JP2016193877A - Photosensitive hair dye - Google Patents

Photosensitive hair dye Download PDF

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JP2016193877A
JP2016193877A JP2015084563A JP2015084563A JP2016193877A JP 2016193877 A JP2016193877 A JP 2016193877A JP 2015084563 A JP2015084563 A JP 2015084563A JP 2015084563 A JP2015084563 A JP 2015084563A JP 2016193877 A JP2016193877 A JP 2016193877A
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hair
hair dye
zinc
acid
photosensitive
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JP6816852B2 (en
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弘之 岩崎
Hiroyuki Iwasaki
弘之 岩崎
昌宏 川上
Masahiro Kawakami
昌宏 川上
浩 中橋
Hiroshi Nakabashi
浩 中橋
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Picaso Cosmetic Laboratory Ltd
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Abstract

PROBLEM TO BE SOLVED: To provide a photosensitive hair dye that inhibits the discoloration of hair after dying.SOLUTION: A hair dye comprises laccaic acid and silver salt.SELECTED DRAWING: None

Description

本発明は、銀塩を含む感光性染毛剤に関する。  The present invention relates to a photosensitive hair dye containing a silver salt.

染毛剤は、性能の面から分類すると、一時染毛料、半永久染毛料、永久染毛剤など、種々に分類される。  Hair dyes are classified into various types such as temporary hair dyes, semi-permanent hair dyes, permanent hair dyes, and the like from the viewpoint of performance.

こられの染毛剤は、染毛の際の環境が厳しく、毛髪の損傷が問題となる。そのような毛髪の損傷が軽減され、安全性の高い染毛剤として、銀塩を用いた感光性染毛剤が、昔から知られている(例えば、特許文献1〜4)。  These hair dyes have a severe environment during hair dyeing, and hair damage becomes a problem. Photosensitive hair dyes using silver salts have been known for a long time as hair dyes with reduced hair damage and high safety (for example, Patent Documents 1 to 4).

しかしながら、上記感光性染毛剤を用いて染毛された毛髪は、パーマ処理または強い光の作用によって緑褐色〜ウグイス色に変色してしまうという問題がある。このように変色してしまうと、再度感光性染毛剤を用いても元の色には戻らない。  However, the hair dyed with the above photosensitive hair dye has a problem that the hair color changes from greenish brown to warbler due to permanent treatment or strong light action. If the color is changed in this way, the original color is not restored even if the photosensitive hair dye is used again.

特開2012−077005号公報JP 2012-077005 A 特開2011−116708号公報JP 2011-116708 A 特開2009−096786号公報JP 2009-096786 A 特開2009−143869号公報JP 2009-143869 A

本発明は、染毛後の毛髪の変色が抑制された感光性染毛剤を提供することを目的とする。  An object of this invention is to provide the photosensitive hair dye in which discoloration of the hair after hair dyeing was suppressed.

本発明の感光性染毛剤は、銀塩と、ラッカイン酸と、を含むことを特徴としている。  The photosensitive hair dye of the present invention is characterized by containing a silver salt and laccaic acid.

本発明の感光性染毛剤によれば、染毛後の毛髪の変色を抑制することができる。  According to the photosensitive hair dye of the present invention, discoloration of hair after hair dyeing can be suppressed.

以下、本発明の実施形態について説明する。  Hereinafter, embodiments of the present invention will be described.

[感光性染毛剤]
本発明の感光性染毛剤は、銀塩と、ラッカイン酸と、を含んでいる。
[Photosensitive hair dye]
The photosensitive hair dye of the present invention contains a silver salt and laccaic acid.

本発明に用いる銀塩としては、硫酸銀、乳酸銀、クエン酸銀等が挙げられる。従来から使われていた硝酸銀は、医薬品原料であることから化粧品、医薬部外品への配合が禁止されており、一般染毛剤として用いるには使用しづらい。これらの中で、染毛効果に優れる点で、硫酸銀が好ましい。  Examples of the silver salt used in the present invention include silver sulfate, silver lactate, and silver citrate. Conventionally used silver nitrate is a raw material for pharmaceuticals, so its incorporation into cosmetics and quasi-drugs is prohibited, and it is difficult to use it as a general hair dye. Among these, silver sulfate is preferable from the viewpoint of excellent hair dyeing effect.

これらの銀塩は、0.01〜2質量%、好ましくは0.1〜1.0質量%の割合で感光性染毛剤に配合される。銀塩の配合割合が0.01質量%未満では、十分な染毛効果が得られず、2質量%を超えると、製剤中で銀塩が析出する可能性がある。  These silver salts are blended in the photosensitive hair dye in a proportion of 0.01 to 2% by mass, preferably 0.1 to 1.0% by mass. If the blending ratio of the silver salt is less than 0.01% by mass, a sufficient hair dyeing effect cannot be obtained, and if it exceeds 2% by mass, the silver salt may be precipitated in the preparation.

本発明の感光性染毛剤は、ラッカイン酸を含む。このラッカイン酸は、好ましくは0.01〜10質量%、より好ましくは0.5〜5質量%の割合で感光性染毛剤に配合される。少なすぎると染色性に劣る場合があり、多すぎる場合にはそれ以上染色効果の向上が見込め無い。  The photosensitive hair dye of the present invention contains laccaic acid. This lacqueric acid is preferably blended in the photosensitive hair dye in a proportion of 0.01 to 10% by mass, more preferably 0.5 to 5% by mass. If the amount is too small, the dyeability may be inferior. If the amount is too large, the dyeing effect cannot be further improved.

また、本発明の感光性染毛剤には、銅塩または亜鉛塩を含有すること好ましい。
上記銅塩としては、グルコン酸銅、塩化第二銅、硫酸銅、PCA銅、アスパラギン酸銅、アセチルチロシネートメチルシラノール銅、アセチルメチオニン銅、アデノシン三リン酸銅、ウスニン酸銅等が挙げられる。
上記亜鉛塩としては、PCA亜鉛、アスコルビン酸亜鉛、アスパラギン酸亜鉛、アセチルメチオニン亜鉛、アデノシン三リン酸亜鉛、ウンデシレン酸亜鉛、クエン酸亜鉛、グリシン亜鉛、グリチルレチン酸亜鉛、グルコン酸亜鉛、ココアルキル硫酸亜鉛、コセス硫酸亜鉛、ステアリン酸亜鉛、パルミチン酸亜鉛、ピコリン酸亜鉛、ピリチオン亜鉛、フェノールスルホン酸亜鉛、ミリスチン酸亜鉛、ラウリン酸亜鉛、ラウロイルアスパラギン酸亜鉛、リシノレイン酸亜鉛、乳酸亜鉛、塩化亜鉛、炭酸亜鉛、硫化亜鉛、硫酸亜鉛、酢酸亜鉛等が挙げられる。
上記銅塩または亜鉛塩は、1種以上、任意の組み合わせで使用することができる。これらの銅塩および亜鉛塩の中でも、グルコン酸銅、グルコン酸亜鉛が特に好ましい。これらの銅塩および亜鉛塩は、好ましくは0.1〜10質量%、より好ましくは0.4〜5質量%の割合で感光性染毛剤に添加される。
上記銅塩または亜鉛塩を添加することにより、染毛色をさらに落ち着いた色にすることができ、また色落ちも防止することができる。
The photosensitive hair dye of the present invention preferably contains a copper salt or a zinc salt.
Examples of the copper salt include copper gluconate, cupric chloride, copper sulfate, PCA copper, copper aspartate, acetyl tyrosinate methyl silanol copper, acetyl methionine copper, adenosine triphosphate copper and usnic acid copper.
Examples of the zinc salt include PCA zinc, zinc ascorbate, zinc aspartate, zinc acetylmethionine, zinc adenosine triphosphate, zinc undecylenate, zinc citrate, glycine zinc, zinc glycyrrhetinate, zinc gluconate, and zinc cocoalkyl sulfate. , Zinc sesame sulfate, zinc stearate, zinc palmitate, zinc picolinate, zinc pyrithione, zinc phenolsulfonate, zinc myristate, zinc laurate, zinc lauroyl aspartate, zinc ricinoleate, zinc lactate, zinc chloride, zinc carbonate Zinc sulfide, zinc sulfate, zinc acetate and the like.
The said copper salt or zinc salt can be used 1 type or more and arbitrary combinations. Among these copper salts and zinc salts, copper gluconate and zinc gluconate are particularly preferable. These copper salts and zinc salts are preferably added to the photosensitive hair dye in a proportion of 0.1 to 10% by mass, more preferably 0.4 to 5% by mass.
By adding the copper salt or the zinc salt, the dyed hair color can be further subdued, and color fading can be prevented.

本発明の感光性染毛剤は、ラッカイン酸による染毛色の赤味を抑制するために、鉄塩を含むことが好ましい。鉄塩は、好ましくは0.01〜5質量%、より好ましくは0.05〜1質量%の割合で感光性染毛剤に添加される。さらに、この鉄塩の安定性を向上させるために、ブドウ糖を0.1〜10質量%程度添加することが好ましい。  The photosensitive hair dye of the present invention preferably contains an iron salt in order to suppress the redness of the hair color due to laccaic acid. The iron salt is preferably added to the photosensitive hair dye in a proportion of 0.01 to 5% by mass, more preferably 0.05 to 1% by mass. Furthermore, in order to improve the stability of the iron salt, it is preferable to add about 0.1 to 10% by mass of glucose.

本発明の感光性染毛剤は、上記銅塩または亜鉛塩に特有の金属臭をマスキングするため、茶乾留液を添加することが好ましい。この茶乾留液は、好ましくは0.01〜10.0質量%、より好ましくは0.1〜5.0質量%の割合で感光性染毛剤に添加される。  In the photosensitive hair dye of the present invention, a tea dry distillation liquid is preferably added to mask the metal odor peculiar to the copper salt or zinc salt. This tea dry distillation liquid is preferably added to the photosensitive hair dye at a ratio of 0.01 to 10.0 mass%, more preferably 0.1 to 5.0 mass%.

本発明の感光性染毛剤は、上記銀塩の安定性を向上させるため、リンゴ酸、フマル酸等の有機酸を添加することが好ましい。この有機酸は、好ましくは0.01〜10.0質量%、より好ましくは0.1〜5.0質量%添加することがより好ましい。  The photosensitive hair dye of the present invention preferably contains an organic acid such as malic acid or fumaric acid in order to improve the stability of the silver salt. This organic acid is preferably added in an amount of 0.01 to 10.0% by mass, more preferably 0.1 to 5.0% by mass.

本発明の感光性染毛剤には、キレート剤が含まれていることが好ましい。このキレート剤としては、ジエチレントリアミン五酢酸、ヒドロキシエタンジホスホン酸、エデト酸、(2S,2’S)−2,2’−(エチレンビスイミノ)ビスコハク酸、1,3−ジアミノ−2−プロパノール−N,N,N’,N’−四酢酸、N,N−ジ(2−ヒドロキシエチル)グリシン、ニトリロトリス(メチレンホスホン酸)、ヒドロキシエチルエチレンジアミン三酢酸、フィチン酸、ポリアスパラギン酸、ポリグルタミン酸、アスパラギン酸二酢酸、グルタミン酸二酢酸、ポリリン酸ナトリウム、メタリン酸ナトリウム、リン酸、ジヒドロキシエチルグリシン、グルコン酸、コハク酸、酒石酸などが挙げられる。この中で、ジエチレントリアミン五酢酸、ヒドロキシエタンジホスホン酸、エデト酸、(2S,2’S)−2,2’−(エチレンビスイミノ)ビスコハク酸、1,3−ジアミノ−2−プロパノール−N,N,N’,N’−四酢酸、N,N−ジ(2−ヒドロキシエチル)グリシン、及びニトリロトリス(メチレンホスホン酸)より選ばれる1種または2種以上が、製剤安定性、毛髪損傷の起こし難さ、及び染毛効果の点から好ましい。
このキレート剤は、好ましくは0.01〜5質量%、より好ましくは0.1〜1質量%の割合で感光性染毛剤に添加される。
The photosensitive hair dye of the present invention preferably contains a chelating agent. Examples of the chelating agent include diethylenetriaminepentaacetic acid, hydroxyethanediphosphonic acid, edetic acid, (2S, 2 ′S) -2,2 ′-(ethylenebisimino) bissuccinic acid, 1,3-diamino-2-propanol- N, N, N ′, N′-tetraacetic acid, N, N-di (2-hydroxyethyl) glycine, nitrilotris (methylenephosphonic acid), hydroxyethylethylenediaminetriacetic acid, phytic acid, polyaspartic acid, polyglutamic acid, Examples include aspartic acid diacetic acid, glutamic acid diacetic acid, sodium polyphosphate, sodium metaphosphate, phosphoric acid, dihydroxyethylglycine, gluconic acid, succinic acid, and tartaric acid. Among them, diethylenetriaminepentaacetic acid, hydroxyethanediphosphonic acid, edetic acid, (2S, 2 ′S) -2,2 ′-(ethylenebisimino) bissuccinic acid, 1,3-diamino-2-propanol-N, One or more selected from N, N ′, N′-tetraacetic acid, N, N-di (2-hydroxyethyl) glycine, and nitrilotris (methylenephosphonic acid) are used for formulation stability and hair damage. It is preferable from the viewpoint of difficulty in raising and the hair dyeing effect.
This chelating agent is preferably added to the photosensitive hair dye in a proportion of 0.01 to 5% by mass, more preferably 0.1 to 1% by mass.

本発明の感光性染毛剤には、安定剤や酸化防止剤として、アスコルビン酸およびその塩、システインおよびその塩を添加することが好ましい。この安定剤や酸化防止剤は、0.01〜10.0質量%添加することが好ましく、0.1〜5.0質量%添加することがより好ましい。  It is preferable to add ascorbic acid and a salt thereof, cysteine and a salt thereof as a stabilizer or an antioxidant to the photosensitive hair dye of the present invention. The stabilizer and the antioxidant are preferably added in an amount of 0.01 to 10.0% by mass, more preferably 0.1 to 5.0% by mass.

本発明の感光性染毛剤に使用される溶媒としては、精製水(水)、エタノール、イソプロピルアルコール、1,3ブチレングリコール、グリセリン、ジプロピレングリコールなどが通常使用されるものであれば使用可能であるが、浸透促進剤としてベンジルアルコール、フェニルエチルアルコール、1,2−ペンタジオール、2−メチル−2,4−ペンタジオール等も溶媒として利用してもよい。  As the solvent used for the photosensitive hair dye of the present invention, purified water (water), ethanol, isopropyl alcohol, 1,3 butylene glycol, glycerin, dipropylene glycol and the like can be used. However, benzyl alcohol, phenylethyl alcohol, 1,2-pentadiol, 2-methyl-2,4-pentadiol, or the like may be used as a solvent as a penetration enhancer.

本発明の感光性染毛剤の形態としては、液状、ゲル状、クリーム状、スティク状、エアゾール等の剤型で製剤化することが可能であるが、用法を考慮するとゲル状又はクリーム状が本発明の効果を発揮されやすく好ましい。  As the form of the photosensitive hair dye of the present invention, it can be formulated in a liquid form, a gel form, a cream form, a stick form, an aerosol form or the like. The effect of the present invention is easily exhibited and is preferable.

本発明の感光性染毛剤には、上記成分以外に他の成分として化粧品や医薬部外品などで配合成分として一般的に用いられる、界面活性剤、油脂類、pH調整剤、保湿剤、溶剤、防腐剤、植物抽出物、抗炎症剤、色素、香料などを適宜配合することができる。  In the photosensitive hair dye of the present invention, surfactants, fats and oils, pH adjusters, humectants, which are generally used as ingredients other than the above ingredients as cosmetic ingredients and quasi drugs, etc. Solvents, preservatives, plant extracts, anti-inflammatory agents, pigments, fragrances and the like can be appropriately blended.

本発明の感光性染毛剤のpHは、2.0〜5.0に調整することが好ましく、2.0〜4.5に調整することが染毛効果を高めるために好ましい。pHは、クエン酸、アルギニン、水酸化ナトリウム等により調整すればよい。
製剤化に必要な公知の成分としては、剤型の種類ごとに適宜設定すればよい。
The pH of the photosensitive hair dye of the present invention is preferably adjusted to 2.0 to 5.0, and preferably adjusted to 2.0 to 4.5 in order to enhance the hair dyeing effect. The pH may be adjusted with citric acid, arginine, sodium hydroxide or the like.
What is necessary is just to set suitably as a well-known component required for formulation for every kind of dosage form.

毛髪への付与は、公知の方法に従い行うことができ、具体的には、直接毛髪に付与する方法、手又はブラシなどの道具を使って毛髪に付与する方法等が挙げられる。
染毛剤の毛髪に付与した後放置する時間は適宜設定することができる。また、染毛剤を洗い流す方法は、公知の方法を用いればよい。
Application to hair can be performed according to a known method, and specific examples include a method of applying directly to hair, a method of applying to hair using tools such as hands or a brush, and the like.
The time to leave after giving to the hair of a hair dye can be set suitably. Moreover, what is necessary is just to use a well-known method for the method of washing away a hair dye.

染毛剤組成物の毛髪への付与量としては、長さ等に応じて適宜設定することができる。  The amount of the hair dye composition applied to the hair can be appropriately set according to the length and the like.

本発明の感光性染毛剤を発色させる光源としては、太陽光、蛍光灯、太陽光蛍光灯(太陽光に近いスペクトル成分を持った蛍光灯)、ブラックライトなど特に拘りはないが、蛍光灯、太陽光蛍光灯、及びブラックライトが好ましく、蛍光灯が特に好ましい。  The light source for coloring the photosensitive hair dye of the present invention is not particularly limited to sunlight, fluorescent lamps, solar fluorescent lamps (fluorescent lamps having spectral components close to sunlight), black light, etc. Solar fluorescent lamps and black lights are preferred, and fluorescent lamps are particularly preferred.

つぎに、本発明の実施例を比較例と共に説明するが、本発明は、下記の実施例に限定されるものではない。  Next, examples of the present invention will be described together with comparative examples, but the present invention is not limited to the following examples.

[染色性試験1]
本発明の実施例および比較例の染毛剤を表1に示す組成にて調製した。なお、各剤のpHも表1に示す。
調製した染毛剤2.0gを、人毛白毛BM−W−A(ビューラックス社製)8cm(0.4g)に均一に塗布し、30W蛍光灯の直下1mに8時間静置した後、3%ラウレス硫酸Na溶液にて洗浄し、風乾した。さらに、染色した毛髪に対して、下記のパーマ処理を施した。
パーマ処理前後の毛髪について、目視にて色を判断した。その結果は表1に示す。
[Dyeability test 1]
The hair dyes of Examples and Comparative Examples of the present invention were prepared with the compositions shown in Table 1. The pH of each agent is also shown in Table 1.
After 2.0 g of the prepared hair dye is uniformly applied to 8 cm (0.4 g) of human white hair BM-WA (Buelux) and left to stand at 1 m directly below a 30 W fluorescent lamp for 8 hours. It was washed with 3% sodium laureth sulfate solution and air-dried. Further, the following perm treatment was applied to the dyed hair.
The color of the hair before and after the perm treatment was judged visually. The results are shown in Table 1.

Figure 2016193877
Figure 2016193877

上記表1に示すように、本実施例にかかる染毛剤は、パーマ処理による緑色への変色が抑制されていることがわかる。  As shown in Table 1 above, it can be seen that the hair dye according to the present example is suppressed from being discolored to green by the permanent treatment.

[パーマ処理]
表2に示す組成の第1剤および第2剤からなるパーマ液を調製した。上記のとおり実施例および比較例で染色した毛髪に第1剤を塗布して15分間放置後、水道水で洗浄し、タオルで水分を拭き取った。その後、毛髪に第2剤を塗布して15分間放置後、水道水で洗浄し、風乾した。

Figure 2016193877
[Perm processing]
A permanent solution composed of the first agent and the second agent having the composition shown in Table 2 was prepared. As described above, the first agent was applied to the hair dyed in the examples and comparative examples, allowed to stand for 15 minutes, washed with tap water, and wiped with a towel. Thereafter, the second agent was applied to the hair and allowed to stand for 15 minutes, then washed with tap water and air dried.
Figure 2016193877

[染色性試験2]
本発明の実施例および比較例の染毛剤を表3に示す組成にて調製した。なお、各剤のpHも表2に示す。
調製した染毛剤2.0gを、人毛白毛BM−W−A(ビューラックス社製)8cm(0.4g)に均一に塗布し、30W蛍光灯の直下1mに24時間静置し、さらに太陽光下に3時間静置した後、3%ラウレス硫酸Na溶液にて洗浄し、風乾した。さらに、染色した毛髪に対して、上記と同様にしてパーマ処理を施した。
パーマ処理前後の毛髪について、染色した毛髪のLabを、カラーリーダーCR−13型(コニカミノルタ社製)を用いて測定(測定結果は3回測定した際の平均値)し、目視にて色を判断した。その結果は表3に示す。
[Dyeability test 2]
The hair dyes of Examples and Comparative Examples of the present invention were prepared with the compositions shown in Table 3. The pH of each agent is also shown in Table 2.
2.0 g of the prepared hair dye is uniformly applied to 8 cm (0.4 g) of human white hair BM-WA (Buelux) and left to stand at 1 m directly under a 30 W fluorescent lamp for 24 hours. Furthermore, after leaving still under sunlight for 3 hours, it was washed with 3% laureth sulfate Na solution and air-dried. Furthermore, perm treatment was performed on the dyed hair in the same manner as described above.
For the hair before and after the perm treatment, the Lab of the dyed hair was measured using a color reader CR-13 type (manufactured by Konica Minolta Co., Ltd.) (the measurement result is an average value when measured three times), and the color was visually observed. It was judged. The results are shown in Table 3.

Figure 2016193877
Figure 2016193877

上記表3に示すように、本実施例にかかる染毛剤は、パーマ処理による色落ちおよび緑色への変色が抑制されていることがわかる。さらに、前記実施例1,2に比べ、鉄化合物を添加することにより赤味が抑制されていることが見て取れた。  As shown in Table 3 above, it can be seen that the hair dye according to this example has suppressed color fading and discoloration to green due to the permanent treatment. Furthermore, it can be seen that redness was suppressed by adding an iron compound as compared to Examples 1 and 2 above.

[染色性試験3]
本発明の実施例の染毛剤を表4に示す組成にて調製した。なお、各剤のpHも表3に示す。
調製した染毛剤2.0gを、人毛白毛BM−W−A(ビューラックス社製)8cm(0.4g)に均一に塗布し、30W蛍光灯の直下1mに24時間静置した後、3%ラウレス硫酸Na溶液にて洗浄し、風乾した。さらに、染色した毛髪に対して、上記と同様にしてパーマ処理を施した。
パーマ処理前後の毛髪について、染色した毛髪のLabを、カラーリーダーCR−13型(コニカミノルタ社製)を用いて測定(測定結果は3回測定した際の平均値)し、目視にて色を判断した。その結果は表4に示す。
[Dyeability test 3]
The hair dye of the Example of this invention was prepared with the composition shown in Table 4. The pH of each agent is also shown in Table 3.
After 2.0 g of the prepared hair dye is uniformly applied to 8 cm (0.4 g) of human white hair BM-WA (Burelux) and left to stand at 1 m directly under a 30 W fluorescent lamp for 24 hours. It was washed with 3% sodium laureth sulfate solution and air-dried. Furthermore, perm treatment was performed on the dyed hair in the same manner as described above.
For the hair before and after the perm treatment, the Lab of the dyed hair was measured using a color reader CR-13 type (manufactured by Konica Minolta Co., Ltd.) (the measurement result is an average value when measured three times), and the color was visually observed. It was judged. The results are shown in Table 4.

Figure 2016193877
Figure 2016193877

上記表4に示すように、本実施例にかかる染毛剤は、パーマ処理による緑色への変色が抑制されていることがわかる。  As shown in Table 4 above, it can be seen that the hair dye according to the present example is suppressed from being discolored to green by the permanent treatment.

Claims (4)

銀塩と、ラッカイン酸と、を含有することを特徴とする感光性染毛剤。  A photosensitive hair dye characterized by containing a silver salt and laccaic acid. 亜鉛塩および銅塩から選択される少なくとも1種の金属塩を含む請求項1に記載の感光性染毛剤。  The photosensitive hair dye of Claim 1 containing the at least 1 sort (s) of metal salt selected from zinc salt and copper salt. 鉄塩を含む請求項2に記載の感光性染毛剤。  The photosensitive hair dye of Claim 2 containing an iron salt. 白髪隠しであることを特徴とする請求項1〜3のいずれか1項に記載の感光性染毛剤。  The photosensitive hair dye according to any one of claims 1 to 3, wherein the photosensitive hair dye is white hair concealment.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04187625A (en) * 1990-11-22 1992-07-06 Katsumi Mizumaki Hair-dyeing agent containing silver halide
JP2008069131A (en) * 2006-09-15 2008-03-27 Kaminomoto Co Ltd Photosensitive acid hair dye composition
JP2009167118A (en) * 2008-01-15 2009-07-30 Sk Planner:Kk Dyeing auxiliary used for dyeing keratin fiber by natural dyestuff

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04187625A (en) * 1990-11-22 1992-07-06 Katsumi Mizumaki Hair-dyeing agent containing silver halide
JP2008069131A (en) * 2006-09-15 2008-03-27 Kaminomoto Co Ltd Photosensitive acid hair dye composition
JP2009167118A (en) * 2008-01-15 2009-07-30 Sk Planner:Kk Dyeing auxiliary used for dyeing keratin fiber by natural dyestuff

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