JPH10195117A - Photocurable composition and method for curing - Google Patents
Photocurable composition and method for curingInfo
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- JPH10195117A JPH10195117A JP35851696A JP35851696A JPH10195117A JP H10195117 A JPH10195117 A JP H10195117A JP 35851696 A JP35851696 A JP 35851696A JP 35851696 A JP35851696 A JP 35851696A JP H10195117 A JPH10195117 A JP H10195117A
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- Prior art keywords
- polymerizable compound
- compound
- photocurable
- photocurable composition
- radical
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、増感された光硬化
性組成物に関し、更に詳しくは、厚膜および酸化チタン
等の顔料が配合された組成物においても良好に光硬化可
能な光触媒組成物に関する。本発明の光硬化性組成物
は、光、電子線、Ｘ線等の活性エネルギー線照射によ
り、硬化することが可能であり、特に長波長感光に優れ
た特性を有するため、光硬化型の塗料、接着剤、インキ
およびフォトレジスト、光造形用の感光性樹脂等へ好適
に用いられる。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a sensitized photocurable composition, and more particularly, to a photocatalyst composition which can be favorably photocured even in a composition containing a thick film and a pigment such as titanium oxide. About things. The photocurable composition of the present invention can be cured by irradiating active energy rays such as light, electron beams, and X-rays, and in particular, has excellent characteristics in long-wavelength photosensitivity. , Adhesives, inks and photoresists, and photosensitive resins for stereolithography.
【０００２】[0002]
【従来の技術】ジアリールヨードニウム塩化合物は、特
開昭５０−１５１９９６号等で、光、電子線、Ｘ線等の
放射線によりエポキシ化合物等のカチオン重合性化合物
を硬化させる触媒として使用できることが記載されてい
る。ジアリールヨードニウム塩化合物は、紫外線硬化に
有効とされる３６０ｎｍよりも長波長にほとんど吸収を
もっていないため、長波長のレーザー光を使用する光造
形や顔料等の添加剤を使用する光硬化性組成物では、硬
化性が著しく低下することが知られている。特に、ヨー
ドニウム塩化合物のＵＶ吸収と吸収が重なる酸化チタン
等のホワイト顔料を多量に含有する光硬化性組成物で
は、ほとんど光硬化しない。この解決方法として増感剤
の検討が行われ、アクリジンオレンジ等の色素が見出さ
れているが、実用的にみて有効ではない。その中でチオ
キサントン類が実用的なものとして有効的と言われてい
るが、ラジカル重合性化合物との組合せにおいて有効か
どうかの報告例はない。2. Description of the Related Art A diaryliodonium salt compound is disclosed in Japanese Patent Application Laid-Open No. 50-151996 and the like, which describes that it can be used as a catalyst for curing a cationically polymerizable compound such as an epoxy compound by radiation such as light, electron beam and X-ray. ing. Since diaryliodonium salt compounds have little absorption at wavelengths longer than 360 nm, which is effective for ultraviolet curing, photocurable compositions using additives such as photolithography or pigments using long-wavelength laser light are not suitable for photocurable compositions. It is known that the curability is significantly reduced. In particular, a photocurable composition containing a large amount of a white pigment such as titanium oxide, in which the UV absorption of the iodonium salt compound and the absorption overlap, hardly undergoes photocuring. As a solution to this, sensitizers have been studied and dyes such as acridine orange have been found, but they are not practically effective. Among them, thioxanthones are said to be effective as practical ones, but there is no report on whether or not they are effective in combination with a radical polymerizable compound.
【０００３】一方、ジアリールヨードニウム塩化合物を
増感剤としてクマリン誘導体等の化合物と組合せて可視
光で機能する光ラジカル触媒として使用できることが知
られている。しかし、これらの増感剤は、極めて高価で
あるとともに、カチオン重合性化合物とラジカル重合性
化合物を各々硬化させるための増感剤であるため、カチ
オン重合性化合物とラジカル重合性化合物のハイブリッ
ド系で使用することは困難である。従って、ハイブリッ
ド系では、光カチオン触媒や光ラジカル触媒を新たに添
加しなくてはならず、これが硬化物の物性を低下や配合
物のコストアップを招く要因となっている。On the other hand, it is known that a diaryliodonium salt compound can be used as a photoradical catalyst which functions with visible light in combination with a compound such as a coumarin derivative as a sensitizer. However, these sensitizers are extremely expensive and are sensitizers for curing the cationically polymerizable compound and the radically polymerizable compound, respectively. Difficult to use. Therefore, in the hybrid system, a photocationic catalyst or a photoradical catalyst must be newly added, and this is a factor that causes a decrease in the physical properties of the cured product and an increase in the cost of the compound.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、これらの事
情からみてなされたもので、光、電子線、Ｘ線等の活性
エネルギー線照射に高感度で感応する光硬化性組成物を
提供すると共に、厚手の膜や顔料を多量に含有する膜で
も短時間で硬化することが可能で、かつ優れた硬化物物
性を有する光硬化性組成物の提供および、カチオン重合
性化合物とラジカル重合性化合物のハイブリッド系で新
たな触媒や増感剤を使用する必要がないため、コスト低
減や硬化物物性の向上が可能な硬化システムを提供する
ことを目的としている。SUMMARY OF THE INVENTION The present invention has been made in view of these circumstances, and provides a photocurable composition which is highly sensitive to irradiation with active energy rays such as light, electron beams, and X-rays. In addition, a photocurable composition that can be cured in a short time even with a thick film or a film containing a large amount of pigment, and has excellent cured physical properties, and a cationically polymerizable compound and a radically polymerizable compound It is an object of the present invention to provide a curing system capable of reducing costs and improving physical properties of a cured product because it is not necessary to use a new catalyst or a sensitizer in the hybrid system.
【０００５】[0005]
【課題を解決するための手段】本発明者は、前記目的を
達成するために鋭意検討したところ、対アニオンが非求
核性であるジアリールヨードニウム塩化合物およびチオ
キサントン誘導体とラジカル重合性化合物、カチオン重
合性化合物の配合物を組み合わせることにより、ラジカ
ル重合性化合物とカチオン重合性化合物の各々の硬化性
を相乗的に向上させることが可能であることを見出し、
短時間で厚手の膜や顔料を多量に含有する膜でも、光、
電子線、Ｘ線等の活性エネルギー線照射により、硬化で
きる光硬化性組成物を完成するに至った。Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and found that a diaryliodonium salt compound having a non-nucleophilic counter anion and a thioxanthone derivative, a radical polymerizable compound, a cationic polymerizable compound, Finding that it is possible to synergistically improve the curability of each of the radically polymerizable compound and the cationically polymerizable compound by combining the compounds of the hydrophilic compounds,
Even in the case of a thick film or a film containing a large amount of pigment in a short time,
A photocurable composition curable by irradiation with an active energy ray such as an electron beam or an X-ray has been completed.
【０００６】[0006]
【発明の実施の形態】本発明は、カチオン重合性化合
物、ラジカル重合性化合物、チオキサントン及びその誘
導体、非求核性の対アニオンを有するジアリールヨード
ニウム塩化合物からなる光硬化性組成物である。本発明
のジアリールヨードニウム塩化合物とは、メチル基、エ
チル基、プロピル基、イソプロピル基、ブチル基、イソ
ブチル基、ｔ−ブチル基、ペンチル基、ヘキシル基、デ
シル基等のアルキル基、シクロヘキシル基等のシクロア
ルキル基、メトキシ基、エトキシ基、プロピル基、ブト
キシ基、ヘキシルオキシ基、デシルオキシ基、ドデシル
オキシ基等のアルコキシ基、フッ素、塩素、臭素、ヨウ
素等のハロゲン原子、ベンゾイル基等カルボニル基、フ
ェニル基、ニトロ基等の置換基で置換されていてもよい
フェニル基やナフチル基を有するものであり、非求核性
の対アニオンとしては、Ｂ（Ｃ6 Ｆ5 ）、ＳｂＦ6 、Ａ
ｓＦ6 、ＰＦ6 またはＢＦ4 等が例示される。本発明の
ジアリールヨードニウム塩化合物の代表例を以下に示
す。但し、式中のＸは、アニオン残基を示す。DETAILED DESCRIPTION OF THE INVENTION The present invention is a photocurable composition comprising a cationically polymerizable compound, a radically polymerizable compound, thioxanthone and its derivatives, and a diaryliodonium salt compound having a non-nucleophilic counter anion. The diaryl iodonium salt compound of the present invention includes a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a hexyl group, an alkyl group such as a decyl group, a cyclohexyl group and the like. Cycloalkyl group, methoxy group, ethoxy group, propyl group, butoxy group, hexyloxy group, decyloxy group, alkoxy group such as dodecyloxy group, halogen atom such as fluorine, chlorine, bromine, iodine, carbonyl group such as benzoyl group, phenyl A phenyl group or a naphthyl group which may be substituted with a substituent such as a nitro group or a nitro group, and the non-nucleophilic counter anions include B (C 6 F 5 ), SbF 6 ,
Examples include sF 6 , PF 6 and BF 4 . Representative examples of the diaryliodonium salt compound of the present invention are shown below. Here, X in the formula represents an anion residue.
【０００７】[0007]
【表１】 [Table 1]
【０００８】[0008]
【表２】 [Table 2]
【０００９】[0009]
【表３】 [Table 3]
【００１０】本発明に使用されるチオキサントン及びそ
の誘導体とは、チオキサントン、イソプロピルチオキサ
ントン、２−クロロチオキサントン、２，４−ジメチル
チオキサントン、２，４−ジエチルチオキサントン、
２，４−ジイソプロピルチオキサントン等のチオキサン
トン誘導体である。本発明に使用されるラジカル重合性
化合物としては、ラジカル重合性のあるモノマー、オリ
ゴマーおよびポリマーなら、その種類を問わず使用可能
であるが、カチオン重合を阻害するアミノ基等の塩基性
の高い官能基を有するものは好ましくない。一般に、モ
ノマーとして、単官能や多官能のアクリレートやメタク
リレートモノマーが、オリゴマーおよびポリマーとし
て、ポリエステルアクリレート、エポキシアクリレー
ト、ポリブタジエンアクリレート、ポリエーテルアクリ
レート等が好適に使用できる。特に、カチオン重合の際
に反応可能な水酸基等の官能基や直接カチオン重合性化
合物と反応するカルボキシル基等の官能基を有するもの
が好ましく使用される。The thioxanthone and its derivatives used in the present invention include thioxanthone, isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone,
Thioxanthone derivatives such as 2,4-diisopropylthioxanthone. As the radical polymerizable compound used in the present invention, monomers, oligomers and polymers having radical polymerizability can be used irrespective of their types, but highly basic functional groups such as amino groups that inhibit cationic polymerization can be used. Those having a group are not preferred. Generally, monofunctional or polyfunctional acrylate or methacrylate monomers can be suitably used as monomers, and polyester acrylate, epoxy acrylate, polybutadiene acrylate, polyether acrylate, etc. can be suitably used as oligomers and polymers. In particular, those having a functional group such as a hydroxyl group capable of reacting during cationic polymerization or a functional group such as a carboxyl group which directly reacts with the cationically polymerizable compound are preferably used.
【００１１】本発明に使用されるカチオン重合性化合物
とは、カチオン重合性のあるモノマー、オリゴマーおよ
びポリマーなら、その種類を問わず使用可能であるが、
脂環型エポキシ化合物、ビニルエーテル化合物、オキセ
タン化合物等が好適に使用できる。本発明に使用される
ラジカル重合性化合物およびカチオン重合性化合物に
は、同一分子内にアクリル等のラジカル重合性基とエポ
キシ等のカチオン重合性基を有するものも含有される。
本発明において、ジアリールヨードニウム塩化合物とラ
ジカル重合性化合物およびカチオン重合性化合物の混合
物との配合割合は、ラジカル重合性化合物とカチオン重
合性化合物の混合物１００部に対し、ジアリールヨード
ニウム塩化合物０．０１〜２０部、好ましくは０．１〜
１０部である。このジアリールヨードニウム塩化合物が
少ないと、ラジカル重合性化合物とカチオン重合性化合
物の混合物の硬化性が低下し、過剰であると硬化物の特
性が低下する。The cationically polymerizable compound used in the present invention may be any cationically polymerizable monomer, oligomer or polymer, regardless of its type.
Alicyclic epoxy compounds, vinyl ether compounds, oxetane compounds, and the like can be suitably used. The radical polymerizable compound and the cationic polymerizable compound used in the present invention include those having a radical polymerizable group such as acrylic and a cationic polymerizable group such as epoxy in the same molecule.
In the present invention, the mixing ratio of the diaryliodonium salt compound and the mixture of the radically polymerizable compound and the cationically polymerizable compound is 100 parts by weight of the mixture of the radically polymerizable compound and the cationically polymerizable compound, and the diaryliodonium salt compound is 0.01 to 0.01 parts. 20 parts, preferably 0.1 to
10 parts. If the amount of the diaryliodonium salt compound is small, the curability of the mixture of the radically polymerizable compound and the cationically polymerizable compound will be reduced, and if it is excessive, the properties of the cured product will be reduced.
【００１２】一方、前記チオキサントン及びその誘導体
とラジカル重合性化合物とカチオン重合性化合物の混合
物との配合割合は、ラジカル重合性化合物とカチオン重
合性化合物の混合物１００部に対し、チオキサントン及
びその誘導体０．１〜１０部、好ましくは０．５〜５部
の割合で配合する。このチオキサントン及びその誘導体
が少ないと、ジアリールヨードニウム塩化合物の光反応
性が低下し、過剰であると組成物の特性が低下する。ま
た、ラジカル重合性化合物とカチオン重合性化合物の混
合の割合は任意に設定できるが、硬化物の物性や硬化収
縮等を考慮すると、フォトレジストに使用する場合を除
けば、カチオン重合性化合物が重合性化合物の５０％以
上であることが好ましい。On the other hand, the mixing ratio of the mixture of the thioxanthone and its derivative, the radically polymerizable compound and the cationically polymerizable compound is 100 parts of the mixture of the radically polymerizable compound and the cationically polymerizable compound and the amount of thioxanthone and its derivative 0.1. It is blended at a ratio of 1 to 10 parts, preferably 0.5 to 5 parts. When the amount of thioxanthone and its derivative is small, the photoreactivity of the diaryliodonium salt compound is reduced, and when it is excessive, the properties of the composition are reduced. In addition, the mixing ratio of the radical polymerizable compound and the cationic polymerizable compound can be arbitrarily set, but in consideration of the physical properties of the cured product, curing shrinkage, and the like, the cationic polymerizable compound is polymerized except when used in a photoresist. It is preferably at least 50% of the active compound.
【００１３】本発明の光硬化性組成物は、光により容易
に硬化することができる。光源としては、低圧水銀灯、
中圧水銀灯、高圧水銀灯、超高圧水銀灯、メタルハライ
ドランプ、クセノンランプ、カーボンアーク灯等が用い
られる。また、半導体レーザー、アルゴンレーザー、Ｈ
ｅ−Ｃｄレーザー等のレーザー光を用いることができ
る。特に、厚膜硬化や酸化チタンのような顔料含有の光
硬化性組成物に使用する際は、ガリウム入りのメタルハ
ライドランプが好適に用いられる。本発明の硬化性組成
物は、α線、β線、γ線、中性子線、Ｘ線、加速電子線
のような電離性放射線によっても容易に硬化することが
できる。The photocurable composition of the present invention can be easily cured by light. As the light source, a low-pressure mercury lamp,
Medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, metal halide lamps, xenon lamps, carbon arc lamps and the like are used. Semiconductor laser, argon laser, H
Laser light such as an e-Cd laser can be used. In particular, when used for thick film curing or a photocurable composition containing a pigment such as titanium oxide, a metal halide lamp containing gallium is preferably used. The curable composition of the present invention can be easily cured by ionizing radiation such as α-ray, β-ray, γ-ray, neutron beam, X-ray, and accelerated electron beam.
【００１４】[0014]
【実施例】以下、本発明を実施例によって更に詳細に説
明する。The present invention will be described in more detail with reference to the following examples.
【００１５】配合物調整 表−１に示したような配合物を調整した。配合物の混合
割合は重量部である。尚、使用した各化合物の入手先を
下記に示す。 ＵＶＲ−６１１０：ＵＣＣ社製脂環型エポキシ ＴＭＰＴ−Ａ：新中村化学工業社製トリメチロールプロ
パントリアクリレート ＲＴＸ：日本化薬社製２，４−ジメチルチオキサントン ＣＲ−５ ８−２：石原産業社製酸化チタンFormulation Preparation Formulations as shown in Table 1 were prepared. Mixing ratios of the formulations are parts by weight. The sources of each compound used are shown below. UVR-6110: UCC's alicyclic epoxy TMPT-A: Shin-Nakamura Chemical Co., Ltd. trimethylolpropane triacrylate RTX: Nippon Kayaku Co., Ltd. 2,4-dimethylthioxanthone CR-5 8-2: Ishihara Sangyo Titanium oxide
【００１６】光硬化性テスト（１） 配合物を、ブリキ板に厚さ５μｍになるように塗布し、
下記の条件で光硬化させた。この時、タックがないもの
には○印、タックが残ったものには×印で、表−２に示
した。 ＵＶ照射機器：アイグラフィックス社製ベルトコンベア
型ＵＶ照射機器 ランプ：８０ｗ／ｃｍ集光型メタルハライドランプ、距
離１０ｃｍ コンベア速度：１００ｍ／分Photocurability Test (1) The composition was applied to a tin plate to a thickness of 5 μm,
Photocured under the following conditions. At this time, those having no tack were marked with a circle, and those having a tack remained with a cross, as shown in Table-2. UV irradiation device: belt conveyor type UV irradiation device manufactured by Eye Graphics Lamp: 80 w / cm condensing metal halide lamp, distance 10 cm Conveyor speed: 100 m / min
【００１７】光硬化性テスト（２） 配合物を、ブリキ板に塗布し、下記の条件で光硬化させ
た。この時、配合物が硬化した厚みを測定し、表−２に
示した。この時、ゲル化するが膜厚を測定できないもの
を△印で示した。 ＵＶ照射機器：アイグラフィックス社製ベルトコンベア
型ＵＶ照射機器 ランプＡ：１２０ｗ／ｃｍ集光型メタルハライドラン
プ、距離１０ｃｍ ランプＢ：１２０ｗ／ｃｍ集光型ガリウム入りメタルハ
ライドランプ、距離１０ｃｍ コンベア速度：１０ｍ／分Photocurability Test (2) The formulation was applied to a tin plate and photocured under the following conditions. At this time, the cured thickness of the composition was measured and is shown in Table-2. At this time, those which gelled but whose film thickness could not be measured were indicated by Δ. UV irradiation equipment: belt conveyor type UV irradiation equipment manufactured by Eye Graphics Co., Ltd. Lamp A: 120 w / cm condensing metal halide lamp, distance 10 cm Lamp B: 120 w / cm condensing gallium-containing metal halide lamp, distance 10 cm Conveyor speed: 10 m / Minute
【００１８】光硬化性テスト（３） 配合物を、ブリキ板に厚さ５μｍになるように塗布し、
下記の条件で光硬化させた。この時、配合物が内部まで
硬化したものは○印、硬化しなかったものには×印で、
表−２に示した。 ＵＶ照射機器：アイグラフィックス社製ベルトコンベア
型ＵＶ照射機器 ランプ：１６０ｗ／ｃｍ集光型ガリウム入りメタルハラ
イドランプ、距離１０ｃｍ コンベア速度：４０ｍ／分Photocurability test (3) The composition was applied to a tin plate to a thickness of 5 μm,
Photocured under the following conditions. At this time, if the compound was cured to the inside, the mark was ○, and if it was not cured, the mark was ×.
The results are shown in Table 2. UV irradiator: belt conveyor type UV irradiator manufactured by Eye Graphics Lamp: 160 w / cm condensing gallium-containing metal halide lamp, distance 10 cm Conveyor speed: 40 m / min
【００１９】[0019]
【表４】 [Table 4]
【００２０】[0020]
【表５】 [Table 5]
【００２１】[0021]
【発明の効果】本発明の光硬化性組成物は、光、電子
線、Ｘ線等の活性エネルギー線照射に高感度で感応する
光硬化性組成物であり、厚膜および酸化チタン等の顔料
が配合された組成物においても良好に短時間で硬化する
ことができ、かつ優れた硬化物物性を有するものであ
る。また、新たな触媒や増感剤を使用しなくてよい硬化
システムのため、コストの低減や硬化物物性の向上が可
能である。The photo-curable composition of the present invention is a photo-curable composition which is highly sensitive to irradiation of active energy rays such as light, electron beams and X-rays, and comprises a thick film and a pigment such as titanium oxide. Can be satisfactorily cured in a short time even in a composition containing the same, and have excellent cured material properties. In addition, since the curing system does not require the use of a new catalyst or sensitizer, it is possible to reduce costs and improve physical properties of a cured product.
Claims (13)
化合物、チオキサントン及びその誘導体、非求核性の対
アニオンを有するジアリールヨードニウム塩化合物から
なる光硬化性組成物。1. A photocurable composition comprising a cationically polymerizable compound, a radically polymerizable compound, thioxanthone and a derivative thereof, and a diaryliodonium salt compound having a non-nucleophilic counter anion.
合物の非求核性の対アニオン残基が、ＳｂＦ6 、Ｐ
Ｆ6 、Ｂ（Ｃ6 Ｆ5 ）の何れかであり、カチオン重合性
化合物がエポキシ化合物、ビニルエーテル化合物、オキ
セタン化合物の何れかであり、ラジカル重合性化合物が
アクリル酸エステル化合物またはメタクリル酸エステル
化合物である光硬化性組成物。2. The diaryliodonium salt compound according to claim 1, wherein the non-nucleophilic counter anion residue is SbF 6 , P
F 6 , B (C 6 F 5 ), the cationically polymerizable compound is an epoxy compound, a vinyl ether compound, or an oxetane compound, and the radically polymerizable compound is an acrylate compound or a methacrylate compound. Certain photocurable compositions.
核性の対アニオン残基が、ＰＦ6 であり、カチオン重合
性化合物が脂環型エポキシであり、ラジカル重合性化合
物がアクリル酸エステル化合物である請求項２の光硬化
性組成物。Non-nucleophilic counter anion residues wherein the diaryl iodonium salt compound is a PF 6, cationically polymerizable compound is a cycloaliphatic epoxy, a radical polymerizable compound is an acrylic ester compound according Item 2. The photocurable composition according to Item 2.
物と顔料からなる光硬化性組成物。4. A photocurable composition comprising the photocurable composition according to claim 2 and a pigment.
化性組成物。5. A photocurable composition wherein the pigment of claim 4 is titanium oxide.
４または請求項５の光硬化性組成物をガリウム入りラン
プで光硬化する光硬化方法。6. A photo-curing method for photo-curing the photo-curable composition according to claim 1, 2, 3, 4, or 5 with a gallium-containing lamp.
ジカル重合性化合物がカチオン重合性化合物の５０％以
下、５％以上の配合割合である光硬化性組成物。7. The photocurable composition according to claim 2, wherein the radical polymerizable compound is 50% or less and 5% or more of the cationic polymerizable compound.
ジカル重合性化合物がアクリル酸エステルまたはメタク
リル酸エステル系であり、ラジカル重合性化合物がカチ
オン重合性化合物の５０％以下、１０％以上の配合割合
である光硬化性インキ組成物。8. The photocurable composition according to claim 2, wherein the radically polymerizable compound is an acrylate or methacrylate ester, and the radically polymerizable compound is 50% or less and 10% or more of the cationically polymerizable compound. A photocurable ink composition having a compounding ratio.
ジカル重合性化合物がアクリル酸エステルまたはメタク
リル酸エステル系であり、ラジカル重合性化合物がカチ
オン重合性化合物の５０％以下、１０％以上の配合割合
である光硬化性フォトレジスト組成物。9. The photocurable composition according to claim 2, wherein the radical polymerizable compound is an acrylate or methacrylate ester, and the radical polymerizable compound is 50% or less of the cationic polymerizable compound and 10% or more of the cationic polymerizable compound. A photocurable photoresist composition having a compounding ratio.
ラジカル重合性化合物がアクリル酸エステルまたはメタ
クリル酸エステル系であり、ラジカル重合性化合物がカ
チオン重合性化合物の９０％以下、５０％以上の配合割
合であるアルカリ現像型光硬化性フォトレジスト組成
物。10. The photocurable composition according to claim 2,
An alkali-developable photocurable photoresist composition in which the radical polymerizable compound is an acrylate or methacrylate ester compound, and the radical polymerizable compound is 90% or less and 50% or more of the cationic polymerizable compound.
ラジカル重合性化合物がアクリル酸エステルまたはメタ
クリル酸エステル系であり、ラジカル重合性化合物がカ
チオン重合性化合物の３０％以下、５％以上の配合割合
である光硬化性接着剤組成物。11. The photocurable composition according to claim 2, wherein
A photocurable adhesive composition in which the radical polymerizable compound is an acrylate or methacrylate ester compound, and the radical polymerizable compound is 30% or less and 5% or more of the cationic polymerizable compound.
化合物の対アニオン残基が、ＳｂＦ6 またはＢ（Ｃ6 Ｆ
5 ）である光触媒組成物をレーザ光で硬化する硬化方
法。12. The diaryliodonium salt compound according to claim 2, wherein the counter anion residue is SbF 6 or B (C 6 F
5 ) A curing method in which the photocatalyst composition is cured by laser light.
〜４２０ｎｍの光で硬化する硬化方法。13. The laser beam according to claim 12, wherein the wavelength of the laser beam is 360.
A curing method of curing with light of ~ 420 nm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35851696A JPH10195117A (en) | 1996-12-27 | 1996-12-27 | Photocurable composition and method for curing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35851696A JPH10195117A (en) | 1996-12-27 | 1996-12-27 | Photocurable composition and method for curing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10195117A true JPH10195117A (en) | 1998-07-28 |
Family
ID=18459728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35851696A Withdrawn JPH10195117A (en) | 1996-12-27 | 1996-12-27 | Photocurable composition and method for curing |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH10195117A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001031892A (en) * | 1999-07-23 | 2001-02-06 | Toyo Ink Mfg Co Ltd | Ultraviolet light-curable type coating composition and its use |
| EP1295899A3 (en) * | 2001-09-06 | 2003-08-27 | Brother Kogyo Kabushiki Kaisha | Active energy beam-curable composition, ink containing the same, and printer accommodating the same ink |
| US6866376B2 (en) | 2001-09-28 | 2005-03-15 | Brother Kogyo Kabushiki Kaisha | Active energy beam-curable composition, ink containing the same, and printer accommodating the same ink |
| JP2009516050A (en) * | 2005-11-16 | 2009-04-16 | ガーバー サイエンティフィック インターナショナル インコーポレイテッド | Photocuring of cationic inks on acidic substrates |
| KR101004276B1 (en) | 2002-10-23 | 2011-01-03 | 스미또모 가가꾸 가부시끼가이샤 | Chemical amplification type positive resist composition |
| WO2011040531A1 (en) | 2009-10-01 | 2011-04-07 | 日立化成工業株式会社 | Material for organic electronics, organic electronic element, organic electroluminescent element, display element using organic electroluminescent element, illuminating device, and display device |
| WO2011132702A1 (en) | 2010-04-22 | 2011-10-27 | 日立化成工業株式会社 | Organic electronic material, polymerization initiator and thermal polymerization initiator, ink composition, organic thin film and production method for same, organic electronic element, organic electroluminescent element, lighting device, display element, and display device |
| JP2014156602A (en) * | 2007-11-30 | 2014-08-28 | Taiyo Holdings Co Ltd | White curable resin composition for print circuit board on which light-emitting device is mounted, cured product of the same, print circuit board comprising the cured product, and reflector for light-emitting device comprising the cured product |
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-
1996
- 1996-12-27 JP JP35851696A patent/JPH10195117A/en not_active Withdrawn
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001031892A (en) * | 1999-07-23 | 2001-02-06 | Toyo Ink Mfg Co Ltd | Ultraviolet light-curable type coating composition and its use |
| EP1295899A3 (en) * | 2001-09-06 | 2003-08-27 | Brother Kogyo Kabushiki Kaisha | Active energy beam-curable composition, ink containing the same, and printer accommodating the same ink |
| US6805439B2 (en) | 2001-09-06 | 2004-10-19 | Brother Kogyo Kabushiki Kaisha | Active energy beam-curable composition, ink containing the same, and printer accommodating the same ink |
| US6866376B2 (en) | 2001-09-28 | 2005-03-15 | Brother Kogyo Kabushiki Kaisha | Active energy beam-curable composition, ink containing the same, and printer accommodating the same ink |
| KR101004276B1 (en) | 2002-10-23 | 2011-01-03 | 스미또모 가가꾸 가부시끼가이샤 | Chemical amplification type positive resist composition |
| JP2009516050A (en) * | 2005-11-16 | 2009-04-16 | ガーバー サイエンティフィック インターナショナル インコーポレイテッド | Photocuring of cationic inks on acidic substrates |
| JP2014156602A (en) * | 2007-11-30 | 2014-08-28 | Taiyo Holdings Co Ltd | White curable resin composition for print circuit board on which light-emitting device is mounted, cured product of the same, print circuit board comprising the cured product, and reflector for light-emitting device comprising the cured product |
| WO2011040531A1 (en) | 2009-10-01 | 2011-04-07 | 日立化成工業株式会社 | Material for organic electronics, organic electronic element, organic electroluminescent element, display element using organic electroluminescent element, illuminating device, and display device |
| WO2011132702A1 (en) | 2010-04-22 | 2011-10-27 | 日立化成工業株式会社 | Organic electronic material, polymerization initiator and thermal polymerization initiator, ink composition, organic thin film and production method for same, organic electronic element, organic electroluminescent element, lighting device, display element, and display device |
| WO2014136900A1 (en) | 2013-03-08 | 2014-09-12 | 日立化成株式会社 | Ionic-compound-containing treatment solution, organic electronic element, and method for manufacturing organic electronic element |
| JP2015199815A (en) * | 2014-04-08 | 2015-11-12 | 川崎化成工業株式会社 | photopolymerizable composition |
| KR20200008115A (en) | 2017-05-17 | 2020-01-23 | 가와사끼가세이고오교 가부시끼가이샤 | Polymer photopolymerization sensitizer |
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