenated polydecene 4.0 4.0 4.0 4.0 4.0 4.0

Experimental example One

After attaching acetyl cysteine, caffeic acid, or aminoethane sulfonic acid to the skin by bioconjugation using PS-IIDQ, the efficacy was confirmed.

2 g of each of the prepared compositions of Comparative Examples 1 to 3 and Examples 1 to 3 was applied to the back of the hand twice daily in the morning and evening for 10 subjects, and the hands after 1 day, 5 days, and 10 days after treatment The skin anti-aging effect was compared on a 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 no effect, 1 very no effect) by integrating the roughness and appearance of the skin.

Experimental results of Examples 1 to 3 and Comparative Examples 1 to 3 (Table 2), compared to Comparative Examples 1 to 3 without PS-IIDQ, Examples 1 to 3 including PS-IIDQ have a covalent bond formation effect It showed a more excellent skin aging improvement effect.

Skin aging improvement effect (5-point scale, n=10 each) Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 1 day after treatment 3.8 3.9 4.0 4.0 3.8 4.1 5 days after treatment 3.5 3.4 3.4 3.9 3.8 4.0 10 days after treatment 3.3 3.2 3.1 3.9 3.7 4.1

Claims (17)

Including a dihydroxyquinoline-based compound represented by Formula 1 and an antioxidant component,
The antioxidant component has a functional group capable of covalently bonding with a protein residue on the skin surface,
The antioxidant component is 0.001 to 50 parts by weight based on 100 parts by weight of the total composition.
Antioxidant cosmetic composition:
[Formula 1]

In Formula 1,
R ₁ represents a water-soluble nonionic polymer, a polymer resin in the form of beads or resins, or silica beads,
R ₂ and R ₃ are the same or different, respectively, and represent any one selected from the group consisting of straight-chain or branched saturated or unsaturated alkyl having 1 to 10 carbon atoms and saturated or unsaturated alkoxy having 1 to 10 carbon atoms.
delete According to claim 1,
The water-soluble nonionic polymer is an antioxidant cosmetic composition having a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
According to claim 1,
The water-soluble nonionic polymer is composed of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivative, starch derivative, dextran and guar gum Antioxidant cosmetic composition of at least one polymer selected from the group.
According to claim 1,
The polymer resin in the form of beads or resin is an antioxidant cosmetic composition having a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
According to claim 1,
The bead-type or resin-type polymer resin is styrene, ethylene, butadiene, acrylonitrile, methyl styrene, terephthalate, ethylene chloride, ether ketone, ether imide, ether sulfone, phthalamide, phenylene ether, phenylene oxide, phenyl An antioxidant cosmetic composition comprising a polymer polymerized with a monomer selected from the group consisting of lensulfide, sulfone, urethane, vinylidene fluoride and tetrafluoroethylene.
According to claim 1,
The silica beads have an average particle diameter of 100 nm to 1 mm antioxidant cosmetic composition.
According to claim 1,
The dihydroxyquinoline-based compound is an antioxidant cosmetic composition of 0.001 to 10 parts by weight based on 100 parts by weight of the total composition.
According to claim 1,
The antioxidant component is an antioxidant cosmetic composition containing a carboxyl group or an amine group in the molecule.
According to claim 1,
The antioxidant component is aminoethane sulfonic acid, acetamidocaproic acid, acetyl benzoyloxy prasterone, acetyl cysteine, 2-acetylhydroquinone, adamantanyl Carbosamido hydroxylbenzamide, aminoethanesulfinic acid, aminopropyl ascorbyl phosphate, angoroside C, anserine, apagenin ( apigenin), arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, butylhydroxyanisol (BHA), butylated hydroxy toluene (BHT) , bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane, bis-(tetramethyl hydroxypiperidinyl) sebacate, butylated xyle Butylated xylenol, t-butylbenzamido hydroxylbenzamide, 4-butylresorcinol, caffeic acid, calcium ascorbate , carnosic acid, carotenoids, chitosan ascorbate, chlorogenic acid, cobalt DNA, Cooper AT P (copper adenosine triphosphate), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine hydrochloride (cysteine HCl), decapeptide-6, deca Peptide-7, decursinol, decyl mercaptomethylimidazole, diamylhydroquinone, di-t-butylhydroquinone , dicetyl thiodipropionate, dicyclopentadiene/t-butylcresol copolymer, digalloyl trioleate, diisooctyl sebacate (diisooctyl sebacate), dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide, dimethoxy di-p-cresol, dimethylmethyl dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, diosmine, diretinyl ether, disodium ascorbyl sulfate, distearyl thiodipropionate, ditridecyl thiodipropionate, dodecyl gallate, dunaliella bar Dunaliella bardawil powder, ellagic acid, epigallocatechin gallate, ergothioneine, eriobotrya japonica leaf protoplasts, erythorbic acid ), ethylbisiminomethylguaiacol manganese chloride, ethyl ferulate, ethylhexyl ferulate, ferulic acid, feruloyl soy glyceride soy glycerides, furfuryl palmitate, genistein glucoside, ginkgo leaf terpenoids, glucosylrutin, glyceryl chromonyl ether, Glyceryl diferulate, hesperetin, hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin, hydroquinone ( hydroquinone), p-hydroxyanisole, hydroxydecyl ubiquinone, hydroxylamine hydrochloride (hydroxylamine HCl), hydroxylamine sulfate, hydroxyphenyl dihydroxy Benzamide (hydroxyphenyl dihydroxybenzamide), inositol hexaniacinate hexaascorbate, isooctyl capri isooctyl caprylate/caprate, isooctyl thioglycolate, isoquercitrin, kaempferol, kojic acid, kojyl glucoside, kojyl methylenedi kojyl methylenedioxycinnamate, black tea extract (kou-cha ekisu), lycopene, madecassoside, magnesium ascorbate, magnolol, manganese adenosine triphosphate (ATP) ), matrine, melatonin, methoxy PEG-7 ascorbic acid, methoxytrimethylphenyl dihydroxyphenyl propanol, methyl-di-t- Methyl di-t-butyl hydroxyhydrocinnamate, methylene di-t-butylcresol, methyl-methacrylate/trimethoxysilylpropyl methacrylate crosspolymer (methyl methacrylate/trimethoxysilylpropyl methacrylate crosspolymer), methyl myristic acid, niacinamide hydroxybenzoate, nictoflorin, nordihydroguaiaretic acid, Octanicotinoyl epigallocatechin gallate, octapeptide-4, oligopeptide-28, Paeonol, palmatine, PEG/PPG-2/5 tocopheryl ether, perillyl alcohol, phenethyl caffeate, Phenylethyl resorcinol, phenylthioglycolic acid, phloretin, phloroglucinol, piceatannol, piperlonguminine, porpyridium Polysaccharide, potassium ascorbyl tocopheryl phosphate, potassium sulfite, PPG-2 tocophereth-5, propyl gallate gallate), protocatechuicaldehyde, puerarin, pyridoxine hydroxybenzoate, pyridyloxide t-butylnitrone, quercetin, le resacetophenone, resorcinol, resveratrol, retinyl formyl aspartamate, rosmarinic acid, rutin, rutinyl succinate ), green tea extract (ryoku-cha ekisu), salnacedin, sodium ascorbate, sodium sulfite, sodium tocopheryl phosphate, sodium escortate erythorbate), Sodium phosphono-pyridoxylidenerhodanine, sodium thioglycolate, sodium zinc histidine dithiooctanamide, sorbityl furfural, Stearyl gallate, succinoyl ascorbate pentapeptide-6, tangeritin, tert-butylhydroquinone (TBHQ), tetrabutyl ethylidinebisphenol, Tetrahydrodemethoxydiferuloylmethane, tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetramethylchroman Tetramethylchromanol glucoside, thioctic acid, thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, thymol trimethoxycinnamate ( thymol trimethoxycinnamate), tococysteamide, tocophereth-5, tocopherol, tocophersolan, tocopheryl acetate, tocoquinone, Toluene, o-tolyl biguanide, totarol, tripropylene Glycol, tris-BHT mesitylene, tris(nonylphenyl)phosphate, trisodium ascorbyl isopalmitate phosphate, tyrosyl Histidine hydrochloride (tyrosyl histidine HCl), ubiquinol, ubiquinone, ulva lactuca powder, oolong tea extract (uuron-cha ekisu), xylyl dibutylbenzofuranone dibutylbenzofuranone, zinc adenosine triphosphate (ATP), zinc dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-phosphate and derivatives thereof At least one antioxidant cosmetic composition selected from the group consisting of.
delete According to claim 1,
Functional groups covalently bonded to the protein include carbodiimide, imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenyl ester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazides, haloacetyls, azides, carbonates, aldehydes, propionaldehydes, butyraldehydes, nitrophenyl carbonates, aziridines, isocyanates, thiocyanates, epoxides, tresylates, succinimides, hydroxysuccinimidyl esters , imidazoles, oxycarbonyl imidazoles, imines, thiols, maleimides, vinylsulfones, ethylenimines, thioethers, acrylonitriles, acrylic acid or methacrylic acid esters, disulfides, ketones, carboxylic acids, and phosphates. One or more antioxidant cosmetic compositions.
delete According to claim 1,
The composition is an antioxidant cosmetic composition further comprising a peptide bond formation reaction promoting additive.
15. The method of claim 14,
The peptide bond formation reaction promoting additive is hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, hydroxyl At least one antioxidant cosmetic composition selected from the group consisting of benzotriazine and oxima.
15. The method of claim 14,
The peptide bond formation reaction promoting additive is an antioxidant cosmetic composition of 0.0001 to 10 parts by weight based on 100 parts by weight of the total composition.
According to claim 1,
The dihydroxyquinoline-based compound and the antioxidant component are formulated as a single agent in an encapsulated form; Antioxidant cosmetic composition formulated with two separate types of dihydroxyquinoline-based compounds and antioxidant components.