KR20140136551A - Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same - Google Patents
Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same Download PDFInfo
- Publication number
- KR20140136551A KR20140136551A KR1020130056236A KR20130056236A KR20140136551A KR 20140136551 A KR20140136551 A KR 20140136551A KR 1020130056236 A KR1020130056236 A KR 1020130056236A KR 20130056236 A KR20130056236 A KR 20130056236A KR 20140136551 A KR20140136551 A KR 20140136551A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- polydialkylsiloxane
- modified urethane
- acrylate compound
- acrylate
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
Abstract
Description
The present invention relates to a process for producing a polydialkylsiloxane-modified urethane-acrylate compound, a polydialkylsiloxane-modified urethane acrylate compound produced thereby, and a coating composition comprising the same.
Generally, in the case of a scratch-resistant coating film, the required physical properties should be excellent and hard.
As a conventional technique for imparting scratch resistance to a coating film, there is a method of coating a surface of a thermosetting resin composition and curing it by heat. There is a disadvantage in that it can not use various substrates because of problems. Further, the thickness of the coating film also has a limitation in forming a coating film, and it takes a long time to cure, resulting in poor workability and easy peeling and extraction.
As a result, a method of applying a resin composition that can be cured by ultraviolet rays for several seconds and applying ultraviolet curing has been developed. Generally, in order to impart scratch resistance to a coating film, an ultraviolet curable resin composition containing epoxy-modified urethane acrylate or polyester acrylate having 2 to 3 functional groups as a main resin is used. However, (H) or more is not obtained. Also, since they do not use a non-reactive solvent, it is difficult to realize a thin film and flexibility is low.
One aspect of the present invention is to provide a process for producing a polydialkylsiloxane-modified urethane-acrylate compound having high hardness and flexibility, a polydialkylsiloxane-modified urethane acrylate compound prepared thereby, and a coating composition comprising the same .
However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other problems not mentioned can be clearly understood by those skilled in the art from the following description.
In order to achieve the above object, an aspect of the present invention is to provide an oligomer having a hydroxy group at both terminal ends and a dialkyl siloxane chain represented by the formula (1) and an oligomer of the diisocyanate compound represented by the formula (2) To produce a urethane compound; And reacting the urethane compound with an acrylate-based compound having a hydroxyl group at the terminal and a method of producing the polydialkylsiloxane-modified urethane acrylate compound.
[Chemical Formula 1]
HO-R 1 - (Si (R 2 ) (R 3 ) -O) x -Si (R 4 ) (R 5 ) -R 1 -OH
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms, and x represents 2 to 200 Lt; / RTI >
(2)
OCN- (CH 2 ) y -NCO
(Wherein y represents an integer of 1 to 10).
Another aspect of the present invention provides a polydialkylsiloxane-modified urethane acrylate compound represented by Formula 4 below.
[Chemical Formula 4]
[NCO- (CH 2) y -NCO ] w - (CH 2) y -NHCOO-R 1 - (Si (R 2) (R 3) -O) x -Si (R 4) (R 5) -R 1 -COONH- (CH 2) y - [NCO- (CH 2) y -NCO] w
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms and x represents an integer of 2 to 200 , Y represents an integer of 1 to 10, and w represents an integer of 2 to 9.)
Another aspect of the present invention provides a coating composition comprising the polydialkylsiloxane-modified urethane acrylate compound, a curing agent, a photoinitiator, and an organic solvent.
According to the present invention, it is possible to provide a coating composition which can be used for various substrates with a high curing rate, thereby providing a coating film having excellent hardness and flexibility.
Hereinafter, a method for producing a polydialkylsiloxane-modified urethane-acrylate compound of the present invention, a polydialkylsiloxane-modified urethane acrylate prepared by the method, Compounds and coating compositions comprising them are described in detail.
The present invention relates to a polydialkylsiloxane-modified urethane acrylate compound which can be used for an ultraviolet curable resin composition capable of imparting high scratch resistance, and a thin film such as a polyethyl terephthalate (PET) film or a polyethylene film, And can impart scratch resistance to the ultraviolet ray-curable resin composition.
In order to prepare the polydialkylsiloxane-modified urethane acrylate compound of the present invention, first, a compound having a hydroxy group at both terminal ends and having a dialkylsiloxane chain represented by the formula (1) is prepared.
[Chemical Formula 1]
HO-R 1 - (Si (R 2 ) (R 3 ) -O) x -Si (R 4 ) (R 5 ) -R 1 -OH
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms, and x represents 2 to 200 Lt; / RTI >
The compound of Formula 1 may be prepared by reacting an alcohol containing a vinyl group (-CH = CH 2 ) and a hydroxyl group (-OH) simultaneously with a polydialkylsiloxane in the presence of a catalyst.
For example, in the case of hydroxypropyl polydimethylsiloxane (HO-PDMS-OH), which is a compound of formula (1), polydimethylsiloxane and aryl alcohol can be prepared by reacting with a platinum catalyst.
The reaction mechanism in this case can be expressed by the following reaction formula 1.
[Reaction Scheme 1]
Next, an oligomer is prepared by polymerizing the diisocyanate compound represented by the general formula (2).
(2)
OCN- (CH 2 ) y -NCO
(Wherein y represents an integer of 1 to 10).
The oligomer may be a subunit of which the diisocyanate compound represented by the formula (2) is repeatedly connected in 3 to 10 rings to form a cyclic structure.
For example, a cyclic hexamethyl diisocyanate trimer can be prepared by repeating the cyclization of three hexamethyl diisocyanates, which are one kind of compounds represented by the general formula (2), as subunits. The mechanism for this can be expressed by the following reaction formula (2).
[Reaction Scheme 2]
The oligomer may be represented by a trimer, a tetramer, a pentamer, a hexamer, or the like depending on the number of subunits to which the oligomer is repeatedly connected.
Next, a urethane compound is prepared by reacting an oligomer of the diisocyanate compound with a siloxane compound having a hydroxy group at both ends and a dialkylsiloxane chain. At this time, the isocyanate group (-N = C = O) attached to the oligomer and the hydroxyl group (-OH) at both ends attached to the siloxane compound undergo urethane reaction to produce a urethane compound.
For example, urethane compounds represented by the product of Scheme 3 can be prepared by subjecting hydroxypropyl polydimethylsiloxane (HO-PDMS-OH) and hexamethyl diisocyanate trimer to urethane reaction.
[Reaction Scheme 3]
Then, a polydialkylsiloxane-modified urethane acrylate compound can be prepared by reacting an urethane compound with an acrylate-based compound having a hydroxy group at the terminal. The acrylate compound having a hydroxy group may be represented by the following general formula (3).
(3)
CH 2 = C (R 4 ) -COO-C n H 2n OH
(Wherein R 4 = H or CH 3 , and n represents an integer of 1 to 30)
Specifically, there may be mentioned hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, hydroxyhexyl acrylate, hydroxyoctyl acrylate, hydroxynonyl acrylate, hydroxypentyl acrylate, hydroxyethyl methacrylate Acrylate, hydroxypropyl methacrylate, hydroxypropyl methacrylate, hydroxybutyl methacrylate, hydroxyhexyl methacrylate, hydroxy octyl methacrylate, hydroxynonyl methacrylate, and hydroxypentyl methacrylate.
In addition, the polydialkylsiloxane-modified urethane acrylate compound prepared through the above process has an acrylate group introduced therein and can be represented by the following formula (4).
[Chemical Formula 4]
[NCO- (CH 2) y -NCO ] w - (CH 2) y -NHCOO-R 1 - (Si (R 2) (R 3) -O) x -Si (R 4) (R 5) -R 1 -COONH- (CH 2) y - [NCO- (CH 2) y -NCO] w
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms and x represents an integer of 2 to 200 , Y represents an integer of 1 to 10, and w represents an integer of 2 to 9.)
For example, when 2-hydroxyethyl methacrylate is reacted with a urethane compound, which is a product of the reaction formula 3, the following polyfunctional polydialkylsiloxane-modified urethane acrylate compound may be prepared through the following reaction formula have.
[Reaction Scheme 4]
In Scheme 4, R represents ethyl methacrylate.
Polydialkylsiloxane modified urethane acrylate compounds contain urethane bonds and are generally flexible. In addition, since it contains silicon, it can be contained in a coating film and can have high hardness characteristics when applied. Above all, in the case of a polyfunctional compound, many functional groups contributing to the crosslinking reaction are hardly cured, have.
A coating composition comprising a curing agent, a photoinitiator, and an organic solvent may be prepared using the polydialkylsiloxane-modified urethane acrylate compound prepared as described above as a main material.
The polydialkylsiloxane-modified urethane acrylate compound contributes to the curability by irradiation with ultraviolet rays, and at the same time, enhances adhesion to the substrate. The content of the polydialkylsiloxane-modified urethane acrylate compound in the coating composition is preferably from 10 to 70% by weight. If the content exceeds 70% by weight, the viscosity or applicability of the composition deteriorates. When the content is less than 10% by weight, it is difficult to obtain the object of the present invention.
For the preparation of the coating compositions of the present invention, the polydialkylsiloxane-modified urethane acrylate compounds of the present invention may be used alone or in combination with other aqueous binders. Such an aqueous binder will, for example, be composed of a polyester, a polyacrylate, a polyepoxide or a polyurethane polymer.
In order to realize a flexible coating film while improving the scratch resistance, the above-mentioned curing agent can be produced by using aliphatic urethane acrylate as a main resin and reacting reactive monomers having 3 to 4 functional groups with reactive monomers having a monofunctional group, So that the reactivity can be improved by absorbing ultraviolet rays of various wavelengths.
The photoinitiator may be any compound known in the art as long as it is a compound capable of decomposing by ultraviolet irradiation to generate radicals and initiate polymerization.
Examples of photoinitiators include benzophenone, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, phenyl-2-hydroxy-2-propyl ketone, 4- methoxybenzophenone, 1- hydroxycyclohexyl Phenyl ketone, and benzyldimethyl ketal. These compounds may be used alone or in combination.
It is preferable that the photoinitiator comprises 0.1 to 10% by weight of the coating composition. If the amount is less than 0.1% by weight, sufficient photo-curing may not be attained and problems such as blocking phenomenon, surface strength and adhesion may occur. If the amount exceeds 10% by weight, the photoinitiator after curing may remain, And problems such as yellowing and light fastness occur.
The organic solvent can be used to realize a thin film by using a coating film as a thin film to give a uniform physical property, to improve the smoothness of the coating film and to improve the wettability of the composition. As the organic solvent, isopropyl alcohol, butyl acetate, methyl ethyl ketone, toluene and the like can be used. In using a solvent, it is preferable to include isopropyl alcohol and butyl acetate in a ratio of 1.5 to 3: 1, and the organic solvent may further include methyl ethyl ketone and toluene.
In addition to the above materials, an antioxidant, an ultraviolet absorber, a light stabilizer, a thermal polymerization inhibitor, a leveling agent, a surfactant, a lubricant and the like may be used together.
Hereinafter, the present invention will be described in detail with reference to Examples. However, the following examples are only for illustrating the present invention in more detail and do not limit the scope of the present invention.
[ Example ]
(One) Of hydroxypropylpolydimethylsiloxane Produce
In order to prepare hydroxypropylpolydimethylsiloxane having hydroxypropyl groups at both ends thereof, a three-necked flask equipped with a stirrer, a reflux condenser and a thermometer was charged with polydimethylsiloxane, hydrogenated aryl alcohol, and platinum catalyst Was added and reacted at 70 ° C for 4 hours to prepare hydroxypropylpolydimethylsiloxane having a hydroxypropyl group at the terminal thereof.
(2) Polydimethylsiloxane Modified Urethane / Acrylate Produce
Hexamethyltriisocyanate trimer, 2-hydroxyethyl methacrylate, and hydroformylpolydimethylsiloxane prepared in (1) above were reacted with a catalyst DBTL to obtain an acrylate group Was prepared. ≪ tb >< TABLE >
(3) Preparation of coating film by ultraviolet irradiation
2 g of a curing agent (Miramer M610), 10 g of a curing agent (Miramer PU600), 0.6 g of a photoinitiator (Irgacure-184), 0.5 g of a urethane-modified polydimethylsiloxane, Methyl (methylethylketone), IPA (isopropylalcohol), and MIBK ) Was coated on a polyethyl terephthalate (PET) film and irradiated with ultraviolet rays at a dose of 300 to 350 mW / cm 2 or 1.5 (mW / cm 2) with a high-pressure mercury lamp having a main wavelength of 365 nm To 1.9 J / cm < 2 > to obtain a cured coating film.
(4) Hardness test
In order to confirm the surface hardness of the ultraviolet cured coating film prepared in the present invention, the hardness of the surface was measured using pencil hardness and the results are shown in Table 1. In Table 1, the surface hardness of the product of the present invention is It is superior to other companies.
(5) Flexibility test
In order to examine the flexibility of the coating film prepared in the same manner as in the above (3), a film having a coating film formed on a steel bar having different thicknesses was rolled to confirm the presence of cracks. As a result of the measurement, it was confirmed that cracks were not generated in the steel bar with a minimum of 50 pie.
Claims (5)
A process for producing a polydialkylsiloxane-modified urethane acrylate compound, which comprises reacting an urethane compound with an acrylate-based compound having a hydroxy group at the terminal.
[Chemical Formula 1]
HO-R 1 - (Si (R 2 ) (R 3 ) -O) x -Si (R 4 ) (R 5 ) -R 1 -OH
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms, and x represents 2 to 200 Lt; / RTI >
(2)
OCN- (CH 2 ) y -NCO
(Wherein y represents an integer of 1 to 10).
Wherein the acrylate compound having a hydroxy group at the terminal is a compound represented by the general formula (3).
(3)
CH 2 = C (R 4 ) -COO-C n H 2n OH
(Wherein R 4 = H or CH 3 , and n represents an integer of 1 to 30)
Wherein the oligomer is a subunit of which the diisocyanate compound is repeatedly connected in 2 to 10 rings to form a cyclic structure.
[Chemical Formula 4]
[NCO- (CH 2) y -NCO ] w - (CH 2) y -NHCOO-R 1 - (Si (R 2) (R 3) -O) x -Si (R 4) (R 5) -R 1 -COONH- (CH 2) y - [NCO- (CH 2) y -NCO] w
(Wherein R 1 represents a divalent organic group having 1 to 30 carbon atoms, R 2 , R 3 , R 4 and R 5, which are the same or different, each represent an organic group having 1 to 10 carbon atoms and x represents an integer of 2 to 200 , Y represents an integer of 1 to 10, and w represents an integer of 2 to 9.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130056236A KR20140136551A (en) | 2013-05-20 | 2013-05-20 | Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020130056236A KR20140136551A (en) | 2013-05-20 | 2013-05-20 | Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140136551A true KR20140136551A (en) | 2014-12-01 |
Family
ID=52456736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020130056236A KR20140136551A (en) | 2013-05-20 | 2013-05-20 | Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20140136551A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101646004B1 (en) * | 2015-10-15 | 2016-08-09 | 유한회사 베리카화장품 | Gel polish composition |
| WO2018088713A1 (en) * | 2016-11-11 | 2018-05-17 | 주식회사 엘지화학 | Curable composition |
| KR102113436B1 (en) * | 2019-11-22 | 2020-05-21 | 서광공업 주식회사 | Anticorrosive coating compositions and valves with anti-corrosion coating formed by the same |
| CN112119353A (en) * | 2018-02-09 | 2020-12-22 | 联合富大有限公司 | Photosensitive binder |
| KR20220116887A (en) * | 2021-02-16 | 2022-08-23 | (주)노루페인트 | Modified-polydialkylsiloxane compound and uv/moisture-curable silicone coating composition including the same |
-
2013
- 2013-05-20 KR KR1020130056236A patent/KR20140136551A/en not_active Application Discontinuation
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101646004B1 (en) * | 2015-10-15 | 2016-08-09 | 유한회사 베리카화장품 | Gel polish composition |
| WO2017065364A1 (en) * | 2015-10-15 | 2017-04-20 | 유한회사 베리카화장품 | Gel polish composition |
| CN107072929A (en) * | 2015-10-15 | 2017-08-18 | 菲莉卡化妆品公司 | Nail polish glue composition |
| JP2017535512A (en) * | 2015-10-15 | 2017-11-30 | ベリカ コスメティックス リミテッドＶａｌｉｋａ Ｃｏｓｍｅｔｉｃｓ Ｌｔｄ． | Gel polish composition |
| WO2018088713A1 (en) * | 2016-11-11 | 2018-05-17 | 주식회사 엘지화학 | Curable composition |
| KR20180052964A (en) * | 2016-11-11 | 2018-05-21 | 주식회사 엘지화학 | Curable composition |
| CN108779332A (en) * | 2016-11-11 | 2018-11-09 | 株式会社Lg化学 | Curable compositions |
| US10577452B2 (en) | 2016-11-11 | 2020-03-03 | Lg Chem, Ltd. | Curable composition |
| CN108779332B (en) * | 2016-11-11 | 2021-06-22 | 株式会社Lg化学 | Curable composition |
| CN112119353A (en) * | 2018-02-09 | 2020-12-22 | 联合富大有限公司 | Photosensitive binder |
| KR102113436B1 (en) * | 2019-11-22 | 2020-05-21 | 서광공업 주식회사 | Anticorrosive coating compositions and valves with anti-corrosion coating formed by the same |
| KR20220116887A (en) * | 2021-02-16 | 2022-08-23 | (주)노루페인트 | Modified-polydialkylsiloxane compound and uv/moisture-curable silicone coating composition including the same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100864349B1 (en) | Actinic Radiation Curable Resin Composition For Film Protection Layer and Film and Optical Sheet Made by Using the Same | |
| KR102385524B1 (en) | Fluorine-containing acryl composition and method for preparing the same, activation energy radiation-curable fluorine-containing composition, and article | |
| KR20140136551A (en) | Method for preaparing polydialkylsiloxane modified urethane-acrylate compound, polydialkylsiloxane modified urethane-acrylate compound prepared thereby and coating composition comprising the same | |
| WO2006095686A1 (en) | Ultraviolet-curable resin composition, ultraviolet-curable coating material, and coated article | |
| JPS6126665A (en) | (meth)acrylic acid ester reformed organopolysiloxane mixture | |
| JP2006328364A (en) | Active energy ray-curable resin composition and article and molded product using the same | |
| JP5566216B2 (en) | Active energy ray-curable resin composition, coating agent composition using the same, and cured coating film | |
| WO2015152110A1 (en) | Urethane (meth)acrylate compound, active-energy-ray-curable resin composition, and coating agent | |
| KR20190025800A (en) | Supporting substrate for flexible display apparatus, method of manufacturing the substrate, and flexible display apparatus having the substrate | |
| KR101942006B1 (en) | Composition For Hard Coating and Hard Coating Film Including Cured Product Of The Same As The Coating Layer | |
| JP6965186B2 (en) | Photocurable resin composition | |
| JP6358789B2 (en) | Active energy ray-curable resin composition and coating agent | |
| US11359110B2 (en) | Radiation curable compositions with anti-stain properties | |
| JP2019085558A (en) | Active energy ray curable resin composition and coating agent | |
| JP6075443B2 (en) | Active energy ray-curable coating composition | |
| JP2016179966A (en) | Photo-curing composition for nail makeup and nail cosmetics | |
| JP2005042001A (en) | Coating composition, method for forming coated film, and coated article | |
| KR20190014233A (en) | Supporting substrate for flexible display apparatus, method of manufacturing the substrate, and flexible display apparatus having the substrate | |
| JP2014065902A (en) | Active energy ray curing resin composition and coating agent | |
| KR102480470B1 (en) | Modified-polydialkylsiloxane compound and uv/moisture-curable silicone coating composition including the same | |
| JP2010180319A (en) | Urethane (meth)acrylate and coating agent containing the same | |
| CN113980240A (en) | UV-curable hyperbranched organic silicon modified polyurethane and coating | |
| JP4109176B2 (en) | Energy ray curable resin composition and paint using the same | |
| WO2019182155A1 (en) | Curable composition, cured product, method for producing cured product, and method for repairing damage of cured product | |
| JP3657037B2 (en) | Active energy ray-curable resin composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| N231 | Notification of change of applicant | ||
| E902 | Notification of reason for refusal | ||
| E902 | Notification of reason for refusal | ||
| E601 | Decision to refuse application |