CA2236277A1 - Aqueous cosmetic composition containing stably solubilized uric acid and water-soluble polymer and method for stably solubilizing uric acid in aqueous cosmetic composition - Google Patents
Aqueous cosmetic composition containing stably solubilized uric acid and water-soluble polymer and method for stably solubilizing uric acid in aqueous cosmetic composition Download PDFInfo
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- CA2236277A1 CA2236277A1 CA002236277A CA2236277A CA2236277A1 CA 2236277 A1 CA2236277 A1 CA 2236277A1 CA 002236277 A CA002236277 A CA 002236277A CA 2236277 A CA2236277 A CA 2236277A CA 2236277 A1 CA2236277 A1 CA 2236277A1
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- uric acid
- cosmetic composition
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
- A61Q5/10—Preparations for permanently dyeing the hair
Abstract
The present invention is directed to an aqueous cosmetic composition containing uric acid in a stably solubilized state together with an acrylic polymer. The composition is adjusted to pH equal to or higher than pK1 of uric acid, in particular, pH 7 or higher by an alkali to solubilize uric acid. A method for stably solubilizing uric acid in an aqueous cosmetic composition is also disclosed.
Description
AQUEOUS COSMETIC COMPOSITION CONTAINING STABLY SOLUBILIZED URIC
ACIDANDWATER-SOLUBLEE'OLYMERANDMETHODFORSTABLY SO~UBILIZING
URIC ~CID IN AQUEOUS COSMETIC COMPOSITION
The present invention xelates to an aqueous cosmetic composition containing stably solubilized uric acid together with a water-soluble polymer, especially, an acrylic polymer, and a method for stab]y solubilizing uric acid in an aqueous cosm~tic composition.
Uric acid as well as its salts and derivatives (hereinafter they are simply referred to as "uric acid"
altogether) are used in various cosmetic compositions as a subst:rate of one of oxidases, uricase, an agent for improving solubility of a dye, a moisturizer stabilizer, an ingredient for preventing skin roughness, an antidandruff ingredient, and the like. For example, JP 61-118312 A discloses a keratin fiber dyeing composition of pH 4 to 10.5 which comprises uric acid as an a~ent for improving solubility of a specific dye, i.e., N-substituted-2-nitro--p-phenylenediamine, an ampholytic surf~ctant and a thickener including polyacrylic acid, and a method for dyeing keratin fiber using the composition. JP
61-18320~ A discloses a cosmetic composition comprising a moisturizer and uric acid as a stabilizer for the moisturizer.
JP 63-246313 A (USP 4,961,925) discloses a hair cosmetic compcsition of pH 7.5 to 8.5 which comprises dielectron reducing 5 oxida.se, uric acid as a donor of the enzyme and the like. JP
1-275511 A discloses a topical composition for external skin use containing uric acid to prevent skin roughness. JP 1-275516 A discloses an antidandruff composition containing uric acid.
JP 8-217652 (EP 0716846 A) discloses an oxidation hair dyeing 10 composition of pH 6.7 to 9.5 which comprises uric acid, potassium hydroxide and/or monoethanolamirle and the like.
On the other hand, sinc:e the water-solubility of uric acid is very low such as about 0.0067%, at present, only a small amount of uric acid can be used in the case of an aqueous 15 solubilized system. :[n addition, in the case of a dispersion system wherein uric ac id is added in excess of its solubility, there are many problems such a<, precipitation of uric acid, limi.ation of containers to be used for packaging end products due to clogging of orifices thereof and the like.
Moreover, although uric acid can be solubilized in water to a certain extent by app:ropriately choosing an alkali, mere solubilization is insufficient for practical use due to such prob.Lems as drip and less fitness for hair or skin upon application, and the like. Then, in practice, it is necessary to add surfactants and polymers in view of suitability for use.
However, in aqueous cosmetic compositions containing surfactants and polymers, no satisfactory technique for stably solubilizing uric acid has yet been found.
One object of the present invention is to provide a techniqueforstablysol.ubilizinguricacidinanaqueouscosmetic compcsition containing uric acid and a water-soluble polymer.
This object as well as other objects and advantages of the present invention will bec:ome apparent to those skilled in the art from the following description with reference to the accompanying drawing.
Fig. 1 illustrates ti1ration curves of a uric acid solut:ion in water with various a.lkalis.
The present inventors have studied intensively the behaviour of uric ac:id in an aqueous cosmetic composition.
As a result, it has been found that uric acid can be stably solubilized in such a composition by combining a specific polymer and an alkali and adjusting pH of the composition to a specific range.
That is, in one aspect, the present invention provides an aqueous cosmetic composition cc,ntaining uric acid in a stably solubilized state which comprises uric acid, an acrylic polymer, an alkali and water, said composition being adjusted to pH equal to or higher than pKl of uric acid, in particular, pH 7 or higher by the alkali to solubilize uric acid.
In another aspect, the present invention provides a method for stably solubilizing uric acid in an aqueous cosmetic compo,itionwhich comprises adjustingpHofthecomposition equal to or higher than pK1 of uric acid, in particular, pH 7 or higher by an alkali to solubilize uric acid.
In the present invention, preferred examples of the acrylic polymer incluc.e carboxyvinyl polymers, copolymers of acrylic and methacrylic acid polymers and alkyls, copolymers of acrylic and methacrylic acid polymers and polyoxyethylene glycol ether of higher alcohols, and betaine type acrylic amphoteric polymers. Preferred examples of the alkali include amines.
According to the presentinvention, a relativelylarge amount of uric acid such as 0.01 to 2.0% by weight can be stably solubilized to provide an aqueous cosmetic composition, for example, hair dyeing composition which exhibits excellent activity of uric acid and sufficient effect of the water-soluble polymer.
The terms "stably solubilizing" and "stably solub-lized state" used herein mean that uric acid is maintained in a solubilized state without separation in a cosmetic composition.
The term "accylic and methacrylic polymer" includes homopolymers and copolymers of acrylic acid, acrylates, methacrylic acid and/o:c methacrylates.
Examples of uric acid to be used in the present inven ion include, in addition to uric acid itself, inorganic salts of uric acid such as sodium urate, potassium urate, calcium urate, sodium hydrogen urate, potassium hydrogen urate, calcium hydrogen urate, etc.; organic salts of uric acid such as ammonium urate, ammonium hydrogen urate, salts of uric acid with various aminoacids, etc.; andvariousuricacidderivativessuch asalkyl modified uric acids (e.g., 3-N-methyl uric acid, 3-N-lauryl uric acid, 7-N-butyl uric acid, 1-N-ethyl uric acid, 9-N-lauryl uric acid, 3,7-N-dimethyluricacid,etc.),uricacidglycosides (e.g., 3-N-ribosyluricacid, "-N-glycosyluricacid, etc.) andthelike.
These uric acid, salts and derivatives can be used alone or in combinatior,and can be used in an amount of, as uric aciditself, O.Olto 2%byweight,F)referablyO.lto 1.3%byweight based on the total weight of the cosmetic composition. When the amount of uric acid is lower than 0.01~ by weight, its activity is incufficient. On the other hand, when the amount of uric acid is morethan 2% byweight, stablesolubilizationthereofis hardly expec1 ed.
The acrylic polymertobe usedin the present invention is not specifically limited and any polymer normally used in cosmetic compositions can be used. Examples thereof include carboxyvinyl polymers mainly composed of acrylic acid; acrylic and methacrylic acid-alkyl copolymers such as copolymers of acrylic and methacrylic acid polymers and alkyls; acrylic and metha_rylic acid polyoxyethylene glycol ether copolymers such as ccpolymers of acrylic and methacrylic acid polymers and polyo~yethylene glycol ethers of higher alcohols (e.g., higher alcohols having 12 to 32 carbon atoms); betaine type acrylic amphoteric polymers; and the like. Preferably, carboxyvinyl polymers, Aculyn ~TM) 22 (copolymer ofacrylicand methacrylic acid polymer and polyoxyethylene glycol ether of stearyl alcohol manufactured and sold by Rhom and Haas Company), CarbopolTM
(acrylic and methacrylic-alkyl copolymer manufactured and sold by B.F. Goodrich Co.), Yukaformer~TM)(copolymer of N-methacryloyloxyethyl N,N--dimethylammonium ~-N-methylcarboxylbetaine and methacrylic acid alkyl ester manuf~ctured and sold by Mitsubishi Chemical Corporation) and the like can bè used. The acrylic polymer can be used alone or in combination in an amount suitable for providing the desired properties to the aqueous cosmetic composition, normally, 0.01 to 10.0% by weight, preferably, 0.1 to 5% by weight based on the totalweight of the composition, though theamount of the acrylic polymer is not specifically limited.
Examples of the alkali to be used in the present invent:ion include amines such as monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), 2-amino-2-methy:L-1-propanol (AMP), 2-amino-2-methyl-1,3-propanediol (AMPD'I, 2-amino-2-hydroxymethyl-1,3-propanediol (AHMPD), monoi,opropanolamine (MIPA), tetrakis(2-hydroxyisopropyl)ethylenediamine (TE) and the like. These alkalis can be used alone or in combination. It is possible to use ammonia and inorganic alkalis such as sodium hydroxide, potassiumhydroxideandthelikeirlsofarastheydonotadversely effect the advantages of the present invention. Although the amount of the alkali to be added to the composition is not speci~ically limited, the amount should be sufficient to adjus_ pH of the composition equal to or higher than pKl of uric i~cid, preferably, pH 7 or higher. Thereby, uric acid can be st~bly solubilized in an aqueous cosmetic composition.
Especially, in the present invention, it is preferred to use an amine as the ~lkali together with the acrylic polymer because uric acid can be solubilized very stably.
According to the present invention, uric acid is added to a major portion of water to be used for the production of the aqueous cosmetic composition and pH of the resultant mixture is adjusted to the desired pH, followed by addition of the acrylic polymerand,ifnecessary, warmingtodissolvethepolymer. Then, otheringredientsareaddedtoobtainthedesiredaqueouscosmetic compositioninvariouspreparationformssuchasgel, paste, cream and t.he like. Thus, an aqueous cosmetic composition for application to hair, sk.in, nails, oral cavity or the like, which conta.ins stably solubilized uric acid together with the acrylic polymer can be obtained.
In the present invention, according to the desired preparation form, sur:Eactants such as anionic surfactants, catio:nic surfactants, nonionic surfactants, etc.; oily agents such as higher alcohols, higher fatty acids, paraffin wax, hydro~arbon oils, ester oils, silicone oils, etc.; hair dyes such as oxidation dyes, direct dyes, etc.; higher alcohols such as glycerin, dipropylene glycol, hexaglycerin, etc.; saccharides such as sorbitol, fruct.ose, reduced maltose, etc.; thickeners;
preservatives; anti-oxidants; UV absorbers; metal chelating agents; enzymes such as uricase; various pharmacologically active ingredients; perfumes; and the like can be appropriately added in so far as they do not adversely effect the advantages of the present invention. It has been found that humectants such higher alcohols and saccharides improve solubilization of uric acid.
The following tests and examples further illustrate the present invention i.n detail but are not to be construed to limit the scope of the present :invention. In the tests and examples, all the "percents (%)" are by weight unless otherwise stated .
Test 1 Effect of various alkalis on solubilization of uric acid In literature, it is said that uric acid has pKl of 5.8 and pK2 of 10.3.
Then, pH titration of uric acid solutions in water was carried out using various al.kalis under the following conditions to prepare pH curves and observe the state of uric acid in the respective solutions.
The results are shown in Table 1 and Fig. 1.
Conditions: Aneachalkalisolution (lOOmM) wasadded to 100 ml of 10 mM uric acid solution in water (20 + 1~C).
Apparatus: pH meter manufactured by HORIBA
Table 1 Alkali pH State of uric acid Ml.A 9 08 dissolved Dl.A 8 02 dissolved Tl.A 7 74 dissolved AI~P 8 87 dissolved AI~PD 8 42 dissolved MrPA 8 96 dissolved T' 8 47 dissolved NaOH 10 00 dissolved KOH 10 14 dissolved As can be se~n from Fig 1 and Table 1, it has been found that uric acid is completely dissolved at a pH range equal to or above its pK1 in the presence of various alkalis to form uniform solubilizedsyscems Althoughuricacidcanbe dissolved by sodium hydroxide or potassium hydroxide, a high pH such as 10 or higher is required to dissolve a large amount of uric acid (0 8% or higher), which is undesirable for a cosmetic composition to be applied to a human being from the viewpoint of irritation Test ~
Effect of combinations of various alkalis and water-soluble polymers on stability of solubilized uric acid in water Various alkal.is were addedto 1% solutions of uric acid in water to completely dissolve uric acid. Then, various water-soluble polymers were mixed with the above uric acid solutions, respective]y, in a final concentration of 2~ to prepare sample solutions (in the case of Carbopol ETD2020, the final concentration of the polymer was 1~). The sample solutions were subjected to repeating cycle of storage at 5~C
for 12 hours and then incubation at 43~C for 12 hours, for 5 days to evaluate whet.her or not the solubilized uric acid.
separated out by mi~ring with the water-soluble polymers according to the following criteria.
A: solubilization of l~ric acid B: separating out of very fine crystals of uric acid C: separati:ng out of uric acid The results are shown in Table 2-A.
Table 2-A
Polymer~
Water HEC xanthan CMC Aculyn Carbopol Carbopol 'con- gum 22 ETD2020 981 t:rol) MEA C BC C A C C
DEA C BC C A C C
AMP C BC C A A A
AMPD C BC C A A A
MIPA C CC C A A A
TE A CC C A C C
NaOH A AA C A C C
*: Water-soluble polymers HEC: hydroxyethyl cellulose CMC: carboxymethyl cellulose Aculyn 22: copolymer of acrylic and methacrylic acid polymer and polyoxyethylene glycol ether of higher alcohol (30%
aqueoussolution) [Acrylates/Steareth-20MethacrylateCopolymer (CTFA ADOPTED NAME)]
Carbopol ETD2020: acrylic and methacrylic acid -polymer-alkyl copolymer [Acrylates/cl030 Alkyl Acrylate CA 02236277 l998-04-28 Crosspolymer]
Carbopol 981: carboxyvinyl polymer As can be seen from Table 2-A, especially, when Aculyn 22 anc.other acrylic polymers were used, stable solubilization of uri.c acid was achieved.
In addition, according to the same method, the effect of a water-scluble polymer on the stability of solubilized uric acicl in water was examined. Namely, monoethanolamine (MEA) was added to 1% solutions of uric acid in water to completely dissolve uric acid. Then, various water-soluble polymers were mixed with the above uric acid soluti.on. The sample solutions were subjected to a repeating cycle of storage at 5~C for 12 hours and then incubation at 430C for 12 hours, for 5 days to evaluate whether or not the solubi.lized uric acid separated out by mixing with the water-solub]e polymers according to the following criteria.
A: solubilization of uric acid B: separating out of uric acid The results are shown in Table 2-B.
CA 02236277 l998-04-28 Table 2-B
Polymer Water Aculyn 22 Yukaformer (control) 204WL
Concentration 10 (%) - 2.0 3.4 11.4 Evaluation A A B A
~5 : Water-soluble polymer Aculyn 22: the same as that in Table 2-A
Yukaformer 204WL: N-Methacryloyloxyethyl N,N-dimethylammonium ~-N-methylcarboxybetaine-alkylmethaCrylate copolymer solution (17.5% aqueous solution) ~0 As can be seen from Table 2-B, Yukaformer 204WL also provided stable solubilization of uric acid.
Test 3 Effect of concentration of acrylic polymer on stability of solubilized uric acid Aculyn 22 was added to aqueous uric acid solutions containing different concentrations of uric acid dissolved with diethanolamine and the resultant mixtures were subjected to a repeating of the above cycle for 5 days to evaluate the state of uric acid according to the same criteria.
The results are shown in Table 3.
CA 02236277 l998-04-28 T~ble 3 Uric acid Aculyn 22 (%) (%) 0 0.2 1.0 1.5 2.0 10 0.4 C A A A A
0.6 C ~ A A A
0.8 C C: A A A
1.0 C C: C C A
A: solubilization of uric acid B: separating out of very fine crystals of uric acid C: separating out of uric acid As can be seen from Table 3, as the concentration of Aculyn 22 is increased, a larger amount of uric acid can be stably solubilized.
Test 4 Effect of various alkalis and Aculyn 22 on stability of solubilized uric acid In order to investigate the ability of various alkalis to solubilize uric acid in the presence of Aculyn 22, 0.5~ or 1.0~ of uric acid was added to water and then various alkalis were added thereto, respectively, until complete solubilization of uric acid was achieved. After addition of alkalis, Aculyn 22 was added to the respective solutions in an amount of 3~ and the CA 02236277 l998-04-28 mixtures were subject to repetition of the above cycle for 15 days. As a control, the uric acid solutions without addition of Aculyn 22 (0%) were also subjected to repetition of the above cycle. Five days and 15 days after initiation of this test, the state of uric acid was evaluated according to the same criteria.
The results are shown in Table 4.
Table 4 Alkali Aculyn Uric Initial 5 days 15 days 22 (%) acid 5(%) MEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
DEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
TEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
AMP 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
AMPD 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
MIPA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
TE 3.0 0.5 A A A
1.0 A A A
0 0.5 A A A
1.0 A A C
CA 02236277 l998-04-28 A: solubilization of uric acid B: separating out.of very fine crystals of uric acid C: separating out: of uric acid As can be seen from Table 4, when 3% of Aculyn 22 was added, uric acid was stably solubilized even 15 days after initiation of the test with any alkali used.
~xam~le 1 One-package hair dye (gel) Ingredient Amount (%) p-Phenylenediamine 1.5 m-Phenylenediamine hydrochloride 0.12 p-Aminophenol 0.6 15 m-Aminophenol 0.08 N-acetyl-1-cysteine 0.08 Aculyn 22 2.5 Sorbitol 5.0 Polyoxyethylene methylglycoside 1.0 20 Polypeptide coconut oil fatty acid 1.0 potassium salt Diethanolamine 0.5 Monoethanolamine pH 9.2 balance Uric acid 1.0 25 Uricase (20 ku/g) 1.0 Purified water balance Total 100.0 According to this formulation, uric acid was added to a part of water to be used and the mixture was adjusted to pH
9.2 with monoethanolamine. Then~ the remaining ingredients were added thereto to obtain the desired hair dye preparation.
This preparation was coated on white hair, which was treated at 30~C for 30 minutes, washed with water, shampooed and then dried. The white hair was dyed to a grayish color.
Fxample 2 Sunscreen milky lotion Ingredient Amount (%) Uric acid 0.1 15 Triethanolamine pH 7.8 balance Aculyn 22 0.3 Hexaglycerin 3.0 Polyoxyethylene(5) alkyl ether 1.0 Decaglycerol monoleate 0.5 20 CetanolTM 0.2 Purified water balance Total 100.0 Uric acid was aclded to water and the mixture was adjusted to pH 7.8 with triethanolamine. Then, the remaining ingredients were added thereto. The mixture was adjusted to pH
7.8 with triethanolamine again to obtain the desired sunscreen milky lotion.
Fx~mple 3 Hand cream Ingredient Amount (%) Uric acid 0.2 Diethanolamine pH 8. 2 balance Stearic acid 14.0 Aculyn 22 0.6 VaselineTM 1.5 Self-emulsifiable glycerol monostearate 2.5 Polyoxyethylene(20)sorbitan monostearate 1.5 Dipropylene glycol 4.0 15 Perfume 0.05 Methylparaben 0.05 Purified water balance Total 100.0 Uric acid was aclded to water and dissolved with diethanolamine. The remaining ingredients except the perfume were added thereto and, if necessary, the mixture was warmed to dissolve the ingredients. After cooling, the perfume was added and pH was adjusted to 8.2 with diethanolamine to obtain the desired hand cream.
Fxample 4 One-package hair dye Ingredient Amount (%) p-Phenylenediamine 0.8 5 p-Aminophenol 0.2 1-Cysteine 0.1 Aculyn 22 2.0 Dipropylene glycol 3.0 Polyoxyethylene(50) hydrogenated 1.0 10 castor oil Uric acid 0.5 Tetrakis(2-hydroxyisopropyl)ethylene- pH 8.5 balance diamine Enzyme (20 ku/g) 1.0 Purified water balance Total 100.0 Uric acid and Aculyn 22 were added to water and the mixture was adjusted to pH 8.5 with tetrakis(2-hydroxyisopropyl)ethylenediamine. Then, the remaining ingredients were added thereto to obtain the desired hair dye preparation.
This preparation was coated on a white hair, which was treated at 30~C for 30 minutes, washed with water, shampooed and then dried. The white hair was dyed to a brownish color.
As described hereinabove, according to the present invention, an aqueous cosmetic composition containing stably solubilized uric acid together with a water-soluble polymer can be obtained.
ACIDANDWATER-SOLUBLEE'OLYMERANDMETHODFORSTABLY SO~UBILIZING
URIC ~CID IN AQUEOUS COSMETIC COMPOSITION
The present invention xelates to an aqueous cosmetic composition containing stably solubilized uric acid together with a water-soluble polymer, especially, an acrylic polymer, and a method for stab]y solubilizing uric acid in an aqueous cosm~tic composition.
Uric acid as well as its salts and derivatives (hereinafter they are simply referred to as "uric acid"
altogether) are used in various cosmetic compositions as a subst:rate of one of oxidases, uricase, an agent for improving solubility of a dye, a moisturizer stabilizer, an ingredient for preventing skin roughness, an antidandruff ingredient, and the like. For example, JP 61-118312 A discloses a keratin fiber dyeing composition of pH 4 to 10.5 which comprises uric acid as an a~ent for improving solubility of a specific dye, i.e., N-substituted-2-nitro--p-phenylenediamine, an ampholytic surf~ctant and a thickener including polyacrylic acid, and a method for dyeing keratin fiber using the composition. JP
61-18320~ A discloses a cosmetic composition comprising a moisturizer and uric acid as a stabilizer for the moisturizer.
JP 63-246313 A (USP 4,961,925) discloses a hair cosmetic compcsition of pH 7.5 to 8.5 which comprises dielectron reducing 5 oxida.se, uric acid as a donor of the enzyme and the like. JP
1-275511 A discloses a topical composition for external skin use containing uric acid to prevent skin roughness. JP 1-275516 A discloses an antidandruff composition containing uric acid.
JP 8-217652 (EP 0716846 A) discloses an oxidation hair dyeing 10 composition of pH 6.7 to 9.5 which comprises uric acid, potassium hydroxide and/or monoethanolamirle and the like.
On the other hand, sinc:e the water-solubility of uric acid is very low such as about 0.0067%, at present, only a small amount of uric acid can be used in the case of an aqueous 15 solubilized system. :[n addition, in the case of a dispersion system wherein uric ac id is added in excess of its solubility, there are many problems such a<, precipitation of uric acid, limi.ation of containers to be used for packaging end products due to clogging of orifices thereof and the like.
Moreover, although uric acid can be solubilized in water to a certain extent by app:ropriately choosing an alkali, mere solubilization is insufficient for practical use due to such prob.Lems as drip and less fitness for hair or skin upon application, and the like. Then, in practice, it is necessary to add surfactants and polymers in view of suitability for use.
However, in aqueous cosmetic compositions containing surfactants and polymers, no satisfactory technique for stably solubilizing uric acid has yet been found.
One object of the present invention is to provide a techniqueforstablysol.ubilizinguricacidinanaqueouscosmetic compcsition containing uric acid and a water-soluble polymer.
This object as well as other objects and advantages of the present invention will bec:ome apparent to those skilled in the art from the following description with reference to the accompanying drawing.
Fig. 1 illustrates ti1ration curves of a uric acid solut:ion in water with various a.lkalis.
The present inventors have studied intensively the behaviour of uric ac:id in an aqueous cosmetic composition.
As a result, it has been found that uric acid can be stably solubilized in such a composition by combining a specific polymer and an alkali and adjusting pH of the composition to a specific range.
That is, in one aspect, the present invention provides an aqueous cosmetic composition cc,ntaining uric acid in a stably solubilized state which comprises uric acid, an acrylic polymer, an alkali and water, said composition being adjusted to pH equal to or higher than pKl of uric acid, in particular, pH 7 or higher by the alkali to solubilize uric acid.
In another aspect, the present invention provides a method for stably solubilizing uric acid in an aqueous cosmetic compo,itionwhich comprises adjustingpHofthecomposition equal to or higher than pK1 of uric acid, in particular, pH 7 or higher by an alkali to solubilize uric acid.
In the present invention, preferred examples of the acrylic polymer incluc.e carboxyvinyl polymers, copolymers of acrylic and methacrylic acid polymers and alkyls, copolymers of acrylic and methacrylic acid polymers and polyoxyethylene glycol ether of higher alcohols, and betaine type acrylic amphoteric polymers. Preferred examples of the alkali include amines.
According to the presentinvention, a relativelylarge amount of uric acid such as 0.01 to 2.0% by weight can be stably solubilized to provide an aqueous cosmetic composition, for example, hair dyeing composition which exhibits excellent activity of uric acid and sufficient effect of the water-soluble polymer.
The terms "stably solubilizing" and "stably solub-lized state" used herein mean that uric acid is maintained in a solubilized state without separation in a cosmetic composition.
The term "accylic and methacrylic polymer" includes homopolymers and copolymers of acrylic acid, acrylates, methacrylic acid and/o:c methacrylates.
Examples of uric acid to be used in the present inven ion include, in addition to uric acid itself, inorganic salts of uric acid such as sodium urate, potassium urate, calcium urate, sodium hydrogen urate, potassium hydrogen urate, calcium hydrogen urate, etc.; organic salts of uric acid such as ammonium urate, ammonium hydrogen urate, salts of uric acid with various aminoacids, etc.; andvariousuricacidderivativessuch asalkyl modified uric acids (e.g., 3-N-methyl uric acid, 3-N-lauryl uric acid, 7-N-butyl uric acid, 1-N-ethyl uric acid, 9-N-lauryl uric acid, 3,7-N-dimethyluricacid,etc.),uricacidglycosides (e.g., 3-N-ribosyluricacid, "-N-glycosyluricacid, etc.) andthelike.
These uric acid, salts and derivatives can be used alone or in combinatior,and can be used in an amount of, as uric aciditself, O.Olto 2%byweight,F)referablyO.lto 1.3%byweight based on the total weight of the cosmetic composition. When the amount of uric acid is lower than 0.01~ by weight, its activity is incufficient. On the other hand, when the amount of uric acid is morethan 2% byweight, stablesolubilizationthereofis hardly expec1 ed.
The acrylic polymertobe usedin the present invention is not specifically limited and any polymer normally used in cosmetic compositions can be used. Examples thereof include carboxyvinyl polymers mainly composed of acrylic acid; acrylic and methacrylic acid-alkyl copolymers such as copolymers of acrylic and methacrylic acid polymers and alkyls; acrylic and metha_rylic acid polyoxyethylene glycol ether copolymers such as ccpolymers of acrylic and methacrylic acid polymers and polyo~yethylene glycol ethers of higher alcohols (e.g., higher alcohols having 12 to 32 carbon atoms); betaine type acrylic amphoteric polymers; and the like. Preferably, carboxyvinyl polymers, Aculyn ~TM) 22 (copolymer ofacrylicand methacrylic acid polymer and polyoxyethylene glycol ether of stearyl alcohol manufactured and sold by Rhom and Haas Company), CarbopolTM
(acrylic and methacrylic-alkyl copolymer manufactured and sold by B.F. Goodrich Co.), Yukaformer~TM)(copolymer of N-methacryloyloxyethyl N,N--dimethylammonium ~-N-methylcarboxylbetaine and methacrylic acid alkyl ester manuf~ctured and sold by Mitsubishi Chemical Corporation) and the like can bè used. The acrylic polymer can be used alone or in combination in an amount suitable for providing the desired properties to the aqueous cosmetic composition, normally, 0.01 to 10.0% by weight, preferably, 0.1 to 5% by weight based on the totalweight of the composition, though theamount of the acrylic polymer is not specifically limited.
Examples of the alkali to be used in the present invent:ion include amines such as monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), 2-amino-2-methy:L-1-propanol (AMP), 2-amino-2-methyl-1,3-propanediol (AMPD'I, 2-amino-2-hydroxymethyl-1,3-propanediol (AHMPD), monoi,opropanolamine (MIPA), tetrakis(2-hydroxyisopropyl)ethylenediamine (TE) and the like. These alkalis can be used alone or in combination. It is possible to use ammonia and inorganic alkalis such as sodium hydroxide, potassiumhydroxideandthelikeirlsofarastheydonotadversely effect the advantages of the present invention. Although the amount of the alkali to be added to the composition is not speci~ically limited, the amount should be sufficient to adjus_ pH of the composition equal to or higher than pKl of uric i~cid, preferably, pH 7 or higher. Thereby, uric acid can be st~bly solubilized in an aqueous cosmetic composition.
Especially, in the present invention, it is preferred to use an amine as the ~lkali together with the acrylic polymer because uric acid can be solubilized very stably.
According to the present invention, uric acid is added to a major portion of water to be used for the production of the aqueous cosmetic composition and pH of the resultant mixture is adjusted to the desired pH, followed by addition of the acrylic polymerand,ifnecessary, warmingtodissolvethepolymer. Then, otheringredientsareaddedtoobtainthedesiredaqueouscosmetic compositioninvariouspreparationformssuchasgel, paste, cream and t.he like. Thus, an aqueous cosmetic composition for application to hair, sk.in, nails, oral cavity or the like, which conta.ins stably solubilized uric acid together with the acrylic polymer can be obtained.
In the present invention, according to the desired preparation form, sur:Eactants such as anionic surfactants, catio:nic surfactants, nonionic surfactants, etc.; oily agents such as higher alcohols, higher fatty acids, paraffin wax, hydro~arbon oils, ester oils, silicone oils, etc.; hair dyes such as oxidation dyes, direct dyes, etc.; higher alcohols such as glycerin, dipropylene glycol, hexaglycerin, etc.; saccharides such as sorbitol, fruct.ose, reduced maltose, etc.; thickeners;
preservatives; anti-oxidants; UV absorbers; metal chelating agents; enzymes such as uricase; various pharmacologically active ingredients; perfumes; and the like can be appropriately added in so far as they do not adversely effect the advantages of the present invention. It has been found that humectants such higher alcohols and saccharides improve solubilization of uric acid.
The following tests and examples further illustrate the present invention i.n detail but are not to be construed to limit the scope of the present :invention. In the tests and examples, all the "percents (%)" are by weight unless otherwise stated .
Test 1 Effect of various alkalis on solubilization of uric acid In literature, it is said that uric acid has pKl of 5.8 and pK2 of 10.3.
Then, pH titration of uric acid solutions in water was carried out using various al.kalis under the following conditions to prepare pH curves and observe the state of uric acid in the respective solutions.
The results are shown in Table 1 and Fig. 1.
Conditions: Aneachalkalisolution (lOOmM) wasadded to 100 ml of 10 mM uric acid solution in water (20 + 1~C).
Apparatus: pH meter manufactured by HORIBA
Table 1 Alkali pH State of uric acid Ml.A 9 08 dissolved Dl.A 8 02 dissolved Tl.A 7 74 dissolved AI~P 8 87 dissolved AI~PD 8 42 dissolved MrPA 8 96 dissolved T' 8 47 dissolved NaOH 10 00 dissolved KOH 10 14 dissolved As can be se~n from Fig 1 and Table 1, it has been found that uric acid is completely dissolved at a pH range equal to or above its pK1 in the presence of various alkalis to form uniform solubilizedsyscems Althoughuricacidcanbe dissolved by sodium hydroxide or potassium hydroxide, a high pH such as 10 or higher is required to dissolve a large amount of uric acid (0 8% or higher), which is undesirable for a cosmetic composition to be applied to a human being from the viewpoint of irritation Test ~
Effect of combinations of various alkalis and water-soluble polymers on stability of solubilized uric acid in water Various alkal.is were addedto 1% solutions of uric acid in water to completely dissolve uric acid. Then, various water-soluble polymers were mixed with the above uric acid solutions, respective]y, in a final concentration of 2~ to prepare sample solutions (in the case of Carbopol ETD2020, the final concentration of the polymer was 1~). The sample solutions were subjected to repeating cycle of storage at 5~C
for 12 hours and then incubation at 43~C for 12 hours, for 5 days to evaluate whet.her or not the solubilized uric acid.
separated out by mi~ring with the water-soluble polymers according to the following criteria.
A: solubilization of l~ric acid B: separating out of very fine crystals of uric acid C: separati:ng out of uric acid The results are shown in Table 2-A.
Table 2-A
Polymer~
Water HEC xanthan CMC Aculyn Carbopol Carbopol 'con- gum 22 ETD2020 981 t:rol) MEA C BC C A C C
DEA C BC C A C C
AMP C BC C A A A
AMPD C BC C A A A
MIPA C CC C A A A
TE A CC C A C C
NaOH A AA C A C C
*: Water-soluble polymers HEC: hydroxyethyl cellulose CMC: carboxymethyl cellulose Aculyn 22: copolymer of acrylic and methacrylic acid polymer and polyoxyethylene glycol ether of higher alcohol (30%
aqueoussolution) [Acrylates/Steareth-20MethacrylateCopolymer (CTFA ADOPTED NAME)]
Carbopol ETD2020: acrylic and methacrylic acid -polymer-alkyl copolymer [Acrylates/cl030 Alkyl Acrylate CA 02236277 l998-04-28 Crosspolymer]
Carbopol 981: carboxyvinyl polymer As can be seen from Table 2-A, especially, when Aculyn 22 anc.other acrylic polymers were used, stable solubilization of uri.c acid was achieved.
In addition, according to the same method, the effect of a water-scluble polymer on the stability of solubilized uric acicl in water was examined. Namely, monoethanolamine (MEA) was added to 1% solutions of uric acid in water to completely dissolve uric acid. Then, various water-soluble polymers were mixed with the above uric acid soluti.on. The sample solutions were subjected to a repeating cycle of storage at 5~C for 12 hours and then incubation at 430C for 12 hours, for 5 days to evaluate whether or not the solubi.lized uric acid separated out by mixing with the water-solub]e polymers according to the following criteria.
A: solubilization of uric acid B: separating out of uric acid The results are shown in Table 2-B.
CA 02236277 l998-04-28 Table 2-B
Polymer Water Aculyn 22 Yukaformer (control) 204WL
Concentration 10 (%) - 2.0 3.4 11.4 Evaluation A A B A
~5 : Water-soluble polymer Aculyn 22: the same as that in Table 2-A
Yukaformer 204WL: N-Methacryloyloxyethyl N,N-dimethylammonium ~-N-methylcarboxybetaine-alkylmethaCrylate copolymer solution (17.5% aqueous solution) ~0 As can be seen from Table 2-B, Yukaformer 204WL also provided stable solubilization of uric acid.
Test 3 Effect of concentration of acrylic polymer on stability of solubilized uric acid Aculyn 22 was added to aqueous uric acid solutions containing different concentrations of uric acid dissolved with diethanolamine and the resultant mixtures were subjected to a repeating of the above cycle for 5 days to evaluate the state of uric acid according to the same criteria.
The results are shown in Table 3.
CA 02236277 l998-04-28 T~ble 3 Uric acid Aculyn 22 (%) (%) 0 0.2 1.0 1.5 2.0 10 0.4 C A A A A
0.6 C ~ A A A
0.8 C C: A A A
1.0 C C: C C A
A: solubilization of uric acid B: separating out of very fine crystals of uric acid C: separating out of uric acid As can be seen from Table 3, as the concentration of Aculyn 22 is increased, a larger amount of uric acid can be stably solubilized.
Test 4 Effect of various alkalis and Aculyn 22 on stability of solubilized uric acid In order to investigate the ability of various alkalis to solubilize uric acid in the presence of Aculyn 22, 0.5~ or 1.0~ of uric acid was added to water and then various alkalis were added thereto, respectively, until complete solubilization of uric acid was achieved. After addition of alkalis, Aculyn 22 was added to the respective solutions in an amount of 3~ and the CA 02236277 l998-04-28 mixtures were subject to repetition of the above cycle for 15 days. As a control, the uric acid solutions without addition of Aculyn 22 (0%) were also subjected to repetition of the above cycle. Five days and 15 days after initiation of this test, the state of uric acid was evaluated according to the same criteria.
The results are shown in Table 4.
Table 4 Alkali Aculyn Uric Initial 5 days 15 days 22 (%) acid 5(%) MEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
DEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
TEA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
AMP 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
AMPD 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
MIPA 3.0 0.5 A A A
1.0 A A A
0 0.5 A C C
1.0 A C C
TE 3.0 0.5 A A A
1.0 A A A
0 0.5 A A A
1.0 A A C
CA 02236277 l998-04-28 A: solubilization of uric acid B: separating out.of very fine crystals of uric acid C: separating out: of uric acid As can be seen from Table 4, when 3% of Aculyn 22 was added, uric acid was stably solubilized even 15 days after initiation of the test with any alkali used.
~xam~le 1 One-package hair dye (gel) Ingredient Amount (%) p-Phenylenediamine 1.5 m-Phenylenediamine hydrochloride 0.12 p-Aminophenol 0.6 15 m-Aminophenol 0.08 N-acetyl-1-cysteine 0.08 Aculyn 22 2.5 Sorbitol 5.0 Polyoxyethylene methylglycoside 1.0 20 Polypeptide coconut oil fatty acid 1.0 potassium salt Diethanolamine 0.5 Monoethanolamine pH 9.2 balance Uric acid 1.0 25 Uricase (20 ku/g) 1.0 Purified water balance Total 100.0 According to this formulation, uric acid was added to a part of water to be used and the mixture was adjusted to pH
9.2 with monoethanolamine. Then~ the remaining ingredients were added thereto to obtain the desired hair dye preparation.
This preparation was coated on white hair, which was treated at 30~C for 30 minutes, washed with water, shampooed and then dried. The white hair was dyed to a grayish color.
Fxample 2 Sunscreen milky lotion Ingredient Amount (%) Uric acid 0.1 15 Triethanolamine pH 7.8 balance Aculyn 22 0.3 Hexaglycerin 3.0 Polyoxyethylene(5) alkyl ether 1.0 Decaglycerol monoleate 0.5 20 CetanolTM 0.2 Purified water balance Total 100.0 Uric acid was aclded to water and the mixture was adjusted to pH 7.8 with triethanolamine. Then, the remaining ingredients were added thereto. The mixture was adjusted to pH
7.8 with triethanolamine again to obtain the desired sunscreen milky lotion.
Fx~mple 3 Hand cream Ingredient Amount (%) Uric acid 0.2 Diethanolamine pH 8. 2 balance Stearic acid 14.0 Aculyn 22 0.6 VaselineTM 1.5 Self-emulsifiable glycerol monostearate 2.5 Polyoxyethylene(20)sorbitan monostearate 1.5 Dipropylene glycol 4.0 15 Perfume 0.05 Methylparaben 0.05 Purified water balance Total 100.0 Uric acid was aclded to water and dissolved with diethanolamine. The remaining ingredients except the perfume were added thereto and, if necessary, the mixture was warmed to dissolve the ingredients. After cooling, the perfume was added and pH was adjusted to 8.2 with diethanolamine to obtain the desired hand cream.
Fxample 4 One-package hair dye Ingredient Amount (%) p-Phenylenediamine 0.8 5 p-Aminophenol 0.2 1-Cysteine 0.1 Aculyn 22 2.0 Dipropylene glycol 3.0 Polyoxyethylene(50) hydrogenated 1.0 10 castor oil Uric acid 0.5 Tetrakis(2-hydroxyisopropyl)ethylene- pH 8.5 balance diamine Enzyme (20 ku/g) 1.0 Purified water balance Total 100.0 Uric acid and Aculyn 22 were added to water and the mixture was adjusted to pH 8.5 with tetrakis(2-hydroxyisopropyl)ethylenediamine. Then, the remaining ingredients were added thereto to obtain the desired hair dye preparation.
This preparation was coated on a white hair, which was treated at 30~C for 30 minutes, washed with water, shampooed and then dried. The white hair was dyed to a brownish color.
As described hereinabove, according to the present invention, an aqueous cosmetic composition containing stably solubilized uric acid together with a water-soluble polymer can be obtained.
Claims (10)
1. An aqueous cosmetic composition which comprises uric acid, an acrylic polymer, an alkali and water, and said composition being adjusted to pH equal to or higher than pK1 of uric acid with the alkali to solubilize uric acid.
2. A composition according to claim 1, wherein the composition is adjusted to pH 7.0 or higher.
3. A composition according to claim 1, wherein the composition containing 0.01 to 2.0% by weight of uric acid.
4. A composition according to claim 1, wherein the acrylic polymer is a carboxyvinyl polymer, an acrylic and methacrylic acid-alkyl copolymer, a copolymer composed of an acrylic and methacrylic acid and a polyoxyethylene glycol ether of a higher alcohol, or a betaine type acrylic amphoteric polymer.
5. A composition according to claim 4, wherein the alkali is an amine.
6. A method for stably solubilizing uric acid in an aqueous cosmetic composition which comprises adjusting pH of the composition equal to or higher than pK1 of uric acid with an alkali to solubilize uric acid.
7. A method according to claim 6, wherein the composition is adjusted to pH 7.0 or higher.
8. A method according to claim 6, wherein the composition containing 0.01 to 2.0% by weight of uric acid.
9. A method according to claim 6, wherein the acrylic polymer is a carboxyvinyl polymer, an acrylic and methacrylic acid-alkyl copolymer, a copolymer composed of an acrylic and methacrylic acid and a polyoxyethylene glycol ether of a higher alcohol, or a betaine type acrylic amphoteric polymer.
10. A method according to claim 9, wherein the alkali is an amine.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11093297A JP3439067B2 (en) | 1997-04-28 | 1997-04-28 | Aqueous cosmetic composition containing stably solubilized uric acid and a water-soluble polymer substance, and a method for stably solubilizing uric acid in an aqueous cosmetic composition |
| JP110932/1997 | 1997-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2236277A1 true CA2236277A1 (en) | 1998-10-28 |
Family
ID=14548264
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002236277A Abandoned CA2236277A1 (en) | 1997-04-28 | 1998-04-28 | Aqueous cosmetic composition containing stably solubilized uric acid and water-soluble polymer and method for stably solubilizing uric acid in aqueous cosmetic composition |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6027719A (en) |
| EP (1) | EP0875241B1 (en) |
| JP (1) | JP3439067B2 (en) |
| KR (1) | KR100348327B1 (en) |
| CN (1) | CN1118276C (en) |
| AT (1) | ATE283683T1 (en) |
| AU (1) | AU714946B2 (en) |
| CA (1) | CA2236277A1 (en) |
| DE (1) | DE69827871T2 (en) |
| TW (1) | TWI225406B (en) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2769214B1 (en) * | 1997-10-03 | 1999-12-17 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2769223B1 (en) * | 1997-10-03 | 2003-08-22 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| FR2769221B1 (en) * | 1997-10-03 | 2000-01-14 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS |
| FR2769218B1 (en) * | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| FR2769222B1 (en) * | 1997-10-03 | 1999-12-31 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| FR2769216B1 (en) * | 1997-10-03 | 1999-12-31 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYEING, PERMANENT DEFORMATION OR DECOLORATION OF KERATINIC FIBERS |
| FR2769211B1 (en) * | 1997-10-03 | 1999-12-24 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2769220B1 (en) * | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| US20020170123A9 (en) * | 1997-10-03 | 2002-11-21 | L'oreal S.A. | Oxidizing composition and uses for dyeing, for permanently reshaping or for bleaching keratin fibres |
| FR2769215B1 (en) * | 1997-10-03 | 1999-12-24 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2769219B1 (en) * | 1997-10-03 | 2000-03-10 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| FR2769210B1 (en) * | 1997-10-03 | 2000-02-11 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2769217B1 (en) * | 1997-10-03 | 2000-03-17 | Oreal | OXIDIZING COMPOSITION AND USES FOR DYING, FOR PERMANENT DEFORMATION OR FOR DECOLORATION OF KERATINIC FIBERS |
| FR2769213B1 (en) * | 1997-10-03 | 1999-12-17 | Oreal | KERATIN FIBER DYEING COMPOSITION AND DYEING METHOD USING THE SAME |
| FR2769835B1 (en) * | 1997-10-22 | 1999-11-26 | Oreal | KERATINIC FIBER OXIDATION DYE COMPOSITION AND DYEING METHOD USING THE SAME |
| US6395269B1 (en) * | 1999-08-16 | 2002-05-28 | Playtex Products, Inc. | Sunscreen lotion or spray composition |
| DE59913340D1 (en) | 1999-12-24 | 2006-05-24 | Schwarzkopf & Henkel K K | AFTER-FOAMING ONE-COMPONENT OXIDATION HAIR COLOR PREPARATION |
| US6774175B2 (en) | 2001-02-16 | 2004-08-10 | L'oreal S.A. | Stabilizing compositions comprising at least two anionic associative polymers, their use for stabilization of non-solid compositions, and compositions comprising at least one stabilizing composition |
| US7070769B2 (en) | 2001-02-16 | 2006-07-04 | L'oreal | Compositions comprising at least two anionic associative polymers and their use for stabilization of an oxidizing solution |
| US6562770B2 (en) * | 2001-03-27 | 2003-05-13 | Colgate-Palmolive Co. | Fragrance-containing gel for delivering fragrance from structured liquid detergent compositions |
| US20020163109A1 (en) * | 2001-04-03 | 2002-11-07 | Raytheon Company | Conformal firing of ceramic radomes |
| US7153496B2 (en) * | 2002-01-18 | 2006-12-26 | Noveon Ip Holdings Corp. | Hair setting compositions, polymers and methods |
| JP2004067647A (en) * | 2002-08-09 | 2004-03-04 | Showa Denko Kk | External preparation for skin |
| GB2450358A (en) * | 2007-06-20 | 2008-12-24 | Roy Arlington Jordan | Alkyl- and alkanolammonium hydroxybenzoate salts for the topical treatment of infection, inflammation and pain |
| JP2009235013A (en) * | 2008-03-28 | 2009-10-15 | Mandom Corp | Hair dye composition |
| JP5546818B2 (en) * | 2009-09-11 | 2014-07-09 | 株式会社マンダム | Hair treatment agent for oxidative hair dye |
| CN112831448B (en) * | 2021-04-02 | 2022-09-23 | 新疆医科大学 | High-uric-acid culture medium for screening intestinal-tract-degrading uric-acid strains and preparation method thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS522917B2 (en) * | 1972-07-15 | 1977-01-25 | ||
| JPS5123294A (en) * | 1974-08-19 | 1976-02-24 | Seishin Seiyaku Kk | Nyosanno anteikaho |
| LU85501A1 (en) * | 1984-08-13 | 1986-03-11 | Oreal | TINCTORIAL COMPOSITION FOR KERATINIC FIBERS CONTAINING AT LEAST ONE NITRO-2 N-SUBSTITUTED PARAPHENYLENEDIAMINE COSOLUBILIZED AND METHOD FOR DYEING KERATINIC FIBERS |
| JPS61183204A (en) * | 1985-02-07 | 1986-08-15 | Riken Vitamin Co Ltd | Cosmetic |
| JP2775154B2 (en) * | 1988-04-26 | 1998-07-16 | 株式会社資生堂 | Anti-skin and anti-aging agents |
| JP2696523B2 (en) * | 1988-04-26 | 1998-01-14 | 株式会社資生堂 | Anti-dandruff agent and hair cosmetic |
| CA2150596A1 (en) * | 1994-12-16 | 1996-06-17 | Yoshio Tsujino | Oxidation hair dye composition |
| DE19547991A1 (en) * | 1995-12-21 | 1997-06-26 | Beiersdorf Ag | Use of combinations of uricase and uric acid |
-
1997
- 1997-04-28 JP JP11093297A patent/JP3439067B2/en not_active Expired - Fee Related
- 1997-07-03 US US08/887,932 patent/US6027719A/en not_active Expired - Fee Related
-
1998
- 1998-04-17 AU AU61949/98A patent/AU714946B2/en not_active Ceased
- 1998-04-24 KR KR1019980014710A patent/KR100348327B1/en not_active IP Right Cessation
- 1998-04-27 DE DE69827871T patent/DE69827871T2/en not_active Expired - Lifetime
- 1998-04-27 EP EP98107657A patent/EP0875241B1/en not_active Expired - Lifetime
- 1998-04-27 AT AT98107657T patent/ATE283683T1/en not_active IP Right Cessation
- 1998-04-28 TW TW087106521A patent/TWI225406B/en active
- 1998-04-28 CN CN98107929A patent/CN1118276C/en not_active Expired - Fee Related
- 1998-04-28 CA CA002236277A patent/CA2236277A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU6194998A (en) | 1998-10-29 |
| DE69827871T2 (en) | 2005-11-24 |
| US6027719A (en) | 2000-02-22 |
| TWI225406B (en) | 2004-12-21 |
| CN1118276C (en) | 2003-08-20 |
| JP3439067B2 (en) | 2003-08-25 |
| AU714946B2 (en) | 2000-01-13 |
| KR19980081705A (en) | 1998-11-25 |
| JPH10298027A (en) | 1998-11-10 |
| CN1200264A (en) | 1998-12-02 |
| EP0875241B1 (en) | 2004-12-01 |
| EP0875241A3 (en) | 1999-03-24 |
| EP0875241A2 (en) | 1998-11-04 |
| KR100348327B1 (en) | 2002-10-31 |
| DE69827871D1 (en) | 2005-01-05 |
| ATE283683T1 (en) | 2004-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |