WO2013031313A1 - Composition for pretreatment for hair coloring - Google Patents
Composition for pretreatment for hair coloring Download PDFInfo
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- WO2013031313A1 WO2013031313A1 PCT/JP2012/063620 JP2012063620W WO2013031313A1 WO 2013031313 A1 WO2013031313 A1 WO 2013031313A1 JP 2012063620 W JP2012063620 W JP 2012063620W WO 2013031313 A1 WO2013031313 A1 WO 2013031313A1
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- hair
- hair color
- composition
- pretreatment composition
- hyaluronic acid
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Classifications
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- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
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- 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
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
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- 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
- A61Q5/10—Preparations for permanently dyeing the hair
Definitions
- the present invention relates to a hair color pretreatment composition, and more particularly to a hair color pretreatment composition that improves the hair dyeing effect during hair coloring and can reduce damage to the hair.
- the hair color may be used multiple times to cause damage to the hair.
- the damaged portion is dyed more and color unevenness occurs, or the hair cannot be dyed to the expected color.
- a pretreatment composition for example, see Patent Document 1.
- a pretreatment agent for hair dye containing a protein hydrolyzate for example, see Patent Document 1.
- the present invention has been made in view of the above-described problems of the prior art, and an object of the present invention is to provide a hair color pretreatment composition capable of improving the hair dyeing effect during hair coloring and reducing damage to the hair. .
- the present inventors formulated polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof into a hair color pretreatment composition to obtain a specific pH.
- a hair color pretreatment composition to obtain a specific pH.
- the hair color pretreatment composition according to the present invention comprises polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof, and has a pH of 7.5 to 10.
- the polyoxyethylene oleyl ether phosphate is preferably represented by the following formula (I).
- n is the average number of added moles of oxyethylene groups.
- the acetylated hyaluronic acid or a salt thereof has a repeating structural unit represented by the following formula (II).
- R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom or an ester-linked acetyl group (however, R 1 , R 2 , R in each repeating structural unit on average) 3 and at least two of R 4 represent an acetyl group), R 5 represents a hydrogen atom or an alkali metal, and k represents a number of 2 or more.
- the composition preferably contains 0.5 to 10% by mass of polyoxyethylene oleyl ether phosphoric acid and 0.0001 to 10% by mass of acetylated hyaluronic acid or a salt thereof.
- n represented by the formula (I) is preferably 1-20.
- the hair color pretreatment composition according to the present invention is a composition comprising polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof and having a pH of 7.5 to 10, and hair color It is possible to provide a hair color pretreatment composition that improves the hair dyeing effect at the time and can reduce damage to the hair.
- the hair color pretreatment composition according to the present invention contains polyoxyethylene oleyl ether phosphate and acetylated hyaluronic acid or salts thereof.
- polyoxyethylene oleyl ether phosphate and acetylated hyaluronic acid or salts thereof are polyoxyethylene oleyl ether phosphate and acetylated hyaluronic acid or salts thereof.
- the polyoxyethylene oleyl ether phosphoric acid is preferably a compound represented by the following formula (I).
- n is the average number of added moles of oxyethylene groups. n is not particularly limited, but is preferably 1 to 20, and more preferably 3 to 10.
- the blending amount of polyoxyethylene oleyl ether phosphoric acid is preferably 0.5 to 10% by mass.
- the blending amount is more preferably 1% by mass or more. When there are too few compounding quantities, it may be inferior to the hair dyeing effect. Further, the blending amount of polyoxyethylene oleyl ether phosphoric acid is more preferably 5% by mass or less. Even if there are too many compounding quantities, the remarkable improvement of an effect may not be seen.
- acetylated hyaluronic acid or its salts An acetylated hyaluronic acid or a salt thereof is a polymer compound in which the hydroxyl group of hyaluronic acid is partially acetylated.
- This acetylated hyaluronic acid is a water-soluble polymer having a moisturizing effect, and is known to have an anti-dandruff and damaging effect when applied for a long time.
- the acetylation rate with respect to the hydroxyl group of acetylated hyaluronic acid or a salt thereof is not particularly limited, but those having a repeating structural unit represented by the following formula (II) can be preferably used.
- R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or an ester-linked acetyl group (however, R 1 , R 2 in each repeating structural unit on average) , R 3 and R 4 each represents an acetyl group).
- R 5 represents a hydrogen atom or an alkali metal.
- k represents a number of 2 or more.
- the degree of acetylation is 1, and in the present invention, acetylated hyaluronic acid having a degree of acetylation of 2 to 4 is preferably used.
- the molecular weight of the acetylated hyaluronic acid used in the present invention is preferably about 10,000 to 1,000,000 in terms of hyaluronic acid.
- the method for producing acetylated hyaluronic acid or salts thereof used in the present invention is, for example, a method in which powdered hyaluronic acid is dispersed in acetic acid and trifluoroacetic anhydride is added as a catalyst to react, and hyaluronic acid is dispersed in acetic acid. Further, there are known a method in which p-toluenesulfonic acid is added and acetic anhydride is further added to react, and a method in which hyaluronic acid is suspended in an acetic anhydride solvent and then concentrated sulfuric acid is added to react (Japanese Patent Laid-open No. Hei 6). -9707, JP-A-8-53501, etc.), these methods can be used, but the method is not limited to the above-mentioned methods.
- the amount of acetylated hyaluronic acid or a salt thereof is preferably 0.0001 to 10% by mass.
- the blending amount is more preferably 0.001% by mass or more, and particularly preferably 0.1% by mass or more. If the amount is too small, the hair dyeing effect may be inferior, or damage to the hair may not be reduced. Further, the blending amount of acetylated hyaluronic acid or a salt thereof is more preferably 5% by mass or less, and particularly preferably 1% by mass or less. If the amount is too large, the viscosity may increase too much.
- the hair color pretreatment composition of the present invention needs to be adjusted to pH 7.5 to 10. If the pH is less than 7.5, the hair dyeing effect is poor. Even if pH exceeds 10, since the remarkable improvement of an effect is not seen, it is unpreferable.
- the pH can be adjusted by using one or more pH adjusting agents.
- pH adjusters include inorganic acids such as phosphoric acid, sulfuric acid, hydrochloric acid, and carbonic acid, alkali metal salts of organic acids such as citric acid, glycolic acid, and tartaric acid, ammonia, monoethanolamine, diethanolamine, and triethanolamine. And organic alkali salts such as aminomethylpropanol.
- the hair color pretreatment composition of the present invention water, protein hydrolyzate, surfactant, humectant such as glycerin, propylene glycol, sorbitol, carboxymethylcellulose, hydroxyethylcellulose as long as the effects of the present invention are not impaired.
- Optional components such as viscosity modifiers such as xanthan gum, lower alcohols, preservatives, and the like can be appropriately blended.
- the hair color pretreatment composition of the present invention is preferably used for pretreatment of an oxidative hair dye type hair color.
- the hair color pretreatment composition of the present invention is applied to the hair before the hair color, and is applied to the hair uniformly by hand, comb, etc., and then rinsed as it is or after being lightly rinsed, then any hair color is used. be able to.
- the hair color pretreatment composition of the present invention preferably uses any hair color as it is after coating.
- the present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
- the blending amount is expressed in mass% with respect to the system in which the component is blended. Prior to the description of the examples, the evaluation method of the test used in the present invention will be described.
- Evaluation (1) Color difference The color difference of the hair before and after the treatment (dry state) was measured using a color difference meter CM-3600 (manufactured by Minolta).
- the present inventors manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 below, and manufactured a hair color pretreatment composition with the composition shown in Table 2 below. did. Then, after wetting 1 g of the black hair bundle with water (Test Example 1-0), or after applying 0.3 g of the pretreatment composition of Test Examples 1-1 to 1-5 to 1 g of the black hair bundle, The hair color was applied by applying 3 g of hair color and allowed to stand for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 2. In the following test examples, the hair color used was a mixture of the first agent and the second agent in a ratio of 1: 1 (each 1.5 g) immediately before use. The pH of the hair color described in Table 1 was 10 (when the first agent and the second agent were mixed).
- the inventors of the present invention manufactured an oxidative hair dye type hair color by the conventional method with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 3 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 3.
- the hair color pretreatment composition of the present invention needs to contain polyoxyethylene oleyl ether phosphate and have a pH of 7.5 to 10.
- the inventors of the present invention manufactured an oxidative hair dye type hair color with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 4 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1) and (2). The results are shown in Table 4.
- the normal method is a method of applying a hair dyeing treatment by applying 0.3 g of the pretreatment composition to 1 g of black hair bundle, then applying 3 g of hair color, and washing after standing for 20 minutes.
- Method X is a method of applying hair coloring treatment by applying 3 g of hair color to 1 g of black hair bundle, applying 0.3 g of the pretreatment composition, and washing after standing for 20 minutes.
- Test Example 3-2 ′ even when the pretreatment composition of the present invention was applied after applying the hair color, the color difference was the same as in the case of no pretreatment (Test Example 3-0), and the hair dyeing effect was improved. I was not able to admit. Therefore, it is necessary to use the hair color pretreatment composition of the present invention before hair color.
- the inventors of the present invention examined the difference in effect when the active ingredient of the pretreatment composition was blended into the hair color.
- the inventors of the present invention manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 and Table 6 below, and the hair color pretreatment composition with the composition shown in Table 7 below. Manufactured.
- the pH of the hair color described in Table 6 was 10 (when the first agent and the second agent were mixed).
- the above-mentioned usual method or the hair dyeing process was carried out without pretreatment. And it evaluated by the said evaluation method (1). The results are shown in Table 7.
- Test Example 3-2 in which the same amount of the active ingredient as the pretreatment composition with Test Example 3-2 was applied as a hair color to a black hair bundle, is a test in which a hair color containing no active ingredient was applied The color difference was not so different from Example 3-0. For this reason, it becomes clear that the active ingredient of the present invention can exhibit an excellent hair dyeing effect when applied before the hair color as a hair color pretreatment composition, rather than being blended into the hair color. It was.
- the following is a formulation example of the hair color pretreatment composition of the present invention.
- the present invention is not limited by this formulation example.
- Formulation Example 1 Liquid composition for hair color pretreatment polyoxyethylene (10) oleyl ether phosphate 2.0% by mass Acetylated sodium hyaluronate 0.01 Arginine 0.4 Hydrolyzed wheat protein 0.1 Ethylparaben 0.2 Methylparaben 0.1 Phenoxyethanol 0.1 Purified water balance (production method) Each component is stirred and mixed at room temperature, homogenized, and manufactured.
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Abstract
The present invention provides a composition for pretreatment for hair coloring, which is capable of improving the hair dyeing effect during hair coloring, while reducing damage to the hair. A composition for pretreatment for hair coloring of the present invention is characterized by containing a polyoxyethylene oleylether phosphate and an acetylated hyaluronic acid or a salt thereof and by having a pH of 7.5-10.
Description
本出願は、２０１１年９月１日付け出願の日本国特許出願２０１１－１９０６１７号の優先権を主張しており、ここに折り込まれるものである。
This application claims the priority of Japanese Patent Application No. 2011-190617 filed on September 1, 2011, and is incorporated herein.
本発明はヘアカラー前処理用組成物に関し、特にヘアカラー時の染毛効果が向上し、毛髪へのダメージを軽減できるヘアカラー前処理用組成物に関する。
The present invention relates to a hair color pretreatment composition, and more particularly to a hair color pretreatment composition that improves the hair dyeing effect during hair coloring and can reduce damage to the hair.
近年、消費者の意識の変化に伴い、毛髪を明るくしたいという要望が高まり、ヘアカラーの市場が拡大している。しかし、ヘアカラーを複数回使用することにより、毛髪へのダメージが懸念される場合がある。また、ダメージが大きい毛髪を染毛すると、ダメージがある部分がより染毛されてしまって色ムラが生じてしまったり、期待した色に染毛することができないという問題もあった。
In recent years, with the change in consumer awareness, the desire to lighten hair has increased and the hair color market has expanded. However, the hair color may be used multiple times to cause damage to the hair. In addition, when hair with great damage is dyed, there is a problem that the damaged portion is dyed more and color unevenness occurs, or the hair cannot be dyed to the expected color.
そこで、毛髪ダメージが大きな消費者であっても、優れた染毛効果を実現するために、ヘアカラーを使用する前に、毛髪を前処理用組成物で処理することが提案されている。
前処理用組成物としては、タンパク質加水分解物を含む染毛用前処理剤が知られている（例えば特許文献１参照）。タンパク質加水分解物により、毛髪のダメージ部分を保護・補修することにより、染毛効果の向上が期待できる。しかしながら、その効果には改善の余地があった。 Therefore, it has been proposed to treat hair with a pretreatment composition before using a hair color in order to achieve an excellent hair dyeing effect, even for consumers with significant hair damage.
As a pretreatment composition, a pretreatment agent for hair dye containing a protein hydrolyzate is known (for example, see Patent Document 1). By protecting and repairing damaged parts of the hair with protein hydrolyzate, an improvement in the hair dyeing effect can be expected. However, there was room for improvement in the effect.
前処理用組成物としては、タンパク質加水分解物を含む染毛用前処理剤が知られている（例えば特許文献１参照）。タンパク質加水分解物により、毛髪のダメージ部分を保護・補修することにより、染毛効果の向上が期待できる。しかしながら、その効果には改善の余地があった。 Therefore, it has been proposed to treat hair with a pretreatment composition before using a hair color in order to achieve an excellent hair dyeing effect, even for consumers with significant hair damage.
As a pretreatment composition, a pretreatment agent for hair dye containing a protein hydrolyzate is known (for example, see Patent Document 1). By protecting and repairing damaged parts of the hair with protein hydrolyzate, an improvement in the hair dyeing effect can be expected. However, there was room for improvement in the effect.
本発明は前記従来技術の課題に鑑み行われたものであり、ヘアカラー時の染毛効果が向上し、毛髪へのダメージを軽減できるヘアカラー前処理用組成物を提供することを目的とする。
The present invention has been made in view of the above-described problems of the prior art, and an object of the present invention is to provide a hair color pretreatment composition capable of improving the hair dyeing effect during hair coloring and reducing damage to the hair. .
本発明者らが前述の問題を解決すべく鋭意研究を行った結果、ポリオキシエチレンオレイルエーテルリン酸とアセチル化ヒアルロン酸又はその塩類をヘアカラー前処理用組成物に配合し、特定のｐＨに調整することにより、ヘアカラー時の染毛効果が向上し、毛髪へのダメージを軽減できることを見出し、本発明を完成するに至った。
As a result of intensive studies to solve the above-mentioned problems, the present inventors formulated polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof into a hair color pretreatment composition to obtain a specific pH. By adjusting, it discovered that the hair dyeing effect at the time of hair coloring was improved and the damage to hair could be reduced, and came to complete this invention.
すなわち、本発明にかかるヘアカラー前処理用組成物は、ポリオキシエチレンオレイルエーテルリン酸と、アセチル化ヒアルロン酸又はその塩類と、を含み、ｐＨが７．５～１０であることを特徴とする。
前記組成物において、ポリオキシエチレンオレイルエーテルリン酸が、下記式（Ｉ）で示されることが好適である。
（式中、ｎはオキシエチレン基の平均付加モル数である。）
前記組成物において、アセチル化ヒアルロン酸又はその塩類が、下記式（ＩＩ）で示される繰り返し構造単位を有することが好適である。
（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は、それぞれ独立に水素原子、又はエステル結合されたアセチル基を示す（ただし、平均して各繰り返し構造単位においてＲ1、Ｒ2、Ｒ3、Ｒ4の少なくとも２個以上がアセチル基を示す）。Ｒ5は水素原子又はアルカリ金属を示す。ｋは２以上の数を示す。）
前記組成物において、ポリオキシエチレンオレイルエーテルリン酸を０．５～１０質量％、アセチル化ヒアルロン酸又はその塩類を０．０００１～１０質量％含むことが好適である。
前記組成物において、式（Ｉ）で示されるｎが１～２０であることが好適である。 That is, the hair color pretreatment composition according to the present invention comprises polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof, and has a pH of 7.5 to 10. .
In the composition, the polyoxyethylene oleyl ether phosphate is preferably represented by the following formula (I).
(In the formula, n is the average number of added moles of oxyethylene groups.)
In the composition, it is preferable that the acetylated hyaluronic acid or a salt thereof has a repeating structural unit represented by the following formula (II).
(In the formula, R 1 , R 2 , R 3 and R 4 each independently represents a hydrogen atom or an ester-linked acetyl group (however, R 1 , R 2 , R in each repeating structural unit on average) 3 and at least two of R 4 represent an acetyl group), R 5 represents a hydrogen atom or an alkali metal, and k represents a number of 2 or more.)
The composition preferably contains 0.5 to 10% by mass of polyoxyethylene oleyl ether phosphoric acid and 0.0001 to 10% by mass of acetylated hyaluronic acid or a salt thereof.
In the composition, n represented by the formula (I) is preferably 1-20.
前記組成物において、ポリオキシエチレンオレイルエーテルリン酸が、下記式（Ｉ）で示されることが好適である。
前記組成物において、アセチル化ヒアルロン酸又はその塩類が、下記式（ＩＩ）で示される繰り返し構造単位を有することが好適である。
前記組成物において、ポリオキシエチレンオレイルエーテルリン酸を０．５～１０質量％、アセチル化ヒアルロン酸又はその塩類を０．０００１～１０質量％含むことが好適である。
前記組成物において、式（Ｉ）で示されるｎが１～２０であることが好適である。 That is, the hair color pretreatment composition according to the present invention comprises polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof, and has a pH of 7.5 to 10. .
In the composition, the polyoxyethylene oleyl ether phosphate is preferably represented by the following formula (I).
In the composition, it is preferable that the acetylated hyaluronic acid or a salt thereof has a repeating structural unit represented by the following formula (II).
The composition preferably contains 0.5 to 10% by mass of polyoxyethylene oleyl ether phosphoric acid and 0.0001 to 10% by mass of acetylated hyaluronic acid or a salt thereof.
In the composition, n represented by the formula (I) is preferably 1-20.
本発明にかかるヘアカラー前処理用組成物は、ポリオキシエチレンオレイルエーテルリン酸と、アセチル化ヒアルロン酸又はその塩類と、を含み、ｐＨが７．５～１０である組成物であり、ヘアカラー時の染毛効果が向上し、毛髪へのダメージを軽減できるヘアカラー前処理用組成物を提供することができる。
The hair color pretreatment composition according to the present invention is a composition comprising polyoxyethylene oleyl ether phosphoric acid and acetylated hyaluronic acid or salts thereof and having a pH of 7.5 to 10, and hair color It is possible to provide a hair color pretreatment composition that improves the hair dyeing effect at the time and can reduce damage to the hair.
本発明にかかるヘアカラー前処理用組成物は、ポリオキシエチレンオレイルエーテルリン酸およびアセチル化ヒアルロン酸又はその塩類を含む。
以下、各成分について詳述する。 The hair color pretreatment composition according to the present invention contains polyoxyethylene oleyl ether phosphate and acetylated hyaluronic acid or salts thereof.
Hereinafter, each component will be described in detail.
以下、各成分について詳述する。 The hair color pretreatment composition according to the present invention contains polyoxyethylene oleyl ether phosphate and acetylated hyaluronic acid or salts thereof.
Hereinafter, each component will be described in detail.
（ポリオキシエチレンオレイルエーテルリン酸）
ポリオキシエチレンオレイルエーテルリン酸は、下記式（Ｉ）で示される化合物であることが好ましい。 (Polyoxyethylene oleyl ether phosphate)
The polyoxyethylene oleyl ether phosphoric acid is preferably a compound represented by the following formula (I).
ポリオキシエチレンオレイルエーテルリン酸は、下記式（Ｉ）で示される化合物であることが好ましい。 (Polyoxyethylene oleyl ether phosphate)
The polyoxyethylene oleyl ether phosphoric acid is preferably a compound represented by the following formula (I).
式（Ｉ）中、ｎはオキシエチレン基の平均付加モル数である。
ｎは特に限定されないが、１～２０であることが好ましく、３～１０であることが特に好ましい。 In formula (I), n is the average number of added moles of oxyethylene groups.
n is not particularly limited, but is preferably 1 to 20, and more preferably 3 to 10.
ｎは特に限定されないが、１～２０であることが好ましく、３～１０であることが特に好ましい。 In formula (I), n is the average number of added moles of oxyethylene groups.
n is not particularly limited, but is preferably 1 to 20, and more preferably 3 to 10.
本発明にかかるヘアカラー前処理用組成物において、ポリオキシエチレンオレイルエーテルリン酸の配合量は、０．５～１０質量％であることが好ましい。配合量は１質量％以上であることがより好ましい。配合量が少なすぎると、染毛効果に劣る場合がある。また、ポリオキシエチレンオレイルエーテルリン酸の配合量は、５質量％以下であることがより好ましい。配合量が多すぎても、効果の顕著な向上が見られない場合がある。
In the hair color pretreatment composition according to the present invention, the blending amount of polyoxyethylene oleyl ether phosphoric acid is preferably 0.5 to 10% by mass. The blending amount is more preferably 1% by mass or more. When there are too few compounding quantities, it may be inferior to the hair dyeing effect. Further, the blending amount of polyoxyethylene oleyl ether phosphoric acid is more preferably 5% by mass or less. Even if there are too many compounding quantities, the remarkable improvement of an effect may not be seen.
（アセチル化ヒアルロン酸又はその塩類）
アセチル化ヒアルロン酸又はその塩類は、ヒアルロン酸の水酸基を部分的にアセチル化した高分子化合物である。このアセチル化ヒアルロン酸は保湿効果を有する水溶性高分子で、長期的に塗布することでフケ・カユミ防止効果を有することが知られている。 (Acetylated hyaluronic acid or its salts)
An acetylated hyaluronic acid or a salt thereof is a polymer compound in which the hydroxyl group of hyaluronic acid is partially acetylated. This acetylated hyaluronic acid is a water-soluble polymer having a moisturizing effect, and is known to have an anti-dandruff and damaging effect when applied for a long time.
アセチル化ヒアルロン酸又はその塩類は、ヒアルロン酸の水酸基を部分的にアセチル化した高分子化合物である。このアセチル化ヒアルロン酸は保湿効果を有する水溶性高分子で、長期的に塗布することでフケ・カユミ防止効果を有することが知られている。 (Acetylated hyaluronic acid or its salts)
An acetylated hyaluronic acid or a salt thereof is a polymer compound in which the hydroxyl group of hyaluronic acid is partially acetylated. This acetylated hyaluronic acid is a water-soluble polymer having a moisturizing effect, and is known to have an anti-dandruff and damaging effect when applied for a long time.
本発明において、アセチル化ヒアルロン酸又はその塩類の水酸基に対するアセチル化率は特に限定されるものでないが、下記式（ＩＩ）で示される繰り返し構造単位を有するものを好適に用いることができる。
In the present invention, the acetylation rate with respect to the hydroxyl group of acetylated hyaluronic acid or a salt thereof is not particularly limited, but those having a repeating structural unit represented by the following formula (II) can be preferably used.
式（ＩＩ）中、Ｒ1、Ｒ2、Ｒ3、Ｒ4は、それぞれ独立に水素原子、又はエステル結合されたアセチル基を示す（ただし、平均して各繰り返し構造単位においてＲ1、Ｒ2、Ｒ3、Ｒ4の少なくとも２個以上がアセチル基を示す）。Ｒ5は水素原子又はアルカリ金属を示す。ｋは２以上の数を示す。
In the formula (II), R 1 , R 2 , R 3 , and R 4 each independently represent a hydrogen atom or an ester-linked acetyl group (however, R 1 , R 2 in each repeating structural unit on average) , R 3 and R 4 each represents an acetyl group). R 5 represents a hydrogen atom or an alkali metal. k represents a number of 2 or more.
上記式（ＩＩ）において、Ｒ1～Ｒ4のうちの１つがアセチル基である場合をアセチル化度１とすると、本発明ではアセチル化度が２～４のアセチル化ヒアルロン酸が好ましく用いられる。
また、本発明に用いられるアセチル化ヒアルロン酸の分子量は、ヒアルロン酸換算で１万～１００万程度が好ましい。 In the above formula (II), assuming that one of R 1 to R 4 is an acetyl group, the degree of acetylation is 1, and in the present invention, acetylated hyaluronic acid having a degree of acetylation of 2 to 4 is preferably used.
The molecular weight of the acetylated hyaluronic acid used in the present invention is preferably about 10,000 to 1,000,000 in terms of hyaluronic acid.
また、本発明に用いられるアセチル化ヒアルロン酸の分子量は、ヒアルロン酸換算で１万～１００万程度が好ましい。 In the above formula (II), assuming that one of R 1 to R 4 is an acetyl group, the degree of acetylation is 1, and in the present invention, acetylated hyaluronic acid having a degree of acetylation of 2 to 4 is preferably used.
The molecular weight of the acetylated hyaluronic acid used in the present invention is preferably about 10,000 to 1,000,000 in terms of hyaluronic acid.
本発明に用いられるアセチル化ヒアルロン酸又はその塩類の製造方法は、例えば、粉末状のヒアルロン酸を酢酸に分散し、触媒として無水トリフルオロ酢酸を加えて反応させる方法、ヒアルロン酸を酢酸に分散し、ｐ－トルエンスルホン酸を加えてさらに無水酢酸を加えて反応させる方法、ヒアルロン酸を無水酢酸溶媒に懸濁させた後、濃硫酸を加えて反応させる方法等が知られており（特開平６－９７０７号公報、特開平８－５３５０１号公報等）、これらの方法により製造することができるが、上記例示の方法に限定されるものでない。
The method for producing acetylated hyaluronic acid or salts thereof used in the present invention is, for example, a method in which powdered hyaluronic acid is dispersed in acetic acid and trifluoroacetic anhydride is added as a catalyst to react, and hyaluronic acid is dispersed in acetic acid. Further, there are known a method in which p-toluenesulfonic acid is added and acetic anhydride is further added to react, and a method in which hyaluronic acid is suspended in an acetic anhydride solvent and then concentrated sulfuric acid is added to react (Japanese Patent Laid-open No. Hei 6). -9707, JP-A-8-53501, etc.), these methods can be used, but the method is not limited to the above-mentioned methods.
本発明にかかるヘアカラー前処理用組成物において、アセチル化ヒアルロン酸又はその塩類の配合量は、０．０００１～１０質量％であることが好ましい。配合量は、０．００１質量％以上であることがより好ましく、０．１質量％以上であることが特に好ましい。配合量が少なすぎると、染毛効果に劣ったり、毛髪へのダメージが軽減できない場合がある。また、アセチル化ヒアルロン酸又はその塩類の配合量は、５質量％以下であることがより好ましく、１質量％以下であることが特に好ましい。配合量が多すぎると、粘性が上がりすぎる場合がある。
In the hair color pretreatment composition according to the present invention, the amount of acetylated hyaluronic acid or a salt thereof is preferably 0.0001 to 10% by mass. The blending amount is more preferably 0.001% by mass or more, and particularly preferably 0.1% by mass or more. If the amount is too small, the hair dyeing effect may be inferior, or damage to the hair may not be reduced. Further, the blending amount of acetylated hyaluronic acid or a salt thereof is more preferably 5% by mass or less, and particularly preferably 1% by mass or less. If the amount is too large, the viscosity may increase too much.
本発明のヘアカラー前処理用組成物は、ｐＨを７．５～１０に調整することが必要である。ｐＨが７．５未満であると、染毛効果に劣る。ｐＨが１０を超えても、効果の顕著な向上が見られないため、好ましくない。
The hair color pretreatment composition of the present invention needs to be adjusted to pH 7.5 to 10. If the pH is less than 7.5, the hair dyeing effect is poor. Even if pH exceeds 10, since the remarkable improvement of an effect is not seen, it is unpreferable.
本発明において、ｐＨの調整は、１種又は２種以上のｐＨ調整剤を用いて行うことができる。
ｐＨ調整剤としては、例えば、リン酸、硫酸、塩酸、炭酸などの無機酸やアミノ酸、クエン酸、グリコール酸、酒石酸などの有機酸のアルカリ金属塩類、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、アミノメチルプロパノールなどの有機アルカリ塩類等が挙げられる。 In the present invention, the pH can be adjusted by using one or more pH adjusting agents.
Examples of pH adjusters include inorganic acids such as phosphoric acid, sulfuric acid, hydrochloric acid, and carbonic acid, alkali metal salts of organic acids such as citric acid, glycolic acid, and tartaric acid, ammonia, monoethanolamine, diethanolamine, and triethanolamine. And organic alkali salts such as aminomethylpropanol.
ｐＨ調整剤としては、例えば、リン酸、硫酸、塩酸、炭酸などの無機酸やアミノ酸、クエン酸、グリコール酸、酒石酸などの有機酸のアルカリ金属塩類、アンモニア、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、アミノメチルプロパノールなどの有機アルカリ塩類等が挙げられる。 In the present invention, the pH can be adjusted by using one or more pH adjusting agents.
Examples of pH adjusters include inorganic acids such as phosphoric acid, sulfuric acid, hydrochloric acid, and carbonic acid, alkali metal salts of organic acids such as citric acid, glycolic acid, and tartaric acid, ammonia, monoethanolamine, diethanolamine, and triethanolamine. And organic alkali salts such as aminomethylpropanol.
本発明のヘアカラー前処理用組成物には、本発明の効果を損なわない範囲で、水、タンパク質加水分解物、界面活性剤、グリセリン、プロピレングリコール、ソルビトールなどの保湿剤、カルボキシメチルセルロース、ヒドロキシエチルセルロース、キサンタンガムなどの粘度調整剤、低級アルコール、防腐剤等の任意成分を適宜配合することができる。
In the hair color pretreatment composition of the present invention, water, protein hydrolyzate, surfactant, humectant such as glycerin, propylene glycol, sorbitol, carboxymethylcellulose, hydroxyethylcellulose as long as the effects of the present invention are not impaired. , Optional components such as viscosity modifiers such as xanthan gum, lower alcohols, preservatives, and the like can be appropriately blended.
本発明のヘアカラー前処理用組成物は、酸化染毛剤型のヘアカラーの前処理に用いることが好ましい。
また、本発明のヘアカラー前処理用組成物は、ヘアカラー前に毛髪に塗布し、手、クシ等によって、毛髪に均一に塗布した後、そのまま又は軽くすすいだ後、任意のヘアカラーを用いることができる。本発明のヘアカラー前処理用組成物は、塗布後、そのまま任意のヘアカラーを用いることが好ましい。 The hair color pretreatment composition of the present invention is preferably used for pretreatment of an oxidative hair dye type hair color.
In addition, the hair color pretreatment composition of the present invention is applied to the hair before the hair color, and is applied to the hair uniformly by hand, comb, etc., and then rinsed as it is or after being lightly rinsed, then any hair color is used. be able to. The hair color pretreatment composition of the present invention preferably uses any hair color as it is after coating.
また、本発明のヘアカラー前処理用組成物は、ヘアカラー前に毛髪に塗布し、手、クシ等によって、毛髪に均一に塗布した後、そのまま又は軽くすすいだ後、任意のヘアカラーを用いることができる。本発明のヘアカラー前処理用組成物は、塗布後、そのまま任意のヘアカラーを用いることが好ましい。 The hair color pretreatment composition of the present invention is preferably used for pretreatment of an oxidative hair dye type hair color.
In addition, the hair color pretreatment composition of the present invention is applied to the hair before the hair color, and is applied to the hair uniformly by hand, comb, etc., and then rinsed as it is or after being lightly rinsed, then any hair color is used. be able to. The hair color pretreatment composition of the present invention preferably uses any hair color as it is after coating.
本発明について、以下に実施例を挙げてさらに詳述するが、本発明はこれにより何ら限定されるものではない。配合量は特記しない限り、その成分が配合される系に対する質量％で示す。
実施例の説明に先立ち本発明で用いた試験の評価方法について説明する。 The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Unless otherwise specified, the blending amount is expressed in mass% with respect to the system in which the component is blended.
Prior to the description of the examples, the evaluation method of the test used in the present invention will be described.
実施例の説明に先立ち本発明で用いた試験の評価方法について説明する。 The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto. Unless otherwise specified, the blending amount is expressed in mass% with respect to the system in which the component is blended.
Prior to the description of the examples, the evaluation method of the test used in the present invention will be described.
評価（１）：色差
処理前後の毛髪（乾燥状態）の色差を、色差計ＣＭ－３６００（ミノルタ社製）を用いて測定を行った。 Evaluation (1): Color difference The color difference of the hair before and after the treatment (dry state) was measured using a color difference meter CM-3600 (manufactured by Minolta).
処理前後の毛髪（乾燥状態）の色差を、色差計ＣＭ－３６００（ミノルタ社製）を用いて測定を行った。 Evaluation (1): Color difference The color difference of the hair before and after the treatment (dry state) was measured using a color difference meter CM-3600 (manufactured by Minolta).
評価（２）：水分保持率
染色した毛束を８０％ＲＨ下で１２時間放置した後、重量（Ｗ１）をカールフィッシャー水分計（三菱化学社製）で測定した。そして、同じ毛束を２時間減圧乾燥した後、重量（Ｗ２）を同様に測定した。これらの測定値を用い、下記式より水分保持率を算出した。
水分保持率（％）＝（Ｗ１－Ｗ２）×１００／Ｗ１ Evaluation (2): Water retention rate The dyed hair bundle was allowed to stand under 80% RH for 12 hours, and then the weight (W1) was measured with a Karl Fischer moisture meter (manufactured by Mitsubishi Chemical Corporation). And after drying the same hair | bristle for 2 hours under reduced pressure, the weight (W2) was measured similarly. Using these measured values, the water retention rate was calculated from the following formula.
Moisture retention (%) = (W1-W2) × 100 / W1
染色した毛束を８０％ＲＨ下で１２時間放置した後、重量（Ｗ１）をカールフィッシャー水分計（三菱化学社製）で測定した。そして、同じ毛束を２時間減圧乾燥した後、重量（Ｗ２）を同様に測定した。これらの測定値を用い、下記式より水分保持率を算出した。
水分保持率（％）＝（Ｗ１－Ｗ２）×１００／Ｗ１ Evaluation (2): Water retention rate The dyed hair bundle was allowed to stand under 80% RH for 12 hours, and then the weight (W1) was measured with a Karl Fischer moisture meter (manufactured by Mitsubishi Chemical Corporation). And after drying the same hair | bristle for 2 hours under reduced pressure, the weight (W2) was measured similarly. Using these measured values, the water retention rate was calculated from the following formula.
Moisture retention (%) = (W1-W2) × 100 / W1
まず、本発明者らは、下記表１に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表２に示す配合組成で、ヘアカラー前処理用組成物を製造した。
そして、黒色毛束１ｇを水で濡らした後（試験例１－０）、もしくは、黒色毛束１ｇに試験例１－１～１－５の前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）で評価を行った。結果を表２に示す。
以下の試験例において、ヘアカラーはいずれも、使用直前に第１剤と第２剤を１：１で（各１．５ｇを）混合したものを使用した。
なお、表１記載のヘアカラーのｐＨ（第１剤および第２剤混合時）は１０であった。 First, the present inventors manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 below, and manufactured a hair color pretreatment composition with the composition shown in Table 2 below. did.
Then, after wetting 1 g of the black hair bundle with water (Test Example 1-0), or after applying 0.3 g of the pretreatment composition of Test Examples 1-1 to 1-5 to 1 g of the black hair bundle, The hair color was applied by applying 3 g of hair color and allowed to stand for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 2.
In the following test examples, the hair color used was a mixture of the first agent and the second agent in a ratio of 1: 1 (each 1.5 g) immediately before use.
The pH of the hair color described in Table 1 was 10 (when the first agent and the second agent were mixed).
そして、黒色毛束１ｇを水で濡らした後（試験例１－０）、もしくは、黒色毛束１ｇに試験例１－１～１－５の前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）で評価を行った。結果を表２に示す。
以下の試験例において、ヘアカラーはいずれも、使用直前に第１剤と第２剤を１：１で（各１．５ｇを）混合したものを使用した。
なお、表１記載のヘアカラーのｐＨ（第１剤および第２剤混合時）は１０であった。 First, the present inventors manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 below, and manufactured a hair color pretreatment composition with the composition shown in Table 2 below. did.
Then, after wetting 1 g of the black hair bundle with water (Test Example 1-0), or after applying 0.3 g of the pretreatment composition of Test Examples 1-1 to 1-5 to 1 g of the black hair bundle, The hair color was applied by applying 3 g of hair color and allowed to stand for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 2.
In the following test examples, the hair color used was a mixture of the first agent and the second agent in a ratio of 1: 1 (each 1.5 g) immediately before use.
The pH of the hair color described in Table 1 was 10 (when the first agent and the second agent were mixed).
（表１）
・第１剤
セトステアリルアルコール ７．０ 質量％
ポリオキシエチレンセチルエーテル ３．０
塩化ステアリルトリメチルアンモニウム １．５
パラフィン ２．０
無水亜硫酸ナトリウム ０．２
パラフェニレンジアミン ０．３
レゾルシン ０．３
メタアミノフェノール ０．００５
５－アミノオルトクレゾール ０．００５
アンモニア ５．０
ｐＨ調整剤 適 量
精製水 残 量
・第２剤
３５％過酸化水素水 １６．５ 質量％
セトステアリルアルコール ３．０
ポリオキシエチレンセチルエーテル ２．０
エデト酸四ナトリウム ０．０２
精製水 残 量 (Table 1)
-1st agent cetostearyl alcohol 7.0 mass%
Polyoxyethylene cetyl ether 3.0
Stearyltrimethylammonium chloride 1.5
Paraffin 2.0
Anhydrous sodium sulfite 0.2
Paraphenylenediamine 0.3
Resorcin 0.3
Metaaminophenol 0.005
5-aminoorthocresol 0.005
Ammonia 5.0
pH adjuster Appropriate amount of purified water Residual amount, second agent 35% hydrogen peroxide solution 16.5% by mass
Cetostearyl alcohol 3.0
Polyoxyethylene cetyl ether 2.0
Edetate tetrasodium 0.02
Purified water balance
・第１剤
セトステアリルアルコール ７．０ 質量％
ポリオキシエチレンセチルエーテル ３．０
塩化ステアリルトリメチルアンモニウム １．５
パラフィン ２．０
無水亜硫酸ナトリウム ０．２
パラフェニレンジアミン ０．３
レゾルシン ０．３
メタアミノフェノール ０．００５
５－アミノオルトクレゾール ０．００５
アンモニア ５．０
ｐＨ調整剤 適 量
精製水 残 量
・第２剤
３５％過酸化水素水 １６．５ 質量％
セトステアリルアルコール ３．０
ポリオキシエチレンセチルエーテル ２．０
エデト酸四ナトリウム ０．０２
精製水 残 量 (Table 1)
-1st agent cetostearyl alcohol 7.0 mass%
Polyoxyethylene cetyl ether 3.0
Stearyltrimethylammonium chloride 1.5
Paraffin 2.0
Anhydrous sodium sulfite 0.2
Paraphenylenediamine 0.3
Resorcin 0.3
Metaaminophenol 0.005
5-aminoorthocresol 0.005
Ammonia 5.0
pH adjuster Appropriate amount of purified water Residual amount, second agent 35% hydrogen peroxide solution 16.5% by mass
Cetostearyl alcohol 3.0
Polyoxyethylene cetyl ether 2.0
Edetate tetrasodium 0.02
Purified water balance
表２によると、ヘアカラー前処理用組成物にポリオキシエチレン（１０）オレイルエーテルリン酸を含むと、色差が大きくなり、染毛効果が向上することがわかった。
また、ポリオキシエチレン（１０）オレイルエーテルリン酸を多く配合した試験例１－５の試料は、その配合量が少ない試験例１－１～１－４の試料よりも色差が小さいことがわかった。 According to Table 2, when polyoxyethylene (10) oleyl ether phosphoric acid was contained in the hair color pretreatment composition, it was found that the color difference was increased and the hair dyeing effect was improved.
Further, it was found that the sample of Test Example 1-5 containing a large amount of polyoxyethylene (10) oleyl ether phosphoric acid had a smaller color difference than the samples of Test Examples 1-1 to 1-4 having a small amount of the compound. .
また、ポリオキシエチレン（１０）オレイルエーテルリン酸を多く配合した試験例１－５の試料は、その配合量が少ない試験例１－１～１－４の試料よりも色差が小さいことがわかった。 According to Table 2, when polyoxyethylene (10) oleyl ether phosphoric acid was contained in the hair color pretreatment composition, it was found that the color difference was increased and the hair dyeing effect was improved.
Further, it was found that the sample of Test Example 1-5 containing a large amount of polyoxyethylene (10) oleyl ether phosphoric acid had a smaller color difference than the samples of Test Examples 1-1 to 1-4 having a small amount of the compound. .
次に、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨを変化させたヘアカラー前処理用組成物を用いて、ヘアカラー時の染毛効果について検討を行った。
本発明者らは、上記表１に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表３に示す配合組成で、ヘアカラー前処理用組成物を製造した。そして、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）で評価を行った。結果を表３に示す。 Next, the hair dyeing effect at the time of hair coloring was examined using a hair color pretreatment composition containing polyoxyethylene oleyl ether phosphoric acid and having a changed pH.
The inventors of the present invention manufactured an oxidative hair dye type hair color by the conventional method with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 3 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 3.
本発明者らは、上記表１に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表３に示す配合組成で、ヘアカラー前処理用組成物を製造した。そして、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）で評価を行った。結果を表３に示す。 Next, the hair dyeing effect at the time of hair coloring was examined using a hair color pretreatment composition containing polyoxyethylene oleyl ether phosphoric acid and having a changed pH.
The inventors of the present invention manufactured an oxidative hair dye type hair color by the conventional method with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 3 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1). The results are shown in Table 3.
表３によると、ポリオキシエチレン（１０）オレイルエーテルリン酸を含む前処理用組成物のｐＨを上げるにつれて、色差が大きくなることがわかった。特にｐＨが７．５以上の場合に、顕著な染毛効果が認められた。
試験例２－４と２－８を比較すると、同じｐＨでは、ポリオキシエチレン（１０）オレイルエーテルリン酸の配合量が多い方が、若干染毛効果が高いことがわかった。
また、前処理用組成物にポリオキシエチレン（３）オレイルエーテルリン酸を含み、ｐＨを８に調整した試験例２－９の試料も、色差が大きいことがわかった。
一方、試験例２－１０および２－１１によると、ポリオキシエチレンオレイルエーテルリン酸を含まず、ｐＨの高い水溶液を前処理用組成物として塗布しても、顕著な色差の向上は見られなかった。
以上のことから、本発明のヘアカラー前処理用組成物は、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨが７．５～１０であることが必要である。 According to Table 3, it was found that the color difference increases as the pH of the pretreatment composition containing polyoxyethylene (10) oleyl ether phosphate is increased. In particular, when the pH was 7.5 or more, a remarkable hair dyeing effect was observed.
A comparison of Test Examples 2-4 and 2-8 showed that the hair dyeing effect was slightly higher when the amount of polyoxyethylene (10) oleyl ether phosphate was larger at the same pH.
It was also found that the sample of Test Example 2-9 in which the pretreatment composition contained polyoxyethylene (3) oleyl ether phosphate and the pH was adjusted to 8 also had a large color difference.
On the other hand, according to Test Examples 2-10 and 2-11, even when an aqueous solution containing no polyoxyethylene oleyl ether phosphoric acid and having a high pH was applied as a pretreatment composition, no significant difference in color difference was observed. It was.
From the above, the hair color pretreatment composition of the present invention needs to contain polyoxyethylene oleyl ether phosphate and have a pH of 7.5 to 10.
試験例２－４と２－８を比較すると、同じｐＨでは、ポリオキシエチレン（１０）オレイルエーテルリン酸の配合量が多い方が、若干染毛効果が高いことがわかった。
また、前処理用組成物にポリオキシエチレン（３）オレイルエーテルリン酸を含み、ｐＨを８に調整した試験例２－９の試料も、色差が大きいことがわかった。
一方、試験例２－１０および２－１１によると、ポリオキシエチレンオレイルエーテルリン酸を含まず、ｐＨの高い水溶液を前処理用組成物として塗布しても、顕著な色差の向上は見られなかった。
以上のことから、本発明のヘアカラー前処理用組成物は、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨが７．５～１０であることが必要である。 According to Table 3, it was found that the color difference increases as the pH of the pretreatment composition containing polyoxyethylene (10) oleyl ether phosphate is increased. In particular, when the pH was 7.5 or more, a remarkable hair dyeing effect was observed.
A comparison of Test Examples 2-4 and 2-8 showed that the hair dyeing effect was slightly higher when the amount of polyoxyethylene (10) oleyl ether phosphate was larger at the same pH.
It was also found that the sample of Test Example 2-9 in which the pretreatment composition contained polyoxyethylene (3) oleyl ether phosphate and the pH was adjusted to 8 also had a large color difference.
On the other hand, according to Test Examples 2-10 and 2-11, even when an aqueous solution containing no polyoxyethylene oleyl ether phosphoric acid and having a high pH was applied as a pretreatment composition, no significant difference in color difference was observed. It was.
From the above, the hair color pretreatment composition of the present invention needs to contain polyoxyethylene oleyl ether phosphate and have a pH of 7.5 to 10.
次に、さらなる成分の配合について検討を行った。
本発明者らは、上記表１に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表４に示す配合組成で、ヘアカラー前処理用組成物を製造した。そして、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）および（２）で評価を行った。結果を表４に示す。 Next, further blending of ingredients was examined.
The inventors of the present invention manufactured an oxidative hair dye type hair color with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 4 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1) and (2). The results are shown in Table 4.
本発明者らは、上記表１に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表４に示す配合組成で、ヘアカラー前処理用組成物を製造した。そして、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置することで染毛した。そして、上記評価方法（１）および（２）で評価を行った。結果を表４に示す。 Next, further blending of ingredients was examined.
The inventors of the present invention manufactured an oxidative hair dye type hair color with the formulation shown in Table 1 above, and manufactured a hair color pretreatment composition with the formulation shown in Table 4 below. Then, after applying 0.3 g of the pretreatment composition to 1 g of the black hair bundle, 3 g of the hair color was applied, and the hair was dyed by being left for 20 minutes. And it evaluated by the said evaluation method (1) and (2). The results are shown in Table 4.
表４によると、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨ８である試験例２－４の試料に、アセチル化ヒアルロン酸を加えると、色差がさらに大きくなることがわかった。また、水分保持率も上昇することから、毛髪へのダメージを軽減できることがわかった。
また、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨ８である試験例２－４の試料に、ヒアルロン酸ナトリウムを加えた場合（試験例３－４）も、色差が大きく、水分保持率も上昇した。しかし、アセチル化ヒアルロン酸を加えた場合に比べると、効果が小さかった。
したがって、本発明のヘアカラー前処理用組成物は、アセチル化ヒアルロン酸又はその塩類を含むことも必要である。 According to Table 4, it was found that when acetylated hyaluronic acid was added to the sample of Test Example 2-4 containing polyoxyethylene oleyl ether phosphate and having a pH of 8, the color difference was further increased. Moreover, since the moisture retention rate also rose, it turned out that the damage to hair can be reduced.
Further, when sodium hyaluronate was added to the sample of Test Example 2-4 containing polyoxyethylene oleyl ether phosphate and having a pH of 8 (Test Example 3-4), the color difference was large and the water retention rate was also increased. . However, the effect was small compared with the case where acetylated hyaluronic acid was added.
Therefore, the hair color pretreatment composition of the present invention also needs to contain acetylated hyaluronic acid or a salt thereof.
また、ポリオキシエチレンオレイルエーテルリン酸を含み、ｐＨ８である試験例２－４の試料に、ヒアルロン酸ナトリウムを加えた場合（試験例３－４）も、色差が大きく、水分保持率も上昇した。しかし、アセチル化ヒアルロン酸を加えた場合に比べると、効果が小さかった。
したがって、本発明のヘアカラー前処理用組成物は、アセチル化ヒアルロン酸又はその塩類を含むことも必要である。 According to Table 4, it was found that when acetylated hyaluronic acid was added to the sample of Test Example 2-4 containing polyoxyethylene oleyl ether phosphate and having a pH of 8, the color difference was further increased. Moreover, since the moisture retention rate also rose, it turned out that the damage to hair can be reduced.
Further, when sodium hyaluronate was added to the sample of Test Example 2-4 containing polyoxyethylene oleyl ether phosphate and having a pH of 8 (Test Example 3-4), the color difference was large and the water retention rate was also increased. . However, the effect was small compared with the case where acetylated hyaluronic acid was added.
Therefore, the hair color pretreatment composition of the present invention also needs to contain acetylated hyaluronic acid or a salt thereof.
次に、ヘアカラー前処理用組成物の使用方法による効果の相違について検討を行った。
本発明者らは、上記表４と同様、試験例３－２の前処理用組成物および表１のヘアカラーを用いて、常法および方法Ｘ（塗布の順番を変えた方法）にて、黒色毛束の処理を行った。そして、上記評価方法（１）で評価を行った。結果を表５に示す。
なお、常法とは、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置後に洗浄することで染毛処理を行う方法である。
また、方法Ｘとは、黒色毛束１ｇにヘアカラー３ｇを塗布した後、前処理用組成物０．３ｇを塗布し、２０分放置後に洗浄することで染毛処理を行う方法である。 Next, the difference in the effect by the usage method of the hair color pretreatment composition was examined.
In the same manner as in Table 4 above, the present inventors used the pretreatment composition of Test Example 3-2 and the hair color of Table 1 by the conventional method and Method X (method in which the order of application was changed), The black hair bundle was processed. And it evaluated by the said evaluation method (1). The results are shown in Table 5.
The normal method is a method of applying a hair dyeing treatment by applying 0.3 g of the pretreatment composition to 1 g of black hair bundle, then applying 3 g of hair color, and washing after standing for 20 minutes.
Method X is a method of applying hair coloring treatment by applying 3 g of hair color to 1 g of black hair bundle, applying 0.3 g of the pretreatment composition, and washing after standing for 20 minutes.
本発明者らは、上記表４と同様、試験例３－２の前処理用組成物および表１のヘアカラーを用いて、常法および方法Ｘ（塗布の順番を変えた方法）にて、黒色毛束の処理を行った。そして、上記評価方法（１）で評価を行った。結果を表５に示す。
なお、常法とは、黒色毛束１ｇに前処理用組成物０．３ｇを塗布した後、ヘアカラー３ｇを塗布し、２０分放置後に洗浄することで染毛処理を行う方法である。
また、方法Ｘとは、黒色毛束１ｇにヘアカラー３ｇを塗布した後、前処理用組成物０．３ｇを塗布し、２０分放置後に洗浄することで染毛処理を行う方法である。 Next, the difference in the effect by the usage method of the hair color pretreatment composition was examined.
In the same manner as in Table 4 above, the present inventors used the pretreatment composition of Test Example 3-2 and the hair color of Table 1 by the conventional method and Method X (method in which the order of application was changed), The black hair bundle was processed. And it evaluated by the said evaluation method (1). The results are shown in Table 5.
The normal method is a method of applying a hair dyeing treatment by applying 0.3 g of the pretreatment composition to 1 g of black hair bundle, then applying 3 g of hair color, and washing after standing for 20 minutes.
Method X is a method of applying hair coloring treatment by applying 3 g of hair color to 1 g of black hair bundle, applying 0.3 g of the pretreatment composition, and washing after standing for 20 minutes.
試験例３－２’によると、ヘアカラー塗布後に本発明の前処理用組成物を塗布しても、前処理しない場合（試験例３－０）と同じ色差であり、染毛効果の向上は認められなかった。
このことから、本発明のヘアカラー用前処理用組成物は、ヘアカラーの前に用いることが必要である。 According to Test Example 3-2 ′, even when the pretreatment composition of the present invention was applied after applying the hair color, the color difference was the same as in the case of no pretreatment (Test Example 3-0), and the hair dyeing effect was improved. I was not able to admit.
Therefore, it is necessary to use the hair color pretreatment composition of the present invention before hair color.
このことから、本発明のヘアカラー用前処理用組成物は、ヘアカラーの前に用いることが必要である。 According to Test Example 3-2 ′, even when the pretreatment composition of the present invention was applied after applying the hair color, the color difference was the same as in the case of no pretreatment (Test Example 3-0), and the hair dyeing effect was improved. I was not able to admit.
Therefore, it is necessary to use the hair color pretreatment composition of the present invention before hair color.
次に、本発明者らは、前処理用組成物の有効成分を、ヘアカラーに配合した場合の効果の相違について検討を行った。
本発明者らは、上記表１および下記表６に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表７に示す配合組成で、ヘアカラー前処理用組成物を製造した。なお、表６記載のヘアカラーのｐＨ（第１剤および第２剤混合時）は１０であった。
そして、上記の常法もしくは前処理なしで染毛処理した。そして、上記評価方法（１）で評価を行った。結果を表７に示す。 Next, the present inventors examined the difference in effect when the active ingredient of the pretreatment composition was blended into the hair color.
The inventors of the present invention manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 and Table 6 below, and the hair color pretreatment composition with the composition shown in Table 7 below. Manufactured. The pH of the hair color described in Table 6 was 10 (when the first agent and the second agent were mixed).
And the above-mentioned usual method or the hair dyeing process was carried out without pretreatment. And it evaluated by the said evaluation method (1). The results are shown in Table 7.
本発明者らは、上記表１および下記表６に示す配合組成で、常法により酸化染毛剤型のヘアカラーを製造し、下記表７に示す配合組成で、ヘアカラー前処理用組成物を製造した。なお、表６記載のヘアカラーのｐＨ（第１剤および第２剤混合時）は１０であった。
そして、上記の常法もしくは前処理なしで染毛処理した。そして、上記評価方法（１）で評価を行った。結果を表７に示す。 Next, the present inventors examined the difference in effect when the active ingredient of the pretreatment composition was blended into the hair color.
The inventors of the present invention manufactured hair dye-type hair color by a conventional method with the composition shown in Table 1 and Table 6 below, and the hair color pretreatment composition with the composition shown in Table 7 below. Manufactured. The pH of the hair color described in Table 6 was 10 (when the first agent and the second agent were mixed).
And the above-mentioned usual method or the hair dyeing process was carried out without pretreatment. And it evaluated by the said evaluation method (1). The results are shown in Table 7.
（表６）
・第１剤
ポリオキシエチレン（１０）オレイルエーテルリン酸 ０．３６ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１８
セトステアリルアルコール ７．０
ポリオキシエチレンセチルエーテル ３．０
塩化ステアリルトリメチルアンモニウム １．５
パラフィン ２．０
無水亜硫酸ナトリウム ０．２
パラフェニレンジアミン ０．３
レゾルシン ０．３
メタアミノフェノール ０．００５
５－アミノオルトクレゾール ０．００５
アンモニア ５．０
ｐＨ調整剤 適 量
精製水 残 量
・第２剤
３５％過酸化水素水 １６．５ 質量％
セトステアリルアルコール ３．０
ポリオキシエチレンセチルエーテル ２．０
エデト酸四ナトリウム ０．０２
精製水 残 量 (Table 6)
-1st agent polyoxyethylene (10) oleyl ether phosphoric acid 0.36 mass%
Acetylated sodium hyaluronate 0.018
Cetostearyl alcohol 7.0
Polyoxyethylene cetyl ether 3.0
Stearyltrimethylammonium chloride 1.5
Paraffin 2.0
Anhydrous sodium sulfite 0.2
Paraphenylenediamine 0.3
Resorcin 0.3
Metaaminophenol 0.005
5-aminoorthocresol 0.005
Ammonia 5.0
pH adjuster Appropriate amount of purified water Residual amount, second agent 35% hydrogen peroxide solution 16.5% by mass
Cetostearyl alcohol 3.0
Polyoxyethylene cetyl ether 2.0
Edetate tetrasodium 0.02
Purified water balance
・第１剤
ポリオキシエチレン（１０）オレイルエーテルリン酸 ０．３６ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１８
セトステアリルアルコール ７．０
ポリオキシエチレンセチルエーテル ３．０
塩化ステアリルトリメチルアンモニウム １．５
パラフィン ２．０
無水亜硫酸ナトリウム ０．２
パラフェニレンジアミン ０．３
レゾルシン ０．３
メタアミノフェノール ０．００５
５－アミノオルトクレゾール ０．００５
アンモニア ５．０
ｐＨ調整剤 適 量
精製水 残 量
・第２剤
３５％過酸化水素水 １６．５ 質量％
セトステアリルアルコール ３．０
ポリオキシエチレンセチルエーテル ２．０
エデト酸四ナトリウム ０．０２
精製水 残 量 (Table 6)
-1st agent polyoxyethylene (10) oleyl ether phosphoric acid 0.36 mass%
Acetylated sodium hyaluronate 0.018
Cetostearyl alcohol 7.0
Polyoxyethylene cetyl ether 3.0
Stearyltrimethylammonium chloride 1.5
Paraffin 2.0
Anhydrous sodium sulfite 0.2
Paraphenylenediamine 0.3
Resorcin 0.3
Metaaminophenol 0.005
5-aminoorthocresol 0.005
Ammonia 5.0
pH adjuster Appropriate amount of purified water Residual amount, second agent 35% hydrogen peroxide solution 16.5% by mass
Cetostearyl alcohol 3.0
Polyoxyethylene cetyl ether 2.0
Edetate tetrasodium 0.02
Purified water balance
試験例３－２との前処理用組成物と同量の有効成分を、ヘアカラーとして黒色毛束に塗布した試験例３－２’’は、有効成分の入っていないヘアカラーを塗布した試験例３－０と、それほど色差が変わらなかった。
このため、本発明の有効成分は、ヘアカラーに配合するのではなく、ヘアカラー前処理用組成物として、ヘアカラーの前に塗布することで、優れた染毛効果を発揮できることが明らかになった。 Test Example 3-2 ″, in which the same amount of the active ingredient as the pretreatment composition with Test Example 3-2 was applied as a hair color to a black hair bundle, is a test in which a hair color containing no active ingredient was applied The color difference was not so different from Example 3-0.
For this reason, it becomes clear that the active ingredient of the present invention can exhibit an excellent hair dyeing effect when applied before the hair color as a hair color pretreatment composition, rather than being blended into the hair color. It was.
このため、本発明の有効成分は、ヘアカラーに配合するのではなく、ヘアカラー前処理用組成物として、ヘアカラーの前に塗布することで、優れた染毛効果を発揮できることが明らかになった。 Test Example 3-2 ″, in which the same amount of the active ingredient as the pretreatment composition with Test Example 3-2 was applied as a hair color to a black hair bundle, is a test in which a hair color containing no active ingredient was applied The color difference was not so different from Example 3-0.
For this reason, it becomes clear that the active ingredient of the present invention can exhibit an excellent hair dyeing effect when applied before the hair color as a hair color pretreatment composition, rather than being blended into the hair color. It was.
以下に、本発明のヘアカラー前処理用組成物の処方例を挙げる。本発明はこの処方例によって限定されるものではない。
The following is a formulation example of the hair color pretreatment composition of the present invention. The present invention is not limited by this formulation example.
処方例１ ヘアカラー前処理用液状組成物
ポリオキシエチレン（１０）オレイルエーテルリン酸 ２．０ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１
アルギニン ０．４
加水分解コムギタンパク質 ０．１
エチルパラベン ０．２
メチルパラベン ０．１
フェノキシエタノール ０．１
精製水 残 量
（製造方法）
各成分を室温で攪拌混合し、均一化を行い、製造する。 Formulation Example 1 Liquid composition for hair color pretreatment polyoxyethylene (10) oleyl ether phosphate 2.0% by mass
Acetylated sodium hyaluronate 0.01
Arginine 0.4
Hydrolyzed wheat protein 0.1
Ethylparaben 0.2
Methylparaben 0.1
Phenoxyethanol 0.1
Purified water balance (production method)
Each component is stirred and mixed at room temperature, homogenized, and manufactured.
ポリオキシエチレン（１０）オレイルエーテルリン酸 ２．０ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１
アルギニン ０．４
加水分解コムギタンパク質 ０．１
エチルパラベン ０．２
メチルパラベン ０．１
フェノキシエタノール ０．１
精製水 残 量
（製造方法）
各成分を室温で攪拌混合し、均一化を行い、製造する。 Formulation Example 1 Liquid composition for hair color pretreatment polyoxyethylene (10) oleyl ether phosphate 2.0% by mass
Acetylated sodium hyaluronate 0.01
Arginine 0.4
Hydrolyzed wheat protein 0.1
Ethylparaben 0.2
Methylparaben 0.1
Phenoxyethanol 0.1
Purified water balance (production method)
Each component is stirred and mixed at room temperature, homogenized, and manufactured.
処方例２ ヘアカラー前処理用乳液状組成物
ポリオキシエチレン（１０）オレイルエーテルリン酸 ２．０ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１
アルギニン ０．４
加水分解コムギタンパク質 ０．１
ミネラルオイル １．０
ポリオキシエチレン硬化ヒマシ油 ０．５
エチルパラベン ０．２
メチルパラベン ０．１
フェノキシエタノール ０．１
カルボマー ０．０５
水酸化ナトリウム 適 量
精製水 残 量
（製造方法）
水溶性成分を水に溶解させ、油と界面活性剤を加えて、ホモミキサーで乳化処理を行い、乳液状組成物を製造する。 Formulation Example 2 Hair Color Pretreatment Milk Composition Polyoxyethylene (10) Oleyl Ether Phosphoric Acid 2.0% by mass
Acetylated sodium hyaluronate 0.01
Arginine 0.4
Hydrolyzed wheat protein 0.1
Mineral oil 1.0
Polyoxyethylene hydrogenated castor oil 0.5
Ethylparaben 0.2
Methylparaben 0.1
Phenoxyethanol 0.1
Carbomer 0.05
Sodium hydroxide Appropriate amount of purified water
A water-soluble component is dissolved in water, oil and a surfactant are added, and an emulsification treatment is performed with a homomixer to produce an emulsion composition.
ポリオキシエチレン（１０）オレイルエーテルリン酸 ２．０ 質量％
アセチル化ヒアルロン酸ナトリウム ０．０１
アルギニン ０．４
加水分解コムギタンパク質 ０．１
ミネラルオイル １．０
ポリオキシエチレン硬化ヒマシ油 ０．５
エチルパラベン ０．２
メチルパラベン ０．１
フェノキシエタノール ０．１
カルボマー ０．０５
水酸化ナトリウム 適 量
精製水 残 量
（製造方法）
水溶性成分を水に溶解させ、油と界面活性剤を加えて、ホモミキサーで乳化処理を行い、乳液状組成物を製造する。 Formulation Example 2 Hair Color Pretreatment Milk Composition Polyoxyethylene (10) Oleyl Ether Phosphoric Acid 2.0% by mass
Acetylated sodium hyaluronate 0.01
Arginine 0.4
Hydrolyzed wheat protein 0.1
Mineral oil 1.0
Polyoxyethylene hydrogenated castor oil 0.5
Ethylparaben 0.2
Methylparaben 0.1
Phenoxyethanol 0.1
Carbomer 0.05
Sodium hydroxide Appropriate amount of purified water
A water-soluble component is dissolved in water, oil and a surfactant are added, and an emulsification treatment is performed with a homomixer to produce an emulsion composition.
Claims (5)
- ポリオキシエチレンオレイルエーテルリン酸と、
アセチル化ヒアルロン酸又はその塩類と、を含み、
ｐＨが７．５～１０であることを特徴とするヘアカラー前処理用組成物。 Polyoxyethylene oleyl ether phosphate,
Acetylated hyaluronic acid or a salt thereof,
A hair color pretreatment composition having a pH of 7.5 to 10. - 請求項１に記載の組成物において、ポリオキシエチレンオレイルエーテルリン酸が、下記式（Ｉ）で示されることを特徴とするヘアカラー前処理用組成物。
- 請求項１又は２に記載の組成物において、アセチル化ヒアルロン酸又はその塩類が、下記式（ＩＩ）で示される繰り返し構造単位を有することを特徴とするヘアカラー前処理用組成物。
- 請求項１～３のいずれかに記載の組成物において、ポリオキシエチレンオレイルエーテルリン酸を０．５～１０質量％、アセチル化ヒアルロン酸又はその塩類を０．０００１～１０質量％含むことを特徴とするヘアカラー前処理用組成物。 The composition according to any one of claims 1 to 3, characterized in that it contains 0.5 to 10% by mass of polyoxyethylene oleyl ether phosphoric acid and 0.0001 to 10% by mass of acetylated hyaluronic acid or salts thereof. A hair color pretreatment composition.
- 請求項２～４のいずれかに記載の組成物において、式（Ｉ）で示されるｎが１～２０であることを特徴とするヘアカラー前処理用組成物。 5. A hair color pretreatment composition according to claim 2, wherein n represented by the formula (I) is 1 to 20.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011190617 | 2011-09-01 | ||
| JP2011-190617 | 2011-09-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2013031313A1 true WO2013031313A1 (en) | 2013-03-07 |
Family
ID=47755830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2012/063620 WO2013031313A1 (en) | 2011-09-01 | 2012-05-28 | Composition for pretreatment for hair coloring |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP5955646B2 (en) |
| WO (1) | WO2013031313A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107789218A (en) * | 2016-09-02 | 2018-03-13 | 株式会社美丽化妆品 | Contaminate hair composition and preparation method thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7033391B2 (en) * | 2016-03-08 | 2022-03-10 | クローダジャパン株式会社 | Hair dye for hair |
| JP6980438B2 (en) * | 2017-07-19 | 2021-12-15 | 株式会社サニープレイス | Hair color treatment method |
| JP7176712B2 (en) * | 2017-07-19 | 2022-11-22 | 株式会社サニープレイス | Hair cosmetic composition |
Citations (3)
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|---|---|---|---|---|
| JPH069707A (en) * | 1992-04-21 | 1994-01-18 | Shiseido Co Ltd | Highly acetylated hyaluronic acid and production thereof |
| JPH0853501A (en) * | 1994-08-11 | 1996-02-27 | Shiseido Co Ltd | Production and purification of acetylated hyaluronic acid |
| JP2010037283A (en) * | 2008-08-06 | 2010-02-18 | Asutaa Biyo:Kk | Hair cosmetic composition |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5874798A (en) * | 1981-10-28 | 1983-05-06 | 花王株式会社 | Shampoo composition |
| JPH03143540A (en) * | 1989-10-26 | 1991-06-19 | Agency Of Ind Science & Technol | New emulsification stabilizer |
| JPH1149649A (en) * | 1997-08-08 | 1999-02-23 | Shiseido Co Ltd | Hair washing agent |
| JPH11228360A (en) * | 1998-02-10 | 1999-08-24 | Shiseido Co Ltd | Hair treating agent composition |
| JP2004018420A (en) * | 2002-06-13 | 2004-01-22 | Mandom Corp | Hair pretreatment agent |
| US7833519B2 (en) * | 2004-09-24 | 2010-11-16 | The Procter & Gamble Company | Method of pre-treatment for hair colourants and bleaches |
| WO2006036747A2 (en) * | 2004-09-24 | 2006-04-06 | The Procter & Gamble Company | Methods of rapid hair dyeing |
| JP2006282512A (en) * | 2005-03-31 | 2006-10-19 | Nakano Seiyaku Kk | Pre-treating agent for hair color |
| JP4995441B2 (en) * | 2005-07-04 | 2012-08-08 | ホーユー株式会社 | Oxidative hair dye composition |
| JP3947756B2 (en) * | 2005-11-11 | 2007-07-25 | ホーユー株式会社 | Oxidative hair dye composition |
| WO2008133267A1 (en) * | 2007-04-24 | 2008-11-06 | Q.P. Corporation | Cationized hyaluronic acid and/or salt thereof, method for producing the same, and hair modifying agent, cuticle repairing agent, skin modifying agent and cosmetic preparation each using the same |
| JP2008290971A (en) * | 2007-05-24 | 2008-12-04 | Croda Japan Kk | Hair-treating composition |
| JP5632150B2 (en) * | 2009-11-10 | 2014-11-26 | 株式会社マンダム | Hair treatment agent |
-
2012
- 2012-05-28 JP JP2012120762A patent/JP5955646B2/en not_active Expired - Fee Related
- 2012-05-28 WO PCT/JP2012/063620 patent/WO2013031313A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH069707A (en) * | 1992-04-21 | 1994-01-18 | Shiseido Co Ltd | Highly acetylated hyaluronic acid and production thereof |
| JPH0853501A (en) * | 1994-08-11 | 1996-02-27 | Shiseido Co Ltd | Production and purification of acetylated hyaluronic acid |
| JP2010037283A (en) * | 2008-08-06 | 2010-02-18 | Asutaa Biyo:Kk | Hair cosmetic composition |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107789218A (en) * | 2016-09-02 | 2018-03-13 | 株式会社美丽化妆品 | Contaminate hair composition and preparation method thereof |
| CN107789218B (en) * | 2016-09-02 | 2020-12-01 | 株式会社美丽化妆品 | Hair dyeing composition and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013063948A (en) | 2013-04-11 |
| JP5955646B2 (en) | 2016-07-20 |
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