Composition For Surface Modification

Abstract

The present invention relates to a composition for surface modification. The composition for surface modification according to the present invention contains a particular carbodiimide-based compound, thus forms a covalent bond without damaging skin, hair, or fabric, and semipermanently provides desired skin or hair surface modification effects or fabric care effects.

Claims

1. A method for modifying the surface of hair or skin, comprising preparing a composition comprising a carbodiimide-based compound represented by Chemical Formula 1, and a hair-modifying component or a skin-modifying component, wherein the hair-modifying component or the skin-modifying component has a carboxyl group; forming a reactive ester by a reaction between the carbodiimide-based compound and the hair-modifying component or the skin-modifying component; and forming a covalent bond by a reaction between the formed reactive ester and a biological amino acid having an amine group in a hair or a skin protein surface: ##STR00024## wherein A each independently represents a monomer selected from structures listed below, R represents hydrogen; C1 to C500 linear, branched, or cyclic hydrocarbon; or aromatic hydrocarbon, wherein a portion of the linear, branched, cyclic or aromatic hydrocarbon molecule includes a double bond, is substituted with one or more elements selected from the group consisting of O, N, S, P, and Si, is substituted in an anionic, cationic, or amphoteric form, or is bonded with a metal ion in a salt form, m is an integer ranging from 1 to 100, ##STR00025## wherein * denotes a connecting position.

2. The method for modifying the surface of hair or skin according to claim 1, wherein the carbodiimide-based compound represented by Chemical Formula 1 is a carbodiimide-based compound represented by Chemical Formula 2: ##STR00026## wherein A each independently represents a monomer selected from structures listed below, m is an integer ranging from 1 to 100, and n is an integer ranging from 1 to 1,000, ##STR00027## wherein * denotes a connecting position.

3. A method for modifying the surface of hair or skin, comprising preparing a composition comprising a carbodiimide-based compound represented by Chemical Formula 3, and a hair-modifying component or a skin-modifying component, wherein the hair-modifying component or the skin-modifying component has a carboxyl group; forming a reactive ester by a reaction between the carbodiimide-based compound and the hair-modifying component or the skin-modifying component ; and forming a covalent bond by a reaction between the formed reactive ester and a biological amino acid having an amine group in a hair or a skin protein surface: ##STR00028## wherein n is an integer ranging from 1 to 130, and m is an integer ranging from 1 to 20.

4. A method for modifying the surface of hair or skin, comprising preparing a composition comprising a carbodiimide-based compound represented by Chemical Formula 1, and a hair-modifying component or a skin-modifying component, wherein the hair-modifying component or the skin-modifying component has an amine group; forming a reactive ester by a reaction between a biological amino acid having a carboxyl group in a hair or a skin protein surface and the carbodiimide-based compound, and forming a covalent bond by a reaction between the formed reactive ester and the hair-modifying component or the skin-modifying component: ##STR00029## wherein A each independently represents a monomer selected from structures listed below, R represents hydrogen; C1 to C500 linear, branched, or cyclic hydrocarbon; or aromatic hydrocarbon, wherein a portion of the linear, branched, cyclic or aromatic hydrocarbon molecule includes a double bond, is substituted with one or more elements selected from the group consisting of O, N, S, P, and Si, is substituted in an anionic, cationic, or amphoteric form, or is bonded with a metal ion in a salt form, m is an integer ranging from 1 to 100, ##STR00030## wherein * denotes a connecting position.

5. The method for modifying the surface of hair or skin according to claim 4, wherein the carbodiimide-based compound represented by Chemical Formula 1 is a carbodiimide-based compound represented by Chemical Formula 2: ##STR00031## wherein A each independently represents a monomer selected from structures listed below, m is an integer ranging from 1 to 100, and n is an integer ranging from 1 to 1,000, ##STR00032## wherein * denotes a connecting position.

6. The method for modifying the surface of hair or skin according to claim 4, wherein the carbodiimide-based compound represented by Chemical Formula 1 is a carbodiimide-based compound represented by Chemical Formula 3: ##STR00033## wherein n is an integer ranging from 1 to 130, and m is an integer ranging from 1to 20.

7. The method for modifying the surface of hair or skin according to claim 1, wherein the hair-modifying component is a component for antioxidation; conditioning; blocking ultraviolet rays; imparting fragrance; applying a dye; bioconjugation; inhibiting bacteria; stimulating hair growth; or stimulating hair regrowth, and the skin-modifying component is a component for antioxidation; conditioning; moisturizing; whitening; blocking ultraviolet rays; imparting fragrance; preventing or improving a wrinkle; keratin care; preventing or improving dandruff/itching; stimulating hair growth; preventing acne or inhibiting bacteria; suppressing body odor; atopic dermatitis care; pore care; epilation; fingernail and toenail care; or bioconjugation, or a component in the form of a dye or a powder.

8. The method for modifying the surface of hair or skin according to claim 1, wherein the hair-modifying component or the skin-modifying component has a functional group capable of covalently bonding with a protein residue in the hair or skin protein surface.

9. The method for modifying the surface of hair or skin according to claim 8, wherein the functional group capable of covalently bonding with a protein residue is one or more selected from the group consisting of imidoesters, aryl azides, diazirines, hydroxymethyl phosphine, pentafluorophenyl esters, pyridyl disulfide, sulfo-hydroxysuccinimide esters, alkoxyamines, hydrazides, haloacetyls, azide, carbonates, aldehydes, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridines, isocyanate, thiocyanate, epoxides, tresylates, succinimide, hydroxysuccinimidyl esters, imidazole, oxycarbonylamidazole, imines, thiols, maleimide, vinyl sulfone, ethyleneimine, thioethers, acrylonitrile, acrylic or methacrylic acid ester, disulfides, and ketones.

10. The method for modifying the surface of hair or skin according to claim 1, wherein the carbodiimide-based compound is comprised at a content of 0.0001 to 10 parts by weight with respect to 100 parts by weight of the composition.

11. The method for modifying the surface of hair or skin according to claim 1, wherein the composition is prepared in the form of a single formulation in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are encapsulated; or in the form of two distinct formulations in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are separated from each other.

12. The method for modifying the surface of hair or skin according to claim 3, wherein the hair-modifying component is a component for antioxidation; conditioning; blocking ultraviolet rays; imparting fragrance; applying a dye; bioconjugation; inhibiting bacteria; stimulating hair growth; or stimulating hair regrowth, and the skin-modifying component is a component for antioxidation; conditioning; moisturizing; whitening; blocking ultraviolet rays; imparting fragrance; preventing or improving a wrinkle; keratin care; preventing or improving dandruff/itching; stimulating hair growth; preventing acne or inhibiting bacteria; suppressing body odor; atopic dermatitis care; pore care; epilation; fingernail and toenail care; or bioconjugation, or a component in the form of a dye or a powder.

13. The method for modifying the surface of hair or skin according to claim 3, wherein the hair-modifying component or the skin-modifying component has a functional group capable of covalently bonding with a protein residue in the hair or skin protein surface.

14. The method for modifying the surface of hair or skin according to claim 13, wherein the functional group capable of covalently bonding with a protein residue is one or more selected from the group consisting of imidoesters, aryl azides, diazirines, hydroxymethyl phosphine, pentafluorophenyl esters, pyridyl disulfide, sulfo-hydroxysuccinimide esters, alkoxyamines, hydrazides, haloacetyls, azide, carbonates, aldehydes, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridines, isocyanate, thiocyanate, epoxides, tresylates, succinimide, hydroxysuccinimidyl esters, imidazole, oxycarbonylamidazole, imines, thiols, maleimide, vinyl sulfone, ethyleneimine, thioethers, acrylonitrile, acrylic or methacrylic acid ester, disulfides, and ketones.

15. The method for modifying the surface of hair or skin according to claim 3, wherein the carbodiimide-based compound is comprised at a content of 0.0001 to 10 parts by weight with respect to 100 parts by weight of the composition.

16. The method for modifying the surface of hair or skin according to claim 3, wherein the composition is prepared in the form of a single formulation in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are encapsulated; or in the form of two distinct formulations in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are separated from each other.

17. The method for modifying the surface of hair or skin according to claim 4, wherein the hair-modifying component or the skin-modifying component has a functional group capable of covalently bonding with a protein residue in the hair or skin protein surface.

18. The method for modifying the surface of hair or skin according to claim 17, wherein the functional group capable of covalently bonding with a protein residue is one or more selected from the group consisting of imidoesters, aryl azides, diazirines, hydroxymethyl phosphine, pentafluorophenyl esters, pyridyl disulfide, sulfo-hydroxysuccinimide esters, alkoxyamines, hydrazides, haloacetyls, azide, carbonates, aldehydes, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridines, isocyanate, thiocyanate, epoxides, tresylates, succinimide, hydroxysuccinimidyl esters, imidazole, oxycarbonylamidazole, imines, thiols, maleimide, vinyl sulfone, ethyleneimine, thioethers, acrylonitrile, acrylic or methacrylic acid ester, disulfides, and ketones.

19. The method for modifying the surface of hair or skin according to claim 4, wherein the carbodiimide-based compound is comprised at a content of 0.0001 to 10 parts by weight with respect to 100 parts by weight of the composition.

20. The method for modifying the surface of hair or skin according to claim 4, wherein the composition is prepared in the form of a single formulation in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are encapsulated; or in the form of two distinct formulations in which the carbodiimide-based compound and the hair-modifying component or the skin-modifying component are separated from each other.

Description

BEST MODE

[0123] Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

COMPARATIVE EXAMPLES 1 TO 8 AND EXAMPLES 1 TO 4

Preparation of Body Cleanser

[0124] Compositions for a body cleanser, which contain sphingosine, amodimethicone, hyaluronic acid, or Red No. 227, which is generally used in a body cleanser as a conditioning component, a component for imparting gloss to skin, a skin moisturizing component, or a dye for skin and nails, respectively, in compositions and quantities as listed in Table 1 below, and include no carbodiimide-based polymer (Comparative Examples 1 to 4); benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked as a carbodiimide-based polymer (Comparative Examples 5 to 8); or 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked polymer which is a carbodiimide-based polymer of the present invention (Examples 1 to 4), were prepared.

TABLE-US-00002 TABLE 1 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative sition Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- (wt %) ple 1 ple 2 ple ple 4 ple 5 ple ple 7 ple ple 1 ple 2 ple 3 ple 4 Water 54  54  54  4 54  54  54  4 P -7 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. 0. EDTA 4Na 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 L  acid 3 3 3 3 3 3 3 3  acid 4 4 4 4 4 4 4 4 4 4 4 Sodium  ether (2 20  20  20  20  20  20  20  20  20  20  moles) sulfate ( %) Co 1 1 1 1 1 15  15  15  1 1 1 1 betaine ( %) F 0. 0.   0.9   0.9   0.9 0. 0. 0. 0.   0.9 0.   0.9 S 1 — — — 1 — — — 1 — — — A — 1 — — — 1 — — — 1 — — H  acid — — 1 — — — 1 — — — 1 —  No. — — — 1 — — — 1 — — — 1  1, - ( - — — — — 1 1 1 1 — — — — - - )- ,  glycol -Me-ether- 1,1- -bis-( - — — — — — — — — 1 1 1 1 )-, ,  glycol -Me- -blocked pH agent Total 100  100  100  100  100  100  100  100  100  100  100  100  indicates data missing or illegible when filed

EXPERIMENTAL EXAMPLE 1

Assessment of Conditioning, Gloss, Moisturizing, and Dyeing Effects

[0125] Each of the compositions for a body cleanser according to Comparative Examples 1 to 8 and Examples 1 to 4 was used to wash a pig skin sample with a size of 2 cm (width)×2 cm (length) ten times to induce surface modification, and each skin sample was washed three times with a 15% sodium lauryl ethyl sulfate solution (surfactant) to remove a component which was not covalently bonded but just adsorbed onto the skin. Afterward, the skin samples thus treated were compared in terms of a skin conditioning effect (sensory evaluation; five-level scale [5:very good, 4:slightly good, 3:moderate, 2:slightly poor, 1:very poor]; n=30), an increment in gloss determined by measuring the reflectivity of light with a skin glossmeter, moisturizing using a skin conditioner, and redness measured with a color meter with those of untreated skin samples, the result of which is shown in Table 2 below.

TABLE-US-00003 TABLE 2 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative rative rative Classifi- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- cation ple 1 ple 2 ple ple 4 ple 5 ple 6 ple 7 ple ple 1 ple 2 ple 3 ple 4 C . — — — 3. — — — 4. — — — effect I  in — .5 — — — 17. — — — 4 .3 — — gloss (%) I  in — — .3 — — — 2 .5 — — — 4 .7 — water (%) I  in — — — .9 — — — 32. — — — 4 . (%) indicates data missing or illegible when filed

[0126] As shown in Table 2, it was confirmed that Examples 1 to 4 including a carbodiimide-based polymer of the present invention exhibited significantly excellent effects of skin conditioning and an increment in gloss, moisturizing, and redness caused by dyeing compared to Comparative Examples 1 to 8.

EXPERIMENTAL EXAMPLE 2

[0127] Compositions for a body cleanser were prepared using the same compositions as in Examples 1 to 4 except that compounds listed in Table 3 below were used instead of the carbodiimide-based compounds used in Examples 1 to 4. For the compositions for a body cleanser, a surface modification effect was assessed through the same method as in Experimental Example 1, the result of which is shown in Table 3 below.

TABLE-US-00004 TABLE 3 Skin condi- Incre- Incre- tioning ment in ment in Incre- (five- skin contained ment in level gloss water redness Compound scale) (%) (%) (%) 1,3-Bis(isocya- 4.3 43.6 46.7 46.3 natomethyl)cyclohexane-, homopolymer, polyethylene glycol mono-Me-ether-blocked Benzene-1,3-diisocyanate-, 4.1 43.2 45.3 44.2 homopolymer, polyethylene glycol mono-Me-ether-blocked Hexamethylene diisocyanate-, 4.0 42.2 44.6 44.1 homopolymer, polyethylene glycol mono-Me-ether-blocked PEG 600 diisocyanate-, 4.6 45.7 47.3 47.6 homopolymer, polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2′- 4.5 45.0 46.9 46.6 diisocyanate-, homopolymer, polyethylene glycol mono-Me-ether-blocked Isophorone diisocyanate-, 4.3 44.5 45.2 46.0 homopolymer, polyethylene glycol mono-Me-ether-blocked

COMPARATIVE EXAMPLES 9 TO 14 AND EXAMPLES 5 TO 7

Preparation of Body Cleanser Composition

[0128] Compositions for a body cleanser, which contain niacinamide, hyaluronic acid, or salicylic acid, which is generally used as a skin whitening component, an anti-wrinkle component, or a keratin care component, respectively, in compositions and quantities as listed in Table 4 below, and include no carbodiimide-based polymer (Comparative Examples 9 to 11); benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked as a carbodiimide-based (Comparative Examples 12 to 14); or 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked polymer which is a carbodiimide-based polymer of the present invention (Example 5 to 7), were prepared.

TABLE-US-00005 TABLE 4 Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative sition Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- (wt %) ple 9 ple ple 11 ple 1 ple 13 ple 1 ple ple 6 ple 7 Water 54  4 4 4 4 4 P -7 0. 0. 0.5 0. 0. 0. 0. 0.5 0. DTA 4Na 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Lauric acid 3 3 3 3 3 M  acid 4 4 4 4 4 4 4 4 4 Sodium  ether (2 20  20  20  20  20  20  20  20  0 moles)  ( 0%) C 1 1 1 1 1 1 15  15  15   ( 0%) 0.   0.9   0.9   0.9   0.9   0.9   0.9   0.9 0. N 1 — — 1 — — 1 — — H  acid — 1 — — 1 — — 1 S  acid — — 1 — — 1 — — 1 , 1, - ( - — — — 1 1 1 — — — - - )-, ,  glycol -Me- -blocked 1,1- - -( - — — — — — — 1 1 1 )-, , -Me-ether-blocked pH amount amount amount amount amount amount amount amount amount Total 100  100  100  100  100  100  100  100  100  indicates data missing or illegible when filed

EXPERIMENTAL EXAMPLE 3

Assessment of Whitening, Wrinkle and Keratin Improvement Effect

[0129] Each group of 10 panelists who thought that they needed to manage whitening, a wrinkle, and keratin was asked to use each of the compositions according to Comparative Examples 9 to 14 and Examples 5 to 7 daily for 20 days and then use a general body cleanser for 10 days. In this case, satisfaction in terms of the degree of improvement immediately after 20 days of use and the persistence of the effect after 10 days was sensorially evaluated based on a five-level scale [5:very good, 4:slightly good, 3:moderate, 2:slightly poor, 1:very poor], the result of which is shown in Table 5 below.

TABLE-US-00006 TABLE 5 Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Classification ple 9 ple 1 ple 11 ple 1 ple 1 ple 14 ple ple ple 7 Whitening (1.7, 2.5) — — (3.5, 3.9) — — (4. , 4.5) — — (improvement, persistence) Wrinkle — (1.9, 2. ) — — (3.7, 4. ) — — (4.5, 4.3) — (improvement, persistence) Keratin — — (1.2, 1.9) — — ( .4, 4.0) — — (4.7, 4.3) (improvement, persistence) indicates data missing or illegible when filed

[0130] As shown in Table 5, it was confirmed that Examples 5 to 7 including a carbodiimide-based polymer of the present invention exhibited significantly excellent effects of whitening, wrinkle care, and keratin care compared to Comparative Examples 9 to 14.

EXPERIMENTAL EXAMPLE 4

[0131] Compositions for a body cleanser were prepared using the same compositions as in Examples 5 to 7 except that compounds listed in Table 6 below were used instead of the carbodiimide-based compound used in Examples 5 to 7. For the compositions for a body cleanser, a surface modification effect was assessed through the same method as in Experimental Example 3, the result of which is shown in Table 6 below.

TABLE-US-00007 TABLE 6 Whitening Wrinkle Keratin (improvement, (improvement, (improvement, persistence) persistence) persistence) Compound (five-level scale) (five-level scale) (five-level scale) 1,3-Bis(isocyanatomethyl)cyclohexane-, (4.0, 4.2) (4.4, 4.0) (4.4, 4.2) homopolymer, polyethylene glycol mono-Me-ether-blocked Benzene-1,3-diisocyanate-, homopolymer, (4.0, 4.1) (4.1, 4.0) (4.3, 4.1) polyethylene glycol mono-Me-ether-blocked Hexamethylene diisocyanate-, (3.9, 4.1) (3.8, 4.0) (4.0, 4.0) homopolymer, polyethylene glycol mono-Me-ether-blocked PEG 600 diisocyanate-, homopolymer, (4.0, 4.2) (4.3, 4.3) (4.5, 4.2) polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2′-diisocyanate-, (4.0, 4.1) (4.2, 4.2) (4.3, 4.2) homopolymer, polyethylene glycol mono-Me-ether-blocked Isophorone diisocyanate-, homopolymer, (3.9, 4.1) (4.0, 4.1) (4.2, 4.1) polyethylene glycol mono-Me-ether-blocked

COMPARATIVE EXAMPLES 15 TO 22 AND EXAMPLES 8 TO 11

Preparation of Shampoo Composition

[0132] Shampoo compositions for hair, which contain stearylamidopropyl amine, phenyl amodimethicone, polylysine, or chitosan polymer, which is generally used in hair shampoo as a conditioning component, a conditioning component for imparting gloss to hair, a conditioning component for enhancing hair thickness, or a hair moisturizing component, respectively, in compositions and quantities as listed in Table 7 below, and include no carbodiimide-based polymer (Comparative Examples 15 to 18); benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked as a carbodiimide-based polymer (Comparative Examples 19 to 22); or 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked which is a carbodiimide-based polymer of the present invention (Examples 8 to 11), were prepared.

TABLE-US-00008 TABLE 7 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative sition Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- (wt %) ple 1 ple 16 ple 17 ple 18 ple 19 ple 20 ple 2 ple ple 8 ple 9 ple 10 ple 11 Water 47   47   47   47   46   4 4 4 4 46   4 Poly -10 0. 0. 0.5 0.5 0. 0. 0. 0. 0. 0. 0. 0. DTA 4Na 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0  (2 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 moles)  ( 0%) .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 .0 ( 0%) F 0. 0.9 0. 0.9 0.9 0.9 0.9 0.9 0. 0.9 0.9 0.9 Stearyl 1.0 — — 1.0 — — 1.0 — — — Phenyl — 1.0 — — 1.0 — — 1.0 — — — — 1.0 — — 1.0 — — 1.0 — — — — 1.0 — — — 1.0 — — — 1.0 B , 1, - ( - — — — 1.0 1.0 1.0 1.0 — — — — -1- )-, ,  glycol -Me- -blocked 1,1- - -( - — — — — — — 1.0 1.0 1.0 1.0 )-, ,  glycol -Me- -blocked pH  agent Total 100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  indicates data missing or illegible when filed

EXPERIMENTAL EXAMPLE 5

Assessment of Conditioning and Moisturizing Effects

[0133] Each of the shampoo compositions according to Examples 8 to 11 and Comparative Examples 15 to 22 was used to wash a hair tress having a length of 12 cm and a weight of 3 g ten times to induce surface modification, and each tress was washed three times with a 15% sodium lauryl ethyl sulfate solution (surfactant) to remove a component which was not covalently bonded but just adsorbed onto the hair. Afterward, the hair tresses thus treated were compared in terms of an increment in effects of conditioning (sensory evaluation; five-level scale [5:very good, 4:slightly good, 3:moderate, 2:slightly poor, 1:very poor]; n=30), gloss (determined by measuring reflectivity of light with a hair glossmeter), hair thickness (measured with an hair thickness measuring apparatus using a laser), and moisturizing (measured with a moisturizing measurement apparatus) with that of untreated hair tresses, the result of which is shown in Table 8 below.

TABLE-US-00009 TABLE 8 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative sition Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- (wt %) ple 1 ple 1 ple 17 ple 18 ple 19 ple 2 ple ple 2 ple ple 9 ple 10 ple 11 C 2. — — — . — — — 4.5 — — — effect I  in — 1. — — — — — — 5 — —  (%) I  in — — 0.2 — — — . — — — 7. — thickness (%) Water — — — 10. — — — 17.2 — — — 2 .6 c  in (%) indicates data missing or illegible when filed

[0134] As shown in Table 8, it was confirmed that Examples 8 to 11 including a carbodiimide-based polymer of the present invention exhibited significantly excellent effects of conditioning, improving gloss, enhancing hair thickness, and moisturizing compared to Comparative Examples 15 to 22.

EXPERIMENTAL EXAMPLE 6

[0135] Shampoo compositions were prepared using the same compositions as in Examples 8 to 11 except that compounds listed in Table 9 below were used instead of the carbodiimide-based compound used in Examples 8 to 11. For the shampoo compositions, a surface modification effect was assessed through the same method as in Experimental Example 5, the result of which is shown in Table 9 below.

TABLE-US-00010 TABLE 9 Hair Increment Increment Water conditioning in hair in hair contained (five-level gloss thickness in hair Compound scale) (%) (%) (%) 1,3-Bis(isocyanatomethyl)cyclohexane-, 4.3 48 7.2 24.3 homopolymer, polyethylene glycol mono-Me-ether-blocked Benzene-1,3-diisocyanate-, homopolymer, 4.1 45 6.9 24.0 polyethylene glycol mono-Me-ether-blocked Hexamethylene diisocyanate-, 4.0 44 6.6 23.6 homopolymer, polyethylene glycol mono-Me-ether-blocked PEG 600 diisocyanate-, homopolymer, 4.6 51 7.0 25.1 polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2′-diisocyanate-, 4.4 49 6.8 24.8 homopolymer, polyethylene glycol mono-Me-ether-blocked Isophorone diisocyanate-, homopolymer, 4.4 47 6.6 24.0 polyethylene glycol mono-Me-ether-blocked

COMPARATIVE EXAMPLES 23 TO 26 AND EXAMPLES 12 TO 13

Preparation of Shampoo Composition

[0136] Shampoo compositions, which contain Red No. 227 generally used in hair shampoo as a dyeing component or lauryl diamine with a structure capable of bonding split hair in compositions and quantities as listed in Table 10 below, and include no carbodiimide-based polymer (Comparative Examples 23 and 24); benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked as a carbodiimide-based polymer (Comparative Examples 25 and 26); or 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked polymer which is a carbodiimide-based polymer of the present invention (Examples 12 and 13), were prepared.

TABLE-US-00011 TABLE 10 Composition Comparative Comparative Comparative Comparative (wt %) Example 23 Example 24 Example 25 Example 26 Example 12 Example 13 Water 47 47 46 46 46 46 Polyquaternium-10 0.5 0.5 0.5 0.5 0.5 0.5 EDTA 4Na 0.05 0.05 0.05 0.05 0.05 0.05 Sodium lauryl ether (2 35.0 35.0 35.0 35.0 35.0 35.0 moles) sulfate (30%) Cocamidopropyl betaine 15.0 15.0 15.0 15.0 15.0 15.0 (30%) Fragrance 0.9 0.9 0.9 0.9 0.9 0.9 Red No. 227 1.0 — 1.0 — 1.0 — Lauryl diamine — 1.0 — 1.0 — 1.0 Benzene, 1,3-bis(1- — — 1.0 1.0 — — isocyanato-1- methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked 1,1′-methylene-bis-(3- — — — — 1.0 1.0 isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked pH controlling agent Suitable Suitable Suitable Suitable Suitable Suitable amount amount amount amount amount amount Total 100.0 100.0 100.0 100.0 100.0 100.0

EXPERIMENTAL EXAMPLE 7

Assessment of Dyeing and Bioconjugation Effects

[0137] Each of the shampoo compositions according to Comparative Examples 23 and 25 and Example 12 was used to wash a white yak hair tress ten times, and each of the shampoo compositions according to Comparative Examples 24 and 26 and Example 13 was used to wash thirty end-split hair strands ten times to induce surface modification, and each tress was washed three times with a 15% sodium lauryl ethyl sulfate solution (surfactant) to remove a component which was not covalently bonded but just adsorbed onto the hair. Afterward, the hair tresses thus treated were compared in terms of an increment in redness using a color meter (in the case of the yak hair) or the repairing of split hair using a microscope (in the case of the split hair), the results of which are shown in Table 11 below.

TABLE-US-00012 TABLE 11 Compa- Compa- Compa- Compa- rative rative rative rative Classifi- Exam- Exam- Exam- Exam- Exam- Exam- cation ple 23 ple 24 ple 25 ple 26 ple 12 ple 13 Increment in 13 — 27 — 49 — redness (%) Bonding rate of — 0 — 35 — 48 split hair (%)

[0138] As shown in Table 11, it was confirmed that Examples 12 and 13 including a carbodiimide-based polymer of the present invention exhibited significantly excellent dyeing and bioconjugation effects compared to Comparative Examples 23 to 25.

EXPERIMENTAL EXAMPLE 8

[0139] Shampoo compositions were prepared using the same compositions as in Examples 12 to 13 except that compounds listed in Table 9 below were used instead of the carbodiimide-based compound used in Examples 12 and 13. For the shampoo compositions, a surface modification effect was assessed through the same method as in Experimental Example 7, the result of which is shown in Table 12 below.

TABLE-US-00013 TABLE 12 Increment in Bonding rate Compound redness (%) of split hair (%) 1,3-Bis(isocyanatomethyl)cyclohexane-, 45 42 homopolymer, polyethylene glycol mono-Me-ether-blocked Benzene-1,3-diisocyanate-, 43 40 homopolymer, polyethylene glycol mono-Me-ether-blocked Hexamethylene diisocyanate-, 40 41 homopolymer, polyethylene glycol mono-Me-ether-blocked PEG 600 diisocyanate-, 47 46 homopolymer, polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2′-diisocyanate-, 45 45 homopolymer, polyethylene glycol mono-Me-ether-blocked Isophorone diisocyanate-, 42 43 homopolymer, polyethylene glycol mono-Me-ether-blocked

COMPARATIVE EXAMPLES 27 TO 32 AND EXAMPLES 14 TO 16

Preparation of Fabric Detergent Composition

[0140] Compositions for a fabric detergent, which contain stearyl amidopropyl amine, amodimethicone, or mono-(6-ethanediamine-6-deoxy)-beta-cyclodextrin, which is generally used in a liquid laundry detergent as a component for preventing static electricity, a component for softening a fabric, or a component for removing an odor, respectively, in compositions and quantities as listed in Table 13 below, and include no carbodiimide-based polymer (Comparative Examples 27 to 29); benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer, polyethylene glycol mono-Me-ether-blocked as a carbodiimide-based polymer (Comparative Examples 30 to 32); or 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked polymer which is a carbodiimide-based polymer of the present invention (Examples 14 to 16), were prepared.

TABLE-US-00014 TABLE 13 Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative Composition Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- (wt %) ple 27 ple ple 29 ple 0 ple 31 ple 2 ple 14 ple 1 ple 16 Water 57.1 57.1 57.1 5 .1 5 .1 56.1 56.1 56.1 56.1 Lauryl 20.0 20.0 20.0 20.0 20.0 20.0 20.0 20.0 20.0 L 7.00 7.00 7.00 7.00 7.00 7.00 7.00 7.00 7.00  (12 moles) L  acid 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 4.0 Sodium 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 10.0 Fragrance 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 Stearyl 1.0 — 1.0 — 1.0 — — amine A — 1.0 — 1.0 — 1.0 — M -( - — — 1.0 — — 1.0 — — 1.0 - - )-beta- , 1, - (1- — — 1.0 1.0 1.0 — — — -1- )-, ,  gylcol -Me- -blocked 1,1′- - -(3- — — — — 1.0 1.0 1.0 )-, ,  glycol -Me- -blocked Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 indicates data missing or illegible when filed

EXPERIMENTAL EXAMPLE 9

Assessment of Effects of Preventing Static Electricity, Softening Fabric, and Removing Odor

[0141] The detergent compositions according to Comparative Examples 27 to 32 and Examples 14 to 16 were used to wash a standard wool fabric with a size of 5 cm (width)×5 cm (length) ten times to induce surface modification, and each wool fabric was washed three times with a 15% sodium lauryl ethyl sulfate solution (surfactant) to remove a component for preventing static electricity, softening a fabric, or removing an odor, which was not covalently bonded but just adsorbed onto the fabric. Afterward, the wool fabrics thus treated were compared in terms of effects of preventing static electricity, softening a fabric, and removing an odor (sensory evaluation; five-level scale [5:very good, 4:slightly good, 3:moderate, 2:slightly poor, 1:very poor]; n=30), the result of which is shown in Table 14 below.

TABLE-US-00015 TABLE 14 Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Exam- Classification ple 27 ple 28 ple 29 ple 30 ple 31 ple 32 ple 14 ple 15 ple 16  electricity 10.2 — — 3 . — — 2.4 — — prevention (%)  effect — 2.7 — — 3. — — 4.3 — ( , five- level ) Odor removal — — 2. — — . — — 4.5 ( , five- level ) indicates data missing or illegible when filed

[0142] As shown in Table 14, it was confirmed that Examples 14 to 16 including a carbodiimide-based polymer of the present invention exhibited significantly excellent effects of preventing static electricity, softening a fabric, and removing an odor compared to Comparative Examples 27 to 32.

EXPERIMENTAL EXAMPLE 10

[0143] Detergent compositions were prepared using the same compositions as in Examples 14 to 16 except that compounds listed in Table 9 below were used instead of the carbodiimide-based compound used in Examples 14 to 16. For the detergent compositions, a surface modification effect was assessed through the same method as in Experimental Example 9, the result of which is shown in Table 15 below.

TABLE-US-00016 TABLE 15 Static Softening electricity effect Odor removal prevention rate (sensibility, five- (sense, five- Compound (%) level scale) level scale) 1,3-Bis(isocyanatomethyl)cyclohexane-, 50.6 4.1 4.3 homopolymer, polyethylene glycol mono-Me-ether-blocked Benzene-1,3-diisocyanate-, homopolymer, 48.2 4.1 4.2 polyethylene glycol mono-Me-ether-blocked Hexamethylene diisocyanate-, homopolymer, 45.3 4.0 4.0 polyethylene glycol mono-Me-ether-blocked PEG 600 diisocyanate-, homopolymer, 50.1 4.2 4.4 polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2′-diisocyanate-, 49.6 4.2 4.1 homopolymer, polyethylene glycol mono-Me-ether-blocked Isophorone diisocyanate-, homopolymer, 48.7 4.1 4.2 polyethylene glycol mono-Me-ether-blocked

PREPARATION EXAMPLE 1

Preparation of Body Cleanser

[0144] Body cleansers as shown in Table 16 below were prepared through a common method of preparing a body cleanser.

TABLE-US-00017 TABLE 16 Composition Conditioning Skin gloss Moisturizing Dyeing Whitening Wrinkle care Keratin care body body body body body body body cleanser cleanser cleanser cleanser cleanser cleanser cleanser Content Content Content Content Content Content Content Raw material (%) (%) (%) (%) (%) (%) (%) Water 52.5 52.5  53 54.5 52.5 53 52.5 Polyquaternium-7 0.5 0.5 0.5 0.5 0.5 0.5 0.5 EDTA 4Na 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Lauric acid 3.0 3.0 3.0 3.0 3.0 3.0 3.0 Myristic acid 4.0 4.0 4.0 4.0 4.0 4.0 4.0 Sodium lauryl ether (2 20.0 20.0  20.0 20.0 20.0 20.0 20.0 moles) sulfate (30%) Cocamidopropyl 15.0 15.0  15.0 15.0 15.0 15.0 15.0 betaine (30%) Fragrance 0.9 0.9 0.9 0.9 0.9 0.9 0.9 Sphingosine 2.0 — — — Amodimethicone — 2.0 — — — — — Red No. 227 — — — 0.2 — — — Niacinamide — — — 2.0 — — Hyaluronic acid 0.5 0.5 2.0 0.5 0.5 2.0 0.5 Salicylic acid — — — — — — 2.0 1,1-methylene-bis-(3- isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked pH controlling agent Suitable Suitable Suitable Suitable Suitable Suitable Suitable amount amount amount amount amount amount amount Total 100.0 100.0  100.0 100.0 100.0 100.0 100.0

PREPARATION EXAMPLE 2

Preparation of Skin Care Products (Whitening Mist, Lotion, Cream, and Pack)

[0145] Each of a mist, a lotion, a cream, and a pack as shown in Table 17 below was prepared through common methods of preparing a mist, a lotion, a cream, and a pack.

TABLE-US-00018 TABLE 17 Whit- Whit- Whit- Whit- ening ening ening ening Composition (wt %) mist lotion cream pack Niacinamide 2.0 2.0 2.0 2.0 1,1′-methylene-bis-(3- 1.0 1.0 1.0 1.0 isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked Glycerine 3.0 3.0 3.0 3.0 Butylene glycol 3.0 3.0 3.0 — Propylene glycol 3.0 3.0 — — Carboxyvinyl polymer 0.1 0.1 0.1 — Polyvinyl alcohol — — — 15.0  PEG-12 nonyl phenyl ether 0.3 — — 0.5 Polysorbate 80 0.5 — — — Polysorbate 60 — 1.5 1.5 1.5 Sorbitan sesquioleate — 1.5 — — Sorbitan stearate — — 0.5 — Liquid paraffin — 0.5 10.0  — Caprylic/capric triglyceride — 5.0 5.0 — Squalane — 5.0 5.0 — Cetearyl glucoside — — 2.0 — Ethanol 10.0  — — — Triethanolamine 0.1 0.1 0.1 — Stearyl alcohol — 1.0 — — Beeswax — 5.0 — — Preservative Suitable Suitable Suitable Suitable amount amount amount amount Fragrance Suitable Suitable Suitable Suitable amount amount amount amount Purified water buffer Re- Re- Re- Re- (pH 5.5) mainder mainder mainder mainder Total 100.0  100.0  100.0  100.0 

PREPARATION EXAMPLE 3

Preparation of Conditioning Shampoo

[0146] A hair conditioning shampoo as shown in Table 18 below was prepared through a common method of preparing a hair shampoo.

TABLE-US-00019 TABLE 18 Raw material Content Water 44.6 Polyquaternium-10 0.5 EDTA 4Na 0.05 Sodium lauryl ether (2 moles) sulfate (30%) 35.0 Cocamidopropyl betaine (30%) 15.0 Fragrance 0.9 Stearyl amidopropyl amine 1.0 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, 1.0 homopolymer, polyethylene glycol mono-Me-ether-blocked pH controlling agent Suitable amount Total 100.0

PREPARATION EXAMPLE 4

Preparation of Hair Product (Conditioning Mist, Lotion, Cream, and Pack)

[0147] Hair conditioning products as shown in Table 19 below were prepared through common methods of preparing a hair conditioning mist, lotion, cream, and pack.

TABLE-US-00020 TABLE 19 Condi- Condi- Condi- Condi- tioning tioning tioning tioning Composition (wt %) mist lotion cream pack Stearyl amidopropyl amine 1 1 1 1 Phenyl amodimethicone 1 1 1 1 Polylysine 1 1 1 1 Chitosan polymer 1 1 1 1 1,1′-methylene-bis-(3- 1 1 1 1 isocyanatocyclohexane)-, homopolymer, polyethylene glycol mono-Me-ether-blocked Glycerine 3 3 3 3 Butylene glycol 3 3 3 — Propylene glycol 3 3 — — Carboxyvinyl polymer 0.1 0.1 0.1 — Polyvinyl alcohol — — — 15 PEG-12 nonyl phenyl ether 0.3 — — 0.5 Polysorbate 80 0.5 — — — Polysorbate 60 — 1.5 1.5 1.5 Sorbitan sesquioleate — 1.5 — — Sorbitan stearate — — 0.5 — Liquid paraffin — 0.5 10 — Caprylic/capric triglyceride — 5 5 — Squalane — 5 5 — Cetearyl glucoside — — 2 — Ethanol 10 — — — Triethanolamine 0.1 0.1 0.1 — Stearyl alcohol — 1 — — Beeswax — 5 — — Preservative Suitable Suitable Suitable Suitable amount amount amount amount Fragrance Suitable Suitable Suitable Suitable amount amount amount amount Purified water buffer (pH 4.5) Re- Re- Re- Re- mainder mainder mainder mainder

PREPARATION EXAMPLE 5

Preparation of Laundry Detergent

[0148] A laundry detergent as shown in Table 20 below was prepared through a common method of preparing a laundry detergent.

TABLE-US-00021 TABLE 20 Raw material Content (%) Water 54.1 Lauryl sulfate 20.0 Laurylalcohol ethoxylate (12 moles) 7.00 Lauric acid 4.0 Sodium triphosphate 10.0 Fragrance 0.9 Stearyl amidopropyl amine 1.0 Amodimethicone 1.0 mono-(6-ethanediamine-6-deoxy)-beta-cyclodextrin 1.0 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, 1.0 homopolymer, polyethylene glycol mono-Me-ether-blocked Total 100.0

PREPARATION EXAMPLE 6

Preparation of Fabric Softener

[0149] A laundry softener as shown in Table 21 below was prepared through a common method of preparing a fabric softener.

TABLE-US-00022 TABLE 21 Raw material Content (%) Water 88 Isostearyl amine 0.5 Distearyl dimethylammonium chloride 5.0 Stearyl amidopropyl amine 1.0 Amodimethicone 1.0 mono-(6-ethanediamine-6-deoxy)-beta-cyclodextrin 1.0 1,1′-methylene-bis-(3-isocyanatocyclohexane)-, 1.0 homopolymer, polyethylene glycol mono-Me-ether-blocked Ethanol 1.0 Preservative, Antimicrobial agent Suitable amount Fragrance Suitable amount Total 100.0

[0150] A composition for surface modification according to the present invention includes a reactive surface-modifying component (or a reactive fabric care component) including a specific functional group capable of covalently bonding with a protein residue of skin, hair, or a fabric and/or a specific carbodiimide-based compound so that covalent bonding is formed without causing damage to skin, hair, or a fabric, and thus a skin or hair surface modification effect or a fabric care effect can be semi-permanently provided.

[0151] While the invention has been shown and described with reference to certain exemplary embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.