COMPOSITION FOR HAIR TREATMENT, CONTAINING OLEFIN-BASED UNSATURATED HYDROCARBON-CONTAINING OIL

Abstract

The present disclosure provides a composition for hair and fiber treatment which supplies a transition metal as a catalyst to a thiol residue formed when hair or fiber is damaged in a process of chemical or physical care, and rapidly and abundantly binds an olefin-based unsaturated hydrocarbon through a thiol-ene reaction, thereby continuously providing smoothness to the hair and fiber.

Claims

1. A method for hair treatment, comprising applying a composition comprising a transition metal catalyst, and an oil comprising olefin-based unsaturated hydrocarbon to a subject in need thereof.

2. The method for hair treatment according to claim 1, wherein the composition has an effect of hair protection, hair recovery, giving conditioning feeling, or prevention of hair oxidation.

3. The method for hair treatment according to claim 1, wherein the transition metal catalyst is one or more selected from the group consisting of monovalent transition metals, divalent transition metals and salts thereof.

4. The method for hair treatment according to claim 1, wherein the transition metal catalyst is one or more selected from the group consisting of copper salts and iron salts.

5. The method for hair treatment according to claim 1, wherein the olefin-based unsaturated hydrocarbon is a C6 to C22 fatty acid comprising at least one unsaturated group.

6. The method for hair treatment according to claim 1, wherein the transition metal catalyst facilitates a thiol-ene reaction between cysteine present in hair and the oil comprising olefin-based unsaturated hydrocarbon.

7. A hair product comprising: a composition comprising a transition metal catalyst, and an oil comprising olefin-based unsaturated hydrocarbon.

8. The hair product according to claim 7, wherein the hair product is selected from the group consisting of bleaching agents, dyes, perm agents, hair treatment agents, hair clinic agents, hair nutrition agents, hair care agents, hair cleaning agents, shampoos, conditioners, hair tonics, hair conditioners, hair lotions, hair gels, hair packs, hair cream, hair essence, hair powder, hair spray, hair oil, hair styling agents, patches, spray and post-dye treatment agents.

9. A method for hair treatment comprising applying a composition comprising (i) an oxidation initiator and (ii) an oil comprising olefin-based unsaturated hydrocarbon to a subject in need thereof.

10. The method for hair treatment according to claim 9, wherein the composition further comprises an oxidation dye.

11. The method for hair treatment according to claim 10, wherein the oxidation dye is one or more selected from the group consisting of phenylene diamine, aminophenol, resorcinol, aminocresol, methylhydroxyethylaminophenol, nitrophenylene diamine and toluene diamine sulfate.

12. The method for hair treatment according to claim 9, wherein the oxidation initiator is one or more selected from the group consisting of hydrogen peroxide, sodium perborate, sodium percarbonate, ammonium persulfate, his maleimidoethoxy ethane, calcium peroxide, ferric chloride, hypochiorous acid, laccase, magnesium peroxide, MEK (methyl ethyl ketone) peroxide, melanin peroxide, ozonized turpentine, phthalimidoperoxycaproic acid, potassium bromate, potassium caroate, potassium chlorate, potassium monopersulfate, potassium persulfate, PVP-hydrogen peroxide, sodium bromate, sodium carbonate peroxide, sodium iodate, sodium perborate, sodium persulfate, strontium peroxide, urea peroxide and zinc peroxide.

13. The method for hair treatment according to claim 9, wherein the olefin-based unsaturated hydrocarbon is an unsaturated fatty acid.

14. The method for hair treatment according to claim 9, wherein the oil comprising olefin-based unsaturated hydrocarbon comprises an unsaturated fatty acid of 50% by weight or more.

15. The method for hair treatment according to claim 9, wherein the oil comprising olefin-based unsaturated hydrocarbon is one or more selected from the group consisting of olive oil, macadamia oil, jojoba oil, meadowfoam oil, argan oil, camelia oil, grape seed oil, sunflower oil, avocado oil, canola oil, corn oil, cottonseed oil, hempseed oil, flaxseed oil, linseed oil, palm oil, peanut oil, safflower oil and soybean oil.

16. The method for hair treatment according to claim 10, wherein the oxidation dye is separated and comprised in the first agent, the oxidation initiator is in the second agent, and the oil comprising olefin-based unsaturated hydrocarbon is in the third agent.

17. The method for hair treatment according to claim 10, wherein the first agent, the second agent and the third agent are mixed immediately before use and applied to hair.

18. The method for hair treatment according to claim 9, wherein the oxidation initiator facilitates a thiol-ene reaction between cysteine present in hair and the oil comprising olefin-based unsaturated hydrocarbon.

19. The method for hair treatment according to claim 9, wherein the composition for hair treatment has an effect of hair protection, hair recovery, giving condition feeling, prevention of hair oxidation, prevention of dye damage and color persistence.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0078] FIG. 1 schematizes the process in which oxidatively damaged hair is recovered through a reaction between olefin oil and thiolene.

[0079] FIG. 2 shows an image of a hair cross-section damage degree.

MODE FOR INVENTION

[0080] Hereinafter, the present disclosure will be described in more detail through examples. These examples are intended only to describe the present disclosure more specifically, and it will be obvious to those skilled in the art to which the present disclosure pertains that the scope of the present disclosure is not limited by these examples.

[0081] Materials and reagents used in the present experimental example were purchased from cosmetic raw material manufacturers and commercial suppliers and used.

Experimental Example

[0082] I. Composition for Hair Treatment Comprising a Metal Catalyst

[0083] 1. Preparation of a Bleaching Agent

TABLE-US-00001 TABLE 1 Use Mixing component Weight ratio (%) First Ammonia water 28% 4 agent MEA 8 Purified water Residual (to 100) Second Hydrogen peroxide 17 agent Turpinal SL 0.17 Olefin-based unsaturated 4 hydrocarbon Metal catalyst 0.4 Purified water Residual (to 100)

[0084] A bleaching agent was prepared as Table 1. To the second agent of this bleaching agent, an oil comprising olefin-based unsaturated hydrocarbon of 4% was added, and a metal catalyst of 0.4% which was 10% thereof was added.

[0085] Treatment of the bleaching agent at twice of the hair weight was performed to a 1 g hair tress for 20 minutes (which is a normal bleaching treatment time), and then it was rinsed with running water at a flow rate of 4 ml/sec for 5 minutes.

[0086] 2. Evaluation of Smoothness Upon Addition According to the Number of Transition Metal Catalyst Ions

TABLE-US-00002 TABLE 2 Comparative Comparative Example Example Example Example Example Example Example Comparative Comparative Experiment example I-1 example I-2 I-1 I-2 I-3 I-4 I-5 I-6 I-7 example I-3 example I-4 Olefin — Olive Olive Olive Olive Olive Olive Olive Olive Olive Olive oil oil oil oil oil oil oil oil oil oil Metal Cu(I) Cu(I) Cu(I) Cu(II) Cu(II) Cu(II) Fe(II) Fe(III) Fe(III) catalyst bromide chloride Iodide sulfate bromide chloride chloride bromide chloride

[0087] As Table 2, Cu and Fe were used and selected as a transition metal catalyst comprised in the second agent of Table 1. As mentioned as the example above, many types of transition metal catalysts exist depending on the counter ion, but bromide and chloride, and iodide were limitedly selected to compare the role of the metal catalysts under conditions of equal chemical binding force. Since a trivalent Cu compound does not exist, with an element having the same counter ion used as Cu in the monovalent and divalent experiments, experiments were performed using Fe.

[0088] However, as defined in Table 3, as iodide which was Example I-2 in the monovalent ion experiment showed a similar result with chloride which was Example I-3, the counter ion compound of iodide was excluded in the divalent and trivalent samples in the present experiment.

[0089] Comparative example I-1 is damaged hair, and Comparative example I-2 is hair containing olefin. Comparative example I-2 was washed for 5 minutes after applying olefin to twice the hair weight.

[0090] For the degree of smoothness of the present experimental samples, the friction force was evaluated using MTT 175 Miniature Tensile Tester (DiaSTRON, GB). After rinsing the treated hair for a few minutes, it was dried with a dryer for 2 minutes, and it was maintained at 25° C. in a constant temperature and humidity room with a humidity of 50% for one day, and the moisture inside the hair was made constant, respectively, and then the friction force was measured in the constant temperature and humidity room and the result was shown in Table 3 below.

[0091] Then, the hair tress was washed with sodium lauryl sulfate, an anionic surfactant, and then the change in the hair surface friction force (%) was calculated as Table 3 by comparing the difference value with the corresponding measured value using this as a reference value. The larger the value, the larger the friction force change value, which reflected the increase smoothness.

TABLE-US-00003 TABLE 3 Comparative Comparative Example Example Example Example Example Example Example Comparative Comparative example I-1 example I-2 I-1 I-2 I-3 I-4 I-5 I-6 I-7 example I-3 example I-4 0 6 11 14 14 6 21 24 20 4 4

[0092] From the result of Table 3, it can be seen that the friction force, which is inversely proportional to the smoothness, is significantly changed and decreased, when modification is made to monovalent or divalent. On the other hand, it can be seen that as Example I-7, Fe obviously reduced the friction force, but as shown in Comparative samples I-3 and I-4, when a trivalent metal catalyst acted, a group bound to fatty acid acted more on the hair, so it had no effect on reducing the friction force. This is because the activation energy of the trivalent radical ion as a catalyst acting on thiol-ene is high and therefore, it does not affect hair cysteine. In addition, it can be seen that it has a rougher surface than Comparative example I-2 without a metal catalyst due to unique metallic feeling of Fe.

[0093] On the other hand, referring to Example I-4, it can be seen that there is a difference in the effect of preventing surface damage depending on the counter ion, even if the same metal ion is a divalent ion. This is because the thiol-ene radical reaction was not promoted as the charge density was relatively low when the counter ion was sulfate, which is hexavalent. Br or Cl series having relatively high charge density are most suitable as a metal catalyst because they sufficiently perform a radical reaction.

[0094] Comparative example I-2 shows friction force similar to that of Example I-4, so it may seem that there is no need for a metal catalyst. However, this is a temporary rather than semi-permanent effect, and it had a conditioning effect due to the oily feeling right after applying oil, but since there was no binding to hair, the oil was washed away after washing, eventually reaching the same value as Comparative example I-1. In order to obtain a high friction force change value only by olefin treatment, an excess of olefin treatment was required than twice the hair weight, and since even this was removed by repeated washing, it was confirmed that this was only a temporary effect.

[0095] Finally, as the result of changing the content by selecting Cu(II) Chloride, which had the best smoothness conditioning effect, it was confirmed that the present metal catalyst had the best efficacy when it was 1% to 15% compared to olefin.

[0096] 3. Pretreatment Agent Preparation and Effect Evaluation

[0097] In the process of bleaching the hair, a metal catalyst was added to the hair. As shown in Table 4 below, before bleaching, that is, before treatment with a bleaching agent, a bleaching pretreatment agent treating a metal catalyst to hair was prepared, and to examine when it was effective to treat the metal catalyst.

TABLE-US-00004 TABLE 4 Use Mixing component Weight ratio (%) Pretreatment Olive oil 4 agent Metal catalyst 0.4 Purified water Residual (to 100)

[0098] As the metal catalyst comprised in the pretreatment agent, those described in Table 5 below were used. As such, pretreatment agents I-8 comprising the metal catalyst with double bond olive oil were prepared, and before using a bleaching agent, which is a peroxide-based hair cosmetic, the degree of smoothness was evaluated through the change in the friction force on the hair surface according to single use of them, and the result was shown in Table 5 below.

TABLE-US-00005 TABLE 5 Pretreatment Pretreatment Pretreatment Pretreatment Pretreatment Pretreatment Pretreatment Pretreatment Experiment agent 1 agent 2 agent 3 agent 4 agent 5 agent 6 agent 7 agent 8 Metal catalyst Cu(I) Cu(I) Cu(I) Cu(II) Cu(II) Fe(II) Fe(III) Fe(III) bromide chloride Iodide bromide chloride chloride bromide chloride Friction force 2 3 3 3 2 3 3 <0 change(%)

[0099] As can be seen in Table 5, it can be seen that when a metal catalyst is pretreated with a double bond group before using a bleaching agent which is a hydroxide-based hair cosmetic, there is no effect in enhancing a thiol-ene reaction. When olive oil or oil is adhered alone, it penetrates due to hydrophobic binding with protein inside hair as studied in the document [Ruetsch, S. B.; Kamath, Y. K.; Rele, A. S.; Mohile, R. B., Secondary ion mass spectrometric investigation of penetration of coconut and mineral oils into human hair fibers: Relevance to hair damage. Journal of Cosmetic Science 2001, 52 (3), 169-184.]. the pretreatment appears to be ineffective as this induces separation from the metal catalyst. Therefore, it can be seen that the metal catalyst is used together with an oxidizing agent, and when the disulfide of the hair is damaged, the thiol-ene reaction should be given immediately.

[0100] 4. Evaluation of Effect Using Alkali Earth Metal Catalyst

[0101] The effect was evaluated using the alkali earth metal catalyst shown in Table 6 below as the metal catalyst comprised in the second agent of Table 1 above. A thiol-ene reaction was caused by one-time use of the bleaching agent comprising the alkali earth metal catalyst, and the reactivity was evaluated by a rate of change in hair surface friction force (%) and shown in Table 6 below.

TABLE-US-00006 TABLE 6 Metal catalyst Beryllium Magnesium Calcium Strontium Change in 2 3 3 3 friction force (%)

[0102] As the result of the experiment, when using the alkali earth metal as a metal catalyst, as Table 6 above, there was no reaction at all. This is because the radical reaction is difficult as electrons are filled up to the s or f orbital in case of the alkali earth metal, whereas the radical reaction is easy to occur as electrons are filled up to the d orbital in case of Cu or Fe, and this promotes the thiol-ene reaction as a metal catalyst.

[0103] 5. Evaluation of Gloss Value, Flexural Strength, and Combing Strength

[0104] In Table 7, gloss was measured by L=100*Sin/S_out*1/W_visual using colorimeter Samba (Samba, Bossa Nova Vision, Fr), and S is the amount of reflection and W is the width (angle) of the measurement range.

[0105] In Table 7, in order to evaluate the rigidity of hair, it was evaluated by using a flexural strength estimator KES-FB2-S (KATO TECH, Japan).

[0106] In Table 7, for the combing strength, the friction force applied during the combing test was evaluated by using MTT 175 Miniature Tensile Tester (DiaSTRONG, GB). It means that as the value increases, the force applied to the comb increases, meaning that the hair is tangled.

[0107] The Examples and Comparative examples of Table 7 mark physical property values of hairs treated with a metal catalyst in the pretreatment agent as Table 5. Comparative example I-5 is non-treated, and Comparative I-6 contains only olefin. Example I-8 and Example I-9 are treated with a pretreatment agent containing Cu(I) Chloride and Cu(II) Chloride with olefin, and Comparative example I-7 is a physical property value experimented with hair treated with the pretreatment agent containing Fe(III) Chloride.

TABLE-US-00007 TABLE 7 Compar- Compar- Compar- ative ative ative exam- exam- Exam- Exam- exam- Sample pleI-5 pleI-6 ple I-8 ple I-9 ple I-7 Gloss value 12 16 32 37 11 Flexural strength 0.46 0.45 0.83 0.94 0.45 (gf*cm) Combing strength 2.73 × 1.03 × 4.24 × 3.28 × 2.15 × (J) 10.sup.−1 10.sup.−1 10.sup.−2 10.sup.−2 10.sup.−1

[0108] In Examples 7 and 8, it can be seen that as the gloss value increases, the flexural strength value increases and the combing strength value also decreases. As can be seen from the above device evaluation, it was confirmed that the monovalent and divalent metal catalyst radicals added in the present disclosure completed the thiol bond of olefin through a catalytic reaction, thereby significantly increasing the conditioning feeling.

[0109] 6. Evaluation of Degree of Damage Inside the Hair when Using Hair Dye

[0110] Finally, in order to evaluate the degree of damage inside the hair when using a hair dye, based on documents [Ryu, S. R.; Jang, W.; Yu, S. I.; Lee, B. H.; Kwon, O. S.; Shin, K., FT-IR Microspectroscopic Imaging of Cross-Sectioned Human Hair during a Bleaching Process. J. Cosmet. Dermatol. Sci. Appl. 2016, 6 (5), 181-190.], a hair section specimen was produced, and the cysteine monoxide produced when hair damage occurs was measured at 1072 cm.sup.−1 to perform IR mapping. Normalization was conducted by taking Amide I as a reference point, and the resulting image of the degree of damage on the hair section was shown in FIG. 2.

[0111] In FIG. 2, the color strength of 1072 cm.sup.−1 of the wavenumber (green: high, blue: low) represents the degree of damage. Only the #1 result image is non-treatment hair, and from #2, oxidative damage is progressed with hair dye. The circle in the figure indicates the hair section.

[0112] As shown in the result of FIG. 2, it can be seen that damage inside the hair was dramatically prevented in the process of dyeing and bleaching or perm oxidation damage, when a divalent copper ion was used as a chloride counter ion as #5.

[0113] II. Composition for Hair Treatment Comprising Oxidation Initiator

[0114] 1. Case of Directly Mixing and Applying Oil to Hair Dye

[0115] The case of directly mixing and applying natural oil having the composition of the unsaturated group of 50% or more and an oil derivative was prepared as a comparative example.

[0116] Specifically, the first oxidation hair dye agent was prepared by heating purified water to 70° C., and then sequentially adding each component, stirring, dissolving and cooling to 50° C. or less, and then adding monoethanol and subsequent components. The second agent was prepared by heating purified water to 70° C. and then sequentially adding each component, stirring, dissolving and cooling to 45° C. or less, and adding hydrogen peroxide and stirring.

[0117] Table 8 below presents the first oxidation hair dye agent and Table 9 represents the second oxidation hair dye agent.

TABLE-US-00008 TABLE 8 Comparative Comparative Comparative Comparative Comparative Comparative Classification example example example example example example (% by weight) II-1-1 II-1-2 II-1-3 II-1-4 II-1-5 II-1-6 Purified water Up to 100 % by weight EDTA .Math. 4Na 0.2 0.2 0.2 0.2 0.2 0.2 Propylene 3.00 3.00 3.00 3.00 3.00 3.00 glycol Sodium sulfite 0.70 0.70 0.70 0.70 0.70 0.70 Cetyl alcohol 4.00 4.00 4.00 4.00 4.00 4.00 Stearyl alcohol 2.00 2.00 2.00 2.00 2.00 2.00 Steatrimonium 2.50 2.50 2.50 2.50 2.50 2.50 chloride Polyoxyethylene 2.50 2.50 3.50 2.50 3.50 3.50 cetyl ether p-phenylene 0.900 0.900 0.900 0.900 0.900 0.900 diamine m- 0.300 0.300 0.300 0.300 0.300 0.300 aminophenol Resorcinol 1.050 1.050 1.050 1.050 1.050 1.050 p-aminophenol 0.300 0.300 0.300 0.300 0.300 0.300 p-amino-o- 0.015 0.015 0.015 0.015 0.015 0.015 cresol 2-methyl-5- 0.005 0.005 0.005 0.005 0.005 0.005 hydroxyethyl aminophenol Monoethanol 6.00 6.00 6.00 6.00 6.00 6.00 amine Polyquatemium- 0.2 0.2 0.2 0.2 0.2 0.2 7 Olive oil 2.0 Meadowfoam 2.0 oil Argan oil 2.0 No oil — Coconut oil 2.0 Hydrogenated 2.0 palm oil pH 10.3 10.4 10.4 10.5 10.4 10.2

TABLE-US-00009 TABLE 9 Component Comparative example Purified water Up to 100% by weight Cetostearyl alcohol 3.00 Polyoxyethylene lauryl ether 0.80 Etidronic acid 0.10 Phosphoric acid 0.10 Sodium monohydrogen phosphate 0.20 Hydrogen peroxide solution 6.0 pH 3.3

[0118] After mixing the first agent of Table 8 and the second agent of Table 9 prepared as above at 1:1 well, it was applied to the hair and it was left for 30 minutes, and then it was washed, and thereby, dyeing was conducted.

[0119] (1) Friction Coefficient Measurement

[0120] The dyed hair was fixed to an acryl tress by 4 g, and then it was measured using a tensile strength measuring instrument (MTT 175) and the result was shown in Table 10 below. It means that the smaller the value, the smoother the surface.

TABLE-US-00010 TABLE 10 Friction Coefficient Comparative Comparative Comparative Comparative Comparative Comparative Evaluation example example example example example example sample II-1-1 II-1-2 II-1-3 II-1-4 II-1-5 II-1-6 Friction 0.65 0.66 0.67 0.74 0.66 0.68 Coefficient

[0121] (2) Measurement of Combing Force

[0122] The dyed hair was fixed to an acryl tress by 4 g, and then it was measured using a tensile strength measuring instrument (MTT 175) and the result was shown in Table 11 below. It means that the smaller the value, the easier combing of the hair without tangling.

TABLE-US-00011 TABLE 11 Combing Force(mJ) Comparative Comparative Comparative Comparative Comparative Comparative Evaluation example example example example example example sample II-1-1 II-1-2 II-1-3 II-1-4 II-1-5 II-1-6 Combing 63 66 64 73 68 67 Force

[0123] (3) Comparative Experiment of Water Loss after Shampoo

[0124] SLES 6% solution was applied to the dyed hair as much as 1/10 of the sample weight, and then it was repeatedly washed under the same condition. During washing, the flow rate was 30 ml/s, and a total of 28 washes were performed assuming 15 seconds of foaming, 40 seconds of massage, 60 seconds of cleaning and 4 weeks of cleaning. The experimental result of measuring the ΔE value was shown in Table 12 below. It means that the smaller the ΔE value, the less the change in the water loss color.

TABLE-US-00012 TABLE 12 Water loss test (ΔE) Comparative Comparative Comparative Comparative Comparative Comparative Evaluation example example example example example example sample II-1-1 II-1-2 II-1-3 II-1-4 II-1-5 II-1-6 Color 1.85 1.71 1.84 2.10 2.01 2.03 change

[0125] (4) Panel Evaluation of Hair Damage after Dyeing

[0126] The dyed hair was evaluated by giving a higher score as 15 professional panels felt less damage through touch evaluation such as hand combing, softness, and the like, and the result was shown in Table 13 below. It was evaluated based on a 5-point scale, and it means that the smaller the value, the easier it was to comb the hair without tangling.

TABLE-US-00013 TABLE 13 Conditioning feeling Comparative Comparative Comparative Comparative Comparative Comparative Evaluation example example example example example example sample II-1-1 II-1-2 II-1-3 II-1-4 II-1-5 II-1-6 Evaluation 3.3 3.4 3.2 2.3 3.4 3.1 score

[0127] 2. Case of Preparing Hair Dye, Oxidation Initiator and Oil Separately and Mixing and Applying Immediately Before Use

[0128] The case of preparing a hair dye, an oxidation initiator and oil separately and mixing them immediately before use was prepared as described in Tables 14˜16. Table 14 represents the first oxidation hair dye agent, and Table 15 represents the second oxidation hair dye agent, and Table 16 represents the third oil agent.

[0129] Specifically, the first oxidation hair dye agent was prepared by heating purified water to 70° C., and then sequentially adding each component, stirring, dissolving and cooling to 50° C. or less, and then adding monoethanol and subsequent components. The second agent was prepared by heating purified water to 70° C. and then sequentially adding each component, stirring, dissolving and cooling to 45° C. or less, and adding hydrogen peroxide and stirring.

TABLE-US-00014 TABLE 14 Classification Example and (% by weight) Comparative example Purified water Up to 100% by weight EDTA•4Na 0.2 Propylene glycol 3.00 Sodium sulfite 0.70 Cetyl alcohol 4.00 Stearyl alcohol 2.00 Steartrimonium chloride 2.50 Polyoxyethylene cetyl ether 2.50 p-phenylene diamine 0.900 m-aminophenol 0.300 Resorcinol 1.050 p-aminophenol 0.300 p-amino-o-cresol 0.015 2-methyl-5-hydroxyethyl 0.005 aminophenol Monoethanol amine 6.00 pH 10.3

TABLE-US-00015 TABLE 15 Example and Component Comparative example Purified water Up to 100% by weight Cetostearyl alcohol 3.00 Polyoxyethylene lauryl ether 0.80 Etidronic acid 0.10 Phosphoric acid 0.10 Sodium monohydrogen 0.20 phosphate Hydrogen peroxide solution 6.0 pH 3.3

TABLE-US-00016 TABLE 16 Comparative Comparative Comparative Classification Example Example Example example example example (% by weight) II-1 11-2 11-3 II-2-1 II-2-2 II-2-3 Olive oil 2.0 Meadowfoam 2.0 oil Argan oil 2.0 No oil — Coconut oil 2.0 Hydrogenated 2.0 palm oil

[0130] Test method, invention effect, and experimental result (Examples and Comparative examples 2-1˜3)

[0131] After mixing the third agent of the comparative example to the first agent and the second agent prepared as above at 1:1 well, it was applied to the hair and it was left for 30 minutes, and then it was washed, and thereby, dyeing was conducted.

[0132] (1) Friction Coefficient Measurement

[0133] The dyed hair was fixed to an acryl tress by 4 g, and then it was measured using a tensile strength measuring instrument (MTT 175) and the result was shown in Table 17 below. It means that the smaller the value, the smoother the surface.

TABLE-US-00017 TABLE 17 Friction Coefficient Evaluation Example Example Example Comparative Comparative Comparative sample II-1 II-2 II-3 example II-2-1 example II-2-2 example II-2-3 Friction 0.57 0.61 0.59 0.71 0.68 0.65 Coefficient

[0134] (2) Measurement of Combing Force

[0135] The dyed hair was fixed to an acryl tress by 4 g, and then it was measured using a tensile strength measuring instrument (MTT 175) and the result was shown in Table 18 below. It means that the smaller the value, the easier combing of the hair without tangling.

TABLE-US-00018 TABLE 18 Combing Force(mJ) Evaluation Example Example Example Comparative Comparative Comparative sample II-1 II-2 II-3 example II-2-1 example II-2-2 example II-2-3 Combing 48 45 50 73 68 67 Force

[0136] (3) Comparative Experiment of Water Loss after Shampoo

[0137] SLES 6% solution was applied to the dyed hair as much as 1/10 of the sample weight, and then it was repeatedly washed under the same condition. During washing, the flow rate was 30 ml/s, and a total of 28 washes were performed assuming 15 seconds of foaming, 40 seconds of massage, 60 seconds of cleaning and 4 weeks of cleaning. The experimental result of measuring the ΔE value was shown in Table 19 below. It means that the smaller the ΔE value, the less the change in the water loss color.

TABLE-US-00019 TABLE 19 Water loss test (ΔE) Evaluation Example Example Example Comparative Comparative Comparative sample II-1 II-2 II-3 example II-2-1 example II-2-2 example II-2-3 Color 0.45 0.51 0.50 1.56 2.14 2.01 change

[0138] (4) Panel Evaluation of Hair Damage after Dyeing

[0139] The dyed hair was evaluated by giving a higher score as 15 professional panels felt less damage through touch evaluation such as hand combing, softness, and the like, and the result was shown in Table 20 below. It was evaluated based on a 5-point scale, and it means that the smaller the value, the easier it was to comb the hair without tangling.

TABLE-US-00020 TABLE 20 Conditioning feeling Evaluation Example Example Example Comparative Comparative Comparative sample II-1 II-2 II-3 example II-2-1 example II-2-2 example II-2-3 Evaluation 4.1 3.8 3.9 2.5 3.2 3.3 score

[0140] judging from the above result, it could be confirmed that a hair dye which applies natural oil that has at least one or more double bonds and has the composition of the unsaturated oil group of 50% or more or a derivative thereof to minimize hair damage and improves the color persistence after dyeing could be prepared.

[0141] 3. Examples of Preferable Bleaching Agents According to the Present Disclosure

[0142] As one preferable example of the present disclosure, as described in Tables 21˜23 below, bleaching agents were prepared. Table 21 shows the first bleaching agent, and Table 22 shows the second bleaching agent and Table 23 shows the third oil agent.

TABLE-US-00021 TABLE 21 Classification (% by weight) Content Purified water Up to 100% by weight EDTA•4Na 0.2 Propylene glycol 3.00 Sodium sulfite 0.70 Cetyl alcohol 4.00 Stearyl alcohol 2.00 Steartrimonium chloride 2.50 Polyoxyethylene cetylether 2.50 Monoethanolamine 6.00 pH 10.3

TABLE-US-00022 TABLE 22 Component Content Purified water Up to 100% by weight Cetostearyl alcohol 3.00 Polyoxyethylene laurylether 0.80 Etidronic acid 0.10 Phosphoric acid 0.10 Sodium monohydrogen 0.20 phosphate Hydrogen peroxide solution 6.0 pH 3.3

TABLE-US-00023 TABLE 23 Classification (% by weight) Content Olive oil 2.0