Cuticle care agents and hair cosmetics containing them

Abstract

This product provides a cuticle care agent that suppresses the peeling of hair cuticles that occurs in daily life, and further suppresses the occurrence of split ends. [Solution] A cuticle peeling inhibitor or split end inhibitor containing a valine derivative or a salt thereof, wherein at least a portion of the active hydrogen of the amino group of valine is substituted with a functional group represented by the following general formula (I) (* indicates the position of bonding to the amino group of valine), and a hair cosmetic containing the same. TIFF2026048576000008.tif43160 (In the formula, R 1 (This represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.)

Description

Technical Field

[0001] The present invention relates to an amino acid derivative or a salt thereof that suppresses cuticle peeling of hair and further suppresses the generation of split ends, and a hair cosmetic containing them.

Background Art

[0002] Hair is constantly exposed to chemical stimuli such as perms and hair colors, environmental stimuli such as ultraviolet rays, drying, and heat from hair dryers, and physical stimuli such as friction of hair during shampooing and blow-drying while wet. In particular, the cuticle, which is the outermost layer of hair, is directly affected by these stimuli and suffers complex and cumulative damage. In damaged hair, defects, peeling, and shedding of the cuticle are observed. As the damage progresses further, most of the cuticle at the hair tip peels off, resulting in the generation of split ends and frayed hair, leading to a severely damaged state. Therefore, suppressing cuticle peeling is very important for maintaining beautiful hair.

[0003] As a technique for improving the state of such damaged cuticles, a hair cosmetic containing specific amino acids (arginine, glycine, alanine, serine, proline, leucine, isoleucine) and highly polymerized amino-modified silicone has been proposed (Patent Document 1). However, it only remains at the observation of the hair surface state by a scanning electron microscope (SEM), and the evaluation of the cuticle peeling suppression effect of hair and the suppression effect on split end generation have not been studied.

[0004] In addition, the present inventors have proposed a hydrolyzed protein derivative or an amino acid derivative that improves the stiffness and smoothness of hair, but it is an invention as a hair moisturizer or whitening agent, and not an invention related to a cuticle care agent (Patent Document 2).

Prior Art Documents

Patent Documents

[0005] [Patent Document 1] Japanese Patent Publication No. 2003-095879 [Patent Document 2] Patent No. 6541118 [Overview of the project] [Problems that the invention aims to solve]

[0006] For consumers, hair coloring and perms have become necessities, and daily hair care routines such as brushing, blow-drying, and using irons apply stretching forces to the hair. When hair is stretched, a phenomenon called cuticle lifting is observed, and cuticle peeling is promoted. Damage also accumulates due to friction from washing the hair. In other words, it is thought that daily hair care routines promote the peeling of hair cuticles, leading to an increase in split ends and breakage.

[0007] Therefore, the object of the present invention is to provide a cuticle care agent that suppresses cuticle peeling that occurs in daily life and further suppresses the occurrence of split ends, as well as a hair cosmetic containing the same. [Means for solving the problem]

[0008] In view of the above circumstances, the inventors conducted thorough research and found that valine derivatives or salts thereof substituted with specific functional groups can solve the above problems, thus completing the present invention.

[0009] The present invention, firstly, is a cuticle peeling inhibitor or split end inhibitor characterized by containing a valine derivative or a salt thereof in which at least a portion of the active hydrogen of the amino group of valine is substituted with a functional group represented by the following general formula (I) (* indicates the position where it is attached to the amino group of valine).

[0010] [ka]

[0011] (In formula (I), R 1 (This represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.)

[0012] The second aspect of the present invention is the cuticle peeling inhibitor or split end generation inhibitor of the first aspect of the present invention, wherein R in the general formula (I) 1 The material is characterized by being a valine derivative or a salt thereof, which has a methyl group having 1 carbon atom. When it is a valine derivative or a salt thereof, it exhibits a superior cuticle peeling inhibitory effect and split end formation inhibitory effect, and therefore falls under this preferred embodiment.

[0013] The cuticle peeling inhibitor or split end inhibitor of the present invention can be incorporated into hair cosmetics, and in particular, the effects of the present invention can be further enhanced and experienced when incorporated into cleansing agents, leave-in treatments, and styling products (claims 3 and 4). [Effects of the Invention]

[0014] The present invention relates to a cuticle peeling inhibitor or split end inhibitor containing a valine derivative having a specific functional group or a salt thereof, and furthermore, by incorporating it into hair cosmetics, it is possible to create cosmetics that suppress the peeling of hair cuticles and the occurrence of split ends. [Brief explanation of the drawing]

[0015] [Figure 1] Figure 1 shows scanning electron microscope (SEM) images of the surface of damaged and permed hair treated with the valine derivative of the present invention and stretched using a tensile fracture testing machine. [Figure 2] Figure 2 shows scanning electron microscope (SEM) images of the surface of damaged and permed hair that was treated with deionized water and stretched using a tensile strength tester. [Figure 3] Figure 3 shows scanning electron microscope (SEM) images of the surface of damaged and permed hair that has been treated with the valine derivative of the present invention and has not been stretched using a tensile fracture testing machine. [Figure 4]Figure 4 is a scanning electron microscope (SEM) photograph of the surface of hair that has not been stretched by a tensile testing machine after being treated with ion-exchanged water for damaged and permed hair. [Figure 5] Figure 5 is a scanning electron microscope (SEM) photograph of the surface of hair that has been stretched by a tensile testing machine after being treated with ion-exchanged water for healthy hair. [Figure 6] Figure 6 is a scanning electron microscope (SEM) photograph of the surface of hair that has not been stretched by a tensile testing machine after being treated with ion-exchanged water for healthy hair.

Mode for Carrying Out the Invention

[0016] The components constituting the cuticle peeling inhibitor or branch hair generation inhibitor of the present invention, and further, the form of the hair cosmetic of the present invention will be specifically described below.

[0017] [Valine Derivative or Its Salt] The valine derivative or its salt constituting the cuticle peeling inhibitor or branch hair generation inhibitor of the present invention can be obtained, for example, by the method described in Example 1 of Patent Document 2 above.

[0018] In the present invention, the form of the salt of the valine derivative is also included. This salt is formed by the carboxylic acid of valine forming a salt, and examples include sodium salt, potassium salt, ammonium salt, triethanolamine salt, monoethanolamine salt, 2-amino-2-methyl-1,3-propanediol salt, 2-amino-2-methyl-1-propanolamine salt, cetearamide ethyldiethylamine salt, etc. Among them, sodium salt and potassium salt are particularly preferred.

[0019] As the valine derivative or its salt of the present invention, a commercially available product containing the display name: Tosylvaline Na can be used. For example, Aminoreact TsV (containing 8% Tosylvaline Na) (trade name, manufactured by Showa Kasei Kogyo Co., Ltd.) can be used.

[0020] The amount of the valine derivative or salt thereof in the hair cosmetic composition of the present invention is preferably 0.01% by mass or more, and more preferably 0.03% by mass or more. The upper limit is preferably 0.5% by mass or less, and more preferably 0.15% by mass or less. If the amount is less than 0.01% by mass, it is difficult to exhibit the cuticle peeling inhibitory effect and split end formation inhibitory effect of the present invention, while if the amount exceeds 0.5% by mass, the effect commensurate with the amount may not be obtained.

[0021] In addition to the above-mentioned components, the hair cosmetic composition of the present invention may contain a wide range of other components commonly used in cosmetics, depending on the application, as long as their effectiveness and stability are not impaired, and can be used individually or in combination of two or more components.

[0022] Ingredients commonly used in cosmetics are not limited to, but include, for example, oily components, surfactants, polymer compounds, texture modifiers, pharmaceuticals, UV absorbers, proteins, protein hydrolysates or derivatives thereof, amino acids or derivatives thereof (excluding the valine derivative of the present invention), antioxidants, metal ion chelating agents, pH adjusters, preservatives, humectants, pigments, colorants, fragrances, and the like.

[0023] Examples of the oily components, surfactants, polymer compounds, texture modifiers, pharmaceuticals, ultraviolet absorbers, proteins, protein hydrolysates or derivatives thereof, amino acids or derivatives thereof (excluding the valine derivative of the present invention), antioxidants, metal ion chelating agents, pH adjusters, preservatives, humectants, pigments, colorants, fragrances, etc., are similar to those described in Publication No. WO2022 / 080287.

[0024] In the hair cosmetic composition of the present invention, it is preferable that it be a cleansing agent, a leave-in treatment, or a styling agent, as these can fully exhibit the effects of the present invention. Examples of cleansing agents include hair shampoo, hair rinse, hair conditioner, in-bath hair treatment, and hair mask; examples of leave-in treatments include hair mist, hair treatment lotion, hair milk, and hair cream; and examples of styling agents include hair foam, hair gel, setting lotion, hair liquid, hair grease, and hair wax. However, the present invention is not limited to these examples. [Examples]

[0025] The present invention will now be specifically described with reference to examples, but the present invention is not limited to these examples.

[0026] Prior to the examples, the test methods and evaluation methods used in each example will be explained. Furthermore, the aqueous solution of the valine derivative of the present invention used in each example was a concentration-adjusted version of Aminoreact TsV (containing 8% tosylvaline Na) manufactured by Seiwa Kasei Co., Ltd.

[0027] [Creating damaged hair] For use in Cuticle Peeling Inhibition Test 1 and Split End Inhibition Tests 1 and 2, damaged hair was prepared by bleaching to ensure a consistent degree of hair damage. Specifically, healthy black hair bundles were immersed in 2% polyoxyethylene(3) lauryl ether sodium sulfate heated to 40°C, left to stand in a heated immersion chamber for 30 minutes, then rinsed with 40°C tap water for 1 minute, towel-dried, and blow-dried. Next, as a bleaching treatment, the hair was immersed in a 1:1 (by weight) mixture of 6% hydrogen peroxide and 2% ammonia water at 30°C for 30 minutes, then rinsed with 40°C tap water. After towel-drying, as an acidic rinse, the hair was immersed in a mixture of 0.1M citric acid and 0.2M disodium hydrogen phosphate for 5 minutes at room temperature, then rinsed with 40°C tap water. Finally, it was immersed in deionized water at room temperature for 10 minutes, then towel-dried and blow-dried. This bleaching procedure was repeated three times.

[0028] [Creating damaged and permed hair] Furthermore, damaged and permed hair was prepared for use in the cuticle peeling inhibition effect 2. Specifically, a 7% aqueous solution of ammonium thioglycolate, adjusted to pH 9.2-9.3 with monoethanolamine, was applied to the damaged hair prepared as described above, and left to stand at room temperature for 15 minutes. After that, it was washed with 40°C tap water for 2 minutes and dried with a towel. Subsequently, a 7% aqueous solution of sodium bromate, adjusted to around pH 6.5 with phosphoric acid solution, was applied, and left to stand at room temperature for 15 minutes. After washing with 40°C tap water for 2 minutes, it was towel-dried and dried with a hairdryer to obtain damaged and permed hair.

[0029] Test Example 1: Cuticle Peeling Inhibition Test 1 Samples treated with an aqueous solution of the valine derivative of the present invention were designated as Example 1, and samples treated with a cyclopentasiloxane dilution of dimethicone (manufactured by Momentive Performance Materials Japan, product name: XF49-601), a well-known hair repair ingredient, were designated as Comparative Example 1. A cuticle peeling inhibition test 1 was then performed using the method described below.

[0030] [Cuticle peeling inhibition test 1] A bundle of damaged hair (15 cm long, 2.2 g in weight) was immersed in an aqueous solution of the valine derivative of the present invention (0.08% as active ingredient) or a diluted solution of dimethicone cyclopentasiloxane (0.08% as active ingredient) at 40°C for 10 minutes, then towel-dried and dried with a hairdryer. 10 mg of hair, with the root end of the bundle cut to approximately 3 cm, and 100 g of deionized water were placed in a glass container and treated in an ultrasonic cleaner (AS ONE AS52TU, oscillation frequency 35 kHz, output 200 W) at 40°C for 30 minutes. After removing the hair and drying it, the number of cuticles on the hair surface was visually measured using a scanning electron microscope (SEM, manufactured by JEOL Ltd.). Furthermore, as a control test, the same procedure was followed except that the valine derivative aqueous solution of the present invention was replaced with ion-exchanged water and ultrasonic treatment was omitted, and the number of cuticles was measured. The cuticle retention rate was calculated from the measured number of cuticles using the following formula. Cuticle retention rate (%) = (A / B) × 100 [In the formula, A is the number of cuticles when treated with the aqueous solution of the valine derivative or the dilute dimethicone solution of the present invention, and B is the number of cuticles when treated with ion-exchanged water.]

[0031] Table 1 shows the results of evaluating the calculated cuticle retention rate according to the evaluation criteria below. The measurement was performed with N=5, and a higher cuticle retention rate indicates a greater cuticle peel suppression effect.

[0032] [Evaluation Criteria] (1) Cuticle peeling suppression effect ◎: Average cuticle retention rate is 95% or higher ○: Average cuticle retention rate is 85% or higher, but less than 95%. △: Average cuticle retention rate is 75% or higher, but less than 85%. ×: Average cuticle retention rate is less than 75%

[0033] [Table 1]

[0034] As is clear from Table 1, hair treated with the valine derivative of the present invention exhibits a superior cuticle peeling inhibitory effect compared to hair treated with dimethicone, which is used as a hair repair component.

[0035] Test Example 2: Cuticle Peeling Inhibition Test 2 In Test Example 1, the effect of suppressing cuticle peeling when hair was damaged by ultrasonic treatment was confirmed, while in Test Example 2, the effect of suppressing cuticle peeling when hair was damaged using a tensile fracture testing machine was confirmed. Cuticle peeling suppression test 2 was performed using the method described below.

[0036] [Cuticle peeling inhibition test 2] Thirty hairs were randomly selected from the prepared damaged / permed hair bundles. For each selected hair, the short diameter and diameter were precisely measured using a hair diameter measuring device (product name: SK2000, manufactured by Kato Tech Co., Ltd.), and the hair cross-sectional area was determined. The hair cross-sectional area was 4700-5300 μm². 2 We selected hairs that met certain criteria and divided them into two groups of five hairs each, ensuring that the average cross-sectional area of ​​each hair was approximately the same. Two separate groups were prepared. One group was immersed in an aqueous solution of the valine derivative of the present invention (0.08% active ingredient) at 40°C for 1 hour, and the other group was immersed in deionized water at 40°C for 1 hour. Afterwards, the hairs were rinsed with running tap water at 40°C for 1 minute, towel-dried, and then dried with a hairdryer. Subsequently, one strand of hair from each group was stretched using a tensile strength tester (product name: KES-G1-SH, manufactured by Kato Tech Co., Ltd.) under the following conditions, and the hair surface was observed using a scanning electron microscope (SEM). Figure 1 shows the results for hair treated with the aqueous solution of the valine derivative of the present invention, and Figure 2 shows the results for hair treated with deionized water.

[0037] Furthermore, damaged and permed hair was treated with the valine derivative aqueous solution of the present invention, and the results of hair that did not stretch when tested with a tensile fracture testing machine are shown in Figure 3. Damaged and permed hair was treated with deionized water, and the results of a tensile strength test on hair that did not stretch are shown in Figure 4. Figure 5 shows the results of hair stretching using a tensile strength tester after treating healthy hair with deionized water. Figure 6 shows the results of testing healthy hair treated with deionized water, using a tensile strength tester to determine if the hair did not stretch.

[0038] [Conditions for a tensile fracture testing machine] One strand of hair treated with the valine derivative aqueous solution of the present invention or ion-exchanged water was placed in a tensile jig with an initial length of 50 mm. Then, it was pulled at a speed of 1 mm / sec until the load on the hair reached 100 gf.

[0039] The results in Figures 2 and 4 show that in hair treated with deionized water, the cuticle on the hair surface peels off when stretched using a tensile strength tester. On the other hand, the results in Figures 1 and 3 clearly show that, compared to the results with ion-exchanged water, the peeling of the cuticle on the hair surface after stretching using a tensile strength tester is suppressed in hair treated with the valine derivative aqueous solution of the present invention. Furthermore, the results in Figures 5 and 6 show that no peeling of the cuticle was observed in healthy hair even when stretched using a tensile strength tester. Therefore, the valine derivative aqueous solution of the present invention can suppress the peeling of the cuticle in hair damaged by, for example, daily hair care activities. Therefore, it is clear that the aqueous solution of the valine derivative of the present invention has an excellent cuticle peeling inhibitory effect, as demonstrated in cuticle peeling inhibition test 2.

[0040] Test Example 3: Effect of suppressing split ends 1 Samples treated with the valine derivative aqueous solution of the present invention (0.08% active ingredient) were designated as Example 2, samples treated with 0.04% active ingredient were designated as Example 3, and samples treated with L-valine aqueous solution (0.08% active ingredient) were designated as Comparative Example 2. Split end inhibition test 1 was performed using the method described below.

[0041] [Split End Inhibition Test 1] A bundle of damaged hair (11 cm in length, 0.4 g in weight) was immersed in an aqueous solution of the valine derivative of the present invention (0.08% or 0.04% of the active ingredient) or an aqueous solution of L-valine (0.08% of the active ingredient) at 40°C for 60 minutes. After rinsing with running water at 40°C for 10 minutes, the hair was towel-dried and then dried with a hairdryer. Furthermore, a control group was created by conducting the same test using only deionized water. The brush was fixed to a three-piece motor, and the treated hair was brushed for 60 minutes. The number of split ends that occurred was visually measured. The measurement was performed with N=3, and the average number of split ends is shown in Table 2.

[0042] [Table 2]

[0043] As is clear from Table 2, using the aqueous solution of the valine derivative of the present invention suppresses the number of split ends compared to the aqueous solution of L-valine without specific functional groups and the Control. In other words, it has become clear that the valine derivative of the present invention has an excellent effect in suppressing the occurrence of split ends.

[0044] Test Example 4: Effect of suppressing split ends 2 The shampoos described in Tables 3 and 4 below were prepared using conventional methods, and the split end inhibition test 2 shown below was conducted. The results are shown in Tables 3 and 4. Note that all values ​​listed in the tables are mass percentages relative to the total mass of the cosmetic product.

[0045] [Split End Inhibition Test 2] The shampoos listed in Tables 3 and 4 were diluted 10 times and immersed in a bundle of damaged hair (11 cm long, 0.4 g in weight) at 40°C for 10 minutes. Afterward, the bundle was rinsed with 40°C tap water for 1 minute, then towel-dried and blow-dried. This process was repeated 6 times (7 times in total). A brush was fixed to a three-piece motor, and the treated hair was brushed for 60 minutes. The number of split ends was visually measured. Measurements were performed with N=3, and the average number of split ends is shown in Tables 3 and 4.

[0046] [Table 3]

[0047] In Table 3, *1: Emal 20C (contains 25% sodium laureth sulfate) (product name, manufactured by Kao Corporation) *2: Amphorex CB-1 (containing 30% cocamidopropyl betaine) (manufactured by Miyoshi Oil & Fat Co., Ltd.) *3: Seisept-H (product name, manufactured by Seiwa Kasei Co., Ltd.) *4: Aminoreact TsV (contains 8% tosylvaline sodium) (product name, manufactured by Seiwa Kasei Co., Ltd.) *5: Dowsil BY 22-055 Emulsion (contains approximately 60% dimethicone) (product name, manufactured by Dow Toray Corporation) It was formulated as such.

[0048] [Table 4]

[0049] In Table 4, *4 and 5 are the same as in Table 3. *6: NIKKOL CMT-30 (contains 30% sodium cocoyl methyl taurate) (product name, manufactured by Nikko Chemicals Co., Ltd.) *7: Amisoft CT-12S (contains 30% TEA cocoyl glutamate) (manufactured by Ajinomoto Healthy Supply Co., Ltd.) *8: Softazoline CPB-R (containing 30% cocamidopropyl betaine) (manufactured by Kawaken Fine Chemical Co., Ltd.) *9: Softazoline LHL-SF (contains 27% sodium lauroamphoacetate) (product name, manufactured by Kawaken Fine Chemical Co., Ltd.) *10: Obazolin LB-SF (contains 35% lauryl betaine) (product name, manufactured by Toho Chemical Industry Co., Ltd.) It was formulated as such.

[0050] As is clear from Tables 3 and 4, the number of split ends in hair treated with the shampoo containing the valine derivative of the present invention is suppressed compared to the number of split ends in hair treated with the Control or Comparative Example shampoos. In other words, it has become clear that the aqueous solution of the valine derivative of the present invention has an excellent effect in suppressing the occurrence of split ends.

[0051] Other examples will be described. A hair conditioner with a high effect in suppressing split ends was obtained by manufacturing using a conventional method.

[0052] Example 6: Hair Conditioner Steartrimonium chloride, water, isopropanol*11 - 3.0% Cetearyl alcohol · 3.0% Steerless -20··0.5% Concentrated glycerin ·· 2.0% Ethoxydimethyl, phenoxyethanol, methylparaben, propylparaben, butylparaben, ethylparaben*3 - 0.3% Tosylvaline Na, BG, Water *4 - 1.0% water...residual *Items 3 and 4 are the same as in Table 3. *11 was formulated as Catinal STC-25W (product name, manufactured by Toho Chemical Industry Co., Ltd.).

Claims

1. A cuticle peeling inhibitor or split end inhibitor characterized by containing a valine derivative or a salt thereof in which at least a portion of the active hydrogen of the amino group of valine is substituted with a functional group represented by the following general formula (I) (* indicates the position of attachment to the amino group of valine). 【Chemistry 1】 (In the formula, R １ (This represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.)

2. In the above general formula (I), R １ The cuticle peeling inhibitor or split end generation inhibitor according to claim 1, characterized in that it contains a valine derivative or a salt thereof in which the valine derivative is a methyl group having 1 carbon atom.

3. A hair cosmetic characterized by containing the cuticle peeling inhibitor or split end generation inhibitor described in claim 1 or 2.

4. The hair cosmetic according to claim 3, characterized in that it is a cleansing agent, a leave-in treatment, and a hair styling agent.

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