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WO2006054792A1 - Agent améliorant l’élasticité et la résistance des cheveux, et préparation cosmétique pour cheveux - Google Patents

Agent améliorant l’élasticité et la résistance des cheveux, et préparation cosmétique pour cheveux Download PDF

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Publication number
WO2006054792A1
WO2006054792A1 PCT/JP2005/021629 JP2005021629W WO2006054792A1 WO 2006054792 A1 WO2006054792 A1 WO 2006054792A1 JP 2005021629 W JP2005021629 W JP 2005021629W WO 2006054792 A1 WO2006054792 A1 WO 2006054792A1
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WO
WIPO (PCT)
Prior art keywords
hair
acid
gene
acetyl
ether
Prior art date
Application number
PCT/JP2005/021629
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English (en)
Japanese (ja)
Inventor
Tsutomu Soma
Masato Iino
Masahiro Tajima
Hirotada Fukunishi
Original Assignee
Shiseido Company, Ltd.
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
Priority claimed from JP2004335918A external-priority patent/JP2006143649A/ja
Priority claimed from JP2004352459A external-priority patent/JP2006160641A/ja
Application filed by Shiseido Company, Ltd. filed Critical Shiseido Company, Ltd.
Publication of WO2006054792A1 publication Critical patent/WO2006054792A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55—Phosphorus compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Definitions

  • the present invention relates to a drug for improving hair tension and hair and a cosmetic for hair containing the drug. More specifically, the present invention relates to a hair-related gene by activating cells of hair and capsule. The present invention relates to a drug that improves hair tension and stiffness by increasing the expression of hair, and a cosmetic for hair containing the drug. Background art
  • Concerns about hair include those related to the health of the roots and hair follicles, such as thin hair and hair loss, and those related to the physical properties of the hair such as hard, soft, non-sticky, split, comb hair, and passac.
  • damage caused by external factors such as perm and bleach treatment, exposure to ultraviolet light, exposure to air pollutants, combing friction, etc. It can be considered that the damage is caused by internal damage and the internal factors in the hair shaft formation.In the latter case, not only the hair quality is improved, but also the hair root and the hair follicle itself. Care is required to improve the health condition, so even if the hair quality of a mouthful is not good, there are various ways to care for it.
  • the hair itself is made up of a cuticle that covers the surface of the hair, fur that occupies the majority of the hair, and the medulla of the center. It has been shown that cutil contributes greatly to the firmness of hair (K. Sogabe et al., J. Soc. C C he m. J apan, V ol. 3 6, No. 3 (2 0 0 2) pp. 2 0 7-2 1 6 "Study on physical properties of hair 1 — Measurement of short diameter and long diameter of hair 3 ⁇ 4 Bending stress evaluation method ").
  • Cuticles are acidic hair keratins Hal, Ha2, basic keratins Hbl, Hb2, and other fiber proteins and modifying enzymes such as transglutaminase, peptidylarginine diminase, and even the granule component trichohyalin It consists of various components such as S100. However, the relationship between each of these components and hair quality, such as hair tension and hair, has not been fully elucidated. If the mechanism that influences the hair quality is fully elucidated at the biochemical and molecular biology levels, it will be possible to provide products that have a more remarkable effect than existing hair improvers.
  • Examples of conventional hair cosmetics that are supposed to impart hair and sash to hair include, for example, a silyl group having a reactive functional group bonded thereto as described in JP-A No. 1 1-3 0 2 1 2 9.
  • S i 10—S i siloxane bond
  • a cell activator containing taurine as an active ingredient is disclosed in Japanese Patent Application Laid-Open No. 2 0 2-9 7 1 1 6, and a cell activator containing N-methyl taurine as an active ingredient and a hair scalp / stiffener are internationally available.
  • Each is described in the published WO 2 0 0 2/0 3 4 2 5 3 publication.
  • the effects of these drugs include hair cell control and hair growth through activation of cell proliferation. Hair extension and hair improvement are described, but the effect of hair extension and hair improvement is still evaluated by the physical property test (torsion torque) of hair. . Therefore, there is a need for a new hair squeeze and hair improver that can be used to evaluate activity at the biochemical and molecular biology levels. Disclosure of the invention
  • the present inventor has investigated the correlation between hair tension (hardness as a scale, more specifically, Young's modulus) and expression of hair-related genes, and found that hair keratin genes, particularly hair keratin H a 2 genes, hair keratin H b 2 gene and / or keratin-related protein KA P 5.1 1-5, more preferably the expression of keratin H a 2 gene, KA P 5.1 gene, We found that the higher the expression of the KA P5.2 gene or KAP5.4 gene, the higher the Young's modulus of the hair, that is, that the hair felted and felt stiff, and the ⁇ hair keratin gene was used as an index.
  • a Japanese patent application has been filed for “a method for evaluating hair quality” (Japanese Patent Application No. 2000- 1 6 4 5 9 6).
  • the present inventor has recently constructed a new assembly system for evaluating the effects of various drugs on the expression of hair-related genes. Using this assembly system, various compounds affect the expression of hair-related genes. As a result of intensive studies on the effect, it was found that certain drug compounds have the effect of increasing the expression of hair-related genes, and the present invention has been completed.
  • the present invention relates to 0-phosphoserine, phosphodaricelic acid, selenium ester, benzyloxycarbonylserine, O-benzene.
  • Lucerin Glycylselin, Acetyldaricin, Glycylglycine, Hipotaurine, Thiotaurine, Methionine methyl ester, Bibutamin U, 2 —Amino 6 — (Methylsulfonyl) benzothiazole, N— (2 —Case 1) 2-aminoaminosulfonic acid, dimethyl 41- (acetylamino) cyclohexane 1,3-dicarboxylate, taurocyanine, thiazolidine 1-2 mono-rubonic acid, 3- (2-benzo) Thiazolylthio) ⁇ 1 monopropans, sodium sulfonate, L-homocerine, N-benzyl-L-serine, H- Ser — V a 1-
  • the present invention also includes: o phosphoserine, phosphodariceric acid, cerethyl ester, benzyloxycarbonyl serine, o-benzyl serine, glycyl serine, acetyl daricin, glycyl glycine, hypotaurine, titaurine, metholine Nin methyl ester, bi-amino M, 2 —amino 6- (methylsulfonyl) benzothiazol, N-(2 —acetamido) 1 2-amino ether sulfonic acid, dimethyl 4 _ (acetylamino) Cyclohexane 1,3 —dicarboxylate, taurocyanine, thiazolidine one 2 —powered rubonic acid, 3 — (2-benzothiazolylthio) 1 1 sodium propanesulfonate, L—homoserine, N—be Njiru L—Serine, H—Ser — V
  • the present invention also provides: o Phosphoserine, phosphoglycerin acid, selenium ester, benzyloxycarbonyl seleline, O-benzylserine, glycylserine, acetylidaricin, glycylglycine, hypotaurine, thiotaurine, methionine Methyl ester, biminine U, 2 —amino-6 — (methylsulfonyl) benzothiazol, N— (2 —acetamido) 1-2 —aminobenzene sulfonic acid, dimethyl 4 mono (acetylylamino) cycloto Xanthone 1,3 —dicarboxylate, taurocyanine, thiazolidine one 2 —strong rubonic acid, 3 — (2 —benzothiazolylthio) 1-1 sodium propanesulfonate, L monohomoserine, N— Benjirou L-Serine
  • the present invention also includes: o phosphoserin, phosphodariceric acid, selenium ester, benzyloxycarbonyl selenium, O-benzylserine, glycylserine, acetylidaricin, glycylglycine, hypotaurine, titaurine, methacryline ONIN METHYL ESTER U, 2 —amino 6 — (methylsulfonyl) benzothiazol, N-(2 —acetamido) 1 2 —amino sulfonic acid, dimethyl 41 (acetylamino) cyclohexane 1 , 3-dicarboxylate, taurocyanine, thiazoline 1 2 —carboxylic acid, 3 — (2 monobenzothiazolylthio) -1 sodium propanesulfonate, L 1 homoselin, N—benzyl 1 L 1 , H—Ser — V a 1 — ⁇
  • the hair patch / scrubbing improver and the cosmetic for hair containing the pharmaceutical compound of the present invention are used in the hair or scalp, so that they penetrate into the hair or are absorbed into the hair follicle, and keratin-related protein KAP in the cell. Increases the expression of 5 and improves hair tension.
  • Figure 1 shows a comparison of the amino acid sequences of putative code proteins of human KAP 5.1-5.1 genes.
  • FIG. 2 shows the expression regulation of the K A P5 gene group.
  • FIG. 3 shows the relationship between the expression level of the hair keratin H a 1 gene and the Young's modulus of the hair.
  • FIG. 4 shows the relationship between the expression level of the hair keratin Ha 2 gene and the Young's modulus of the hair.
  • FIG. 5 shows the relationship between the expression level of the hair keratin Hb2 gene and the Young's modulus of the hair.
  • Figure 6 shows the relationship between the expression level of KAP5.2 gene and the Young's modulus of hair. .
  • FIG. 7 shows the relationship between the expression level of KAP 5.1 and KAP 5.4 genes and the Young's modulus of hair.
  • Figure 8 shows the construction and configuration of KA P5.1 Repo overnight plasmid.
  • Figure 8 — A shows PCR amplification of DNA fragment containing KA P 5.1 gene and KA P 5.2 gene
  • Figure 8 — B shows report of amplified DNA fragment, plasmid vector p GL— 3 Indicates closing to basic.
  • Fig. 9 is a construction diagram of the KA P5.1 repo overnight plasmid following Fig. 8, showing deletion of the KAP 5.1 gene translation region (after the start codon) by subcloning. Best Mode for Carrying Out the Invention
  • the present invention relates to a drug and a cosmetic for hair that improve hair lashes and hair by activating cells of hair and hair follicles, and more specifically, by increasing expression of hair-related genes. Based on the activity evaluation at the biochemical and molecular biology level, more specifically, a novel hair squeeze / scrubbing improver and hair cosmetics based on the expression control effect of the keratin-related protein KAP 5 gene It is to be provided.
  • the hair keratin Ha 2 gene (NCBI GenBANK Source “X90761”) codes for an acidic protein that is a member of the keratin gene family. Hair keratin H a 2 is type I keratin, and heterodimerizes with type II keratin to form hair, nails and the like. Type I keratin is located in chromosome 17Q12-Q21.
  • the hair keratin H b 2 gene (NCBI GenBANK Source “Y19207”) encodes a basic protein that is a member of the keratin gene family. Hair keratin H b 2 is type II keratin, which is heterodimerized with type I keratin to form hair and nails. Type II keratin is located in chromosome 12cil3 region.
  • AC CESSION: AP000867) is a human EST whose base sequence is already known, and no function has been reported. The relationship between increased KAP 5.1-5 gene expression and hair firmness was unclear.
  • the putative protein encoded by the KA.P5.2 gene is a cystine-rich (about 35.5%) and is a low molecular amino acid, glycine.
  • the KAP ⁇ .1 to 5.5 genes are a group of genes having a relatively high homology to each other belonging to the family KAP5 family of keratin-related proteins.
  • the high degree of homology between the amino acid sequences of the putative proteins encoded by each gene is shown in Fig. 1 and Table 2 below. it is obvious.
  • the present inventor has found that keratin H a 2, H b 2 gene, hyal keratin related protein KAP 5.1, KAP 5.2, A Among the ⁇ .4 genes, a reporter assembly system was newly constructed to evaluate the effect of various drugs on the expression of hair-related genes, especially for the ⁇ ⁇ ⁇ .1 gene. Using this Atsy system, we examined the effects of various compounds on the expression of ⁇ ⁇ ⁇ 5.1 genes. As a result, it was found that certain pharmaceutical compounds have the effect of increasing the expression of the KA 51 gene.
  • the K A P 5.1 to 5.5 genes are a group of genes having a relatively high homology with each other belonging to the human keratin-related protein K A P 5 family.
  • the promoter region sequence of the KAP 5.1 gene and the promoter region sequences of other KAP ⁇ . 2-5.5 genes are very close to each other. It is likely that they are equivalent. Therefore, it is highly likely that a drug that enhances the expression of the K A ⁇ 5.1 gene also enhances the expression of other K A P5 genes.
  • the higher the expression level of the KAP 5.1 gene the statistically significant increase in the Young's modulus of the hair. 1. Drugs that increase gene expression increase hair hardness and improve hair tension.
  • the hair cosmetics and hair cosmetics that are expected to have an effect of improving the hair are agents that have been found to have an effect of enhancing the expression of hair-related genes in the examples described later.
  • agents that have been found to have an effect of enhancing the expression of hair-related genes in the examples described later.
  • Serine, Glycine Cystine and its derivatives, precursors are:
  • other sulfur-containing amino acids are included in the hair cosmetics and hair cosmetics that are expected to have an effect of improving the hair.
  • Serine, glycine, cystine and its derivatives, and precursors belong to the following: Phospho L-serine), Phosphoglycerin acid, Phosphohydroxypyruvate, Selenium ester, Benzyloxycarboxylated serine derivatives (Z-serine derivatives), Benzylinserine (H-Ser -OB z 1), glycycylline, acetylidaricin (N-acetylidylicin), glycylglycine, pharmaceutically acceptable salts thereof, such as barium phosphoglycerate, acetylsylline (N-acetyl) DL selenium, O-acetyl L-serine), selenium methyl ester, cystine, acetyl cysteine, homocysteic acid, pharmaceutically acceptable
  • benzyloxycarbonylated selenium derivatives examples include benzyloxycarbonylselin (Z—Ser— ⁇ H), benzyloxycarbonyl mono-N-methylserine (Z—).
  • preferable drugs to be included in hair cosmetics are:
  • Glycylacerine acetylidaricin, glycyl U-sin, pharmaceutically acceptable salts thereof such as benzylserine inn salt (H-
  • Ser-OB zl ⁇ HC 1 phosphoglycerin ha, Um, serine, acetyl selenium, serine methyl ester, dalysin, cystine, cystine, acetyl cystine, homocystic acid, methionine, dartathione, folic acid Vitamin B 6, vitamin B 12, adenosine, dibutyl cAMP and the like.
  • those belonging to other sulfur-containing anoic acids include methionine, hypotaurine, thiothurine, methionine methyl ester, and vitamin U (methylmethionine sulfonium salt, for example, Methyl methionine sulfone chloride, bromide, iodide), and pharmaceutically acceptable salts thereof, such as methionine methyl ester hydrochloride.
  • preferable drugs to be included in hair cosmetics are methionine, hypotaurine, thiotaurine, methionine methyl ester, vitamin U chloride (methylmethionine sulfochloride).
  • those belonging to the biminines include folic acid, vitamin ⁇ 6 (pyridoxine, Doxal, pyridoxamin), vitamin B 12 (also called balamin, including cyanocobalamin, methylcobalamin, adenosylcobalamin, etc.), pharmaceutically acceptable salts thereof such as sodium folate Rium salt, pyridoxine hydrochloride, etc. are included.
  • adenylate cyclase activation substance include adenosine, dibutyl c A ⁇ ⁇ , dimethyl 4- (acetylamino) cyclohexane 1,3-dicarboxylate, and these pharmaceuticals
  • Pharmaceutically acceptable salts such as dibutyl cAMP sodium phosphate.
  • preferable drugs to be included in hair cosmetics are dibutyl C. AMP, dimethyl 4- (acetylamino) cyclohexane-1,3-dicarboxylate, and its pharmaceutically acceptable drugs. Salt.
  • “Pharmaceutically acceptable salt” refers to a salt that retains substantially the same biological activity as a drug compound and is not toxic.
  • examples of such salts include, but are not limited to, (1) a hydrogen ion of an acid group such as a strong lpoxyl group, a phosphoric acid group, etc. contained in a drug compound, sodium, strong rhodium, calcium Salts substituted with cations such as metal ions such as magnesium ions and aluminum ions, (2) inorganic acids
  • Examples of pharmaceutically acceptable salts include barium phosphodariselic acid, selethyl ester hydrochloride, methysine ester ester hydrochloride, ⁇ -benzylserine hydrochloride (H-Ser — ⁇ B z 1 ⁇ HC 1), benzoxycarbonoline benzene selenium hydrochloride (Z—Ser OB zl 'HC l), etc. ,
  • the drug compound of the present invention may be an optical isomer when an optical isomer exists.
  • the drug compound of the present invention can include any of L-form, D-form, a mixture thereof and a racemic mixture.
  • enantiomeric isomers can exist when one or more chiral centers are present in a pharmaceutical compound
  • diastereoisomers can exist when two or more chiral centers exist.
  • the pharmaceutical compounds of the present invention can include any of the enantiomers, diastereoisomers, mixtures thereof and racemic mixtures.
  • the dosage form of the hair cosmetic composition containing the pharmaceutical compound of the present invention is not particularly limited, and may be any form commonly used for improving hair stiffness. Examples include liquid, emulsion, emulsified cream, cream, jewel, wax, mist, foam, aerosol and the like.
  • the cosmetic for hair of the present invention can be applied as products such as hair liquid, hair tonic, hair cream, moose, treatment, hair restorer, shampoo, rinse, cream, milky lotion, pack, and the like.
  • the compounding amount of the pharmaceutical compound of the present invention depends on the dosage form of the hair cosmetic, but is generally from 0.001 to 20% by mass, preferably from 0.01 to 5% by mass in the total amount of the hair cosmetic. %.
  • the hair cosmetic composition of the present invention contains, as necessary, general cosmetic ingredients of cosmetics, quasi-drugs, and pharmaceuticals as long as the effects of the present invention are not impaired.
  • General ingredients include, for example, powder components, liquid fats and oils, solid fats and oils, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, ester oils, silicone oils, anionic surfactants, cationic surfactants, amphoteric surfactants, Nonionic surfactant, moisturizer, water-soluble polymer, thickener, film agent, UV absorber, sequestering agent, lower alcohol, polyhydric alcohol, sugar, amino acid, organic amine, polymer emulsion PH preparation agent, skin nutrition, agent, vitamin, antioxidant, antioxidant aid, fragrance, water, etc.
  • blended is as follows. Hair cosmetics are produced by a conventional method according to the intended dosage form by blending one or more of the following ingredients as required.
  • Inorganic powders talc, kaolin, mica, sericite (sericite), muscovite, phlogopite, synthetic mica, saucite, biotite, permquilite, magnesium carbonate, calcium carbonate, aluminum silicate, silicate Calcium, calcium silicate, magnesium silicate, strontium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate (baked gypsum), phosphoric acid power, ruthenium, fluorine apatite, Droxyapatite, ceramic powder, metal sarcophagus (zinc myristate, calcium palmitate, aluminum stearate), boron nitride.
  • Organic powder Polyamide resin powder (Nylon powder), Polyethylene powder, Polymethylmethyl methacrylate powder, Polystyrene powder, Copolymer resin powder of styrene and acrylic acid, Benzoguanamine resin powder, Polytetrafluoroethylene Powder, cellulose powder.
  • Inorganic pigments Inorganic white pigments (titanium dioxide, zinc oxide), inorganic red pigments ⁇ iron oxide (bengala), iron titanate ⁇ , inorganic brown pigments ( ⁇ iron monoxide), inorganic yellow pigments (yellow iron oxide, Ocher), inorganic black pigment (Black iron oxide, low-order titanium oxide), inorganic purple pigment (mango violet, cobalt violet), inorganic green pigment (chromium oxide, chromium hydroxide, cobalt titanate), inorganic blue pigment (ultraviolet) Pearl pigments (titanium oxide coating strength, titanium oxide coating bismuth chloride chloride, titanium oxide coating talc, colored oxide coating strength, bismuth oxide chloride, fish scale foil).
  • inorganic white pigments titanium oxide coating bismuth chloride chloride, titanium oxide coating talc, colored oxide coating strength, bismuth oxide chloride, fish scale foil.
  • Metal powder pigment (Aluminum powder, Kappa powder).
  • Organic pigment Red 2 01, Red 2 02, Red 2 04, Red 2 05, Red 2 2 0, Red 2 2 6, Red 2 2 8, Red 4 0 5 , Orange 20 3, orange 2 0 4, yellow 2 0 5, yellow 4 0 1, and blue 4 0 4, red 3, red 1 0 4, red 1 0 6, red 2 7, Red 2 30, Red 4 0 1, Red 5 0 5, Orange 2 0 5, Yellow 4, Yellow 5, Yellow 2 0 2, Yellow 2 0 3, Green 3 No., Blue No. 1, Natural pigment (Chlorophyll, _Carotene).
  • Liquid oils and fats Apogade oil, camellia oil, Yuichi Toru oil, Macadamiana oil, corn oil, mink oil, olive oil, rapeseed oil, egg yolk oil, sesame oil, Pacific oil, wheat germ oil, Southern Power oil, Castor oil, Amani oil, Safflower oil, Cottonseed oil, Eno oil, Soybean oil, Peanut oil, Teaseed oil, Kaya oil, Rice bran oil, Sinagiri oil, Nippon Kiri oil, Jojoba oil, Germ oil , Triglycerin.
  • Solid fats cocoa butter, coconut oil, horse fat, hardened coconut oil, palm oil, beef tallow, sheep fat, hardened beef tallow, palm kernel oil, pork tallow, beef bone fat, mallow wax core oil, hardened oil, cattle Leg fat, mole, hardened castor oil.
  • Wax beeswax, candelilla wax, cotton wax, carnauba wax, beveri wax, warts evening wax, whale wax, montan wax, nukarou, lanolin, kapok wax, lanolin acetate, liquid lanolin, sugarcane wax, ranoli Fatty acid isopropyl, lauryl hexyl, reduced Norin, jojoba wax, rigid lanolin, shellac wax, polyoxyethylene (hereinafter referred to as “P0 E”) lanolin alcohol ether, P0 E lanolin alcohol acetate, P0 E cholesterol ether Lanolin fatty acid polyethylene lenglycol, POE hydrogenated lanolin alcohol ether.
  • P0 E polyoxyethylene
  • Hydrocarbon oil Fluid paraffin, ozokerite, squalene, pristane, noraffine, ceresin, squalene, ⁇ , selenium, microcrystalline wax.
  • Higher fatty acids lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylenic acid, tall oil fatty acid, isostearic acid, linoleic acid, linoleic acid, eicosapentaene Acid (EPA), docosahexaenoic acid (DHA).
  • Higher alcohols straight chain alcohols (lauryl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, myristyl alcohol, old rail alcohol, cetostearyl alcohol), branched chain alcohol (batyl alcohol, 2-decyltetradecinol) , Lanolin alcohol, cholesterol, phytosterol, hexyl dodecanol, isostearyl alcohol, octyldodecanol).
  • Ester oil isopropyl myristate, cetyl octanoate, octyldodecyl myristate, isopropyl palmitate, ptyl stearate, hexyl laurate, myristyl myristate, decyl oleate, hexyldecyl dimethyloctanoate, Cetyl lactate, myristyl lactate, lanolin acetate, isocetyl stearate, isocetyl isostearate, cholesteryl hydroxosterate, ethylene glycol di-2-ethylhexylate, dipentaerythritol Fatty acid ester, N-alkyl monoisostearate Glycol, neopentyldarlicol dicaprate, disostearyl phosphonate, G 2 -glycerin heptylundecanoate, tri 2 -trimethylolprop
  • Silicone oil Chain polysiloxane (dimethylpolysiloxane, methylphenylpolysiloxane, diphenylpolysiloxane), cyclic polysiloxane (octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexylsiloxane) ), 3D network silicone resin, silicone rubber, modified polysiloxane (amino modified polysiloxane, polyether modified polysiloxane, alkyl modified polysiloxane, fluorine modified polysiloxane).
  • Anionic surfactant Fatty acid soap (sodium laurate, sodium palmitate), higher alkyl sulfate (lauri) Sodium sulfate, potassium lauryl sulfate), alkyl ether sulfate ester (POE—triethanolamine lauryl sulfate, PE—sodium lauryl sulfate), N-acyl sarcosinic acid (lauracyl sarcosine) Trimethyl), higher fatty acid amidsulfonates (N-trimethyl-Toly-N—methyl tauronium sodium, palm oil fatty acid methyl tauronium donatium, lauryl methyl trivalent sodium), phosphorus Acid ester salt (POE—Nayl rail ether phosphate), POE—Oleyl ether phosphate, POE—Stearyl ether phosphate, Sulfoconate (di-2-ethylhexyl sulphosuccinate) Sodium, mono-lauroyl
  • Cationic surfactant Alkyltrimethylammonium salt (stearyltrimethylammonium chloride, lauryltrimethylan chloride) ), Alkylpyridinium salts (cetylpyridinium chloride), distearyldimethylammonium dimethylammonium chloride, poly (N, N'-dimethyl-3,5-methylenepiperidinium), quaternary alkyls Ammonium salt, alkyldimethyl benzylammonium salt, alkylisoquinoline salt, dialmolyphonium salt, P ⁇ E —alkylamine, alkylamine salt, polyamine fatty acid derivative, amyl alcohol fatty acid derivative, benzalkonium chloride, chloride Benzetonium.
  • Alkyltrimethylammonium salt stearyltrimethylammonium chloride, lauryltrimethylan chloride
  • Alkylpyridinium salts cetylpyridinium chloride
  • Amphoteric surfactants Imidazoline-based amphoteric surfactants (2 —undesyl, N, N, N — (hydroxyxetylcarboxymethyl) 1 2 —Imidazolin sodium, 2 —cocoyl 1 2 —imidazolinini Umhi de loxyside— 1 devoted lupoxychyloxy 2 sodium salt), betaine surfactant (2 — heptodecyl N — carboxymethyl N — hydroxicheil midazolinium Lauryl dimethylaminoacetic acid, alkyl betaine, amide, sulfone.
  • sorbitan fatty acid ester (sorbitan monooleate, sorbitan monoisostearate, sorbitan monomonolate, sorbitan monopalmitate, sorbitan monomonostearate, sorbitan monostearate, sorbitan monostearate, sorbitanate Liooleate, Penyu—2-Ethylhexyl diglyceride sorbitan, tetra-2-ethyl hexyl diglycerol sorbitan, glycerin polyglycerin fatty acid (mono cottonseed oil fatty acid glycerin, monoel glycerin monophenol) Glycerin sesquioleate, glycerin monostearate,, '— oleic acid pyroglutamate glycerin monostearate glycerin phosphonate), propylene glycol fatty acid ester (monostearin)
  • Hydrophilic nonionic surfactants P ⁇ E—Sorbi evening fatty acid ester (POE—Sorby evening mono-oleate, POE—Sorby evening mono-stearate, P ⁇ E—Sorbi evening mono-oleate, P ⁇ E—Sorbi evening mono-oleate) ), POE sorbite fatty acid ester (POE 1 sorbite monolaurate, P0E—Sorbit monolayer, P0E_Sorbiten pen oleate, P0E—sorbite mono stearate), POE—glycerin Fatty acid esters (P0E—glycerin monostearate ⁇ , POE—glycerin monoisostere— ⁇ , POE—glycerin tristearate, etc.), POE—fatty acid ester (P0E — Distearate, POE—monodiolate, ethylene glycol distearate), POE—alkyl ether P ⁇ E-lauryl
  • Moisturizer Polyethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, xylitol, sorbitol, maltitol, chondroitin sulfate, hyaluronic acid, mucoitin sulfate, caronic acid, atelocollagen , Cholesteryl 1 1 2 — Hydroxylate stearate, sodium lactate, bile salt, dl —pyrrolidone carboxylate, short chain soluble collagen, diglycerin (E ⁇ ) PO adduct, Isaiyobara extract , Sawtooth extract, melilot extract.
  • Natural water-soluble polymers Plant-based polymers ⁇ Gum Arabic, Tragacan Gum, Galactan, Guagam, Charab gum, Cara gum, Carrageenan, Pectin, Kanten, Quince seed (Malmo mouth), Argecoloy (Katsusowes) ), Starch (rice, corn, potato, wheat), glycyrrhizic acid ⁇ , microbial polymers (xanthan gum, dextran, succinoglucan, bullulan), animal polymers (collagen, casein, albumin, gelatin) )
  • Semi-synthetic water-soluble polymers starch polymers (carboxymethyl starch, methylhydroxypropyl starch), cellulose polymers (methylcellulose, ethylcellulose, methylhydroxypropylcellulose, hydroxyxetylcellulose, cellulose sulfate) Sodium, hydroxypropylcellulose, carboxymethylcellulose, carboxymethylcellulose sodium, crystalline cellulose, cellulose powder), alginic acid polymer (sodium alginate, Propylene glycol ester alginate).
  • Synthetic water-soluble polymers Vinyl polymers (Polyvinyl alcohol, Polyvinyl methyl ether, Polyvinylpyrrolidone, Carboxyvinyl polymer), Polyoxyethylene polymers (Polyethylene glycol 20, 0 00, Polyoxyethylene polyoxypropylene copolymer of 40, 0 0 0, 60 0, 0 0), acrylic polymer (poly (sodium acrylate), poly (ethylene chloride), poly (acrylic amide)), polyethylene Imin, a cationic polymer.
  • Vinyl polymers Polyvinyl alcohol, Polyvinyl methyl ether, Polyvinylpyrrolidone, Carboxyvinyl polymer
  • Polyoxyethylene polymers Polyethylene glycol 20, 0 00, Polyoxyethylene polyoxypropylene copolymer of 40, 0 0 0, 60 0, 0 0
  • acrylic polymer poly (sodium acrylate), poly (ethylene chloride), poly (acrylic amide)
  • polyethylene Imin a cationic polymer.
  • Thickeners gum arabic, carrageenan, cara gum, gum tragacanth, carob gum, quince seed (malmite), casein, dextrin, gelatin, sodium pectate, sodium aradate, methylcellulose , Ethylcellulose, CMC, Hydroxy Shetylcellulose, Hydroxypropylcellulose, PVA, PVM, PVP, Sodium polyacrylic acid, Carpoxyvinyl polymer, Mouth candy Bean gum, Guar gum, Evening marine Amber gum, dialkyldimethylammonium cellulose sulfate, xanthan gum, magnesium aluminum silicate, bentonite, hectolite, kalic acid Al Mg (veegum), labonite, anhydrous key acid.
  • UV absorbers Benzoic acid UV absorbers ⁇ Paraaminobenzoic acid (hereinafter abbreviated as PABA), PABA monoglycerin ester, N, N-dipropoxy PABA ethyl ester, N, N-diethoxy PABA ethyl ester, N, N-dimethyl PABA ethyl ester , N, N-dimethyl PABA butyl ester, N, N-dimethyl PABA ethyl ester ⁇ , anthranilic acid UV absorber (homomethyl-N_acetyl anthranilate), salicylic acid UV absorber (amyl salicylate, menthyl salicylate) , Homomentil salicylate, Octyl salicylate, Phenyl salicylate, P-isopropanol phenyl salicylate
  • Cinnamic acid UV absorbers octylcinnamate, ethyl 4-monoisopropyl cinnamate, methyl-2,5-diisopropylcinnamate, ethyl-2,4-diiso-oral pilcinnamone, methyl
  • Sequestrants 1—Hydroxetane-1 1-diphosphoshonic acid, 1-Hydroxetane 1, 1 —Diphosphonic acid tetrasodium salt, Nedatium edetate, Trina edetate 3 h U Kum, edet Tetrasodium acid, sodium citrate, sodium polyphosphate, sodium metal phosphate, gluconic acid, phosphoric acid, citrate, ascorbic acid
  • Polyhydric alcohol Dihydric alcohol (ethylenic U coal, propylene glycol, trimethylene glycol, 12-butylene glycol, 1,3_butylene glycol, teramethylene glycol, 2, 3—butylene glycol, Pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol 31, octylene glycol, trihydric alcohol (glycerin, U methylol bread), tetrahydric alcohol (pen erythritol (1 , 2, 6-hexanetriol) ⁇ , pentahydric alcohol (xylitol), hexahydric alcohol (sorbitol J, mannitol), polyhydric alcohol polymer (diethylene glycol, dipropylene glycol, triethylene glycol, Polypropylene glycol, tetraethylene Recalls, Jiguriseri down, polyethylene glycol, Application Benefits glycerin, Te Bok Raguriseri emissions, poly glycerin),
  • Ash sugar D—Glyceryl Aldehi F, Sidroxylase N
  • Five-carbon sugar L-arabinosis, D—Xylose, L—Liquisose D—Aarabinose, D—Liposose, D—Librose, D—Xylulose, L—Xylulose, Hexet Sugar
  • pentose sugar aldoheptose, heprose
  • octose sugar kullose
  • deoxysugar 2—deoxy D—lipose 6—Deoxy: L monogalactose, 6—Deoxy: L
  • Origo sugar sucrose, danthianose, umbelliferose, lac Tooth, Planteose, Isolicnose,, a- ⁇ Rehalose, Raffinose, Lyquinose, Unpilycin, Stachiosperno 'course.
  • Polysaccharides Cellulose, quinceid, chondroitin sulfate, denpung, galactan, dermatan sulfate, glycogen, gum arabic, heparan sulfate, hyaluronic acid, tragacanth gum, keratan sulfate, chondroitin, xanthan gum, mucoitin sulfate, guagam Dex ⁇ ⁇ orchid, keratosulfate, Locus ⁇ Bingham, succinoglucan, carolinic acid.
  • Amino acid Neutral amino acid (threonine), basic amino acid (hydroxylidine).
  • Facilsarcocinium (Lauroylsarcocinnatrium), Acylglutamate, Facil ⁇ -Aranine, Pyrrolidonecarboxylic acid.
  • Organic amines monoethanolamine, jejunolamine, triethanolamine, morpholine, trisopropanolamine, 2-amino-2-methyl-1,3-propanediol, 2-amino One 2-Methyl-1-propanol.
  • Polymer emulsion Acrylic resin emulsion, Polyacrylic acid ethyl emulsion, Acrylic resin solution, Polyacrylic alkyl ester emulsion, Polyvinyl acetate resin emulsion, Natural rubber latex.
  • Preparation agent Sodium lactate monolactate, sodium citrate succinate, sodium succinate-succinate.
  • Vitamin vitamin A, vitamin B1, vitamin B2, vitamin C, vitamin E, derivatives thereof, pantothenic acid and derivatives, biotin, nicotinic acid amide.
  • Antioxidants Tocopherol, dibutylhydroxytoluene, butylhydroxyanisole, gallic acid ester.
  • Antioxidant auxiliaries phosphoric acid, citrate, ascorbic acid, maleic acid, malonic acid, succinic acid, fumaric acid, kefaline, hexamate phosphate, phytic acid, ethylenediaminetetraacetic acid.
  • Hair dye Acrylic resin alkanolamine liquid.
  • Propellant Various liquefied petroleum gas (LPG), such as liquefied gas such as LPG, dimethyl ether, liquefied oil gas and dimethyl ether, mainly composed of propane, buvene, isobutane, nitrogen gas and carbon dioxide gas Compressed gas.
  • LPG liquefied petroleum gas
  • dimethyl ether liquefied oil gas and dimethyl ether
  • propane propane, buvene, isobutane, nitrogen gas and carbon dioxide gas Compressed gas.
  • Preservatives Ethylparaben, Butylparaben
  • Anti-inflammatory agents Darityrrhizic acid derivative, Glycyrrhetinic acid derivative
  • Whitening agent placenta extract, saxifrage extract, alptin
  • various extracts opac, oo-ren, sicon, peonies, sempri, ba
  • RNA extract I S0GEN Natural Gene
  • Chloroform 200 1 was added and sufficiently stirred again with a Portex mixer, and then centrifuged (15000 rm, 15 minutes) with a small microcentrifuge to recover about 500 1 of an aqueous phase containing RNA.
  • 50 ⁇ 1 3M sodium acetate and 1 etaprecipitate were added and stirred thoroughly.
  • Detection and quantification are performed by mixing the synthesized cDNA, a primer specific to the gene to be detected and quantified, and real-time PCR reagent (Roche), and performing real-time PCR at 350S in the light cycler system.
  • a gene fragment was amplified.
  • PCR product ⁇ ⁇ ⁇ ⁇ 1 1 copy equivalent similarly to the width increase of Ri by the real-time PCR to prepare a calibration curve, detection and quantification contained in the sample
  • the expression level of the gene to be converted was calculated as the number of copies per unit (lg) of RNA.
  • Constant temperature a constant humidity chamber (25 ° C, humidity 50%)
  • the hair diameter measuring device SK-2000 Kerto Tech / Shiseido
  • the hair diameter measuring device SK-2000 Kerto Tech / Shiseido using laser light is used to measure the long and short diameters of hair samples by 2 ⁇ intervals.
  • the bending stress of hair samples was measured in a constant temperature and humidity chamber (25 ° C, humidity 50%) using a torque sensing type bending stress measuring device KES-SH (Kato Tech).
  • the bending speed was set to 0. Scnf i / sec., And the bending stress (M) of each hair sample at the curvature (p) ⁇ 1.0 to 2.0 cm-1 was measured.
  • the hair diameter and bending stress were measured for each hair sample, and the Young's modulus (E) of each hair sample was calculated by the following formula using the second moment of inertia (I).
  • the cross section second moment (I) is expressed by the following equation.
  • ⁇ ⁇ /-a 3 ⁇ b (a is the short radius of hair, b is the long radius of hair)
  • Hair keratin H a 1 gene -0.134
  • Panel 1 Measure the hardness (Young's modulus) of one person's hair as described above.
  • the plies used are as follows:
  • FIG. Figure 7 shows the average value and standard deviation (p ⁇ 0.05) of “high Young's modulus hair” (High) and “low Young's modulus hair” (Low).
  • ⁇ indicates that there is a sigh difference in the gang rate between the group and the“ low bang rate hair ”group.
  • Fig. 7 (b) shows the ⁇ high Young's modulus hair ”(High) and“ Low Yang's hair J (Low)
  • KA P5.1 and KA P 5.4 genes are significantly increased. Became clear. Therefore, KAP 5. Measurements of 1 and KA P5.4 gene expression were also significant.
  • the KA P5.1 to 5.5 genes (SEQ ID NOs: 1 to 5) belong to the keratin-related protein KA P5 family and are relatively high homology genes. The high degree of homology between the amino acid sequences of the putative proteins encoded by each gene is apparent from FIG. 1 and Table 1 described above.
  • each putative protein encoded by the KAP 5.1-5 gene is all cysteine-rich and contains abundant low-molecular amino acids glycine and serine. It can easily penetrate between keratin fibers without forming secondary structures such as ox, and it is also possible to form many hydrogen bonds due to the ⁇ group of many cerine residues. It is thought that it greatly contributes to the mechanical strength.
  • a portion of the 1-5 gene predicted coding protein The amino acid composition is as shown in Table 2.
  • each gene fragment of ⁇ 5 was amplified in the form of T7 polymerase promoter sequence added to the antisense side.
  • Each amplified gene fragment was purified with a commercially available kit (Wizard SV Gel and PCR clean-up System: Promega) and then specific for each KAP5 gene using T7 polymerase and DI G RNA labeling kit (Roche). A lipoprobe was prepared. . Identification of the expression site of each KAP gene
  • NA fragment Approximately 15 kb D containing KAP 5.1 gene and KA P5.2 gene
  • the NA fragment is composed of NM—F 1 primer (SEQ ID NO: 2 2) and R 2 ⁇ primer (SEQ ID NO: 2 3) with recognition sites for restriction enzymes Not I and M 1 u I at the 5 ′ end.
  • SEQ ID NO: 2 2 A commercially available human genomic DNA (obtained from Pr. Omega) was used as a saddle and was amplified by PCR (Fig. 8-A).
  • the NM—F 1 primer (SEQ ID NO: 2 2) and R 2 primer (SEQ ID NO: 2.3) are as shown in the table below.
  • the numbers shown in the table indicate the position of the sequence number of HO sapiens genomic DNA, chromosome 11c 1 one: RP 11-684B2, coniplete sequences. ACCESSI ON: AP000867.5.
  • the amplified DNA fragment is double-quenched with restriction enzymes M 1 u I and N he I and separated by agarose gel electrophoresis.
  • Step 1 Subclamate the SacI / NcoI fragment (15 4 bp, Fig. 9) to pGL-3bbasic.
  • Step 2 Insert a SacI fragment (approximately 4.0 kbp, Fig. 9) into the resulting plasmid, and repo overnight containing the 5 'upstream region of KAP 5.1 (SEQ ID NO: 24).
  • SEQ ID NO: 24 The 5 'upstream region of KAP 5.1
  • IORS Immortalized outer root sheath cells
  • the cultured Io RS cells were constructed according to the manual of Effectene Trnsfection Reagent (QIAGEN) and the reporter plasmid pGL 3 — KA P 5.1 (firef 1 yluciferase) and a commercially available internal standard plus S de p RL
  • the drugs used in the test are as follows:
  • H-Ser-O B z 1-HC 1 obtained from S I GMA, L
  • Acetyldaricin obtained from Nacalai Tesque, L
  • Glycylglycine obtained from SIGMA, L
  • Vitamin U chloride obtained from Tokyo Kasei
  • Colline chloride obtained from Wako Pure Chemical
  • O-acetylcellulose obtained from SIGMA, L
  • Serine methyl ester obtained from A 1 drich, L, purity 98%, hydrochloride
  • 'Glycine obtained from Nacalai Testa, purity 9 9%
  • Acetylcystine obtained from S I GMA, L, purity 9 9%
  • Homocysteic acid obtained from S I GMA, L, purity 9 9%
  • Methionine obtained from Wako Pure Chemical, L, purity 9 9%
  • Dalyu thione reduced form obtained from S I GMA, L, purity 9 9%
  • Folic acid obtained from Wako Pure Chemical, purity 98 to 100%
  • Adenosine obtained from S I GMA, purity 9 9%
  • Dibutyl c AMP obtained from SI GMA, purity 9 7%, N 6 , 2, 1 0-dibutyryl adenosine 3 ', 5'-cyclic monophosphate sodium salt) (K—S FM (—)).
  • Vitamin U chloride 111 (lOppm), 127 (lOOppm)
  • Formulation examples of the cosmetic for hair of the present invention are shown below.
  • the blending amount is mass%.
  • the hardness of the wax was measured by I-Techno Engineering Co., Ltd. Powerhouse Dome Ichiya / Max ME-4 15 (Diameter: 5.6 mm; Speed: 7 sec Z inch; Load: 20 0 0 g; Temperature: 37 ° C).
  • the viscosity was measured at a single cylinder type rotational viscometer manufactured by Shibaura System Co., Ltd. at 1 2 8 7 temperature 30 ° C.
  • High viscosity products such as jewel, tritment, etc. are VS-HI type (No. 6/10 rpm), mist, hair liquid, moose,., Hair tonic, hair growth VS-A type 1 (Low Yuichi No. 1/6 Orp. Pm) was used for the low-viscosity agent.
  • Formulation example Formulation example
  • a wax containing the drug of the present invention was prepared by a conventional method according to the following formulation. Emulsified wax, hardness 20 This wax had a good feeling of use, and an improvement in the feel of a sticker was observed.
  • a wax containing the drug of the present invention was prepared by a conventional method according to the following formulation. Emulsified wax, hardness 20 This wax had a good feeling of use, and an improvement in the feel of a sticker was observed. ' ⁇
  • a mist containing the drug of the present invention was prepared by a conventional method.
  • Mist aerosol
  • viscosity 5 This mist had a good feeling of use, and an improvement in the feel of the beam was observed.
  • a mist containing the drug of the present invention was prepared by a conventional method.
  • Mist aerosol
  • viscosity 5 This mist had a good feeling of use, and an improvement in the feel of the beam and stiffness was observed.
  • a jewel containing the drug of the present invention was prepared by a conventional method. Transparent solid (die), viscosity 3 0 0 0 0. This jewel has a good feeling of use, and an improvement in the feel of the beam is seen.
  • a jewel containing the drug of the present invention was prepared by a conventional method. Transparent solid (die), viscosity 3 0 0 0 0. This jewel has a good feeling of use, and has an improved feeling of tension and stiffness.
  • Glycerin 5 Behenyl alcohol 1
  • a hair kit containing the drug of the present invention was prepared by a conventional method. Transparent solid, viscosity 8. This hair liquid has a good feeling of use, and an improved feeling of elasticity and stiffness has been observed.
  • a hair kit containing the drug of the present invention was prepared by a conventional method. Transparent solid, viscosity 8. This hair liquid feels good There was also an improvement in the feel of the beam.
  • a treatment containing the agent of the present invention was prepared by a conventional method.
  • This treatment had a good feeling of use, and an improvement in the feel of the beam was observed.
  • an ointment containing the agent of the present invention was prepared by a conventional method.
  • This treatment has a good feeling of use, and an improvement in the feel of the beam is observed.
  • a mousse containing the drug of the present invention was prepared by a conventional method.
  • a mousse containing the drug of the present invention was prepared by a conventional method.
  • Propellant Formulation example 7.1 Hair tonic
  • a satellite containing the drug of the present invention was prepared by a conventional method. Transparent liquid, viscosity 7. This hair tonic also feels good There was good improvement in the feeling of stiffness and stiffness.
  • a satellite containing the drug of the present invention was prepared by a conventional method.
  • a hair restorer containing the agent of the present invention was prepared by a conventional method. Transparent liquid, viscosity 7. This hair-restoring agent also had a good feeling of use, and an improvement in the feel of agitation and strain was observed.
  • a hair restorer containing the drug of the present invention is prepared by a conventional method. Prepared. Transparent liquid, viscosity 7. This hair-restoring agent had a good feeling of use, and an improvement in a feeling of elasticity and stiffness was observed.
  • the hair paste / scrubbing improver and hair cosmetic of the present invention can improve hair paste / strain by being used for the hair or scalp and penetrating into the hair or absorbed by the hair follicle. Yes, it is useful as a beauty method.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention a pour objet un agent améliorant l'élasticité et la résistance des cheveux. Ledit agent comprend au titre de principe actif, au moins un composé sélectionné au sein du groupe constitué par la N-acétyl-DL-sérine, la O-acétyl-L-sérine, la N-acétylglycine, la O-phospho-L-sérine, l’acide phosphoglycérique, la glycylsérine, et des sels de qualité pharmaceutique des composés précédents. La présente invention a également pour objet une préparation cosmétique pour cheveux.
PCT/JP2005/021629 2004-11-19 2005-11-18 Agent améliorant l’élasticité et la résistance des cheveux, et préparation cosmétique pour cheveux WO2006054792A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2004-335918 2004-11-19
JP2004335918A JP2006143649A (ja) 2004-11-19 2004-11-19 毛髪はり・こし改善剤
JP2004-352459 2004-12-06
JP2004352459A JP2006160641A (ja) 2004-12-06 2004-12-06 毛髪はり・こし改善剤および毛髪用化粧料

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0386812A (ja) * 1989-08-16 1991-04-11 Unilever Nv 化粧組成物
JPH05139947A (ja) * 1991-04-10 1993-06-08 Ruey J Yu ２−ヒドロキシカルボン酸及び関連化合物を含有する組成物、並びに皮膚科学的老化徴候を緩和するための方法
JPH05255386A (ja) * 1991-02-06 1993-10-05 L'oreal Sa グリシル−セリンのアミドジペプチド誘導体の界面活性剤または水和剤としての利用および新規アミドジペプチド
JPH11508542A (ja) * 1995-06-26 1999-07-27 ハンス・シュヴァルツコプフ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンディットゲゼルシャフト ヘアケア剤を少なくとも１種含有する染毛剤
JP2000000089A (ja) * 1998-06-15 2000-01-07 Shiseido Co Ltd 不死化ヒト外毛根鞘細胞及びそれを用いた育毛剤評価法
JP2001089330A (ja) * 1999-09-17 2001-04-03 Kyowa Hakko Kogyo Co Ltd 育毛剤
JP2002534369A (ja) * 1999-01-08 2002-10-15 ルーイ・ジエイ・ユー Ｎ−アセチルアルドースアミン又はｎ−アセチルアミノ酸からなる局所療法用組成物
WO2003042387A1 (fr) * 2001-11-13 2003-05-22 Keio University Nouvelles proteines associees a la keratine des poils

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0386812A (ja) * 1989-08-16 1991-04-11 Unilever Nv 化粧組成物
JPH05255386A (ja) * 1991-02-06 1993-10-05 L'oreal Sa グリシル−セリンのアミドジペプチド誘導体の界面活性剤または水和剤としての利用および新規アミドジペプチド
JPH05139947A (ja) * 1991-04-10 1993-06-08 Ruey J Yu ２−ヒドロキシカルボン酸及び関連化合物を含有する組成物、並びに皮膚科学的老化徴候を緩和するための方法
JPH11508542A (ja) * 1995-06-26 1999-07-27 ハンス・シュヴァルツコプフ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンディットゲゼルシャフト ヘアケア剤を少なくとも１種含有する染毛剤
JP2000000089A (ja) * 1998-06-15 2000-01-07 Shiseido Co Ltd 不死化ヒト外毛根鞘細胞及びそれを用いた育毛剤評価法
JP2002534369A (ja) * 1999-01-08 2002-10-15 ルーイ・ジエイ・ユー Ｎ−アセチルアルドースアミン又はｎ−アセチルアミノ酸からなる局所療法用組成物
JP2001089330A (ja) * 1999-09-17 2001-04-03 Kyowa Hakko Kogyo Co Ltd 育毛剤
WO2003042387A1 (fr) * 2001-11-13 2003-05-22 Keio University Nouvelles proteines associees a la keratine des poils

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