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 for hair or skin modification, wherein the composition comprises a carbodiimide-based compound represented by Chemical Formula 2 below, and a hair-modifying component or a skin-modifying component, wherein the hair-modifying component or the skin-modifying component does not include a peptide; and treating hair or skin with the composition for hair or skin modification: ##STR00024## 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, ##STR00025## wherein * denotes a connecting position.

2. A method for modifying the surface of hair or skin, comprising: preparing a composition for hair or skin modification, wherein the composition comprises a carbodiimide-based compound represented by Chemical Formula 3 below, and a hair-modifying component or a skin-modifying component, wherein the hair-modifying component or the skin-modifying component does not include a peptide; and treating hair or skin with the composition for hair or skin modification: ##STR00026## wherein n is an integer ranging from 1 to 130, and m is an integer ranging from 1 to 20.

3. 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.

4. 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 carboxyl group, a hydroxyl group, a phosphate group, or an amine group in a molecule thereof.

5. 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 a skin surface.

6. The method for modifying the surface of hair or skin according to claim 5, 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.

7. 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.

8. The method for modifying the surface of hair or skin according to claim 2, 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.

9. The method for modifying the surface of hair or skin according to claim 2, wherein the hair-modifying component or the skin-modifying component has a carboxyl group, a hydroxyl group, a phosphate group, or an amine group in a molecule thereof.

10. The method for modifying the surface of hair or skin according to claim 2, wherein the hair-modifying component or the skin-modifying component has a functional group capable of covalently bonding with a protein residue in a hair surface.

11. The method for modifying the surface of hair or skin according to claim 10, 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.

12. The method for modifying the surface of hair or skin according to claim 2, 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

(1) 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

(2) 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.

(3) TABLE-US-00002 TABLE 1 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative Exam- Exam- Exam- Exam- sition Example Example Example Example Example Example Example Example ple ple ple ple (wt %) 1 2 3 4 5 6 7 8 1 2 3 4 Water 55   55   55   55   54   54   54   54   54   54   54   54   Poly- 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 quarte- nium-7 EDTA  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05 4Na Laurie 3   3   3   3   3   3   3   3   3   3   3   3   acid Myristic 4   4   4   4   4   4   4   4   4   4   4   4   acid Sodium 20   20   20   20   20   20   20   20   20   20   20   20   lauryl ether (2 moles) sulfate (30%) Cocami- 15   15   15   15   15   15   15   15   15   15   15   15   dopropyl betaine (30%) Fragrance 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 Sphingo- 1   — — — 1   — — — 1   — — — sine Amodime- — 1   — — — 1   — — — 1   — — thicone Hyalu- — — 1   — — — 1   — — — 1   — ronic acid Red — — — 1   — — — 1   — — — 1   No. 227 Benzene — — — — 1   1   1   1   — — — — 1,3-bis(1- isocyanato- 1-methyl- ethyl)- homopolymer, polyethylene glycol mono Me-ether- blocked 1,1- — — — — — — — — 1   1   1   1   methylene- bis-(3- isocyanato- cyclohexane)-, homopolymer, polyethylene glycol mono- Me-ether- blocked pH Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable controlling amount amount amount amount amount amount amount amount amount amount amount amount agent Total 100    100    100    100    100    100    100    100    100    100    100    100   

Experimental Example 1: Assessment of Conditioning, Gloss, Moisturizing, and Dyeing Effects

(4) 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.

(5) TABLE-US-00003 TABLE 2 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Classifi- rative rative rative rative rative rative rative rative Exam- Exam- Exam- Exam- cation Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 ple 1 ple 2 ple 3 ple 4 Conditioning 2.7 — — — 3.9 — — — 4.7 — — — effect Increment — 3.5 — — — 17.6 — — — 46.3 — — in gloss (%) Increment — — 2.3 — — — 26.5 — — — 48.7 — in contained water (%) Increment — — — 15.9 — — — 32.3 — — — 48.6 in redness (%)

(6) 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

(7) 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.

(8) TABLE-US-00004 TABLE 3 Skin Increment in conditioning Increment in contained Increment in (five-level skin gloss water redness Compound scale) (%) (%) (%) 1,3-Bis(isocyanatomethyl)cyclohexane-, 4.3 43.6 46.7 46.3 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-, homopolymer, 4.6 45.7 47.3 47.6 polyethylene glycol mono-Me-ether-blocked Diphenylmethane-2,2-diisocyanate-, 4.5 45.0 46.9 46.6 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

(9) 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.

(10) TABLE-US-00005 TABLE 4 Compo- Compa- Compa- Compa- Compa- Compa- Compa- sition rative rative rative rative rative rative Exam- Exam- Exam- (wt %) Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 ple 5 ple 6 ple 7 Water 55 55 55 54 54 54 54 54 54 Polyquater- 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 nium-7 EDTA 4Na 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 Lauric acid 3 3 3 3 3 3 3 3 3 Myristic 4 4 4 4 4 4 4 4 4 acid Sodium 20 20 20 20 20 20 20 20 20 lauryl ether (2 moles) sulfate (30%) Cocami 15 15 15 15 15 15 15 15 15 dopropyl betaine (30%) Fragrance 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 0.9 Niacinamide 1 — — 1 — — 1 — — Hyaluronic — 1 — — 1 — — 1 acid Salicylic — — 1 — — 1 — — 1 acid Benzene, — — — 1 1 1 — — — 1,3-bis(1- isocyanato-1- methylethyl)-, homopolymer, polyethylene glycol mono- Me-ether- blocked 1,1- — — — — — — 1 1 1 methylene- bis-(3- isocyanato- cyclohexane)-, homopolymer, polyethylene glycol mono- Me-ether- blocked pH Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable controlling amount amount amount amount amount amount amount amount amount agent Total 100 100 100 100 100 100 100 100 100

Experimental Example 3: Assessment of Whitening, Wrinkle and Keratin Improvement Effect

(11) 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.

(12) TABLE-US-00006 TABLE 5 Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative Exam- Exam- Exam- Classification Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 ple 5 ple 6 ple 7 Whitening (1.7, 2.5) — — (3.5, 3.9) — — (4.2, 4.5) — — (improvement, persistence) Wrinkle — (1.9, 2.3) — — (3.7, 4.0) — — (4.5, 4.3) — (improvement, persistence) Keratin — — (1.2, 1.9) — — (3.4, 4.0) — — (4.7, 4.3) (improvement, persistence)

(13) 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

(14) 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.

(15) TABLE-US-00007 TABLE 6 Whitening Wrinkle Keratin (improvement, (improvement, (improvement, persistence) persistence) persistence) (five-level (five-level (five-level Compound scale) scale) 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

(16) 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.

(17) TABLE-US-00008 TABLE 7 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative sition Example Example Example Example Example Example Example Example Exam- Exam- Exam- Exam- (wt %) 15 16 17 18 19 20 21 22 ple 8 ple 9 ple 10 ple 11 Water 47   47   47   47   46   46   46   46   46   46   46   46   Polyquater- 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 nium-10 EDTA 4Na  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.05 Sodium 35.0  35.0  35.0  35.0  35.0  35.0  35.0  35.0  35.0  35.0  35.0  35.0  lauryl ether (2 moles) sulfate (30%) Cocamido- 15.0  15.0  15.0  15.0  15.0  15.0  15.0  15.0  15.0  15.0  15.0  15.0  propyl betaine (30%) Fragrance 0.9 0.9 0.9 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 — — — amidopro- pyl amine Phenyl amodi- — 1.0 — — 1.0 — — 1.0 — — methicone Polylysine — — 1.0 — — 1.0 — — 1.0 — Chitosan — — — 1.0 — — — 1.0 — — — 1.0 polymer Benzene — — — 1.0 1.0 1.0 1.0 — — — — 1,3-bis(1- isocyanato-1- methylethyl)-, homopolymer, polyethylene glycol mono- Me-ether- blocked 1,1- methylene- bis-(3- isocyanato- cyclohexane)-, homopolymer, polyethylene glycol mono- Me-ether- blocked pH Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable Suitable controlling amount amount amount amount amount amount amount amount amount amount amount amount 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 

Experimental Example 5: Assessment of Conditioning and Moisturizing Effects

(18) 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.

(19) TABLE-US-00009 TABLE 8 Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compa- Compo- rative rative rative rative rative rative rative rative sition Example Example Example Example Example Example Example Example Exam- Exam- Exam- Exam- (wt %) 15 16 17 18 19 20 21 22 ple 8 ple 9 ple 10 ple 11 Conditioning 2.3 — — — 3.7 — — — 4.5 — — — effect Increment — 1.2 — — — 28 — — — 53 — — in gloss (%) Increment — — 0.23 — — — 3.6 — — — 7.3 — in thickness (%) Water — — — 10.3 — — — 17.2 — — — 25.6 contained in hair (%)

(20) 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

(21) 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.

(22) 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

(23) 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.

(24) 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

(25) 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.

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

(27) 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

(28) 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.

(29) TABLE-US-00013 TABLE 12 Bonding Increment in rate of redness split hair Compound (%) (%) 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

(30) 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.

(31) TABLE-US-00014 TABLE 13 Compa- Compa- Compa- Compa- Compa- Compa- Composition rative rative rative rative rative rative Exam- Exam- Exam- (wt %) Example 27 Example 28 Example 29 Example 30 Example 31 Example 32 ple 14 ple 15 ple 16 Water 57.1  57.1  57.1  56.1  56.1  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  sulfate Laurylalcohol 7.0 7.0 7.0 7.0 7.0 7.0 7.0 7.0 7.0 ethoxylate (12 moles) Lauric 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  triphosphate 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 — — amidopropyl amine Amodime- — 1.0 — 1.0 — 1.0 — thicone Mono-(6- — — 1.0 — — 1.0 — — 1.0 ethanediamine- 6-deoxy)-beta- cyclodextrin Benzene, — — 1.0 1.0 1.0 — — — 1,3-bis(1- isocyanato-1- methylethyl)-, homopolymer, polyethylene gylcol mono- Me-ether- blocked 1,1- — — — — 1.0 1.0 1.0 methylene- bis-(3- isocyanato- cyclohexane)-, homopolymer, polyethylene glycol mono- Me-ether- blocked Total 100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0  100.0 

Experimental Example 9: Assessment of Effects of Preventing Static Electricity, Softening Fabric, and Removing Odor

(32) 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.

(33) TABLE-US-00015 TABLE 14 Compa- Compa- Compa- Compa- Compa- Compa- rative rative rative rative rative rative Exam- Exam- Exam- Classification Example 27 Example 28 Example 29 Example 30 Example 31 Example 32 ple 14 ple 15 ple 16 Static 10.2 — — 38.6 — — 52.4 — — electricity prevention rate (%) Softening — 2.7 — — 3.9 — — 4.3 — effect (sensibility, five-level scale) Odor — — 2.5 — — 3.9 — — 4.5 removal (sense, five-level scale)

(34) 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

(35) 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.

(36) TABLE-US-00016 TABLE 15 Static Softening electricity effect Odor prevention (sensibility, removal rate five-level (sense, five- Compound (%) 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

(37) Body cleansers as shown in Table 16 below were prepared through a common method of preparing a body cleanser.

(38) TABLE-US-00017 TABLE 16 Conditioning Skin gloss Moisturizing Dyeing Whitening Wrinkle care Keratin care body body body body body body body Composition cleanser cleanser cleanser cleanser cleanser cleanser cleanser Raw material Content Content Content Content Content Content Content (%) (%) (%) (%) (%) (%) (%) 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 lauly1 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)

(39) 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.

(40) TABLE-US-00018 TABLE 17 Whitening Whitening Whitening Whitening 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 (pH 5.5) Remainder Remainder Remainder Remainder Total 100.0  100.0  100.0  100.0 

Preparation Example 3: Preparation of Conditioning Shampoo

(41) A hair conditioning shampoo as shown in Table 18 below was prepared through a common method of preparing a hair shampoo.

(42) 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)

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

(44) TABLE-US-00020 TABLE 19 Conditioning Conditioning Conditioning Conditioning 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) Remainder Remainder Remainder Remainder

Preparation Example 5: Preparation of Laundry Detergent

(45) A laundry detergent as shown in Table 20 below was prepared through a common method of preparing a laundry detergent.

(46) 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

(47) A laundry softener as shown in Table 21 below was prepared through a common method of preparing a fabric softener.

(48) 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

(49) 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.

(50) 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.