KR20180017459A - Cosmetics compositions for antioxidant - Google Patents

Abstract

The present invention relates to an antioxidant cosmetic composition. According to the present invention, the antioxidant cosmetic composition contains antioxidant components having specific functional groups capable of forming covalent bonds with protein residues on a surface of skin, and thus forms the covalent bond without damaging skin, thereby ensuring desirable and semipermanent antioxidant effects.

Description

[0001] Cosmetics compositions for antioxidant [

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

In general, the antioxidant of cosmetics has 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 ultraviolet exposure.

It is also defined that quasi-drugs do not have the purpose of use, such as affecting the structure and function of the body, rather than being used for the treatment or prevention of diseases, even though they have an effect on the human body.

Antioxidant cosmetics are generally used for preparing antioxidant cosmetics, bases, points, antioxidant cosmetics for nails, body antioxidant cosmetics such as cleansing, sun care, sun tanning, and shampoo-pre-shampoo compositions, shampoos, Cosmetic preparations that can be used for hair such as rinses, treatments, waxes, sprays, mousses, hair lotions, essences, hair creams, permanent hair dyes, temporary hair dyes, When used for skin and hair, it is only a temporary effect until the next cleaning after the treatment, but there is always the hassle of reprocessing after cleaning.

Patent Document 1 discloses a non-aqueous personal care product for skin or hair, which comprises a non-water-based functional group capable of forming a covalent bond with a hair or a protein residue on the surface of a skin, such as carbonate, aldehyde, propionaldehyde, But are not limited to, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, A hydroxysuccinimidyl ester, an imidazole, an oxycarbonylamidazole, an imine, a thiol, a maleimide, a vinylsulfone, For example, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic ester, (Wherein R is any one selected from the group consisting of alkyl, aryl, aralkyl, cyclic and unsaturated rings, and X is I, Br or Cl) represented by the following formula And a water-based part containing a conditioning component having at least one selected from the group consisting of the above-mentioned various kinds of functional groups, (1.9 to 3.1%) and skin keratin (3.1 to 6.9%) in the amino acids of the proteins constituting the hair or the skin, ~ 18%) and skin keratin (2.3 ~ 3.8%) are targeted and reacted, so that the reaction efficiency is lowered. There is a problem in that it must be synthesized.

Korean Patent Publication No. 2008-0064467

It is an object of the present invention to provide an antioxidant cosmetic composition which can continuously impart antioxidative effects without damaging the skin.

As means for solving the above problems, the present invention relates to an aminium compound; And an antioxidant component.

As another means for solving the above problems, the present invention provides an antioxidant cosmetic composition further comprising a peptide binding-promoting additive in the composition.

The antioxidant cosmetic composition according to the present invention contains a reactive antioxidant component and / or an aminium compound which has a specific functional group capable of covalent bonding with the protein residues of the skin, thereby forming a covalent bond without damaging the skin to provide a semi-permanent antioxidative effect give. It also provides an effective antioxidant effect, including a peptide bond formation promoting additive.

The present invention relates to an antioxidant cosmetic composition comprising an aminium compound and an antioxidant component.

The antioxidant cosmetic composition according to the present invention can maximize the antioxidative effect by, for example, reacting an existing antioxidant component with an aminium compound to form a covalent bond with the skin protein through a reactive antioxidant component bound with aminium .

The aminium 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 entire cosmetic composition. When the content is less than 0.001 part by weight, there is a problem that continuous skin antioxidative effect is hardly exhibited. If the content exceeds 10 parts by weight, the aminium compound, which exists excessively beyond the reaction site existing on the skin, There is a problem that it can act as a component that is lost and does not help to improve persistence.

In the present invention, the term 'antioxidative effect' refers to the action of free radicals or reactive oxygen species (ROS), which are highly reactive according to oxidative stress caused by intracellular metabolism or ultraviolet rays, Oxidation is inhibited. By removing free radicals or reactive oxygen species, damage of cells can be reduced, and skin aging can be exhibited.

The antioxidant component used in the present invention may be selected from the group consisting of aminoethanesulfonic acid (taurine), acetamidocaproic acid, acetyl benzoyloxy prasterone, acetyl cysteine, (2-acetylhydroquinone), adamantanylcarboxamido hydroxylbenzamide, aminoethanesulfinic acid, aminopropyl ascorbyl phosphate, angoroside C ), Anserine, apigenin, arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, BHA (butylhydroxyanisol), BHT (Butylated Hydroxy Toluene), bis-hydroxyethyl tocopherylsuoyl amido hydroxypropane (bis-hydroxyethyl tocopheryl succ inoylamido hydroxypropane, bis- (tetramethylhydroxypiperidinyl) sebacate, butylated xylenol, t-butylbenzamidohydroxybenzamide (t-butylbenzamido hydroxybenzamide, 4-butylresorcinol, caffeic acid, calcium ascorbate, carnosic acid, carotenoids, chitosan ascorbate, ), Chlorogenic acid, cobalt DNA, copper adenosine triphosphate (ATP), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine The compounds of the present invention may be used in combination with other excipients such as cysteine HCl, decapeptide-6, decapeptide-7, decursinol, decyl mercaptomethylimidazole, But are not limited to, diamylhydroquinone, di-t-butylhydroquinone, dicetyl thiodipropionate, dicyclopentadiene / t-butylcresol but are not limited to, copolymers, digalloyl trioleate, diisooctyl sebacate, dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide Dimethoxy di-p-cresol, dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, tocopheryl methylsilanol, diosmine, diretinyl ether, disodium ascorbyl sulfate, distearyl thiophosphate, odipropionate, ditridecyl thiodipropionate, dodecyl gallate, dunaliella bardawil powder, ellagic acid, epigallocatechin gallate (see, for example, erythropoietin, epigallocatechin gallate, ergothioneine, eriobotrya japonica leaf protoplasts, erythorbic acid, ethylbisiminomethylguaiacol manganese chloride, but are not limited to, ethyl ferulate, ethylhexyl ferulate, ferulic acid, feruloyl soy glycerides, furfuryl palmitate, genistein glucoside, Ginkgo leaf terpenoids, glucosylrutin, glyceryl chromonyl ether, glyceryl diethyl ether, But are not limited to, glyceryl diferulate, hesperetin, hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin, hydroquinone, p-hydroxyanisole, hydroxydecyl ubiquinone, hydroxylamine HCl, hydroxylamine sulfate, hydroxyphenyl dihydroxybenzamide (hereinafter referred to as " hydroxyphenyl dihydroxybenzamide, inositol hexaniacinate hexaascorbate, isooctyl caprylate / caprate, isooctyl thioglycolate, isoquercitrin, Kaempferol, kojic acid, kojyl glucoside, < RTI ID = 0.0 > Manganese adenosine triphosphate (MTP), manganese adenosine triphosphate (ATP), and the like, as well as the compounds of the present invention, such as kojyl methylenedioxycinnamate, kou-cha ekisu, lycopene, madecassoside, magnesium ascorbate, magnolol, Methine PEG-7 ascorbic acid, methoxytrimethylphenyl dihydroxyphenyl propanol, methyl-di-t-butylhydroperoxide, Methyl di-t-butylcresol, methyl-methacrylate / trimethoxysilylpropylmethacrylate crosspolymer (methyl (methyl) di-t- butylhydrocinnamate, methylene di- methacrylate / trimethoxysilylpropyl methacrylate crosspolymer), methyl myristic acid, niacinamide hydroxybenzoate, nictoflorin, nordi Nordihydroguaiaretic acid, octanicotinoyl epigallocatechin gallate, octapeptide-4, oligopeptide-28, and paranolic acid. PPG-2/5 tocopheryl ether, perillyl alcohol, phenethyl caffeate, phenylethyl ether, and the like. But are not limited to, phenylethyl resorcinol, phenylthioglycolic acid, phloretin, phloroglucinol, piceatannol, piperlonguminine, Potassium ascorbyl tocopheryl phosphate, potassium sulfite, PPG-2 tocophereth-5, propyl gallate, and the like. , Protocatechal caldhide (protoc atorvastatin, atechuicaldehyde, puerarin, pyridoxine hydroxybenzoate, phyridyloxide t-butylnitrone, quercetin, resacetophenone, resorcinol, 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 erythorbate, sodium phosphono-pyridoxine Sodium phosphono-pyridoxylidenerhodanine, sodium thioglycolate, sodium zinc histidine dithiooctanamide, sorbitol ferulic acid (sor barium furfural, stearyl gallate, succinoyl ascorbate pentapeptide-6, tangeritin, tert-butylhydroquinone (TBHQ), tetrabutylethylidine bisphenol tetrabutyl ethylidinebisphenol, tetrahydrodemethoxydiferuloylmethane, tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetramethylbutyl dihydroxybenzamide, But are not limited to, tetramethylchromanol glucoside, thioctic acid, thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, Thymol trimethoxycinnamate, tococysteamide, tocopheresis-5 ( tocophereth-5, tocopherol, tocophersolan, tocopheryl acetate, tocoquinone, toluene, o-tolyl biguanide, Butyrol, tripropylene glycol, tris-BHT mesitylene, tris (nonylphenyl) phosphate, trisodium ascorbyl isopalmitate phosphate (trisodium ascorbyl isopalmitate phosphate, tyrosyl histidine HCl, ubiquinol, ubiquinone, ulva lactuca powder, uuron-cha ekisu, Xylyl dibutylbenzofuranone, zinc adenosine triphosphate (ATP), zinc dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-phosphine Agent (zinc pyridoxal 5-phosphate) and but be at least one selected from the group consisting of derivatives thereof, and the like.

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 entire cosmetic composition. When the content is less than 0.001, the effect is insufficient and there is a limit. When the content is more than 50 parts by weight, there is a problem in formulation and stabilization.

Particularly, in the present invention, the antioxidant component can increase the reaction efficiency with the aminium 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 covalent bonding with protein residues on the skin surface.

The functional groups covalently bonded to the protein include carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, But are not limited to, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, Selected from the group consisting of imidazole, oxycarbonyl imidazole, imine, thiol, maleimide, vinyl sulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate It may be more than one, but it is not limited anymore.

In addition, the protein may comprise reactive residues of thiol, hydroxyl, carboxyl or amine.

The aminium compound may be a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,

R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,

R ₃ to R ₆ are each the same or different and are alkyl or heterocycloalkyl,

X is oxygen, sulfur or a void form directly attached between R ₂ and aminium.

 (2)

In Formula 2,

R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,

R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,

R ₃ and R ₄ are each the same or different and are alkyl or heterocycloalkyl,

X is oxygen, sulfur or a void form directly attached between R ₂ and ammonium,

X ₁ is oxygen or sulfur;

(3)

In Formula 3,

R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,

R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,

R ₃ to R ₅ are each the same or different and are alkyl or heterocycloalkyl,

X is oxygen, sulfur or a void form directly attached between R ₂ and ammonium,

X ₁ is oxygen or sulfur.

The alkyl may have 1 to 10 carbon atoms and preferably 3 or less carbon atoms.

The R ₃ to R ₆ may have a symmetrical structure or a symmetric structure.

In particular, when R ₃ to R ₆ are a symmetrical structure, R ₃ and R _4, R ₅ and R ₆ are cycloalkyl having 4 to 8 carbon atoms connected to each other, or R ₃ and R ₆ are each methyl or ethyl R ₄ , R ₅ may be a cycloalkyl having 4 to 8 carbon atoms linked to each other, and the cycloalkyl may be a bispyrrolidino group, a bispiperidino group, an imidazolium group or a pyrimidinium group.

When R ₃ to R ₆ have an asymmetric structure, they may be compounds represented by Formula 2 or Formula 3.

The water-soluble nonionic polymer preferably has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da. When the molecular weight is 300,000 Da or more, the proportion of the aminium compound that induces covalent bonding is too small to exhibit its efficacy.

The water-soluble nonionic polymer may specifically be selected from the group consisting of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran and guar gum And at least one polymer selected from the group consisting of

The bead or resin type polymer preferably has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da. When the molecular weight is more than 300,000 Da, the proportion of the aminium compound that induces covalent bond is too small to exhibit the efficacy.

The bead-shaped or resin-type polymer resin may specifically include a resin such as styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, ether ketone, etherimide, ether sulfone, phthalamide, phenylene ether, , Phenylene sulfide, sulfone, urethane, vinylidene fluoride, and tetrafluoroethylene.

The polymer beads preferably have an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 占 퐉, more preferably 1 占 퐉 to 100 占 퐉, and most preferably 1 占 퐉 to 70 占 퐉 . If the diameter of the polymer bead is less than 100 nm, safety problems may occur on the skin surface. If the diameter of the polymer bead is larger than 1 mm, there is a problem in formulation and stabilization.

The silica beads preferably have an average particle diameter of 100 nm to 1 mm, preferably 100 nm to 100 占 퐉, more preferably 1 占 퐉 to 100 占 퐉, and most preferably 1 占 퐉 to 70 占 퐉 . If the diameter of the silica beads is less than 100 nm, safety problems may occur on the surface of the skin. If the diameter of the silica beads is larger than 1 mm, there is a problem in formulation and stabilization.

In one preferred embodiment of the antioxidant cosmetic composition according to the present invention, an antioxidant component having a carboxyl group is made into a reactive ester antioxidant component having a direct bioactivity, or an amino acid ex in an excessive amount in skin keratin (15.5 to 23.5% Aspartic acid, and glutamic acid) can be reactively esterified to form a form that can be targeted by an antioxidant component including an amine group, thereby increasing the reaction efficiency and significantly enhancing the effect. In a more preferred embodiment, the antioxidant component having a carboxyl group or a skin protein is firstly reacted with a polymeric aminium compound of the formula (1) first to form a reactive ester, and an antioxidant component Or by reacting with an amine on the skin surface, an excellent antioxidative effect can be obtained.

The reaction scheme 1 shows a reaction scheme in which the antioxidant component molecule having a carboxyl group reacts with an aminium compound to form a reactive ester and then reacts with an amino acid having an amine moiety to form a covalent bond.

 [Reaction Scheme 1]

As shown in Reaction Scheme 2, asparaginic acid and glutamic acid, which are carboxylamino group-bearing biosynthetic amino acids on the surface of skin proteins, first react with an aminium compound to form a reactive ester, and then react with a whitening component having an amine residue to form a covalent bond Respectively.

In the following Reaction Scheme 2, asparaginic acid and glutamic acid, which are carboxylamino group-bearing biological amino acids on the surface of the skin, first react with an aminium compound to form a reactive ester, and then react with an antioxidant component having an amine residue to form a covalent bond Respectively.

 [Reaction Scheme 2]

Using the aminium compound, the antioxidant component adhered to the skin by protein and peptide bond can be maintained permanently attached to the skin without being removed from the skin by a cleaning method such as a soap and a cleanser.

The present invention also relates to a pharmaceutical composition comprising an antioxidant component selected from the group consisting of a carbodiimide, an imidoester, an aryl azide, a diazirine, a hydroxymethylphosphine, a pentafluorophenyl ester, a pyridyl disulfide, a sulfohydroxysuccinimide ester, But are not limited to, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, Selected from the group consisting of imidazole, oxycarbonyl imidazole, imine, thiol, maleimide, vinyl sulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate A reactive antioxidant component having a functional group covalently bonded to at least one protein . ≪ / RTI >

For example, the reaction may include an antioxidant component to which an aminium compound produced by the first reaction of an aminium compound is coupled as shown in Reaction Scheme 1 above. In addition, the present invention may include an antioxidant cosmetic composition containing the above-mentioned reactive antioxidant component.

In the antioxidative cosmetic composition according to the present invention, it is preferable to use at least one compound selected from the group consisting of hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, One or more peptide bond formation reaction promoting additives selected from the group consisting of hydroxybenzotriazine and oximarine. 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 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 the chemical reaction is saturated, so that the product is not economical and does not contribute to the stability of the product. When used below 0.0001, little or no help is given to reactivity.

In order to further enhance the effect of the antioxidant cosmetic composition according to the present invention, fatty acids such as palmitic acid and stearic acid, fatty alcohols, long chain alkyl quaternary ammonium salts of straight chain and branched chain, and the like The cationic surfactant, the cationic cellulose, the cationic guar, the cationic polymer such as cationized polyvinylpyrrolidone, and the like may be mixed together with the silicone to make the preparation easier. In order to formulate the composition into a cosmetic preparation, it is also possible to formulate cosmetics such as a solvent, a surfactant, a thickener, a stabilizer, a preservative, a colorant, a pH adjuster, a metal ion sequestrant, a pearlizing agent, an appearance improver, an emollient, Components may be incidentally included. The ingredients for the formulation may be used in an amount of 40 to 99 parts by weight based on 100 parts by weight of the total composition.

The antioxidant cosmetic composition according to the present invention can be used for the formulation of an antioxidant cosmetic composition including a component having antioxidant function having a functional group. Examples of application of the hair product include a shampoo composition, a shampoo, a rinse, a treatment, a wax, a gel, a spray, a mousse, a hair lotion, a hair pack, a hair essence, a hair cream, a research hair dye, Non-woven fabric, sheet, and the like. Application examples of the skin product generally include basic cosmetics (lotion, serum, essence, lotion, cream, etc.) for arranging and protecting skin, color cosmetics (makeup base, foundation, powder, Cleansing lotion, cleansing cream, cleansing gel, pack, cosmetics, etc.), makeup for hand and toenails (manicure, nutrient, Mask, soap, cleansing tissue, etc.), sun care cosmetics, body cosmetics (body lotion, shower gel, body cream, body oil, etc.).

More preferably, the antioxidant cosmetic composition according to the present invention contains an aminium compound and at the same time contains an antioxidant component having a reactive functional group. When the activity of the above preparation is lowered in the aqueous system, It may be easier to mix with a buffer for pH control just before use, or may be brought into contact with water during the washing process. Examples of non-aqueous formulations include liquid, sheet, powder, tablet, oil, wax, ampoule, gel and the like which are used as ordinary non-aqueous cosmetic preparations. In addition, the aminium-based compound and the antioxidant component can be formulated into a single agent in an encapsulated form or a two-part form of each separately. In addition, a method of blocking a derivative having a reactive functional group and an antioxidative functional component from moisture by encapsulation can also be used.

In order to increase the antioxidative effect of the skin antioxidant cosmetic composition according to the present invention, a combination of 2-basic acid ester oil such as dioctyl citrate, dioctyl adipate, diethyl sebacate and the like, polyol, polyethylene glycol, propylene glycol, Silane glycols, butanediol and their isomers, glycerol, benzyl alcohol, ethoxydiglycol and derivatives thereof. The above-mentioned solvents increase the permeability of hair or skin and are used as a solvent of a poorly soluble substance. More preferably, the solvent used for increasing the activity-maintaining effect 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 illustrative of the present invention, and the present invention is not limited to the following examples.

Example  1 and Comparative Example  1: Antioxidant cosmetics ( 100 g ) Formulation Manufacturing

A cream pack type mask pack was prepared with the composition and contents shown in Table 1 below.

The raw materials 3 to 13 were heated to 70 ° C and homogeneously mixed at 1500 rpm for 5 minutes using a homomixer. The oil phase components 15 to 24 dissolved in advance by heating at 70 DEG C were added to the mixed water phase and homogeneously mixed at 3500 rpm for 5 minutes using a homomixer. Thereafter, the temperature was lowered to 50 ° C, and a neutralizing agent, an aminium compound, Polystyrene supported O- (Benzotriazol-1-yl) -N, N, N ', N'-tetramethyluronium (PS- -Hydroxybenzotriazole (HOBt) 2 and fragrance 14 were added and homogeneously mixed with a homomixer for 3 minutes, followed by defoaming, filtration and cooling.

The PS-TBTU is a polymer resin having a weight average molecular weight of 200,000 Da, wherein R ₁ is represented by the following formula (4) (m + n + x + y: z = 99: 1) ; R ₂ is benzotriazole-yl, R ₃ to R ₆ are methyl groups, and X is an oxygen atom. The z is a crosslinker that is not attached to a specific site and connects the polymers in a random manner, and Tetrahedron Letters 41 (2000) 2463-2466 and / or Chem. Rev. 2011, 111, 6557-6602.

[Chemical Formula 4]

ingredient Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 PS-TBTU - - - 0.1 0.1 0.1 HOBt - - - 0.01 0.01 0.01 Acetylcysteine 2.0 - - 2.0 - 2.0 Caffeic acid - 2.0 - - 2.0 - Aminoethanesulfonic acid - - 2.0 - - 2.0 glycerin 6.0 6.0 6.0 6.0 6.0 6.0 DPG 3.0 3.0 3.0 3.0 3.0 3.0 1,3-butylene glycol 2.0 2.0 2.0 2.0 2.0 2.0 Urea / HEPES 0.8 0.8 0.8 0.8 0.8 0.8 antiseptic 1.0 1.0 1.0 1.0 1.0 1.0 Anti-inflammatory agent 2.0 2.0 2.0 2.0 2.0 2.0 Carbomer 0.2 0.2 0.2 0.2 0.2 0.2 Xanthan gum 0.05 0.05 0.05 0.05 0.05 0.05 corrector 0.28 0.28 0.28 0.28 0.28 0.28 Purified water To 100 To 100 To 100 To 100 To 100 To 100 Beauty 0.1 0.1 0.1 0.1 0.1 0.1 Cetearyl alcohol 2.5 2.5 2.5 2.5 2.5 2.5 Glyceryl stearate 1.2 1.2 1.2 1.2 1.2 1.2 PEG-100 stearate 0.3 0.3 0.3 0.3 0.3 0.3 PEG-40 stearate 0.5 0.5 0.5 0.5 0.5 0.5 Stearic acid 0.3 0.3 0.3 0.3 0.3 0.3 Cyclohexasiloxane 6.0 6.0 6.0 6.0 6.0 6.0 Petaerythrityl tetraethylhexanoate 3.0 3.0 3.0 3.0 3.0 3.0 Dimethicone 5.0 5.0 5.0 5.0 5.0 5.0 Macadamia oil 2.0 2.0 2.0 2.0 2.0 2.0 Hydrogenated polydecene 4.0 4.0 4.0 4.0 4.0 4.0

Experimental Example  One

Acetylcysteine, caffeic acid, and aminoethanesulfonic acid were attached to the skin by bioconjugation using PS-TBTU, and the efficacy was confirmed.

Two grams of each of the compositions of Comparative Examples 1 to 3 and Examples 1 to 3 were applied to 10 subjects on the back of the hand twice daily in the morning and evening, and after 1 day, 5 days, and 10 days after the treatment, (5 excellent, 4 slightly excellent, 3 no difference, 2 no effect, 1 very no effect), and the skin aging prevention effect was compared with the sensory evaluation.

Compared with the results (Table 2) of Examples 1 to 3 and Comparative Examples 1 to 3 and Comparative Examples 1 to 3 that did not include PS-IIDQ, Examples 1 to 3 including PS-TBTU had a covalent bond formation effect And showed better skin aging improvement effect.

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

Claims (17)

An antioxidant cosmetic composition comprising an aminium compound and an antioxidant component.
The method according to claim 1,
Wherein the aminium compound is a compound represented by the following general formula (1), (2) or (3):
[Chemical Formula 1]

R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,
R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,
R ₃ to R ₆ are each the same or different and are alkyl or heterocycloalkyl,
X is oxygen, sulfur or a void form directly attached between R ₂ and aminium.
(2)

In Formula 2,
R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,
R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,
R ₃ and R ₄ are each the same or different and are alkyl or heterocycloalkyl,
X is oxygen, sulfur or a void form directly attached between R2 and < RTI ID = 0.0 >
X ₁ is oxygen or sulfur;
(3)

In Formula 3,
R ₁ represents a water-soluble nonionic polymer, a polymer resin in bead or resin form, or a silica bead,
R ₂ is a group selected from triazole, triazolopyridine, benzotriazole, benzotriazolyl, triazine, triazinyl, benzotriazine, benzotriazinyl, azabenzotriazine, azabenzotriazinyl, azabenzotriazole, Triazolyl, pentafluorophenyl, pentafluorothiophenyl, nitrophenyl, oxopyridyl, azabenzotriazole, succinimido, dicyanomethylideneamino, cyanoethoxycarbonylmethyleneamino, norbornenedicarboximido, ≪ RTI ID = 0.0 > phthalimido, < / RTI > and oxypyrrolidine,
R ₃ to R ₅ are each the same or different and are alkyl or heterocycloalkyl,
X is oxygen, sulfur or a void form directly attached between R ₂ and ammonium,
X ₁ is oxygen or sulfur.
3. The method of claim 2,
Wherein the water-soluble nonionic polymer has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
3. The method of claim 2,
The water-soluble nonionic polymer may be at least one selected from the group consisting of polyethylene glycol, polyvinyl alcohol, polyethylene oxide, polyacrylonitrile, polyvinylpyrrolidone, polyisopropylacrylamide, cellulose derivatives, starch derivatives, dextran, Lt; RTI ID = 0.0 > 1, < / RTI >
3. The method of claim 2,
Wherein the bead or resin type polymer resin has a weight average molecular weight of 1,000 Da or more and less than 300,000 Da.
3. The method of claim 2,
The bead or resin type polymer resin may be selected from the group consisting of styrene, ethylene, butadiene, acrylonitrile, methylstyrene, terephthalate, ethylene chloride, ether ketone, etherimide, ether sulfone, phthalamide, phenylene ether, Wherein the antioxidant is a polymer polymerized with monomers selected from the group consisting of lignosulfide, sulphone, urethane, vinylidene fluoride and tetrafluoroethylene.
3. The method of claim 2,
Wherein the silica beads have an average particle diameter of 100 nm to 1 mm.
The method according to claim 1,
Wherein the dihydroxyquinoline-based compound is 0.001 to 10 parts by weight based on 100 parts by weight of the total composition.
The method according to claim 1,
Wherein the antioxidant component comprises a carboxyl group or an amine group in the molecule.
The method according to claim 1,
Wherein the antioxidant component is selected from the group consisting of aminoethanesulfonic acid (taurine), acetamidocaproic acid, acetyl benzoyloxy prasterone, acetyl cysteine, 2-acetyl hydroquinone (2 aminopropyl ascorbyl phosphate, angoroside C, anserine hydrochloride, and the like. The term " hydroxymethyl " arginine, apigenin, arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, BHA (butylhydroxyanisol) , Butylated Hydroxy Toluene (BHT), bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane e), bis- (tetramethyl hydroxypiperidinyl sebacate), butylated xylenol, t-butylbenzamido hydroxylbenzamide 4-butylresorcinol, caffeic acid, calcium ascorbate, carnosic acid, carotenoids, chitosan ascorbate, chitosan ascorbate, Chlorogenic acid, cobalt DNA, copper adenosine triphosphate (ATP), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine hydroxides, Decapeptide-6, decapeptide-7, decursinol, decyl mercaptomethylimidazole, diamylhydroquinone (dicyclohexylcarbodiimide), and the like. diamylhydroquinone), Di-t-butylhydroquinone, dicetyl thiodipropionate, dicyclopentadiene / t-butylcresol copolymer, di-t-butylhydroquinone, But are not limited to, digalloyl trioleate, diisooctyl sebacate, dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide, dimethoxy di- but are not limited to, dimethoxy di-p-cresol, dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, Diisomine, diretinyl ether, disodium ascorbyl sulfate, distearyl thiodipropionate, diethanolamine, Dodecyl gallate, dunaliella bardawil powder, ellagic acid, epigallocatechin gallate, ergodextrin, dodecyl gallate, Erythropoietin, ergothioneine, eriobotrya japonica leaf protoplasts, erythorbic acid, ethylbisiminomethylguaiacol manganese chloride, ethyl ferulate, But are not limited to, ethylhexyl ferulate, ferulic acid, feruloyl soy glycerides, furfuryl palmitate, genistein glucoside, ginkgo leaf terpenoids, glucosylrutin, glyceryl chromonyl ether, glyceryl < RTI ID = 0.0 > hydroquinone, hydroperoxide, hydroperoxide, hydrogen peroxide, diferulate, hesperetin, hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin, hydroquinone, P-hydroxyanisole, hydroxydecyl ubiquinone, hydroxylamine hydrochloride, hydroxylamine sulfate, hydroxyphenyl dihydroxybenzamide, hydroxyphenyl dihydroxybenzamide, Isocetyl caprylate / caprate, isooctyl thioglycolate, isoquercitrin, campperol (caprolactam, caprolactam, caprolactam, caprolactam, caprolactam, caprolactam, kaempferol, kojic acid, kojyl glucoside, kojyl methylein, nedioxycinnamate, kou-cha ekisu, lycopene, madecassoside, magnesium ascorbate, magnolol, manganese adenosine triphosphate (ATP), matrine matrine, melatonin, methoxy PEG-7 ascorbic acid, methoxytrimethylphenyl dihydroxyphenyl propanol, methyl-di-t-butylhydroxyhydrocinene Methyl di-t-butylhydrocnamate, methylene di-t-butylcresol, methyl methacrylate / trimethoxysilylpropyl methacrylate cross polymer (methyl methacrylate / trimethoxysilylpropyl methacrylate crosspolymer, methyl myristic acid, niacinamide hydroxybenzoate, nictoflorin, nordihydroguaiac, Nordihydroguaiaretic acid, octanicotinoyl epigallocatechin gallate, octapeptide-4, oligopeptide-28, paeonol, palmatine, (PEG / PPG-2/5 tocopheryl ether), perillyl alcohol, phenethyl caffeate, phenylethyl resorcinol, resorcinol, phenylthioglycolic acid, phloretin, phloroglucinol, piceatannol, piperlonguminine, porphyridium polysaccharide, , Potassium ascorbyl tocopheryl phosphate, potassium sulfite, PPG-2 tocophereth-5, propyl gallate, protocatechal caldera, Protocatechuicaldehyde, Puerarin, pyridoxine hydroxybenzoate, phyridyloxide t-butylnitrone, quercetin, resacetophenone, resorcinol, The compounds of the present invention may be used in combination with other medicaments such as resveratrol, retinyl formyl aspartamate, rosmarinic acid, rutin, rutinyl succinate, ryoku-cha ekisu, but are not limited to, salnacedin, sodium ascorbate, sodium sulfite, sodium tocopheryl phosphate, sodium erythorbate, sodium phosphono-pyridoxylidene fodonin sodium phosphono-pyridoxylidenerhodanine, sodium thioglycolate, sodium zinc histidine dithiooctanamide, sorbityl furfural, Stearyl gallate, succinoyl ascorbate pentapeptide-6, tangeritin, tert-butylhydroquinone (TBHQ), tetrabutyl ethylidine bisphenol, tetra Examples of the solvent include tetrahydrodemethoxydiferuloylmethane, tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetramethylmethanol, But are not limited to, tetramethylchromanol glucoside, thioctic acid, thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, thymol trimethoxycinnamate trimethoxycinnamate, tococysteamide, tocophereth-5, Tocopherol, tocophersolan, tocopheryl acetate, tocoquinone, toluene, o-tolyl biguanide, totarol, tocopherol, Triprophylene glycol, tris-BHT mesitylene, tris (nonylphenyl) phosphate, trisodium ascorbyl isopalmitate phosphate, The extract of tyrosyl histidine HCl, ubiquinol, ubiquinone, ulva lactuca powder, uuron-cha ekisu, xylyl dibutylbenzofuranone xylyl dibutylbenzofuranone, zinc adenosine triphosphate (ATP), zinc dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-p wherein the antioxidant composition is at least one selected from the group consisting of phosphate and derivatives thereof.
The method according to claim 1,
Wherein the antioxidant component has a functional group capable of covalently bonding to protein residues on the skin surface.
12. The method of claim 11,
The functional groups covalently bonded to the protein include carbodiimide, imidoesters, aryl azides, diazylines, hydroxymethylphosphines, pentafluorophenyl esters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy amines, But are not limited to, hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, Selected from the group consisting of imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide, ketone, carboxylic acid and phosphate At least one antioxidant cosmetic composition.
In the first aspect,
Wherein the antioxidant component is 0.001 to 50 parts by weight based on 100 parts by weight of the total composition.
In the first aspect,
Wherein the composition further comprises a peptide bond formation reaction promoting additive.
15. The method of claim 14,
The peptide bond formation reaction promoting additive may be at least one selected from the group consisting of hydroxysuccinimide, hydroxycarboximide, hydroxytriazole, hydroxybenzotriazole, hydroxypyridinone, hydroxyphenylbenzimidazole, hydroxyindolinone, hydroxy Wherein the antioxidant composition is at least one selected from the group consisting of benzotriazines and oximes.
15. The method of claim 14,
Wherein the peptide bond formation reaction promoting additive is 0.0001 to 10 parts by weight based on 100 parts by weight of the total composition.
The method according to claim 1,
An aminium-based compound and an antioxidant component are formulated into a single preparation in an encapsulated form; Wherein the aminium compound and the antioxidant component are separated from each other.