JPH0425251B2 - - Google Patents
Info
- Publication number
- JPH0425251B2 JPH0425251B2 JP58018240A JP1824083A JPH0425251B2 JP H0425251 B2 JPH0425251 B2 JP H0425251B2 JP 58018240 A JP58018240 A JP 58018240A JP 1824083 A JP1824083 A JP 1824083A JP H0425251 B2 JPH0425251 B2 JP H0425251B2
- Authority
- JP
- Japan
- Prior art keywords
- hair
- waving
- weight
- neutralizing
- reducing agent
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/22—Peroxides; Oxygen; Ozone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Cosmetics (AREA)
Description
本発明は毛髪、特に人の毛髪をウエービングか
けし又は伸ばすための組成物およびその用法に関
する。特に本発明は組成物および毛髪を整髪又は
改良状態におく上記方法に関する。
毛髪のウエーブかけ又はウエーブ伸ばし(しば
しば“パーマネント”処理ともいう)は普通毛髪
中のケラチンの2硫化物結合を還元又は裂開する
薬剤(以後“還元剤”という、または還元剤を含
む組成物は以後“還元用”又は“ウエービング”
“組成物”又は“ローシヨン”という)を応用し
て内部弾性又は他の抵抗なしに毛髪に形をつけた
後ケラチン結合を再生する中和剤を応用して毛髪
をその望む新形に固定するのである。一般に中和
剤は過酸化水素水溶液などの様な酸化性溶液であ
る。
還元性ローシヨンによる毛髪のウエーブかけと
伸ばしとは別に、強アルカリを普通糊状又はクリ
ーム状で使う毛髪のいわゆる弛緩がある。アルカ
リの作用機構は普通のパーマネントウエーブかけ
と伸ばしにおける還元剤の作用機構とはちがう。
後者の場合ケラチンの2硫化物結合は裂開され中
和剤によつて戻されるまでそのままでいるが、苛
性アルカリ処理の場合ケラチンの2硫化物結合は
1硫化物結合に変えられ次の酸による“中和”は
単に残留塩基の酸との普通の中和である。故に本
明細書で使う“ウエーブかけ”および“伸ばし”
は強塩基による毛髪の弛緩を考えていない。
毛髪をメルカプタン、亜硫酸塩又はホスフイン
の様な還元剤によるウエーブかけ又は伸ばしは殆
んど必ず毛髪の感触をわるくし、もつれさせとか
しにくくする。このことはすべての毛髪型にあて
はまり、特にウエーブかけ前漂白、染髪した又は
長期大気にさらした毛髪には厄介である。これを
軽減する普通の方法はウエーブした毛髪をアルキ
ル−ジメチルベンジルハロゲン化物、砿油乳濁
液、ラノリン等の様な整髪剤で処理することであ
る。この種の整髪剤は普通ウエーブかけ又は伸ば
し法の中和工程に使われている。この整髪用組成
物は毛髪の感触をよくしとかし易くするが、その
効果は一時的で洗髪すれば全く失なわれる。
ソコールの米国特許第3912808号は還元剤とポ
リジメチルジアリルアンモニウム塩化物、陽イオ
ン性重合体を含むウエービングローシヨンを使う
毛髪のウエーブかけ又は伸ばし法を発表してい
る。本特許の方法は工業製品に使われ、この応用
に関して試験し比較された。ポリジメチルジアリ
ルアンモニウム塩化物は本発明には使用されてい
ない。
ヒシユングらの米国特許第4175572号は他のも
のと共にポリジメチルジアリルアンモニウム塩化
物も含む苛性アルカリ毛髪弛緩剤に関するもの
で、ウエーブかけ又は伸ばしに関するものでな
い。重合体はアルカリ性弛緩剤と別に又はその応
用前又は後にも使用できる。酸性洗髪は過剰アル
カリ性溶液除去のため弛緩又は条件処理後に使う
とされている。最終洗髪工程又はその組成物につ
いては述べられていないしまたそれは条件処理法
の一部ではないとしている。この意味で中和用組
成物中に陽イオン性表面活性剤を使う上記米国特
許第3912808号に基づく市販製品に等しいと考え
られる。これに反し本発明はポリジメチルアリル
アンモニウム塩化物を使わない他に毛髪の存在で
調整用沈澱を生成する陽イオン性表面活性剤の存
在を特に必要とする。更に本発明は強アルカリ弛
緩剤組成物に関しては有用ではない。
今や毛髪のウエーブかけ又は伸ばし法において
普通の技法に特別効果があり反復洗髪にも持続す
る耐久性毛髪調整法が発見されたのである。この
方法は毛髪を還元剤とクレアクワツト−1(下に
詳述する)と呼ばされる陽イオン性重合体の有効
量を含むウエービング水性組成物で処理した後上
記毛髪を酸化剤と陰イオン性表面活性剤を含む水
性中和用組成物で処理することより成る。ウエー
ブかけ(又は伸ばし)における初めの還元工程と
つづく中和工程および成分の独特な組合せの結果
として反復洗髪にも安定な調整性複合物が毛髪中
に生成される。
したがつて本発明の目的は毛髪を反復洗髪にも
耐える状態に保つウエーブかけ又は伸ばし法を提
供することにある。
本発明の目的は上記の方法を行なう便利な組成
物を提供することにある。
本発明の更に詳細な目的は本明細書および特許
請求範囲から明白となるであろう。
下記明細書と特許請求範囲において可能な場合
は薬品を化粧品香料協会の化粧品成分辞典中にあ
るCTFA名で記載する。
本発明の目的に有用なクレアクワツト−1と呼
ばれる陽イオン性重合体を説明する前にこれと類
似の他型の陽イオン性重合体についてまず述べ、
その後にクレアクワツト−1について述べる。こ
れの陽イオン性重合体の分子量は重量平均基準で
表わしている。稍好ましい他型はポリクオーター
ニウムー1、オニツクスケミカルス社からオナマ
ーM(以後オナマーという)の名で市販されてい
る第4級化されたエタノールアミン末端基をもつ
重合体第4級化されたジメチルブテニルアンモニ
ウム塩化物であり式:
をもつといわれる。上式のnは分子量に比例した
カージナル数でありまた分子量は800乃至5000、
好ましくは1000乃至3500である。
他型の陽イオン性重合体はそれ自体知られた方
法で製造される第4級化されたポリビニルアミン
の重合体および共重合体である。これらは次の反
復単位:
(式中R1、R2およびR3は同種基又は異種基で
もよく炭素原子1乃至20をもつアルキル基を表わ
し、かつX-はよう化物又は塩化物の様なハロゲ
ン化物の化粧品に使用される陰イオンを表わす)
から構成されると信じられている。分子量は3000
乃至150000が好ましい。この重合体は以後
“QPVAMINE”という。例として反復単位:
で構成されると信じられているトリメチルポリビ
ニルアンモニウム硫酸塩をあげることができる。
これは平均分子量約50000をもつ。
別の他型陽イオン性物質はそれ自体知られた方
法で製造される第4級化されたポリ−4−ビニル
ピリジンの重合体がある。これは一般式:
(式中Rは炭素原子1乃至20をもつアルキル基
を表わしかつX-はハロゲン化物、硫酸塩又はカ
ルボキシレイトの様な化粧品に使用される陰イオ
ンを表わす)をもつ。これはまた約5000乃至約
500000の分子量をもつ。この重合体は以後
“QPVP”という。
この型の陽イオン性重合体の例として次式:
をもちまた平均分子量約50000をもつポリビニル
メチルピリジニウムよう化物がある。
本発明によつて特別によい結果がえられること
が発見された陽イオン性重合体はポリ(メタクリ
ル−アミドプロピルトリメチルアンモニウム塩化
物)で、これはテキサコケミカルス社から
MAPTACとして市販されている対応する単量体
をそれ自体知られた方法で重合して製造される。
この重合体は反復単位:
(式中nは分子量に比例する)で構成されてい
るといわれている。分子量は5000乃至500000が好
ましい。この重合体は以後“クレアクワツト−
1”という。
上記のとおり特定の陽イオン性重合体クレアク
ワツト−1がこの方法に使われる還元性ローシヨ
ンに含まれる。還元性ローシヨン中に含まれる陽
イオン性重合体の量は望む結果によつて幾分変ら
れるが、普通還元性ローシヨン全重量を基準とし
て約0.2乃至約10重量%、最適範囲約1乃至約5
重量%である。
陽イオン性重合体が本発明に使用できるかどう
か予想するに陽イオン性重合体の構造特性や知ら
れた物理化学特性は使用できない。したがつて多
くの陽イオン性重合体は本明細書に発表されたも
のの代りに使用した場合毛髪の耐久調整剤に不適
当とわかつた。不十分とわかつた陽イオン性重合
体のいくつかには
第4級化ポリ−2−ビニルピリジン;
アジピン酸とエポキシプロピルジエチレントリ
アミン共重合体(ヘラクレス ケミカル社よりデ
ルセツト101の名で市販);
アジピン酸とジメチルアミノヒドロキシプロピ
ルジエチレントリアミン共重合体(サンドズ社よ
りカータレチツクF−4の名で市販);
ポリ(N−(3−ジメチルアミノ)プロピル)−
N′−(3−(エチレンオキシエチレンジメチルア
ミノ)プロピル)ウレア2塩化物(ラミノール
ケミカル社からミラノールA15の名で市販);
クオーターニウム−23.ジメチルサルフエイト
およびビニルピロリドンとジメチルアミノエチル
メタクリレイトの共重合体の反応によつて生成さ
れた第4級アンモニウム重合体(GAF社からガ
フクワツト755Nの名で市販);クオーターニウム
−19.エピクロロヒドリンと反応させた後トリメ
チルアミンで第4級化したヒドロキシエチルセル
ロースの重合体(ユニオン カーバイド社からポ
リマーJR−400の名で市販);
加水分解したコラーゲン蛋白質の第4級アンモ
ニウム誘導体(クロダ社からクロテインQの名で
市販);
クオーターニウム−39.アクリルアミドとベー
タ−メタクリルオキシエチルトリメチルアンモニ
ウムメトサルフエイトの共重合体(ハーキユルス
ケミカル社からレテン205Mの名で市販);
アミノエチルアクリレイトホスフエイとアクリ
レイトの共重合体(ナシヨナル スターチ社から
カトレツクスの名で市販)および
ジメチルジアリルアンモニウム塩化物とアクリ
ルアミドの共重合体であるクオーターニウム−41
(メルク社からメルクワツト−550の名で市販)
がある。
陽イオン性重合体の他に本発明に使われるウエ
ーブかけ又は還元性ローシヨンはウエービングロ
ーシヨンに普通使われる他の普通成分も含むこと
ができる。故にローシヨン用賦形剤は1又は2以
上の還元剤の混合された水性賦形剤である。毛髪
のウエーブかけ又はウエーブ伸ばしに便利な還元
剤はこの分野で多数知られている。例としてチオ
グリコール酸、システイン、チオ乳酸、ナトリウ
ム−、カリウム−およびアンモニウム亜硫酸塩お
よび重亜硫酸塩、トリス(ヒドロキシエチルホス
フイン)がある。本発明はすべてのウエーブかけ
およびウエーブ伸ばし組成物と共に使用できる
が、本発明の好ましい形では使用される還元剤は
チオグリコール酸とアルカリ金属塩、例えば亜硫
酸のナトリウム塩(例えば亜硫酸塩と重亜硫酸
塩)である。
ウエービングローシヨン中に含まれる還元剤量
も選んだ還元剤と望む結果によつて幾分変えられ
る。しかし普通ウエービングローシヨンはその全
重量を基準として約0.5乃至約20重量%の還元剤
を含む。還元剤がローシヨン全重量の約2乃至約
10重量%のとき最適結果がえられる。組成物のど
の成分についても本明細書と特許請求範囲中に使
われる“有効量”とは使用目的を達するに効果あ
る量を意味する。一般に与えられた濃度範囲に重
要性があるのでなくまた本発明は特定濃度にある
のでなくむしろ成分自体にあるのである。最も有
効な量は実用試験で決定できる。
更にウエービングローシヨンはまた芳香料、ア
ルカリ化剤および他の普通のウエービングローシ
ヨン成分を含むことができる。殆んどのローシヨ
ンは約5乃至約10のPH範囲をもつ。
本発明の調整方式の第2の重要成分は中和用ロ
ーシヨンの一部を構成する両性又は陰イオン性清
浄剤である。本発明の使用に適する多数の両性清
浄剤がある。しかし2種の清浄剤が特に有効とわ
かつている。第1種のものは式:
(式中Rは炭素原子10乃至18をもつ長鎖脂肪族
基を表わす)で表わされる。この化合物の代表例
はRがココナツト脂肪族基である場合である。こ
の性質をもつ物質はアンホテリツク−2として知
られミラノールCZMSFの名で市販されている。
両性清浄剤の第2種は本発明目的に特に効果が
あり式:
R−NH−CH2−CH2−COOH
(式中Rは炭素原子10乃至18をもつ長鎖脂肪族
アルキル基を表わす)で表わされる。この様な清
浄剤例の式中のRはラウリルとミリスチル脂肪族
アルキル基の混合物である。この物質はラウラミ
ノプロピオン酸として知られデリフアツト170℃
の名で市販されている。
すべての両性表面活性剤が適当であるとは限ら
なかつた。ベタイン類は本発明には使用できなか
つた。ベタインは両性イオン性化合物なので両性
イオン性表面活性剤は適当しないと予想された
が、使用できる両性イオン性表面活性剤があつ
た。明細書と特許請求の範囲に使用する“両性表
面活性剤製品”とは本発明において適当する両性
表面活性剤を表わす。
両性表面活性剤が“両性表面活性剤製品”であ
るかどうかはその水溶液を本発明の陽イオン性重
合体の1種のアルカリ性PH溶液中に加えて簡単に
普通の方法で決定できる。もし沈澱が生じたなら
ば両性表面活性剤は“両性表面活性剤製品”であ
る。両性表面活性剤はそのpKa値以上で陰イオン
性となるので、明細書と特許請求の範囲に使用す
る“陰イオン性表面活性剤”とは陰イオン性表面
活性剤と両性表面活性剤製品の両方を包含するの
である。
試験したすべての陰イオン性清浄剤は本発明に
使用できるとわかつている。即ちアルキルスルホ
ネイト、アルキルサルフエイト、スルホネイト化
およびサルフエイト化アルキルエーテル並びに長
鎖カルボン酸(鎖長を少なくともC10まで)の塩
は調整性複合物を生成する。本発明において有用
な陰イオン性清浄剤の例にはラウリル硫酸ナトリ
ウム、ラウリルエーテル硫酸ナトリウム、ラウリ
ル硫酸TEA、ステアリン酸ナトリウム等がある。
本発明の中和用ローシヨン中に含まれる両性又
は陰イオン性清浄剤の量は経済性と望む結果によ
つて幾分変る。しかしこの量は普通、中和用ロー
シヨン全重量を基準として約0.2乃至約50重量%、
好ましくは約0.5乃至約20重量%の範囲でよいで
あろう。
中和用ローシヨンはまた普通毛髪ウエーブかけ
又は毛髪伸ばし法に使われる様な中和用ローシヨ
ンに用いられる他の成分を入れることができる。
再び賦形剤は普通ウエービングローシヨンを頭に
つけた時それに含まれている還元剤の作用を“中
和する”に役立つ酸化剤を含む賦形水液である。
この目的をする多数の酸化剤はこの分野の知識あ
る者には知られている。これには過酸化水素、臭
素酸ナトリウムとカリウム、過ほう酸ナトリウム
等がある。
中和用ローシヨン中に含まれる酸化剤量も再び
選んだ酸化剤と望む結果によつて幾分変えられ
る。大ていこの量は中和用ローシヨン全重量基準
で約0.2乃至約20重量%である。
本発明における好ましい酸化剤量は中和用ロー
シヨン全重量の約1乃至約10重量%である。
上記の他に中和用ローシヨン中に入れうる他成
分中に有機酸と無機酸(例えばりん酸、くえん酸
等)がある。中和用ローシヨンのPHは普通約2乃
至約10の範囲内であるが、但し両性表面活性剤を
使う場合のPHはもつと塩基性側となる。
両性表面活性剤が塩基性PHにおいては陰イオン
性であるので中和用組成物のPHが両性表面活性剤
製品のpKa値以上である場合は本明細書や特許請
求範囲で使う“陰イオン性表面活性剤”は両性表
面活性剤製品を包含する。
本発明の組成物は列挙した陽イオン性重合体の
少なくとも1種と還元剤を含むウエービングロー
シヨンを入れたびんと還元剤と陰イオン性表面活
性剤を含む還元性溶液を入れた他のびんの2容器
の包装品の形で便利に市販できる。
次の実施例は本発明の特性を更に十分に例証す
るためのものであるが、本発明の範囲を限定する
ものではない。
実施例 1
ウエービングローシヨン―次の組成をもつ毛髪
用ウエービングローシヨンを製造した:
重量%
アンモニウムチオグリコレイト 7.0
モノエタノールアミン 3.5
香 料 0.1
クレアクワツト−1 3.0
水を加え全量 100.0
中和用ローシヨン―次の組成をもつローシヨン
を製造した:
重量%
ラウリル硫酸アンモニウム 3.0
過酸化水素 1.4
りん酸 0.1
水を加え全量 100.0
上記試料の他にそれぞれ陽イオン性重合体と陰
イオン性清浄剤を使わずウエービングローシヨン
と中和用ローシヨンを製造した。
白人処女毛髪4ふさを同じ温度、時間条件のも
とで処理した後洗浄中和した。これらを1/2イン
チ棒に巻きその内2個は重合体含有ウエービング
ローシヨンで飽和させまた他の2個は陽イオン性
重合体なしのウエービングローシヨンで飽和させ
た。4個全部をサランラツプに巻き35℃のオーブ
ンに20分間入れた。時間後ウエービングローシヨ
ンを洗いおとし棒にまいたまま試料を中和用溶液
で5分間処理した。ラウリル硫酸アンモニウムを
含む中和用溶液でウエーブしたふさ2個(1個は
重合体入り液でウエーブかけしたものと1個は重
合体なし液で処理したもの)を処理し、他の2個
はラウリル硫酸アンモニウムを含まない中和用液
で処理した。
重合体を含むウエービングローシヨンを用いか
つ陰イオン性表面活性剤を含む中和用液を用いて
ウエーブした毛ふさの場合のみ柔軟であり光輝あ
りかつ調整されていることがわかつた。この効果
は少なくとも4回の洗浄に耐えて耐久力あるとわ
かつた。
実施例 2
ウエービングローシヨン
毛髪のケラチン中のジサルフアイド結合を還元
するために次の組成をもつ毛髪ウエービングロー
シヨンをつくつた。
The present invention relates to compositions and methods for waving or straightening hair, particularly human hair. In particular, the present invention relates to compositions and methods described above for conditioning or improving hair. Hair waving or waving (often referred to as "permanent" treatment) usually involves the use of agents (hereinafter referred to as "reducing agents" or compositions containing reducing agents) that reduce or cleave the disulfide bonds of keratin in the hair. Hereinafter referred to as “for reduction” or “waving”
After applying a "composition" or "lotion" to shape the hair without internal elasticity or other resistance, a neutralizing agent that regenerates the keratin bonds is applied to fix the hair in the desired new shape. It is. Generally, the neutralizing agent is an oxidizing solution such as an aqueous solution of hydrogen peroxide. Apart from the waving and straightening of the hair with reducing lotions, there is the so-called relaxation of the hair using strong alkalis, usually in the form of pastes or creams. The mechanism of action of alkali is different from that of reducing agents in ordinary permanent waving and stretching.
In the latter case, the disulfide bonds in keratin remain intact until they are cleaved and restored by the neutralizing agent, whereas in the case of caustic treatment, the disulfide bonds in keratin are converted to monosulfide bonds and are then cleaved by the acid. "Neutralization" is simply the ordinary neutralization of the residual base with an acid. Therefore, "waving" and "stretching" as used herein
did not consider the relaxation of hair by strong bases. Waving or straightening hair with reducing agents such as mercaptans, sulfites or phosphines almost always makes the hair feel rough and difficult to comb. This applies to all hair types and is particularly troublesome for hair that has been bleached, dyed or exposed to the atmosphere for long periods before waving. A common method to alleviate this is to treat wavy hair with hair styling products such as alkyl-dimethylbenzyl halides, mustard oil emulsions, lanolin, and the like. Hair conditioners of this type are commonly used in the neutralization step of waving or straightening methods. Although this hair styling composition improves the feel of the hair and makes it easier to comb, the effect is temporary and completely disappears after the hair is washed. Sokol, US Pat. No. 3,912,808, discloses a method for waving or straightening hair using a waving lotion containing a reducing agent and polydimethyldiallylammonium chloride, a cationic polymer. The method of this patent has been used on industrial products and has been tested and compared for this application. Polydimethyldiallylammonium chloride is not used in the present invention. U.S. Pat. No. 4,175,572 to Hisiyung et al. is directed to a caustic hair relaxant containing, among other things, polydimethyldiallylammonium chloride, and is not directed to waving or straightening. The polymer can be used separately from the alkaline relaxant or before or after its application. Acidic hair washing is said to be used after hair relaxation or conditioning to remove excess alkaline solution. There is no mention of the final hair washing step or its composition, nor does it state that it is part of the conditioning method. In this sense it is considered to be equivalent to the commercial product based on the above-mentioned US Pat. No. 3,912,808, which uses a cationic surfactant in the neutralizing composition. In contrast, the present invention, in addition to not using polydimethylallylammonium chloride, specifically requires the presence of a cationic surfactant that forms a conditioning precipitate in the presence of hair. Furthermore, the present invention is not useful with strong alkaline relaxant compositions. A durable hair conditioning method has now been discovered that has special benefits over the usual techniques of waving or straightening hair and that lasts through repeated washings. This method involves treating the hair with a waving aqueous composition that includes a reducing agent and an effective amount of a cationic polymer called Clairquat-1 (described in more detail below) and then treating the hair with an oxidizing agent and an anionic surface. treatment with an aqueous neutralizing composition containing an activator. As a result of the initial reduction step during waving (or straightening) followed by the neutralization step and the unique combination of ingredients, a conditioning complex is produced in the hair that is stable to repeated washings. It is therefore an object of the present invention to provide a method of waving or straightening hair that will keep the hair in a condition that will withstand repeated washings. It is an object of the present invention to provide a convenient composition for carrying out the above method. Further details of the objects of the invention will become apparent from the specification and claims. In the following specification and claims, where possible, drugs will be described by their CTFA names as found in the Cosmetic Ingredients Dictionary of the Cosmetic Fragrance and Fragrance Association. Before explaining the cationic polymer called Clairquat-1, which is useful for the purpose of the present invention, we will first discuss other types of cationic polymers similar to this.
After that, I will talk about Clairquat-1. The molecular weight of this cationic polymer is expressed on a weight average basis. Another slightly preferred type is Polyquaternium-1, a quaternized polymer with quaternized ethanolamine end groups, commercially available from Onyx Chemicals under the name Onamer M (hereinafter referred to as Onamer). Dimethylbutenyl ammonium chloride has the formula: It is said to have n in the above formula is a cardinal number proportional to the molecular weight, and the molecular weight is 800 to 5000,
Preferably it is 1000 to 3500. Other types of cationic polymers are polymers and copolymers of quaternized polyvinylamine, which are prepared in a manner known per se. These are the following repeating units: (In the formula, R 1 , R 2 and R 3 may be the same or different groups and represent an alkyl group having 1 to 20 carbon atoms, and (represents an anion)
It is believed to consist of Molecular weight is 3000
150,000 to 150,000 is preferable. This polymer is hereinafter referred to as "QPVAMINE". Repeat unit as an example: One example is trimethylpolyvinylammonium sulfate, which is believed to be composed of
It has an average molecular weight of about 50,000. Another type of cationic material is a polymer of quaternized poly-4-vinylpyridine, which is prepared in a manner known per se. This is the general formula: (wherein R represents an alkyl group having 1 to 20 carbon atoms and X - represents an anion used in cosmetics such as a halide, sulfate or carboxylate). This also ranges from about 5,000 to about
It has a molecular weight of 500,000. This polymer is hereinafter referred to as "QPVP". An example of this type of cationic polymer is: There is also polyvinylmethylpyridinium iodide with an average molecular weight of about 50,000. A cationic polymer that has been found to give particularly good results in accordance with the present invention is poly(methacryl-amidopropyltrimethylammonium chloride), available from Texaco Chemicals.
It is produced by polymerizing the corresponding monomer, commercially available as MAPTAC, in a manner known per se.
This polymer has repeating units: (In the formula, n is proportional to the molecular weight.) The molecular weight is preferably 5,000 to 500,000. This polymer was later referred to as “Clairquat”.
1". As mentioned above, the specific cationic polymer Clairquat-1 is included in the reducing lotion used in this method. The amount of cationic polymer included in the reducing lotion depends on the desired result. Although it varies somewhat, it usually ranges from about 0.2% to about 10% by weight, based on the total weight of the reducing lotion, with an optimal range of about 1% to about 5%.
Weight%. The structural properties and known physicochemical properties of cationic polymers cannot be used to predict whether they can be used in the present invention. Therefore, many cationic polymers have been found to be unsuitable as hair conditioning agents when used in place of those disclosed herein. Some of the cationic polymers that have been found to be unsatisfactory include: quaternized poly-2-vinylpyridine; adipic acid and epoxypropyldiethylenetriamine copolymer (commercially available from Hercules Chemical Company under the name Delcet 101); adipic acid and dimethylaminohydroxypropyldiethylenetriamine copolymer (commercially available from Sandoz Company under the name Cartalechik F-4); poly(N-(3-dimethylamino)propyl)-
N'-(3-(ethyleneoxyethylenedimethylamino)propyl)urea dichloride (laminol
Quaternium-23. A quaternary ammonium polymer produced by the reaction of dimethyl sulfate and a copolymer of vinylpyrrolidone and dimethylaminoethyl methacrylate (commercially available from GAF Chemical Co. under the name Milanol A15); Quaternium-23. Quaternium-19. Polymer of hydroxyethyl cellulose reacted with epichlorohydrin and then quaternized with trimethylamine (commercially available from Union Carbide under the name Polymer JR-400); hydrated Quaternary ammonium derivative of degraded collagen protein (commercially available from Croda under the name Crotein Q); Quaternium-39. Copolymer of acrylamide and beta-methacryloxyethyltrimethylammonium methosulfate (Reten 205M from Hercules Chemical) (commercially available under the name Catrex); a copolymer of aminoethyl acrylate phosphate and acrylate (commercially available from National Starch under the name Catrex); and Quaternium-41, a copolymer of dimethyldiallylammonium chloride and acrylamide.
(commercially available from Merck & Co. under the name Melwatt-550). In addition to the cationic polymer, the waving or reducing lotion used in the present invention can also contain other common ingredients commonly used in waving lotions. Therefore, the lotion vehicle is an aqueous vehicle mixed with one or more reducing agents. Many reducing agents useful in waving or straightening hair are known in the art. Examples are thioglycolic acid, cysteine, thiolactic acid, sodium, potassium and ammonium sulfites and bisulfites, tris(hydroxyethylphosphine). Although the invention can be used with all waving and wave stretching compositions, in the preferred form of the invention the reducing agent used is thioglycolic acid and an alkali metal salt, such as the sodium salt of sulfite (e.g. sulfite and bisulfite). ). The amount of reducing agent included in the waving lotion will also vary somewhat depending on the reducing agent selected and the desired result. However, waving lotions typically contain from about 0.5% to about 20% by weight of reducing agent, based on their total weight. The reducing agent accounts for about 2 to about 20% of the total weight of the lotion.
Optimal results are obtained at 10% by weight. As used herein and in the claims, "effective amount" of any component of a composition means an amount effective to achieve its intended use. In general, there is no significance in the concentration ranges given, and the invention lies not in the specific concentrations, but rather in the ingredients themselves. The most effective amount can be determined through practical trials. Additionally, waving lotions can also contain fragrances, alkalizing agents and other common waving lotion ingredients. Most lotions have a PH range of about 5 to about 10. The second key component of the formulation of the present invention is the amphoteric or anionic detergent that forms part of the neutralizing lotion. There are a number of amphoteric detergents suitable for use in the present invention. However, two types of detergents have been found to be particularly effective. The first type has the formula: (wherein R represents a long-chain aliphatic group having 10 to 18 carbon atoms). A typical example of this compound is where R is a coconut aliphatic group. A material with this property is known as Amphoterik-2 and is commercially available under the name Milanor CZMSF. A second type of amphoteric detergent is particularly effective for the purposes of the present invention and has the formula: R-NH- CH2 - CH2 -COOH, where R represents a long chain aliphatic alkyl group having 10 to 18 carbon atoms. It is expressed as R in the formula of such exemplary detergents is a mixture of lauryl and myristyl aliphatic alkyl groups. This substance is known as lauraminopropionic acid and has a temperature of 170°C.
It is marketed under the name. Not all amphoteric surfactants were suitable. Betaines could not be used in the present invention. Since betaine is a zwitterionic compound, it was expected that zwitterionic surfactants would not be suitable, but there were zwitterionic surfactants that could be used. As used in the specification and claims, "ampholyte surfactant product" refers to amphoteric surfactants suitable in the present invention. Whether an amphoteric surfactant is an "ampholyte surfactant product" can be easily determined in a conventional manner by adding its aqueous solution to an alkaline PH solution of one of the cationic polymers of the present invention. If precipitation occurs, the amphoteric surfactant is an "ampholytic surfactant product." Since amphoteric surfactants become anionic above their pKa value, "anionic surfactants" as used in the specification and claims refer to anionic surfactants and amphoteric surfactant products. It encompasses both. All anionic detergents tested have been found to be usable in the present invention. Thus alkyl sulfonates, alkyl sulfates, sulfonated and sulfated alkyl ethers, and salts of long chain carboxylic acids (chain length at least up to C 10 ) form tunable complexes. Examples of anionic detergents useful in the present invention include sodium lauryl sulfate, sodium lauryl ether sulfate, TEA lauryl sulfate, sodium stearate, and the like. The amount of amphoteric or anionic detergent included in the neutralizing lotions of this invention will vary somewhat depending on economics and desired results. However, this amount typically ranges from about 0.2% to about 50% by weight, based on the total weight of the neutralizing lotion.
Preferably it will range from about 0.5 to about 20% by weight. The neutralizing lotion can also contain other ingredients commonly used in neutralizing lotions such as those used in hair waving or hair straightening procedures.
Again, the excipient is usually an excipient aqueous solution containing an oxidizing agent that helps to "neutralize" the effects of the reducing agent contained in the waving lotion when it is applied to the head.
Numerous oxidizing agents for this purpose are known to those skilled in the art. These include hydrogen peroxide, sodium and potassium bromate, and sodium perborate. The amount of oxidizing agent included in the neutralizing lotion will also vary somewhat depending on the oxidizing agent chosen and the desired result. The amount of the lubricant is from about 0.2 to about 20% by weight, based on the total weight of the neutralizing lotion. The preferred amount of oxidizing agent in the present invention is from about 1 to about 10% by weight of the total weight of the neutralizing lotion. In addition to the above, other ingredients that may be included in neutralizing lotions include organic and inorganic acids (eg, phosphoric acid, citric acid, etc.). The pH of neutralizing lotions is usually within the range of about 2 to about 10, unless an amphoteric surfactant is used, so that the pH tends to be more basic. Since ampholytic surfactants are anionic at basic pH, if the pH of the neutralizing composition is greater than or equal to the pKa value of the amphoteric surfactant product, it is considered an “anionic” product as used herein and in the claims. "Surfactant" includes amphoteric surfactant products. The composition of the invention comprises a bottle containing a waving lotion containing at least one of the listed cationic polymers and a reducing agent and another containing a reducing solution containing a reducing agent and an anionic surfactant. It is conveniently available commercially in a two-bottle package. The following examples are intended to more fully illustrate the characteristics of the invention, but are not intended to limit the scope of the invention. Example 1 Waving lotion - A hair waving lotion was produced with the following composition: wt% ammonium thioglycolate 7.0 monoethanolamine 3.5 fragrance 0.1 Claire quat - 1 3.0 total volume with water 100.0 neutralizing lotion - A lotion was prepared with the following composition: % by weight ammonium lauryl sulfate 3.0 Hydrogen peroxide 1.4 Phosphoric acid 0.1 Added water to a total volume of 100.0 In addition to the above samples, cationic polymers and anionic detergents were not used, respectively. Glossion and neutralizing lotion were manufactured. Four strands of Caucasian virgin hair were treated under the same temperature and time conditions and then washed and neutralized. These were wound into 1/2 inch rods, two of which were saturated with polymer-containing waving lotion and the other two with waving lotion without cationic polymer. All four pieces were wrapped in saran wrap and placed in a 35°C oven for 20 minutes. After a period of time, the waving lotion was rinsed off and the sample was treated with a neutralizing solution for 5 minutes while still on the rod. Two waved tassels (one waved with a solution with polymer and one treated with a solution without polymer) were treated with a neutralizing solution containing ammonium lauryl sulfate, and the other two were treated with a neutralizing solution containing lauryl sulfate. Treated with a neutralizing solution that does not contain ammonium sulfate. It was found that only hair tresses waved with a waving lotion containing a polymer and a neutralizing solution containing an anionic surfactant were soft, shiny and conditioned. This effect was found to be durable, withstanding at least four washes. Example 2 Waving Lotion A hair waving lotion having the following composition was prepared to reduce disulfide bonds in hair keratin.
【表】【table】
【表】
上記4種のウエービングローシヨンの各試料
5.25gをNICE ‘N EASY Hair Color
Shade No.122で予め染色した天然褐色毛髪の毛
髪束3.5gに加えた。次いでこれらの毛髪束のそ
れぞれをプラスチツクに包んだ約1cmの直径のウ
エービング棒に巻きつけ、38℃で1時間放置し
た。その後にそれぞれの毛髪束を水道水で1分間
洗浄し、棒から除いた。
上記のように処理した毛髪束を次いで中和用ロ
ーシヨンで処理した。
中和用ローシヨン
成 分 濃度(重量%)
臭素酸ナトリウム 10.0
炭酸ナトリウム 1.0
ナトリウムアルフア 5.0
ナトリウムラウリルエーテルサルフエート 2.50
芳香剤 0.50
水(脱イオン水)を加えて 全量100
梳毛性
中和用ローシヨンによる毛髪のケラチン中のジ
サルフアイド結合の再形成後に、それぞれの毛髪
束を洗浄し、毛髪の品質検査の専門家のパネルの
判定によつて梳毛性を等級分けした。
梳毛性1は毛髪束を櫛でとかすのが最も困難な
ものを表わし、コンデイシヨニング効果のないも
のに等しい。梳毛性5は毛髪束を櫛でとかすのが
最も容易であるもの、すなわち高度にコンデイシ
ヨニングされた毛髪の品質に相当するものを表わ
す。その中間は数値の低いものほど梳毛性がわる
く、数値が大きいものほど梳毛性が良好である。
ウエービングローシヨン 梳毛性
クレアクワツト−1を使用したもの 4〜5
メルクオート550を使用したもの 1
クロテインを使用したもの 1
カルタレチン F4を使用したもの 1
陽イオン重合体を使用しなかつたもの 1
上記のデータからクレアクワツト−1は他の陽
イオン性重合体に比べて著しくすぐれたコンデイ
シヨニング効果を与えることがわかる。
本発明を特定例について記載したが本発明の真
意を逸脱しない限り多くの変更又は修正を行なう
ことも可能なのである。[Table] Each sample of the above four types of waving lotion
5.25g NICE 'N EASY Hair Color
Added to 3.5 g of natural brown hair tresses pre-dyed with Shade No. 122. Each of these hair tresses was then wrapped around a plastic-wrapped waving rod approximately 1 cm in diameter and left at 38°C for 1 hour. Each hair tress was then washed with tap water for 1 minute and removed from the wand. The hair tresses treated as described above were then treated with a neutralizing lotion. Neutralizing lotion ingredient concentration (wt%) Sodium bromate 10.0 Sodium carbonate 1.0 Sodium alpha 5.0 Sodium lauryl ether sulfate 2.50 Fragrance 0.50 Add water (deionized water) Total amount 100 Combing property Neutralizing lotion removes hair After reformation of the disulfide bonds in the keratin, each hair tress was washed and graded for cardability as judged by a panel of hair quality testing experts. Combability 1 represents the most difficult hair strand to comb and is equivalent to no conditioning effect. Combability 5 represents the easiest hair tress to comb, ie corresponds to the quality of highly conditioned hair. In the middle, the lower the number, the worse the combability, and the higher the number, the better the combability. Waving Lotion Worsted Clairquat-1 4-5 Mercquart 550 1 Crotein 1 Cartaletin F4 1 No cationic polymer 1 The above The data show that CREAQUAT-1 provides significantly superior conditioning effects compared to other cationic polymers. Although the invention has been described with respect to specific embodiments, it is understood that many changes and modifications can be made without departing from the spirit of the invention.
Claims (1)
イオン性重合体の有効量を含む水性ウエービン
グ組成物で毛髪を処理した後 (b) 上記毛髪を酸化剤と陰イオン性表面活性剤を
含む水性中和用組成物で処理する 工程より成ることを特徴とする反復洗髪にも調整
状態を保持する毛髪のウエーブかけ又はウエーブ
伸ばし法。 2 上記ウエービング組成物がその全重量を基準
として0.5乃至20重量%の上記還元剤と0.2乃至10
重量%の上記陽イオン性重合体を含み、また上記
中和用組成物がその全重量を基準として0.2乃至
20重量%の酸化剤と0.2乃至50重量%の上記表面
活性剤を含む特許請求の範囲第1項に記載の方
法。 3 (a) 上記還元剤がチオグリコール酸又は亜硫
酸のアルカリ金属塩であり、 (b) 上記イオン性重合体が分子量5000乃至500000
をもつクレアクワツト−1であり、 (c) 上記酸化剤が過酸化水素又は臭素酸ナトリウ
ム又はカリウムであり、かつ (d) 上記表面活性剤がラウリル硫酸ナトリウム又
はアンモニウムである 特許請求の範囲第1項又は2項に記載の方法。 4 ウエービング組成物重量を基準として (a) 0.5乃至20重量%の還元剤および (b) クレアクワツト−1と呼ばれる陽イオン性重
合体0.2乃至10重量%を含むことを特徴とする
毛髪のウエーブかけ又はウエーブ伸ばしに便利
な水性毛髪ウエービング組成物。 5 還元剤およびクレアクワツト−1と呼ばれる
陽イオン性重合体の水溶液より成るウエービング
ローシヨンを入れた1の容器と中和剤および陰イ
オン性表面活性剤の水溶液より成る中和用ローシ
ヨンを入れた1の容器との2容器入り包装品であ
ることを特徴とする毛髪のウエーブかけ又はウエ
ーブ伸ばし用の2部分包装品。[Claims] 1 (a) A reducing agent and a repeating unit of the following formula (b) After treating the hair with an aqueous waving composition containing an effective amount of a cationic polymer called Clairquat-1, where n is a number proportional to molecular weight, the hair is treated with an oxidizing agent. 1. A method for waving or straightening hair which maintains its conditioned state even after repeated hair washing, comprising the step of treating the hair with an aqueous neutralizing composition comprising: and an anionic surfactant. 2 The waving composition contains 0.5 to 20% by weight of the reducing agent and 0.2 to 10% by weight based on the total weight of the waving composition.
% by weight of the above-mentioned cationic polymer, and the above-mentioned neutralizing composition contains 0.2 to
A method according to claim 1, comprising 20% by weight of oxidizing agent and 0.2 to 50% by weight of said surfactant. 3 (a) the reducing agent is thioglycolic acid or an alkali metal salt of sulfite; (b) the ionic polymer has a molecular weight of 5,000 to 500,000;
(c) the oxidizing agent is hydrogen peroxide or sodium or potassium bromate; and (d) the surfactant is sodium lauryl sulfate or ammonium sulfate. Or the method described in Section 2. 4. Hair waving, characterized in that it contains (a) 0.5 to 20% by weight of a reducing agent and (b) 0.2 to 10% by weight of a cationic polymer called Clairquat-1, based on the weight of the waving composition. An aqueous hair waving composition convenient for stretching waves. 5 Container 1 containing a waving lotion consisting of a reducing agent and an aqueous solution of a cationic polymer called Clairequat-1 and a neutralizing lotion consisting of an aqueous solution of a neutralizing agent and an anionic surfactant. A two-part package for waving or straightening hair, characterized in that it is a two-container package containing one container and one container.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34668482A | 1982-02-08 | 1982-02-08 | |
| US346684 | 2003-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58150506A JPS58150506A (en) | 1983-09-07 |
| JPH0425251B2 true JPH0425251B2 (en) | 1992-04-30 |
Family
ID=23360566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58018240A Granted JPS58150506A (en) | 1982-02-08 | 1983-02-08 | Hair treatment together with waving or de-waving at one time and hair waving composition |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS58150506A (en) |
| BE (1) | BE895854A (en) |
| BR (1) | BR8300583A (en) |
| CA (1) | CA1190857A (en) |
| CH (1) | CH660114A5 (en) |
| DE (1) | DE3303346A1 (en) |
| DK (1) | DK51883A (en) |
| ES (1) | ES519303A0 (en) |
| FR (1) | FR2521004B1 (en) |
| GB (1) | GB2114616B (en) |
| GR (1) | GR77409B (en) |
| IE (1) | IE53928B1 (en) |
| IT (1) | IT1203648B (en) |
| MX (1) | MX158289A (en) |
| NL (1) | NL8300412A (en) |
| NZ (1) | NZ203095A (en) |
| SE (1) | SE461436B (en) |
| ZA (1) | ZA83863B (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU578780B2 (en) * | 1985-02-04 | 1988-11-03 | Chesebrough-Pond's Inc. | Hair waving and straightening compositions of matter |
| CA1266829A (en) * | 1985-02-07 | 1990-03-20 | Du Yung Hsiung | Permanent wave neutralizer composition and method |
| US4656043A (en) * | 1985-09-13 | 1987-04-07 | Richardson-Vicks Inc. | Peroxide-containing conditioning shampoo |
| JP2568083B2 (en) * | 1987-05-18 | 1996-12-25 | 政夫 齋藤 | Permanent method |
| US4996997A (en) * | 1988-02-19 | 1991-03-05 | Amethyst Investment Group, Inc. | Permanent waving process and compositions |
| EP0356508A4 (en) * | 1988-02-19 | 1990-10-03 | Amethyst Investment Group, Inc. | Permanent wave process and compositions |
| JPH0624946A (en) * | 1989-12-08 | 1994-02-01 | L'oreal Sa | Reducing cosmetic composition |
| FR2657254B1 (en) * | 1990-01-19 | 1992-04-10 | Oreal | REDUCING COSMETIC COMPOSITION FOR PERMANENT HAIR, BASED ON N-ACETYLCYSTEAMINE AND A CATIONIC POLYMER, AND ITS USE IN A PERMANENT HAIR DEFORMATION PROCESS. |
| FR2655541B1 (en) * | 1989-12-08 | 1992-02-21 | Oreal | REDUCING COSMETIC COMPOSITION FOR PERMANENT HAIR, BASED ON CYSTEAMINE AND A CATIONIC POLYMER, AND USE THEREOF IN A PROCESS OF PERMANENT DEFORMATION OF HAIR. |
| US5415856A (en) * | 1990-05-08 | 1995-05-16 | Preemptive Advertising Inc. | Hair treatment compositions containing disaccharides |
| JP2516284B2 (en) * | 1991-04-04 | 1996-07-24 | 花王株式会社 | Two-component hair treatment composition and hair treatment method |
| FR2675379A1 (en) * | 1991-04-16 | 1992-10-23 | Oreal | Hair-care composition for shaping the hair and corresponding hair-shaping process |
| JP2523418B2 (en) * | 1991-08-13 | 1996-08-07 | 花王株式会社 | Two-agent keratinous fiber treating agent composition |
| GB2312444A (en) * | 1996-04-27 | 1997-10-29 | R & C Products Pty Ltd | Keratin fibre modification using quaternary ammonium compounds |
| US6125856A (en) * | 1999-04-21 | 2000-10-03 | Phild Co., Ltd. | Hair repair, styling, and straightening process |
| US6805136B2 (en) | 2001-11-02 | 2004-10-19 | Kenra, Llc | Hair relaxer |
| US6723308B2 (en) | 2001-11-02 | 2004-04-20 | Kenra, Llc | Hair clarifying treatment |
| DE10338883A1 (en) * | 2003-08-23 | 2005-03-24 | Hans Schwarzkopf & Henkel Gmbh & Co. Kg | Process for smoothing keratin-containing fibers |
| FR2997848B1 (en) * | 2012-11-09 | 2015-01-16 | Oreal | COMPOSITION COMPRISING A DICARBONYL DERIVATIVE AND A METHOD FOR SMOOTHING THE HAIR THEREFROM |
| EP4119122A1 (en) | 2021-07-13 | 2023-01-18 | Kao Germany GmbH | Process for permanent waving keratin fibers |
| PL441751A1 (en) * | 2022-07-17 | 2024-01-22 | Uniwersytet Jagielloński | New cationic polymers with selective fungicidal properties |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2980657A (en) * | 1954-07-06 | 1961-04-18 | Rohm & Haas | Quaternary ammonium compounds of polymers of acrylamido type and methods for making them |
| FR2010319A1 (en) * | 1968-06-07 | 1970-02-13 | Roehm & Haas Gmbh | |
| US3912808A (en) * | 1970-02-25 | 1975-10-14 | Gillette Co | Hair waving and straightening process and composition containing water-soluble amino and quaternary ammonium polymers |
| US3986825A (en) * | 1972-06-29 | 1976-10-19 | The Gillette Company | Hair coloring composition containing water-soluble amino and quaternary ammonium polymers |
| US4027008A (en) * | 1975-05-14 | 1977-05-31 | The Gillette Company | Hair bleaching composition containing water-soluble amino and quaternary ammonium polymers |
| JPS5261237A (en) * | 1975-11-13 | 1977-05-20 | Oreal | New cosmetic compound on basis of quaternarized polymer |
| LU76955A1 (en) * | 1977-03-15 | 1978-10-18 | ||
| US4366827A (en) * | 1979-12-28 | 1983-01-04 | Societe Anonyme Dite: L'oreal | Procedure for the permanent reshaping of hair, and composition intended for carrying out said procedure |
| FR2472382A1 (en) * | 1979-12-28 | 1981-07-03 | Oreal | PERMANENT HAIR DEFORMATION PROCESS |
| CA1138341A (en) * | 1980-01-23 | 1982-12-28 | Leszek J. Wolfram | Waving composition from a reducing agent and cationic polymer |
-
1983
- 1983-01-26 NZ NZ203095A patent/NZ203095A/en unknown
- 1983-01-26 CA CA000420294A patent/CA1190857A/en not_active Expired
- 1983-01-27 ES ES519303A patent/ES519303A0/en active Granted
- 1983-01-28 MX MX196086A patent/MX158289A/en unknown
- 1983-02-02 DE DE19833303346 patent/DE3303346A1/en not_active Withdrawn
- 1983-02-03 NL NL8300412A patent/NL8300412A/en not_active Application Discontinuation
- 1983-02-04 GR GR70409A patent/GR77409B/el unknown
- 1983-02-04 FR FR8301781A patent/FR2521004B1/en not_active Expired
- 1983-02-07 BR BR8300583A patent/BR8300583A/en unknown
- 1983-02-07 IE IE238/83A patent/IE53928B1/en not_active IP Right Cessation
- 1983-02-07 CH CH684/83A patent/CH660114A5/en not_active IP Right Cessation
- 1983-02-07 SE SE8300626A patent/SE461436B/en not_active IP Right Cessation
- 1983-02-07 IT IT47676/83A patent/IT1203648B/en active
- 1983-02-07 GB GB08303349A patent/GB2114616B/en not_active Expired
- 1983-02-08 BE BE0/210079A patent/BE895854A/en not_active IP Right Cessation
- 1983-02-08 DK DK51883A patent/DK51883A/en not_active Application Discontinuation
- 1983-02-08 ZA ZA83863A patent/ZA83863B/en unknown
- 1983-02-08 JP JP58018240A patent/JPS58150506A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8501971A1 (en) | 1984-12-16 |
| ES519303A0 (en) | 1984-12-16 |
| IT8347676A0 (en) | 1983-02-07 |
| CA1190857A (en) | 1985-07-23 |
| SE461436B (en) | 1990-02-19 |
| FR2521004A1 (en) | 1983-08-12 |
| AU547971B2 (en) | 1985-11-14 |
| SE8300626D0 (en) | 1983-02-07 |
| AU1091683A (en) | 1983-08-18 |
| GR77409B (en) | 1984-09-13 |
| IE830238L (en) | 1983-08-08 |
| JPS58150506A (en) | 1983-09-07 |
| GB2114616A (en) | 1983-08-24 |
| GB2114616B (en) | 1985-12-18 |
| GB8303349D0 (en) | 1983-03-09 |
| SE8300626L (en) | 1983-08-09 |
| DE3303346A1 (en) | 1983-10-13 |
| FR2521004B1 (en) | 1987-01-23 |
| BE895854A (en) | 1983-08-08 |
| IE53928B1 (en) | 1989-04-12 |
| ZA83863B (en) | 1983-11-30 |
| NL8300412A (en) | 1983-09-01 |
| CH660114A5 (en) | 1987-03-31 |
| DK51883D0 (en) | 1983-02-08 |
| IT1203648B (en) | 1989-02-15 |
| BR8300583A (en) | 1983-11-08 |
| NZ203095A (en) | 1986-10-08 |
| MX158289A (en) | 1989-01-20 |
| DK51883A (en) | 1983-08-09 |
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