KR20150135293A - Uv-curing light-blocking composition - Google Patents
Uv-curing light-blocking composition Download PDFInfo
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- KR20150135293A KR20150135293A KR1020157026238A KR20157026238A KR20150135293A KR 20150135293 A KR20150135293 A KR 20150135293A KR 1020157026238 A KR1020157026238 A KR 1020157026238A KR 20157026238 A KR20157026238 A KR 20157026238A KR 20150135293 A KR20150135293 A KR 20150135293A
- Authority
- KR
- South Korea
- Prior art keywords
- ultraviolet
- light
- curable
- shielding
- composition
- Prior art date
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- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/064—Polymers containing more than one epoxy group per molecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
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- G—PHYSICS
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- G02B5/00—Optical elements other than lenses
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2289—Oxides; Hydroxides of metals of cobalt
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2293—Oxides; Hydroxides of metals of nickel
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Abstract
본 발명은, 자외선 경화성이며, 막 두께가 두껍고, 충분히 경화된 차광성 경화물을 형성할 수 있는 자외선 경화성 차광용 조성물을 제공하는 것을 목적으로 한다. 본 발명은, 자외선 경화성 화합물과, 산화니켈 및 산화코발트를 포함하는 유리 충전재를 포함하는 자외선 경화성 차광용 조성물이다.An object of the present invention is to provide an ultraviolet curable light-shielding composition capable of forming a light-shielding cured product which is ultraviolet curable and has a large film thickness and is sufficiently cured. The present invention is a composition for shielding ultraviolet curable light comprising a ultraviolet ray curable compound and a glass filler containing nickel oxide and cobalt oxide.
Description
본 발명은, 가시광을 유효하게 차폐하고, 그리고 자외선 경화성이 우수한 차광용 조성물에 관한 것이다.The present invention relates to a light-shielding composition effectively shielding visible light and having excellent ultraviolet curing properties.
반도체 장치, 표시 장치, 전자 광학 기기, 발광 장치, 포장 재료, 카메라 등의 광학 렌즈, 그 밖의 각양각색의 각종 용도에 있어서 차광성 재료가 널리 사용되고 있다. 예를 들어 특허문헌 1에는, 특정한 금속 산화물 조성을 갖는 내열성이 우수한 자외선 투과 열선 흡수 유리를, 수지 경화용 자외선 조사 장치의 유리 필터로서 사용하는 것이 개시되어 있다.Light-shielding materials are widely used in various applications such as semiconductor devices, display devices, electro-optical devices, light emitting devices, packaging materials, optical lenses such as cameras, and various other applications. For example, Patent Document 1 discloses the use of an ultraviolet ray-transmitting heat ray absorbing glass having a specific metal oxide composition and excellent heat resistance as a glass filter of an ultraviolet ray irradiator for resin curing.
또한, 각종 수지는 그의 특성에 따라 성형, 경화, 접착 등의 각종 가공을 실시할 수 있으며, 또한 각종 기능 성분을 배합함으로써 그의 기능을 수지에 부여할 수 있기 때문에, 상기 차광성 재료로서, 차광성을 갖는 물질을 수지에 배합함으로써 당해 수지에 차광 기능을 부여한 차광성 수지 조성물이 널리 사용되고 있다. 또한, 어떠한 파장의 광에 대한 차광성이 요구되는지는 용도에 따라 상이하다.In addition, various resins can be subjected to various processes such as molding, curing, and adhesion according to their properties, and their functions can be imparted to the resin by compounding various functional components. Therefore, as the light-shielding material, A light-shielding resin composition to which a light-shielding function is imparted to the resin is widely used. Also, the light shielding property for light of a certain wavelength is required depending on the use.
그 중에서도, 표시 장치 관련의 차광성 재료, 광학 렌즈용 차광성 재료, 컬러 필터용 블랙 매트릭스 및 렌즈 시트용 블랙 스트라이프 등과 같은 가시광선에 대한 차광성이 요구되는 차광성 재료에 대해서는, 종래 카본 블랙이나 아세틸렌 블랙, 콜타르, 또는 흑색 색소 전구체 등을 각종 수지에 배합한 것이 개발되어 오고 있다(예를 들어 특허문헌 2 및 3). Among these, a light-shielding material requiring shielding against visible light, such as a light-shielding material relating to a display device, a light-shielding material for an optical lens, a black matrix for a color filter and a black stripe for a lens sheet, Acetylene black, coal tar, black pigment precursors, and the like have been developed in various resins (for example, Patent Documents 2 and 3).
그러나, 이들의 자외선 경화성 수지에 각종 흑색 색소를 혼합한 차광성 수지 조성물은 자외선까지 흡수하여 버리기 때문에, 자외선을 조사하여도 수지 조성물의 심부까지 경화시킬 수 없으며, 막 두께가 두꺼워 차광성인, 충분히 경화된 경화물을 얻을 수 없었다. 그 때문에 상기와 같은 수지 조성물에 대해서는 실용도가 확대되지 않았다.However, since the light-shielding resin composition obtained by mixing various black pigments with these ultraviolet ray-curable resins absorbs ultraviolet rays, even if irradiated with ultraviolet rays, it can not be hardened to the core of the resin composition. The resulting cured product could not be obtained. Therefore, the practical use of the resin composition as described above has not been increased.
이러한 문제점에 관하여 본원 출원인은, 광경화성 수지 100중량부, 및 해당 광경화성 수지의 경화물의 굴절률과의 굴절률의 차가 0.1 이상이 되는 굴절률을 갖고, 해당 광경화성 수지에 대하여 비상용성이며 분산성을 갖는 화합물 입자 1 내지 20중량부를 포함하고, 흑색 안료를 포함하지 않는 광경화성 차광 수지 조성물이며, 해당 화합물 입자의 입경이 0.1 내지 100㎛이며, 0.5㎛의 막 두께에 있어서, 광경화성 차광 수지 조성물의 경화물이 1％ 이하인, 300 내지 800nm에 있어서의 광투과율을 갖는 광경화성 차광 수지 조성물을 개발하여, 특허를 취득하였다(특허문헌 4). 상기 화합물이란, 특정한 금속 산화물이나 특정한 수지이다.In view of such a problem, the applicant of the present invention has found that a resin composition which has a refractive index such that the difference in refractive index between the photo-curing resin and the refractive index of the cured product of the photo-curing resin is 0.1 or more, 1 to 20 parts by weight of a compound particle and not containing a black pigment, wherein the compound particle has a particle size of 0.1 to 100 탆 and a film thickness of 0.5 탆, wherein the light-curable light- A light-curable light-shielding resin composition having a light transmittance of 300 to 800 nm and having a cargo of 1% or less was developed and patented (Patent Document 4). The compound is a specific metal oxide or a specific resin.
본 발명은, 특허문헌 4에 기재된 발명과는 상이한 구성에 의해, 자외선 경화성이며, 막 두께가 두껍고, 충분히 경화된 차광성 경화물을 형성할 수 있는 자외선 경화성 차광용 조성물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide an ultraviolet-curable light-shielding composition capable of forming a light-shielding cured product which is ultraviolet curable and has a large thickness and is sufficiently cured by a constitution different from the invention described in Patent Document 4 .
예를 들어 디스플레이 등의 표시 장치나 광학 렌즈 등의 광학 기기 부재에 있어서 사용되는, 가시광선에 대한 차광성이 요구되는 차광성 재료에 대해서는, 기본적으로 눈으로 감지할 수 있는 가시광만 차단할 수 있으면 되고, 자외선에 관한 차광성의 유무는 대부분의 경우 문제가 되지 않는다.For a light-shielding material, which is used, for example, in a display device such as a display or an optical device such as an optical lens, and which requires shielding property against visible light, basically, only visible light which can be detected by eyes can be blocked , The presence or absence of light shielding against ultraviolet rays is not a problem in most cases.
따라서 본 발명자는, 상기와 같이 가시광은 흡수하여 차단하지만, 자외선은 투과하는 특성을 상기 재료에 부여함으로써 상기 과제를 해결할 수 있을 것이라는 발상하에, 그러한 특성을 갖는 특정한 유리 충전재를 사용함으로써, 막 두께가 두껍고, 충분히 경화된 차광성 경화물을 형성할 수 있는 자외선 경화성 차광용 조성물이 얻어지는 것을 발견하여, 본 발명을 완성하기에 이르렀다.Therefore, the inventor of the present invention has found that by using a specific glass filler having such characteristics under the idea that the visible light is absorbed and blocked as described above, but the above-mentioned problem can be solved by imparting a property of transmitting ultraviolet rays to the material, It has been found that an ultraviolet-curable light-shielding composition capable of forming a thick, sufficiently cured light-blocking cured product can be obtained, and the present invention has been accomplished.
즉 본 발명의 요지는, 이하와 같다.That is, the gist of the present invention is as follows.
(1) 자외선 경화성 화합물과, 산화니켈 및 산화코발트를 포함하는 유리 충전재를 포함하는 자외선 경화성 차광용 조성물.(1) A composition for shielding ultraviolet light-curable light comprising a ultraviolet curable compound, and a glass filler comprising nickel oxide and cobalt oxide.
(2) 상기 자외선 경화성 차광용 조성물에 있어서의 유리 충전재의 함유량이 5 내지 95중량％인, 상기 (1)에 기재된 자외선 경화성 차광용 조성물.(2) The ultraviolet-curable light-shielding composition according to (1), wherein the content of the glass filler in the ultraviolet-curable light-shielding composition is 5 to 95% by weight.
(3) 광중합 개시제를 더 포함하는, 상기 (1) 또는 (2)에 기재된 자외선 경화성 차광용 조성물.(3) The ultraviolet-curable light-shielding composition according to the above (1) or (2), further comprising a photopolymerization initiator.
(4) 상기 자외선 경화성 화합물이 (메트)아크릴레이트 올리고머 및 (메트)아크릴레이트 단량체를 포함하는, 상기 (1) 내지 (3) 중 어느 하나에 기재된 자외선 경화성 차광용 조성물.(4) The ultraviolet-curable light-shielding composition according to any one of (1) to (3), wherein the ultraviolet-curing compound comprises a (meth) acrylate oligomer and a (meth) acrylate monomer.
(5) 상기 유리 충전재의 굴절률과, 상기 자외선 경화성 차광용 조성물로부터 고체 성분을 제거하여 얻어지는 자외선 경화성 조성물의 경화물의 굴절률의 차가 -0.03 내지 +0.03인, 상기 (3) 또는 (4)에 기재된 자외선 경화성 차광용 조성물.(5) The ultraviolet ray curing method according to the above (3) or (4), wherein the difference between the refractive index of the glass filler and the refractive index of the cured product of the ultraviolet curable composition obtained by removing the solid component from the ultraviolet curable light shielding composition is from -0.03 to +0.03. Curable light-shielding composition.
(6) 상기 광중합 개시제로서 자외광 개시제 및 가시광 개시제를 포함하고, 상기 가시광 개시제의 상기 자외선 경화성 차광용 조성물에 있어서의 함유량이 0.01 내지 0.15중량％인, 상기 (3) 내지 (5) 중 어느 하나에 기재된 자외선 경화성 차광용 조성물.(6) The photocurable composition according to any one of (3) to (5), wherein the photopolymerization initiator comprises an ultraviolet light initiator and a visible light initiator, and the content of the visible light initiator in the composition for ultraviolet- Wherein the ultraviolet-curable light-shielding composition is an ultraviolet curable light-shielding composition.
(7) 상기 유리 충전재 이외의 충전재를 포함하고, 상기 충전재의 굴절률과, 상기 자외선 경화성 차광용 조성물로부터 고체 성분을 제거하여 얻어지는 자외선 경화성 조성물의 경화물의 굴절률의 차의 절댓값이 0.06 이상이며, 상기 충전재의 상기 자외선 경화성 차광용 조성물에 있어서의 함유량이 0.5 내지 5중량％인, 상기 (3) 내지 (6) 중 어느 하나에 기재된 자외선 경화성 차광용 조성물.(7) a filler other than the glass filler, wherein the absolute value of the difference between the refractive index of the filler and the refractive index of the cured product of the ultraviolet curable composition obtained by removing the solid component from the ultraviolet curable light shielding composition is 0.06 or more, The composition for shielding ultraviolet-curing light-shielding according to any one of (3) to (6), wherein the content of the ultraviolet-curable light-shielding composition in the ultraviolet-curable light-shielding composition is 0.5 to 5% by weight.
(8) 상기 유리 충전재의 평균 입경이 0.5 내지 150㎛인, 상기 (1) 내지 (7) 중 어느 하나에 기재된 자외선 경화성 차광용 조성물.(8) The ultraviolet-curable light-shielding composition according to any one of (1) to (7), wherein the glass filler has an average particle diameter of 0.5 to 150 탆.
(9) 상기 (1) 내지 (8) 중 어느 하나에 기재된 자외선 경화성 차광용 조성물의 경화물.(9) A cured product of the ultraviolet-curable light-shielding composition according to any one of (1) to (8).
(10) 상기 (9)에 기재된 경화물을 갖는 광학 기기 부재.(10) An optical device member having the cured product described in (9) above.
본 발명에 따르면, 특허문헌 4에 기재된 발명과는 상이한 구성의, 자외선 경화성이며, 막 두께가 두껍고, 충분히 경화된 차광성 경화물을 형성할 수 있는 자외선 경화성 차광용 조성물이 제공된다.According to the present invention, there is provided an ultraviolet-curable light-shielding composition capable of forming a light-shielding cured product which is different from the invention described in Patent Document 4 and which is ultraviolet curable and has a large thickness and is sufficiently cured.
이하, 본 발명에 대하여 상세하게 설명한다.Hereinafter, the present invention will be described in detail.
[자외선 경화성 차광용 조성물] [UV-curable light-shielding composition]
<자외선 경화성 화합물> <UV Curable Compound>
본 발명의 자외선 경화성 차광용 조성물(이하 「본 발명의 조성물」이라고도 함)은 자외선 경화성 화합물을 포함하고 있으며, 자외선의 조사에 의해 경화시킬 수 있다. 또한 본 명세서에 있어서 자외선이란, 파장 250nm 이상 400nm 미만의 범위의 광을 가리킨다.The ultraviolet-curable light-shielding composition (hereinafter also referred to as " composition of the present invention ") of the present invention contains an ultraviolet-curable compound and can be cured by irradiation with ultraviolet rays. In the present specification, ultraviolet rays indicate light in a wavelength range of 250 nm or more and less than 400 nm.
상기 자외선 경화성 화합물로서는, 자외선의 조사에 의해 경화 반응(중합 반응, 가교 반응 등)을 일으키는 종래 공지된 화합물을 특별히 제한 없이 사용할 수 있으며, 그의 예로서는 (메트)아크릴레이트 올리고머, (메트)아크릴레이트 단량체, 에폭시 올리고머, 에폭시 단량체, 옥세탄 올리고머, 옥세탄 단량체 등을 들 수 있다. 또한, 본 명세서에 있어서 「(메트)아크릴레이트」란, 메타크릴레이트 또는 아크릴레이트를 의미하고, 「(메트)아크릴」란, 메타크릴 또는 아크릴을 의미하고, 「(메트)아크릴로일」이란, 메타크릴로일 또는 아크릴로일을 의미한다. 또한, 상기 자외선 경화성 화합물은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.As the ultraviolet ray curable compound, conventionally known compounds which cause a curing reaction (polymerization reaction, crosslinking reaction, etc.) by irradiation of ultraviolet rays can be used without particular limitation, and examples thereof include (meth) acrylate oligomer, (meth) acrylate monomer , Epoxy oligomers, epoxy monomers, oxetane oligomers, oxetane monomers and the like. In the present specification, the term "(meth) acrylate" means methacrylate or acrylate, "(meth) acryl" means methacryl or acryl, and "(meth) acryloyl" , Methacryloyl or acryloyl. The ultraviolet curable compounds may be used alone or in combination of two or more.
((메트)아크릴레이트 올리고머) ((Meth) acrylate oligomer)
상기 (메트)아크릴레이트 올리고머는 밀착성 등의 특성을 갖고, 당해 화합물로서는 종래 공지된 자외선 경화성인 것이 사용 가능하지만, 그의 예로서는 우레탄(메트)아크릴레이트 올리고머, 에폭시(메트)아크릴레이트 올리고머, 폴리에스테르(메트)아크릴레이트 및 폴리에테르(메트)아크릴레이트 올리고머를 들 수 있다.The (meth) acrylate oligomer has properties such as adhesion and the like, and conventionally known UV curable ones can be used. Examples thereof include urethane (meth) acrylate oligomer, epoxy (meth) acrylate oligomer, polyester (Meth) acrylate and polyether (meth) acrylate oligomer.
((메트)아크릴레이트 단량체) ((Meth) acrylate monomer)
상기 (메트)아크릴레이트 단량체에는, (메트)아크릴로일기를 갖지만 (메트)아크릴기는 포함하지 않는 화합물도 포함되는 것으로 한다. 또한 (메트)아크릴레이트 단량체는 본 발명의 조성물의 점도나 접착성, 경화성 등을 조정하는 것이며,The (meth) acrylate monomer includes a compound having a (meth) acryloyl group but not a (meth) acryl group. The (meth) acrylate monomer is used to adjust the viscosity, adhesion, curability and the like of the composition of the present invention,
그의 구체예로서는,As specific examples thereof,
메틸(메트)아크릴레이트, 에틸(메트)아크릴레이트, n-프로필(메트)아크릴레이트, n-부틸(메트)아크릴레이트, t-부틸(메트)아크릴레이트, 이소부틸(메트)아크릴레이트, 에틸헥실(메트)아크릴레이트, 이소데실(메트)아크릴레이트, n-헥실(메트)아크릴레이트, 스테아릴(메트)아크릴레이트, 라우릴(메트)아크릴레이트, 트리데실(메트)아크릴레이트, 에톡시에틸(메트)아크릴레이트, 메톡시에틸(메트)아크릴레이트, 글리시딜(메트)아크릴레이트, 부톡시에틸(메트)아크릴레이트, 2-히드록시에틸(메트)아크릴레이트, 2-히드록시프로필(메트)아크릴레이트, 2-메톡시에틸(메트)아크릴레이트, 2-에톡시에톡시에틸(메트)아크릴레이트, 디시클로펜테닐옥시에틸(메트)아크릴레이트, 페녹시벤질(메트)아크릴레이트, 메톡시디에틸렌글리콜(메트)아크릴레이트, 에톡시디에틸렌글리콜(메트)아크릴레이트, 메톡시디프로필렌글리콜(메트)아크릴레이트, 옥타플루오로펜틸(메트)아크릴레이트, N,N-디메틸아미노에틸(메트)아크릴레이트, N,N-디에틸아미노에틸(메트)아크릴레이트, 알릴(메트)아크릴레이트, 1,3-부탄디올(메트)아크릴레이트, 1,4-부탄디올(메트)아크릴레이트, (메트)아크릴로일모르폴린, 1,6-헥산디올(메트)아크릴레이트, 폴리에틸렌글리콜디(메트)아크릴레이트, 디에틸렌글리콜디(메트)아크릴레이트, 네오펜틸글리콜디(메트)아크릴레이트, 트리에틸렌글리콜디(메트)아크릴레이트, 트리프로필렌글리콜디(메트)아크릴레이트, 히드록시피발산에스테르, 네오펜틸글리콜디(메트)아크릴레이트, 트리메틸올프로판디(메트)아크릴레이트, 1,3-비스(히드록시에틸)-5,5-디메틸히단토인, 3-메틸펜탄디올(메트)아크릴레이트, α,ω-디아크릴비스디에틸렌글리콜프탈레이트, 트리메틸올프로판트리(메트)아크릴레이트, 펜타에리트리트(메트)아크릴레이트, 펜타에리트리트헥사(메트)아크릴레이트, 디펜타에리트리트모노히드록시펜타(메트)아크릴레이트, 펜타에리트리톨트리(메트)아크릴레이트, 펜타에리트리톨테트라(메트)아크릴레이트, 트리히드록시에틸이소시아누레이트의 트리(메트)아크릴레이트, 디펜타에리트리톨헥사(메트)아크릴레이트;(Meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, n-butyl (Meth) acrylate, isodecyl (meth) acrylate, n-hexyl (meth) acrylate, stearyl (meth) acrylate, lauryl Acrylates such as ethyl (meth) acrylate, methoxyethyl (meth) acrylate, glycidyl (meth) acrylate, butoxyethyl (meth) acrylate, 2- (Meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethoxyethyl (meth) acrylate, dicyclopentenyloxyethyl , Methoxydiethylene glycol (meth) acrylate, ethoxydiethyl (Meth) acrylate, methoxydipropylene glycol (meth) acrylate, octafluoropentyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, (Meth) acrylate, 1,6-hexanediol (meth) acrylate, allyl (meth) acrylate, Acrylate, diethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) (Meth) acrylate, 1,3-bis (hydroxyethyl) -5,5-dimethylhydantoin, 3-ethylhexyl acrylate, hydroxypivalic acid ester, neopentyl glycol di Methylpentanediol (meth) acrylate,?,? - dia (Meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol monohydroxypenta (meth) acrylate, pentaerythritol tri Tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate of pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, trihydroxy ethyl isocyanurate;
이들의 EO 및/또는 PO 부가물;Their EO and / or PO adducts;
α,ω-테트라알릴비스트리메틸올프로판테트라히드로프탈레이트, 2-히드록시에틸(메트)아크릴로일포스페이트, 트리메틸올프로판트리(메트)아크릴레이트, 에틸렌글리콜디(메트)아크릴레이트, 테트라에틸렌글리콜디(메트)아크릴레이트, 폴리에틸렌글리콜디(메트)아크릴레이트, 1,4-부탄디올디(메트)아크릴레이트, 1,6-헥산디올디(메트)아크릴레이트, 네오펜틸글리콜디(메트)아크릴레이트, 디(메트)아크릴옥시에틸포스페이트, N-비닐피롤리돈 및(meth) acrylate, trimethylol propane tri (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethylene glycol di (Meth) acrylate, polyethylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di Di (meth) acryloxyethyl phosphate, N-vinylpyrrolidone, and
이들의 광반응성 관능기를 갖는 올리고머를 들 수 있다.And oligomers having these photoreactive functional groups.
(에폭시 올리고머) (Epoxy oligomer)
상기 에폭시 올리고머로서는, 예를 들어As the epoxy oligomer, for example,
비페놀, 비스페놀 A, 수소 첨가 비스페놀 A, 비스페놀 F, 비스페놀 AD, 비스페놀 S, 테트라메틸비스페놀 A, 테트라메틸비스페놀 F, 테트라클로로비스페놀 A, 테트라브로모비스페놀 A 등의 비스페놀류의 디글리시딜에테르류;The diglycidyl ether of bisphenols such as biphenol, bisphenol A, hydrogenated bisphenol A, bisphenol F, bisphenol AD, bisphenol S, tetramethyl bisphenol A, tetramethyl bisphenol F, tetrachlorobisphenol A and tetrabromobisphenol A Ryu;
페놀노볼락, 크레졸노볼락, 브롬화페놀노볼락, 오르토크레졸노볼락 등의 노볼락 수지의 폴리글리시딜에테르류;Polyglycidyl ethers of novolac resins such as phenol novolac, cresol novolak, brominated phenol novolac, and orthocresol novolak;
에틸렌글리콜, 폴리에틸렌글리콜, 폴리프로필렌글리콜, 부탄디올, 1,6-헥산디올, 네오펜틸글리콜, 트리메틸올프로판, 1,4-시클로헥산디메탄올, 비스페놀 A의 에틸렌옥시드 부가물, 비스페놀 A의 프로필렌옥시드 부가물 등의 알킬렌글리콜류의 디글리시딜에테르류;Ethylene glycol, ethylene glycol, polyethylene glycol, polypropylene glycol, butanediol, 1,6-hexanediol, neopentyl glycol, trimethylol propane, 1,4-cyclohexanedimethanol, ethylene oxide adduct of bisphenol A, Diglycidyl ethers of alkylene glycols such as a seed adduct;
헥사히드로프탈산의 글리시딜에스테르나 다이머산의 디글리시딜에스테르 등의 글리시딜에스테르류;Glycidyl esters such as glycidyl esters of hexahydrophthalic acid and diglycidyl esters of dimeric acid;
3,4-에폭시시클로헥실메틸-3',4'-에폭시시클로헥산카르복실레이트, 3,4-에폭시시클로헥실에틸-3',4'-에폭시시클로헥산카르복실레이트, 3,4-에폭시-6-메틸시클로헥실-3',4'-에폭시-6'-메틸시클로헥산카르복실레이트, 비닐시클로헥센디옥시드, 3,4-에폭시-4-메틸시클로헥실-2-프로필렌옥시드, 2-(3,4-에폭시시클로헥실-5,5-스피로-3,4-에폭시)시클로헥산-m-디옥산, 비스(3,4-에폭시시클로헥실)아디페이트, 비스(3,4-에폭시시클로헥실메틸)아디페이트, 락톤 변성 3,4-에폭시시클로헥실메틸-3',4'-에폭시시클로헥산카르복실레이트, 메틸렌비스(3,4-에폭시시클로헥산), 에틸렌비스(3,4-에폭시시클로헥산카르복실레이트), 디시클로펜타디엔디에폭시드, 비스(3,4-에폭시시클로헥실)에테르, 비스(3,4-에폭시시클로헥실메틸)에테르, 테트라(3,4-에폭시시클로헥실메틸)부탄테트라카르복실레이트, 비스(3,4-에폭시시클로헥실메틸)-4,5-에폭시테트라히드로프탈레이트, 비스(3,4-에폭시시클로헥실)디에틸실록산 등의 지환식 에폭시 화합물; 및Epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate, 3,4-epoxycyclohexylethyl-3', 4'-epoxycyclohexanecarboxylate, 3,4- 6-methylcyclohexanecarboxylate, vinylcyclohexene dioxide, 3,4-epoxy-4-methylcyclohexyl-2-propylene oxide, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-m-dioxane, bis (3,4-epoxycyclohexyl) adipate, bis Epoxycyclohexylmethyl-3 ', 4'-epoxycyclohexanecarboxylate, methylenebis (3,4-epoxycyclohexane), ethylenebis (3,4-epoxy (3,4-epoxycyclohexylmethyl) ether, tetra (3,4-epoxycyclohexylmethyl) ether, bis (3,4-epoxycyclohexylmethyl) Butanetetracar Alicyclic epoxy compounds such as bis (3,4-epoxycyclohexylmethyl) -4,5-epoxy tetrahydrophthalate and bis (3,4-epoxycyclohexyl) diethylsiloxane; And
이들 광반응성 관능기를 갖는 올리고머를 예시할 수 있다.And oligomers having these photoreactive functional groups can be exemplified.
(에폭시 단량체) (Epoxy monomer)
상기 에폭시 단량체로서는, 예를 들어 알릴글리시딜에테르, 2-에틸헥실글리시딜에테르, 페닐글리시딜에테르, p-t-부틸페닐글리시딜에테르 및 디브로모페닐글리시딜에테르를 들 수 있다.Examples of the epoxy monomer include allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, pt-butylphenyl glycidyl ether and dibromophenyl glycidyl ether .
(옥세탄 올리고머) (Oxetane oligomer)
상기 옥세탄 올리고머로서는, 예를 들어 옥세타닐기를 갖는 실세스퀴옥산 유도체 등을 들 수 있다.Examples of the oxetane oligomer include silsesquioxane derivatives having an oxetanyl group and the like.
(옥세탄 단량체) (Oxetane monomer)
상기 옥세탄 단량체로서는, 예를 들어 1,4-비스{[(3-에틸-3-옥세타닐)메톡시]메틸}벤젠, 3-에틸-3-{[3-에틸옥세탄-3-일]메톡시}메틸}옥세탄, 3-에틸헥실옥세탄, 3-에틸-3-히드록시옥세탄, 3-에틸-3-히드록시메틸옥세탄, 3-에틸-3-히드록시에틸옥세탄, 4,4'-비스((3-에틸-3-옥세타닐)메톡시메틸)비페닐 및 (3-에틸-3-옥세타닐)메톡시메틸(메트)아크릴레이트를 들 수 있다.Examples of the oxetane monomer include 1,4-bis {[(3-ethyl-3-oxetanyl) methoxy] methyl} benzene, 3- Ethyl-3-hydroxymethyloxetane, 3-ethyl-3-hydroxyoxymethyloxetane, 3-ethylhexyloxycetane, Cetane, 4,4'-bis ((3-ethyl-3-oxetanyl) methoxymethyl) biphenyl and (3-ethyl-3-oxetanyl) methoxymethyl (meth) acrylate .
이상 설명한, 본 발명의 조성물의 구성 성분인 자외선 경화성 화합물로서는, 피착체와의 접착성 등의 관점에서 (메트)아크릴레이트 올리고머 및 (메트)아크릴레이트 단량체가 바람직하다.As the ultraviolet ray curable compound which is the constituent component of the composition of the present invention described above, (meth) acrylate oligomer and (meth) acrylate monomer are preferable from the viewpoint of adhesion with an adherend.
(자외선 경화성 화합물의 함유량) (Content of ultraviolet ray curable compound)
본 발명의 자외선 경화성 차광용 조성물(100중량％ 중)에 있어서의 자외선 경화성 화합물의 함유량은, 조성물이 충분히 경화되고, 또한 유리 충전재가 그의 기능을 충분히 발휘할 수 있는 만큼의 양을 함유시키는 관점에서 통상 10 내지 99.9중량％, 바람직하게는 20 내지 80중량％, 더욱 바람직하게는 20 내지 70중량％이다.The content of the ultraviolet-curable compound in the ultraviolet-curable light-shielding composition (in 100% by weight) of the present invention is generally from the viewpoint of containing the sufficient amount that the composition is sufficiently cured and the glass filler sufficiently exhibits its function 10 to 99.9% by weight, preferably 20 to 80% by weight, more preferably 20 to 70% by weight.
<유리 충전재> <Glass filler>
본 발명의 자외선 경화성 차광용 조성물은, 산화니켈 및 산화코발트를 포함하는 유리 충전재를 포함하고 있다. 이것은 가시광선을 흡수하고 자외선을 투과하는 특성을 갖고 있다. 이러한 유리 충전재를 포함함으로써, 본 발명의 조성물에 자외선을 조사하면, 그것이 조성물 중의 성분에 의해 흡수되는 것이 일어나기 어려워, 조성물의 경화 반응에 효과적으로 이용된다. 동시에 상기 유리 충전재는 가시광선을 흡수하는 기능을 갖고 있기 때문에, 본 발명의 조성물은 충분한 막 두께에서의 충분한 경화와, 경화물에 있어서의 높은 가시광선 차광성을 양립할 수 있다. 산화니켈 및 산화코발트를 유리 충전재의 형태로 하지 않고, 양자를 단순히 조성물에 첨가한 것만으로는, 이러한 효과는 얻어지지 않는다.The ultraviolet curable light-shielding composition of the present invention comprises a glass filler comprising nickel oxide and cobalt oxide. It absorbs visible light and transmits ultraviolet light. By including such a glass filler, irradiation of ultraviolet rays to the composition of the present invention hardly causes absorption by the components in the composition, and is effectively used for the curing reaction of the composition. At the same time, since the glass filler has a function of absorbing visible light, the composition of the present invention can achieve both sufficient curing at a sufficient film thickness and high visible light shielding property at a cured product. This effect can not be obtained simply by adding nickel oxide and cobalt oxide to the composition without forming them in the form of a glass filler.
상기 유리 충전재에 포함되는 산화코발트로서는, CoO 및 Co2O3 모두 사용 가능하고, 그들의 혼합물인 Co3O4도 사용할 수 있다.As the cobalt oxide contained in the glass filler, both CoO and Co 2 O 3 can be used, and Co 3 O 4, which is a mixture thereof, can also be used.
상기 유리 충전재에 있어서의 산화코발트의 구성 비율은, 가시광선의 흡수 능 및 자외선의 투과능의 관점에서 바람직하게는 1 내지 20중량％이고, 보다 바람직하게는 3 내지 15중량％이다. 산화니켈에 대해서도 마찬가지의 관점에서, 상기 유리 충전재에 있어서의 그의 구성 비율은 바람직하게는 0.1 내지 5중량％이고, 보다 바람직하게는 0.3 내지 3중량％이다.The constituent ratio of cobalt oxide in the glass filler is preferably 1 to 20% by weight, more preferably 3 to 15% by weight in view of the absorptivity of visible ray and the transmittance of ultraviolet rays. From the same viewpoint, nickel oxide is preferably 0.1 to 5% by weight, more preferably 0.3 to 3% by weight in the glass filler.
보다 심부까지 경화시키는 관점에서, 상기 유리 충전재와 자외선 경화성 화합물의 굴절률은 동등한 것이 바람직하다. 산화니켈 및 산화코발트 및 그 밖의 유리 충전재의 구성 성분(예를 들어, 이산화규소, 산화알루미늄, 산화붕소, 산화나트륨, 산화리튬, 산화바륨, 산화칼슘, 산화안티몬)을 조정함으로써, 굴절률을 적절히 조정할 수 있다. 그 밖에 필요로 되는 특성에 따라 적절히 유리 충전재의 구성 성분을 조정함으로써, 상기 유리 충전재에 당해 특성을 부여할 수 있다.From the viewpoint of curing to the deep portion, it is preferable that the refractive indices of the glass filler and the ultraviolet curing compound are equal. It is possible to appropriately adjust the refractive index by adjusting the components (e.g., silicon dioxide, aluminum oxide, boron oxide, sodium oxide, lithium oxide, barium oxide, calcium oxide and antimony oxide) of nickel oxide and cobalt oxide and other glass fillers . By appropriately adjusting the constituent components of the glass filler according to other necessary characteristics, the glass filler can be given such properties.
또한, 심부 경화성의 관점에서, 상기 유리 충전재와 베이스 수지 경화물의 굴절률 차(유리 충전재의 굴절률-베이스 수지 경화물의 굴절률)는 -0.03 내지 +0.03인 것이 바람직하고, 0 내지 0.02인 것이 보다 바람직하다. 또한, 베이스 수지 경화물이란, 본 발명의 조성물을 구성하는 각 성분 중, 베이스가 되는 경화 성분, 즉 본 발명의 조성물로부터 유리 충전재 등의 고체 성분을 제거한, 자외선 경화성 화합물 및 후술하는 광중합 개시제 등을 포함하는 자외선 경화성 조성물을 경화시켜 얻어진 경화물을 가리킨다. 또한, 상기 고체 성분이란, 본 발명의 조성물에 있어서 고체 상태로 존재하는 물질이며, 단체(單體)에서는 고체이지만, 본 발명의 조성물 중에서는 예를 들어 자외선 경화성 화합물에 용해되어 존재하는 물질을 포함하지 않는다.Further, from the viewpoint of deep-part curability, the refractive index difference (the refractive index of the glass filler-the refractive index of the cured product of the base resin) of the glass filler and the base resin cured product is preferably -0.03 to +0.03, more preferably 0 to 0.02. The base resin cured product refers to a cured component that becomes a base among the respective components constituting the composition of the present invention, that is, an ultraviolet curable compound obtained by removing a solid component such as a glass filler from the composition of the present invention and a photopolymerization initiator Quot; refers to a cured product obtained by curing an ultraviolet-curing composition containing a curing agent. The solid component refers to a substance which exists in a solid state in the composition of the present invention and is solid in a single body but includes a substance which is dissolved in, for example, an ultraviolet curing compound in the composition of the present invention I never do that.
예를 들어 자외선 경화성 차광용 조성물의 구성 성분이 메타크릴레이트 올리고머 10중량부, 아크릴레이트 단량체 10중량부, 에폭시 올리고머 10중량부, 유리 충전재 30중량부, 광중합 개시제 2중량부인 경우에는, 베이스 수지 경화물이란, 메타크릴레이트 올리고머 10중량부, 아크릴레이트 단량체 10중량부, 에폭시 올리고머 10중량부, 광중합 개시제 2중량부를 포함하는 자외선 경화성 조성물의 경화물이다.For example, when 10 parts by weight of a methacrylate oligomer, 10 parts by weight of an acrylate monomer, 10 parts by weight of an epoxy oligomer, 30 parts by weight of a glass filler and 2 parts by weight of a photopolymerization initiator, The cargo is a cured product of an ultraviolet curable composition comprising 10 parts by weight of a methacrylate oligomer, 10 parts by weight of an acrylate monomer, 10 parts by weight of an epoxy oligomer, and 2 parts by weight of a photopolymerization initiator.
또한 상기 굴절률은, 파장 633nm의 광에 대한 굴절률로 하고, 그의 측정 방법은 이하와 같다. 베이스가 되는 경화 성분의 조성물을 0.5mm 두께가 되도록 PET 필름과 슬라이드 글라스에 끼워 넣고, 메탈 할라이드 램프(아이그라픽스제 ECS-301)로 6000mJ/cm2의 광을 조사하여 경화시키고, 경화막을 상기 PET 필름으로부터 박리하여 굴절률 시험편을 제작한다. 이 시험편의 파장 633nm의 광에 대한 굴절률을, 프리즘 커플러(메트리콘사제 MODEL2010)를 사용하여 측정한다.The refractive index is a refractive index with respect to light having a wavelength of 633 nm, and the measurement method thereof is as follows. The composition of the cured component serving as the base was sandwiched between a PET film and a slide glass so as to have a thickness of 0.5 mm and cured by irradiating light of 6000 mJ / cm 2 with a metal halide lamp (ECG-301 manufactured by Sigma-Aldrich) And peeled from the film to prepare a refractive index test piece. The refractive index of this test piece with respect to light having a wavelength of 633 nm is measured using a prism coupler (MODEL2010 manufactured by Metricon).
본 발명에 사용되는 유리 충전재의 평균 입경은, 당해 유리 충전재의 본 발명의 조성물 및 그의 경화물 중에 있어서의 양호한 분산성의 관점에서 0.5 내지 150㎛인 것이 바람직하다. 또한, 본 명세서에 있어서 평균 입경이란 메디안 직경(D50)이다.The average particle diameter of the glass filler used in the present invention is preferably 0.5 to 150 mu m from the viewpoint of good dispersion of the glass filler in the composition of the present invention and its cured product. In the present specification, the average particle diameter is the median diameter (D50).
상기 유리 충전재는 공지된 방법에 의해 제조 가능하고, 예를 들어 용융 급냉법, 기상 합성법 또는 졸-겔법 등의 일반적인 방법에 의해 각종 원료로부터 유리를 제조한 후, 이것을 분쇄 공정에 가하여, 필요에 따라 체로 입경을 가지런하게 하여, 분말상의 유리 충전재를 얻을 수 있다. 또한, 이들의 분쇄 공정에서의 분쇄의 정도를 조절함으로써, 얻어지는 유리 충전재의 평균 입경을 조절할 수 있다.The glass filler can be produced by a known method, for example, a glass is produced from various raw materials by a general method such as a melt quenching method, a vapor phase synthesis method, or a sol-gel method, and the glass is added to a grinding step, The glass filler in the form of a powder can be obtained by arranging the particles with a sieve. By controlling the degree of pulverization in the pulverizing step, the average particle diameter of the obtained glass filler can be controlled.
본 발명에 있어서, 이상 설명한 유리 충전재는 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다. 또한 본 발명의 조성물(100중량％ 중)에 있어서의 유리 충전재의 함유량은, 목적으로 하는 경화물의 막 두께나 유리 충전재 중의 산화니켈 및 산화코발트의 양 등에 따라 변동될 수 있지만, 충분한 가시광선의 차광 효과와 경화 성분의 충분한 경화 반응을 양립하는 관점에서, 바람직하게는 5 내지 95중량％, 보다 바람직하게는 10 내지 80중량％, 더욱 바람직하게는 10 내지 70중량％이다.In the present invention, the above-mentioned glass fillers may be used singly or in combination of two or more. The content of the glass filler in the composition (in 100 wt%) of the present invention may vary depending on the film thickness of the desired cured product, the amount of nickel oxide and cobalt oxide in the glass filler, etc. However, Is preferably 5 to 95% by weight, more preferably 10 to 80% by weight, and still more preferably 10 to 70% by weight, from the viewpoint of satisfactory curing reaction of the curing component.
<광중합 개시제> <Photopolymerization initiator>
본 발명의 자외선 경화성 차광용 조성물을 효과적으로 경화시키기 위해, 통상 본 발명의 조성물에 광중합 개시제를 배합한다.In order to effectively cure the UV-curable light-shielding composition of the present invention, a photopolymerization initiator is usually added to the composition of the present invention.
상기 광중합 개시제로서는, 종래 그의 용도에 사용되고 있는 화합물을 특별히 제한 없이 사용할 수 있으며, 그의 구체예로서는,As the photopolymerization initiator, a compound conventionally used for its use can be used without any particular limitation. As specific examples thereof,
벤조페논, 디아세틸, 벤질, 벤조인, ω-브로모아세토페논, 클로로아세톤, 아세토페논, 2,2-디에톡시아세토페논, 2,2-디메톡시-2-페닐아세톤, p-디메틸아미노아세토페논, p-디메틸아미노프로피오페논, 2-클로로벤조페논, p,ｐ'-비스디에틸아미노벤조페논, 미힐러 케톤, 벤조인메틸에테르, 벤조인이소부틸에테르, 벤조인-n-부틸에테르, 벤질디메틸케탈, 1-히드록시시클로헥실페닐케톤, 2-히드록시-2-메틸-1-온, 1-(4-이소프로필페닐)-2-히드록시-2-메틸프로판-1-온, 메틸벤조일포르메이트, 2,2-디에톡시아세토페논 및 4-N,N'-디메틸아세토페논류 등의 카르보닐기계 광중합 개시제; 디페닐디술피드 및 디벤질디술피드 등의 술피드계 광중합 개시제; 벤조퀴논 및 안트라퀴논 등의 퀴논계 광중합 개시제; 아조비스이소부티로니트릴 및 2,2'-아조비스프로판 등의 아조계 광중합 개시제 등의 자외광 개시제, 및Benzophenone, diacetyl, benzyl, benzoin, omega -bromoacetophenone, chloroacetone, acetophenone, 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetone, p- Phenol, p-dimethylaminopropiophenone, 2-chlorobenzophenone, p, p'-bisdiethylaminobenzophenone, Michler's ketone, benzoin methyl ether, benzoin isobutyl ether, benzoin- , Benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-one, 1- (4-isopropylphenyl) , Methyl benzoyl formate, 2,2-diethoxyacetophenone, and 4-N, N'-dimethyl acetophenone; A sulfide-based photopolymerization initiator such as diphenyl disulfide and dibenzyl disulfide; Quinone-based photopolymerization initiators such as benzoquinone and anthraquinone; An azo-based photopolymerization initiator such as azobisisobutylonitrile and 2,2'-azobispropane, and
2-벤질-2-디메틸아미노-1-(4-모르폴리노페닐)-부탄-1-온, 2-디메틸아미노-2-(4-메틸-벤질)-1-(4-모르폴리노페닐)-부탄-1-온, 비스(2,4,6-트리메틸벤조일)-페닐포스핀옥시드, 2,4,6-트리메틸벤조일-디페닐포스핀옥시드 등의 가시광 개시제를 들 수 있다.2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholinophenyl) ) -Butan-1-one, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide.
광중합 개시제의 사용량은, 자외선 경화성 화합물의 경화 반응을 효과적으로 행하는 관점에서, 통상 자외선 경화성 화합물 100중량부에 대하여 0.1 내지 10중량부, 바람직하게는 0.5 내지 5중량부이다.The amount of the photopolymerization initiator to be used is generally 0.1 to 10 parts by weight, preferably 0.5 to 5 parts by weight, based on 100 parts by weight of the ultraviolet-curing compound, from the viewpoint of effectively curing the ultraviolet-curing compound.
또한, 심부 경화성의 관점에서는, 본 발명의 자외선 경화성 차광용 조성물은, 자외광 개시제 및 가시광 개시제 양쪽을 포함하고, 상기 가시광 개시제의 자외선 경화성 차광용 조성물에 있어서의 함유량이 0.01 내지 0.15중량％인 것이 바람직하다.From the viewpoint of deep-part curability, the composition for light-shielding ultraviolet-curable light of the present invention comprises both an ultraviolet light initiator and a visible light initiator, and the content of the visible light initiator in the ultraviolet light- desirable.
<그 밖의 성분> ≪ Other components >
본 발명의 광경화성 차광용 조성물은, 목적에 따라 그 밖의 공지된 첨가제, 예를 들어 상기 유리 충전재 이외의 충전재, 산화 방지제, 광안정제, 실란 커플링제, 열중합 금지제, 레벨링제, 계면활성제, 착색제, 보존 안정제, 가소제, 활제, 용매, 노화 예방제, 습윤성 개량제, 이형제 등을 더 함유할 수 있다. 또한, 본 발명의 조성물은, 경화물의 가시광선의 광투과성을 저하시키기 위해, 유기·무기 착색 안료를 본 발명의 효과를 손상시키지 않는 범위에서(자외선 경화성 화합물 100중량부에 대하여, 예를 들어 수 중량부 이하, 특히 1중량부 이하) 첨가할 수 있다.The photo-curable light-shielding composition of the present invention may contain other known additives such as fillers other than the glass filler, antioxidants, light stabilizers, silane coupling agents, thermal polymerization inhibitors, leveling agents, A stabilizer, a plasticizer, a lubricant, a solvent, an antioxidant, a wettability improver, a release agent, and the like. In order to lower the light transmittance of the visible light ray of the cured product, the composition of the present invention may be added to the organic or inorganic colored pigment in an amount that does not impair the effect of the present invention (for example, Not more than 1 part by weight, especially not more than 1 part by weight).
특히 본 발명의 조성물은, 상기 유리 충전재 이외의 특정한 충전재를 0.5 내지 5중량％ 포함하는 것이, 상기 조성물의 심부 경화성에 끼치는 영향을 최소한으로 하면서 차광성을 높이는 관점에서 바람직하다. 그 충전재란, 상기 충전재의 굴절률과 베이스 수지 경화물의 굴절률의 차(충전재의 굴절률-베이스 수지 경화물의 굴절률)의 절댓값이 0.06 이상인 충전재이다. 상기 베이스 수지 경화물의 정의 및 그의 굴절률의 측정 방법은 상기에서 설명한 바와 같다.In particular, the composition of the present invention preferably contains 0.5 to 5% by weight of a specific filler other than the glass filler from the viewpoint of enhancing the light shielding property while minimizing the influence on the deep curing property of the composition. The filling material is a filler having a full value of a difference between the refractive index of the filler and the refractive index of the base resin cured product (the refractive index of the filler - the refractive index of the cured product of the base resin) of 0.06 or more. The definition of the base resin cured product and the method of measuring the refractive index thereof are as described above.
이러한 충전재로서는, 상기 베이스 수지 경화물과의 굴절률 차의 조건을 만족하는(그리고 0.5 내지 5중량％의 범위로 함유되는) 한, 공지된 각종 충전재가 사용 가능하며, 특별히 제한되지 않는다.As the filler, various known fillers may be used so long as the filler satisfies the condition of the refractive index difference with respect to the base resin cured product (and is contained in the range of 0.5 to 5 wt%), and is not particularly limited.
<자외선 경화성 차광용 조성물의 제조 방법> ≪ Method for producing UV-curable light-shielding composition >
본 발명의 자외선 경화성 차광용 조성물은, 이상 설명한 각 성분을 통상의 방법에 의해 혼합하여 제조할 수 있다. 각 성분의 첨가 순서는 특별히 한정되지 않는다.The ultraviolet-curable light-shielding composition of the present invention can be produced by mixing the components described above by conventional methods. The order of addition of each component is not particularly limited.
[자외선 경화성 차광용 조성물의 용도] [Use of UV-curable light-shielding composition]
본 발명의 자외선 경화성 차광용 조성물은, 자외선의 조사에 의해 효과적으로 경화된다. 특히 차광성 물질로서, 가시광선을 흡수하면서도 자외선을 투과하는 특정한 유리 충전재를 포함하고 있기 때문에, 조사한 자외선이 효과적으로 조성물의 경화에 사용되고, 경화를 위해 조사한 자외선이 조성물에 흡수되는 것이 일어나기 어렵다.The ultraviolet-curable light-shielding composition of the present invention is effectively cured by irradiation with ultraviolet rays. Particularly, as a light-shielding material, since it contains a specific glass filler that transmits ultraviolet rays while absorbing visible light, the irradiated ultraviolet rays are effectively used for curing the composition, and ultraviolet rays irradiated for curing are hardly absorbed by the composition.
그 때문에 본 발명의 조성물에 따르면, 넓은 범위의 막 두께, 예를 들어 0.5mm 이상(통상 10mm 이하) 범위의 막 두께의 경화물을 형성하는 것이 가능하다. 자외선 경화의 조건은, 조성물의 조성이나 목적으로 하는 막 두께 등에 따라 변화될 수 있지만, 예를 들어 자외선 경화성 화합물로서 우레탄아크릴레이트 올리고머 및 메타크릴레이트 단량체를 사용하고, 산화니켈 및 산화코발트를 포함하는 유리 충전재를 사용하고, 원하는 막 두께가 2mm인 경우, 자외선 조사량은 3000 내지 6000mJ/cm2이다.Therefore, according to the composition of the present invention, it is possible to form a cured product having a wide range of film thickness, for example, a film thickness in the range of 0.5 mm or more (usually 10 mm or less). The conditions of ultraviolet curing may vary depending on the composition of the composition and the intended film thickness. For example, it is possible to use a urethane acrylate oligomer and a methacrylate monomer as ultraviolet curable compounds, When a glass filler is used and the desired film thickness is 2 mm, the ultraviolet radiation dose is 3000 to 6000 mJ / cm 2 .
또한, 본 발명의 조성물이 광중합 개시제로서 가시광 개시제를 포함하고 있는 경우에는, 자외광 이외에 가시광도 조사함으로써, 보다 효과적으로 경화 반응을 일으키고, 보다 심부까지 경화시킬 수 있다.In addition, when the composition of the present invention contains a visible light initiator as a photopolymerization initiator, visible light is irradiated in addition to ultraviolet light to cause a curing reaction more effectively, and the cured portion can be further hardened.
본 발명의 조성물로부터 얻어진 경화물에 있어서는, 자외선 경화성 화합물이 중합 반응이나 가교 반응 등에 의해 경화되어 강고한 구조를 형성하고 있으며, 그의 경화체 중에 유리 충전재가 균일하게 분산되어 있는 것으로 생각되고, 이 유리 충전재에 의해 상기 경화물에 가시광선 차광 기능이 부여되어 있다.In the cured product obtained from the composition of the present invention, it is considered that the ultraviolet ray curable compound is cured by a polymerization reaction or a crosslinking reaction to form a strong structure and the glass filler is uniformly dispersed in the cured product thereof, The cured product is provided with a visible light shielding function.
그 때문에 상기 경화물은 가시광선의 차광성이 우수하고, 예를 들어 두께 0.5mm에서의 파장 500nm 광의 투과율이 통상 1％ 이하, 바람직하게는 0 내지 0.1％이다.For this reason, the cured product is excellent in the light shielding property of the visible light. For example, the transmittance of light having a wavelength of 500 nm at a thickness of 0.5 mm is usually 1% or less, preferably 0 to 0.1%.
이와 같이 넓은 범위의 막 두께가 실현 가능하며, 가시광선에 대하여 우수한 차광성을 갖는 경화물을 형성하는 점에서, 본 발명의 조성물의 경화물은 광범위한 용도, 예를 들어 광학 기기 부재에 있어서의 차광성 재료, 구체적으로는 표시 장치의 차광 밀봉제 등에 사용할 수 있다.The cured product of the composition of the present invention can be used in a wide range of applications, for example, in the case of an optical device member, in view of forming a cured product having such a wide range of film thickness and excellent light shielding property against visible light A light-shielding material for a display device, and the like.
실시예 Example
이하, 실시예 및 비교예에 의해 본 발명을 보다 상세하게 설명하지만, 본 발명은 이들에 의해 전혀 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited thereto at all.
<유리 충전재의 제조> ≪ Preparation of glass filler &
공지된 방법에 따라, 이하의 표 1에 나타내는 화학 조성의 각종 유리 충전재를 제조하였다. 또한, 유리 충전재 UVG-1C, UVG-6C, UVG-9C, UVG-10C 및 UVG-12C의 평균 입경(메디안 직경)은 모두 6.7㎛이다.Various glass fillers having the chemical compositions shown in Table 1 below were prepared according to known methods. The average particle diameters (median diameters) of the glass fillers UVG-1C, UVG-6C, UVG-9C, UVG-10C and UVG-12C were all 6.7 탆.
<심부 경화의 평가> ≪ Evaluation of deep hardening &
이하의 실시예 및 비교예에서 제조한 자외선 경화성 차광용 조성물의 심부 경화는, 이하와 같이 하여 평가하였다.The deep curing of the ultraviolet curable light shielding composition prepared in the following examples and comparative examples was evaluated as follows.
6mmφ 흑색 튜브에 제조한 조성물을 넣고, 상기 튜브 위로부터 고압 수은 램프(하마마쯔 호토니크스제 LC5)로 300mW/cm2의 자외선을 12초간 조사하였다(자외선 조사량: 3600mJ/cm2). 얻어진 경화물을 상기 튜브로부터 취출하여, 마이크로미터로 그의 두께를 측정하였다.The composition prepared in a 6 mm diameter black tube was placed and irradiated with ultraviolet rays of 300 mW / cm 2 for 12 seconds (ultraviolet ray irradiation amount: 3600 mJ / cm 2 ) from above the tube through a high pressure mercury lamp (LC5 manufactured by Hamamatsu Corporation). The obtained cured product was taken out from the tube and its thickness was measured with a micrometer.
<투과율의 평가> ≪ Evaluation of transmittance &
실시예 및 비교예에서 제조한 자외선 경화성 차광용 조성물의 경화물의 투과율은, 이하와 같이 하여 평가하였다.The transmittance of the cured product of the ultraviolet-curable light-shielding composition prepared in Examples and Comparative Examples was evaluated as follows.
조성물을 0.5mm 두께가 되도록 슬라이드 글라스에 끼워 넣고, 메탈 할라이드 램프(아이그라픽스제 ECS-301)로 6000mJ/cm2의 광을 조사하여 경화시켜, 투과율 시험편을 제작하였다. 이 시험편의 파장 500nm의 광에 대한 투과율을, 자외 가시 분광 광도계(닛본 분꼬우제 V-570)를 사용하여 측정하였다.The composition was sandwiched in a slide glass to a thickness of 0.5 mm and cured by irradiating light of 6000 mJ / cm 2 with a metal halide lamp (ECS-301, manufactured by Sigma-Aldrich) to prepare a transmittance test piece. The transmittance of the test piece to light having a wavelength of 500 nm was measured using an ultraviolet visible spectrophotometer (Nippon Bunko Co., Ltd. V-570).
<굴절률의 평가> <Evaluation of Refractive Index>
베이스 수지 경화물의 굴절률은, 이하와 같이 하여 평가하였다. 베이스가 되는 경화 성분의 조성물을 0.5mm 두께가 되도록 PET 필름과 슬라이드 글라스에 끼워 넣고, 메탈 할라이드 램프(아이그라픽스제 ECS-301)로 6000mJ/cm2의 광을 조사하여 경화시키고, 경화막을 상기 PET 필름으로부터 박리하여 굴절률 시험편을 제작하였다. 이 시험편의 파장 633nm의 광에 대한 굴절률을, 프리즘 커플러(메트리콘사제 MODEL2010)를 사용하여 측정하였다.The refractive index of the base resin cured product was evaluated as follows. The composition of the cured component serving as the base was sandwiched between a PET film and a slide glass so as to have a thickness of 0.5 mm and cured by irradiating light of 6000 mJ / cm 2 with a metal halide lamp (ECG-301 manufactured by Sigma-Aldrich) And peeled from the film to prepare a refractive index test piece. The refractive index of this test piece with respect to light having a wavelength of 633 nm was measured using a prism coupler (MODEL 2010 manufactured by Metricon).
[비교예 1 내지 4 및 실시예 1 내지 3] [Comparative Examples 1 to 4 and Examples 1 to 3]
이하의 표 2에 나타내는 조성으로 각종 성분을 혼합하여, 비교예 1 내지 4 및 실시예 1 내지 3의 자외선 경화성 차광용 조성물을 제조하였다. 이들 각각에 대하여, 심부 경화 및 투과율의 평가를 행하였다. 결과를 표 2에 함께 나타낸다.The compositions shown in the following Table 2 were mixed with various components to prepare the ultraviolet-curable light-shielding compositions of Comparative Examples 1 to 4 and Examples 1 to 3. Each of these was subjected to evaluation of deep curing and transmittance. The results are shown together in Table 2.
표 2로부터, 차광성 물질로서 청색 안료 및 카본 블랙을 배합한 비교예 1 및 2의 자외선 경화성 차광용 조성물로부터는, 막 두께가 두꺼운 경화물이 얻어지지 않는 것, From Table 2, it can be seen from the compositions for comparison of the ultraviolet-curable light shielding compositions of Comparative Examples 1 and 2 in which a blue pigment and carbon black as a light-shielding material are blended that a cured product having a thick film thickness can not be obtained,
산화니켈 및 산화코발트를 포함하는 유리 충전재를 배합한 실시예 1 내지 3의 자외선 경화성 차광용 조성물로부터는, 막 두께가 두꺼운 경화물이 얻어지고, 게다가 이 경화물은 비교예 1 및 2의 경화물과 동등 정도의 차광성을 달성하고 있는 것,The cured product having a thick film thickness was obtained from the ultraviolet curable light shielding compositions of Examples 1 to 3 in which a glass filler containing nickel oxide and cobalt oxide was blended. In addition, the cured product obtained in Comparative Examples 1 and 2 A light-shielding property equivalent to that of the light-
또한 산화니켈 및 산화코발트를 유리 충전재의 형태가 아니라, 단체로 양쪽을 배합한 비교예 3 및 4의 자외선 경화성 차광용 조성물에서는, 막 두께가 두꺼운 경화물이 얻어지지 않는 것을 알 수 있었다.It was also found that a cured product having a thick film thickness could not be obtained in the compositions for the ultraviolet-curable light shielding compositions of Comparative Examples 3 and 4 in which both nickel oxide and cobalt oxide were incorporated in the form of a glass filler.
[실시예 4 내지 21] [Examples 4 to 21]
이하의 표 3에 나타내는 조성으로 각종 성분을 혼합하여, 실시예 4 내지 21의 자외선 경화성 차광용 조성물을 제조하였다. 이들 각각에 대하여, 심부 경화, 투과율 및 베이스 수지 경화물의 굴절률의 평가를 행하였다. 결과를 표 3에 함께 나타내고, 또한 실시예 2의 데이터를 참고로 함께 나타낸다.Various components were mixed in the composition shown in the following Table 3 to prepare the ultraviolet curable light shielding compositions of Examples 4 to 21. For each of these, the deep cure, the transmittance and the refractive index of the cured base resin were evaluated. The results are shown together in Table 3 and the data of Example 2 are also referred to together.
실시예 4, 6 내지 21과 실시예 2 및 5를 비교하면, 유리 충전재와 베이스 수지 경화물의 굴절률 차를 -0.03 내지 +0.03으로 컨트롤하면, 심부 경화성을 높일 수 있는 것을 알 수 있었다.Comparing Examples 4, 6 to 21 and Examples 2 and 5, it was found that the depth curability can be improved by controlling the refractive index difference between the glass filler and the base resin cured product to -0.03 to +0.03.
실시예 11, 12, 15 내지 21과 실시예 10, 13 및 14를 비교하면, 본 발명의 조성물이 자외광 개시제 및 가시광 개시제를 포함하고, 또한 가시광 개시제의 상기 조성물에 있어서의 함유량을 0.01 내지 0.15중량％로 함으로써, 심부 경화성을 더욱 높일 수 있는 것을 알 수 있었다.Comparing Examples 11, 12, 15 to 21 and Examples 10, 13 and 14, it can be seen that the composition of the present invention contains an ultraviolet light initiator and a visible light initiator, and the content of the visible light initiator in the composition is 0.01 to 0.15 By weight%, it was found that deep portion curability can be further enhanced.
실시예 13 내지 15와 실시예 19 내지 21을 비교하면, 본 발명에 사용되는 유리 충전재 이외의 충전재이며, 베이스 수지 경화물과의 굴절률 차의 절댓값이 0.06 이상인 것을 함유량 0.5 내지 5중량％로 배합하면, 심부 경화성에 그다지 영향을 주지 않고, 차광성을 크게 높일 수 있는 것을 알 수 있었다.When Examples 13 to 15 and Examples 19 to 21 are compared, it is understood that when a filler other than the glass filler used in the present invention and having an absolute value of the difference in refractive index between the base resin cured product and the base resin cured product is 0.06 or more at a content of 0.5 to 5% , It can be seen that the shading property can be greatly increased without significantly affecting the deep curing property.
Claims (10)
상기 충전재의 굴절률과, 상기 자외선 경화성 차광용 조성물로부터 고체 성분을 제거하여 얻어지는 자외선 경화성 조성물의 경화물의 굴절률의 차의 절댓값이 0.06 이상이며,
상기 충전재의 상기 자외선 경화성 차광용 조성물에 있어서의 함유량이 0.5 내지 5중량％인 자외선 경화성 차광용 조성물.7. The optical element according to any one of claims 3 to 6, further comprising a filler other than the glass filler,
The absolute value of the difference between the refractive index of the filler and the refractive index of the cured product of the ultraviolet curable composition obtained by removing the solid component from the ultraviolet curable light shielding composition is 0.06 or more,
Wherein the content of the filler in the ultraviolet-curable light-shielding composition is 0.5 to 5% by weight.
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