JP2020109061A - Heating permanent-wave treatment method and hair treatment agent - Google Patents

Abstract

To provide a heating permanent-wave treatment method and a hair treatment agent that improve the shortcoming of heat damage of heating permanent-wave treatment.SOLUTION: A heating permanent-wave treatment method has a step for reduction with a reductant, a step for hair reinforcing with a hair treatment agent containing levulinic acid, an intermediate water washing step, a winding step, a heating step, a step for oxidation with an oxidizer, and a water washing step.SELECTED DRAWING: None

Description

The present invention also relates to a heating permanent wave treatment method and a hair treatment agent capable of reducing damage due to heat.

A general heating permanent wave can form a curl on hair by the action of a reducing agent as a main component and a heating and oxidizing agent. Specifically, a keratin protein for hair using a first agent containing a reducing agent such as thioglycolic acid or a salt thereof, cysteamine or a salt thereof, and an alkaline agent such as ammonia water, monoethanolamine, ammonium hydrogencarbonate, and arginine. After reductively cleaving the disulfide bond existing in the above, it is washed with water, wrapped around a heatable electric heating rod and heated, and left to dry while applying heat. Then, the heatable electric heating rod is removed, and the hair is treated with a second agent containing an oxidizing agent such as hydrogen peroxide or sodium bromate as a main component to oxidize and re-form disulfide groups and fix the hair in a curled shape. However, in the curl thus obtained, the hair becomes stiff and the feel is deteriorated, and damage due to heat occurs, and the curl finish is not sufficient.

As a highly effective heating permanent wave, a method of forming a curl on hair by using an electric heating rod that can be heated by energization has been proposed. For example, in Patent Document 1, a step (1) of applying a first agent for permanent wave containing a reducing agent to hair, leaving it for 5 to 20 minutes to sufficiently soften the hair, and then washing with water (2) A step of gently wiping off the water content of the hair after washing with water and winding the hair around a rod that can be heated by energization (3) A step of energizing the rod around which the hair is wound to heat the rod and leaving it at 80 to 140°C for 1 to 20 minutes (4) A step of applying the second agent for permanent wave containing an oxidant to the hair wound around the rod or the hair removed from the rod, leaving it for 1 to 15 minutes, then washing with water and drying is disclosed. ing. According to this method, the hair is not damaged by reduction/oxidation and a strong wave can be applied to the hair, but the damage to the hair due to heating cannot be sufficiently eliminated.

Further, in Patent Document 2, a perm first agent applying step of applying a first permanent agent to unwound hair and a accelerating treatment of the first permanent agent for hair applied with the first permanent agent Perm first agent accelerating step, perm first agent removing step to wash applied perm first agent from hair, winding treatment step for winding hair after water washing step on rod equipped with heat generating device, and fever heating rod And a rod heating step of heating the hair, and a perm second agent treatment step of removing the wound hair from the rod and applying the perm second agent to the rod-out hair to treat the hair with the second permanent agent. In the permanent wave treatment method, the step of accelerating the first perm agent is performed on the hair in which the first perm agent is applied and is in a non-rolling state by an indirect heat treatment accelerator. This is a step of promoting the treatment with the first perm agent to reduce and open the S—S bond in the hair by heating from a position away from the hair, and emits infrared rays and far infrared rays as this indirect heat treatment accelerator. A heating device equipped with a heater is moved around the subject's head to heat the hair, and an indirect heat treatment accelerator that accelerates the treatment, and hot air is introduced into the hood or cap to heat the hair. At least one selected from the group consisting of an indirect heat treatment accelerator for performing the above is used, and in the above-mentioned perm second agent treatment step, the perm second agent containing an oxidizing agent as a main component is applied to the hair. The first perm agent is 1,3-butylene glycol, urea, cysteamine hydrochloride, hydrolyzed keratin, hydrolyzed silk, sodium laureth-4 acetate, which closes S-S bonds in hair. , Hydroxyethyl cellulose, ethanolamine, pentasodium pentateate, sodium lauryl sulfate, and methylparaben, and the second perm agent is sodium bromate, jojoba oil, hydrolyzed keratin, mineral oil, cetrimonium chloride, isopropanol. , Oleth-30, oleth-7, oleth-50, oleth-20, oleth-15, oleyl alcohol, lauryltrimonium chloride, sorbic acid, sodium hydroxide and phosphoric acid A wave treatment method is disclosed. With this method, it is possible to form a good curl, and in particular, to form a curl with a rounded and rich feeling, and even after the perm treatment, when the user later sets the hair with a hair dryer at home etc., Good curl can be restored, but damage to hair due to heating cannot be sufficiently eliminated. Further, before the above-mentioned perm first agent application step, it has been shown that an acidic pretreatment liquid can be sufficiently applied, in particular, since the damaged portion with a large degree of damage is inclined to alkali. It is disclosed that the pretreatment liquid of (3) preferably has a pH of around 3 (pH 2 to 4) and is mixed with an acid such as levulinic acid, citric acid, or lactic acid as a main component, but generally, the degree of damage is large. The purpose is to protect the damaged part and to mitigate the action of the first permanent agent, and there is no description about reducing the damage caused by heat in the part forming the curl.

JP 2004-262798 A Patent No. 4426985

The present invention has been made in view of the above-mentioned drawbacks of the prior art, and an object of the present invention is to provide a heating permanent wave treatment method and a hair treatment agent that can reduce damage due to heat that hardens the hair and reduces the feel.

The present inventors have conducted extensive studies to solve the above-mentioned problems, and as a result, a reducing step using a reducing agent → a hair strengthening step using a hair treating agent containing levulinic acid → an intermediate water washing step → a winding step → a heating step → an oxidizing agent The inventors have found that a heat permanent wave treatment method and a hair treatment agent characterized by comprising an oxidation step and a water washing step can reduce damage due to heat, and have completed the present invention. Although levulinic acid is known to have a pH adjusting action and is widely used in cosmetics, its effect of reducing damage due to heat has not been known. Further, in Japanese Patent No. 4648492, the first step reduction step → winding step → second step reduction step → first step oxidation step of applying an acid rinse agent containing levulinic acid → intermediate water washing step → bonding time step → second step A method is disclosed in which a stepwise oxidation process, a rod-out process, a shampoo process, and a blowing process are sequentially performed. In this method, it is disclosed that after the reduction step, an acid rinse agent containing levulinic acid is applied, but the purpose of the acid rinse agent containing levulinic acid is to reduce damage to hair due to reduction/oxidation and It has good curl durability and texture, and achieves a light curl finish, and there is no description about the effect of strengthening hair and reducing heat damage.

That is, the heating permanent wave treatment method and the hair treatment agent of the present invention are (1-1) a reducing step of applying a first permanent agent containing a reducing agent to the hair. (2-1) applying a hair treatment agent containing levulinic acid, a hair strengthening step, (3-1) rinsing and/or washing hair with hot water, an intermediate water washing step, and (3-2) winding on a heating rod, Winding step, (3-3) heating at 60 to 100°C, heating step, (4-1) applying a second permanent agent containing an oxidizing agent, oxidizing step, and (5-1) rinsing with hot water , Washing process. It is characterized by comprising the reduction step, the hair strengthening step, the oxidation step, and the water washing step.

The heating permanent wave treatment method and hair treatment agent of the present invention can reduce damage due to heat.

The heating permanent wave treatment method of the present invention essentially includes a hair strengthening step using a hair treatment agent containing levulinic acid. Hereinafter, the present invention will be described in detail.

(1-1) Applying a perm first agent containing a reducing agent to the hair. In the reducing step, the reducing agent content, pH, alkalinity, and time are set according to the degree of damage to the hair to ensure sufficient hair. Reduce to.

(2-1) In the hair strengthening step of applying a hair treatment agent containing levulinic acid, the content of levulinic acid is 0.1 to 3.0% by weight, preferably 0, relative to the total amount of the hair treatment agent. It is 0.5 to 2.0% by weight. If it is less than 0.1% by weight, the coating amount becomes too large and it takes too much time, while if it exceeds 3.0% by weight, the curling effect is lowered.

In addition to levulinic acid, other components commonly used in cosmetics, pharmaceuticals and the like can be optionally added to the hair treatment agent within a range that does not impair the effects of the present invention. Examples of such components include cationic polymers, anionic polymers, nonionic polymers, amphoteric polymers, polyhydric alcohols, sugars, amino acids, peptides, proteins, sequestering agents, oils, powder components, cationic interfaces. An activator, an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a pH adjuster, a thickener, a powder component, a fragrance, a powder component, a pigment, water and the like can be contained.

The dosage form of this hair treatment agent is not particularly limited as long as the desired effect is sufficiently exhibited, and for example, liquid, emulsion, gel, foam, cream, and other dosage forms can be adopted. It may be diluted with water before use.

(2-1) As a hair strengthening step of applying a hair treatment agent containing levulinic acid, it is desirable to apply 500 mL to 3,000 mL of a hair treatment agent evenly and sufficiently. The coating amount is determined by the extent of the desired curl formation, the pH of the first permanent agent and the alkalinity. (1-1) The residual alkali after the reduction step is neutralized (removed), and the swollen hair is gradually contracted. After that, levulinic acid further strengthens the hair. Due to the strengthened hair, operability is improved in the intermediate water washing step (3-1) of rinsing and/or washing hair with hot water, which will be described later, and operability in the step of drying (3-2a). In the heating step of heating at (3-3) 60 to 100° C., curl formation and reduction of damage due to heat can both be achieved. The effect of levulinic acid for strengthening hair is due to the structure having a carbonyl group and a carboxyl group. Similarly, glyoxylic acid having a carbonyl group and a carboxyl group is also found to have the effect of strengthening hair, but it has a color-fading action of the hair color and is not suitable as a hair treatment agent for heating permanent wave.

(3-1) Rinse and/or wash hair with hot water, and thoroughly wash away the hair treatment agent containing the first perm agent and levulinic acid in the intermediate water washing step.
(3-2) A water-washing step is carried out by gently wiping off the water on the hair after washing with water, and winding the hair in a heating lot, preferably in a state of being towel dried.
(3-3) In the heating step of heating at 60 to 100° C., the heating temperature and the degree of drying are adjusted according to the desired curl. The higher the heating temperature and the more fully dried, the stronger the curl is formed.

(4-1) Applying the second permanent agent containing an oxidizing agent, in the oxidizing step, the hair is wound around the heating rod and/or the hair removed from the heating rod is applied and sufficiently oxidized.

(5-1) Rinse with hot water and thoroughly wash away the second perm agent in the washing process.

Furthermore, in order to improve the curling effect between (3-1) rinsing and/or washing hair with hot water, intermediate washing step and (3-2) winding around a heating rod and winding step, (3-2a) Conditioning with a brush or the like while drying with a dryer, or drying while conditioning hair with a hair styling or hair straightening iron having a surface temperature of 100 to 200° C., and (3-2b) curl formation. It is also possible to add a step of applying the substance using a spray, an applicator, a brush or the like and then rewetting.

The aqueous composition contains water as an essential component, and in addition to water, other components usually used in cosmetics, pharmaceuticals and the like can be optionally added within a range that does not impair the effects of the present invention. Examples of such components include cationic polymers, anionic polymers, nonionic polymers, amphoteric polymers, polyhydric alcohols, sugars, amino acids, peptides, proteins, sequestering agents, oils, powder components, cationic interfaces. It may contain an activator, an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a pH adjuster, a thickener, a powder component, a fragrance, a powder component, a dye and the like.

In addition, before applying the hair treatment agent containing (2-1) levulinic acid, the hair treatment agent containing (2-1a) maleic acid may be applied, and the hair strengthening step may be performed in two stages.

The blending amount of maleic acid is 2.0 to 7.0% by weight, preferably 3.5 to 5.5% by weight, based on the total amount of the hair treatment agent. When the blending amount is less than 2.0% by weight, the effect of reducing the damage due to heat cannot be obtained. On the other hand, when the blending amount exceeds 7.0% by weight, the reduction of the damage due to heat corresponding to the blending amount is reduced. The improvement of the effect cannot be expected.

The hair treatment agent has a pH in the range of 2.5 to 4.5, preferably in the range of 3.0 to 4.0. If the pH is less than 2.5, the astringent action of hair becomes strong and the curling effect cannot be improved, and if the pH exceeds 4.5, the astringent effect of the hair becomes weak and the curling effect is improved. I can't.
As the alkaline agent for adjusting the pH to the above range, inorganic bases such as sodium hydroxide and potassium hydroxide, organic bases such as triethanolamine and isopropanolamine and basic amino acids, preferably primary ethanol such as monoethanolamine Primary amines can be used.

As another preferred component, (lanes 40-Na maleate/styrene sulfonic acid) copolymer may be added, and the blending amount is 0.2 to 1.5% by weight based on the total amount of the hair treatment agent, preferably Is 0.5 to 1.0% by weight. If the blending amount is less than 0.2% by weight, the effect of reducing the damage due to heat and the improvement of the curl nest cannot be obtained. It cannot be expected to reduce the damage and improve the curl effect.

In the hair treatment agent, in addition to maleic acid, a primary amine, and a (lanes 40-Na maleate/styrene sulfonic acid) copolymer, other components usually used in cosmetics, pharmaceuticals, etc. can be used. It can be optionally added within a range that does not impair it. Examples of such components include cationic polymers, anionic polymers, nonionic polymers, amphoteric polymers, polyhydric alcohols, sugars, amino acids, peptides, proteins, sequestering agents, oils, powder components, cationic interfaces. An activator, an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a pH adjuster, a thickener, a powder component, a fragrance, a powder component, a pigment, water and the like can be contained.

The dosage form of this hair treatment agent is not particularly limited as long as the desired effect is sufficiently exhibited, and for example, liquid, emulsion, gel, foam, cream, and other dosage forms can be adopted. It may be diluted with water before use.

Hereinafter, the present invention will be described in more detail with reference to specific examples, but the present invention is not limited to the following examples. Further, the compounding amount in the following examples and the like is shown by weight% unless otherwise specified.

(Examples 1-4 and Comparative Examples 1-2)
A hair treatment composition having the composition shown in Table 1 below was prepared by stirring and mixing each component in purified water until the components were uniform.
The effect of reducing the damage due to heat and the curling effect of the heating permanent wave treatment method and the hair treatment agent containing levulinic acid were evaluated according to the following evaluation criteria.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) Applying 8 mL of a perm first agent containing thioglycolic acid and leaving for 10 minutes, a reducing step, and (2-1) applying 50 mL of a hair treatment agent containing levulinic acid, a hair strengthening step, (3-1) washing hair, intermediate washing step, (3-2) winding around a heating rod having a diameter of about 20 mm, winding step, and (3-3) heating step of heating at 80° C. and sufficiently drying, (4-1) Remove the heating rod, apply 15 mL of the second agent of perm containing hydrogen peroxide, leave for 8 minutes, and oxidize step, and (5-1) rinse with hot water, wash process to form curl did.
The evaluation of the feeling was carried out both when it was wet and when it was dry, and evaluated according to the following evaluation criteria. The curling effect was evaluated according to the following evaluation criteria when the hair bundle was sufficiently wet and then left at room temperature for 24 hours in a hanging state and sufficiently dried. Furthermore, the difference between the curling effect when wet and the curling effect when dry was evaluated according to the following evaluation criteria. All evaluations were carried out by 3 people who have 10 years of experience as beauticians.

<Evaluation criteria for feel (comparison with untreated hair)>
The better the feel, the less the damage caused by heat.
1. Feel firmness 2. Feel a little firmness 3. 3. Feels almost the same, but does not feel stiff. 4. Feels the same, but does not feel stiff. Smoothness and no firmness <Criteria effect evaluation criteria when dry>
The higher the curl forming power, the higher the curl effect. Weak curl formation 2. Curl formation which is slightly weak 3. Slightly strong curl formation 4. Slightly strong curl formation 5. Curls are formed 6. High curl formation <Evaluation criteria for the difference between curling effect when wet and curling effect when dry>
The heating permanent wave has a higher curling effect when it is dried than a curling effect when it is wet. The smaller the difference, the easier it is to create a style and the higher the curling effect is.
1. I feel a big difference 2. Feel the difference 3. 3. A slight difference, but not a concern 4. Almost no difference 5. Feel no difference

As shown in Examples 1 to 4, when a hair strengthening step of applying a hair treatment agent containing levulinic acid was performed, excellent feel and sufficient curling effect were obtained. On the other hand, as shown in Comparative Example 1, when levulinic acid was not included and the hair strengthening step was not performed, the feel was insufficient, and the difference in curling effect between wet and dry conditions. was there. Further, as shown in Comparative Example 2, when the concentration of levulinic acid is out of the range, the curling effect when dried is insufficient, and the difference between the curling effect when wet and when it is dried. was there.

(Example 5 and Comparative Examples 3 to 5)
A hair treatment composition having the composition shown in Table 2 below was prepared by stirring and mixing each component in purified water until the components were uniform.
The effect of reducing the damage due to heat and the curling effect of the heating permanent wave treatment method and the hair treatment agent containing levulinic acid were evaluated according to the above evaluation criteria.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) 8 mL of a first permanent agent containing thioglycolic acid is applied and left for 10 minutes, a reducing step, and (2-1) 50 mL of a hair treatment agent having the composition shown in Table 2 is applied. Strengthening step, (3-1) washing hair, intermediate washing step, (3-2) winding around a heating rod having a diameter of about 20 mm, winding step, and (3-3) heating at 80° C. and sufficiently drying, Heating process, (4-1) Remove from heating rod, apply 15 mL of second permanent agent containing hydrogen peroxide, leave for 8 minutes, oxidation process, (5-1) Rinse with hot water, wash process , Formed a curl.

As shown in Example 5, when a hair strengthening step of applying a hair treatment agent containing levulinic acid was performed, excellent feel and sufficient curling effect were obtained. On the other hand, as shown in Comparative Examples 3 to 5, in the case of the hair treatment agent containing an acid other than levulinic acid, the feel is insufficient and the curling effect when dried is insufficient and/or wet. There was a difference in curling effect between when it was dry and when it was dry.

A hair treatment composition having the composition listed in Example 5 was prepared by stirring and mixing each component with purified water until the components were uniform.
The effect of reducing the damage due to heat and the curling effect of the heating permanent wave treatment method and the hair treatment agent containing levulinic acid were evaluated according to the above evaluation criteria.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) Apply 8 mL of a perm first agent containing thioglycolic acid, leave for 10 minutes, and perform a reduction step, and (2-1) apply 50 mL of a hair treatment agent having the composition listed in Example 5, Hair strengthening step, (3-1) washing hair, intermediate washing step, (3-2) winding around a heating rod with a diameter of about 20 mm, winding step, and (3-3) heating at 80° C. and drying, heating Step, (4-1) Remove from heating rod, apply 15 mL of second permanent agent containing hydrogen peroxide, leave for 8 minutes, oxidation step, (5-1) Rinse with hot water, wash step ( 3-1) Washing hair, intermediate washing step, and (3-2) winding around a heating rod with a diameter of about 20 mm, and (3-1a) drying step with a brush while drying with a dryer, and a drying step, (3-1b) A curl was formed by adding a process of uniformly applying water with a spray to the desired range of curl formation and then rewetting.

As shown in Example 6, the curl effect is improved by adding the (3-1a) drying step and the (3-1b) rewetting step.

(Examples 7 to 15 and Comparative Examples 6 to 9)
A hair treatment composition having the composition shown in Table 4 below was prepared by stirring and mixing each component in purified water until the components were uniform.
The heating permanent wave treatment method, the hair treatment agent containing levulinic acid, and the hair treatment agent containing maleic acid were evaluated for the effect of reducing damage caused by heat and the curling effect according to the following evaluation criteria.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) Apply 8 mL of the first permanent agent containing thioglycolic acid, leave for 10 minutes, reduce step, and (2-1a) Apply 3 mL of hair treatment agent containing maleic acid, first step hair strengthening Process, (2-1) applying 50 mL of a hair treatment agent containing 1.5% levulinic acid, a second stage hair strengthening process, (3-1) washing hair, intermediate washing process, (3-1a) Drying process with a brush while drying with a dryer, (3-1b) process of uniformly applying water with a spray to the extent desired for curl formation, and rewetting, (3-2) heating rod with a diameter of about 20 mm Winding step, (3-3) heating at 80°C and drying, (3-3) heating step, and (4-1) removing from the heating rod, applying 15 mL of the second agent for perm containing hydrogen peroxide, and 8 minutes Curling was formed in the oxidation step of leaving it to stand, (5-1) rinsing with hot water, and the washing step with water.

<Evaluation criteria for feel>
Comparison with the case without the step (2-1a) 1. Harden 2. Equivalent 3. Further reduced hardness 4. Supple feel 5. Very supple feel <Evaluation criteria for curl effect when dry>
Comparison with the case without the step (2-1a) 1. Curling reduction 2. Equivalent 3. The curl becomes slightly stronger 4. Curl becomes stronger 5. Curling becomes stronger <Evaluation criteria for difference between curling effect when wet and curling effect when dry>
Comparison with the case without the step (2-1a) 1. The difference widens 2. Equivalent 3. The difference is slightly smaller. 4. The difference is small 5. The difference is very small

As shown in Examples 7 to 15, when using a hair treatment agent in which maleic acid was adjusted to 2.0 to 7.0% by weight and the pH was adjusted to a range of 2.5 to 4.5, sufficient feel and touch were obtained. An improvement in curling effect was obtained. On the other hand, as shown in Comparative Examples 6 to 9, when the concentration and/or pH of maleic acid was out of the range, the improvement in feel and/or curling effect was insufficient.

(Examples 16 to 24)
A hair treatment composition having the composition shown in Table 5 below was prepared by stirring and mixing each component in purified water until the components were uniform.
The heating permanent wave treatment method, the hair treatment agent containing levulinic acid, and the hair treatment agent containing maleic acid were evaluated for the effect of reducing damage caused by heat and the curling effect according to the above-mentioned evaluation criteria.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) Apply 8 mL of the first permanent agent containing thioglycolic acid, leave it for 10 minutes, reduce step, and (2-1a) Apply 3 mL of a hair treatment agent containing maleic acid, first step hair strengthening Step, (2-1) applying 50 mL of a hair treatment agent containing 1.5% of levulinic acid, a second step hair strengthening step, (3-1) washing hair, intermediate washing step, (3-1a) Drying process with a brush while drying with a dryer, (3-1b) process of spraying water evenly in the desired range for curl formation and rewetting, and (3-2) heating rod with a diameter of about 20 mm Winding step, (3-3) heating at 80°C and drying, (3-3) heating step, and (4-1) removing from the heating rod, applying 15 mL of the second agent for perm containing hydrogen peroxide, and 8 minutes Curling was formed in the oxidation step of leaving it to stand, rinsing with (5-1) hot water, and the washing step of water.

As shown in Examples 16 to 24, when a hair treatment agent in which maleic acid was adjusted to 2.0 to 7.0% by weight and pH was adjusted to a range of 2.5 to 4.5 with monoethanolamine was used. A sufficient feeling and improvement in curling effect were obtained.

(Examples 25 to 26 and Comparative Example 10)
A hair treatment composition having the composition shown in Table 6 below was prepared by stirring and mixing each component in purified water until the components were uniform.
The heating permanent wave treatment method and the hair treatment agent containing levulinic acid, the hair treatment agent containing maleic acid and the (Lanes 40-Na maleate/styrene sulfonic acid) copolymer, were used to evaluate the effect of reducing damage caused by heat and the curling effect as follows. It was evaluated according to the standard.

<Evaluation of heat damage and curling effect>
Human hair (Chinese) was trimmed to have a length of 15 cm, and a hair bundle having a weight of 3 g was prepared. Then, each hair bundle was washed with a commercially available shampoo, and then dyed twice with a commercially available 8-level brown hair color, and the moisture-removed hair bundle was used as a test hair bundle.
(1-1) Applying 8 mL of a perm first agent containing thioglycolic acid and leaving it for 10 minutes, a reducing step and (2-1a) maleic acid and (lanes 40-Na maleic acid/styrene sulfonic acid) copolymer A first step hair strengthening step of applying 3 mL of a hair treatment agent containing, and (2-1) a second step hair strengthening step of applying 50 mL of a hair treatment agent containing 1.5% of levulinic acid; ) Washing hair, intermediate washing step, (3-1a) arranging with a brush while drying with a dryer, drying step, and (3-1b) applying curl-forming water evenly with a spray and wetting again Step, (3-2) winding around a heating rod with a diameter of about 20 mm, winding step, (3-3) heating at 80° C. and sufficiently drying, and (4-1) removing from the heating rod, A curl was formed in the oxidation step of applying 15 mL of the second permanent agent containing hydrogen peroxide and leaving it for 8 minutes, and in the (5-1) hot water rinsing step.

<Evaluation criteria for feel>
Comparison with Example 20 1. Harden 2. Equivalent 3. Further reduced hardness 4. Supple feel 5. Very supple feel <Evaluation criteria for curl effect when dry>
Comparison with Example 20 1. Curling reduction 2. Equivalent 3. The curl becomes slightly stronger 4. Curl becomes stronger 5. Curling becomes stronger <Evaluation criteria for difference between curling effect when wet and curling effect when dry>
Comparison with Example 20 1. The difference widens 2. Equivalent 3. Somewhat less 4. 4. Very few

As shown in Examples 25 to 26, when the hair treatment agent to which the (Lanes 40-Na maleate/styrene sulfonic acid) copolymer was added was used, sufficient feel and improvement in curling effect were obtained. On the other hand, as shown in Comparative Example 10, when the concentration of the (Lanes 40-Na maleate/styrene sulfonic acid) copolymer was out of the range, the feel and curling effect were not sufficiently improved.

Claims (6)

(1-1) A reducing step of applying a permanent wave first agent containing a reducing agent to the hair. (2-1) applying a hair treatment agent containing levulinic acid, a hair strengthening step, (3-1) rinsing and/or washing hair with hot water, an intermediate water washing step, and (3-2) winding on a heating rod, Winding step, (3-3) heating at 60 to 100° C., heating step, and (4-1) oxidation step of applying permanent wave second agent containing oxidant. (5-1) Rinse with hot water and wash with water. A heating permanent wave treatment method comprising the reduction step, the hair strengthening step, the oxidation step, and a water washing step. (3-1) Rinsing and/or hair washing with hot water, intermediate washing step, (3-2) winding around a heating rod, winding step, (3-2a) drying step, (3-2b) curl formation The method for heating permanent wave treatment according to claim 1, wherein a step of re-wetting with the aqueous composition is uniformly added to the desired range. The hair permanent treatment method according to claim 1 or 2, wherein the hair treatment agent applied in (2-1) contains levulinic acid in an amount of 0.1 to 3.0% by weight. (2-1) Before applying the hair treatment agent containing levulinic acid, (2-1a) contains maleic acid in an amount of 2.0 to 7.0% by weight and has a pH of 2.5 to 4.5. The heating permanent wave treatment method according to any one of claims 1 to 3, wherein a hair treatment agent is applied and the hair strengthening step is performed in two stages. The heat permanent wave treatment method according to claim 4, wherein the component for adjusting the pH of the hair treatment agent containing maleic acid according to claim 4 to 2.5 to 4.5 is a primary amine. .. The hair treatment agent containing maleic acid according to claim 4 or 5, further comprising 0.2 to 1.5% of (lanes 40-Na maleate/styrene sulfonic acid) copolymer. Or the heating permanent wave treatment method according to item 5.