KR101761489B1 - One-component type paint composition with superior scratch resistance - Google Patents
One-component type paint composition with superior scratch resistance Download PDFInfo
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- KR101761489B1 KR101761489B1 KR1020150187891A KR20150187891A KR101761489B1 KR 101761489 B1 KR101761489 B1 KR 101761489B1 KR 1020150187891 A KR1020150187891 A KR 1020150187891A KR 20150187891 A KR20150187891 A KR 20150187891A KR 101761489 B1 KR101761489 B1 KR 101761489B1
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- South Korea
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- polyol resin
- coating composition
- carbamate group
- scratch
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Classifications
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- C09D7/125—
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/005—Dendritic macromolecules
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention relates to a polyurethane resin composition comprising a carbamate group-containing acrylic polyol resin, a hyperbranched structure carbamate group-containing polyester polyol resin, a curing agent, and a curing catalyst and is excellent in acid resistance and scratch resistance. Particularly, Scratch-resistant one-pack coating composition capable of ensuring excellent elasticity, flexibility and scratch resistance even in the case of a scratch-resistant coating film.
Description
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a high-scratch scratch-resistant one-pack coating composition.
In the automotive coating industry, top coats can consist of a base coat, a clear coat or a monocoat. The color and clear coating system applying a clear coat after applying a base coat to impart color to a substrate is a finishing process of a commonly used automotive paint and has a performance sufficient to withstand various and stringent conditions required for an automobile Is required.
While ether curing systems coated with a hydroxyl-functional resin and an aminoplast, which have been used in conventional one-part thermosetting coating compositions, provide excellent coating properties, ether bonds formed by curing mechanisms are well known to have poor acid resistance , Coating compositions based on a curing structure having a carbamate functional group as one of the methods for solving such problems have been known in the art. The effects obtained from a thermosetting coating composition incorporating a carbamate curing structure include improved transparency, high DOI (durability), improved scratch resistance as well as securing flexibility with improved durability and hardness.
U.S. Patent Application No. 1994-241925 discloses a coating composition comprising a carbamate acrylic resin / melamine or a carbamate melamine / oxizolidine block dodecylbenzyl sulfonic acid (DDBSA) catalyst, wherein the coating composition is applied as a one-pack coating composition And has a high hardness but is flexible and has excellent chemical resistance.
U.S. Patent Application No. 1999-378319 also discloses a process for producing a polymer having a carbamate functional group, which comprises reacting a polymer or oligomer having a hydroxy functional group with a low molecular weight alkyl carbamate to produce a carbamate polymer, A process for producing carbamate polyesters has been disclosed.
In addition, U.S. Patent Application Publication No. 2003-0009052 discloses a coating composition comprising a carbamate-modified acrylic resin, a carbamate-modified polyester, a melamine, and a curing agent, and in particular, a carbamate polyester is an essential component of the patent. And then reacted with a carbamate to obtain a rheology control agent (RCA), that is, a sagging synergistic effect.
However, when the above-mentioned coating compositions are applied to a one-pack type clear coating composition using a melamine curing agent, there is a problem that the physical properties of the cured coating film are poor in elasticity, flexibility or scratch resistance.
Accordingly, there is still a demand for a coating composition which is superior to the conventional one-pack coating material when applied to a one-pack transparent coating material using a melamine curing agent, and which can ensure excellent physical properties of the coating film and scratch resistance.
The present invention relates to a polyurethane resin composition comprising a carbamate group-containing acrylic polyol resin, a hyperbranched structure carbamate group-containing polyester polyol resin, a curing agent, and a curing catalyst and is excellent in acid resistance and scratch resistance. Particularly, It is an object of the present invention to provide a high-scratch one-pack coating composition which can secure excellent elasticity, flexibility and scratch resistance even in the case of a scratch-resistant coating.
The high-scratch one-pack coating composition of the present invention comprises a resin, a curing agent, a curing catalyst, and an organic solvent, wherein the resin comprises 30 to 70% by weight of a carbamate group-containing acrylic polyol resin based on 100% by weight of the coating composition; And 5 to 25% by weight of a hyperbranched structure carbamate group-containing polyester polyol resin.
The scratch-resistant one-pack type coating composition of the present invention has an equivalent or superior acid resistance and scratch resistance as compared with the conventional one-pack type coating, and is excellent in elasticity, flexibility and scratch resistance even when the coating film is cured by applying it as a one- It is possible to secure property.
Hereinafter, the present invention will be described in more detail.
The high-scratch one-pack coating composition of the present invention comprises a resin, a curing agent, a curing catalyst, and an organic solvent, wherein the resin comprises 30 to 70% by weight of a carbamate group-containing acrylic polyol resin based on 100% by weight of the coating composition; And 5 to 25% by weight of a hyperbranched structure carbamate group-containing polyester polyol resin.
The coating composition of the present invention has a solids content of 50 to 70% by weight and a viscosity of 20 to 40 seconds based on the Ford Cup # 4. If the viscosity is less than 20 seconds, problems such as falling down on the vertical surface may occur. If the viscosity exceeds 40 seconds, a load may be applied to the sprayer, which may cause the sprayer to fail. The appearance may be inhibited.
The carbamate group-containing acrylic polyol resin used in the coating composition of the present invention may have a solid content of 50 to 80% by weight and a carbamate group equivalent of 400 to 700 on a solid weight basis. The carbamoate group-containing acrylic polyol resin may have a weight average molecular weight of 3,000 to 10,000, a glass transition temperature of -30 to 30 占 폚, and a hydroxyl value of 30 to 70 mgKOH based on the solid content weight. When the carbazole-group-containing acrylic polyol resin satisfies the above-mentioned equivalent and hydroxyl value, it is possible to obtain suitable mechanical properties in application of the coating film. Although not particularly limited, the carbazolyl group-containing acrylic polyol resin may contain an organic solvent, Can be prepared using unsaturated monomers, nonfunctional acrylic monomers, acrylic monomers containing hydroxyl groups, alkyl carbamates and tin-based catalysts.
Ethylenically unsaturated monomers may include, but are not limited to, styrene and its derivatives, butadiene, and acrylic or methacrylic acid esters of C1 to C12 alkyl.
The non-functional acrylic monomer may be selected from the group consisting of methyl methacrylate, ethyl methacrylate, isobutyl methacrylate, n-butyl methacrylate, tertiary butyl methacrylate, n-hexyl methacrylate, 2- ethylhexyl methacrylate, Acrylate, methacrylate, cyclohexyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, isobutyl acrylate, n-butyl acrylate, tertiary butyl acrylate, 2-ethylhexyl acrylate, Isobornyl acrylate, cyclohexyl acrylate, and the like can be used.
The monomer containing a hydroxyl group is preferably selected from the group consisting of 2-hydroxyethyl methacrylate, hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, , Caprylic methacrylate, caprolactone acrylate, caprolactone methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, polypropylene modified acrylate, polypropylene modified methacrylic Methylmethacrylate, 2,2,4-trimethyl-1,3-pentanediol monoacrylate, 2,2,4-trimethyl-1,3-pentanediol monoacrylate, , 4-trimethyl-1,3-pentanediol monomethacrylate, isobornyl acrylate, isobornyl methacrylate and the like can be used.
The coating composition of the present invention comprises 30 to 70% by weight, for example 35 to 65% by weight, for example 40 to 60% by weight, of a carbamate group-containing acrylic polyol resin based on 100% by weight of the total composition. When the content of the carbamoyl group-containing acrylic polyol resin is too small, there is a problem that the chemical properties such as chemical resistance are impaired. When the content is too large, there is a problem that the coating film becomes too hard such as resistance to chipping. If the content of the carbamate-containing acrylic polyol resin is out of the above range, the mechanical properties and workability in manufacturing and coating may be lowered.
The coating composition of the present invention comprises a polyester polyol resin containing a hyperbranched structure carbamate group. The hyperbranched structure carbamate group-containing polyester polyol resin of the present invention means that a polyester resin containing three or more carbamate groups in an isocyanate compound is bonded in a branched structure.
The hyperbranched structure carbamate group-containing polyester polyol resin used in the coating composition of the present invention may have a solid content of 50 to 80% by weight and a carbamate group equivalent of 500 to 800 on a solid weight basis. The hyperbranched structure carbamate group-containing polyester polyol resin may have a weight average molecular weight of 5,000 to 20,000 and a hydroxyl value of 30 to 70 mgKOH based on the solid weight.
Although not specifically limited, the hyperbranched structure carbamate group-containing polyester polyol resin can be produced using an organic solvent, a polyhydric alcohol, a polyvalent acid, an alkyl carbamate, a tin catalyst, and an isocyanate compound.
Polyhydric alcohols include glycols, dihydric alcohols, trihydric alcohols, tetravalent alcohols and the like. Examples of the polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,4-butanediol, 2,3-butanediol, 1,6-hexanediol, dimethylene glycol, trimethylolpropane , Neopentyl glycol, and the like.
Examples of the polyvalent acid include maleic anhydride, fumaric acid, citraconic anhydride, tetrahydrophthalic anhydride, isophthalic acid, terephthalic acid, hexahydrophthalic acid, adipic acid, sebacic acid, azelaic acid, and anhydrides thereof.
The isocyanate compound may be selected from isocyanate monomers such as toluene diisocyanate, hexamethylene diisocyanate, methylene diphenyl diisocyanate, and methylene bis (4-cyclohexyl isocyanate), and a dimer or trimer of the above monomers.
The coating composition of the present invention may contain from 5 to 25% by weight, for example from 8 to 22% by weight, for example from 12 to 18% by weight, of a hyperbranched structure carbamate group-containing polyester polyol resin based on 100% . When the content of the hyperbranched structure carbamate group-containing polyester polyol resin is too small, it is difficult to obtain excellent elasticity, flexibility and scratch resistance of the coating film, and when the content is too large, it is difficult to secure the hardness of the coating film.
As the curing agent used in the coating composition of the present invention, a melamine compound can be used, and for example, a compound selected from the group consisting of hexamethylol melamine, hexamethoxymethyl melamine, hexabutoxymethyl melamine, and combinations thereof can be used have.
The coating composition of the present invention may contain 6 to 25% by weight, for example 8 to 22% by weight, for example 12 to 18% by weight, of the curing agent based on 100% by weight of the total composition. When the content of the curing agent is less than 6% by weight, the hardness and the solvent resistance are affected by incomplete curing when the curing agent reacts with the main resin. When the content exceeds 25% by weight, the curing agent is affected by physical properties such as adhesiveness and impact resistance And an unreacted melamine compound may remain in the coating film, thereby adversely affecting other physical properties.
The curing catalyst used in the coating composition of the present invention may be selected from the group consisting of dodecylbenzenesulfonic acid, sulfonic acid, dinonylnaphthalene disulfonic acid, dinonylnaphthalenesulfonic acid, and combinations thereof.
The coating composition of the present invention may contain 0.1 to 5% by weight, for example 0.3 to 3% by weight, for example 0.5 to 2% by weight, of the curing catalyst based on 100% by weight of the total composition. Outside of the above range, the mechanical properties may be deteriorated due to incomplete curing.
The organic solvent used in the coating composition of the present invention is not particularly limited and may be selected from the group consisting of coco sol # 100, butanol, 1-methoxy-2-propyl acetate, ethyl ethoxypropionate, Can be used. The coating composition of the present invention may contain 5 to 30% by weight, for example 10 to 27% by weight, for example 15 to 23% by weight, of an organic solvent based on 100% by weight of the total composition. If it is out of the above range, the manufacturing and coating workability may be deteriorated.
The coating composition of the present invention may further comprise at least one additive selected from the group consisting of a surface conditioner, a light stabilizer, a weathering additive, an appearance control agent, a defoaming agent and a leveling agent. Although not specifically limited, the coating composition of the present invention may contain 0.01 to 20% by weight of the additive based on 100% by weight of the total composition.
Hereinafter, the present invention will be described more specifically by way of examples. However, these examples are provided only for the understanding of the present invention, and the scope of the present invention is not limited to these examples in any sense.
[ Example ]
One. Synthetic example One: Carbamate group Containing acrylic polyol resin (A)
215 parts by weight of Cocosol # 100 was introduced into a synthetic four-necked flask equipped with a thermometer, a stirrer, a condenser and a heating device, and the temperature was raised to the reflux temperature (165 ° C). After refluxing was stabilized, 206 parts by weight of 2-hydroxyethyl acrylate, 190 parts by weight of styrene monomer, 100 parts by weight of n-butyl acrylate and 40 parts by weight of alphamethylstyrene dimer were uniformly mixed and 15 parts by weight of tertiary butyl peroxybenzoate And 40 parts by weight of Cocosol # 100 were uniformly mixed and homogeneously separated for 180 minutes and 195 minutes, respectively, followed by refluxing for 60 minutes. After completion of the holding, the mixture was diluted with coco sol # 100, and the reaction product was cooled to 80 캜. 80 parts by weight of methylcarbamate and 1.3 parts by weight of dibutyltin oxide were added thereto, and methanol eluted at about 145 캜 was collected separately. After collecting about 30 parts by weight of methanol, nitrogen was injected, and the remaining methyl carbamate was removed for 1 hour, and the reaction was terminated by cooling. Thus, a carbamate group-containing acrylic polyol resin having a solid content of 63%, a viscosity of Z2, a hydroxyl value of 50 mgKOH, a weight average molecular weight of 5,000, a glass transition temperature of 10 ° C and a carbamate group equivalent of 600 on a solid basis weight was obtained .
2. Comparative Synthetic Example 1: Preparation of acrylic polyol resin (B)
215 parts by weight of Cocosol # 100 was inserted into a synthetic four-necked flask equipped with a stirrer, a thermometer and a stirrer, and the temperature was raised to the reflux temperature (165 ° C). After stabilizing the reflux, 203 parts by weight of hydroxypropyl acrylate, 152 parts by weight of styrene monomer, 132 parts by weight of n-butyl methacrylate, 127 parts by weight of n-butyl acrylate, 10 parts by weight of tertiary butyl peroxybenzoate, 100, 52 parts by weight were homogeneously and separately added for 180 minutes and 195 minutes, followed by refluxing for 60 minutes. Diluted with coco sol # 100, and the reaction product was cooled to 60 캜 to obtain an acrylic polyol resin having a solid content of 70%.
3. Synthetic example 2: Hyperbranch structure Carbamate group contain polyester Preparation of polyol resin (C)
A synthetic four-necked flask equipped with a thermometer, a stirrer, a condenser, a packed column and a heating device was charged with 90 parts by weight of trimethylolpropane, 250 parts by weight of neopentyl glycol, 380 parts by weight of hexahydrophthalic anhydride, 0.5 part by weight were added and the temperature was gradually raised. After the molten product was melted, stirring was performed to gradually raise the temperature to 230 ° C while removing the condensed water. While maintaining the temperature at 230 占 폚 until the acid value became 10, when the acid value became 10 or less, the mixture was cooled to 80 占 폚, and 90 parts by weight of methyl carbamate was added and the temperature was gradually raised to 145 占 폚. The condensed methanol was removed and cooled to 60 캜 when the hydroxyl value became 60 or less. 80 parts by weight of coco sol # 100, 70 parts by weight of ethoxyethyl propionate and 55 parts by weight of hexamethylene diisocyanate trimer (Desmudur N-3300) were fed at 60 占 폚 and NCO% Lt; / RTI > After the maintenance, the reaction solution was diluted with coco sol # 100 and the reaction was terminated. Thus, a hyperbranched structure carbamate group-containing polyester polyol resin having a solid content of 70%, a carbamate group equivalent of 700 on a solid weight basis, a weight average molecular weight of 12,000, a viscosity of Z3 and a hydroxyl value of 55 was obtained.
4. Comparative Synthetic Example 2: Carbamate group contain polyester Preparation of polyol resin (D)
A synthetic four-necked flask equipped with a thermometer, a stirrer, a condenser, a packed column and a heating device was charged with 90 parts by weight of trimethylolpropane, 250 parts by weight of neopentyl glycol, 380 parts by weight of hexahydrophthalic anhydride, And the temperature was gradually raised to 165 ° C. After the molten product was melted, stirring was performed to gradually raise the temperature to 230 ° C while removing the condensed water. After maintaining the acid value at 230 ° C until the acid value became 10, the acid value was lowered to 10 or lower, followed by cooling to 80 ° C, and the reaction was terminated while diluting with cocosol # 100. As a result, a resin having a solid content of 70%, a viscosity Y and a hydroxyl value of 157 was obtained.
5. Preparation of Coating Composition
Examples 1 to 3 and Comparative Examples 1 to 5 were each prepared in the composition shown in Table 1 and mixed with stirring at 1500 rpm for 20 minutes or more to prepare a coating composition. Respectively.
Hardener: Alkylated melamine (Cymel 1161)
Curing catalyst: Dodecylbenzenesulfonic acid (Nacure XP 221)
Surface conditioner: silicone surfactant (BYK-331 10% sol'n)
Light stabilizer: hindered amine light stabilizer (Tinuvin 123)
UV absorber: Tinuvin 384
- Coating condition
① Handgun spray
② Nozzle diameter: 1.5mm, air pressure: 4.5kgf / cm 2
③ The distance between the nozzle inlet and the specimen is kept constant in the range of 2 ~ 30 cm, and it moves horizontally at the speed of 40 ~ 50cm / sec.
④ After painting, measure the physical properties (hardness, adhesion, water resistance, acid resistance, alkali resistance, solvent resistance, etc.) of the coating film after curing at 130 ° C for 20 minutes
- How to measure property
(1) Hardness
- Measuring method: Measured by pencil hardness method (hardness measurement which does not damage the coating with each pencil of 3B, 2B, B, HB, F, H,
(3B, 2B, B, HB, F, H, 2H, 3H:
(2) Adhesiveness
- Measuring method: Completely painted specimens are treated with heat-treated CYCLE and left at room temperature for 24 hours.
- Heat treatment CYCLE: The process of leaving at room temperature for 20 minutes at 150 ℃ for 20 minutes is repeated 3 times
(M-1, M-2, M-3, M-4,
(3) Water resistance
- Measuring method: The specimens are immersed in a constant temperature water bath at 40 ℃ for 240 hours and then left at room temperature for 1 hour.
- Judgment method: After the test, the appearance should be free of softening, whitening, gloss defect, peeling, swelling, discoloration, and there should be no difference in appearance between the immersed part and the immersed part, and the total peeled area should be less than 5%.
(M-1, M-2, M-3, M-4,
(4) Acid resistance
- Measuring method: 0.2 mL of 0.1 N sulfuric acid is added dropwise to the test specimen, and the temperature of the gradient oven is set at 35 to 40 ° C., followed by heating for 150 minutes.
- Judgment method: Determine whether the highest temperature at which damage does not occur is determined as the acid resistance temperature by checking the occurrence of etching, staining, and blistering on the test specimen where the sulfuric acid solution is dropped.
(5) Scratch resistance
- Measurement method: 10 round trips using Amtec Kistler equipment.
- Determination method: The initial 20-degree gloss of the specimen is measured, and the 20-degree gloss is measured after 10 round trips. The gloss before the measurement is divided by the gloss after the measurement to calculate the gloss retention rate.
(6) Solvent resistance
- Measuring method: Put the cotton cloth with test solvent (XYLENE) on the specimen and scrape 4 times with 2Kg force every 1 minute to record the time when the lower layer coat appears.
As can be seen from Table 2, Examples 1 to 3, which are high-scratch one-pack coating compositions of the present invention, have physical properties such as hardness, adhesion, water resistance and acid resistance comparable or superior to those of Comparative Examples 1 to 3 , And exhibited excellent effects in terms of elasticity, flexibility, scratch resistance and solvent resistance as compared with Comparative Examples 1 to 5. That is, when the one-pack type scratch-resistant coating composition of the present invention was used, it was confirmed that elasticity and flexibility were improved due to excellent scratch resistance.
Claims (6)
Based on 100% by weight of the coating composition,
30 to 70% by weight of a carbamate group-containing acrylic polyol resin; And
5 to 25% by weight of a hyperbranched structure carbamate group-containing polyester polyol resin;
Wherein the one-part scratch-resistant one-part type coating composition comprises:
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150187891A KR101761489B1 (en) | 2015-12-28 | 2015-12-28 | One-component type paint composition with superior scratch resistance |
| JP2018534132A JP6688893B2 (en) | 2015-12-28 | 2016-12-27 | One-pack coating composition with high scratch resistance |
| CN201680076872.3A CN108473817B (en) | 2015-12-28 | 2016-12-27 | One-pack type coating composition having excellent scratch resistance |
| PCT/KR2016/015336 WO2017116118A1 (en) | 2015-12-28 | 2016-12-27 | Highly scratch resistant one-pack type paint composition |
| US16/066,515 US10683436B2 (en) | 2015-12-28 | 2016-12-27 | One-component type paint composition with superior scratch resistance |
| EP16882070.2A EP3399002B1 (en) | 2015-12-28 | 2016-12-27 | Highly scratch resistant one-pack type paint composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020150187891A KR101761489B1 (en) | 2015-12-28 | 2015-12-28 | One-component type paint composition with superior scratch resistance |
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| Publication Number | Publication Date |
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| KR20170077955A KR20170077955A (en) | 2017-07-07 |
| KR101761489B1 true KR101761489B1 (en) | 2017-07-26 |
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| KR1020150187891A KR101761489B1 (en) | 2015-12-28 | 2015-12-28 | One-component type paint composition with superior scratch resistance |
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| KR102160972B1 (en) * | 2018-02-08 | 2020-09-29 | 주식회사 케이씨씨 | Coating composition |
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