JP7388456B2 - Active energy ray-curable resin composition, cured product, laminate, and lens - Google Patents
Active energy ray-curable resin composition, cured product, laminate, and lens Download PDFInfo
- Publication number
- JP7388456B2 JP7388456B2 JP2021575842A JP2021575842A JP7388456B2 JP 7388456 B2 JP7388456 B2 JP 7388456B2 JP 2021575842 A JP2021575842 A JP 2021575842A JP 2021575842 A JP2021575842 A JP 2021575842A JP 7388456 B2 JP7388456 B2 JP 7388456B2
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- JP
- Japan
- Prior art keywords
- active energy
- energy ray
- resin composition
- curable resin
- meth
- Prior art date
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- 239000011347 resin Substances 0.000 claims description 27
- 229920005989 resin Polymers 0.000 claims description 27
- 239000000412 dendrimer Substances 0.000 claims description 7
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- 125000004122 cyclic group Chemical group 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 description 24
- 239000003999 initiator Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 22
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- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000001552 radio frequency sputter deposition Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/023—Optical properties
-
- 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
- B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
-
- 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
- C08J7/06—Coating with compositions not containing macromolecular substances
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/005—Dendritic macromolecules
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/11—Anti-reflection coatings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F9/00—Registration or positioning of originals, masks, frames, photographic sheets or textured or patterned surfaces, e.g. automatically
- G03F9/70—Registration or positioning of originals, masks, frames, photographic sheets or textured or patterned surfaces, e.g. automatically for microlithography
- G03F9/7003—Alignment type or strategy, e.g. leveling, global alignment
- G03F9/7042—Alignment for lithographic apparatus using patterning methods other than those involving the exposure to radiation, e.g. by stamping or imprinting
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Laminated Bodies (AREA)
Description
本発明は、活性エネルギー線硬化性樹脂組成物、硬化物、積層体及びレンズに関する。 The present invention relates to an active energy ray-curable resin composition, a cured product, a laminate, and a lens.
近年、紫外線等の活性エネルギー線により硬化可能な活性エネルギー線硬化性樹脂組成物や、熱により硬化可能な熱硬化性樹脂組成物などの硬化性樹脂組成物は、インキ、塗料、コーティング剤、接着剤、光学部材等の分野において広く用いられている。なかでも、前記光学部材の分野において、スマートフォンや車載カメラに用いるレンズ用樹脂として好適に用いられている。前記レンズ用樹脂の成形方法として、レンズモジュールの薄型化と生産効率の向上に繋がることから、光インプリントを用いた製造プロセスの検討が盛んになされている。前記光インプリントは、未硬化樹脂をウエハー等の基材上に塗布した後、レンズ金型で挟み込むことで形状転写し、光硬化することにより数百個のウエハーレベルレンズ成形を一度に可能とする方法である In recent years, curable resin compositions such as active energy ray-curable resin compositions that can be cured by active energy rays such as ultraviolet rays and thermosetting resin compositions that can be cured by heat have been widely used in inks, paints, coatings, and adhesives. It is widely used in the fields of chemicals, optical components, etc. Among these, in the field of optical members, it is suitably used as a resin for lenses used in smartphones and in-vehicle cameras. As a method for molding the lens resin, a manufacturing process using optical imprinting is being actively studied because it leads to thinning of the lens module and improvement of production efficiency. The optical imprint method enables the molding of hundreds of wafer-level lenses at once by coating an uncured resin onto a base material such as a wafer, then sandwiching it between lens molds to transfer the shape, and then curing it with light. This is the way to do it.
前記光インプリントに用いられる樹脂としては、ウレタン（メタ）アクリレートを含有する硬化性樹脂組成物が知られているが（例えば、特許文献１参照。）、レンズ成形後、レンズ上層を反射防止膜で被覆して用いた場合、半田リフローなどの熱処理時にクラックが生じる等の問題があった。 A curable resin composition containing urethane (meth)acrylate is known as the resin used for the optical imprinting (see, for example, Patent Document 1), but after lens molding, the upper layer of the lens is coated with an antireflection film. When used as a coating, there were problems such as cracks occurring during heat treatment such as solder reflow.
そこで、反射防止膜等の無機層成膜後の半田リフロー処理時に、無機層のクラック発生を抑制可能な優れた耐クラック性を有する樹脂層形成用材料が求められていた。 Therefore, there has been a need for a material for forming a resin layer that has excellent crack resistance that can suppress the occurrence of cracks in the inorganic layer during solder reflow treatment after forming an inorganic layer such as an antireflection film.
本発明が解決しようとする課題は、樹脂層及び無機層を有する積層体において、無機層のクラック発生を抑制可能な優れた耐クラック性を有する樹脂層形成用活性エネルギー線硬化性樹脂組成物、前記活性エネルギー線硬化性樹脂組成物の硬化物、積層体及び前記積層体からなるレンズを提供することである。 The problem to be solved by the present invention is to provide an active energy ray-curable resin composition for forming a resin layer that has excellent crack resistance that can suppress the occurrence of cracks in the inorganic layer in a laminate having a resin layer and an inorganic layer. The object of the present invention is to provide a cured product of the active energy ray-curable resin composition, a laminate, and a lens made of the laminate.
本発明者らは、上記課題を解決するため鋭意検討を行った結果、（メタ）アクリロイル基を有する多分岐型高分子化合物を含有する活性エネルギー線硬化性樹脂組成物を用いることによって、上記課題を解決できることを見出し、本発明を完成させた。 As a result of intensive studies to solve the above problems, the present inventors have solved the above problems by using an active energy ray-curable resin composition containing a hyperbranched polymer compound having a (meth)acryloyl group. The present invention was completed based on the discovery that the problem can be solved.
すなわち、本発明は、樹脂層及び無機層を有する積層体の樹脂層形成用活性エネルギー線硬化性樹脂組成物であって、前記活性エネルギー線硬化性樹脂組成物が、（メタ）アクリロイル基を有する多分岐型高分子化合物（Ａ）を含有するものであることを特徴とする樹脂層形成用活性エネルギー線硬化性樹脂組成物、前記活性エネルギー線硬化性樹脂組成物の硬化物、積層体及び前記積層体からなるレンズに関するものである。 That is, the present invention provides an active energy ray-curable resin composition for forming a resin layer of a laminate having a resin layer and an inorganic layer, wherein the active energy ray-curable resin composition has a (meth)acryloyl group. An active energy ray-curable resin composition for forming a resin layer, containing a hyperbranched polymer compound (A), a cured product of the active energy ray-curable resin composition, a laminate, and the above. This invention relates to a lens made of a laminate.
本発明の活性エネルギー線硬化性樹脂組成物は、樹脂層及び無機層を有する積層体において、無機層のクラック発生を抑制することができることから、光インプリントによるレンズ製造に好適に用いることができる。 The active energy ray-curable resin composition of the present invention can suppress the occurrence of cracks in the inorganic layer in a laminate having a resin layer and an inorganic layer, and therefore can be suitably used for manufacturing lenses by optical imprinting. .
本発明の活性エネルギー線硬化性樹脂組成物は、（メタ）アクリロイル基を有する多分岐型高分子化合物（Ａ）を含有することを特徴とする。 The active energy ray-curable resin composition of the present invention is characterized by containing a hyperbranched polymer compound (A) having a (meth)acryloyl group.
なお、本発明において、「（メタ）アクリロイル」とは、アクリロイル及び／またはメタクリロイルを意味する。また、「（メタ）アクリレート」とは、アクリレート及び／またはメタクリレートを意味する。さらに、「（メタ）アクリル」とは、アクリル及び／またはメタクリルを意味する。 In addition, in the present invention, "(meth)acryloyl" means acryloyl and/or methacryloyl. Moreover, "(meth)acrylate" means acrylate and/or methacrylate. Furthermore, "(meth)acrylic" means acrylic and/or methacrylic.
前記（メタ）アクリロイル基を有する多分岐型高分子化合物（Ａ）としては、例えば、デンドリマー構造（樹枝状構造）を有する化合物（以下、「デンドリマー」と称することがある。）、ハイパーブランチ構造（超分岐構造）を有する化合物（以下、「ハイパーブランチ」または「ハイパーブランチポリマー」と称することがある。）、スター構造を有する化合物等が挙げられる。 Examples of the hyperbranched polymer compound (A) having a (meth)acryloyl group include a compound having a dendrimer structure (dendrimer structure) (hereinafter sometimes referred to as "dendrimer"), a hyperbranched structure ( Examples include compounds having a hyperbranched structure (hereinafter sometimes referred to as "hyperbranched" or "hyperbranched polymer"), compounds having a star structure, and the like.
前記デンドリマー構造を有する化合物の市販品としては、例えば、大阪有機化学工業株式会社製「ビスコート＃１０００ＬＴ」、ＭＩＷＯＮ社製「Ｍｉｒａｍｅｒ ＳＰ１１０６」が挙げられる。これらのデンドリマー構造を有する化合物は、単独で用いることも２種以上を併用することもできる。 Examples of commercially available compounds having the dendrimer structure include "Viscoat #1000LT" manufactured by Osaka Organic Chemical Industry Co., Ltd. and "Miramer SP1106" manufactured by MIWON. These compounds having a dendrimer structure can be used alone or in combination of two or more.
前記ハイパーブランチ構造を有する化合物の市販品としては、例えば、Ａｒｋｅｍａ社製「ＣＮ２３０２」、「ＣＮ２３０３」、「ＣＮ２３０４」、ＩＧＭ社製「Ｐｈｏｔｏｍｅｒ ５５００」等が挙げられる。これらのハイパーブランチ構造を有する化合物は、単独で用いることも２種以上を併用することもできる。 Examples of commercially available compounds having the hyperbranched structure include "CN2302," "CN2303," and "CN2304" manufactured by Arkema, and "Photomer 5500" manufactured by IGM. These compounds having a hyperbranched structure can be used alone or in combination of two or more.
前記多分岐型高分子化合物（Ａ）の１分子当たりの平均（メタ）アクリロイル基数は、無機層のクラック発生を抑制可能な優れた耐クラック性を有する活性エネルギー線硬化性樹脂組成物が得られることから、６～６４個の範囲がより好ましく、１０～３２個の範囲が特に好ましい。 The average number of (meth)acryloyl groups per molecule of the hyperbranched polymer compound (A) makes it possible to obtain an active energy ray-curable resin composition that has excellent crack resistance that can suppress the generation of cracks in the inorganic layer. Therefore, the range of 6 to 64 is more preferable, and the range of 10 to 32 is particularly preferable.
前記多分岐型高分子化合物（Ａ）の重量平均分子量（Ｍｗ）は、無機層のクラック発生を抑制可能な優れた耐クラック性を有する活性エネルギー線硬化性樹脂組成物が得られることから、５００～３０，０００の範囲が好ましく、１，０００～１０，０００の範囲がより好ましい。なお、本発明において、重量平均分子量（Ｍｗ）は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）法により測定した値を示す。 The weight average molecular weight (Mw) of the hyperbranched polymer compound (A) is 500, since an active energy ray-curable resin composition having excellent crack resistance that can suppress the generation of cracks in the inorganic layer is obtained. The range is preferably from 1,000 to 10,000, more preferably from 1,000 to 10,000. In the present invention, the weight average molecular weight (Mw) indicates a value measured by gel permeation chromatography (GPC).
前記多分岐高分子化合物（Ａ）の２５℃での粘度は、１０ｍＰａ・ｓ～１，５００ｍＰａ・ｓの範囲が好ましく、１００ｍＰａ・ｓ～１，０００ｍＰａ・ｓの範囲がより好ましい。なお、本発明において、粘度は、Ｅ型粘度計にて測定した値を示す。 The viscosity of the hyperbranched polymer compound (A) at 25° C. is preferably in the range of 10 mPa·s to 1,500 mPa·s, more preferably in the range of 100 mPa·s to 1,000 mPa·s. In addition, in this invention, a viscosity shows the value measured with the E-type viscometer.
前記多分岐型高分子化合物（Ａ）の製造方法としては、特に制限されず、適宜公知の方法により製造することができる。例えば、中心コア分子に世代ごとに分子を結合させて分岐を形成するダイバージェント法、予め合成した枝部分をコア分子に結合させるコンバージェント法、２以上の反応点Ｂを有する分岐部分と別の反応点Ａを有するつなぎ部分とを１分子内に持つモノマーＡＢｘを用いて１段階で合成する方法等が挙げられる。なかでも、前記ダイバージェント法が好ましく、例えば、多価アルコールと、１つ以上のカルボキシル基及び２つ以上の水酸基を有する化合物とを、エステル化反応させることで多分岐ポリエステルポリオールを得、次いで、末端の水酸基と（メタ）アクリル酸とを反応させる方法にて製造することが好ましい。 The method for producing the hyperbranched polymer compound (A) is not particularly limited, and can be produced by any known method as appropriate. For example, the divergent method involves bonding molecules to a central core molecule in each generation to form a branch, the convergent method involves bonding pre-synthesized branch parts to the core molecule, and Examples include a method of synthesizing in one step using a monomer ABx having a linking moiety having a reaction point A in one molecule. Among these, the divergent method is preferred; for example, a polyhydric alcohol and a compound having one or more carboxyl groups and two or more hydroxyl groups are subjected to an esterification reaction to obtain a hyperbranched polyester polyol, and then, It is preferable to manufacture by a method of reacting a terminal hydroxyl group with (meth)acrylic acid.
本発明の樹脂層形成用活性エネルギー線硬化性樹脂組成物における前記多分岐型高分子化合物（Ａ）の含有量は、樹脂層形成用活性エネルギー線硬化性樹脂組成物全体を１００質量部とした場合に１～８０質量部であることが好ましく、耐クラック性が向上することから５～４５質量部であることがより好ましく、１０～３５質量部であると更に耐クラック性が向上するため特に好ましい。 The content of the multibranched polymer compound (A) in the active energy ray curable resin composition for forming a resin layer of the present invention is based on 100 parts by mass of the entire active energy ray curable resin composition for forming a resin layer. In this case, the amount is preferably 1 to 80 parts by mass, more preferably 5 to 45 parts by mass because it improves crack resistance, and especially 10 to 35 parts by mass because it further improves crack resistance. preferable.
前記多価アルコールとしては、例えば、グリセリン、トリメチロールプロパン、ジトリメチロールプロパン、トリメチロールエタン、ジトリメチロールエタン、トリス（２－ヒドロキシエチル）イソシアヌレート、１，２，４－ブタントリオール、ペンタエリスリトール、ジペンタエリスリトール、ソルビトール、マンニトール、及びこれらのアルキレンオキサイド付加物もしくはカプロラクトン付加物等が挙げられる。これらの多価アルコールは、単独で用いることも２種以上を併用することもできる。 Examples of the polyhydric alcohol include glycerin, trimethylolpropane, ditrimethylolpropane, trimethylolethane, ditrimethylolethane, tris(2-hydroxyethyl)isocyanurate, 1,2,4-butanetriol, pentaerythritol, and ditrimethylolpropane. Examples include pentaerythritol, sorbitol, mannitol, and alkylene oxide adducts or caprolactone adducts thereof. These polyhydric alcohols can be used alone or in combination of two or more.
前記１つ以上のカルボキシル基及び２つ以上の水酸基を有する化合物としては、例えば、２，３－ジヒドロキシプロピオン酸、２，２－ジメチロールプロピオン酸、２，２－ジメチロールブタン酸、酒石酸、２，３－ジヒドロキシ安息香酸、２，４－ジヒドロキシ安息香酸、２，５－ジヒドロキシ安息香酸、２，６－ジヒドロキシ安息香酸、３，４－ジヒドロキシ安息香酸、３，５－ジヒドロキシ安息香酸、３，５－ビス（２－ヒドロキシエトキシ）安息香酸、２，６－ジヒドロキシ－４－メチル安息香酸、３，５－ジヒドロキシ－４－メチル安息香酸、シトラジン酸、２，３－ジヒドロキシフェニル酢酸、２，４－ジヒドロキシフェニル酢酸、２，５－ジヒドロキシフェニル酢酸、２，６－ジヒドロキシフェニル酢酸、３，４－ジヒドロキシフェニル酢酸、３，５－ジヒドロキシフェニル酢酸、及びこれらの誘導体等が挙げられる。これらの化合物は、単独で用いることも２種以上を併用することもできる。 Examples of the compound having one or more carboxyl groups and two or more hydroxyl groups include 2,3-dihydroxypropionic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, tartaric acid, , 3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 2,5-dihydroxybenzoic acid, 2,6-dihydroxybenzoic acid, 3,4-dihydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 3,5 -bis(2-hydroxyethoxy)benzoic acid, 2,6-dihydroxy-4-methylbenzoic acid, 3,5-dihydroxy-4-methylbenzoic acid, citrazic acid, 2,3-dihydroxyphenylacetic acid, 2,4- Examples include dihydroxyphenylacetic acid, 2,5-dihydroxyphenylacetic acid, 2,6-dihydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, 3,5-dihydroxyphenylacetic acid, and derivatives thereof. These compounds can be used alone or in combination of two or more.
前記多分岐ポリエステルポリオールとしては、上述のとおり、多価アルコールと、1つ以上のカルボキシル基及び２つ以上の水酸基を有する化合物とを、エステル化反応させて得る以外に、市販品を用いることもできる。 As the hyperbranched polyester polyol, as described above, in addition to obtaining it by esterifying a polyhydric alcohol and a compound having one or more carboxyl groups and two or more hydroxyl groups, commercially available products may also be used. can.
前記多分岐ポリエステルポリオールの市販品としては、例えば、パーストープ社製「ＢＯＬＴＯＲＮ Ｈ２０」、「ＢＯＬＴＯＲＮ Ｈ３０」、「ＢＯＬＴＯＲＮ Ｈ４０」、「ＢＯＬＴＯＲＮ Ｈ３１１」、「ＢＯＬＴＯＲＮ Ｈ２００３」、「ＢＯＬＴＯＲＮ Ｈ２００４」、「ＢＯＬＴＯＲＮ Ｐ５００」、「ＢＯＬＴＯＲＮ Ｐ５０１」、「ＢＯＬＴＯＲＮ Ｐ１０００」等が挙げられる。 Examples of commercially available hyperbranched polyester polyols include "BOLTORN H20", "BOLTORN H30", "BOLTORN H40", "BOLTORN H311", "BOLTORN H2003", "BOLTORN H2004", and "BOLTORN P50" manufactured by Perstorp. 0" , "BOLTORN P501", "BOLTORN P1000", etc.
本発明の活性エネルギー線硬化性樹脂組成物としては、必要に応じて、光重合開始剤を含有することもできる。 The active energy ray-curable resin composition of the present invention may also contain a photopolymerization initiator, if necessary.
前記光重合開始剤としては、例えば、１－ヒドロキシシクロヘキシルフェニルケトン、２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン、１－〔４－（２－ヒドロキシエトキシ）フェニル〕－２－ヒドロキシ－２－メチル－１－プロパン－１－オン、チオキサントン及びチオキサントン誘導体、２，２′－ジメトキシ－１，２－ジフェニルエタン－１－オン、ジフェニル（２，４，６－トリメトキシベンゾイル）ホスフィンオキシド、２，４，６－トリメチルベンゾイルジフェニルホスフィンオキシド、ビス（２，４，６－トリメチルベンゾイル）フェニルホスフィンオキシド、２－メチル－１－（４－メチルチオフェニル）－２－モルフォリノプロパン－１－オン、２－ベンジル－２－ジメチルアミノ－１－（４－モルホリノフェニル）－１－ブタノン等が挙げられる。 Examples of the photopolymerization initiator include 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)phenyl]-2- Hydroxy-2-methyl-1-propan-1-one, thioxanthone and thioxanthone derivatives, 2,2'-dimethoxy-1,2-diphenylethan-1-one, diphenyl(2,4,6-trimethoxybenzoyl)phosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1- and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone.
前記その他の光重合開始剤の市販品としては、例えば、「Ｏｍｎｉｒａｄ－１１７３」、「Ｏｍｎｉｒａｄ－１８４」、「Ｏｍｎｉｒａｄ－１２７」、「Ｏｍｎｉｒａｄ－２９５９」、「Ｏｍｎｉｒａｄ－３６９」、「Ｏｍｎｉｒａｄ－３７９」、「Ｏｍｎｉｒａｄ－９０７」、「Ｏｍｎｉｒａｄ－４２６５」、「Ｏｍｎｉｒａｄ－１０００」、「Ｏｍｎｉｒａｄ－６５１」、「Ｏｍｎｉｒａｄ－ＴＰＯ」、「Ｏｍｎｉｒａｄ－８１９」、「Ｏｍｎｉｒａｄ－２０２２」、「Ｏｍｎｉｒａｄ－２１００」、「Ｏｍｎｉｒａｄ－７５４」、「Ｏｍｎｉｒａｄ－７８４」、「Ｏｍｎｉｒａｄ－５００」、「Ｏｍｎｉｒａｄ－８１」（ＩＧＭ社製）、「カヤキュア－ＤＥＴＸ」、「カヤキュア－ＭＢＰ」、「カヤキュア－ＤＭＢＩ」、「カヤキュア－ＥＰＡ」、「カヤキュア－ＯＡ」（日本化薬株式会社製）、「バイキュア－１０」、「バイキュア－５５」（ストウファ・ケミカル社製）、「トリゴナルＰ１」（アクゾ社製）、「サンドレイ１０００」（サンドズ社製）、「ディープ」（アプジョン社製）、「クオンタキュア－ＰＤＯ」、「クオンタキュア－ＩＴＸ」、「クオンタキュア－ＥＰＤ」（ワードブレンキンソップ社製）、「Ｒｕｎｔｅｃｕｒｅ－１１０４」（Ｒｕｎｔｅｃ社製）等が挙げられる。これらの光重合開始剤は、単独で用いることも、２種以上を併用することもできる。 Examples of commercially available photopolymerization initiators include "Omnirad-1173," "Omnirad-184," "Omnirad-127," "Omnirad-2959," "Omnirad-369," and "Omnirad-379." , "Omnirad-907", "Omnirad-4265", "Omnirad-1000", "Omnirad-651", "Omnirad-TPO", "Omnirad-819", "Omnirad-2022", "Omnirad-2100", " "Omnirad-754", "Omnirad-784", "Omnirad-500", "Omnirad-81" (manufactured by IGM), "Kayacure-DETX", "Kayacure-MBP", "Kayacure-DMBI", "Kayacure-EPA" ”, “Kayacure-OA” (manufactured by Nippon Kayaku Co., Ltd.), “Bicure-10”, “Bicure-55” (manufactured by Stouffer Chemical Co., Ltd.), “Trigonal P1” (manufactured by Akzo Corporation), “Sandray 1000” ( Sandoz), ``Deep'' (Upjohn), ``Quantacure-PDO'', ``Quantacure-ITX'', ``Quantacure-EPD'' (Ward Blenkinsop), ``Runtecure-1104'' (Runtec) (manufactured by a company), etc. These photopolymerization initiators can be used alone or in combination of two or more.
前記光重合開始剤の含有量は、例えば、活性エネルギー線硬化性樹脂組成物の溶剤以外の成分の合計中に０．０５～１０質量％の範囲であることが好ましく、０．１～５質量％の範囲であることがより好ましい。 The content of the photopolymerization initiator is preferably in the range of 0.05 to 10% by mass, for example, in the total of components other than the solvent of the active energy ray-curable resin composition, and 0.1 to 5% by mass. % range is more preferable.
また、前記光重合開始剤は、光増感剤と併用することもできる。 Further, the photopolymerization initiator can also be used in combination with a photosensitizer.
前記光増感剤としては、例えば、アミン化合物、尿素化合物、含硫黄化合物、含燐化合物、含塩素化合物、ニトリル化合物等が挙げられる。 Examples of the photosensitizer include amine compounds, urea compounds, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, and nitrile compounds.
また、本発明の活性エネルギー線硬化性樹脂組成物としては、必要に応じて、カーボネート構造を有する（メタ）アクリル化合物、環状構造を有する（メタ）アクリル化合物、一分子中に１又は２個の（メタ）アクリロイル基及び一分子中にアルキレングリコール構造を有する化合物を含有することもできる。 In addition, the active energy ray-curable resin composition of the present invention may optionally contain a (meth)acrylic compound having a carbonate structure, a (meth)acrylic compound having a cyclic structure, or one or two acrylic compounds in one molecule. It can also contain a (meth)acryloyl group and a compound having an alkylene glycol structure in one molecule.
前記カーボネート構造を有する（メタ）アクリル化合物としては、例えば、ポリカーボネートポリオールと、（メタ）アクリル酸及び／又は（メタ）アクリル酸エステルとを反応させたもの等が挙げられる。 Examples of the (meth)acrylic compound having a carbonate structure include those obtained by reacting a polycarbonate polyol with (meth)acrylic acid and/or (meth)acrylic acid ester.
前記ポリカーボネートボリオールとしては、例えば、水酸基を２個以上有する化合物と炭酸エステルとの反応物等が挙げられる。 Examples of the polycarbonate polyol include a reaction product of a compound having two or more hydroxyl groups and a carbonate ester.
前記水酸基を２個以上有する化合物としては、例えば、エチレングリコール、プロピレングリコール、１，３－プロパンジオール、１，４－ブタンジオール、１，３－ブタンジオール、１，２－ブタンジオール、２－メチル－１，３－プロパンジオール、１，５－ペンタンジオール、ネオペンチルグリコール、１，６－ヘキサンジオール、１，５－ヘキサンジオール、３－メチル－１，５－ペンタンジオール、１，７－ヘプタンジオール、１，８－オクタンジオール、１，９－ノナンジオール、１，８－ノナンジオール、２－エチル－２－ブチル－１，３－プロパンジオール、１，１０－デカンジオール、１，１２－ドデカンジオール、１，４－シクロヘキサンジメタノール、１，３－シクロヘキサンジメタノール、トリメチロールプロパン、トリメチロールエタン、グリセリン等を用いることができる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the compound having two or more hydroxyl groups include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 2-methyl -1,3-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,5-hexanediol, 3-methyl-1,5-pentanediol, 1,7-heptanediol , 1,8-octanediol, 1,9-nonanediol, 1,8-nonanediol, 2-ethyl-2-butyl-1,3-propanediol, 1,10-decanediol, 1,12-dodecanediol , 1,4-cyclohexanedimethanol, 1,3-cyclohexanedimethanol, trimethylolpropane, trimethylolethane, glycerin, etc. can be used. These compounds can be used alone or in combination of two or more.
前記炭酸エステルとしては、例えば、ジメチルカーボネート、ジエチルカーボネート、ジフェニルカーボネート、エチレンカーボネート、プロピレンカーボネート等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the carbonate ester include dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, and the like. These compounds can be used alone or in combination of two or more.
前記（メタ）アクリル酸エステルとしては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ－プロピル（メタ）アクリレート、ｎ－ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｎ－ペンチル（メタ）アクリレート、ｎ－ヘキシル（メタ）アクリレート、ｎ－ヘプチル（メタ）アクリレート、ｎ－オクチル（メタ）アクリレート、２－エチルヘキシル（メタ）アクリレート、ノニル（メタ）アクリレート、デシル（メタ）アクリレート、ドデシル（メタ）アクリレート、メトキシポリエチレングリコールモノ（メタ）アクリレート、オクトキシポリエチレングリコール・ポリプロピレングリコールモノ（メタ）アクリレート、ラウロキシポリエチレングリコールモノ（メタ）アクリレート、ステアロキシポリエチレングリコールモノ（メタ）アクリレート、フェノキシポリエチレングリコールモノ（メタ）アクリレート、フェノキシポリエチレングリコール・ポリプロピレングリコールモノ（メタ）アクリレート、ノニルフェノキシポリプロピレングリコールモノ（メタ）アクリレート、ノニルフェノキシポリ（エチレングリコール・プロピレングリコール）モノ（メタ）アクリレート、２－パーフルオロヘキシルエチル（メタ）アクリレート等を用いることができる。これらの（メタ）アクリル酸エステルは単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic ester include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, n-pentyl ( meth)acrylate, n-hexyl(meth)acrylate, n-heptyl(meth)acrylate, n-octyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, nonyl(meth)acrylate, decyl(meth)acrylate, dodecyl( meth)acrylate, methoxypolyethylene glycol mono(meth)acrylate, octoxypolyethylene glycol/polypropylene glycol mono(meth)acrylate, lauroxypolyethylene glycol mono(meth)acrylate, stearoxypolyethylene glycol mono(meth)acrylate, phenoxypolyethylene glycol mono(meth)acrylate (meth)acrylate, phenoxypolyethylene glycol/polypropylene glycol mono(meth)acrylate, nonylphenoxypolypropylene glycol mono(meth)acrylate, nonylphenoxypoly(ethylene glycol/propylene glycol) mono(meth)acrylate, 2-perfluorohexylethyl ( Meta)acrylate etc. can be used. These (meth)acrylic esters can be used alone or in combination of two or more.
また、前記カーボネート構造を有する（メタ）アクリル化合物の市販品としては、例えば、宇部興産株式会社製「ＵＨ－１００ＤＡ」、「ＵＭ－９０（１／３）ＤＡ」、「ＵＭ－９０（１／１）ＤＡ」、「ＵＭ－９０（３／１）ＤＡ」、「ＵＨ－１００ＤＭ」、「ＵＭ－９０（１／３）ＤＭ」、「ＵＭ－９０（１／１）ＤＭ」、「ＵＭ－９０（３／１）ＤＭ」等が挙げられる。 In addition, as commercially available (meth)acrylic compounds having the carbonate structure, for example, "UH-100DA", "UM-90 (1/3) DA", and "UM-90 (1/3)" manufactured by Ube Industries, Ltd. 1) DA", "UM-90 (3/1) DA", "UH-100DM", "UM-90 (1/3) DM", "UM-90 (1/1) DM", "UM- 90 (3/1) DM".
前記環状構造を有する（メタ）アクリル化合物としては、例えば、モノシクロアルカン構造、ベンゼン環、トリシクロデカン構造、ジシクロペンテニル構造、イソボルニル構造、酸素原子をヘテロ原子とする複素環構造等を有する（メタ）アクリル化合物を用いることができる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having a cyclic structure include a monocycloalkane structure, a benzene ring, a tricyclodecane structure, a dicyclopentenyl structure, an isobornyl structure, a heterocyclic structure having an oxygen atom as a heteroatom, etc. Meth)acrylic compounds can be used. These compounds can be used alone or in combination of two or more.
前記モノシクロアルカン構造を有する（メタ）アクリル化合物としては、例えば、シクロヘキシル（メタ）アクリレート、１，４－シクロヘキサンジメタノールモノアクリレート等を用いることができる。これらの化合物は単独で用いることも２種以上を併用することもできる。 As the (meth)acrylic compound having a monocycloalkane structure, for example, cyclohexyl (meth)acrylate, 1,4-cyclohexanedimethanol monoacrylate, etc. can be used. These compounds can be used alone or in combination of two or more.
前記ベンゼン環を有する（メタ）アクリル化合物としては、例えば、ベンジル（メタ）アクリレート、フェノキシ（メタ）アクリレート、フェノキシエチル（メタ）アクリレート、ノニルフェノキシポリエチレングリコール（メタ）アクリレート等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having a benzene ring include benzyl (meth)acrylate, phenoxy (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, and the like. These compounds can be used alone or in combination of two or more.
前記トリシクロデカン（ジシクロペンタニル）構造を有する（メタ）アクリル化合物としては、例えば、ジシクロペンタニル（メタ）アクリレ－ト、ジシクロペンタニルオキシエチル（メタ）アクリレ－ト、ジメチロールトリシクロデカンジ（メタ）アクリレート、トリシクロデカンジオールジ（メタ）アクリレート、トリシクロデカンジメタノールジ（メタ）アクリレート等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having the tricyclodecane (dicyclopentanyl) structure include dicyclopentanyl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, and dimethylol trichloride. Examples include cyclodecane di(meth)acrylate, tricyclodecanediol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, and the like. These compounds can be used alone or in combination of two or more.
前記ジシクロペンテニル構造を有する（メタ）アクリル化合物としては、例えば、ジシクロペンテニル（メタ）アクリレ－ト、ジシクロペンテニルオキシエチル（メタ）アクリレ－ト等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having the dicyclopentenyl structure include dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, and the like. These compounds can be used alone or in combination of two or more.
前記イソボルニル構造を有する（メタ）アクリル化合物としては、例えば、イソボルニル（メタ）アクリレート、イソボルニルジ（メタ）アクリレート等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having an isobornyl structure include isobornyl (meth)acrylate, isobornyl di(meth)acrylate, and the like. These compounds can be used alone or in combination of two or more.
前記酸素原子をヘテロ原子とする複素環構造等を有する（メタ）アクリル化合物としては、例えば、環状トリメチルロールプロパンホルマールアクリレート、（２－メチル－２－エチル－１，３－ジオキソラン－４－イル）メチル（メタ）アクリレート、（３－エチルオキセタン－３－イル）メチル（メタ）アクリレート、テトラヒドロフルフリル（メタ）アクリレート、ネオペンチルグリコール変性トリメチロールプロパンジ（メタ）アクリレート等が挙げられる。これらの化合物は単独で用いることも２種以上を併用することもできる。 Examples of the (meth)acrylic compound having a heterocyclic structure in which the oxygen atom is a heteroatom include cyclic trimethylolpropane formal acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl) Examples include methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, neopentyl glycol-modified trimethylolpropane di(meth)acrylate, and the like. These compounds can be used alone or in combination of two or more.
前記一分子中に１又は２個の（メタ）アクリロイル基及び一分子中にアルキレングリコール構造を有する化合物としては、一分子中に１又は２個の（メタ）アクリロイル基及びアルキレングリコール構造を必須として有するものである。 The compound having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule must have one or two (meth)acryloyl groups and an alkylene glycol structure in one molecule. It is something that you have.
前記アルキレングリコール構造としては、例えば、１，２－エタンジオール（エチレングリコール）、１，３－プロパンジオール、１，４－ブタンジオール、１，５－ペンタンジオール、１，６－ヘキサンジオール、１，７－ヘプタンジオール、１，８－オクタンジオール、１，９－ノナンジオール、１，１０－デカンジオール、１，２－プロパンジオール（プロピレングリコール）、１，２－ブタンジオール、１，３－ブタンジオール、２，３－ブタンジオール、２－メチル－１，３－プロパンジオール、１，２－ペンタンジオール、１，３－ペンタンジオール、１，４－ペンタンジオール、２，４－ペンタンジオール、２，２－ジメチル－１，３－プロパンジオール（ネオペンチルグリコール）、３－メチル－１，３－ブタンジオール、２－メチル－１，３－ブタンジオール、１，２－ヘキサンジオール、１，５－ヘキサンジオール、２，５－ヘキサンジオール、３－メチル－１，５－ペンタンジオール、２，３－ジメチル－２，３－ブタンジオール、２－エチル－２－メチル－１，３－プロパンジオール、１，２－ヘプタンジオール、２－メチル－２－プロピル－１，３－プロパンジオール、２，４－ジメチル－２，４－ペンタンジオール、３，６－オクタンジオール、２，２，４－トリメチル－１，３－ペンタンジオール、２，５－ジメチル－２，５－ヘキサンジオール、２－エチル－１，３－ヘキサンジオール、１，２－ノナンジオール、１，８－ノナンジオール、２，８－ノナンジオール、２－ブチル－２－エチル－１，３－プロパンジオール、２，４－ジエチル－１，５－ペンタンジオール、１，２－デカンジオール、２，２－ジイソブチル－１，３－プロパンジオール等が挙げられる。これらのアルキレングリコール構造は、一分子中に１種のみで有することも、２種以上を有することもできる。 Examples of the alkylene glycol structure include 1,2-ethanediol (ethylene glycol), 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1, 7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,2-propanediol (propylene glycol), 1,2-butanediol, 1,3-butanediol , 2,3-butanediol, 2-methyl-1,3-propanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 2,4-pentanediol, 2,2 -Dimethyl-1,3-propanediol (neopentyl glycol), 3-methyl-1,3-butanediol, 2-methyl-1,3-butanediol, 1,2-hexanediol, 1,5-hexanediol , 2,5-hexanediol, 3-methyl-1,5-pentanediol, 2,3-dimethyl-2,3-butanediol, 2-ethyl-2-methyl-1,3-propanediol, 1,2 -heptanediol, 2-methyl-2-propyl-1,3-propanediol, 2,4-dimethyl-2,4-pentanediol, 3,6-octanediol, 2,2,4-trimethyl-1,3 -pentanediol, 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 1,2-nonanediol, 1,8-nonanediol, 2,8-nonanediol, 2 -butyl-2-ethyl-1,3-propanediol, 2,4-diethyl-1,5-pentanediol, 1,2-decanediol, 2,2-diisobutyl-1,3-propanediol, etc. . One molecule may contain only one kind of these alkylene glycol structures, or two or more kinds thereof.
また、前記一分子中に１又は２個の（メタ）アクリロイル基及び一分子中にアルキレングリコール構造を有する化合物の市販品としては、例えば、ＭＩＷＯＮ社製「Ｍｉｒａｍｅｒ Ｍ１７０」、「Ｍｉｒａｍｅｒ Ｍ２０２」、「Ｍｉｒａｍｅｒ Ｍ２１０」、「Ｍｉｒａｍｅｒ Ｍ２１６」、「Ｍｉｒａｍｅｒ Ｍ２２０」、「Ｍｉｒａｍｅｒ Ｍ２２２」、「Ｍｉｒａｍｅｒ Ｍ２３２」、「Ｍｉｒａｍｅｒ Ｍ２８０」、「Ｍｉｒａｍｅｒ Ｍ２８２」、「Ｍｉｒａｍｅｒ Ｍ２８４」、「Ｍｉｒａｍｅｒ Ｍ２８６」、「Ｍｉｒａｍｅｒ Ｍ２０４０」、「Ｍｉｒａｍｅｒ Ｍ２３１」、「Ｍｉｒａｍｅｒ Ｍ２３３」、「Ｍｉｒａｍｅｒ Ｍ２３５」、「Ｍｉｒａｍｅｒ Ｍ２８１」、「Ｍｉｒａｍｅｒ Ｍ２８３」、新中村化学工業株式会社製「ＮＫエステル Ａ－３０Ｇ」、「ＮＫエステル Ａ－９０Ｇ」、「ＮＫエステル Ａ－１３０Ｇ」、「ＮＫエステル ＡＭ－３０ＰＧ」、「ＮＫエステル Ａ－２００」、「ＮＫエステル Ａ－４００」、「ＮＫエステル Ａ－６００」、「ＮＫエステル ＡＰＧ－１００」、「ＮＫエステル ＡＰＧ－２００」、「ＮＫエステル ＡＰＧ－４００」、「ＮＫエステル ＡＰＧ－７００」、「ＮＫエステル Ａ－ＰＴＭＧ－６５」、「ＮＫエステル Ｍ－２０Ｇ」、「ＮＫエステル Ｍ－３０Ｇ」、「ＮＫエステル Ｍ－４０Ｇ」、「ＮＫエステル Ｍ－９０Ｇ」、「ＮＫエステル Ｍ－１３０Ｇ」、「ＮＫエステル Ｍ－３０ＰＧ」、「ＮＫエステル ＥＨ－４Ｅ」、「ＮＫエステル Ｂ－２０Ｇ」、「ＮＫエステル Ｓ－１２Ｅ」、「ＮＫエステル ２Ｇ」、「ＮＫエステル ３Ｇ」、「ＮＫエステル ４Ｇ」、「ＮＫエステル ９Ｇ」、「ＮＫエステル １４Ｇ」、「ＮＫエステル ３ＰＧ」、「ＮＫエステル ９ＰＧ」、共栄社化学株式会社製「ライトエステルＢＣ」、「ライトエステル１３０ＭＡ」、「ライトエステルＢＣ」、「ライトエステル２ＥＧ」、「ライトエステル３ＥＧ」、「ライトエステル４ＥＧ」、「ライトエステル９ＥＧ」、「ライトエステル１４ＥＧ」、「ライトアクリレートＥＣ－Ａ」、「ライトアクリレートＭＴＧ－Ａ」、「ライトアクリレートＥＨＤＧ－ＡＴ」、「ライトアクリレート１３０Ａ」、「ライトアクリレートＤＰＭ－Ａ」、「ライトアクリレートＰ２Ｈ－Ａ」、「ライトアクリレートＰ－２００Ａ」、「ライトアクリレート３ＥＧ－Ａ」、「ライトアクリレート４ＥＧ－Ａ」、「ライトアクリレート９ＥＧ－Ａ」、「ライトアクリレート１４ＥＧ－Ａ」、「ライトアクリレートＰＴＭＧＡ－２５０」、日立化成株式会社製「ファンクリルＦＡ－２４０Ａ」、「ファンクリルＦＡ－Ｐ２４０Ａ」、「ファンクリルＦＡ－Ｐ２７０Ａ」、「ファンクリルＦＡ－ＰＴＧ９Ａ」、「ファンクリルＦＡ－４００Ｍ（１００）」、「ファンクリルＦＡ－２４０Ｍ」、「ファンクリルＦＡ－ＰＴＧ９Ｍ」、第一工業製薬株式会社製「ニューフロンティア ＭＥ－３」、「ニューフロンティア ＭＥ－４Ｓ」、「ニューフロンティア ＭＰＥ－６００」、「ニューフロンティア ＰＥ－２００」、「ニューフロンティア ＰＥ－３００」、「ニューフロンティア ＰＥ－４００」、「ニューフロンティア ＰＥ－６００」、「ニューフロンティア ＭＰＥＭ－４００」、「ニューフロンティア ＴＥＧＤＭＡ」、日本化薬株式会社製「ＫＡＹＡＲＡＤ ＰＥＧ４００ＤＡ」、「ＫＡＹＡＲＡＤ ＰＥＧ４００ＤＡ」、大阪有機化学工業株式会社製「ビスコート＃１９０」、「ビスコート＃ＭＴＧ」、「ＭＰＥ４００Ａ」、「ＭＰＥ５５０Ａ」、「ビスコート＃３１０ＨＰ」等が挙げられる。 In addition, as commercially available compounds having one or two (meth)acryloyl groups in one molecule and an alkylene glycol structure in one molecule, for example, "Miramer M170", "Miramer M202", and "Miramer M202" manufactured by MIWON. Miramer M210", "Miramer M216", "Miramer M220", "Miramer M222", "Miramer M232", "Miramer M280", "Miramer M282", "Miramer M284", "M Miramer M286", "Miramer M2040", " "Miramer M231", "Miramer M233", "Miramer M235", "Miramer M281", "Miramer M283", "NK Ester A-30G", "NK Ester A-90G", "NK Ester" manufactured by Shin-Nakamura Chemical Co., Ltd. A-130G", "NK Ester AM-30PG", "NK Ester A-200", "NK Ester A-400", "NK Ester A-600", "NK Ester APG-100", "NK Ester APG- 200", "NK Ester APG-400", "NK Ester APG-700", "NK Ester A-PTMG-65", "NK Ester M-20G", "NK Ester M-30G", "NK Ester M- 40G", "NK Ester M-90G", "NK Ester M-130G", "NK Ester M-30PG", "NK Ester EH-4E", "NK Ester B-20G", "NK Ester S-12E" , "NK Ester 2G", "NK Ester 3G", "NK Ester 4G", "NK Ester 9G", "NK Ester 14G", "NK Ester 3PG", "NK Ester 9PG", "Light" manufactured by Kyoeisha Chemical Co., Ltd. Ester BC", "Light Ester 130MA", "Lite Ester BC", "Lite Ester 2EG", "Lite Ester 3EG", "Lite Ester 4EG", "Lite Ester 9EG", "Lite Ester 14EG", "Light Acrylate EC" -A”, “Light Acrylate MTG-A”, “Light Acrylate EHDG-AT”, “Light Acrylate 130A”, “Light Acrylate DPM-A”, “Light Acrylate P2H-A”, “Light Acrylate P-200A”, "Light Acrylate 3EG-A", "Light Acrylate 4EG-A", "Light Acrylate 9EG-A", "Light Acrylate 14EG-A", "Light Acrylate PTMGA-250", "Fancryl FA-" manufactured by Hitachi Chemical Co., Ltd. 240A”, “Fankryl FA-P240A”, “Fankryl FA-P270A”, “Fankryl FA-PTG9A”, “Fankryl FA-400M (100)”, “Fankryl FA-240M”, “Fankryl FA -PTG9M”, “New Frontier ME-3”, “New Frontier ME-4S”, “New Frontier MPE-600”, “New Frontier PE-200”, “New Frontier PE-300” manufactured by Daiichi Kogyo Seiyaku Co., Ltd. , "New Frontier PE-400", "New Frontier PE-600", "New Frontier MPEM-400", "New Frontier TEGDMA", Nippon Kayaku Co., Ltd. "KAYARAD PEG400DA", "KAYARAD PEG400DA", Osaka Organic Chemical Examples include "Viscoat #190", "Viscoat #MTG", "MPE400A", "MPE550A", and "Viscoat #310HP" manufactured by Kogyo Co., Ltd.
さらに、本発明の活性エネルギー線硬化性樹脂組成物としては、必要に応じて、ウレタン（メタ）アクリレート、エポキシ（メタ）アクリレート、アクリル（メタ）アクリレート等を含有することもできる。 Furthermore, the active energy ray-curable resin composition of the present invention can also contain urethane (meth)acrylate, epoxy (meth)acrylate, acrylic (meth)acrylate, etc., if necessary.
本発明の硬化物は、例えば、前記活性エネルギー線硬化性樹脂組成物に、活性エネルギー線を照射することで得ることができる。前記活性エネルギー線としては、例えば、紫外線、電子線、α線、β線、γ線等の電離放射線が挙げられる。また、前記活性エネルギー線として、紫外線を用いる場合、紫外線による硬化反応を効率よく行う上で、窒素ガス等の不活性ガス雰囲気下で照射してもよく、空気雰囲気下で照射してもよい。 The cured product of the present invention can be obtained, for example, by irradiating the active energy ray-curable resin composition with active energy rays. Examples of the active energy ray include ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays. Further, when ultraviolet rays are used as the active energy rays, in order to efficiently perform the curing reaction by ultraviolet rays, the irradiation may be performed in an inert gas atmosphere such as nitrogen gas, or in an air atmosphere.
紫外線発生源としては、実用性、経済性の面から紫外線ランプが一般的に用いられている。具体的には、低圧水銀ランプ、高圧水銀ランプ、超高圧水銀ランプ、キセノンランプ、ガリウムランプ、メタルハライドランプ、太陽光、ＬＥＤ等が挙げられる。 As a source of ultraviolet light, an ultraviolet lamp is generally used from the viewpoint of practicality and economy. Specifically, low-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, xenon lamps, gallium lamps, metal halide lamps, sunlight, LEDs, etc. can be mentioned.
前記活性エネルギー線の積算光量は、特に制限されないが、１００～１０，０００ｍＪ／ｃｍ２であることが好ましく、３００～８，０００ｍＪ／ｃｍ２であることがより好ましい。積算光量を上記範囲内とすることで、光量不足による硬化不良、及び光量過剰による硬化物の劣化を抑制できる。The cumulative amount of active energy rays is not particularly limited, but is preferably 100 to 10,000 mJ/cm 2 , more preferably 300 to 8,000 mJ/cm 2 . By setting the cumulative light amount within the above range, curing failure due to insufficient light amount and deterioration of the cured product due to excessive light amount can be suppressed.
なお、前記活性エネルギー線の照射は、一段階で行ってもよいし、二段階以上に分けて行ってもよい。 Note that the irradiation with the active energy rays may be performed in one step, or may be performed in two or more steps.
前記硬化物のアッベ数νＤは、色収差を抑制できる観点から、５３以上であることが好ましく、５５～６０の範囲であることがより好ましい。 The Abbe number νD of the cured product is preferably 53 or more, more preferably in the range of 55 to 60, from the viewpoint of suppressing chromatic aberration.
また、前記硬化物の波長５８９ｎｍにおける屈折率ｎＤは、１．４８以上であることが好ましく、１．４９～１．５５の範囲がより好ましい。 Further, the refractive index nD of the cured product at a wavelength of 589 nm is preferably 1.48 or more, and more preferably in the range of 1.49 to 1.55.
本発明の積層体は、前記硬化物からなる樹脂層と、無機層とを有するものである。また、必要に応じて、基材を有していてもよい。 The laminate of the present invention has a resin layer made of the cured product and an inorganic layer. Moreover, it may have a base material if necessary.
前記無機層としては、無機化合物からなる層をいい、一般に、反射防止、耐擦り傷性等の機能を有するものである。 The inorganic layer is a layer made of an inorganic compound, and generally has functions such as antireflection and scratch resistance.
前記無機化合物としては、例えば、金属酸化物、複酸化物、金属窒化物、金属フッ化物、複フッ化物、ケイ素酸化物、ケイ素窒化物、及びそれらの混合物等が挙げられる。 Examples of the inorganic compound include metal oxides, double oxides, metal nitrides, metal fluorides, double fluorides, silicon oxides, silicon nitrides, and mixtures thereof.
前記金属としては、例えば、リチウム、ナトリウム、マグネシウム、アルミニウム、チタン、イットリウム、インジウム、スズ、ジルコニウム、ニオブ、セリウム、ハフニウム、タンタル、等が挙げられる。 Examples of the metal include lithium, sodium, magnesium, aluminum, titanium, yttrium, indium, tin, zirconium, niobium, cerium, hafnium, tantalum, and the like.
前記無機層を反射防止膜層として用いる場合、前記反射防止膜層は単層であってもよいが、低屈折率層と、高屈折率層とを有していてもよい。また、低屈折率層と高屈折率層は、それぞれ１層でも複数層であってもよい。なお、低屈折率層と高屈折率層の積層順序も特に限定されない。 When the inorganic layer is used as an antireflection layer, the antireflection layer may be a single layer, or may include a low refractive index layer and a high refractive index layer. Further, each of the low refractive index layer and the high refractive index layer may be one layer or multiple layers. Note that the stacking order of the low refractive index layer and the high refractive index layer is not particularly limited either.
前記高屈折率層に用いる無機化合物としては、例えば、チタン酸ランタン（ＬａＴｉＯ３）、酸化ジルコニウム（ＺｒＯ２）、酸化チタン（ＴｉＯ２）、酸化タンタル（Ｔａ２Ｏ５）、酸化ニオブ（Ｎｂ２Ｏ５）、酸化ハフニウム（ＨｆＯ２）、酸化セリウム（ＣｅＯ２）、酸化イットリウム（Ｙ２Ｏ３）、及びそれらの混合物等が挙げられる。Examples of the inorganic compound used in the high refractive index layer include lanthanum titanate (LaTiO 3 ), zirconium oxide (ZrO 2 ), titanium oxide (TiO 2 ), tantalum oxide (Ta 2 O 5 ), and niobium oxide (Nb 2 ) . O 5 ), hafnium oxide (HfO 2 ), cerium oxide (CeO 2 ), yttrium oxide (Y 2 O 3 ), and mixtures thereof.
前記低屈折率層に用いる無機化合物としては、例えば、フッ化マグネシウム（ＭｇＦ２）、二酸化ケイ素（ＳｉＯ２）、フッ化アルミニウム（ＡｌＦ３）、及びそれらの混合物等が挙げられる。Examples of the inorganic compound used in the low refractive index layer include magnesium fluoride (MgF 2 ), silicon dioxide (SiO 2 ), aluminum fluoride (AlF 3 ), and mixtures thereof.
前記無機層は、前記樹脂層の表面に成膜することで得られるものである。前記無機層の成膜方法は、特に制限されず、適宜公知の成膜方法を用いることができるが、物理蒸着（ＰＶＤ）または化学蒸着（ＣＶＤ）により成膜することが好ましい。 The inorganic layer is obtained by forming a film on the surface of the resin layer. The method for forming the inorganic layer is not particularly limited, and any known film forming method may be used as appropriate, but it is preferable to form the inorganic layer by physical vapor deposition (PVD) or chemical vapor deposition (CVD).
前記成膜方法は、成膜工程の一貫性及び簡素化の観点から、前記物理蒸着（ＰＶＤ）を用いることがより好ましく、例えば、真空蒸着、イオンプレーティング、スパッタリング等の方法が挙げられる。 The film forming method is preferably the physical vapor deposition (PVD) from the viewpoint of consistency and simplification of the film forming process, and examples thereof include methods such as vacuum evaporation, ion plating, and sputtering.
前記真空蒸着としては、例えば、抵抗加熱方式、高周波誘導加熱方式、電子ビーム加熱方式等を用いることができる。 As the vacuum deposition, for example, a resistance heating method, a high frequency induction heating method, an electron beam heating method, etc. can be used.
前記スパッタリングは、ＤＣスパッタでもＲＦスパッタでもよく、マグネトロンスパッタでもイオンビームスパッタでもよい。また、平行平板ターゲット方式でも対向ターゲット方式でもよい。また、真空チャンバー内に導入する気体としては、例えば、アルゴン、クリプトン、酸素、窒素、等が挙げられ、各々単独でも２種以上を混合して用いてもよい。 The sputtering may be DC sputtering or RF sputtering, magnetron sputtering or ion beam sputtering. Further, a parallel plate target method or a facing target method may be used. Furthermore, examples of the gas introduced into the vacuum chamber include argon, krypton, oxygen, nitrogen, and the like, and each may be used alone or in combination of two or more.
前記無機層の膜厚は、目的とする機能により適宜調整し得るが、反射防止機能を目的とする場合、１０ｎｍ～５，０００ｎｍの範囲が好ましく、無機層の膜強度と生産性の観点から、１００ｎｍ～２，０００ｎｍの範囲がより好ましく、２５０ｎｍ～１，０００ｎｍの範囲が特に好ましい。 The film thickness of the inorganic layer can be adjusted as appropriate depending on the intended function, but when the purpose is antireflection function, it is preferably in the range of 10 nm to 5,000 nm, and from the viewpoint of the film strength and productivity of the inorganic layer, The range of 100 nm to 2,000 nm is more preferable, and the range of 250 nm to 1,000 nm is particularly preferable.
前記基材としては、例えば、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート等のポリエステル系樹脂；ポリプロピレン、ポリエチレン、ポリメチルペンテン等のポリオレフィン系樹脂；セルロースアセテート（ジアセチルセルロース、トリアセチルセルロース等）、セルロースアセテートプロピオネート、セルロースアセテートブチレート、セルロースアセテートプロピオネートブチレート、セルロースアセテートフタレート、硝酸セルロース等のセルロース系樹脂；ポリメチルメタクリレート等のアクリル系樹脂；ポリ塩化ビニル、ポリ塩化ビニリデン等の塩化ビニル系樹脂；ポリビニルアルコール；エチレン一酢酸ビニル共重合体；ポリスチレン；ポリアミド；ポリカーボネート；ポリスルホン；ポリエーテルスルホン；ポリエーテルエーテルケトン；ポリイミド、ポリエーテルイミド等のポリイミド系樹脂；ノルボルネン系樹脂（例えば、日本ゼオン株式会社製「ゼオノア」）、変性ノルボルネン系樹脂（例えば、ＪＳＲ株式会社製「アートン」）、環状オレフィン共重合体（例えば、三井化学株式会社製「アペル」）などの樹脂フィルム；シリコン、シリコンカーバイド、シリコンナイトライド、サファイア、アルミニウムナイトライド、リン化ガリウム、ヒ化ガリウム、リン化インジウム、窒化ガリウム等の半導体ウエハー；石英ガラス、ホウケイ酸ガラス、ソーダ石灰ガラス、ケイ酸塩ガラス、光学ガラス（クラウンガラス、フリントガラス）等のガラスなどを用いることができる。 Examples of the base material include polyester resins such as polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate; polyolefin resins such as polypropylene, polyethylene, and polymethylpentene; cellulose acetate (diacetyl cellulose, triacetyl cellulose, etc.), and cellulose. Cellulose resins such as acetate propionate, cellulose acetate butyrate, cellulose acetate propionate butyrate, cellulose acetate phthalate, cellulose nitrate; acrylic resins such as polymethyl methacrylate; vinyl chloride such as polyvinyl chloride and polyvinylidene chloride polyvinyl alcohol; ethylene monovinyl acetate copolymer; polystyrene; polyamide; polycarbonate; polysulfone; polyether sulfone; polyether ether ketone; polyimide resins such as polyimide and polyetherimide; Resin films such as "Zeonor" manufactured by JSR Corporation), modified norbornene resins (e.g. "Arton" manufactured by JSR Corporation), cyclic olefin copolymers (e.g. "APEL" manufactured by Mitsui Chemicals Co., Ltd.); silicone, silicon carbide , silicon nitride, sapphire, aluminum nitride, gallium phosphide, gallium arsenide, indium phosphide, gallium nitride, etc.; quartz glass, borosilicate glass, soda lime glass, silicate glass, optical glass (crown glass, flint glass), etc. can be used.
前記フィルム基材に本発明の活性エネルギー線硬化性組成物を塗工する方法としては、例えば、ダイコート、マイクログラビアコート、グラビアコート、ロールコート、コンマコート、エアナイフコート、キスコート、スプレーコート、ディップコート、スピンナーコート、刷毛塗り、シルクスクリーンによるベタコート、ワイヤーバーコート、フローコート、ディスペンサー、インクジェット印刷、スクリーン印刷、オフセット印刷等が挙げられる。 Examples of methods for coating the active energy ray-curable composition of the present invention on the film base include die coating, microgravure coating, gravure coating, roll coating, comma coating, air knife coating, kiss coating, spray coating, and dip coating. , spinner coating, brush coating, solid coating by silk screen, wire bar coating, flow coating, dispenser, inkjet printing, screen printing, offset printing, etc.
本発明のレンズは、前記積層体からなるものである。 The lens of the present invention is made of the laminate described above.
前記レンズの製造方法としては、例えば、活性エネルギー線硬化性樹脂組成物を、ウエハーやセンサー基板上に塗布し、金型等を用いて所望の形状となるように活性エネルギー線を照射することで前記活性エネルギー線硬化性樹脂組成物を硬化させたのち、未硬化部分を有機溶剤で洗い流し、物理蒸着等によって無機層を活性エネルギー線硬化性樹脂組成物の硬化物表面に成膜させて得られた積層体を所望の形状に裁断する方法等が挙げられる。 As a method for manufacturing the lens, for example, an active energy ray-curable resin composition is applied onto a wafer or a sensor substrate, and active energy rays are irradiated using a mold or the like to form a desired shape. After curing the active energy ray curable resin composition, the uncured portion is washed away with an organic solvent, and an inorganic layer is formed on the surface of the cured product of the active energy ray curable resin composition by physical vapor deposition or the like. Examples include a method of cutting a laminate into a desired shape.
前記有機溶剤としては、例えば、メチルエチルケトン、アセトン、イソブチルケトン、シクロペンタノン、シクロヘキサノン等のケトン系溶剤；テトラヒドロフラン、ジオキソラン、ジオキサン等の環状エーテル系溶剤；酢酸メチル、酢酸エチル、酢酸ブチル等のエステル系溶剤；トルエン、キシレン、ソルベントナフサ等の芳香族系溶剤；シクロヘキサン、メチルシクロヘキサン等の脂環式炭化水素系溶剤；カルビトール、セロソルブ、メタノール、イソプロパノール、ブタノール、プロピレングリコールモノメチルエーテル等のアルコール系溶剤；アルキレングリコールモノアルキルエーテル、ジアルキレングリコールモノアルキルエーテル、ジアルキレングリコールモノアルキルエーテルアセテート等のグリコールエーテル系溶剤などが挙げられる。これらの有機溶剤は、単独で用いることも２種以上を併用することもできる。 Examples of the organic solvent include ketone solvents such as methyl ethyl ketone, acetone, isobutyl ketone, cyclopentanone, and cyclohexanone; cyclic ether solvents such as tetrahydrofuran, dioxolane, and dioxane; and ester solvents such as methyl acetate, ethyl acetate, and butyl acetate. Solvents: Aromatic solvents such as toluene, xylene, and solvent naphtha; Alicyclic hydrocarbon solvents such as cyclohexane and methylcyclohexane; Alcohol solvents such as carbitol, cellosolve, methanol, isopropanol, butanol, and propylene glycol monomethyl ether; Examples include glycol ether solvents such as alkylene glycol monoalkyl ether, dialkylene glycol monoalkyl ether, and dialkylene glycol monoalkyl ether acetate. These organic solvents can be used alone or in combination of two or more.
以下、実施例と比較例とにより、本発明を具体的に説明する。 Hereinafter, the present invention will be specifically explained with reference to Examples and Comparative Examples.
なお、本実施例において、重量平均分子量（Ｍｗ）は、ゲル・パーミエーション・クロマトグラフィー（ＧＰＣ）を用い、下記の条件により測定した値である。 In this example, the weight average molecular weight (Mw) is a value measured using gel permeation chromatography (GPC) under the following conditions.
測定装置 ； 東ソー株式会社製 ＨＬＣ－８２２０
カラム ； 東ソー株式会社製ガードカラムＨＸＬ－Ｈ
＋東ソー株式会社製 ＴＳＫｇｅｌ Ｇ５０００ＨＸＬ
＋東ソー株式会社製 ＴＳＫｇｅｌ Ｇ４０００ＨＸＬ
＋東ソー株式会社製 ＴＳＫｇｅｌ Ｇ３０００ＨＸＬ
＋東ソー株式会社製 ＴＳＫｇｅｌ Ｇ２０００ＨＸＬ
検出器 ； ＲＩ（示差屈折計）
データ処理：東ソー株式会社製 ＳＣ－８０１０
測定条件： カラム温度 ４０℃
溶媒 テトラヒドロフラン
流速 １．０ｍｌ／分
標準 ；ポリスチレン
試料 ；樹脂固形分換算で０．４質量％のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの（１００μｌ）Measuring device: HLC-8220 manufactured by Tosoh Corporation
Column: Guard column H XL -H manufactured by Tosoh Corporation
+TSKgel G5000HXL manufactured by Tosoh Corporation
+TSKgel G4000HXL manufactured by Tosoh Corporation
+TSKgel G3000HXL manufactured by Tosoh Corporation
+TSKgel G2000HXL manufactured by Tosoh Corporation
Detector; RI (differential refractometer)
Data processing: Tosoh Corporation SC-8010
Measurement conditions: Column temperature 40℃
Solvent Tetrahydrofuran
Flow rate 1.0ml/min Standard: Polystyrene Sample: 0.4% by mass of tetrahydrofuran solution (calculated as resin solid content) filtered through a microfilter (100μl)
（合成例１：アクリロイル基を有する多分岐型高分子化合物（Ａ－１）の製造）
パーシャルコンデンサー、温度計、攪拌棒を具備した反応釜にトリメチロールプロパン１３４質量部、ジメチロールプロピオン酸２，５００質量部、パラトルエンスルホン酸１５質量部を仕込み１００℃下にて攪拌し、均一な液状混合溶融物とした。次いで、トルエン１００質量部を注入後１４０℃に昇温し、トルエンを還流しつつ発生する水を共沸により系外に留去した。次いで、１４０℃で３時間反応を継続した後、系外へトルエンを留去し、多分岐ポリエステルポリオール（ａ）を得た。多分岐ポリエステルポリオール（ａ）の重量平均分子量は１，８００であった。(Synthesis Example 1: Production of a hyperbranched polymer compound (A-1) having an acryloyl group)
134 parts by mass of trimethylolpropane, 2,500 parts by mass of dimethylolpropionic acid, and 15 parts by mass of paratoluenesulfonic acid were placed in a reaction vessel equipped with a partial condenser, a thermometer, and a stirring bar, and stirred at 100°C to form a homogeneous mixture. It was made into a liquid mixed melt. Next, 100 parts by mass of toluene was injected and the temperature was raised to 140° C., and water generated while refluxing the toluene was distilled out of the system by azeotropy. Next, after continuing the reaction at 140° C. for 3 hours, toluene was distilled out of the system to obtain a hyperbranched polyester polyol (a). The weight average molecular weight of the hyperbranched polyester polyol (a) was 1,800.
次いで、パーシャルコンデンサー、温度計、攪拌棒を具備した反応釜に、多分岐ポリエステルポリオール（ａ）１００質量部とアクリル酸８０質量部、メトキノン０．２６質量部、パラトルエンスルホン酸１．７０質量部、トルエン１２０質量部を仕込み、反応温度１１０℃でトルエンを還流しながら水を共沸により系外に除いた。次いで、１１０℃で５時間反応を継続した後、反応混合物を２０質量％の水酸化ナトリウム水溶液で中和し、食塩水で３回洗浄した。最後に系外へトルエンを減圧蒸留して、アクリロイル基を有する多分岐型高分子化合物（Ａ－１）を得た。このアクリロイル基を有する多分岐型高分子化合物（Ａ－１）の重量平均分子量は２，６００であった。 Next, 100 parts by mass of hyperbranched polyester polyol (a), 80 parts by mass of acrylic acid, 0.26 parts by mass of methoquinone, and 1.70 parts by mass of paratoluenesulfonic acid were placed in a reaction vessel equipped with a partial condenser, a thermometer, and a stirring bar. , 120 parts by mass of toluene were charged, and water was removed from the system by azeotropy while toluene was refluxed at a reaction temperature of 110°C. After continuing the reaction at 110° C. for 5 hours, the reaction mixture was neutralized with a 20% by mass aqueous sodium hydroxide solution and washed three times with brine. Finally, toluene was distilled out of the system under reduced pressure to obtain a hyperbranched polymer compound (A-1) having an acryloyl group. The weight average molecular weight of this hyperbranched polymer compound (A-1) having an acryloyl group was 2,600.
（実施例１：活性エネルギー線硬化性樹脂組成物（１）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）８５質量部、トリシクロデカンジメタノールジメタクリレート（新中村化学工業株式会社製「ＮＫ エステル ＤＣＰ」）１０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１）を得た。(Example 1: Preparation of active energy ray-curable resin composition (1))
In a 200 mL brown bottle, 5 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) 85 parts by mass, tricyclodecane dimethanol dimethacrylate ("NK Ester DCP" manufactured by Shin-Nakamura Chemical Co., Ltd.) 10 parts by mass, and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended, and the mixture was heated at 60°C. Active energy ray curable composition (1) was obtained by heating for 30 minutes to uniformly dissolve and defoam.
（実施例２：活性エネルギー線硬化性樹脂組成物（２）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）８０質量部、トリシクロデカンジメタノールジメタクリレート（新中村化学工業株式会社製「ＮＫ エステル ＤＣＰ」）１５質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（２）を得た。(Example 2: Preparation of active energy ray-curable resin composition (2))
In a 200 mL brown bottle, 5 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) 80 parts by mass, 15 parts by mass of tricyclodecane dimethanol dimethacrylate ("NK Ester DCP" manufactured by Shin-Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended, and the mixture was heated at 60 °C. Active energy ray curable composition (2) was obtained by heating for 30 minutes to uniformly dissolve and defoam.
（実施例３：活性エネルギー線硬化性樹脂組成物（３）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）１０質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）７５質量部、トリシクロデカンジメタノールジメタクリレート（新中村化学工業株式会社製「ＮＫ エステル ＤＣＰ」）１５質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１）を得た。(Example 3: Preparation of active energy ray-curable resin composition (3))
In a 200 mL brown bottle, 10 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) 75 parts by mass, 15 parts by mass of tricyclodecane dimethanol dimethacrylate ("NK Ester DCP" manufactured by Shin-Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended, and the mixture was heated at 60°C. Active energy ray curable composition (1) was obtained by heating for 30 minutes to uniformly dissolve and defoam.
（実施例４：活性エネルギー線硬化性樹脂組成物（４）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）４５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）５５質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（４）を得た。(Example 4: Preparation of active energy ray-curable resin composition (4))
In a 200 mL brown bottle, 45 parts by mass of the hyperbranched polymer compound (A-1) having acryloyl groups obtained in Synthesis Example 1, polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) 55 parts by mass, 1 part by mass of a photopolymerization initiator (Runtech Chemical Co., Ltd. "Runtecure 1104"), heated at 60°C for 30 minutes to uniformly dissolve and defoam, to form an active energy ray-curable composition ( 4) was obtained.
（実施例５：活性エネルギー線硬化性樹脂組成物（５）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）７０質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）３０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（５）を得た。(Example 5: Preparation of active energy ray-curable resin composition (5))
In a 200 mL brown bottle, 70 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) 30 parts by mass and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended and heated at 60°C for 30 minutes to uniformly dissolve and defoam, thereby creating an active energy ray-curable composition ( 5) was obtained.
（実施例６：活性エネルギー線硬化性樹脂組成物（６）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）６０質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（６）を得た。(Example 6: Preparation of active energy ray-curable resin composition (6))
In a 200 mL brown bottle, 60 parts by mass of the hyperbranched polymer compound (A-1) having acryloyl groups obtained in Synthesis Example 1, polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) 40 parts by mass and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended, heated at 60°C for 30 minutes to uniformly dissolve, and defoam to form an active energy ray-curable composition ( 6) was obtained.
（実施例７：活性エネルギー線硬化性樹脂組成物（７）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）５０質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）５０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（７）を得た。(Example 7: Preparation of active energy ray-curable resin composition (7))
In a 200 mL brown bottle, 50 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) 50 parts by mass, 1 part by mass of a photopolymerization initiator (Runtech Chemical Co., Ltd. "Runtecure 1104"), heated at 60°C for 30 minutes to uniformly dissolve and defoam, to form an active energy ray-curable composition ( 7) was obtained.
（実施例８：活性エネルギー線硬化性樹脂組成物（８）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）６５質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（８）を得た。(Example 8: Preparation of active energy ray-curable resin composition (8))
In a 200 mL brown bottle, 35 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) 65 parts by mass, 1 part by mass of a photopolymerization initiator (Runtech Chemical Co., Ltd. "Runtecure 1104") were mixed, heated at 60°C for 30 minutes to uniformly dissolve and defoam, thereby creating an active energy ray-curable composition ( 8) was obtained.
（実施例９：活性エネルギー線硬化性樹脂組成物（９）の調製）
２００ｍＬ褐色ビンに合成例１で得たアクリロイル基を有する多分岐型高分子化合物（Ａ－１）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（９）を得た。(Example 9: Preparation of active energy ray-curable resin composition (9))
In a 200 mL brown bottle, 35 parts by mass of the hyperbranched polymer compound (A-1) having an acryloyl group obtained in Synthesis Example 1, polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) 45 parts by mass, 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin-Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.), An active energy ray-curable composition (9) was obtained by heating the mixture for a few minutes to uniformly dissolve it and defoaming it.
（実施例１０：活性エネルギー線硬化性樹脂組成物（１０）の調製）
２００ｍＬ褐色ビンにアクリロイル基を有するデンドリマー型高分子化合物（大阪有機化学工業株式会社製「ビスコート＃１０００ＬＴ」）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１０）を得た。(Example 10: Preparation of active energy ray-curable resin composition (10))
A 200 mL brown bottle contains 35 parts by mass of a dendrimer type polymer compound having an acryloyl group ("Viscoat #1000LT" manufactured by Osaka Organic Chemical Industry Co., Ltd.), polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) ), 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin-Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.), and heated at 60°C. The active energy ray-curable composition (10) was obtained by heating for 30 minutes to uniformly dissolve and defoam.
（実施例１１：活性エネルギー線硬化性樹脂組成物（１１）の調製）
２００ｍＬ褐色ビンにアクリロイル基を有するハイパーブランチ型高分子化合物（Ａｒｋｅｍａ社製「ＣＮ２３０２」）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１１）を得た。(Example 11: Preparation of active energy ray-curable resin composition (11))
In a 200 mL brown bottle, 35 parts by mass of a hyperbranched polymer compound having an acryloyl group (“CN2302” manufactured by Arkema) and 45 parts by mass of polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) , 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended and heated at 60 ° C. for 30 minutes. By uniformly dissolving and defoaming, an active energy ray-curable composition (11) was obtained.
（実施例１２：活性エネルギー線硬化性樹脂組成物（１２）の調製）
２００ｍＬ褐色ビンにアクリロイル基を有するハイパーブランチ型高分子化合物（Ａｒｋｅｍａ社製「ＣＮ２３０３」）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１２）を得た。(Example 12: Preparation of active energy ray-curable resin composition (12))
In a 200 mL brown bottle, 35 parts by mass of a hyperbranched polymer compound having an acryloyl group (“CN2303” manufactured by Arkema), 45 parts by mass of polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) , 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin Nakamura Chemical Co., Ltd.) and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended, and heated at 60 ° C. for 30 minutes. By uniformly dissolving and defoaming, an active energy ray-curable composition (12) was obtained.
（実施例１３：活性エネルギー線硬化性樹脂組成物（１３）の調製）
２００ｍＬ褐色ビンにアクリロイル基を有するハイパーブランチ型高分子化合物（Ａｒｋｅｍａ社製「ＣＮ２３０４」）３５質量部、ポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性組成物（１３）を得た。(Example 13: Preparation of active energy ray-curable resin composition (13))
In a 200 mL brown bottle, 35 parts by mass of a hyperbranched polymer compound having an acryloyl group ("CN2304" manufactured by Arkema), 45 parts by mass of polycarbonate diacrylate ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) , 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin Nakamura Chemical Co., Ltd.), and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended and heated at 60 ° C. for 30 minutes. By uniformly dissolving and defoaming, an active energy ray-curable composition (13) was obtained.
（比較例１：活性エネルギー線硬化性樹脂組成物（Ｒ１）の調製）
２００ｍＬ褐色ビンにポリカーボネートジアクリレート（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）８１質量部、トリシクロデカンジメタノールジメタクリレート（新中村化学工業株式会社製「ＮＫ エステル ＤＣＰ」）１９質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」）１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性樹脂組成物（Ｒ１）を得た。(Comparative Example 1: Preparation of active energy ray-curable resin composition (R1))
81 parts by mass of polycarbonate diacrylate (“UM-90 (1/3) DA” manufactured by Ube Industries, Ltd.) and tricyclodecane dimethanol dimethacrylate (“NK Ester DCP” manufactured by Shin-Nakamura Chemical Industries, Ltd.) in a 200 mL brown bottle. 19 parts by mass and 1 part by mass of a photopolymerization initiator (Runtech Chemical Co., Ltd. "Runtecure 1104") were mixed and heated at 60°C for 30 minutes to uniformly dissolve and degas, thereby creating an active energy ray-curable resin composition. Product (R1) was obtained.
（比較例２：活性エネルギー線硬化性樹脂組成物（Ｒ２）の調製）
２００ｍＬ褐色ビンにジペンタエリスリトールヘキサアクリレート（共栄社化学株式会社製「Ａ－ＤＰＨ６Ａ」）３５質量部、（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」）１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性樹脂組成物（Ｒ２）を得た。(Comparative Example 2: Preparation of active energy ray-curable resin composition (R2))
In a 200 mL brown bottle, 35 parts by mass of dipentaerythritol hexaacrylate ("A-DPH6A" manufactured by Kyoeisha Chemical Co., Ltd.), 45 parts by mass ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.), polyethylene glycol di 20 parts by mass of acrylate ("NK Ester A-400" manufactured by Shin-Nakamura Chemical Co., Ltd.) and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were mixed and heated at 60°C for 30 minutes to homogenize. An active energy ray-curable resin composition (R2) was obtained by dissolving the active energy ray-curable resin composition (R2) and defoaming.
（比較例３：活性エネルギー線硬化性樹脂組成物（Ｒ３）の調製）
２００ｍＬ褐色ビンにポリペンタエリスリトールポリアクリレート（大阪有機化学工業株式会社製「ビスコート＃８０２」）３５質量部、（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」）１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性樹脂組成物（Ｒ３）を得た。(Comparative Example 3: Preparation of active energy ray-curable resin composition (R3))
In a 200 mL brown bottle, 35 parts by mass of polypentaerythritol polyacrylate ("Viscoat #802" manufactured by Osaka Organic Chemical Industry Co., Ltd.), 45 parts by mass ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.), polyethylene 20 parts by mass of glycol diacrylate ("NK Ester A-400" manufactured by Shin Nakamura Chemical Co., Ltd.) and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were blended and heated at 60 ° C. for 30 minutes. By uniformly dissolving and defoaming, an active energy ray-curable resin composition (R3) was obtained.
（比較例４：活性エネルギー線硬化性樹脂組成物（Ｒ４）の調製）
２００ｍＬ褐色ビンにポリペンタエリスリトールポリアクリレート（新中村化学工業株式会社製「ＮＫ エステル ＴＰＯＡ－３０」）３５質量部、（宇部興産株式会社製「ＵＭ－９０（１／３）ＤＡ」）４５質量部、ポリエチレングリコールジアクリレート（新中村化学工業株式会社製「ＮＫ エステル Ａ－４００」）２０質量部、光重合開始剤（Ｒｕｎｔｅｃｈ Ｃｈｅｍｉｃａｌ社製「Ｒｕｎｔｅｃｕｒｅ１１０４」）１質量部配合し、６０℃で３０分加温して均一に溶解し、脱泡することで、活性エネルギー線硬化性樹脂組成物（Ｒ４）を得た。(Comparative Example 4: Preparation of active energy ray-curable resin composition (R4))
35 parts by mass of polypentaerythritol polyacrylate ("NK Ester TPOA-30" manufactured by Shin Nakamura Chemical Co., Ltd.), 45 parts by mass ("UM-90 (1/3) DA" manufactured by Ube Industries, Ltd.) in a 200 mL brown bottle. , 20 parts by mass of polyethylene glycol diacrylate ("NK Ester A-400" manufactured by Shin-Nakamura Chemical Co., Ltd.) and 1 part by mass of a photopolymerization initiator ("Runtecure 1104" manufactured by Runtech Chemical Co., Ltd.) were mixed and heated at 60°C for 30 minutes. An active energy ray-curable resin composition (R4) was obtained by heating, uniformly dissolving, and defoaming.
上記の実施例及び比較例で得られた活性エネルギー線硬化性樹脂組成物を用いて、下記の評価を行った。評価結果を表１および表２に記載する。 The following evaluations were performed using the active energy ray-curable resin compositions obtained in the above Examples and Comparative Examples. The evaluation results are shown in Tables 1 and 2.
［屈折率の測定方法］
実施例及び比較例で得られた活性エネルギー線硬化性組成物を三角プリズム型（厚さ５ｍｍ、１辺の長さ１０ｍｍ）に流し込み、アイグラフィックス株式会社製ベルトコンベアー式紫外線照射装置（１２０Ｗメタルハライドランプ）を使用して、３，０００ｍＪ／ｃｍ２の紫外線を照射して三角プリズム形状の硬化物を作製した。得られた硬化物を株式会社島津製作所製カルニュー精密屈折計「ＫＰＲ－３０００」を使用して屈折率を測定した。なお、硬化物の屈折率（ｎＤ）に最も近い屈折率（ｎＤ）を有するマッチング液を適宜選択して用いた。[Refractive index measurement method]
The active energy ray-curable compositions obtained in Examples and Comparative Examples were poured into a triangular prism shape (thickness 5 mm, side length 10 mm), and a belt conveyor type ultraviolet irradiation device (120W metal halide A triangular prism-shaped cured product was produced by irradiating ultraviolet rays of 3,000 mJ/cm 2 using a lamp). The refractive index of the obtained cured product was measured using a Karnew precision refractometer "KPR-3000" manufactured by Shimadzu Corporation. Note that a matching liquid having a refractive index (nD) closest to that of the cured product was appropriately selected and used.
［アッベ数の測定方法］
実施例および比較例で得られた活性エネルギー線硬化性組成物を三角プリズム型（厚さ５ｍｍ、１辺の長さ１０ｍｍ）に流し込み、アイグラフィックス株式会社製ベルトコンベアー式紫外線照射装置（１２０Ｗメタルハライドランプ）を使用して、３，０００ｍＪ／ｃｍ２の紫外線を照射して三角プリズム形状の硬化物を作製した。得られた硬化物を株式会社島津製作所製カルニュー精密屈折計「ＫＰＲ－３０００」を使用してアッベ数を測定した。なお、硬化物の屈折率（ｎＤ）に最も近い屈折率（ｎＤ）を有するマッチング液を適宜選択して用いた。[Method of measuring Abbe number]
The active energy ray-curable compositions obtained in Examples and Comparative Examples were poured into a triangular prism shape (thickness 5 mm, side length 10 mm), and a belt conveyor type ultraviolet irradiation device (120W metal halide A triangular prism-shaped cured product was produced by irradiating ultraviolet rays of 3,000 mJ/cm 2 using a lamp). The Abbe number of the obtained cured product was measured using a Carnew precision refractometer "KPR-3000" manufactured by Shimadzu Corporation. Note that a matching liquid having a refractive index (nD) closest to that of the cured product was appropriately selected and used.
（実施例１４：積層体（１）の作製）
実施例１で得た活性エネルギー線硬化性樹脂組成物（１）を、シランカップリング剤（信越化学工業株式会社製「ＫＢＭ－５１０３」）により密着処理を施したガラス基板上にスポイトを用いて滴下し、金型で挟み込み、ＬＥＤ光照射装置（岩崎電気株式会社製「ＬＨＰＵＶ３６５」）を用いて、照射強度５０ｍＷ／ｃｍ２、積算光量４５０ｍＪ／ｃｍ２で半硬化させ、金型を離形した。得られた半硬化物上の未硬化の樹脂組成物を、シクロペンタノンを溶剤として用いて洗い流したのち、同ＬＥＤ照射装置を用いて、照射強度５０ｍＷ／ｃｍ２、積算光量７５５０ｍＪ／ｃｍ２で完全に硬化させた。次いで、１００℃に熱したオーブン内に硬化物を入れて、９０分間のアニール処理を行い硬化物を得た。こうして得られた硬化物を、マグネトロンスパッタ装置（株式会社島津製作所製「ＨＳＲ－５２２」）を用いて、ターゲット：ＳｉＯ２、導入ガス：Ａｒ、ガス流量：１５ｓｃｃｍ、室温２５℃、スパッタ時間：５５ｍｉｎの条件でスパッタリングを行い、前記硬化物の表面上に、ＳｉＯ２膜を０．６μｍの厚さで積層して積層体（１）を得た。(Example 14: Production of laminate (1))
Using a dropper, the active energy ray-curable resin composition (1) obtained in Example 1 was placed on a glass substrate that had been subjected to adhesion treatment with a silane coupling agent ("KBM-5103" manufactured by Shin-Etsu Chemical Co., Ltd.). It was dropped, sandwiched between molds, and semi-cured using an LED light irradiation device (LHPUV365 manufactured by Iwasaki Electric Co., Ltd.) at an irradiation intensity of 50 mW/cm 2 and an integrated light amount of 450 mJ/cm 2 , and the mold was released. . After washing off the uncured resin composition on the obtained semi-cured product using cyclopentanone as a solvent, it was irradiated with the same LED irradiation device at an irradiation intensity of 50 mW/cm 2 and an integrated light amount of 7550 mJ/cm 2 . fully cured. Next, the cured product was placed in an oven heated to 100° C. and annealed for 90 minutes to obtain a cured product. The thus obtained cured product was sputtered using a magnetron sputtering device ("HSR-522" manufactured by Shimadzu Corporation), target: SiO 2 , introduced gas: Ar, gas flow rate: 15 sccm, room temperature 25°C, sputtering time: 55 min. Sputtering was performed under the following conditions, and a 0.6 μm thick SiO 2 film was laminated on the surface of the cured product to obtain a laminate (1).
（実施例１５：積層体（２）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（２）を用いた以外は、実施例１４と同様にして積層体（２）を得た。(Example 15: Production of laminate (2))
A laminate (2) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (2) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例１６：積層体（３）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（３）を用いた以外は、実施例１４と同様にして積層体（３）を得た。(Example 16: Production of laminate (3))
A laminate (3) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (3) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例１７：積層体（４）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（４）を用いた以外は、実施例１４と同様にして積層体（４）を得た。(Example 17: Production of laminate (4))
A laminate (4) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (4) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例１８：積層体（５）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（５）を用いた以外は、実施例１４と同様にして積層体（５）を得た。(Example 18: Production of laminate (5))
A laminate (5) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (5) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例１９：積層体（６）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（６）を用いた以外は、実施例１４と同様にして積層体（６）を得た。(Example 19: Production of laminate (6))
A laminate (6) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (6) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２０：積層体（７）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（７）を用いた以外は、実施例１４と同様にして積層体（７）を得た。(Example 20: Production of laminate (7))
A laminate (7) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (7) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２１：積層体（８）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（８）を用いた以外は、実施例１４と同様にして積層体（８）を得た。(Example 21: Production of laminate (8))
A laminate (8) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (8) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２２：積層体（９）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（９）を用いた以外は、実施例１４と同様にして積層体（９）を得た。(Example 22: Production of laminate (9))
A laminate (9) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (9) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２３：積層体（１０）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（１０）を用いた以外は、実施例１４と同様にして積層体（１０）を得た。
(Example 23: Production of laminate (10))
A laminate (10) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (10) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２４：積層体（１１）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（１１）を用いた以外は、実施例１４と同様にして積層体（１１）を得た。(Example 24: Production of laminate (11))
A laminate (11) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (11) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２５：積層体（１２）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（１２）を用いた以外は、実施例１４と同様にして積層体（１１）を得た。(Example 25: Production of laminate (12))
A laminate (11) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (12) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（実施例２６：積層体（１３）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（１３）を用いた以外は、実施例１４と同様にして積層体（１３）を得た。(Example 26: Production of laminate (13))
A laminate (13) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (13) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（比較例５：積層体（Ｒ１）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（Ｒ１）を用いた以外は、実施例１４と同様にして積層体（Ｒ１）を得た。(Comparative Example 5: Production of laminate (R1))
A laminate (R1) was produced in the same manner as in Example 14, except that the active energy ray curable resin composition (R1) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（比較例６：積層体（Ｒ２）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（Ｒ２）を用いた以外は、実施例１４と同様にして積層体（Ｒ２）を得た。(Comparative Example 6: Production of laminate (R2))
A laminate (R2) was produced in the same manner as in Example 14, except that the active energy ray curable resin composition (R2) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（比較例７：積層体（Ｒ３）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（Ｒ３）を用いた以外は、実施例１１と同様にして積層体（Ｒ３）を得た。(Comparative Example 7: Production of laminate (R3))
A laminate (R3) was produced in the same manner as in Example 11, except that the active energy ray curable resin composition (R3) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
（比較例８：積層体（Ｒ４）の作製）
実施例１４で用いた活性エネルギー線硬化性樹脂組成物（１）に代えて、活性エネルギー線硬化性樹脂組成物（Ｒ４）を用いた以外は、実施例１４と同様にして積層体（Ｒ４）を得た。(Comparative Example 8: Production of laminate (R4))
A laminate (R4) was prepared in the same manner as in Example 14, except that the active energy ray curable resin composition (R4) was used in place of the active energy ray curable resin composition (1) used in Example 14. I got it.
上記の実施例及び比較例で得られた積層体を用いて、下記の評価を行った。 The following evaluations were performed using the laminates obtained in the above Examples and Comparative Examples.
［耐クラック性の評価方法］
実施例１１から２０で得られた積層体（１）から（１０）、及び比較例８から１４で得られた積層体（Ｒ１）から（Ｒ７）を、１７５℃に加温したオーブンに入れ、５分間熱処理を行った後、積層体（無機層）の表面をマイクロスコープ（株式会社キーエンス製「ＶＨＸ９００」）で観察し、下記の基準に従い評価した。
○：積層体表面にクラックが生じなかった。
△：積層体表面に１～３本クラックが生じた。
×：積層体表面に４本以上のクラックが生じた。[Crack resistance evaluation method]
The laminates (1) to (10) obtained in Examples 11 to 20 and the laminates (R1) to (R7) obtained in Comparative Examples 8 to 14 were placed in an oven heated to 175°C, After heat treatment for 5 minutes, the surface of the laminate (inorganic layer) was observed with a microscope ("VHX900" manufactured by Keyence Corporation) and evaluated according to the following criteria.
○: No cracks were generated on the surface of the laminate.
Δ: 1 to 3 cracks were generated on the surface of the laminate.
×: Four or more cracks were generated on the surface of the laminate.
実施例１１から２０で得られた積層体（１）から（１０）、及び比較例８から１４で得られた積層体（Ｒ１）から（Ｒ７）の評価結果を表３および表４に示す。 The evaluation results of the laminates (1) to (10) obtained in Examples 11 to 20 and the laminates (R1) to (R7) obtained in Comparative Examples 8 to 14 are shown in Tables 3 and 4.
表１及び３に示した実施例１から２６は、（メタ）アクリロイル基を有する多分岐型高分子化合物（Ａ）を含有する活性エネルギー線硬化性樹脂組成物の例である。当該活性エネルギー線硬化性樹脂組成物からなる樹脂層を有する積層体は、前記樹脂層上に成膜した無機層のクラック発生を抑制し、優れた耐クラック性を有することが確認できた。 Examples 1 to 26 shown in Tables 1 and 3 are examples of active energy ray-curable resin compositions containing the (meth)acryloyl group-containing hyperbranched polymer compound (A). It was confirmed that a laminate having a resin layer made of the active energy ray-curable resin composition suppressed the occurrence of cracks in the inorganic layer formed on the resin layer and had excellent crack resistance.
一方、比較例１から８は、（メタ）アクリロイル基を有する多分岐型高分子化合物（Ａ）を含有しない活性エネルギー線硬化性樹脂組成物の例である。当該活性エネルギー線硬化性樹脂組成物からなる樹脂層を有する積層体は、１７５℃で５分間の熱処理後、表面に４本以上のクラックが生じたことから、前記樹脂層上に成膜した無機層のクラック発生を抑制する耐クラック性は著しく不十分であることが確認できた。 On the other hand, Comparative Examples 1 to 8 are examples of active energy ray-curable resin compositions that do not contain the (meth)acryloyl group-containing hyperbranched polymer compound (A). The laminate having a resin layer made of the active energy ray-curable resin composition had four or more cracks on the surface after heat treatment at 175°C for 5 minutes. It was confirmed that the crack resistance, which suppresses the occurrence of cracks in the layer, was extremely insufficient.
Claims (6)
前記多分岐型高分子化合物（Ａ）が、デンドリマー構造を有する化合物、ハイパーブランチ構造を有する化合物、及びスター構造を有する化合物からなる群より選ばれる１種以上であり、
前記多分岐型高分子化合物（Ａ）の重量平均分子量は１０００～１００００の範囲であり、
前記多分岐型高分子化合物（Ａ）の含有量が、樹脂層形成用活性エネルギー線硬化性樹脂組成物全体を１００質量部に対して、１～８０質量部であり、
カーボネート構造を有する（メタ）アクリル化合物、環状構造を有する（メタ）アクリル化合物、一分子中に１又は２個の（メタ）アクリロイル基及び一分子中にアルキレングリコール構造を有する化合物のいずれか１つ又は複数をさらに含有し、
前記のカーボネート構造を有する（メタ）アクリル化合物、環状構造を有する（メタ）アクリル化合物、一分子中に１又は２個の（メタ）アクリロイル基及び一分子中にアルキレングリコール構造を有する化合物の合計含有量が樹脂層形成用活性エネルギー線硬化性樹脂組成物全体を１００質量部に対して、３０～９５質量部である
樹脂層形成用活性エネルギー線硬化性樹脂組成物。 An active energy ray-curable resin composition for forming a resin layer of a laminate having a resin layer and an inorganic layer, wherein the active energy ray-curable resin composition is a hyperbranched polymer compound having a (meth)acryloyl group. It contains (A) ,
The hyperbranched polymer compound (A) is one or more selected from the group consisting of a compound having a dendrimer structure, a compound having a hyperbranched structure, and a compound having a star structure,
The weight average molecular weight of the hyperbranched polymer compound (A) is in the range of 1000 to 10000,
The content of the hyperbranched polymer compound (A) is 1 to 80 parts by mass based on 100 parts by mass of the entire active energy ray-curable resin composition for forming a resin layer,
Any one of a (meth)acrylic compound having a carbonate structure, a (meth)acrylic compound having a cyclic structure, a compound having one or two (meth)acryloyl groups in one molecule, and an alkylene glycol structure in one molecule. or further contains a plurality of
Total content of the above-mentioned (meth)acrylic compound having a carbonate structure, (meth)acrylic compound having a cyclic structure, 1 or 2 (meth)acryloyl groups in one molecule, and a compound having an alkylene glycol structure in one molecule. The amount is 30 to 95 parts by mass based on 100 parts by mass of the entire active energy ray-curable resin composition for forming a resin layer.
Active energy ray-curable resin composition for forming a resin layer.
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| JP2011074280A (en) | 2009-09-30 | 2011-04-14 | Fujifilm Corp | Star polymer, and curable resin composition |
| JP2013204011A (en) | 2012-03-29 | 2013-10-07 | Osaka Gas Chem Kk | Hard coat resin composition, cured product of the same, and method of manufacturing cured product |
| WO2014157590A1 (en) | 2013-03-29 | 2014-10-02 | Hoya株式会社 | Coating composition |
| WO2018105441A1 (en) | 2016-12-08 | 2018-06-14 | Dic株式会社 | Active-energy-beam-curable resin composition, and laminate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2021157632A1 (en) | 2021-08-12 |
| WO2021157632A1 (en) | 2021-08-12 |
| TW202130668A (en) | 2021-08-16 |
| KR20220139873A (en) | 2022-10-17 |
| CN115066329A (en) | 2022-09-16 |
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