JPS6084283A - ２，４―ジアミノ―６―〔（２´―フエニルイミダゾリル）―エチル〕―ｓ―トリアジン並びにその製法並びにそれを用いるポリエポキシ硬化法 - Google Patents
２，４―ジアミノ―６―〔（２´―フエニルイミダゾリル）―エチル〕―ｓ―トリアジン並びにその製法並びにそれを用いるポリエポキシ硬化法Info
- Publication number
- JPS6084283A JPS6084283A JP19274483A JP19274483A JPS6084283A JP S6084283 A JPS6084283 A JP S6084283A JP 19274483 A JP19274483 A JP 19274483A JP 19274483 A JP19274483 A JP 19274483A JP S6084283 A JPS6084283 A JP S6084283A
- Authority
- JP
- Japan
- Prior art keywords
- diamino
- ethyl
- triazine
- phenylimidazolyl
- formula
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 229920000647 polyepoxide Polymers 0.000 title abstract description 3
- 238000000034 method Methods 0.000 title description 6
- ZJECWRIHDKPJLJ-UHFFFAOYSA-N 4-(2-aminoethyl)-6-(2-phenyl-1H-imidazol-5-yl)-1,3,5-triazin-2-amine Chemical compound NCCC1=NC(=NC(=N1)N)C=1N=C(NC1)C1=CC=CC=C1 ZJECWRIHDKPJLJ-UHFFFAOYSA-N 0.000 title 1
- 238000007259 addition reaction Methods 0.000 claims abstract description 6
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001723 curing Methods 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 abstract description 2
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 240000005109 Cryptomeria japonica Species 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- -1 phenylimidazolyl Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940079101 sodium sulfide Drugs 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274483A JPS6084283A (ja) | 1983-10-14 | 1983-10-14 | ２，４―ジアミノ―６―〔（２´―フエニルイミダゾリル）―エチル〕―ｓ―トリアジン並びにその製法並びにそれを用いるポリエポキシ硬化法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19274483A JPS6084283A (ja) | 1983-10-14 | 1983-10-14 | ２，４―ジアミノ―６―〔（２´―フエニルイミダゾリル）―エチル〕―ｓ―トリアジン並びにその製法並びにそれを用いるポリエポキシ硬化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6084283A true JPS6084283A (ja) | 1985-05-13 |
| JPH0160470B2 JPH0160470B2 (enrdf_load_stackoverflow) | 1989-12-22 |
Family
ID=16296332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19274483A Granted JPS6084283A (ja) | 1983-10-14 | 1983-10-14 | ２，４―ジアミノ―６―〔（２´―フエニルイミダゾリル）―エチル〕―ｓ―トリアジン並びにその製法並びにそれを用いるポリエポキシ硬化法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6084283A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391681A (en) * | 1992-06-05 | 1995-02-21 | Ciba-Geigy Corporation | Curable compositions based on epoxy resins or mixtures of epoxy resins and polyisocyanates containing trisimidazolyl triazines |
| JP2017100984A (ja) * | 2015-12-01 | 2017-06-08 | 四国化成工業株式会社 | イミダゾール化合物、エポキシ樹脂の硬化剤およびエポキシ樹脂組成物 |
-
1983
- 1983-10-14 JP JP19274483A patent/JPS6084283A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391681A (en) * | 1992-06-05 | 1995-02-21 | Ciba-Geigy Corporation | Curable compositions based on epoxy resins or mixtures of epoxy resins and polyisocyanates containing trisimidazolyl triazines |
| JP2017100984A (ja) * | 2015-12-01 | 2017-06-08 | 四国化成工業株式会社 | イミダゾール化合物、エポキシ樹脂の硬化剤およびエポキシ樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0160470B2 (enrdf_load_stackoverflow) | 1989-12-22 |
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