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JPH0460581B2 - - Google Patents
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JPH0460581B2 - - Google Patents

Info

Publication number
JPH0460581B2
JPH0460581B2 JP63205622A JP20562288A JPH0460581B2 JP H0460581 B2 JPH0460581 B2 JP H0460581B2 JP 63205622 A JP63205622 A JP 63205622A JP 20562288 A JP20562288 A JP 20562288A JP H0460581 B2 JPH0460581 B2 JP H0460581B2
Authority
JP
Japan
Prior art keywords
hair
dye
weight
diaminophenol
present
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.)
Expired - Lifetime
Application number
JP63205622A
Other languages
Japanese (ja)
Other versions
JPH0253715A (en
Inventor
Mitsuhiko Kino
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.)
Hoyu Co Ltd
Original Assignee
Hoyu Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoyu Co Ltd filed Critical Hoyu Co Ltd
Priority to JP20562288A priority Critical patent/JPH0253715A/en
Publication of JPH0253715A publication Critical patent/JPH0253715A/en
Publication of JPH0460581B2 publication Critical patent/JPH0460581B2/ja
Granted legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/415Aminophenols

Landscapes

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

Description

【発明の詳細な説明】[Detailed description of the invention]

[産業上の利用分野] 本発明は自動酸化型一剤式染毛剤に関するもの
である。 [従来技術とその問題点] 従来、例えば、パラフエニレンジアミンやパラ
トルイレンジアミンを主剤とする第1剤と酸化剤
を主剤とする第2剤からなる二剤式酸化染毛剤が
広く利用されている。このタイプの染毛剤は種々
の色調の染毛ができる上、染毛力及び堅牢性に優
れている。 ところが、これら染毛剤は使用直前に第1剤と
第2剤とを均一混合する必要があり、素人が個人
で染毛処理する場合には、操作的に面倒であり、
しかも、刺激性が比較的に強いため、特にアレル
ギー体質の人に対して適用できないと言う欠点が
ある。 また、酸性染料や塩基性染料を用いる溶媒染色
により毛髪を染色する半永久染毛剤、金属塩と多
価フエノールを用いる金属染毛剤、更に、カーボ
ンブラツクや顔料などを用いる一時塗毛型染毛剤
などの各種染毛剤も知られているが、これらの染
毛剤は上記の二剤式酸化染毛剤に比べて刺激が少
なく、アレルギー体質の人でも利用できるが、い
ずれも、高い染着性及び堅牢性は期待できず、色
調面でも十分とは言えない。 一方、酸化染毛剤として用いられる酸化染料は
必ずしも、酸化剤を主剤とする第2剤を用いなく
ても、空気中の酸素により徐々に自動酸化され、
発色することが知られている。要するに、この場
合には、使用時において、第1剤と第2剤とを混
合する操作が不要となる。しかしながら、従来の
酸化染料の場合には、発色に時間を要するばかり
か、毛髪への染着力は弱く、しかも、色調も不自
然であり第三者に対して違和感を与える結果とな
る。 [発明の課題と解決手段] 本発明者は上記実情に鑑み、酸化剤を用いなく
てもよい自動酸化型の染毛剤において、毛髪を濃
色に、且つ自然に染色することのできる染毛剤を
得るべく種々検討したところ、ある特定のパラフ
エニレンジアミン誘導体と2,4−ジアミノフエ
ノールとを混合した酸化染料を用いることによ
り、短時間のうちに高い染着力で良好な色調に毛
髪を染色することができ、しかも、毛髪の損傷や
地肌への刺激も極めて少ないことを見い出し、本
発明を完成するに至つた。 すなわち、本発明の要旨は、酸化染料として、
2,4−ジアミノフエノール又はその塩と下記一
般式[] (式中、R1及びR2は水素原子、アルキル基又
はヒドロキシアルキル基を表わすが、R1とR2の
両方が水素原子であることはない。)で示される
パラフエニレンジアミン誘導体又はその塩とを含
有することを特徴とする自動酸化型一剤式染毛剤
に存する。 以下、本発明を詳細に説明する。 本発明における前示一般式[]において、
R1及びR2で表わされるアルキル基又はヒドロキ
シアルキル基の炭素数は好ましくは1〜3であ
る。前示一般式[]で示されるパラフエニレン
ジアミン誘導体の具体例としては、例えば、N−
メチルパラフエニレンジアミン、N,N−ジメチ
ルパラフエニレンジアミン、N−エチルパラフエ
ニレンジアミン、N,N−ジエチルパラフエニレ
ンジアミン、N−エチル−β−ヒドロキシエチル
パラフエニレンジアミン、N,N−ビスヒドロキ
シエチルパラフエニレンジアミンなどが挙げら
れ、特に好ましくは、N−エチル−β−ヒドロキ
シエチルパラフエニレンジアミン、N,N−ビス
ヒドロキシエチルパラフエニレンジアミンであ
る。また、これらの塩としては、通常、硫酸塩、
塩酸塩、酢酸塩などが挙げられる。 本発明では上述のパラフエニレンジアミン誘導
体と2,4−ジアミノフエノール又はその塩とを
併用することを必須の要件とするものである。す
なわち、この酸化染料は単独使用でも自動酸化さ
れるものの、単独の場合には、短時間で良好に発
色せず、染着力も弱く色調が不自然なものである
が、両者を併用した場合には、極めて優れた自動
酸化ができ、良好な染毛処理を行なうことができ
るのである。 2,4−ジアミノフエノールの塩としては、パ
ラフエニレンジアミン誘導体の場合と同様に、例
えば、硫酸塩、塩酸塩、酢酸塩などが挙げられ
る。2,4−ジアミノフエノール又はその塩に対
するパラフエニレンジアミン誘導体又はその塩の
使用割合は、通常、0.1〜5モル倍、好ましくは
0.5〜2モル倍である。この使用割合はあまり大
きすぎても、また、あまり小さすぎても、優れた
自動酸化による良好な染毛処理が期待できない。 本発明において、染毛剤への酸化染料の配合量
は、通常、0.01〜10重量%、好ましくは0.1〜6
重量%である。なお、本発明は上記の酸化染料の
他に、例えば、ニトロ染料や酸性染料を少量、配
合しても差し支えない。 本発明の染毛剤は通常、水性媒体をベースとす
るが、染料成分以外に例えば、ポリオキシエチレ
ンアルキルエーテル、ポリオキシエチレンアルキ
ルアミン脂肪酸アミド等の界面活性剤、グリセリ
ン、プロピレングリコール等の保湿剤、ラノリ
ン、スクワラン、流動パラフイン等の油性成分、
亜硫酸塩、アスコルビン酸等の安定剤、カルボキ
シメチルセルロース等の増粘剤、アンモニア、ア
ルカノールアミン等のアルカリ剤、高級アルコー
ル、香料、噴射剤、などの公知の配合剤を必要に
応じて適宜、配合することができる。また、染毛
剤の形態は通常、ローシヨンタイプ又は泡状タイ
プである。 本発明の自動酸化型一剤式染毛剤を使用する場
合には、酸化剤を用いることなく、本発明の染毛
剤をそのまま直接、染色すべき毛髪に塗布し、そ
の後、例えば、10〜60分程度、放置することによ
り、空気中の酸素の作用によつて毛髪を染色する
ことができる。染毛処理後は常法に従つて洗髪
し、次いで、乾燥することにより染毛を完了する
ことができる。また、染料濃度が低い場合は、毛
髪に塗布してから半日〜2日間放置することによ
り、染毛することができる。 [実施例] 次に、本発明を実施例により更に具体的に説明
するが、本発明はその要旨を超えない限り、以下
の実施例の記述に限定されるものではない。 実施例1〜4及び比較例1〜7 (染毛剤の処方) パラフエニレンジアミン誘導体 2,4−ジアミノフエノール 第1表に示す通り 無水亜硫酸ナトリウム 0.3重量% モノエタノールアミン 0.3重量% ヒドロキシエチルセルロース 2.0量% 精製水で100%とする。 上記のように調製した各染毛剤をヤギの白色毛
束に塗布し、室温下で、1時間放置した後、水洗
し染毛処理を行ない、染毛後の毛髪を下記の基準
により評価した結果を第1表に示した。 (評価基準) 1……ほとんど染まらない 2……うすい灰色に染まる 3……灰褐色に染まる 4……褐色に染まる 5……黒褐色に染まる
[Industrial Field of Application] The present invention relates to an auto-oxidizing one-component hair dye. [Prior art and its problems] Conventionally, for example, two-part oxidative hair dyes consisting of a first part whose main ingredient is paraphenylene diamine or paratolylene diamine and a second part whose main ingredient is an oxidizing agent have been widely used. has been done. This type of hair dye can dye hair in various tones and has excellent hair dyeing power and fastness. However, with these hair dyes, it is necessary to uniformly mix the first and second agents immediately before use, which is cumbersome for amateurs who dye their hair by themselves.
Moreover, it has the disadvantage that it is not particularly suitable for people with allergies because it is relatively irritating. In addition, semi-permanent hair dyes that dye hair by solvent dyeing using acidic or basic dyes, metal hair dyes that use metal salts and polyvalent phenols, and temporary hair dyes that use carbon black or pigments. Although these hair dyes are less irritating than the two-component oxidative hair dyes mentioned above and can be used by people with allergies, they are all expensive dyes. The adhesion and fastness cannot be expected, and the color tone is also not satisfactory. On the other hand, oxidative dyes used as oxidative hair dyes are not necessarily automatically oxidized by oxygen in the air, even without the use of a second agent containing an oxidizing agent as the main ingredient.
It is known to produce color. In short, in this case, there is no need to mix the first agent and the second agent during use. However, in the case of conventional oxidation dyes, not only does it take a long time to develop color, but the dyeing power to hair is weak, and the color tone is unnatural, giving third parties a sense of discomfort. [Problems to be solved by the invention and means for solving the problem] In view of the above circumstances, the present inventor has developed an auto-oxidizing hair dye that does not require the use of an oxidizing agent and is capable of dyeing hair darkly and naturally. After conducting various studies to obtain a dye, we found that by using an oxidation dye that is a mixture of a certain paraphenylenediamine derivative and 2,4-diaminophenol, it was possible to dye hair with high dyeing power and a good color tone in a short period of time. The present inventors have discovered that the dye can be dyed, and that it causes very little damage to the hair and very little irritation to the skin, leading to the completion of the present invention. That is, the gist of the present invention is that as an oxidation dye,
2,4-diaminophenol or its salt and the following general formula [] (In the formula, R1 and R2 represent a hydrogen atom, an alkyl group, or a hydroxyalkyl group, but both R1 and R2 are not hydrogen atoms.) Contains a paraphenylenediamine derivative or a salt thereof. An auto-oxidizing one-component hair dye characterized by: The present invention will be explained in detail below. In the general formula [] in the present invention,
The alkyl group or hydroxyalkyl group represented by R1 and R2 preferably has 1 to 3 carbon atoms. Specific examples of paraphenylenediamine derivatives represented by the general formula [] include N-
Methylparaphenylenediamine, N,N-dimethylparaphenylenediamine, N-ethylparaphenylenediamine, N,N-diethylparaphenylenediamine, N-ethyl-β-hydroxyethylparaphenylenediamine, N,N -bishydroxyethylparaphenylenediamine and the like, particularly preferably N-ethyl-β-hydroxyethylparaphenylenediamine and N,N-bishydroxyethylparaphenylenediamine. In addition, these salts usually include sulfates,
Examples include hydrochloride and acetate. In the present invention, it is essential to use the above paraphenylene diamine derivative and 2,4-diaminophenol or a salt thereof in combination. In other words, although this oxidation dye is automatically oxidized even when used alone, when used alone, the color does not develop well in a short period of time, the dyeing power is weak, and the color tone is unnatural.However, when both are used together, It has excellent auto-oxidation properties and can be used to dye hair well. Examples of the salt of 2,4-diaminophenol include sulfate, hydrochloride, acetate, etc., as in the case of paraphenylenediamine derivatives. The ratio of paraphenylenediamine derivative or its salt to 2,4-diaminophenol or its salt is usually 0.1 to 5 times by mole, preferably
It is 0.5 to 2 times the mole. If this usage ratio is too large or too small, a good hair dyeing process due to excellent autooxidation cannot be expected. In the present invention, the amount of oxidation dye added to the hair dye is usually 0.01 to 10% by weight, preferably 0.1 to 6% by weight.
Weight%. In addition, in the present invention, in addition to the above-mentioned oxidation dye, for example, a small amount of nitro dye or acid dye may be blended. The hair dye of the present invention is usually based on an aqueous medium, but in addition to the dye component, there are surfactants such as polyoxyethylene alkyl ether and polyoxyethylene alkylamine fatty acid amide, and humectants such as glycerin and propylene glycol. , oily ingredients such as lanolin, squalane, and liquid paraffin,
Known compounding agents such as stabilizers such as sulfites and ascorbic acid, thickeners such as carboxymethylcellulose, alkali agents such as ammonia and alkanolamines, higher alcohols, fragrances, and propellants are appropriately blended as necessary. be able to. Moreover, the form of hair dye is usually a lotion type or a foam type. When using the auto-oxidizing one-component hair dye of the present invention, the hair dye of the present invention is directly applied to the hair to be dyed without using an oxidizing agent, and then, for example, By leaving it for about 60 minutes, hair can be dyed by the action of oxygen in the air. After the hair dyeing process, hair dyeing can be completed by washing the hair according to a conventional method and then drying the hair. If the dye concentration is low, hair can be dyed by applying it to the hair and leaving it for half a day to two days. [Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to the description of the following Examples unless it exceeds the gist thereof. Examples 1 to 4 and Comparative Examples 1 to 7 (Formulation of hair dye) Paraphenylene diamine derivative 2,4-diaminophenol As shown in Table 1 Anhydrous sodium sulfite 0.3% by weight Monoethanolamine 0.3% by weight Hydroxyethyl cellulose 2.0 Amount % Make 100% with purified water. Each of the hair dyes prepared above was applied to white goat hair strands, left for 1 hour at room temperature, washed with water and dyed, and the dyed hair was evaluated according to the following criteria. The results are shown in Table 1. (Evaluation criteria) 1... Hardly dyed 2... Stained to pale gray 3... Stained to grayish brown 4... Stained to brown 5... Stained to blackish brown

【表】 第1表の結果より、2,4−ジアミノフエノー
ルを併用した場合(実施例1〜4)には良好な染
毛結果であるが、これを併用しない場合(比較例
1〜4)には、実質的な染毛がなされていないこ
とが判る。また、パラフエニレンジアミン自身を
用いた場合(比較例5)よりも本発明の実施例の
方が優れていることが判る。一方、2,4−ジア
ミノフエノール単独の場合(比較例7)も十分な
染毛処理とは言えないことが判る。 2−メトキシ−パラフエニレンジアミンと2,
4−ジアミノフエノールとを併用した場合(比較
例8)には、本発明で特定するパラフエニレンジ
アミン誘導体と2,4−ジアミノフエノールとを
併用した場合(実施例1〜4)に対し、染毛効果
が劣ることが判る。 実施例 5(ローシヨンタイプの例) N−エチル−β−ヒドロキシエチルパラフエニ
レンジアミン硫酸塩 0.56重量% 2,4−ジアミノフエノール硫酸塩 0.44重量% グリセリン 5重量% エタノール 10重量% モノエタノールアミン 0.5重量% カーボポール940 0.2重量% 精製水で100%にする。 この染毛剤をヤギの白色毛束に塗布し、室温
下、1時間放置した後、水洗し乾燥すると毛束は
良好な暗褐色に染まつた。 実施例 6(泡状タイプの例) N,N−ビスヒドロキシエチルパラフエニレン
ジアミン硫酸塩 0.6重量% 2,4−ジアミノフエノール硫酸塩 0.4重量% ステアリルアルコール 1.5重量% 臭化セチルトリメチルアンモニウム 0.5重量% ポリオキシエチレン(7.5)ノニルフエニルエー
テル 2.0重量% メチルフエニルポリシロキサン 0.5重量% グリセリン 2.0重量% エタノール 0.5重量% トリエタノールアミン 0.5重量% ポリビニルピロリドン 2.0重量% 噴射剤(フロン12/フロン114) 9.0重量% 精製水で100%とし、次いで、この染毛剤をアル
ミ缶に充填した。 これをヤギの白色毛束に塗布し、1時間放置し
た後、水洗し乾燥すると毛束は良好な灰黒色に染
まつた。 [発明の効果] 本発明の自動酸化型一剤式染毛剤によれば、酸
化染料として、特定のパラフエニレンジアミン誘
導体と2,4−ジアミノフエノールとを併用する
ことにより、空気中での酸化、発色が短時間で極
めて良好に行なわれ、自然な濃色の染毛を実施す
ることができる。また、染毛処理による染着力及
び堅牢性も優れており、更に、地肌への刺激も少
ないので好ましい。
[Table] From the results in Table 1, good hair dyeing results are obtained when 2,4-diaminophenol is used in combination (Examples 1 to 4), but when it is not used in combination (Comparative Examples 1 to 4) It can be seen that there is no substantial hair dyeing. Furthermore, it can be seen that the example of the present invention is superior to the case where paraphenylenediamine itself is used (Comparative Example 5). On the other hand, it can be seen that the case of using 2,4-diaminophenol alone (Comparative Example 7) cannot be said to be a sufficient hair dyeing treatment. 2-methoxy-paraphenylenediamine and 2,
When 4-diaminophenol was used in combination (Comparative Example 8), the dyeing result was lower than when the paraphenylenediamine derivative specified in the present invention and 2,4-diaminophenol were used together (Examples 1 to 4). It can be seen that the hair effect is inferior. Example 5 (Example of lotion type) N-ethyl-β-hydroxyethylparaphenylenediamine sulfate 0.56% by weight 2,4-diaminophenol sulfate 0.44% by weight Glycerin 5% by weight Ethanol 10% by weight Monoethanolamine 0.5 Weight% Carbopol 940 0.2% by weight Make 100% with purified water. This hair dye was applied to a white goat hair strand, left to stand at room temperature for 1 hour, washed with water and dried, resulting in a good dark brown color to the hair strand. Example 6 (foam type example) N,N-bishydroxyethylparaphenylenediamine sulfate 0.6% by weight 2,4-diaminophenol sulfate 0.4% by weight Stearyl alcohol 1.5% by weight Cetyltrimethylammonium bromide 0.5% by weight Polyoxyethylene (7.5) nonyl phenyl ether 2.0% by weight Methylphenyl polysiloxane 0.5% by weight Glycerin 2.0% by weight Ethanol 0.5% by weight Triethanolamine 0.5% by weight Polyvinylpyrrolidone 2.0% by weight Propellant (Freon 12/Freon 114) 9.0 Weight % The hair dye was made up to 100% with purified water, and then filled into aluminum cans. This was applied to a bunch of white goat hair, left for one hour, washed with water, and dried, resulting in a good gray-black color. [Effects of the Invention] According to the auto-oxidizing one-component hair dye of the present invention, by using a specific paraphenylenediamine derivative and 2,4-diaminophenol as oxidation dyes, Oxidation and color development occur extremely well in a short period of time, making it possible to dye hair in natural dark colors. In addition, it is preferable because it has excellent dyeing power and fastness during hair dyeing treatment, and is less irritating to the scalp.

Claims (1)

【特許請求の範囲】 1 酸化染料として、2,4−ジアミノフエノー
ル又はその塩と下記一般式[] (式中、R1及びR2は水素原子、アルキル基又
はヒドロキシアルキル基を表わすが、R1とR2の
両方が水素原子であることはない。)で示される
パラフエニレンジアミン誘導体又はその塩とを含
有することを特徴とする自動酸化型一剤式染毛
剤。
[Claims] 1. As an oxidation dye, 2,4-diaminophenol or a salt thereof and the following general formula [] (In the formula, R1 and R2 represent a hydrogen atom, an alkyl group, or a hydroxyalkyl group, but both R1 and R2 are not hydrogen atoms.) Contains a paraphenylenediamine derivative or a salt thereof. An auto-oxidizing single-component hair dye that is characterized by:
JP20562288A 1988-08-18 1988-08-18 Autoxidation one-pack hair-dye Granted JPH0253715A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20562288A JPH0253715A (en) 1988-08-18 1988-08-18 Autoxidation one-pack hair-dye

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20562288A JPH0253715A (en) 1988-08-18 1988-08-18 Autoxidation one-pack hair-dye

Publications (2)

Publication Number Publication Date
JPH0253715A JPH0253715A (en) 1990-02-22
JPH0460581B2 true JPH0460581B2 (en) 1992-09-28

Family

ID=16509933

Family Applications (1)

Application Number Title Priority Date Filing Date
JP20562288A Granted JPH0253715A (en) 1988-08-18 1988-08-18 Autoxidation one-pack hair-dye

Country Status (1)

Country Link
JP (1) JPH0253715A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0372821B1 (en) * 1988-11-30 1995-03-08 Nec Corporation Liquid crystal display panel with reduced pixel defects
JPH0386813A (en) * 1989-02-20 1991-04-11 Kao Corp Air oxidation type hair dyeing agent composition of one-agent type
JPH07309732A (en) * 1994-05-17 1995-11-28 Hoyu Co Ltd Aerosol type hair dye
JP4312980B2 (en) 2001-12-26 2009-08-12 花王株式会社 Hair dye composition
JP4030934B2 (en) * 2003-07-28 2008-01-09 ホーユー株式会社 Aerosol hair dye

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5218258A (en) * 1975-08-01 1977-02-10 Daiei Denki Seisakusho:Kk Magnetism sellection control gear
US4104021A (en) * 1976-05-28 1978-08-01 Combe Incorporated Process for dyeing hair in which the depth of shade is gradually increased in successive treatments
FR2460663A1 (en) * 1979-07-10 1981-01-30 Oreal TINCTORIAL COMPOSITION FOR HAIR BASED ON PARAPHENYLENE DIAMINES
FR2460664A1 (en) * 1979-07-10 1981-01-30 Oreal TINCTORIAL HAIR COMPOSITIONS BASED ON PARAPHENYLENEDIAMINE AND ORTHOAMINOPHENOL
EP0074243B1 (en) * 1981-09-03 1986-11-26 Unilever Plc Hair dye composition
JPS6242916A (en) * 1985-08-19 1987-02-24 Sunstar Inc Gray hair dye
JPS62126114A (en) * 1985-11-26 1987-06-08 Kindai Kagaku Kk Hair dye

Also Published As

Publication number Publication date
JPH0253715A (en) 1990-02-22

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