JPH0219576A - Dyeing composition for keratinous fiber - Google Patents

Dyeing composition for keratinous fiber

Info

Publication number
JPH0219576A
JPH0219576A JP63169571A JP16957188A JPH0219576A JP H0219576 A JPH0219576 A JP H0219576A JP 63169571 A JP63169571 A JP 63169571A JP 16957188 A JP16957188 A JP 16957188A JP H0219576 A JPH0219576 A JP H0219576A
Authority
JP
Japan
Prior art keywords
substance
dyeing composition
coupling
dyeing
hair
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
JP63169571A
Other languages
Japanese (ja)
Other versions
JP2526099B2 (en
Inventor
Jiro Kawase
川瀬　次朗
Tsutomu Mano
真野　勉
Michio Obayashi
大林　道夫
Daisuke Misu
大介 三栖
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Priority to JP63169571A priority Critical patent/JP2526099B2/en
Publication of JPH0219576A publication Critical patent/JPH0219576A/en
Application granted granted Critical
Publication of JP2526099B2 publication Critical patent/JP2526099B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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

Abstract

PURPOSE:To obtain the subject composition, containing a specific developing substance and coupling substance and capable of dyeing keratinous fiber, such as hair, to a strong color tone with a high saturation. CONSTITUTION:A color developing substance consisting of a triaminopyrimidine derivative expressed by formula I or II or a salt (e.g. inorganic acid or organic acid salt) is combined with a coupling substance, e.g. a substance selected from resorcin, 2-methylresorcin and 4-chlororesorcin (forming orange to red color tone by this combination) or with 4-propyl-2,6-diaminopyridine or 3,4-dimethyl-2,6- diaminopyridine (forming bright yellow by this combination), etc., and converted into a creamy or emulsion form to dye keratinous fiber, such as hair, with excellent fastness to light and washing. Thereby, dyeing of a wide range of color tone from yellow to red to further gray to dark brown can be carried out by combination of the various developing substances with the coupling components.

Description

【発明の詳細な説明】 ｃ座業上の利用分野〕 本発明は染色組成物に関し、更に詳細には毛受等の角質
繊維を高彩度に染色することができる角質繊維染色組成
物に関する。DETAILED DESCRIPTION OF THE INVENTION (c) Field of sedentary use] The present invention relates to a dyeing composition, and more particularly to a horny fiber dyeing composition capable of dyeing horny fibers such as hair flaps with high chroma.

〔従来の技術〕[Conventional technology]

毛髪等の角質繊維の染色には、従来よシ顕色吻質とカツ
プリング物質を組み合せて用いる、いわゆる酸化染色剤
が広く使用されている。この酸化染色剤は顕色物質とカ
ツプリング物質の酸化カッｆリングによって生じる、い
わゆる酸化色素が毛髪等を強く染色することを利用した
ものでめる。そして顕色物質としては、一般にｐ−フェ
ニレンシアミン誘導体、ｐ−アミンフェノール銹導体、
シアミノビリシン誘導体、４−７ミノビラゾロン誘導体
、複素環状ヒドラゾン等が使用されている。For dyeing keratinous fibers such as hair, so-called oxidative dyes, which are conventionally used in combination with color-developing proboscis and coupling substances, have been widely used. This oxidative dye utilizes the fact that the so-called oxidized dye, which is produced by oxidative cuffing of a color developing substance and a coupling substance, strongly dyes hair and the like. The color developing substances are generally p-phenylenecyamine derivatives, p-aminephenol rust conductors,
Cyaminoviricin derivatives, 4-7 minovirazolone derivatives, heterocyclic hydrazones, and the like are used.

〔発明が解決しようとする課題〕[Problem to be solved by the invention]

しかしながら、従来の酸化染色剤は、彩度、染着力およ
び盛ろう性において未だ満足すべきものではなかった。However, conventional oxidation dyes are still unsatisfactory in terms of chroma, dyeing power, and waxability.

〔課題を解決するための手段〕[Means to solve the problem]

そこで本発明者らは前記問題点を解決すべく種々検討を
重ねた結果、顕色物質として特定のトリアミノビリミシ
ン誘導体を使用することによシ、角質繊維を高彩度で強
い色調に染色することが可能となり、かつその染色は優
れた堅ろう性を有することを見出し、本発明を完成した
。The inventors of the present invention have conducted various studies to solve the above-mentioned problems, and have found that by using a specific triamino birimicin derivative as a color developer, horny fibers can be dyed in strong colors with high saturation. The present invention has been completed based on the discovery that this dyeing is possible and has excellent fastness.

すなわち、本発明は顕色物質およびカップリング物質を
含有する染色組成物において、顕色物質が、次の一般式
（Ｉ）または（１′）で表わされるトリアミノピリミジ
ン誘導体く以下化合’ＩＩ！ｌ　（Ｉ）と称する）であ
ることを特徴とする角質繊維染色組成物を提供するもの
である。That is, the present invention provides a dyeing composition containing a color developer and a coupling substance, wherein the color developer is a triaminopyrimidine derivative represented by the following general formula (I) or (1') or a compound 'II! 1 (referred to as I)).

本発明に使用される化合物（１）の塩としては、塩酸、
硫酸、リン酸等の無機酸または、炭素数１〜２０の直鎖
もしくは分岐アルキル基を有するカルメン酸、ヒドロキ
シカルボン酸、−リヒドロキシカルボン嫉、スルホン酸
等の有機酸が挙げられ、塩酸、硫酸、リン酸、酢酸、プ
ロピオン酸、乳酸、クエン酸等が好ましい。The salt of compound (1) used in the present invention includes hydrochloric acid,
Examples include inorganic acids such as sulfuric acid and phosphoric acid, and organic acids such as carmenic acid, hydroxycarboxylic acid, -lyhydroxycarboxylic acid, and sulfonic acid having a linear or branched alkyl group having 1 to 20 carbon atoms. Hydrochloric acid, sulfuric acid, etc. , phosphoric acid, acetic acid, propionic acid, lactic acid, citric acid and the like are preferred.

本発明染色組成物に使用されるカップリング物質として
は、通常酸化染毛剤に慣用されているものであれば特に
制限されないが、例えばα−す７トール、０−クレゾー
ル、　ｍ　−クレゾール、２，６−ジメチルフェノール
、２．５−ジメチルフェノール、３，４−ジメチルフェ
ノール、３，５−ジメチルフェノール、ベンズカテキン
、ピロガロール、１．５−ジヒドロキシナフタレン、１
，７−ジヒドロキシナフタレン、５−アミノ−２−メチ
ルフェノール、ヒドロキノン、２，４−ゾアミノアニン
ール、ｍ−トルイレンシアミン、４−アミンフェノール
、レゾルシン、レゾルシンモノメチルエーテル、ｍ−フ
ェニレンシアミン、１−フェニル−３−）ｆルー５−ピ
ラゾロン、１−フェニル−３−アミノ−５−ピラゾロン
、１−フェニル−３，５−ゾケトービラゾリゾン、１−
メチル−７−ゾメチル−アミノ−４−ヒドロキシキノロ
ン−２，１−アミノ−３−アセチル−アセトアミノ−４
−二トロベンゾール、１−アミノ−３−シアンアセチル
−アミノ−４−ニトロ−ペンゾール、ｍ−アミンフェノ
ール、４−クロロレゾルシン、２−メチルレゾルシン、
２．４−Ｐアミノフェノキシエタノール、２，６−ジア
ミノビリジン、３，５−シアミノ−トリフロロメチルベ
ンゼン、２，４−シアミノ−フロロベンゼン、３．５−
シアミノ−フロロベンゼン、２．４−シアミノ−６−ヒ
ドロキシピリミジン、２，４．６−トリアミノビリミシ
ン、２−アミノ−４，６−ジヒドロキシピリミジン、４
−アミノ−２，６−ジヒドロキシビリミジン、４，６−
ゾアミノー２−ヒドロキシピリミジン、ｐ−ニトロ−〇
−フェニレンシアミン、２−アミノ−５−ニトロフェノ
ール、ｐ−ニトロ−ｍ−フェニレンシアミン、〇−二ヒ
トローｐ−フェニレンシアミン２−アミノ−４−ニトロ
フェノール等が挙げられる。The coupling substance used in the dyeing composition of the present invention is not particularly limited as long as it is commonly used in oxidative hair dyes, but examples include α-su7toll, 0-cresol, m-cresol, 2 , 6-dimethylphenol, 2.5-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, benzcatechin, pyrogallol, 1.5-dihydroxynaphthalene, 1
, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, hydroquinone, 2,4-zoaminoaninol, m-tolylenecyamine, 4-aminephenol, resorcin, resorcin monomethyl ether, m-phenylenecyamine, 1-phenyl-3-)f-5-pyrazolone, 1-phenyl-3-amino-5-pyrazolone, 1-phenyl-3,5-zoketovirazolizone, 1-
Methyl-7-zomethyl-amino-4-hydroxyquinolone-2,1-amino-3-acetyl-acetamino-4
-nitrobenzole, 1-amino-3-cyanoacetyl-amino-4-nitro-penzole, m-aminephenol, 4-chlororesorcin, 2-methylresorcin,
2.4-P aminophenoxyethanol, 2,6-diaminopyridine, 3,5-cyamino-trifluoromethylbenzene, 2,4-cyamino-fluorobenzene, 3.5-
Cyamino-fluorobenzene, 2,4-cyamino-6-hydroxypyrimidine, 2,4,6-triaminovirimicin, 2-amino-4,6-dihydroxypyrimidine, 4
-amino-2,6-dihydroxypyrimidine, 4,6-
Zoamino-2-hydroxypyrimidine, p-nitro-〇-phenylenecyamine, 2-amino-5-nitrophenol, p-nitro-m-phenylenecyamine, 〇-dihtro p-phenylenecyamine 2-amino-4- Examples include nitrophenol.

本発明に使用される顕色物質は、レゾルシン系のカップ
リング物質と組み合せることによシ高彩度の赤系色調が
得られ、特にレゾルシン、２−メチルレゾルシン、４−
クロロレゾルシンをカップリング物質とすると、高彩度
のオレンゾル赤の色調が得られる。また、本発明に使用
される顕色物質を、シアミノビリシン系のカップリング
物質と組み合わせることによシアざやかな黄色が得られ
、特に４−ゾロビル−２，６−ジアミノピリジン、３゜
４−ジメチル−２，６−ゾアミノビリジンをカップリン
グ物質として用いると高彩度の黄色が得られる。When the color developing substance used in the present invention is combined with a resorcinol-based coupling substance, a red tone with high chroma can be obtained, and in particular, resorcinol, 2-methylresorcinol, 4-
When chlororesorcinol is used as a coupling substance, a highly saturated orensol red color tone can be obtained. In addition, by combining the color developing substance used in the present invention with a cyaminobilicin-based coupling substance, a bright yellow color can be obtained, and in particular, 4-zorobyl-2,6-diaminopyridine, 3゜4-dimethyl- When 2,6-zoaminopyridine is used as a coupling substance, a highly saturated yellow color is obtained.

本発明の染色組成物中の顕色物質とカップリング物質の
配合割合は、一方の成分が他方に比べ過剰となっていて
もさしつかえないが、モル比で１：０．５〜１：２程度
であることが好ましい。また顕色物質およびカップリン
グ物質は、ともに単独でも二櫨以上を組み合せても使用
することができる。The mixing ratio of the color developing substance and the coupling substance in the dyeing composition of the present invention may be in excess of one component compared to the other, but the molar ratio is approximately 1:0.5 to 1:2. It is preferable that Further, the color developing substance and the coupling substance can be used alone or in combination of two or more.

また本発明の染色組成物には所望の色調を得るため必要
でめれば、更に公知の顕色物質、通常の１染性染料等を
配合することができる。Further, the dyeing composition of the present invention may further contain known color developing substances, common one-color dyes, and the like, if necessary, in order to obtain a desired color tone.

本発明染色組成物は、空気中の酸素によっても酸化カッ
プリングを生起し、毛髪等を染色するが、化学的酸化剤
を添加することによシ酸化カツプリングを生起させるの
が好ましい。特に好ましい酸化剤としては、過酸化水素
：過酸化水素が尿素、メラミン又は５！ＩｒＩＲナトリ
ウムに付加した生成物；このような過酸化水素付加物と
過酸化カリウムー二硫酸との混合物等が挙げられる。The dyeing composition of the present invention also causes oxidative coupling with oxygen in the air and dyes hair, etc., but it is preferable to cause oxidative coupling by adding a chemical oxidizing agent. Particularly preferred oxidizing agents include hydrogen peroxide: hydrogen peroxide is urea, melamine or 5! Products added to IrIR sodium; mixtures of such hydrogen peroxide adducts and potassium peroxide-disulfuric acid, and the like.

本発明の染色組成物は通常、クリーム、エマルション、
グル、溶液等の剤型で提供されるのが好ましい。このよ
うな剤型とするには、前記顕色物質およびカップリング
物質に、通常化粧品分野において用いられる湿潤剤（乳
化剤）、可溶化剤、増粘剤、安定化剤、感触向上剤、整
髪基剤、香料等を添加し、常法に従って製造すればよい
。ここで用いられる湿調剤（乳化剤）としては、例えば
アルキルベンゼンスルホネート、脂肪アルコールサルフ
ェート、アルキルスルホネート、脂肪酸アルカノールア
ミド、エチレンオキシドと脂肪アルコールとの付加生成
物等が挙げられる。また増粘剤としては、例えばメチル
セルロース、デンプン、高級脂肪アルコール、ノＱラフ
イン油、脂肪酸等が挙げられ、安定化剤としては、例え
ば亜硫酸塩等の還元剤、ヒドロキノン酵導体、キレート
剤等が挙げられ、感触向上剤、整髪基剤としては、例え
ばシリコーン、高級アルコール、各種非イオン界面活性
剤等の油剤、各種のカチオンビリマー等が挙げられる。The dyeing composition of the present invention is usually a cream, an emulsion,
It is preferably provided in a dosage form such as a gel or a solution. In order to form such a dosage form, in addition to the color developer and the coupling substance, wetting agents (emulsifiers), solubilizers, thickeners, stabilizers, feel improvers, and hair styling groups, which are commonly used in the cosmetics field, are added. It may be manufactured according to a conventional method by adding agents, fragrances, etc. Examples of the moisture conditioner (emulsifier) used here include alkylbenzene sulfonates, fatty alcohol sulfates, alkyl sulfonates, fatty acid alkanolamides, addition products of ethylene oxide and fatty alcohols, and the like. Further, examples of thickeners include methyl cellulose, starch, higher fatty alcohols, No-Q rough oil, fatty acids, etc., and examples of stabilizers include reducing agents such as sulfites, hydroquinone fermentation conductors, chelating agents, etc. Examples of feel improvers and hair styling bases include silicones, higher alcohols, oils such as various nonionic surfactants, and various cationic birimers.

これらの剤をにおける顕色物質とカップリング物質の配
合量は、合計で０．２〜５重童チ（以下単にチで示す）
、特に１〜３チが好ましい。湿潤剤（乳化剤）は通常０
．５〜３０チ、増粘剤は０．１〜２５チ配合されるのが
好ましい。The total amount of the color developing substance and coupling substance in these agents is 0.2 to 5 times the amount (hereinafter simply referred to as ``chi'').
, particularly preferably 1 to 3 inches. Wetting agent (emulsifier) is usually 0
．． Preferably, the amount of thickener is 0.1 to 25.

またこれらの剤槃において、組成物全体の−は８〜１０
程度に調整されるのが好ましい。In addition, in these formulations, the - of the entire composition is 8 to 10.
It is preferable to adjust it to a certain degree.

本発明染色組成物を用いて角質繊維の染色を実施するに
は、例えば本発明染色組成物に酸化剤を添加して酸化カ
ップリングを行い染色液を調製し、この染色液を角質繊
維に適用し、１０〜５０分、好ましくは２５〜３５分前
後の作用時間をおいて角質繊維を洗浄した後乾燥するこ
とにより行なわれる。ここで染色液の適用は１５〜４０
℃で行なわれる。In order to dye horny fibers using the dyeing composition of the present invention, for example, an oxidizing agent is added to the dyeing composition of the present invention to perform oxidative coupling to prepare a dyeing solution, and this dyeing solution is applied to the horny fibers. The keratinous fibers are then washed for an action time of 10 to 50 minutes, preferably 25 to 35 minutes, and then dried. Here, the application of staining solution is 15 to 40
It is carried out at ℃.

〔発明の効果〕〔Effect of the invention〕

本発明の染色組成物を用いて角質繊維を染色すれば、顕
色物質とカッｆ　リング物質の組み合せにより黄〜赤〜
青さらに灰色〜黒褐色まで幅広い染色が可能であシ、そ
の色調は高彩度である。特に、レゾルシン系のカップリ
ング物質と組み合せることによシ高彩度の赤系色調が、
またアミノビリシン系のカップリング物質と組み合せる
ことによシ高彩度の黄色が得られる。しかも得られた色
調は良好な耐光性、耐洗浄性及び耐摩擦性を有している
。When keratinous fibers are dyed using the dyeing composition of the present invention, the combination of color developing substance and cuffing substance produces yellow to red color.
It is possible to dye a wide range of colors from blue to gray to blackish brown, and the color tones are highly saturated. In particular, when combined with a resorcinol-based coupling substance, a highly saturated red tone can be created.
In addition, by combining it with an aminobilicin-based coupling substance, a highly saturated yellow color can be obtained. Moreover, the obtained color tone has good light fastness, wash resistance and abrasion resistance.

〔実施例〕〔Example〕

次に実施例を挙げて本発明の詳細な説明するが、本発明
はこれによって制限されるものではない。EXAMPLES Next, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.

実施例１ ベース組成： （３ｂ） オレイン酸 オレインはジェタノールアミド　　　　　　　　　８オ
レイルアルコール エタノール　　　　　　　　　　　　１５ゾロピレング
リコール　　　　　　　　　　　　１０塩化アンモニウ
ム　　　　　　　　　　　　　　　３２５チアンモニア
　　　　　　　　　　　　　　　７水　　　　　　　　
　　　　　　　　　　　　　　　３５上記組成からなる
ベース１００を中に４゜５．６−１リアミノ−２（１）
１）−ビリミシンチオン０．０１モル及び表１に示すカ
ツプリング物質０．０１モルを混入した。次いで組成物
の−をアンモニアにて９．５に調整することによシ、本
発明染色組成物を製造した。Example 1 Base composition: (3b) Oleic acid is jetanolamide 8 Oleyl alcohol ethanol 15 Zoropylene glycol 10 Ammonium chloride 325 Thiammonia 7 Water
35 4゜5.6-1 riamino-2 (1) in the base 100 consisting of the above composition
1) 0.01 mol of -virimisynthione and 0.01 mol of the coupling substance shown in Table 1 were mixed. Next, the - of the composition was adjusted to 9.5 with ammonia to produce a dyeing composition of the present invention.

本発明染色組成物１００ｔに対し、等重量の６％過酸化
水素水溶液を加えて染色液を調製した。この染色液を白
毛混じシの入毛に塗布し、３０℃で３０分間放置した。A dyeing solution was prepared by adding an equal weight of 6% hydrogen peroxide aqueous solution to 100 tons of the dyeing composition of the present invention. This dye solution was applied to the hair of a mixed white hair and left at 30° C. for 30 minutes.

次いで毛髪を通常のシャンプーで洗浄し、乾燥した。The hair was then washed with regular shampoo and dried.

得られた染色の色調を観察した結果を表１に示す。Table 1 shows the results of observing the color tone of the obtained dyeing.

以下余白Margin below

Claims (1)

【特許請求の範囲】 １、顕色物質およびカツプリング物質を含有する染色組
成物において、顕色物質が、次の一般式（ I ）または
（ I ′） ▲数式、化学式、表等があります▼（ I ） ▲数式、化学式、表等があります▼（ I ′） で表わされるトリアミノピリミジン誘導体またはその塩
であることを特徴とする角質繊維染色組成物。 ２、カツプリング物質が、レゾルシン、２−メチルレゾ
ルシン及び４−クロロレゾルシンからなる群より選ばれ
る１種もしくは２種以上を含有するものである請求項１
の角質繊維染色組成物。 ３、カツプリング物質が、４−プロピル−２，６−ジア
ミノピリジン、３，４−ジメチル−２，６−ジアミノピ
リジンの一方または両方を含有するものである請求項１
の角質繊維染色組成物。[Claims] 1. In the dyeing composition containing a color developer and a coupling substance, the color developer has the following general formula (I) or (I') ▲Mathematical formula, chemical formula, table, etc.▼( I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I') A keratin fiber dyeing composition characterized by being a triaminopyrimidine derivative or a salt thereof. 2. Claim 1, wherein the coupling substance contains one or more selected from the group consisting of resorcin, 2-methylresorcin, and 4-chlororesorcin.
horny fiber dyeing composition. 3. Claim 1, wherein the coupling substance contains one or both of 4-propyl-2,6-diaminopyridine and 3,4-dimethyl-2,6-diaminopyridine.
horny fiber dyeing composition.
JP63169571A 1988-07-07 1988-07-07 Keratin fiber dyeing composition Expired - Fee Related JP2526099B2 (en)

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