JPH0768105B2 - Hair treatment composition - Google Patents
Hair treatment compositionInfo
- Publication number
- JPH0768105B2 JPH0768105B2 JP4095405A JP9540592A JPH0768105B2 JP H0768105 B2 JPH0768105 B2 JP H0768105B2 JP 4095405 A JP4095405 A JP 4095405A JP 9540592 A JP9540592 A JP 9540592A JP H0768105 B2 JPH0768105 B2 JP H0768105B2
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- JP
- Japan
- Prior art keywords
- hair
- present
- group
- treatment composition
- examples
- 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.)
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Description
【０００１】[0001]
【産業上の利用分野】本発明は毛髪処理剤組成物に関
し、更に詳しくは、毛髪の損傷や手指・頭皮に対する刺
激や肌荒れを抑制し、かつ持続的セットや毛髪の改質が
可能な毛髪処理剤組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair treatment composition, and more particularly, to a hair treatment capable of suppressing damage to the hair, irritation to the fingers and scalp and rough skin, and capable of continuously setting and modifying the hair. Agent composition.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】毛髪処
理において、毛髪の持続的なセットや毛髪の改質を目的
としてケラチン還元性化合物が広く使用されている。2. Description of the Related Art In hair treatment, keratin-reducing compounds are widely used for the purpose of continuously setting hair and modifying hair.
【０００３】しかし、上記目的を十分に達成するために
は、かなりの量のケラチン還元性化合物を必要とする。
その結果、毛髪が非可逆的損傷を受け、その強度、外
観、感触等が損なわれたり、また手指・頭皮等に刺激や
肌荒れがもたらされるなどの副作用が生じることとな
る。なぜなら、皮膚組織は毛髪組織に比べルーズであ
り、また、毛髪表面近傍は強固で外来物質を浸透させに
くい構造を有することから、毛髪内部で十分な還元を起
こすに足るケラチン還元性化合物の配合は皮膚や毛髪表
面に対し毛髪内部に対する以上の作用をもたらすことと
なるからである。However, in order to fully achieve the above objectives, a considerable amount of keratin-reducing compounds is required.
As a result, the hair is irreversibly damaged, and its strength, appearance, feel, etc. are impaired, and side effects such as irritation and rough skin on fingers, scalp, etc. occur. Because skin tissue is looser than hair tissue, and since the vicinity of the hair surface has a strong structure that makes it difficult for foreign substances to permeate, blending of a keratin-reducing compound sufficient to cause sufficient reduction inside hair is not possible. This is because it causes the above-mentioned effects on the skin and the surface of the hair on the inside of the hair.
【０００４】そこで、上記目的を達成するとともに、ケ
ラチン還元性化合物による副作用を抑制するため、該化
合物の毛髪内部への浸透促進に着目した対策がなされて
いる。例えば尿素添加、ラクトン類の添加（特開昭５１
−６１６４２号公報）、カーボネート又はカーバメート
類の添加（特公昭５６−３２９６４号公報、特公昭５４
−６６１３号公報）、イミダゾリジン−２−オン類の添
加（特開昭５２−１５１７３８号公報）等が挙げられ
る。しかしながら、これらの手段はいずれも効果や安定
性が十分なものではなく、毛髪損傷や手指・頭皮に対す
る刺激や肌荒れを低レベルに抑制しつつ、毛髪の持続的
セットや改質を行うという目的は未だ達成されていな
い。Therefore, in order to achieve the above-mentioned object and to suppress the side effects of the keratin-reducing compound, measures have been taken with a focus on promoting the penetration of the compound into the hair. For example, urea addition, addition of lactones (JP-A-51)
-61642), addition of carbonates or carbamates (JP-B-56-32964, JP-B-54)
-6613), addition of imidazolidin-2-ones (JP-A-52-151738), and the like. However, none of these means have sufficient effects and stability, and the purpose of continuously setting and modifying the hair while suppressing hair damage, irritation to the fingers and scalp and rough skin to a low level. It has not been achieved yet.
【０００５】[0005]
【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、ケラチン還元性化合物及び
特定のアルコール類を含む組成物が毛髪内部に速やかに
浸透して毛髪内部を還元し得ること、しかも毛髪損傷や
手指・頭皮に対する刺激、肌荒れ等を低レベルに抑制し
得ることを見出し、本発明を完成するに至った。Means for Solving the Problems The inventors of the present invention have made extensive studies in view of such circumstances, and as a result, a composition containing a keratin-reducing compound and a specific alcohol quickly penetrates into the hair to reduce the inside of the hair. It has been found that the present invention is capable of suppressing hair damage, irritation to fingers and scalp, and rough skin at a low level, and thus completed the present invention.
【０００６】すなわち、本発明は、下記成分（Ａ）及び
（Ｂ） （Ａ）ケラチン還元性化合物の１種又は２種以上 （Ｂ）下記一般式（１）で表わされる化合物の１種又は
２種以上 R1(OCnH2n)mOH （１） （式中、Ｒ1 はフェニル基、ベンジル基、アルコキシフ
ェニル基、ナフチル基又はアルコキシナフチル基を示
し、ｍは０又は１の数を示し、ｎは０〜３の数を示す）
を含有することを特徴とする毛髪処理剤組成物を提供す
るものである。That is, the present invention provides the following components (A) and (B) one or more of (A) keratin-reducing compounds (B) one or two of the compounds represented by the following general formula (1). Or more R 1 (OC n H 2n ) m OH (1) (In the formula, R 1 represents a phenyl group, a benzyl group, an alkoxyphenyl group, a naphthyl group or an alkoxynaphthyl group, and m represents a number of 0 or 1. , N is a number from 0 to 3)
The present invention provides a hair treatment composition comprising:
【０００７】本明細書において、ケラチン還元性化合物
とは、毛髪の構造タンパク質であるケラチンに対し還元
能を有する化合物をいう。本発明に使用されるケラチン
還元性化合物としては、好ましくは、チオグリコール
酸、チオグリコール酸誘導体、チオグリコール酸又はチ
オグリコール酸誘導体の塩、システイン、システイン誘
導体、システイン又はシステイン誘導体の塩、下記一般
式（２）で表わされるチオグリセリルアルキルエーテ
ル、その誘導体及びそれらの塩、下記一般式（３）で表
わされるメルカプトアルキルアミド、その誘導体及びそ
れらの塩等が挙げられ、これらの１種又は２種以上が配
合される。In the present specification, the keratin-reducing compound means a compound having a reducing ability for keratin which is a structural protein of hair. The keratin reducing compound used in the present invention is preferably thioglycolic acid, a thioglycolic acid derivative, a salt of thioglycolic acid or a thioglycolic acid derivative, cysteine, a cysteine derivative, a salt of cysteine or a cysteine derivative, and the following general compounds. Examples thereof include thioglyceryl alkyl ether represented by the formula (2), its derivative and salts thereof, mercaptoalkylamide represented by the following general formula (3), its derivative and salts thereof, and one or two of these. The above is compounded.
【０００８】[0008]
【化１】 [Chemical 1]
【０００９】（式中、Ｒは水素原子、炭素数１〜４の直
鎖状若しくは分岐鎖状のアルキル基又はＲ′−Ｏ−Ｒ″
を示す。ここでＲ′及びＲ″は、それぞれ炭素数１〜４
の直鎖状又は分岐鎖状のアルキル基を示す。）(In the formula, R is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or R'-O-R ".
Indicates. Here, R ′ and R ″ are each a carbon number of 1 to 4
Is a linear or branched alkyl group. )
【００１０】[0010]
【化２】 [Chemical 2]
【００１１】（式中、ｌは０〜５の数を示し、ｍは０〜
３の数を示し、ｎは２〜５の数を示す。但し、ｌとｍと
が同時に０であることはない。）(Wherein l represents a number from 0 to 5 and m represents 0 to 5).
3 shows the number of 3 and n shows the number of 2-5. However, l and m are not 0 at the same time. )
【００１２】これらのうち、特に好ましい例としては、
チオグリコール酸、チオグリコール酸のグリセリルエス
テル、Ｌ−システイン、Ｄ−システイン、Ｎ−アシルシ
ステインこれらシステイン類のアンモニウム塩、４級ア
ンモニウム塩及びモノエタノールアミン、ジエタノール
アミン、トリエタノールアミン等のアミン塩、エトキシ
ヒドロキシプロパンチオール、メトキシエトキシヒドロ
キシプロパンチオール、イソプロポキシエトキシヒドロ
キシプロパンチオール等のチオグリセリルアルキルエー
テル、メルカプトエチルプロパナミド、メルカプトエチ
ルグルコンアミドなどが挙げられる。Among these, particularly preferable examples are:
Thioglycolic acid, glyceryl ester of thioglycolic acid, L-cysteine, D-cysteine, N-acylcysteine Ammonium salts of these cysteines, quaternary ammonium salts and amine salts such as monoethanolamine, diethanolamine and triethanolamine, ethoxy Examples thereof include thioglyceryl alkyl ethers such as hydroxypropanethiol, methoxyethoxyhydroxypropanethiol, and isopropoxyethoxyhydroxypropanethiol, mercaptoethylpropanamide, and mercaptoethylgluconamide.
【００１３】成分（Ａ）の配合量は、本発明組成物全量
中０．１〜２０重量％（以下、単に％という）が好まし
い。０．１％未満では還元が十分には行われず、２０％
を超えて配合してもより大きな効果は得られないばかり
か皮膚や毛髪に損傷が生じるおそれがあり好ましくな
い。The content of the component (A) is preferably 0.1 to 20% by weight (hereinafter simply referred to as "%") in the total amount of the composition of the present invention. If it is less than 0.1%, the reduction is not sufficiently performed, and 20%
If the amount exceeds the above range, not only a greater effect cannot be obtained, but also the skin and hair may be damaged, which is not preferable.
【００１４】本発明に使用される成分（Ｂ）の化合物は
下記一般式（１） R1(OCnH2n)mOH （１） （式中、Ｒ1 はフェニル基、ベンジル基、アルコキシフ
ェニル基、ナフチル基又はアルコキシナフチル基を示
し、ｍは０又は１の数を示し、ｎは０〜３の数を示す）
で表わされる。The compound of the component (B) used in the present invention is represented by the following general formula (1) R 1 (OC n H 2n ) m OH (1) (wherein R 1 is a phenyl group, a benzyl group or an alkoxyphenyl group). Group, naphthyl group or alkoxynaphthyl group, m represents a number of 0 or 1, and n represents a number of 0 to 3)
It is represented by.
【００１５】これらの好ましい具体例としては、ベンジ
ルアルコール、ベンジルオキシエタノール等が挙げられ
る。Preferred specific examples thereof include benzyl alcohol and benzyloxyethanol.
【００１６】成分（Ｂ）の配合量は本発明組成物全量中
０．０５〜５０．０％が好ましい。０．０５％未満では
効果が十分には得られず、５０．０％を超えて配合して
もより大きな効果は得られない。The content of the component (B) is preferably 0.05 to 50.0% in the total amount of the composition of the present invention. If it is less than 0.05%, the effect is not sufficiently obtained, and if it exceeds 50.0%, a larger effect cannot be obtained.
【００１７】本発明には、更に成分（Ｃ）として炭素数
１〜４の直鎖状又は分岐鎖状のアルコール、ジオール及
びトリオール並びに炭素数１〜４の直鎖状又は分岐鎖状
のアルキル基を有するＮ−アルキルピロリドンから選ば
れる１種又は２種以上を配合することが特に好ましい。In the present invention, further, as the component (C), a linear or branched alcohol, diol and triol having 1 to 4 carbon atoms and a linear or branched alkyl group having 1 to 4 carbon atoms. It is particularly preferable to mix one or more selected from N-alkylpyrrolidone having
【００１８】成分（Ｃ）の具体例としては、エタノー
ル、１−プロパノール、２−プロパノール、エチレング
リコール、プロピレングリコール、イソプレングリコー
ル、１，３−ブタンジオール、グリセリン、Ｎ−メチル
ピロリドン等が挙げられる。Specific examples of the component (C) include ethanol, 1-propanol, 2-propanol, ethylene glycol, propylene glycol, isoprene glycol, 1,3-butanediol, glycerin and N-methylpyrrolidone.
【００１９】成分（Ｃ）の配合量は、本発明組成物全量
中０．５〜５０．０％、特に１．０〜５０．０％である
ことが好ましい。The content of the component (C) is preferably 0.5 to 50.0%, more preferably 1.0 to 50.0% in the total amount of the composition of the present invention.
【００２０】本発明の毛髪処理剤組成物には、本発明の
効果を妨げない範囲内で、一般に毛髪用化粧料に使用さ
れる添加剤、例えば各種界面活性剤、油剤、保湿剤、毛
髪保護剤、感触向上剤、色素、香料、増粘剤、溶解剤、
紫外線防止剤、消炎剤、育毛成分等を配合することがで
きる。The hair treatment composition of the present invention contains additives generally used in hair cosmetics, such as various surfactants, oils, moisturizers and hair protectants, within a range that does not impair the effects of the present invention. Agents, touch improvers, dyes, fragrances, thickeners, solubilizers,
An anti-UV agent, an anti-inflammatory agent, a hair-growth component and the like can be added.
【００２１】本発明の毛髪処理剤組成物のpHは３．０〜
９．５の範囲にあることが好ましく、４．０〜９．０の
範囲がより好ましい。pHが３．０未満又は９．５を超え
る場合には皮膚や毛髪に損傷を与えるおそれがあるため
好ましくない。The pH of the hair treatment composition of the present invention is 3.0-.
It is preferably in the range of 9.5, and more preferably in the range of 4.0 to 9.0. If the pH is lower than 3.0 or higher than 9.5, the skin or hair may be damaged, which is not preferable.
【００２２】本発明の毛髪処理剤組成物は、常法により
製造することができ、パーマネントウェーブ剤、ストレ
ートパーマ剤、持続性毛髪セット剤、持続性柔軟化剤、
縮毛矯正剤等の用途に供することができる。特に、還元
性物質によって毛髪内シスチン結合を開裂させるパーマ
ネントウェーブ剤として用いることが好ましい。The hair treatment composition of the present invention can be produced by a conventional method and includes a permanent wave agent, a straight perm agent, a long-lasting hair setting agent, a long-lasting softening agent,
It can be used for applications such as a hair straightening agent. In particular, it is preferably used as a permanent waving agent that cleaves cystine bonds in hair with a reducing substance.
【００２３】[0023]
【発明の効果】本発明の毛髪処理剤組成物中のケラチン
還元性化合物は、マイルドな還元剤種を低濃度かつ中性
付近のpHで、といった穏和な条件下にあっても、速やか
に毛髪内部へと浸透し還元作用を行う。従って、本発明
の毛髪処理剤組成物は、持続的に毛髪をセットし、かつ
改質する効果をもたらすとともに、毛髪表面や皮膚に与
える損傷を最小限度に抑制することができるものであ
る。EFFECTS OF THE INVENTION The keratin-reducing compound in the hair treatment composition of the present invention is capable of quickly producing hair even under mild conditions such as low concentration of mild reducing agent species and pH around neutrality. It penetrates into the interior and performs a reducing action. Therefore, the hair treatment composition of the present invention has the effects of continuously setting and modifying the hair, and can minimize damage to the hair surface and the skin.
【００２４】[0024]
【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、本発明はこれらに限定されるものではない。EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto.
【００２５】実施例１〜３及び比較例１〜３ 同一人由来の未処理毛髪を、常法により調製した。表１
に組成を示す本発明品（実施例１〜３）及び比較品（比
較例１〜３）にそれぞれ１５分間浸漬した後、ミクロト
ームで輪切りにし、断面をメルカプト基と特異的に結合
する蛍光色素Ｎ−（７−ジメチルアミノ−４−メチルク
マリニル）マレイミドで染色し、蛍光顕微鏡で観察し
た。観察結果を、毛髪中心まで還元が進んでいるもの：
◎、毛髪内部に還元が及んでいるが不十分なもの：△、
還元が毛髪表面に留まっているもの：×として表１に示
す。Examples 1 to 3 and Comparative Examples 1 to 3 Untreated hair from the same person was prepared by a conventional method. Table 1
Each of the present invention products (Examples 1 to 3) and the comparative products (Comparative Examples 1 to 3) having the composition shown in Table 1 is immersed for 15 minutes, then cut into slices with a microtome, and the cross section thereof is a fluorescent dye N that specifically binds to a mercapto group. It was stained with-(7-dimethylamino-4-methylcoumarinyl) maleimide and observed with a fluorescence microscope. The observation results show that the reduction has proceeded to the hair center:
◎, The reduction is within the hair but is insufficient: △,
The reduction remained on the hair surface: shown in Table 1 as x.
【００２６】次に、上記本発明品及び比較品をそれぞれ
健常男性１０名の前腕内側にそれぞれ塗布し、自然乾燥
した。上記塗布〜自然乾燥を５回繰り返し、それぞれに
ついての刺激の程度を観察した。観察結果を、明らかな
発赤がみられた者：−２、わずかに発赤がみられた者：
−１、発赤がみられなかった者：０として１０名につい
ての平均値を併せて表１に示した。Next, the above-mentioned product of the present invention and the comparative product were applied to the insides of the forearms of 10 healthy males, respectively, and naturally dried. The above application to natural drying was repeated 5 times, and the degree of irritation for each was observed. Observed results were as follows: -2, obvious redness, -2, slight redness:
-1, No redness was observed: The average value of 10 persons as 0 is also shown in Table 1.
【００２７】[0027]
【表１】 [Table 1]
【００２８】表１に示されるように、本発明品は毛髪内
部まで十分に改質されている一方、皮膚刺激が著しく低
減されている。As shown in Table 1, the product of the present invention is sufficiently modified to the inside of the hair, while the skin irritation is significantly reduced.
【００２９】実施例４〜５及び比較例４〜６ 表２に組成を示す本発明品（実施例４〜５）及び比較品
（比較例４〜６）を常法に従い調製した。これらについ
て、パーマネントウェーブ処理におけるカール形成能の
指標である毛髪の伸長応力緩和測定を行った。すなわ
ち、同一人由来の未処理毛髪を上記本発明品及び比較品
にそれぞれ３０分間浸漬後の応力緩和率測定結果を、７
０％以上：◎、３０〜７０％：△、３０％以下：×とし
て併せて表２に示す。Examples 4 to 5 and Comparative Examples 4 to 6 Inventive products (Examples 4 to 5) and comparative products (Comparative Examples 4 to 6) whose compositions are shown in Table 2 were prepared by a conventional method. For these, the elongation stress relaxation measurement of the hair, which is an index of the curl forming ability in the permanent wave treatment, was measured. That is, the untreated hair derived from the same person was dipped in the above-mentioned product of the present invention and the comparative product for 30 minutes, and the stress relaxation rate measurement result was
Table 2 also shows 0% or more: ⊚, 30 to 70%: Δ, 30% or less: ×.
【００３０】[0030]
【表２】 [Table 2]
【００３１】表２に示されるように、本発明品は伸長応
力緩和率が大であり、パーマネントに適するものである
ことがわかる。As shown in Table 2, it can be seen that the product of the present invention has a large elongation stress relaxation rate and is suitable for permanent.
【００３２】実施例６〜９及び比較例７〜９ 表３に組成を示す本発明品（実施例６〜９）及び比較品
（比較例７〜９）を常法に従い調製した。Examples 6 to 9 and Comparative Examples 7 to 9 Inventive products (Examples 6 to 9) and comparative products (Comparative Examples 7 to 9) whose compositions are shown in Table 3 were prepared by a conventional method.
【００３３】同一人由来の毛髪をそれぞれ重さ２０ｇの
毛髪束にし、市販のノーマルヘア用パーマネントウェー
ブ剤を用い標準的条件でウェーブをかけた。このウェー
ブヘアの毛束に本発明品又は比較品をそれぞれ２０ｇ塗
布し、よくコーミングした。Hairs from the same person were made into hair bundles each weighing 20 g, and waved under standard conditions using a commercially available permanent waving agent for normal hair. 20 g of the product of the present invention or 20 g of the comparative product was applied to each hair bundle of the wave hair and combed well.
【００３４】これらを１５分間放置後、それぞれに臭素
酸ナトリウム水（臭素酸ナトリウム８ｇ，精製水９２
ｇ）を塗布し、１０分間放置後洗い流した。上記毛束を
自然乾燥後、美容師が目視にてウェーブの伸び具合を判
断した。観察結果を、十分にウェーブが伸びているも
の：◎、少しウェーブが残っているもの：△、ウェーブ
の伸びが不十分であるもの：×として表３に示す。After leaving these for 15 minutes, sodium bromate water (8 g of sodium bromate, purified water
g) was applied, left for 10 minutes and then washed off. After the hair bundle was naturally dried, a hairdresser visually judged the extent of wave expansion. The observation results are shown in Table 3 where the wave is sufficiently extended: ⊚, a little wave remains: Δ, and the wave is insufficiently extended: ×.
【００３５】更に、それぞれの毛束を２回シャンプーし
た後毛髪をサンプリングし、毛髪表面を走査型電子顕微
鏡で観察した。観察したキューティクルの状態を、未処
理毛と同様、剥離がみられないもの：◎、一部に剥離が
みられるもの：△、おびただしい剥離がみられるもの：
×として表３に併せて示す。Further, each hair bundle was shampooed twice and then the hair was sampled, and the hair surface was observed with a scanning electron microscope. Similar to the untreated hair, the observed cuticles show no peeling: ◎, some peeling: △, copious peeling:
It is also shown in Table 3 as x.
【００３６】[0036]
【表３】 [Table 3]
【００３７】表３に示されるように、本発明品は毛髪表
面に損傷を与えることなく、十分にウェーブを伸ばすこ
とが可能であることがわかる。As shown in Table 3, it is understood that the product of the present invention can sufficiently extend the wave without damaging the hair surface.
Claims (1)
から選ばれる１種又は２種以上 （Ｂ）下記一般式（１）で表わされる化合物の１種又は
２種以上 Ｒ１（ＯＣｎＨ２ｎ）ｍＯＨ （１） （式中、Ｒ１はフェニル基、ベンジル基、アルコキシフ
ェニル基、ナフチル基又はアルコキシナフチル基を示
し、ｍは０又は１の数を示し、ｎは０〜３の数を示す） （Ｃ）炭素数１〜４の直鎖状又は分岐鎖状のアルキル基
を有するＮ−アルキルピロリドンの１種又は２種以上を
含有することを特徴とする毛髪処理剤組成物。1. The following components (A), (B) and (C): (A) one or more selected from cysteine, cysteine derivatives and salts thereof (B) in the following general formula (1) One or more compounds represented by R 1 (OC n H 2n ) m OH (1) (In the formula, R 1 represents a phenyl group, a benzyl group, an alkoxyphenyl group, a naphthyl group or an alkoxynaphthyl group, and m Represents a number of 0 or 1 and n represents a number of 0 to 3) (C) One or two kinds of N-alkylpyrrolidone having a linear or branched alkyl group having 1 to 4 carbon atoms A hair treatment composition comprising the above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4095405A JPH0768105B2 (en) | 1992-04-15 | 1992-04-15 | Hair treatment composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4095405A JPH0768105B2 (en) | 1992-04-15 | 1992-04-15 | Hair treatment composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05294812A JPH05294812A (en) | 1993-11-09 |
| JPH0768105B2 true JPH0768105B2 (en) | 1995-07-26 |
Family
ID=14136768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4095405A Expired - Fee Related JPH0768105B2 (en) | 1992-04-15 | 1992-04-15 | Hair treatment composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0768105B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE210975T1 (en) * | 1994-06-23 | 2002-01-15 | Procter & Gamble | TOPICAL PREPARATIONS CONTAINING N-ACETYL-L-CYSTEIN |
| JP3514011B2 (en) * | 1995-10-07 | 2004-03-31 | 花王株式会社 | Hair treatment composition |
| SE522531C2 (en) * | 1999-11-24 | 2004-02-17 | Micronic Laser Systems Ab | Method and apparatus for labeling semiconductors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2528702B2 (en) * | 1988-12-28 | 1996-08-28 | 花王株式会社 | Heating type hair treatment agent |
| JPH02200617A (en) * | 1989-01-31 | 1990-08-08 | Tomiyuki Komiyama | Hair dyeing agent and hair dyeing agent used together for hair dyeing and cold permanent wave |
| JPH05262627A (en) * | 1992-03-23 | 1993-10-12 | Osaka Aerosol Ind Corp | 1st agent composition for aerosol-type permanent wave lotion |
-
1992
- 1992-04-15 JP JP4095405A patent/JPH0768105B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05294812A (en) | 1993-11-09 |
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