JPH0563471B2 - - Google Patents
Info
- Publication number
- JPH0563471B2 JPH0563471B2 JP61174444A JP17444486A JPH0563471B2 JP H0563471 B2 JPH0563471 B2 JP H0563471B2 JP 61174444 A JP61174444 A JP 61174444A JP 17444486 A JP17444486 A JP 17444486A JP H0563471 B2 JPH0563471 B2 JP H0563471B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- urea
- compound
- methylimidazole
- amz
- 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 - Lifetime
Links
- -1 2-methylimidazolyl-ethyl group Chemical group 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- QKVROWZQJVDFSO-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)ethanamine Chemical compound CC1=NC=CN1CCN QKVROWZQJVDFSO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 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
- 239000013078 crystal Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- DKCWQRKXTQSULZ-UHFFFAOYSA-N 1h-imidazole;urea Chemical class NC(N)=O.C1=CNC=N1 DKCWQRKXTQSULZ-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IRHQJXPLAMGGSU-UHFFFAOYSA-N n-[1-(2-methyl-1h-imidazol-5-yl)ethyl]acetamide Chemical compound CC(=O)NC(C)C1=CN=C(C)N1 IRHQJXPLAMGGSU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
産業上の利用分野
本発明は新規なイミダゾール尿素化合物、該化
合物の合成方法および該化合物を有効成分とする
ポリエポキシ樹脂硬化剤に関するものである。
本発明によつてえられる化合物は新規物質であ
り、しかもポリエポキシ樹脂の硬化剤として利用
されるものである。
発明が解決しようとする問題点
ポリエポキシ樹脂の硬化剤として各種のイミダ
ゾール化合物が今日使用されている。中でも、中
温速硬化性を有し、かつ高熱変形温度を有する硬
化物を与えると云う長所を有する理由で２−メチ
ルイミダゾール、２−エチル−４−メチルイミダ
ゾールあるいは２−フエニルイミダゾール等が多
用されている。しかしこれらのイミダゾールを硬
化剤として配合したポリエポキシ樹脂のポツトラ
イフは残念ながら室温で僅か１日以内と甚だ短
い。
本発明者等は、ポツトライフの短いことを欠点
と考え、前述の長所を損なうことなくポツトライ
フの延長をしようとするものである。
問題点を解決するための手段
本発明者等は、鋭意研究の結果、１−アミノエ
チル−２−メチルイミダゾールと尿素または炭酸
ガスからえられるある種のイミダゾール尿素化合
物がポリエポキシ樹脂に対する硬化剤として速硬
化性と比較的長いポツトライフを示すことを見い
出し、このものの提供により前記の問題点を解決
することが出来た。
以下、順を追つて問題点解決のための手段につ
いて説明する。
先ずイミダゾール尿素化合物の出発物質となる
１−アミノエチル−イミダゾール化合物の合成方
法について述べる。
ジエチレントリアミンと酢酸を加熱し、縮合反
応により生成する水を系外に留去することにより
１−アセチルアミノエチル−２−メチルイミダゾ
リンがえられる。次いで、このものをニツケル触
媒下で加熱して脱水素することにより、１−アセ
チルアミノエチル−２−メチルイミダゾールがえ
られる。ついで、このものを苛性アルカリと水で
加水分解してアセチル基をはずすと１−アミノエ
チル−２−メチルイミダゾールがえられる（特願
昭61−39723号参照）。
この１−アミノエチル−２−メチルイミダゾー
ル（以下AMZと略称する）と所定量の尿素また
は炭酸ガスを加熱することによりイミダゾール尿
素化合物がえられる。これらを反応式、、
及びにより説明すれば次の通りである。
INDUSTRIAL APPLICATION FIELD The present invention relates to a novel imidazole urea compound, a method for synthesizing the compound, and a polyepoxy resin curing agent containing the compound as an active ingredient. The compound obtained by the present invention is a new substance, and moreover, it can be used as a curing agent for polyepoxy resins. Problems to be Solved by the Invention Various imidazole compounds are used today as curing agents for polyepoxy resins. Among them, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, etc. are often used because they have the advantage of providing a cured product that has medium-temperature rapid curing properties and a high heat distortion temperature. ing. Unfortunately, however, the pot life of polyepoxy resins containing imidazole as a curing agent is extremely short, being only one day at room temperature. The inventors of the present invention consider the short pot life to be a drawback, and attempt to extend the pot life without sacrificing the above-mentioned advantages. Means for Solving the Problems As a result of intensive research, the present inventors have found that certain imidazole urea compounds obtained from 1-aminoethyl-2-methylimidazole and urea or carbon dioxide gas can be used as curing agents for polyepoxy resins. It has been found that this material exhibits fast curing properties and a relatively long pot life, and by providing this product, the above-mentioned problems can be solved. Hereinafter, means for solving the problems will be explained step by step. First, a method for synthesizing a 1-aminoethyl-imidazole compound, which is a starting material for an imidazole urea compound, will be described. 1-acetylaminoethyl-2-methylimidazoline is obtained by heating diethylenetriamine and acetic acid and distilling water produced by the condensation reaction out of the system. Next, this product is dehydrogenated by heating under a nickel catalyst to obtain 1-acetylaminoethyl-2-methylimidazole. This product is then hydrolyzed with caustic alkali and water to remove the acetyl group, yielding 1-aminoethyl-2-methylimidazole (see Japanese Patent Application No. 39723/1983). An imidazole urea compound can be obtained by heating this 1-aminoethyl-2-methylimidazole (hereinafter abbreviated as AMZ) and a predetermined amount of urea or carbon dioxide gas. These are the reaction formulas,
The explanation is as follows.
【表】【table】
【表】
次に前述の反応式、、及びで示される
各反応の態様について述べる。
反応式：等モルのAMZと尿素を気泡計を備え
た反応容器中内温120ないし130℃でNH3
発生のやむ迄、すなわち１時間加熱するこ
とにより内容物は固化する。冷却後、内容
物（モノ尿素体）を常法の再結晶法によつ
て精製する。
反応式：モル比２のAMZとモル比１の尿素を
気泡計を備えた反応容器中で内温165℃で
NH3発生のやむ迄、すなわち２時間加熱
したのち、系を冷却し、内容物（ビス尿素
体）を再結晶法によつて精製する。
反応式：等モルのモノ尿素体とAMZを気泡計
を備えた反応容器中で内温155ないし165℃
でNH3発生のやむ迄、すなわち１時間加
熱したのち、系を冷却し、内容物（ビス尿
素体）を再結晶法によつて精製する。
反応式：オートクレーブ中でAMZと過剰の炭
酸ガスを250℃で２時間加熱したのち、系
を冷却し、内容物（ビス尿素体）を再結晶
法によつて精製する。
次に本発明の方法によつてえられる各目的物の
性質を示す。
２−メチルイミダゾリル−１−エチル尿素（モリ
尿素体）
構造式
融点172〜174℃（エタノール）。水及びメタノ
ールに易溶、エタノールに可溶。TLC（シリカ
Ｇ／EtOH，I2発色）：Rf0.24〜0.37
νKBr
cm-1：3370（21），3080（（41），2960（49），2910
（50）1670（24），1593（28），1560（20），
1525（50）1500（48），1468（60），1445（54），
1426（38）1382（58），1364（38），1350（40），
1278（35）1235（68），1150（48），1140（50），
1115（65）1078（54），1058（67），986（59），
935（74）920（75），850（73），775（73），738
（38）670（45）
但しカツコ内は透過率％を示す。
NMR（D2O）：δ7.00，Ｓ，1H；6.86，Ｓ，1H；
4.00，ｔ（Ｊ＝６Hz），2H；3.40，ｔ（Ｊ＝
６Hz），2H；2.31，Ｓ，3H
Mass：ｍ／e168（M+），124（AMZ−１），108
（AMZ−NH2−２），96，95，87，83，
81，68，55，45，43
ビス−（２−メチルイミダゾリル−１−エチル）
尿素（ビス尿素体）
構造式
融点182〜185℃（水）。塩基性の無色針状結晶
水に可溶、メタノールおよびエタノールに易溶。
TLC（シリカＧ，MeOH，I2）：Rr0.13〜0.25
νKBr
cm-1：3360（20），3150（29），3000（40），2960
（43）2930（43），2260（66），1623（23），
1566（24）1525（37），1494（33），1465（47），
1445（40）1426（35），1368（42），1354（38），
1278（29）1260（36），1235（45），1177（57），
1155（46）1138（40），1090（56），1062（54），
1033（55）983（50），934（65），915（66），
765（46）740（34），662（37）あ
NMR（CD3OD）：δ6.94，ｄ（Ｊ＝２Hz），2H；
6.79，ｄ（Ｊ＝２Hz），2H；3.97，ｔ（Ｊ＝
６Hz），4H；3.34，ｔ（Ｊ＝６Hz），4H；
2.31，Ｓ，6H
Mass：ｍ／e276（M+），194，181，152，151，
125，109，108，96，95，82，80，68，54，
41
発明の効果
次に、本発明の方法によつてえられるモノおよ
びビス尿素体のエポキシ樹脂〔商品名「エピコー
ト828」（油化シエルエポキシ製）〕に対する150℃
の硬化時間とポツトライフを２−メチルイミダゾ
ール、２−エチル−４−メチルイミダゾールおよ
び２−フエニルイミダゾールのそれらと対比して
表示する。[Table] Next, the embodiments of each reaction represented by the above-mentioned reaction formula, and are described. Reaction formula: equimolar amounts of AMZ and urea are mixed into NH 3 at an internal temperature of 120 to 130°C in a reaction vessel equipped with a bubble meter.
The contents solidify by heating until the generation stops, that is, for one hour. After cooling, the contents (monourea compound) are purified by a conventional recrystallization method. Reaction formula: AMZ with a molar ratio of 2 and urea with a molar ratio of 1 are mixed at an internal temperature of 165°C in a reaction vessel equipped with a bubble meter.
After heating until NH 3 generation stops, that is, for 2 hours, the system is cooled and the contents (bisurea compound) are purified by a recrystallization method. Reaction formula: Equal moles of monourea and AMZ are placed in a reaction vessel equipped with a bubble meter at an internal temperature of 155 to 165℃.
After heating for 1 hour until NH 3 generation stops, the system is cooled and the contents (bisurea compound) are purified by recrystallization. Reaction formula: After heating AMZ and excess carbon dioxide gas at 250°C for 2 hours in an autoclave, the system is cooled and the contents (bisurea compound) are purified by recrystallization. Next, the properties of each object obtained by the method of the present invention will be shown. 2-Methylimidazolyl-1-ethylurea (molyurea) Structural formula Melting point 172-174℃ (ethanol). Easily soluble in water and methanol, soluble in ethanol. TLC (Silica G/EtOH, I 2 color development): Rf0.24-0.37 νKBr cm -1 : 3370 (21), 3080 ((41), 2960 (49), 2910
(50) 1670 (24), 1593 (28), 1560 (20),
1525 (50) 1500 (48), 1468 (60), 1445 (54),
1426 (38) 1382 (58), 1364 (38), 1350 (40),
1278 (35) 1235 (68), 1150 (48), 1140 (50),
1115 (65) 1078 (54), 1058 (67), 986 (59),
935 (74) 920 (75), 850 (73), 775 (73), 738
(38) 670 (45) However, the inside of the cutout indicates transmittance %. NMR (D 2 O): δ7.00, S, 1H; 6.86, S, 1H;
4.00, t (J = 6Hz), 2H; 3.40, t (J =
6Hz), 2H; 2.31, S, 3H Mass: m/e168 (M + ), 124 (AMZ-1), 108
(AMZ−NH 2 −2), 96, 95, 87, 83,
81,68,55,45,43 Bis-(2-methylimidazolyl-1-ethyl)
Urea (bisurea) structural formula Melting point 182-185℃ (water). Basic colorless needle crystals Soluble in water, easily soluble in methanol and ethanol. TLC (Silica G, MeOH, I 2 ): Rr0.13-0.25 νKBr cm -1 : 3360 (20), 3150 (29), 3000 (40), 2960
(43) 2930 (43), 2260 (66), 1623 (23),
1566 (24) 1525 (37), 1494 (33), 1465 (47),
1445 (40) 1426 (35), 1368 (42), 1354 (38),
1278 (29) 1260 (36), 1235 (45), 1177 (57),
1155 (46) 1138 (40), 1090 (56), 1062 (54),
1033 (55) 983 (50), 934 (65), 915 (66),
765 (46) 740 (34), 662 (37) A NMR (CD 3 OD): δ6.94, d (J = 2 Hz), 2H;
6.79, d (J = 2Hz), 2H; 3.97, t (J =
6Hz), 4H; 3.34, t (J=6Hz), 4H;
2.31, S, 6H Mass: m/e276 (M + ), 194, 181, 152, 151,
125, 109, 108, 96, 95, 82, 80, 68, 54,
41 Effects of the Invention Next, the mono- and bi-urea epoxy resin obtained by the method of the present invention [trade name "Epicote 828" (manufactured by Yuka Ciel Epoxy)] was tested at 150°C.
The cure times and pot lives of 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole are shown in comparison with those of 2-methylimidazole, 2-ethyl-4-methylimidazole and 2-phenylimidazole.
【表】【table】
【表】
実施例 １
AMZ0.08モル（10.0ｇ）および尿素0.08モル
（4.8ｇ）の２者からなる系に気泡計を付し、内温
120〜130℃でNH3ガスの発生がやむ迄、すなわ
ち１時間加熱した。NH3ガス発生終了の間際に
系内は固化した。冷却後、内容物をエタノールで
再結晶してm.P.170〜172℃の粗目的物モノ尿素
体0.047モル（7.9ｇ、収率59モル％）をえた。
実施例 ２
AMZ0.04モル（5.0ｇ）および尿素0.02モル
（1.2ｇ）の２者よりなる系に気泡計を付し、内温
165℃で２時間加熱した。この間NH3ガスの連続
発生が認められた。NH3ガス発生終了後、系を
放冷し、析出結晶を水で再結晶し、粗目的物ビス
尿素体0.0145モル（4.0ｇ、収率73モル％）をえ
た。
実施例 ３
モノ尿素体0.023モル（4.0ｇ）および
AMZ0.023モル（2.9ｇ）の２者からなる系を内温
155〜165℃でNH3ガス発生のやむ迄、すなわち
１時間加熱したのち、内容物を水で３回再結晶
し、目的物ビス尿素体（m.P.182〜185℃）0.016
モル（4.5ｇ、収率69.5モル％）をえた。
実施例 ４
AMZ1.0モル（125ｇ）および固形炭酸0.11モル
（50ｇ）を手早く330mlオートクレーブに封入し、
250℃で２時間振盪加熱した。最高ゲージ圧100気
圧が観察された。オートクレーブを放冷したの
ち、内容物を取出し、エタノールで再結晶して
m.P.168〜172℃の粗目的物モノ尿素体0.6モル
（101ｇ、収率60モル％）をえた。
実施例 ５
エピコート828（ビスフエノールＡのジグリシジ
ルエーテル型エポキシ樹脂、油化シエルエポキシ
製）の100重量部に対しモノ尿素体あるいはビス
尿素体を４重量部配合し、各配合物を75℃で２時
間加熱硬化させ、ついで150℃で４時間ポスト硬
化させた硬化物の性質を次示する。[Table] Example 1 A bubble meter was attached to a system consisting of 0.08 mol (10.0 g) of AMZ and 0.08 mol (4.8 g) of urea, and the internal temperature was measured.
The mixture was heated at 120 to 130° C. until the generation of NH 3 gas stopped, that is, for 1 hour. The inside of the system solidified just before the end of NH 3 gas generation. After cooling, the contents were recrystallized with ethanol to obtain 0.047 mol (7.9 g, yield 59 mol %) of a crude monourea compound having an mP of 170 to 172°C. Example 2 A bubble meter was attached to a system consisting of 0.04 mol (5.0 g) of AMZ and 0.02 mol (1.2 g) of urea, and the internal temperature was measured.
Heated at 165°C for 2 hours. During this period, continuous generation of NH 3 gas was observed. After the generation of NH 3 gas was completed, the system was allowed to cool, and the precipitated crystals were recrystallized with water to obtain 0.0145 mol (4.0 g, yield 73 mol %) of the crude target bis-urea compound. Example 3 0.023 mol (4.0 g) of monourea compound and
A system consisting of 0.023 mol (2.9 g) of AMZ is heated internally.
After heating at 155-165℃ until NH 3 gas generation stops, that is, for 1 hour, the contents are recrystallized with water three times to obtain the target bisurea compound (mP 182-185℃) 0.016
mol (4.5 g, yield 69.5 mol%). Example 4 1.0 mol (125 g) of AMZ and 0.11 mol (50 g) of solid carbonic acid were quickly sealed in a 330 ml autoclave.
It was heated with shaking at 250°C for 2 hours. A maximum gauge pressure of 100 atmospheres was observed. After cooling the autoclave, take out the contents and recrystallize with ethanol.
0.6 mol (101 g, yield 60 mol%) of the crude target monourea compound with mP of 168-172°C was obtained. Example 5 4 parts by weight of monourea or bis-urea were added to 100 parts by weight of Epicote 828 (diglycidyl ether type epoxy resin of bisphenol A, manufactured by Yuka Shell Epoxy), and each mixture was heated at 75°C. The properties of the cured product, which was heat-cured for 2 hours and then post-cured at 150°C for 4 hours, are shown below.
【表】【table】
Claims (1)
ゾリル−エチル基を表わす。〕 で示されるイミダゾール尿素化合物。 ２ 式 で示される１−β−アミノエチル−２−メチルイ
ミダゾールと尿素を加熱することを特徴とする特
許請求の範囲１に記載のイミダゾール尿素化合物
の合成方法。 ３ 一般式 〔式中、Ｒは前記のとおりである。〕 で示されるイミダゾール尿素化合物を有効成分と
するポリエポキシ樹脂硬化剤。[Claims] 1. General formula [In the formula, R represents a hydrogen atom or a 2-methylimidazolyl-ethyl group. ] An imidazole urea compound represented by 2 formulas The method for synthesizing an imidazole urea compound according to claim 1, which comprises heating 1-β-aminoethyl-2-methylimidazole and urea. 3 General formula [In the formula, R is as described above. ] A polyepoxy resin curing agent containing an imidazole urea compound shown as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61174444A JPS6330471A (en) | 1986-07-23 | 1986-07-23 | Novel imidazoleurea compound, synthesis thereof and curing method for polyepoxy resin using said compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61174444A JPS6330471A (en) | 1986-07-23 | 1986-07-23 | Novel imidazoleurea compound, synthesis thereof and curing method for polyepoxy resin using said compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6330471A JPS6330471A (en) | 1988-02-09 |
| JPH0563471B2 true JPH0563471B2 (en) | 1993-09-10 |
Family
ID=15978610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61174444A Granted JPS6330471A (en) | 1986-07-23 | 1986-07-23 | Novel imidazoleurea compound, synthesis thereof and curing method for polyepoxy resin using said compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6330471A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH036214A (en) * | 1989-06-02 | 1991-01-11 | Shin Etsu Chem Co Ltd | Epoxy resin composition for semiconductor sealing and semiconductor device |
| JP2010180162A (en) * | 2009-02-05 | 2010-08-19 | Asahi Kasei E-Materials Corp | Imidazole compound composition of micropowder shape, and epoxy resin composition |
| JP2011207854A (en) * | 2010-03-30 | 2011-10-20 | Asahi Kasei E-Materials Corp | Imidazole compound and hardening epoxy resin composition containing the same |
| EP3135709B1 (en) * | 2015-08-31 | 2018-01-10 | ATOTECH Deutschland GmbH | Imidazoyl urea polymers and their use in metal or metal alloy plating bath compositions |
| CN106432085A (en) * | 2016-10-08 | 2017-02-22 | 中国石油大学(华东) | Carbamido contained bis-imidazoline corrosion inhibitor and preparation method thereof |
| CN110698405A (en) * | 2019-11-01 | 2020-01-17 | 长春铭孚水处理技术有限公司 | Preparation method of novel imidazoline alkylguanidine corrosion inhibition bactericide |
-
1986
- 1986-07-23 JP JP61174444A patent/JPS6330471A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6330471A (en) | 1988-02-09 |
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