JPH0347185A - Spiroepoxide diacrylate compound - Google Patents
Spiroepoxide diacrylate compoundInfo
- Publication number
- JPH0347185A JPH0347185A JP1181489A JP18148989A JPH0347185A JP H0347185 A JPH0347185 A JP H0347185A JP 1181489 A JP1181489 A JP 1181489A JP 18148989 A JP18148989 A JP 18148989A JP H0347185 A JPH0347185 A JP H0347185A
- Authority
- JP
- Japan
- Prior art keywords
- tetraoxaspiro
- undecane
- diacrylate
- compound
- bis
- 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
- -1 diacrylate compound Chemical class 0.000 title description 9
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 239000011347 resin Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000004386 diacrylate group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 3
- 239000008199 coating composition Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000000976 ink Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- PVCPWBCCWVKROB-UHFFFAOYSA-N 3-[3-(2-carboxyethyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propanoic acid Chemical compound C1OC(CCC(=O)O)OCC21COC(CCC(O)=O)OC2 PVCPWBCCWVKROB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 150000003077 polyols Chemical class 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
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、塗料、印刷インキ、 レジスト等の感光性樹
脂原料として有用な速硬化性であり、塗膜強度、密着性
および耐候成に優れた生成物を得ることの出来る新規ス
ピロエポキシジアクリレート化合物に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention is a fast-curing material useful as a photosensitive resin raw material for paints, printing inks, resists, etc., and has excellent coating film strength, adhesion, and weather resistance. The present invention relates to novel spiroepoxy diacrylate compounds from which products can be obtained.
く従来の技術及び問題点〉
従来、エポキシアクリレート樹脂どしては、ビスフェノ
ールＡ形エポキシ樹脂、ノボラック型エポキシ樹脂、エ
ポキシ化ポリブタジェンなどが知られている。これらの
アクリレートは、耐熱性、耐薬品性に優れた性能を示す
、しかし、これらは分子内に共役二重結合を有している
ために耐候性が悪いという欠点を有する。また、アクリ
ル化エポキシ樹脂の塗膜物性は、ベースとなるエピキシ
樹脂の構造によるところが大きい０本発明のスピロエポ
キシジアクリレートは１分子内に硬く、耐候性およびか
とう性のあるスピロ骨格、接着性に優れたエポキシ基由
来の水酸基、光架橋性を有するアクリル基を有しており
、耐候性、接着性、塗膜強度に優れた感光性樹脂になる
と考えられる。BACKGROUND ART AND PROBLEMS> Conventionally, as epoxy acrylate resins, bisphenol A type epoxy resins, novolac type epoxy resins, epoxidized polybutadiene, etc. are known. These acrylates exhibit excellent heat resistance and chemical resistance, but have a drawback of poor weather resistance because they have a conjugated double bond in their molecules. In addition, the physical properties of the coating film of acrylated epoxy resin largely depend on the structure of the base epixy resin.The spiroepoxy diacrylate of the present invention has a hard, weather-resistant and resilient spiro skeleton within one molecule, and has excellent adhesive properties. It has excellent hydroxyl groups derived from epoxy groups and acrylic groups with photocrosslinking properties, and is thought to be a photosensitive resin with excellent weather resistance, adhesiveness, and coating strength.
〈発明が解決しようとする課題〉
本発明の課題は、耐候性、接着性、塗膜強度に優れた感
光性樹脂化合物を提供する事である。<Problems to be Solved by the Invention> An object of the present invention is to provide a photosensitive resin compound that has excellent weather resistance, adhesiveness, and coating strength.
く課題を解決するための手段〉
本発明者らは、耐候性、接着性、塗膜強度に優れた感光
性樹脂素材について鋭意検討の結果、これまでにエポキ
シ樹脂との硬化物に優れた耐候性、接着性、可どう性、
を与えることが知られているスピロ環を有するジカルボ
ン酸をスピロエポキシビスアクリレートに誘導する事に
より、・該化合物が！！！膜物性に優れた感光性樹脂硬
化物を与えることを見いだし本発明を完成した。Means for Solving the Problems> As a result of intensive studies on photosensitive resin materials with excellent weather resistance, adhesion, and coating strength, the present inventors have so far found that cured products with epoxy resins have excellent weather resistance. properties, adhesion, flexibility,
By deriving a spiro ring-containing dicarboxylic acid known to give spiroepoxy bisacrylate, the compound can be! ! ! The present invention was completed by discovering that a photosensitive resin cured product having excellent film properties can be obtained.
すなわち、本発明は、一般式：
はＨまたはＣＨ３を表す、）で示されるスピロエポキシ
ジアクリレート化合物である。That is, the present invention is a spiroepoxy diacrylate compound represented by the general formula: represents H or CH3.
本発明のスピロエポキシジアクリレート化合物は、公知
の方法によって得る事が出来る。すなわち、スピロジカ
ルボン酸にエピクロルヒドリンを加えスピロジグリシジ
ルエステルとした後、触媒の存在下、アクリル酸または
メタクリル酸と反応させることにより得ることができる
。また、アクリル酸またはメタクリル酸とエピクロルヒ
ドリンを反応させグリシジルエステルとした後、触媒の
存在下、スピロジカルボン酸と反応させることにより得
ることもできる０例えば、スピロジカルボン酸に三級ア
ミンの存在下、当量のグリシジルメタクリレートな無溶
媒で８０〜１２０”Ｃの温度で反応させる事により得る
ことができる。The spiroepoxy diacrylate compound of the present invention can be obtained by a known method. That is, it can be obtained by adding epichlorohydrin to spirodicarboxylic acid to form spirodiglycidyl ester, and then reacting it with acrylic acid or methacrylic acid in the presence of a catalyst. It can also be obtained by reacting acrylic acid or methacrylic acid with epichlorohydrin to form a glycidyl ester, and then reacting it with spirodicarboxylic acid in the presence of a catalyst. It can be obtained by reacting glycidyl methacrylate without a solvent at a temperature of 80 to 120''C.
本発明に用いることの出来るスピロジカルボン酸として
は、 ３，９−ジカルボキ゛シー２． ４． ８゜１０
−テトラオキサスピロ（５，５）ウンデカン、３．９−
ビス（カルボキシメチル） −２，４，８゜１０−テト
ラオキサスピロ（５，５）ウンデカン、３．９−ビス（
２−カルボキシエチル）−２，４゜８．１０−テトラオ
キサスピロ（５，５）ウンデカン、 ３，９−ビス（３
−カルボキシプロピル）−２，４，８，１０−テトラオ
キサスピロ〔５゜５〕ウンデカン、３，９−ビス（４−
カルボキシブチル）−２，４，８，１０−テトラオキサ
スピロ（５，５） ウンデカン、３．９−ビス（５−カ
ルボキシペンチル） −２，４，８，１０−テトラオキ
サスピロ（５，５）ウンデカンを用いることが出来る。Examples of spirodicarboxylic acids that can be used in the present invention include 3,9-dicarboxylic acids2. 4. 8°10
-Tetraoxaspiro(5,5)undecane, 3.9-
Bis(carboxymethyl) -2,4,8゜10-tetraoxaspiro(5,5)undecane, 3,9-bis(
2-carboxyethyl)-2,4゜8.10-tetraoxaspiro(5,5)undecane, 3,9-bis(3
-carboxypropyl)-2,4,8,10-tetraoxaspiro[5゜5]undecane, 3,9-bis(4-
carboxybutyl)-2,4,8,10-tetraoxaspiro(5,5) undecane, 3,9-bis(5-carboxypentyl)-2,4,8,10-tetraoxaspiro(5,5) Undecane can be used.
また、アクリル酸誘導体としては、アクリル酸、メタク
リル酸を用いることができる。Further, as the acrylic acid derivative, acrylic acid and methacrylic acid can be used.
又、本反応に用いるエステル化触媒としては、主にトリ
エチルアミン、ベンジルジメチルアミン等の３級アミン
、またはその無機、有機酸の塩が用いられるが、１級、
２級アミン及びその塩を用いることもできる。その使用
量は、原料カルボン酸当り０．０１〜５部が用いられる
０本発明のスピロエポキシジアクリレートは、粘度調節
剤である種々の単官能及び多官能アクリレートと共に使
用することができる。Ｍアクリレートとしては、種々の
ポリオールのモ人 ジ、 トリアクリレートまたは、・
メタクリレートが用いられる０例えばヒドロキシアル
キルアクリレート、アルキレンポリオールポリアクリレ
ート、およびポリオキシアルキレングリコールジアクリ
レート、または、それらのメタクリレートが用いられる
。光開始剤としてはアセトフェノン系、ベンゾイン系、
ベンゾフェノン系チオキサンソン系、の物が用い−られ
る。以下１本発明を実施例をもって説明する。In addition, as the esterification catalyst used in this reaction, tertiary amines such as triethylamine and benzyldimethylamine, or their inorganic or organic acid salts are mainly used, but primary,
Secondary amines and their salts can also be used. The amount used is 0.01 to 5 parts per starting carboxylic acid. The spiroepoxy diacrylate of the present invention can be used with various monofunctional and polyfunctional acrylates as viscosity modifiers. M acrylates include various polyol monoacrylates, triacrylates, or...
For example, hydroxyalkyl acrylate, alkylene polyol polyacrylate, and polyoxyalkylene glycol diacrylate, or their methacrylates are used. Photoinitiators include acetophenone, benzoin,
Benzophenone-based thioxanthone-based products are used. The present invention will be explained below with reference to examples.
〈実施例〉
実施例１
３．９−ビス（２−カルボキシエチル）２、 ４． ８
． １０−テトラオキサスピロ（５，５）ウンデカン２
０ｇにグリシジルメタクリレート１８、 ７ｇ、）リエ
チルアミン０．２ｍｌを加え８０℃で５時間、続いて１
００℃で５時間かくはんし３，９−ビス（２−カルボキ
シエチル）−２゜４、 ８． １０−テトラオキサスピ
ロ（５，５）ウンデカンのエポキシジアクリレートを得
た。収率は定量的であった。ＮＭＲｌ ＩＲを図に示す
。<Example> Example 1 3.9-bis(2-carboxyethyl) 2, 4. 8
．． 10-tetraoxaspiro(5,5)undecane 2
Add 0.2 ml of glycidyl methacrylate (18.7 g) and ethylamine to 0.0 g at 80°C for 5 hours,
Stir at 00°C for 5 hours to prepare 3,9-bis(2-carboxyethyl)-2°4, 8. Epoxy diacrylate of 10-tetraoxaspiro(5,5)undecane was obtained. The yield was quantitative. NMRl IR is shown in the figure.
実施例２
３．９−ビス（２−カルボキシエチル）−２、４，８，
１０−テトラオキサスピロ（５，５）ウンデカンのエポ
キシジアクリレート６０重量部とトリメチロールプロパ
ン２０重量部、ベンゾインイソプロピルエーテル０．
８重量部を均一に溶解させ感光性樹脂組成物とした。こ
の組成物をアルミニウム版の上にキャストし、４００Ｗ
の高圧水銀灯で５分及び１０分間露光し、塗膜の硬化速
度及び塗膜硬度を測定した。結果を表−１に示す。Example 2 3.9-bis(2-carboxyethyl)-2,4,8,
60 parts by weight of epoxy diacrylate of 10-tetraoxaspiro(5,5)undecane, 20 parts by weight of trimethylolpropane, and 0.0 parts by weight of benzoin isopropyl ether.
8 parts by weight were uniformly dissolved to obtain a photosensitive resin composition. This composition was cast onto an aluminum plate and 400W
The coating film was exposed to light for 5 and 10 minutes using a high-pressure mercury lamp, and the curing speed and coating hardness of the coating film were measured. The results are shown in Table-1.
比較例１
ビス（カルボキシエチル）テトラオキサスピロウンデカ
ンのエポキシジアクリレートの代わりにヘキサンジオー
ルジアクリレートを用いる他は実施例２と同様の実験を
行った。結果を表−１に示す。Comparative Example 1 An experiment similar to Example 2 was conducted except that hexanediol diacrylate was used instead of the epoxy diacrylate of bis(carboxyethyl)tetraoxaspiroundecane. The results are shown in Table-1.
表−１塗膜の硬化の程度および塗膜硬度（１）Ｏ： 硬
化 Δニ一部硬化 Ｘ： 未硬化（２）高圧水銀灯 ４
００Ｗで１０分硬化した物の塗膜硬度
〈発明の効果〉
本発明のスピロエポキシジアクリレート誘導体は塗料用
感光性樹脂として用いた場合、速硬化性及び硬化物の塗
膜硬度に優れていた。Table-1 Degree of cure of coating film and coating film hardness (1) O: Cured Partially cured X: Uncured (2) High pressure mercury lamp 4
Coating film hardness of product cured at 00W for 10 minutes <Effect of the invention> When the spiroepoxy diacrylate derivative of the present invention was used as a photosensitive resin for paint, it was excellent in fast curing property and coating film hardness of the cured product.
図１、図２は１本発明で得られた３、９−ビス（２−カ
ルボキシエチル） −２，４，８，１０−テトラオキサ
スピロ（５，５）ウンデカ、ンのエポキシジアクリレー
トのＮＭＲｌ及びＩＲである。Figures 1 and 2 show the NMR ratio of epoxy diacrylate of 3,9-bis(2-carboxyethyl)-2,4,8,10-tetraoxaspiro(5,5)undecane obtained in the present invention. and IR.
Claims (1)
たはＣＨ３を表す。）で示されるスピロエポキシジアク
リレート化合物。 ２）ｎは１、ｍは１または２で示される特許請求項１）
記載のスピロエポキシジアクリレート化合物。 ３）一般式： ▲数式、化学式、表等があります▼ （式中ｎは１〜５、ｍは０〜５の整数を表し、ＲはＨま
たはＣＨ３を表す、）で示されるスピロエポキシジアク
リレート化合物を１〜７０部含有して成る感光性樹脂塗
料組成物。[Claims] 1) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, n represents an integer of 1 to 5, m represents an integer of 0 to 5, and R represents H or CH3.) Spiroepoxy diacrylate compounds shown. 2) Patent claim 1 in which n is 1 and m is 1 or 2)
Spiroepoxy diacrylate compounds as described. 3) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, n represents an integer of 1 to 5, m represents an integer of 0 to 5, and R represents H or CH3) Spiroepoxy diacrylate A photosensitive resin coating composition comprising 1 to 70 parts of a compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1181489A JPH0347185A (en) | 1989-07-13 | 1989-07-13 | Spiroepoxide diacrylate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1181489A JPH0347185A (en) | 1989-07-13 | 1989-07-13 | Spiroepoxide diacrylate compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0347185A true JPH0347185A (en) | 1991-02-28 |
Family
ID=16101655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1181489A Pending JPH0347185A (en) | 1989-07-13 | 1989-07-13 | Spiroepoxide diacrylate compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0347185A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4930465A (en) * | 1972-06-16 | 1974-03-18 | ||
| JPS6099181A (en) * | 1983-11-02 | 1985-06-03 | Toagosei Chem Ind Co Ltd | Curable composition |
| JPS6268862A (en) * | 1985-09-19 | 1987-03-28 | Toyo Ink Mfg Co Ltd | Coating composition curable with actinic radiation |
-
1989
- 1989-07-13 JP JP1181489A patent/JPH0347185A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4930465A (en) * | 1972-06-16 | 1974-03-18 | ||
| JPS6099181A (en) * | 1983-11-02 | 1985-06-03 | Toagosei Chem Ind Co Ltd | Curable composition |
| JPS6268862A (en) * | 1985-09-19 | 1987-03-28 | Toyo Ink Mfg Co Ltd | Coating composition curable with actinic radiation |
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