TW201802172A - Active energy ray-curable resin composition for optical article, cured body, and optical sheet - Google Patents
Active energy ray-curable resin composition for optical article, cured body, and optical sheet Download PDFInfo
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- TW201802172A TW201802172A TW106108626A TW106108626A TW201802172A TW 201802172 A TW201802172 A TW 201802172A TW 106108626 A TW106108626 A TW 106108626A TW 106108626 A TW106108626 A TW 106108626A TW 201802172 A TW201802172 A TW 201802172A
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- TW
- Taiwan
- Prior art keywords
- active energy
- energy ray
- meth
- acrylate
- polymerizable compound
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- 230000003287 optical effect Effects 0.000 title claims abstract description 54
- 239000011342 resin composition Substances 0.000 title abstract description 42
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- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000003999 initiator Substances 0.000 claims abstract description 12
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- 125000003118 aryl group Chemical group 0.000 claims description 19
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 105
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- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000004711 α-olefin Substances 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
本發明係關於應用了照射活性能量射線所致之硬化反應之使用於鑄模聚合的光學物品用活性能量射線硬化型樹脂組成物，及使該組成物硬化而得之光學片。The present invention relates to an active energy ray-curable resin composition for an optical article used for polymerizing a mold, which uses a curing reaction caused by irradiation of active energy rays, and an optical sheet obtained by curing the composition.
應用了照射活性能量射線所致之硬化反應的技術係廣泛地應用於塗料、光阻材料、印墨、黏著劑等。雖然以前一般而言有厚度數μm左右之膜厚的應用技術，於近年來利用了活性能量射線硬化型樹脂組成物可進行無溶劑塗布之優點，或藉由照射產生立即之硬化反應的優點，讓以數十μm以上之膜厚來製作特定之形狀的加工、塗布技術受到注目，且有人將光造型法或光鑄模聚合法等投入實際運用。 其中，光鑄模聚合法係例如對於經賦予微細形狀之母模填充(整批注入)活性能量射線硬化型樹脂組成物，介隔母模，藉由紫外線等使該樹脂組成物硬化之方法，可精密且大量地製造母模的複製。The technology that applies the hardening reaction caused by irradiation of active energy rays is widely used in coatings, photoresist materials, printing inks, adhesives, and the like. Although conventionally there are generally applied technologies with a film thickness of about several μm, in recent years, the advantages of active energy ray-curable resin composition can be applied without solvent, or the advantage of immediate curing reaction by irradiation, Attention has been paid to processing and coating techniques for producing specific shapes with a film thickness of several tens of μm or more, and some people have put the optical modeling method or the photo-casting polymerization method into practical use. Among them, the photo-mold polymerization method is, for example, a method of filling (mass injection) an active energy ray-curable resin composition through a master mold having a fine shape, and curing the resin composition by ultraviolet rays through the master mold. Replicas of master molds are made precisely and in large quantities.
伴隨著設備之小型化、輕量化，上述光鑄模聚合法係適用於在塑膠基材上具有由樹脂硬化物構成之微細且複雜之凹凸表現形狀的具形狀之光學片(例如，稜鏡透鏡片或菲涅耳透鏡片等)、透鏡、稜鏡等塑膠物品或光學物品之製造的方法。對於在藉由該光鑄模聚合法製造塑膠物品或光學物品時所使用之活性能量射線硬化型樹脂組成物要求優良之硬化性，且對於製造之硬化物要求模再現性(將硬化物從母模剝離時，從模轉印而得之微細形狀不會缺損或變形之性質)或耐刮性。此外，獲得之硬化物為光學片時，常常與擴散薄膜等其它薄膜進行疊層，此時也會要求尺寸安定性或減低捲曲性。然而，光鑄模聚合法等藉由光之聚合有聚合時的硬化收縮大，有就尺寸安定性或耐捲曲性為不良之情事。Along with the miniaturization and weight reduction of the equipment, the above-mentioned photo-mold polymerization method is suitable for shaped optical sheets (for example, 稜鏡 lens sheets) having a fine and complicated concave-convex shape composed of a resin hardened material on a plastic substrate. Or Fresnel lens sheet, etc.), lenses, cymbals and other plastic or optical articles. The active energy ray-curable resin composition used when manufacturing a plastic article or an optical article by the photo-mold polymerization method requires excellent hardenability, and requires mold reproducibility for the produced hardened product (removing the hardened product from the master mold). At the time of peeling, the fine shape transferred from the mold is not damaged or deformed) or scratch resistance. In addition, when the obtained hardened material is an optical sheet, it is often laminated with another film such as a diffusion film, and in this case, dimensional stability or curl reduction is also required. However, in the photo-mold polymerization method and the like, the curing shrinkage during polymerization is large by the polymerization of light, and there is a case where the dimensional stability and curl resistance are not good.
就硬化性優良，獲得之硬化物的模再現性也優良之光學物品用活性能量射線硬化型樹脂組成物而言，例如已有許多含有環氧(甲基)丙烯酸酯或胺甲酸乙酯(urethane)(甲基)丙烯酸酯之活性能量射線硬化型樹脂組成物之報告。具體而言，已知有例如含有雙酚A型環氧(甲基)丙烯酸酯、單官能(甲基)丙烯酸酯、2官能(甲基)丙烯酸酯及重量平均分子量為9.5萬之丙烯酸樹脂等聚合物成分，且硬化後之折射率為1.55以上的稜鏡透鏡用游離輻射線硬化型樹脂組成物(例如，參照專利文獻1)、或其含有：含有式(1)表示之化合物之具有聚合性不飽和雙鍵的單體、將聚合性不飽和單體聚合而得之重量平均分子量為2,000~100,000且聚合物結構中含有聚合性不飽和雙鍵之聚合物、及光聚合起始劑，且該單體與聚合物之含量為特定之比率(例如，參照專利文獻2)的一種光學物品用活性能量射線硬化型樹脂組成物。As for the active energy ray-curable resin composition for optical articles, which has excellent hardenability and excellent mold reproducibility of the obtained hardened product, for example, many epoxy (meth) acrylates or urethanes are contained. ) Report of active energy ray-curable resin composition of (meth) acrylate. Specifically, for example, bisphenol A epoxy (meth) acrylate, monofunctional (meth) acrylate, bifunctional (meth) acrylate, and acrylic resin having a weight average molecular weight of 95,000 are known. Free-radiation-curable resin composition (for example, refer to Patent Document 1) for a fluorene lens having a polymer component and a refractive index of 1.55 or more after curing, or a polymer containing a compound represented by the formula (1) Monomers with unsaturated double bonds, polymers with polymerizable unsaturated monomers having a weight average molecular weight of 2,000 to 100,000 and polymerizable unsaturated double bonds in the polymer structure, and photopolymerization initiators, An active energy ray-curable resin composition for an optical article in which the content of the monomer and the polymer is a specific ratio (for example, refer to Patent Document 2).
【化1】
然而，在上述專利文獻1中記載之稜鏡透鏡用游離輻射線硬化型樹脂組成物，該聚合物成分不會鍵結至硬化反應所產生之交聯結構。因此，聚合物成分之含量多時有硬化性變差的傾向。此外，在專利文獻2中記載之光學物品用活性能量射線硬化型樹脂組成物，雖然模再現性優良但有時有就尺寸安定性或捲曲性而言為不良的情況。 [先前技術文獻] [專利文獻]However, in the free radiation-curable resin composition for a holmium lens described in Patent Document 1, the polymer component is not bonded to a cross-linked structure generated by a curing reaction. Therefore, when the content of the polymer component is large, the curability tends to deteriorate. In addition, the active energy ray-curable resin composition for an optical article described in Patent Document 2 may have poor mold reproducibility but may be inferior in terms of dimensional stability and curlability. [Prior Art Literature] [Patent Literature]
[專利文獻1] 日本特開平11-240926號公報 [專利文獻2] 日本特開2010-60890號公報[Patent Document 1] Japanese Patent Laid-Open No. 11-240926 [Patent Document 2] Japanese Patent Laid-Open No. 2010-60890
[發明所欲解決之課題] 本發明之課題係提供模再現性、耐刮性優良、且就尺寸安定性或捲曲性而言為優良之光學物品用活性能量射線硬化型樹脂組成物、硬化物、及使光學物品用活性能量射線硬化型樹脂組成物硬化而得之光學片。 [解決課題之手段][Problems to be Solved by the Invention] An object of the present invention is to provide an active energy ray-curable resin composition and a cured product for an optical article which are excellent in mold reproducibility and scratch resistance and are excellent in dimensional stability and curlability. And an optical sheet obtained by curing an active energy ray-curable resin composition for optical articles. [Means for solving problems]
一般而言，若降低組成物中之活性能量射線聚合性基的濃度，因為交聯密度下降，故硬化收縮減低，可抑制捲曲性。但在另一方面，耐刮性等機械物性也會下降。然而本案發明者們在深入研究之結果，發現藉由使組成物中之環氧乙烷濃度及具有2個以上之活性能量射線聚合性基的聚合性化合物的量為特定之範圍，可解決上述課題。 本案發明者們發現，藉由使用於結構中具有環氧乙烷骨架之具2個以上活性能量射線聚合性基的聚合性化合物，將柔軟之環氧乙烷基有效地導入至硬化物之主鏈，能減低在硬化時發生之內部應力也就是硬化收縮，結果可獲得維持了耐刮性且還抑制了捲曲性之硬化物。In general, if the concentration of the active energy ray polymerizable group in the composition is decreased, the crosslinking density is reduced, so that the curing shrinkage is reduced, and the curlability can be suppressed. On the other hand, mechanical properties such as scratch resistance also decrease. However, as a result of intensive studies by the inventors of the present case, it was found that the above-mentioned problems can be solved by setting the ethylene oxide concentration in the composition and the amount of the polymerizable compound having two or more active energy ray polymerizable groups to a specific range. Topic. The inventors of this case have discovered that by using a polymerizable compound having two or more active energy ray polymerizable groups having an ethylene oxide skeleton in the structure, a flexible ethylene oxide group is effectively introduced into the main body of the hardened material. Chains can reduce the internal stress that occurs during hardening, that is, hardening shrinkage. As a result, a hardened product that maintains scratch resistance and also suppresses curling can be obtained.
也就是說，本發明係提供一種光學物品用活性能量射線硬化性組成物，該光學物品用活性能量射線硬化性組成物含有活性能量射線聚合性化合物及光聚合起始劑，且 (1) 含有具2個以上之活性能量射線聚合性基且具有環氧乙烷基的聚合性化合物，且該環氧乙烷基之重量濃度相對於該活性能量射線聚合性化合物之全部量為6.0~15.0重量%； (2) 具2個以上之活性能量射線聚合性基之聚合性化合物之含量相對於該活性能量射線聚合性化合物之全部量為30~70重量%。That is, the present invention provides an active energy ray-curable composition for an optical article. The active energy ray-curable composition for an optical article contains an active energy ray-polymerizable compound and a photopolymerization initiator, and (1) contains A polymerizable compound having two or more active energy ray polymerizable groups and an ethylene oxide group, and the weight concentration of the ethylene oxide group is 6.0 to 15.0 weight based on the total amount of the active energy ray polymerizable compound. %; (2) The content of the polymerizable compound having two or more active energy ray polymerizable groups is 30 to 70% by weight relative to the total amount of the active energy ray polymerizable compound.
此外，本發明提供將上述記載之光學物品用活性能量射線硬化性組成物藉由活性能量射線使其硬化而得之硬化物。Moreover, this invention provides the hardened | cured material obtained by hardening | curing the active-energy-ray-curable composition for optical articles as described above by active energy rays.
此外，本發明提供將上述記載之光學物品用活性能量射線硬化性組成物藉由活性能量射線使其硬化而得之光學片。 [發明之效果]The present invention also provides an optical sheet obtained by curing the active energy ray-curable composition for an optical article described above with an active energy ray. [Effect of the invention]
藉由本發明，可獲得模再現性、耐刮性優良、且就尺寸安定性或耐捲曲性而言為優良之稜鏡透鏡片或菲涅耳透鏡片等具有微細之表面形狀的光學片。According to the present invention, an optical sheet having a fine surface shape such as a fluorene lens sheet or a Fresnel lens sheet, which is excellent in mold reproducibility and scratch resistance and is excellent in dimensional stability or curl resistance, can be obtained.
(活性能量射線聚合性化合物) 於本發明使用之活性能量射線聚合性化合物係： (1) 含有具2個以上之活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物作為必要成分；且 (2) 具2個以上之活性能量射線聚合性基之聚合性化合物之含量相對於該活性能量射線聚合性化合物之全部量為30~70重量%。(Active energy ray polymerizable compound) The active energy ray polymerizable compound used in the present invention is: (1) A polymerizable compound having two or more active energy ray polymerizable groups and having an ethylene oxide group as an essential component And (2) the content of the polymerizable compound having two or more active energy ray polymerizable groups is 30 to 70% by weight relative to the total amount of the active energy ray polymerizable compound.
(1) 具有2個以上活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物 就本發明中使用之具有2個以上活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物而言，並沒有特別之限定，可使用公知者。 (其中，在本發明中，二(甲基)丙烯酸酯表示具有2個(甲基)丙烯醯基之化合物，三(甲基)丙烯酸酯表示具有3個(甲基)丙烯醯基之化合物，多(甲基)丙烯酸酯表示具有2個以上(甲基)丙烯醯基之化合物，(甲基)丙烯酸酯表示丙烯酸酯及甲基丙烯酸酯之總稱，(甲基)丙烯醯基表示丙烯醯基及甲基丙烯醯基之總稱。此外，有時會將環氧乙烷簡稱為EO)(1) A polymerizable compound having two or more active energy ray polymerizable groups and having an oxirane group The polymerizable compound having two or more active energy ray polymerizable groups and having an oxirane group used in the present invention The compound is not particularly limited, and a known one can be used. (In the present invention, di (meth) acrylate means a compound having two (meth) acrylfluorenyl groups, and tri (meth) acrylate means a compound having three (meth) acrylfluorenyl groups, Poly (meth) acrylate means a compound having two or more (meth) acryl groups, (meth) acrylate means a general term for acrylates and methacrylates, and (meth) acryl groups means acryl groups And methacrylfluorene. In addition, ethylene oxide is sometimes referred to as EO)
可舉例如乙二醇二(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、四乙二醇二(甲基)丙烯酸酯、七乙二醇二(甲基)丙烯酸酯等將具有環氧乙烷基之二醇與(甲基)丙烯酸進行反應而得之環氧乙烷基改性二(甲基)丙烯酸酯、或Examples thereof include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, Heptaethylene glycol di (meth) acrylate, etc. Ethylene oxide-modified di (meth) acrylate obtained by reacting a diol having an ethylene oxide group with (meth) acrylic acid, or
三羥甲基丙烷之環氧乙烷改性多(甲基)丙烯酸酯、二(三羥甲基)丙烷之環氧乙烷改性多(甲基)丙烯酸酯、新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯、二新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯、四羥甲基甲烷之環氧乙烷改性多(甲基)丙烯酸酯等將具有環氧乙烷基之多元醇與(甲基)丙烯酸反應而得之環氧乙烷基改性多(甲基)丙烯酸酯、或Ethylene oxide modified poly (meth) acrylate of trimethylolpropane, ethylene oxide modified poly (meth) acrylate of bis (trimethylol) propane, epoxy of neopentyl tetraol Ethane-modified poly (meth) acrylate, ethylene oxide-modified poly (meth) acrylate of dipentaerythritol, ethylene oxide-modified poly (meth) acrylate of tetramethylolmethane Ethylene oxide-modified poly (meth) acrylates obtained by reacting a polyol having an ethylene oxide group with (meth) acrylic acid, or
環氧乙烷基改性環氧多(甲基)丙烯酸酯、環氧乙烷基改性胺甲酸乙酯多(甲基)丙烯酸酯、環氧乙烷基改性聚酯多(甲基)丙烯酸酯等環氧乙烷改性多(甲基)丙烯酸酯寡聚物等。Ethylene oxide modified epoxy poly (meth) acrylate, ethylene oxide modified urethane poly (meth) acrylate, ethylene oxide modified polyester poly (methyl) Ethylene oxide modified poly (meth) acrylate oligomers and the like.
上述環氧乙烷基之重量濃度相對於上述活性能量射線聚合性化合物之全部量為6.0~15.0重量%。藉由使該重量濃度為該範圍，可兼具捲曲性及耐刮性等機械物性。其中，上述環氧乙烷基之重量濃度宜為6.5~10.0重量%，最好宜為7.0~9.0重量%。The weight concentration of the ethylene oxide group is 6.0 to 15.0% by weight based on the total amount of the active energy ray polymerizable compound. When the weight concentration is within this range, mechanical properties such as curlability and scratch resistance can be combined. Among them, the weight concentration of the above ethylene oxide group is preferably 6.5 to 10.0% by weight, and most preferably 7.0 to 9.0% by weight.
在上述具2個以上之活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物中，宜使用三羥甲基丙烷之環氧乙烷改性多(甲基)丙烯酸酯、二(三羥甲基)丙烷之環氧乙烷改性多(甲基)丙烯酸酯、新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯、二新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯、四羥甲基甲烷之環氧乙烷改性多(甲基)丙烯酸酯等之將具有環氧乙烷基之多元醇與(甲基)丙烯酸進行反應而得之環氧乙烷基改性多(甲基)丙烯酸酯，最好宜使用二新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯。Among the above polymerizable compounds having two or more active energy ray-polymerizable groups and having an ethylene oxide group, it is preferable to use trimethylolpropane-modified ethylene (meth) acrylate, di (meth) acrylate, Ethylene oxide modified poly (meth) acrylate of trimethylol) propane, ethylene oxide modified poly (meth) acrylate of neopentyl tetraol, ethylene oxide of dipentaerythritol Modified poly (meth) acrylates, ethylene oxide-modified poly (meth) acrylates of tetramethylolmethane, and the like The obtained ethylene oxide-modified poly (meth) acrylate is preferably an ethylene oxide-modified poly (meth) acrylate of dipentaerythritol.
(2) 具有2個以上之活性能量射線聚合性基之聚合性化合物 就本發明中使用之具有2個以上之活性能量射線聚合性基之聚合性化合物而言，並沒有特別之限定，可使用公知之化合物。 可舉例如1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,5-戊二醇二(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、1,8-辛二醇二(甲基)丙烯酸酯、1,9-壬二醇二(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、或(2) The polymerizable compound having two or more active energy ray polymerizable groups The polymerizable compound having two or more active energy ray polymerizable groups used in the present invention is not particularly limited and can be used Well-known compounds. For example, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,5-pentanediol di (meth) acrylate, 3- Methyl-1,5-pentanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,8-octyl Glycol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, tricyclodecanedimethanol di (meth) acrylate, ethylene glycol di (meth) acrylate, or
具有2個以上活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物、具有環氧乙烷基以外之環氧烷基之聚合性化合物，例如丙二醇二(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、四丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、羥基三甲基乙酸新戊二醇二(甲基)丙烯酸酯、對於羥基三甲基乙酸新戊二醇加成己內酯而得之化合物之二(甲基)丙烯酸酯、新戊二醇己二酸二(甲基)丙烯酸酯、或Polymerizable compounds having two or more active energy ray polymerizable groups and ethylene oxide groups, and polymerizable compounds having alkylene oxide groups other than ethylene oxide groups, such as propylene glycol di (meth) acrylate, Propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, tetrapropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, 1,3-butanediol di (meth) acrylate ) Acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, new Pentylene glycol di (meth) acrylate, hydroxytrimethylacetic acid neopentyl glycol di (meth) acrylate, two compounds obtained by adding caprolactone to hydroxytrimethylacetic acid neopentyl glycol ( (Meth) acrylate, neopentyl glycol adipate di (meth) acrylate, or
三羥甲基丙烷三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、二新戊四醇之多(甲基)丙烯酸酯、對於三羥甲基丙烷、二(三羥甲基)丙烷、新戊四醇、二新戊四醇、四羥甲基甲烷加成了1~20莫耳之環氧乙烷以外的環氧烷而得之含羥基化合物等之具有3個以上羥基之化合物與(甲基)丙烯酸形成3分子以上之酯鍵結而得之化合物等、或Trimethylolpropane tri (meth) acrylate, neopentaerythritol tri (meth) acrylate, poly (meth) acrylate of dipentaerythritol, for trimethylolpropane, bis (trihydroxy) (Methyl) propane, neopentaerythritol, dipentaerythritol, and tetramethylolmethane are obtained by adding 1 to 20 mol of ethylene oxide other than alkylene oxide. Compounds obtained by the above hydroxyl compound forming (3) or more ester bonds with (meth) acrylic acid, or
藉由將選自於由雙酚A型環氧樹脂、雙酚F型環氧樹脂、一部分經鹵素取代之雙酚A型環氧樹脂、一部分經鹵素取代之雙酚F型環氧樹脂、氫化雙酚A型環氧樹脂、及此等之混合物構成之群組中之1種以上的環氧樹脂與多莫耳之(甲基)丙烯酸反應而得之雙酚型的環氧(甲基)丙烯酸酯或苯酚酚醛清漆型之環氧(甲基)丙烯酸酯、甲酚酚醛清漆型之環氧(甲基)丙烯酸酯、萘骨架之環氧(甲基)丙烯酸酯或此等之混合物、或By selecting from bisphenol A type epoxy resin, bisphenol F type epoxy resin, part of halogen-substituted bisphenol A type epoxy resin, part of halogen-substituted bisphenol F type epoxy resin, hydrogenation Bisphenol A epoxy resin, and a mixture of one or more epoxy resins in the group consisting of these bisphenol A epoxy resins and domoral (meth) acrylic acid. Epoxy (meth) acrylates of the acrylate or phenol novolak type, epoxy (meth) acrylates of the cresol novolak type, epoxy (meth) acrylates of the naphthalene skeleton or mixtures thereof, or
藉由多元醇與具有環狀結構之有機多異氰酸酯與多莫耳之含羥基(甲基)丙烯酸酯反應而得之胺甲酸乙酯(甲基)丙烯酸酯、藉由具有環狀結構之二醇與有機多異氰酸酯與多莫耳之含羥基(甲基)丙烯酸酯的反應而得之胺甲酸乙酯(甲基)丙烯酸酯、藉由具有環狀結構之有機多異氰酸酯與多莫耳之含羥基(甲基)丙烯酸酯之反應而得之胺甲酸乙酯(甲基)丙烯酸酯等。Urethane (meth) acrylate obtained by reacting a polyol with an organic polyisocyanate having a cyclic structure and a hydroxy-containing (meth) acrylate of Domor, and a diol having a cyclic structure A urethane (meth) acrylate obtained by reacting with an organic polyisocyanate and a hydroxy-containing (meth) acrylate of Domol, an organic polyisocyanate having a cyclic structure, and a hydroxyl group of Domor Urethane (meth) acrylate and the like obtained by the reaction of (meth) acrylate.
上述具有2個以上活性能量射線聚合性基之聚合性化合物可使用1種亦可混合多種使用。The polymerizable compound having two or more active energy ray polymerizable groups may be used alone or in combination.
如同前述，在本發明中，上述具有2個以上活性能量射線聚合性基之聚合性化合物相對於上述活性能量射線聚合性化合物之全部量必須為30~70重量%。在該範圍，尤其可獲得耐捲曲性、耐刮性等機械特性之平衡優良的硬化物。其中，具有2個以上活性能量射線聚合性基之聚合性化合物為40~60重量%較為理想。As described above, in the present invention, the amount of the polymerizable compound having two or more active energy ray polymerizable groups with respect to the total amount of the active energy ray polymerizable compound must be 30 to 70% by weight. Within this range, a hardened product having a good balance of mechanical properties such as curl resistance and scratch resistance can be obtained. Among them, the polymerizable compound having two or more active energy ray polymerizable groups is preferably 40 to 60% by weight.
(具有芳香族基之聚合性化合物) 在本發明中，使用具有芳香族基之聚合性化合物、具有環狀脂肪族結構之聚合性化合物、具有雜環結構之聚合性化合物、苯乙烯系化合物、具有直鏈狀脂肪族結構之聚合性化合物等，可獲得耐刮性或對於光學片為必要性能之高折射率而較為理想。例如，上述具有芳香族基之聚合性化合物之含量宜為使芳香族基之重量濃度相對於上述活性能量射線聚合性化合物之全部量為30~60重量%，其中宜為30~50重量%。(Polymerizable compound having an aromatic group) In the present invention, a polymerizable compound having an aromatic group, a polymerizable compound having a cyclic aliphatic structure, a polymerizable compound having a heterocyclic structure, a styrene-based compound, The polymerizable compound and the like having a linear aliphatic structure are preferable in order to obtain scratch resistance or a high refractive index necessary for optical sheets. For example, the content of the polymerizable compound having an aromatic group is preferably such that the weight concentration of the aromatic group is 30 to 60% by weight relative to the total amount of the active energy ray polymerizable compound, and 30 to 50% by weight is preferable.
就上述具有芳香族基之聚合性化合物而言，可舉例如具有芳香環之(甲基)丙烯酸酯類等。就具有芳香環之(甲基)丙烯酸酯類而言，可舉例如(甲基)丙烯酸苄醯氧基乙酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯基乙酯、(甲基)丙烯酸苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯、2-苯基-2-(4-丙烯醯氧基苯基)丙烷、2-苯基-2-(4-丙烯醯氧基烷氧基苯基)丙烷、(甲基)丙烯酸2,4,6-三氯苯酯、(甲基)丙烯酸2,4,6-三溴苯酯、(甲基)丙烯酸2,4,6-三氯苄酯、(甲基)丙烯酸2,4,6-三溴苄酯、(甲基)丙烯酸2,4,6-三氯苯氧基乙酯、(甲基)丙烯酸2,4,6-三溴苯氧基乙酯、(甲基)丙烯酸鄰苯基苯酚(多)乙氧酯、(甲基)丙烯酸對苯基苯酚(多)乙氧酯等。Examples of the polymerizable compound having an aromatic group include (meth) acrylates having an aromatic ring. Examples of the (meth) acrylates having an aromatic ring include benzyloxyethyl (meth) acrylate, benzyl (meth) acrylate, phenylethyl (meth) acrylate, and (methyl) ) Phenoxyethyl acrylate, phenoxydiethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, 2-phenyl-2- (4- Acrylic methoxyphenyl) propane, 2-phenyl-2- (4-propyleneoxyoxyalkoxyphenyl) propane, 2,4,6-trichlorophenyl (meth) acrylate, (methyl ) 2,4,6-tribromophenyl acrylate, 2,4,6-trichlorobenzyl (meth) acrylate, 2,4,6-tribromobenzyl (meth) acrylate, (meth) acrylic acid 2,4,6-trichlorophenoxyethyl, 2,4,6-tribromophenoxyethyl (meth) acrylate, o-phenylphenol (poly) ethoxylate (meth) acrylate, ( P-phenylphenol (poly) ethoxylate, etc.).
就上述具有環狀脂肪族結構之聚合性化合物而言，可舉例如具有環狀脂肪族之(甲基)丙烯酸酯類。就具有環狀脂肪族(甲基)丙烯酸酯類而言，可舉例如(甲基)丙烯酸環己酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊烯基氧基乙酯、(甲基)丙烯酸四氫糠(tetrahydrofurfuryl)酯、環氧丙基環碳酸酯(甲基)丙烯酸酯、二(甲基)丙烯酸三環癸烷二羥甲酯等。Examples of the polymerizable compound having a cyclic aliphatic structure include (meth) acrylates having a cyclic aliphatic. Examples of the cyclic aliphatic (meth) acrylates include cyclohexyl (meth) acrylate, isoamyl (meth) acrylate, dicyclopentyl (meth) acrylate, and (meth) ) Dicyclopentenyloxyethyl acrylate, tetrahydrofurfuryl (meth) acrylate, epoxypropylcyclocarbonate (meth) acrylate, tricyclodecanedi (meth) acrylate Hydroxymethyl and so on.
就上述苯乙烯系化合物而言，可舉例如苯乙烯、α-甲基苯乙烯、氯苯乙烯等。Examples of the styrene-based compound include styrene, α-methylstyrene, and chlorostyrene.
就上述雜環系化合物而言，可舉例如N-乙烯基吡咯啶酮、N-乙烯基己內酯、丙烯醯基啉、參(2-羥乙基)異氰尿酸酯(isocyanurate)、參(羥丙基)異氰尿酸酯及將1~20莫耳之環氧烷或ε己內酯對於此等進行開環加成而得之含羥基化合物等具有羥基之化合物與(甲基)丙烯酸形成酯鍵而得之具有異三聚氰酸結構的化合物等。Examples of the heterocyclic compound include N-vinylpyrrolidone, N-vinylcaprolactone, acrylomethinoline, ginseng (2-hydroxyethyl) isocyanurate, Ginseng (hydroxypropyl) isocyanurate and hydroxy-containing compounds such as hydroxy-containing compounds obtained by ring-opening addition of 1 to 20 moles of alkylene oxide or ε-caprolactone, and (methyl ) A compound having an isotricyanic acid structure obtained from the formation of an ester bond of acrylic acid.
(具2個以上活性能量射線聚合性基且具有環氧乙烷基，且具有芳香族基之聚合性化合物) 此外，當然也宜使用上述具2個以上活性能量射線聚合性基且具有環氧乙烷基，且具有芳香族基之聚合性化合物。就如此之聚合性化合物而言，可列舉為環氧乙烷基改性環氧多(甲基)丙烯酸酯之環氧乙烷改性雙酚A環氧多(甲基)丙烯酸酯、環氧乙烷改性雙酚F環氧多(甲基)丙烯酸酯、環氧乙烷改性雙酚S環氧多(甲基)丙烯酸酯等。此等之環氧乙烷基改性環氧多(甲基)丙烯酸酯所具有之環氧乙烷基係1分子中於平均值具有1~30個重複單元數較為理想。(Polymer compound having two or more active energy ray polymerizable groups and having an oxirane group and an aromatic group) In addition, it is of course preferable to use the above-mentioned two or more active energy ray polymerizable groups and having an epoxy group. A polymerizable compound having an ethane group and an aromatic group. Examples of such polymerizable compounds include ethylene oxide-modified epoxy poly (meth) acrylate, ethylene oxide-modified bisphenol A epoxy poly (meth) acrylate, and epoxy resin. Ethane-modified bisphenol F epoxy poly (meth) acrylate, ethylene oxide-modified bisphenol S epoxy poly (meth) acrylate, and the like. These ethylene oxide-modified epoxy poly (meth) acrylates have an ethylene oxide group of 1 molecule having an average number of 1 to 30 repeating units per molecule.
上述具有環氧乙烷基及2個以上活性能量射線聚合性基之聚合性化合物可使用1種，也可混合多種使用。混合多種使用時，例如雙酚A之環氧乙烷加成之二丙烯酸酯與二新戊四醇之環氧乙烷加成物之丙烯酸酯的組合、或雙酚A之環氧乙烷加成之二丙烯酸酯與三羥甲基丙烷之環氧乙烷加成物之丙烯酸酯的組合較為理想。The polymerizable compound having an ethylene oxide group and two or more active energy ray polymerizable groups may be used singly or in combination. When used in combination, for example, a combination of bisphenol A ethylene oxide addition diacrylate and dipentaerythritol ethylene oxide addition acrylate, or bisphenol A ethylene oxide addition The combination of the diacrylate and the acrylate of the ethylene oxide adduct of trimethylolpropane is preferable.
本發明之硬化性組成物推測是藉由於交聯結構中納入環氧乙烷鏈，而可獲得就捲曲性而言為優良且兼具機械物性(耐刮性等)之硬化物者。使用於交聯結構中未納入環氧乙烷鏈，具有如懸吊於側鏈之環氧乙烷骨架的單官能聚合性化合物時，因為交聯密度下降，雖然捲曲性受到抑制但有可能無法獲得兼具機械物性之硬化物。 考慮此等情事，具2個以上活性能量射線聚合性基且具有環氧乙烷基之聚合性化合物係在多個活性能量射線聚合性基之間存在有環氧乙烷鏈如此之結構較為理想。The curable composition of the present invention is presumed to be able to obtain a cured product which is excellent in curlability and has both mechanical properties (scratch resistance, etc.) by incorporating an ethylene oxide chain in the crosslinked structure. When used for a monofunctional polymerizable compound that does not incorporate an ethylene oxide chain in a crosslinked structure and has an ethylene oxide skeleton suspended from a side chain, the crosslink density may be reduced and the curlability may be suppressed, but it may not be possible. Obtain a hardened material with both mechanical and physical properties. In consideration of these circumstances, a polymerizable compound having two or more active energy ray polymerizable groups and having an ethylene oxide group is preferably a structure having an ethylene oxide chain between a plurality of active energy ray polymerizable groups. .
(其他之聚合性化合物) 在本發明中，併用具有1個活性能量射線聚合性基之聚合性化合物(有時稱為單官能單體)較為理想。就單官能單體而言並沒有特別之限定，可使用公知之單體。(Other polymerizable compounds) In the present invention, it is preferable to use a polymerizable compound (sometimes referred to as a monofunctional monomer) having one active energy ray polymerizable group in combination. The monofunctional monomer is not particularly limited, and known monomers can be used.
可使用例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二烷酯、(甲基)丙烯酸十四烷酯、(甲基)丙烯酸十六烷酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸十八烷酯、(甲基)丙烯酸二十二烷酯等具有碳數1~22之烷基的(甲基)丙烯酸酯類；(甲基)丙烯酸羥乙酯、(甲基)丙烯酸羥丙酯、(甲基)丙烯酸甘油酯、内酯改性(甲基)丙烯酸羥乙酯、(甲基)丙烯酸聚乙二醇酯、(甲基)丙烯酸聚丙二醇酯等具有羥烷基之丙烯酸酯類等之具有烷基之(甲基)丙烯酸酯類、或For example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate can be used , Octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, tetradecyl (meth) acrylate, (meth) acrylic acid (Meth) acrylic acid having an alkyl group having 1 to 22 carbons, such as cetyl ester, stearyl (meth) acrylate, stearyl (meth) acrylate, behenyl (meth) acrylate, etc. Esters; hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, glyceryl (meth) acrylate, lactone-modified hydroxyethyl (meth) acrylate, polyethylene glycol (meth) acrylate Alkyl esters (meth) acrylates having alkyl groups, such as acrylates having hydroxyalkyl groups, such as alcohol esters, polypropylene glycol (meth) acrylates, or
(甲基)丙烯酸環氧丙酯、α-乙基(甲基)丙烯酸環氧丙酯、α-正丙基(甲基)丙烯酸環氧丙酯、α-正丁基(甲基)丙烯酸環氧丙酯、(甲基)丙烯酸-3,4-環氧丁酯、(甲基)丙烯酸-4,5-環氧戊酯、(甲基)丙烯酸-6,7-環氧戊酯、α-乙基(甲基)丙烯酸-6,7-環氧戊酯、(甲基)丙烯酸β-甲基環氧丙酯、(甲基)丙烯酸-3,4-環氧基環己酯、內酯改性(甲基)丙烯酸-3,4-環氧基環己酯、乙烯基環氧己烯氧化物等具有聚合性不飽和雙鍵及環氧基之聚合性化合物、Glycidyl (meth) acrylate, Glycidyl α-ethyl (meth) acrylate, Glycidyl α-n-propyl (meth) acrylate, Glycol α-n-butyl (meth) acrylate Oxypropyl ester, -3,4-epoxybutyl (meth) acrylate, -4,5-epoxypentyl (meth) acrylate, -6,7-epoxypentyl (meth) acrylate, α -Ethyl (meth) acrylic acid-6,7-epoxyamyl ester, (meth) acrylic acid β-methylepoxypropyl ester, (meth) acrylic acid 3,4-epoxycyclohexyl ester, internal Ester-modified (meth) acrylic acid 3,4-epoxy cyclohexyl ester, vinyl epoxyhexene oxide and other polymerizable compounds having polymerizable unsaturated double bonds and epoxy groups,
(甲基)丙烯酸、(甲基)丙烯酸β-羧基乙酯、2-丙烯醯氧基乙基琥珀酸、2-丙烯醯氧基乙基鄰苯二甲酸、2-丙烯醯氧基乙基六氫鄰苯二甲酸及此等之內酯改性物等具有酯鍵之不飽和單羧酸、馬來酸等具有聚合性不飽和雙鍵及羧基之聚合性單體、(Meth) acrylic acid, β-carboxyethyl (meth) acrylate, 2-propenyloxyethyl succinic acid, 2-propenyloxyethyl phthalic acid, 2-propenyloxyethylhexade Unsaturated monocarboxylic acids having an ester bond such as hydrogen phthalic acid and modified lactones thereof, polymerizable unsaturated double bonds having a polymerizable unsaturated bond such as maleic acid and a carboxyl group,
富馬酸二甲酯、富馬酸二乙酯、富馬酸二丁酯、伊康酸二甲酯、伊康酸二丁酯、富馬酸甲基乙酯、富馬酸甲基丁酯、伊康酸甲基乙酯等不飽和二羧酸酯類、Dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl ikonate, dibutyl ikonate, methyl ethyl fumarate, methyl butyl fumarate , Unsaturated dicarboxylic acid esters such as methyl ethyl iconate,
苯乙烯、α-甲基苯乙烯、氯苯乙烯等苯乙烯衍生物類；丁二烯、異戊二烯、戊二烯、二甲基丁二烯等二烯系化合物類；氯乙烯、溴乙烯等鹵化乙烯和鹵化亞乙烯類；甲基乙烯基酮、丁基乙烯基酮等不飽和酮類；乙酸乙烯酯、丁酸乙烯酯等乙烯酯類；甲基乙烯基醚、丁基乙烯基醚等乙烯基醚類；丙烯腈、甲基丙烯腈、氰化亞乙烯等氰化乙烯類；丙烯醯胺或其酸醇取代醯胺類；N-苯基馬來醯亞胺、N-環己基馬來醯亞胺等N-取代馬來醯亞胺類；Styrene derivatives such as styrene, α-methylstyrene and chlorostyrene; butadiene, isoprene, pentadiene, dimethyl butadiene and other diene compounds; vinyl chloride, bromine Halogenated ethylene and vinylidene halides such as ethylene; unsaturated ketones such as methyl vinyl ketone and butyl vinyl ketone; vinyl esters such as vinyl acetate and vinyl butyrate; methyl vinyl ether and butyl vinyl Vinyl ethers such as ether; vinyl cyanide such as acrylonitrile, methacrylonitrile, and vinyl cyanide; acrylamide or its acid alcohol substituted amidine; N-phenylmaleimide, N-ring N-substituted maleimides such as hexylmaleimide;
氟化乙烯、偏二氟乙烯、三氟乙烯、氯三氟乙烯、溴三氟乙烯、五氟丙烯或六氟丙烯等含氟α-烯烴類；或三氟甲基三氟乙烯基醚、五氟乙基三氟乙烯基醚或七氟丙基三氟乙烯基醚等(全)氟烷基之碳數為1至18之(全)氟烷基・全氟乙烯基醚類；(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、(甲基)丙烯酸1H,1H,2H,2H-十七氟癸酯或(甲基)丙烯酸全氟乙氧基乙酯等(全)氟烷基之碳數為1至18的(甲基)丙烯酸(全)氟烷酯類等含氟之乙烯性不飽和單體類；Fluorinated α-olefins such as fluorinated ethylene, vinylidene fluoride, trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, pentafluoropropylene or hexafluoropropylene; or trifluoromethyl trifluorovinyl ether, pentafluoroethylene (Per) fluoroalkyl and perfluorovinyl ethers having a carbon number of 1 to 18, such as fluoroethyltrifluorovinyl ether or heptafluoropropyltrifluorovinyl ether; (methyl) ) 2,2,2-trifluoroethyl acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, (methyl ) 1H, 1H, 2H, 2H-heptadecafluorodecyl or (per) fluorofluoroethoxyethyl (meth) acrylate, etc. (meth) acrylic acid having a carbon number of 1 to 18 (all ) Fluorinated ethylenically unsaturated monomers such as fluoroalkyl esters;
γ-甲基丙烯醯氧基丙基三甲氧基矽烷等含矽基之(甲基)丙烯酸酯類；(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸N,N-二乙基胺基乙酯或(甲基)丙烯酸N,N-二乙基胺基丙酯等(甲基)丙烯酸N,N-二烷基胺基烷酯；γ-Methacryloxypropyltrimethoxysilane and other silicon-containing (meth) acrylates; N, N-dimethylaminoethyl (meth) acrylate, N (meth) acrylate N, N-diethylaminoethyl (meth) acrylate, N-diethylaminoethyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate;
(甲基)丙烯酸磷乙酯(phosphoethyl (meth)acrylate)、(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸N,N-二乙基胺基乙酯或(甲基)丙烯酸N,N-二乙基胺基丙酯、二[(甲基)丙烯醯氧基乙基]磷酸酯、三[(甲基)丙烯醯氧基乙基]磷酸酯等。Phosphoethyl (meth) acrylate, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, or N, N-diethylaminopropyl (meth) acrylate, di [(meth) acryloxyethyl] phosphate, tri [(meth) acryloxyethyl] phosphate, and the like.
其中，就理想之單官能單體而言，可舉例如式(1)表示之1官能(甲基)丙烯酸酯。Among them, as the ideal monofunctional monomer, for example, a monofunctional (meth) acrylate represented by the formula (1) may be mentioned.
【化2】
(式(1)中，R1 係氫原子，R2 係氫原子或甲基，n之平均值係1~5之數。) 可藉由例如將對苯基苯酚或鄰苯基苯酚與環氧乙烷或環氧丙烷的反應物，和(甲基)丙烯酸反應來獲得式(1)表示之化合物。對苯基苯酚或鄰苯基苯酚與環氧乙烷或環氧丙烷的反應物可輕易地從市面上取得。可使用例如三洋化成(股)製，NEWPOL OPE-20(使2莫耳環氧乙烷對於1莫耳鄰苯基苯酚反應而得者。)、NEWPOL OPE-40(使4莫耳環氧乙烷對於1莫耳鄰苯基苯酚反應而得者。)等。(In formula (1), R 1 is a hydrogen atom, R 2 is a hydrogen atom or a methyl group, and the average value of n is a number from 1 to 5.) For example, p-phenylphenol or o-phenylphenol and a ring can be used. A reactant of ethylene oxide or propylene oxide is reacted with (meth) acrylic acid to obtain a compound represented by the formula (1). Reactants of p-phenylphenol or o-phenylphenol with ethylene oxide or propylene oxide are readily available on the market. For example, made by Sanyo Chemical Co., Ltd., NEWPOL OPE-20 (obtained by reacting 2 moles of ethylene oxide with 1 mole of o-phenylphenol.), NEWPOL OPE-40 (makes 4 moles of ethylene oxide by 1 mole of o-phenylphenol reaction.) And so on.
就上述單官能單體而言，可使用1種亦可混合多種使用。混合多種使用時，例如(甲基)丙烯酸鄰苯基苯酚(多)乙氧酯與(甲基)丙烯酸苯氧基(多)乙氧酯之組合，就確保高折射率及與基材薄膜的黏合性上較為理想。此外，(甲基)丙烯酸鄰苯基苯酚(多)乙氧酯與丙烯酸苯氧基苄酯的組合就賦予高折射率、低黏度及復原性(稜鏡)的方面較為理想。These monofunctional monomers may be used singly or in combination. When used in combination, for example, the combination of o-phenylphenol (poly) ethoxy (meth) acrylate and phenoxy (poly) ethoxy (meth) acrylate ensures high refractive index and It is ideal in adhesiveness. In addition, a combination of o-phenylphenol (poly) ethoxylate (meth) acrylate and phenoxybenzyl acrylate is preferable in terms of imparting high refractive index, low viscosity, and resilience (i).
在本發明中，上述單官能單體在不損害本發明之效果的範圍內使用較為理想。具體而言，在相對於上述活性能量射線聚合性化合物之全部量為30~70重量%之範圍內較為理想。其中，單官能單體為40~60重量%，就同時實現作業性(低黏度化)與機械物性兩者上較為理想。In the present invention, the monofunctional monomer is preferably used within a range that does not impair the effects of the present invention. Specifically, it is preferable to be in a range of 30 to 70% by weight based on the total amount of the active energy ray polymerizable compound. Among them, the monofunctional monomer is 40 to 60% by weight, and it is desirable to achieve both workability (low viscosity) and mechanical properties.
(光聚合起始劑) 就本發明中使用之光聚合起始劑而言，可舉例如二苯基酮、3,3’-二甲基-4-甲氧基二苯基酮、4,4’-雙二甲基胺基二苯基酮、4,4’-雙二乙基胺基二苯基酮、4,4’-二氯二苯基酮、米其勒酮(Michler's ketone)、3,3’,4,4’-四(三級丁基過氧化羰基)二苯基酮等二苯基酮類；(Photopolymerization initiator) Examples of the photopolymerization initiator used in the present invention include diphenyl ketone, 3,3'-dimethyl-4-methoxydiphenyl ketone, 4'-bisdimethylaminodiphenyl ketone, 4,4'-bisdiethylaminodiphenyl ketone, 4,4'-dichlorodiphenyl ketone, Michler's ketone , 3,3 ', 4,4'-tetrakis (tert-butylperoxycarbonyl) diphenyl ketone and other diphenyl ketones;
氧雜蒽酮(xanthone)、噻吨酮(thioxanthone)、2-甲基噻吨酮、2-氯噻吨酮、2,4-二乙基噻吨酮等氧雜蒽酮、噻吨酮類；安息香(Benzoin)、安息香甲醚、安息香乙醚、安息香異丙醚等醯偶姻醚(acyloin ether)類；Xanthone, thioxanthone, 2-methylthioxanthone, 2-chlorothioxanthone, 2,4-diethylthioxanthone and other xanthone, thioxanthone ; Benzoin, benzoin methyl ether, benzoin ether, benzoin isopropyl ether and other acyloin ethers;
二苯乙二酮(benzil)、聯乙醯等α-二酮類；二硫化四甲基秋蘭姆(tetramethylthiuram disulfide)、對甲苯二硫化物等硫化物類；4-二甲基胺基苯甲酸、4-二甲基胺基苯甲酸乙酯等苯甲酸類；Α-diketones such as benzil and diethylpyrene; sulfides such as tetramethylthiuram disulfide and p-toluene disulfide; 4-dimethylaminobenzene Benzoic acids such as formic acid, ethyl 4-dimethylaminobenzoate;
3,3’-羰基-雙(7-二乙基胺基)香豆素、1-羥基環己基苯基酮、2,2’-二甲氧基-1,2-二苯基乙-1-酮、2-甲基-1-[4-(甲硫基)苯基]-2-啉基丙-1-酮、2-苄基-2-二甲基胺基-1-(4-啉基苯基)-丁-1-酮、2-羥基-2-甲基-1-苯基丙-1-酮、2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦、1-[4-(2-羥基乙氧基)苯基]-2-羥基-2-甲基-1-丙-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙-1-酮、1-(4-十二烷基苯基)-2-羥基-2-甲基丙-1-酮、4-苯甲醯基-4’-甲基二甲基硫化物、2,2’-二乙氧基苯乙酮、苄基二甲基縮酮、苄基-β-甲氧基乙基縮醛、鄰苯甲醯基苯甲酸甲酯、雙(4-二甲基胺基苯基)酮、對二甲基胺基苯乙酮、α,α-二氯-4-苯氧基苯乙酮、戊基-4-二甲基胺基苯甲酸酯、2-(鄰氯苯基)-4,5-二苯基咪唑基二聚體、2,4-雙-三氯甲基-6-[二-(乙氧基羰基甲基)胺基]苯基-S-三氮雜苯、2,4-雙-三氯甲基-6-(4-乙氧基)苯基-S-三氮雜苯、2,4-雙-三氯甲基-6-(3-溴-4-乙氧基)苯基-S-三氮雜苯蔥醌、2-三級丁基蔥醌、2-戊基蔥醌、β-氯蔥醌等。3,3'-carbonyl-bis (7-diethylamino) coumarin, 1-hydroxycyclohexylphenyl ketone, 2,2'-dimethoxy-1,2-diphenylethyl-1 -Ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-olinylpropan-1-one, 2-benzyl-2-dimethylamino-1- (4- (Phenylphenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2,4,6-trimethylbenzylidene diphenylphosphine oxide, Bis (2,4,6-trimethylbenzyl) phenylphosphine oxide, 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propane -1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- (4-dodecylphenyl) -2-hydroxy-2- Methylpropan-1-one, 4-benzylidene-4'-methyldimethylsulfide, 2,2'-diethoxyacetophenone, benzyldimethylketal, benzyl- β-methoxyethyl acetal, methyl ortho-benzoyl benzoate, bis (4-dimethylaminophenyl) ketone, p-dimethylaminoacetophenone, α, α-dichloro 4-phenoxyacetophenone, pentyl-4-dimethylaminobenzoate, 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer, 2,4 -Bis-trichloromethyl-6- [di- (ethoxycarbonylmethyl) amino] phenyl-S-triazabenzene, 2,4-bis-trichloromethyl- 6- (4-ethoxy) phenyl-S-triazabenzene, 2,4-bis-trichloromethyl-6- (3-bromo-4-ethoxy) phenyl-S-triazine Heteroquinone, 2-tert-butyl allium quinone, 2-pentyl allium quinone, β-chloroallium quinone and the like.
上述光聚合起始劑可使用1種亦可混合多種使用。其使用量雖然沒有特別之限制，為了保持感度良好，防止結晶析出、塗膜物性之劣化等，相對於本發明之光學物品用活性能量射線硬化型樹脂組成物100重量份宜使用0.05~20重量份，其中為0.1~10重量份特別理想。These photopolymerization initiators may be used singly or in combination. Although its use amount is not particularly limited, in order to maintain good sensitivity, prevent crystal precipitation, and deterioration of coating film properties, it is preferable to use 0.05 to 20 parts by weight relative to 100 parts by weight of the active energy ray-curable resin composition for optical articles of the present invention Parts, with 0.1 to 10 parts by weight being particularly preferred.
其中，選自1-羥基環己基苯基酮、2-羥基-2-甲基-1-苯基丙-1-酮、1-[4-(2-羥基乙氧基)苯基]-2-羥基-2-甲基-1-丙-1-酮、噻吨酮及噻吨酮衍生物、2,2’-二甲氧基-1,2-二苯基乙-1-酮、2,4,6-三甲基苯甲醯基二苯基氧化膦、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦、2-甲基-1-[4-(甲硫基)苯基]-2-啉基-1-丙烷酮、2-苄基-2-二甲基胺基-1-(4-啉基苯基)-丁-1-酮之群組中之1種或2種以上之混合系，就為了獲得硬化性高之光學物品用活性能量射線硬化型樹脂組成物而言特別理想。Among them, selected from 1-hydroxycyclohexylphenyl ketone, 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-diphenylethyl-1-one, 2 , 4,6-trimethylbenzylidene diphenylphosphine oxide, bis (2,4,6-trimethylbenzylidene) phenylphosphine oxide, 2-methyl-1- [4- ( Methylthio) phenyl] -2-olinyl-1-propanone, 2-benzyl-2-dimethylamino-1- (4-olinylphenyl) -but-1-one One or two or more of these mixed systems are particularly preferable in order to obtain an active energy ray-curable resin composition for optical articles having high curability.
進一步地，本發明之光學物品用活性能量射線硬化型樹脂組成物可於上述光聚合起始劑中併用各種光敏劑。就光敏劑而言，可舉例如胺類、尿素類、含硫化合物、含磷化合物、含氯化合物或腈類或其他含氮化合物等。Further, the active energy ray-curable resin composition for an optical article of the present invention can be used in combination with various photosensitizers in the photopolymerization initiator. Examples of the photosensitizer include amines, ureas, sulfur-containing compounds, phosphorus-containing compounds, chlorine-containing compounds, nitriles, and other nitrogen-containing compounds.
使用了本發明之光學物品用活性能量射線硬化型樹脂組成物的物品之製造中，紫外線等活性能量射線常常是通過為支撐體之透明基材面進行照射。因此，光聚合起始劑宜為在長波長區域具有吸光能力之起始劑，例如在紫外線為360~450nm之範圍發揮光起始功能之光聚合起始劑較為理想。In the production of an article using the active energy ray-curable resin composition for an optical article of the present invention, active energy rays such as ultraviolet rays are often irradiated through a transparent substrate surface of a support. Therefore, the photopolymerization initiator is preferably an initiator having a light absorption ability in a long wavelength region, for example, a photopolymerization initiator that exhibits a photoinitiation function in a range of 360 to 450 nm in ultraviolet rays is preferable.
本發明之光學物品用活性能量射線硬化型樹脂組成物就改良黏度或對於透明基板之黏著性等目的而言，亦可併用樹脂等。可舉例如甲基丙烯酸甲酯樹脂、甲基丙烯酸甲酯系共聚物等丙烯酸樹脂；聚苯乙烯、甲基丙烯酸甲酯-苯乙烯系共聚物；聚酯樹脂；聚氨酯(polyurethane)樹脂；聚丁二烯或丁二烯-丙烯腈系共聚物等聚丁二烯樹脂；雙酚型環氧樹脂、苯氧基樹脂或酚醛清漆型環氧樹脂等環氧樹脂等。The active energy ray-curable resin composition for an optical article of the present invention may be used in combination with a resin or the like for the purpose of improving viscosity or adhesiveness to a transparent substrate. Examples include acrylic resins such as methyl methacrylate resin and methyl methacrylate-based copolymers; polystyrene, methyl methacrylate-styrene copolymers; polyester resins; polyurethane resins; polybutylene Polybutadiene resins such as diene or butadiene-acrylonitrile copolymers; epoxy resins such as bisphenol-type epoxy resins, phenoxy resins or novolac-type epoxy resins.
本發明之光學物品用活性能量射線硬化型樹脂組成物的黏度為了可均勻地塗布至母模，進一步地使其可複製具有微細結構之母模，在25℃係100~30000mPa･s之範圍較為理想，其中係150~20000mPa･s特別理想。即使為上述範圍以外之黏度，只要採取控制樹脂組成物之溫度以調整黏度等之方法仍可以使用。The viscosity of the active energy ray-curable resin composition for an optical article of the present invention is to be uniformly applied to a master mold, and further, it can be replicated to a master mold having a fine structure. Ideal, especially 150 ~ 20,000mPa ･ s. Even if the viscosity is outside the above range, it can be used by controlling the temperature of the resin composition to adjust the viscosity and the like.
本發明之光學物品用活性能量射線硬化型樹脂組成物之酸價(將於樣本1g中存在之酸成分依循規定之方法進行中和時需要的氫氧化鉀的毫克數)為5.0mgKOH/g以下因為會成為可獲得環境安定性優良之硬化物的光學物品用活性能量射線硬化型樹脂組成物故較為理想，為0mgKOH/g~3.0mgKOH/g特別理想。The acid value of the active energy ray-curable resin composition for optical articles of the present invention (the number of milligrams of potassium hydroxide required to neutralize the acid component present in 1 g of the sample according to a prescribed method) is 5.0 mgKOH / g or less An active energy ray-curable resin composition for an optical article that can obtain a cured product having excellent environmental stability is desirable, and it is particularly preferably from 0 mgKOH / g to 3.0 mgKOH / g.
本發明之光學物品用活性能量射線硬化型樹脂組成物在對於形成在基材上之硬化樹脂成形層更進一步要求耐光性的情況等，因應需求可添加紫外線吸收劑。進一步地，在塗膜之改質，或改善塗布適性、從母模之離模性的情況，也可添加抗氧化劑、矽系添加劑、氟系添加劑、流變控制劑、消泡劑、離模劑、矽烷偶聯劑、抗靜電劑、防霧劑、著色劑等。In the case where the active energy ray-curable resin composition for an optical article of the present invention further requires light resistance for a cured resin forming layer formed on a substrate, an ultraviolet absorber may be added as required. Further, when the coating film is modified, or the coating suitability is improved, and the mold release from the master mold is improved, antioxidants, silicon-based additives, fluorine-based additives, rheology control agents, defoamers, and mold release can be added. Agents, silane coupling agents, antistatic agents, anti-fog agents, colorants, etc.
就紫外線吸收劑而言，可舉例如2-[4-{(2-羥基-3-十二烷氧基丙基)氧基}-2-羥基苯基]-4,6-雙(2,4-二甲基苯基)-1,3,5-三氮雜苯、2-[4-{(2-羥基-3-十三烷氧基丙基)氧基}-2-羥基苯基]-4,6-雙(2,4-二甲基苯基)-1,3,5-三氮雜苯等三氮雜苯衍生物、2-(2’-(xanthene)羧基-5’-甲基苯基)苯并三唑、2-(2’-鄰硝基苄氧基-5’-甲基苯基)苯并三唑、2-羧基-4-十二烷氧基二苯基酮、2-鄰硝基苄氧基-4-十二烷氧基二苯基酮等。As the ultraviolet absorber, for example, 2- [4-{(2-hydroxy-3-dodecyloxypropyl) oxy} -2-hydroxyphenyl] -4,6-bis (2, 4-dimethylphenyl) -1,3,5-triazabenzene, 2- [4-{(2-hydroxy-3-tridecyloxypropyl) oxy} -2-hydroxyphenyl ] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazabenzene and other triazabenzene derivatives, 2- (2'- (xanthene) carboxy-5'-methylphenyl) benzotriazole, 2- (2'-o-nitrobenzyloxy-5'-methylphenyl) benzotriazole, 2- Carboxy-4-dodecyloxydiphenyl ketone, 2-o-nitrobenzyloxy-4-dodecyloxydiphenyl ketone, and the like.
就抗氧化劑而言，可舉例如受阻酚系抗氧化劑、受阻胺系抗氧化劑、有機硫系抗氧化劑、磷酸酯系抗氧化劑等。Examples of the antioxidant include hindered phenol-based antioxidants, hindered amine-based antioxidants, organic sulfur-based antioxidants, and phosphate-based antioxidants.
就矽系添加劑而言，可舉例如二甲基聚矽氧烷、甲基苯基聚矽氧烷、環狀二甲基聚矽氧烷、甲基氫聚矽氧烷、聚醚改性二甲基聚矽氧烷共聚物、聚酯改性二甲基聚矽氧烷共聚物、氟改性二甲基聚矽氧烷共聚物、胺基改性二甲基聚矽氧烷共聚物等具有烷基或苯基之聚有機矽氧烷類。As for the silicon-based additive, for example, dimethyl polysiloxane, methylphenyl polysiloxane, cyclic dimethyl polysiloxane, methyl hydrogen polysiloxane, polyether-modified disiloxane Methyl polysiloxane copolymer, polyester modified dimethyl polysiloxane copolymer, fluorine modified dimethyl polysiloxane copolymer, amine modified dimethyl polysiloxane copolymer, etc. Polyorganosiloxanes having alkyl or phenyl groups.
就如上述之各種添加劑的使用量而言，考慮充分發揮其效果，且不妨害紫外線硬化之範圍，相對於該光學物品用活性能量射線硬化型樹脂組成物100重量份，各別為0.01~10重量份之範圍較為理想。Regarding the use amounts of the various additives as described above, it is considered that the effect is fully exerted and the range of ultraviolet curing is not hindered. Each of the additives is 0.01 to 10 parts by weight with respect to 100 parts by weight of the active energy ray-curable resin composition for optical articles. A range of parts by weight is preferable.
本發明之光學物品用活性能量射線硬化型樹脂組成物雖然因應需求可含有溶劑，但因為溶劑含有率少者可獲得不容易污染作業環境之光學物品用活性能量射線硬化型樹脂組成物故較為理想。具體而言，本發明之光學物品用活性能量射線硬化型樹脂組成物中之溶劑含有率宜為1重量%以下。Although the active energy ray-curable resin composition for an optical article of the present invention may contain a solvent according to demand, it is preferable that the active energy ray-curable resin composition for an optical article that does not easily pollute the working environment can be obtained if the solvent content is low. Specifically, the solvent content of the active energy ray-curable resin composition for an optical article of the present invention is preferably 1% by weight or less.
本發明之光學物品用活性能量射線硬化型樹脂組成物係適用於薄膜狀、片狀、板狀之透明基材上設置了由樹脂硬化物構成之成形樹脂層之結構的各種物品的材料。其中，在使用於透鏡等透明性為必要之物品的製造中時，組合各樹脂組成物成分來使用使在厚度200±25μm之硬化物中400~900nm的波長區域之透光率成為80%以上，宜為85%以上較為理想。The active energy ray-curable resin composition for an optical article of the present invention is a material suitable for various articles having a structure in which a resin layer formed of a cured resin is provided on a film-like, sheet-like, or plate-shaped transparent substrate. Among them, when used in the manufacture of articles where transparency is necessary, such as lenses, the resin composition components are used in combination so that the light transmittance in the wavelength range of 400 to 900 nm in a hardened material having a thickness of 200 ± 25 μm becomes 80% or more It should be more than 85%.
(硬化物) 本發明之硬化物係使本發明之光學物品用活性能量射線硬化型樹脂組成物硬化而得者。該硬化物為了具有在對於賦予了微細形狀之樹脂硬化層施加之壓力小的情況具有不會變形之程度的硬度，且在短時間施加強的壓力之情況形狀也不會崩壞(不會硬脆裂)，在25℃之動態黏彈性的彈性係數宜為2500~ 3000MPa，更宜為2700~2900MPa。 同樣地關於捲曲，因為彈性係數越高越容易展現硬化收縮造成之影響，考慮物性平衡設計為上述範圍內較為理想。(Hardened product) The hardened product of the present invention is obtained by hardening the active energy ray-curable resin composition for an optical article of the present invention. This hardened product has a degree of hardness that does not deform when the pressure applied to the resin hardened layer to which a fine shape is given is small, and the shape does not collapse when a strong pressure is applied for a short time (no hardening) Brittle crack), the elastic coefficient of dynamic viscoelasticity at 25 ℃ should be 2500 ~ 3000MPa, more preferably 2700 ~ 2900MPa. As for the curl, the higher the coefficient of elasticity, the easier it is to exhibit the influence caused by hardening and shrinkage. It is ideal to consider the physical property balance within the above range.
就控制捲曲性之因素而言，也可列舉在動態黏彈性之tan δ max。Tan δ max之峰值係展示在交聯結構之交聯點間分子量的分布，峰值低且寬的情況，因為交聯點間分子量之分布廣，硬化收縮分散，故就捲曲性而言為良好，峰值高且尖銳之情況，因為交聯點間分子量之分布均勻，硬化時會一下子全部產生收縮，就捲曲性而言會惡化故較不理想。在該點，關於耐刮性，藉由使交聯點間分子量之分布變廣，因為可提高樹脂硬化物之韌性，在與強度、彈性係數維持平衡之範圍內設計使Tan δ max之峰值低更為理想。As for the factors controlling the curlability, tan δ max of dynamic viscoelasticity can also be cited. The peak of Tan δ max shows the distribution of molecular weight between the cross-linking points of the cross-linked structure. The peak is low and wide. Because the molecular weight distribution between the cross-linking points is wide and the hardening shrinks and disperses, it is good in terms of curlability. It is not ideal that the peaks are high and sharp because the molecular weight distribution between the crosslinking points is uniform, and all of them will shrink at once during hardening, which will deteriorate the curlability. At this point, regarding the scratch resistance, by widening the molecular weight distribution between the crosslinking points, the toughness of the resin hardened product can be improved, and the peak value of Tan δ max is designed to be low within a range that maintains a balance with strength and elastic coefficient. More ideal.
其中，在本發明中，動態黏彈性係使用Rheometoric Scientific公司製之「RSAII」作為黏彈性測定裝置，測定條件為升溫速度3℃/Min，頻率3.5Hz之條件下測定而得之值。Among them, in the present invention, the dynamic viscoelasticity is a value obtained by measuring under the conditions of a temperature rise rate of 3 ° C./Min and a frequency of 3.5 Hz using “RSAII” manufactured by Rhometoric Scientific Corporation as a viscoelasticity measuring device.
(硬化方法) 使本發明之光學物品用活性能量射線硬化型樹脂組成物硬化的活性能量射線係指電磁波或帶電粒子束中，具有可將分子聚合、交聯之能量量子者，可舉例如可見光、紫外線、X射線等電磁波、或電子束等帶電粒子束。此等之中，就實用上常使用的有可見光、紫外線。為紫外線時，可使用超高壓汞燈、高壓汞燈、低壓汞燈、碳弧、黑光燈、金屬鹵化物燈等光源。(Hardening method) The active energy ray that hardens the active energy ray-curable resin composition for an optical article of the present invention refers to an electromagnetic wave or a charged particle beam that has an energy quantum capable of polymerizing and cross-linking molecules. Examples include visible light. , Electromagnetic waves such as ultraviolet rays, X-rays, or charged particle beams such as electron beams. Among these, visible light and ultraviolet light are often used in practical applications. In the case of ultraviolet light, light sources such as ultra-high-pressure mercury lamps, high-pressure mercury lamps, low-pressure mercury lamps, carbon arcs, black light lamps, and metal halide lamps can be used.
(光學片) 就製造本發明之光學片的方法而言，可列舉將本發明之光學物品用活性能量射線硬化型樹脂組成物填充至具有必要之微細形狀的母模上後，使空氣不會混入地將塑膠基材加壓疊層使其黏合至所填充之該樹脂組成物上，從塑膠基材側照射紫外線等活性能量射線使該樹脂組成物硬化後，從母模離模之方法等。此外還可舉例如將該樹脂組成物連續地填充至輥狀之母模後，使空氣不會混入地將塑膠基材連續地黏合至所填充之該樹脂組成物上，從塑膠基材側照射紫外線等活性能量射線使該樹脂組成物硬化後，從輥狀之母模離模之連續製造的方法等。(Optical sheet) The method for manufacturing the optical sheet of the present invention includes filling an active energy ray-curable resin composition for an optical article of the present invention into a master mold having a necessary fine shape, and preventing air from flowing. A method of mixing and laminating a plastic substrate under pressure to adhere to the filled resin composition, and irradiating an active energy ray such as ultraviolet rays from the plastic substrate side to harden the resin composition, and then removing the mold from the master mold, etc. . In addition, for example, after continuously filling the resin composition into a roll-shaped master mold, the plastic substrate is continuously adhered to the filled resin composition without being mixed with air, and irradiated from the plastic substrate side A method for continuously manufacturing the resin composition by curing the resin composition with active energy rays such as ultraviolet rays, and then releasing the mold from a roll-shaped master mold.
就此方式中可使用之薄膜狀、片狀、板狀之透明基材而言，可舉例如聚對苯二甲酸乙二酯(PET)、聚萘二甲酸乙二酯(PEN)等聚酯樹脂、三乙酸纖維素、聚碳酸酯樹脂、甲基丙烯酸甲酯系共聚物等丙烯酸樹脂、苯乙烯樹脂、聚碸樹脂、聚醚碸樹脂、氯化乙烯樹脂、聚甲基丙烯酸醯亞胺樹脂等。此外，雖然不是塑膠基材，但也可同樣地使用玻璃基材等無機基材。 [實施例]As the film-like, sheet-like, and plate-like transparent substrate that can be used in this method, for example, polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN) can be mentioned. , Acrylic resins such as cellulose triacetate, polycarbonate resin, methyl methacrylate copolymers, styrene resins, polyfluorene resins, polyether resins, vinyl chloride resins, polymethacrylic acid imine resins, etc. . Although not a plastic substrate, an inorganic substrate such as a glass substrate can be used in the same manner. [Example]
以下列舉實施例及比較例來更具體地說明本發明。例中的「份」及「%」若無特別指明之情況下，全部皆為重量基準。Examples and comparative examples are given below to explain the present invention more specifically. Unless otherwise specified, "parts" and "%" in the examples are all based on weight.
(光學物品用活性能量射線硬化性組成物之調整) 藉由下列表1所示之摻合調整組成物。此外，各成分之該環氧乙烷基的重量濃度及芳香族基之重量濃度係藉由各結構成分之結構式算出。(Adjustment of active energy ray-curable composition for optical articles) The composition was adjusted by blending as shown in Table 1 below. The weight concentration of the ethylene oxide group and the weight concentration of the aromatic group of each component are calculated from the structural formula of each structural component.
【表1】
表中簡稱如同下述。 UNIDIC V-5500 (DIC公司製，BPA型環氧丙烯酸酯) 芳香環量：33.7%，EO鏈含量：0% TMP3EO-3A：三羥甲基丙烷之EO改性 (n=3) 三丙烯酸酯 芳香環量：0%，EO鏈含量：18% BPA4EO-2A：BPA之EO改性 (n=4) 二丙烯酸酯 芳香環量：30.5%，EO鏈含量：31.2% 丙烯酸鄰苯氧基苯基乙酯 芳香環量：58.2%，EO鏈含量：16.4% 丙烯酸苯氧基乙酯 芳香環量：40.6%，EO鏈含量：20.8% 丙烯酸苄酯 芳香環量：48.1%，EO鏈含量：0% DP6A/DP5A=6/4：二新戊四醇六丙烯酸酯/二新戊四醇五丙烯酸酯=6/4 芳香環量：0%，EO鏈含量：0% DP-EO-6A/DP-EO-5A=6/4：二新戊四醇之EO改性六丙烯酸酯/二新戊四醇之EO改性五丙烯酸酯=6/4 (EO聚合度：0.85) 芳香環量：0%，EO鏈含量：26.7% I-184：1-羥基-環己基苯基酮 (光起始劑) IRGACURE184 [BASF公司製]The abbreviations in the table are as follows. UNIDIC V-5500 (manufactured by DIC, BPA type epoxy acrylate) Aromatic ring content: 33.7%, EO chain content: 0% TMP3EO-3A: EO modification of trimethylolpropane (n = 3) triacrylate Aromatic ring content: 0%, EO chain content: 18% BPA4EO-2A: EO modification of BPA (n = 4) Diacrylate aromatic ring content: 30.5%, EO chain content: 31.2% o-phenoxyphenyl acrylate Amount of aromatic ring of ethyl ester: 58.2%, content of EO chain: 16.4% Amount of aromatic ring of phenoxyethyl acrylate: 40.6%, content of EO chain: 20.8% Amount of aromatic ring of benzyl acrylate: 48.1%, content of EO chain: 0% DP6A / DP5A = 6/4: dinepentaerythritol hexaacrylate / dinepentaerythritol pentaacrylate = 6/4 aromatic ring content: 0%, EO chain content: 0% DP-EO-6A / DP- EO-5A = 6/4: EO modified hexaacrylate of dipentaerythritol / EO modified pentaacrylate of dipentaerythritol = 6/4 (EO polymerization degree: 0.85) Aromatic ring content: 0% , EO chain content: 26.7% I-184: 1-hydroxy-cyclohexylphenyl ketone (light initiator) IRGACURE184 [manufactured by BASF]
(硬化物之製作方法及評價方法) 硬化物之製作方法及評價方法係如以下之方式來進行。(Manufacturing method and evaluation method of hardened | cured material) The manufacturing method and evaluation method of hardened | cured material were performed as follows.
＜動態黏彈性測定 Tg、儲存彈性模數、tan δ max(峰高度)之測定＞ (硬化物之製作方法) 於玻璃板滴加實施例或比較例之樹脂組成物，藉由旋轉塗布器塗布使膜厚成為100μm後，於氮氣環境下進行UV照射來製作硬化塗膜。照射條件係藉由EYE GRAPHICS Co., Ltd.製之金屬鹵化物燈以累積光量1000mJ/cm2 來進行。之後，從玻璃板剝離為硬化物之樹脂薄膜，裁切為3mm×50mm作為試驗片。<Dynamic viscoelasticity measurement Tg, storage elastic modulus, tan δ max (peak height) measurement> (Method for producing hardened product) The resin composition of the example or comparative example was dropped onto a glass plate, and applied by a spin coater. After setting the film thickness to 100 μm, UV irradiation was performed in a nitrogen atmosphere to produce a cured coating film. The irradiation conditions were performed using a metal halide lamp manufactured by EYE GRAPHICS Co., Ltd. at a cumulative light amount of 1000 mJ / cm 2 . After that, the cured resin film was peeled from the glass plate and cut into 3 mm × 50 mm as a test piece.
(動態黏彈性測定) 樹脂薄膜之Tg、儲存彈性模數、及tan δ max(峰部高度)之測定係使用Rheometoric Scientific公司製之「RSAII」作為黏彈性測定裝置，以升溫速度：3℃/Min，頻率：3.5Hz之測定條件來進行。(Dynamic viscoelasticity measurement) The Tg, storage elastic modulus, and tan δ max (peak height) of the resin film were measured using "RSAII" manufactured by Rhometoric Scientific Corporation as a viscoelasticity measuring device, and the temperature rising rate was 3 ° C Min, frequency: 3.5 Hz.
＜捲曲性評價＞ 將75μm之PET薄膜(東洋紡公司製：COSMOSINE A4300)作為基材，塗布實施例或比較例之樹脂組成物，在氮氣環境下進行UV照射(照射條件為藉由EYE GRAPHICS Co., Ltd.製之金屬鹵化物燈，累積光量1000mJ/cm2 )，製作稜鏡片(節距20μm)。 將製作而得之稜鏡片裁切為5cm方形，於室溫放置1天後，藉由捲尺以公厘(millimeter)單位量測4個角落之翹曲(捲曲)程度，將4個角落的合計值作為捲曲性之指標。值越低表示越沒有捲曲。在本評價中，只要是10mm以下便判定為合格。<Evaluation of curlability> A 75 μm PET film (manufactured by Toyobo Cosmosine A4300) was used as a substrate, and the resin composition of the example or the comparative example was coated, and UV irradiation was performed in a nitrogen atmosphere (irradiation conditions were determined by EYE GRAPHICS Co. , Ltd. made a metal halide lamp with a cumulative light amount of 1000 mJ / cm 2 ) to produce a cymbal (pitch 20 μm). The produced cymbal was cut into a 5 cm square, and after standing at room temperature for 1 day, the degree of warpage (curl) of the 4 corners was measured by a tape measure in millimeter units, and the total of the 4 corners was calculated. The value serves as an index of curlability. Lower values indicate less curl. In this evaluation, if it is 10 mm or less, it is judged as a pass.
＜耐刮性＞ 在藉由與上述相同之條件所製得之稜鏡片上重疊偏光薄膜，並於其上放置砝碼。於該狀態僅拉動稜鏡片，以目視觀察對於稜鏡片表面造成傷痕之程度。 改變砝碼之重量進行試驗，將不會造成傷痕之最大重量(g)作為耐刮性之值。值越高，耐刮性越優良。在本評價中，只要是100g以上便判定為合格。<Scratch resistance> A polarizing film is laminated on a cymbal produced under the same conditions as above, and a weight is placed thereon. In this state, only the cymbal was pulled to visually observe the extent of the damage to the cymbal surface. The test was performed by changing the weight of the weight, and the maximum weight (g) that does not cause scratches was taken as the value of scratch resistance. The higher the value, the better the scratch resistance. In this evaluation, if it is 100 g or more, it is judged as a pass.
實施例及比較例之結果表示於表2。The results of the examples and comparative examples are shown in Table 2.
【表2】
該結果，實施例1~3之光學物品用活性能量射線硬化性組成物之硬化物就捲曲性及耐刮性而言為優良。尤其是使用了二新戊四醇之環氧乙烷改性多(甲基)丙烯酸酯的實施例1及實施例2於耐刮性非常地優良。反觀比較例1~3因為任一者之環氧乙烷基的濃度皆在6重量%以下，耐刮性差。此外，比較例3之DMA儲存彈性模數(25℃)為3000非常地高，可知其就捲曲性而言為不良。As a result, the hardened | cured material of the active-energy-ray-curable composition for optical articles of Examples 1-3 was excellent in curlability and scratch resistance. In particular, Examples 1 and 2 using ethylene oxide-modified poly (meth) acrylates using dipentaerythritol were very excellent in scratch resistance. In contrast, in Comparative Examples 1 to 3, since the concentration of the ethylene oxide group in each of them was 6% by weight or less, the scratch resistance was poor. In addition, the DMA storage elastic modulus (25 ° C) of Comparative Example 3 was extremely high at 3000, and it was found that it was inferior in curlability.
無no
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