JP3053939B2 - Keratinized fiber dyeing composition - Google Patents

Keratinized fiber dyeing composition

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Publication number
JP3053939B2
JP3053939B2 JP3333495A JP33349591A JP3053939B2 JP 3053939 B2 JP3053939 B2 JP 3053939B2 JP 3333495 A JP3333495 A JP 3333495A JP 33349591 A JP33349591 A JP 33349591A JP 3053939 B2 JP3053939 B2 JP 3053939B2
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JP
Japan
Prior art keywords
substance
dyeing composition
fiber dyeing
present
coupling
Prior art date
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JP3333495A
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Japanese (ja)
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JPH05163124A (en
Inventor
真彦 小川
次朗 川瀬
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Kao Corp
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Kao Corp
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Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【産業上の利用分野】本発明は染色組成物に関し、更に
詳細には毛髪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。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dyeing composition, and more particularly to a keratinous fiber dyeing composition capable of dyeing keratinous fibers such as hair with high chroma.

【０００２】[0002]

【従来の技術】毛髪等の角質繊維の染色には、従来より
顕色物質とカッ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
は顕色物質とカップリング物質の酸化カップリングによ
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ある。ここでは顕色物質として、
一般にｐ−フェニレンジアミン誘導体、ｐ−アミノフェ
ノール誘導体、ジアミノピリジン誘導体、４−アミノピ
ラゾロン誘導体、複素環状ヒドラゾン等が使用されてき
ている。2. Description of the Related Art For dyeing keratinous fibers such as hair, a so-called oxidation dye, which uses a combination of a color developing substance and a coupling substance, has been widely used. This oxidative dye utilizes the fact that a so-called oxidative dye, which is generated by oxidative coupling of a color developing substance and a coupling substance, strongly dyes hair and the like. Here, as a developer,
Generally, p-phenylenediamine derivatives, p-aminophenol derivatives, diaminopyridine derivatives, 4-aminopyrazolone derivatives, heterocyclic hydrazones and the like have been used.

【０００３】[0003]

【発明が解決しようとする課題】しかしながら、前記従
来の酸化染色剤は、彩度、染着力及び堅ろう性において
満足すべきものは少ない。これらの点を改良すべきもの
としてトリアミノピリミジン誘導体を含有する染色剤が
提案されている（特開平２−１９５７６号公報）が、中
性付近pH領域での溶解性に劣る、製剤上難がある等の問
題点は未だ払拭されてはいない。However, the above-mentioned conventional oxidative dyes are not satisfactory in color saturation, dyeing power and fastness. In order to improve these points, a dye containing a triaminopyrimidine derivative has been proposed (JP-A-2-19576), but it has poor solubility in a pH region near neutrality and is difficult to formulate. The problems such as have not been eliminated yet.

【０００４】[0004]

【課題を解決するための手段】本発明者らは、かかる実
情に鑑み、鋭意検討した結果、顕色物質として後述の特
定のトリアミノピリミジン誘導体を使用することにより
従来品よりも低pHで溶解でき製剤の容易な、しかも染色
効果にすぐれる角質繊維染色剤の得られることを見出
し、本発明を完成するに至った。Means for Solving the Problems In view of such circumstances, the present inventors have conducted intensive studies. As a result, the use of a specific triaminopyrimidine derivative described later as a color developing substance enables the dissolution at a lower pH than conventional products. The present inventors have found that a keratinous fiber dye which is easy to prepare and has excellent dyeing effect can be obtained, and the present invention has been completed.

【０００５】すなわち、本発明は、顕色物質及びカップ
リング物質を含有する角質繊維染色組成物において、該
顕色物質が下記式（１）That is, the present invention relates to a keratinous fiber dyeing composition containing a color developing substance and a coupling substance, wherein the color developing substance is represented by the following formula (1):

【０００６】[0006]

【化２】 Embedded image

【０００７】で表わされる２，４，５−トリアミノ−６
−クロロピリミジン又はその塩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。2,4,5-triamino-6 represented by
-It provides a keratinous fiber dyeing composition characterized by being chloropyrimidine or a salt thereof.

【０００８】本発明に使用される化合物（１）は、例え
ば「ジャーナル オブ オーガニック ケミストリー」
２７巻、４５１８〜４５２３頁（１９６２年）に記載の
方法に従い製造することができる。The compound (1) used in the present invention is, for example, “Journal of Organic Chemistry”
27, 4518-4523 (1962).

【０００９】また、本発明に使用される化合物（１）の
塩としては、塩酸、硫酸、リン酸等の無機酸との塩、又
は炭素数１〜２０の直鎖もしくは分岐アルキル基を有す
るカルボン酸、ヒドロキシカルボン酸、ポリヒドロキシ
カルボン酸、スルホン酸等の有機酸との塩が挙げられ、
塩酸、硫酸、リン酸、酢酸、プロピオン酸、乳酸、クエ
ン酸等との塩が好ましい。The salt of the compound (1) used in the present invention may be a salt with an inorganic acid such as hydrochloric acid, sulfuric acid or phosphoric acid, or a carboxylic acid having a linear or branched alkyl group having 1 to 20 carbon atoms. Acids, hydroxycarboxylic acids, polyhydroxycarboxylic acids, salts with organic acids such as sulfonic acid,
Salts with hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, propionic acid, lactic acid, citric acid and the like are preferred.

【００１０】本発明角質繊維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−ナフ
トール、ｏ−クレゾール、ｍ−クレゾール、２，５−ジ
メチルフェノール、２，６−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−ジアミノアニソール、ｍ−トルイレンジアミン、４
−アミノフェノール、レゾルシン、レゾルシンモノメチ
ルエーテル、ｍ−フェニレンジアミン、１−フェニル−
３−メチル−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−ジケト−
ピラゾリジン、１−メチル−７−ジメチル−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−ニトロベンゾール、１−アミノ−
３−シアンアセチル−アミノ−４−ニトロ−ベンゾー
ル、ｍ−アミノフェノール、４−クロロレゾルシン、２
−メチルレゾルシン、２，４−ジアミノフェノキシエタ
ノール、２，６−ジアミノピリジン、３，５−ジアミノ
−トリフロロメチルベンゼン、２，４−ジアミノ−フロ
ロベンゼン、３，５−ジアミノ−フロロベンゼン、２，
４−ジアミノ−６−ヒドロキシピリミジン、２，４，６
−トリアミノピリミジン、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
ピリミジン、４，６−ジアミノ−２−ヒドロキシピリミ
ジン、ｐ−ニトロ−ｏ−フェニレンジアミン、２−アミ
ノ−５−ニトロフェノール、ｐ−ニトロ−ｍ−フェニレ
ンジアミン、ｏ−ニトロ−ｐ−フェニレンジアミン、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 keratinous fiber dyeing composition of the present invention is not particularly limited as long as it is generally used for oxidative hair dyes. For example, α-naphthol, o-cresol, m- Cresol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,
4-dimethylphenol, 3,5-dimethylphenol, benzcatechin, pyrogallol, 1,5-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 5
-Amino-2-methylphenol, hydroquinone, 2,
4-diaminoanisole, m-toluylenediamine, 4
-Aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 1-phenyl-
3-methyl-5-pyrazolone, 1-phenyl-3-amino-5-pyrazolone, 1-phenyl-3,5-diketo-
Pyrazolidine, 1-methyl-7-dimethyl-amino-4
-Hydroxyquinolone-2,1-amino-3-acetyl-acetoamino-4-nitrobenzol, 1-amino-
3-cyanoacetyl-amino-4-nitro-benzol, m-aminophenol, 4-chlororesorcin, 2
-Methylresorcin, 2,4-diaminophenoxyethanol, 2,6-diaminopyridine, 3,5-diamino-trifluoromethylbenzene, 2,4-diamino-fluorobenzene, 3,5-diamino-fluorobenzene, 2,
4-diamino-6-hydroxypyrimidine, 2,4,6
-Triaminopyrimidine, 2-amino-4,6-dihydroxypyrimidine, 4-amino-2,6-dihydroxypyrimidine, 4,6-diamino-2-hydroxypyrimidine, p-nitro-o-phenylenediamine, 2-amino -5-nitrophenol, p-nitro-m-phenylenediamine, o-nitro-p-phenylenediamine, 2
-Amino-4-nitrophenol and the like.

【００１１】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り高彩度
の赤系色調が得られる。特にレゾルシン、２−メチルレ
ゾルシン及び４−クロロレゾルシンから選ばれる少なく
とも１種をカップリング物質とすると、高彩度のオレン
ジ〜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、ジアミノピリジン系のカップリング物質と組
み合わせることによりあざやかな黄色が得られる。特に
４−プロピル−２，６−ジアミノピリジン及び３，４−
ジメチル−２，６−ジアミノピリジンの一方又は双方を
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 high chroma reddish color tone can be obtained. In particular, when at least one selected from resorcinol, 2-methylresorcinol and 4-chlororesorcinol is used as the coupling substance, a high chroma orange-red color tone is obtained. In addition, a vivid yellow color can be obtained by combining the color developing substance used in the present invention with a diaminopyridine-based coupling substance. In particular, 4-propyl-2,6-diaminopyridine and 3,4-
When one or both of dimethyl-2,6-diaminopyridine is used as a coupling substance, a highly saturated yellow is obtained.

【００１２】本発明角質繊維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
質及びカップリング物質は、ともに単独でも二種以上を
組み合せても使用することができる。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あれば、更に公
知の顕色物質、通常の直染性染料等を配合することがで
きる。The mixing ratio of the color developing substance and the coupling substance in the keratinous fiber dyeing composition of the present invention may be in excess of one component as compared with the other, but the molar ratio is 1: 1:
It is preferably about 0.5 to 1: 2. Further, the color-developing substance and the coupling substance can be used either alone or in combination of two or more. The dyeing composition of the present invention may further contain a known color developing substance, a normal direct dye or the like, if necessary to obtain a desired color tone.

【００１３】本発明角質繊維染色組成物は、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り酸化カップ
リングを生起させるものが好ましい。特に好ましい酸化
剤としては、過酸化水素；過酸化水素か尿素、メラミン
又は硼酸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−二硫酸との混合物等が
挙げられる。The keratinous fiber dyeing composition of the present invention causes oxidative coupling even by oxygen in the air and dyes hair, etc., but preferably generates oxidative coupling by adding a chemical oxidizing agent. . Particularly preferred oxidizing agents include hydrogen peroxide; hydrogen peroxide or a product obtained by adding urea, melamine, or sodium borate; a mixture of such a hydrogen peroxide adduct and potassium peroxide-disulfuric acid.

【００１４】本発明角質繊維染色組成物は通常、クリー
ム、エマルジョン、ゲル、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
及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潤剤（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、パラフィン油、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
ン誘導体、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、各種のカチオンポリマ
ー等が挙げられる。The keratinous fiber dyeing composition of the present invention is usually preferably provided in the form of a cream, emulsion, gel, solution or the like. In order to obtain such a dosage form, the developing substance and the coupling substance are added to a wetting agent (emulsifier), a solubilizer, a thickener, a stabilizer, a feel improver, and a hair styling agent which are usually used in the cosmetics field. An agent, a fragrance and the like may be added to produce according to a conventional method. Examples of the wetting agent (emulsifier) used here include alkylbenzene sulfonate,
Fatty alcohol sulfates, alkyl sulfonates,
Fatty acid alkanolamides, addition products of ethylene oxide and fatty alcohols and the like can be mentioned. Examples of the thickener include methyl cellulose, starch, higher fatty alcohols, paraffin oil, fatty acids, and the like. Examples of the stabilizer include a reducing agent such as sulfite, a hydroquinone derivative, a chelating agent, and the like. Examples of the improving agent and the hair styling base include silicones, higher alcohols, oils such as various nonionic surfactants, and various cationic polymers.

【００１５】これらの剤型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重量％（以下単
に％で示す）、特に１〜３％が好ましい。湿潤剤（乳化
剤）は通常０．５〜３０％、増粘剤は０．１〜２５％配
合されるのが好ましい。[0015] In these dosage forms, the compounding amount of the color developing substance and the coupling substance is preferably 0.2 to 5% by weight (hereinafter simply indicated as%), particularly preferably 1 to 3%. It is preferable that the wetting agent (emulsifier) is usually blended in an amount of 0.5 to 30%, and the thickener is incorporated in an amount of 0.1 to 25%.

【００１６】またこれらの剤型において、組成物全体の
pHは６〜１１程度に調整されるのが好ましい。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。ここで染
色液の適用は１５〜４０℃で行なわれる。In these dosage forms, the composition as a whole
The pH is preferably adjusted to about 6 to 11. In order to dye keratinous 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 keratinous fibers. Then, the keratinous fibers are washed and dried after an action time of about 10 to 50 minutes, preferably about 25 to 35 minutes. Here, the application of the staining solution is carried out at 15 to 40 ° C.

【００１７】[0017]

【発明の効果】本発明角質繊維染色組成物は、従来より
も低pHで溶解可能で製剤の容易な、しかも染色性の向上
したものである。そして、本発明の染色組成物を用いて
角質繊維を染色すれば、顕色物質とカップリング物質と
の組み合せにより黄〜赤〜青更に灰色〜黒褐色まで幅広
い染色が可能であり、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
り高彩度の赤系色調が、またアミノピリジン系のカップ
リング物質と組み合せることにより高彩度の黄色が得ら
れる。しかも得られた染色は光、洗浄及び摩擦等に対し
優れた耐変褪色性を示す。Industrial Applicability The keratinous fiber dyeing composition of the present invention can be dissolved at a lower pH than in the prior art, is easy to prepare, and has improved dyeing properties. Then, if the keratinous fiber is dyed using the dyeing composition of the present invention, a wide range of dyeing from yellow to red to blue and further gray to blackish brown is possible by a combination of a color developing substance and a coupling substance, and the color tone is high chroma. It is. In particular,
Combination with a resorcinol-based coupling substance produces a highly-saturated reddish tone, and combination with an aminopyridine-based coupling substance produces a highly-saturated yellow. Moreover, the obtained dyeing shows excellent resistance to discoloration and fading to light, washing and rubbing.

【００１８】[0018]

【実施例】以下に本発明を実施例により具体的に説明す
るが、本発明はそれらにより限定されるものではない。EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the invention thereto.

【００１９】実施例１ 下記組成のベースを調製した。 Example 1 A base having the following composition was prepared.

【００２０】上記ベース１００ｇ中に、２，４，５−ト
リアミノ−６−クロロピリミジンを０．０１モル及び表
１に示すカップリング物質をそれぞれ０．０１モル混入
し、次いでそれぞれのpHを１０として、本発明角質繊維
染色組成物１〜１３を調製した。In 100 g of the above base, 0.01 mol of 2,4,5-triamino-6-chloropyrimidine and 0.01 mol of the coupling substance shown in Table 1 were mixed respectively. The inventive keratinous fiber dyeing compositions 1 to 13 were prepared.

【００２１】上記各組成物１００ｇ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
色液を白毛混じりの人毛に塗布し、３０℃で３０分間放
置した。次いで毛髪を通常のシャンプーで洗浄し、乾燥
した。得られた染色の色調を観察した結果を表１に示
す。For 100 g of each of the above compositions, an equal weight of 6
% Aqueous hydrogen peroxide solution was added to prepare a staining solution. This dyeing solution was applied to human hair mixed with white hair, and left at 30 ° C. for 30 minutes. The hair was then washed with normal shampoo and dried. Table 1 shows the results of observing the color tone of the obtained dye.

【００２２】[0022]

【表１】 [Table 1]

【００２３】実施例２ 実施例１記載の組成ベース１００ｇ中に本発明に使用の
化合物（１）及び下記式（２）で表わされる化合物をそ
れぞれ０．０１モル混入させた。Example 2 To 100 g of the composition base described in Example 1, 0.01 mol of the compound (1) used in the present invention and 0.01 mol of the compound represented by the following formula (2) were mixed.

【００２４】[0024]

【化３】 Embedded image

【００２５】更に、両者にはカップリング剤としてレゾ
ルシンをそれぞれ０．０１モル混入せしめ、本発明品及
び比較品組成物を得た。次いでそれぞれの組成物のpHを
アンモニアを用いて７、１０及び１１に調整した。Further, 0.01 mol of resorcinol was mixed in each of them as a coupling agent to obtain a product of the present invention and a comparative product. The pH of each composition was then adjusted to 7, 10 and 11 with ammonia.

【００２６】それぞれの組成物の各pHにおける溶解性を
下記の判定基準により判定した。 ○：完全に溶解する。 ×：ほとんど溶解しない。 結果を表２に示す。The solubility of each composition at each pH was determined according to the following criteria. ：: Completely dissolved. X: Almost no dissolution. Table 2 shows the results.

【００２７】[0027]

【表２】 [Table 2]

【００２８】表２より明らかなごとく、本発明組成物
は、広範囲のpH領域において良好な溶解性を示す。As is apparent from Table 2, the composition of the present invention shows good solubility in a wide range of pH.

フロントページの続き (56)参考文献 特開 平２−174710（ＪＰ，Ａ) 特開 昭52−130930（ＪＰ，Ａ) 特開 昭50−88242（ＪＰ，Ａ) 特開 昭57−183710（ＪＰ，Ａ) 特開 平２−172909（ＪＰ，Ａ) 特開 昭56−36406（ＪＰ，Ａ) 特開 平２−19576（ＪＰ，Ａ) 特表 平５−500224（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) A61K 7/13 Continuation of the front page (56) References JP-A-2-174710 (JP, A) JP-A-52-130930 (JP, A) JP-A-50-88242 (JP, A) JP-A-57-183710 (JP) JP-A-2-172909 (JP, A) JP-A-56-36406 (JP, A) JP-A-2-19576 (JP, A) Japanese Translation of PCT Application No. 5-500224 (JP, A) (58) Field surveyed (Int.Cl. 7 , DB name) A61K 7/13

Claims (3)

(57)【特許請求の範囲】(57) [Claims] 【請求項１】 顕色物質及びカップリング物質を含有す
る角質繊維染色組成物において、該顕色物質が、下記式
（１） 【化１】 で表わされる２，４，５−トリアミノ−６−クロロピリ
ミジン又はその塩であることを特徴とする角質繊維染色
組成物。1. A keratinous fiber dyeing composition containing a color developing substance and a coupling substance, wherein the color developing substance is represented by the following formula (1): A keratinous fiber dyeing composition, which is 2,4,5-triamino-6-chloropyrimidine represented by the formula: or a salt thereof. 【請求項２】 カップリング物質が、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
より選ばれる少なくとも１種を含むものである請求項１
記載の角質繊維染色組成物。2. The coupling substance is resorcinol, 2-
2. A composition comprising at least one selected from the group consisting of methylresorcinol and 4-chlororesorcinol.
A keratinous fiber dyeing composition according to the above. 【請求項３】 カップリング物質が、４−プロピル−
２，６−ジアミノピリジン及び３，４−ジメチル−２，
６−ジアミノピリジンの一方又は双方を含むものである
請求項１記載の角質繊維染色組成物。3. The method according to claim 1, wherein the coupling substance is 4-propyl-
2,6-diaminopyridine and 3,4-dimethyl-2,
The keratinous fiber dyeing composition according to claim 1, which comprises one or both of 6-diaminopyridine.
JP3333495A 1991-12-17 1991-12-17 Keratinized fiber dyeing composition Expired - Fee Related JP3053939B2 (en)

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JPH05163124A JPH05163124A (en) 1993-06-29
JP3053939B2 true JP3053939B2 (en) 2000-06-19

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