KR20160131329A - Permanent wave composition comprising glutathione, and permanent wave set having the same - Google Patents

Permanent wave composition comprising glutathione, and permanent wave set having the same Download PDF

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KR20160131329A
KR20160131329A KR1020150063377A KR20150063377A KR20160131329A KR 20160131329 A KR20160131329 A KR 20160131329A KR 1020150063377 A KR1020150063377 A KR 1020150063377A KR 20150063377 A KR20150063377 A KR 20150063377A KR 20160131329 A KR20160131329 A KR 20160131329A
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hair
agent
glutathione
cysteamine
composition
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KR1020150063377A
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Korean (ko)
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KR101721939B1 (en
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양바오로
박병권
최아람
이지원
박진오
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유씨엘 주식회사
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64Proteins; Peptides; Derivatives or degradation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22Peroxides; Oxygen; Ozone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair

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  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

More particularly, the present invention relates to a pharmaceutical composition having superior perming action but less hair damage, and more particularly, to a pharmaceutical composition containing at least one reducing compound selected from thioglycolic acid and cysteamine and glutathione And a set of the phamms comprising the same. INDUSTRIAL APPLICABILITY The present invention has an effect of having an excellent permanent action without damaging the hair.

Description

FIELD OF THE INVENTION The present invention relates to a pharmaceutical composition containing glutathione,

The present invention relates to a pharmaceutical composition having excellent permanent action and little hair damage, and a pharmaceutical set comprising the same.

The hair is composed of keratin composed mainly of 18 amino acids, cysteine is about 16% of the amino acids in the keratin, and the shape of the hair is mainly formed by fixing cystine by disulfide bonding with cystine.

In the permanent processing of the hair (in particular, the waving permanent hair processing), hair is treated with a permanent liquid (or treatment liquid) containing a reducing agent to cut or cleave disulfide bonds in the keratin, To form a rod of a desired shape, and then applying an oxidizing agent thereto again to build up a disulfide bond between the cysteamine and fix it. By this method, the hair can be straightened or curled.

As the reducing agent of the perm solution, for example, thioglycolic acid, cysteine, cysteamine, glyceryl thioglycolate, thiolactic acid and the like are used. Typically, a perm solution containing thioglycolic acid and a perm solution containing cysteamine are used.

The perm solution containing thioglycolic acid is excellent in the action of perming the hair to be processed, but the hair is remarkably damaged due to its strong action against the hair as compared with the cysteamine. Therefore, use of hair is particularly limited in damaged hair, such as discolored and dyed hair. In addition, when thioglycolic acid is used, the degree of formation of permanent hair and hair follicle is different, and the hair becomes frizzy, the tip is split, and the frizz is increased.

On the other hand, a permanent solution containing cysteamine has a low degree of damage to hair, but it is difficult to roll hair with a normal rod because the action of perming the hair is weak, This is being limited. In addition, in the case of damaged hair, permanent processing is more difficult than healthy hair. Also, when cysteamine is used, the ends of the hair are cracked or broken, and gloss is lost. In addition, even if a cysteamine, which is generally thought to be less damaging to hair, is applied 2 to 3 times, a permanent phenomenon may occur after the cysteamine is dried, (flaking).

Conventional techniques for preventing hair damage and achieving an excellent permanent formation effect can be understood with reference to Patent Documents 1 to 4 below. As a result, the entire contents of Patent Documents 1 to 4 are cited and incorporated as prior art in this specification.

Japanese Patent Application Laid-Open No. 11-500147 (Patent Document 1) discloses an oxidizing composition containing an oxidizing agent such as a ceramide compound and an aqueous hydrogen peroxide solution, and a method of decolorizing or perming hair using the same.

Korean Patent Publication No. 1995-0007905 (Patent Document 2) discloses a hair wave preparation which is hypo-hygroscopic and has a good wave formation, a hair wave preparation containing a thioglyceryl acyl ether or 1-phenyl-2-mercaptoethanol as a main component ≪ / RTI >

Korean Patent Laid-Open Publication No. 2015-0015213 (Patent Document 3) discloses a method of applying a filler to coat a filler with several or fewer hairs that have a high degree of damage depending on the degree of damage of the hair.

Korean Patent Laid-Open Publication No. 2013-0058877 (Patent Document 4) discloses a pesticide additive composition which neutralizes toxicities contained in hair dyeing agents and tobacco drugs and removes an unpleasant smell. Examples of such additives include dietary sulfur, loess, chitosan, molasses, honey, The fermentation broth was prepared by adding the fermented broth to the fermentation broth and then adding the fermented broth to the fermentation broth by adding deep seawater, myrtle leaf, green tea leaf, chestnut husk, mulberry leaf extract, aloe extract, licorice extract, licorice, pineapple extract, , Black tea extract, coffee bean extract, plum extract, and yucca extract are diluted in diatomaceous earth and heated to be aged. Then, the above aging solution is added with persimmon vinegar, plum vinegar, propolis, eucalyptus leaf oil, lemon oil, And a pesticide additive composition prepared by diluting peppermint and then aging.

However, there is a lot of room for improvement in improving the permanent effect of the hair, which is damaged even by the above-mentioned pharmaceutical composition and permer method, and prevention of hair damage due to permanent processing.

JP P11-500147A (1999.01.06.) KR 1995-0007905 B1 (1995.07.21.) KR 10-2015-0015213E (2015.02.10.) KR 10-2013-0058877 A (2013.06.05.)

Therefore, further from the above-mentioned prior art, it is an object of the present invention to provide a pharm composition and a set of pharmes which have excellent permanent action without damaging the hair.

The present invention is characterized in that it contains at least one reducing compound selected from thioglycolic acid and cysteamine and glutathione in order to solve the above-described problems of the prior art and to provide better hair damage prevention and permanent effect ≪ / RTI >

The present invention also provides a pharmaceutical composition, wherein the glutathione is contained in an amount of 1.5 wt% or less based on the total weight of the composition.

Also, the present invention provides a pharmaceutical composition, wherein the reducing compound is contained in a weight ratio of thioglycolic acid: cysteamine = 1: 0.1-4.

The present invention also provides a pharmaceutical composition, wherein the pH of the pharmaceutical composition is within the range of 7 to 9.5.

Also, the reducing agent 1 of the filler composition of the present invention; And a second oxidizing agent of a composition comprising at least one oxidizing compound selected from hydrogen peroxide, bromate, perborate, and perchlorate.

INDUSTRIAL APPLICABILITY The present invention has an effect of having an excellent permanent action without damaging the hair.

Fig. 1 and Fig. 2 show a wave formation test mechanism by the Kirby method in the wave formation efficiency measurement.

Hereinafter, the present invention will be described in detail.

According to an aspect of the present invention,

At least one reducing compound selected from thioglycolic acid and cysteamine, and glutathione.

The thioglycolic acid and the cysteamine are more preferably selected because they have good ability to form a hair wave, as compared with other reducing compounds self-evident to those of ordinary skill in the art (hereinafter referred to as "those skilled in the art"). In other words, thioglycolic acid has a strong reducing power, and cysteamine has a small hair-penetrating ability due to its small molecular size, and thus has a small effect on pH. Therefore, cysteamine is more preferably selected as a more preferable material than other materials.

In particular, in the present invention, it is preferable that the thioglycolic acid: cysteamine is contained in a weight ratio of 1: 0.1-4. Because the perm solution containing the thioglycolic acid is excellent in the function of perming the hair to be processed, the hair is remarkably damaged due to strong action on the hair as compared with the cysteamine, and damage such as discoloration and dyed hair, The use of thioglycolic acid is particularly limited in severe hair. In addition, the use of thioglycolic acid results in a difference in the degree of permanent formation of the hair ends and the hair follicles, resulting in hair becoming frizzy, cracked, This tendency is reflected by the increase of its content. On the other hand, a permanent solution containing cysteamine has a low degree of damage to hair, but it is difficult to roll hair with a normal rod because the action of perming the hair is weak, And in addition, in the case of damaged hair, permanent processing is more difficult than healthy hair. Further, when the cysteamine is used, the end of the head becomes cracked or broken, the hair becomes uneven, and when the permanent is applied 2 to 3 times, the permanent does not easily occur. As a result, There is a need to limit the upper limit of the content. In summary, when the content of cysteamine relative to thioglycolic acid is less than 0.1, hair damage occurs severely, and when the content is more than 4, the wave forming efficiency is extremely lowered. A more detailed understanding of this may be made through the following examples and experiments.

In addition to the above-mentioned thioglycolic acid or cysteamine, the reducing compound may include, but not limited to, a known reducing agent widely used in the art and known to those skilled in the art. Examples thereof include cysteamine, Glyceryl thioglycolate, and thio lactic acid.

The glutathione is a compound represented by the molecular formula C 10 H 17 N 3 SO 6 , which is contained in almost all living cells such as animals and yeast in nature, and is a nodular polypeptide which plays an important role in the redox reaction in vivo.

In particular, in the present invention, glutathione is included as an essential component in the pharmaceutical composition, with the surprising discovery that glutathione, a known substance, can minimize hair damage. In addition, cysteamine, cysteine, and the like in the reducing compound tends to be easily converted into a substance insoluble in water when it comes into contact with air. When such an oxidation reaction occurs, not only the efficiency of forming a wave of the reducing compound decreases, The resulting oxides can adversely affect hair and scalp and the like and cause skin troubles. Under the surprising discovery that glutathione is included in the filler composition to enhance storage stability, glutathione is added to the filler composition as an essential component . A more detailed understanding of this may be made through the following examples and experiments.

The glutathione is preferably contained in an amount of 1.5 wt% or less based on the total weight of the composition. If it is contained in an amount of more than 1.5% by weight, not only the wave-forming efficiency is greatly lowered but also the scalp discoloration is caused as compared with the degree of improvement of the hair enhancing effect, which is not preferable. In addition, the minimum content of glutathione should be at least 0.001% by weight, preferably at least 0.01% by weight, more preferably at least 0.1% by weight, and may exhibit the effect of containing glutathione. A more detailed understanding of this may be made through the following examples and experiments.

The pH of the pharmacological composition is preferably in the range of 7 to 9.5. If the pH is less than 7, the reducing power of the reducing compound may be weakened. If the pH is more than 9.5, the hair may be severely damaged.

According to another aspect of the present invention,

And the above-mentioned pharmacological composition is made into a reducing first agent and, in addition, an oxidizing second agent.

As the oxidizing second agent, known oxidizing compounds known to those skilled in the art may be used without limitation, and examples thereof include at least one oxidizing compound selected from hydrogen peroxide, bromate, perborate, and perchlorate.

In the present invention, as a more preferable oxidizing compound, one selected from hydrogen peroxide and bromate can be used.

The oxidative second agent can be formed into a disulfide bond between cysteine and then fixed, whereby the hair can be straightened or curled.

Hereinafter, the present invention will be described in more detail by way of examples. It is to be understood that the following embodiments are for the purpose of illustration only and are not intended to limit the scope of the present invention.

Example

As shown in each of Tables 1 to 3 below, a reducing agent 1 and an oxidizing agent were prepared.

1st  My

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Ethidonic acid 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Monoethanolamine 2.7 2.7 2.7 2.7 2.7 2.7 2.7 Cysteamine - 0.5 1.5 2.5 2.0 4.0 5.0 Thioglycolic acid 5.0 4.5 3.5 2.5 3.0 1.0 - Laurez-23 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Flavoring agent 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Purified water Balance Balance Balance Balance Balance Balance Balance

Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Ethidonic acid 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Monoethanolamine 2.7 2.7 2.7 2.7 2.7 2.7 2.7 Cysteamine 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Thioglycolic acid 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Glutathione 0.1 0.3 0.5 1.0 1.5 2.0 2.5 Laurez-23 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Flavoring agent 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Purified water Balance Balance Balance Balance Balance Balance Balance

Second article

Example 15 Example 16 Propylene glycol 1.0 1.0 Phosphoric acid 0.05 0.01 Sodium phosphate 0.2 0.1 Laurez-23 0.5 0.5 Flavoring agent 0.1 0.1 Hydrogen peroxide water (35%) 7.0 - Sodium bromate - 8.0 Purified water Balance Balance

Experimental Example

The hair of a teenager was wrapped with 3 to 5 ml of shampoo, and the hair was closed again with 3 to 5 ml of shampoo by sufficiently foaming and then wiped with a towel to dry.

Subsequently, 20 ml of water was sprayed on the reductive first agent (wrapped with a rod), covered with a cap, irradiated with a low-temperature far-infrared ray, and irradiated with about 25 After standing for a minute, it was confirmed that one rod was peeled and curled.

Thereafter, 40 ml of water was lightly sprayed, the water was removed lightly with a towel, the oxidizing agent was applied, and allowed to stand for 5 minutes. After that, the same oxidizing agent was applied and allowed to stand for 5 to 7 minutes Loaded out.

Measurement of Wave Formation Efficiency

The measurement of the wave forming efficiency was carried out by the wave forming test instrument of FIGS. 1 and 2 by the Kirby method.

A bundle of 15 to 20 cm long healthy hair swatches was fixed on one side of the plastic appliance of Fig. 1, and was staggered alternately with a pin bar to fix the other side.

The hair fixed on the pin bar was placed in a charlet containing the reducing agent first solution of Examples 1 to 14 and allowed to stand in a constant temperature bath at 25 占 폚 for 20 minutes. After the apparatus was removed from the sharlet, the reducing agent first agent solution was washed with running water, and then the apparatus was placed in a charette containing the oxidative agent solution of Example 15 or 16, and left in a 25 ° C thermostatic chamber for 20 minutes. After leaving the plastic apparatus, the plastic apparatus was taken out and washed with flowing water, and the fixed hair was loosened and dried, and the formed hair was fixed naturally on the glass plate with the scale, and the wave formation efficiency was calculated according to the following equation (1) 10.

Figure pat00001

Where a is the distance between the first and sixth rods of the instrument, b is the distance between the five mountains of the wavy hair, c is the straight line between the five mountains of the wavy hair, .

Hair Damaged  Measure

1) 15 ~ 20 cm of decolorized hair, dyed hair, normal hair piece (Swatch) was shampooed and towel-dried. Towel After uniformly applying the reducing agent 1 solution to the dried hair, it was wound on the rod with a constant force, left for 20 minutes, washed with water flowing in the rod state, uniformly coated with the oxidizing agent solution, left for 20 minutes, After washing with flowing water and drying, hair pieces treated with reducing agent 1 and oxidative agent 2 and hair pieces before treatment were rubbed with a sump method and observed with a microscope to observe the damage level of the cuticle layer The results are shown in Tables 7 to 10 below.

2) The hair of the same model as that used in the above 1) was divided into two halves (Half Test) and shampooed. The reducing agent 1 was uniformly applied to the dried hair, and the hair was wound on the rod with a constant force. After washing with running water and uniformly applying the oxidizing agent solution, the solution was allowed to stand for 20 minutes. Then, the rod was washed with flowing water, dried, and compared with the combing against the hair pieces treated with the reducing agent 1 and the oxidizing agent 2. The results are shown in Table 4 below.

sign Judgment Criteria - No damage + Weak damage ++ Severe damage +++ Severe damage

scalp Discoloration  Measure

The skin around the hair of the back of the ear was cleanly washed with soap and the first reducing agent of the first reducing agent was applied to the coin size for 20 to 30 minutes or 48 hours and then washed with water. Table 10 shows the results. The subjects were 10 ~ 50 male and female. The computed spectrophotometer was used to compare the color of the scalp before and after the procedure. The results are shown in Table 5 below.

sign Judgment Criteria - No discoloration + Slight discoloration ++ Slight discoloration +++ A clear discoloration

Exhaust  Measure whether

Twenty persons were subjected to sensory evaluation with each piece of swatch (Swatch) after completion of the wave formation efficiency test (①).

Using the reducing agent 1 of Examples 1 to 14 and the oxidizing agent 2 of Example 15, the hair was divided into two halves in center hair of female model hair of 10th, 20th, 30th, 40th, After the permanent wave, sensory evaluation was performed by a professional hairdresser. The results of the sensory evaluation were obtained by the direct sensory test according to the following Table 6.

Odor too Sensitivity of odor 0 Odorless (does not detect odor at all) None One Detecting odor (detecting a little odor) Threshold 2 Normal odor (detect odor of moderate degree) Moderate 3 Strong odor (strong odor detection) Strong 4 Extreme odor (very strong odor detection) Very Strong 5 Unbearable odor (unbearable odor) Over Strong

The measurement results are shown in Tables 7 to 10 below.

First agent:
Example 1
+
The second agent:
Example 15
First agent:
Example 2
+
The second agent:
Example 15
First agent:
Example 3
+
The second agent:
Example 15
First agent:
Example 4
+
The second agent:
Example 15
First agent:
Example 5
+
The second agent:
Example 15
First agent:
Example 6
+
The second agent:
Example 15
First agent:
Example 7
+
The second agent:
Example 15
Wave forming efficiency 73.80% 74.50% 75.30% 78.20% 81.50% 75.20% 73.50% Whether the hair is damaged +++ +++ ++ ++ ++ + + Whether the scalp is discolored - - - - - - - Whether 4 4 3 2 One One 0

First agent:
Example 8
+
The second agent:
Example 15
First agent:
Example 9
+
The second agent:
Example 15
First agent:
Example 10
+
The second agent:
Example 15
First agent:
Example 11
+
The second agent:
Example 15
First agent:
Example 12
+
The second agent:
Example 15
First agent:
Example 13
+
The second agent:
Example 15
First agent:
Example 14
+
The second agent:
Example 15
Wave forming efficiency 81.50% 82.40% 83.50% 82.20% 81.40% 75.00% 65.30% Whether the hair is damaged - - - - - - - Whether the scalp is discolored - - - - - + + Whether One One One One One One One

First agent:
Example 1
+
The second agent:
Example 16
First agent:
Example 2
+
The second agent:
Example 16
First agent:
Example 3
+
The second agent:
Example 16
First agent:
Example 4
+
The second agent:
Example 16
First agent:
Example 5
+
The second agent:
Example 16
First agent:
Example 6
+
The second agent:
Example 16
First agent:
Example 7
+
The second agent:
Example 16
Wave forming efficiency 71.80% 72.30% 74.30% 76.60% 80.20% 73.40% 71.20% Whether the hair is damaged +++ +++ ++ ++ ++ + + Whether the scalp is discolored - - - - - - - Whether 4 4 3 2 One One 0

First agent:
Example 8
+
The second agent:
Example 16
First agent:
Example 9
+
The second agent:
Example 16
First agent:
Example 10
+
The second agent:
Example 16
First agent:
Example 11
+
The second agent:
Example 16
First agent:
Example 12
+
The second agent:
Example 16
First agent:
Example 13
+
Second agent: Example 16
First agent:
Example 14
+
The second agent:
Example 16
Wave forming efficiency 80.20% 81.00% 81.30% 80.00% 79.30% 71.00% 63.20% Whether the hair is damaged - - - - - - - Whether the scalp is discolored - - - - - + + Whether One One One One One One One

Storage stability experiment

The storage stability test was carried out on Example 8 containing glutathione and Example 5 not containing glutathione (experimental conditions: storage at room temperature), and the results are shown in Table 11 below.

Storage period (1 day) Shelf life (3 months) Shelf life (6 months) Example 8 3 3 2.8 Example 5 3 2.5 2

Claims (5)

At least one reducing compound selected from thioglycolic acid and cysteamine, and glutathione. The pharmaceutical composition according to claim 1, wherein the glutathione is contained in an amount of 1.5 wt% or less based on the total weight of the composition. [Claim 3] The pharmaceutical composition according to claim 1, wherein the reducing compound is contained in a weight ratio of thioglycolic acid: cysteamine = 1: 0.1-4. The flux composition of claim 1, wherein the pH of the flux composition is in the range of 7 to 9.5. A reducing first agent of the pump element composition of any one of claims 1 to 4; And
A second oxidizing agent of a composition comprising at least one oxidizing compound selected from hydrogen peroxide, bromate, perborate, and perchlorate.
KR1020150063377A 2015-05-06 2015-05-06 Permanent wave composition comprising glutathione, and permanent wave set having the same KR101721939B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220050389A (en) * 2020-10-16 2022-04-25 주식회사 삼인케미칼 Acid perm agents for damaged hair using cysteamine thioglycholate

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5362487A (en) * 1992-01-10 1994-11-08 Helene Curtis, Inc. Cysteamine permanent wave composition and method
KR950007905B1 (en) 1986-03-03 1995-07-21 가오 가부시끼가이샤 Hair waving agent
JPH11500147A (en) 1995-10-20 1999-01-06 ロレアル Novel oxidizing composition and novel hair permanent deformation or bleaching method
US20120269758A1 (en) * 2011-04-21 2012-10-25 Paul Alfred Cornwell Hair styling
KR20130058877A (en) 2011-11-28 2013-06-05 이정옥 Perm chemical composition and its manufacturing method
KR20150015213A (en) 2013-07-31 2015-02-10 함기형 Perm chemical coating method of hair containing

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR950007905B1 (en) 1986-03-03 1995-07-21 가오 가부시끼가이샤 Hair waving agent
US5362487A (en) * 1992-01-10 1994-11-08 Helene Curtis, Inc. Cysteamine permanent wave composition and method
JPH11500147A (en) 1995-10-20 1999-01-06 ロレアル Novel oxidizing composition and novel hair permanent deformation or bleaching method
US20120269758A1 (en) * 2011-04-21 2012-10-25 Paul Alfred Cornwell Hair styling
KR20130058877A (en) 2011-11-28 2013-06-05 이정옥 Perm chemical composition and its manufacturing method
KR20150015213A (en) 2013-07-31 2015-02-10 함기형 Perm chemical coating method of hair containing

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220050389A (en) * 2020-10-16 2022-04-25 주식회사 삼인케미칼 Acid perm agents for damaged hair using cysteamine thioglycholate

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