JP7105198B2 - 組成物 - Google Patents
組成物 Download PDFInfo
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- JP7105198B2 JP7105198B2 JP2018556748A JP2018556748A JP7105198B2 JP 7105198 B2 JP7105198 B2 JP 7105198B2 JP 2018556748 A JP2018556748 A JP 2018556748A JP 2018556748 A JP2018556748 A JP 2018556748A JP 7105198 B2 JP7105198 B2 JP 7105198B2
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- diene
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- 239000011593 sulfur Substances 0.000 claims description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
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- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 6
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- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
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- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/048—Polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
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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
- B32B27/00—Layered products comprising a layer of synthetic resin
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- 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
- 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
-
- 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
- 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
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
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- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
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- C08K13/02—Organic and inorganic ingredients
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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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
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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
- C08K3/02—Elements
- C08K3/06—Sulfur
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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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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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
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J109/00—Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons
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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
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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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- C09J115/00—Adhesives based on rubber derivatives
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
- G02B3/0006—Arrays
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/13338—Input devices, e.g. touch panels
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06F—ELECTRIC DIGITAL DATA PROCESSING
- G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
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- Liquid Crystal (AREA)
Description
<1>下記(A)~(D)を含有する組成物。
(A)(メタ)アクリロイル基を有し、かつ、ジエン系又は水素添加されたジエン系の骨格を有するオリゴマー100質量部
(B)(メタ)アクリロイル基を有さず、かつ、ジエン系又は水素添加されたジエン系の骨格を有するオリゴマーが700質量部を超える量
(C)フェノキシアルキレングリコール(メタ)アクリレート
(D)光重合開始剤
設定温度:40℃
カラム構成:東ソー社製「TSKguardcolumn MP(×L)」6.0mmID×4.0cm1本、及び東ソー社製「TSK-GELMULTIPOREHXL-M」
7.8mmID×30.0cm(理論段数16,000段)2本、計3本(全体として理論段数32,000段)
サンプル注入量:100μl(試料液濃度1mg/ml)
送液圧力:39kg/cm2
検出器:RI検出器
R6-S-R7
(式(4)中、R6、R7は任意の置換基を示す。)
表1に示す組成の硬化性樹脂組成物を調製し、評価した。結果を表1に示した。
表2に示す組成の硬化性樹脂組成物を調製し、評価した。結果を表2に示した。
表3に示す組成の硬化性樹脂組成物をダム剤やフィル剤として使用し、評価した。結果を表3に示した。
(A-1)1,2-ポリブタジエンオリゴマー(日本曹達社製「TE-2000」、構造は下記式(5)参照)(GPCによるポリスチレン換算の数平均分子量2000)
(なお式(5)中、nは正の整数である。)
(A-2)イソプレンオリゴマー(クラレ社製「UC-102」)(GPCによるポリスチレン換算の数平均分子量19000、イソプレン重合物の無水マレイン酸付加物と2-ヒドロキシエチルメタクリレートとのエステル化物オリゴマー、式(2)にてYはエチレン基、R4はメチル基)
(B-1)イソプレンオリゴマー(クラレ社製「LIR-30」)(GPCによるポリスチレン換算の数平均分子量28000)
(B-2)ブタジエンオリゴマー(クラレ社製「LBR-307」)(GPCによるポリスチレン換算の数平均分子量8000)
(B-3)ブタジエンオリゴマー(クラレ社製「LBR-305」)(GPCによるポリスチレン換算の数平均分子量30000)
(B-4)ブタジエンオリゴマー(クレイバレー社製「Ricon-130」)(GPCによるポリスチレン換算の数平均分子量2500)
(C-1)ノニルフェノキシポリエチレングリコール(n=4)アクリレート(東亞合成社製「M-113」) (式(1)にてn=4、R3はノニル基)
(C-2)ノニルフェノキシポリエチレングリコール(n=8)アクリレート(日立化成工業社製「FA-318A」) (式(1)にてn=8、R3はノニル基)
(C-3)ノニルフェノキシポリエチレン(n=1)グリコールアクリレート(東亞合成社製「M-111」) (式(1)にてn=1、R3はノニル基)
(D-1)1-ヒドロキシシクロヘキシルフェニルケトン(チバスペシャリティケミカル社製「Irgacure184」)
(D-2)2,4,6-トリメチルベンゾイル-ジフェニル-フォスフィンオキサイド(チバスペシャリティケミカル社製「DarocurTPO」)
同一分子内にフェノール基及び硫黄を有する酸化防止剤として、以下の化合物を選択した。
(E-1)4,6-ビス(ドデシルチオメチル)-О-クレゾール(BASF社製「Irganox1726」)
フェノール系酸化防止剤として、以下の化合物を選択した。
(E-2)ベンゼンプロパン酸、3,5-ビス(1,1-ジメチルエチル)-4-ヒドロキシ-、C7-C9側鎖アルキルエステル(BASF社製「Irganox1135」)
硫黄系酸化防止剤として、以下の化合物を選択した。
(E-3)ジドデシル3,3’-チオジプロピオネート(BASF社製「IrganoxPS800FD」)
(F-1)γ-メタクリロキシプロピルトリメトキシシラン(信越シリコーン社製「KBM-503」)
(F-2)デシルトリメトキシシラン(信越シリコーン社製「KBM-3103C」)
硬化収縮率=((硬化物比重-液比重)/硬化物比重)×100(%)
(硬化率)=[100-((硬化後の、炭素と炭素の二重結合の吸収スペクトルの強度)/(硬化前の、炭素と炭素の二重結合の吸収スペクトルの強度))]×100(%)
Claims (21)
- 下記(A)~(E)を含有する組成物。
(A)(メタ)アクリロイル基を有し、かつ、ジエン系又は水素添加されたジエン系の骨格を有するオリゴマー100質量部
(B)(メタ)アクリロイル基を有さず、かつ、ジエン系又は水素添加されたジエン系の骨格を有するオリゴマーが700質量部を超える量
(C)フェノキシアルキレングリコール(メタ)アクリレート300質量部以上500質量部以下
(D)光重合開始剤
(E)同一分子内にフェノール基と硫黄を有する酸化防止剤であるか、又は、フェノール基を有する酸化防止剤と硫黄を有する酸化防止剤の組み合わせである、酸化防止剤 - (A)成分のジエン系又は水素添加されたジエン系の骨格が、ポリブタジエン、ポリイソプレン、ポリブタジエンの水素添加物、及びポリイソプレンの水素添加物からなる群から選ばれる1種以上の骨格である請求項1又は2に記載の組成物。
- (B)成分のジエン系又は水素添加されたジエン系の骨格が、ポリブタジエン、ポリイソプレン、ポリブタジエンの水素添加物、及びポリイソプレンの水素添加物からなる群から選ばれる1種以上の骨格である請求項1~3のうちのいずれか1項に記載の組成物。
- (A)成分の分子量が500~70000である請求項1~4のうちのいずれか1項に記載の組成物。
- (B)成分の分子量が500~70000である請求項1~5のうちのいずれか1項に記載の組成物。
- 更に、(F)シランカップリング剤を含有する請求項1~6のうちのいずれか1項に記載の組成物。
- 硬化収縮率が2.0%以下である請求項1~7のうちのいずれか1項に記載の組成物。
- 組成物をダム剤とフィル剤として使用する場合、ダム剤とフィル剤の400nm透過率差が1%以下、屈折率差が0.01以下である請求項1~8のうちのいずれか1項に記載の組成物。
- 1000mJ/cm2以上の紫外線照射により、幅1mm以上の光非透過部を硬化できる請求項1~9のうちのいずれか1項に記載の組成物。
- 請求項1~10のうちのいずれか1項に記載の組成物を含有する硬化性樹脂組成物。
- 請求項1~11のうちのいずれか1項に記載の組成物を含有する接着剤組成物。
- 用途がレンズ用接着剤である請求項12に記載の接着剤組成物。
- 請求項12又は13に記載の接着剤組成物の硬化体。
- 請求項14に記載の硬化体により被覆又は接合された被着体を含む複合体。
- 請求項15に記載の被着体がトリアセチルセルロース、フッ素系ポリマー、ポリエステル、ポリカーボネート、ポリオレフィン、ガラス、金属からなる群から選ばれる1種以上である複合体。
- 請求項12又は13に記載の接着剤組成物により接合された被着体を含むタッチパネル積層体。
- 請求項12又は13に記載の接着剤組成物により接合された被着体を含む液晶パネル積層体。
- 請求項17に記載のタッチパネル積層体を含むディスプレイ。
- 請求項18に記載の液晶パネル積層体を含むディスプレイ。
- 請求項12又は13に記載の接着剤組成物により接合されたレンズを含むレンズ積層体。
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JP2014148606A (ja) | 2013-01-31 | 2014-08-21 | Denki Kagaku Kogyo Kk | 硬化性樹脂組成物 |
JP2015054938A (ja) | 2013-09-13 | 2015-03-23 | 電気化学工業株式会社 | 硬化性樹脂組成物 |
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