DE2120516A1 - Verfahren zum Härten von Polyepoxiden - Google Patents
Verfahren zum Härten von PolyepoxidenInfo
- Publication number
- DE2120516A1 DE2120516A1 DE19712120516 DE2120516A DE2120516A1 DE 2120516 A1 DE2120516 A1 DE 2120516A1 DE 19712120516 DE19712120516 DE 19712120516 DE 2120516 A DE2120516 A DE 2120516A DE 2120516 A1 DE2120516 A1 DE 2120516A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolidine
- anhydride
- glycidyl ether
- curing
- adduct
- 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
- 229920000647 polyepoxide Polymers 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000499 gel Substances 0.000 description 8
- -1 epoxide compounds Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000003213 activating effect Effects 0.000 description 4
- 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 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- DWZBSOVYCROKJR-UHFFFAOYSA-N 4-(2-methylphenyl)butan-1-ol Chemical compound CC1=CC=CC=C1CCCCO DWZBSOVYCROKJR-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 1
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical compound CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000428199 Mustelinae Species 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000019589 hardness Nutrition 0.000 description 1
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- JKXONPYJVWEAEL-UHFFFAOYSA-N oxiran-2-ylmethyl acetate Chemical compound CC(=O)OCC1CO1 JKXONPYJVWEAEL-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- PTLZMJYQEBOHHM-UHFFFAOYSA-N oxiran-2-ylmethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC1CO1 PTLZMJYQEBOHHM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- QZRSVBDWRWTHMT-UHFFFAOYSA-M silver;3-carboxy-3,5-dihydroxy-5-oxopentanoate Chemical compound [Ag+].OC(=O)CC(O)(C([O-])=O)CC(O)=O QZRSVBDWRWTHMT-UHFFFAOYSA-M 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120516 DE2120516A1 (de) | 1971-04-27 | 1971-04-27 | Verfahren zum Härten von Polyepoxiden |
| IT2335072A IT955167B (it) | 1971-04-27 | 1972-04-19 | Procedimento per indurire poliepossidi |
| GB1909372A GB1359089A (en) | 1971-04-27 | 1972-04-25 | Process for curing polyepoxides |
| FR7214826A FR2134536A1 (enExample) | 1971-04-27 | 1972-04-26 | |
| AT366972A AT320286B (de) | 1971-04-27 | 1972-04-26 | Verfahren zum Härten von Polyepoxyden |
| BE782740A BE782740A (fr) | 1971-04-27 | 1972-04-27 | Procede perfectionne pour durcir des polyepoxydes |
| NL7205759A NL7205759A (enExample) | 1971-04-27 | 1972-04-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120516 DE2120516A1 (de) | 1971-04-27 | 1971-04-27 | Verfahren zum Härten von Polyepoxiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2120516A1 true DE2120516A1 (de) | 1972-11-02 |
Family
ID=5806033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120516 Pending DE2120516A1 (de) | 1971-04-27 | 1971-04-27 | Verfahren zum Härten von Polyepoxiden |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT320286B (enExample) |
| BE (1) | BE782740A (enExample) |
| DE (1) | DE2120516A1 (enExample) |
| FR (1) | FR2134536A1 (enExample) |
| GB (1) | GB1359089A (enExample) |
| IT (1) | IT955167B (enExample) |
| NL (1) | NL7205759A (enExample) |
-
1971
- 1971-04-27 DE DE19712120516 patent/DE2120516A1/de active Pending
-
1972
- 1972-04-19 IT IT2335072A patent/IT955167B/it active
- 1972-04-25 GB GB1909372A patent/GB1359089A/en not_active Expired
- 1972-04-26 AT AT366972A patent/AT320286B/de active
- 1972-04-26 FR FR7214826A patent/FR2134536A1/fr not_active Withdrawn
- 1972-04-27 BE BE782740A patent/BE782740A/xx unknown
- 1972-04-27 NL NL7205759A patent/NL7205759A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1359089A (en) | 1974-07-10 |
| FR2134536A1 (enExample) | 1972-12-08 |
| IT955167B (it) | 1973-09-29 |
| NL7205759A (enExample) | 1972-10-31 |
| AT320286B (de) | 1975-02-10 |
| BE782740A (fr) | 1972-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2211469C3 (de) | Verfahren zur Herstellung eines Epoxyharz-Härtungsmittels und Verwendung des so hergestellten Mittels | |
| EP0000605A1 (de) | Härtungsmittel für wässerige Epoxydharzdispersionen, deren Herstellung und Verwendung | |
| DE2846123A1 (de) | Verfahren zur herstellung gehaerteter formkoerper auf basis von epoxidharzen und harz-haerter-zusammensetzungen | |
| DE2059329A1 (de) | Lagerbestaendige Epoxyharzmasse | |
| DE1520862B2 (de) | Verfahren zur herstellung von formkoerpern | |
| DE1106071B (de) | Verfahren zum Haerten von Polyepoxyden | |
| DE2139290A1 (de) | Hartbare Epoxidharzzusammensetzungen | |
| DE1283420B (de) | Thixotrope UEberzugsmittel | |
| DE1906515A1 (de) | Haertbare Mischungen aus Epoxidharzen und cyclischen Harnstoffderivaten | |
| DE2732816A1 (de) | Kunstharz auf polyepoxid-grundlage und verfahren zu seiner herstellung | |
| DE1808670A1 (de) | Haertbare Mischungen aus Epoxidharzen,Dicyandiamid und Aminbeschleunigern | |
| DE1954466A1 (de) | Haertbare Mischungen aus Epoxidharzen und zwei heterocyclische Kerne enthaltenden diprimaeren Diaminen | |
| DE2120516A1 (de) | Verfahren zum Härten von Polyepoxiden | |
| DE1770832A1 (de) | Verfahren zur Herstellung von Formkoerpern und UEberzuegen aus Polyepoxid-Mischungen | |
| EP0176484A2 (de) | Diäthylphenyl-biguanid enthaltende härtbare Gemische und deren Verwendung | |
| DE2122955A1 (de) | Verfahren zum Härten von Epoxidharzen | |
| DE3610757C2 (enExample) | ||
| DE2949401A1 (de) | Produkte aus einem polyepoxid und zweikernigen hydantoinverbindungen | |
| DE2640410A1 (de) | Lagerstabile, pulverfoermige ueberzugsmittel | |
| DE2126478A1 (de) | Neue härtbare Epoxidharzmischungen | |
| DE3616708C2 (enExample) | ||
| DE2166606C3 (de) | Heißhärtbare, feste Epoxidharzmassen | |
| DE1804364A1 (de) | Verfahren zum Haerten von Epoxyverbindungen | |
| DE2024395B2 (de) | Hartbare Mischungen aus Epoxidharz und Biguanid | |
| EP0643103B1 (de) | Härtbare Bindemittel |