JP4046570B2 - Hair cosmetics - Google Patents
Hair cosmetics Download PDFInfo
- Publication number
- JP4046570B2 JP4046570B2 JP2002223325A JP2002223325A JP4046570B2 JP 4046570 B2 JP4046570 B2 JP 4046570B2 JP 2002223325 A JP2002223325 A JP 2002223325A JP 2002223325 A JP2002223325 A JP 2002223325A JP 4046570 B2 JP4046570 B2 JP 4046570B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acid
- hair
- component
- polymer
- 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
- 239000003676 hair preparation Substances 0.000 title description 7
- 229920000642 polymer Polymers 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000002537 cosmetic Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 239000004475 Arginine Substances 0.000 claims description 15
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 15
- 239000000470 constituent Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 239000004471 Glycine Substances 0.000 claims description 9
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 9
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 8
- 235000004279 alanine Nutrition 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 239000002453 shampoo Substances 0.000 claims description 8
- 102000011782 Keratins Human genes 0.000 claims description 6
- 108010076876 Keratins Proteins 0.000 claims description 6
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- 239000006260 foam Substances 0.000 claims description 3
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 229960003121 arginine Drugs 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
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- 229940024606 amino acid Drugs 0.000 description 9
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- 150000001413 amino acids Chemical class 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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- 239000000843 powder Substances 0.000 description 6
- 230000002335 preservative effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 239000008213 purified water Substances 0.000 description 6
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
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- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000004909 Moisturizer Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
- 239000008266 hair spray Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
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- 229940057995 liquid paraffin Drugs 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- 230000001333 moisturizer Effects 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 229960003975 potassium Drugs 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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Description
【０００１】
【産業上の利用分野】
本発明は毛髪化粧料に関し、更に詳しく言えば水分或いはつやの経時的維持率に優れた毛髪化粧料に関する。
【０００２】
【従来の技術】
従来から毛髪にしっとりした感触や美しいつや感を付与したりするために、毛髪化粧料には保湿剤やつや出し剤が配合されている。通常、保湿剤としては、プロピレングリコール、グリセリン、尿素、ソルビトール、アルキレンオキサイドが付加したアルコール等が挙げられる。また、つや出し剤としては、シリコーン、エステル油、加水分解蛋白質、ポリオール、高級アルコール等が挙げられる。
【０００３】
又その一方、毛髪化粧料の適用による毛髪に与える負荷は決して小さくなく、それ故一度付与したしっとりした感触や美しいつや感を出来るだけ長時間維持できるものが望ましい。しかしながらこれら従来の保湿剤或いはつや出し剤は、単なる保湿効果或いはつや出し効果においては優れているものの、その保湿効果又はつや出し効果の経時的な維持という点については充分なものはなかった。
【０００４】
【発明が解決しようとする課題】
本発明は保湿効果の経時的維持率及び／又はつやの経時的維持率に優れた毛髪化粧料を提供することを課題とする。
【０００５】
【課題を解決するための手段】
斯かる実状に鑑み、本発明者らは鋭意研究を行った結果、特定の高分子と化合物とを含有する毛髪化粧料が保湿効果の経時的維持率及び／又はつやの経時的維持率に優れていることを見出し本発明を完成させるに至った。
【０００６】
すなわち本発明は下記（Ａ）及び（Ｂ）を含有する毛髪化粧料を提供する。
（Ａ）式（４）又は（５）で表される化合物又はその塩を構成単量体として用い、重合又は共重合してなる高分子又はその塩から選ばれる１種乃至は２種以上。
【０００７】
【化３】
（Ｂ）アルギニン、グリシン、アラニン及びケラチンから選ばれる１種乃至は２種以上。
【０００９】
【発明の実施の形態】
以下、本発明を詳細に説明する。
【００１０】
＜１＞成分（Ａ）
成分（Ａ）は、式（１）で表される化合物又はその塩を構成単量体として用い、重合又は共重合してなる、高分子又はその塩から選ばれる１種乃至は２種以上を指す。
【００１１】
【化８】
【００１２】
ここで式（１）中のＲ１は水素原子又はメチル基を表し、Ｒ２はアミノ酸残基を表す。Ｒ２のアミノ酸残基としては、そのアミノ酸は通常知られているアミノ酸であれば特段の限定を受けず、具体的には例えば、グリシン、アラニン、グルタミン、リジン、アルギニン等が挙げられる。これらのうち、リジン残基が特に好ましい。それはこのものを構成単量体として含有する高分子又は塩を用いた際、本発明の毛髪化粧料における保湿効果の経時的維持率及び／又はつやの経時的維持率の点で特に優れているからである。
【００１３】
式（１）で表される化合物又はその塩のうち、式（２）〜（６）で表される化合物又はその塩等がより好ましいものとして挙げられ、式（４）、式（５）で表される化合物が特に好ましい。それはこれらの化合物を用いた際に、本発明の効果がより優れているからである。
【００１４】
【化９】
【００１５】
【化１０】
【００１６】
【化１１】
【００１７】
【化１２】
【００１８】
【化１３】
【００１９】
式（１）で表される化合物の塩については、毛髪に適用する際に不都合を生じない範囲内では特段の限定を受けない。具体的には、例えば、塩酸、硫酸、硝酸、燐酸等の鉱酸塩、クエン酸、シュウ酸、フマル酸、マレイン酸、ギ酸、酢酸、メタンスルホン酸、ベンゼンスルホン酸、パラトルエンスルホン酸等の有機酸塩、炭酸塩、ナトリウム、カリウム等のアルカリ金属塩、カルシウム、マグネシウム等のアルカリ土類金属塩、等の塩が挙げられる。
【００２０】
式（１）で表される化合物又はその塩は常法に従って製造することが出来る。具体的には例えばアクリル酸又はメタクリル酸とアミノ酸とを縮合させればよい。塩の作製は常法に準じて為されれば良く、例えば、式（１）で表される化合物と酸又は塩基を適切な比率で有機又は無機溶媒中で混合してやればよい。
【００２１】
成分（Ａ）の高分子又はその塩は、式（１）で表される化合物又はその塩を構成単量体として用い、重合又は共重合してなる高分子又はその塩からなる１種乃至は２種以上である。
【００２２】
当該高分子は、式（１）で表される化合物又はその塩を構成単量体として用い、重合又は共重合してなるものである。ここで式（１）で表される化合物又はその塩を１種用いても良いし、２種以上用いても構わない。ここで２種以上用いた際高分子鎖の配列状態は本発明の効果を損なわない限りにおいてグラフト共重合体、ブロック共重合体、ランダム共重合体の何れであっても構わない。
【００２３】
さらに式（１）で表される化合物又はその塩のみを用いて重合又は共重合したものであっても良いし、本発明の効果を損なわない範囲で式（１）で表される化合物又はその塩以外に他の化合物を併せて構成単量体として用いて重合又は共重合しても良い。その様な併用可能な構成単量体としては、化粧品や皮膚外用剤等で一般に用いられている高分子の高分子鎖を構成する単量体であれば特段の限定を受けず、具体的には例えば、エチレン、ビニルアルコール、アクリル酸、アクリル酸エステル、メタクリル酸、メタクリル酸エステル等が挙げられる。式（１）で表される化合物又はその塩以外に他の化合物を併せて用いる際、高分子鎖の配列状態は本発明の効果を損なわない限りにおいてグラフト共重合体、ブロック共重合体、ランダム共重合体の何れであっても構わない。
【００２４】
重合又は共重合に用いる化合物又はその塩全体における式（１）で表される化合物又はその塩の占める比率は、併用する他の化合物の種類などによって異なるが、１０重量％以上が好ましく、５０重量％以上がより好ましく、式（１）で表される化合物又はその塩のみを単量体とする場合が特に好ましい。これは、式（１）で表される化合物又はその塩の割合が低くなるに従って、本発明の効果の発現も小さくなるからである。これらの化合物を常法に準じて重合させれば成分（Ａ）の高分子又はその塩が製造できる。具体的には、重合開始剤存在下で溶液重合乃至は乳化重合等を行えばよい。
【００２５】
塩に関しては、生理的に許容されるものであれば特段の限定を受けず、具体的には例えば、塩酸、硫酸、硝酸、燐酸等の鉱酸塩、クエン酸、シュウ酸、フマル酸、マレイン酸、ギ酸、酢酸、メタンスルホン酸、ベンゼンスルホン酸、パラトルエンスルホン酸等の有機酸塩、炭酸塩、ナトリウム、カリウム等のアルカリ金属塩、カルシウム、マグネシウム等のアルカリ土類金属塩等の塩が挙げられる。塩の作製については、単量体に塩を用いることで得ることもできるし、高分子化の後に塩形成してもよい。
【００２６】
かくして得られた高分子は高分子鎖中に式（７）で表される部分構造を有する。従って、式（１）中のＲ１は式（７）中のＲ３に、式（１）中のＲ２は式（７）中のＲ４にそれぞれ対応する。すなわち、式（７）におけるＲ３とＲ４の形態は、式（１）におけるＲ１とＲ２の形態と同様である。
【００２７】
【化１４】
【００２８】
式（７）中のＲ３は水素原子又はメチル基を表す。Ｒ４はアミノ酸残基を表す。ここでＲ４の好ましい形態は、前記した式（１）中のＲ３の形態と同様である。
【００２９】
式（７）中、Ｒ４はアミノ酸残基を表す。アミノ酸残基としては、そのアミノ酸は通常知られているアミノ酸であれば特段の限定を受けず、具体的には例えば、グリシン、アラニン、グルタミン、リジン、アルギニン等が挙げられる。これらのうち、リジン残基が特に好ましく、それはこの構造式の場合本発明の効果の発揮の点で特に優れているからである。
【００３０】
式（７）で表される部分構造を有する高分子の塩については特段の限定を受けない。具体的には、例えば、塩酸、硫酸、硝酸、燐酸等の鉱酸塩、クエン酸、シュウ酸、フマル酸、マレイン酸、ギ酸、酢酸、メタンスルホン酸、ベンゼンスルホン酸、パラトルエンスルホン酸等の有機酸塩、炭酸塩、ナトリウム、カリウム等のアルカリ金属塩、カルシウム、マグネシウム等のアルカリ土類金属塩、等の塩が挙げられる。
【００３１】
式（７）で表される部分構造のうち、好ましいものとして式（８）〜（１３）で表される部分構造等から選ばれる１種又は２種以上等が挙げられる。これは、式（２）で表される化合物を構成単量体として用いて重合させてなる高分子又はその塩が式（８）に示す部分構造を有するからであり、同様に式（３）〜（６）で表される化合物が式（９）〜（１２）で表される部分構造式に対応するからである。また、式（２）と式（６）で表される化合物を共重合した高分子も優れているが、このものは式（１３）で表される部分構造式を有し、そのため式（１３）で表される部分構造式も好ましい。
【００３２】
【化１５】
【００３３】
【化１６】
【００３４】
【化１７】
【００３５】
【化１８】
【００３６】
【化１９】
【００３７】
【化２０】
【００３８】
成分（Ａ）の高分子の分子量は、５千〜１００万であることが好ましく、１万〜１０万であることがさらに好ましい。これは、分子量がこの範囲にあるときに使用感や毛髪に対する作用等の面で優れているからである。
【００３９】
成分（Ａ）の製造例を以下に述べる。
【００４０】
＜１＞製造例１ アラニン−メタクリル酸アミド・ポリマー
（式（２）で表される化合物を構成単量体として用い、重合してなるもの；このものは式（８）で表される部分構造式を高分子鎖中に有する）
〔１〕アラニン−メタクリル酸アミド〔式（２）で表される化合物〕
炭酸カリウム５５．２８ｇを蒸留水２００ｍｌに溶解し、これにＤ，Ｌ−α−アラニン１７．８２ｇを溶解した。氷冷下、激しく撹拌しながら、メタクリル酸クロリド２３．００ｇを約２０分で滴下し、そのまま約２時間激しく撹拌した。反応液に濃塩酸を加え、ｐＨを１〜２にした後、食塩を飽和させ酢酸エチル２００ｍｌで３回抽出した。酢酸エチル層を、無水硫酸ナトリウムで乾燥後濃縮。酢酸エチルで再結晶化を行い、得られた結晶を濾取、乾燥した。
白色結晶 １９．９６ｇ
〔２〕ポリマー化
得られた結晶８．３５ｇを蒸留水５０ｍｌ、メタノール５０ｍｌに溶解し、窒素ガスを３０分通気した後、過硫酸カリウム１００ｍｇ（０．３７ｍｍｏｌ）を加え溶解させた後、３時間加熱環流した。室温まで冷却した後、アセトン中に注ぎ、沈殿を析出させた。上澄を捨て、再度アセトンを加えて撹拌し、析出物を濾取、乾燥し、目的ポリマーを得た。
白色粉末 ６．６８ｇ
【００４１】
＜２＞製造例２ グルタミン−メタクリル酸アミド・ポリマー
（式（３）で表される化合物を構成単量体として用い、重合してなるもの；このものは式（９）で表される部分構造式を高分子鎖中に有する）
〔１〕グルタミン−メタクリル酸アミド〔式（２）で表される化合物〕
炭酸カリウム３４．５５ｇを蒸留水１００ｍｌに溶解し、これにＬ−グルタミン７．３０ｇを溶解し、さらにアセトニトリル２０ｍｌを加えた。激しく撹拌しながら、メタクリル酸クロリド１０．４５ｇを約１０分で滴下し、そのまま約２時間激しく撹拌した。反応液を濃塩酸でｐＨを１〜２にした後、食塩を飽和させ酢酸エチル１００ｍｌで２回洗浄した。得られた水層を、酢酸エチル／イソプロパノール＝１／１ １００ｍｌで３回抽出した。酢酸エチル／イソプロパノール層を合わせて濃縮し、シリカゲルカラム精製（シリカゲル３０ｇ、クロロホルム／メタノール＝２／１で溶出）し、必要画分を集め、濃縮した。
無色シロップ状 ７．４７ｇ
〔２〕ポリマー化
得られたシロップ７．４７ｇを蒸留水５０ｍｌ、メタノール５０ｍｌに溶解し、窒素ガスを１時間通気した後、過硫酸カリウム１００ｍｇを加え溶解した後、３時間加熱環流した。室温まで冷却した後、イソプロパノール中に注ぎ、析出物を濾取、乾燥し、目的ポリマーを得た。
白色粉末 ６．３５ｇ
【００４２】
＜３＞製造例３ リジン−メタクリル酸アミド・ポリマー
（（式（４）又は式（５）で表される化合物を構成単量体として用い、重合してなるもの；このものは式（１０）又は式（１１）で表される部分構造式を高分子鎖中に有する）
〔１〕リジン−メタクリル酸アミド〔式（４）又は式（５）で表される化合物〕炭酸水素カリウム５．５１ｇを蒸留水１００ｍｌに溶解し、これにリジン塩酸塩９．１３ｇを溶解し、さらにアセトン８０ｍｌを加えた。氷冷下、激しく撹拌しながら、メタクリル酸クロリド５．２３ｇを約１０分で滴下し、そのまま約２時間激しく撹拌した。反応液を濃塩酸でｐＨ１〜２にした後、食塩を加え飽和させた。この水層を酢酸エチル１００ｍｌで２回洗浄した後、酢酸エチル／イソプロパノール＝１／２ １００ｍｌで３回洗浄した。酢酸エチル／イソプロパノール層を合わせて、減圧下５０ｍｌ程度に濃縮し、イソプロパノール５００ｍｌを加え、約２００ｍｌに再度濃縮した。析出した食塩を濾過で除き、濾液を濃縮した。
無色シロップ状 ５．５３ｇ
〔２〕ポリマー化
得られたリジン−モノ−メタクリル酸アミド塩酸塩５．５３ｇを蒸留水５０ｍｌに溶解し、窒素ガスを３０分通気した後、過硫酸カリウム１００ｍｇ（０．３７ｍｍｏｌ）を加え溶解させた後、３時間加熱環流した。室温まで冷却した後、アセトン中に注ぎ、沈殿を析出させた。上澄を捨て、再度アセトンを加えて撹拌し、析出物を濾取、乾燥し、目的ポリマーを得た。
白色粉末 ４．２０ｇ
【００４３】
＜４＞製造例４ アルギニン−メタクリル酸アミド・ポリマー
（（式（６）で表される化合物を構成単量体として用い、重合してなるもの；このものは式（１２）で表される部分構造式を高分子鎖中に有する）
〔１〕アルギニン−メタクリル酸アミド〔式（６）で表される化合物〕
炭酸カリウム２７．６４ｇを蒸留水２００ｍｌに溶解し、これにアルギニン塩酸塩２１．０７ｇを溶解し、さらにアセトン８０ｍｌを加えた。氷冷下、激しく撹拌しながら、メタクリル酸クロリド１０．４６ｇを約１０分で滴下し、そのまま１時間激しく撹拌した。反応液を濃塩酸でｐＨ１とし、食塩を飽和させた。この水層を酢酸エチル３００ｍｌで３回洗浄した後、酢酸エチル／イソプロパノール＝１／１ ２００ｍｌで３回抽出した。酢酸エチル／イソプロパノール層を合わせて、減圧下１００ｍｌ程度に濃縮し、イソプロパノール４００ｍｌを加え、約２００ｍｌに再度濃縮した。析出した食塩を濾過で除き、濾液を濃縮した。
無色シロップ状 ２１．８０ｇ
〔２〕ポリマー化
得られたアルギニンメタクリル酸アミド塩酸塩４．８４ｇを蒸留水４０ｍｌに溶解し、窒素ガスを１時間通気した後、過硫酸カリウム６０ｍｇを加え溶解させ、３時間加熱環流した。室温まで冷却した後、アセトン中に注ぎ、沈殿を析出させた。上清を捨て、再度アセトンを加えて撹拌し、析出物を濾取、乾燥し、目的ポリマーを得た。
白色粉末 ３．０５ｇ
【００４４】
＜５＞製造例５ アラニン−メタクリル酸アミド／アルギニン−メタクリル酸アミド（＝７：３）・コポリマー
（式（２）及び式（６）で表される化合物を構成単量体として用い、重合してなるもの；このものは式（１３）で表される部分構造式を高分子鎖中に有する）
アルギニンメタクリル酸アミド塩酸塩１０．５３ｇと先に示したアラニン−メタクリル酸アミド１３．９０ｇを蒸留水１００ｍｌに溶解し、窒素ガスを１時間通気した後、過硫酸カリウム２５０ｍｇを加え溶解させ、３時間加熱環流した。室温まで冷却した後、アセトン中に注ぎ、沈殿を析出させた。上清を捨て、再度アセトンを加えて撹拌し、析出物を濾取、乾燥し、目的ポリマーを得た。
白色粉末 ２０．９０ｇ
【００４５】
上記の如くして得られた成分（Ａ）の高分子又はその塩は、毛髪構造の乱れた部分により強く化学的に親和し、より強く吸着する。そしてこの作用により損傷毛髪に対して保護又は改善作用を有することが開示されている（再公表特許ＷＯ００／３２５６０）。しかしながら、このものが単独で或いは他の物質と組み合わることで保湿効果及び／又はつやを経時的に維持できることについては何ら記載されておらず、更に前記した開示情報と他の公知情報から本発明の効果を導き出すことは容易ではない。
【００４６】
＜２＞成分（Ｂ）
成分（Ｂ）は、アミノ酸、ケラチン、遊離ペプチド、遊離コラーゲンから選ばれる１種乃至は２種以上を指す。
【００４７】
ここで成分（Ｂ）に於けるアミノ酸としては、一般に用いられているものであれば特段の限定を受けないが具体例を挙げると、グリシン、アラニン、バリン、ロイシン、イソロイシン、セリン、トレオニン、システイン、シスチン、メチオニン、アスパラギン酸、グルタミン酸、リシン、アルギニン、フェニルアラニン、チロシン、ヒスチジン、トリプトファン、プロリン、オキシプロリン、β−アラニン、γ−アミノ酪酸、アントラニル酸、ｍ−アミノ安息香酸、ｐ−アミノ安息香酸等が挙げられる。
またケラチンとしては一般に用いられているものであれば特段の限定を受けない。
また遊離ペプチドとしては一般に用いられているものであれば特段の限定を受けないが具体例を挙げるとエステル化ポリペプチド、カチオニックペプチド、４級化ポリペプチド、油溶性ポリペプチド等が挙げられる。
また遊離コラーゲンとしては一般に用いられているものであれば特段の限定を受けない。
【００４８】
斯かる成分（Ｂ）の中ではアミノ酸がより好ましく、アルギニンが特に好ましい。それはこのものを用いた際に本発明の効果が最も優れて発揮されるからである。
【００４９】
成分（Ｂ）には保湿効果或いはつや出し効果を示すものがある。しかしながら、成分（Ｂ）単独で或いは成分（Ｂ）以外の物質と組み合わることで保湿効果及び／又はつやを経時的に維持できることについては未だ知られていない。更に、成分（Ｂ）と成分（Ａ）を組み合わせることで、本発明の効果が発現することについて何人も容易に導き出すことは出来ない。
【００５０】
＜３＞本発明の毛髪化粧料
本発明の毛髪化粧料は成分（Ａ）と成分（Ｂ）を共に含有する。
【００５１】
本発明の毛髪化粧料における、前記成分（Ａ）と成分（Ｂ）それぞれの含有率は、本発明の効果が発揮される限りに於いて特段の限定を受けないが、成分（Ａ）の含有率は０．０００１〜１重量％がより好ましく、０．００１〜０．１重量％が特に好ましい。また、本発明の毛髪化粧料における成分（Ｂ）の含有率は０．０００１〜１重量％がより好ましく、０．００１〜０．１重量％が特に好ましい。成分（Ａ）と成分（Ｂ）の比率は、本発明の効果が損なわれない限りにおいて特段の限定を受けないが、
１：１００００〜１００００：１の範囲が一般的であり、１：１００〜１００：１の範囲がより好ましく、１：１０〜１０：１の範囲が特に好ましい。これらの範囲を超えて一方の比率が高くなると本発明の効果の発現が不充分になる。
【００５２】
更に本発明の毛髪化粧料には上記の必須構成成分以外に、所望に応じて本発明の効果を損なわない量的、質的範囲内で、通常毛髪化粧料に用いられる成分を含有することが出来る。斯かる成分として例えば、油脂、炭化水素、エステル類、シリコーン、高級アルコール等の油分；エタノール、イソプロパノール等のアルコール類；アニオン性界面活性剤、カチオン性界面活性剤、非イオン性界面活性剤、両性界面活性剤等の界面活性剤；グリセリン、ポリエチレングリコール、ジエチレングリコールモノエチルエーテル、プロピレングリコール、ジプロピレングリコール、１，３−ブチレングリコール、キシリトール、グルコース、ソルビトール、マルチトール、ピロリドンカルボン酸、ポリオキシエチレンアルキルグルコシド、ポリオキシプロピレンアルキルグルコシド等の保湿剤；スクワレン、ラノリン、パーフルオロポリエーテル、カチオン性ポリマー等の感触向上剤；メチルセルロース、カルボキシビニルポリマー、ヒドロキシエチルセルロース、ポリオキシエチレングリコールジステアレート、キサンタンガム、ポリオキシアルキレンソルビタンエステル等の粘度調整剤；エチレンジアミン四酢酸（ＥＤＴＡ）、ホスホン酸塩類等のキレート剤；エチレングリコールモノステアレート、エチレングリコールジステアレート等のパール化剤；薬剤；ｐＨ調整剤；香料；色素；紫外線吸収剤；紫外線散乱剤；アクリル系樹脂、シリコーン樹脂、ポリビニルピロリドン等の樹脂；ジブチルヒドロキシトルエン等の酸化防止剤；トリクロサン、トリクロロカルバン等の殺菌剤；グリチルリチン酸カリウム、酢酸トコフェロール等の抗炎症剤；ジンクピリチオン、オクトピロックス、ヒドロキシピロリドン誘導体等の抗フケ剤；メチルパラベン、エチルパラベン、ブチルパラベン等の防腐剤；ビオチン、パントテン酸、レシチン、ゼラチン等の動植物抽出物又はその誘導体；ビタミン又はその前駆対等の栄養成分；γ−オリザノール、デキストラン硫酸ナトリウム、ニコチン酸誘導体等の血行促進剤；硫黄、チアントール等の抗脂漏剤；ナイロン、ポリエチレン等のポリマー微粉体；その他Ｅｎｃｙｃｌｏｐｅｄｅａ ｏｆ Ｓｈａｍｐｏｏ Ｉｎｇｒｅｄｉｅｎｔｓ（Ｍｉｃｅｌｌｅｐｒｅｓｓ，１９８５）に収載されている成分等が挙げられる。
【００５３】
本発明の化粧料としては、毛髪に適用される化粧料の全てが含まれ、それらを具体的に例示すれば、例えばプレシャンプー剤、シャンプー、ヘアリンス、リンスインシャンプー、ヘアパック、ヘアコンディショナー、ヘアトリートメント、セットローション、ブロースタイリングローション、ヘアスプレー、泡状スタイリング剤、ジェル状スタイリング剤、ヘアリキッド、ヘアトニック、ヘアクリーム、一時染毛剤、永久染毛剤、ヘアワックス等が挙げられる。これらの中でもシャンプー、ヘアリンス、ヘアパック、ブロースタイリングローション、泡状スタイリング剤、ジェル状スタイリング剤がより好ましい。さらに本発明のこれら毛髪化粧料は通常の方法に従って製造することができ、例えば、必須構成成分と前記任意成分を室温又は加熱下で混合攪拌することにより製造でき、乳化系、水溶液、ゲル、ペースト状とすることができる。
【００５４】
【実施例】
以下、本発明を実施例により更に詳しく説明する。但し本発明が下記実施例によって限定されないことは言うまでもない。
【００５５】
実施例１〜４
＜本発明の毛髪化粧料の保湿効果の経時的維持率とつやの経時的維持率の測定＞
従来の保湿剤（プロピレングリコール、グリセリン、尿素、ソルビトール、ポリエチレングリコール２００；以下順に比較例１〜比較例５とする）、従来のつや出し剤（シリコーン、エステル油、加水分解蛋白質、ポリオール、高級アルコール；以下順に比較例６〜比較例１０とする）、成分（Ａ）単独（製造例３のポリマー、製造例４のポリマー；以下順に比較例１１、比較例１２とする）、成分（Ｂ）単独（アルギニン、グリシン、アラニン、ケラチン、エステル化ポリペプチド、遊離コラーゲン；以下順に比較例１３〜比較例１８とする）、並びに成分（Ａ）と成分（Ｂ）の組み合わせ（本発明の毛髪化粧料：製造例３のポリマーとアルギニン、グリシン、アラニン、ケラチンの組み合わせ；以下順に実施例１〜４とする、参考の毛髪化粧料：製造例３のポリマーとエステル化ポリペプチド、遊離コラーゲンの組み合わせ及び製造例４のポリマーとアルギニン、グリシン、アラニン、ケラチン、エステル化ポリペプチド、遊離コラーゲンの組み合わせ；以下順に参考例１〜参考例８とする）をサンプルに用いて、保湿効果、保湿効果の維持、つや、つやの維持について測定した。実験方法は、１０ｃｍの毛髪１ｇに各サンプルの濃度が１％になるように塗布し、塗布前後の水分量、つやを測定しその上昇率を算出した。水溶性のものは水溶液１％とし、油溶性のものは２−エチルヘキサン酸の１％溶液をサンプル溶液とし、コントロール（２−エチルヘキサン酸のみ）との差をとって算出した。水分量の測定にはファインコスメティック社製アクアチェッカーＨＣ−１０００を、つやの測定には日本電色社製ＧＬＯＳＳ ＭＥＴＥＲ ＶＧ２０００を用いた。測定結果を表１に記す。
【００５６】
【表１】
表１の結果から、従来の保湿剤（比較例１〜比較例５）及び従来のつや出し剤（比較例６〜比較例１０）と比較して、成分（Ａ）と成分（Ｂ）を組み合わせてなる実施例１〜実施例４、参考例１〜８は保湿効果の経時的維持及び／又はつやの経時的維持において優れていることが判った。又、成分（Ａ）単独（比較例１１と比較例１２）及び成分（Ｂ）単独（比較例１３〜比較例１８）と比較しても、成分（Ａ）と成分（Ｂ）を組み合わせてなる実施例１〜実施例４は保湿効果の経時的維持及び／又はつやの経時的維持において優れていることが判った。さらに、成分（Ａ）と成分（Ｂ）を組み合わせてなるものは、成分（Ａ）単独乃至は成分（Ｂ）単独の各々が有する保湿効果、保湿効果の経時的維持、つや出し効果、つや出し効果の経時的維持を単に相加的に発現したのではなく、各々が持つ効果を相乗的に発揮したことが判った。
【００５８】
また、成分（Ａ）の中でも、製造例３のポリマー即ちリジン−メタクリル酸アミド又はその塩を構成単量体として用い、重合又は共重合してなる高分子又はその塩が特に優れていることが判った。成分（Ｂ）に関しては、アミノ酸が優れていることが判り、中でもアルギニンが特に優れていることが判った。
【００５９】
以下にその他の実施例を挙げる。
【００６０】
参考例９ ヘアリンス
（１）塩化セチルトリメチルアンモニウム ０．６ 重量％
（２）セトステアリルアルコール（Ｃ１６／Ｃ１８＝６／４） ４．０
（３）ジメチルポリシロキサン（５ｃｓ） ３．０
（４）グリセロールモノステアリン酸 １．０
（５）流動パラフィン ３．０
（６）製造例１のポリマー ０．０１
（７）アルギニン ０．０１
（８）グリセロールモノステアレート １．０
（９）グリセリン ５．０
（１０）プロピレングリコール ５．０
（１１）防腐剤 適量
（１２）色素 適量
（１３）香料 適量
（１４）精製水 残余
＜製法＞（１４）に（１）、（６）〜（１３）を加熱混合し、（５）に（２）〜（４）を加熱混合し、両者を混合、乳化した。
＜評価＞このリンスをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６１】
参考例１０ ヘアトリートメントクリーム
（１）塩化ベヘニルトリメチルアンモニウム ３．０ 重量％
（２）セトステアリルアルコール（Ｃ１６／Ｃ１８＝６／４） ６．５
（３）ベヘニルアルコール ２．０
（４）ジメチルポリシロキサン（２０ｃｓ） ３．０
（５）２−オクチルドデカノール ２．０
（６）ポリオキシエチレン硬化ヒマシ油誘導体 ０．３
（エチレンオキサイド６０モル付加物）
（７）ポリオキシエチレンステアリルエーテル １．０
（エチレンオキシド４モル付加物）
（８）大豆レシチン ０．５
（９）流動パラフィン ３．０
（１０）製造例２のポリマー ０．０３
（１１）グリシン ０．０３
（１２）グリセリン １０．０
（１３）ジプロピレングリコール ５．０
（１４）防腐剤 適量
（１５）色素 適量
（１６）香料 適量
（１７）精製水 残余
＜製法＞（１７）に（１）、（１０）〜（１６）を加熱混合し、（５）及び（９）の混合物に（２）〜（４）及び（６）〜（８）を加熱混合し、両者を混合、乳化した。
＜評価＞このヘアトリートメントクリームをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６２】
実施例５ ヘアリンス
（１）ステアリン酸ジエチルアミノエチルアミド ０．６ 重量％
（２）セチルアルコール ２．０
（３）ステアリルアルコール １．０
（４）ジメチルポリシロキサン（５ｃｓ） ３．０
（５）グリセロールモノステアリン酸 １．０
（６）流動パラフィン ３．０
（７）製造例３のポリマー ０．００５
（８）ケラチン ０．００５
（９）グリセロールモノステアレート １．０
（１０）グリセリン ５．０
（１１）プロピレングリコール ５．０
（１２）Ｌ−グルタミン酸 ０．６
（１３）防腐剤 適量
（１４）色素 適量
（１５）香料 適量
（１６）精製水 残余
＜製法＞（１６）に（１）、（７）〜（１５）を加熱混合し、（６）に（２）〜（５）を加熱混合し、両者を混合、乳化した。
＜評価＞このリンスをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６３】
参考例１１ ヘアトリートメントクリーム
（１）ステアリン酸ジメチルアミノプロピルアミド ３．０ 重量％
（２）セチルアルコール ６．５
（３）ベヘニルアルコール ２．０
（４）ステアリン酸 ２．０
（５）ジメチルポリシロキサン（２０ｃｓ） ３．０
（６）２−オクチルドデカノール ２．０
（７）ポリオキシエチレン硬化ヒマシ油誘導体 ０．３
（エチレンオキサイド６０モル付加物）
（８）ポリオキシエチレンステアリルエーテル １．０
（エチレンオキシド４モル付加物）
（９）流動パラフィン ３．０
（１０）製造例４のポリマー ０．０００５
（１１）エステル化ポリペプチド ０．００５
（１２）グリセリン １０．０
（１３）ジプロピレングリコール ５．０
（１４）Ｌ−グルタミン酸 １．０
（１５）防腐剤 適量
（１６）色素 適量
（１７）香料 適量
（１８）精製水 残余
＜製法＞（１８）に（１）、（１０）〜（１７）を加熱混合し、（５）及び（９）の混合物に（２）〜（４）及び（６）〜（８）を加熱混合し、両者を混合、乳化した。
＜評価＞このヘアトリートメントクリームをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６４】
参考例１２ ヘアシャンプー
（１）ラウリル硫酸ナトリウム ８．０ 重量％
（２）ラウリル硫酸トリエタノールアミン ５．０
（３）ヤシ油脂肪酸アミドプロピルベタイン ４．０
（４）ジステアリン酸エチレングリコール ２．０
（５）プロピレングリコール １０．０
（６）製造例３のポリマー ０．０００３
（７）遊離コラーゲン ０．０１
（８）防腐剤 適量
（９）色素 適量
（１０）香料 適量
（１１）精製水 残余
＜製法＞（１１）に（１）〜（１０）を順次添加し、加熱混合した後、冷却した。
＜評価＞このヘアシャンプーをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６５】
実施例６ ヘアスプレー
（１）エタノール ７５．０ 重量％
（２）デカメチルシクロポリシロキサン ５．０
（３）ポリオキシエチレン硬化ヒマシ油（４０Ｅ．Ｏ．） １．０
（４）製造例３のポリマー ０．０１
（５）アルギニン ０．０００３
（６）メチルポリシロキサン（２５℃ １０ｍＰａ・ｓ） ０．２
（７）メントール ０．１
（８）防腐剤 適量
（９）精製水 残余
＜製法＞（１）に（２）〜（９）を順に加え加温、攪拌した後、室温に戻して原液を調製した。原液６７％に対して液化石油ガスを３３％加えてヘアースプレーを調製した。
＜評価＞このヘアスプレーをサンプルに用いて実施例１〜４と同様にして評価すると、このものは保湿効果の経時的維持とつや出し効果の経時的維持共に優れていることが判った。
【００６６】
【発明の効果】
本発明によれば、保湿効果の経時的維持率及び／又はつやの経時的維持率に優れた毛髪化粧料を提供することが出来た。[0001]
[Industrial application fields]
The present invention relates to a hair cosmetic, and more particularly to a hair cosmetic excellent in moisture or gloss retention over time.
[0002]
[Prior art]
Conventionally, moisturizers and polishes are blended in hair cosmetics in order to give the hair a moist feel and a beautiful gloss. Usually, examples of the humectant include propylene glycol, glycerin, urea, sorbitol, alcohol added with alkylene oxide, and the like. Examples of the glossing agent include silicone, ester oil, hydrolyzed protein, polyol, and higher alcohol.
[0003]
On the other hand, the load applied to the hair due to the application of the hair cosmetic is never small, and therefore it is desirable to maintain the moist feel and beautiful gloss once applied as long as possible. However, although these conventional moisturizing agents or polishes are excellent in mere moisturizing effect or glossing effect, they have not been sufficient in terms of maintaining the moisturizing effect or glossing effect over time.
[0004]
[Problems to be solved by the invention]
An object of the present invention is to provide a hair cosmetic that is excellent in the retention rate of the moisturizing effect over time and / or the retention rate of gloss over time.
[0005]
[Means for Solving the Problems]
In view of such a situation, the present inventors have conducted intensive research, and as a result, hair cosmetics containing a specific polymer and a compound are excellent in the retention rate of moisturizing effect and / or the retention rate of gloss over time. As a result, the present invention has been completed.
[0006]
That is, this invention provides the hair cosmetics containing the following (A) and (B).The
(A)Represented by formula (4) or (5)One or more selected from a polymer or a salt thereof obtained by polymerization or copolymerization using a compound or a salt thereof as a constituent monomer.
[0007]
[Chemical Formula 3]
(B)Arginine, glycine, alanine and keratin1 type selected from or 2 or more types.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
[0010]
<1> Component (A)
Component (A) is a compound represented by formula (1) or a salt thereof as a constituent monomer, and includes one or more selected from a polymer or a salt obtained by polymerization or copolymerization. Point to.
[0011]
[Chemical 8]
[0012]
Here, R1 in formula (1) represents a hydrogen atom or a methyl group, and R2 represents an amino acid residue. The amino acid residue of R2 is not particularly limited as long as the amino acid is a commonly known amino acid, and specific examples include glycine, alanine, glutamine, lysine, arginine and the like. Of these, lysine residues are particularly preferred. When using a polymer or salt containing this as a constituent monomer, the hair cosmetic composition of the present invention is particularly excellent in terms of the retention rate over time and / or the retention rate over time of the gloss. It is.
[0013]
Among the compounds represented by the formula (1) or salts thereof, the compounds represented by the formulas (2) to (6) or salts thereof are more preferred, and in the formulas (4) and (5) The compounds represented are particularly preferred. This is because the effects of the present invention are more excellent when these compounds are used.
[0014]
[Chemical 9]
[0015]
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[0016]
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[0017]
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[0018]
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[0019]
The salt of the compound represented by the formula (1) is not particularly limited as long as it does not cause inconvenience when applied to hair. Specifically, for example, mineral acid salts such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, citric acid, oxalic acid, fumaric acid, maleic acid, formic acid, acetic acid, methanesulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid, etc. Examples thereof include salts of organic acid salts, carbonates, alkali metal salts such as sodium and potassium, and alkaline earth metal salts such as calcium and magnesium.
[0020]
The compound represented by the formula (1) or a salt thereof can be produced according to a conventional method. Specifically, for example, acrylic acid or methacrylic acid may be condensed with an amino acid. The preparation of the salt may be performed according to a conventional method. For example, the compound represented by the formula (1) and an acid or base may be mixed in an organic or inorganic solvent at an appropriate ratio.
[0021]
The polymer of the component (A) or a salt thereof is a kind or a salt of a polymer or a salt thereof obtained by polymerization or copolymerization using the compound represented by the formula (1) or a salt thereof as a constituent monomer. 2 or more types.
[0022]
The polymer is obtained by polymerization or copolymerization using a compound represented by the formula (1) or a salt thereof as a constituent monomer. Here, one type of compound represented by the formula (1) or a salt thereof may be used, or two or more types may be used. Here, when two or more kinds are used, the arrangement state of the polymer chains may be any of a graft copolymer, a block copolymer, and a random copolymer as long as the effects of the present invention are not impaired.
[0023]
Furthermore, it may be polymerized or copolymerized using only the compound represented by the formula (1) or a salt thereof, or the compound represented by the formula (1) or a compound thereof as long as the effects of the present invention are not impaired. In addition to the salt, other compounds may be combined and used as a constituent monomer for polymerization or copolymerization. Such a constituent monomer that can be used in combination is not particularly limited as long as it is a monomer that constitutes a polymer chain of a polymer that is generally used in cosmetics and external preparations for skin. Examples thereof include ethylene, vinyl alcohol, acrylic acid, acrylic acid ester, methacrylic acid, and methacrylic acid ester. When other compounds are used in addition to the compound represented by the formula (1) or a salt thereof, the alignment state of the polymer chain may be a graft copolymer, a block copolymer, a random copolymer as long as the effects of the present invention are not impaired. Any of copolymers may be used.
[0024]
The proportion of the compound represented by formula (1) or the salt thereof in the compound used for polymerization or copolymerization or the salt thereof as a whole varies depending on the type of other compounds used in combination, but is preferably 10% by weight or more, and 50% by weight. % Or more is more preferable, and the case where only the compound represented by the formula (1) or a salt thereof is used as a monomer is particularly preferable. This is because the effect of the present invention becomes smaller as the proportion of the compound represented by the formula (1) or a salt thereof becomes lower. If these compounds are polymerized according to a conventional method, the polymer of component (A) or a salt thereof can be produced. Specifically, solution polymerization or emulsion polymerization may be performed in the presence of a polymerization initiator.
[0025]
The salt is not particularly limited as long as it is physiologically acceptable, and specifically, for example, mineral acid salts such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, citric acid, oxalic acid, fumaric acid, maleic acid. Acid, formic acid, acetic acid, methanesulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid and other organic acid salts, carbonates, alkali metal salts such as sodium and potassium, and alkaline earth metal salts such as calcium and magnesium Can be mentioned. As for the preparation of the salt, it can be obtained by using a salt as the monomer, or the salt may be formed after the polymerization.
[0026]
The polymer thus obtained has a partial structure represented by the formula (7) in the polymer chain. Therefore, R1 in formula (1) corresponds to R3 in formula (7), and R2 in formula (1) corresponds to R4 in formula (7). That is, the forms of R3 and R4 in Formula (7) are the same as the forms of R1 and R2 in Formula (1).
[0027]
Embedded image
[0028]
R3 in Formula (7) represents a hydrogen atom or a methyl group. R4 represents an amino acid residue. Here, the preferable form of R4 is the same as the form of R3 in the aforementioned formula (1).
[0029]
In formula (7), R4 represents an amino acid residue. The amino acid residue is not particularly limited as long as the amino acid is a commonly known amino acid, and specific examples include glycine, alanine, glutamine, lysine, arginine and the like. Of these, a lysine residue is particularly preferable because this structural formula is particularly excellent in terms of exerting the effects of the present invention.
[0030]
The polymer salt having the partial structure represented by the formula (7) is not particularly limited. Specifically, for example, mineral acid salts such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, citric acid, oxalic acid, fumaric acid, maleic acid, formic acid, acetic acid, methanesulfonic acid, benzenesulfonic acid, paratoluenesulfonic acid, etc. Examples thereof include salts of organic acid salts, carbonates, alkali metal salts such as sodium and potassium, and alkaline earth metal salts such as calcium and magnesium.
[0031]
Of the partial structures represented by the formula (7), one or more selected from the partial structures represented by the formulas (8) to (13) are preferable. This is because a polymer obtained by polymerization using a compound represented by the formula (2) as a constituent monomer or a salt thereof has a partial structure represented by the formula (8). Similarly, the formula (3) This is because the compound represented by (6) corresponds to the partial structural formulas represented by formulas (9) to (12). A polymer obtained by copolymerizing the compounds represented by the formulas (2) and (6) is also excellent, but this has a partial structural formula represented by the formula (13). ) Is also preferred.
[0032]
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[0033]
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[0034]
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[0035]
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[0036]
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[0037]
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[0038]
The molecular weight of the component (A) polymer is preferably 5,000 to 1,000,000, more preferably 10,000 to 100,000. This is because when the molecular weight is in this range, it is excellent in terms of use feeling and action on hair.
[0039]
Production examples of component (A) will be described below.
[0040]
<1> Production Example 1 Alanine-methacrylamide polymer
(A compound obtained by polymerization using a compound represented by the formula (2) as a constituent monomer; this has a partial structural formula represented by the formula (8) in the polymer chain)
[1] Alanine-methacrylamide [compound represented by formula (2)]
55.28 g of potassium carbonate was dissolved in 200 ml of distilled water, and 17.82 g of D, L-α-alanine was dissolved in this. With vigorous stirring under ice cooling, 23.00 g of methacrylic acid chloride was added dropwise in about 20 minutes, and the mixture was vigorously stirred for about 2 hours. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 1-2, and then the salt was saturated and extracted three times with 200 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. Recrystallization was performed with ethyl acetate, and the obtained crystals were collected by filtration and dried.
White crystals 19.96g
[2] Polymerization
8.35 g of the obtained crystal was dissolved in 50 ml of distilled water and 50 ml of methanol, nitrogen gas was passed through for 30 minutes, 100 mg (0.37 mmol) of potassium persulfate was added and dissolved, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, it was poured into acetone to precipitate a precipitate. The supernatant was discarded, acetone was added again and stirred, and the precipitate was collected by filtration and dried to obtain the target polymer.
White powder 6.68g
[0041]
<2> Production Example 2 Glutamine-methacrylic acid amide polymer
(A compound obtained by polymerization using a compound represented by formula (3) as a constituent monomer; this has a partial structural formula represented by formula (9) in the polymer chain)
[1] Glutamine-methacrylamide [compound represented by formula (2)]
34.55 g of potassium carbonate was dissolved in 100 ml of distilled water, 7.30 g of L-glutamine was dissolved therein, and 20 ml of acetonitrile was further added. While stirring vigorously, 10.45 g of methacrylic acid chloride was dropped in about 10 minutes, and the mixture was stirred vigorously for about 2 hours. The reaction solution was adjusted to pH 1-2 with concentrated hydrochloric acid, saturated with sodium chloride, and washed twice with 100 ml of ethyl acetate. The obtained aqueous layer was extracted three times with 100 ml of ethyl acetate / isopropanol = 1/1. The ethyl acetate / isopropanol layers were combined and concentrated, followed by silica gel column purification (elution with silica gel 30 g, chloroform / methanol = 2/1), and the necessary fractions were collected and concentrated.
Colorless syrup 7.47g
[2] Polymerization
7.47 g of the obtained syrup was dissolved in 50 ml of distilled water and 50 ml of methanol, and nitrogen gas was passed through for 1 hour, and then 100 mg of potassium persulfate was added and dissolved, followed by heating under reflux for 3 hours. After cooling to room temperature, it was poured into isopropanol, and the precipitate was collected by filtration and dried to obtain the target polymer.
White powder 6.35g
[0042]
<3> Production Example 3 Lysine-methacrylamide polymer
((A compound obtained by polymerization using a compound represented by formula (4) or formula (5) as a constituent monomer; this is a partial structural formula represented by formula (10) or formula (11) (In the polymer chain)
[1] Lysine-methacrylic acid amide [compound represented by formula (4) or formula (5)] 5.51 g of potassium hydrogen carbonate was dissolved in 100 ml of distilled water, and 9.13 g of lysine hydrochloride was dissolved therein. A further 80 ml of acetone was added. While vigorously stirring under ice cooling, 5.23 g of methacrylic acid chloride was added dropwise in about 10 minutes, and the mixture was vigorously stirred for about 2 hours. The reaction solution was adjusted to pH 1-2 with concentrated hydrochloric acid, and then saturated with sodium chloride. The aqueous layer was washed twice with 100 ml of ethyl acetate and then washed three times with 100 ml of ethyl acetate / isopropanol = 1/2. The ethyl acetate / isopropanol layers were combined and concentrated under reduced pressure to about 50 ml, 500 ml of isopropanol was added, and the mixture was concentrated again to about 200 ml. Precipitated sodium chloride was removed by filtration, and the filtrate was concentrated.
5.53 g of colorless syrup
[2] Polymerization
5.53 g of the resulting lysine-mono-methacrylic acid amide hydrochloride was dissolved in 50 ml of distilled water, aerated with nitrogen gas for 30 minutes, and then dissolved in 100 mg (0.37 mmol) of potassium persulfate for 3 hours. Heated to reflux. After cooling to room temperature, it was poured into acetone to precipitate a precipitate. The supernatant was discarded, acetone was added again and stirred, and the precipitate was collected by filtration and dried to obtain the target polymer.
White powder 4.20g
[0043]
<4> Production Example 4 Arginine-methacrylic acid amide polymer
((A compound obtained by polymerization using a compound represented by formula (6) as a constituent monomer; this has a partial structural formula represented by formula (12) in the polymer chain)
[1] Arginine-methacrylamide [compound represented by formula (6)]
27.64 g of potassium carbonate was dissolved in 200 ml of distilled water, 21.07 g of arginine hydrochloride was dissolved therein, and 80 ml of acetone was further added. While vigorously stirring under ice cooling, 10.46 g of methacrylic acid chloride was dropped in about 10 minutes, and the mixture was vigorously stirred for 1 hour. The reaction solution was adjusted to pH 1 with concentrated hydrochloric acid and saturated with sodium chloride. The aqueous layer was washed three times with 300 ml of ethyl acetate and extracted three times with 200 ml of ethyl acetate / isopropanol = 1/1. The ethyl acetate / isopropanol layers were combined, concentrated to about 100 ml under reduced pressure, 400 ml of isopropanol was added, and the mixture was concentrated again to about 200 ml. Precipitated sodium chloride was removed by filtration, and the filtrate was concentrated.
Colorless syrup 21.80g
[2] Polymerization
4.84 g of the resulting arginine methacrylic acid amide hydrochloride was dissolved in 40 ml of distilled water, nitrogen gas was passed through for 1 hour, 60 mg of potassium persulfate was added and dissolved, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, it was poured into acetone to precipitate a precipitate. The supernatant was discarded, acetone was added again and stirred, and the precipitate was collected by filtration and dried to obtain the desired polymer.
White powder 3.05g
[0044]
<5> Production Example 5 Alanine-methacrylamide / arginine-methacrylamide (= 7: 3) copolymer
(A compound obtained by polymerizing compounds represented by formula (2) and formula (6) as constituent monomers; this has a partial structural formula represented by formula (13) in the polymer chain. )
Arginine methacrylic acid amide hydrochloride 10.53 g and the alanine-methacrylic acid amide 13.90 g shown above were dissolved in 100 ml of distilled water, nitrogen gas was passed through for 1 hour, and then 250 mg of potassium persulfate was added and dissolved for 3 hours. Heated to reflux. After cooling to room temperature, it was poured into acetone to precipitate a precipitate. The supernatant was discarded, acetone was added again and stirred, and the precipitate was collected by filtration and dried to obtain the desired polymer.
White powder 20.90g
[0045]
The polymer of the component (A) or a salt thereof obtained as described above has a stronger chemical affinity and more strongly adsorbs to the disordered part of the hair structure. It is disclosed that this action has a protective or improving action on damaged hair (Republished Patent WO 00/32560). However, it is not described at all that the moisturizing effect and / or gloss can be maintained over time by using this alone or in combination with other substances. Further, the present invention is based on the disclosed information and other known information. It is not easy to derive the effect.
[0046]
<2> Component (B)
A component (B) points out 1 type, or 2 or more types chosen from an amino acid, keratin, a free peptide, and free collagen.
[0047]
Here, the amino acid in component (B) is not particularly limited as long as it is generally used, but specific examples include glycine, alanine, valine, leucine, isoleucine, serine, threonine, cysteine. , Cystine, methionine, aspartic acid, glutamic acid, lysine, arginine, phenylalanine, tyrosine, histidine, tryptophan, proline, oxyproline, β-alanine, γ-aminobutyric acid, anthranilic acid, m-aminobenzoic acid, p-aminobenzoic acid Etc.
The keratin is not particularly limited as long as it is generally used.
The free peptide is not particularly limited as long as it is generally used, but specific examples include esterified polypeptide, cationic peptide, quaternized polypeptide, oil-soluble polypeptide and the like.
The free collagen is not particularly limited as long as it is generally used.
[0048]
Among such components (B), amino acids are more preferred, and arginine is particularly preferred. This is because the effect of the present invention is most excellent when this material is used.
[0049]
Some of the components (B) exhibit a moisturizing effect or a glossing effect. However, it is not yet known that the moisturizing effect and / or gloss can be maintained over time by using the component (B) alone or in combination with a substance other than the component (B). Furthermore, by combining the component (B) and the component (A), no one can easily derive that the effect of the present invention is manifested.
[0050]
<3> Hair cosmetic of the present invention
The hair cosmetic composition of the present invention contains both component (A) and component (B).
[0051]
In the hair cosmetic composition of the present invention, the content of each of the component (A) and the component (B) is not particularly limited as long as the effect of the present invention is exhibited, but the content of the component (A) The rate is more preferably 0.0001 to 1% by weight, and particularly preferably 0.001 to 0.1% by weight. Further, the content of the component (B) in the hair cosmetic composition of the present invention is more preferably 0.0001 to 1% by weight, particularly preferably 0.001 to 0.1% by weight. The ratio of the component (A) to the component (B) is not particularly limited as long as the effect of the present invention is not impaired.
The range of 1: 10000 to 10000: 1 is common, the range of 1: 100 to 100: 1 is more preferred, and the range of 1:10 to 10: 1 is particularly preferred. If one ratio exceeds this range, the effect of the present invention will be insufficiently exhibited.
[0052]
Furthermore, the hair cosmetic composition of the present invention may contain, in addition to the above essential components, components that are usually used in hair cosmetic compositions within the quantitative and qualitative ranges that do not impair the effects of the present invention as desired. I can do it. Examples of such components include oils such as fats and oils, hydrocarbons, esters, silicones, higher alcohols; alcohols such as ethanol and isopropanol; anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric Surfactants such as surfactants; glycerin, polyethylene glycol, diethylene glycol monoethyl ether, propylene glycol, dipropylene glycol, 1,3-butylene glycol, xylitol, glucose, sorbitol, maltitol, pyrrolidone carboxylic acid, polyoxyethylene alkyl Moisturizers such as glucosides and polyoxypropylene alkyl glucosides; touch improvers such as squalene, lanolin, perfluoropolyether, cationic polymers; methylcellulose, carboxyvinyl polymer , Hydroxyethylcellulose, polyoxyethylene glycol distearate, viscosity modifiers such as xanthan gum, polyoxyalkylene sorbitan ester; chelating agents such as ethylenediaminetetraacetic acid (EDTA) and phosphonates; ethylene glycol monostearate, ethylene glycol distearate Pearling agents such as rate; drugs; pH adjusting agents; fragrances; dyes; UV absorbers; UV scattering agents; resins such as acrylic resins, silicone resins, and polyvinylpyrrolidone; antioxidants such as dibutylhydroxytoluene; triclosan, trichloro Bactericides such as Calvin; anti-inflammatory agents such as potassium glycyrrhizinate and tocopherol acetate; anti-dandruff agents such as zinc pyrithione, octopirox and hydroxypyrrolidone derivatives; methylparaben and ethylparaben Preservatives such as butylparaben; animal and plant extracts or derivatives thereof such as biotin, pantothenic acid, lecithin and gelatin; nutritional components such as vitamins or precursors thereof; Anti-seborrheic agents such as sulfur and thianthol; fine polymer powders such as nylon and polyethylene; and other components listed in Encyclopedia of Shampoo Ingredients (Micellepress, 1985).
[0053]
The cosmetics of the present invention include all cosmetics applied to the hair. Specific examples thereof include pre-shampoos, shampoos, hair rinses, rinse-in shampoos, hair packs, hair conditioners, hair treatments. , Set lotions, blow styling lotions, hair sprays, foam styling agents, gel styling agents, hair liquids, hair tonics, hair creams, temporary hair dyes, permanent hair dyes, hair waxes and the like. Among these, shampoos, hair rinses, hair packs, blow styling lotions, foam styling agents, and gel styling agents are more preferable. Furthermore, these hair cosmetics of the present invention can be produced according to a usual method, for example, by mixing and stirring the essential components and the optional components at room temperature or under heating, and emulsifying system, aqueous solution, gel, paste Can be used.
[0054]
【Example】
Hereinafter, the present invention will be described in more detail with reference to examples. However, it goes without saying that the present invention is not limited to the following examples.
[0055]
Examples 1-4
<Measurement of the retention rate over time and the retention rate over time of the moisturizing effect of the hair cosmetic composition of the present invention>
Conventional moisturizer (propylene glycol, glycerin, urea, sorbitol, polyethylene glycol 200; hereinafter referred to as Comparative Example 1 to Comparative Example 5), conventional polish (silicone, ester oil, hydrolyzed protein, polyol, higher alcohol; In the following order, Comparative Example 6 to Comparative Example 10), Component (A) alone (polymer of Production Example 3, Polymer of Production Example 4; hereinafter referred to as Comparative Example 11 and Comparative Example 12), Component (B) alone ( Arginine, glycine, alanine, keratin, esterified polypeptide, free collagen; hereinafter referred to as Comparative Examples 13 to 18 in order, and a combination of component (A) and component (B) (hair cosmetic composition of the present invention: production) Example 3 polymer with arginine, glycine, alanine, keratinReference hair cosmetics in the following order in the order of Examples 1 to 4: The polymer and the polymer of Production Example 3Combination of stealized polypeptide and free collagen and combination of polymer of Production Example 4 with arginine, glycine, alanine, keratin, esterified polypeptide and free collagen;Reference Example 1 to Reference Example 8) Was used as a sample, and the moisturizing effect, maintenance of moisturizing effect, gloss, and maintenance of gloss were measured. In the experiment method, the sample was applied to 1 g of 10 cm of hair so that the concentration of each sample was 1%, the moisture content before and after application, and the gloss were measured, and the rate of increase was calculated. The water-soluble one was 1% aqueous solution, and the oil-soluble one was 1% solution of 2-ethylhexanoic acid as a sample solution, and the difference from the control (2-ethylhexanoic acid only) was calculated. Aquatic Checker HC-1000 manufactured by Fine Cosmetics was used for the moisture measurement, and GLOSS METER VG2000 manufactured by Nippon Denshoku Co., Ltd. was used for the gloss measurement. The measurement results are shown in Table 1.
[0056]
[Table 1]
From the results in Table 1, in comparison with the conventional moisturizer (Comparative Examples 1 to 5) and the conventional polish (Comparative Examples 6 to 10), the component (A) and the component (B) are combined. Example 1 to implementationExample 4, Reference Examples 1-8Was found to be excellent in maintaining the moisturizing effect over time and / or maintaining the gloss over time. Further, even when compared with component (A) alone (Comparative Example 11 and Comparative Example 12) and component (B) alone (Comparative Examples 13 to 18), the component (A) and component (B) are combined. Example 1 to Example4Was found to be excellent in maintaining the moisturizing effect over time and / or maintaining the gloss over time. Further, the combination of the component (A) and the component (B) is a combination of the component (A) alone or the component (B) each having the moisturizing effect, maintaining the moisturizing effect over time, the glossing effect, and the glossing effect. It was found that the maintenance over time was not merely expressed additively, but the effects of each were exhibited synergistically.
[0058]
Among components (A), the polymer of Production Example 3, that is, lysine-methacrylamide or a salt thereof, is used as a constituent monomer, and a polymer or a salt obtained by polymerization or copolymerization is particularly excellent. understood. Regarding the component (B), it was found that amino acids were excellent, and arginine was particularly excellent.
[0059]
Other examples are given below.
[0060]
Reference Example 9 Hair rinse
(1) Cetyltrimethylammonium chloride 0.6% by weight
(2) Cetostearyl alcohol (C16 / C18 = 6/4) 4.0
(3) Dimethylpolysiloxane (5cs) 3.0
(4) Glycerol monostearic acid 1.0
(5) Liquid paraffin 3.0
(6) Polymer of Production Example 1 0.01
(7) Arginine 0.01
(8) Glycerol monostearate 1.0
(9) Glycerin 5.0
(10) Propylene glycol 5.0
(11) Preservative appropriate amount
(12) Appropriate amount of dye
(13) Appropriate perfume
(14) Purified water residue
<Production Method> (1) and (6) to (13) were heated and mixed in (14), (2) to (4) were heated and mixed in (5), and both were mixed and emulsified.
<Evaluation> Examples 1 to 3 using this rinse as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0061]
Reference Example 10 Hair treatment cream
(1) Behenyltrimethylammonium chloride 3.0% by weight
(2) Cetostearyl alcohol (C16 / C18 = 6/4) 6.5
(3) Behenyl alcohol 2.0
(4) Dimethylpolysiloxane (20cs) 3.0
(5) 2-octyldodecanol 2.0
(6) Polyoxyethylene hydrogenated castor oil derivative 0.3
(Ethylene oxide 60 mol adduct)
(7) Polyoxyethylene stearyl ether 1.0
(Ethylene oxide 4 mol adduct)
(8) Soy lecithin 0.5
(9) Liquid paraffin 3.0
(10) Polymer of Production Example 2 0.03
(11) Glycine 0.03
(12) Glycerin 10.0
(13) Dipropylene glycol 5.0
(14) Preservative appropriate amount
(15) Dye appropriate amount
(16) Perfume appropriate amount
(17) Purified water residue
<Production method> (1), (10) to (16) are heated and mixed to (17), and (2) to (4) and (6) to (8) are heated to the mixture of (5) and (9). The two were mixed and emulsified.
<Evaluation> Examples 1 to 3 using this hair treatment cream as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0062]
Example 5 Hair rinse
(1) Diethylaminoethylamide stearate 0.6% by weight
(2) Cetyl alcohol 2.0
(3) Stearyl alcohol 1.0
(4) Dimethylpolysiloxane (5cs) 3.0
(5) Glycerol monostearic acid 1.0
(6) Liquid paraffin 3.0
(7) Polymer of Production Example 3 0.005
(8) Keratin 0.005
(9) Glycerol monostearate 1.0
(10) Glycerin 5.0
(11) Propylene glycol 5.0
(12) L-glutamic acid 0.6
(13) Preservative appropriate amount
(14) Appropriate amount of dye
(15) Perfume appropriate amount
(16) Purified water residue
<Manufacturing method> (1), (7) to (15) were heated and mixed to (16), (2) to (5) were heated and mixed to (6), and both were mixed and emulsified.
<Evaluation> Examples 1 to 3 using this rinse as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0063]
Reference Example 11 Hair treatment cream
(1) Dimethylaminopropylamide stearate 3.0% by weight
(2) Cetyl alcohol 6.5
(3) Behenyl alcohol 2.0
(4) Stearic acid 2.0
(5) Dimethylpolysiloxane (20cs) 3.0
(6) 2-octyldodecanol 2.0
(7) Polyoxyethylene hydrogenated castor oil derivative 0.3
(Ethylene oxide 60 mol adduct)
(8) Polyoxyethylene stearyl ether 1.0
(Ethylene oxide 4 mol adduct)
(9) Liquid paraffin 3.0
(10) Polymer of Production Example 4 0.0005
(11) Esterified polypeptide 0.005
(12) Glycerin 10.0
(13) Dipropylene glycol 5.0
(14) L-glutamic acid 1.0
(15) Preservative appropriate amount
(16) Dye appropriate amount
(17) Appropriate amount of perfume
(18) Purified water residue
<Production method> (1), (10) to (17) are heated and mixed with (18), and (2) to (4) and (6) to (8) are heated to the mixture of (5) and (9). The two were mixed and emulsified.
<Evaluation> Examples 1 to 3 using this hair treatment cream as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0064]
Reference Example 12 Hair shampoo
(1) Sodium lauryl sulfate 8.0 wt%
(2) Lauryl sulfate triethanolamine 5.0
(3) Palm oil fatty acid amidopropyl betaine 4.0
(4) Ethylene glycol distearate 2.0
(5) Propylene glycol 10.0
(6) Polymer of Production Example 3 0.0003
(7) Free collagen 0.01
(8) Preservative appropriate amount
(9) Dye appropriate amount
(10) Perfume appropriate amount
(11) Purified water residue
<Production Method> (1) to (10) were sequentially added to (11), heated and mixed, and then cooled.
<Evaluation> Examples 1 to 3 using this hair shampoo as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0065]
Example 6 hair spray
(1) Ethanol 75.0% by weight
(2) Decamethylcyclopolysiloxane 5.0
(3) Polyoxyethylene hydrogenated castor oil (40E.O.) 1.0
(4) Polymer of Production Example 3 0.01
(5) Arginine 0.0003
(6) Methyl polysiloxane (25 ° C., 10 mPa · s) 0.2
(7) Menthol 0.1
(8) Preservative appropriate amount
(9) Purified water residue
<Production Method> (2) to (9) were added to (1) in order, and the mixture was heated and stirred, and then returned to room temperature to prepare a stock solution. A hair spray was prepared by adding 33% of liquefied petroleum gas to 67% of the stock solution.
<Evaluation> Examples 1 to 3 using this hair spray as a sample4When this was evaluated in the same manner, it was found that this product was excellent in both maintaining the moisturizing effect over time and maintaining the gloss effect over time.
[0066]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, the hair cosmetics which were excellent in the temporal maintenance rate of the moisturizing effect and / or the temporal maintenance rate of the gloss could be provided.
Claims (4)
（Ａ）式（４）又は（５）で表される化合物又はその塩を構成単量体として用い、重合又は共重合してなる高分子又はその塩から選ばれる１種乃至は２種以上。
（Ｂ）アルギニン、グリシン、アラニン及びケラチンから選ばれる１種乃至は２種以上。
(A) One type or two or more types selected from polymers or salts obtained by polymerization or copolymerization using a compound represented by the formula (4) or (5) or a salt thereof as a constituent monomer.
(B) One or more selected from arginine, glycine, alanine and keratin .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2002223325A JP4046570B2 (en) | 2002-07-31 | 2002-07-31 | Hair cosmetics |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2002223325A JP4046570B2 (en) | 2002-07-31 | 2002-07-31 | Hair cosmetics |
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| Publication Number | Publication Date |
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| JP2004059540A JP2004059540A (en) | 2004-02-26 |
| JP2004059540A5 JP2004059540A5 (en) | 2005-05-12 |
| JP4046570B2 true JP4046570B2 (en) | 2008-02-13 |
Family
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Cited By (1)
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|---|---|---|---|---|
| US10835469B2 (en) | 2014-04-25 | 2020-11-17 | The Procter And Gamble Company | Method of inhibiting copper deposition on hair |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5155688B2 (en) * | 2008-02-20 | 2013-03-06 | ホーユー株式会社 | Hair treatment composition and hair treatment method |
| JP2015214592A (en) * | 2012-09-11 | 2015-12-03 | 味の素株式会社 | Temperature-responsive polymer and method for manufacturing the same |
| WO2014185464A1 (en) * | 2013-05-15 | 2014-11-20 | ライオン株式会社 | Emulsion based hair cosmetic |
| US9586063B2 (en) | 2014-04-25 | 2017-03-07 | The Procter & Gamble Company | Method of inhibiting copper deposition on hair |
| US9642788B2 (en) | 2014-04-25 | 2017-05-09 | The Procter & Gamble Company | Shampoo composition comprising gel matrix and histidine |
| US11786447B2 (en) | 2016-06-30 | 2023-10-17 | The Procter & Gamble Company | Conditioner composition comprising a chelant |
| US11246816B2 (en) | 2016-06-30 | 2022-02-15 | The Procter And Gamble Company | Shampoo compositions comprising a chelant |
| US20180000706A1 (en) | 2016-06-30 | 2018-01-04 | The Procter & Gamble Company | Conditioner Composition Comprising a Chelant |
| US20180000705A1 (en) | 2016-06-30 | 2018-01-04 | The Procter & Gamble Company | Shampoo Compositions Comprising a Chelant |
| US20180000715A1 (en) | 2016-06-30 | 2018-01-04 | The Procter & Gamble Company | Hair Care Compositions For Calcium Chelation |
| CN108203484B (en) | 2016-12-20 | 2022-03-01 | 罗门哈斯公司 | Latex functionalized with arginine-functionalized monomer building blocks |
| EP3613834B1 (en) | 2018-08-24 | 2026-04-01 | The Procter & Gamble Company | Treatment compositions comprising low levels of an oligoamine |
| EP3613835A1 (en) | 2018-08-24 | 2020-02-26 | The Procter & Gamble Company | Treatment compositions comprising a surfactant system and an oligoamine |
| JPWO2020116393A1 (en) * | 2018-12-03 | 2021-10-14 | 東洋紡株式会社 | Hair and improvement material |
| JP7348739B2 (en) * | 2019-03-29 | 2023-09-21 | 株式会社コーセー | Oil-in-water composition for hair |
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2002
- 2002-07-31 JP JP2002223325A patent/JP4046570B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10835469B2 (en) | 2014-04-25 | 2020-11-17 | The Procter And Gamble Company | Method of inhibiting copper deposition on hair |
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| JP2004059540A (en) | 2004-02-26 |
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