JPS58167568A - Photopolymerizable imide monomer - Google Patents

Photopolymerizable imide monomer

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Publication number
JPS58167568A
JPS58167568A JP5084582A JP5084582A JPS58167568A JP S58167568 A JPS58167568 A JP S58167568A JP 5084582 A JP5084582 A JP 5084582A JP 5084582 A JP5084582 A JP 5084582A JP S58167568 A JPS58167568 A JP S58167568A
Authority
JP
Japan
Prior art keywords
formula
photopolymerizable
heat
imide
improved
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.)
Pending
Application number
JP5084582A
Other languages
Japanese (ja)
Inventor
Mitsuo Yoshihara
吉原 三男
Keichu Morikawa
森川 敬忠
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nitto Denko Corp
Original Assignee
Nitto Electric Industrial Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nitto Electric Industrial Co Ltd filed Critical Nitto Electric Industrial Co Ltd
Priority to JP5084582A priority Critical patent/JPS58167568A/en
Publication of JPS58167568A publication Critical patent/JPS58167568A/en
Pending legal-status Critical Current

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  • Polymerisation Methods In General (AREA)

Abstract

NEW MATERIAL:A photopolymerizable imide monomer shown by the formula II (R is bifunctional organic group). USE:Useful as a raw material for forming a cured material of a heat-resitant resin. Having a cinnamoyl group sharply inductive by light rays in the molecule, having improved photosetting properties, improved stability as a photosetting composition in a solution state, not being gelatinized in a short period even by allowing it to stand at room temperature. Providing a material to be bonded with improved adhesiveness, forming a cured material of a heat-resistant resin having improved characteristics such as heat resistance, electrical insulating properties, water vapor resistance, chemical resistance, etc. after photosetting. PROCESS:An imide-amine shown by the formula II is reacted with a cinnamic acid shown by the formula III (X is hydroxyl group, alkoxy, preferably 1-5C alkoxy or halogen) or its derviative in an organic solvent such as N,N-dimethylformamide, etc. or in the absence of a solvent, to give a compound shown by the formulaI. The amount of the compound shown by the formula III is 1.7-2.2 times the molar quantity of the compound shown by the formula II.

Description

【発明の詳細な説明】 本発明は、光重合性イミド単量体に関する。[Detailed description of the invention] The present invention relates to photopolymerizable imide monomers.

近年、耐熱性感光性樹脂は、電気・電子工業の分野にお
いて、被覆保護材料、絶縁材料、ソルダーレジスト、接
着剤、耐熱性フォトレジスト等として広く利用されてい
る。
In recent years, heat-resistant photosensitive resins have been widely used in the electrical and electronic industries as covering materials, insulating materials, solder resists, adhesives, heat-resistant photoresists, and the like.

このような耐熱性感光性樹脂は、その本来の特性として
、光硬化性と光硬化後の耐熱性にすぐれているのみなら
ず、被着体に対して良好な接着性を有することが要求さ
れ、更に絶縁特性、耐湿性、耐薬品性等の緒特性にもす
ぐれていることが要求される。また、一方において、無
公害、省資源の観点から、無溶剤系にて、又は僅かの溶
剤の使用量にて皮膜形成能を有し、且つ、使用前に経日
的にゲル化する等の支障をきたさないことが要求される
Such heat-resistant photosensitive resins are required not only to have excellent photocurability and heat resistance after photocuring, but also to have good adhesion to adherends. Furthermore, it is required to have excellent properties such as insulation properties, moisture resistance, and chemical resistance. On the other hand, from the viewpoint of non-pollution and resource saving, it is possible to form a film in a solvent-free system or with a small amount of solvent, and to gel over time before use. It is required that no hindrance be caused.

しかし、従来より知られている耐熱性感光性樹脂はこれ
らの要求特性のいずれをも満足させるものは少なく、一
般に光硬化性にすぐれるものは保存安定性に劣る傾向に
あり、また、被着体に対する接着性に欠けるものが多い
However, there are few conventionally known heat-resistant photosensitive resins that satisfy all of these required properties, and those with excellent photocurability tend to have poor storage stability, and also have poor adhesion. Many of them lack adhesion to the body.

本発明は上記した問題を解決するためになされたもので
あって、保存安定性、感光性、被着体に対する接着性の
いずれにもすぐれるのみならず、光硬化後には耐熱性は
か、前記した緒特性のいずれをも満足する耐熱性樹脂硬
化体を形成する新規且つ有用な光重合性イミド単量体を
提供することを目的とする。また、本発明は、上記した
ような光重合性イミド単量体を製造する方法及び上記し
たような耐熱性樹脂硬化体を形成する光硬化性組成物を
提供することを目的とする。
The present invention was made to solve the above problems, and it not only has excellent storage stability, photosensitivity, and adhesion to adherends, but also has poor heat resistance after photocuring. The object of the present invention is to provide a new and useful photopolymerizable imide monomer that forms a heat-resistant cured resin that satisfies all of the above-mentioned properties. Another object of the present invention is to provide a method for producing the above-mentioned photopolymerizable imide monomer and a photocurable composition that forms the above-mentioned heat-resistant resin cured product.

本発明による光重合性イミド単量体は、一般式(但し、
Rは2価の有機基を示す。) で表される。
The photopolymerizable imide monomer according to the present invention has the general formula (however,
R represents a divalent organic group. ).

上記一般式において、Rは好ましくは2価の脂肪族、芳
香族又は脂環族の炭化水素基を表し、好ましい具体例と
して、炭素数2−20のアルキレフJi、jtl数6−
20のフェニレン基、アルキルフェニレン基、次の一般
式 %式% の2価の有機基を示す。) で表される有機基、並びにシクロヘキシレン基及びアル
キルシクロへキシレン基等を挙げることができる。
In the above general formula, R preferably represents a divalent aliphatic, aromatic or alicyclic hydrocarbon group, and preferable specific examples include Alkirev Ji having 2-20 carbon atoms, jtl having 6-
20 represents a phenylene group, an alkylphenylene group, and a divalent organic group of the following general formula %. ), a cyclohexylene group, an alkylcyclohexylene group, and the like.

上記のような光重合性イミド単量体は、本発明に従って
、一般式 (但し、Rは前記と同じである。) で表されるイミドアミンと一般式 (但し、Xは水酸基、アルコキシ基、好ましくは炭素数
1−5のアルコキシ基、又はハロゲンを示す。) で表されるケイヒ酸又はその誘導体を有機溶剤中又は無
溶剤下で反応させることによって得られる。
According to the present invention, the photopolymerizable imide monomer as described above is an imidoamine represented by the general formula (wherein R is the same as above) and a general formula (where X is a hydroxyl group, an alkoxy group, preferably represents an alkoxy group having 1 to 5 carbon atoms or a halogen.

ケイヒ酸の誘導体としては、具体的にはケイヒ酸メチル
エステルやケイヒ酸クロリド等が用いられるが、好まし
くは穏やかな反応条件下に反応が速やかに進行するケイ
ヒ酸クロリドが用いられる。
As the derivative of cinnamic acid, specifically, cinnamic acid methyl ester, cinnamic acid chloride, etc. are used, but cinnamic acid chloride, which reacts rapidly under mild reaction conditions, is preferably used.

ケイヒ酸又はその誘導体は、−F記イミドアルコールに
対シて1.7〜2.2倍モル、好ましくは2倍モル量を
反応させる。
The cinnamic acid or its derivative is reacted in an amount of 1.7 to 2.2 times the molar amount, preferably 2 times the molar amount, relative to the -F imide alcohol.

有機溶剤としては反応物及び反応生成物のいずれをも溶
解し得るものが好ましく用いられ、具体的にはN、N−
ジメチルホルムアミド、N、N−ジメヂルアセトアミド
、N−メチル−2−ピロリドン、ヘキサメチレンホスホ
ルアミド、ジメチルスルホキシド等の極性非プロトン性
有機溶剤が好ましく用いられる。また、クレゾール、塩
化メチレン等もこれら単独で、又は上記溶剤との混合溶
剤として好ましく用いられる。尚、ケイヒ酸誘導体とし
てケイヒ酸クロリドを用いる場合にはトリメチルアミン
、ジエチルアミン、トリエチルアミン、トリプロピルア
ミン、ピリジン、シクロヘキシルアミン等のアミンを脱
塩酸剤として用いるのが有利である。この場合、反応は
通常、5〜70℃の温度で円滑に進行する。反応に要す
る時間は通常、1〜20時間である。反応後、反応溶液
に生成物の非溶剤、代表的には水を加えることによって
生成物であるイミド化合物を沈殿として得ることができ
る。
As the organic solvent, one that can dissolve both the reactant and the reaction product is preferably used, and specifically, N, N-
Polar aprotic organic solvents such as dimethylformamide, N,N-dimedylacetamide, N-methyl-2-pyrrolidone, hexamethylenephosphoramide, and dimethyl sulfoxide are preferably used. Cresol, methylene chloride, etc. are also preferably used alone or as a mixed solvent with the above solvents. When using cinnamic acid chloride as the cinnamic acid derivative, it is advantageous to use amines such as trimethylamine, diethylamine, triethylamine, tripropylamine, pyridine, and cyclohexylamine as the dehydrochlorination agent. In this case, the reaction usually proceeds smoothly at a temperature of 5 to 70°C. The time required for the reaction is usually 1 to 20 hours. After the reaction, the product imide compound can be obtained as a precipitate by adding a non-solvent for the product, typically water, to the reaction solution.

上記反応に用いるイミドアミンは既に知られており、通
常、1.2.3.4−ブタンテトラカルボン酸又はその
酸無水物に1.3〜2.5倍モル、好ましくは2倍モル
量の一般式 %式% (但し、Rは前記と同じである。) で表されるジアミンを有機溶剤中で、又は無溶剤下に加
熱下に反応させることによって得られる(特公昭53−
47837号)。溶剤を用いる場合は、前記した極性非
プロトン性有機溶剤やクレゾール等が好ましく用いられ
る。上記ジアミンとしては、例えば、m−フェニレンジ
アミン、p−フェニレンジアミン、4.4’−ジアミノ
ジフェニルメタン、4.4’−ジアミノジフェニルエタ
ン、4.4゛−ジアミノジフェニルプロパン、4.4′
−ジアミノジフェニルエーテル、3.4′−ジアミノジ
フェニルエーテル、ベンジジン、3.4’−ジメトキシ
ベンジジン、4,4′−ジアミノジフェニルスクフイド
、4.4’−ジアミノジフェニルスルホン、3.3’−
ジアミノジフェニルスルホン、p−ビス(4−アミノフ
ェノキシ)ベンゼン、m−ビス(4−アミノフェノキシ
)ベンゼ/、4.4′−ジアミノビフェニル、m−キシ
リレンジアミン、p−キシリレンジアミン、ビス(4−
アミノシクロヘキシル)メタン、ヘキサメチレンジアミ
ン、ヘプタメチレンジアミン、オクタメチレンジアミン
、ノナメヂレンジアミン、4゜4′−ジメチルへブタジ
アミン、3−メトキシへブタメチレンジアミン、2,1
1−ジアミノドデカン、1.1−ジアミノシクロヘキサ
ン、2.2’−ジアミノジエチルエーテル、2.2′−
ジアミノジエチルチオエーテル、3.3’−ジアミノジ
プロポキシエタン、2,6−ジアミツビリジン、グアナ
ミン、2,5−ジアミノ−1,3,4−オキサジアゾー
ル、2−(3’−アミノフェニル)−5−アミノベンゾ
キサゾール、ビス(4−アミノフェニル)ジエチルシラ
ン等が用いられる。
The imidoamine used in the above reaction is already known, and usually, 1.3 to 2.5 times the mole, preferably 2 times the mole amount of imidoamine to 1.2.3.4-butanetetracarboxylic acid or its acid anhydride. It is obtained by reacting a diamine represented by the formula % formula % (where R is the same as above) under heating in an organic solvent or in the absence of a solvent (Japanese Patent Publication No. 1973-
No. 47837). When a solvent is used, the above-mentioned polar aprotic organic solvents, cresol, and the like are preferably used. Examples of the diamine include m-phenylenediamine, p-phenylenediamine, 4.4'-diaminodiphenylmethane, 4.4'-diaminodiphenylethane, 4.4'-diaminodiphenylpropane, 4.4'
-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, benzidine, 3,4'-dimethoxybenzidine, 4,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfone, 3,3'-
Diaminodiphenylsulfone, p-bis(4-aminophenoxy)benzene, m-bis(4-aminophenoxy)benzene/, 4,4'-diaminobiphenyl, m-xylylenediamine, p-xylylenediamine, bis(4-aminophenoxy)benzene, −
aminocyclohexyl)methane, hexamethylene diamine, heptamethylene diamine, octamethylene diamine, nonamethylene diamine, 4゜4'-dimethyl hebutadiamine, 3-methoxy hebutamethylene diamine, 2,1
1-diaminododecane, 1.1-diaminocyclohexane, 2.2'-diaminodiethyl ether, 2.2'-
Diaminodiethylthioether, 3,3'-diaminodipropoxyethane, 2,6-diamitubiridine, guanamine, 2,5-diamino-1,3,4-oxadiazole, 2-(3'-aminophenyl)-5- Aminobenzoxazole, bis(4-aminophenyl)diethylsilane, etc. are used.

本発明による光重合性イミド単量体は、通常、有機溶剤
に適宜の光増感剤と共に溶解した組成物として使用に供
される。このための有機溶剤としては、前記した極性非
プロトン性溶剤のほか、テトラヒドロフラン等が好まし
く用いられるが、本発明の光重合性イミド単量体及び用
いる光増感剤を溶解し、且つ、塗布等の作業性を阻害し
ない限りは特に制限されることなく、種々の溶剤を用い
ることができる。また、光増感剤も従来より知られてい
るものが適宜に用いられる。その具体例としてベンゾイ
ン、ベンゾインメチルエーテル、ベンゾインエチルエー
テル、ベンゾインプロピルエーテル、ベンゾフェノン、
ベンジル、ベンジルジメチルケタール等のカルボニル化
合物、ベンジルスルフィドのような有機イオウ化合物、
ある種のハロゲン化合物や光還元性染料等を挙げること
ができる。しかし、これらに限定されるものではない。
The photopolymerizable imide monomer according to the present invention is usually used as a composition dissolved in an organic solvent together with a suitable photosensitizer. In addition to the above-mentioned polar aprotic solvents, tetrahydrofuran and the like are preferably used as organic solvents for this purpose. Various solvents can be used without particular restriction as long as they do not impair workability. Furthermore, conventionally known photosensitizers can be used as appropriate. Specific examples include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzophenone,
Carbonyl compounds such as benzyl and benzyl dimethyl ketal, organic sulfur compounds such as benzyl sulfide,
Examples include certain halogen compounds and photoreducible dyes. However, it is not limited to these.

光増感剤は、通常、上記光重合性イミド単量体100重
量部について001〜7重量部、好ましくは1〜5重量
部用いられる。
The photosensitizer is usually used in an amount of 0.01 to 7 parts by weight, preferably 1 to 5 parts by weight, per 100 parts by weight of the photopolymerizable imide monomer.

更に、本発明の光硬化性組成物は、必要に応じてビニル
単量体、ジビニル単量体、アクリル酸単量体、メタクリ
ル酸単量体等の重合性単量体や、不飽和ポリエステル樹
脂等の重合性樹脂を含有していてもよく、また、充填剤
、接着助剤等を含有していてもよい。
Furthermore, the photocurable composition of the present invention may contain polymerizable monomers such as vinyl monomers, divinyl monomers, acrylic acid monomers, methacrylic acid monomers, and unsaturated polyester resins, if necessary. It may contain polymerizable resins such as, fillers, adhesion aids, etc.

本発明の光硬化性組成物は、従来、・知られているもの
と同様に使用することができ、例えば、バーコーター、
アプリケータ、スピンナ等によって被着体に塗布後、紫
外線を照射して光硬化させれば、強靭で耐熱性にすぐれ
る皮膜を形成する。
The photocurable composition of the present invention can be used in the same manner as conventionally known ones, such as bar coaters,
After applying it to an adherend using an applicator, spinner, etc., it is photocured by irradiating it with ultraviolet rays to form a tough and heat-resistant film.

本発明による光重合性イミド単量体は、鋭敏に光に感応
するシンナモイル基を分子内に有するので、光硬化性に
すぐれると共に、溶液状態の光硬化性組成物として保存
安定性やこすぐれ、室温に放置しても、短期間にゲル化
することがない。また、被着体に対する接着性にもすぐ
れるのみならず、イミド基を分子内に有するので、光硬
化後には耐゛熱性はか、前記した緒特性のいずれをも満
足する耐熱性樹脂硬化体を形成する。
The photopolymerizable imide monomer according to the present invention has a cinnamoyl group that is sensitive to light in its molecule, so it has excellent photocurability, and as a photocurable composition in a solution state, it has excellent storage stability and scratches. Even if left at room temperature, it will not gel in a short period of time. In addition, it not only has excellent adhesion to adherends, but also has an imide group in the molecule, so after photocuring, it is a heat-resistant cured resin that satisfies all of the above properties. form.

以下に本発明の実施例を挙げるが、本発明はこれら実施
例により何ら限定されるものではない。
Examples of the present invention are listed below, but the present invention is not limited to these Examples in any way.

実施例1 攪拌機、冷却器及び温度針を備えた300m1容量の四
つロフラスコに1.2,3.4−ブタンテトラカルボン
酸8.19 g (0,035モル)、ジアミノジフェ
ニルメタン1386g(0,07モル)及びN−メチル
−2−ピロリドン70gを仕込み、150〜210℃の
温度で2時間反応させて、前記一般式において アルコールのN−メチル−2−ピロリドン溶液ヲ得た。
Example 1 8.19 g (0,035 mol) of 1,2,3,4-butanetetracarboxylic acid and 1386 g (0,07 mol) and N-methyl-2-pyrrolidone (70 g) were charged and reacted at a temperature of 150 to 210° C. for 2 hours to obtain a solution of alcohol in N-methyl-2-pyrrolidone in the general formula.

次に、この溶液の温度を20℃にまで冷却した後、これ
にケイヒ酸クロリド11.66 g  (0,07モル
)及びトリエチルアミン10gを添加、溶解させ、温度
を約20〜25℃の範囲に保ちながら0 5時間反応させた。この後、反応溶液に水を加えて、本
発明による光重合性イミド単量体を沈殿として得、これ
を十分に洗滌した。
Next, after cooling the temperature of this solution to 20°C, 11.66 g (0.07 mol) of cinnamic acid chloride and 10 g of triethylamine were added and dissolved therein, and the temperature was adjusted to a range of about 20 to 25°C. The reaction was carried out for 0.5 hours while maintaining the temperature. Thereafter, water was added to the reaction solution to obtain a photopolymerizable imide monomer according to the present invention as a precipitate, which was thoroughly washed.

この単量体10gをN−メチル−2−ピロリドン3gに
溶解させ、更にベンゾフェノン0.3gを溶解させて、
光硬化性組成物Aを得た。
10 g of this monomer was dissolved in 3 g of N-methyl-2-pyrrolidone, and further 0.3 g of benzophenone was dissolved.
A photocurable composition A was obtained.

実施例2 実施例1と同様のフラスコに1.2,3.4−ブタンテ
トラカルボン#8.19g<0.035モル)、m−キ
シリレンジアミン9.52 g (0,07モル)及び
N−メチル−2−ピロリドン70gを仕込み、夏30〜
200℃の温度で3時間反応させて、前ミンのN−メチ
ル−2−ピロリドン溶液を得た。
Example 2 In a flask similar to Example 1, 1,2,3,4-butanetetracarvone #8.19 g (<0.035 mol), m-xylylenediamine 9.52 g (0.07 mol) and N - Prepare 70g of methyl-2-pyrrolidone, summer 30~
The mixture was reacted at a temperature of 200° C. for 3 hours to obtain a solution of Zenmin in N-methyl-2-pyrrolidone.

次に、この溶液の温度を20℃にまで冷却した後、これ
にケイヒ酸クロリド11.66 g (0,07モル)
及びトリエチルアミン10gを添加、溶解させ、温度を
約20〜23℃の範囲に保ちながら1 7時間反応させた。この後、反応溶液に水を加えて、本
発明による光重合性イミド単量体を沈殿として得、これ
を十分に洗滌した。
Next, after cooling the temperature of this solution to 20°C, 11.66 g (0.07 mol) of cinnamic acid chloride was added to it.
and 10 g of triethylamine were added and dissolved, and the mixture was reacted for 17 hours while maintaining the temperature in the range of about 20 to 23°C. Thereafter, water was added to the reaction solution to obtain a photopolymerizable imide monomer according to the present invention as a precipitate, which was thoroughly washed.

この単1体10 gをN−メチル−2−ピロリドン3g
に溶解させ、更にベンゾフェノン0.3gを溶解させて
、光硬化性組成物Bを得た。
10 g of this single substance was mixed with 3 g of N-methyl-2-pyrrolidone.
A photocurable composition B was obtained by further dissolving 0.3 g of benzophenone.

実施例3 実施例1と同様のフラスコに1.2,3.4−ブタンテ
トラカルボン#8.19g (0,035モル)、ヘキ
サメチレンジアミン8.12g(0,07モル)及びヘ
キサメチレンホスホルアミド70gを仕込み、140〜
190℃の温度で3時間反応させて、前記一般式におい
てR=   −(C11)−であるイ6 ミドアミンのN−メチル−2−とロリドン溶液を得た。
Example 3 In a flask similar to Example 1, 8.19 g (0,035 mol) of 1,2,3,4-butanetetracarboxylic acid, 8.12 g (0,07 mol) of hexamethylene diamine, and hexamethylene phosphor were added. Prepare 70g of amide, 140~
The reaction was carried out at a temperature of 190°C for 3 hours to obtain a solution of N-methyl-2- and lolidone of i6 midoamine, where R = -(C11)- in the general formula.

次に、この溶液の温度を20℃にまで冷却した後、これ
にケイヒ酸クロリド11.66 g (0,07モル)
及びトリエチルアミン10gを添加、溶解させ、温度を
約20〜25℃の範囲に保ちながら7時間反応させた。
Next, after cooling the temperature of this solution to 20°C, 11.66 g (0.07 mol) of cinnamic acid chloride was added to it.
and 10 g of triethylamine were added and dissolved, and the mixture was reacted for 7 hours while maintaining the temperature in the range of about 20 to 25°C.

この後、反応溶液に水を加え2 て、本発明による光重合性イミド単量体を沈殿として得
、これを十分に洗滌した。
Thereafter, water was added to the reaction solution to obtain a photopolymerizable imide monomer according to the present invention as a precipitate, which was thoroughly washed.

この単量体10gをN−メチル−2−ピロリドン3gに
溶解させ、更にベンゾフェノン0.3gを溶解させて、
光硬化性組成物Cを得た。
10 g of this monomer was dissolved in 3 g of N-methyl-2-pyrrolidone, and further 0.3 g of benzophenone was dissolved.
A photocurable composition C was obtained.

このようにして得た光硬化性組成物A、B及びCについ
て次の特性試験を行った。
The following characteristic tests were conducted on the photocurable compositions A, B, and C thus obtained.

(11保存安定性 各組成物をN−メチル−2−ピロリドンにイミド単量体
が50重重量になるように溶解混合し、これを室温で放
置したが、いずれの場合にも30日以上にわたってゲル
化が生しなかった。
(11 Storage stability) Each composition was dissolved and mixed in N-methyl-2-pyrrolidone so that the imide monomer was 50% by weight, and the mixture was left at room temperature. No gelation occurred.

(2)光硬化性 各組成物を厚み50μmの銅箔上にバーコーターにて1
0μmの厚さに塗布した後、lQcm離れた位置から8
0W/cmの高圧水銀灯2本を5分間照射し、光硬化さ
せたところ、いずれの場合にも指触にて十分に乾燥硬化
した皮膜が形成されていた。
(2) Apply each photocurable composition on a 50 μm thick copper foil using a bar coater.
After coating to a thickness of 0μm, apply 8cm from a position 1Qcm away.
When the film was photocured by irradiation with two 0 W/cm high pressure mercury lamps for 5 minutes, a film that was sufficiently dry and hardened to the touch was formed in each case.

(3)接着性 3 上記のようにして光硬化させた塗膜を21角にクロスカ
ットし、粘着テープ(日東電気工業株式会社製No、2
9)を貼着して剥離したが、クロスカット100個中、
剥離個数はいずれの場合にも0であった。
(3) Adhesiveness 3 The coating film photocured as above was cross-cut into 21 squares, and adhesive tape (No. 2, manufactured by Nitto Electric Industry Co., Ltd.)
9) was pasted and peeled off, but out of 100 crosscuts,
The number of peeled pieces was 0 in all cases.

(4)耐熱性 前記のようにして光硬化させた塗膜を150℃の温度で
120分間加熱して、塗膜の状態を観察したが、いずれ
の場合にも塗膜に剥離、劣化等の異常は認められなかっ
た。
(4) Heat resistance The coating film photocured as described above was heated at a temperature of 150°C for 120 minutes and the condition of the coating film was observed. No abnormality was observed.

(5)  ハンダ耐熱性 前記のようにし電光硬化させた塗膜を260±5℃のハ
ンダ浴φに10秒間浸漬した後、塗膜の状態を観察した
が、いずれの場合にも塗膜に剥離、劣化等の異常は認め
られなかった。
(5) Solder heat resistance After the coating film cured by lightning as described above was immersed in a solder bath φ at 260±5°C for 10 seconds, the condition of the coating film was observed, but in all cases, the coating film did not peel off. No abnormalities such as deterioration were observed.

(6)耐湿性 前記のようにして光硬化させた塗膜を40℃、90%R
Hの条件下に120時間放置した後、塗膜の状態を観察
したが、いずれの場合にも塗膜に剥離、劣化等の異常は
認められなかった。
(6) Moisture resistance The coating film photocured as described above was heated at 40°C and 90% R.
After being left under the conditions of H for 120 hours, the state of the coating film was observed, and no abnormality such as peeling or deterioration was observed in the coating film in any case.

4 (7)耐薬品性 前記のようにして光硬化させた塗膜をトルエン、テトラ
ヒドロフラン、エタノールの各溶剤中に250℃の温度
で1時間浸漬した後、塗膜の状態を観察したが、いずれ
の場合にも塗膜に異常は認められなかった。
4 (7) Chemical resistance After the coating film photocured as described above was immersed in each solvent of toluene, tetrahydrofuran, and ethanol at a temperature of 250°C for 1 hour, the state of the coating film was observed. No abnormality was observed in the coating film in this case either.

特許出願人 日東電気工業株式会社 5Patent applicant: Nitto Electric Industry Co., Ltd. 5

Claims (1)

【特許請求の範囲】 (11一般式 (但し、Rは2価の有機基を示す。) で表される光重合性5イミド単量体。 (2)Rが2価の脂肪族、芳香族又は脂環族の炭化水素
基であることを特徴とする特許請求の範囲第1項記載の
光重合性イミド単量体。
[Claims] (11) A photopolymerizable 5-imide monomer represented by the general formula (wherein, R represents a divalent organic group). (2) R is a divalent aliphatic or aromatic group. The photopolymerizable imide monomer according to claim 1, which is an alicyclic hydrocarbon group.
JP5084582A 1982-03-29 1982-03-29 Photopolymerizable imide monomer Pending JPS58167568A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5084582A JPS58167568A (en) 1982-03-29 1982-03-29 Photopolymerizable imide monomer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5084582A JPS58167568A (en) 1982-03-29 1982-03-29 Photopolymerizable imide monomer

Publications (1)

Publication Number Publication Date
JPS58167568A true JPS58167568A (en) 1983-10-03

Family

ID=12870060

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5084582A Pending JPS58167568A (en) 1982-03-29 1982-03-29 Photopolymerizable imide monomer

Country Status (1)

Country Link
JP (1) JPS58167568A (en)

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