JPH0692390B2 - 4 (5)-(2 ▲ '▼, 4 ▲' ▼ -diamino-s-triazinyl-6 ▲ '▼) -imidazole compound and its synthesis method, and epoxy resin curing method - Google Patents
4 (5)-(2 ▲ '▼, 4 ▲' ▼ -diamino-s-triazinyl-6 ▲ '▼) -imidazole compound and its synthesis method, and epoxy resin curing methodInfo
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- JPH0692390B2 JPH0692390B2 JP8472690A JP8472690A JPH0692390B2 JP H0692390 B2 JPH0692390 B2 JP H0692390B2 JP 8472690 A JP8472690 A JP 8472690A JP 8472690 A JP8472690 A JP 8472690A JP H0692390 B2 JPH0692390 B2 JP H0692390B2
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- triazinyl
- diamino
- methanol
- epoxy resin
- imidazole
- Prior art date
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は新規な４（５）−（２′,4′−ジアミノ−ｓ−
トリアジニル−６′）−イミダゾール化合物及びその合
成方法に関するものである。The present invention relates to a novel 4 (5)-(2 ', 4'-diamino-s-
TECHNICAL FIELD The present invention relates to a triazinyl-6 ′)-imidazole compound and a method for synthesizing the same.
本発明化合物は、エポキシ樹脂の硬化剤あるいは硬化促
進剤として使用される。また本発明化合物は生物活性を
期待できる化学構造を有しているので、医薬あるいは農
薬分野において有望なものと考えられる。The compound of the present invention is used as a curing agent or curing accelerator for epoxy resins. Further, since the compound of the present invention has a chemical structure capable of expecting biological activity, it is considered to be promising in the fields of medicine or agrochemicals.
発明が解決しようとする課題 今日、各種のイミダゾール化合物がエポキシ樹脂の硬化
剤あるいは硬化促進剤として使用されている。また一方
では、トリアジン化合物の一種であるメラミンもエポキ
シ樹脂の良好な硬化剤として使用されているが、このも
のは硬化時間が長い欠点がある。Problems to be Solved by the Invention Today, various imidazole compounds are used as curing agents or curing accelerators for epoxy resins. On the other hand, melamine, which is one of the triazine compounds, is also used as a good curing agent for epoxy resins, but this has the drawback that the curing time is long.
この発明の主たる目的は、イミダゾール環及びトリアジ
ン環を直接結合させることにより、両者の特性を併せも
った新規な硬化剤あるいは硬化促進剤を提供することに
ある。A main object of the present invention is to provide a novel curing agent or curing accelerator having both properties by directly bonding the imidazole ring and the triazine ring.
課題を解決するための手段 本発明者等は、このような事情に鑑み鋭意研究を重ねた
結果、４（５）−シアノイミダゾール化合物及びジシア
ンジアミドを、ジメチルスルフォキシド（DMSO）等の溶
媒中で苛性アルカリの共存下に加熱し、反応生成物を常
法に従って精製することにより４（５）−（２′,4′−
ジアミノ−ｓ−トリアジニル−６′）−イミダゾール化
合物が得られることを見い出し、本発明を完遂するに至
った。本発明の実施におて原料として用いられる４
（５）−シアノイミダゾール化合物は、イミダゾール−
ジチオカルボン酸とアンモニアとの反応により得られる
チオカルバモイルイミダゾール化合物を、脱硫化水素さ
せることによって容易に得られる。（特願平1-339100号
明細書参照） ４（５）−シアノ−イミダゾール化合物及びジシアンジ
アミドの反応を式で示せば次のとおりである。Means for Solving the Problems As a result of intensive studies conducted by the present inventors in view of such circumstances, the 4 (5) -cyanoimidazole compound and dicyandiamide were dissolved in a solvent such as dimethylsulfoxide (DMSO). By heating in the presence of caustic and purifying the reaction product according to a conventional method, 4 (5)-(2 ', 4'-
It was found that a diamino-s-triazinyl-6 ')-imidazole compound was obtained, and the present invention was completed. Used as a raw material in the practice of the present invention 4
The (5) -cyanoimidazole compound is an imidazole-
The thiocarbamoylimidazole compound obtained by the reaction of dithiocarboxylic acid and ammonia can be easily obtained by dehydrosulfurization. (See Japanese Patent Application No. 1-339100) The reaction of the 4 (5) -cyano-imidazole compound and dicyandiamide can be represented by the following formula.
本発明の４（５）−（２′,4′−ジアミノ−ｓ−トリア
ジニル−６′）−イミダゾール化合物の性質は次に示す
とおりである。 The properties of the 4 (5)-(2 ', 4'-diamino-s-triazinyl-6')-imidazole compound of the present invention are as follows.
４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−イミダゾール m.p.＞280℃（水）、塩基性無色結晶、水及びメタノー
ルに可溶、アセトンに難溶。4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-imidazole mp> 280 ° C (water), basic colorless crystals, soluble in water and methanol, sparingly soluble in acetone.
TLC（シリカ，メタノール，I2発色）:Rf0.55〜0.65 NMR（ＣD3OD）：δ7.79,s,1H（イミダゾール ２位）;
7.77,s,1H（イミダゾール ５位） Mass:m/e177（M+）,150（M+−Ｃ−NH）,108,94,93,68,6
6,43,28 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−メチルイミダゾール m.p.＞250℃（水）、弱塩基性無色結晶、熱水に可溶、
メタノール及びエタノールに難溶。TLC (silica, methanol, I 2 color development): Rf 0.55 to 0.65 NMR (CD 3 OD): δ 7.79, s, 1H (imidazole 2 position);
7.77, s, 1H (Imidazole 5th position) Mass: m / e177 (M + ), 150 (M + -C-NH), 108,94,93,68,6
6,43,28 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-2-Methylimidazole mp> 250 ° C (water), weakly basic colorless crystals, soluble in hot water,
Poorly soluble in methanol and ethanol.
TLC（シリカ，メタノール，I2発色）:Rf0.50〜0.60 NMR（DMSO−d6）：δ12.10,br.s,1H（イミダゾール １
位）;7.44,s,1H（５位）;6.57,s,4H（ＮH2）;2.31,s,3H
（メチル） Mass:m/e192（M+＋１）,191（M+）,190,150,108〜106,8
4,80,68,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−エチルイミダゾール m.p.285〜288℃（水）、弱塩基性無色結晶、水及びメタ
ノールに可溶、アセトンに難溶。TLC (silica, methanol, I 2 color development): Rf 0.50 to 0.60 NMR (DMSO-d 6 ): δ12.10, br.s, 1H (imidazole 1
); 7.44, s, 1H (5th); 6.57, s, 4H (NH 2 ); 2.31, s, 3H
(Methyl) Mass: m / e192 (M + +1), 191 (M + ), 190,150,108 to 106,8
4,80,68,43 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-2-Ethylimidazole mp285-288 ° C (water), weakly basic colorless crystals, soluble in water and methanol, sparingly soluble in acetone.
TLC（シリカ，アセトン，I2発色）:Rf0.0〜0.10 NMR（ＣD3OD）：δ7.63,s,1H（５位）;2.78,q,2H（メチ
レン）;1.31,t,3H（メチル） Mass:m/e205（M+）,190（M+−NH）,120,106,68,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−ウンデシルイミダゾール m.p.158〜162℃（メタノール）、塩基性無色結晶、メタ
ノールに可溶、水に不溶。TLC (silica, acetone, I 2 color development): Rf0.0 to 0.10. NMR (CD 3 OD): δ7.63, s, 1H (5th position); 2.78, q, 2H (methylene); 1.31, t, 3H (methyl) Mass: m / e205 (M + ), 190 (M + -NH), 120,106,68,43 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-2-Undecylimidazole mp158-162 ° C (methanol), basic colorless crystals, soluble in methanol, insoluble in water.
TLC（シリカ，アセトン，I2発色）:Rf0.11〜0.28 NMR（DMSO−d6）：δ7.45,s,1H（５位）;6.53,s,4H（−
ＮH2）;2.62,t（Ｊ＝7Hz）,2H（α−メチレン）;1.63,b
r.s,2H（β−メチレン）;1.23,s,16H（中間メチレン）;
0.85,t（Ｊ＝6Hz）,3H（末端メチル） Mass:m/e331（M+）,246（M+−C6H13）,204（M+−C
9H19）,191（M+−C10H20）,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−ヘプタデシルイミダゾール m.p.160〜163℃（メタノール）、弱塩基性淡黄色結晶、
メタノール及びアセトンに可溶、水に難溶。TLC (silica, acetone, I 2 color development): Rf 0.11 to 0.28 NMR (DMSO-d 6): δ7.45, s, 1H (5 -position); 6.53, s, 4H ( -
NH 2); 2.62, t ( J = 7Hz), 2H (α- methylene); 1.63, b
rs, 2H (β-methylene); 1.23, s, 16H (intermediate methylene);
0.85, t (J = 6Hz) , 3H ( terminal methyl) Mass: m / e331 (M +), 246 (M + -C 6 H 13), 204 (M + -C
9 H 19 ), 191 (M + —C 10 H 20 ), 43 4 (5)-(2 ′, 4′-diamino-s-triazinyl-
6 ')-2-heptadecyl imidazole mp160-163 ° C (methanol), weakly basic pale yellow crystals,
Soluble in methanol and acetone, sparingly soluble in water.
TLC（シリカ，メタノール，I2発色）:Rf0.40〜0.55 NMR（ＣD3OD）：δ7.74〜7.62,d,1H（５位）;2.70,br.
s,2H（α−メチレン）;1.71,br.s,2H（β−メチレン）;
1.28,s,28H（中間メチレン）;0.89,t,3H（末端メチル） Mass:m/e415（M+）,246（M+−C12H25）,204（M+−C15H
31）,191（M+−C16H33）,107,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−フェニルイミダゾール m.p.305〜310℃（メタノール）、中性無色結晶、メタノ
ールに可溶、アセトンに難溶、水に不溶。TLC (silica, methanol, I 2 color development): Rf 0.40 to 0.55 NMR (CD 3 OD): δ 7.74 to 7.62, d, 1H (5th position); 2.70, br.
s, 2H (α-methylene); 1.71, br.s, 2H (β-methylene);
1.28, s, 28H (intermediate methylene); 0.89, t, 3H (terminal methyl) Mass: m / e 415 (M + ), 246 (M + −C 12 H 25 ), 204 (M + −C 15 H
31), 191 (M + -C 16 H 33), 107,43 4 (5) - (2 ', 4'- diamino -s- triazinyl -
6 ')-2-Phenylimidazole mp305-310 ℃ (methanol), neutral colorless crystals, soluble in methanol, sparingly soluble in acetone, insoluble in water.
TLC（シリカ，メタノール，I2発色）:Rf0.65〜0.75 NMR（DMSO−d6）：δ12.86,s,1H（１位）;8.14,d,2H
（フェニル）;7.80,d,1H（５位）;7.46,m,3H（フェニ
ル）;6.66,s,4H（−ＮH2） Mass:m/e253（M+）,210,169,150,104,99,43,31 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−５（４）−メチルイミダゾール m.p.285〜286℃（水）、塩基性無色結晶、熱水及びメタ
ノールに可溶。TLC (silica, methanol, I 2 color development): Rf 0.65 to 0.75 NMR (DMSO-d 6 ): δ 12.86, s, 1H (1st position); 8.14, d, 2H
(Phenyl); 7.80, d, 1H ( 5 -position); 7.46, m, 3H (phenyl); 6.66, s, 4H ( -NH 2) Mass: m / e253 (M +), 210,169,150,104,99,43,31 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-5 (4) -methylimidazole mp285-286 ℃ (water), basic colorless crystals, soluble in hot water and methanol.
TLC（シリカ，アセトン，I2発色）:Rf0.08〜0.20 NMR（ＣD3OD）：δ7.63,s,1H（２位）;2.61,s,3H（メチ
ル） Mass:m/e191（M+）,107,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−2,5（４）−ジメチルイミダゾール m.p.147〜149℃（水）、弱塩基性無色結晶、熱水に可
溶、メタノール及びアセトンに不溶。TLC (silica, acetone, I 2 color development): Rf 0.08 to 0.20 NMR (CD 3 OD): δ7.63, s, 1H (2nd position); 2.61, s, 3H (methyl) Mass: m / e191 (M + ), 107,43 4 (5)-(2 ', 4) ′ -Diamino-s-triazinyl-
6 ')-2,5 (4) -dimethylimidazole mp147-149 ° C (water), weakly basic colorless crystals, soluble in hot water, insoluble in methanol and acetone.
TLC（シリカ，アセトン，I2発色）:Rf0.00〜0.20 NMR（ＣD3OD）：δ2.54,s,3H（５位メチル）;2.35,s,3H
（２位メチル） Mass:m/e206（M+＋１）,205（M+）,204,154,137,122-12
0,111,97〜93,85,80,79,69,68,54〜52,43,42,28,26 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−エチル−５（４）−メチルイミダゾール m.p.55〜58℃（水）、弱塩基性無色結晶、水、メタノー
ル、エタノール及びアセトンに可溶、アセトニトリルに
難溶。TLC (silica, acetone, I 2 color development): Rf 0.00 to 0.20 NMR (CD 3 OD): δ2.54, s, 3H (5-methyl); 2.35, s, 3H
(2nd methyl) Mass: m / e206 (M + +1), 205 (M + ), 204,154,137,122-12
0,111,97 to 93,85,80,79,69,68,54 to 52,43,42,28,26 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-2-Ethyl-5 (4) -methylimidazole mp 55-58 ° C (water), weakly basic colorless crystals, soluble in water, methanol, ethanol and acetone, sparingly soluble in acetonitrile.
TLC（シリカ，アセトン，I2発色）:Rf0.10〜0.17 NMR（ＣD3OD）：δ2.70,q（Ｊ＝8Hz）,2H（α−メチレ
ン）;2.56,s,3H（４位メチル）;1.29,t（Ｊ＝8Hz）,3H
（２位メチル） Mass:m/e219（M+）,204（M+−ＣH3）,134,43 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−ウンデシル−５（４）−メチルイミダゾー
ル塩酸塩 m.p.230〜237℃（メタノール）、酸性無色結晶、 TLC（シリカ，メタノール，I2発色）:Rf0.60〜0.80 NMR（ＣD3OD）：δ3.01,t,2H（α−メチレン）;2.76,s,
3H（５位メチル）;1.82,m,2H（β−メチレン）;1.28,m,
16H（中間メチレン）;0.89,t,3H（末端メチル） Mass:m/e345（M+）,260（M+−C6H13）,218（M+−C
9H19）,205（M+−C10H20）,120,85,43,36 ４（５）−（２′,4′−ジアミノ−ｓ−トリアジニル−
６′）−２−フェニル−５（４）−メチルイミダゾール m.p.165〜167℃（メタノール）、弱塩基性無色結晶、メ
タノール及びアセトンに難溶、水に不溶。TLC (silica, acetone, I 2 color development): Rf 0.10 to 0.17 NMR (CD 3 OD): δ 2.70, q (J = 8Hz), 2H (α-methylene); 2.56, s, 3H (4th methyl); 1.29, t (J = 8Hz), 3H
(Methyl 2-position) Mass: m / e 219 (M + ), 204 (M + -CH 3 ), 134,43 4 (5)-(2 ', 4'-diamino-s-triazinyl-
6 ')-2-Undecyl-5 (4) -methylimidazole hydrochloride mp230~237 ℃ (methanol), acidic colorless crystals, TLC (silica, methanol, I 2 color): Rf0.60～0.80 NMR (CD 3 OD): δ3.01, t, 2H (α-methylene); 2.76, s,
3H (methyl at 5-position); 1.82, m, 2H (β-methylene); 1.28, m,
16H (intermediate methylene); 0.89, t, 3H (terminal methyl) Mass: m / e 345 (M + ), 260 (M + −C 6 H 13 ), 218 (M + −C)
9 H 19), 205 (M + -C 10 H 20), 120,85,43,36 4 (5) - (2 ', 4'- diamino -s- triazinyl -
6 ')-2-Phenyl-5 (4) -methylimidazole mp165-167 ° C (methanol), weakly basic colorless crystals, sparingly soluble in methanol and acetone, insoluble in water.
TLC（シリカ，アセトン，I2発色）:Rf0.40〜0.55 NMR（DMSO−d6）：δ12.52,s,1H（１位）;8.10,s,1Hと
7.95,s,1Hと7.32〜7.44,m,3H（フェニル）;6.55,s,4H
（−ＮH2）;2.59,s,3H（５位メチル） Mass:m/e268（M+＋１）,267（M+）,266,183,164、122,1
04,89,77,69,68,43 実施例１〜11 表１に示した所定の各種シアノイミダゾール化合物0.1
モルを所定量のジシアンジアミド（DICY）及び苛性カリ
とともに、ジメチルスルフォキシド中で、同表に示す所
定条件下に反応させ、所定の後処理を行い、目的物を得
た。TLC (silica, acetone, I 2 color development): Rf 0.40 to 0.55 NMR (DMSO-d 6 ): δ 12.52, s, 1H (1st position); 8.10, s, 1H
7.95, s, 1H and 7.32 ~ 7.44, m, 3H (phenyl); 6.55, s, 4H
(-NH 2 ); 2.59, s, 3H (methyl at the 5th position) Mass: m / e 268 (M + +1), 267 (M + ), 266,183,164, 122,1
04,89,77,69,68,43 Examples 1 to 11 Various predetermined cyanoimidazole compounds shown in Table 1 0.1
A predetermined amount of dicyandiamide (DICY) and caustic potash were allowed to react with each other in dimethyl sulfoxide under the predetermined conditions shown in the same table, and a predetermined post-treatment was carried out to obtain the desired product.
その結果を表１に示すとおりである。The results are shown in Table 1.
実施例12〜13 エポキシ樹脂（旭化成工業（株）製、エピ−ビス型エポ
キシ樹脂、商品名:AER-331）100重量部に、充填剤とし
てシリカ粉末（電気化学工業（株）製、溶融シリカ、商
品名:DF-44）100重量部及び硬化剤として本発明化合物
５重量部を混合し、石川式攪拌ライ潰機（（株）石川製
作所製）を用いて60分間練り合わせて配合物を調製し
た。この配合物の熱硬化性（150℃におけるゲル化時
間）等の物性は表２に示すとおりである。 Examples 12 to 13 Epoxy resin (Asahi Kasei Co., Ltd., epi-bis type epoxy resin, trade name: AER-331) 100 parts by weight, silica powder as a filler (manufactured by Denki Kagaku Kogyo KK, fused silica) Product name: DF-44) 100 parts by weight and 5 parts by weight of the compound of the present invention as a curing agent are mixed, and the mixture is kneaded for 60 minutes using an Ishikawa type stirring rye crusher (manufactured by Ishikawa Seisakusho Co., Ltd.) to prepare a mixture. did. Physical properties such as thermosetting property (gelling time at 150 ° C.) of this compound are shown in Table 2.
なお、熱硬化は配合物を金属製型枠に流し込み、80℃の
温度で２時間予備硬化させたのち、150℃の温度で４時
間ポストキュアを行ったものである。In the thermosetting, the composition was poured into a metal mold, pre-cured at a temperature of 80 ° C. for 2 hours, and then post-cured at a temperature of 150 ° C. for 4 hours.
Claims (4)
アジニル−６′）−イミダゾール化合物。 1. A general formula 4 (5)-(2 ′, 4′-diamino-s-triazinyl-6 ′)-imidazole compound represented by
シアンジアミドを、苛性アルカリを含む溶媒中で加熱す
ることを特徴とする４（５）−（２′,4′−ジアミノ−
ｓ−トリアジニル−６′）−イミダゾール化合物の合成
方法。2. General formula [However, R 2 and R 4 are the same as above. ] The 4 (5) -cyanoimidazole compound and dicyandiamide represented by the formula (4) are heated in a solvent containing caustic alkali, and 4 (5)-(2 ', 4'-diamino-
Method for synthesizing s-triazinyl-6 ')-imidazole compounds.
ることを特徴とする請求項（２）に記載の方法。3. The method according to claim 2, wherein dimethyl sulfoxide is used as the solvent.
リアジニル−６′）−イミダゾール化合物を硬化剤ある
いは硬化促進剤として用いることを特徴とするエポキシ
樹脂の硬化方法。4. A method for curing an epoxy resin, which comprises using a 4 (5)-(2 ', 4'-diamino-s-triazinyl-6')-imidazole compound as a curing agent or a curing accelerator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8472690A JPH0692390B2 (en) | 1990-03-29 | 1990-03-29 | 4 (5)-(2 ▲ '▼, 4 ▲' ▼ -diamino-s-triazinyl-6 ▲ '▼) -imidazole compound and its synthesis method, and epoxy resin curing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8472690A JPH0692390B2 (en) | 1990-03-29 | 1990-03-29 | 4 (5)-(2 ▲ '▼, 4 ▲' ▼ -diamino-s-triazinyl-6 ▲ '▼) -imidazole compound and its synthesis method, and epoxy resin curing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03284675A JPH03284675A (en) | 1991-12-16 |
| JPH0692390B2 true JPH0692390B2 (en) | 1994-11-16 |
Family
ID=13838695
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|---|---|---|---|
| JP8472690A Expired - Fee Related JPH0692390B2 (en) | 1990-03-29 | 1990-03-29 | 4 (5)-(2 ▲ '▼, 4 ▲' ▼ -diamino-s-triazinyl-6 ▲ '▼) -imidazole compound and its synthesis method, and epoxy resin curing method |
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| Country | Link |
|---|---|
| JP (1) | JPH0692390B2 (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5085061B2 (en) | 2006-06-30 | 2012-11-28 | ポリプラスチックス株式会社 | Polyacetal resin composition |
| JP2008156504A (en) | 2006-12-25 | 2008-07-10 | Polyplastics Co | Polyacetal resin composition |
| JP5480471B2 (en) | 2007-12-26 | 2014-04-23 | ポリプラスチックス株式会社 | Polyacetal resin composition |
| DE102008018967A1 (en) | 2008-04-16 | 2009-10-22 | Ticona Gmbh | Oxymethylene polymers, process for their preparation and their use |
| CN108485175A (en) | 2010-10-14 | 2018-09-04 | 塞拉尼斯销售德国有限公司 | The polyformaldehyde of glass fiber reinforcement |
| US8840976B2 (en) | 2010-10-14 | 2014-09-23 | Ticona Llc | VOC or compressed gas containment device made from a polyoxymethylene polymer |
| MX344215B (en) | 2010-10-14 | 2016-12-07 | Celanese Sales Germany Gmbh | Coupled glass-fiber reinforced polyoxymethylene. |
| EP2581408B1 (en) | 2011-10-14 | 2015-07-29 | Ticona GmbH | Tribologically modified glass-fiber reinforced polyoxymethylene |
| US8968858B2 (en) | 2011-12-30 | 2015-03-03 | Ticona Llc | Printable molded articles made from a polyoxymethylene polymer composition |
| EP2647666A1 (en) | 2012-04-05 | 2013-10-09 | Ticona GmbH | Tribologically modified polyoxymethylene |
| EP2653497B1 (en) | 2012-04-17 | 2015-01-28 | Ticona GmbH | Weather resistant polyoxymethylene compositions |
| WO2014097270A1 (en) | 2012-12-20 | 2014-06-26 | Ticona Gmbh | Fiber reinforced polyoxymethylene composition with improved thermal properties |
| US9745467B2 (en) | 2012-12-27 | 2017-08-29 | Ticona, Llc | Impact modified polyoxymethylene composition and articles made therefrom that are stable when exposed to ultraviolet light |
| WO2015019777A1 (en) * | 2013-08-05 | 2015-02-12 | 三菱瓦斯化学株式会社 | Benzoguanamine compound having aminomethyl group or salt thereof, and method for producing same |
| EP3341439A1 (en) | 2015-09-30 | 2018-07-04 | Celanese Sales Germany GmbH | Low friction squeak free assembly |
| US11015031B2 (en) | 2017-06-16 | 2021-05-25 | Celanese Sales Germany Gmbh | Reinforced polyoxymethylene composition with low emissions |
-
1990
- 1990-03-29 JP JP8472690A patent/JPH0692390B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03284675A (en) | 1991-12-16 |
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