JP2020114927A - 光硬化樹脂組成物およびその用途 - Google Patents
光硬化樹脂組成物およびその用途 Download PDFInfo
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- JP2020114927A JP2020114927A JP2020073400A JP2020073400A JP2020114927A JP 2020114927 A JP2020114927 A JP 2020114927A JP 2020073400 A JP2020073400 A JP 2020073400A JP 2020073400 A JP2020073400 A JP 2020073400A JP 2020114927 A JP2020114927 A JP 2020114927A
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- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 1
- MABAWBWRUSBLKQ-UHFFFAOYSA-N ethenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C=C MABAWBWRUSBLKQ-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- DYFMAHYLCRSUHA-UHFFFAOYSA-N ethenyl-tris(2-methylpropoxy)silane Chemical compound CC(C)CO[Si](OCC(C)C)(OCC(C)C)C=C DYFMAHYLCRSUHA-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- MDLRQEHNDJOFQN-UHFFFAOYSA-N methoxy(dimethyl)silicon Chemical compound CO[Si](C)C MDLRQEHNDJOFQN-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- UOMUPDCRXJLVGR-UHFFFAOYSA-N propane-1,2,2-triol Chemical compound CC(O)(O)CO UOMUPDCRXJLVGR-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08F290/068—Polysiloxanes
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—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 C09J159/00 - C09J187/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
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- C—CHEMISTRY; METALLURGY
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
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- C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
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- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C08L2205/00—Polymer mixtures characterised by other features
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- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
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- Adhesives Or Adhesive Processes (AREA)
- Liquid Crystal (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
Description
40%≦S60/S0<80%
実施例および比較例の光硬化樹脂組成物を離型処理されたフィルムの間に塗布した後、メタルハライドUVランプ(D−bulb)を利用して365nm波長の紫外線を200mW/cm2の強さおよび4000mJ/cm2の光量で照射して、硬化後の厚さが1mmとなるように硬化した。前記硬化物をカットして直径8mmおよび厚さ1mmの円形サンプルを製造した後、TA instruments社のARES−G2 Rheometerを利用して弾性モジュラス(G’)を測定した。
−測定温度:25℃
−測定変形(strain):5%
−測定モード:周波数掃引モード(frequency sweep mode)
実施例および比較例の光硬化樹脂組成物を離型処理されたフィルムの間に塗布した後、LEDランプを利用して395nm波長の光を100mW/cm2の強さおよび200mJ/cm2の光量で照射して、硬化後の厚さが1mmとなるように硬化した。前記硬化物をカットして直径8mmおよび厚さ1mmの円形サンプルを製造した後、TA instruments社のARES−G2 Rheometerを利用して弾性モジュラス(G’)を測定した。
−測定温度:25℃
−測定変形(strain):5%
−測定モード:周波数掃引モード
実施例および比較例の光硬化樹脂組成物に対してTA instruments社のARES−G2 Rheometerを利用して粘度を測定した。
−測定温度:25℃
−測定変形(strain):10%
−測定モード:周波数掃引モード
−測定セルの直径:8mm
実施例および比較例の光硬化樹脂組成物を離型処理されたフィルムの間に塗布した後、LEDランプを利用して395nm波長の光を100mW/cm2の強さおよび200mJ/cm2の光量で照射して、硬化後の厚さが1mmとなるように硬化した。前記硬化物をカットして直径8mmおよび厚さ1mmの円形サンプルを製造した後、TA instruments社のARES−G2 Rheometerを利用して、25℃で5%せん断変形を加えながら60秒間応力を測定した。応力緩和(=Elastic Portion、%)は、初期応力S0と比べて60秒後の応力S60の比率S60/S0(%)で計算される。
ソダライムガラス(1T、150mm×150mm)基板にディスペンサーを利用して実施例および比較例の光硬化樹脂組成物を塗布して幅2mmのダムを塗布した。LEDランプを利用して395nm波長の光を100mW/cm2の強さおよび200mJ/cm2の光量で照射して仮硬化した。仮硬化したダムの内側にダムと同じ光硬化樹脂組成物2gを塗布した後、ソダライムガラス(1T、150mm×150mm)基板を10Kgの圧力で合着した。合着性能の評価基準は、下記の通りである。
−○:ダムとフィルの境界面にバブルが発生せず、ダム形状および面積が維持される
−△:ダムとフィルの境界面にバブルが発生せず、ダム形状および面積の維持が十分でない
−×:合着時にダムの復元力によってダムとフィルの境界面にバブルが発生する
機器
温度計、撹拌器、水冷コンデンサ、窒素ガス
フラスコに化学式Aのポリジメチルシロキサンジオール(Silaplane FM−4411、チッソ社)350g、イソホロンジイソシアネート112g(イソシアネート基含有量37.8%)、ジブチルスズジラウレート1gを60℃で5時間反応させた。次に、ヒドロキシエチルアクリレート9.8gおよびラウリルアルコール15.6gを滴下し、そのまま反応を継続して、イソシアネート基が失われた時点で反応を終了した。
機器
温度計、撹拌器、水冷コンデンサ、窒素ガス
フラスコに化学式Aのポリジメチルシロキサンジオール(Silaplane FM−4411、チッソ社)350g、イソホロンジイソシアネート102.7g(イソシアネート基含有量37.8%)、ジブチルスズジラウレート1gを60℃で5時間反応させた。次に、ヒドロキシエチルアクリレート4.9g、ヒドロキシブチルアクリレート6.1gおよびラウリルアルコール7.4gを滴下し、そのまま反応を継続して、イソシアネート基が失われた時点で反応を終了した。
非反応性シリコーンオリゴマー(B1)として下記化学式Bのモノヒドロキシルポリシロキサン(FM−0411、チッソ社)を準備した。
機器
温度計、撹拌器、水冷コンデンサ、窒素ガス
フラスコに化学式Aのポリジメチルシロキサンジオール(Silaplane FM−4411、チッソ社)350g、イソホロンジイソシアネート124.4g(イソシアネート基含有量37.8%)、ジブチルスズジラウレート1gを60℃で5時間反応させた。次に、ラウリルアルコール52.2gを滴下し、そのまま反応を継続して、イソシアネート基が失われた時点で反応を終了した。
光硬化樹脂組成物の製造
反応性シリコーンオリゴマー(A)、非反応性シリコーンオリゴマー(B)、モノマー(C)およびその他添加剤(D)を下記表1の比率で配合して光硬化樹脂組成物を製造した。
20 第2光学部材
30 硬化物
40 スペーサー
Claims (19)
- 下記数式1の条件を満たす光硬化樹脂組成物:
[数式1]
40%≦S60/S0<80%
前記数式1で、S0は、前記光硬化樹脂組成物に395nm波長の光を100mW/cm2の強さおよび200mJ/cm2の光量で照射して、硬化後に5%のせん断変形(shear strain)を加えたときの初期応力であり、S60は、60秒後の応力である。 - 前記光硬化樹脂組成物は、反応性シリコーンオリゴマー20重量部〜70重量部、非反応性シリコーンオリゴマー20重量部〜50重量部および第1モノマーとしてエチルエーテル系アクリレート0.5重量部〜5重量部を含む、請求項1に記載の光硬化樹脂組成物。
- 前記反応性シリコーンオリゴマーは、ポリシロキサン主鎖の末端にウレタン結合を介して一つ以上の反応性官能基を有する化合物である、請求項2に記載の光硬化樹脂組成物。
- 前記反応性官能基は、(メタ)アクリル基を含む、請求項3に記載の光硬化樹脂組成物。
- 前記反応性シリコーンオリゴマーは、二官能シリコーンオリゴマーを含む、請求項2に記載の光硬化樹脂組成物。
- 前記反応性シリコーンオリゴマーは、一官能または三官能以上のシリコーンオリゴマーをさらに含む、請求項5に記載の光硬化樹脂組成物。
- 前記反応性シリコーンオリゴマーの重量平均分子量(Mw)は、10,000〜100,000である、請求項2に記載の光硬化樹脂組成物。
- 前記非反応性シリコーンオリゴマーは、ポリシロキサン主鎖の末端ケイ素に連結された水素、アルキル基またはアルコキシ基を有する化合物である、請求項2に記載の光硬化樹脂組成物。
- 前記非反応性シリコーンオリゴマーは、ポリシロキサン主鎖の末端にウレタン結合を介して水素、アルキル基またはアルコキシ基を有する化合物である、請求項2に記載の光硬化樹脂組成物。
- 前記非反応性シリコーンオリゴマーの重量平均分子量(Mw)は、10,000〜50,000である、請求項2に記載の光硬化樹脂組成物。
- 前記エチルエーテル系アクリレートは、下記化学式3または化学式4で表示される、請求項2に記載の光硬化樹脂組成物:
- 前記光硬化樹脂組成物は、第2モノマーとしてアルキルアクリレートまたはヒドロキシアルキルアクリレートをさらに含み、前記第1モノマーおよび第2モノマーの総合計の比率は、前記光硬化樹脂組成物100重量部に対して3重量部〜30重量部である、請求項2に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、光開始剤をさらに含む、請求項2に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、シランカップリング剤または酸化防止剤をさらに含む、請求項2に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、炭素数2〜4のアルコキシ反復単位を含む三官能以上の(メタ)アクリレート、三官能以上の(メタ)アクリレートおよび平均粒子のサイズが50nm〜150nm範囲であるシリカナノ粒子の固形分を30重量%以上含む、請求項1に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、395nm波長の光を100mW/cm2の強さおよび200mJ/cm2の光量で照射して、硬化後に5%のせん断変形を加えたとき、1Hzおよび25℃で測定された弾性モジュラスが1,500Pa〜10,000Paである、請求項1に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、365nm波長の光を200mW/cm2の強さおよび4000mJ/cm2の光量で照射して、硬化後に5%のせん断変形を加えたとき、1Hzおよび25℃で測定された弾性モジュラスが10,000Pa〜100,000Paである、請求項1に記載の光硬化樹脂組成物。
- 前記光硬化樹脂組成物は、1Hzおよび25℃で測定された粘度が1,000cp〜10,000cpである、請求項1に記載の光硬化樹脂組成物。
- 請求項1に記載光硬化樹脂組成物の硬化物および前記硬化物を媒介として付着した少なくとも2個以上の光学部材を含むディスプレイ装置。
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KR102236088B1 (ko) * | 2019-05-03 | 2021-04-05 | 주식회사 이그잭스 | 점접착제 조성물, 이를 이용한 디스플레이 장치의 제조방법 및 디스플레이 장치 |
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