JPH08143431A - Pretreating agent for dyeing hair - Google Patents
Pretreating agent for dyeing hairInfo
- Publication number
- JPH08143431A JPH08143431A JP31256294A JP31256294A JPH08143431A JP H08143431 A JPH08143431 A JP H08143431A JP 31256294 A JP31256294 A JP 31256294A JP 31256294 A JP31256294 A JP 31256294A JP H08143431 A JPH08143431 A JP H08143431A
- Authority
- JP
- Japan
- Prior art keywords
- antibody
- hair
- avidin
- biotin
- dyeing
- 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.)
- Pending
Links
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- Cosmetics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、アビジンまたはビオチ
ン結合顔料を染毛剤として使用するに際し、事前に使用
される所のもので、皮膚に結合せず毛髪を選択的に染毛
可能な染毛効果が期待できる染毛用前処理剤に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention is used in advance when using an avidin- or biotin-bonded pigment as a hair dye, and is a dye capable of selectively dyeing hair without binding to the skin. The present invention relates to a pretreatment agent for hair dye, which is expected to have a hair effect.
【０００２】[0002]
【従来の技術】従来より、毛髪を選択的に染毛可能な染
毛剤として、毛髪の構成成分に対する抗体である抗毛髪
抗体を利用した染毛剤が開発されている（特開平６−２
２７９５５号公報参照）。2. Description of the Related Art Heretofore, as a hair dye capable of selectively dyeing hair, a hair dye using an anti-hair antibody which is an antibody against a constituent component of hair has been developed (JP-A-6-2).
No. 27955).
【０００３】しかし、この抗毛髪抗体を利用した染毛剤
は、染色率は高いものの、染色成分として顔料を用いた
場合、抗体が、抗体活性部位で顔料に結合している場合
もあるため、使用した抗体量に見合う結合力を発揮しに
くく、染毛剤としての色持ちに乏しい傾向がある，とい
う欠点を有していた。However, although a hair dye using this anti-hair antibody has a high dyeing rate, when a pigment is used as a dyeing component, the antibody may be bound to the pigment at the antibody active site. It has the drawback that it is difficult to exert a binding force commensurate with the amount of antibody used and that it tends to be poor in color retention as a hair dye.
【０００４】一方、アビジンおよびビオチンはその特異
的結合を利用し、研究用試薬，臨床検査薬に利用されて
きた。例えば、ビオチン化した抗体に酵素標識したアビ
ジンを結合させ酵素活性を測定することによる抗原抗体
反応の高感度検出法が報告されている（J. Histochem.
Cytochem.,27巻, 1131頁, 1979年参照）。しかし、アビ
ジン・ビオチンを染毛剤として用いる報告はない。On the other hand, avidin and biotin have been used as research reagents and clinical test agents by utilizing their specific binding. For example, a highly sensitive method for detecting an antigen-antibody reaction by binding an enzyme-labeled avidin to a biotinylated antibody and measuring the enzyme activity has been reported (J. Histochem.
See Cytochem., 27, 1131, 1979). However, there are no reports of using avidin / biotin as a hair dye.
【０００５】[0005]
【発明が解決しようとする課題】本発明者らは、上述の
欠点を解消すべく鋭意研究を行った結果、ビオチン化
（又はアビジン化）した抗体を、前処理剤として毛髪に
適用した後に、アビジン化（又はビオチン化）した顔料
を施与することで、抗毛髪抗体の毛髪結合力を十分発揮
できるとともに、抗体を用いずにアビジン・ビオチンだ
けで染毛を行うよりも高い染毛効果が得られることを見
出し、本発明を完成したものであって、その目的とする
ところは、高い染毛率と優れた抗体の結合性を達成し得
る、染毛用前処理剤を提供するにある。DISCLOSURE OF INVENTION Problems to be Solved by the Invention As a result of intensive studies to eliminate the above-mentioned drawbacks, the present inventors have found that after applying a biotinylated (or avidinized) antibody to hair as a pretreatment agent, By applying an avidinized (or biotinylated) pigment, the hair-binding strength of the anti-hair antibody can be sufficiently exerted, and a higher hair dyeing effect than that obtained by dyeing with avidin / biotin alone without using an antibody is obtained. The present invention has been found to be obtained, and the present invention has been completed. An object of the invention is to provide a pretreatment agent for hair dyeing, which can achieve a high hair dyeing rate and excellent antibody binding properties. .
【０００６】[0006]
【課題を解決するための手段】上述の目的は、ビオチン
またはアビジンを結合させた抗毛髪抗体を含有すること
を特徴とする染毛用前処理剤によって達成される。The above-mentioned object is achieved by a pretreatment agent for hair dyeing, characterized by containing an anti-hair antibody conjugated with biotin or avidin.
【０００７】本発明に用いられるアビジンは、鶏卵白を
はじめ、主に鳥類の卵白に存在し、ビオチン（ビタミン
Ｈ）と極めて高い親和性を有する分子量約68,000の糖蛋
白質である。The avidin used in the present invention is a glycoprotein having a molecular weight of about 68,000, which is present mainly in avian egg whites such as chicken egg whites and has a very high affinity for biotin (vitamin H).
【０００８】本発明に用いられるビオチンは、ビタミン
Ｈとも呼ばれる公知の水溶性ビタミンで、アビジンと結
合する性質を有している。The biotin used in the present invention is a known water-soluble vitamin also called vitamin H and has a property of binding to avidin.
【０００９】本発明に用いられる抗毛髪抗体とは、ヒト
毛髪に対して免疫活性を有する抗体のことであり、この
ようなものとしては、例えば着色の目的となる毛髪を構
成している各種の成分に対する抗体が挙げられる。この
ような抗体は、例えば毛髪ケラチン蛋白質、毛髪キュー
ティクル蛋白質、毛髪マトリックス蛋白質あるいはそれ
らの断片等を抗原として動物を免疫することにより得ら
れる。更に、動物の爪、体毛、羽毛等、又はそれらから
の抽出物や断片等を免疫することによっても得られる
が、種差等を考慮すれば、人間の毛髪、体毛が好まし
く、特に毛髪を構成している各種の成分が最も好まし
い。The anti-hair antibody used in the present invention is an antibody having an immunological activity on human hair. Examples of such an antibody include various kinds of hair constituting the hair to be colored. Antibodies to the components are included. Such an antibody can be obtained, for example, by immunizing an animal with a hair keratin protein, a hair cuticle protein, a hair matrix protein or a fragment thereof as an antigen. Further, it can be obtained by immunizing animal nails, body hair, feathers, etc., or extracts or fragments thereof, etc., but considering the difference in species, human hair, body hair is preferable, and particularly hair is constituted. The various ingredients mentioned are most preferred.
【００１０】免疫に用いられる動物としては、牛、馬、
羊、山羊、兎、ニワトリ等から適当な家畜を選ぶことが
できる。Animals used for immunization include cattle, horses,
Appropriate livestock can be selected from sheep, goats, rabbits, chickens and the like.
【００１１】抗体は、これらの動物の常乳又は初乳、血
清、あるいは卵黄等より得ることができるが、牛の常乳
又は初乳あるいは卵黄より得られる抗体が、大量に取得
できるため好ましい。The antibody can be obtained from the normal milk or colostrum of these animals, serum, egg yolk, etc., but the antibody obtained from bovine normal milk or colostrum or egg yolk is preferable because a large amount can be obtained.
【００１２】以上述べた抗体原料からの抗体の精製は公
知の方法に従えばよく、例えば適当な方法により脂質を
除いたのち、硫安分画法あるいはアルコール沈澱法ある
いは膜分離法などにより精製し、粗精製抗体を得ること
ができる。必要ならばイオン交換クロマトグラフィーや
ゲル濾過クロマトグラフィー等で更に精製を行ない精製
抗体を得ることができる。更に必要ならば免疫に用いた
抗原をリガンドとするアフィニティークロマトグラフィ
ーを行なうことにより、高純度精製抗体を得ることがで
きる。Purification of the antibody from the above-mentioned antibody raw material may be carried out by a known method. For example, after removing the lipid by an appropriate method, the antibody is purified by the ammonium sulfate fractionation method, the alcohol precipitation method or the membrane separation method. A crudely purified antibody can be obtained. If necessary, further purification can be performed by ion exchange chromatography, gel filtration chromatography or the like to obtain a purified antibody. Further, if necessary, high-purity purified antibody can be obtained by performing affinity chromatography using the antigen used for immunization as a ligand.
【００１３】又、目的とする抗体を産生する抗体産生細
胞とミエローマ細胞の融合細胞から、モノクローン抗体
として抗体を得ることもできる。Further, an antibody can be obtained as a monoclonal antibody from a fused cell of an antibody-producing cell producing a desired antibody and a myeloma cell.
【００１４】以上のようにして得られた抗体は、パパイ
ンあるいはペプシン等の酵素で処理し、免疫グロブリン
のＦｃ部分を除去した抗体断片としてもよい。又、２−
メルカプトエタノールで抗体を還元して得られるＨ鎖や
Ｌ鎖を用いてもよい。The antibody thus obtained may be an antibody fragment obtained by treating with an enzyme such as papain or pepsin to remove the Fc portion of immunoglobulin. Also, 2-
An H chain or L chain obtained by reducing the antibody with mercaptoethanol may be used.
【００１５】又、免疫した動物の脾臓細胞あるいはリン
パ球からクローニングされた免疫グロブリン遺伝子断片
を導入した微生物あるいは培養細胞の産物であってもよ
い。Further, it may be a product of a microorganism or a cultured cell into which an immunoglobulin gene fragment cloned from a spleen cell or lymphocyte of an immunized animal has been introduced.
【００１６】本発明に用いられる、抗毛髪抗体に対して
免疫活性を有する抗体は、上記の抗毛髪抗体を得るため
に免疫した動物と同種の動物由来抗体やその断片等を抗
原として、異種の動物を免疫することによって得られ
る。例えば、抗毛髪抗体を牛乳から得た場合は、牛由来
の抗体を牛以外の動物、例えば兎やニワトリ等に免疫す
ればよい。又、抗毛髪抗体に対して免疫活性を有するモ
ノクローナル抗体も使用することができる。更に、２−
メルカプトエタノールで抗体を還元して得られるＨ鎖や
Ｌ鎖を用いてもよい。これらの抗毛髪抗体に対して免疫
活性を有する抗体は、先に述べた抗毛髪抗体の場合と同
様にして精製することができる。このようにして得られ
た抗体は、パパインあるいはペプシン等の酵素で処理
し、免疫グロブリンのＦｃ部分を除去した抗体断片とし
てもよい。The antibody having an immunological activity against the anti-hair antibody used in the present invention is heterologous with an antibody derived from an animal of the same species as the animal immunized to obtain the anti-hair antibody or a fragment thereof as an antigen. Obtained by immunizing an animal. For example, when the anti-hair antibody is obtained from milk, an animal other than cow, such as rabbits and chickens, may be immunized with the bovine-derived antibody. Further, a monoclonal antibody having an immunological activity against the anti-hair antibody can also be used. Furthermore, 2-
An H chain or L chain obtained by reducing the antibody with mercaptoethanol may be used. Antibodies having immunological activity against these anti-hair antibodies can be purified in the same manner as the above-mentioned anti-hair antibodies. The antibody thus obtained may be an antibody fragment obtained by treating with an enzyme such as papain or pepsin to remove the Fc portion of immunoglobulin.
【００１７】得られた抗毛髪ケラチン抗体は，表皮ケラ
チンと反応せず毛髪由来のケラチンと特異的に反応する
（日本皮膚科学会雑誌,104巻,855頁, 1994年参照）ので
毛髪に選択的に結合することが期待できる。The obtained anti-hair keratin antibody does not react with epidermal keratin but specifically reacts with hair-derived keratin (see Japanese Dermatological Association Magazine, 104, 855, 1994) and is therefore selective for hair. Can be expected to be combined with.
【００１８】本発明で用いられるビオチン結合抗毛髪抗
体は、以下の様にして製造する。毛髪に効率よくビオチ
ンを結合させるには、予めビオチンのカルボキシル基を
活性化したビオチンアミドカプリエ─ト N-ヒドロキシ
スクシンイミド エステルなどを抗毛髪抗体の遊離のア
ミノ基に導入するのが望ましい。これらの活性化ビオチ
ンは、抗毛髪抗体に対し1/100 〜10倍量を加え攪拌する
ことにより容易に反応し、ゲルろ過法や透析などの方法
で未反応物は容易に除去できる。The biotin-conjugated anti-hair antibody used in the present invention is manufactured as follows. In order to efficiently bind biotin to hair, it is desirable to introduce biotinamide capryate N-hydroxysuccinimide ester or the like in which the carboxyl group of biotin is previously activated into the free amino group of the anti-hair antibody. These activated biotins easily react by adding 1/100 to 10 times the amount of anti-hair antibody and stirring, and unreacted substances can be easily removed by a method such as gel filtration or dialysis.
【００１９】つぎに、本発明で用いられるアビジン結合
抗毛髪抗体の製造方法について説明する。抗毛髪抗体と
アビジンは、通常蛋白質の複合体を作製するのに用いら
れるグルタルアルデヒドなどの架橋剤を用いて行うこと
もできるが、抗毛髪抗体同士またはアビジン同士の結合
を少なくし抗毛髪抗体に効率よくアビジンを結合させる
には、予め抗毛髪抗体またはアビジンにN-スクシンイミ
ジル-3-(2-ピリジルジチオ）プロピオネート（SPDP）を
遊離のアミノ基に導入後、還元剤処理することにより遊
離のスルフヒドリル基を生成させ、N-スクシンイミジル
-3-(2-ピリジルジチオ）プロピオネート（SPDP）または
スクシンイミジル-4-(p-マレイミドフェニル）ブチレー
ト（SMPB）を遊離のアミノ基に導入したアビジンまたは
抗毛髪抗体と反応させることが望ましい。Next, a method for producing the avidin-conjugated anti-hair antibody used in the present invention will be described. Anti-hair antibody and avidin can also be performed by using a cross-linking agent such as glutaraldehyde that is usually used for preparing a protein complex, but anti-hair antibody can be reduced by reducing the binding between anti-hair antibodies or avidin. In order to efficiently bind avidin, N-succinimidyl-3- (2-pyridyldithio) propionate (SPDP) was introduced into the free amino group of anti-hair antibody or avidin in advance, and then free sulfhydryl was prepared by treating with a reducing agent. N-succinimidyl generating group
It is desirable to react -3- (2-pyridyldithio) propionate (SPDP) or succinimidyl-4- (p-maleimidophenyl) butyrate (SMPB) with avidin or an anti-hair antibody introduced into the free amino group.
【００２０】以上のようにして得られた本発明の染毛用
前処理剤で処理した毛髪は、下記のアビジンまたはビオ
チンを結合した顔料により特異的に着色することができ
る。染毛用前処理剤がアビジン結合抗毛髪抗体の場合に
は、ビオチン結合顔料を、染毛用前処理剤がビオチン結
合抗毛髪抗体の場合には、アビジン結合顔料を用いる。The hair treated with the pretreatment agent for hair dyeing of the present invention obtained as described above can be specifically colored with the following avidin- or biotin-bonded pigment. When the pretreatment agent for hair dye is an avidin-conjugated anti-hair antibody, a biotin-conjugated pigment is used, and when the pretreatment agent for hair dye is a biotin-conjugated anti-hair antibody, an avidin-conjugated pigment is used.
【００２１】アビジン結合着色料は、アビジンを物理的
吸着又は化学結合により着色料に結合させた後、着色料
を洗浄し、過剰のアビジンを除くことによって得られ
る。The avidin-bonded colorant is obtained by binding avidin to the colorant by physical adsorption or chemical bonding, and then washing the colorant to remove excess avidin.
【００２２】ビオチン結合着色料は、次のようにして作
製することができる。活性化ビオチンで着色料上の遊離
の官能基に直接導入することができるが、予め、ウシ血
清アルブミンをビオチン化してこれを着色料に吸着させ
ることもできる。次にこれを洗浄し、過剰のビオチン化
ウシ血清アルブミンを除くことによってビオチン結合着
色料が得られる。ウシ血清アルブミンをビオチン化して
用いる場合は、チタンブラック等の顔料の分散性が良好
な状態で充分な量のビオチンが顔料表面に導入できるの
で、顔料の毛髪への結合が強固となり好ましい。The biotin-bonded colorant can be prepared as follows. Although it is possible to directly introduce free functional groups on the colorant with activated biotin, it is also possible to biotinate bovine serum albumin in advance and adsorb it to the colorant. This is then washed and the excess biotinylated bovine serum albumin is removed to give the biotin-conjugated colorant. When bovine serum albumin is used after being biotinylated, a sufficient amount of biotin can be introduced onto the pigment surface in a state in which the pigment such as titanium black has good dispersibility, and thus the pigment is strongly bonded to hair, which is preferable.
【００２３】着色料としては、色素，顔料，又は高分子
化合物に包接された色素等が挙げられ、高分子化合物と
しては、ポリスチレン等の合成高分子ポリマー，リポソ
ーム等が挙げられる。Examples of the colorant include dyes, pigments, and dyes included in a polymer compound, and examples of the polymer compound include synthetic polymer polymers such as polystyrene and liposomes.
【００２４】[0024]
【実施例】以下、実施例によって本発明を更に詳細に説
明する。The present invention will be described in more detail with reference to the following examples.
【００２５】実施例に先立って、抗毛髪抗体の作製方法
および染毛剤の評価に用いた染毛試験の方法について記
載する。Prior to the examples, a method for producing an anti-hair antibody and a hair dye test method used for evaluating a hair dye will be described.
【００２６】１．抗毛髪抗体の作製方法 日本畜産学会報，62巻,580頁，1994年に記載の方法に従
って、以下の通り、抗ケラチン抗体を作製した。1. Method for Producing Anti-Hair Antibody Anti-keratin antibody was produced as follows according to the method described in Japanese Society of Animal Science, Volume 62, 580, 1994.
【００２７】健常毛髪10ｇを洗浄後、8M尿素および 0.2
M 2-メルカプトエタノールを含む0.2Mトリス塩酸緩衝液
（pH 9.2）2.5l中で50℃，１時間の抽出操作を繰り返し
て得られた抽出液を遠心した。上清に400gトリス溶液76
0ml に200gのモノヨード酢酸溶液を加え、室温遮光下で
１時間攪拌反応させた。7ml の2-メルカプトエタノール
を加えて反応を止め、充分量の水に対して透析後、２μ
ｍのフィルターを通し透過液を得た。この透過液４容量
部に0.5M酢酸ナトリウム緩衝液(pH 4.2)１容量部を添加
し、酢酸でpH 4.2に調整し毛髪ケラチンを等電点沈殿さ
せた。遠心して得た沈殿を生理食塩水に溶解し、２μｍ
のフィルターを通し除菌後、限外濾過膜で濃縮して毛髪
ケラチン抗原を得た。After washing 10 g of healthy hair, 8 M urea and 0.2
The extract obtained by repeating the extraction operation at 50 ° C. for 1 hour in 2.5 l of 0.2 M Tris-HCl buffer (pH 9.2) containing M 2-mercaptoethanol was centrifuged. 400 g Tris solution 76 in the supernatant
200 g of monoiodoacetic acid solution was added to 0 ml, and the mixture was reacted with stirring for 1 hour under room temperature light shielding. Stop the reaction by adding 7 ml of 2-mercaptoethanol, dialyze against a sufficient amount of water and then add 2μ.
and a permeate was obtained. To 4 parts by volume of this permeate, 1 part by volume of 0.5 M sodium acetate buffer (pH 4.2) was added, and the pH was adjusted to 4.2 with acetic acid to precipitate the hair keratin isoelectrically. The precipitate obtained by centrifugation is dissolved in physiological saline and 2 μm
After sterilization through a filter of No. 1 and concentration with an ultrafiltration membrane, a hair keratin antigen was obtained.
【００２８】毛髪ケラチン抗原を生理食塩水に溶解（蛋
白質濃度20mg/ml)し、フロインドの完全アジュバンドと
等容混合し油中水型のエマルジョンを作製した。このエ
マルジョン5.0ml を出産２か月前の妊娠ホルスタイン牛
の首に皮下投与した。その後10日間隔で、フロインドの
不完全アジュバンドで作製した初回免疫と同量の抗原を
含んだエマルジョンを、１〜３回目の追加免疫は皮下投
与で、４，５回目は筋注にて投与した。The hair keratin antigen was dissolved in physiological saline (protein concentration: 20 mg / ml) and mixed with Freund's complete adjuvant in an equal volume to prepare a water-in-oil emulsion. 5.0 ml of this emulsion was subcutaneously administered to the neck of a pregnant Holstein cow two months before birth. After 10 days, an emulsion containing the same amount of antigen as the initial immunization prepared with Freund's incomplete adjuvant was administered subcutaneously for the 1st to 3rd boosters and intramuscularly for the 4th and 5th boosters. did.
【００２９】免疫した牛の初乳を出産後３日間補集し
た。クリームセパレーターを用いて、初乳より脂肪層を
除き、脱脂乳を得た。この脱脂乳に0.1N塩酸を加えpHを
4.5 に調整し、カゼインを沈殿させた。沈殿物を濾布で
除いた後、2,500 ×g の連続遠心操作で上清を得た。中
和した後33％飽和になるように硫酸アンモニウムを加
え、抗体を塩析させた。2,500 ×g の連続遠心操作で沈
殿を集め、生理リン酸緩衝液に溶解した。得られた溶液
を10mMのリン酸緩衝液(pH 7.5)に対して透析し、同緩衝
液にて平衡化した 2ｌのDEAEセルロースカラム(DE-52，
ワットマン製）に５回に分けてアプライした。同緩衝液
にて、非吸着の蛋白を洗い流した後、50mM塩化ナトリウ
ム含有の同緩衝液で抗体を溶出させ抗体200gを得た。こ
の抗体の純度は90％以上であった。この抗体を、毛髪ケ
ラチンを常法にて結合させた400ml のアフィニティ担体
（アフィゲル15，バイオラッド社）に５回に分けて供し
た。アフィニティ担体に結合した抗毛髪抗体を、0.2Mグ
リシン塩酸緩衝液(pH 2.5)で溶出させ、直ちに3Mトリス
溶液にてpHを８付近に調整し、毛髪ケラチン抗原に対し
て特異的に結合する抗毛髪ケラチン抗体を得た。以下、
単に抗ケラチン抗体と記載する。Colostrum of the immunized cow was collected for 3 days after delivery. The fat layer was removed from the colostrum using a cream separator to obtain skim milk. Add 0.1N hydrochloric acid to this skim milk to adjust the pH.
It was adjusted to 4.5 and casein was precipitated. After removing the precipitate with a filter cloth, a supernatant was obtained by continuous centrifugation at 2,500 × g. After neutralization, ammonium sulfate was added to reach 33% saturation, and the antibody was salted out. The precipitate was collected by continuous centrifugation at 2,500 xg and dissolved in physiological phosphate buffer. The obtained solution was dialyzed against 10 mM phosphate buffer (pH 7.5) and equilibrated with the same buffer, 2 l of DEAE cellulose column (DE-52,
Whatman) was applied 5 times. After washing off non-adsorbed protein with the same buffer, the antibody was eluted with the same buffer containing 50 mM sodium chloride to obtain 200 g of the antibody. The purity of this antibody was 90% or more. This antibody was applied to 400 ml of an affinity carrier (Affigel 15, Bio-Rad Co.) to which hair keratin was bound by a conventional method, in 5 batches. The anti-hair antibody bound to the affinity carrier was eluted with 0.2 M glycine-hydrochloric acid buffer (pH 2.5), and the pH was immediately adjusted to about 8 with 3 M Tris solution, and the anti-hair antibody that specifically bound to the hair keratin antigen was bound. Hair keratin antibody was obtained. Less than,
It is simply described as an anti-keratin antibody.
【００３０】２．染毛試験方法 （１）アビジン結合顔料の作製 チタンブラック10Ｓ（三菱金属社製）１ｇに20mlの蒸留
水を加え、超音波にて分散させた。この分散液にカルボ
キシル基を持ったジルコアルミネ−トカップリング剤
（タイプＣ，Manchem 社製）15μl を添加し、室温にて
２時間攪拌した。この分散液を40℃に加温しながら、エ
バポレ−タ−にて減圧乾固した後、110 ℃で10分間乾燥
させた。ジルコアルミネ−トカップリング剤処理したチ
タンブラック10mgを精製水１mlに分散し、塩酸でpHを5.
0 に調整した後0.002M EDC水溶液１mlを加え室温で２時
間攪拌した。20℃で12000rpm，20分間遠心した後上清を
捨て精製水１mlに再分散した。これに、アビジン３mgを
生理リン酸緩衝液１mlに溶解し加え４℃で一昼夜攪拌し
た。遠心して未反応のアビジンを除き0.1%牛血清アルブ
ミンを含む生理リン酸緩衝液に分散した。再び遠心し0.
1%牛血清アルブミンを含む生理リン酸緩衝液に再分散し
室温で１時間放置した後、0.1%牛血清アルブミンおよび
0.1%ポリオキシエチレンソルビタンモノラウレ−ト（Tw
een 20）を含む生理リン酸緩衝液に分散してアビジン結
合顔料を得た。2. Hair dyeing test method (1) Preparation of avidin-bonded pigment 20 ml of distilled water was added to 1 g of titanium black 10S (manufactured by Mitsubishi Metals Co., Ltd.) and dispersed by ultrasonic waves. To this dispersion was added 15 μl of a zircoaluminate coupling agent having a carboxyl group (Type C, manufactured by Manchem), and the mixture was stirred at room temperature for 2 hours. The dispersion was dried under reduced pressure with an evaporator while heating at 40 ° C, and then dried at 110 ° C for 10 minutes. 10 mg of titanium black treated with a zircoaluminate coupling agent was dispersed in 1 ml of purified water, and the pH was adjusted to 5 with hydrochloric acid.
After adjusting to 0, 1 ml of 0.002M EDC aqueous solution was added and stirred at room temperature for 2 hours. After centrifugation at 12000 rpm for 20 minutes at 20 ° C., the supernatant was discarded and redispersed in 1 ml of purified water. Avidin (3 mg) was dissolved in physiological phosphate buffer (1 ml), and the mixture was stirred at 4 ° C. for 24 hours. After centrifugation, unreacted avidin was removed and the mixture was dispersed in a physiological phosphate buffer containing 0.1% bovine serum albumin. Centrifuge again for 0.
After redispersion in physiological phosphate buffer containing 1% bovine serum albumin and leaving it at room temperature for 1 hour, 0.1% bovine serum albumin and
0.1% polyoxyethylene sorbitan monolaurate (Tw
een 20) and dispersed in a physiological phosphate buffer solution to obtain an avidin-bonded pigment.
【００３１】（２）ビオチン化ウシ血清アルブミン結合
顔料の作製 ウシ血清アルブミン１mgを生理リン酸緩衝液（pH 7.2）
１mlに溶解した後、0.2 mlの1M炭酸水素ナトリウムを加
えpHを9.0 とした。予め、ジメチルスルホキシドに溶解
したビオチンアミドカプリエ−ト N-ヒドロキシスクシ
ンイミド エステル（50mg/ml)を40μl 加え、一晩４℃
で振とうした。この反応液を生理リン酸緩衝液（pH 7.
2）で平衡化したSephadex G-25 (Pharmacia社製）にか
け、素通り画分に溶出するビオチン化ウシ血清アルブミ
ンを集めた。なお、結合したビオチンをMetohds Enzymo
l. 18A巻,418頁, 1970年に記載の方法により定量した結
果、ウシ血清アルブミン１分子あたり 1.8分子のビオチ
ンが結合していた。(2) Preparation of biotinylated bovine serum albumin binding pigment 1 mg bovine serum albumin was added to physiological phosphate buffer (pH 7.2)
After dissolving in 1 ml, pH was adjusted to 9.0 by adding 0.2 ml of 1M sodium hydrogen carbonate. 40 μl of biotinamide capryate N-hydroxysuccinimide ester (50 mg / ml) previously dissolved in dimethyl sulfoxide was added, and the mixture was kept overnight at 4 ° C.
I shook it up. This reaction solution was added to physiological phosphate buffer (pH 7.
It was applied to Sephadex G-25 (manufactured by Pharmacia) equilibrated in 2) and biotinylated bovine serum albumin that was eluted in the flow-through fraction was collected. In addition, the bound biotin was treated with Metohds Enzymo
As a result of quantification by the method described in L. 18A, page 418, 1970, 1.8 molecules of biotin were bound per molecule of bovine serum albumin.
【００３２】ジルコアルミネ−トカップリング剤処理し
たチタンブラック10mgを精製水１mlに分散し、塩酸でpH
を5.0 に調整した後0.002M EDC水溶液１mlを加え室温で
２時間攪拌した。20℃で12000rpm，20分間遠心した後上
清を捨て精製水１mlに再分散した。これに、ビオチン化
ウシ血清アルブミン１mgを生理リン酸緩衝液１mlに溶解
し加え４℃で一昼夜攪拌した。遠心して未反応のアビジ
ンを除き0.1%牛血清アルブミンを含む生理リン酸緩衝液
に分散した。再び遠心し0.1%牛血清アルブミンを含む生
理リン酸緩衝液に再分散し室温で１時間放置した後、0.
1%牛血清アルブミンおよび0.1%ポリオキシエチレンソル
ビタンモノラウレ−ト（Tween 20）を含む生理リン酸緩
衝液に分散してビオチン化ウシ血清アルブミン結合顔料
を得た。10 mg of titanium black treated with a zircoaluminate coupling agent was dispersed in 1 ml of purified water, and the pH was adjusted with hydrochloric acid.
After adjusting to 5.0, 1 ml of 0.002M EDC aqueous solution was added and stirred at room temperature for 2 hours. After centrifugation at 12000 rpm for 20 minutes at 20 ° C., the supernatant was discarded and redispersed in 1 ml of purified water. To this, 1 mg of biotinylated bovine serum albumin was dissolved in 1 ml of physiological phosphate buffer, and the mixture was stirred at 4 ° C. for 24 hours. After centrifugation, unreacted avidin was removed and the mixture was dispersed in a physiological phosphate buffer containing 0.1% bovine serum albumin. Centrifuge again, redisperse in physiological phosphate buffer containing 0.1% bovine serum albumin, leave at room temperature for 1 hour, then
The pigment was dispersed in a physiological phosphate buffer containing 1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20) to obtain a biotinylated bovine serum albumin-bound pigment.
【００３３】（３）染毛試験 アビジン結合顔料，または、ビオチン化ウシ血清アルブ
ミン結合顔料を0.1%牛血清アルブミンおよび0.1%ポリオ
キシエチレンソルビタンモノラウレ−ト（Tween 20）を
含む生理リン酸緩衝液で 0.1％（顔料重量）に分散した
後、その１mlを、ヒト白髪毛束（50mg）を１％メルカプ
トエタノールで30℃，10分間処理後精製水で洗浄した還
元毛髪に加え１時間回転させた。ついで0.05％Tween 20
を含む生理食塩水で洗浄し乾燥した。(3) Hair dyeing test Avidin-conjugated pigment or biotinylated bovine serum albumin-conjugated pigment was added to physiological phosphate buffer containing 0.1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20). Disperse to 0.1% (pigment weight) with a liquid, and add 1 ml of the human hair bundle (50 mg) to 1% mercaptoethanol at 30 ° C for 10 minutes, then add to the reduced hair washed with purified water and rotate for 1 hour. It was Then 0.05% Tween 20
It was washed with a physiological saline solution containing and dried.
【００３４】染毛操作を行った後、目視により着色度
を、下記の基準により判定した。 ４・・・著しく濃い黒色に染まった。 ３・・・濃い黒色に染まった。 ２・・・黒色に染まった。 １・・・薄い黒色に染まった。 ０・・・全く染まらなかった。After the hair dyeing operation, the degree of coloring was visually evaluated according to the following criteria. 4 ... It was dyed in a remarkably dark black color. 3 ... It was dyed in a dark black color. 2 ... It was dyed black. 1 ... It was dyed in a light black color. 0 ... It didn't stain at all.
【００３５】実施例１（ビオチン化抗ケラチン抗体含有
染毛用前処理剤の作製） （１）ビオチン化抗ケラチン抗体の作製 抗ケラチン抗体１mgを生理リン酸緩衝液（pH 7.2）１ml
に溶解した後、0.2 mlの1M炭酸水素ナトリウムを加えpH
を9.0 とした。予め、ジメチルスルホキシドに溶解した
ビオチンアミドカプリエ−ト N-ヒドロキシスクシンイ
ミド エステル（50mg/ml)を40μl 加え、一晩４℃で振
とうした。この反応液を生理リン酸緩衝液（pH 7.2）で
平衡化したSephadex G-25 (Pharmacia社製）にかけ、素
通り画分に溶出するビオチン化抗体を集めた。なお、結
合したビオチンをMetohds Enzymol. 18A巻,418頁, 1970
年に記載の方法により定量した結果、抗ケラチン抗体１
分子あたり 8.0分子のビオチンが結合していた。Example 1 (Preparation of pretreatment agent for hair dye containing biotinylated anti-keratin antibody) (1) Preparation of biotinylated anti-keratin antibody 1 mg of anti-keratin antibody was added to 1 ml of physiological phosphate buffer (pH 7.2)
Then, add 0.2 ml of 1M sodium hydrogen carbonate to the pH.
Was set to 9.0. 40 μl of biotinamide capryate N-hydroxysuccinimide ester (50 mg / ml) previously dissolved in dimethyl sulfoxide was added, and the mixture was shaken overnight at 4 ° C. This reaction solution was applied to Sephadex G-25 (manufactured by Pharmacia) equilibrated with physiological phosphate buffer (pH 7.2) to collect biotinylated antibodies that were eluted in the flow-through fraction. The bound biotin was bound to Metohds Enzymol. 18A, 418, 1970.
Anti-keratin antibody 1 as a result of quantification by the method described in
8.0 molecules of biotin were bound per molecule.
【００３６】（２）染毛用前処理剤の調製 ビオチン化抗ケラチン抗体を0.1%牛血清アルブミンおよ
び0.1%ポリオキシエチレンソルビタンモノラウレ−ト
（Tween 20）を含む生理リン酸緩衝液に溶解し、染毛用
前処理剤を調製した。(2) Preparation of pretreatment agent for hair dye Biotinylated anti-keratin antibody was dissolved in physiological phosphate buffer containing 0.1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20). Then, a pretreatment agent for hair dyeing was prepared.
【００３７】比較例１（ビオチン含有染毛用前処理剤の
作製） ビオチン化抗ケラチン抗体と同量のビオチンを0.1%牛血
清アルブミンおよび0.1%ポリオキシエチレンソルビタン
モノラウレ−ト（Tween 20）を含む生理リン酸緩衝液に
溶解し染毛用前処理剤を調製した。Comparative Example 1 (Preparation of biotin-containing pretreatment agent for hair dye) The same amount of biotin as the biotinylated anti-keratin antibody was added to 0.1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20). A pretreatment agent for hair dye was prepared by dissolving it in a physiological phosphate buffer solution containing.
【００３８】試験例１（ビオチン化抗体含有染毛用前処
理剤により処理したヒト白髪のアビジン結合顔料による
染毛試験） 実施例１の方法で作製したビオチン化抗ケラチン抗体
（１０または１００μｇ／ｍｌ）含有染毛用前処理剤，
または、比較例１の方法で作製したビオチン含有染毛用
前処理剤１mlをヒト白髪毛束（50mg）に加え１時間回転
させた。ついで0.05％Tween 20を含む生理食塩水で洗浄
した後、アビジン結合顔料で染毛試験を行った。試験結
果を表１に示した。Test Example 1 (Hair dyeing test of human gray hair treated with a biotinylated antibody-containing pretreatment agent for hair dye using an avidin-bonded pigment) The biotinylated anti-keratin antibody prepared by the method of Example 1 (10 or 100 μg / ml) ) Pretreatment agent for hair dye,
Alternatively, 1 ml of the biotin-containing pretreatment agent for hair dye prepared by the method of Comparative Example 1 was added to a human white hair bundle (50 mg) and the mixture was rotated for 1 hour. Then, after washing with a physiological saline containing 0.05% Tween 20, a hair dyeing test was carried out using an avidin-bonded pigment. The test results are shown in Table 1.
【００３９】[0039]
【表１】 [Table 1]
【００４０】実施例１のビオチン化抗ケラチン抗体含有
染毛用前処理剤によって処理したヒト毛髪は、アビジン
結合顔料で充分に着色された。これに対し、比較例１の
ビオチン含有染毛用前処理剤によって処理したヒト毛髪
は、アビジン結合顔料で着色されなかった。Human hair treated with the pretreatment agent for hair dye containing the biotinylated anti-keratin antibody of Example 1 was sufficiently colored with the avidin-bonded pigment. In contrast, human hair treated with the biotin-containing pretreatment agent for hair dye of Comparative Example 1 was not colored with the avidin-bonded pigment.
【００４１】実施例２（アビジン─抗ケラチン抗体コン
ジュゲート含有染毛用前処理剤の作製） （１）アビジン─抗ケラチン抗体コンジュゲートの作製 アビジン10mgを 0.3M NaClおよび0.5%n-ブタノールを含
む0.05M 炭酸緩衝液（pH 9.0）1ml に溶解し、予め、ジ
メチルホルムアミドに溶解したN-スクシンイミジル-3-
(2-ピリジルジチオ）プロピオネート（SPDP）（6mg/ml)
を25μl 加え、30分間室温で振とうした。この反応液
を生理リン酸緩衝液（pH 7.2）で平衡化したCW-35 (1.5
×5.5cm,東ソー社製）にかけ，素通り画分に溶出する P
DP化アビジン(3ml) を集めた。Example 2 (Preparation of pretreatment agent for hair dye containing avidin-anti-keratin antibody conjugate) (1) Preparation of avidin-anti-keratin antibody conjugate Avidin 10 mg containing 0.3M NaCl and 0.5% n-butanol N-succinimidyl-3-dissolved in 1 ml of 0.05M carbonate buffer (pH 9.0) and previously dissolved in dimethylformamide
(2-Pyridyldithio) propionate (SPDP) (6mg / ml)
Was added at 25 μl and shaken for 30 minutes at room temperature. This reaction solution was equilibrated with physiological phosphate buffer (pH 7.2) to give CW-35 (1.5
X 5.5 cm, manufactured by Tosoh Corporation) and elute in the flow-through fraction P
DP-Avidin (3 ml) was collected.
【００４２】抗ケラチン抗体12.5mgを 0.3M NaClおよび
0.5%n-ブタノールを含む0.05M 炭酸緩衝液（pH 9.0）1
2.5mlに溶解し、予め、ジメチルホルムアミドに溶解し
たN-スクシンイミジル-3-(2-ピリジルジチオ）プロピオ
ネート（SPDP）（6mg/ml) を16.2μl 加え、30分間室温
で振とうした。この反応液を0.1M NaCl を含む0.1M酢酸
緩衝液（pH 4.5）で平衡化したCW-35 (1.5×5.5cm,東ソ
ー社製）にかけ、素通り画分に溶出する PDP化抗体(3m
l) を集めた。これにジチオスレイトール46.3mgを加
え、30分間室温で振とうした。この反応液を窒素置換し
た生理リン酸緩衝液（pH 7.2）で平衡化したCW-35 (1.5
×5.5cm,東ソー社製）に２回に分けてかけ、素通り画分
に溶出するチオプロピオニル抗体(3ml×2)を集めた。12.5 mg of anti-keratin antibody was added to 0.3 M NaCl and
0.05M carbonate buffer (pH 9.0) containing 0.5% n-butanol 1
After dissolving in 2.5 ml, 16.2 μl of N-succinimidyl-3- (2-pyridyldithio) propionate (SPDP) (6 mg / ml) previously dissolved in dimethylformamide was added, and the mixture was shaken at room temperature for 30 minutes. This reaction solution was applied to CW-35 (1.5 x 5.5 cm, manufactured by Tosoh Corporation) equilibrated with 0.1 M acetate buffer (pH 4.5) containing 0.1 M NaCl, and the PDP-conjugated antibody (3 m
l) collected. To this, 46.3 mg of dithiothreitol was added and shaken for 30 minutes at room temperature. This reaction solution was equilibrated with a physiological phosphate buffer solution (pH 7.2) that had been replaced with nitrogen, and CW-35 (1.5
(× 5.5 cm, manufactured by Tosoh Corporation) was divided into two portions, and the thiopropionyl antibody (3 ml × 2) eluted in the flow-through fraction was collected.
【００４３】上述の方法で得た PDP化アビジン1.5ml に
チオプロピオニル抗体 6mlを加えた後、30分間室温で振
とうした。この反応液を生理リン酸緩衝液（pH 7.2）で
平衡化したSephacryl S-300 (2.8×19cm, Pharmacia 社
製）にかけ、素通り画分に溶出するアビジン─抗ケラチ
ン抗体コンジュゲート(35ml)を集めた。この溶液をＳＤ
Ｓ−１０％ポリアクリルアミドゲル電気泳動により分析
したところアビジンおよび抗ケラチン抗体より高分子の
アビジン─抗ケラチン抗体コンジュゲートのバンドが確
認された（図１）。6 ml of the thiopropionyl antibody was added to 1.5 ml of the PDP-modified avidin obtained by the above method, and the mixture was shaken at room temperature for 30 minutes. This reaction solution was applied to Sephacryl S-300 (2.8 × 19 cm, manufactured by Pharmacia) equilibrated with physiological phosphate buffer (pH 7.2), and the avidin-anti-keratin antibody conjugate (35 ml) eluted in the flow-through fraction was collected. It was SD this solution
When analyzed by S-10% polyacrylamide gel electrophoresis, a high molecular avidin-anti-keratin antibody conjugate band was confirmed as compared with avidin and anti-keratin antibody (FIG. 1).
【００４４】なお、PDP 化アビジンとチオプロピオニル
抗体の反応により遊離するピリジン-2- チオンの343nm
の吸光度から推定した結果、抗ケラチン抗体１分子あた
り 1.1分子のビオチンが結合していた。343 nm of pyridine-2-thione released by the reaction of PDP-modified avidin and thiopropionyl antibody
As a result of estimation from the absorbance of 1., 1.1 molecule of biotin was bound to 1 molecule of the anti-keratin antibody.
【００４５】（２）染毛用前処理剤の調製 アビジン─抗ケラチン抗体コンジュゲートを0.1%牛血清
アルブミンおよび0.1%ポリオキシエチレンソルビタンモ
ノラウレ−ト（Tween 20）を含む生理リン酸緩衝液に溶
解し染毛用前処理剤を調製した。(2) Preparation of pretreatment agent for hair dye Physiological phosphate buffer containing 0.1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20) containing avidin-antikeratin antibody conjugate To prepare a pretreatment agent for hair dye.
【００４６】比較例２（アビジン含有染毛用前処理剤の
作製） アビジンを、0.1%牛血清アルブミンおよび0.1%ポリオキ
シエチレンソルビタンモノラウレ−ト（Tween 20）を含
む生理リン酸緩衝液に溶解し染毛用前処理剤を調製し
た。Comparative Example 2 (Preparation of pretreatment agent for hair dye containing avidin) Avidin was added to a physiological phosphate buffer containing 0.1% bovine serum albumin and 0.1% polyoxyethylene sorbitan monolaurate (Tween 20). A pretreatment agent for hair dye was prepared by dissolving.
【００４７】試験例２（アビジン化─抗ケラチン抗体コ
ンジュゲート含有染毛用前処理剤により処理したヒト白
髪のビオチン化ウシ血清アルブミン結合顔料による染毛
試験） 実施例２の方法で作製したアビジン─抗ケラチン抗体コ
ンジュゲート含有染毛用前処理剤，または、比較例２の
方法で作製したアビジン含有染毛用前処理剤１mlをヒト
白髪毛束（50mg）に加え１時間回転させた。ついで0.05
％Tween 20を含む生理食塩水で洗浄した後、ビオチン化
ウシ血清アルブミン結合顔料で染毛試験を行った。試験
結果を表２に示した。Test Example 2 (Avidinization—Hair Dyeing Test of Human White Hair Treated with Pretreatment Agent for Hair Dye Containing Anti-Keratin Antibody Conjugate with Biotinylated Bovine Serum Albumin Binding Pigment) Avidin prepared by the method of Example 2 1 ml of the pretreatment agent for hair dye containing an anti-keratin antibody conjugate or the pretreatment agent for hair dye containing avidin prepared by the method of Comparative Example 2 was added to a human hair bundle (50 mg) and rotated for 1 hour. Then 0.05
After washing with physiological saline containing% Tween 20, a hair dyeing test was performed with a biotinylated bovine serum albumin binding pigment. The test results are shown in Table 2.
【００４８】[0048]
【表２】 [Table 2]
【００４９】実施例２のアビジン─抗ケラチン抗体コン
ジュゲート含有染毛用前処理剤によって処理したヒト毛
髪は、比較例２のアビジン含有染毛用前処理剤によって
処理したヒト毛髪に比べよく着色された。The human hair treated with the avidin-anti-keratin antibody conjugate-containing pretreatment agent for hair dye of Example 2 was colored better than the human hair treated with the avidin-containing pretreatment agent for hair dye of Comparative Example 2. It was
【００５０】[0050]
【発明の効果】本発明の染毛用前処理剤を用いれば、予
め抗体を結合させてから顔料を施与するため、抗毛髪抗
体の特異性を十分発揮させることが可能であるととも
に、アビジン・ビオチンだけで染毛を行うよりも、高い
染毛効果が得られる。When the pretreatment agent for hair dyeing of the present invention is used, the antibody is bound in advance and then the pigment is applied, so that the specificity of the anti-hair antibody can be sufficiently exerted, and at the same time, avidin・ Higher hair dyeing effect than hair dyeing with biotin.
【図１】実施例２で作成したアビジン−抗ケラチン抗体
コンジュゲートの電気泳動の結果を表す図面代用写真で
ある。第１レーンはホスホリラ−ゼｂ（94,000）ウシ血
清アルブミン（67,000），オボアルブミン（43,000），
炭酸脱水酵素（30,000），α−ラクトアルブミン（14,4
00），第２レーンはアビジン，第３レーンは抗ケラチン
抗体，第４レーンはアビジン─抗ケラチン抗体コンジュ
ゲートの分析結果である。FIG. 1 is a drawing-substituting photograph showing a result of electrophoresis of an avidin-anti-keratin antibody conjugate prepared in Example 2. Lane 1 is phosphorylase b (94,000) bovine serum albumin (67,000), ovalbumin (43,000),
Carbonic anhydrase (30,000), α-lactalbumin (14,4
00), the second lane is avidin, the third lane is an anti-keratin antibody, and the fourth lane is an avidin-anti-keratin antibody conjugate.
フロントページの続き (72)発明者 平岡 淳一郎 神奈川県小田原市寿町５丁目３番28号 鐘 紡株式会社生化学研究所内Front Page Continuation (72) Inventor Junichiro Hiraoka 5-3 28, Kotobuki-cho, Odawara-shi, Kanagawa Kanebo Co., Ltd.
Claims (1)
毛髪抗体を含有することを特徴とする染毛用前処理剤。1. A pretreatment agent for hair dyeing, which comprises an anti-hair antibody bound to biotin or avidin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31256294A JPH08143431A (en) | 1994-11-22 | 1994-11-22 | Pretreating agent for dyeing hair |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31256294A JPH08143431A (en) | 1994-11-22 | 1994-11-22 | Pretreating agent for dyeing hair |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08143431A true JPH08143431A (en) | 1996-06-04 |
Family
ID=18030712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31256294A Pending JPH08143431A (en) | 1994-11-22 | 1994-11-22 | Pretreating agent for dyeing hair |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08143431A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7220405B2 (en) * | 2003-09-08 | 2007-05-22 | E. I. Du Pont De Nemours And Company | Peptide-based conditioners and colorants for hair, skin, and nails |
| US7285264B2 (en) * | 2003-09-08 | 2007-10-23 | E.I. Du Pont De Nemours And Company | Peptide-based body surface coloring reagents |
| US7807141B2 (en) | 2003-09-08 | 2010-10-05 | E.I. Du Pont De Nemours And Company | Peptide-based oral care surface reagents for personal care |
| JP2012522057A (en) * | 2009-03-30 | 2012-09-20 | ジヨンソン・アンド・ジヨンソン・コンシユーマー・カンパニーズ・インコーポレーテツド | Peptide-based systems for the delivery of cosmetic agents |
| JP2013543865A (en) * | 2010-11-15 | 2013-12-09 | エイボン プロダクツ インコーポレーテッド | Good cosmetics fixed biologically |
-
1994
- 1994-11-22 JP JP31256294A patent/JPH08143431A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7220405B2 (en) * | 2003-09-08 | 2007-05-22 | E. I. Du Pont De Nemours And Company | Peptide-based conditioners and colorants for hair, skin, and nails |
| US7285264B2 (en) * | 2003-09-08 | 2007-10-23 | E.I. Du Pont De Nemours And Company | Peptide-based body surface coloring reagents |
| US7790147B2 (en) | 2003-09-08 | 2010-09-07 | E. I. Du Pont De Nemours And Company | Peptide-based conditioners and colorants for hair, skin, and nails |
| US7807141B2 (en) | 2003-09-08 | 2010-10-05 | E.I. Du Pont De Nemours And Company | Peptide-based oral care surface reagents for personal care |
| US8475772B2 (en) | 2003-09-08 | 2013-07-02 | E I Du Pont De Nemours And Company | Peptide-based oral care surface reagents for personal care |
| JP2012522057A (en) * | 2009-03-30 | 2012-09-20 | ジヨンソン・アンド・ジヨンソン・コンシユーマー・カンパニーズ・インコーポレーテツド | Peptide-based systems for the delivery of cosmetic agents |
| JP2013543865A (en) * | 2010-11-15 | 2013-12-09 | エイボン プロダクツ インコーポレーテッド | Good cosmetics fixed biologically |
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