JP2578010B2 - Photosensitive resin composition and method for adjusting its sensitivity - Google Patents
Photosensitive resin composition and method for adjusting its sensitivityInfo
- Publication number
- JP2578010B2 JP2578010B2 JP2158275A JP15827590A JP2578010B2 JP 2578010 B2 JP2578010 B2 JP 2578010B2 JP 2158275 A JP2158275 A JP 2158275A JP 15827590 A JP15827590 A JP 15827590A JP 2578010 B2 JP2578010 B2 JP 2578010B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- resin composition
- photosensitive resin
- photosensitive
- polyvinyl alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- Compositions Of Macromolecular Compounds (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、水で現像可能な印刷板、特にスクリーン印
刷板の製造に用いることができる感光性樹脂組成物及び
その感度調節方法に関する。Description: TECHNICAL FIELD The present invention relates to a photosensitive resin composition which can be used for producing a water-developable printing plate, particularly a screen printing plate, and a method for adjusting the sensitivity thereof.
従来、印刷板、特にスクリーン印刷板製造用の水溶性
感光材料としては、ジアゾニウ塩、アジド基含有物質、
重フロム酸塩等が知られている。しかし、これらの感光
材料は、保存安定性が悪いこと、感度が低いこと、或は
公害問題を生じること等の問題点を有していた。Conventionally, as a water-soluble photosensitive material for manufacturing a printing plate, particularly a screen printing plate, a diazonium salt, an azide group-containing substance,
Heavy from-formates and the like are known. However, these photosensitive materials have problems such as poor storage stability, low sensitivity, and pollution problems.
これに対して、特公昭56−40814号公報に開示される
ように、スチリルピリジニウム基及び／又はスチリルキ
ノリニウム基を付加してポリビニルアルコール誘導体か
らなる水溶性感光材料が知られている。この物質は、光
架橋性を有し、非常に高感度、高解像性を備え、しかも
保存安定性に優れる等の多くの利点を有している。On the other hand, as disclosed in JP-B-56-40814, a water-soluble photosensitive material comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinolinium group is added is known. This substance has many advantages such as photocrosslinkability, very high sensitivity and high resolution, and excellent storage stability.
しかし、前記感光性ポリビニルアルコール誘導体は従
来のジアゾニウム塩等に比べて感動が高過ぎるために、
これによるスクリーン印刷版の製版時における露光時間
が非常に短くなり、逆に露光時間の管理が困難である等
の問題があった。However, since the photosensitive polyvinyl alcohol derivative is too sensitive compared to conventional diazonium salts and the like,
As a result, there has been a problem that the exposure time at the time of plate making of the screen printing plate becomes extremely short, and conversely, it is difficult to control the exposure time.
本発明の課題は、任意に感度調節されると共に露光時
間の管理が容易な、感光性ポリビニルアルコール誘導体
からなる感光性樹脂組成物を提供することにある。ま
た、本発明の別の課題は、感光性ポリビニルアルコール
誘導体からなる感光性樹脂組成物の感度を任意に調節す
る方法を提供することにある。An object of the present invention is to provide a photosensitive resin composition comprising a photosensitive polyvinyl alcohol derivative, the sensitivity of which is arbitrarily adjusted and the exposure time is easily controlled. Another object of the present invention is to provide a method for arbitrarily adjusting the sensitivity of a photosensitive resin composition comprising a photosensitive polyvinyl alcohol derivative.
本発明者らは、上記の課題を解決すべく検討を重ねた
結果、感光性ポリビニルアルコール誘導体に特定の光架
橋性化合物を添加することにより、本来の特性である優
れた水溶性、解像性及び保存安定性等を損なわずに、感
度を任意に調節できることを見いだし、本発明を完成す
るに至った。The present inventors have conducted various studies to solve the above-mentioned problems, and as a result, by adding a specific photocrosslinkable compound to a photosensitive polyvinyl alcohol derivative, excellent water solubility and resolution which are original characteristics The inventors have found that the sensitivity can be adjusted arbitrarily without impairing the storage stability and the like, and have completed the present invention.
即ち、本発明は、スチリルピリジニウム基及び／又は
スチリルキノリニウム基を付加したポリビニルアルコー
ル誘導体からなる感光性樹脂組成物に、 一般式［Ｉ］ （式中、Ｒは水素原子、ハロゲン、低級アルキル基又は
アルコキシ基を示し、Ａは 一般式［II］、［III］または［IV］ で表される基を示し、前記一般式［II］、［III］及び
［IV］中のR1は水素原子、アルキル基又はアラルキル基
を示し、これらはヒドロキシル基、カルバモイル基、エ
ーテル結合、不飽和結合を含んでもよく、R2は水素原子
又は低級アルキル基本を示し、Ｂは炭素数１〜６の直鎖
状又は分岐状アルキレン基を示し、X-は陰イオンを示
す）で表されるジオレフィン型化合物を添加したことを
特徴とする感光性樹脂組成物を提供するものであり、同
時にスチリルピリジニウム基及び／又はスチリルキノニ
ウム基を付加したポリビニルアルコール誘導体からなる
感光性樹脂組成物の感度調節方法にも提供する。That is, the present invention provides a photosensitive resin composition comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinolinium group is added, a compound represented by the general formula [I]: (Wherein, R represents a hydrogen atom, a halogen, a lower alkyl group or an alkoxy group, and A represents a general formula [II], [III] or [IV] Wherein R 1 in the general formulas [II], [III] and [IV] represents a hydrogen atom, an alkyl group or an aralkyl group, and these are a hydroxyl group, a carbamoyl group, an ether bond, R 2 represents a hydrogen atom or a lower alkyl group, B represents a linear or branched alkylene group having 1 to 6 carbon atoms, and X − represents an anion. Provided is a photosensitive resin composition characterized by adding a diolefin type compound, and at the same time, the sensitivity of a photosensitive resin composition comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinonium group is added. The adjustment method is also provided.
本発明に使用される感光性ポリビニルアルコール誘導
体は、 一般式［Ｖ］ （式中、ｍは１〜６の整数を示し、ｎは０又は１を示
し、Ｒ及びＡは前記と同義である）で表される構成単位
を有し、具体例として、ケン化度60モル％以上のポリビ
ニルアルコールの他、酢酸ビニルとこれと共重合可能な
単量体との共重合体のケン化物、及びこれらの部分アセ
タール化物等の水酸基に、アセタール化又はアセタール
交換反応によってスチリルビリジニウム基又はスチリル
キノリウム基を付加したものを挙げることができる。The photosensitive polyvinyl alcohol derivative used in the present invention has the general formula [V] (Wherein, m represents an integer of 1 to 6, n represents 0 or 1, and R and A have the same meanings as described above). In addition to polyvinyl alcohol in an amount of at least mol%, a hydroxyl group such as a saponified product of a copolymer of vinyl acetate and a monomer copolymerizable therewith, or a partially acetalized product thereof, is subjected to acetalization or acetal exchange reaction to form a styryl polymer. Those to which a dinium group or a styrylquinolium group is added can be mentioned.
本発明において添加される一般式［Ｉ］で表されるジ
オレフィン型化合物として、例えば次のような化合物を
挙げることができる。Examples of the diolefin type compound represented by the general formula [I] to be added in the present invention include the following compounds.
前記ジオレフィン型化合物は、例えば、フタルアルデ
ヒドと 一般式［VI］、［VII］又は［VIII］ （式中、R1、R2、Ｂ及びX-は前記と同義である） で表される四級塩とを塩基性触媒の存在下に縮合させる
ことにより得られる。このとき、一般式［VI］、［VI
I］又は［VIII］の化合物はフタルアルデヒドの約２倍
モル量使用することが好ましい。 The diolefin type compound is, for example, phthalaldehyde and a compound of the general formula [VI], [VII] or [VIII] (Wherein R 1 , R 2 , B and X − have the same meanings as described above) in the presence of a basic catalyst. At this time, the general formulas [VI], [VI
The compound of the formula [I] or [VIII] is preferably used in a molar amount about twice as much as that of the phthalaldehyde.
また、該ジオレフィン型化合物は、感光性ポリビニル
アルコール誘導体の製造原料であるホルミル基を有する
スチリルピリジニウム塩又はスチリルキノリニウム塩の
合成時における副生成物としても得られる。Further, the diolefin type compound is also obtained as a by-product during the synthesis of a styrylpyridinium salt or a styrylquinolinium salt having a formyl group, which is a raw material for producing a photosensitive polyvinyl alcohol derivative.
これらのジオレフィン型化合物は、感光性ポリビニル
アルコール誘導体に対して0.01〜20重量％の範囲で添加
することが好ましく、添加量を加減することにより所望
の感度に容易に調節することができる。These diolefin type compounds are preferably added in the range of 0.01 to 20% by weight based on the photosensitive polyvinyl alcohol derivative, and the desired sensitivity can be easily adjusted by adjusting the amount of addition.
本発明に係る感光性樹脂組成物には、前記感光性ポリ
ビニルアルコール誘導体及びジオレフィン型化合物以外
に、必要に応じて、通常用いられる種々の添加剤、例え
ば重合体エマルジョン、光重合性不飽和化合物、光重合
開始剤等を配合することができさらに無機質固形物、界
面活性剤、着色剤、消泡剤等も任意に使用できる。In the photosensitive resin composition according to the present invention, in addition to the photosensitive polyvinyl alcohol derivative and the diolefin type compound, if necessary, various additives commonly used, for example, a polymer emulsion, a photopolymerizable unsaturated compound , A photopolymerization initiator and the like, and an inorganic solid, a surfactant, a coloring agent, an antifoaming agent and the like can be optionally used.
重合体エマルジョンとして、酢酸ビニウエマルジョ
ン、アクリル系エマルジョン、エチレン−酢酸ビニルエ
マルジョン、エチレン−アクリルエマルジョン、SBRラ
テックス、塩化ビニルエマルジョン、塩化ビニリデンエ
マルジョン、シリコン樹脂エマルジョン等を挙げること
ができる。光重合性不飽和化合物として、アクリロイル
基、メタクリロイル基、ビニルエーテル基、アクリルア
ミド基、メタクリルアミド基等の光活性基を１個以上有
するものを挙げることができる。また、光重合開始剤と
しては、上記の光重合性不飽和化合物の光重合のために
使用するものは殆ど全て使用できる。Examples of the polymer emulsion include a vinyl acetate emulsion, an acrylic emulsion, an ethylene-vinyl acetate emulsion, an ethylene-acryl emulsion, an SBR latex, a vinyl chloride emulsion, a vinylidene chloride emulsion, and a silicone resin emulsion. Examples of the photopolymerizable unsaturated compound include those having at least one photoactive group such as an acryloyl group, a methacryloyl group, a vinyl ether group, an acrylamide group, and a methacrylamide group. As the photopolymerization initiator, almost all of those used for photopolymerization of the photopolymerizable unsaturated compound can be used.
本発明に係る感光性樹脂組成物は、常法に従ってスク
リーン上に塗布し、乾燥した後、露光、現像することに
よりスクリーン印刷版を製造することができる。また、
該感光性樹脂組成物をプラスチックフィルム上に塗布し
てスクリーン製版用既感光性フィルムを作成し、該フィ
ルムをスクリーン版面に水等を用いて貼付け乾燥した
後、露光、現像してスクリーン印刷版を製造することも
できる。The photosensitive resin composition according to the present invention can be applied on a screen according to a conventional method, dried, exposed, and developed to produce a screen printing plate. Also,
The photosensitive resin composition is applied on a plastic film to prepare a photosensitive film for screen plate making, the film is adhered to the screen plate surface using water or the like, dried and then exposed and developed to form a screen printing plate. It can also be manufactured.
以下、本発明の実施例を比較例と対比させて説明する
が、本発明はこれらに限定されるものではない。Hereinafter, examples of the present invention will be described in comparison with comparative examples, but the present invention is not limited to these examples.
〈実施例１〉 ポリビニルアルコール（平均重合度1700、ケン化度88
モル％）に、アセタール化反応によりＮ−メチル−４−
（ｐ−ホルミルスチリル）ピリジニウムメトサルフェー
トを付加して、反応液を大量のアセトンに注加し、樹脂
を沈殿させ、これをメタノールで十分に洗浄し、乾燥し
てスチリルピリジニウム基を付加（1.2モル％）したポ
リビニルアルコール誘導体を得た。<Example 1> Polyvinyl alcohol (average degree of polymerization 1700, degree of saponification 88
Mol%), N-methyl-4-
After adding (p-formylstyryl) pyridinium methosulfate, the reaction solution was poured into a large amount of acetone to precipitate a resin, which was sufficiently washed with methanol and dried to add a styrylpyridinium group (1.2 moles). %) Of a polyvinyl alcohol derivative.
該ポリビニルアルコール誘導体の12.5％水溶液30重量
部に、エチレン−酢酸ビニルエマルジョン（商品名「エ
バディックEP−11」、大日本インキ化学工業社製）（固
形分55％）17重量部、及び下記のジオレフィン型化合物 の１％水溶液１重量部を添加混合して感光液とした。To 30 parts by weight of a 12.5% aqueous solution of the polyvinyl alcohol derivative, 17 parts by weight of ethylene-vinyl acetate emulsion (trade name “Evadic EP-11”, manufactured by Dainippon Ink and Chemicals, Inc.) (solid content: 55%) and the following: Diolefin type compound 1 part by weight of a 1% aqueous solution was added and mixed to obtain a photosensitive solution.
前記感光液を、230メッシュのポリエステルスクリー
ン版にバケットを用いて３回塗布及び乾燥（30〜40℃）
を繰り返し、厚さ15μｍ（スクリーン厚さを含まない）
の感光膜を形成した。The photosensitive solution is applied to a 230-mesh polyester screen plate three times using a bucket and dried (30 to 40 ° C).
Repeatedly, thickness 15μm (excluding screen thickness)
Was formed.
前記スクリーン版の感光膜にプリント配線用ポジフィ
ルムを真空蒸着し、4KWの超高圧水銀灯（オーク社製）
で1mの距離から露光時間を種々変えて露光した。その
後、ポジフィルムを除去し、20℃の水に２分間浸漬後、
20℃の水で２分間シャワー洗浄して未露光部分を洗い流
し、乾燥してスクリーン印刷版を得た。A positive film for printed wiring is vacuum-deposited on the photosensitive film of the screen plate, and a 4KW ultra-high pressure mercury lamp (manufactured by Oak)
Exposure was performed at various exposure times from a distance of 1 m. After that, remove the positive film, immerse in water at 20 ° C for 2 minutes,
Unexposed portions were washed away by shower washing with water at 20 ° C. for 2 minutes, and dried to obtain a screen printing plate.
前記印刷版の解像性等を各露光時間において比較した
ところ、最良の結果を与える露光時間（最適露光時間）
は30秒であった。この印刷版は、耐水性及び耐溶剤性も
良好であり、線幅70μｍの解像力を有し、これを用い
て、エッチングレジスト（商品名「プラスファインPER
−149B」、互応化学工業社製）で基板の銅面に印刷しと
ころ、にじみ、かすれがなく、良好な印刷性を示した。When the resolution and the like of the printing plate are compared at each exposure time, the exposure time that gives the best result (optimum exposure time)
Was 30 seconds. This printing plate has good water resistance and solvent resistance and has a resolving power of a line width of 70 μm, and is used for etching resist (trade name “Plus Fine PER”).
-149B "(manufactured by Ryo Kagaku Kogyo Co., Ltd.) and printed on the copper surface of the substrate, showing no bleeding or blurring and showing good printability.
なお、本実施例で得られた感光液は、液状或はスクリ
ーン版に感光膜を形成した状態で１年間保存しても問題
なく製版に使用でき、良好な保存安定性を示した。The photosensitive liquid obtained in this example was usable for plate making without any problem even when stored for one year in a liquid state or in a state where a photosensitive film was formed on a screen plate, and showed good storage stability.
〈実施例２〉 ジオレフィン型化合物の１％水溶液１重量部を４重量
部とした以外は、実施例１と同様にして感光液を調製
し、スクリーン印刷版を得た。<Example 2> A photosensitive liquid was prepared in the same manner as in Example 1 except that 1 part by weight of a 1% aqueous solution of a diolefin-type compound was changed to 4 parts by weight to obtain a screen printing plate.
製版時における最適露光時間は80秒であった。この印
刷版は、耐水性及び耐溶剤性も良好であり、線幅70μｍ
の解像力を有し、これを用いて、エッチングレジスト
（商品名「プラスファイン PER−149B」、互応化学工
業社製）で基板の銅面に印刷したところ、にじみ、かす
れがなく、良好な印刷性を示した。The optimal exposure time during plate making was 80 seconds. This printing plate has good water resistance and solvent resistance, and has a line width of 70 μm.
When printed on the copper surface of a substrate with an etching resist (trade name “Plus Fine PER-149B”, manufactured by Yoyo Kagaku Kogyo Co., Ltd.), good printability with no bleeding or blurring showed that.
なお、本実施例で得られた感光液も、実施例１と同様
に、液状或はスクリーン版に感光膜を形成した状態で１
年間保存しても問題なく製版に使用でき、良好な保存安
定性を示した。The photosensitive liquid obtained in this example was also used in the same manner as in Example 1 except that the photosensitive film was formed on a liquid or a screen plate.
It can be used for plate making without any problem even if stored for a year, and showed good storage stability.
〈比較例１〉 ジオレフィン型化合物を添加しなかった以外は、実施
例１と同様にして感光液を調製し、スクリーン印刷板を
得た。<Comparative Example 1> A photosensitive liquid was prepared in the same manner as in Example 1 except that the diolefin-type compound was not added, and a screen printing plate was obtained.
しかし、製版時における最適露光時間は10秒以下であ
り、適正な印刷版を再現性よく作成することが困難であ
った。However, the optimal exposure time at the time of plate making is 10 seconds or less, and it has been difficult to produce an appropriate printing plate with good reproducibility.
以上のように、本発明では、スチリルピリジニウム基
及び／又はスチリルキノリニウム基を付加したポリビニ
ルアルコール誘導体からなる感光性樹脂組成物の感度
を、ジオレフィン型化合物の添加により、本来の特性を
損なうことなく任意に調節でき、露光時間の管理が容易
になると共に所望の印刷版を再現性よく製造することが
できる。As described above, in the present invention, the sensitivity of a photosensitive resin composition comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinolinium group is added impairs the original characteristics by the addition of a diolefin-type compound. The printing plate can be adjusted arbitrarily without exposure, the exposure time can be easily controlled, and a desired printing plate can be manufactured with good reproducibility.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭60−247637（ＪＰ，Ａ) 特開 昭61−17142（ＪＰ，Ａ) 特開 昭62−250440（ＪＰ，Ａ) ────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-60-247637 (JP, A) JP-A-61-17142 (JP, A) JP-A-62-250440 (JP, A)
Claims (2)
ルキノリニウム基を付加したポリビニルアルコール誘導
体からなる感光性樹脂組成物に、 一般式［Ｉ］ （式中、Ｒは水素原子、ハロゲン、低級アルキル基又は
アルコキシ基を示し、Ａは 一般式［II］、［III］又は［IV］ で表される基を示し、前記一般式［II］、［III］及び
［IV］中のR1は水素原子、アルキル基又はアラルキル基
を示し、これらはヒドロキシル基、カルバモイル基、エ
ーテル結合、不飽和結合を含んでもよく、R2は水素原子
又は低級アルキル基を示し、Ｂは炭素数１〜６の直鎖状
又は分岐状アルキレン基を示し、X-は陰イオンを示す）
で表されるジオレフィン型化合物を添加したことを特徴
とする感光性樹脂組成物。1. A photosensitive resin composition comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinolinium group is added, a compound represented by the general formula [I]: (Wherein, R represents a hydrogen atom, a halogen, a lower alkyl group or an alkoxy group, and A represents a general formula [II], [III] or [IV] Wherein R 1 in the general formulas [II], [III] and [IV] represents a hydrogen atom, an alkyl group or an aralkyl group, and these are a hydroxyl group, a carbamoyl group, an ether bond, R 2 may represent a hydrogen atom or a lower alkyl group, B may represent a linear or branched alkylene group having 1 to 6 carbon atoms, and X − represents an anion.
A photosensitive resin composition comprising a diolefin compound represented by the formula:
ルキノルニウム基を付加したポリビニルアルコール誘導
体からなる感光性樹脂組成物に請求項１記載の一般式
［Ｉ］で表示されるジオレフィン型化合物を添加するこ
とを特徴とする感光性樹脂組成物の感度調節方法。2. The diolefin type compound represented by the general formula [I] according to claim 1 is added to a photosensitive resin composition comprising a polyvinyl alcohol derivative to which a styrylpyridinium group and / or a styrylquinolnium group is added. A method for adjusting the sensitivity of a photosensitive resin composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2158275A JP2578010B2 (en) | 1990-06-17 | 1990-06-17 | Photosensitive resin composition and method for adjusting its sensitivity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2158275A JP2578010B2 (en) | 1990-06-17 | 1990-06-17 | Photosensitive resin composition and method for adjusting its sensitivity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0451046A JPH0451046A (en) | 1992-02-19 |
| JP2578010B2 true JP2578010B2 (en) | 1997-02-05 |
Family
ID=15668046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2158275A Expired - Fee Related JP2578010B2 (en) | 1990-06-17 | 1990-06-17 | Photosensitive resin composition and method for adjusting its sensitivity |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2578010B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4754098B2 (en) * | 2001-05-29 | 2011-08-24 | 日本化学工業株式会社 | Viologen derivative having the same chemical structure as a liquid crystal compound and applicable as an electron transporting EL device and method for producing the same |
-
1990
- 1990-06-17 JP JP2158275A patent/JP2578010B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0451046A (en) | 1992-02-19 |
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