JP2011037729A - Hair modifier, and hair cosmetic improving volume feeling of hair containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a hair modifier which imparts sufficient volume feeling to keratin fiber such as a hair, and also is excellent in durability and feeling. <P>SOLUTION: The hair modifier composition includes: an amphoteric surfactant expressed by (A) formula (1) where R<SP>1</SP>is a 10-18C alkyl group or alkenyl group; and amino alcohol expressed by (B) formula (2) where R<SP>1</SP>is a 10-18C alkyl group or alkenyl group. In the hair modifier composition, the compounding weight ratio of an A ingredient to a B ingredient is 99:1 to 80:20. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

  The present invention gives a persistent and voluminous feel to softened or weak hair that has been damaged by chemical treatment such as perm, bleach, hair color, etc., and makes it softer and softer. The present invention relates to a hair modifier composition that can be used and a hair cosmetic composition that improves the volume of hair containing the same.

  Hair is damaged by living environment such as ultraviolet rays and free chlorine, and human behavior such as hair care and hair makeup. In washing damaged hair, it is known that the surfactant, which is the main component of shampoo, elutes sebum and hair constituent proteins of the hair and weakens the hair.

In recent years, the frequency of cold perms, hair coloring, hair bleaching, and the like has increased, and chemical treatment with chemicals has promoted elution and structural change of hair constituent proteins, which has spurred damage.
Such weakened damaged hair and naturally thin and soft hair have a problem of difficulty in styling because there is no volume feeling.

  Styling is a particularly important factor for women in hair and makeup behavior, and cosmetics and makeup methods that give hair a sense of volume have been developed and reported.

(1) A method of combining an anionic surfactant and a polyvalent metal salt (Patent Document 1)
(2) A method of combining an organic solvent and an aromatic compound (Patent Document 2)
(3) A method using a film forming agent such as silicones, peptides and polymers (for example, Patent Document 3)

  Among these conventional techniques, (1) and (2) aim at reinforcing the inside of the hair, and (3) is a technique aimed at reinforcing the hair surface.

  On the other hand, the present inventors have revealed that the compounds used in the present invention have the following performance. (Patent Document 4)

  That is, (i) excellent compatibility with other surfactants, (ii) viscosity building is possible by combining other surfactants, and (iii) a specific range especially with sulfur-containing anions Has a special rheological property in which the viscosity does not decrease even when diluted, and (iv) the discoloration of the dyed hair is less than other surfactants despite having normal detergency It is known that it has characteristics such as being less, (v) capturing free chlorine, and reducing the influence of free chlorine on the human body.

Japanese Patent Laid-Open No. 06-172138 Japanese Patent No. 2119260 Japanese Patent Laid-Open No. 60-112710 US Publication No. 2007-0265181

  However, with regard to the cosmetics aimed at the conventional hair modification effect, the method (1) takes time until the effect is obtained, and the effect is not sufficient. The elasticity is improved, and this elasticity has the property that it can be maintained for a long period of time. However, there is a drawback in that it cannot be added in a large amount to the compounded product at the same time because there are restrictions on the compounding, and the compounded formulation is limited.

  The method (3) is the most commonly used method, but has the drawback that the hair improving effect is lost by washing the hair after treating it once.

  Accordingly, there has been a demand for a hair modifier that imparts a sufficient volume feeling to keratinous fibers such as hair and is excellent in sustainability and feel.

  The inventors of the present invention made a hair cosmetic containing a specific amphoteric surfactant composition and a hair improver containing a specific amino alcohol in a specific ratio and made it into a monitor test. I got a response that a feeling came out. Further, as a result of intensive studies, it was confirmed that the specific amphoteric surfactant composition has an effect of increasing hair such as adhering to the surface of the hair and at the same time has an effect of imparting flexibility to the hair, thereby completing the present invention. .

That is, the present invention
(1) (A) General formula (1)

[However, in the above formula (1), ^{R 1} represents an alkyl group or alkenyl group having 10 to 18 carbon atoms. ]
An amphoteric surfactant represented by
(B) General formula (2)

[In the above formula (2), R1 is an alkyl or alkenyl group having 10 to 18 carbon atoms]
The hair modifier composition characterized by containing the amino alcohol shown by these, and the compounding weight ratio of A component and B component is 99: 1-80: 20.

(2) A hair cosmetic comprising the hair modifier composition according to (1).
It is about.

  The present invention provides a hair makeup that gives a sense of volume to a hair that has been damaged by chemical treatment such as perm, bleach, hair color, etc. You can get a fee.

It is a photograph of the hair | bristle bundle which shows the antistatic effect of an Example. The photo shows the results of SAMPLE01, SAMPLE02, SAMPLE03, and SAMPLE04 from the left.

  Hereinafter, embodiments of the present invention will be described.

  The amphoteric surfactants represented by the general formulas (1) and (2) of the present invention will be described in detail.

  The amphoteric surfactant represented by the general formula (1) can be obtained by a method in which an amine is reacted with an epoxyalkane and then betaine-ized with a halocarboxylic acid as shown in the following chemical formula.

[However, R ¹ is the same as the previous definition]
Preferable examples of the amphoteric surfactant represented by the general formula (1) include N- (2-hydroxydodecyl) -N-hydroxyethyl-N-methylglycine, N- (2-hydroxydecyl) -N-hydroxyethyl. -N-methylglycine, N- (2-hydroxyundecyl) -N-hydroxyethyl-N-methylglycine.
The compound of the general formula (2) is also a raw material of the general formula (1) before quaternization with monochloroacetic acid, but is an essential component in the present invention.

When the betaine of the general formula (1) is produced by a production method (for example, Production Example 1 or Production Example 2) that is usually performed, the amine represented by the general formula (2) may remain as an unreacted product in an amount of 5 to 10%. However, the mixing ratio of the compounds of the general formula (1) and the general formula (2) including the unreacted product is preferably 99: 1 to 80:20.
When the compound of the general formula (1) and the compound of the general formula (2) is too much of the compound of the general formula (2) with respect to 99: 1 to 80:20, the compound of the general formula (2) is water-soluble. This is not preferable because the low temperature stability is impaired.

The mixing ratio of the compounds of the general formula (1) and the general formula (2) is not preferable when the compound of the general formula (2) is too small relative to 99: 1 to 80:20 because the effect of imparting volume feeling is weakened.
In addition, inorganic salts, glycolic acid and the like are contained as by-products of the betainization reaction, and these are more preferably removed by topping treatment, electrodialysis treatment, and reverse osmosis membrane treatment.

The hair cosmetic composition containing the hair modifier composition of the present invention can be appropriately selected from dosage forms such as transparent liquid, gel, cream, emulsion, mousse, shampoo, rinse, treatment, conditioner, It can be in the form of a hair liquid, hair growth lotion or the like.
The addition amount of the hair modifier composition of the present invention to each dosage form is preferably 0.5 to 30% by weight when the outer phase is hydrophilic, and is blended at a ratio of 0.5 to 10% by weight when the outer phase is lipophilic. It is preferable to do.

  When the amount of the hair modifier composition of the present invention is less than the above range, the effect of the invention is not preferable, and when it exceeds the above range, the stability of various dosage forms may be problematic. It is not preferable. In any case, the composition of the present invention can carry out a higher blending amount than the conventional hair modifier, and its application range is wide.

  The hair cosmetics of the present invention include animals, plants, fish shellfish, microorganism-derived extracts, powder components, liquid fats and oils, solid fats and oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones, anionic surface activity Agents, cationic surfactants, amphoteric surfactants other than general formula (1), nonionic surfactants, humectants, water-soluble polymers, thickeners, coating agents, UV absorbers, flame retardants, metal sequestering agents , Lower alcohols, sugars, amino acids, organic amines, synthetic resin emulsions, pH adjusters, skin nutrients, vitamins, antioxidants, antioxidant auxiliaries, perfumes and deep sea water as needed. Two or more may be used.

The contents of the present invention will be described in more detail with reference to examples.
Production Example 1 General Formula (2) N-2-Hydroxyalkyl-N-2-hydroxyethyl-N-methylamine In a 2-liter 4-neck flask, 504.0 g of N-Me-monoethanolamine (1.05 equivalent of epoxy) ), The temperature was raised to 80 ° C., 1256.8 g (6.39 mol) of C12,14 epoxy (manufactured by Daicel, AOEX24 DG-009) was added dropwise over 3 hours, and the mixture was stirred at 80 ° C. overnight. The epoxy residue is N. D. After confirming that the excess amine was distilled off with a vacuum pump at 80 ° C., 1735 g of N-2-hydroxyalkyl-N-2-hydroxyethyl-N-methylamine was obtained.

Production example 2 General formula (1) N-2-hydroxyalkyl-N-2-hydroxyethyl-N-methylglycine aqueous solution Next, N-2-hydroxyalkyl-N- was added to a 5-liter four-necked flask. 810.1 g (2.98 mol) of 2-hydroxyethyl-N-methylamine and 1961 g of water were added and the temperature was raised to 70 ° C. An 80% aqueous solution of sodium monochloroacetate (493.0 g, 1.4 equivalents of amine) and 400 g of NaOH 48% (1.2 equivalents of monochloroacetic acid) were added dropwise over 2 hours in the range of pH = 7-8. The temperature was raised to 97 ° C., and aging was carried out for 17 hours while appropriately adding 40 g of 48% NaOH (0.1 equivalent of monochloroacetic acid) in the range of pH = 7-8. After cooling to room temperature, water was added, and an N-2-hydroxyalkyl-N-2-hydroxyethyl-N-methylglycine aqueous solution was taken up with a total weight of 3775 g. Dry residue = 35.4%, NaCl = 6.3%, active ingredient (dry residue-NaCl) = 29.1%, glycolic acid = 2.8%, betaine yield from HPLC (UV) = 92% Therefore There will be 8% of the remainder of general formula (2).
H1-NMR of the product of Production Example 2 measured in heavy water 0.9 ppm 3H
1.3-1.5 ppm 20H
3.4ppm 3H
3.5-4.3 ppm 9H

Production Example 3 Desalted N-2-Hydroxyalkyl-N-2-hydroxyethyl-N-methylglycine aqueous solution The N-2-hydroxyalkyl-N-2-hydroxyethyl-N-methylglycine aqueous solution prototyped in Production Example 2 was prepared. The RO membrane was treated to make the N-2-hydroxyalkyl-N-2-hydroxyethyl-N-methylglycine aqueous solution the same concentration, and the salinity was reduced to 1.5%.

Examples 1-2 and Comparative Examples 1-4
As a compound of hair increasing effect production examples 1 to 3 and comparison,
Perisea L-30 Dilauroyl glutamic acid ricin Na (manufactured by Asahi Kasei Chemicals),
Promois EFLS (manufactured by Seiwa Kasei Co., Ltd.)
An experiment on the effect of increasing hair was conducted on commercially available hair modifiers.

The thickness of the hair was measured with an electron microscope.
Fourteen straight hairs were selected from a bleached hair bundle (BR · 3 manufactured by Beaulux Co., Ltd., length 10 cm, weight 1 g), and fixed to an electron microscope measurement stage. 28 places were measured and the initial hair diameter was measured.
Adjust 200g of hair treatment agent with the blending ratio shown in the table below, dive each stage so that the soaking time is 5 minutes, then rinse with 1L of tap water for 1 minute x 2 times, depressurize the glock with a vacuum pump to 10 Dried for minutes. 28 points were measured with an electron microscope, and the top and under of the change in thickness were cut at 4 points, and the measured values at 20 points were statistically processed.
Furthermore, the same sample was continuously dipped so that the total dipping time was 15 minutes and 30 minutes, and the change in the size of the various samples was examined. It is a percentage notation of the diameter increased with the initial as 100.
Moreover, the hair bundle for sensory evaluation was immersed in this test measurement solution for 5 minutes, rinsed in running tap water for 2 minutes, and the dry touch after natural drying <hair surface feel> was evaluated. Evaluation was performed by sensory evaluation with 5 panelists based on the treated hair of Comparative Example 2.

Sensory evaluation criteria <hair surface feel>
I feel that the feel is superior to Comparative Example 2. The 3-point feel is equivalent to Comparative Example 2. 2-point feel is inferior to Comparative Example 2.
9 to 11 reference points total ○
Reference point total 5-8 points ×
The results evaluated and described in the table are shown in the table.

  Although the hair diameter was most increased by the compound of Comparative Example 4 (Production Example 1), the sensory evaluation after dipping the hair bundle showed that the hair surface was poor in touch and the hair was stiff. The homogeneity of adhesion to the hair surface was poor, and it was found that the performance was insufficient as a hair quality improving agent. There was no difference in the feel of the hair bundle of Comparative Example 2, which was another hair modifier and a blank.

  The increase rate of the hair diameter is most excellent in Example 1 except for Comparative Example 4, and it is considered that excellent absorption or penetration into the hair occurs in a short time. That is, in the present invention, it is necessary that both betaine represented by the general formula (1) and an amine represented by the general formula (2) are blended.

Elastic recovery and softening of hair
Since the composition of the present invention was found to be excellent in the effect of increasing hair, how the mechanical parameters of the hair change due to the increase effect was determined using a pure bending tester (KESFB2-S type, manufactured by Kato Tech Co., Ltd.). Measured.
The stress [B value (gf · cm ² / cm)] during the bending was measured. This B value is a numerical value indicating the bending elasticity when one of the hairs is fixed and bent at a constant speed, and the higher the numerical value, the harder the hair (the stronger the spring).
First, bending stress was measured for healthy hair and strong damaged (bleach) hair.

  Healthy hair shows a softer value than bleached hair. Considering this fact and the measurement of tensile stress, considering that healthy hair generally has a higher breaking stress than bleached hair, the internal structure of bleached hair has defects and the flexibility of hair fibers is lost. Interpreted as having a hard elasticity.

The bleached hair was immersed in the solution of Example 1 for 30 minutes, rinsed twice, and then naturally dried in a constant temperature and humidity chamber at 20 ° C. and a humidity of 60%, and then the bending stress was measured. As a result, it has been found that when bleached hair is treated with the composition of the present invention, the elastic strength decreases and acts in the direction of softening damaged hair.
Furthermore, the following formula was used to evaluate how close the viscoelastic properties of bleached hair were to healthy hair by the composition of the present invention.

  As is apparent from the results in Table 3, it means that the elasticity is brought close to healthy hair by causing the composition of Example 1 to act on the bleached hair. This means that the composition of the present invention thickens the hair of bleached hair and at the same time brings the elastic property close to that of healthy hair. When bleach hair is treated with a normal film-forming component or oil / fat component, the hair may increase, but the elastic property acts in the direction of hardening, whereas the composition of the present invention softens the elastic property. There are features that affect the direction.

Maintenance experiment of hair enhancement effect Confirmation of performance maintenance performance by washing after application of hair treatment agent As a feature of the composition of the present invention, hair treatment agent is extremely reduced even after shampooing after treatment once on hair. Less was revealed by measuring the hair diameter after shampooing.

Fourteen straight hairs were selected from a hair bundle of a bleached hair bundle (BR.3 manufactured by Beaulux Co., Ltd., length 10 cm, weight 1 g), and fixed to an electron microscope measurement stage. 28 places were measured and the initial hair diameter was measured.
Next, the bleached hair bundle is immersed in the treatment solution of Example 1 for 30 minutes, rinsed twice, and then naturally dried in a constant temperature and humidity chamber at 20 ° C. and a humidity of 60%, and 14 straight hairs are selected from the hair bundle, The sample was fixed on an electron microscope measurement stage. 28 places were measured and the hair increasing effect was measured.
Next, the hair bundle is immersed in a simple shampoo solution of SLES 5.0% (pH 6.0) for 30 minutes, rinsed twice, and then air-dried in a constant temperature and humidity chamber at 20 ° C. and 60% humidity, and directly from the hair bundle. 14 hairs were selected and fixed on an electron microscope measurement stage. 28 places were measured and the shampoo tolerance diameter was measured.

  As a comparative example, various hair diameters were measured using the method described above except that a 1% lauryltrimethylammonium chloride solution was used instead of the treatment liquid of Example 1, and the percentage notation of the diameter increased with the initial as 100. To do. The results of confirming how the hair increasing effect is changed by shampooing are shown below.

  Both the lauryltrimethylammonium chloride solution and the treatment solution of Example 1 show 4 to 5% hair increase effect, but it can be seen that the increase effect is reduced by the simple shampoo solution treatment. However, since the increase effect of the treatment liquid of Example 1 is not a negative value, the hair increase effect may be increased by repeatedly using the composition of the present invention or the hair cosmetic containing the same. There is.

The antistatic effect strength damage (bleach) hair was dipped in various surfactant solutions (concentration 0.5%, pH 6) for 6 hours and rinsed. After drying, combing was performed 5 times with a resin comb.
The result of the photograph shown in FIG. 1 was obtained. Except for SAMPLE02, it can be seen that the hair is charged by combing and the tip of the hair is spreading.

  When each hair bundle was subjected to sensory evaluation, the sensory evaluation of the hair bundle treated with the hair treatment agent of the present invention was the most excellent. In the sensory evaluation of the hair bundle, evaluations such as “soft” and “good finger sliding” were obtained. It was.

SAMPLE01 Washing only
SAMPLE02 Treatment agent of the present invention Example 2 used
SAMPLE03 POE lauryl sulfate
SAMPLE04 Cocoamide Betaine

That is, the composition of the present invention has an effect of increasing hair, particularly with respect to damaged hair, has the effect of restoring its viscoelasticity to healthy hair, has an antistatic effect after drying, and is excellent in bundling by brushing. Improve the feel to be soft and slippery. Furthermore, since the effect of the composition of the present invention is excellent in shampoo resistance, it has been found from the Examples that a synergistic improvement effect can be expected by cumulatively treating the hair with the composition of the present invention.
The following is an example of a hair cosmetic formulation formulated with the composition of the present invention.

Example 3 Pearl-like shampoo N-lauroylalanine arginine salt using the hair modifier composition of the present invention 12.0
Polyoxyethylene lauryl ether sulfate triethanolamine salt 4.0
Visco Safe ^(R) LMPE (Note 1) 3.5
Palm oil fatty acid monoethanolamide 1.0
Amphoteric surfactant of Production Example 2 6.0
Cationized cellulose 0.1
Cationized guar gum 0.1
Polyoxypropylene palm oil fatty acid isopropanolamide 3.0
Ethylene glycol distearate2.0
Amount of citric acid pH 6.5 Methylparaben 0.5
Piroctone olamine 0.3
Glycyrrhizic acid 2K 0.3
EDTA 0.1
Sodium chloride 0.5
Fragrance 0.3
Purified water to 100%
Note 1: Made by Kawaken Fine Chemical Co., Ltd.
This shampoo is a prescription composition containing 6.0% of an amphoteric compound of general formula 1 and an amine of general formula 2 in a ratio of 91.3: 8.7.

Example 4 Transparent shampoo using the hair modifier composition of the present invention
Sodium polyoxyethylene lauryl ether sulfate (3EO) 5.0
Amine of Production Example 1 1.0
Amphoteric surfactant of Production Example 2 10.0
Palm oil fatty acyl-L-glutamic acid triethanolamine 1.0
Lauroyl sarcosine sodium 3.5
Lauroylamidoamine oxide 1.0
Hydroxypropyl methylcellulose 0.2
Behenyl alcohol 1.0
Propylene glycol 3.0
ε-polylysine 0.5
Polyoxyethylene behenyl ether 0.1
Hydroxyethanediphosphonic acid 0.1
Fragrance 0.1
Amount of malic acid pH 6.5 to purified water to 100%
This shampoo is a prescription composition containing 11.0% of an amphoteric compound of general formula 1 and an amine of general formula 2 in a ratio of 80.4: 19.6.

Example 5 Hair conditioner using the hair modifier composition of the present invention A component and B component are separately heated to 80 degrees, added to component A and emulsified, cooled to 60 degrees and cooled to C component. It was created by the procedure of blending.
A Stearyltrimethylammonium chloride 2.00
A Polyoxyethylene (2 mol) oleyl ether 2.00
A Glycerol monostearate 1.00
A ethylene glycol monostearate2.00
A Squalane 1.00
A Astaxanthin 0.01
A BHT 0.01
B Methylparapen 0.10
B Serine 0.50
B Sodium hyaluronate 0.50
B Polyoxyethylene (60 mol) hydrogenated castor oil 2.00
B Amine of Production Example 1 0.50
B. Amphoteric surfactant of Production Example 2 5.00
C fragrance 0.10
B Purified water to 100%
This hair conditioner is a prescription composition containing 5.5% of an amphoteric compound of general formula 1 and an amine of general formula 2 in a ratio of 80.4: 19.6.

Example 6 Hair Growth Lotion Minoxidil 2.0 Using the Hair Modifier Composition of the Present Invention
Isopropyl alcohol 50.0
Ethanol 10.0
Amine of Production Example 1 0.5
Amphoteric surfactant of Production Example 2 5.0
Lauric acid diethanolamide 0.5
Purified water to 100%
This hair growth lotion is a prescription composition containing 5.5% of an amphoteric compound of general formula 1 and an amine of general formula 2 in a ratio of 80.4: 19.6.

  The cosmetic for hair containing the hair modifier composition of the present invention can be appropriately selected from dosage forms such as transparent liquid, gel, cream, emulsion, mousse and the like, shampoo, rinse, treatment, conditioner It can be in the form of a hair liquid or the like.

Claims (2)

(A) General formula (1)
[However, in the above formula (1), ^{R 1} represents an alkyl group or alkenyl group having 10 to 18 carbon atoms. ]
An amphoteric surfactant represented by
(B) General formula (2)
[In the above formula (2), R ¹ is an alkyl or alkenyl group having 10 to 18 carbon atoms]
The hair modifier composition characterized by containing the amino alcohol shown by these, and the compounding weight ratio of A component and B component is 99: 1-80: 20. A hair cosmetic comprising the hair modifier composition according to claim 1.