KR101813250B1 - Uv-curable coating composition and transparent film manufacturing method using the same - Google Patents
Uv-curable coating composition and transparent film manufacturing method using the same Download PDFInfo
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- KR101813250B1 KR101813250B1 KR1020150181502A KR20150181502A KR101813250B1 KR 101813250 B1 KR101813250 B1 KR 101813250B1 KR 1020150181502 A KR1020150181502 A KR 1020150181502A KR 20150181502 A KR20150181502 A KR 20150181502A KR 101813250 B1 KR101813250 B1 KR 101813250B1
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/08—Homopolymers or copolymers of acrylic acid esters
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- 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
- C09D183/04—Polysiloxanes
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Abstract
The present invention relates to an ultraviolet ray curable coating composition having excellent abrasion resistance and a method of forming a coating film. The ultraviolet ray curable coating composition mainly comprises a urethane acrylate oligomer, a multifunctional acrylate monomer and an additive capable of compensating for surface characteristics, Siloxane compounds. The composition having such a composition can improve the scratch resistance and abrasion resistance of the surface of a conventional UV-curable coating layer (hardness, slipperiness, etc.) by the polydimethylsiloxane compound, thereby maintaining the quality of a plastic molded article or a film.
Description
More particularly, the present invention relates to a UV-curable coating composition capable of forming a transparent coating film for hard coating or protection on electronic products, and a method for forming a transparent coating film using the UV-curable coating composition .
In recent years, the touch screen has not been widely used in electronic products such as televisions, computers, and mobile phones. However, due to the recent increase in the use of touch screens and the increase in the range of mobile phones represented by navigation and smart phones in daily life, Problems such as breakage of an image display device and deterioration of visibility due to various scratches are raised.
In addition, many thermosetting or thermoplastic plastic products have been developed to replace the commonly used display glass parts in order to assure the design freedom of various display products. These parts have abrasion resistance, including scratch resistance, Therefore, many developments have been made to supplement this.
As a method for solving this problem, there is a method in which the hardness of the ultraviolet curable coating liquid is increased, the abrasion resistance is supplemented, and the protective film is directly coated on a plastic product or coated on polyethylene terephthalate (PET) or polycarbonate (PC)
In the case of the ultraviolet curable coating liquid used for such a coating, it is composed of an organic hybrid type or urethane acrylate oligomer, a multi-functional acrylate monomer, and other additives. However, it is not satisfactory in terms of abrasion resistance to date.
This is because the basic constituent does not achieve appropriate surface slip and hardness, and the additive to be supplemented is not durable and has a limited role in supplementing abrasion.
SUMMARY OF THE INVENTION Accordingly, the present invention has been made keeping in mind the above problems occurring in the prior art, and it is an object of the present invention to provide an ultraviolet curable coating composition capable of forming a transparent protective coating film having properties such as high hardness and high strength.
Another object of the present invention is to provide a method for forming a transparent coating film having properties such as high hardness and high strength.
Another object of the present invention is to provide a transparent coating film having properties such as high hardness and high strength formed using a UV curable coating composition.
The ultraviolet curable coating composition according to one embodiment for realizing the object of the present invention includes 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, 0.5 to 10 parts by weight of a reactive initiator and 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
Another embodiment of the present invention for realizing the object of the present invention is a UV curable coating composition comprising 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, 0.5 to 10 parts by weight, 1 to 40 parts by weight of a compound containing inorganic particles, and 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
In one embodiment, the polydimethylsiloxane compound having an acrylate group includes at least one selected from the following Structural Formula 1, Structural Formula 2 and Structural Formula 3 below.
- [Structural Formula 2]
(-CH 3 ), a phenyl group (-C 6 H 5 ), a hydrogen group (-H) and a trifluoromethyl group (-CF 3 ) in the structural formula 1, the structural formula 2 and the structural formula 3, . ≪ / RTI >
In one embodiment, the ultraviolet curable coating composition may further comprise 0.01 to 2 parts by weight of an additive for imparting antifoaming properties and improving the processability.
In one embodiment, the polydimethylsiloxane compound having an acrylate group may be at least one selected from a polydimethylpolysiloxane compound having a diacrylate group, a polydimethylpolysiloxane compound having a monoacrylate group, and a polydimethylpolysiloxane compound having a tetraacrylate group .
In order to form the transparent coating film according to one embodiment of the present invention, 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer 0.5 to 10 parts by weight of a photoreactive initiator, and 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group. Thereafter, the ultraviolet curable coating composition is coated on the object and then the ultraviolet curable coating is formed.
In order to form the transparent coating film according to another embodiment of the present invention, 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer 0.5 to 10 parts by weight of a photoreactive initiator, 1 to 40 parts by weight of a compound containing inorganic particles, and 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group. Thereafter, the ultraviolet curable coating composition is coated on the object and then the ultraviolet curable coating is formed.
Since the ultraviolet ray curable coating composition having the above composition has superior abrasion resistance as compared with conventional ultraviolet ray curable coating compositions, a clear coating film for protecting an image display device having excellent abrasion resistance including scratch resistance can be formed on a transparent plastic film or a film surface .
Hereinafter, the present invention will be described in more detail. While the invention is susceptible to various modifications and alternative forms, specific embodiments thereof are further described in the text. It should be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but includes all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.
In this application, the terms "comprises" or "having", etc. are intended to specify the presence of stated features, components, steps, processes, compositions, or combinations thereof in the specification, and not to limit the presence or addition of one or more other features or components, Steps, processes, compositions, or combinations thereof, which are not intended to be limiting.
Also, unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.
UV curable coating composition
The ultraviolet curable coating composition for forming a protective transparent coating film having properties such as high hardness and high strength according to the present invention may contain, as an example, urethane acrylate oligomer having a weight average molecular weight of less than 10,000, monofunctional and polyfunctional acrylate monomer, An initiator and a polydimethylsiloxane compound comprising an acrylate group.
More specifically, the ultraviolet curable coating composition comprises 10 to 70 parts by weight of a urethane acrylate oligomer, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, 0.5 to 10 parts by weight of a photoreactive initiator and a polydimethylsiloxane compound 0.2 to 5 parts by weight.
As an example, the urethane acrylate oligomer is a urethane acrylate oligomer having from 2 to 10 acrylate functional groups in the molecular structure, and has a weight average molecular weight of 10,000 or less.
When the weight-average molecular weight of the urethane acrylate oligomer is 10,000 or more, the transparent coating film formed by curing is softened, so that it is difficult to realize appropriate hardness and strength, so that the abrasion resistance is lowered. As a result, it is unsuitable for use as a protective coating film for an image display device.
In particular, the ultraviolet curing type coating composition used in the present invention is mainly composed of constituent materials having a molecular weight of less than 10,000, thereby improving the processability at the time of coating.
If the amount of the urethane acrylate oligomer used is less than 10 parts by weight based on 100 parts by weight of the ultraviolet curing type coating composition excluding the solvent, there may be no problem in terms of processability, but problems such as cracking of the formed coating film occur, Hardness may not be realized, and if it exceeds 70 parts by weight, the processability during coating may deteriorate or the additional characteristics of the composition may be insufficient. Therefore, it is preferable to use the urethane acrylate oligomer within the range of 10 to 70 parts by weight for the ultraviolet curable coating composition.
Specific examples of the monofunctional and polyfunctional acrylate monomers include caprolactone acrylate, benzyl acrylate, tetrahydrofurfuryl acrylate, stearyl acrylate, lauryl acrylate, 1,4-butanediol di (meth) acrylate Acrylate, dicyclopentanyl di (meth) acrylate, caprolactone-modified dicyclopentenyl di (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, (Meth) acrylate, 1,6-hexadiol diacrylate, trimethylolpropane tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, , Pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate Agent, the polyol poly (meth) acrylate, bisphenol A- diglycidyl ether di (meth) acrylate, urethane (meth) acrylate, glycerol trimethacrylate, etc., but is not necessarily limited in this respect. They are used together with urethane acrylate oligomer having two or more functionalities and can be used alone or in combination. Of these monomers, one to four monofunctional acrylate monomers including monofunctional acrylates of one to three and pentaerythritol triacrylate can be used together.
If the amount of the monofunctional and multifunctional acrylate monomers used is less than 20 parts by weight based on the amount of the ultraviolet curing type coating composition excluding the solvent, the process may have poor processability or additional characteristics of the composition may be insufficient. If the amount is more than 80 parts by weight, There may be no problem but cracks or the like of the formed coating film may occur or the desired strength and hardness may not be realized. Therefore, it is preferable to use the monofunctional and multifunctional acrylate monomer within the range of 20 to 80 parts by weight.
The photoreactive initiator used for initiating the radical polymerization may be selected from acetophenones, benzophenones, ketals, disulfide compounds, fluoramine compounds, and the like.
Specific examples thereof include 1-hydroxy-cyclohexylphenol-ketone, 2-methyl-1- [4- (methylthio) phenyl] -2- morpholinopropane- 2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) 2-methylpropan-1-one, benzophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy- 2-ethylanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-methylthioxanthone, 4-dimethylthioxanthone, 2,4-diethylthioxanthone, and the like. These initiators may be used alone or in combination of two or more. The UV-curable coating composition is preferably used in an amount of 0.5 to 10 parts by weight per 100 parts by weight of the photoreactive initiator.
The polydimethylsiloxane compound having an acrylate group is included in the composition to improve abrasion resistance. The polydimethylsiloxane basic skeleton structure includes an acrylate group, and the acrylate group may include four .
The polydimethylsiloxane compound containing the acrylate group is included in the ultraviolet curable coating composition in the form of a central additive. The core composition of the ultraviolet curable coating liquid is coated on the substrate to impart abrasion resistance, hardness, strength, abrasion resistance and scratch resistance It will play a role of increasing the enemy. Particularly, the polydimethylsiloxane compound having an acrylate group is preferably a polydimethylsiloxane having a central structure and having an acrylate group attached thereto in a number of 1 to 4 in the molecular structure, more preferably two.
The polydimethylsiloxane compound containing the acrylate group may be represented by the following structural formula.
- [Structural Formula 2]
In the polydimethylsiloxane compounds represented by Structural Formula 1, Structural Formula 2 and Structural Formula 3, Y, Z or Z 'represents a methyl group (-CH 3 ), a phenyl group (-C 6 H 5 ), a hydrogen group (-H) And a methyl group (-CF 3 ).
If the amount of the polydimethylsiloxane compound containing an acrylate group is less than 0.2 part by weight based on the content of the ultraviolet curable coating composition excluding the solvent, the characteristics can not be sufficiently expressed. If the amount is more than 5 parts by weight, It is possible to cause a problem such as a decrease in strength. Therefore, it is more preferable to use the polydimethylsiloxane compound containing an acrylate group in the range of 0.2 to 5 parts by weight and the range of 0.2 to 2 parts by weight in the ultraviolet curable coating composition.
In one embodiment, the ultraviolet curable coating composition may contain 0.01 to 2 parts by weight of an additive for imparting antifoaming property and improving the processability.
Further, the ultraviolet curable coating composition may be used by mixing at least one organic solvent to improve the viscosity and the coating composition of the composition.
Examples of the organic solvent include alcohols such as methanol, ethanol, and isopropanol, and methyl ethyl ketone, methyl isobutyl ketone, xylene, toluene, acetate, etc., but not always limited thereto, have.
The ultraviolet curable coating composition according to another embodiment comprises 10 to 70 parts by weight of a urethane acrylate oligomer, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, 0.5 to 10 parts by weight of a photoreactive initiator, 1 to 40 parts by weight of an acrylate group and 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
The compound containing the inorganic particles is a functional material for adjusting the hardness of the transparent coating film formed by the UV curable coating composition, adjusting the refractive index and adjusting the shrinkage ratio, and can be selected within the range of about 1 to 60 parts by weight, Preferably in the range of about 1 to 40 parts by weight.
Examples of the inorganic particles included in the inorganic particle-containing compound include titanium dioxide, silicon dioxide, indium oxide, tin oxide, aluminum oxide, zinc sulfide, etc., which are present as colloidal particles in an organic solvent. The compound containing the inorganic particles may be obtained by introducing a chemical bond to the inorganic particles to introduce a urethane group, an acrylate group, a silanol group, or the like on the molecular structure. It is preferable to use those inorganic particles that do not aggregate in spherical shape of 10 to 300 nm.
In another embodiment, the compound containing the inorganic particles may be a compound having an organic-inorganic component in the form of a polymer, which is not in the form of particles, using a sol-gel reaction. Lt; RTI ID = 0.0 > C, < / RTI >
Specific examples of the urethane acrylate oligomer, the monofunctional and polyfunctional acrylate monomer, the photoreactive initiator, the polydimethylsiloxane compound containing an acrylate group, the organic solvent, etc., which are applied for preparing the ultraviolet curable coating composition, .
Transparency Coating film And method for forming the same
In order to manufacture a transparent coating film for protecting the surface of the transparent plastic material for optical devices according to an embodiment of the present invention, an ultraviolet curable coating composition is prepared (S110).
The curable coating composition according to the first embodiment used in the step S110 comprises 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, And 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
The curable coating composition according to the second embodiment comprises 10 to 70 parts by weight of a urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer, 0.5 to 10 parts by weight of a photoreactive initiator, And 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
Subsequently, the ultraviolet curable coating composition is coated on the object (S120).
In step S120, the target object may include a plastic material or a plastic film used in an image display apparatus. In addition, when coating the composition on the object, the ultraviolet curable coating composition of one embodiment or the ultraviolet curable coating composition of the second embodiment may be selected and used.
Subsequently, a transparent coating film for protecting the object is formed on the object by performing an ultraviolet curing process (S130).
The transparent coating film formed by the above-described method has a thickness of 0.1 to 100 mu m, preferably 5 to 50 mu m. The transparent coating film thus formed can be formed on a transparent plastic material for optical or plastic film to greatly improve the abrasion resistance and scratch resistance of the transparent plastic material for optical use.
Hereinafter, the present invention will be described in more detail with reference to specific examples and comparative examples. It is to be understood by those skilled in the art that these examples are for illustrative purposes only and that the scope of the present invention is not limited by these examples without departing from the gist of the present invention.
Example 1)
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, , 4 parts by weight of hydroxyimethylacetophenone as a photoinitiator, 0.5 part by weight of a polydimethylpolysiloxane compound having a diacrylate group represented by the structural formula 1, and 0.5 part by weight of a defoaming agent for removing air bubbles were mixed to prepare an ultraviolet curable coating liquid composition.
Example 2)
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, 4 parts by weight of hydroxydimethylacetophenone as a photoinitiator, 0.5 parts by weight of a polydimethylpolysiloxane compound having a monoacrylate group of the structural formula 2, and 0.5 parts by weight of a defoamer for removing bubbles were mixed to prepare an ultraviolet curable coating liquid composition.
Example 3)
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, , 4 parts by weight of hydroxydimethylacetophenone as a photoinitiator, 0.5 parts by weight of a polydimethylpolysiloxane compound having a monoacrylate group represented by the structural formula 3, and 0.5 parts by weight of a defoamer for removing bubbles were mixed to prepare an ultraviolet curable coating liquid composition.
Comparative Example 1)
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, , 4 parts by weight of hydroxy dimethyl acetophenone as a photoinitiator, and 0.5 part by weight of a defoaming agent for removing bubbles were mixed to prepare an ultraviolet curable coating liquid composition.
Comparative Example 2
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, , 4 parts by weight of hydroxydimethylacetophenone as a photoinitiator, 0.1 part by weight of a polydimethylpolysiloxane compound having a diacrylate group of the structural formula 1, and 0.5 part by weight of a defoamer for removing air bubbles were mixed to prepare a UV curable coating liquid composition.
Comparative Example 3
40 parts by weight of a polyfunctional urethane acrylate oligomer having a weight average molecular weight of less than 10,000, 5 parts by weight of isobornyl acrylate, 10 parts by weight of 1,6-hexadiol diacrylate, 20 parts by weight of pentaerythritol tetraacrylate, , 4 parts by weight of hydroxy dimethyl acetophenone as a photoinitiator, 0.5 part by weight of a silicone compound having a diacrylate group, and 0.5 part by weight of a defoaming agent for removing bubbles were mixed to prepare an ultraviolet curable coating liquid composition.
Evaluation of physical properties of ultraviolet curable coating liquid composition
The ultraviolet curable coating liquid compositions prepared in Examples 1 to 3 and Comparative Examples 1 to 3 were coated on polycarbonate (PC) substrates having a thickness of 680 탆 with bar bars 12, respectively, and ultraviolet curing with a light quantity of 350 mJ After that, specimens having a transparent coating layer having a thickness of 20 mu m were prepared. Then, the abrasion resistance test of the prepared specimens was carried out as follows.
Vibration abrasion test
A vibration abrasion tester, which is one of the methods for abrasion test, was used. A specimen was put into a tank of a certain size containing a mixture of two different medias and a compound, and vibration was applied to the surface of the specimen for a certain period of time. .
Light intensity measurement (ΔE)
The brightness, reflectance, chromaticity coordinates, and illuminance changes were measured using the CM-2600d manufactured by Minolta Co., Ltd., by measuring the optical characteristics of the specimen before and after the vibration abrasion test and the specimen after the test, and the results are shown in Table 1 Respectively.
Table 1) Change of ΔE
In addition, it was confirmed from the results of vibration abrasion test for 20 minutes that Example 1 and Example 2 had better abrasion resistance than the other specimens. Therefore, it was confirmed that when the proper amount of the polydimethylpolysiloxane compound having an acrylate group is used, the abrasion resistance of the transparent coating film is increased.
Claims (13)
20 to 80 parts by weight of a monofunctional and polyfunctional acrylate monomer;
0.5 to 10 parts by weight of a photoreactive initiator;
1 to 40 parts by weight of at least one inorganic particle selected from titanium dioxide, silicon dioxide, indium oxide, tin oxide, aluminum oxide and zinc sulfide; And
And 0.2 to 5 parts by weight of a polydimethylsiloxane compound containing an acrylate group.
(-CH 3 ), a phenyl group (-C 6 H 5 ), a hydrogen group (-H) and a trifluoromethyl group (-CF 3 ) in the structural formula 1, the structural formula 2 and the structural formula 3, , X is an integer of 1 or more, and n is an integer of 1 to 3.)
Coating the ultraviolet curable coating composition on a subject; And
And performing a UV curing process to form a transparent coating film on the object.
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