JPH0565330A - Modified epoxy resin having 2-oxazolidinone ring - Google Patents
Modified epoxy resin having 2-oxazolidinone ringInfo
- Publication number
- JPH0565330A JPH0565330A JP25441391A JP25441391A JPH0565330A JP H0565330 A JPH0565330 A JP H0565330A JP 25441391 A JP25441391 A JP 25441391A JP 25441391 A JP25441391 A JP 25441391A JP H0565330 A JPH0565330 A JP H0565330A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- epoxy
- ring
- oxazolidinone ring
- resin
- 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
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Epoxy Resins (AREA)
Abstract
(57)【要約】 （修正有）
【目的】熱硬化型で、硬化に際し揮散性成分を副生しな
い新しいタイプの変性エポキシ樹脂を提供する。
【構成】原料としてビスフェノールＡ型エポキシ樹脂ま
たはノボラック型エポキシ樹脂を使用し、これにカルバ
ミン酸エステルを反応させる。エポキシ環が２−オキサ
ゾリジノン環へ変換され、下記式のような変性エポキシ
樹脂が得られる。この樹脂は例えばポリアミンとの反応
によって硬化する。
（式中、ｎは０，または１〜１０の整数）(57) [Summary] (Modified) [Purpose] To provide a new type of modified epoxy resin which is a thermosetting type and does not produce a volatile component as a by-product upon curing. [Structure] A bisphenol A type epoxy resin or a novolac type epoxy resin is used as a raw material, and a carbamic acid ester is reacted with this. The epoxy ring is converted to a 2-oxazolidinone ring to obtain a modified epoxy resin represented by the formula below. This resin cures, for example, by reaction with polyamines. (In the formula, n is 0 or an integer of 1 to 10)
Description
【０００１】[0001]
【本発明の背景】エポキシ樹脂は、そのすぐれた物理的
および化学的性質のため、塗料、接着剤、封止剤、成形
材料その他として広く使用されている。エポキシ樹脂自
体はポリアミン系または酸無水物系硬化剤を使用する
か、ルイス酸等を触媒とするイオン重合によって硬化さ
れる。エポキシ樹脂のエポキシ環をアクリル酸やメタク
リル酸で開環し、ラジカル重合可能なエチレン性不飽基
を導入したエポキシアクリレート樹脂は、エポキシ樹脂
本来の硬化メカニズムと異なるメカニズムによって硬化
する変性エポキシ樹脂である。BACKGROUND OF THE INVENTION Epoxy resins are widely used as paints, adhesives, encapsulants, molding compounds and others due to their excellent physical and chemical properties. The epoxy resin itself is cured by using a polyamine-based or acid anhydride-based curing agent or by ionic polymerization using a Lewis acid or the like as a catalyst. Epoxy acrylate resin, in which the epoxy ring of epoxy resin is opened with acrylic acid or methacrylic acid and radically polymerizable ethylenically unsaturated group is introduced, is a modified epoxy resin that cures by a mechanism different from the original curing mechanism of epoxy resin. ..
【０００２】本発明は、ポリアミンとの反応によって硬
化（重合）し得るが、硬化に際し揮散性副生物を発生せ
ず、しかも常温ではポリアミンと反応しない新しいタイ
プの変性エポキシ樹脂を提供することを課題とする。The present invention aims to provide a new type of modified epoxy resin which can be cured (polymerized) by a reaction with a polyamine but does not generate a volatile by-product upon curing and does not react with a polyamine at room temperature. And
【０００３】[0003]
【本発明の開示】本発明によれば、ビスフェノールＡ型
エポキシ樹脂またはノボラック型エポキシ樹脂に、少な
くともエポキシ環に対し当量のカルバミン酸エステルを
反応させ、エポキシ環を２−オキサゾリジノン環に変換
することを特徴とするエポキシ樹脂の変性方法が提供さ
れる。DISCLOSURE OF THE INVENTION According to the present invention, a bisphenol A type epoxy resin or a novolak type epoxy resin is reacted with at least an equivalent amount of a carbamate ester to the epoxy ring to convert the epoxy ring into a 2-oxazolidinone ring. A featured epoxy resin modification method is provided.
【０００４】本発明はまた、かかる変性によって得られ
る変性エポキシ樹脂に関し、該変性樹脂は、ビスフェノ
ールＡ型エポキシ樹脂を原料とする場合、式ＩThe present invention also relates to a modified epoxy resin obtained by such modification, and when the modified resin is made of a bisphenol A type epoxy resin as a raw material, it has the formula I
【化３】 （式中、ｎは０，または１〜１０の整数）で表すことが
できる。[Chemical 3] (In the formula, n is 0 or an integer of 1 to 10).
【０００５】ノボラック型エポキシ樹脂を原料とする場
合、本発明の変性エポキシ樹脂は、式IIWhen a novolac type epoxy resin is used as a raw material, the modified epoxy resin of the present invention has the formula II
【化４】 （式中、Ｒは水素またはメチル、ｍは１〜１０の整数）
で表すことができる。[Chemical 4] (In the formula, R is hydrogen or methyl, m is an integer of 1 to 10)
Can be expressed as
【０００６】[0006]
【詳細な議論】本発明によるエポキシ樹脂の変性方法を
特性基の反応によって示すと以下のようになる。Detailed Discussion The method for modifying an epoxy resin according to the present invention is shown below by the reaction of a characteristic group.
【０００７】[0007]
【化５】 [Chemical 5]
【０００８】原料であるビスフェノール型エポキシ樹脂
およびノボラック型エポキシ樹脂は良く知られており、
前者はビスフェノールＡとエピクロルヒドリンとの反
応、後者はフェノール，ｏ−，ｍ−またはｐ−クレゾー
ルまたはそれらの混合物とホルムアルデヒドとの縮合反
応によって得られるノボラックにエピクロルヒドリンを
反応させることによって得られる。The bisphenol type epoxy resin and novolac type epoxy resin which are raw materials are well known,
The former is obtained by reacting bisphenol A with epichlorohydrin, and the latter is obtained by reacting epichlorohydrin with novolac obtained by condensation reaction of phenol, o-, m- or p-cresol or a mixture thereof with formaldehyde.
【０００９】本発明において使用されるビスフェノール
Ａ型エポキシ樹脂としてはエピコート８２７（商品名，
油化シェルエポキシ（株），エポキシ当量１８０−１９
０）、エピコート１００１（商品名，油化シェルエポキ
シ（株），エポキシ当量４５０−５００）、エピコート
１０１０（商品名，油化シェルエポキシ（株），エポキ
シ当量３０００−５０００）等が挙げられ、また、フェ
ノールノボラック型エポキシ樹脂としては、エピコート
１５２（商品名，油化シェルエポキシ（株），エポキシ
当量１７２−１７９）が、クレゾールノボラック型エポ
キシ樹脂としては、エピコート１８０Ｓ６５（商品名，
油化シェルエポキシ（株），エポキシ当量２０５−２２
０）等が挙げられる。The bisphenol A type epoxy resin used in the present invention is Epicoat 827 (trade name,
Yuka Shell Epoxy Co., Ltd., epoxy equivalent 180-19
0), Epicoat 1001 (trade name, Yuka Shell Epoxy Co., Ltd., epoxy equivalent 450-500), Epicoat 1010 (trade name, Yuka Shell Epoxy Co., Ltd., epoxy equivalent 3000-5000) and the like. As the phenol novolac type epoxy resin, Epicoat 152 (trade name, Yuka Shell Epoxy Co., Ltd., epoxy equivalent 172-179) is used, and as the cresol novolac type epoxy resin, Epicoat 180S65 (trade name,
Yuka Shell Epoxy Co., Ltd., epoxy equivalent 205-22
0) and the like.
【００１０】また、これらのエポキシ樹脂と反応させる
カルバミン酸エステルとしては、カルバミン酸メチル、
カルバミン酸エチル、カルバミン酸イソプロピル、カル
バミン酸ブチル、カルバミン酸ベンジル、カルバミン酸
フェニル、カルバミン酸−２−ヒドロキシエチル等が挙
げられる。Carbamates to be reacted with these epoxy resins include methyl carbamate,
Examples thereof include ethyl carbamate, isopropyl carbamate, butyl carbamate, benzyl carbamate, phenyl carbamate, and 2-hydroxyethyl carbamate.
【００１１】エポキシ樹脂に対するカルバミン酸エステ
ルの使用量は、エポキシ環に対して少なくとも当量でな
ければならない。反応によって副生するアルコールは減
圧下留去するか、または窒素ガスのような不活性ガスの
吹込みによって系から除去する。The amount of carbamic acid ester used with respect to the epoxy resin must be at least equivalent to the epoxy ring. The alcohol by-produced by the reaction is removed from the system by distillation under reduced pressure or by blowing an inert gas such as nitrogen gas.
【００１２】この反応は、触媒として第三級アミンとス
ズ化合物との組合せを使用することによって促進し得
る。The reaction can be promoted by using a combination of a tertiary amine and a tin compound as a catalyst.
【００１３】触媒として使用される第三級アミンとして
は、脂肪族アミン、芳香族アミン、含窒素複素環等が挙
げられ、Ｎ，Ｎ−ジメチルベンジルアミン、Ｎ，Ｎ−ジ
メチルアニリン、トリエチルアミン、Ｎ，Ｎ−ジメチル
シクロヘキシルアミン、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラメ
チルエチレンジアミン、Ｎ−メチルモルホリン、１，４
−ジアザビシクロ〔２．２．２〕オクタン、１，８−ジ
アザビシクロ〔５．４．０〕−７−ウンデセン、ピリジ
ン、キノリン、イミダゾール等が使用される。Examples of the tertiary amine used as a catalyst include aliphatic amines, aromatic amines, nitrogen-containing heterocycles, N, N-dimethylbenzylamine, N, N-dimethylaniline, triethylamine, N , N-dimethylcyclohexylamine, N, N, N ′, N′-tetramethylethylenediamine, N-methylmorpholine, 1,4
-Diazabicyclo [2.2.2] octane, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, quinoline, imidazole and the like are used.
【００１４】また、第三級アミンと併用されるスズ化合
物としては、ジラウリル酸ジ−ｎ−ブチルスズ、塩化第
一スズ、オクテン酸スズ、ジブチルスズオキシド、ジオ
クチルスズオキシド、１，３−ジアセトキシテトラブチ
ルジスタノキサン、１，３−ジクロルテトラブチルジス
タノキサン、ジブチルジブトキシスズ等が挙げられる。As the tin compound used in combination with the tertiary amine, di-n-butyltin dilaurate, stannous chloride, tin octenoate, dibutyltin oxide, dioctyltin oxide, 1,3-diacetoxytetrabutyl. Examples thereof include distannoxane, 1,3-dichlorotetrabutyl distannoxane, dibutyl dibutoxy tin, and the like.
【００１５】両触媒の添加量は、ぞれぞれ、出発原料の
０．０１−５．０重量％が好ましく、特に０．１−３．
０重量％が好ましい。The amount of each catalyst added is preferably 0.01 to 5.0% by weight of the starting material, and particularly 0.1-3.
0% by weight is preferred.
【００１６】反応温度は１００℃−１８０℃が好まし
く、１００℃以下では反応速度が非常に遅く、また、１
８０℃以上であると副反応が起きる危険性がある。反応
時間は０．２−１０時間、好ましくは０．５時間から５
時間である。The reaction temperature is preferably 100 ° C. to 180 ° C., and the reaction rate is very slow below 100 ° C.
If it is higher than 80 ° C, there is a risk of side reaction. The reaction time is 0.2-10 hours, preferably 0.5 hours to 5 hours.
It's time.
【００１７】本反応は、反応に関与しない溶剤等の共存
下でも実施可能であるが、工業的な利用を考えた場合、
特に必要としない場合は溶剤等を使用する必要はない。This reaction can be carried out in the coexistence of a solvent or the like which does not participate in the reaction, but when considering industrial use,
It is not necessary to use a solvent or the like unless otherwise required.
【００１８】以下、実施例により本発明を詳細に説明す
るが、本発明は、これに限定されるものではない。Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.
【００１９】実施例１ 冷却器、攪拌器、温度計、デカンター及び窒素源を備え
た反応器にエポキシ当量１８０のビスフェノールＡ型エ
ポキシ樹脂（商品名，エピコート８２７；油化シェルエ
ポキシ（株））１８０ｇ、カルバミン酸エチル８９ｇ、
Ｎ，Ｎ−ジメチルベンジルアミン２ｇ及びジラウリル酸
ジ−ｎ−ブチルスズ２ｇを貯え、窒素ガスを吹込みなが
ら１３０℃で２時間反応させ、副生するエタノール４６
ｇを除去し、無色透明な粘稠液体を得た。このものは、
ＩＲ測定の結果、オキサゾリジノン環のカルボニル基に
基づく１７４０ｃｍ-1の吸収が認められ、また、エポキ
シ基に基づく９０５ｃｍ-1の吸収、およびカルバミン酸
エチルのカルボニル基に基づく１７２０ｃｍ-1の吸収が
消失しており、目的とするオキサゾリジノン環含有樹脂
の生成を確認した。Example 1 180 g of a bisphenol A type epoxy resin (trade name, Epicoat 827; Yuka Shell Epoxy Co., Ltd.) having an epoxy equivalent of 180 in a reactor equipped with a condenser, a stirrer, a thermometer, a decanter and a nitrogen source. 89 g of ethyl carbamate,
2 g of N, N-dimethylbenzylamine and 2 g of di-n-butyltin dilaurylate were stored and reacted at 130 ° C. for 2 hours while blowing nitrogen gas to produce by-produced ethanol 46.
g was removed to obtain a colorless transparent viscous liquid. This one is
Result of IR measurement, absorption of 1740 cm -1 based on the carbonyl group of the oxazolidinone ring is observed, also, the absorption of 905cm -1 based on epoxy group, and the absorption of 1720 cm -1 based on the carbonyl group of ethyl carbamate disappeared It was confirmed that the desired oxazolidinone ring-containing resin was produced.
【００２０】実施例２ 冷却器、攪拌器、温度計、デカンター及び窒素源を備え
た反応器にエポキシ当量４７５のビスフェノールＡ型エ
ポキシ樹脂（商品名，エピコート１００１；油化シェル
エポキシ（株））１９０ｇおよびカルバミン酸エチル３
５．６ｇをキシレン６９．１ｇに溶解させ、Ｎ，Ｎ−ジ
メチルベンジルアミン３．４ｇ及びジラウリル酸ジ−ｎ
−ブチルスズ３．４ｇを加え、窒素ガスを吹込み、１４
０℃で１時間反応させ、副生するエタノール１８．４ｇ
を除去した。得られた樹脂溶液を室温まで冷却し、黄色
透明固体を得た。このものは、ＩＲ測定の結果、エポキ
シ基に基づく９０５ｃｍ-1の吸収、およびカルバミン酸
エチルのカルボニル基に基づく１７２０ｃｍ-1の吸収が
消失しており、オキサゾリジノン環のカルボニル基に基
づく１７４０ｃｍ-1の吸収が認められており、目的とす
るオキサゾリジノン環含有樹脂の生成を確認した。Example 2 190 g of a bisphenol A type epoxy resin (trade name, Epicoat 1001; Yuka Shell Epoxy Co., Ltd.) having an epoxy equivalent of 475 in a reactor equipped with a condenser, a stirrer, a thermometer, a decanter and a nitrogen source. And ethyl carbamate 3
Dissolving 5.6 g in 69.1 g of xylene, 3.4 g of N, N-dimethylbenzylamine and di-n-dilauryl acid were used.
-Butyltin (3.4 g) was added, and nitrogen gas was blown in to
React at 0 ° C for 1 hour, by-product ethanol 18.4g
Was removed. The obtained resin solution was cooled to room temperature to obtain a yellow transparent solid. As a result of IR measurement, the absorption of 905 cm −1 based on the epoxy group and the absorption of 1720 cm −1 based on the carbonyl group of ethyl carbamate disappeared, and this product showed that the absorption of 1740 cm −1 based on the carbonyl group of the oxazolidinone ring disappeared. Absorption was observed, and formation of the desired oxazolidinone ring-containing resin was confirmed.
【００２１】実施例３ 冷却器、攪拌器、温度計、デカンター及び窒素源を備え
た反応器にエポキシ当量４０００のビスフェノールＡ型
エポキシ樹脂（商品名，エピコート１０１０；油化シェ
ルエポキシ（株））４００ｇおよびカルバミン酸エチル
８．９ｇをキシレン１００ｇに溶解させ、Ｎ，Ｎ−ジメ
チルベンジルアミン０．８ｇおよびジラウリル酸ジ−ｎ
−ブチルスズ０．８ｇを加え、窒素ガスを吹込み、１４
０℃で１時間反応させ、副生するエタノール４．６ｇを
除去した。得られた樹脂溶液を室温まで冷却し、黄色透
明固体を得た。このものは、ＩＲ測定の結果、エポキシ
基に基づく９０５ｃｍ-1の吸収、およびカルバミン酸エ
チルのカルボニル基に基づく１７２０ｃｍ-1の吸収が消
失し、オキサゾリジノン環のカルボニル基に基づく１７
４０ｃｍ-1の吸収が認められており、目的とするオキサ
ゾリジノン環含有樹脂の生成を確認した。Example 3 400 g of bisphenol A type epoxy resin (trade name, Epicoat 1010; Yuka Shell Epoxy Co., Ltd.) having an epoxy equivalent of 4000 in a reactor equipped with a condenser, a stirrer, a thermometer, a decanter and a nitrogen source. And 8.9 g of ethyl carbamate are dissolved in 100 g of xylene, 0.8 g of N, N-dimethylbenzylamine and di-n-dilauryl acid are added.
-Butyltin 0.8g was added, and nitrogen gas was blown into it.
The reaction was carried out at 0 ° C for 1 hour to remove 4.6 g of by-product ethanol. The obtained resin solution was cooled to room temperature to obtain a yellow transparent solid. As a result of IR measurement, the absorption of 905 cm −1 based on the epoxy group and the absorption of 1720 cm −1 based on the carbonyl group of ethyl carbamate disappeared, and this product was determined to be 17% based on the carbonyl group of the oxazolidinone ring.
Absorption at 40 cm -1 was confirmed, confirming the formation of the desired oxazolidinone ring-containing resin.
【００２２】実施例４ 冷却器、攪拌器、温度計、デカンター及び窒素源を備え
た反応器にエポキシ当量２２０のクレゾールノボラック
型エポキシ樹脂（商品名，エピコート１８０Ｓ６５；油
化シェルエポキシ（株））２２０ｇにカルバミン酸エチ
ル８９ｇ、Ｎ，Ｎ−ジメチルベンジルアミン５．２ｇお
よびジラウリル酸ジ−ｎ−ブチルスズ５．２ｇを加えた
後、副生するエタノールを留去しながら１５０℃で加熱
を続け、２時間の加熱により理論量のエタノール４６ｇ
を留去させた。得られた樹脂溶液はＩＲ測定の結果、エ
ポキシ基に基づく９０５ｃｍ-1の吸収、およびカルバミ
ン酸エチルのカルボニル基に基づく１７２０ｃｍ-1の吸
収が消失し、オキサゾリジノン環のカルボニル基に基づ
く１７４０ｃｍ-1の吸収が認められており、目的とする
オキサゾリジノン環含有樹脂の生成を確認した。Example 4 220 g of a cresol novolac type epoxy resin (trade name, Epicoat 180S65; Yuka Shell Epoxy Co., Ltd.) having an epoxy equivalent of 220 in a reactor equipped with a cooler, a stirrer, a thermometer, a decanter and a nitrogen source. After adding 89 g of ethyl carbamate, 5.2 g of N, N-dimethylbenzylamine and 5.2 g of di-n-butyltin dilaurate to the mixture, heating was continued at 150 ° C. for 2 hours while distilling off by-produced ethanol. The theoretical amount of ethanol by heating 46g
Was distilled off. As a result of IR measurement, the obtained resin solution showed that the absorption at 905 cm −1 based on the epoxy group and the absorption at 1720 cm −1 based on the carbonyl group of ethyl carbamate disappeared, and the absorption at 1740 cm −1 based on the carbonyl group of the oxazolidinone ring disappeared. Absorption was observed, and formation of the desired oxazolidinone ring-containing resin was confirmed.
Claims (3)
ボラック型エポキシ樹脂に、少なくともエポキシ環に対
し当量のカルバミン酸エステルを反応させ、エポキシ環
を２−オキサゾリジノン環に変換することを特徴とする
エポキシ樹脂の変性方法。1. A modification of an epoxy resin, which comprises reacting a bisphenol A type epoxy resin or a novolac type epoxy resin with at least an equivalent amount of a carbamate ester to the epoxy ring to convert the epoxy ring into a 2-oxazolidinone ring. Method.
−オキサゾリジノン環を有する変性エポキシ樹脂。2. Formula I: (Wherein n is 0 or an integer of 1 to 10) 2
-A modified epoxy resin having an oxazolidinone ring.
で表される２−オキサゾリジノン環を有する変性エポキ
シ樹脂。3. Formula II: (In the formula, R is hydrogen or methyl, m is an integer of 1 to 10)
A modified epoxy resin having a 2-oxazolidinone ring represented by:
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25441391A JPH0565330A (en) | 1991-09-05 | 1991-09-05 | Modified epoxy resin having 2-oxazolidinone ring |
| EP92115104A EP0530812B1 (en) | 1991-09-05 | 1992-09-03 | Thermosetting resinous composition containing polyfunctional oxazolidinone component and polyamine component |
| EP95109833A EP0677515A1 (en) | 1991-09-05 | 1992-09-03 | Method for preparing 2-oxazolidinone derivatives |
| DE69210919T DE69210919T2 (en) | 1991-09-05 | 1992-09-03 | Thermosetting resin mixture containing a polyfunctional oxazolidone component and a polyamine component |
| US07/941,297 US5237021A (en) | 1991-09-05 | 1992-09-04 | Thermosetting resinous composition containing polyfunctional oxazolidinone component and polyamine component |
| US08/051,906 US5324797A (en) | 1991-09-05 | 1993-04-26 | Thermosetting resinous composition containing polyfunctional oxazolidinone terminated epoxy resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25441391A JPH0565330A (en) | 1991-09-05 | 1991-09-05 | Modified epoxy resin having 2-oxazolidinone ring |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0565330A true JPH0565330A (en) | 1993-03-19 |
Family
ID=17264632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25441391A Pending JPH0565330A (en) | 1991-09-05 | 1991-09-05 | Modified epoxy resin having 2-oxazolidinone ring |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0565330A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013194016A (en) * | 2012-03-22 | 2013-09-30 | Kuraray Co Ltd | Method for producing 5-allyloxymethyl-2-oxazolidinone |
-
1991
- 1991-09-05 JP JP25441391A patent/JPH0565330A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013194016A (en) * | 2012-03-22 | 2013-09-30 | Kuraray Co Ltd | Method for producing 5-allyloxymethyl-2-oxazolidinone |
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