KR102006947B1 - Cosmetics Compositions for antioxidant - Google Patents

Cosmetics Compositions for antioxidant Download PDF

Info

Publication number
KR102006947B1
KR102006947B1 KR1020130152313A KR20130152313A KR102006947B1 KR 102006947 B1 KR102006947 B1 KR 102006947B1 KR 1020130152313 A KR1020130152313 A KR 1020130152313A KR 20130152313 A KR20130152313 A KR 20130152313A KR 102006947 B1 KR102006947 B1 KR 102006947B1
Authority
KR
South Korea
Prior art keywords
acid
antioxidant
cosmetic composition
sodium
phosphate
Prior art date
Application number
KR1020130152313A
Other languages
Korean (ko)
Other versions
KR20150066805A (en
Inventor
김시원
손성길
김지현
강택균
이상민
Original Assignee
주식회사 엘지생활건강
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지생활건강 filed Critical 주식회사 엘지생활건강
Priority to KR1020130152313A priority Critical patent/KR102006947B1/en
Publication of KR20150066805A publication Critical patent/KR20150066805A/en
Application granted granted Critical
Publication of KR102006947B1 publication Critical patent/KR102006947B1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • A61K8/355Quinones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67Vitamins
    • A61K8/676Ascorbic acid, i.e. vitamin C
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/736Chitin; Chitosan; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers

Abstract

The present invention relates to an antioxidant cosmetic composition.
The antioxidant cosmetic composition according to the present invention contains an antioxidant substance having a specific functional group capable of covalently bonding with a protein residue on the skin or hair surface, thereby forming a covalent bond without damaging the skin or hair, thereby providing a semipermanently desired antioxidant effect.

Description

Cosmetics Compositions for antioxidant

The present invention relates to a reactive antioxidant and an antioxidant cosmetic composition having a functional group binding to a protein.

In general, the antioxidant of cosmetics has the ability to significantly reduce or prevent the phenomenon that the skin function and structure damaged and burned out by the oxidative action, and to restore the damaged skin due to UV exposure.

In addition, quasi-drugs are defined as having a mild action and not used for the treatment or prevention of diseases, but do not have a purpose for use such as affecting the structure and function of the body.

Antioxidant cosmetics are generally used to prepare and protect the skin. Antioxidant cosmetics for base, base, point, nail make-up Antioxidant cosmetics and body antioxidant cosmetics such as washing, sun care and sun tanning, pre-shampoo composition, shampoo, It may include all cosmetic preparations that can be used on hair, such as rinses, treatments, waxes, sprays, mousses, hair lotions, essences, hair creams, permanent hair dyes, temporary hair dyes, and pumps. When used as a ingredient in skin and hair, it provides only a temporary effect until the next cleaning after the treatment, and there is always a hassle to be reprocessed after the cleaning.

Patent document 1 relates to a non-aqueous personal care product for skin or hair, wherein a functional group capable of covalently bonding to protein residues on the hair or skin surface in a non-aqueous part is 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, Group consisting of disulfide, ketone and functional group represented by RX (R is any one selected from the group consisting of alkyl, aryl, aralkyl, ring and unsaturated ring, X is I, Br or Cl) Although it comprises a conditioning component having any one or more selected from the non-aqueous part and the water-based part, and discloses a personal care product for hair or skin, characterized in that the mixture is used immediately before use, but the various functional groups In the case of the target, lysine, which is harmful to the human body or contains a small amount of amino acids in the protein constituting the hair or skin, such as hair (1.9-3.1%) and skin keratin (3.1-6.9%), or hair (16.6) ~ 18%) and the skin keratin (2.3 ~ 3.8%) of the target cysteine to react because the reaction efficiency is reduced and each material There is a problem that must be synthesized.

Korean Unexamined Patent No. 2008-0064467

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

As a means for solving the above problems, the present invention provides an antioxidant cosmetic composition comprising a carbodiimide compound and an antioxidant.

As another means for solving the above problems, the present invention is an antioxidant, carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, pyridyl disulfide, sulfo-hydride Provided is a reactive antioxidant that binds a functional group covalently bound to one or more hair or skin surfaces selected from the group consisting of oxysuccinimide esters, alkoxy amines, hydrazides, haloacetyls and azides.

As another means for solving the above problems, the present invention provides an antioxidant cosmetic composition comprising the reactive antioxidant material.

The antioxidant cosmetic composition according to the present invention contains reactive antioxidants and / or carbodiimide-based compounds incorporating specific functional groups capable of covalently binding to protein residues of hair or skin, thereby forming covalent bonds without damaging the hair or skin. It provides semi-permanent antioxidant effects.

The present invention relates to an antioxidant cosmetic composition comprising a carbodiimide compound and an antioxidant.

Antioxidant cosmetic composition according to the present invention, for example, by reacting a carbodiimide-based compound to a known antioxidant material through a reactive antioxidant compound of carbodiimide groups to form a covalent bond with the protein of the hair or skin Can be maximized.

The carbodiimide-based compound may be included in an amount of 0.001 to 10% by weight, 0.01 to 7% by weight, or 0.1 to 5% by weight based on 100% by weight of the total cosmetic composition. If the content thereof is less than 0.001% by weight, there is a problem that it is difficult to show a continuous antioxidant effect. If the content exceeds 10% by weight, the carbodiimide-based compound that is excessively present beyond the reaction site present in the hair or skin does not react with the hair or skin. There is a problem that can act as a component that does not help to improve the sustainability by reacting with the agonist in a poor state.

In the present invention, the 'antioxidative effect' refers to a cell caused by free radicals or reactive oxygen species (ROS) that are highly reactive due to oxidative stress caused by intracellular metabolism or ultraviolet light. It refers to inhibiting oxidation, and by removing free radicals or reactive oxygen species, it is possible to reduce the damage of the cells to exhibit the anti-aging effect of the skin.

Antioxidants used in the present invention significantly reduce or prevent the phenomenon of destruction and exhaustion of skin function and structure damaged by oxidation, such as extracts derived from natural products such as copper, plants, minerals, fermented extracts, amino acids, peptides, proteins, etc. It may include, but is not limited to, antioxidant components having the ability to do so. For example, acetamidocaproic acid, acetyl benzoyloxy prasterone, acetyl cysteine, 2-acetylhydroquinone, adamantanylcarbosamido hydride Adamantanylcarboxamido hydroxylbenzamide, aminoethanesulfinic acid, aminopropyl ascorbyl phosphate, angoroside C, anserine, apigenin, arbutin arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, BHA (butylhydroxyanisol), butylated hydroxy toluene (BHT), bis-hydro Bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane, bis-tetramethyl hydroxypyridinyl sebacate (b is- (tetramethyl hydroxypiperidinyl) sebacate), butylated xylenol, t-butylbenzamido hydroxylbenzamide, 4-butylresorcinol, caffeine Caffeic acid, calcium ascorbate, carnosic acid, carotenoids, chitosan ascorbate, chlorogenic acid, cobalt DNA , Copper adenosine triphosphate (ATP), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine HCl, decapeptide-6 , Decapeptide-7, decursinol, decyl mercaptomethylimidazole, diamylhydroquinone, di-t-butylhydroquinone butylhydroquinone), dicetyl thio Propionate (ditetyl thiodipropionate), dicyclopentadiene / t-butylcresol copolymer, digaloyl trioleate, diisooctyl sebacate, Dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide, dimethoxy di-p-cresol, dimethylmethoxy chromamann ( dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, diosmine, diretinyl ether, disodium ascorbyl sulfate (disodium ascorbyl sulfate), distearyl thiodipropionate, ditridecyl thiodipropionate, dode Dodecyl gallate, dunaliella bardawil powder, ellagic acid, epigallocatechin gallate, ergothioneine, loquat leaf protoplasts eriobotrya japonica leaf protoplasts, erythorbic acid, ethylbisiminomethylguaiacol manganese chloride, ethyl ferulate, ethylhexyl ferulate, and phenulic acid ferulic acid, feruloyl soy glycerides, furyl palmitate, genistein glucoside, ginkgo leaf terpenoids, glucosylrutin , Glyceryl chromonyl ether, glyceryl diferulate, hesperetin, hexyloxy trimethylphenol ( hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin, hydroquinone, p-hydroxyanisole, hydroxydecyl ubiquinone ), Hydroxyamine hydrochloride (hydroxylamine HCl), hydroxylamine sulfate, hydroxyphenyl dihydroxybenzamide, inosinol hexaniacinate hexaascorbate, Isooctyl caprylate / caprate, isooctyl thioglycolate, isoquercitrin, kaempferol, kojic acid, kojyl glucoside, Kojyl methylenedioxycinnamate, black tea extract (kou-cha ekisu), lycopene, Decassoside, magnesium ascorbate, magnolol, manganese adenosine triphosphate, matrine, melatonin, methoxy PEG-7 ascorbic acid PEG-7 ascorbic acid), methoxytrimethylphenyl dihydroxyphenyl propanol, methyl di-t-butyl hydroxyhydrocinnamate, methylene di-t-butyl Methylene di-t-butylcresol, methyl methacrylate / trimethoxysilylpropyl methacrylate crosspolymer, methyl myristic acid, niacinamide hydride Niacinamide hydroxybenzoate, nictoflorin, nordihydroguaiaretic acid, octanicotinoyl epigaloca Octanicotinoyl epigallocatechin gallate, octapeptide-4, oligopeptide-28, paeonol, palmatine, PEG / PPG-2 / 5 tocopheryl PEG / PPG-2 / 5 tocopheryl ether, perillyl alcohol, phenethyl caffeate, phenylethyl resorcinol, phenylthioglycolic acid, flore Phloretin, phloroglucinol, piceatannol, piperlonguminine, porphyridium polysaccharide, potassium ascorbyl tocopheryl phosphate , Potassium sulfite, PPG-2 tocophereth-5, propyl gallate, protocatechuicaldehyde, puerarin, pyridoxine Hydrobenzoate (pyridoxine hydr) oxybenzoate, pyridyloxide t-butylnitrone, quercetin, resacetophenone, resorcinol, resveratrol, retinyl formyl aspara 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-pyridoxylidenerhodanine, sodium thioglycorate (sodium thioglycolate), sodium zinc histidine dithiooctanamide, sorbityl furfural, stearyl gallate, succinoyl ascorbate penta Peptide-6 (succinoyl ascorbate pentapeptide-6), tangeritin, tert-butylhydroquinone (TBHQ), tetrabutyl ethylidinebisphenol, tetrahydrodemethoxydiferuloylmethane, tetrahydro Tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetramethylchromanol glucoside, thioctic acid, Thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, thymol trimethoxycinnamate, tococysteamide, tocophereamide Tocophereth-5, tocopherol, tocophersolan, tocopheryl acete Tocopheryl acetate, tocoquinone, toluene, o-tolyl biguanide, totarol, triprophylene glycol, tris-BHT mesitylene tris-BHT mesitylene, tris (nonylphenyl) phosphate, trisodium ascorbyl isopalmitate phosphate, tyrosyl histidine HCl, ubiquinol (ubiquinol), ubiquinone, ulva lactuca powder, ooron-cha ekisu, xylyl dibutylbenzofuranone, zinc aTP (zinc adenosine triphosphate), zinc Zinc dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-phosphate and derivatives thereof More than can.

The antioxidant substance is preferably used in 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 thereof is less than 0.001 part by weight, there is a problem of effective performance limitation, and if it exceeds 50 parts by weight, there is a problem in formulation and formulation stabilization.

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

In addition, the antioxidant in the present invention may have a functional group capable of covalently bonded to protein residues on the hair or skin surface.

The functional group covalently bonded with the protein is carbodiimide, imido ester, aryl azide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, Hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl ester , Imidazole, oxycarbonyl amidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone This is not restrictive.

In addition, the protein may include a reactive moiety of thiol, hydroxyl, carboxyl or amine.

The carbodiimide-based compound is a generic term for a compound containing a structure represented by the following formula (1) in a molecule.

[Formula 1]

-N = C = N-

The carbodiimide-based compound preferably includes at least 1 to 1000 structures of Formula 1, more preferably 1 to 100 structures represented by Formula 1 in a molecule, It is more preferable to include 1 to 10 structures represented in the molecule.

In this case, when the number of carbodiimide groups represented by the formula (1) in one molecule exceeds 1000, the viscosity of the raw material is too large, the molecular weight is too large, and the reaction sites that can react too much are excessively large, and The molecule | numerator which has a bodyimide group becomes so large that the problem which efficiency falls by covering the part which shows the functional effect of the molecule which has a substantial function arises.

Specific examples of the carbodiimide-based compound in the present invention may be a compound represented by the following formula (2), n is 4 and m is 11 in the formula (2) is benzene, 1,3, -bis (1- Isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block (Benzene, 1,3-bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono- Me-ether-blocked) (hereinafter referred to as polymer type carbodiimide compound of Formula 2).

(2)

Figure 112019057789943-pat00005

In Formula 2, n is 1 to 100, m is 1 to 100.

In another embodiment of the carbodiimide-based compound in the present invention, as a compound represented by the following formula (3), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide HCl (1-Ethyl-3- (3-dimethylaminopropyl) carbodiimideHCl) can be used.

(3)

Figure 112013112470474-pat00002

In a preferred embodiment of the antioxidant cosmetic composition according to the present invention, the antioxidant material having a carboxyl group is made in the form of a reactive ester antioxidant having direct bioreactivity, or hair (17.5 to 21.9%) and skin keratin (15.5 to 23.5%). Reactive esterification of amino acids (ex, aspartic acid, glutamic acid) present in the reaction to form reactive ester forms (reactive antioxidants) using carbodiimide compounds that can be targeted by antioxidants containing amine groups By increasing the effect can be significantly increased. In addition, carbodiimides, imidoesters, arylazides, diazirines, hydroxymethyl phosphines, pentafluorophenylesters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, alkoxy, which may target other amino acids Antioxidant substances containing functional groups such as amines, hydrazides, haloacetyls, and azides in the molecule may be used to further enhance the effect.

In a more preferred embodiment, the polymer form carbodiimide-based compound of formula (2) or 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, first on the surface of the protein of the antioxidant molecule or skin or hair having a carboxyl group. Carbodiimide-based compounds such as hydrochloric acid (1-ethyl-3- (3-dimethylaminopropyl) carbodiimide.HCl) are first reacted to form a reactive ester, and the reactive ester functional groups react with an antioxidant having an amine in the molecule. Or by reacting with amines on the hair or skin surface, an excellent antioxidant effect can be obtained. In the reaction, the reaction may be preferably performed at a pH of 2 to 10, more preferably at a pH of 3 to 9, and most preferably at a pH of 4 to 5 in an acidic to weakly acidic aqueous solution. The most reaction efficiency can be increased. The reaction is completed within 1 to 30 minutes.

In Reaction Scheme 1, an antioxidant (an antioxidant functional component) molecule having a carboxyl group is first reacted with a carbodiimide-based compound to form a reactive ester, followed by reaction with an amino acid of a living body having an amine residue to form a covalent bond. Indicated.

[Reaction Scheme 1]

Figure 112013112470474-pat00003

In the following Scheme 2, aspartic acid and glutamic acid, which are biological amino acids having a carboxyl group on the surface of the protein, are first reacted with a carbodiimide-based compound to form a reactive ester, followed by reaction with an antioxidant (an antioxidant functional component) having an amine residue to form a covalent bond. The reaction schematic to form is shown.

[Reaction Scheme 2]

Figure 112013112470474-pat00004

Carbodiimide-based compounds increase the reaction efficiency of hair proteins with antioxidants, and the reactive antioxidants bound to the hair do not come off during normal washing due to shampoos, detergents, soaps, etc. and are almost permanently attached to the hair. State can be maintained.

The reaction scheme is a representative example of hair, and can be applied to skin and the like in addition to hair.

The present invention also provides carbodiimide groups, imidoesters, arylazides, diazirines, hydroxymethyl phosphines, pentafluorophenylesters, pyridyl disulfides, sulfo-hydroxysuccinimide esters, and alkoxy amines in antioxidants. , Hydrazide, haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl At least one protein selected from the group consisting of esters, imidazoles, oxycarbonyl amidazoles, imines, thiols, maleimides, vinylsulfones, ethyleneimines, thioethers, acrylonitrile, acrylic acid or methacrylic acid esters, disulfides and ketones It may include a reactive antioxidant material bonded to a functional group covalently bonded with.

For example, as shown in Scheme 1, the carbodiimide-based compound may include an antioxidant (reactive antioxidant) to which a carbodiimide group is bonded. In addition, the present invention may include an antioxidant cosmetic composition comprising the reactive antioxidant material.

In the antioxidant cosmetic composition according to the present invention, in order to incidentally increase the effect, a cationized interface such as fatty acids such as palmitic acid and stearic acid, fatty alcohols, long-chain alkyl quaternary ammonium salts such as linear and branched chains, etc. Formulation may be facilitated by mixing with an active agent, cationic cellulose, cationic guar, cationic polymer such as cationic polyvinylpyrrolidone, silicone, and the like. In addition, to formulate into cosmetic formulations for the formulation of cosmetics such as solvents, surfactants, thickeners, stabilizers, preservatives, colorants, pH adjusters, metal ion sequestrants, colorants, pearlescent agents, cosmetics, pigments, powder particles, etc. Components may be incidentally included. The component for the formulation may be used 40 to 99 parts by weight based on 100 parts by weight of the total composition.

Antioxidant cosmetic composition according to the present invention can be used in the formulation of an antioxidant cosmetic composition containing the component of the antioxidant function having a functional group.

Examples of application of skin products generally include skin care, basic cosmetics (cosmetics, serums, essences, lotions, creams), color cosmetics (makeup base, foundation, powder, eye shadow, lip gloss, lipstick, lip balm, etc.) , Makeup for nails (nail polish, nutrients, reinforcing agents, top coats, etc.), cleaning cosmetics (foam cleansing, cleansing oil, cleansing lotion, cleansing cream, cleansing gel, pack, mask, soap, cleansing tissue, etc.), sun care It can include both cosmetics and body cosmetics (body lotions, shower gels, body creams, body oils, etc.), and even hair, such as shampoos, rinses, treatments, hair packs, hair essences, waxes, gels, sprays, etc. All formulations may be included.

More preferably, the antioxidant cosmetic composition according to the invention comprises an antioxidant substance containing a carbodiimide compound and at the same time a reactive functional group, and when the above agent is degraded in water, its activity in a non-aqueous formulation is reduced. It is easier to maintain and can be reacted by mixing with a buffer to adjust pH just before use, or by contacting with water during cleaning. Examples of non-aqueous formulations include liquid form, sheet form, powder powder form, tablet form, oil, wax, ampoule, gel and the like used as conventional non-aqueous cosmetic preparations. In addition, the carbodiimide-based compound and the antioxidant may be formulated as a single agent in encapsulated form or as two agents in separate forms, respectively. In addition, a method of blocking derivatives in a form in which a reactive functional group and an antioxidant functional component are combined through encapsulation may also be used.

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

Hereinafter, the present invention will be described in detail with reference to Examples and Experimental Examples. However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the present invention is not limited to the following Examples and Experimental Examples.

Example  1 to 6 and Comparative Example  1-3

The antioxidant compositions of Examples 1 to 6 and Comparative Examples 1 to 3 were prepared using the compositions and contents shown in Table 1 below, and 2 g of each of the prepared compositions was applied to the back of the hand twice daily in the morning and evening. Sensory performance of 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 no effect, 1 very no effect) by combining roughness and appearance condition of the hand and the like after 1 day, 5 days, and 10 days after the treatment. The skin anti-aging effect was compared.

Category (% by weight) Comparative Example 1 Comparative Example 2 Comparative Example
3
Example 1 Example 2 Example 3 Example 4 Example 5 Example 6
Distilled water 49.0 49.0 49.0 48.0 48.0 48.0 48.0 48.0 48.0 Acetylcysteine 1.0 - - 1.0 - - 1.0 - - Caffeic acid - 1.0 - - 1.0 - - 1.0 - Aminoethanesulfonic acid - - 1.0 - - 1.0 - - 1.0 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide. Hydrochloric acid - - - 1.0 1.0 1.0 - - - Benzene, 1,3, -bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block - - - - - - 1.0 1.0 1.0 Buffer (pH 4.5) 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 Sum 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0

Experimental results of Examples 1 to 6 and Comparative Examples 1 to 3 (Table 2), Examples 1 to 6 containing carbodiimide compared to carbodiimide compared to Comparative Examples 1 to 3 not containing carbodiimide The bond formation effect showed a better skin aging effect.

Skin aging improvement effect (5-point scale, n = 10 people each) Comparative Example 1 Comparative Example 2 Comparative Example 3 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 1 day after processing 3.8 3.9 4.0 4.0 3.8 4.1 3.8 4.0 3.9 5 days after treatment 3.5 3.4 3.4 3.9 3.8 4.0 3.9 3.9 4.0 10 days after treatment 3.3 3.2 3.1 3.9 3.7 4.1 4.1 4.2 4.1

Formulation example : Antioxidant (for improving skin aging) Cosmetics  Produce

According to the conventional cosmetic preparation method, to prepare an antioxidant cosmetic with the ingredients and contents of Table 3 below.

Component (% by weight) toilet water Lotion cream  pack Acetylcysteine 0.5 0.5 0.5 0.5 Caffeic acid 0.5 0.5 0.5 0.5 Aminoethanesulfonic acid 0.5 0.5 0.5 0.5 Benzene, 1,3, -bis (1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-meth-ether-block 1.0 1.0 1.0 1.0 glycerin 3.0 3.0 3.0 3.0 Butylene glycol 3.0 3.0 3.0 - Propylene glycol 3.0 3.0 - - Carboxyvinyl polymer 0.1 0.1 0.1 - Polyvinyl alcohol - - - 15.0 Phage-12 nonylphenyl ether 0.3 - - 0.5 Polysorbate 80 0.5 - - - Polysorbate 60 - 1.5 1.5 1.5 Sorbitacecequioleate - 1.5 - - Sorbitan stearate - - 0.5 - Liquid paraffin - 0.5 10.0 - Caprylic / capric triglyceride - 5.0 5.0 - Squalane - 5.0 5.0 - Cetearylglucoside - - 2.0 - ethanol 10.0 - - - Triethanolamine 0.1 0.1 0.1 - Cetearyl alcohol - 1.0 - - Wax - 5.0 - - antiseptic Suitable amount Suitable amount Suitable amount Suitable amount Spices Suitable amount Suitable amount Suitable amount Suitable amount Buffer (pH 4.5) Balance Balance Balance Balance Sum 100 100 100 100

Claims (9)

A carbodiimide compound represented by the following formula (2); And an antioxidant cosmetic composition comprising an antioxidant having a functional group capable of covalently bonded to protein residues on the hair or skin surface:
(2)
Figure 112019057789943-pat00006

In the above formula (2), n is 1 to 100 and m is 1 to 100.
The method of claim 1,
The antioxidant substance is an antioxidant cosmetic composition comprising a carboxyl group or an amine group in the molecule.
The method of claim 1,
The antioxidant is acetamidocaproic acid (acetamidocaproic acid), acetyl benzoyloxy prasterone (acetyl benzoyloxy prasterone), acetyl cysteine, 2-acetylhydroquinone (2-acetylhydroquinone), adamantanylcarbosamido hydride Adamantanylcarboxamido hydroxylbenzamide, aminoethanesulfinic acid, aminopropyl ascorbyl phosphate, angoroside C, anserine, apigenin, arbutin arbutin, alpha-albutin, ascorbic acid, asiaticoside, benzoquanamine, BHA (butylhydroxyanisol), butylated hydroxy toluene (BHT), bis-hydro Bis-hydroxyethyl tocopherylsuccinoylamido hydroxypropane, bis-tetramethyl hydroxypyridinyl seba Bis- (tetramethyl hydroxypiperidinyl) sebacate, butylated xylenol, t-butylbenzamido hydroxylbenzamide, 4-butylresorcinol , Caffeic acid, calcium ascorbate, carnosic acid, carotenoids, chitosan ascorbate, chlorogenic acid, cobalt diene DNA), copper adenosine triphosphate (ATP), copper pyridoxal 5-phosphate, curcumin, cysteine, cysteine HCl, decapeptide-6 6), decapeptide-7, decursinol, decyl mercaptomethylimidazole, diamylhydroquinone, di-t-butylhydroquinone (di- t-butylhydroquinone) Thiodipropionate, dicyclopentadiene / t-butylcresol copolymer, digaloyl trioleate, diisooctyl sebacate ), Dilauryl thiodipropionate, dimethoxybenzamido phenylhydroxylacetamide, dimethoxy di-p-cresol, dimethylmethoxy chromman Dimethylmethoxy chromanol, dimyristyl thiodipropionate, dioleyl tocopheryl methylsilanol, diosmine, diretinyl ether, dishotin ascor Disodium ascorbyl sulfate, distearyl thiodipropionate, ditridecyl thiodipropiona te), dodecyl gallate, dunaliella bardawil powder, ellagic acid, epigallocatechin gallate, ergothioneine, loquat Eriobotrya japonica leaf protoplasts, erythorbic acid, ethylbisiminomethylguaiacol manganese chloride, ethyl ferulate, ethylhexyl ferulate , Ferulic acid, feruloyl soy glycerides, furyl palmitate, genistein glucoside, ginkgo leaf terpenoids, glucosyl Glucosylrutin, glyceryl chromonyl ether, glyceryl diferulate, hesperetin, hexyloxy tree Hexyloxy trimethylphenol, honokiol, hydrolyzed proanthocyanidin, hydroquinone, p-hydroxyanisole, hydroxydecyl ubiquinone (hydroxydecyl ubiquinone), hydroxyamine hydrochloride (hydroxylamine HCl), hydroxylamine sulfate, hydroxyphenyl dihydroxybenzamide, inosinol hexanacinate hexaascinate hexaascorbate, isooctyl caprylate / caprate, isooctyl thioglycolate, isoquercitrin, kaempferol, kojic acid, kojyl glucoside glucoside, kojyl methylenedioxycinnamate, black tea extract (kou-cha ekisu), lycopene (ly copene, madecassoside, magnesium ascorbate, magnolol, manganese adenosine triphosphate, matrine, melatonin, methoxy PEG-7 ascorbate Methoxy PEG-7 ascorbic acid, methoxytrimethylphenyl dihydroxyphenyl propanol, methyl di-t-butyl hydroxyhydrocinnamate, methylene di- m-ethylene di-t-butylcresol, methyl methacrylate / trimethoxysilylpropyl methacrylate crosspolymer, methyl myristic acid, Niacinamide hydroxybenzoate, nictoflorin, nordihydroguaiaretic acid, octanicotinoyl Octanicotinoyl epigallocatechin gallate, octapeptide-4, oligopeptide-28, paeonol, palmatine, PEG / PPG-2 / 5 toco Peryl ether (PEG / PPG-2 / 5 tocopheryl ether), perillyl alcohol, phenethyl caffeate, phenylethyl resorcinol, phenylthioglycolic acid, Phloretin, phloroglucinol, piceatannol, piperlonguminine, porphyridium polysaccharide, potassium ascorbyl tocopheryl phosphate ), Potassium sulfite, PPG-2 tocophereth-5, propyl gallate, protocatechuicaldehyde, puerarin, Pyridoxin hydrobenzoate (pyri doxine hydroxybenzoate, pyridyloxide t-butylnitrone, quercetin, resacetophenone, resorcinol, resveratrol, retinyl formyl as Paratin (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-pyridoxylidenerhodanine, sodium thioglyco Sodium thioglycolate, sodium zinc histidine dithiooctanamide, sorbityl furfural, stearyl gallate, succinoyl ascorbe Succinoyl ascorbate pentapeptide-6, tangeritin, tert-butylhydroquinone (TBHQ), tetrabutyl ethylidinebisphenol, tetrahydrodemethoxydiferuloylmethane, Tetrahydrocurcumin diacetate, tetrahydrodiferuloylmethane, tetramethylbutyl dihydroxybenzamide, tetramethylchromanol glucoside, thioxtic acid ), Thiodiglycol, thiolactic acid, thiosalicylic acid, thioaurine, thymol trimethoxycinnamate, tococysteamide, Tocophereth-5, tocopherol, tocophersolan, tocopher Tocopheryl acetate, tocoquinone, toluene, o-tolyl biguanide, totarol, triprophylene glycol, tris-BHT mesitylene tris-BHT mesitylene, tris (nonylphenyl) phosphate, trisodium ascorbyl isopalmitate phosphate, tyrosyl histidine HCl, ubiquinol (ubiquinol), ubiquinone, ulva lactuca powder, ooron-cha ekisu, xylyl dibutylbenzofuranone, zinc aTP (zinc adenosine triphosphate), zinc Zen in the group consisting of dibutyldithiocarbamate, zinc fructose diphosphate, zinc pyridoxal 5-phosphate and derivatives thereof At least one antioxidant cosmetic composition selected.
delete The method of claim 1,
The functional group covalently bonded with the protein is imidoester, arylazide, diazirine, hydroxymethyl phosphine, pentafluorophenylester, pyridyl disulfide, sulfo-hydroxysuccinimide ester, alkoxy amine, hydrazide, Haloacetyl, azide, carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, succinimide, hydroxysuccinimidyl ester, imidazole, At least one antioxidant cosmetic composition selected from the group consisting of oxycarbonyl amidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic acid or methacrylic acid ester, disulfide and ketone.
The method of claim 1,
Antioxidant cosmetic composition comprising 0.001 to 10% by weight of the carbodiimide compound in 100% by weight of the total composition.
The method of claim 1,
Carbodiimide-based compounds and antioxidants are formulated in a single agent in encapsulated form; An anti-oxidant cosmetic composition formulated with a two agent in which a carbodiimide compound and an antioxidant substance are separated from each other.
delete delete
KR1020130152313A 2013-12-09 2013-12-09 Cosmetics Compositions for antioxidant KR102006947B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020130152313A KR102006947B1 (en) 2013-12-09 2013-12-09 Cosmetics Compositions for antioxidant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020130152313A KR102006947B1 (en) 2013-12-09 2013-12-09 Cosmetics Compositions for antioxidant

Publications (2)

Publication Number Publication Date
KR20150066805A KR20150066805A (en) 2015-06-17
KR102006947B1 true KR102006947B1 (en) 2019-08-02

Family

ID=53515033

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020130152313A KR102006947B1 (en) 2013-12-09 2013-12-09 Cosmetics Compositions for antioxidant

Country Status (1)

Country Link
KR (1) KR102006947B1 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6842419B2 (en) * 2015-09-02 2021-03-17 株式会社林原 Topical skin for reducing yellowing
KR101701881B1 (en) * 2015-11-11 2017-02-02 주식회사 엘지생활건강 Functional composition for surface modification
KR102502512B1 (en) * 2015-12-23 2023-02-22 주식회사 엘지생활건강 Cosmetics compositions for antioxidant
KR102494611B1 (en) * 2015-12-29 2023-01-31 주식회사 엘지생활건강 Composition for improving skin conditions comprising Ethyl ferulate
CN106109270B (en) * 2016-06-20 2019-05-21 陕西畅想制药有限公司 A kind of anti-aging cosmetics composition and preparation method thereof
CN108299613B (en) * 2017-12-29 2019-07-26 合肥科天水性科技有限责任公司 A kind of antimicrobial form anion aqueous polyurethane resin and preparation method thereof
CN108852996A (en) * 2018-09-20 2018-11-23 北京原肽干细胞医学研究院有限公司 A kind of skin Essence and preparation method thereof for skin repair
KR102302400B1 (en) 2019-06-27 2021-09-14 주식회사 코스메카코리아 Cosmetic compositions having Antioxidant effect comprising Phloretin, Fragaria Vesca (Strawberry) Leaf Extract and Leontopodium Alpinum Callus Culture Extract
US20230277425A1 (en) * 2020-07-08 2023-09-07 Lg Household & Health Care Ltd. Hydroquinone stabilizing composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002013773A2 (en) * 2000-08-16 2002-02-21 Unilever Plc Cosmetic composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101351467B1 (en) 2007-01-05 2014-01-16 주식회사 엘지생활건강 Mixed-type Personal Care Product for Skin or Hair

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002013773A2 (en) * 2000-08-16 2002-02-21 Unilever Plc Cosmetic composition

Also Published As

Publication number Publication date
KR20150066805A (en) 2015-06-17

Similar Documents

Publication Publication Date Title
KR102006947B1 (en) Cosmetics Compositions for antioxidant
KR101663053B1 (en) Composition for hair surface modification
KR101663055B1 (en) Composition for skin surface modification
KR101453217B1 (en) Cosmetics compositions for humectant
KR20150143698A (en) Antioxidant compositions and methods of using same
KR102502512B1 (en) Cosmetics compositions for antioxidant
KR102006952B1 (en) Cosmetics compositions for prevention and improvement of wrinkle
KR20180017459A (en) Cosmetics compositions for antioxidant
KR20150066807A (en) Cosmetics compositions for skin whitening t
JP2019108303A (en) Skin external composition, composition for suppressing functional deterioration of ultraviolet absorber, and method of suppressing functional deterioration of ultraviolet absorber
JP2014084298A (en) Skin external composition for body odor suppression
KR20170114539A (en) Cosmetics compositions for antioxidant
KR20150004963A (en) Cosmetic Composition for the Skin Whitening Comprising the Lapachol
KR102006954B1 (en) Functional compositions comprising microcapsule inclusion compound
CN105726351B (en) Synergistic compositions, formulations and related methods for reducing ultraviolet-induced lipid peroxidation
JPH11222412A (en) Skin preparation for external use
KR101462692B1 (en) Skin whitening cosmetics
KR102010440B1 (en) Functional compositions comprising microcapsule
ES2700426T3 (en) Compounds derived from 3- (alkylthio) propenoic acid, and its application in cosmetics
KR20130089559A (en) Anti-aging composition
KR102160306B1 (en) skin whitening agent
KR101786606B1 (en) cosmetics containing tetrandrine
KR102084521B1 (en) Compositions for prevention and improvement of acne
KR20230095381A (en) Cosmetic composition comprising Actinidia fruit extract, actinidia flower extract and actinidia stem extract, and method for manufacturing the same
KR101434446B1 (en) Composition for External Application to the Skin Using an Extract of Dictyota dichotoma

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant