JP2001081013A - Sound hair agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a sound hair agent for preventing damaging of hair and curing damaged hair, having effects to recover beauty and health inherent to the hair and safe to human body by bringing the agent to contain an ammonium salt and a specific compound. SOLUTION: This sound hair agent contains an ammonium salt, its ion and one or more species of ingredients selected from compounds expressed by the formula [R1 to R3 are each H, OH, a (substituted) lower alkoxy or the like; R4 and R5 are each H, OH, an (OH or amino substituted) lower alkyl or aryl, carboxy or the like; R6 and R7 are each H, an (OH substituted) lower alkyl, a lower alkylcarbonyl, aryl, or aralky], (e.g. L-arginine, etc.), their ions and salts. Preferably, the compound of the formula is L-arginine and the agent further contains another compound expressed by the formula (e.g. ethanolamine, etc.), and a natural preparation (e.g. a rice preparation, etc.), in addition to L-arginine and the ammonium salt.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a hair restoring agent and a drug containing the same.

[0002]

2. Description of the Related Art Hair is absorbed from the outside by ultraviolet rays and other rays, air pollution, chemical substances, etc., and from inside the body, additives and pesticides are taken in from foods, changes in eating habits, mental stress, etc. In addition, due to the wrong brushing method or the treatment of shampoo, perm, hair color, or the like, it is easily damaged and tends to be damaged. Such hair has no gloss, firmness or firmness in appearance, and may have split ends or cut hairs.

[0003] In order to cope with such a hair trouble, a method of temporarily replenishing moisture or a method of coating with oil has conventionally been taken. Did not make him healthy.
In addition, when used for hair, they are easily adhered to the scalp when used, and therefore, those that have no irritation and no side effects and are highly safe are required. Therefore, there is a long-awaited need for materials that make hair fundamentally healthy and have proven safety.

[0004]

SUMMARY OF THE INVENTION Accordingly, the present invention provides a method for preventing damaged hair by improving the damaged hair and restoring beautiful and healthy hair by allowing the active ingredient to reach the core of the hair. Healing hair, natural beauty of hair,
An object of the present invention is to provide a hair cleansing agent that has an effect of restoring health and that is safe for the human body.

[0005]

DISCLOSURE OF THE INVENTION The present invention provides an ammonium salt and its ion and a compound represented by the formula (1):

Embedded image (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a carboxyl group, a guanidino group, or guanidino A lower alkyl group substituted with a group;
R ₄ and R ₅ each independently represent a hydrogen atom, a hydroxyl group, a lower alkyl group or an aryl group which may be substituted with a hydroxyl group or an amino group, or a carboxyl group;
Alternatively, R ₄ and R ₅ together form a carbonyl group with an adjacent carbon atom; R ₆ and R ₇ each independently represent a hydrogen atom or a lower alkyl group which may be substituted by a hydroxyl group. Or a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ may have a substituent that forms a 5-membered ring with an adjacent atom. Wherein the nitrogen atom in the formula may be quaternized with a lower alkyl group), their ions and their pharmaceutically acceptable salts. (1) a hair lightening agent containing one or more components.

Further, the present invention provides a compound represented by the formula (1)
-Arginine, ethanolamine, 2-methoxyethylamine, O-phosphorylethanolamine, 2-ethylaminoethanol, diethanolamine, 2-dimethylaminoethanol, choline, 2-amino-2-hydroxymethyl-1,3-propanediol, noradrenaline , Phenethylamine, ethylenediamine, taurine,
Phosphatidylethanolamine, N- (2-hydroxyethyl) acetamide, 2- (methylamino) ethanol, 2-anilinoethanol, 2- (benzylamino) ethanol, 3-amino-1-propanol, 2-
(2) related to the hair-healing agent (1), which is selected from the group consisting of amino-1-butanol, putrescine, DL-pyroglutamic acid and triethanolamine.

Further, the present invention relates to L-arginine, an ion thereof and / or a pharmaceutically acceptable salt thereof; an ammonium salt and an ion thereof and a compound of the formula (1) ′:

Embedded image (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ An alkylene group which may have a substituent which forms a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. And (3) the hair soothing agent (1), which comprises one or more components selected from the group consisting of: those ions and their pharmaceutically acceptable salts.

[0008] The present invention also relates to an ammonium salt and / or an ion thereof;

Embedded image (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ An alkylene group which may have a substituent which forms a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. And (2) at least one component selected from the group consisting of their ions and their pharmaceutically acceptable salts.

Furthermore, the present invention relates to L-arginine, an ion thereof and / or a pharmaceutically acceptable salt thereof; an ammonium salt and / or an ion thereof;

Embedded image (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ An alkylene group which may have a substituent which forms a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. (5) The above-mentioned hair restoring agent (1), which comprises at least one component selected from the group consisting of: ions thereof, and pharmaceutically acceptable salts thereof.

Further, the present invention provides a compound of the formula (1) '
Ethanolamine, 2-methoxyethylamine, O-phosphorylethanolamine, 2-ethylaminoethanol, diethanolamine, 2-dimethylaminoethanol, choline, 2-amino-2-hydroxymethyl-1,
3-propanediol, noradrenaline, phenethylamine, ethylenediamine, taurine, phosphatidylethanolamine, N- (2-hydroxyethyl) acetamide, 2- (methylamino) ethanol, 2-anilinoethanol, 2- (benzylamino) ethanol,
(6) related to the hair-healing agent (3) to (5), which is selected from the group consisting of 3-amino-1-propanol, 2-amino-1-butanol, putrescine, DL-pyroglutamic acid and triethanolamine. .

[0011] The present invention also relates to (7), which relates to the aforementioned hair-healing agents (1) to (6), further containing a natural product preparation.

Furthermore, the present invention relates to (8), wherein the natural product preparation is a rice preparation, (8).

[0013] The present invention also relates to the above-mentioned hair cleansing agent (1).
(9) A pharmaceutical, quasi-drug or cosmetic product containing any of (8) to (8).

[0014]

DESCRIPTION OF THE PREFERRED EMBODIMENTS First, the definitions of the terms used in the present specification will be described.

"Lower alkyl group" and "lower alkyl"
Is a linear or branched alkyl group having 1 to 10, preferably 1 to 5 carbon atoms, such as a methyl group and an ethyl group. The “lower alkoxy group” is a group in which an oxygen atom is bonded to the lower alkyl group, and examples include a methoxy group and an ethoxy group. "Aryl group"
It has 6 to 18 carbon atoms, preferably 6 to 10 carbon atoms, such as a phenyl group and an α-naphthyl group. The “aralkyl group” is a group in which the above-mentioned aryl group is bonded to the above-mentioned lower alkyl group, and examples thereof include a benzyl group and a phenylyl group. "Substituent" of "may have a substituent" is not particularly limited, for example, a hydroxyl group,
Examples include an amino group and a carboxyl group.

"Pharmaceutically acceptable salts" are pharmaceutically acceptable, for example, hydrochloride, hydrobromide, sulfate, citrate, acetate, maleate, succinate. Acid salts,
Methanesulfonate, p-toluenesulfonate and the like. Further, “ammonium salt” means a pharmaceutically acceptable ammonium salt, for example, hydrochloride, hydrobromide, sulfate, citrate, acetate, maleate, succinate Methanesulfonate, p-toluenesulfonate and the like.

"Natural product preparation" refers to a natural product (eg,
(Biocomponents, plant components) as raw materials. For example, a natural product is squeezed, an acid / alkali extract of the natural product, a hydrate of the natural product, an organic solvent extract of the natural product, an enzymatic reaction / fermented product of the natural product, and the like.

[0018] The term "hair soundening" of the hair soundening agent according to the present invention means that the active ingredient reaches the core of the hair to make the hair healthy. Therefore, it does not mean a temporary effect, that is, for example, temporarily replenishing water or temporarily eliminating hair trouble by coating with oil.

Next, the hair lightening agent according to the present invention will be described.

First, the active ingredients of the hair conditioner according to the present invention include (i) one or more ammonium salts (including ions), (ii) one or more ammonium salts (including ions) and one or more ammonium salts (including ions). There are three embodiments: a combination of the compound of the formula (1) (including a salt and an ion) and (iii) one or more compounds of the formula (1) (including a salt and an ion).

First, among the compounds of the formula (1), preferred compounds of the formula (1) are those wherein R ₁ , R ₂ and R ₃ are each independently substituted with a hydrogen atom, a hydroxyl group or a hydroxyl group. also aryl group, an amino group, a hydroxyl group or an optionally substituted lower alkyl group with an amino group, a carboxyl group, a guanidino group, or a lower alkyl group substituted with a guanidino group; R _4, R ₅ are, Each independently represents a hydrogen atom,
Hydroxyl or optionally substituted lower alkyl group with an amino group, or a carboxyl group, or, R ₄
And R ₅ together form a carbonyl group together with an adjacent carbon atom; R ₆ and R ₇ each independently represent a hydrogen atom, a lower alkyl group which may be substituted by a hydroxyl group, a lower alkylcarbonyl group; R ₆ represents a group or an aryl group, or R ₆ together with R _{2 represents} 5
It is an alkylene group which may have a substituent which forms a member ring; and a nitrogen atom in the formula is a compound which may be quaternized by a lower alkyl group.

More preferred compounds of formula (1) are R ₁ ,
R ₂ and R ₃ each independently represent a hydrogen atom, a hydroxyl group, an aryl group optionally substituted with a hydroxyl group, an amino group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a carboxyl group, a guanidino group; R ₄ represents a carboxyl group or R ₄ and R _{5 taken} together to form a carbonyl group with adjacent carbon atoms; R ₅ represents a carbonyl group or a lower alkyl group substituted with a guanidino group; a hydrogen atom, a carboxyl group, or represents a lower alkyl group which may be substituted with a hydroxyl group or an amino group; R _6, R ₇
Each independently represents a hydrogen atom, a lower alkyl group, a lower alkylcarbonyl group, or an aryl group which may be substituted with a hydroxyl group, or R ₆ together with R _{2 represents} an adjacent atom Represents an alkylene group which may have a substituent which forms a 5-membered ring with the above; and a compound in which a nitrogen atom in the formula may be quaternized by a lower alkyl group.

Further preferred compounds of formula (1) are R ₁ ,
R ₂ and R ₃ are each independently substituted with a hydrogen atom, a hydroxyl group, an aryl group optionally substituted with a hydroxyl group, a lower alkyl group optionally substituted with a hydroxyl group, a guanidino group, or a guanidino group. R represents a lower alkyl group;
₄ represents a carboxyl group; R ₅ represents a hydrogen atom, a carboxyl group, or a lower alkyl group optionally substituted with a hydroxyl group; R ₆ and R ₇ each independently represent a hydrogen atom, or A lower alkyl group which may be substituted with a hydroxyl group; and a compound in which a nitrogen atom in the formula may be quaternized with a lower alkyl group.

Even more preferred compounds of formula (1) are
₁ is a hydroxyl group, a lower alkyl group, a guanidino group, or
A lower alkyl group substituted with a guanidino group;
R ₂ and R ₃ each independently represent a hydrogen atom, a hydroxyl group, or
Be substituted with a hydroxyl group show a lower alkyl group or an aryl group; R ₄ is a carboxyl group; R ₅
Represents a hydrogen atom, a carboxyl group, or a lower alkyl group which may be substituted with a hydroxyl group; R ₆ and R ₇ each independently represent a lower atom which may be substituted with a hydrogen atom or a hydroxyl group. An alkyl group; a compound in which a nitrogen atom in the formula may be quaternized by a lower alkyl group.

The most preferred compound of formula (1) is R
₁ represents a guanidino group or a lower alkyl group substituted with a guanidino group; R ₂ and R ₃ each independently represent a hydrogen atom, a hydroxyl group, a lower alkyl group or an aryl group which may be substituted with a hydroxyl group; R ₄ represents a carboxyl group; R ₅ represents a hydrogen atom or a lower alkyl group which may be substituted with a hydroxyl group; R ₆ and R ₇ each independently represent a hydrogen atom, or Represents a lower alkyl group which may be substituted with a hydroxyl group; and a nitrogen atom in the formula is
A compound which may be quaternized with a lower alkyl group.

In another preferred compound of the formula (1) and the compound of the formula (1) ', R ₁ , R ₂ and R ₃ each independently have a hydrogen atom, a hydroxyl group or a substituent. May be a lower alkoxy group, an aryl group which may be substituted with a hydroxyl group, an amino group, a lower alkyl group which may be substituted with a hydroxyl group or an amino group, a guanidino group, or a lower alkyl group substituted with a guanidino group R ₄ , R
₅ each independently represents a hydrogen atom, a hydroxyl group, or a lower alkyl group or an aryl group which may be substituted with a hydroxyl group or an amino group; R ₆ and R ₇ each independently represent a hydrogen atom, A lower alkyl group or a lower alkylcarbonyl group which may be substituted with a hydroxyl group; and a compound in which a nitrogen atom in the formula may be quaternized with a lower alkyl group.

More preferred compounds of the formulas (1) and (1) 'are those wherein R ₁ , R ₂ and R ₃ are each independently a hydrogen atom,
A hydroxyl group, an aryl group which may be substituted with a hydroxyl group, an amino group, or a lower alkyl group which may be substituted with a hydroxyl group or an amino group; R ₄ and R ₅ each independently represent a hydrogen atom, A hydroxyl group or a lower alkyl group which may be substituted with a hydroxyl group; R ₆ and R ₇ each independently represent a hydrogen atom or a lower alkyl group which may be substituted with a hydroxyl group; , Wherein the nitrogen atom in the formula may be quaternized with a lower alkyl group.

In a further preferred compound of the formula (1) and the compound of the formula (1) ′, R ₁ , R ₂ and R ₃ are each independently substituted with a hydrogen atom, a hydroxyl group or a hydroxyl group. Represents an aryl group or a lower alkyl group which may be substituted;
R ₄ and R ₅ each independently represent a hydrogen atom, a hydroxyl group, or
A lower alkyl group which may be substituted with a hydroxyl group;
R ₆ and R ₇ each independently represent a hydrogen atom or a lower alkyl group which may be substituted with a hydroxyl group; and the nitrogen atom in the formula is quaternized with a lower alkyl group. May also be a compound.

In another most preferred compound of the formula (1) and the compound of the formula (1) ', R ₁ , R ₂ and R ₃ are each independently substituted with a hydrogen atom, a hydroxyl group or a hydroxyl group. R ₄ and R ₅ each independently represent an aryl group,
A hydrogen atom, a hydroxyl group, or an alkyl group having 1 to 3 carbon atoms which may be substituted with a hydroxyl group; R ₆ and R ₇ each independently represent a hydrogen atom or a hydroxyl group; A good lower alkyl group; and wherein the nitrogen atom in the formula is
A compound which may be quaternized with a lower alkyl group.

The hair conditioner according to the present invention preferably comprises a plurality of active ingredients, particularly preferably L-arginine (including salts and ions) and ammonium salts (including ions) and / or formulas. (1) '(including salts and ions). In this case, the ratio between the amount of L-arginine and the amount of the ammonium salt and / or the compound of the formula (1) ′ (the total amount thereof, if there is more than one) varies depending on the degree of hair damage, 1000: 1 by weight ratio
1: 100 is preferable, and 100: 1 to 1:10 is more preferable. In addition, the amount of ammonium salt (including ions) and the compound of formula (1) '(when salts and ions are also included, the amount of ammonium salt and the compound of formula (1)' (the total amount thereof when there are a plurality thereof)) The ratio varies depending on the degree of damage to the hair and the like, but is preferably 100: 1 to 1: 100 by weight, more preferably 10: 1 to 1:10.
When all of the arginine amount, the ammonium salt, and the compound of the formula (1) ′ are contained, those which are preferable for the above two components and those which combine the ranges mentioned as more preferable apply.

Further, a natural product preparation may be further contained. Here, the natural product preparation is preferably a plant preparation, and more preferably a cereal preparation (for example, rice, barley, wheat, barley, rye, enbaku, fly, foam, acne), particularly Preferably it is a rice preparation. Here, "rice" which is a raw material of the rice preparation is not particularly limited. That is, any kind and kind of rice may be used, and if it is derived from rice, for example, brown rice, white rice, a crushed product thereof, red bran, or white bran may be used. Germinated rice may be used. Then, the rice as a raw material may be subjected to treatments such as grinding, dipping, steaming, roasting, etc. Further, extraction, decomposition (by enzymes, koji, etc.), and fermentation (organic acid fermentation, alcohol fermentation, etc.) May be applied. Most preferred is a fermented rice extract.

As an example of a natural product preparation, rice, crushed rice or rice bran is added to water, and a starch-degrading enzyme or further a protease is added and reacted. After the reaction, yeast is added, and saccharification and fermentation are performed. What is obtained by performing it is mentioned.
In addition, rice, crushed rice and rice bran are added, and at least one of amylolytic enzyme, proteolytic enzyme and lipase is added,
Examples include those obtained by performing extraction by heating and heating, or by repeating these reactions twice or more. Further, those obtained by fermenting animals and plants or microorganisms or fermenting them after adding fermentable sugars may be mentioned. In addition, water is added to animals and plants or microorganisms, if necessary, and one or more of amylolytic enzymes, proteolytic enzymes and lipases are added, and the mixture is heated and heated to perform extraction, or these reactions are further performed. Those obtained by repeating twice or more are exemplified.

Here, the natural product preparation may or may not contain all or a part of the compound of the formula (1), but may contain essential components in the natural product preparation. May or may not be added with the essential components contained therein.

[0034] The hair soundening agent according to the present invention preferably has an alcohol concentration of 0 to 10 (v / v)%. The alcohol concentration is measured according to the prescribed analysis method of the NTA.

[0035] The hair sanitizing agent of the present invention can be used as pharmaceuticals, quasi-drugs, and cosmetics. For example, shampoo,
It is available in the form of a rinse, treatment, hair tonic, hair liquid, mousse. When used in such a wet form, the active ingredient may be dispersed or dissolved depending on the application. In addition, depending on the application, commonly used compounding components (for example, a surfactant in the case of shampoo)
May be added, and another drug may be used in combination. Also, the method of use and dosage can be used in the same manner as existing products. For example, when used as a shampoo, wet the hair,
Apply while whisking so that the shampoo spreads over the entire hair, wash and rinse off with water or hot water. The amount used may be such that the shampoo spreads over the entire hair, and may be appropriately increased or decreased according to the amount and length of the hair.

[0036]

According to the present invention, the active ingredient reaches the core of the hair by using the hair conditioner according to the present invention. For example, the cuticle on the outside of the hair is made sound and the inside of the hair is made sound. . That is, due to the soundness of the cuticle, there is no cuticle turning, peeling or chipping,
The arrangement pattern also becomes regular, the surface of the hair becomes smooth, the natural shine of the hair is born, and due to the soundness of the inside of the hair, it is not too hard, too soft, strength, elasticity, elasticity Gives you ideal hair quality. Thus, unlike the case of temporarily moisturizing or covering the surface with oil, by using the hair-healing agent to make the outside and the inside of the hair healthy, it is not a temporary moisturizing, You can regain the original beautiful and healthy hair. More specifically, it retains freshness, makes the hair soft, stiff, and elastic; has a dry, antistatic effect; improves split ends and cuts; smoothes the surface of the hair; Street,
Good combing; Prevents discoloration of hair color and hair manicure; Improved perm; Easy styling and good hairstyle; No excessive volume.

[0037]

[EXAMPLE] Test Example 1 Recovery test of damaged hair made artificially (hair soundening effect, cuticle sounding effect, soundness inside hair) To see the effect on damaged hair artificially by perm treatment Creates damaged hair and restores the damaged hair before and after using the hair conditioner of the present invention by the dipping method,
I saw the effect of cuticle improvement.

Sample: Example 1 (1% aqueous solution of L-arginine) L-arginine (manufactured by Nacalai Tesque, Inc.) 1.00 g Add purified water to make the total amount 100.00 g. ｛In addition, in addition to this example, an appropriate amount of a pH adjuster (hydrochloric acid, caustic soda) is appropriately added so that the pH of all of Examples 2 to 13 below becomes 6 to 6.8. ｝

Example 2 (1% aqueous solution of ethanolamine) Ethanolamine (manufactured by Nacalai Tesque, Inc.) 0.10 g Purified water is added to make the total amount 100.00 g.

Example 3 (1% aqueous ammonia) 28% aqueous ammonia (manufactured by Wako Pure Chemical Industries, Ltd.) 3.57 mL Purified water is added to bring the total amount to 100.00 g. If necessary, hydrochloric acid and sodium hydroxide are added to adjust the pH to 6.0.
Adjust to 6.8.

Example 4 (L-arginine 1% + ethanolamine 0.1%) L-arginine (manufactured by Nakarai Tesque Co., Ltd.) 1.00 g Ethanolamine (manufactured by Nakarai Tesque Co., Ltd.) 1.00 g Purified water was added. The total amount is 100.00 g.

Example 5 (L-arginine 1% + ethanolamine 0.1% + 0.1% ammonia water) L-arginine (manufactured by Nakarai Tesque) 1.00 g Ethanolamine (manufactured by Nakarai Tesque) 0 .10 g 28% aqueous ammonia (manufactured by Wako Pure Chemical Industries, Ltd.) 0.36 mL Add purified water to make the total amount 100.00 g.

Object: Hair bundle (human hair)

Perm solution: for cold two-bath hair straightener (commercially available)

Test Method: (1) One commercially available perm solution (thioglycolate) is applied to the hair bundle and left for 5 minutes. (2) After 5 minutes, the hair tress is thoroughly rinsed with tap water. (3) Wipe off moisture on the hair bundle with a cloth. (4) Apply 2 permanent agents (hydrogen peroxide) to the hair bundle and
Leave for a minute. (5) After 5 minutes, the hair tress is thoroughly rinsed with tap water. (6) After natural drying at room temperature, one hair bundle is loosely tied to form a knot. The knot is magnified and observed with a microscope (after perm treatment and before use of the embodiment). (7) The hair bundle after the permanent treatment is immersed in the sample. After 8 hours, remove and rinse thoroughly with tap water, dry at room temperature and loosely tie one of the tresses to form a knot. (8) Observe and enlarge the knot with a microscope (after perm treatment / after use of examples).

Judgment method: The feeling of the hair tress and the observation by a microscope (test equipment: OLYMPUS OVM1000NM, MODEL OVM-SAD) were used to determine the effect of hair damage recovery before and after the use of the examples.
The cuticle improvement effect is evaluated on a scale of 10 (the higher the numerical value, the higher the effect).

Test results: The results of the judgment are shown in Table 1. In addition, FIGS. 1 and 2 show enlarged photographs of a knot of a hair knot before and after using the hair smoothing agents of Examples 3 and 5.
It was shown to. L-arginine, ethanolamine, and ammonia water each have a hair-healthy effect even when used alone,
It shows that the effect is further enhanced by combining a plurality.

[0048]

[Table 1]

Test Example 2 Recovery test of damaged hair made artificially (hair restoration effect, cuticle restoration effect, sound restoration inside hair)
In order to see the effect on damaged hair, damaged hair was artificially created by perm treatment, and the effect of recovering damaged hair before and after using the hair sanitizing agent of the present invention and the effect of improving cuticles by the rinse-off method were examined. .

Sample: Example 6 (Rice preparation containing 0.03% L-arginine) 1 kg of white rice was ground by a grinder. 3000mL of water
And α-amylase 7.5 g, protease 8.0 g,
After adding 8.0 g of peptidase, the mixture was heated to 55 ° C., and left at that temperature for 10 hours. Thereafter, the temperature was gradually increased, and boiling extraction was performed for 5 minutes. And 2
After cooling to 0 ° C., pressure filtration was performed, and citric acid was added to the filtrate to lower the pH to 3.3. 8.0 g of acidic protease and 8.0 g of acid carboxypeptidase
Was added and reacted at 55 ° C. for 10 hours. Then 70
The mixture was heated to ℃ and filtered by cooling to obtain 2700 mL of a product containing 354 mg / L of L-arginine (the concentration of L-arginine was about 0.03%).

Example 7 (rice preparation containing 0.03% L-arginine + 1% L-arginine) Example 6 (containing 0.03% L-arginine from rice) 90.00 mL L-arginine (Nacalai) (Manufactured by Tesque Corporation) 1.00 g Purified water is added to make the total amount 100.00 g.

Example 8 (rice preparation containing 0.03% L-arginine + 0.1% L-arginine + 0.1% ethanolamine) Example 6 (containing 0.03% L-arginine from rice) 90.00 mL L-arginine (manufactured by Nakarai Tesque) 0.10 g Ethanolamine (manufactured by Nakarai Tesque) 0.10 g Add purified water to make the total amount 100.00 g.

Object: Hair bundle (human hair)

Perm solution: for cold two-bath hair straightener (commercially available)

Test method: (1) One commercially available perm solution (thioglycolate) is applied to the hair bundle and left for 5 minutes. (2) After 5 minutes, the hair tress is thoroughly rinsed with tap water. (3) Wipe off moisture on the hair bundle with a cloth. (4) Apply 2 permanent agents (hydrogen peroxide) to the hair bundle and
Leave for a minute. (5) After 5 minutes, the hair tress is thoroughly rinsed with tap water. (6) After natural drying at room temperature, loosely tie one of the hair bundles to form a knot. The knot is magnified and observed with a microscope (after perm treatment and before use of the embodiment). (7) The hair bundle after the permanent treatment is immersed in the sample. Take out after 10 minutes, rinse thoroughly with tap water and dry at room temperature.
This is repeated 15 times. Dry at room temperature and loosely tie one of the tresses to form a knot. (8) Observe and enlarge the knot with a microscope (after perm treatment / after use of examples).

Judgment method: A hair damage recovery effect and a cuticle improvement effect before and after the use of the hair soundening agent of the example were evaluated on a scale of 10 based on the feel of the hair bundle and observation with a microscope (the higher the numerical value, the higher the value). High effect). Table 2 shows the judgment results.
It was shown to. In addition, FIG. 3 shows enlarged photographs of the knot of the hair before and after using the hair smoothing agent of Example 7.

[0057]

[Table 2]

Results: As shown in Table 2, the addition of the rice preparation to L-arginine, ethanolamine, and aqueous ammonia further enhances the hair soundening effect as compared with the case where the rice preparation is used alone.

Test Example 3 Sensory Test (Hair Soundening Effect) In order to examine the hair soundening effect, five persons in a group of shampoos of the hair cleansing agent according to the present invention and the comparative example were used for one day for damaged hair. Used once in the usual way and self-evaluated. The state of the hair after 10 days of use was evaluated on a 10-point scale (the higher the value, the higher the effect).

Evaluation items: Brightness, freshness, ease of styling, softness, stiffness, elasticity, split ends, cut hair, improvement Comprehensive evaluation (brightness of hair, freshness, ease of styling, holding of hair style, hair Softness, stiffness,
Comprehensive evaluation of elasticity, dryness, split ends, broken hairs, smooth surface, finger passing, comb passing)

Samples: Example 9 (0.1% L-arginine + 0.1% ethanolamine + 10% rice preparation containing 0.03% L-arginine + shampoo formulation) L-arginine (Nacalai Tesque, Inc.) 0.10 g Ethanolamine (manufactured by Nacalai Tesque, Inc.) 0.10 g Example 6 (containing 0.03% of L-arginine from rice) 10.00 mL Sodium alkyl ether sulfate 20.00 g Lauric acid diethanolamide 4 0.000 g Propylene glycol 3.00 g Sodium benzoate 0.18 g Fragrance 0.30 g

Example 10 (Wheat preparation containing 0.02% of L-arginine) 500 g of wheat was pulverized by a pulverizer. Add 200 water
0 mL, 2 g of α-amylase, 2 g of β-amylase, and 1 g of protease were added, and the mixture was heated to 55 ° C. and left at that temperature for 15 hours. Thereafter, the temperature was gradually raised, and the mixture was steamed for 5 minutes, cooled to 50 ° C., 1 g of acidic protease was added, and reacted at 50 ° C. overnight. Thereafter, the mixture was heated to 70 ° C., cooled, and filtered, and 152 mg
1850 mL of product containing / L L-arginine were obtained.

Example 11 (Wheat preparation containing 0.1% L-arginine + 0.1% ammonia water + 0.02% L-arginine + shampoo formulation) L-arginine (manufactured by Nacalai Tesque, Inc.) 0.10 g 28% aqueous ammonia (manufactured by Wako Pure Chemical Industries, Ltd.) 0.36 mL Example 10 (containing 0.02% of L-arginine from wheat) 20.00 mL sodium alkyl ether sulfate 20.00 g lauric acid diethanolamide 4.00 g propylene Glycol 3.00 g Sodium benzoate 0.18 g Fragrance 0.30 g Add purified water to make the total amount 100.00 g.

Example 12 (Soybean preparation containing 0.03% of L-arginine) 300 g of soybean was pulverized by a pulverizer, and 100 g of water was added thereto.
0 mL, 2 g of α-amylase, 2 g of lipase, and 2 g of cellulase were added, and the mixture was heated to 55 ° C. and left at that temperature for 3.5 hours. Thereafter, the temperature was gradually raised, and after steaming for 5 minutes, cooled, filtered, and 332 mg
320 mL of product containing / L of L-arginine were obtained (the concentration of L-arginine is about 0.03%). Example 13 (Soy preparation containing 0.03% L-arginine + 0.1% ethanolamine + 0.1% aqueous ammonia +
Shampoo formulation)

Example 12 (containing 0.03% of L-arginine from soybean) 20.00 mL Ethanolamine (manufactured by Nacalai Tesque, Inc.) 0.10 g 28% aqueous ammonia (manufactured by Wako Pure Chemical Industries, Ltd.) 0.36 mL Sodium alkyl ether sulfate 20.00 g Lauric acid diethanolamide 4.00 g Propylene glycol 3.00 g Sodium benzoate 0.18 g Fragrance 0.30 g Add purified water to make the total amount 100.00 g.

Comparative Example 1 (Shampoo type) Sodium alkyl ether sulfate 20.00 g Diethanolamide laurate 4.00 g Propylene glycol 3.00 g Sodium benzoate 0.18 g Fragrance 0.30 g Purified water was added to make the total amount 100.00 g. And

[0067]

[Table 3]

Test results: As shown in Table 3, the use of the hair conditioner of the present invention restores damaged hair, reveals natural shine, original shine of hair, and maintains freshness.
Styling becomes easy, and softness, firmness,
It became clear that the hair became elastic, the split ends and cut hairs were improved, the surface of the hair became smooth, and the fingers and combs became better. In addition, it was found that the hair color and hair manicure were hardly removed and the color retention was improved and the perm was improved by continuous use. From this, it was clarified that the hair sanitizing agent of the present invention reaches the core of the hair, makes the outside and inside sound healthy, and makes the whole hair sound.

[Brief description of the drawings]

FIG. 1 is a microscope enlarged photograph of a hair knot before (A) and after (B) use of a hair cleansing agent (Example 3).

FIG. 2 is a microscope enlarged photograph of a hair knot before (A) and after (B) use of a hair cleansing agent (Example 5).

FIG. 3 is a microscope enlarged photograph of a hair knot before (A) and after (B) use of the hair cleansing agent (Example 7).

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C083 AA021 AA022 AB032 AB081 AB082 AB102 AC122 AC242 AC482 AC521 AC541 AC542 AC581 AC582 AC691 AC782 CC31 CC33 CC38 EE29

Claims (9)

[Claims] 1. Ammonium salt and its ion and formula (1): (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a carboxyl group, a guanidino group, or guanidino A lower alkyl group substituted with a group;
R ₄ and R ₅ each independently represent a hydrogen atom, a hydroxyl group, a lower alkyl group or an aryl group which may be substituted with a hydroxyl group or an amino group, or a carboxyl group;
Alternatively, R ₄ and R ₅ together form a carbonyl group with an adjacent carbon atom; R ₆ and R ₇ each independently represent a hydrogen atom or a lower alkyl group which may be substituted by a hydroxyl group. Or a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ may have a substituent that forms a 5-membered ring with an adjacent atom. Wherein the nitrogen atom in the formula may be quaternized with a lower alkyl group), their ions and their pharmaceutically acceptable salts are selected from the group consisting of A hair-healing agent containing one or more components. 2. The method according to claim 1, wherein the compound of formula (1) is L-arginine,
Ethanolamine, 2-methoxyethylamine, O-phosphorylethanolamine, 2-ethylaminoethanol, diethanolamine, 2-dimethylaminoethanol, choline, 2-amino-2-hydroxymethyl-1,
3-propanediol, noradrenaline, phenethylamine, ethylenediamine, taurine, phosphatidylethanolamine, N- (2-hydroxyethyl) acetamide, 2- (methylamino) ethanol, 2-anilinoethanol, 2- (benzylamino) ethanol,
The hair cleansing agent according to claim 1, which is selected from the group consisting of 3-amino-1-propanol, 2-amino-1-butanol, putrescine, DL-pyroglutamic acid and triethanolamine. 3. L-arginine, an ion thereof and / or a pharmaceutically acceptable salt thereof; an ammonium salt and an ion thereof and a compound of the formula (1) ′: (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ A alkylene group which may have a substituent forming a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. 2. The hair cleansing agent according to claim 1, comprising one or more components selected from the group consisting of: an ion thereof, and a pharmaceutically acceptable salt thereof. 4. An ammonium salt and / or an ion thereof; formula (1) ′: (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ A alkylene group which may have a substituent forming a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. 2. The hair cleansing agent according to claim 1, comprising one or more components selected from the group consisting of: an ion thereof, and a pharmaceutically acceptable salt thereof. 5. L-arginine, an ion thereof and / or a pharmaceutically acceptable salt thereof; an ammonium salt and / or
Or an ion thereof; Formula (1) ′: embedded image (Wherein, R ₁ , R ₂ and R ₃ each independently represent a hydrogen atom,
Hydroxyl group, a lower alkoxy group which may have a substituent,
A phosphoryloxy group, an aryl group optionally substituted with a hydroxyl group, an amino group, a sulfonic acid group, a phosphatidyloxy group, a lower alkyl group optionally substituted with a hydroxyl group or an amino group, a guanidino group, or a guanidino group It showed a lower alkyl group; R _4, R ₅ are each independently hydrogen atom, a hydroxyl group, or a hydroxyl group or an optionally substituted lower alkyl group or an aryl group with an amino group, or, R ₄ And R ₅ together form a carbonyl group with adjacent carbon atoms; R ₆ , R ₇
Each independently represents a hydrogen atom, a lower alkyl group which may be substituted with a hydroxyl group, a lower alkylcarbonyl group, an aryl group, or an aralkyl group, or R ₆ together with R ₂ A alkylene group which may have a substituent forming a 5-membered ring with an adjacent atom; and a nitrogen atom in the formula may be quaternized by a lower alkyl group. 2. The hair cleansing agent according to claim 1, comprising one or more components selected from the group consisting of: an ion thereof, and a pharmaceutically acceptable salt thereof. 6. The compound of the formula (1) ′ is ethanolamine, 2-methoxyethylamine, O-phosphorylethanolamine, 2-ethylaminoethanol, diethanolamine, 2-dimethylaminoethanol, choline,
-Amino-2-hydroxymethyl-1,3-propanediol, noradrenaline, phenethylamine, ethylenediamine, taurine, phosphatidylethanolamine, N- (2-hydroxyethyl) acetamide, 2-
(Methylamino) ethanol, 2-anilinoethanol, 2- (benzylamino) ethanol, 3-amino-
The hair cleansing agent according to any one of claims 3 to 5, which is selected from the group consisting of 1-propanol, 2-amino-1-butanol, putrescine, DL-pyroglutamic acid, and triethanolamine. 7. The method according to claim 1, further comprising a natural product preparation.
7. The hair lightening agent according to any one of items 1 to 6. 8. The method according to claim 7, wherein the natural product preparation is a rice preparation. 9. A pharmaceutical, quasi-drug or cosmetic comprising the hair-healing agent according to claim 1.