TW201819424A - Active-energy-beam curable composition and film using same - Google Patents
Active-energy-beam curable composition and film using same Download PDFInfo
- Publication number
- TW201819424A TW201819424A TW106117793A TW106117793A TW201819424A TW 201819424 A TW201819424 A TW 201819424A TW 106117793 A TW106117793 A TW 106117793A TW 106117793 A TW106117793 A TW 106117793A TW 201819424 A TW201819424 A TW 201819424A
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- TW
- Taiwan
- Prior art keywords
- meth
- acrylate
- mass
- curable composition
- active energy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000000178 monomer Substances 0.000 claims abstract description 53
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- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 23
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 3
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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
-
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- B32—LAYERED PRODUCTS
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Abstract
Description
本發明係關於能藉由塗布在薄膜的表面並使其硬化，而在薄膜表面形成具有高折射率與高抗靜電性的硬塗層之活性能量線硬化性組成物及使用其之薄膜。 The present invention relates to an active energy ray-curable composition capable of forming a hard coat layer having a high refractive index and a high antistatic property on a surface of a film by being applied to a surface of a film and hardening it, and a film using the film.
使用於液晶顯示器(LCD)、有機EL顯示器(OLED)、電漿顯示器(PDP)等平面顯示器(FPD)表面之抗反射(LR)薄膜，係藉由在薄膜基材上形成折射率差大的2層之多層結構(基材/高折射率層/低折射率層)來實現。此等各層，為了防止在抗反射薄膜的製造過程中刮傷，要求高耐擦傷性，並且為了防止薄膜的汙染與防止黏結，還要求高抗靜電性。又，抗反射薄膜為光學薄膜，因此各層也被要求高透明性。 An anti-reflection (LR) film used on a surface of a flat panel display (FPD) such as a liquid crystal display (LCD), an organic EL display (OLED), or a plasma display (PDP) is formed by forming a refractive index difference on a film substrate. A two-layer multilayer structure (substrate/high refractive index layer/low refractive index layer) is realized. These layers are required to have high scratch resistance in order to prevent scratching during the production process of the antireflection film, and high antistatic properties are required in order to prevent contamination of the film and prevention of adhesion. Further, since the antireflection film is an optical film, each layer is also required to have high transparency.
上述要求的特性之中，作為賦予抗靜電性的手法，提案有使用摻合具有四級銨鹽之樹脂的材料(例如參照專利文獻1~3。)。然而，這些材料並非是高折射率的材料。 Among the above-mentioned characteristics, a material in which a resin having a quaternary ammonium salt is blended is proposed as a method for imparting antistatic properties (see, for example, Patent Documents 1 to 3). However, these materials are not high refractive index materials.
因此，尋求能形成具有高折射率與高抗靜電性的硬塗層之活性能量線硬化性組成物。 Therefore, an active energy ray-curable composition capable of forming a hard coat layer having a high refractive index and high antistatic property has been sought.
專利文獻1 日本特開2012-102166號公報 Patent Document 1 Japanese Patent Laid-Open Publication No. 2012-102166
專利文獻2 日本特開2008-013636號公報 Patent Document 2 Japanese Patent Laid-Open Publication No. 2008-013636
專利文獻3 日本特開2008-255184號公報 Patent Document 3 Japanese Patent Laid-Open Publication No. 2008-255184
本發明所欲解決之課題係提供能形成兼具高折射率與高抗靜電性的硬塗層之活性能量線硬化性組成物及使用其之薄膜。 An object of the present invention is to provide an active energy ray-curable composition capable of forming a hard coat layer having both a high refractive index and a high antistatic property, and a film using the same.
本案發明人等為了解決上述課題戮力研究的結果，發現藉由在活性能量線硬化性組成物中摻合特定的高折射率聚合性單體、具有脂環結構及四級銨鹽之樹脂等，能形成兼具高折射率與高抗靜電性之硬塗層，而完成本發明。 In order to solve the problem of the above-mentioned problems, the inventors of the present invention found that a specific high refractive index polymerizable monomer, a resin having an alicyclic structure and a quaternary ammonium salt, and the like are blended in the active energy ray-curable composition. The present invention can be completed by forming a hard coat layer having both a high refractive index and a high antistatic property.
亦即，本發明提供一種活性能量線硬化性組成物及使用其之薄膜，其中該活性能量線硬化性組成物的特徵為含有：折射率為1.55以上之高折射率聚合性單體(A)、多官能聚合性單體(B)、具有脂環結構與四級銨鹽之樹脂(C)、與有機溶劑(D)。 That is, the present invention provides an active energy ray-curable composition characterized by containing a high refractive index polymerizable monomer having a refractive index of 1.55 or more (A), and a film using the same A polyfunctional polymerizable monomer (B), a resin (C) having an alicyclic structure and a quaternary ammonium salt, and an organic solvent (D).
本發明之活性能量線硬化性組成物藉由塗布於薄膜表面並硬化，能在薄膜表面形成具有高折射率與高抗靜電性之硬塗層。因此，本發明之活性能量線硬化性組成物的硬化塗膜在作為抗反射薄膜的材料上非常有用。 The active energy ray-curable composition of the present invention can be formed on the surface of the film by hard coating to form a hard coat layer having a high refractive index and high antistatic property on the surface of the film. Therefore, the cured coating film of the active energy ray-curable composition of the present invention is very useful as a material for the antireflection film.
又，具有包括本發明之活性能量線硬化性組成物的硬化塗膜之硬塗層的薄膜，能合適地使用作為用於液晶顯示器(LCD)、有機EL顯示器(OLED)、電漿顯示器(PDP)等平面顯示器(FPD)之光學薄膜。進而，由於在用於這些用途時亦具有優良的抗靜電性，因此能抑制灰塵等的附著。此外，在將此薄膜用於液晶顯示器等的情形，也能防止因產生的靜電造成之顯示器的故障。 Further, a film having a hard coat layer comprising a hard coat film of the active energy ray-curable composition of the present invention can be suitably used as a liquid crystal display (LCD), an organic EL display (OLED), and a plasma display (PDP). An optical film of a flat panel display (FPD). Further, since it has excellent antistatic properties when used for these applications, adhesion of dust or the like can be suppressed. Further, in the case where the film is used for a liquid crystal display or the like, the malfunction of the display due to the generated static electricity can be prevented.
本發明之活性能量線硬化性組成物係含有：折射率為1.55以上之高折射率聚合性單體(A)、多官能聚合性單體(B)、具有脂環結構及四級銨鹽之樹脂(C)、與有機溶劑(D)。 The active energy ray-curable composition of the present invention contains a high refractive index polymerizable monomer (A) having a refractive index of 1.55 or more, a polyfunctional polymerizable monomer (B), an alicyclic structure, and a quaternary ammonium salt. Resin (C) and organic solvent (D).
前述聚合性單體(A)只要是硬化前的折射率在1.55以上的高折射率者即可，較佳可列舉出例如：具有2~6個芳香環之芳香族系聚合性單體、茀系聚合性單體等。又，作為前述聚合性單體(A)的具體例，可列舉出：以下述通式(1)所表示之化合物；(甲基)丙烯酸鄰苯基苄酯、(甲基)丙烯酸對苯基苄酯等之具有苯基苄基之(甲基)丙烯酸酯化合物；苯基苯酚EO丙烯酸酯等之具有苯基苯酚基之(甲基)丙烯酸酯化合物；丙氧化雙酚A二(甲基)丙烯酸酯、乙氧化雙酚A二(甲基)丙烯酸酯、具有伸氧乙基(oxyethylene)之雙酚A二(甲基)丙烯酸酯、具有伸 氧乙基之雙酚A三(甲基)丙烯酸酯等之具有範圍在2~4個的(甲基)丙烯醯基之雙酚化合物等。這些聚合性單體(A)可使用1種，也可2種以上併用。這些之中，從控制折射率的觀點來看，較佳為使用選自包含以下述通式(1)所表示之化合物、具有苯基苄基之(甲基)丙烯酸酯化合物、及具有範圍在2~4個的(甲基)丙烯醯基之雙酚化合物之群組中之1種以上單體；更佳為：單獨用以下述通式(1)所表示之化合物、併用以下述通式(1)所表示之化合物及具有苯基苄基之(甲基)丙烯酸酯化合物、單獨用具有範圍在2~4個的(甲基)丙烯醯基之雙酚化合物。又，在併用以下述通式(1)所表示之化合物與具有苯基苄基之(甲基)丙烯酸酯化合物的情形，其質量比較佳在30/70~70/30之範圍。 The polymerizable monomer (A) may be a high refractive index having a refractive index of 1.55 or more before curing, and is preferably an aromatic polymerizable monomer having 2 to 6 aromatic rings, for example. It is a polymerizable monomer or the like. In addition, specific examples of the polymerizable monomer (A) include a compound represented by the following formula (1); o-phenylbenzyl (meth)acrylate; p-phenyl (meth)acrylate; a (meth) acrylate compound having a phenyl benzyl group such as a benzyl ester; a (meth) acrylate compound having a phenylphenol group such as a phenylphenol EO acrylate; a bisphenol A di(methyl) acrylate Acrylate, ethoxylated bisphenol A di(meth)acrylate, bisphenol A di(meth)acrylate having oxyethylene, bisphenol A tri(methyl) having an oxygen-extended ethyl group A bisphenol compound having a (meth) acrylonitrile group having a range of 2 to 4, such as an acrylate. These polymerizable monomers (A) may be used singly or in combination of two or more kinds. Among these, from the viewpoint of controlling the refractive index, it is preferred to use a compound selected from the group consisting of the following formula (1), a (meth) acrylate compound having a phenylbenzyl group, and One or more monomers of the group of 2 to 4 (meth)acrylonitrile-based bisphenol compounds; more preferably: a compound represented by the following formula (1) alone, and used in the following formula (1) A compound represented by the formula and a (meth) acrylate compound having a phenylbenzyl group, and a bisphenol compound having a (meth) acrylonitrile group in a range of 2 to 4, used alone. Further, in the case where the compound represented by the following formula (1) and the (meth) acrylate compound having a phenylbenzyl group are used in combination, the quality thereof is preferably in the range of 30/70 to 70/30.
(式(1)中，R1、R2分別表示氫基或甲基，m、n分別表示0~5之整數)。 (In the formula (1), R 1 and R 2 each represent a hydrogen group or a methyl group, and m and n each represent an integer of 0 to 5).
另外，本發明中，「(甲基)丙烯酸酯」係指丙烯酸酯與甲基丙烯酸酯中的一者或兩者，「(甲基)丙烯醯」係指丙烯醯與甲基丙烯醯中的一者或兩者。 In the present invention, "(meth) acrylate" means one or both of acrylate and methacrylate, and "(meth) propylene oxime" means propylene oxime and methacryl oxime. One or both.
前述聚合性單體(B)為多官能聚合性單體，在1分子中具有2個以上聚合性基者。前述聚合性基只要是碳-碳雙鍵之乙烯基、(甲基)丙烯醯基等基即可，而從硬化性優良來看，較佳為(甲基)丙烯醯基。 The polymerizable monomer (B) is a polyfunctional polymerizable monomer, and has two or more polymerizable groups in one molecule. The polymerizable group may be a group such as a vinyl group of a carbon-carbon double bond or a (meth)acryl fluorenyl group, and is preferably a (meth) acrylonitrile group from the viewpoint of excellent curability.
作為具有(甲基)丙烯醯基之前述聚合性單體(B)，可列舉出例如：1,4-丁二醇二(甲基)丙烯酸酯、3-甲基-1,5-戊二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、2-甲基-1,8-辛二醇二(甲基)丙烯酸酯、2-丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、三環癸烷二甲醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯等2元醇的二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、參(2-羥乙基)異三聚氰酸酯的二(甲基)丙烯酸酯、對1莫耳新戊二醇加成4莫耳以上的環氧乙烷或環氧丙烷所得到之二醇的二(甲基)丙烯酸酯、對1莫耳雙酚A加成2莫耳環氧乙烷或環氧丙烷所得到之二醇的二(甲基)丙烯酸酯、三羥甲丙烷三(甲基)丙烯酸酯、環氧乙烷改性三羥甲丙烷三(甲基)丙烯酸酯、環氧丙烷改性三羥甲丙烷三(甲基)丙烯酸酯、二-三羥甲丙烷三(甲基)丙烯酸酯、二-三羥甲丙烷四(甲基)丙烯酸酯、參(2-(甲基)丙烯醯氧基乙基)異三聚氰酸酯、新戊四醇三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇三(甲基)丙烯酸酯、二新戊四醇四(甲基)丙烯酸酯、二新戊四醇 五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。這些多官能聚合性單體(B)可使用1種，也可2種以上併用。又，這些多官能聚合性單體(B)之中，從提升本發明之活性能量線硬化性組成物的硬化塗膜之耐擦傷性來看，較佳為二新戊四醇六(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯。 The polymerizable monomer (B) having a (meth) acrylonitrile group may, for example, be 1,4-butanediol di(meth)acrylate or 3-methyl-1,5-pentane. Alcohol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 2-methyl-1,8-octanediol di Methyl) acrylate, 2-butyl-2-ethyl-1,3-propanediol di(meth) acrylate, tricyclodecane dimethanol di(meth) acrylate, ethylene glycol di(methyl) 2 yuan such as acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate Di(meth)acrylate of alcohol, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, bis(2-hydroxyethyl)isocyanate Acrylate, bis(meth) acrylate of diol obtained by adding 4 moles of ethylene oxide or propylene oxide to 1 mole of neopentyl glycol, plus 1 mole bisphenol A Di(meth) acrylate, trimethylolpropane of diol obtained as 2 moles of ethylene oxide or propylene oxide (Meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide modified trimethylolpropane tri (meth) acrylate, di-trimethylolpropane tri ( Methyl) acrylate, di-trimethylolpropane tetra(meth) acrylate, gin(2-(methyl) propylene methoxyethyl) isocyanate, neopentyl alcohol tris(methyl) Acrylate, neopentyl alcohol tetra(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol five (a) Acrylate, dipentaerythritol hexa(meth)acrylate, and the like. These polyfunctional polymerizable monomers (B) may be used singly or in combination of two or more kinds. Further, among these polyfunctional polymerizable monomers (B), from the viewpoint of improving the scratch resistance of the cured coating film of the active energy ray-curable composition of the present invention, dipentaerythritol hexa(methyl) is preferred. ) acrylate, dipentaerythritol penta (meth) acrylate, neopentyl alcohol tetra (meth) acrylate, neopentyl alcohol tri (meth) acrylate.
又，本發明之活性能量線硬化性組成物中也可摻合胺甲酸酯(甲基)丙烯酸酯來作為除了前述聚合性單體(A)及前述聚合性單體(B)以外之聚合性成分。前述胺甲基酸酯(甲基)丙烯酸酯(E)為使聚異氰酸酯(e1)與具有羥基之(甲基)丙烯酸酯(e2)進行反應所得者。 Further, in the active energy ray-curable composition of the present invention, a urethane (meth) acrylate may be blended as a polymerization other than the polymerizable monomer (A) and the polymerizable monomer (B). Sexual ingredients. The amine methyl ester (meth) acrylate (E) is obtained by reacting a polyisocyanate (e1) with a (meth) acrylate having a hydroxyl group (e2).
作為前述聚異氰酸酯(e1)，可列舉出脂肪族聚異氰酸酯與芳香族聚異氰酸酯，但從能減少本發明之活性能量線硬化性組成物的硬化塗膜之著色來看，較佳為脂肪族聚異氰酸酯。 The polyisocyanate (e1) may, for example, be an aliphatic polyisocyanate or an aromatic polyisocyanate. However, from the viewpoint of reducing the color of the cured coating film of the active energy ray-curable composition of the present invention, aliphatic polycondensation is preferred. Isocyanate.
前述脂肪族聚異氰酸酯為除了異氰酸酯基以外的部位係由脂肪族烴所構成之化合物。作為此脂肪族聚異氰酸酯的具體例，可列舉出：六亞甲基二異氰酸酯、離胺酸二異氰酸酯、離胺酸三異氰酸酯等脂肪族聚異氰酸酯；降莰烷二異氰酸酯、異佛酮二異氰酸酯、亞甲雙(4-環己基異氰酸酯)、1,3-雙(異氰酸基甲基)環己烷、2-甲基-1,3-二異氰酸基環己烷、2-甲基-1,5-二異氰酸基環己烷等脂環式聚異氰酸酯等。又，將前述脂肪族聚異氰酸酯或脂環式聚異氰酸酯三聚化而成的三聚物也可使用 作為前述脂肪族聚異氰酸酯。又，這些脂肪族聚異氰酸酯可單獨使用1種，也可2種以上併用。 The aliphatic polyisocyanate is a compound composed of an aliphatic hydrocarbon other than the isocyanate group. Specific examples of the aliphatic polyisocyanate include aliphatic polyisocyanates such as hexamethylene diisocyanate, quaternary acid diisocyanate, and isocyanuric acid triisocyanate; norbornane diisocyanate and isophorone diisocyanate; Methylene bis(4-cyclohexyl isocyanate), 1,3-bis(isocyanatomethyl)cyclohexane, 2-methyl-1,3-diisocyanatocyclohexane, 2-methyl An alicyclic polyisocyanate such as -1,5-diisocyanatocyclohexane or the like. Further, a terpolymer obtained by trimerizing the above aliphatic polyisocyanate or alicyclic polyisocyanate can also be used as the above aliphatic polyisocyanate. In addition, these aliphatic polyisocyanates may be used alone or in combination of two or more.
在前述脂肪族聚異氰酸酯之中，為了提升塗膜的耐擦傷性，脂肪族聚異氰酸酯之中較佳為直鏈脂肪族烴的二異氰酸酯之六亞甲基二異氰酸酯、脂環式二異氰酸酯之降莰烷二異氰酸酯、異佛酮二異氰酸酯。 Among the above aliphatic polyisocyanates, in order to improve the scratch resistance of the coating film, among the aliphatic polyisocyanates, a diisocyanate of a linear aliphatic hydrocarbon is preferably a hexamethylene diisocyanate or an alicyclic diisocyanate. Decane diisocyanate, isophorone diisocyanate.
前述(甲基)丙烯酸酯(e2)為具有羥基與(甲基)丙烯醯基之化合物。作為此(甲基)丙烯酸酯(e2)的具體例，可列舉出：(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丙酯、(甲基)丙烯酸2-羥丁酯、(甲基)丙烯酸4-羥丁酯、1,5-戊二醇單(甲基)丙烯酸酯、1,6-己二醇單(甲基)丙烯酸酯、新戊二醇單(甲基)丙烯酸酯、羥基三甲基乙酸新戊二醇單(甲基)丙烯酸酯等的2元醇之單(甲基)丙烯酸酯；三羥甲丙烷二(甲基)丙烯酸酯、環氧乙烷(EO)改性三羥甲丙烷(甲基)丙烯酸酯、環氧丙烷(PO)改性三羥甲丙烷二(甲基)丙烯酸酯、丙三醇二(甲基)丙烯酸酯、三聚異氰酸雙(2-(甲基)丙烯醯氧基乙基)羥乙基異三聚氰酸酯等的3元醇之單或二(甲基)丙烯酸酯，或者是將這些醇性羥基的一部分以ε-己內酯加以改性而成的有羥基之單及二(甲基)丙烯酸酯；新戊四醇三(甲基)丙烯酸酯、二-三羥甲丙烷三(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯等的具有1官能的羥基與3官能以上的(甲基)丙烯醯基之化合物，或者是將該化合物進一步以ε-己內酯加以改性而成的有羥基之多官能(甲基)丙烯酸酯；二丙二醇單(甲基)丙烯酸酯、二乙二醇單(甲基)丙烯 酸酯、聚丙二醇單(甲基)丙烯酸酯、聚乙二醇單(甲基)丙烯酸酯等具有氧伸烷基(oxyalkylene)鏈之(甲基)丙烯酸酯；聚乙二醇-聚丙二醇單(甲基)丙烯酸酯、聚氧伸丁基-聚氧伸丙基單(甲基)丙烯酸酯等具有嵌段結構的氧伸烷基鏈之(甲基)丙烯酸酯；聚(乙二醇-伸丁二醇)單(甲基)丙烯酸酯、聚(丙二醇-伸丁二醇)單(甲基)丙烯酸酯等具有無規結構的氧伸烷基鏈之(甲基)丙烯酸酯等。這些(甲基)丙烯酸酯(e2)可使用1種，也可2種以上併用。 The aforementioned (meth) acrylate (e2) is a compound having a hydroxyl group and a (meth) acrylonitrile group. Specific examples of the (meth) acrylate (e2) include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 2-hydroxybutyl (meth)acrylate. Ester, 4-hydroxybutyl (meth)acrylate, 1,5-pentanediol mono(meth)acrylate, 1,6-hexanediol mono(meth)acrylate, neopentyl glycol mono(A) Mono(meth)acrylate of a dihydric alcohol such as acrylate, hydroxytrimethylacetic acid neopentyl glycol mono(meth)acrylate; trimethylolpropane di(meth)acrylate, epoxy B Alkane (EO) modified trimethylolpropane (meth) acrylate, propylene oxide (PO) modified trimethylolpropane di(meth) acrylate, glycerol di(meth) acrylate, trimer a mono- or di-(meth) acrylate of a trihydric alcohol such as bis(2-(methyl) propylene methoxyethyl) hydroxyethyl isocyanurate, or an alcoholic hydroxyl group a part of hydroxy-containing mono- and di(meth) acrylates modified with ε-caprolactone; neopentyl alcohol tri(meth) acrylate, di-trimethylolpropane tri(methyl) a monofunctional hydroxyl group of acrylate, dipentaerythritol penta (meth) acrylate, etc. a compound having a trifunctional or higher (meth) acrylonitrile group, or a polyfunctional (meth) acrylate having a hydroxyl group modified by further modifying the compound with ε-caprolactone; dipropylene glycol mono (methyl) Acrylate, diethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, etc. having an oxyalkylene chain (A) Acrylate; poly(ethylene glycol)-polypropylene glycol mono(meth)acrylate, polyoxybutylene-polyoxyl-propyl mono(meth)acrylate, etc. (Meth) acrylate; poly(ethylene glycol-butanediol) mono(meth)acrylate, poly(propylene glycol-butanediol) mono(meth)acrylate, etc. A (meth) acrylate of an alkyl chain or the like. These (meth) acrylates (e2) may be used alone or in combination of two or more.
前述胺甲酸酯(甲基)丙烯酸酯(e2)之中，為了能提升本發明之活性能量線硬化性組成物的硬化塗膜之耐擦傷性，較佳為在1分子中具有4個以上(甲基)丙烯醯基者。為了使前述胺甲酸酯(甲基)丙烯酸酯(E)成為在1分子中具有4個以上(甲基)丙烯醯基者，作為前述(甲基)丙烯酸酯(e2)，較佳為具有2個以上(甲基)丙烯醯基者。作為此種(甲基)丙烯酸酯(e2)，可列舉出例如：三羥甲丙烷二(甲基)丙烯酸酯、環氧乙烷改性三羥甲丙烷二(甲基)丙烯酸酯、環氧丙烷改性三羥甲丙烷二(甲基)丙烯酸酯、丙三醇二(甲基)丙烯酸酯、雙(2-(甲基)丙烯醯氧基乙酯)羥乙基異三聚氰酸酯、新戊四醇三(甲基)丙烯酸酯、二-三羥甲丙烷三(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯等。對於1種前述脂肪族聚異氰酸酯，這些(甲基)丙烯酸酯(e2)可使用1種，也可2種以上併用。又，這些(甲基)丙烯酸酯(e2)之中，為了能提升耐擦傷性，較佳為新戊四醇三(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯。 Among the urethane (meth) acrylates (e2), in order to improve the scratch resistance of the cured coating film of the active energy ray-curable composition of the present invention, it is preferred to have four or more in one molecule. (Methyl) acrylonitrile. In order to make the urethane (meth) acrylate (E) have four or more (meth) acrylonitrile groups in one molecule, it is preferred that the (meth) acrylate (e2) has Two or more (meth) acrylonitrile groups. Examples of such a (meth) acrylate (e2) include trimethylolpropane di(meth)acrylate, ethylene oxide-modified trimethylolpropane di(meth)acrylate, and epoxy. Propane modified trimethylolpropane di(meth)acrylate, glycerol di(meth)acrylate, bis(2-(methyl)propenyloxyethyl)hydroxyethyl isomeric cyanurate , pentaerythritol tri(meth)acrylate, di-trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and the like. One type of these (meth) acrylates (e2) may be used for one type of the above-mentioned aliphatic polyisocyanate, or two or more types may be used in combination. Further, among these (meth) acrylates (e2), pentaerythritol tri(meth)acrylate and dipentaerythritol penta (meth) acrylate are preferable in order to improve the scratch resistance.
前述聚異氰酸酯(e1)與前述(甲基)丙烯酸酯(e2)的反應能以常規方法的胺甲酸酯化反應來進行。又，為了促進胺甲酸酯化反應的進行，較佳在胺甲酸酯化觸媒的存在下進行胺甲酸酯化反應。作為前述胺甲酸酯化觸媒，可列舉出例如：吡啶、吡咯、三乙胺、二乙胺、二丁胺等的胺化合物；三苯膦、三乙膦等的磷化合物；二月桂酸二丁基錫、三月桂酸辛基錫、二乙酸辛基錫、二乙酸二丁基錫、辛酸錫等的有機錫化合物、辛酸鋅等的有機鋅化合物等。 The reaction of the aforementioned polyisocyanate (e1) with the aforementioned (meth) acrylate (e2) can be carried out by a conventional urethanation reaction. Further, in order to promote the progress of the urethanation reaction, it is preferred to carry out the urethanation reaction in the presence of a urethane catalyst. Examples of the urethane-based catalyst include an amine compound such as pyridine, pyrrole, triethylamine, diethylamine or dibutylamine; a phosphorus compound such as triphenylphosphine or triethylphosphine; and dilauric acid. An organic tin compound such as dibutyltin, octyltin trilaurate, octyltin diacetate, dibutyltin diacetate or tin octylate, or an organic zinc compound such as zinc octylate.
又，本發明之活性能量線硬化性組成物中，可視需要使用環氧(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯、聚醚(甲基)丙烯酸酯等作為除前述聚合性單體(A)、前述聚合性單體(B)及胺甲酸酯(甲基)丙烯酸酯(E)以外之聚合性成分。作為前述環氧(甲基)丙烯酸酯，可列舉出例如：藉由使(甲基)丙烯酸與雙酚型環氧樹脂、酚醛型環氧樹脂、聚甲基丙烯酸環氧丙酯等進行反應並酯化所得到者。又，作為前述聚酯(甲基)丙烯酸酯，可列舉出例如：藉由使(甲基)丙烯酸與將多元羧酸與多元醇聚縮合所得到之兩末端為羥基的聚酯進行反應並酯化所得到者，或是藉由使(甲基)丙烯酸與在多元羧酸上加成了環氧烷而成者進行反應並酯化所得到者。此外，作為前述聚醚(甲基)丙烯酸酯，可舉出例如：使(甲基)丙烯酸與聚醚多元醇進行反應並酯化所得到者。 Further, in the active energy ray-curable composition of the present invention, an epoxy (meth) acrylate, a polyester (meth) acrylate, a polyether (meth) acrylate or the like may be used as the above-mentioned polymerizable single sheet, if necessary. A polymerizable component other than the body (A), the polymerizable monomer (B), and the urethane (meth) acrylate (E). Examples of the epoxy (meth) acrylate include reacting (meth)acrylic acid with a bisphenol epoxy resin, a novolac epoxy resin, polyglycidyl methacrylate, and the like. Esterification obtained. Moreover, as the polyester (meth) acrylate, for example, a polyester obtained by polycondensing (meth)acrylic acid with a polyvalent carboxylic acid and a polyhydric alcohol and having a hydroxyl group at both ends thereof may be reacted and esterified. The obtained one is obtained by reacting and esterifying (meth)acrylic acid with an alkylene oxide added to a polyvalent carboxylic acid. Further, examples of the polyether (meth) acrylate include those obtained by reacting and esterifying (meth)acrylic acid with a polyether polyol.
前述樹脂(B)為具有脂環結構及四級銨鹽之樹脂。 The above resin (B) is a resin having an alicyclic structure and a quaternary ammonium salt.
作為前述樹脂(C)之製造方法，可舉出例如：以具有脂環結構的聚合性單體(c1)及具有四級銨鹽的聚合性單體(c2)作為必要成分，並使前述聚合性單體(c1)及前述聚合性單體(c2)與能共聚合的聚合性單體(c3)共聚合之方法。 The method for producing the resin (C) is, for example, a polymerizable monomer (c1) having an alicyclic structure and a polymerizable monomer (c2) having a quaternary ammonium salt as essential components, and the polymerization is carried out. A method of copolymerizing a monomer (c1) and the polymerizable monomer (c2) with a copolymerizable polymerizable monomer (c3).
前述聚合性單體(c1)為具有脂環結構之聚合性單體。就前述脂環結構而言，可列舉出例如：環丙烷環、環丁烷環、環戊烷環、環己烷環、環庚烷環、環辛烷環、環壬烷環、環癸烷環等單環脂環結構；雙環十一烷環、十氫萘(decalin)環、三環[5.2.1.02,6]癸烷環、雙環[4.3.0]壬烷環、三環[5.3.1.1]十二烷環、三環[5.3.1.1]十二烷環、螺[3.4]辛烷環等多環脂環結構等。又，作為前述聚合性單體(c1)的具體例，可列舉出：(甲基)丙烯酸環己酯、1,4-環己烷二甲醇單(甲基)丙烯酸酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊烯基氧基乙酯、(甲基)丙烯酸二環戊酯等。這些聚合性單體(c1)可使用1種，也可2種以上併用。 The polymerizable monomer (c1) is a polymerizable monomer having an alicyclic structure. The alicyclic structure may, for example, be a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclodecane ring or a cyclodecane. Cyclic monocyclic alicyclic structure; bicyclo undecane ring, decaline ring, tricyclo[5.2.1.0 2,6 ]decane ring, bicyclo[4.3.0]decane ring, tricyclo[5.3 .1.1] Polycyclic alicyclic structures such as dodecane ring, tricyclo[5.3.1.1] dodecane ring, spiro[3.4]octane ring, and the like. Moreover, specific examples of the polymerizable monomer (c1) include cyclohexyl (meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, and (meth)acrylic acid. Isodecyl ester, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, and the like. These polymerizable monomers (c1) may be used alone or in combination of two or more.
作為前述聚合性單體(c2)，可列舉出例如：氯化2-[(甲基)丙烯醯氧基]乙基三甲基銨、氯化3-[(甲基)丙烯醯氧基]丙基三甲基銨等相對陰離子為氯離子(chloride)者；溴化2-[(甲基)丙烯醯氧基]乙基三甲基銨、溴化3-[(甲基)丙烯醯氧基]丙基三甲基銨等相對陰離子為溴離子者；甲基苯磺酸2-[(甲基)丙烯醯氧基]乙基三甲基銨、甲磺酸2-[(甲基)丙烯醯氧基]乙基三甲基銨、甲基苯磺酸3-[(甲基)丙烯醯氧基]丙基三甲基銨、甲磺酸 3-[(甲基)丙烯醯氧基]丙基三甲基銨、甲磺酸2-[(甲基)丙烯醯氧基]乙基三甲基銨、甲磺酸3-[(甲基)丙烯醯氧基]丙基三甲基銨等相對陰離子為非鹵素類者等。這些聚合性單體(c2)可使用1種，也可2種以上併用。 Examples of the polymerizable monomer (c2) include 2-[(methyl)acryloxycarbonyl]ethyltrimethylammonium chloride and 3-[(meth)acryloxycarbonyl] chloride. The relative anion such as propyltrimethylammonium is chloride; 2-[(meth)acryloxy]ethyltrimethylammonium bromide, 3-[(meth)acrylofluorene bromide a relative anion such as propyltrimethylammonium is bromide; 2-[(methyl)propenyloxy]ethyltrimethylammonium methanesulfonate, 2-[(methyl) methanesulfonate Propylene oxime]ethyltrimethylammonium, 3-[(meth)acryloxy]propyltrimethylammonium benzenesulfonate, 3-[(meth) propylene oxime methanesulfonate ]propyltrimethylammonium, 2-[(methyl)propenyloxy]ethyltrimethylammonium methanesulfonate, 3-[(methyl)propenyloxy]propyltrimethyl methanesulfonate A relative anion such as ammonium is a non-halogen type or the like. These polymerizable monomers (c2) may be used alone or in combination of two or more.
作為前述聚合性單體(c3)，可列舉出例如：(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸正戊酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸正庚酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二酯等(甲基)丙烯酸烷酯；甲氧基聚乙二醇單(甲基)丙烯酸酯、辛氧基聚乙二醇．聚丙二醇單(甲基)丙烯酸酯、十二烷氧基聚乙二醇單(甲基)丙烯酸酯、十八烷氧基聚乙二醇單(甲基)丙烯酸酯、苯氧基聚乙二醇單(甲基)丙烯酸酯、苯氧基聚乙二醇．聚丙二醇單(甲基)丙烯酸酯、壬基苯氧基聚丙二醇單(甲基)丙烯酸酯、壬基苯氧基聚(乙二醇．丙二醇)單(甲基)丙烯酸酯等聚伸烷二醇的單(甲基)丙烯酸酯；(甲基)丙烯酸2-全氟己基乙酯等具有氟化烷基的(甲基)丙烯酸酯等。這些聚合性單體(c3)可使用1種，也可2種以上併用。 Examples of the polymerizable monomer (c3) include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, and n-butyl (meth)acrylate. Isobutyl methacrylate, n-amyl (meth) acrylate, n-hexyl (meth) acrylate, n-heptyl (meth) acrylate, n-octyl (meth) acrylate, 2-(meth) acrylate Ethylhexyl ester, decyl (meth)acrylate, decyl (meth)acrylate, alkyl (meth)acrylate such as dodecyl (meth)acrylate; methoxypolyethylene glycol mono(methyl) Acrylate, octyloxy polyethylene glycol. Polypropylene glycol mono(meth)acrylate, dodecyloxy polyethylene glycol mono(meth)acrylate, octadecyloxy polyethylene glycol mono(meth)acrylate, phenoxypolyethylene Alcohol mono (meth) acrylate, phenoxy polyethylene glycol. Polypropylene glycol mono (meth) acrylate, nonyl phenoxy polypropylene glycol mono (meth) acrylate, nonyl phenoxy poly (ethylene glycol propylene glycol) mono (meth) acrylate, etc. A mono(meth)acrylate of an alcohol; a (meth)acrylate having a fluorinated alkyl group such as 2-perfluorohexylethyl (meth)acrylate; and the like. These polymerizable monomers (c3) may be used alone or in combination of two or more.
前述聚合性單體(c3)之中，從能更進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，較佳為聚伸烷二醇的單(甲基)丙烯酸酯，更佳為甲氧基聚乙二醇單(甲基)丙烯酸酯。又，具有氟化烷基的(甲基)丙烯酸酯，從具有進一步提升本發明之活 性能量線硬化性組成物的硬化塗膜之抗靜電性的效果來看同樣為較佳的。 Among the polymerizable monomers (c3), from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention, a monomethyl group of a polyalkylene glycol is preferred. Acrylate, more preferably methoxypolyethylene glycol mono(meth)acrylate. Further, the (meth) acrylate having a fluorinated alkyl group is also preferable from the viewpoint of the effect of further improving the antistatic property of the cured coating film of the linear curable composition of the present invention.
在前述聚伸烷二醇的單(甲基)丙烯酸酯之中，從能更進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，成為前述聚伸烷二醇的單(甲基)丙烯酸酯之原料的聚伸烷二醇的數量平均分子量較佳為在200~8,000之範圍者，更佳為在300~6,000之範圍者，再更佳為在400~4,000之範圍者，特佳為在400~2,000之範圍者。 Among the mono(meth)acrylates of the above-mentioned polyalkylene glycol, the above-mentioned polyalkylene oxide is obtained from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. The number average molecular weight of the polyalkylene glycol of the raw material of the mono(meth)acrylate of the alcohol is preferably in the range of 200 to 8,000, more preferably in the range of 300 to 6,000, and even more preferably in the range of 400 to 6,000. The range of 4,000 is particularly good for those in the range of 400 to 2,000.
前述樹脂(C)的原料總量中前述聚合性單體(c1)的比率，從能更進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，較佳在5~55質量%之範圍，更佳在10~50質量%之範圍，再更佳在12~45質量%之範圍。 The ratio of the polymerizable monomer (c1) in the total amount of the raw materials of the resin (C) is preferably from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. The range of 5 to 55 mass% is more preferably in the range of 10 to 50 mass%, and more preferably in the range of 12 to 45 mass%.
又，前述樹脂(C)的原料總量中前述聚合性單體(c2)的比率，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，較佳在30~90質量%之範圍，更佳在40~80質量%之範圍，再更佳在45~70質量%之範圍。 In addition, the ratio of the polymerizable monomer (c2) in the total amount of the raw materials of the resin (C) is preferably from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. It is in the range of 30 to 90% by mass, more preferably in the range of 40 to 80% by mass, and even more preferably in the range of 45 to 70% by mass.
另外，在使用前述聚伸烷二醇的單(甲基)丙烯酸酯作為前述聚合性單體(c3)之情形，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，前述樹脂(C)的原料總量中聚伸烷二醇的單(甲基)丙烯酸酯的比率較佳在5~60質量%之範圍，更佳在10~50質量%之範圍，再更佳在20~40質量%之範圍。 In addition, in the case where the mono(meth)acrylate of the above-mentioned polyalkylene glycol is used as the polymerizable monomer (c3), the resistance of the cured coating film which can further enhance the active energy ray-curable composition of the present invention is further enhanced. The ratio of the mono(meth) acrylate of the polyalkylene glycol in the total amount of the raw materials of the resin (C) is preferably in the range of 5 to 60% by mass, more preferably 10 to 50% by mass. The range is more preferably in the range of 20 to 40% by mass.
又，在使用前述具有氟化烷基的(甲基)丙烯酸酯作為前述聚合性單體(c3)之情形，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，前述樹脂(C)的原料總量中具有氟化烷基的(甲基)丙烯酸酯的比率較佳在0.1~20質量%之範圍，更佳在0.5~10質量%之範圍，再更佳在1~5質量%之範圍。 Further, in the case where the (meth) acrylate having a fluorinated alkyl group is used as the polymerizable monomer (c3), the antistatic coating of the cured coating film capable of further enhancing the active energy ray-curable composition of the present invention is further improved. The ratio of the (meth) acrylate having a fluorinated alkyl group in the total amount of the raw materials of the resin (C) is preferably in the range of 0.1 to 20% by mass, more preferably 0.5 to 10% by mass. More preferably in the range of 1 to 5 mass%.
前述樹脂(C)的重量平均分子量，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，較佳在1,000~100,000之範圍，更佳在2,000~50,000之範圍，再更佳在3,000~30,000之範圍。另外，本發明中的重量平均分子量係以凝膠滲透層析(GPC)法測定的用聚苯乙烯換算之值。 The weight average molecular weight of the resin (C) is preferably in the range of 1,000 to 100,000, more preferably 2,000 to 50,000, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. The range is even better in the range of 3,000 to 30,000. Further, the weight average molecular weight in the present invention is a value in terms of polystyrene measured by a gel permeation chromatography (GPC) method.
前述樹脂(C)的摻合量，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，相對於前述聚合性單體(A)及前述聚合性單體(B)的合計100質量份，較佳在0.1~30質量份之範圍，更佳在0.5~20質量份之範圍，再更佳在1~10質量份之範圍，特佳在1.5~7質量份之範圍。 The amount of the resin (C) blended is from the polymerizable monomer (A) and the aforementioned polymerizable sheet in view of the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention. The total amount of the body (B) is 100 parts by mass, preferably in the range of 0.1 to 30 parts by mass, more preferably in the range of 0.5 to 20 parts by mass, still more preferably in the range of 1 to 10 parts by mass, particularly preferably in the range of 1.5 to 7 parts by mass. The range of parts by mass.
前述有機溶劑(D)只要是可溶解本發明之活性能量線硬化性組成物中的其它成分之溶劑即可無特別限制地使用。又，從能進一步提升本發明之活性能量線硬化性組成物的硬化塗膜之抗靜電性來看，較佳為漢森(Hansen)溶解度參數中的分散項(δD)在15.5~16.1MPa0.5之範圍、極化(polarization)項(δP)在6.3~10.4MPa0.5之範圍、氫鍵項(δH)在5.1~11.6MPa0.5之範圍者。 The organic solvent (D) is not particularly limited as long as it is a solvent which can dissolve other components in the active energy ray-curable composition of the present invention. Further, from the viewpoint of further improving the antistatic property of the cured coating film of the active energy ray-curable composition of the present invention, it is preferred that the dispersion term (δD) in the Hansen solubility parameter is 15.5 to 16.1 MPa 0.5 The range, polarization term (δP) is in the range of 6.3 to 10.4 MPa 0.5 , and the hydrogen bond term (δH) is in the range of 5.1 to 11.6 MPa 0.5 .
另外，漢森溶解度參數的定義與計算記載於Charles M.Hansen著作的「漢森溶解度參數；使用者手册(CRC Press,2007)」中。又，藉由使用電腦軟體「漢森溶解度參數實踐(Hansen Solubility Parameters in Practice，HSPiP)」，即使是關於文獻中沒有記載參數值的有機溶劑，也能自其化學結構推算漢森溶解度參數。本發明中，對於文獻中有記載參數值的有機溶劑係使用該值，而關於文獻中沒有記載參數值的有機溶劑則係用使用HSPiP版本4.1.06推算出的參數值。 In addition, the definition and calculation of Hansen solubility parameters are described in the "Hansen Solubility Parameters; User Manual (CRC Press, 2007)" by Charles M. Hansen. Further, by using the computer software "Hansen Solubility Parameters in Practice (HSPiP)", the Hansen solubility parameter can be estimated from the chemical structure even if it is an organic solvent in which no parameter value is described in the literature. In the present invention, the value is used for the organic solvent in which the parameter value is described in the literature, and the organic solvent in which the parameter value is not described in the literature is the parameter value estimated using HSPiP version 4.1.06.
前述有機溶劑(D)可以使用1種有機溶劑，也可併用2種以上有機溶劑作為混合溶劑使用。在併用2種以上之情形，可使用將各個有機溶劑的漢森溶解度參數的3個參數加權平均之值成為上述範圍內之組合。 One type of the organic solvent may be used as the organic solvent (D), or two or more types of organic solvents may be used in combination as a mixed solvent. When two or more types are used in combination, the weighted average of the three parameters of the Hansen solubility parameter of each organic solvent can be used as a combination within the above range.
於併用2種以上有機溶劑來使用作為前述有機溶劑(D)之情形，作為調整至該漢森溶解度參數之範圍的方法，可舉出例如：乙醇(δD=15.8MPa0.5、δP=8.8MPa0.5、δH=19.4MPa0.5)等醇溶劑，與甲乙酮(δD=16.0MPa0.5、δP=9.0MPa0.5、δH=5.1MPa0.5)等酮溶劑的組合，也可舉出前述酮類溶劑與乙酸甲酯(δD=15.5MPa0.5、δP=7.2MPa0.5、δH=7.6MPa0.5)等酯溶劑的組合。又，除了此醇溶劑與酮溶劑的組合以外，藉由在前述有機溶劑(D)中進一步含有3~40質量%的二丙酮醇(δD=15.8MPa0.5、δP=8.2MPa0.5、δH=10.8MPa0.5)、乙醯丙酮(δD=16.1MPa0.5、δP=10.0MPa0.5、δH=6.2MPa0.5)、二甲基卡必醇(dimethyl carbitol)(δD=15.7MPa0.5、 δP=6.1MPa0.5、δH=6.5MPa0.5)、丙二醇單甲基醚乙酸酯(δD=15.6MPa0.5、δP=5.6MPa0.5、δH=9.8MPa0.5)等之沸點100~180℃之高沸點溶劑，可提升塗布穩定性，防止硬化塗膜產生裂痕，且能使塗膜外觀優良，故較佳。 In the case where the organic solvent (D) is used in combination with two or more kinds of organic solvents, as a method of adjusting the range of the Hansen solubility parameter, for example, ethanol (δD = 15.8 MPa 0.5 , δP = 8.8 MPa 0.5) , δH = 19.4MPa 0.5) a solvent like an alcohol, and methyl ethyl ketone (δD = 16.0MPa 0.5, δP = 9.0MPa 0.5, compositions δH = 5.1MPa 0.5), ketone solvents, the ketone solvent may include methyl acetate and A combination of ester solvents such as (δD = 15.5 MPa 0.5 , δP = 7.2 MPa 0.5 , δH = 7.6 MPa 0.5 ). Further, in addition to the combination of the alcohol solvent and the ketone solvent, the organic solvent (D) further contains 3 to 40% by mass of diacetone alcohol (δD = 15.8 MPa 0.5 , δP = 8.2 MPa 0.5 , δH = 10.8). MPa 0.5), acetyl acetone (δD = 16.1MPa 0.5, δP = 10.0MPa 0.5, δH = 6.2MPa 0.5), dimethyl carbitol (dimethyl carbitol) (δD = 15.7MPa 0.5, δP = 6.1MPa 0.5, δH=6.5MPa 0.5 ), propylene glycol monomethyl ether acetate (δD=15.6MPa 0.5 , δP=5.6MPa 0.5 , δH=9.8MPa 0.5 ) and other high boiling point solvents with boiling point of 100~180°C can improve coating stability. It is preferable to prevent cracking of the hardened coating film and to make the coating film excellent in appearance.
本發明之活性能量線硬化性組成物中的前述有機溶劑(D)之摻合量，較佳為設成成為適用於後述的塗布方法之黏度的量。 The blending amount of the organic solvent (D) in the active energy ray-curable composition of the present invention is preferably an amount which is suitable for the viscosity of a coating method to be described later.
又，本發明之活性能量線硬化性組成物在塗布於基材上後，能藉由照射活性能量線形成硬化塗膜。此活性能量線係指紫外線、電子射線、α線、β線、γ線等游離輻射線。於照射紫外線作為活性能量線而形成硬化塗膜之情形，較佳在本發明之活性能量線硬化性組成物中添加光聚合起始劑(F)來提升硬化性。另外，若有需要也可進一步添加光敏劑(G)來提升硬化性。另一方面，在使用電子射線、α線、β線、γ線等游離輻射線的情形，即使沒有使用光聚合起始劑(F)或光敏劑(G)，也會快速地硬化，所以無需特別添加光聚合起始劑(F)或光敏劑(G)。 Further, after application to the substrate, the active energy ray-curable composition of the present invention can form a cured coating film by irradiation with an active energy ray. The active energy ray refers to an ultraviolet ray, an electron ray, an alpha ray, a beta ray, a gamma ray, or the like. In the case where ultraviolet light is irradiated as an active energy ray to form a cured coating film, it is preferred to add a photopolymerization initiator (F) to the active energy ray-curable composition of the present invention to improve the hardenability. Further, a photosensitizer (G) may be further added if necessary to enhance the hardenability. On the other hand, in the case of using an ion beam such as an electron beam, an α line, a β line, or a γ line, even if the photopolymerization initiator (F) or the photosensitizer (G) is not used, it hardens rapidly, so it is not necessary. A photopolymerization initiator (F) or a photosensitizer (G) is added in particular.
作為前述光聚合起始劑(F)，可列舉出例如：二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙-1-酮、寡聚{2-羥基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙酮}、苄基二甲縮酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙-1-酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、1-羥基環己基苯基酮、2-甲基-2-啉基(4-硫甲基苯基)丙-1-酮、2-苯甲基-2-二甲胺基-1-(4-啉基苯基)-丁酮等的苯乙酮系化合 物；苯偶姻、苯偶姻甲基醚、苯偶姻異丙醚等的苯偶姻系化合物；氧化2,4,6-三甲基苯偶姻二苯基膦、氧化雙(2,4,6-三甲基苯甲醯)-苯基膦等的氧化醯基膦系化合物；二苯乙二酮(benzil)(聯苯甲醯)、甲基苯基乙醛酸酯(methyl phenyl glyoxy ester)、羥苯乙酸2-(2-羥基乙氧基)乙酯、羥苯乙酸2-(2-側氧-2-苯基乙醯氧基乙氧基)乙酯等的二苯乙二酮系化合物；二苯基酮、鄰苯甲醯苯甲酸甲酯-4-苯基二苯基酮、4,4’-二氯二苯基酮、羥基二苯基酮、4-苯甲醯基-4’-甲基-二苯基硫醚、丙烯酸化二苯基酮、3,3’,4,4’-四(三級丁過氧羰基)二苯基酮、3,3’-二甲基-4-甲氧基二苯基酮、2,4,6-三甲基二苯基酮、4-甲基二苯基酮等的二苯甲酮系化合物；2-異丙基噻噸酮、2,4-二甲基噻噸酮、2,4-二乙基噻噸酮、2,4-二氯噻噸酮等的噻噸酮系化合物；米其勒酮(Michler's Ketone)、4,4’-二乙胺基二苯基酮等的胺基二苯基酮系化合物；10-丁基-2-氯吖啶酮、2-乙基蒽醌、9,10-菲醌、莰醌(camphorquinone)、1-[4-(4-苯甲醯基苯基氫硫基)苯基]-2-甲基-2-(4-甲苯基磺醯基)丙-1-酮等。這些光聚合起始劑(F)可使用1種，也可2種以上併用。 The photopolymerization initiator (F) may, for example, be diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, or oligomeric {2-hydroxy- 2-methyl-1-[4-(1-methylvinyl)phenyl]acetone}, benzyl dimethyl ketal, 1-(4-isopropylphenyl)-2-hydroxy-2-methyl Propion-1-one, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- Phytyl (4-thiomethylphenyl) propan-1-one, 2-benzyl-2-dimethylamino-1-(4- An acetophenone-based compound such as phenylphenyl)-butanone; a benzoin-based compound such as benzoin, benzoin methyl ether or benzoin isopropyl ether; 2,4,6-trimethyl oxide a phthalylphosphine-based compound such as diphenylphosphine, bis(2,4,6-trimethylbenzhydrazide)-phenylphosphine, or benzil (benzil)醯), methyl phenyl glyoxy ester, 2-(2-hydroxyethoxy)ethyl hydroxyphenylacetate, 2-(2-oxo-2-phenyl phenyl) a diphenylethylenedione compound such as decyloxyethoxy)ethyl ester; diphenyl ketone, methyl phthalic acid benzoate-4-phenyldiphenyl ketone, 4,4'-dichloro bis Phenyl ketone, hydroxydiphenyl ketone, 4-benzylidene-4'-methyl-diphenyl sulfide, acrylated diphenyl ketone, 3,3', 4,4'-tetra (three-stage Butyroxycarbonyl)diphenyl ketone, 3,3'-dimethyl-4-methoxydiphenyl ketone, 2,4,6-trimethyldiphenyl ketone, 4-methyldiphenyl Benzophenone-based compound such as ketone; 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone Such thioxanthone compounds; Michler's Ketone , an aminodiphenyl ketone compound such as 4,4'-diethylaminodiphenyl ketone; 10-butyl-2-chloroacridone, 2-ethyl hydrazine, 9,10-phenanthrenequinone , camphorquinone, 1-[4-(4-benzylidenephenylhydrothio)phenyl]-2-methyl-2-(4-methylsulfonyl)propan-1-one Wait. These photopolymerization initiators (F) may be used alone or in combination of two or more.
又，作為前述光敏劑(G)，可列舉出例如：二乙醇胺、N-甲基二乙醇胺、三丁胺等的三級胺化合物；鄰甲苯硫脲等的脲化合物；二乙基二硫代磷酸鈉、s-苄基異硫脲鎓-對甲苯磺酸鹽等的硫化合物等。 Further, examples of the photosensitizer (G) include a tertiary amine compound such as diethanolamine, N-methyldiethanolamine or tributylamine; a urea compound such as o-toluene thiourea; and diethyldithio A sulfur compound such as sodium phosphate or s-benzylisothiouronium-p-toluenesulfonate.
上述光聚合起始劑(F)及光敏劑(G)的使用量，相對於本發明之活性能量線硬化性組成物中之包含 前述聚合性單體(A)及前述聚合性單體(B)之聚合性成分合計100質量份，較佳各為0.05~20質量份，更佳為0.5~10質量%。 The photopolymerization initiator (F) and the photosensitizer (G) are used in an amount of the polymerizable monomer (A) and the polymerizable monomer (B) in the active energy ray-curable composition of the present invention. The polymerizable component is preferably 100 parts by mass, preferably 0.05 to 20 parts by mass, more preferably 0.5 to 10% by mass.
本發明之活性能量線硬化性組成物中，作為除了上述成分(A)~(G)以外之其它摻合物，依照用途、要求特性，可摻合：聚合抑制劑、表面調理劑、抗靜電劑、消泡劑、黏度調節劑、光穩定劑、耐候穩定劑、耐熱穩定劑、紫外線吸收劑、抗氧化劑、調平劑、有機顏料、無機顏料、顏料分散劑、矽珠、有機珠等的添加劑；氧化矽、氧化鋁、氧化鈦、氧化鋯、五氧化二銻等的無機填充劑等。這些其他摻合物可使用1種，也可2種以上併用。 In the active energy ray-curable composition of the present invention, as a blend other than the above components (A) to (G), it may be blended according to the use and required characteristics: a polymerization inhibitor, a surface conditioner, and an antistatic property. Agent, antifoaming agent, viscosity regulator, light stabilizer, weathering stabilizer, heat stabilizer, ultraviolet absorber, antioxidant, leveling agent, organic pigment, inorganic pigment, pigment dispersant, bead, organic beads, etc. Additives; inorganic fillers such as cerium oxide, aluminum oxide, titanium oxide, zirconium oxide, and antimony pentoxide. These other blends may be used alone or in combination of two or more.
本發明之薄膜係藉由將本發明之活性能量線硬化性組成物塗布在薄膜基材的至少一面上，然後照射活性能量線而形成硬化塗膜所得到者。 The film of the present invention is obtained by applying the active energy ray-curable composition of the present invention to at least one surface of a film substrate and then irradiating the active energy ray to form a cured coating film.
作為本發明之薄膜中使用的前述薄膜基材之材質，較佳為透明性高的樹脂，可列舉出例如：聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯、聚萘二甲酸乙二酯等的聚酯系樹脂；聚丙烯、聚乙烯、聚甲基戊烯-1等的聚烯烴系樹脂；乙酸纖維素(二乙酸纖維素、三乙酸纖維素等)、乙酸丙酸纖維素、乙酸丁酸纖維素、乙酸丙酸丁酸纖維素、乙酸鄰苯二甲酸纖維素、硝酸纖維素等的纖維素系樹脂；聚甲基丙烯酸甲酯等的丙烯酸酯系樹脂；聚氯乙烯、聚偏二氯乙烯等的氯乙烯系樹脂；聚乙烯醇；乙烯/乙酸乙烯酯共聚物；聚苯乙烯；聚醯胺；聚 碳酸酯；聚碸；聚醚碸；聚醚醚酮；聚醯亞胺、聚醚醯亞胺等的聚醯亞胺系樹脂；降莰烯系樹脂(例如日本Zeon股份有限公司製「ZEONOR」)、改性降莰烯系樹脂(例如JSR股份有限公司製「ARTON」)、環烯烴共聚物(例如三井化學股份有限公司製「APEL」)等。此外，也可使用將2種以上的由這些樹脂所形成之基材貼合而成者。 The material of the film substrate used in the film of the present invention is preferably a resin having high transparency, and examples thereof include polyethylene terephthalate, polybutylene terephthalate, and polynaphthalene. a polyester resin such as ethylene formate; a polyolefin resin such as polypropylene, polyethylene or polymethylpentene-1; cellulose acetate (diacetate, cellulose triacetate, etc.), and propionic acid acetate Cellulose resin such as cellulose, cellulose acetate butyrate, cellulose acetate butyrate, cellulose acetate phthalate or nitrocellulose; acrylate resin such as polymethyl methacrylate; polychlorinated Vinyl chloride resin such as ethylene or polyvinylidene chloride; polyvinyl alcohol; ethylene/vinyl acetate copolymer; polystyrene; polyamine; polycarbonate; polyfluorene; polyether oxime; polyether ether ketone; Polyimine-based resin such as polyimine or polyether phthalimide; decene-based resin (for example, "ZEONOR" manufactured by Zeon Co., Ltd.), and modified norbornene-based resin (for example, JSR Co., Ltd.) "ARTON"), cyclic olefin copolymer (such as Mitsui Chemicals Co., Ltd. Limited system "APEL") and so on. Further, it is also possible to use a combination of two or more kinds of substrates formed of these resins.
又，前述薄膜基材可為膜狀也可為片狀，其厚度較佳在20~500μm之範圍。又，在使用膜狀的基材薄膜之情形，其厚度較佳在20~200μm之範圍，更佳在30~150μm之範圍，再更佳在40~130μm之範圍。藉由將薄膜基材的厚度設在該範圍，即便是在利用本發明之活性能量線硬化性組成物於薄膜的單面上設置硬塗層之情形，也變得容易抑制捲曲。 Further, the film substrate may be in the form of a film or a sheet, and the thickness thereof is preferably in the range of 20 to 500 μm. Further, in the case of using a film-like base film, the thickness thereof is preferably in the range of 20 to 200 μm, more preferably in the range of 30 to 150 μm, still more preferably in the range of 40 to 130 μm. By setting the thickness of the film substrate in this range, it is easy to suppress curl even when a hard coat layer is provided on one surface of the film by the active energy ray-curable composition of the present invention.
作為將本發明之活性能量線硬化性組成物塗布在前述薄膜基材上之方法，可列舉出例如：模塗布、微凹版塗布、凹版塗布、滾筒塗布、缺角輪塗布、氣刀塗布、吻合式塗布(kiss coating)、噴塗、浸漬塗布、旋塗、刷塗、利用絲網印刷之滿版塗布、線棒塗布、流塗等。 The method of applying the active energy ray-curable composition of the present invention to the film substrate may, for example, die coating, micro gravure coating, gravure coating, roll coating, corner wheel coating, air knife coating, and bonding. Kiss coating, spray coating, dip coating, spin coating, brush coating, full-size coating by screen printing, wire bar coating, flow coating, and the like.
又，於在本發明之活性能量線硬化性組成物中包含有機溶媒之情形，為了在將活性能量線硬化性組成物塗布於基材薄膜上後且照射活性能量線前，使有機溶媒揮發、並且使前述樹脂(B)偏析在塗膜表面，較佳進行加熱或室溫乾燥。作為加熱乾燥之條件，只要是有機溶劑會揮發之條件，則不特別限定，但通常較佳在溫度 50~100℃之範圍，且時間在0.5~10分鐘之範圍進行加熱乾燥。 Further, in the case where the active energy ray-curable composition of the present invention contains an organic solvent, the organic solvent is volatilized before the active energy ray-curable composition is applied onto the base film and before the active energy ray is irradiated. Further, the resin (B) is segregated on the surface of the coating film, preferably heated or dried at room temperature. The conditions for the heat drying are not particularly limited as long as the organic solvent volatilizes. However, it is usually preferably heated at a temperature of from 50 to 100 ° C for a period of from 0.5 to 10 minutes.
作為使本發明之活性能量線硬化性組成物硬化的活性能量線，如上所述有紫外線、電子射線、α射線、β射線、γ射線等游離輻射線。此時，在使用紫外線作為活性能量線的情形，作為照射該紫外線的裝置，可列舉出例如：低壓汞燈、高壓汞燈、超高壓汞燈、金屬鹵化物燈、無電極燈(融合燈(fusion lamp))、化學燈、黑光燈、汞-氙燈、短弧燈、氦‧鎘雷射、氬雷射、太陽光、LED燈等。 As the active energy ray which hardens the active energy ray-curable composition of the present invention, as described above, there are free radiation such as ultraviolet rays, electron rays, α rays, β rays, and γ rays. In this case, when ultraviolet rays are used as the active energy ray, examples of the apparatus for illuminating the ultraviolet ray include a low-pressure mercury lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, and an electrodeless lamp (fusion lamp ( Fusion lamp)), chemical lamp, black light, mercury-xenon lamp, short arc lamp, cesium cadmium laser, argon laser, sunlight, LED lamp, etc.
於前述薄膜基材上形成本發明之活性能量線硬化性組成物的硬化塗膜時的硬化塗膜之膜厚，從使硬化塗膜的硬度充分，且能抑制因塗膜的硬化收縮造成的薄膜捲曲來看，較佳在1~30μm之範圍，更佳在3~15μm之範圍，再更佳在4~10μm之範圍。 The film thickness of the cured coating film when the cured coating film of the active energy ray-curable composition of the present invention is formed on the film substrate, the hardness of the cured coating film is sufficient, and the curing shrinkage of the coating film can be suppressed. The thickness of the film is preferably in the range of 1 to 30 μm, more preferably in the range of 3 to 15 μm, and even more preferably in the range of 4 to 10 μm.
以下，利用實施例更具體地說明本發明。 Hereinafter, the present invention will be more specifically described by way of examples.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入53.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、29.3質量份的甲基丙烯酸環己酯、14.6質量份的甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、1.9質量份的丙烯酸2-全氟己基乙酯、0.5 質量份的甲基丙烯酸、50質量份的甲醇及10質量份的丙二醇單甲基醚(以下簡稱為「PGME」。)。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C-1)的45質量%溶液。所得到的樹脂(C-1)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 53.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride, 29.3 parts by mass of cyclohexyl methacrylate, and 14.6 parts by mass of methoxypolyethylene were added to the flask. Alcohol methacrylate ("BLEMMER PME-1000" manufactured by Nippon Oil Co., Ltd.; number of repeating units n≒23, molecular weight of 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, and 0.5 parts by mass of methacrylic acid 50 parts by mass of methanol and 10 parts by mass of propylene glycol monomethyl ether (hereinafter referred to as "PGME"). Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C-1) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C-1) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入53.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、14.6質量份的甲基丙烯酸環己酯、29.3質量份的甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、1.9質量份的甲基丙烯酸2-全氟己基乙酯、0.5質量份的甲基丙烯酸、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C-2)的45質量%溶液。所得到的樹脂(C-2)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 53.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride, 14.6 parts by mass of cyclohexyl methacrylate, and 29.3 parts by mass of methoxypolyethylene were added to the flask. Alcohol methacrylate ("BLEMMER PME-1000" manufactured by Nippon Oil Co., Ltd.; number of repeating units n≒23, molecular weight of 1,000), 1.9 parts by mass of 2-perfluorohexylethyl methacrylate, 0.5 parts by mass of A Acrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C-2) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C-2) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後， 在燒瓶中加入53.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、14.6質量份的甲基丙烯酸環己酯、29.3質量份的甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、1.9質量份的丙烯酸2-全氟己基乙酯、0.5質量份的甲基丙烯酸、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C-3)的45質量%溶液。所得到的樹脂(C-3)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 53.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride, 14.6 parts by mass of cyclohexyl methacrylate, and 29.3 parts by mass of methoxypolyethylene were added to the flask. Alcohol methacrylate ("BLEMMER PME-1000" manufactured by Nippon Oil Co., Ltd.; number of repeating units n≒23, molecular weight of 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, and 0.5 part by mass of methacrylic acid 50 parts by mass of methanol and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C-3) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C-3) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入53.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、43.9質量份的甲基丙烯酸環己酯、1.9質量份的丙烯酸2-全氟己基乙酯、0.5質量份的甲基丙烯酸、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C-4)的45質量%溶液。所得到的樹脂(C-4)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 53.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride, 43.9 parts by mass of cyclohexyl methacrylate, and 1.9 parts by mass of 2-perfluorohexyl acrylate were added to the flask. Ethyl ester, 0.5 parts by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C-4) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C-4) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入54.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、19.9質量份的甲基丙烯酸環己酯、24.9質量份的甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、0.5質量份的甲基丙烯酸、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C-5)的45質量%溶液。所得到的樹脂(C-5)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 54.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride, 19.9 parts by mass of cyclohexyl methacrylate, and 24.9 parts by mass of methoxypolyethylene were added to the flask. Alcohol methacrylate ("BLEMMER PME-1000" manufactured by NOF Corporation; number of repeating units n≒23, molecular weight: 1,000), 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C-5) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C-5) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入54.0質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、44.1質量份的甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、1.9質量份的丙烯酸2-全氟己基乙酯、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使 其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C’-1)的45質量%溶液。所得到的樹脂(C’-1)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 54.0 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride and 44.1 parts by mass of methoxypolyethylene glycol methacrylate (Nippon Oil Co., Ltd.) were added to the flask. "BLEMMER PME-1000"; repeating unit number n≒23, molecular weight 1,000), 1.9 parts by mass of 2-perfluorohexylethyl acrylate, 50 parts by mass of methanol, and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C'-1) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C'-1) had a weight average molecular weight of 10,000.
在配備有攪拌裝置、回流冷凝管及氮氣導入管之燒瓶中導入氮氣，以氮氣取代燒瓶內的空氣。然後，在燒瓶中加入54.7質量份的氯化2-(甲基丙烯醯氧基)乙基三甲基銨、44.8質量份甲氧基聚乙二醇甲基丙烯酸酯(日油股份有限公司製「BLEMMER PME-1000」；重複單元數n≒23、分子量1,000)、0.5質量份的甲基丙烯酸、50質量份的甲醇及10質量份的PGME。接下來，花費30分鐘滴入以2.4質量份的PGME溶解0.1質量份的聚合起始劑(偶氮雙異丁腈)而成的溶液後，使其於65℃反應3小時。接下來，加入甲醇進行稀釋，得到具有脂環結構及四級銨鹽之樹脂(C’-2)的45質量%溶液。所得到的樹脂(C’-2)的重量平均分子量為1萬。 Nitrogen gas was introduced into a flask equipped with a stirring device, a reflux condenser, and a nitrogen introduction tube, and the air in the flask was replaced with nitrogen. Then, 54.7 parts by mass of 2-(methacryloxy)ethyltrimethylammonium chloride and 44.8 parts by mass of methoxypolyethylene glycol methacrylate (manufactured by Nippon Oil Co., Ltd.) were added to the flask. "BLEMMER PME-1000"; repeating unit number n≒23, molecular weight 1,000), 0.5 part by mass of methacrylic acid, 50 parts by mass of methanol, and 10 parts by mass of PGME. Next, a solution obtained by dissolving 0.1 part by mass of a polymerization initiator (azobisisobutyronitrile) in 2.4 parts by mass of PGME was added dropwise thereto over 30 minutes, and then reacted at 65 ° C for 3 hours. Next, methanol was added and diluted to obtain a 45 mass% solution of a resin (C'-2) having an alicyclic structure and a quaternary ammonium salt. The obtained resin (C'-2) had a weight average molecular weight of 10,000.
上述所得到的樹脂(C-1)~(C-5)、(C’-1)及(C’-2)之重量平均分子量係藉由凝膠滲透層析(GPC)法依下述條件測定。 The weight average molecular weights of the resins (C-1) to (C-5), (C'-1) and (C'-2) obtained above are determined by gel permeation chromatography (GPC) according to the following conditions. Determination.
測定裝置：高速GPC裝置(TOSOH股份有限公司製「HLC-8220GPC」) Measuring device: High-speed GPC device ("HLC-8220GPC" manufactured by TOSOH Co., Ltd.)
管柱：將TOSOH股份有限公司製的下述管柱串聯連接來使用。 Pipe column: The following pipe strings manufactured by TOSOH Co., Ltd. are connected in series and used.
「TSKgel G5000」(7.8mmI.D.×30cm)×1支 "TSKgel G5000" (7.8mmI.D.×30cm) × 1
「TSKgel G4000」(7.8mmI.D.×30cm)×1支 "TSKgel G4000" (7.8mmI.D.×30cm) × 1
「TSKgel G3000」(7.8mmI.D.×30cm)×1支 "TSKgel G3000" (7.8mmI.D.×30cm) × 1
「TSKgel G2000」(7.8mmI.D.×30cm)×1支 "TSKgel G2000" (7.8mmI.D.×30cm) × 1
檢測器：RI(微差折射計) Detector: RI (differential refractometer)
管柱溫度：40℃ Column temperature: 40 ° C
沖提液：四氫呋喃(THF) Effervescent solution: tetrahydrofuran (THF)
流速：1.0mL/分鐘 Flow rate: 1.0 mL/min
注入量：100μL(試料濃度0.4質量%之四氫呋喃溶液) Injection amount: 100 μL (sample concentration 0.4% by mass in tetrahydrofuran solution)
標準試料：使用下述標準聚苯乙烯製作檢量線。 Standard sample: A calibration curve was prepared using the following standard polystyrene.
(標準聚苯乙烯) (standard polystyrene)
TOSOH股份有限公司製「TSKgel標準聚苯乙烯A-500」 "TSKgel Standard Polystyrene A-500" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯A-1000」 "TSKgel Standard Polystyrene A-1000" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯A-2500」 "TSKgel Standard Polystyrene A-2500" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯A-5000」 "TSKgel Standard Polystyrene A-5000" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-1」 "TSKgel Standard Polystyrene F-1" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-2」 "TSKgel Standard Polystyrene F-2" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-4」 "TSKgel Standard Polystyrene F-4" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-10」 "TSKgel Standard Polystyrene F-10" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-20」 "TSKgel Standard Polystyrene F-20" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-40」 "TSKgel Standard Polystyrene F-40" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-80」 "TSKgel Standard Polystyrene F-80" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-128」 "TSKgel Standard Polystyrene F-128" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-288」 "TSKgel Standard Polystyrene F-288" manufactured by TOSOH Co., Ltd.
TOSOH股份有限公司製「TSKgel標準聚苯乙烯F-550」 "TSKgel Standard Polystyrene F-550" manufactured by TOSOH Co., Ltd.
將17質量份的高折射率聚合性單體(9,9-雙[4-(2-丙烯醯氧基乙氧基)苯基]茀，折射率1.616)(以下簡稱為「單體(A-1)」。)、17質量份的高折射率聚合性單體(丙烯酸鄰苯基苄酯與丙烯酸對苯基苄酯的等量混合物，折射率1.591，苯基)(以下簡稱為「單體(A-2)」。)、66質量份的多官能丙烯酸酯混合物(64質量%的二新戊四醇六丙烯酸酯、17質量%的二新戊四醇五丙烯酸酯、19質量%的二新戊四醇四丙烯酸酯之混合物)(以下簡稱 為「單體(B-1)」。)、6.7質量份的製造例1所得到之樹脂(C-1)的45質量%溶液(以樹脂(C-1)計為3質量份)、5質量份的光聚合起始劑(BASF Japan股份有限公司「Irgacure 184」；1-羥基環己基苯基酮)、40質量份的甲乙酮(以下簡稱為「MEK」。)及60質量份的PGME均勻混合，得到非揮發性成分50質量%的活性能量線硬化性組成物(1)。 17 parts by mass of a high refractive index polymerizable monomer (9,9-bis[4-(2-acryloxyethoxy)phenyl)anthracene, refractive index of 1.616) (hereinafter referred to as "monomer (A) -1)"), 17 parts by mass of a high refractive index polymerizable monomer (equal mixture of o-phenyl benzyl acrylate and p-phenyl benzyl acrylate, refractive index 1.591, phenyl) (hereinafter referred to as "single" (A-2)"), 66 parts by mass of a polyfunctional acrylate mixture (64% by mass of dipentaerythritol hexaacrylate, 17% by mass of dipentaerythritol pentaacrylate, 19% by mass a mixture of dipentaerythritol tetraacrylate (hereinafter referred to as "monomer (B-1)") and 6.7 parts by mass of a 45 mass% solution of the resin (C-1) obtained in Production Example 1 The resin (C-1) is 3 parts by mass), 5 parts by mass of a photopolymerization initiator (BASF Japan Co., Ltd. "Irgacure 184"; 1-hydroxycyclohexyl phenyl ketone), and 40 parts by mass of methyl ethyl ketone (below) For example, "MEK" is simply referred to as 60 parts by mass of PGME, and an active energy ray-curable composition (1) having a nonvolatile component content of 50% by mass is obtained.
除了變更為表1~3中所示之組成以外，與實施例1同樣地進行，得到活性能量線硬化性組成物(2)~(7)。 The active energy ray-curable compositions (2) to (7) were obtained in the same manner as in Example 1 except that the compositions shown in Tables 1 to 3 were changed.
除了變更為表3中所示的組成以外，與實施例1同樣地進行，得到活性能量線硬化性組成物(R1)及(R2)。 The active energy ray-curable compositions (R1) and (R2) were obtained in the same manner as in Example 1 except that the composition shown in Table 3 was changed.
另外，表1~3中記載的縮寫表示下述者。 In addition, the abbreviations described in Tables 1-3 represent the following.
單體(A-3)：DIC股份有限公司製「UNIDIC EQS-1179」(雙酚A型多官能丙烯酸酯，折射率1.555) Monomer (A-3): "UNIDIC EQS-1179" manufactured by DIC Corporation (bisphenol A type polyfunctional acrylate, refractive index: 1.555)
DMC：碳酸二甲酯 DMC: dimethyl carbonate
使用上述實施例1~7及比較例1~2所得到的活性能量線硬化性組成物(1)~(7)、(R1)~(R2)，進行下述試驗、測定。 The active energy ray-curable compositions (1) to (7) and (R1) to (R2) obtained in the above Examples 1 to 7 and Comparative Examples 1 and 2 were subjected to the following tests and measurements.
將活性能量線硬化性組成物以棒塗機以成為膜厚5μm的方式塗布在厚度60μm的三乙酸纖維素(TAC) 薄膜(FUJIFILM股份有限公司製)，於60℃乾燥1.5分鐘後，在空氣環境下使用紫外線照射裝置(EYE GRAPHICS股份有限公司製，高壓汞燈)以照射光量3kJ/m2照射，得到具有硬化塗膜之TAC薄膜作為評價用樣本。 The active energy ray-curable composition was applied to a cellulose acetate triacetate (TAC) film (manufactured by FUJIFILM Co., Ltd.) having a thickness of 60 μm in a bar coater at a film thickness of 5 μm, and dried at 60 ° C for 1.5 minutes in the air. In the environment, an ultraviolet irradiation device (manufactured by EYE GRAPHICS Co., Ltd., a high-pressure mercury lamp) was used to irradiate at a light amount of 3 kJ/m 2 to obtain a TAC film having a cured coating film as a sample for evaluation.
對上述得到之評價用樣本之硬化塗膜的表面，依據JIS試驗方法K5600-5-4：1999，測定鉛筆硬度。 The pencil hardness of the surface of the cured coating film of the sample for evaluation obtained above was measured in accordance with JIS Test Method K5600-5-4:1999.
對上述得到之評價用樣本，依據JIS試驗方法K7136：2000，使用霧度計(日本電色工業股份有限公司製「NDH2000」)測定霧度值。 For the sample for evaluation obtained above, the haze value was measured using a haze meter ("NDH2000" manufactured by Nippon Denshoku Industries Co., Ltd.) in accordance with JIS Test Method K7136:2000.
對上述得到之評價用樣本，依據JIS試驗方法K7142：2014的A方法，使用阿貝折射儀(ATAGO股份有限公司製「DR-M2」)測定折射率。 The sample for evaluation obtained above was measured for refractive index according to the A method of JIS test method K7142:2014 using an Abbe refractometer ("DR-M2" manufactured by ATAGO Co., Ltd.).
對上述得到之評價用樣本的硬化塗膜的表面，依據JIS試驗方法K6911-1995，使用高阻抗率計(三菱化學ANALYTECH股份有限公司製「Hiresta-UP MCP-HT450」)，以施加電壓500V、測定時間10秒測定表面電阻值。 The surface of the cured coating film of the sample for evaluation obtained above was subjected to a high-impedance meter ("Hiresta-UP MCP-HT450" manufactured by Mitsubishi Chemical Corporation ANALYTECH Co., Ltd.) in accordance with JIS test method K6911-1995, and a voltage of 500 V was applied. The surface resistance value was measured for 10 seconds.
將上述測定的結果示於表1~3。 The results of the above measurements are shown in Tables 1 to 3.
由表1~3中所示的評價結果可以確認到，實施例1~7的本發明之活性能量線硬化性組成物的硬化塗膜的折射率高，表面電阻值也為10的9~10次方等級，抗靜電性亦高。 From the evaluation results shown in Tables 1 to 3, it was confirmed that the cured coating film of the active energy ray-curable composition of the present invention of Examples 1 to 7 has a high refractive index and a surface resistance value of 10 to 10 of 10 The level of the secondary is also high in antistatic properties.
另一方面，比較例1及2為使用不具有脂環結構而具有四級銨鹽之樹脂之例子。雖然這些折射率都高，但其表面電阻值都超過10的13次方，可確認抗靜電性差。 On the other hand, Comparative Examples 1 and 2 are examples in which a resin having a quaternary ammonium salt and having no alicyclic structure is used. Although these refractive indexes were high, the surface resistance values exceeded the 13th power of 10, and it was confirmed that the antistatic property was poor.
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