Composition for hair

Abstract

The present invention relates to: an organosilane compound; a hair coloring composition comprising same; and a hair coloring shampoo comprising same. Also, the present invention relates to a composition for hair. By comprising an organosilane compound having a specific structure, the composition according to the present invention can achieve the effects of preventing and reducing hair frizz, preventing thermal damage to hair, and styling hair.

Description

Hair composition

[0001] The present invention relates to a hair composition.

[0002] Changing the shape and color of keratin fibers, especially hair, is an important area of ​​modern cosmetics. To change hair color, professionals apply various coloring systems depending on the desired color. Oxidation dyes are typically used for permanent, intensive coloring with good fastness properties and good gray coverage. These dyes typically contain an oxidation dye precursor, a so-called developer component, and a coupler component, which react under the influence of an oxidizing agent such as hydrogen peroxide to form the actual dye. Oxidation dyes are characterized by extremely long-lasting coloration.

[0003] When using direct dyes, the pre-cured dye diffuses from the colorant into the hair fibers. Colors obtained with direct dyes have a shorter shelf life and faster washability compared to oxidative hair dyes. Colors obtained with direct dyes typically remain on hair for 5 to 20 washes.

[0004] The use of coloring pigments is known for short-term color changes in hair and / or skin. Color pigments are generally understood to be insoluble coloring substances. They exist insoluble in dye formulations in the form of small particles and are deposited only on the outer surface of hair fibers and / or skin. Therefore, they can be removed without residue by washing them several times with a detergent containing surfactants. Various products of this type are available on the market under the brand name "hair mascara."

[0005] For hair dyes that require particularly long-lasting color, oxidative dyes have traditionally been the only option. However, despite numerous optimization attempts, the unpleasant ammonia or amine odor from oxidative dyes has not been completely eliminated. Furthermore, hair damage associated with the use of oxidative dyes negatively impacts the hair of users.

[0006] Accordingly, a need has arisen for a dyeing system with fastness properties comparable to oxidative dyeing. Specifically, excellent color strength (dyeing power) and wash fastness (dyeing durability) properties are required, while avoiding the use of oxidative dye precursors typically used for this purpose. Furthermore, a technique has been pursued that enables highly durable fixation of pigments known from the state of the art to hair. The pigments incorporated into keratin materials should not be separated from the keratin materials, even after repeated washings (e.g., hair washing).

[0007] Hair is a human tissue that does not naturally regenerate after exposure to the elements. However, in pursuit of beauty, people continually subject their hair to chemical damage, such as dyeing, bleaching, or perming, as well as physical damage, such as excessive brushing or heating. This excessive damage can cause hair to become brittle, dull, and frizzy.

[0008] Hairstyling is the process of altering the appearance of hair, either to enhance its attractiveness or to enhance its appearance. In modern society, where the pursuit of aesthetic individuality is on the rise, interest in hair styling has significantly increased. To achieve this, people often use heat tools like hair dryers and curling irons, or resort to chemical treatments like perms or dyeing.

[0009] In particular, hair styling using heat tools is common, but depending on the temperature of the heat tool and the time and power of applying heat to the hair, the hair may be damaged by high heat, the styling may not be done properly, or the styling may quickly come undone and the hair may return to its original shape.

[0010] Therefore, before using heat tools, it's important to use hair products that protect hair from damage and aid in styling. Existing hair products, such as hair essences, are limited in their ability to add softness and shine to hair. Hair styling products, such as waxes and sprays, leave hair feeling sticky and stiff, making natural styling difficult. Furthermore, they wash off easily, limiting their effectiveness in protecting hair from high-temperature heat tools or assisting in styling.

[0011] Previous studies, such as Patent Document 0001 US10716748 and Patent Document 0002 CN101945643, used high molecular silicone compounds to form a film on the hair surface to protect hair from heat. However, large amounts of product are required to achieve an appropriate effect, and the effect of forming a film is only to temporarily reduce friction caused by heat tools or improve texture, and does not fundamentally protect hair from damage. Furthermore, there are limitations in assisting hair styling using heat tools.

[0012] There are also studies such as Patent Document 0003 JP7010457 that use polymer compounds other than silicone, but this also does not deviate much from the film-forming technology, so the heat damage prevention effect is not particularly excellent. In addition, polymer compounds that provide a setting effect, which are generally used in hair styling products, also have limitations in that the effect is temporary, and natural styling is difficult due to the stickiness, stiffness, and hardness of use, and it is difficult to expect a great heat protection effect for the hair.

[0013] Frizz is a general term for the phenomenon of hair unintentionally rising, sticking out, or becoming unnaturally curled. Frizz not only negatively affects aesthetics, but also makes styling, such as straightening or aligning hair, difficult. Furthermore, frizz can be unpleasant to the touch, making daily life inconvenient. Frizz is generally known to be caused primarily by moisture within the hair or external moisture, but damage to the hair due to various other factors can also cause frizz.

[0014] It is generally known that hair frizz is caused by moisture. Therefore, existing technologies have generally used moisture-regulating methods to reduce the effects of moisture. Patents such as Patent Document 0004 EP3868444 and Patent Document 0005 EP3383356 are representative examples, and specifically, a combination of 2-Hexyl-1-decanol, which can produce synergy with salicylic acid and its derivatives, was used. In addition, Patent Document 0006 EP3697501 attempted to control moisture and achieve an anti-frizz effect using N-Formyl Amino Acid. However, most of these moisture-regulating technologies for reducing frizz are not effective enough to satisfy consumers, and the effects are short-lived, requiring repeated use.

[0015] Another way to reduce frizz is to style hair using polymers. Patent document 0007 EP3322486 is an example of such a method. However, this type of styling-based frizz reduction method has the disadvantage of making hair stiff and sticky due to the polymer-based nature of the method, as well as the inconvenience of requiring additional styling products.

[0016] In addition, it is widely known that coating the surface of the hair with oil reduces frizz, but this not only causes a sticky and greasy feeling due to the oil, but also causes problems such as shine.

[0017] In addition, the possibility of reducing hair frizz using alkoxysilane has been mentioned in patent documents 0008 US 2013-067860 and 0009 US 2020-0206122, but in the case of the technology, the reactivity is relatively low due to the structural characteristics of the materials used, and it is insufficient to obtain a frizz reduction effect that is sufficient to satisfy consumers.

[0018] Therefore, although anti-frizz effects can be achieved through existing technologies, the effects are not only insufficient to satisfy consumers, but also have poor durability. Therefore, although frizz can be temporarily reduced, there is a corresponding discomfort (stickiness, stiffness, etc.), and the inconvenience of requiring repeated use to maintain the effect occurs.

[0019] The present invention provides a hair coloring composition comprising at least one organic silane compound.

[0020] In addition, the present invention provides a hair coloring shampoo comprising the hair coloring composition.

[0021] In addition, the present invention provides a hair coloring method including a step of washing hair with the hair coloring shampoo.

[0022] The present invention relates to a hair composition, and more particularly, to a hair composition for preventing or improving hair frizz and preventing hair from heat damage and for hair styling, comprising as an active ingredient an organic silane compound having a structure in which two or more tertiary amines are linked to each other, the organic silane compound having four or more silicon atoms constituting an alkoxysilane or silanol residue at a terminal portion within the molecule and six or more carbon atoms at a central portion within the molecule.

[0023] These compounds can form covalent bonds with hair due to heat at the terminal portion of the molecule, and by implementing the properties of silane into the hair, they can reduce hair frizz and ensure the sustainability of frizz reduction, thereby achieving an anti-frizz effect that is different from existing technologies. In addition, they have hydrophobic properties that can provide moisture resistance, so when styling hair using heat tools, they can protect hair from heat by combining with hair, making the desired hairstyle faster and stronger, and making the hairstyle last longer.

[0024] The present invention provides a compound represented by the following chemical formula 1a:

[0025] [Chemical Formula 1a]

[0026]

[0027] In the above chemical formula 1a,

[0028] X1 and X2 are each independently O or -(CH2)-,

[0029] a to c are each independently an integer from 1 to 5,

[0030] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0031] n is an integer from 2 to 5,

[0032] m is an integer from 1 to 3.

[0033] In addition, the present invention provides a hair coloring composition comprising at least one organic silane compound represented by the chemical formula 1a.

[0034] The present invention provides a hair coloring composition comprising at least one organic silane compound represented by the following chemical formula 1b:

[0035] [Chemical Formula 1b]

[0036]

[0037] In the above chemical formula 1b,

[0038] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0039] R3 is one or more C 1-10 Alkyl-substituted amine; C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 Heterocycloalkyl; substituted or unsubstituted C 6-20 Aryl; or C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl,

[0040] m is an integer from 1 to 3,

[0041] n1b is an integer from 2 to 5,

[0042] n2b is an integer from 0 to 5.

[0043] The present invention provides a compound represented by the following chemical formula 1c:

[0044] [Chemical Formula 1c]

[0045]

[0046] In the above chemical formula 1c,

[0047] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0048] x is an integer of 2 or 3,

[0049] m is an integer from 1 to 3,

[0050] n1 is an integer from 0 to 5,

[0051] n2 is an integer from 1 to 5.

[0052] In addition, the present invention provides a hair coloring composition comprising at least one organic silane compound represented by the chemical formula 1c.

[0053] The present invention provides a compound represented by the following chemical formula 1d:

[0054] [Chemical Formula 1d]

[0055]

[0056] In the above chemical formula 1d,

[0057] x is an integer of 2 or 3,

[0058] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0059] n is an integer from 2 to 5,

[0060] m is an integer from 1 to 3.

[0061] In addition, the present invention provides a hair coloring composition comprising at least one organic silane compound represented by the chemical formula 1d.

[0062] In addition, the present invention provides a hair coloring method comprising a step of applying the hair coloring composition to hair.

[0063] In addition, the present invention provides a hair coloring shampoo comprising the hair coloring composition.

[0064] In addition, the present invention provides a hair coloring method comprising a step of washing hair with the hair coloring shampoo.

[0065] The present invention provides a hair composition comprising one or more selected from the group consisting of organic silane compounds represented by the following chemical formulae 1e to 3e.

[0066] [Chemical Formula 1e]

[0067]

[0068] [Chemical Formula 2e]

[0069]

[0070] [Chemical Formula 3e]

[0071]

[0072] In the above chemical formulas 1e to 3e

[0073] x is an integer of 2 or 3,

[0074] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0075] m is an integer from 1 to 3.

[0076] n is an integer from 2 to 5,

[0077] n1 is an integer from 0 to 5,

[0078] n2 is an integer from 1 to 5,

[0079] X1 and X2 are each independently O or -(CH2)-,

[0080] a to c are each independently an integer from 1 to 5.

[0081] In addition, the present invention provides a hair composition for preventing or improving hair frizz.

[0082] The present invention also provides a method for preventing or improving hair frizz, comprising the step of treating hair with a hair composition.

[0083] In addition, the present invention provides a hair composition for preventing heat damage to hair and for styling hair.

[0084] The present invention also provides a method for preventing heat damage to hair and styling hair, comprising a step of treating hair with a hair composition.

[0085] The organic silane compound represented by the chemical formula described above can be used for hair coloring purposes, and when included in a hair coloring composition, can improve the coloring power and / or coloring durability.

[0086] In addition, the composition according to the present invention contains an organic silane compound having a specific structure, thereby preventing and improving hair frizz, preventing heat damage to hair, and achieving a hair styling effect.

[0087] Figure 1 is a graph showing the area fraction of frizzy hair (FAF%) of hair applied with comparative examples and examples according to the present invention (-Experiment e-).

[0088] Figure 2 is a photo of light irradiation of hair applied with a comparative example and an example according to Experimental Example 1 of the present invention (-Experiment e-).

[0089] Figure 3 is a graph showing the rate of change in hair frizziness according to comparative examples and examples of the present invention (-Experiment e-).

[0090] Figure 4 is a photo of light irradiation of hair applied with a comparative example and an example according to Experimental Example 2 of the present invention (-Experiment e-).

[0091] Hereinafter, the present invention will be described in more detail to help understand the present invention.

[0092] The terminology used herein is for the purpose of describing exemplary embodiments only and is not intended to limit the present invention. The singular expression includes the plural expression unless the context clearly indicates otherwise. In this specification, it should be understood that the terms "comprise," "include," or "have" indicate the presence of a feature, step, component, or combination thereof, but do not preclude the possibility of the presence or addition of one or more other features, steps, components, or combinations thereof.

[0093] The present invention is susceptible to various modifications and takes various forms. Specific embodiments are illustrated and described in detail below. However, this is not intended to limit the present invention to specific disclosed forms, but rather to encompass all modifications, equivalents, and alternatives falling within the spirit and technical scope of the present invention.

[0094] Additionally, the technical terminology used herein is for the purpose of describing specific embodiments only and is not intended to limit the present invention. Furthermore, the singular forms used herein also include the plural forms, unless the context clearly dictates otherwise.

[0095] The term "hair coloring" of the present invention refers to expressing a new color in hair using a composition including a dye, etc., and may specifically include blackening hair, deepening hair color from light to dark, or preventing hair from whitening (including covering gray hair). This 'hair coloring' differs in its mechanism from that of conventional 'hair dyeing'. The principle of conventional hair dyeing is that the alkaline component of the hair dye swells the hair or lifts the hair surface cuticle, and when a pigment precursor penetrates into the lifted hair, an oxidizing agent such as hydrogen peroxide bleaches the melanin in the hair and simultaneously reacts with the pigment precursor to dye the hair. On the other hand, the hair coloring composition including an organic silane compound and / or a dye according to the present invention acts as a coloring compound on the surface of keratin materials such as hair, skin, fingernails, and toenails, thereby enhancing dye deposition. Due to the enhanced deposition, the dyeing power and / or dyeing durability are excellent, coloring the keratin surface in brown, dark brown, or black, etc. The above organic silane compound can contribute to the formation of the film through oligomerization or polymerization.

[0096] When the hair composition containing the organic silane compound of the present invention is applied to the hair, the properties of the silane can be semi-permanently implemented in the hair by binding to the hair. In particular, when the silane having the hydrophobic structure of the present invention is left on the hair, the hair becomes hydrophobic, which leads to the effect of preventing changes in hair moisture due to the external environment such as the atmosphere, and ultimately, it is expected to result in the appearance of an anti-frizz effect. In addition, when the hair is applied to the hair, the organic silane compound of the present invention has a heat protection effect, so that the hair is effectively protected from strong heat during hair styling, and the styling is assisted so that the hair style can be formed quickly and maintained for a long time.

[0097] Additionally, normal hair has a lipid layer represented by 18-MEA at the outermost cuticle, and this lipid layer is damaged by various damaging factors (heat, UV rays, etc.) encountered in daily life. This can cause negative phenomena such as frizz, roughness, and dullness that are not observed in normal hair. At this time, when the silane compound of the present invention is combined with damaged hair, the damaged hair can be transformed (restored) to resemble normal hair, thereby resolving the phenomena caused by hair damage.

[0098] The above effects were confirmed through experimental examples and examples.

[0099] The term "substituted or unsubstituted" as used herein means a group that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylphosphine group; or a heteroaryl group containing at least one of N, O, and S atoms, or a substituted or unsubstituted group in which two or more substituents among the above-mentioned substituents are linked. For example, the "substituent linked with two or more substituents" may be a biphenyl group. That is, a biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are connected. For example, the term "substituted or unsubstituted" means "unsubstituted, or substituted with deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy, C 6-20 C containing aryl and one or more heteroatoms of N, O and S 2-20The term "substituted with one or more, for example, 1 to 5, substituents selected from the group consisting of heteroaryl" can be understood to mean "substituted with one or more, for example, 1 to 5, substituents." In addition, the term "substituted with one or more, for example, 1 to 5, substituents" in the present specification can be understood to mean "substituted with one to 5, for example, 1 to 2, or 2, substituents."

[0100] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0101]

[0102] In the present specification, the ester group may have the oxygen of the ester group substituted with a straight-chain, branched-chain, or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may have the following structural formula, but is not limited thereto.

[0103]

[0104] In this specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0105]

[0106] In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc.

[0107] In this specification, the boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, etc.

[0108] In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0109] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, Examples include, but are not limited to, 4-methylhexyl and 5-methylhexyl.

[0110] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

[0111] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[0112] In the present specification, heterocycloalkyl refers to a cyclic substituent of heteroalkyl, and means a substituent in which at least one carbon in cycloalkyl is replaced with at least one of heteroatoms O, N, Si, and S. The carbon number of heterocycloalkyl is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heterocycloalkyl groups include, but are not limited to, 1-(1,2,5,6-tetrahydropyridyl), 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-morpholinyl, 3-morpholinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, 1-piperazinyl, 2-piperazinyl, and the like.

[0113] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0114] In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted, It can be, but is not limited to, the following.

[0115] In the present specification, a heteroaryl group is a heteroaryl group containing at least one of O, N, Si, and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 20. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group, There are, but are not limited to, phenothiazinyl groups and dibenzofuranyl groups.

[0116] In this specification, the aryl group among the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the examples of the aryl group described above. In this specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the alkyl group described above. In this specification, the heteroaryl among the heteroarylamine may be applied to the description of the heteroaryl group described above. In this specification, the alkenyl group among the aralkenyl group is the same as the examples of the alkenyl group described above. In this specification, the description of the aryl group described above may be applied to the arylene except that it is a divalent group. In this specification, the description of the heteroarylene described above may be applied to the heteroaryl group except that it is a divalent group. In this specification, the description of the aryl group or the cycloalkyl group described above may be applied to the hydrocarbon ring except that it is not a monovalent group but is formed by combining two substituents. In this specification, the description of the heteroaryl group described above may be applied, except that the heteroaryl is not monovalent and is formed by combining two substituents.

[0117] The present invention provides an organic silane compound represented by the following chemical formula 1a:

[0118] [Chemical Formula 1a]

[0119]

[0120] In the above chemical formula 1a,

[0121] X1 and X2 are each independently O or -(CH2)-,

[0122] a to c are each independently an integer from 1 to 5,

[0123] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0124] n is an integer from 2 to 5,

[0125] m is an integer from 1 to 3.

[0126] Preferably, a to c may be integers from 2 to 4.

[0127] Preferably, R1 and R2 are each independently substituted or unsubstituted C 1-5 It may be alkyl. More preferably, R1 and R2 may each independently be methyl or ethyl. Most preferably, R1 and R2 may each be ethyl.

[0128] Preferably, R1 and R2 can be the same.

[0129] Preferably, n can be 3.

[0130] Preferably, m can be 3.

[0131] Preferably, the organic silane compound represented by the above chemical formula 1a may be represented by the following chemical formula 1a-1 or chemical formula 1a-2:

[0132] [Chemical Formula 1a-1]

[0133]

[0134] [Chemical Formula 1a-2]

[0135] .

[0136] The present invention includes a hair coloring composition comprising at least one organic silane compound represented by the above chemical formula 1a.

[0137] The present invention provides a hair coloring composition comprising at least one organic silane compound represented by the following chemical formula 1b:

[0138] [Chemical Formula 1b]

[0139]

[0140] In the above chemical formula 1b,

[0141] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0142] R3 is one or more C 1-10Alkyl-substituted amine; C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 Heterocycloalkyl; substituted or unsubstituted C 6-20 Aryl; or C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl,

[0143] m is an integer from 1 to 3,

[0144] n1b is an integer from 2 to 5,

[0145] n2b is an integer from 0 to 5.

[0146] Preferably, R1 and R2 can each independently be methyl, ethyl, propyl, butyl, pentyl, or hexyl. More preferably, R1 and R2 can each independently be methyl or ethyl. Most preferably, R1 and R2 can each be ethyl.

[0147] Preferably, R3 is one or more C 1-5 Alkyl-substituted amine; C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-10 Heterocycloalkyl; substituted or unsubstituted C 6-10 C comprising at least one selected from the group consisting of aryl; or unsubstituted N, O and S; 2-10 It may be heteroaryl. More preferably, R3 may be imidazolyl, 1-methylpiperazinyl, or diethylamine.

[0148] Preferably, m can be 3.

[0149] Preferably, n1b can be 3.

[0150] Preferably, n2b can be 3.

[0151] Preferably, the organic silane compound represented by the above chemical formula 1b may be any one selected from the following group.

[0152]

[0153] The present invention provides an organic silane compound represented by the following chemical formula 1c:

[0154] [Chemical Formula 1c]

[0155]

[0156] In the above chemical formula 1c,

[0157] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0158] x is an integer of 2 or 3,

[0159] m is an integer from 1 to 3,

[0160] n1 is an integer from 0 to 5,

[0161] n2 is an integer from 1 to 5.

[0162] Preferably, the organic silane compound represented by the above chemical formula 1c may be represented by the following chemical formula 1c-1 or 1c-2:

[0163] [Chemical Formula 1c-1]

[0164]

[0165] [Chemical Formula 1c-2]

[0166]

[0167] In the above chemical formulas 1c-1 and 1c-2,

[0168] R1, R2, m, n1 and n2 are as defined in the above chemical formula 1c.

[0169] Preferably, R1 and R2 can each independently be methyl, ethyl, propyl, butyl, pentyl, or hexyl. More preferably, R1 and R2 can each be ethyl.

[0170] Preferably, m may be 2 or 3. More preferably, m may be 3.

[0171] Preferably, n1 can be 1.

[0172] Preferably, n2 can be 3.

[0173] Preferably, the organic silane compound represented by the above chemical formula 1c can be represented by the following chemical formula 1c-3 or 1c-4.

[0174] [Chemical Formula 1c-3]

[0175]

[0176] [Chemical Formula 1c-4]

[0177] .

[0178] The present invention includes a hair coloring composition comprising at least one organic silane compound represented by the above chemical formula 1c.

[0179] The compounds represented by the above chemical formulas 1a to 1c can be prepared, for example, by an amine substitution reaction. The reactor for the amine substitution reaction can be modified as known in the art. The above preparation method can be further detailed in the preparation examples described below.

[0180] The present invention provides an organic silane compound represented by the following chemical formula 1d:

[0181] [Chemical Formula 1d]

[0182]

[0183] In the above chemical formula 1d,

[0184] x is an integer of 2 or 3,

[0185] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0186] n is an integer from 2 to 5,

[0187] m is an integer from 1 to 3.

[0188] Preferably, the organic silane compound represented by the above chemical formula 1d may be represented by any one of the following chemical formulas 1d-1 to 1d-3:

[0189] [Chemical formula 1d-1]

[0190]

[0191] [Chemical formula 1d-2]

[0192]

[0193] [Chemical formula 1d-3]

[0194]

[0195] In the above chemical formulas 1d-1 to 1d-3,

[0196] R1, R2, m and n are as defined in the above chemical formula 1d.

[0197] Preferably, R1 and R2 can each independently be methyl, ethyl, propyl, butyl, pentyl, or hexyl. More preferably, R1 and R2 can each be ethyl.

[0198] Preferably, n may be 2 or 3. More preferably, n may be 3.

[0199] Preferably, m may be 2 or 3. More preferably, m may be 3.

[0200] Preferably, the organic silane compound represented by the above chemical formula 1d may be any one selected from the following group:

[0201] .

[0202] The present invention includes a hair coloring composition comprising at least one organic silane compound represented by the chemical formula 1d.

[0203] The compound represented by the above chemical formula 1d can be prepared, for example, from a benzene derivative having a carbonyl chloride substituent. The compound represented by the above chemical formula 1d can be prepared by reacting a benzene derivative having a carbonyl chloride substituent with an amine having an organic silane substituent. A more specific preparation method can be further specified in the preparation examples described below.

[0204] The above 'hair coloring' is as described above. Preferably, the above 'hair coloring' may include hair browning or blackening, or hair whitening prevention.

[0205] Preferably, the hair coloring composition may contain the organic silane compound represented by the chemical formula 1 in an amount of 0.001 wt% or more and 10 wt% or less based on the total weight. Preferably, it is 0.01 wt% or more, 0.05 wt% or more, 0.1 wt% or more, 0.5 wt% or more, or 1 wt% or more, and may be 8 wt% or less, 6 wt% or less, 5 wt% or less, 4 wt% or less, 3 wt% or less, or 2 wt% or less.

[0206] When the content of the organic silane compound is less than 0.001 wt% based on the total weight of the hair coloring composition, the dyeing power and dyeing durability are not sufficiently enhanced, and when it exceeds 10 wt%, not only does the viscosity of the composition increase rapidly, but it also causes inconvenience to consumers when using the hair coloring composition and causes a problem of causing a rough texture to the hair.

[0207] The above hair coloring composition may further include, but is not limited to, one or more selected from a dye, a cationic polymer compound, a surfactant, a pH adjusting agent, a buffering agent, a preservative, a fragrance, a moisturizer, a viscosity adjusting agent, a chelating agent, an aliphatic alcohol, and a vitamin. The dye, the cationic polymer compound, the surfactant, the pH adjusting agent, the buffering agent, the preservative, the fragrance, the moisturizer, the viscosity adjusting agent, the chelating agent, and the aliphatic alcohol are as described below.

[0208] More specifically, the dye may be used without particular limitation as long as it is commonly used in the art, and generally includes at least one selected from basic dyes such as Basic Red 51, Basic Blue 99, and Basic Brown 16, and acid dyes such as Acid Red 52 and Acid Red 92, and in addition, any pigment or the like commonly used in the art may be used without particular limitation, and may be selected from natural dyes and artificially synthesized dyes.

[0209] The cationic polymer compound refers to any polymer containing a cationic group and / or a group capable of being ionized by a cationic group, and can be used without particular limitation as long as it is commonly used in the art. The cationic polymer compound is selected from those containing a unit including a primary, secondary, tertiary and / or quaternary amine group, and this may form a part of the polymer main chain or may be maintained by a side chain substituent directly bonded to the polymer main chain. In particular, the cationic polymer compound is preferably a polymerizable quaternary ammonium salt, and for example, any one or more selected from the group consisting of polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-11, polyquaternium-15, polyquaternium-16, polyquaternium-28, polyquaternium-44, polyquaternium-46 and polyquaternium-47 can be used.

[0210] The above surfactant may be an alkyl sulfate (AS), an alkyl ether sulfate (AES), a sodium alkane sulfonate (SAS), an alkyl trimethyl ammonium halide, an alkyl pyridinium halide, an alkyl imidazolium halide, a polyethylene oxide-based surfactant, a polyvinyl-based water-soluble polymer, etc., and non-limiting examples thereof include sodium dodecyl sulfate (SDS), sodium octylbenzene sulfonate (NaOBS), sodium dodecylbenzene sulfonate (SDBS), ammonium lauryl sulfate (ALS), and Triton. It may be at least one selected from, but is not limited to, X-100 (Triton X-100), polyvinyl pyrrolidone (PVP), and cocamidopropyl betaine (CAPB).

[0211] The above pH adjusting agent is for adjusting the pH of the aqueous dye composition, and any agent commonly used in the art may be used without particular limitation, and any one or more selected from sodium hydroxide, potassium hydroxide, triethanolamine, hydrous or anhydrous citric acid, and sodium citrate may be used.

[0212] The above buffering agent may be used without particular limitation as long as it is commonly used in the art, and any one or two or more selected from salicylic acid, sodium salicylate, lactic acid, and sodium lactate may be used.

[0213] The above preservative may be used without particular limitation as long as it is commonly used in the art, and may include at least one selected from among methylparaben, propylparaben, phenoxyethanol, methyl p-hydroxybenzoate, and ethyl p-hydroxybenzoate, and the above fragrance may be used without particular limitation as long as it is commonly used in the art, and may be selected from natural fragrances or artificial synthetic fragrances.

[0214] The above moisturizer can be used without any particular limitation as long as it is commonly used in the art, and commonly used ingredients including glycols such as polyethylene glycol and oils can be used.

[0215] The viscosity modifier may be used without particular limitation as long as it is commonly used in the art, and may be one or more selected from hydroxyethyl cellulose, sodium chloride, poly stearate, and sodium carboxymethyl cellulose. The chelating agent may be used without particular limitation as long as it is commonly used in the art, and tetrasodium EDTA may be used. The fatty alcohol may be used without particular limitation as long as it is commonly used in the art, and one or more fatty alcohols having 16 to 22 carbon atoms, such as cetyl alcohol, stearyl alcohol, or behenyl alcohol, may be selected and used. The vitamin may be used to supplement nutrition to hair.

[0216] Meanwhile, the hair coloring composition according to the present invention may contain water in addition to the aforementioned components. The water may be purified water such as ion-exchanged water or distilled water. The content is not particularly limited, but any amount sufficient to sufficiently dissolve or disperse the aforementioned components may be used.

[0217] The above hair coloring composition may be in the form of a shampoo, hair conditioner, hair treatment, hair lotion, hair gel, hair pack, hair cream or hair essence, but is not limited thereto.

[0218] Meanwhile, the present invention provides a hair coloring method comprising a step of applying the hair coloring composition to hair.

[0219] The method may further include a step of applying the hair coloring composition to the hair and leaving it for 0.1 to 30 minutes, and specifically, the hair can be colored brown, dark brown, or black even with only a very short period of time of 0.1 to 5 minutes, more specifically, 0.1 to 3 minutes, or 1 to 3 minutes. At this time, the application method is not particularly limited, and methods such as immersing the hair in the hair coloring composition or spraying the hair coloring composition onto the hair can be used.

[0220] Meanwhile, the present invention provides a hair coloring method comprising a step of washing hair with the hair coloring composition. The step of washing hair may be performed for 1 to 10 minutes, or 1 to 5 minutes, or 1 to 3 minutes, but is not limited thereto.

[0221] For example, a hair coloring shampoo comprising the hair coloring composition may be provided.

[0222] The above hair coloring shampoo may further include one or more selected from the above-described dyes, cationic polymer compounds, surfactants, pH regulators, buffers, preservatives, fragrances, moisturizers, viscosity regulators, chelating agents, aliphatic alcohols, and vitamins, but is not limited thereto.

[0223] By adding a hair coloring composition to a commonly used shampoo composition in this way to manufacture a hair coloring shampoo, a shampoo capable of coloring hair darkly while shampooing daily is provided. When using the hair coloring shampoo according to the present invention, the pigment is more effectively absorbed into the hair during the daily shampooing process, thereby coloring the hair, so that additional coloring occurs instead of the hair color fading phenomenon, thereby preventing the hair color fading phenomenon that occurs most commonly during the shampooing process. In addition, when using the hair coloring shampoo, not only is the conventional dyeing process time that takes tens of minutes or more unnecessary, but periodic additional treatments due to growing hair, etc. are not required, so convenience is greatly increased, and the hair can be colored darkly while minimizing hair damage in a short period of time.

[0224] For example, the hair coloring method may include a step of washing hair with the hair coloring shampoo.

[0225] The above hair washing step can be performed for 1 to 10 minutes, or 1 to 5 minutes, or 1 to 3 minutes, but is not limited thereto.

[0226] The present invention provides a hair composition comprising one or more selected from the group consisting of organic silane compounds represented by the following chemical formulae 1e to 3e.

[0227] [Chemical Formula 1e]

[0228]

[0229] [Chemical Formula 2e]

[0230]

[0231] [Chemical Formula 3e]

[0232]

[0233] In the above chemical formulas 1e to 3e

[0234] x is an integer of 2 or 3,

[0235] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0236] m is an integer from 1 to 3.

[0237] n is an integer from 2 to 5,

[0238] n1 is an integer from 0 to 5,

[0239] n2 is an integer from 1 to 5,

[0240] X1 and X2 are each independently O or -(CH2)-,

[0241] a to c are each independently an integer from 1 to 5.

[0242] In the above chemical formula 1e,

[0243] The above x is an integer of 2 or 3,

[0244] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0245] m is an integer from 1 to 3,

[0246] n is an integer from 2 to 5.

[0247] The organic silane compound represented by the above chemical formula 1e may be represented by any one of the following chemical formulas 1e-1 to 1e-3:

[0248] [Chemical formula 1e-1]

[0249]

[0250] [Chemical formula 1e-2]

[0251]

[0252] [Chemical formula 1e-3]

[0253]

[0254] In the above chemical formulas 1e-1 to 1e-3,

[0255] R1, R2, m and n are as defined in the above chemical formula 1e.

[0256] In the above chemical formula 1e, preferably, R1 and R2 can each independently be methyl, ethyl, propyl, butyl, pentyl, or hexyl. More preferably, R1 and R2 can each be ethyl.

[0257] In the above chemical formula 1e, m may be 2 or 3. More preferably, m may be 3.

[0258] In the above chemical formula 1e, n may be 2 or 3. More preferably, n may be 3.

[0259] The organic silane compound represented by the above chemical formula 1e may be any one selected from the following group:

[0260]

[0261] In the above chemical formula 2e,

[0262] The above x is an integer of 2 or 3,

[0263] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0264] m is an integer from 1 to 3,

[0265] n1 is an integer from 0 to 5,

[0266] n2 is an integer from 1 to 5.

[0267] The organic silane compound represented by the above chemical formula 2e may be represented by either the following chemical formula 2e-1 or 2e-2:

[0268] [Chemical formula 2e-1]

[0269]

[0270] [Chemical formula 2e-2]

[0271]

[0272] In the above chemical formulas 2e-1 and 2e-2,

[0273] R1, R2, m, n1 and n2 are as defined in the above chemical formula 2e.

[0274] In the above chemical formula 2e, preferably, R1 and R2 can each independently be methyl, ethyl, propyl, butyl, pentyl, or hexyl. More preferably, R1 and R2 can each be ethyl.

[0275] In the above chemical formula 2e, preferably, m may be 2 or 3. More preferably, m may be 3.

[0276] In the above chemical formula 2e, preferably, n1 may be 1.

[0277] In the above chemical formula 2e, n2 may be 3.

[0278] The organic silane compound represented by the above chemical formula 2e may be any one selected from the following group:

[0279] .

[0280] In the above chemical formula 3e

[0281] R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl,

[0282] m is an integer from 1 to 3,

[0283] n is an integer from 2 to 5,

[0284] X1 and X2 are each independently O or -(CH2)-,

[0285] a to c are each independently an integer from 1 to 5.

[0286] In the above chemical formula 3e, preferably, a to c may be integers of 2 to 4.

[0287] In the above chemical formula 3e, preferably, R1 and R2 are each independently substituted or unsubstituted C 1-5 It may be alkyl. More preferably, R1 and R2 may each independently be methyl or ethyl. Most preferably, R1 and R2 may each be ethyl.

[0288] In the above chemical formula 3e, preferably, R1 and R2 can be the same as each other.

[0289] In the above chemical formula 3e, preferably, m may be 3.

[0290] In the above chemical formula 3e, preferably, n may be 3.

[0291] The organic silane compound represented by the above chemical formula 3e may be represented by either the following chemical formula 3e-1 or 3e-2:

[0292] [Chemical formula 3e-1]

[0293]

[0294]

[0295] [Chemical formula 3e-2]

[0296] .

[0297] The hair composition of the present invention provides a hair composition for preventing or improving hair frizz.

[0298] In the present invention, the effect of "preventing or improving hair frizz" means that the area corresponding to the frizz portion in the hair is reduced. For example, a lower frizz change rate value of the hair measured according to Equation 1e below means a better frizz reduction effect. The frizz change rate value of the hair can be confirmed by quantifying the degree of change in hair frizz using the area fraction of the frizzed hair (Frizz Area Fraction, degree of frizz, FAF) measured according to Equation 2e below. At this time, the frizz change rate value of the hair according to Equation 1e means the ratio of the FAF Value after washing to the initial FAF Value (before washing), and a larger value means that the FAF Value after washing increases, which means that the Frizz (frizz) increases due to the washing process. All of the above measurements can be performed under conditions of a temperature of 25°C, a relative humidity of 50%, and a dark room. In the following equation 2e, the area fraction of frizzy hair (Frizz Area Fraction, FAF) is determined by the equation 2e, and the “frizz area” in the equation 2e is a portion where light transmittance is 50% or more when light is irradiated to the hair using a Bolero-Lite (BOSSA NOVA VISION, USA) device, the area of ​​the neat hair (Bulk area) is a portion where light transmittance is less than 50%, and the area fraction of frizzy hair (FAF) means the area ratio occupied by the frizzy portion in the entire hair area.

[0299] [Formula 1e]

[0300]

[0301] [Equation 2e]

[0302]

[0303] In the present invention, the rate of change in the stiffness calculated by the above formula 1e may be 40% or less, 30% or less, or 10% or less.

[0304] The hair composition of the present invention provides a hair composition for preventing heat damage to hair and for styling hair.

[0305] In the present invention, the "prevention of heat damage to hair" effect can be confirmed by the difference in tensile strength of hair treated with hot air from a dryer and hair treated with a curling iron. In the experimental examples and examples of the present invention, the hair to which the examples were applied showed an increase in tensile strength of at least 20% and at most 30% compared to the comparative examples. The "hair styling" effect was confirmed by the hair setting power calculated by the following equation 3e. In the experimental examples and examples of the present invention, the hair to which the examples were applied showed an increase in hair setting power of at least 10% and at most 30% compared to the comparative examples. All of the above measurements can be performed under conditions of a temperature of 25°C, a relative humidity of 50%, and a dark room.

[0306] [Formula 3e]

[0307]

[0308] In the present invention, the organic silane compounds represented by the chemical formulas 1e to 3e can be expressed as follows.

[0309] Silane 1e, sample Ae

[0310] N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine

[0311] ;

[0312] Silane 2e, sample Be

[0313] N,N'-(1,4-phenylenebis(methylene))bis(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine)

[0314] ;

[0315] Silane 3e, sample Ce

[0316] N1,N1,N3,N3,N5,N5-hexakis(3-(triethoxysilyl)propyl)benzene-1,3,5-tricarboxamide

[0317] ;

[0318] Silane 4e, sample De

[0319] N1,N1,N12,N12-tetrakis(3-(triethoxysilyl)propyl)dodecane-1,12-diamine

[0320] ;

[0321] Silane 5e, sample Ee

[0322] N,N',N''-(benzene-1,3,5-triyltris(methylene))tris(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine)

[0323] ;

[0324] Silane 6e, sample Fe

[0325] N1,N1,N4,N4-tetrakis(3-(triethoxysilyl)propyl)terephthalamide

[0326] ;

[0327] Silane 7e, sample Ge

[0328] N1,N1,N3,N3-tetrakis(3-(triethoxysilyl)propyl)isophthalamide

[0329] .

[0330] The above hair composition may be in the form of a hair tonic, a hair conditioner, a hair essence, a hair lotion, a hair nourishing lotion, a hair shampoo, a hair rinse, a hair treatment, a hair cream, a hair nourishing cream, a hair moisture cream, a hair massage cream, a hair wax, a hair aerosol, a hair pack, a hair nourishing pack, a hair soap, a hair cleansing foam, a hair mist, a hair oil, a hair drying agent, a hair preservative, a hair dye, a hair waving agent, a hair bleaching agent, a hair gel, a hair glaze, a hair dressing agent, a hair lacquer, a hair moisturizer, a hair mousse or a hair spray, but any formulation that can be applied to hair is possible. For example, when the formulation of the cosmetic composition of the present invention is a paste, cream or gel, animal oil, vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as a carrier component.

[0331] In addition, when the formulation of the cosmetic composition of the present invention is a solution or emulsion, a solubilizer or an emulsifier is used as a carrier component, and for example, water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, dipropylene glycol, butylene glycol, 1,3-butyl glycol oil, glycerol aliphatic ester, PEG-8, polyethylene glycol, or sorbitan can be used.

[0332] Additionally, when the cosmetic composition of the present invention is in the form of a spray, it may additionally include a propellant such as chlorofluorohydrocarbon, propane, butane or dimethyl ether.

[0333] Additionally, the hair composition may be of a wash-off or leave-on type.

[0334] In the present invention, “wash-off” means applying a product to a substrate such as skin or hair, and then wiping it off with water or the like when it dries or is absorbed.

[0335] In the present invention, “leave-on” means that the product is applied to a substrate such as skin or hair and then not wiped off.

[0336] The above hair composition may further include one or more selected from the group consisting of behentrimonium chloride, behentrimonium methosulfate, distearyldimonium chloride, polyquaternium-10, hydrolyzed keratin, hydrolyzed collagen, cocobetaine, and dimethicone, and any ingredient that can be included in a formulation typically applied to hair may be included.

[0337] The hair composition of the present invention can be applied to known hair compositions in addition to the components described above, and may additionally include additives commonly used in the art, as long as they do not impair the effectiveness of the composition. The additives may include both natural and synthetic additives.

[0338] The above additives refer to ingredients such as organic raw materials, plant and plant-derived raw materials, animal and animal-derived raw materials, mineral and mineral-derived raw materials, and water. For example, it may include auxiliary agents and carriers commonly used in the field of cosmetics, such as pearl agents, thickeners, viscosity modifiers, pH modifiers, fatty substances, organic solvents, solubilizers, thickeners and gelling agents, softeners, antioxidants, suspending agents, stabilizers, foaming agents, fragrances, surfactants, ionic or nonionic emulsifiers, fillers, sequestering agents and chelating agents, preservatives, preservatives, vitamins, blocking agents, humectants, essential oils, dyes, pigments, fragrances, hydrophilic or lipophilic active agents, lipid vesicles, or any other ingredients commonly used in cosmetics.

[0339] In the present invention, "natural additive" means a natural product or a natural product obtained from a natural product, a natural product or a natural product-derived component simply modified, or a natural product or a natural product-derived component including a synthetic component among natural components, and excludes a synthetic component synthesized by an artificial method rather than a natural component.

[0340] The above natural raw materials may refer to, for example, cosmetic raw materials of natural origin that meet the organic standards and eco-friendly certification grades set by the country or equivalent thereto.

[0341] The above eco-friendly certification standards refer to compositions composed of ingredients grown and processed in an eco-friendly manner, excluding synthetic processes. Representative eco-friendly certifications include France's ecocert, Europe's Cosmos, the United States' USDA (US Department of Agriculture), Germany's BDIH (Association of German Industries and Trading Firms), and Japan's JAS (Japanese Association of Standards). In response to recent consumer needs for eco-friendly products, each country is developing various eco-friendly certification systems that certify the safety of ingredients or products. Although each country shows partial differences in detailed figures and scope, etc., the overall scope of eco-friendly certification for the primary components of raw materials and ingredients is globally unified. Natural ingredients derived from nature are included in the category of eco-friendly organic ingredients, and other semi-processed ingredients are categorized as PPAI (Physically Processed Agro Ingredient) and CPAI (Chemically Processed Agro Ingredient), and only raw materials that meet these standards are certified by Ecocert, Cosmos, or USDA.

[0342] In the present invention, the "nationally certified organic and eco-friendly raw materials and ingredients" refer to cosmetic raw materials and compositions that meet or can meet the nationally prescribed organic and eco-friendly certification standards and thus meet the nationally prescribed organic and eco-friendly grades. In the present invention, the synthetic additive refers to raw materials that have undergone a chemical synthesis process rather than being of natural origin.

[0343] The present invention also provides a method for preventing or improving hair frizz; or preventing heat damage and styling hair; comprising a step of applying the hair composition of the present invention to hair.

[0344] The method may further include a step of heating the hair at a temperature of 40° C. to 250° C. The step of heating the hair may be performed using any one of the following devices, and the hair may be heated at a temperature in the above range with the following devices.

[0345] Blow dryer, flat iron, hair dryer, heat lamp, heat wand, heating hood, heating cap, heating rod, curling iron, crimping iron, thermostat, heating curlers / rods or steam curlers.

[0346] In the above method, the hair composition may be applied to the hair immediately before or after at least one of the following.

[0347] - Chemical treatment of hair,

[0348] - If your hair has been chemically damaged,

[0349] - If the hair has been mechanically damaged,

[0350] - If your hair has been heat damaged, or

[0351] - If the hair has been damaged by environmental factors.

[0352] The composition may contain one or more selected from the group consisting of organic silane compounds represented by the above chemical formulae 1e to 3e in an amount of 0.0001 wt% to 10 wt% based on the total weight of the composition. Although not limited thereto, in one specific embodiment of the present invention, the composition may contain the composition of the present invention in an amount of 0.0001 wt% to 5 wt% (preferably 0.0001 wt% to 1 wt%) based on the total weight of the composition. Within the above range, better prevention and improvement of hair frizz, prevention of hair heat damage, and hair styling effects can be expected.

[0353] Hereinafter, the present invention will be described in more detail to aid understanding. However, the following examples are merely illustrative of the present invention, and the content of the present invention is not limited to the following examples.

[0354] -Experiment a-

[0355] Manufacturing Example 1a

[0356]

[0357] Bis(3-triethoxysilylpropyl)amine (19.67 g), triethylamine (9.20 ml), and 1,2-bis(2-chloroethoxy)ethane (4.12 g) were placed in a flask and stirred at 100°C for 24 hours. After the reaction was completed, 50 ml of hexane was added and stirred for 5 minutes. Then, solid byproducts were removed through a celite filter, and the hexane solution was distilled under reduced pressure to remove all of them. Finally, the final product in the form of a brown oil was obtained.

[0358] 1H NMR (500 MHz, CDCl3): δ 3.81 (q, 24H), 3.59 - 3.48 (m, 8H), 2.66 (t, 4H), 2.49 - 2.39 (m, 8H), 1.58 - 1.45 (m, 8H), 1.24 (t, 36H), 0.63 - 0.54 (m, 8H).

[0359] Manufacturing Example 2a

[0360]

[0361] Bis(3-triethoxysilylpropyl)amine (19.67 g), triethylamine (9.20 ml), and 1,12-dibromododecane (7.22 g) were placed in a flask and stirred at 50°C for 24 hours. After the reaction was completed, 50 ml of hexane was added and stirred for 5 minutes. The solid byproducts were removed through a celite filter, and the hexane solution was distilled under reduced pressure to remove all of them. Finally, the final product in the form of a brown oil was obtained.

[0362] 1 H NMR (500 MHz, CDCl3): δ 3.82 (q, 24H), 2.41-2.38 (m, 12H), 1.55 - 1.51 (m, 8H), 1.43 - 1.40 (m, 6H), 1.26 - 1.22 (m, 14H), 1.22 (t, 36H), 0.60 - 0.56 (m, 8H).

[0363] Example 1a

[0364] Using the previously prepared organosilane compound, hair coloring compositions (hair cleanser cosmetics; shampoos) of Examples 1a to 6a and Comparative Examples 1a to 3a were prepared with the compositions shown in Tables 1 to 3 below. Specifically, an amphoteric surfactant was first added, followed by sequential addition of a cationic polymer compound and an organosilane compound and dissolving them for 20 minutes. After stirring at 400 rpm at room temperature (25°C) for 30 minutes, a dye was added, heated to 40°C, and stirred thoroughly for 30 minutes. Thereafter, a pH adjuster and a chelating agent were added, and a thickener was sequentially added 10 minutes later. Thereafter, a hair coloring composition was prepared by stirring at 200 rpm for 30 minutes.

[0365] Ingredients (% by weight) Comparative Example 1a Example 1a Example 2a Purified water 89.25 87.25 87.25 Dye Basic Brown No. 16 0.20.20.2 Acid Red No. 52 --- Prickly Pear Extract --- Organosilane Compound Preparation Example 1a-2- Preparation Example 2a --2 Cationic Polymer Compound Polyquaternium-7 0.30.30.3 Zwitterionic Surfactant Cocamidopropyl Betaine 10 10 10 Thickener Hydroxyethylcellulose 0.05 0.05 0.05 Sodium Chloride 0.05 0.05 0.05 pH Regulator Hydrogen Citric Acid 0.10 10.1 Chelating Agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0366] Ingredients (% by weight) Comparative Example 2a Example 3a Example 4a Purified water 89.05 87.05 87.05 Dye Basic Brown No. 16 --- Acid Red No. 52 0.4 0.4 0.4 Extract of sesame seeds --- Organosilane compound Preparation Example 1a-2 Preparation Example 2a --2 Cationic polymer compound Polyquaternium-7 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 pH regulator Hydrogen citric acid 0.10 10.1 Chelating agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0367] Ingredients (% by weight) Comparative Example 3a Example 5a Example 6a Purified water 88.45 86.45 86.45 Dye Basic Brown No. 16 --- Acid Red No. 52 --- Gaja extract 111 Organosilane compound Preparation Example 1a-2- Preparation Example 2a --2 Cationic polymer compound Polyquaternium-7 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 pH regulator Hydrogen citric acid 0.10 10.1 Chelating agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0368] Experimental example

[0369] (1) Evaluation of hair dyeing power (coloring power)

[0370] In order to confirm the dyeing power of hair treated with the shampoos manufactured in Examples 1a to 6a and Comparative Examples 1a to 3a, yak hair (1 g of yak hair, Phoenix Korea) was washed with a 15 wt% Sodium Laureth Sulfate (SLES) aqueous solution corresponding to 10% of the tress weight, and then dried with a dryer to prepare a dry state. The color of the prepared yak hair was measured for initial color values ​​(L0, a0, b0) before dyeing using a colorimeter (Agera Spectrophotometer, HunterLab, light source D65 / 10).

[0371] The shampoo composition manufactured in each example and comparative example was applied in an amount equivalent to 10% of the weight of the hair tresses, and then the shampoo was evenly applied by hand for 1 minute to create a lather and left for 3 minutes. After this time, the dyed yak hair was rinsed with running lukewarm water at room temperature for 1 minute. The hair tresses were squeezed by hand to remove moisture, and then excess moisture was removed with a towel and dried using a dryer. This process was repeated a total of 3 times, and the color of the dried yak hair was measured with a colorimeter to determine the color values ​​(L1, a1, b1) after dyeing. In order to calculate the color change before / after dyeing, the color change (△E0) was calculated according to the following equation 1.

[0372] [Formula 1]

[0373]

[0374] L in Equation 1 O is the brightness before dyeing, L1 is the brightness after dyeing, and the higher the value, the brighter it is. a is Green to red, and a higher value indicates red, and a lower value indicates green. a0 is the value before dyeing, and a1 is the value after dyeing. b is Blue to yellow, and a higher value indicates yellow, and a lower value indicates blue. b0 is the value before dyeing, and b1 is the value after dyeing. △E0 indicates the dyeing power by the color change before / after dyeing. The results are shown in Table 4.

[0375] Comparative Example 1aExample 1aExample 2aDyeing power20.77±0.7825.20±0.5125.29±2.95Comparative Example 2aExample 3aExample 4aDyeing power14.56±0.2520.05±0.7519.98±1.32Comparative Example 3aExample 5aExample 6aDyeing power4.45±1.346.94±0.337.01±0.74

[0376] As observed in Table 4, it was observed that the dyeing power was greatly improved in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1a and 2a, basic dyes were used, in Examples 3a and 4a, acidic dyes were used, and in Examples 5a and 6a, natural dyes were used, and in all cases, an increase in dyeing power was observed, and it was discovered that the alkoxysilane compound can greatly increase the dyeing effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that dyeing power enhancement can be realized by adding the alkoxysilane compound of the present invention.

[0377] In addition, the degree of dyeing power enhancement effect was found to vary depending on the example, which can be seen as the structure of the alkoxysilane compound affecting the dyeing power enhancement effect.

[0378] (2) Dyeing durability evaluation

[0379] To evaluate the durability of dyeing, dyed hair tresses (yak hair, phoenix) were prepared. The dyed hair tresses were prepared using the same method as in Experimental Example (1). To observe the durability of dyeing, the dyeing power (△E1) was calculated according to Equation 2.

[0380] After dyeing, wet the hair with water, apply 10% of the hair weight of regular shampoo (Debon Charming Shampoo, LG Household & Health Care), and lather by hand for 1 minute to evenly distribute the shampoo. Then, rinse with running lukewarm water (room temperature) for 1 minute. Squeeze the hair tresses by hand to remove moisture, remove excess moisture with a towel, and dry using a dryer. This process was repeated 7 times, and the color of the dried yak hair was measured with a colorimeter to determine the color values ​​(L2, a2, b2) after washing. In order to calculate the color change before / after washing, the color change (△E1) was calculated according to Equation 2 below.

[0381] [Formula 2]

[0382]

[0383] L O L2 represents the brightness before dyeing, L0 represents the brightness after washing, a0 represents the green to red value before dyeing, and a2 represents the green to red value after washing. b0 represents the blue to yellow value before dyeing, and b2 represents the blue to yellow value after washing.

[0384] Next, in order to calculate the dyeing durability, the dyeing durability (%) was calculated according to Equation 3 below.

[0385] [Formula 3]

[0386] Dyeing durability (%) = (△E1 / △E0) * 100

[0387] Dye durability (%) indicates the degree to which color is maintained without fading (color loss) due to washing. A higher value indicates higher dye durability. The results are shown in Table 5.

[0388] Comparative Example 2a, Example 3a, Example 4a, Dyeing Durability (%) 3.848.288.99 Comparative Example 3a, Example 5a, Example 6a, Dyeing Durability (%) 5.137.127.38

[0389] As observed in Table 5, it was confirmed that the dyeing durability was increased in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added.

[0390] -Experiment b-

[0391] Manufacturing Example 1b

[0392]

[0393] Bis(3-triethoxysilylpropyl)amine (3 eq., 24.05 g), triethylamine (2 eq., 13.9 ml), and 1-bromo-3-chloropropane (2 eq., 15.74 g) were added to 20 ml of MeCN and stirred at 40°C overnight. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. After distillation, the final intermediate in the form of a brown oil was obtained.

[0394] The intermediate (1 eq., 18.81 g), triethylamine (2 eq., 13.9 ml), and imidazole (3 eq., 9.2 g) were added to 20 ml of MeCN and stirred at 100 °C for 4 hours. After completion of the reaction, MeCN was removed, 50 ml of hexane was added, and the mixture was stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. The final product in the form of a brown oil was then obtained through distillation.

[0395] 1H NMR (500 MHz, CDCl3): 7.35 (s, 1H), 6.93 (s, 1H), 6.80 (s, 1H), 3.94 - 3.78 (m, 2H), 3.70 (q, J = 7.0 Hz, 12H), 2.69 - 2.45 (m, 2H), 2.29 (s, 4H), 1.78 (s, 2H), 1.40 (s, 4H), 1.11 (t, J = 7.0 Hz, 18H), 0.55 - 0.36 (m, 4H).

[0396] Manufacturing Example 2b

[0397]

[0398] Bis(3-triethoxysilylpropyl)amine (3 eq., 24.05 g), triethylamine (2 eq., 13.9 ml), and 1-bromo-3-chloropropane (2 eq., 15.74 g) were added to 20 ml of MeCN and stirred at 40°C overnight. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. After distillation, the final intermediate in the form of a brown oil was obtained.

[0399] The intermediate (1 eq., 18.81 g), triethylamine (2 eq., 13.9 ml), and 1-methylpiperazine (3 eq., 13.5 g) were added to 20 ml of MeCN and stirred at 100°C for 4 hours. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. The final product in the form of a brown oil was then obtained through distillation.

[0400] 1H NMR (500 MHz, CDCl3): δ 3.81 (q, J = 7.0 Hz, 12H), 2.58 - 2.36 (m, 12H), 2.35 - 2.30 (m, 4H), 2.28 (s, 3H), 1.63 (dd, J = 8.8, 6.2 Hz, 2H), 1.52 (dt, J = 16.1, 8.0 Hz, 4H), 1.22 (t, J = 7.0 Hz, 18H), 0.62 - 0.50 (m, 4H).

[0401] Manufacturing Example 3b

[0402]

[0403] Bis(3-triethoxysilylpropyl)amine (3 eq., 24.05 g), triethylamine (2 eq., 13.9 ml), and 1-bromo-3-chloropropane (2 eq., 15.74 g) were added to 20 ml of MeCN and stirred at 40°C overnight. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. After distillation, the final intermediate in the form of a brown oil was obtained.

[0404] The intermediate (1 eq., 18.81 g), triethylamine (2 eq., 13.9 ml), and diethylamine (3 eq., 9.87 g) were added to 20 ml of MeCN and stirred at 100 °C for 4 hours. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. The final product in the form of a brown oil was then obtained through distillation.

[0405] 1H NMR (500 MHz, CDCl3): δ 3.81 (q, J = 7.0 Hz, 12H), 2.51 (dd, J = 13.9, 6.9 Hz, 4H), 2.46 - 2.34 (m, 8H), 1.62 - 1.49 (m, 6H), 1.22 (t, J = 7.0 Hz, 18H), 1.02 (t, J = 7.1 Hz, 4H), 0.62 - 0.50 (m, 4H).

[0406] Manufacturing Example 4b

[0407]

[0408] Add 7.2 g (45.8 mmol) of 1-bromo-3-chloropropane, 15 g (35.2 mmol) of Bis[3-(triethoxysilyl)propyl]amine, and 7.1 g (70.4 mmol) of triethylamine to a round-bottom flask and stir at 80°C for 16 hours. Monitor with GC / FID until all starting materials have disappeared, then lower the temperature to room temperature. Add 7.9 g (91.6 mmol) of morpholine, 3.6 g (35.2 mmol) of triethylamine, and 30 ml of acetonitrile to the reaction mixture. Raise the temperature to 70°C and react for 6 hours. Cool the reaction mixture to room temperature, dilute with 100 ml of hexane, stir the diluted mixture for 30 minutes, and extract the hexane layer. (acetonitrile: lower layer, hexane: upper layer) After repeating the above extraction process about 3 times, the solvent was removed from the collected hexane layer by reduced pressure distillation, and the final product in the form of a light yellow oil was obtained.

[0409] 1 H NMR (500 MHz, CDCl3) δ 3.78 (q, 12H), 3.69 (m, 4H), 2.31-2.40 (m, 12H), 1.51-1.60 (m, 6H), 1.20 (t, 18H), 0.56 (m, 4H).

[0410] Manufacturing Example 5b

[0411]

[0412] Add 7.2 g (45.8 mmol) of 1-bromo-3-chloropropane, 15 g (35.2 mmol) of Bis[3-(triethoxysilyl)propyl]amine, and 7.1 g (70.4 mmol) of triethylamine to a round-bottom flask and stir at 80°C for 16 hours. Monitor with GC / FID until all starting materials have disappeared, then lower the temperature to room temperature. Add 6.3 g (91.6 mmol) of triazole, 3.6 g (35.2 mmol) of triethylamine, and 30 ml of acetonitrile to the reaction mixture. Increase the temperature to 70°C and react for 6 hours. Cool the reaction mixture to room temperature, dilute with 100 ml of hexane, stir the diluted mixture for 30 minutes, and extract the hexane layer. (acetonitrile: lower layer, hexane: upper layer) After repeating the above extraction process about 3 times, the solvent was removed from the collected hexane layer by reduced pressure distillation, and the final product in the form of a light yellow oil was obtained.

[0413] 1 H NMR (500 MHz, CDCl3) δ 8.06 (s, 1H), 7.91 (s, 1H), 4.21 (t, 2H), 3.80 (q, 12H), 2.37 (m, 6H), 1.98 (m, 2H), 1.48 (m, 4H), 1.20 (t, 18H), 0.56 (m, 4H).

[0414] Example 1b

[0415] Using the previously prepared organosilane compounds, hair coloring compositions (hair cleanser cosmetics; shampoos) of Examples 1b to 12b and Comparative Examples 1b to 3b were prepared with the compositions shown in Tables 6 to 8 below. Specifically, an amphoteric surfactant was first added, followed by sequential addition of a cationic polymer compound and an organosilane compound and dissolving them for 20 minutes. After stirring at 400 rpm at room temperature (25°C) for 30 minutes, a dye was added, heated to 40°C, and stirred sufficiently for 30 minutes. Thereafter, a pH adjuster and a chelating agent were added, and a thickener was sequentially added 10 minutes later. Thereafter, a hair coloring composition was prepared by stirring at 200 rpm for 30 minutes.

[0416] Ingredients (% by weight) Comparative Example 1b Example 1b Example 2b Example 3b Example 4b Purified water 89.25 87.25 87.25 87.25 87.25 Dye Basic Brown No. 16 0.20.20.20.20.2 Acid Red No. 52 Perilla extract Organic silane compound Preparation Example 1b-2 Preparation Example 2b-2 Preparation Example 3b-2 Preparation Example 4b2 Cationic polymer compound Polyquaternium-7 0.30.30.30.30.3 Zwitterionic surfactant Cocamidopropyl betaine 10 10 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 0.05 0.05 pH Regulator Function Citric Acid 0.10.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.050.05 Total 100100100100100

[0417] Ingredients (% by weight) Comparative Example 2b Example 5b Example 6b Example 7b Example 8b Purified water 89.05 87.05 87.05 87.05 87.05 Dye Basic Brown 16 Acid Red 52 0.4 0.4 0.4 0.4 0.4 0.4 Extract of sesame oil Organic silane compound Preparation Example 1b-2 Preparation Example 2b-2 Preparation Example 3b-2 Preparation Example 4b2 Cationic polymer compound Polyquaternium-7 0.3 0.3 0.3 0.3 0.3 Zwitterionic surfactant Cocamidopropyl betaine 10 10 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 0.05 0.05 pH Regulator Function Citric Acid 0.10.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.050.05 Total 100100100100100

[0418] Ingredients (% by weight) Comparative Example 3b Example 9b Example 10b Example 11b Example 12b Purified water 88.4586.4586.4586.4586.45 Dye Basic brown 16 Acidic red 52 Prickly ash extract 11111 Organosilane compound Preparation Example 1b-2 Preparation Example 2b-2 Preparation Example 3b-2 Preparation Example 4b2 Cationic polymer compound Polyquaternium-7 0.30.30.30.30.3 Zwitterionic surfactant Cocamidopropyl betaine 1010101010 Thickener Hydroxyethyl cellulose 0.050.050.050.050.05 Sodium chloride 0.050.050.050.050.05 pH Regulator Function Citric Acid 0.10.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.050.05 Total 100100100100100

[0419] Experimental example

[0420] (1) Evaluation of hair dyeing power (coloring power)

[0421] In order to confirm the dyeing power of hair treated with the shampoos prepared in Examples 1b to 12b and Comparative Examples 1b to 3b, the same hair dyeing power (coloring power) evaluation as in Experiment a was performed, and the results are shown in Table 9 below.

[0422] Comparative Example 1bExample 1bExample 2bExample 3bExample 4bDyeing power 20.77±0.7824.46±0.1827.73±0.9826.17±0.9726.31±0.69Comparative Example 2bExample 5bExample 6bExample 7bExample 8bDyeing power 14.56±0.2518.11±0.6620.24±0.6521.38±1.8221.98±0.43Comparative Example 3bExample 9bExample 10bExample 11bExample 12bDyeing power 4.45±1.347.22±2.348.99±1.138.07±0.718.08±1.04

[0423] As observed in Table 9, it was observed that the dyeing power was greatly improved in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1b to 4b, basic dyes were used, in Examples 5b to 8b, acidic dyes, and in Examples 9b to 12b, natural dyes were used, and in all cases, an increase in dyeing power was observed, which revealed that the alkoxysilane compound can greatly increase the dyeing effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that dyeing power enhancement can be realized by adding the alkoxysilane compound of the present invention.

[0424] In addition, the order of the dyeing power enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound affecting the dyeing power enhancement effect.

[0425] (2) Dyeing durability evaluation

[0426] In order to evaluate the durability of the dyeing, the same evaluation as the dyeing durability of Experiment a was performed, and the results are shown in Table 10 below.

[0427] Comparative Example 1bExample 1bExample 2bExample 3bExample 4bDyeing Durability (%) 47.3755.0848.1548.2056.19Comparative Example 2bExample 5bExample 6bExample 7bExample 8bDyeing Durability (%) 3.8411.5316.2214.2614.33Comparative Example 3bExample 9bExample 10bExample 11bExample 12bDyeing Durability (%) 5.137.468.588.457.01

[0428] As observed in Table 10, it was observed that the dyeing durability was increased in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1b to 4b, basic dyes were used, in Examples 5b to 8b, acidic dyes were used, and in Examples 9b to 12b, natural dyes were used, and in all cases, the dyeing durability was observed to be increased, and it was discovered that the alkoxysilane compound can significantly increase the dyeing durability effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that the dyeing durability can be enhanced by adding the alkoxysilane compound of the present invention.

[0429] In addition, the order of the dyeing durability enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound having a great influence on the dyeing durability enhancement effect.

[0430] -Experiment c-

[0431] Manufacturing Example 1c

[0432]

[0433] Bis(3-triethoxysilylpropyl)amine (2.1 eq., 19.67 g), triethylamine (3 eq., 9.20 ml), and 1,4-bis(chloromethyl)benzene (1 eq., 3.85 g) were stirred at 150°C for 6 hours. After completion of the reaction, 50 ml of hexane was added and stirred for 5 minutes. Then, solid byproducts were removed through a Celite filter, and the hexane solution was completely removed by distillation under reduced pressure. Finally, the final product in the form of a brown oil was obtained.

[0434] 1H NMR (500 MHz, CDCl3): δ 7.22 (s, 4H), 3.82 - 3.76 (m, 24H), 3.53 (s, 4H), 2.46 - 2.33 (m, 8H), 1.66 - 1.50 (m, 8H), 1.21 (t, J = 7.0 Hz, 36H), 0.60 - 0.52 (m, 8H).

[0435] Manufacturing Example 2c

[0436]

[0437] Bis(3-triethoxysilylpropyl)amine (3.1 eq., 14.80 g), triethylamine (5 eq., 7.81 ml), and 1,3,5-tris(bromomethyl)benzene (1 eq., 4.00 g) were added to 25 ml of MeCN and stirred at 50°C overnight. After completion of the reaction, MeCN was removed, and 50 ml of hexane was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed through distillation under reduced pressure. Finally, the final product in the form of a yellow oil was obtained.

[0438] 1H NMR (500 MHz, CDCl3): δ 7.12 (s, 3H), 3.86 - 3.74 (m, 42H), 2.52 - 2.28 (m, 12H), 1.59 - 1.52 (m, 12H), 1.27 - 1.16 (m, 48H), 0.54 (t, J = 15.9 Hz, 12H).

[0439] Example 1c

[0440] Using the previously prepared organic silane compound, hair coloring compositions (hair cleanser cosmetics; shampoos) of Examples 1c to 9c and Comparative Examples 1c to 3c were prepared with the compositions shown in Tables 11 to 13 below. Specifically, an amphoteric surfactant was added first, and then a cationic polymer compound and an organic silane compound were sequentially added and dissolved for 20 minutes. After stirring at 400 rpm at room temperature (25°C) for 30 minutes, a dye was added, heated to 40°C, and stirred sufficiently for 30 minutes. Thereafter, a pH adjuster and a chelating agent were added, and a thickener was sequentially added 10 minutes later. Thereafter, a hair coloring composition was prepared by stirring at 200 rpm for 30 minutes.

[0441] Ingredients (% by weight) Comparative Example 1c Example 1c Example 2c Purified water 89.25 87.25 87.25 Dye Basic brown No. 16 0.2 0.2 0.2 Acid red No. 52 Perilla extract Organic silane compound Preparation Example 1c-2 Preparation Example 2c-2 Cationic polymer compound Polyquaternium-7 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 pH regulator Hydrogen citric acid 0.10 10.1 Chelating agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0442] Ingredients (% by weight) Comparative Example 2c Example 3c Example 4c Purified water 89.05 87.05 87.05 Dye Basic Brown 16 Acid Red 52 0.4 0.4 0.4 Extract of sesame oil Organic silane compound Preparation Example 1c-2 Preparation Example 2c-2 Cationic polymer compound Polyquaternium-7 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 pH regulator Hydrogen citric acid 0.10 10.1 Chelating agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0443] Ingredients (% by weight) Comparative Example 3c Example 5c Example 6c Purified water 88.45 86.45 86.45 Dye Basic brown 16 Acidic red 52 Prickly ash extract 111 Organosilane compound Preparation Example 1c-2 Preparation Example 2c-2 Cationic polymer compound Polyquaternium-7 0.30.30.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 pH regulator Hydrogen citric acid 0.10.10.1 Chelating agent Tetrasodium EDTA 0.05 0.05 0.05 Total 100 100 100

[0444] Experimental example

[0445] (1) Evaluation of hair dyeing power (coloring power)

[0446] In order to confirm the dyeing power of hair treated with the shampoos manufactured in Examples 1c to 6c and Comparative Examples 1c to 3c, the same hair dyeing power (coloring power) evaluation as in Experiment a was performed, and the results are shown in Table 14 below.

[0447] Comparative Example 1cExample 1cExample 2cDyeing power20.77±0.7824.40±1.8926.20±1.62Comparative Example 2cExample 3cExample 4cDyeing power14.56±0.2516.72±0.8821.41±1.02Comparative Example 3cExample 5cExample 6cDyeing power4.45±1.347.11±1.268.24±0.97

[0448] As observed in Table 14, it was observed that the dyeing power was greatly improved in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1c and 2c, basic dyes were used, in Examples 3c and 4c, acidic dyes were used, and in Examples 5c and 6c, natural dyes were used, and in all cases, an increase in dyeing power was observed, and it was discovered that the alkoxysilane compound can greatly increase the dyeing effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that dyeing power enhancement can be realized by adding the alkoxysilane compound of the present invention.

[0449] In addition, the order of the dyeing power enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound affecting the dyeing power enhancement effect.

[0450] (2) Dyeing durability evaluation

[0451] In order to evaluate the durability of the dyeing, the same evaluation as the dyeing durability of Experiment a was performed, and the results are shown in Table 15 below.

[0452] Comparative Example 1c Example 1c Example 2c Dyeing Durability (%) 47.3754.6551.85 Comparative Example 2c Example 3c Example 4c Dyeing Durability (%) 3.8413.4317.24 Comparative Example 3c Example 5c Example 6c Dyeing Durability (%) 5.139.018.99

[0453] As observed in Table 15, it was observed that the dyeing durability was increased in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1c and 2c, basic dyes were used, in Examples 3c and 4c, acidic dyes were used, and in Examples 5c and 6c, natural dyes were used. In all cases, the dyeing durability was observed to be increased, and it was discovered that the alkoxysilane compound can significantly increase the dyeing durability effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that the dyeing durability can be enhanced by adding the alkoxysilane compound of the present invention.

[0454] In addition, the order of the dyeing durability enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound having a great influence on the dyeing durability enhancement effect.

[0455] -Experiment d-

[0456] Manufacturing Example 1d

[0457]

[0458] Bis(3-triethoxysilylpropyl)amine (3 eq., 24.05 g) and triethylamine (6 eq., 15.75 ml) were added to 20 ml of dichloromethane, and then benzene-1,3,5-tricarbonyl trichloride (1 eq., 5.0 g) dissolved in 60 ml of dichloromethane was slowly added at 0 ℃ over 10 minutes. The mixture was warmed to room temperature and stirred for 24 hours. After completion of the reaction, dichloromethane was removed, and 50 ml of toluene was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed by distillation under reduced pressure. Finally, the final product in the form of a yellow oil was obtained.

[0459] 1H NMR (500 MHz, CDCl3): δ 7.19 (s, 3H), 3.61 (dd, J = 33.1, 6.5 Hz, 36H), 3.16 (d, J = 115.1 Hz, 12H), 1.49 (d, J = 77.3 Hz, 12H), 1.15 - 0.82 (m, 54H), 0.33 (d, J = 134.0 Hz, 12H).

[0460] Manufacturing Example 2d

[0461]

[0462] Bis(3-triethoxysilylpropyl)amine (2.1 eq., 35.2 g) and triethylamine (3 eq., 16.48 ml) were added to 40 ml of dichloromethane, and then terephthaloyl chloride (1 eq., 8.0 g) dissolved in 80 ml of dichloromethane was slowly added at 0 ℃ over 10 minutes. The mixture was warmed to room temperature and stirred for 24 hours. After completion of the reaction, dichloromethane was removed, 50 ml of toluene was added, and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was distilled under reduced pressure to remove all of them. Finally, the final product in the form of a yellow oil was obtained.

[0463] 1H NMR (500 MHz, CDCl3): δ 7.37 (s, 4H), 3.80 (ddt, J = 26.9, 13.9, 6.9 Hz, 24H), 3.32 (dt, J = 153.1, 7.3 Hz, 8H), 1.81 - 1.53 (m, 8H), 1.31 - 1.13 (m, 36H), 0.72 - 0.31 (m, 8H).

[0464] Manufacturing example 3d

[0465]

[0466] Bis(3-triethoxysilylpropyl)amine (2.1 eq., 35.2 g) and triethylamine (3 eq., 16.48 ml) were added to 40 ml of dichloromethane, and then isophthaloyl dichloride (1 eq., 8.0 g) dissolved in 80 ml of dichloromethane was slowly added at 0 ℃ over 10 minutes. The mixture was warmed to room temperature and stirred for 24 hours. After completion of the reaction, dichloromethane was removed, and 50 ml of toluene was added and stirred for 5 minutes. Solid byproducts were removed through a Celite filter, and the hexane solution was completely removed by distillation under reduced pressure. Finally, the final product in the form of a yellow oil was obtained.

[0467] 1H NMR (500 MHz, CDCl3): δ 7.37 (td, J = 6.4, 4.5 Hz, 4H), 3.80 (ddq, J = 31.3, 13.8, 7.0 Hz, 24H), 3.51 - 3.11 (m, 8H), 1.81 - 1.53 (m, 8H), 1.21 (ddd, J = 15.5, 14.1, 6.8 Hz, 36H), 0.72 - 0.31 (m, 8H).

[0468] Examples 1d to 9d and Comparative Examples 1d to 3d

[0469] Using the previously prepared organic silane compound, hair coloring compositions (hair cleanser cosmetics; shampoos) of Examples 1d to 9d and Comparative Examples 1d to 3d were prepared with the compositions shown in Tables 16 to 18 below. Specifically, an amphoteric surfactant was first added, followed by sequential addition of a cationic polymer compound and an organic silane compound and dissolving them for 20 minutes. After stirring at 400 rpm at room temperature (25°C) for 30 minutes, a dye was added, heated to 40°C, and stirred sufficiently for 30 minutes. Thereafter, a pH adjuster and a chelating agent were added, and a thickener was sequentially added 10 minutes later. Thereafter, a hair coloring composition was prepared by stirring at 200 rpm for 30 minutes.

[0470] Ingredients (% by weight) Comparative Example 1d Example 1d Example 2d Example 3d Purified water 89.25 87.25 87.25 87.25 7.25 Dye Basic Brown No. 16 0.2 0.2 0.2 0.2 0.2 Acid Red No. 52 ----Purple extract ----Organic silane compound Preparation Example 1d-2-- Preparation Example 2d--2- Preparation 3d---2 Cation polymer compound Polyquaternium-7 0.3 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 0.05 pH Regulator Function Citric Acid 0.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.05 Total 100100100100

[0471] Ingredients (% by weight) Comparative Example 2d Example 4d Example 5d Example 6d Purified water 89.05 87.05 87.05 87.05 Dye Basic Brown No. 16----Acid Red No. 52 0.4 0.4 0.4 0.4 Extract of sesame seeds----Organic silane compound Preparation Example 1d-2-- Preparation Example 2d--2- Preparation Example 3d---2 Cation polymer compound Polyquaternium-7 0.3 0.3 0.3 0.3 Amphoteric surfactant Cocamidopropyl betaine 10 10 10 10 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 0.05 pH Regulator Function Citric Acid 0.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.05 Total 100100100100

[0472] Ingredients (% by weight) Comparative Example 3d Example 7d Example 8d Example 9d Purified water 88.45 86.45 86.45 86.45 Dye Basic Brown No. 16----Acid Red No. 52----Purple extract 1111 Organosilane compound Preparation Example 1d-2-- Preparation Example 2d--2- Preparation Example 3d---2 Cationic polymer compound Polyquaternium-7 0.30.30.30.3 Amphoteric surfactant Cocamidopropyl betaine 10101010 Thickener Hydroxyethyl cellulose 0.05 0.05 0.05 0.05 Sodium chloride 0.05 0.05 0.05 0.05 pH Regulator Function Citric Acid 0.10.10.10.1 Chelating Agent Tetrasodium EDTA 0.050.050.050.05 Total 100100100100

[0473] Experimental example

[0474] (1) Evaluation of hair dyeing power (coloring power)

[0475] In order to confirm the dyeing power of hair treated with the shampoos manufactured in Examples 1d to 9d and Comparative Examples 1d to 3d, the same hair dyeing power (coloring power) evaluation as in Experiment a was performed, and the results are shown in Table 19 below.

[0476] Comparative Example 1d Example 1d Example 2d Example 3d Dyeing power 20.77±0.78 24.90±1.29 23.51±1.44 25.71±1.82 Comparative Example 2d Example 4d Example 5d Example 6d Dyeing power 14.56±0.25 17.99±0.37 18.01±1.23 20.23±0.41 Comparative Example 3d Example 7d Example 8d Example 9d Dyeing power 4.45±1.3 47.17±0.1 26.75±0.2 27.55±0.34

[0477] As observed in Table 19, it was observed that the dyeing power was greatly improved in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1d to 3d, basic dyes were used, in Examples 4d to 6d, acidic dyes were used, and in Examples 7d to 9d, natural dyes were used. In all cases, an increase in dyeing power was observed, and it was discovered that the alkoxysilane compound can greatly increase the dyeing effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that dyeing power enhancement can be realized by adding the alkoxysilane compound of the present invention.

[0478] In addition, the order of the dyeing power enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound affecting the dyeing power enhancement effect.

[0479] (2) Dyeing durability evaluation

[0480] In order to evaluate the durability of the dyeing, the same evaluation as the durability evaluation of the above -Experiment a- was performed, and the results are shown in Table 20 below.

[0481] Comparative Example 1d Example 1d Example 2d Example 3d Dyeing Durability (%) 47.375 3.374 9.28 5 1.01 Comparative Example 2d Example 4d Example 5d Example 6d Dyeing Durability (%) 3.84 13.07 14.85 14.15 Comparative Example 3d Example 7d Example 8d Example 9d Dyeing Durability (%) 5.1 36.4 48.9 47.66

[0482] As observed in Table 20, it was observed that the dyeing durability was increased in the examples in which the alkoxysilane compound was added compared to the comparative examples in which the alkoxysilane compound was not added. In Examples 1d to 3d, basic dyes were used, in Examples 4d to 6d, acidic dyes were used, and in Examples 7d to 9d, natural dyes were used. In all cases, the dyeing durability was observed to be increased, and it was discovered that the alkoxysilane compound can significantly increase the dyeing durability effect when applied to hair regardless of the type of dye. Therefore, it was confirmed through this that the dyeing durability can be enhanced by adding the alkoxysilane compound of the present invention.

[0483] In addition, the order of the dyeing durability enhancement effect was different depending on the example, which can be seen as the structure of the alkoxysilane compound having a great influence on the dyeing durability enhancement effect.

[0484] -Experiment e-

[0485] Experimental Example 1e. Effect of organic silane compounds on hair frizz reduction.

[0486] Silane 1e, sample Ae

[0487] N,N'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine

[0488] ;

[0489] Silane 2e, sample Be

[0490] N,N'-(1,4-phenylenebis(methylene))bis(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine)

[0491] ;

[0492] Silane 3e, sample Ce

[0493] N1,N1,N3,N3,N5,N5-hexakis(3-(triethoxysilyl)propyl)benzene-1,3,5-tricarboxamide

[0494] ;

[0495] Silane 4e, sample De

[0496] N1,N1,N12,N12-tetrakis(3-(triethoxysilyl)propyl)dodecane-1,12-diamine

[0497] ;

[0498] Silane 5e, sample Ee

[0499] N,N',N''-(benzene-1,3,5-triyltris(methylene))tris(3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine)

[0500] ;

[0501] Silane 6e, sample Fe

[0502] N1,N1,N4,N4-tetrakis(3-(triethoxysilyl)propyl)terephthalamide

[0503] ;

[0504] Silane 7e, sample Ge

[0505] N1,N1,N3,N3-tetrakis(3-(triethoxysilyl)propyl)isophthalamide

[0506] .

[0507] Experimental Example 1e-1. Evaluation of Anti-Frizz Effect

[0508] To evaluate the effect of the above-mentioned organosilane compound on reducing hair frizz, hair tresses (2 g, Beaulax, Asian Hair) were produced. The produced tresses were washed with a sodium laureth sulfate (SLES) solution to remove impurities, and the prepared tresses were stored overnight under constant temperature and humidity conditions before use.

[0509] Next, a hair cleanser and a hair treatment agent were prepared according to the compositions in Table 21. The prepared hair tresses were washed with the hair cleanser, then the hair was squeezed by hand to remove moisture, and then excess moisture was removed using a towel. Afterwards, the hair treatment agent was applied to wet hair in an amount equivalent to 5% of the hair weight, spread evenly by hand for 1 minute, and then dried using a hair dryer with hot air for 2 minutes. The hair treatment process using the above-described cleanser and treatment agent was repeated a total of 6 times, and the hair tresses were treated with a curling iron (230℃) for the 3rd and 6th treatments. The hair tresses that had been treated were stored overnight under constant temperature and humidity conditions, and then the hair frizz value was measured. The frizz degree according to the treatment with the compositions in Table 21 is shown in Figures 1 and 2. The frizz degree (FAF%) was calculated according to Equation 2e.

[0510] Classification (wt %) Comparative Example 1e Comparative Example 2e Example 1e Example 2e Example 3e Example 4e Example 5e Example 6e Example 7e Hair Cleanser SLES 15 Purified Water 85 Hair Treatment Ethanol 100 959 59 59 59 59 59 59 53-Aminopropyltriethoxysilane (APTES)-5-------Silane 1e--5------Silane 2e---5-----Silane 3e----5----Silane 4e-----5---Silane 5e------5--Silane 6e-------5-Silane 7e--------5

[0511] [Equation 2e]

[0512]

[0513] As shown in Figures 1 and 2, it can be confirmed that the degree of frizz (FAF%) is lower in both Comparative Example 2e and the Examples, which are treated with silane, compared to Comparative Example 1e, which is not treated with silane. This means that the characteristics of hair change due to the treatment with silane, ultimately resulting in the effect of reducing frizz.

[0514] In addition, the effect of reducing the degree of frizziness is strongest in Example 5e, followed by Example 7e, Example 4e, Example 3e, Example 1e, Example 2e, Example 6e, and Comparative Example 2e in that order. This means that the effect of improving frizziness varies depending on the structural characteristics of the silane. Accordingly, it was confirmed that the frizziness of hair can be significantly reduced by changing the structural characteristics of the silane.

[0515] In addition, the improvement in the fluffiness of the example is more excellent than that of Comparative Example 2 using a conventionally known silane compound, which means that the silane having a specific structure has an excellent fluffiness reduction effect compared to the existing technology.

[0516] Experimental Example 1e-2. Evaluation of the Durability of the Anti-Frizz Effect

[0517] An experiment was conducted to confirm the sustainability of the frizz-reduction effect. Similarly, hair tresses (2 g, Beaulax, Asian Hair) were prepared and washed with a sodium laureth sulfate (SLES) solution to remove impurities. The prepared tresses were stored overnight under constant temperature and humidity conditions (25°C, 50% RH) before use.

[0518] Next, a hair cleanser and a hair treatment agent were prepared as per the compositions in Table 21. The prepared hair tresses were washed with the hair cleanser, then the hair was squeezed by hand to remove moisture, and then excess moisture was removed using a towel. Afterwards, the hair treatment agent was applied to wet hair in an amount equivalent to 5% of the hair weight, spread evenly by hand for 1 minute, and then dried using a hair dryer with hot air for 2 minutes. The hair treatment process using the above-described cleanser and treatment agent was repeated a total of 6 times, and the hair tresses were treated with a curling iron (230℃) for the 3rd and 6th treatments. The hair tresses that had undergone all treatments were stored overnight under constant temperature and humidity conditions, and the initial value of the hair frizziness was measured. At this time, the frizziness degree (FAF%) was calculated according to Equation 2e. Next, the hair cleanser was applied to the hair as per the compositions in Table 21, washed, dried, and stored overnight under constant temperature and humidity conditions. This process was repeated a total of five times, and the hair frizziness after repeated washing was measured. The rate of change in hair frizziness was then calculated and compared according to Equation 1e below. The results are shown in Table 22 and Figures 3 and 4.

[0519] Comparative Example 1eComparative Example 2eExample 1eExample 2eExample 3eExample 4eExample 5eExample 6eExample 7eInitial FAF Value (%)24.6922.5819.6221.1317.8617.1116.4922.1817.05After washing FAF Value (%)38.2332.5721.1129.2019.6221.8121.2531.1119.27Change in Boothness (%)54.8344.237.638.199.8427.4728.8940.2613.04

[0520] [Formula 1e]

[0521]

[0522] As shown in the above Figures 3 and 4, it was observed that the examples treated with the silane compound of the present invention showed a smaller change in frizziness after washing compared to the comparative examples. This means that hair treated with the silane compound of the present invention has resistance to changes in frizziness due to washing, and it can be seen that the treatment with the silane compound of the present invention provides a semi-permanent change in frizziness.

[0523] Experimental Example 2e. Effect of organic silane compounds on hair heat damage prevention and hair styling.

[0524] Experimental Example 2e-1. Evaluation of Hair Heat Protection Effect

[0525] Hair tresses (2 g, 25 cm, Beaulax, Asian Hair) were produced, and Comparative Examples 1e to 4e and Examples 1e to 7e were prepared according to the compositions in Table 23. The tresses were washed with a 15% Sodium Laureth Sulfate (SLES) solution corresponding to 10% of the weight, dried with a dryer, and stored under constant temperature and humidity conditions (25 °C, 50% RH) for one day.

[0526] As prepared as above, SLES was applied in an amount of 10% of the weight of the tresses, washed, and then the hair was squeezed by hand to remove moisture and then excess moisture was removed using a towel. Thereafter, Comparative Examples 1e to 4e and Examples 1e to 7e in an amount of 5% of the weight of the tresses were applied to wet hair, spread evenly by hand for 1 minute, and then dried using a dryer with hot air (90°C) for 2 minutes. The process of treating the hair using the above-described cleansing and treating agents was repeated a total of 6 times, and after the 3rd and 6th treatments, the hair tresses were straightened twice from the root to the tip using a curling iron (230°C). The hair tresses that had undergone all treatments were stored under constant temperature and humidity conditions for one day, and then the thickness and tensile strength of the hair were measured, and the results are shown in Table 4. Hair thickness was measured using a Laser Scan Micrometer (LSM-6200, LSM-501S, Mitutoyo, Japan), and hair tensile testing was performed using a Miniature Tensile Tester (MTT175, Dia-stron, UK). All measurements were performed under constant temperature and humidity conditions.

[0527] Classification (wt %) Comparative Example 1e Comparative Example 2e Comparative Example 3e Comparative Example 4e Example 1e Example 2e Example 3e Example 4e Example 5e Example 6e Example 7e Hair Cleanser SELS 15 Purified Water 85 Hair Treatment Ethanol 100 959 59 59 59 59 59 59 59 59 59 3-Aminopropyltriethoxysilane (APTES)-5---------Bis[3-(triethoxysilyl)propyl]amine--5--------Tris[3-(triethoxysilyl)propyl]amine---5-------Silane 1e----5------Silane 2e-----5-----Silane 3e------5----Silane 4e-------5---Silane 5e--------5---Silane 6e---------5-Silane 7e----------5

[0528] Comparative Example 1e Comparative Example 2e Comparative Example 3e Comparative Example 4e Example 1e Example 2e Example 3e Example 4e Example 5e Example 6e Example 7e Tensile strength (Mpa) 273.83 267.33 281.70 282.11 335.54 343.17 355.74 352.34 340.82 341.86 337.93

[0529] As shown in Table 24, it can be confirmed that the hair tensile strength is higher in Examples 1e to 7e treated with the silane compound of the present invention than in Comparative Examples 1e to 4e. This means that the composition of the present invention exhibits an effect of protecting hair from weakening due to a decrease in tensile strength caused by heat when applied to the hair.

[0530] Experimental Example 2e-2. Increased Hair Heat Styling Effect

[0531] Hair tresses (2.5 g, 25 cm, Beaulax, Asian Hair) were produced, and Comparative Examples 1e to 4e and Examples 1e to 7e were prepared according to the compositions in Table 3. The tresses were washed with a 15% Sodium Laureth Sulfate (SLES) solution corresponding to 10% of the weight, dried with a dryer, and stored under constant temperature and humidity conditions (25°C, 50% RH) for one day.

[0532] As prepared as above, SLES in an amount of 10% of the weight of the tresses was applied to the hair tresses, washed, and then the hair was squeezed by hand to remove moisture and then excess moisture was removed using a towel. Thereafter, Comparative Examples 1e to 4e and Examples 1e to 7e in an amount of 5% of the weight of the tresses were applied to wet hair and spread evenly by hand for 1 minute. Next, the tresses were diagonally rolled and fixed in a cylindrical aluminum can with a diameter of 2.7 cm and dried in a dry oven (90°C) for 10 minutes. The hair tresses that had undergone all treatments were taken out, released from the can, and hung vertically to measure the total length of the tresses. All measurements were performed under constant temperature and humidity conditions. The hair setting power was calculated according to Equation 3e, and the results are shown in Table 25.

[0533] [Formula 3e]

[0534]

[0535] Comparative Example 1e Comparative Example 2e Comparative Example 3e Comparative Example 4e Example 1e Example 2e Example 3e Example 4e Example 5e Example 6e Example 7e Hair Setting Power (%) 36.73 37.09 37.96 38.27 47.31 42.74 45.20 40.50 41.65 42.25 41.92

[0536] As shown in Table 25, it can be confirmed that the hair setting power is higher in Examples 1e to 7e treated with the silane compound of the present invention compared to Comparative Examples 1e to 4e. This means that the composition of the present invention exhibits the effect of allowing the hair to be better styled (produced) when styling hair with heat by treating the hair.

[0537] Experimental Example 2e-3. Increased hair heat styling durability

[0538] Hair tresses (2.5 g, 25 cm, Beaulax, Asian Hair) were produced, and Comparative Examples 1e to 4e and Examples 1e to 7e were prepared according to the compositions in Table 23. The tresses were washed with a 15% Sodium Laureth Sulfate (SLES) solution corresponding to 10% of the weight, dried with a dryer, and stored under constant temperature and humidity conditions (25°C, 50% RH) for one day.

[0539] As prepared as above, SLES in an amount of 10% of the weight of the tresses was applied to the hair tresses, washed, and then the hair was squeezed by hand to remove moisture and then excess moisture was removed using a towel. Thereafter, Comparative Examples 1e to 4e and Examples 1e to 7e in an amount of 5% of the weight of the tresses were applied to wet hair and spread evenly by hand for 1 minute. Next, the tresses were diagonally rolled and fixed in a cylindrical aluminum can with a diameter of 2.7 cm and dried in a dry oven (180°C) for 10 minutes. The hair tresses that had undergone all treatments were taken out, released from the can, and hung vertically. After 20 hours, the total length of the tresses was measured, and the results are shown in Table 26. All measurements were performed under constant temperature and humidity conditions.

[0540] Comparative Example 1e Comparative Example 2e Comparative Example 3e Comparative Example 4e Example 1e Example 2e Example 3e Example 4e Example 5e Example 6e Example 7e Length of tresses after 20 hours of curling (cm) 21.26 20.69 20.56 19.88 17.69 18.86 18.14 18.61 18.65 17.95 18.22

[0541] As shown in Table 26, it can be confirmed that the tresses length was shorter after 20 hours of curling in Examples 1e to 7e treated with the silane compound of the present invention compared to Comparative Examples 1e to 4e. This means that the composition of the present invention, when applied to hair, exhibits the effect of making the style last longer when styling hair with heat.

Claims

1. An organic silane compound represented by the following chemical formula 1a: [Chemical Formula 1a] In the above chemical formula 1a, X1 and X2 are each independently O or -(CH2)-, a to c are each independently an integer from 1 to 5, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, n is an integer from 2 to 5, m is an integer from 1 to 3.

2. In paragraph 1, a to c are integers from 2 to 4, Organosilane compounds.

3. In paragraph 1, R1 and R2 are each ethyl, Organosilane compounds.

4. In paragraph 1, n is 3 people, Organosilane compounds.

5. In paragraph 1, m is 3 people, Organosilane compounds.

6. In paragraph 1, The organic silane compound represented by the above chemical formula 1a is represented by the following chemical formula 1a-1 or chemical formula 1a-2, Organosilane compounds: [Chemical Formula 1a-1] [Chemical Formula 1a-2] .

7. Containing at least one organic silane compound represented by the following chemical formula 1a, Composition for hair coloring: [Chemical Formula 1a] In the above chemical formula 1a, X1 and X2 are each independently O or -(CH2)-, a to c are each independently an integer from 1 to 5, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, n is an integer from 2 to 5, m is an integer from 1 to 3.

8. In paragraph 7, a to c are integers from 2 to 4, Composition for hair coloring.

9. In paragraph 7, R1 and R2 are each ethyl, Composition for hair coloring.

10. In paragraph 7, n is 3 people, Composition for hair coloring.

11. In paragraph 7, m is 3 people, Composition for hair coloring.

12. In paragraph 7, The organic silane compound represented by the above chemical formula 1a is represented by the following chemical formula 1a-1 or chemical formula 1a-2, Composition for hair coloring: [Chemical Formula 1a-1] [Chemical Formula 1a-2] .

13. In paragraph 7, The above hair coloring agent is for hair browning or blackening, or for preventing whitening. Composition for hair coloring.

14. In paragraph 7, The above hair coloring composition comprises an organic silane compound represented by the above chemical formula 1 in an amount of 0.001 wt% or more and 10 wt% or less based on the total weight. Composition for hair coloring.

15. The hair coloring composition of Article 7 is a shampoo, hair conditioner, hair treatment, hair lotion, hair gel, hair pack, hair cream, or hair essence. Composition for hair coloring.

16. A method comprising applying a hair coloring composition according to any one of claims 7 to 15 to hair. How to color hair.

17. Comprising a step of washing hair with a hair coloring composition according to any one of claims 7 to 15. How to color hair.

18. An organic silane compound represented by the following chemical formula 1b: [Chemical Formula 1b] In the above chemical formula 1b, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, R3 is one or more C 1-10 Alkyl-substituted amine; C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 Heterocycloalkyl; substituted or unsubstituted C 6-20 Aryl; or C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl, m is an integer from 1 to 3, n1b is an integer from 2 to 5, n2b is an integer from 0 to 5.

19. In paragraph 18, R1 and R2 are each independently methyl or ethyl, Organosilane compounds.

20. In paragraph 18, R1 and R2 are each ethyl, Organosilane compounds.

21. In paragraph 18, R3 is imidazolyl, 1-methylpiperazinyl, or diethylamine, Organosilane compounds.

22. In paragraph 18, m is 3 people, Organosilane compounds.

23. In paragraph 18, n1b is 3 people, Organosilane compounds.

24. In paragraph 18, n2b is 3 people, Organosilane compounds.

25. In paragraph 18, The organic silane compound represented by the above chemical formula 1b is one selected from the following group: Organosilane compounds: .

26. Containing at least one organic silane compound represented by the following chemical formula 1b, Composition for hair coloring: [Chemical Formula 1b] In the above chemical formula 1b, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, R3 is one or more C 1-10 Alkyl-substituted amine; C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 Heterocycloalkyl; substituted or unsubstituted C 6-20 Aryl; or C comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl, m is an integer from 1 to 3, n1b is an integer from 2 to 5, n2b is an integer from 0 to 5.

27. In paragraph 26, The organic silane compound represented by the above chemical formula 1b is one selected from the following group: Composition for hair coloring: .

28. In paragraph 26, The above hair coloring is for hair browning or blackening, or for preventing whitening, Composition for hair coloring.

29. In paragraph 26, The above hair coloring composition comprises an organic silane compound represented by the above chemical formula 1 in an amount of 0.001 wt% or more and 10 wt% or less based on the total weight. Composition for hair coloring.

30. The hair coloring composition of Article 26 is a shampoo, hair conditioner, hair treatment, hair lotion, hair gel, hair pack, hair cream, or hair essence. Composition for hair coloring.

31. A method comprising applying a hair coloring composition according to any one of claims 26 to 30 to hair. How to color hair.

32. A step of washing hair with a hair coloring composition according to any one of claims 26 to 30, How to color hair.

33. An organic silane compound represented by the following chemical formula 1c: [Chemical Formula 1c] In the above chemical formula 1c, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, x is an integer of 2 or 3, m is an integer from 1 to 3, n1 is an integer from 0 to 5, n2 is an integer from 1 to 5.

34. In paragraph 33, The organic silane compound represented by the above chemical formula 1c is represented by the following chemical formula 1c-1 or 1c-2, Organosilane compounds: [Chemical Formula 1c-1] [Chemical Formula 1c-2] In the above chemical formulas 1c-1 and 1c-2, R1, R2, m, n1 and n2 are as defined in Article 33.

35. In paragraph 33, R1 and R2 are each ethyl, Organosilane compounds.

36. In paragraph 33, m is 3 people, Organosilane compounds.

37. In paragraph 33, n1 is 1 person, Organosilane compounds.

38. In paragraph 33, n2 is 3 people, Organosilane compounds.

39. In paragraph 33, The organic silane compound represented by the above chemical formula 1c is represented by the following chemical formula 1c-3 or 1c-4, Organosilane compounds: [Chemical Formula 1c-3] [Chemical Formula 1c-4] .

40. Containing at least one organic silane compound represented by the following chemical formula 1c, Composition for hair coloring: [Chemical Formula 1c] In the above chemical formula 1c, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, x is an integer of 2 or 3, m is an integer from 1 to 3, n1 is an integer from 0 to 5, n2 is an integer from 1 to 5.

41. In paragraph 40, R1 and R2 are each ethyl, Composition for hair coloring.

42. In paragraph 40, m is 3 people, Composition for hair coloring.

43. In paragraph 40, n1 is 1 person, Composition for hair coloring.

44. In paragraph 40, n2 is 3 people, Composition for hair coloring.

45. In paragraph 40, The organic silane compound represented by the above chemical formula 1c is represented by the following chemical formula 1c-3 or 1c-4, Composition for hair coloring: [Chemical Formula 1c-3] [Chemical Formula 1c-4] .

46. ​​In paragraph 40, The above hair coloring is for hair browning or blackening, or for preventing whitening, Composition for hair coloring.

47. In paragraph 40, The above hair coloring composition comprises an organic silane compound represented by the above chemical formula 1 in an amount of 0.001 wt% or more and 10 wt% or less based on the total weight. Composition for hair coloring.

48. The hair coloring composition of Article 40 is a shampoo, hair conditioner, hair treatment, hair lotion, hair gel, hair pack, hair cream, or hair essence. Composition for hair coloring.

49. A method comprising applying a hair coloring composition according to any one of claims 40 to 48 to hair. How to color hair.

50. A step of washing hair with a hair coloring composition according to any one of claims 40 to 48, How to color hair.

51. An organosilane compound represented by the following chemical formula 1d: [Chemical Formula 1d] In the above chemical formula 1d, x is an integer of 2 or 3, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, n is an integer from 2 to 5, m is an integer from 1 to 3.

52. In paragraph 51, The organic silane compound represented by the above chemical formula 1d is represented by any one of the following chemical formulas 1d-1 to 1d-3: Organosilane compounds: [Chemical formula 1d-1] [Chemical formula 1d-2] [Chemical formula 1d-3] In the above chemical formulas 1d-1 to 1d-3, R1, R2, m and n are as defined in Article 51.

53. In paragraph 51, R1 and R2 are each ethyl, Organosilane compounds.

54. In paragraph 51, n is 3 people, Organosilane compounds.

55. In paragraph 51, m is 3 people, Organosilane compounds.

56. In paragraph 51, The organic silane compound represented by the above chemical formula 1d is one selected from the following group: Organosilane compounds: .

57. Comprising at least one organic silane compound represented by the following chemical formula 1d, Composition for hair coloring: [Chemical Formula 1d] In the above chemical formula 1d, x is an integer of 2 or 3, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, n is an integer from 2 to 5, m is an integer from 1 to 3.

58. According to claim 57, R1 and R2 are each ethyl, A composition for hair coloring.

59. According to claim 57, n is 3, A composition for hair coloring.

60. According to claim 57, m is 3, A composition for hair coloring.

61. According to claim 57, The organosilane compound represented by the formula 1d is any one selected from the following group, A composition for hair coloring: .

62. According to claim 57, The hair coloring is for hair browning or blackening, or includes prevention of whitening, A composition for hair coloring.

63. According to claim 57, The composition for hair coloring contains the organosilane compound represented by the formula 1 in an amount of 0.001% by weight or more and 10% by weight or less based on the total weight, A composition for hair coloring.

64. The composition for hair coloring according to claim 57 is shampoo, hair conditioner, hair treatment, hair lotion, hair gel, hair pack, hair cream or hair essence, A composition for hair coloring.

65. A method for hair coloring, comprising the step of applying the composition for hair coloring according to any one of claims 57 to 64 to the hair, A method for hair coloring.

66. A method for hair coloring, comprising the step of washing the hair with the composition for hair coloring according to any one of claims 57 to 64, A method for hair coloring. A composition for preventing heat damage of hair and for hair styling, comprising one or more selected from the group consisting of organosilane compounds represented by the following formulas 1e to 3e: [Formula 1e] [Formula 2e] [Formula 3e] In the above formulas 1e to 3e x is an integer of 2 or 3, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, m is an integer from 1 to 3. n is an integer from 2 to 5, n1 is an integer from 0 to 5, n2 is an integer from 1 to 5, X1 and X2 are each independently O or -(CH2)-, a to c are each independently an integer from 1 to 5.

68. According to claim 67, The organic silane compound represented by the above chemical formula 1e is a composition for preventing heat damage to hair and for styling hair represented by any one of the following chemical formulas 1e-1 to 1e-3: [Chemical formula 1e-1] [Chemical formula 1e-2] [Chemical formula 1e-3] . In the above chemical formulas 1e-1 to 1e-3, R1, R2, m and n are as defined in the above chemical formula 1e.

69. In paragraph 67, The organic silane compound represented by the above chemical formula 1e is a composition for preventing heat damage to hair and for styling hair, which is selected from the following group: .

70. In paragraph 67, The organic silane compound represented by the above chemical formula 2e is a composition for preventing heat damage to hair and for styling hair represented by either the chemical formula 2e-1 or 2e-2 below: [Chemical formula 2e-1] [Chemical formula 2e-2] In the above chemical formulas 2e-1 and 2e-2, R1, R2, m, n1 and n2 are as defined in the above chemical formula 2e.

71. In paragraph 67, The organic silane compound represented by the above chemical formula 2e is a composition for preventing heat damage to hair and for styling hair, which is selected from the following group: .

72. In paragraph 67, The organic silane compound represented by the above chemical formula 3e is a composition for preventing heat damage to hair and for styling hair represented by either the chemical formula 3e-1 or 3e-2 below: [Chemical formula 3e-1] [Chemical formula 3e-2] .

73. In paragraph 67, The above composition is a composition for preventing heat damage to hair and for hair styling, which increases the tensile strength by 20% or more compared to hair not treated with the composition.

74. In paragraph 67, The above composition is a composition for preventing heat damage to hair and for styling hair in the form of a hair tonic, a hair conditioner, a hair essence, a hair lotion, a hair nutrition lotion, a hair shampoo, a hair rinse, a hair treatment, a hair cream, a hair nutrition cream, a hair moisture cream, a hair massage cream, a hair wax, a hair aerosol, a hair pack, a hair nutrition pack, a hair soap, a hair cleansing foam, a hair mist, a hair oil, a hair drying agent, a hair preservation treatment agent, a hair dye, a hair waving agent, a hair bleaching agent, a hair gel, a hair glaze, a hair dressing agent, a hair lacquer, a hair moisturizer, a hair mousse or a hair spray.

75. In paragraph 67, The above composition is a composition for preventing heat damage to hair and for styling hair, which is a wash-off or leave-on type.

76. In paragraph 67, The composition is a composition for preventing heat damage to hair and for styling hair, comprising 0.0001 wt% to 10 wt% of an organic silane compound represented by the chemical formulae 1e to 3e based on the total weight of the composition.

77. A method for preventing heat damage to hair and styling hair, comprising the step of treating hair with a composition according to claim 67.

78. In paragraph 77, A method for preventing heat damage to hair and styling hair, further comprising a step of heating hair at a temperature of 40°C to 250°C.

79. In paragraph 78, The step of heating the hair is performed using one of the following devices to prevent heat damage to the hair and to style the hair: Blow dryer, flat iron, hair dryer, heat lamp, heat wand, heating hood, heating cap, heating rod, curling iron, crimping iron, thermostat, heating curlers / rods or steam curlers.

80. In paragraph 77, The composition is applied to the hair immediately before or after at least one of the following: - Chemical treatment of hair, - If your hair has been chemically damaged, - If the hair has been mechanically damaged, - If your hair has been heat damaged, or - If the hair has been damaged by environmental factors.

81. A hair composition comprising one or more selected from the group consisting of organic silane compounds represented by the following chemical formulae 1e to 3e: [Chemical Formula 1e] [Chemical Formula 2e] [Chemical Formula 3e] In the above chemical formulas 1e to 3e x is an integer of 2 or 3, R1 and R2 are each independently substituted or unsubstituted C 1-10 It is alkyl, m is an integer from 1 to 3. n is an integer from 2 to 5, n1 is an integer from 0 to 5, n2 is an integer from 1 to 5, X1 and X2 are each independently O or -(CH2)-, a to c are each independently an integer from 1 to 5.

82. In paragraph 81, The organic silane compound represented by the above chemical formula 1e is a hair composition represented by any one of the following chemical formulas 1e-1 to 1e-3: [Chemical formula 1e-1] [Chemical formula 1e-2] [Chemical formula 1e-3] . In the above chemical formulas 1e-1 to 1e-3, R1, R2, m and n are as defined in the above chemical formula 1e.

83. In paragraph 81, The organic silane compound represented by the above chemical formula 1e is a hair composition selected from the following group:

84. In paragraph 81, The organic silane compound represented by the above chemical formula 2e is a hair composition represented by either the following chemical formula 2e-1 or 2e-2: [Chemical formula 2e-1] [Chemical formula 2e-2] In the above chemical formulas 2e-1 and 2e-2, R1, R2, m, n1 and n2 are as defined in the above chemical formula 2e.

85. In paragraph 81, The organic silane compound represented by the above chemical formula 2e is a hair composition selected from the following group: .

86. In paragraph 81, The organic silane compound represented by the above chemical formula 3e is a hair composition represented by either the following chemical formula 3e-1 or 3e-2: [Chemical formula 3e-1] [Chemical formula 3e-2] .

87. In paragraph 81, The above hair composition is a hair composition for preventing or improving hair frizz.

88. In paragraph 87, The above hair composition is a hair composition having a hair frizz change rate of 40% or less according to the following formula 1e: [Formula 1e] [Equation 2e] In the above equation 1e, The initial FAF Value is the Frizz Area Fraction (FAF) value of the hair treated with the hair composition according to Article 81. The FAF Value after washing is the FAF value after washing and drying the hair treated with the hair composition according to Article 81. The above Frizz Area Fraction (FAF) of the above-mentioned frizzy hair is determined by the above-mentioned Equation 2e. The frizzy hair area (Frizz area) in the above-mentioned Equation 2e is a portion where the light transmittance is 50% or more when light is irradiated to the hair using a Bolero-Lite (BOSSA NOVA VISION, USA) device, the area of ​​the neat hair (Bulk area) is a portion where the light transmittance is less than 50%, and the area fraction of the frizzy hair (FAF) means the ratio of the area occupied by the frizzy portion to the total area of ​​the hair.

89. In paragraph 87, The above hair composition is a hair composition in the form of a hair tonic, a hair conditioner, a hair essence, a hair lotion, a hair nutrition lotion, a hair shampoo, a hair rinse, a hair treatment, a hair cream, a hair nutrition cream, a hair moisture cream, a hair massage cream, a hair wax, a hair aerosol, a hair pack, a hair nutrition pack, a hair soap, a hair cleansing foam, a hair mist, a hair oil, a hair drying agent, a hair preservation treatment agent, a hair dye, a hair waving agent, a hair bleaching agent, a hair gel, a hair glaze, a hair dressing agent, a hair lacquer, a hair moisturizer, a hair mousse or a hair spray.

90. In paragraph 87, The above hair composition is a hair composition of the wash-off or leave-on type.

91. In paragraph 87, The above hair composition comprises an organic silane compound represented by the chemical formulas 1e to 3e in an amount of 0.0001 wt% to 10 wt% based on the total weight of the composition.

92. A method for preventing or improving hair frizz, comprising the step of treating hair with a hair composition according to Article 87.

93. In paragraph 92, A method for preventing or improving hair frizz, further comprising the step of heating the hair at a temperature of 40°C to 250°C.

94. In paragraph 93, A method for preventing or improving hair frizz, wherein the step of heating the hair is performed using one of the following devices: Blow dryer, flat iron, hair dryer, heat lamp, heat wand, heating hood, heating cap, heating rod, curling iron, crimping iron, thermostat, heating curlers / rods or steam curlers.

95. In paragraph 92, The above hair composition is applied to the hair immediately before or after at least one of the following: - Chemical treatment of hair, - If your hair has been chemically damaged, - If the hair has been mechanically damaged, - If your hair has been heat damaged, or - If the hair has been damaged by environmental factors.

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