Polymer compounds and their applications

Abstract

The present invention relates to a polymer compound that can be chemically bonded to the surface of an inorganic nanopowder to modify the surface, and applications thereof. More specifically, the present invention relates to a polymer compound that can be easily and quickly chemically bonded to the surface of an inorganic nanoparticle powder to modify the surface of the inorganic nanoparticles and form a polymer coating layer, and that can be produced economically and efficiently, and applications thereof.

Description

[Technical Field]

[0001] The present invention relates to a polymer compound that can chemically bond to the surface of inorganic nanopowder to modify the surface, and applications thereof. More specifically, the present invention relates to a polymer compound that can easily and quickly undergo a chemical bonding reaction with the surface of inorganic nanoparticle powder to modify the surface of inorganic nanoparticles and form a polymer coating layer, and that can be produced economically and efficiently, and applications thereof. [Background technology]

[0002] Inorganic nanoparticle powders commonly used in the cosmetics industry are primarily titanium dioxide (TiO2) or zinc oxide (ZnO). These inorganic nanoparticle powders are primarily used as pigments in skin-toning cream formulations and as inorganic sunscreens in sunscreen products. Recently, global warming due to ozone layer depletion and increased skin exposure to UV rays have led to rapid growth. To protect skin from these increased UV rays, the sunscreen market has grown rapidly by more than 10% annually. Sunscreen products use dispersion formulation systems based on inorganic nanoparticles and organic UV absorbers to protect skin from UV rays. These sunscreen products must also provide effective UV protection while also providing a lightweight feel, smooth application, and a clean finish. However, while inorganic nanoparticle powders are important materials for UV scattering, their high density and strong interparticle interactions can negatively impact all other performance characteristics. Therefore, attempts have been made to improve the surface properties of inorganic nanoparticle powders to improve their skin stability and dispersibility and enhance product performance. While efforts have been made to improve dispersion instability through organic and silica coatings, the fundamental problem remains. To improve the intrinsic properties of inorganic materials, new coating technologies based on organic materials are needed, but no coating technology that satisfies both productivity and product performance has yet been developed.

[0003] Attempts have been made to use materials such as fatty acids, silicones, amino acids, and fluorine compounds to coat the surface of inorganic nanopowders (TiO2, ZnO) commonly used in conventional cosmetic formulations. However, these materials have the following problems: Fatty acid coatings reduce oil resistance to sebum, causing shine and discoloration; silicone coatings leave the skin feeling dry and rough; amino acid coatings reduce water and oil resistance and make the skin feel heavy; and fluorine compound coatings cause the cosmetics to feel stuffy, unnatural, and difficult to mold. To address these issues of poor skin compatibility, efforts are being made to develop new inorganic nanopowder coating technologies.

[0004] In particular, techniques have been reported for forming a uniform thin layer of biocompatible molecules on the surface of inorganic nanopowder to enhance favorable usability, such as skin adhesion, moisturizing, and adhesiveness (e.g., Patent Document 1; Non-Patent Document 1). However, the polymerization methods used in these techniques for coating inorganic nanopowder surface molecules are surface growth polymerization and surface deposition polymerization, which limit the thickness of the surface thin film of inorganic nanopowder. They require a surface initiator linker, resulting in low polymerization efficiency and limitations on the incorporation of hydrophobic monomers into the polymer structure to improve skin adhesion. Furthermore, production requires expensive, multi-step processes, which poses various disadvantages, such as reduced productivity, making development difficult. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent No. 10-1767207 [Non-patent literature]

[0006] [Non-Patent Document 1] Polymer, 54 (21), 2013, 5609-5614 Summary of the Invention [Problem to be solved by the invention]

[0007] The object of the present invention is to provide a polymer compound that can easily and quickly undergo a chemical bonding reaction with the surface of inorganic nanoparticle powder used in cosmetic preparations, thereby modifying the surface of the inorganic nanoparticles and forming a polymer coating layer, and that can be produced economically and efficiently, and applications thereof. [Means for solving the problem]

[0008] In order to achieve the above object, the present invention provides a compound represented by the following formula (1): [ka] (In the formula, R' may be the same or different and each independently represents hydrogen or a methyl group; R1 is a group containing a phosphorylcholine-like phospholipid structure, R2 is independently hydrogen; an alkoxy group; an amino group; an epoxy group; or a C1-C20 aliphatic hydrocarbon group or a C6-C20 aromatic hydrocarbon group which is unsubstituted or substituted with one or more functional groups; R3 is independently an alkyl group, an alkoxy group, an epoxy group, a hydroxy group, or a C1 to C20 aliphatic hydrocarbon group or a C6 to C20 aromatic hydrocarbon group substituted or unsubstituted with an acid functional group; R4 is a C1 to C10 aliphatic hydrocarbon group, R5, R6, and R7 are the same or different and each independently represent hydrogen; or a C1-C20 aliphatic hydrocarbon group or a C6-C20 aromatic hydrocarbon group which is substituted or unsubstituted with an alkyl group, an alkoxy group, an epoxy group, a hydroxy group, or an acid functional group; R8 and R9 are the same or different and each independently represent hydrogen; or a group containing a hydroxy, carboxylic acid, or alkoxy functional group, provided that at least one of R8 and R9 contains a hydroxy, carboxylic acid, or alkoxy functional group; W, X, Y, and Z are the molar fractions of the corresponding repeating units and are each independently 0 to 1, provided that at least one of W and X is greater than 0, and W+X+Y+Z=1.

[0009] According to another aspect of the present invention, there is provided an inorganic nanopowder having a surface to which the polymer compound of the present invention is chemically bonded.

[0010] According to yet another aspect of the present invention, there is provided a powder formulation containing the inorganic nanopowder of the present invention. [Effects of the Invention]

[0011] The polymer compound of the present invention can easily and quickly undergo a chemical bonding reaction with the surface of inorganic nanoparticle powder used in cosmetic preparations to modify the surface of the inorganic nanoparticles and form a polymer coating layer.The polymer production process does not require expensive steps or complex multi-step production processes, making it very economical and contributing to improved productivity. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 1 is an HR-TEM image of inorganic nanopowder produced in Coating Example 21 of the present invention, showing the formation of a polymer layer on the surface of TiO2 coated with polymer compound 1. [Figure 2] 1 shows the XPS analysis results of the inorganic nanopowder prepared in Coating Example 21 of the present invention, showing the difference in the bond energy (O1S, Ti2p) values ​​of the TiO2 surface before and after coating, proving that the chemical bond between the polymer compound and the TiO2 surface is well established. [Figure 3] 1 shows HR-TEM images of inorganic nanopowders produced in Coating Examples 21 to 28 and Comparative Examples 1 and 2 of the present invention. BEST MODE FOR CARRYING OUT THE INVENTION

[0013] The present invention will now be described in more detail.

[0014] The polymer compound of the present invention is represented by the following formula (1): [ka] (In the formula, R' may be the same or different and each independently represents hydrogen or a methyl group, R1 is a group containing a phosphorylcholine-like phospholipid structure, R2 is independently hydrogen; an alkoxy group; an amino group; an epoxy group; or a C1-C20 aliphatic hydrocarbon group or a C6-C20 aromatic hydrocarbon group which is unsubstituted or substituted with one or more functional groups; R3 is independently an alkyl group, an alkoxy group, an epoxy group, a hydroxy group, or a C1 to C20 aliphatic hydrocarbon group or a C6 to C20 aromatic hydrocarbon group substituted or unsubstituted with an acid functional group; R4 is a C1 to C10 aliphatic hydrocarbon group, R5, R6, and R7 are the same or different and each independently represent hydrogen; or a C1-C20 aliphatic hydrocarbon group or a C6-C20 aromatic hydrocarbon group which is substituted or unsubstituted with an alkyl group, an alkoxy group, an epoxy group, a hydroxy group, or an acid functional group; R8 and R9 are the same or different and each independently represent hydrogen; or a group containing a hydroxy, carboxylic acid, or alkoxy functional group, provided that at least one of R8 and R9 contains a hydroxy, carboxylic acid, or alkoxy functional group; W, X, Y, and Z are the mole fractions of the corresponding repeating units, and each independently ranges from 0 to 1, provided that at least one of W and X is greater than 0, and W+X+Y+Z=1.

[0015] In one embodiment, in the formula (1), R1 is represented by the following formula (2): [ka] (wherein a is an integer of 0 to 2, b is an integer from 2 to 4, R 10 , R 11 and R 12 are the same or different and each independently represent hydrogen, a C1-C6 hydrocarbon group, or -(CH2) n represents an —OH group, where n is an integer of 1 to 6. It may also be a group containing a phosphorylcholine-like phospholipid structure represented by the following formula:

[0016] In one embodiment, in the formula (1), the alkyl group may be a C1 to C20 alkyl group or a C3 to C20 cycloalkyl group, the alkoxy group may be a C1 to C20 alkoxy group or a C3 to C20 cycloalkoxy group, the acid functional group may be a carboxylic acid group, and the aliphatic hydrocarbon group may be a saturated or unsaturated aliphatic hydrocarbon group.

[0017] In one embodiment, in the formula (1), the functional group substituted on the C1 to C20 aliphatic hydrocarbon group or the C6 to C20 aromatic hydrocarbon group may be an alkoxy group, an aryloxy group, an ether group, a halogen group, an isocyanate group, a lactone group, a hydroxy group, or an acid functional group.

[0018] In the formula (1), W is 0 to 1, and more specifically, it may be 0.01 or more, 0.05 or more, or 0.1 or more, or may be 1 or less, 0.99 or less, 0.95 or less, 0.9 or less, 0.85 or less, or 0.8 or less, but is not limited thereto.

[0019] In the formula (1), X is 0 to 1, and more specifically, may be 0.01 or more, 0.05 or more, or 0.1 or more, or may be 1 or less, 0.9 or less, 0.8 or less, 0.7 or less, 0.6 or less, or 0.5 or less, but is not limited thereto.

[0020] In the formula (1), Y is 0 to 1, and more specifically, it may be 0.01 or more, 0.05 or more, or 0.1 or more, or may be 1 or less, 0.95 or less, 0.9 or less, 0.85 or less, or 0.8 or less, but is not limited thereto.

[0021] In the formula (1), Z is 0 to 1, and more specifically, may be 0.01 or more, 0.02 or more, or 0.05 or more, or may be 1 or less, 0.9 or less, 0.8 or less, 0.7 or less, 0.6 or less, or 0.5 or less, but is not limited thereto.

[0022] In one embodiment, the unsaturated phospholipid monomer providing the repeating unit represented by the mole fraction W in the formula (1) is, for example, 2-((meth)acryloyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 3-((meth)acryloyloxy)propyl-2'-(trimethylammonio)ethyl phosphate, 4-((meth)acryloyloxy)butyl-2'-(trimethylammonio)ethyl phosphate, 5-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 6-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 7-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 8-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 9-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 10-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 11-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 12-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 13-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 14-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 15-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 16-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 17-((meth)acryloyloxy)pentyl-2'-( 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(triethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tripropylammonio)ethyl phosphate, 2-((meth)acryloyloxy)ethyl-2'-(tributylammonio)ethyl phosphate, 2-((meth)acryloyloxy)propyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)butyl-2 '-(Trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)pentyl-2'-(trimethylammonio)ethyl phosphate, 2-((meth)acryloyloxy)hexyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(p-vinylbenzyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(p-vinyl benzoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(styryloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(p-vinylbenzyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(vinyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonyl)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(acryloylamino)ethyl-2'-(trimethylammonio)ethyl phosphate,2-(Vinylcarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(allyloxycarbonylamino)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(buteroyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, 2-(crotonoyloxy)ethyl-2'-(trimethylammonio)ethyl phosphate, ethyl-(2'-trimethylammonioethylphosphorylethyl) fumarate, butyric acid and may be one or more selected from the group consisting of hydroxyethyl-(2'-trimethylammonioethylphosphorylethyl)fumarate, hydroxyethyl-(2'-trimethylammonioethylphosphorylethyl)fumarate, ethyl-(2'-trimethylammonioethylphosphorylethyl)fumarate, butyl-(2'-trimethylammonioethylphosphorylethyl)fumarate, and hydroxyethyl-(2'-trimethylammonioethylphosphorylethyl)fumarate.

[0023] In one embodiment, in the formula (1), R2 is, for example, hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, lauryl, tetradecyl, hexadecyl, isobornyl, dicyclopentanyl, dicyclopentenyl, benzyl, 2-methoxyethyl, 2-ethoxyethyl, succinyl, monoalkyl succinate, monoalkyl fumarate, glycidyl, 3,4-epoxybutyl, 2,3-epoxycyclohexyl, 3,4-epoxycyclohexylmethyl, 3-methyloxetane-3-methyl, 3-ethyloxetane-3-methyl, NH2, NHCH3, allyl, 2-hydroxyethyl, 3-oxypropylmethyldimethoxysilane, tetrahydrofurfuryl, ethylene glycol disilane, and 2-isocyanatoethyl, 4-morpholine, phenyl glycidyl ether, phenoxydiethylene glycol, methoxypolyethylene glycol, 2-[4-(-1-methyl-1-phenylethyl)-phenoxy]ethyl, t-butyl, 2-oxypropyl hexahydrophthalate, γ-butyrolactone, propoxyethyl, n-isobutoxymethyl, 2-oxyethyl phthalate, 1,1,1,3,3,3-hexafluoroisopropyl, octafluoropentyl, tetrafluoropropyl, heptadecafluorodecyl, and tribromophenyl.

[0024] In one embodiment, in the formula (1), R3 may be, for example, independently selected from the group consisting of phenyl, p-methylphenyl, and p-acetoxyphenyl.

[0025] In one embodiment, in the formula (1), R4 may be, for example, a methylene group or an ethylene group.

[0026] In one embodiment, in the formula (1), R5, R6 and R7 are, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, vinyl, methacryloxymethyl, 2-methacryloxyethyl, 3-methacryloxypropyl, 3-methacryloxypropyl, 3-methacryloxypropyl, acryloxymethyl, 2-acryloxyethyl, 3-acryloxypropyl, 3-acryloxypropyl, 3-acryloxypropyl, 3-glycidyloxypropyl, 2-epoxycyclohexylethyl, 3-epoxycyclohexylpropyl, and OR. 12 (where R 12 is hydrogen, methyl, ethyl, or propyl.

[0027] The polymer compound of the present invention can be produced by any one of known polymerization methods such as radical polymerization, cationic polymerization, anionic polymerization, and condensation polymerization, but radical polymerization is preferred from the viewpoint of ease of production and economy. Alternatively, the polymer compound can be produced by mixing the monomers with a polymerization solvent, heating to an appropriate temperature depending on the half-life temperature of the thermal initiator used, and then removing oxygen under a nitrogen atmosphere.

[0028] Polymerization conditions for polymer compounds may vary in polymerization time and temperature depending on the type of thermal initiator used. As the radical polymerization initiator, a commonly known thermal initiator can be used, more specifically, 2,2'-azobisisobutyronitrile, 2,2'-azobis-2,4-dimethylvaleronitrile, 2,2'-azobis-(4-methoxy-2,4-dimethylvaleronitrile), benzoyl peroxide, lauroyl peroxide, t-butyl peroxypivalate, 1,1'-bis-(bis-t-butylperoxy)cyclohexane, 1,1'-azobis(cyclohexane-1-carbonitrile), 4,4'-azobis(4-cyanovaleric acid), dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis[2-methyl-N-(2-hydroxyethyl) ) propionamide, 2,2'-azobis(N-butyl-2-methylpropionamide, 2,2'-azobis[2-(2-imidazolinyl)propane]dihydrochloride, 2,2'-azobis[2-(2-imidazolinyl)propane, 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 4,4'-azobis(4-cyanovaleric acid), 2,2'-azobis[N-(2-carboxyethyl)-2-methylpropionamidine]tetrahydrate, dimethyl-2,2'-azobis(2-methylpropionate), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), and the like may be used alone or in combination of two or more.

[0029] In one embodiment, a commonly known chain transfer agent may be used to adjust the weight average molecular weight (Mw) of the polymer during the preparation of the polymer compound. More specifically, 1-dodecanethiol, octadecanethiol, pentaerythritol tetrakis(3-mercaptobutyrate), 1,3,5-tris(3-mercaptobutyroethyl)-1,3,5-triazine-2,4,6-trione, thioglycolic acid, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropyldimethoxysilane, 3-mercaptopropyldiethoxysilane, 2-mercaptopropionic acid, 3-mercaptopropionic acid, etc. may be used.

[0030] In one embodiment, the weight-average molecular weight (Mw, g / mol) of the polymer compound of the present invention may be 1,000 to 200,000 g / mol, and the polydispersity index (PDI) may be 1.0 to 20. More specifically, the weight-average molecular weight (Mw) may be 5,000 to 100,000 g / mol, and the polydispersity index (PDI) may be 1.0 to 10. More specifically, the weight-average molecular weight (Mw) may be 10,000 to 50,000 g / mol, and the polydispersity index (PDI) may be 1.0 to 5.0, but these examples are not limited thereto. Furthermore, the polymer compound of the present invention may be a homopolymer or a random copolymer in which the sequence of each polymer unit is not limited, but these examples are not limited thereto.

[0031] For polymer polymerization, a suitable solvent can be used taking into consideration the compatibility with the monomers, initiator, chain transfer agent, and other additives. Examples of suitable solvents include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methyl phenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl- Ketones such as 2-pentanone, methyl n-propyl ketone, methyl n-butyl ketone, methyl n-amyl ketone, 2-heptanol, etc.; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, etc.; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, etc.; alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc.; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.2-Alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionic acid esters such as methyl methyl 2-oxy-2-propionate and methyl ethyl 2-oxy-2-propionate; monooxymonocarboxylic acid alkyl esters of 2-alkoxy-2-propionic acid methyl alkyl esters such as methyl methyl 2-methoxy-2-propionate and methyl ethyl 2-ethoxy-2-propionate; ethyl 2-hydroxypropionate, methyl ethyl 2-hydroxy-2-propionate, ethyl hydroxyacetate, and 2-hydroxy-3-methylbutanoic acid methyl esters; ketone acid esters such as ethyl pyruvate; and N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. A single solvent or a mixture of two or more solvents can be used.

[0032] The polymer compound of the present invention easily and quickly undergoes a chemical bonding reaction with the surface of inorganic nanoparticle powders used in cosmetic preparations, and can therefore modify the surface of the inorganic nanoparticle powders and form a polymer coating layer.

[0033] Therefore, according to another aspect of the present invention, there is provided an inorganic nanopowder having a surface to which the polymer compound of the present invention is chemically bonded. In one embodiment, the inorganic nanopowder may be an inorganic nanomaterial (e.g., titanium dioxide, zinc oxide, mica, sericite, kaolin, silicic anhydride, boron nitride, or talc having an average particle size of 100 nm or less) having a coating layer of the polymer compound of the present invention on its surface.

[0034] According to yet another aspect of the present invention, there is provided a powder formulation comprising the inorganic nanopowder of the present invention.

[0035] In one embodiment, the powder formulation may be, but is not limited to, a powder for blocking ultraviolet rays, a powder for cosmetics, or a powder for coloring.

[0036] The present invention will be described in more detail below with reference to examples and comparative examples, which, however, are not intended to limit the scope of the present invention in any way.

[0037] Example Examples 1 to 20 <Polymerization of polymer compounds> Polymerization was carried out using the types and ratios of monomers A to E shown in Table 1 below, as well as the types and amounts (parts by weight relative to 100 parts by weight of the total monomers) of thermal initiators and chain transfer agents shown in Table 1 below. Polymerization conditions included a three-neck round-bottom flask, absolute ethanol as the polymerization solvent, and dissolution so that the solids content of the mixture was 35 parts by weight. Polymerization was carried out at elevated temperature. After polymerization was completed, 100 ppm of t-butylhydroquinone (t-BHQ) was added as a polymerization inhibitor to prevent further polymerization. The weight-average molecular weight (Mw) and polydispersity index (PDI) at the end of polymerization are shown in Table 1 below. The weight-average molecular weight (Mw) and polydispersity index (PDI) were controlled using a chain transfer agent.

[0038] [Ingredients used] A: 2-methacryloyloxyethyl phosphorylcholine B: 3-trimethoxypropyl methacrylate C: tert-butyl methacrylate D: Methyl methacrylate E: Allyltriethoxysilane F: 2,2'-azobisisobutyronitrile G: 4,4'-azobis(4-cyanovaleric acid) H: 3-mercaptopropyltrimethoxysilane I: 1-dodecanethiol

[0039] [Table 1]

[0040] Examples 21 to 28 <Evaluation of TiO2 coating using polymer compounds> Each of the polymer compounds 1, 2, 6, 7, 9, 12, 15, and 17 in Table 1 prepared as described above was coated onto a titanium dioxide surface under the conditions shown in Table 2 below. The titanium dioxide used was commercially available. After coating, HR-TEM analysis was performed to confirm whether a polymer compound layer had formed on the titanium dioxide surface, and XPS analysis was performed to confirm the transfer of binding energy values. The results are shown in Table 2 below.

[0041] Comparative Examples 1-2 The titania surface was coated with each of the polymer compounds of the following formulas (3) and (4), and the results were evaluated in the same manner as above. The results are shown in Table 2 below. [ka] TiO2 surface coating and cleaning test The TiO2 surface coating and cleaning processes were performed as follows. First, in the coating process, 97 g of TiO2 was placed in a beaker and 100 g of anhydrous ethanol solvent was added. The mixture was homogenized by high-speed stirring using a homodisperse mixer at room temperature. Next, 3 g of polymer compound was added in four batches while stirring using a homodisperse mixer. After homogenization by stirring for 10 minutes at room temperature, the resulting mixture was dried on aluminum foil at 100°C for 12 hours, then pulverized in a hammer mill and filtered through a 60-mesh filter. After the coating process was completed, in the cleaning process, 30 g of TiO2 coated on 200 mL of PET sample was added to 120 g of ionized water in a bottle. The mixture was then stirred at high speed for 1 hour and centrifuged (3000 rpm, 10 minutes) to precipitate the inorganic powder. The clear upper layer was then removed, and the solid lower layer was transferred to aluminum foil and dried at 100°C for 12 hours. The dried TiO2 powder was then finely ground in a bowl and stored.

[0042] Confirmation of the formation of a polymer compound coating layer on the TiO2 surface (TEM image confirmation) To confirm whether the coating of the polymer compound on the inorganic nanopowder (TiO2) surface after the coating and cleaning processes had progressed well, measurements were taken using an HR-TEM. On the other hand, cases in which a polymer layer was formed and observed in the TEM image even after strong cleaning treatment were indicated by an "O", and cases in which the polymer layer was not formed and was washed away, resulting in no polymer layer being observed, were indicated by an "X".

[0043] Confirmation of the presence or absence of chemical bonds of polymer compounds on the TiO2 surface (confirmation by XPS analysis) XPS analysis was used to confirm whether the polymer compound was chemically bonded well to the TiO2 surface through a chemical reaction. X-ray photoelectron spectroscopy (XPS) is one of the most widely used techniques for surface analysis. Because the bond energy measured using XPS is element-specific, it can be used to analyze the elements of the sample. Because the bond energy varies depending on the chemical bond state, information about the chemical bond state can be obtained. The bond energy of the O1S level and the Ti2p level of TiO2 were confirmed. Changes in surface modification due to chemical bonding are expressed as shifts in the bond energy value of each level, allowing the presence or absence of surface coating to be confirmed. A significant shift in bond energy value of 0.3 eV or greater is considered significant. Observed shifts in bond energy value are indicated by "○," and no shifts are indicated by "X."

[0044] [Table 2]

Claims

1. 10 to 80 mol % of polymerized units of monomer W, which is 2-methacryloyloxyethyl phosphorylcholine, relative to 100 mol % of all monomers; 20 to 50 mol % of polymerized units of a monomer X selected from 3-trimethoxypropyl methacrylate, tert-butyl methacrylate, and methyl methacrylate, based on 100 mol % of all monomers; 0 to 45 mol % of polymerized units of monomer Z, which is allyltriethoxysilane, based on 100 mol % of all monomers; A polymeric compound comprising: At least one terminal group of the polymer compound is a hydroxy group, a carboxylic acid group, or an alkoxy group. High molecular compound.

2. An inorganic nanopowder having a surface to which the polymer compound according to claim 1 is chemically bonded.

3. A powder formulation comprising the inorganic nanopowder according to claim 2.

4. 4. The powder preparation according to claim 3, which is a powder for blocking ultraviolet rays, a powder for cosmetics, or a powder for color toning.

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