DE2264286C3 - Verwendung von 1,3,6,8-Tetraaza- tricyclo-4,4,11·6 .l3·8 - dodecan als Härter bei der Herstellung von Epoxidpolyaddukten - Google Patents
Verwendung von 1,3,6,8-Tetraaza- tricyclo-4,4,11·6 .l3·8 - dodecan als Härter bei der Herstellung von EpoxidpolyadduktenInfo
- Publication number
- DE2264286C3 DE2264286C3 DE19722264286 DE2264286A DE2264286C3 DE 2264286 C3 DE2264286 C3 DE 2264286C3 DE 19722264286 DE19722264286 DE 19722264286 DE 2264286 A DE2264286 A DE 2264286A DE 2264286 C3 DE2264286 C3 DE 2264286C3
- Authority
- DE
- Germany
- Prior art keywords
- epoxy
- ttc
- hardener
- dodecane
- mol
- 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
Links
- 239000004593 Epoxy Substances 0.000 title claims description 23
- 239000004848 polyfunctional curative Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 7
- 239000003607 modifier Substances 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 description 12
- 235000019589 hardness Nutrition 0.000 description 11
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 5
- 239000004312 hexamethylene tetramine Substances 0.000 description 5
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 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 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002991 molded plastic Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000003110 molding sand Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
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 (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722264286 DE2264286C3 (de) | 1972-12-30 | 1972-12-30 | Verwendung von 1,3,6,8-Tetraaza- tricyclo-4,4,11·6 .l3·8 - dodecan als Härter bei der Herstellung von Epoxidpolyaddukten |
| IT3141273A IT1001798B (it) | 1972-12-30 | 1973-11-16 | Procedimento per la fabbricazione di prodotti induriti a base di prodotti di poliaddizione di epossidi |
| NL7317200A NL7317200A (enrdf_load_html_response) | 1972-12-30 | 1973-12-14 | |
| JP462674A JPS4999699A (enrdf_load_html_response) | 1972-12-30 | 1973-12-26 | |
| GB5976373A GB1400350A (en) | 1972-12-30 | 1973-12-27 | Epoxide polyadducts |
| FR7346863A FR2212366B3 (enrdf_load_html_response) | 1972-12-30 | 1973-12-28 | |
| BE139383A BE809242A (fr) | 1972-12-30 | 1973-12-28 | Procede de preparation de produits durcis a base de polyepoxydes d'addition |
| US05/632,420 US4024109A (en) | 1972-12-30 | 1975-11-17 | Process for preparing cured epoxide polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722264286 DE2264286C3 (de) | 1972-12-30 | 1972-12-30 | Verwendung von 1,3,6,8-Tetraaza- tricyclo-4,4,11·6 .l3·8 - dodecan als Härter bei der Herstellung von Epoxidpolyaddukten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2264286A1 DE2264286A1 (de) | 1974-07-11 |
| DE2264286B2 DE2264286B2 (de) | 1978-05-18 |
| DE2264286C3 true DE2264286C3 (de) | 1979-01-04 |
Family
ID=5865857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722264286 Expired DE2264286C3 (de) | 1972-12-30 | 1972-12-30 | Verwendung von 1,3,6,8-Tetraaza- tricyclo-4,4,11·6 .l3·8 - dodecan als Härter bei der Herstellung von Epoxidpolyaddukten |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4999699A (enrdf_load_html_response) |
| BE (1) | BE809242A (enrdf_load_html_response) |
| DE (1) | DE2264286C3 (enrdf_load_html_response) |
| FR (1) | FR2212366B3 (enrdf_load_html_response) |
| GB (1) | GB1400350A (enrdf_load_html_response) |
| IT (1) | IT1001798B (enrdf_load_html_response) |
| NL (1) | NL7317200A (enrdf_load_html_response) |
-
1972
- 1972-12-30 DE DE19722264286 patent/DE2264286C3/de not_active Expired
-
1973
- 1973-11-16 IT IT3141273A patent/IT1001798B/it active
- 1973-12-14 NL NL7317200A patent/NL7317200A/xx not_active Application Discontinuation
- 1973-12-26 JP JP462674A patent/JPS4999699A/ja active Pending
- 1973-12-27 GB GB5976373A patent/GB1400350A/en not_active Expired
- 1973-12-28 FR FR7346863A patent/FR2212366B3/fr not_active Expired
- 1973-12-28 BE BE139383A patent/BE809242A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2212366A1 (enrdf_load_html_response) | 1974-07-26 |
| DE2264286A1 (de) | 1974-07-11 |
| NL7317200A (enrdf_load_html_response) | 1974-07-02 |
| GB1400350A (en) | 1975-07-16 |
| FR2212366B3 (enrdf_load_html_response) | 1976-10-22 |
| IT1001798B (it) | 1976-04-30 |
| BE809242A (fr) | 1974-06-28 |
| DE2264286B2 (de) | 1978-05-18 |
| JPS4999699A (enrdf_load_html_response) | 1974-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| AH | Division in |
Ref country code: DE Ref document number: 2265453 Format of ref document f/p: P |
|
| 8339 | Ceased/non-payment of the annual fee |