NO120903B - - Google Patents
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- Publication number
- NO120903B NO120903B NO0398/68A NO39868A NO120903B NO 120903 B NO120903 B NO 120903B NO 0398/68 A NO0398/68 A NO 0398/68A NO 39868 A NO39868 A NO 39868A NO 120903 B NO120903 B NO 120903B
- Authority
- NO
- Norway
- Prior art keywords
- aniline
- formaldehyde
- liquid
- curing agent
- condensate
- Prior art date
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 36
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 34
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 30
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical group NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 14
- 239000004848 polyfunctional curative Substances 0.000 claims description 13
- 229920000647 polyepoxide Polymers 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 8
- -1 alicyclic amines Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- KSNRDYQOHXQKAB-UHFFFAOYSA-N 2,2,4-trimethyl-3,4-dihydro-1h-quinoline Chemical compound C1=CC=C2C(C)CC(C)(C)NC2=C1 KSNRDYQOHXQKAB-UHFFFAOYSA-N 0.000 claims 1
- 239000012897 dilution medium Substances 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 36
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 33
- 229920005989 resin Polymers 0.000 description 23
- 239000011347 resin Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 15
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XGOKOSVLIDVVSC-UHFFFAOYSA-N 1-methyl-4-propan-2-ylcyclohexane-1,2-diamine Chemical compound CC(C)C1CCC(C)(N)C(N)C1 XGOKOSVLIDVVSC-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 150000002118 epoxides Chemical group 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000374 eutectic mixture Substances 0.000 description 2
- 230000005496 eutectics Effects 0.000 description 2
- 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 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003332 Epotuf® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical class C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68507767A | 1967-11-22 | 1967-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120903B true NO120903B (xx) | 1970-12-21 |
Family
ID=24750690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO0398/68A NO120903B (xx) | 1967-11-22 | 1968-02-01 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3539659A (xx) |
| BE (1) | BE713280A (xx) |
| CH (1) | CH496649A (xx) |
| DE (1) | DE1745551B1 (xx) |
| DK (1) | DK117391B (xx) |
| FR (1) | FR1564129A (xx) |
| GB (1) | GB1244858A (xx) |
| NL (1) | NL6801724A (xx) |
| NO (1) | NO120903B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2160124A1 (de) * | 1971-01-08 | 1972-08-24 | Monster Molding Ltd | Verfahren zum Rotationspressen von Formkörpern bei Raumtemperatur |
| US4104357A (en) * | 1973-01-10 | 1978-08-01 | Monster Molding, Inc. | Method of rotational molding about plural axes at low rotational speeds |
| US4422944A (en) * | 1980-04-07 | 1983-12-27 | Nalco Chemical Company | Cationic polymers suitable for reducing turbidity in low turbidity waters |
| GB8521845D0 (en) * | 1985-09-03 | 1985-10-09 | Permabond Adhesives | Initiator compositions |
| US5264525A (en) * | 1986-08-28 | 1993-11-23 | National Starch And Chemical Investment Holding Corporation | Initiator compositions for two part acrylic adhesives |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511913A (en) * | 1950-06-20 | Compositions of resinous epoxides | ||
| BE556372A (xx) * | 1956-04-04 | |||
| GB882016A (en) * | 1957-05-17 | 1961-11-08 | Leicester Lovell & Co Ltd | Improvements in or relating to curing agents for epoxide resins |
| DE1041244B (de) * | 1957-07-11 | 1958-10-16 | Solvay Werke Gmbh | Verfahren zum Haerten von Epoxyharzen |
| US3014007A (en) * | 1958-05-09 | 1961-12-19 | Borden Co | Composition comprising an epoxy resin, an aniline-formaldehyde resin, a liquid polysulfide polymer and a phenolic curing accelerator |
| US3071559A (en) * | 1958-07-07 | 1963-01-01 | Gen Aniline & Film Corp | Heat curable epoxy ether resin employing meta-chlor-aniline-formaldehyde hardener and process of curing the same |
| NL262658A (xx) * | 1960-03-22 | |||
| US3207813A (en) * | 1962-02-09 | 1965-09-21 | Harvel Res Corp | Novel polyepoxide compositions of matter and methods and steps for producing the same |
| US3315010A (en) * | 1962-05-23 | 1967-04-18 | Gen Aniline & Film Corp | Mixture of an epoxy resin and an o-toluidine-aldehyde condensate |
| US3310602A (en) * | 1962-07-26 | 1967-03-21 | Borden Co | Curing epoxide resins with aromatic amine-aldehyde coordination complexes |
-
1967
- 1967-11-22 US US685077A patent/US3539659A/en not_active Expired - Lifetime
-
1968
- 1968-02-01 NO NO0398/68A patent/NO120903B/no unknown
- 1968-02-07 NL NL6801724A patent/NL6801724A/xx unknown
- 1968-02-21 DE DE19681745551 patent/DE1745551B1/de active Pending
- 1968-02-27 DK DK77368AA patent/DK117391B/da unknown
- 1968-03-29 FR FR1564129D patent/FR1564129A/fr not_active Expired
- 1968-04-02 CH CH486268A patent/CH496649A/fr not_active IP Right Cessation
- 1968-04-05 BE BE713280D patent/BE713280A/xx unknown
- 1968-11-22 GB GB55581/68A patent/GB1244858A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1564129A (xx) | 1969-04-18 |
| US3539659A (en) | 1970-11-10 |
| DK117391B (da) | 1970-04-20 |
| GB1244858A (en) | 1971-09-02 |
| NL6801724A (xx) | 1969-05-27 |
| CH496649A (fr) | 1970-09-30 |
| BE713280A (xx) | 1968-10-07 |
| DE1745551B1 (de) | 1972-05-31 |
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