COMPOSITION FOR TREATING HAIR OR FIBERS, COMPRISING ALKYL KETENE COMPOUND

Abstract

The present invention relates to composition for hair or fiber comprising an alkyl ketene compound.

The composition according to the present invention includes an alkyl ketene compound capable of covalently bonding with a protein residue on a surface of hair or fibers, and the alkyl ketene compound can form a covalent bond with the hair or fiber to provide beneficial effects, such as long-lasting conditioning.

Claims

1. A hair treatment composition comprising an alkyl ketene compound represented by Chemical Formula 1: ##STR00004## in Chemical Formula 1, R.sub.1 and R.sub.2 are each independently a saturated or unsaturated alkyl having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid having 1 to 40 carbon atoms.

2. The composition of claim 1, wherein R.sub.1 and R.sub.2 are each independently a straight-chain or branched-chain saturated or unsaturated alkyl having 8 to 22 carbon atoms or a straight-chain or branched-chain saturated or unsaturated fitly acid having 8 to 22 carbon atoms.

3. The composition of claim 1, wherein R.sub.1 and R.sub.2 are each independently a straight chain saturated or unsaturated alkyl having 16 to 18 carbon atoms or 18-methyleicosanoic acid (18-MEA).

4. The composition of claim 1, wherein the alkyl ketene compound is included in an amount of 0.0001 to 10 parts by weight based on a total weight of the hair treatment composition.

5. The composition of claim 1, wherein the alkyl ketene compound is applied to hair to form a covalent bond with the hair.

6. The composition of claim 1, further comprising one or more selected from the group consisting of a cationic surfactant and an anionic surfactant.

7. A method of conditioning hair, comprising treating the hair with the hair treatment composition of claim 1.

8. The method of claim 7, wherein the alkyl ketene compound in the hair treatment composition forms a covalent bond with the hair.

9. The method of claim 7, wherein treatment on the hair is performed at a temperature of 20 to 250° C.

10. A hair treatment product for preventing or improving thermal damage, comprising the hair treatment composition of claim 1.

11. A use of a composition comprising an alkyl ketene compound represented by Chemical Formula 1 for manufacture of a hair treatment product: ##STR00005## in Chemical Formula 1, R.sub.1 and R.sub.2 are each independently a saturated or unsaturated alkyl having 1 to 40 carbon atoms or a saturated or unsaturated fatty acid having 1 to 40 carbon atoms.

12. The use of claim 11, wherein R.sub.1 and R.sub.2 are each independently a straight-chain or branched-chain saturated or unsaturated alkyl having 8 to 22 carbon atoms or a straight-chain or branched-chain saturated or unsaturated fatty acid having 8 to 22 carbon atoms.

13. The use of claim 11, wherein R.sub.1 and R.sub.2 are each independently a straight-chain saturated or unsaturated alkyl having 16 to 18 carbon atoms or 18-methyleicosanoic acid (18-MEA).

14. The use of claim 11, wherein the alkyl ketene compound is included in an amount of 0.0001 to 10 parts by weight based on a total weight of the hair treatment composition.

15. The use of claim 11, wherein the alkyl ketene compound is applied to hair to form a covalent bond with the hair.

16. The use of claim 11, wherein the composition further comprises one or more selected from the group consisting of a cationic surfactant and an anionic surfactant.

Description

MODES OF THE INVENTION

[0075] Hereinafter, the present invention will be described in detail by way of Examples. The following Examples merely illustrate the present invention, but the scope of the present invention is not limited by the following Examples. The examples are merely provided to complete the disclosure of the present invention and to fully convey the scope of the invention to those skilled in the art, and the invention is only defined by the scope of the claims.

[0076] Hereinafter, materials used in the Examples and Comparative Examples of the present invention were purchased and used from general raw material purchasing places.

EXAMPLES

Preparation Example 1. Preparation of Hair Treatment Composition (Examples 1 to 8 and Comparative Examples 1 to 6)

[0077] Hair treatment compositions (Examples 1 to 8 and Comparative Examples 1 to 6) including the components in Tables 1 and 2 below were prepared. In Table 2 below, an alkyl ketene compound is a compound having a structure of Chemical Formula 1, and R.sub.1 and R.sub.2 are described.

[0078] First, a fatty acid or an alkyl ketene compound, a nonionic emulsifier, and a thickener were added to purified water, heated to 70° C., sufficiently stirred, and then cooled to room temperature (25° C.) to prepare a composition.

TABLE-US-00001 TABLE 1 Content Component (% by weight) Nonionic emulsifier Glycerin fatty acid ester 0.25 Polyoxyethylene fatty acid ester 0.25 Thickener Higher alcohol 5.0 Fatty acid or alkyl See Table 2 Comparative ketene compound Example: 3.0 Example: 1.5 Water to 100

TABLE-US-00002 TABLE 2 Classifi- Fatty acid or alkyl ketene compound cation R.sub.1 and R.sub.2 Compound name Comparative Fatty acid (C14) Myristic acid Example 1 Comparative Fatty acid (C16) Palmitic acid Example 2 Comparative Fatty acid (C18) Stearic acid Example 3 Comparative Fatty acid (C16 50% + — Example 4 C18 50%) Comparative Fatty acid (C18-MEA) 18-methyleicosanoic acid Example 5 Comparative Fatty acid (C16 50% + — Example 6 C18-MEA 50%) Example 1 Alkyl (R.sub.1, R.sub.1; C12-16) ketene C12-16 alkyl ketene dimer Example 2 Alkyl (R.sub.1, R.sub.2; C16-18) ketene C16-18 alkyl ketene dimer Example 3 Alkyl (R.sub.1, R.sub.2; C16) ketene C16 alkyl ketene dimer Example 4 Alkyl (R.sub.1, R.sub.2; C18) ketene C18 alkyl ketene dimer Example 5 Alkyl (R.sub.1; C16, R.sub.2; C18) C16 alkyl/C18 alkyl ketene Ketene dimer Example 6 Alkyl (R.sub.1, R.sub.2; C18-MEA) 18-methyleicosanoyl ketene ketene dimer Example 7 Alkyl (R.sub.1; C16, R.sub.2; C16 alkyl/18- C18-MEA) ketene methleicosanoyl ketene dimer Example 8 Alkyl (R.sub.1; C18-MEA, R.sub.2; 18-methleicosanoyl/C16 C16) ketene alkyl ketene dimer

Experimental Example 1. Comparison of Conditioning Effects of Hair Treatment Compositions

[0079] (1) Method

[0080] 1 g of each prepared hair treatment composition of Examples 1 to 8 and Comparative Examples 1 to 6 was evenly applied on about 4 g of a hair tress, left at room temperature for 30 minutes to induce a reaction, and an initial conditioning effect (hair smoothness satisfaction immediately after use_satisfaction 1) was compared by washing with running water and shampoo first.

[0081] Thereafter, shampooing was performed once a day, and after 10 days, a hair conditioning effect (satisfaction with hair smoothness after shampooing 10 times_satisfaction 2) was compared.

[0082] The conditioning effect was evaluated and compared by sensory evaluation on a 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 ineffective, 1 very ineffective).

[0083] (2) Results

[0084] The satisfaction evaluation results are shown in Table 3 below.

[0085] As shown in Table 3, it can be confirmed that Examples 1 to 8 using an alkyl ketene compound exhibited better conditioning effects and sustained conditioning effects than Comparative Examples 1 to 6 not including the alkyl ketene compound.

TABLE-US-00003 TABLE 3 Satisfaction Comp Comp. Comp. Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. (n = 10) Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 1 2 3 4 5 6 7 8 Satisfaction 3.0 3.0 3.5 3.5 3.5 3.5 4.0 4.0 4.0 4.5 4.0 5.0 4.5 4.5 1 Satisfaction 2.5 2.5 2.5 2.5 2.8 2.8 3.0 3.0 3.0 3.3 3.0 3.5 3.3 3.3 2 Ex.: Example Comp. Ex.: Comparative Example

Experimental Example 2. Comparison of Conditioning Effects of Hair Treatment Compositions According to Treatment Temperature

[0086] (1) Method Using the compositions of Examples 1 to 8, 1 g of each composition was evenly applied on about 4 g of a hair tress, and dried with a hair dryer at a temperature of 80 to 100° C. for 5 minutes to apply heat.

[0087] After treatment, hair was first washed with running water and shampoo, and an initial conditioning effect (hair smoothness satisfaction immediately after use_satisfaction 1) was compared.

[0088] Thereafter, shampooing was performed once a day, and after 10 days, a hair conditioning effect (satisfaction with hair smoothness after shampooing 10 times_satisfaction 2) was compared.

[0089] The conditioning effect was evaluated and compared by sensory evaluation on a 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 ineffective, 1 very ineffective).

[0090] (2) Results

[0091] The satisfaction evaluation results are shown in Table 4 below.

[0092] As shown in Table 4, it can be confirmed that a hair tress containing the alkyl ketene compounds of Examples and treated at 80 to 100° C. for 5 minutes using a hair dryer has relatively excellent conditioning effects and durability compared to the case of drying at room temperature using the same composition.

[0093] Accordingly, it can be confirmed that when heat treatment conditions are added, covalent bond formation efficiency between an alkyl ketene compound and hair is better, resulting in a better conditioning effect and a lasting effect. That is, when a composition according to the present invention is used, hair is not damaged by heat, but a surprising effect of further improving the conditioning effect is shown.

TABLE-US-00004 TABLE 4 Satisfaction Example Example Example Example Example Example Example Example (n = 10) 1 2 3 4 5 6 7 8 Satisfaction 4.0 4.0 4.0 4.5 4.0 5.0 4.5 4.5 1 Satisfaction 3.5 3.5 3.5 4.0 3.5 4.0 4.0 4.0 2

Preparation Example 2. Preparation of Fiber Treatment Composition (Examples 9 to 16 and Comparative Examples 7 to 12)

[0094] Fiber treatment compositions (Examples 9 to 16 and Comparative Examples 7 to 12) including the components in Tables 5 and 6 below were prepared. In Table 6 below, an alkyl ketene compound is a compound having a structure of Chemical Formula 1, and R.sub.1 and R.sub.2 are described.

[0095] First, a fatty acid or an alkyl ketene compound, a nonionic emulsifier, and ethanol were added to purified water, heated to 70° C., sufficiently stirred, and then cooled to room temperature (25° C.) to prepare a composition.

TABLE-US-00005 TABLE 5 Content Component (% by weight) Nonionic emulsifier Polyoxyethylene sorbitan fatty 0.5 acid ester Polyoxyethylene alkylphenyl ether 0.3 Fatty acid or alkyl See Table 6 Comparative ketene compound Example: 2.0 Example: 1.0 Ethanol 0.5 Water to 100

TABLE-US-00006 TABLE 6 Classifi- Fatty acid or alkyl ketene compound cation R.sub.1 and R.sub.2 Compound Comparative Fatty acid (C14) Myristic acid Example 7 Comparative Fatty acid (C16) Palmitic acid Example 8 Comparative Fatty acid (C18) Stearic acid Example 9 Comparative Fatty acid (C16 50% + — Example 10 C18 50%) Comparative Fatty acid (C18-MEA) 18-methyleicosanoic acid Example 11 Comparative Fatty acid (C16 50% + — Example 12 C18-MEA 50%) Example 9 Alkyl (R.sub.1, R.sub.1; C12-16) ketene C12-16 alkyl ketene dimer Example 10 Alkyl (R.sub.1, R.sub.2; C16-18) ketene C16-18 alkyl ketene dimer Example 11 Alkyl (R.sub.1, R.sub.2; C16) ketene C16 alkyl ketene dimer Example 12 Alkyl (R.sub.1, R.sub.2; C18) ketene C18 alkyl ketene dimer Example 13 Alkyl (R.sub.1; C16, R.sub.2; C18) C16 alkyl/C18 alkyl ketene Ketene dimer Example 14 Alkyl (R.sub.1, R.sub.2; 18-methyleicosanoyl C18-MEA) ketene ketene dimer Example 15 Alkyl (R.sub.1; C16, R.sub.2; C16 alkyl/18- C18-MEA) ketene methleicosanoyl ketene dimer Example 16 Alkyl (R.sub.1; C18-MEA, R.sub.2; 18-methleicosanoyl/C16 C16) ketene alkyl ketene dimer

Experimental Example 3. Comparison of Conditioning Effects of Fiber Treatment Compositions

[0096] (1) Method

[0097] 1 g of each prepared fiber treatment composition of Examples 8 to 16 and Comparative Examples 7 to 12 was evenly applied on standard wool fiber having a width×length of 20 cm×20 cm, left at room temperature for 30 minutes to induce a reaction, and an initial fiber softening effect (satisfaction of fiber softness immediately after use_satisfaction 1) was compared after washing with flowing water and detergent and drying.

[0098] Then, after washing with laundry detergent three times and drying, a fiber softening effect (fiber softness satisfaction after washing three times_satisfaction 2) was compared.

[0099] The fiber softening effect was evaluated and compared by sensory evaluation on a 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 ineffective, 1 very ineffective).

[0100] (2) Results

[0101] The satisfaction evaluation results are shown in Table 7 below.

[0102] As shown in Table 7, it can be confirmed that Examples 1 to 8 using an alkyl ketene compound exhibited better fiber softening effects and sustained fiber softening effects than Comparative Examples 7 to 12 not including the alkyl ketene compound.

TABLE-US-00007 TABLE 7 Satisfaction Comp. Comp. Comp. Comp. Comp. Comp. Ex. Ex. Ex. Ex. Ex. Ex. Ex. Ex. (n = 10) Ex. 7 Ex. 8 Ex. 9 Ex. 10 Ex. 11 Ex. 12 9 10 11 12 13 14 15 16 Satisfaction 3.0 3.3 3.5 3.5 3.5 3.5 3.8 4.0 3.8 4.0 4.5 5.0 4.8 4.8 1 Satisfaction 2.5 2.5 2.5 2.5 3.0 3.0 3.3 3.3 3.3 3.5 3.5 3.8 3.5 3.5 2 Comp. Ex.: Comparative Example Ex.: Example

Experimental Example 4. Comparison of Conditioning Effects of Fiber Treatment Compositions According to Treatment Temperature

[0103] (1) Method

[0104] 1 g of each composition of Examples 9 to 16 was evenly applied on 1 g of standard wool fiber having a width×length of 20 cm×20 cm and the resultant was ironed for 1 minute with an iron at a temperature of about 150 to 170° C. to induce a reaction by heat.

[0105] After that, an initial fiber softening effect (fiber softness satisfaction immediately after use_satisfaction 1) was compared by washing with running water and detergent first.

[0106] Then, after washing with laundry detergent three times and drying, a fiber softening effect (fiber softness satisfaction after washing three times_satisfaction 2) was compared.

[0107] The fiber softening effect was evaluated and compared by sensory evaluation on a 5-point scale (5 very good, 4 slightly good, 3 no difference, 2 ineffective, 1 very ineffective).

[0108] (2) Results

[0109] The satisfaction evaluation results are shown in Table 8 below.

[0110] As shown in Table 8, wool fiber including an alkyl ketene compound and treated with an iron at 150 to 170° C. for 1 minute was evaluated as having better fiber softening effects and durability than when dried at room temperature using the same composition.

[0111] Accordingly, it can be confirmed that when heat treatment conditions are added, covalent bond formation efficiency between an alkyl ketene compound and wool fiber is better, resulting in a better fiber softening effect and a lasting effect. That is, when a composition according to the present invention is used, the fiber is not damaged by heat, but a surprising effect of further improving the conditioning effect is shown.

TABLE-US-00008 TABLE 8 Satisfaction Example Example Example Example Example Example Example Example (n = 10) 9 10 11 12 13 14 15 16 Satisfaction 3.8 4.0 3.8 4.0 4.5 5.0 4.8 4.8 1 Satisfaction 3.5 3.5 3.5 3.8 4.0 4.3 4.0 4.0 2

[0112] Additionally, compositions according to the Examples showed similar effects even when heat treatment was applied using a clothes dryer (LG Electronics-RH16VS).

Preparation Example 3. Preparation of Fiber Treatment Composition (Examples 17 to 23 and Comparative Examples 13 to 18)

[0113] Fiber treatment compositions (Examples 17 to 23 and Comparative Examples 13 to 18) including the components in Tables 9 and 10 below were prepared.

[0114] Alkylether sulfates, alkylbenzene sulfonates and soap are anionic surfactants, Dialkyldimethyl ammonium salts, alkyl imidazolinium salts and esterquats are cationic surfactants, and polyoxyethylene sorbitan fatty acid ester is a nonionic surfactant.

[0115] In addition, a C12-16 alkyl ketene dimer was used as an alkyl ketene compound.

[0116] First, an anionic surfactant or a cationic surfactant, a nonionic surfactant, and an alkyl ketene compound were added to purified water, heated to 70° C., and sufficiently stirred. Thereafter, the temperature was lowered to 40° C., and the mixture was sufficiently stirred by adding a fragrance, and then cooled to room temperature (25° C.) to prepare a composition.

TABLE-US-00009 TABLE 9 Example Example Example Example Example Example Example Component 17 18 19 20 21 22 23 Alkyl ketene 2.5 2.5 2.5 2.5 2.5 2.5 5.0 compound Alkylether sulfate 2.5 — — — — — — Alkylbenzene — 2.5 — — — — — sulfonate soap — — 2.5 — — — — Dialkyl dimethyl — — — 2.5 — — — ammonium salt Alkyl — — — — 2.5 — — imidazolinium salt Esterquat — — — — — 2.5 — Polyoxyethylene 0.5 0.5 0.5 0.5 0.5 0.5 0.5 sorbitan fatty acid ester Fragrance 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Purified water Balance Balance Balance Balance Balance Balance Balance

TABLE-US-00010 TABLE 10 Comparative Comparative Comparative Comparative Comparative Comparative Example Example Example Example Example Example Component 13 14 15 16 17 18 Alkylether 5.0 — — — — — sulfate Alkylbenzene — 5.0 — — — — sulfonate soap — — 5.0 — — — Dialkyldimethyl — — — 5.0 — — ammonium salt Alky1 — — — — 5.0 — imidazolinium salt Esterquat — — — — — 5.0 Polyoxyethylene 0.5 0.5 0.5 0.5 0.5 0.5 sorbitan fatty acid ester Fragrance 0.5 0.5 0.5 0.5 0.5 0.5 Purified water Balance Balance Balance Balance Balance Balance

Experimental Example 5. Evaluation of Fiber Property Improvement Effect According to Combination of Alkyl Ketene Compound and Surfactant

[0117] For compositions of Examples 17 to 23, sensory evaluation (Residual fragrance strength, flexibility), stiffness, coefficient of friction, contact angle, and shrinkage were evaluated.

[0118] Sample treatment proceeded as follows.

[0119] First, a fiber treatment composition was diluted 10 times.

[0120] A standard cotton cloth (E-211, Center For Testmaterials BV, Netherlands) having a width×length of 8 cm×8 cm was immersed in the diluted fiber treatment composition, and stirred with a magnetic bar at a speed of 400 rpm and 35° C. for 1 hour. After that, the cotton cloth was taken out, rinsed with running tap water for 3 minutes, wiped dry with a kitchen towel, and put into a drying oven at 60° C. to dry for 2 hours. After storage for 24 hours under conditions of 25° C. and 50% RH, a test for each evaluation item was conducted.

[0121] (1) Sensory Evaluation

[0122] {circle around (1)} Method

[0123] (a) Sensory evaluation was performed on intensity and softness of the fragrance remaining on the cotton cloth after sample treatment, and a score from 1 to 5 was given. The evaluation was performed by experienced panelists, and an average value of 10 repetitions was obtained.

[0124] (b) In addition, the cotton cloth was treated with a 15% SLES solution three times in the same manner as the sample treatment method, washed and dried three times, and sensory evaluation was performed in the same manner as in (a). [0125] Residual fragrance strength 1 almost no scent, 2 weak scent, 3 moderate scent, 4 strong scent, 5 very strong scent [0126] Flexibility: 1 very stiff, 2 moderately stiff, 3 normal, 4 moderately flexible, 5 very flexible

[0127] {circle around (2)} Result

[0128] The sensory evaluation results are shown in Tables 11 and 12 below.

[0129] As shown in the tables, it can be confirmed that Example 23 using an alkyl ketene compound alone and Examples 17 to 22 using an alkyl ketene compound and a surfactant together have higher residual fragrance strength and flexibility scores compared to Comparative Example. In particular, it can be confirmed that when the alkyl ketene compound and the surfactant are used together, it has better residual fragrance strength and flexibility.

[0130] These results maintained the above trend even after washing.

TABLE-US-00011 TABLE 11 Example Example Example Example Example Example Example Classification 17 18 19 20 21 22 23 Residual after 4.3 4.3 4.5 4.5 4.5 4.5 4.0 treatment fragrance After 3 2.5 2.5 2.5 2.5 2.5 2.5 2.0 strength washes (points) Flexibility after 4.0 4.0 4.3 4.5 4.3 4.5 4.0 (points) treatment After 3 3.3 3.3 3.3 3.5 3.3 3.3 3.0 washes

TABLE-US-00012 TABLE 12 Comparative Comparative Comparative Comparative Comparative Comparative Example Example Example Example Example Example Classification 13 14 15 16 17 18 Residual after 3.0 3.0 3.3 3.3 3.3 3.3 fragrance treatment strength After 3 1.0 1.0 1.0 1.0 1.0 1.0 (points) washes Flexibility after 3.0 3.0 2.8 3.5 3.3 3.5 (points) treatment After 3 2.0 2.0 2.0 2.3 2.3 2.3 washes

[0131] (2) Stiffness Evaluation

[0132] {circle around (1)} Method

[0133] (a) After sample treatment, the two facing sides of the cotton cloth are spread and fixed evenly on the two axes of a device (KES-FB2-S Pure Bending Tester, Kato Tech, Japan), and one axis is in a fixed state while the other axis rotates, and the moment M (gf cm/cm) applied when the cotton cloth is bent was recorded according to the curvature K (cm.sup.−1) of the cotton cloth (Rotation range: K=±2.5 cm.sup.−1, rotation speed: 0.5 cm.sup.−1/sec).

[0134] (b) A slope value_1 was obtained through linear fitting for a section where the moment change amount was constant within the range of curvature K=0 to 2.5 cm.sup.−1.

[0135] (c) The cotton cloth was rotated 90 degrees and processes (a) and (b) were repeated to obtain a slope value_2.

[0136] (d) Slope values_1 and 2 were geometrically averaged and expressed as stiffness (gf cm.sup.2/cm) (average of 10 repetitions).

[0137] (e) In addition, the cotton cloth was treated with a 15% SLES solution three times in the same manner as the sample treatment method, washed and dried three times, and then stiffness was evaluated in the same manner as in (a) to (d) (average of 10 repetitions).

[0138] This experiment was performed at 25° C. and 50% RH.

[0139] {circle around (2)} Result

[0140] Stiffness evaluation results are shown in Tables 13 and 14 below.

[0141] As shown in the tables, it can be confirmed that Example 23 using an alkyl ketene compound alone and Examples 17 to 22 using an alkyl ketene compound and a surfactant together have lower stiffness and are more flexible compared to Comparative Examples, and in particular, an effect is more excellent when an alkyl ketene compound and a surfactant are used together.

[0142] These results maintained the above trend even after washing. The results are similar to the above-mentioned flexibility sensory evaluation results.

TABLE-US-00013 TABLE 13 Example Example Example Example Example Example Example Classification 17 18 19 20 21 22 23 Stiffness After 0.757 0.726 0.735 0.642 0.654 0.667 0.801 (gf treatment cm.sup.2/cm) After 3 0.697 0.686 0.704 0.608 0.606 0.622 0.772 washes

TABLE-US-00014 TABLE 14 Comparative Comparative Comparative Comparative Comparative Comparative example example example example example example Classification 13 14 15 16 17 18 Stiffness After 1.104 1.080 1.048 0.956 0.938 0.923 (gf treatment cm.sup.2/cm) After 3 0.974 0.959 0.944 0.845 0.869 0.850 washes

[0143] (3) Coefficient of Friction Evaluation

[0144] {circle around (1)} Method

[0145] (a) A dedicated rubber probe, and a weight applying 200 g of normal force were installed on a friction tester (mTT175, Dia-Stron, UK), and a cotton cloth treated with a sample was spread flat and fixed to a moving plate of a device. The rubber probe was brought into contact with one end of the cotton cloth, and the frictional force generated between the rubber probe and the cotton cloth was recorded according to the position of the cotton cloth while moving the moving plate at a speed of 200 mm/min. The coefficient of friction was obtained from the average value of the frictional force and normal force in a specific range of the cotton cloth (average of 10 repetitions).

[0146] (b) In addition, the cotton cloth was treated with a 15% SLES solution three times in the same manner as the sample treatment method, washed and dried three times, and then a coefficient of friction was evaluated in the same manner as in (a) (average of 10 repetitions).

[0147] This experiment was performed at 25° C. and 50% RH.

[0148] {circle around (2)} Result

[0149] Coefficient of friction evaluation results are shown in Tables 15 and 16 below.

[0150] As shown in the tables, it can be confirmed that Example 23 using an alkyl ketene compound alone and Examples 17 to 22 using an alkyl ketene compound and a surfactant together has a low coefficient of friction, and the fiber surface is less damaged and softer compared to Comparative Examples, and in particular, an effect is more excellent when an alkyl ketene compound and a surfactant are used together.

[0151] These results maintained the above trend even after washing.

TABLE-US-00015 TABLE 15 Example Example Example Example Example Example Example Classification 17 18 19 20 21 22 23 Coefficient After 0.7818 0.7735 0.7680 0.6128 0.6160 0.6271 0.8306 of friction treatment After 3 0.9067 0.9004 0.8911 0.7972 0.8113 0.8043 0.9372 washes

TABLE-US-00016 TABLE 16 Comparative Comparative Comparative Comparative Comparative Comparative example example example example example example Classification 13 14 15 16 17 18 Coefficient After 1.0703 1.0445 1.0230 0.9195 0.9122 0.9039 of treatment friction After 3 1.0898 1.0812 1.0771 1.0669 1.0780 1.0804 washes

[0152] (4) Contact Angle

[0153] {circle around (1)} Method

[0154] (a) After sample treatment, a cotton cloth was spread flat and placed on a parallel plate, then 10 μL of distilled water was dropped on each of 5 random locations, and images of the resulting droplets were taken using a Drop Shape Analyzer (DSA100, Kruss, Germany) and the contact angle was measured (average of 10 repetitions).

[0155] (b) In addition, the cotton cloth was treated with a 15% SLES solution three times in the same manner as the sample treatment method, washed and dried three times, and then a contact angle was evaluated in the same manner as in (a) (average of 10 repetitions).

[0156] This experiment was performed at 25° C. and 50% RH.

[0157] {circle around (2)} Result

[0158] The contact angle evaluation results are shown in Table 17 below.

[0159] In Comparative Examples 13 to 18, in which only a surfactant was treated, the droplet was completely absorbed into the cotton cloth, so that contact angle measurement was not possible.

[0160] However, Example 23 using the alkyl ketene compound alone and Examples 17 to 22 using an alkyl ketene compound and a surfactant together showed a contact angle of 30° or more, through which it could be confirmed that a fiber surface was hydrophobic. In addition, it can be confirmed that surface hydrophobicity is maintained to some extent even after washing.

[0161] In particular, Examples 17 to 22 using an alkyl ketene compound and a surfactant show a contact angle close to 90° and a high contact angle even after washing, so that a long-lasting conditioning effect can be imparted through imparting hydrophobicity, which is the purpose of the present invention.

TABLE-US-00017 TABLE 17 Example Example Example Example Example Example Example Classification 17 18 19 20 21 22 23 Contact After 87.04 87.75 89.71 89.96 89.03 90.26 67.92 angle treatment After 3 80.57 81.21 79.95 82.10 80.63 81.25 44.84 washes

[0162] (5) Shrinkage Evaluation

[0163] {circle around (1)} Method

[0164] (a) A fiber treatment composition prepared in Examples 17 to 23 and Comparative Examples 13 to 18 was used to treat standard wool fiber (537, Testfibers, Inc., USA).

[0165] A treatment method is the same as a treatment method described above in Experimental Example 5.

[0166] (b) After unfolding the wool fiber and holding one end of the wool fiber with tongs inside a device (Volume tester (Bolero Lite, BOSSA NOVA VISION, USA)) and suspending it, a picture was taken with a camera and an area of the wool fiber was measured, and the degree of shrinkage compared to an original area (8 cm×8 cm) was expressed as shrinkage (%) (average of 10 repetitions).

[0167] (c) In addition, the wool fiber was treated with a 15% SLES solution three times in the same manner as the sample treatment method, washed and dried three times, and then shrinkage was evaluated in the same manner as in (b) (average of 10 repetitions).

[0168] {circle around (2)} Result

[0169] The shrinkage evaluation results are shown in Tables 18 and 19 below.

[0170] As shown in the tables, it can be seen that Example 23 using the alkyl ketene compound alone and Examples 17 to 22 using the alkyl ketene compound and a surfactant together had a low shrinkage rate and high fiber shrinkage prevention ability compared to the Comparative Example. In particular, it can be confirmed that the effect is more excellent when the alkyl ketene compound and the surfactant are used together.

[0171] These results maintained the above trend even after washing.

TABLE-US-00018 TABLE 18 Example Example Example Example Example Example Example Classification 17 18 19 20 21 22 23 Shrinkage After  4.41  3.88  3.50  3.04  3.95 3.48  5.57 (%) treatment After 3 11.91 12.41 11.30 10.39 10.71 9.88 14.16 washes

TABLE-US-00019 TABLE 19 Comparative Comparative Comparative Comparative Comparative Comparative Example Example Example Example Example Example Classification 13 14 15 16 17 18 Shrinkage After 23.71 24.14 21.77  7.57  7.73  7.34 (%) treatment After 3 28.82 28.96 27.59 27.29 28.36 26.70 washes

INDUSTRIAL APPLICABILITY

[0172] Since the hair or fiber treatment composition according to the present invention contains an alkyl ketene compound capable of covalently bonding with protein residues of hair or fibers, the alkyl ketene compound forms a covalent bond with the protein residues without damaging hair or fibers, and beneficial effects, such as long-lasting conditioning can be provided by imparting permanent hydrophobicity.

[0173] In addition, the hair or fiber treatment composition according to the present invention can prevent and/or improve damage to hair or fibers caused by heat.

[0174] In addition, the hair or fiber treatment composition according to the present invention can maintain a residual fragrance in hair or fibers, and can enhance flexibility, softness, hydrophobicity or an anti-shrinkage property.