DE2631034C3 - Verfahren zur Herstellung eines Gemisches aus Di-(aminophenyl)-methan und oligomeren Polymethylenpolyphenylpolyaminen - Google Patents
Verfahren zur Herstellung eines Gemisches aus Di-(aminophenyl)-methan und oligomeren PolymethylenpolyphenylpolyaminenInfo
- Publication number
- DE2631034C3 DE2631034C3 DE2631034A DE2631034A DE2631034C3 DE 2631034 C3 DE2631034 C3 DE 2631034C3 DE 2631034 A DE2631034 A DE 2631034A DE 2631034 A DE2631034 A DE 2631034A DE 2631034 C3 DE2631034 C3 DE 2631034C3
- Authority
- DE
- Germany
- Prior art keywords
- aniline
- mixture
- weight
- formaldehyde
- temperature
- 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
- 238000000034 method Methods 0.000 title claims description 53
- 239000000203 mixture Substances 0.000 title claims description 53
- 229920000768 polyamine Polymers 0.000 title claims description 15
- 229920006389 polyphenyl polymer Polymers 0.000 title claims description 15
- -1 polymethylene Polymers 0.000 title claims description 12
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 129
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 106
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000011949 solid catalyst Substances 0.000 claims description 24
- 239000010457 zeolite Substances 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000005909 Kieselgur Substances 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 4
- 150000007854 aminals Chemical class 0.000 description 31
- 150000003939 benzylamines Chemical class 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000004927 clay Substances 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 14
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 12
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910021536 Zeolite Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 238000003822 preparative gas chromatography Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 229960000892 attapulgite Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052625 palygorskite Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000582 polyisocyanurate Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VASMRQAVWVVDPA-UHFFFAOYSA-N 1,3,5-triphenyl-1,3,5-triazinane Chemical compound C1N(C=2C=CC=CC=2)CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 VASMRQAVWVVDPA-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 235000012215 calcium aluminium silicate Nutrition 0.000 description 1
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- CRPOUZQWHJYTMS-UHFFFAOYSA-N dialuminum;magnesium;disilicate Chemical compound [Mg+2].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] CRPOUZQWHJYTMS-UHFFFAOYSA-N 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052677 heulandite Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000000080 wetting agent Substances 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/598,794 US4039580A (en) | 1975-07-24 | 1975-07-24 | Process for preparing di(aminophenyl)methanes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2631034A1 DE2631034A1 (de) | 1977-02-10 |
| DE2631034B2 DE2631034B2 (de) | 1980-01-31 |
| DE2631034C3 true DE2631034C3 (de) | 1981-12-03 |
Family
ID=24396940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2631034A Expired DE2631034C3 (de) | 1975-07-24 | 1976-07-09 | Verfahren zur Herstellung eines Gemisches aus Di-(aminophenyl)-methan und oligomeren Polymethylenpolyphenylpolyaminen |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4039580A (OSRAM) |
| JP (1) | JPS5214754A (OSRAM) |
| BE (1) | BE844461A (OSRAM) |
| BR (1) | BR7604755A (OSRAM) |
| DD (1) | DD126295A5 (OSRAM) |
| DE (1) | DE2631034C3 (OSRAM) |
| ES (1) | ES449690A1 (OSRAM) |
| FR (1) | FR2318903A1 (OSRAM) |
| GB (1) | GB1501574A (OSRAM) |
| IT (1) | IT1066037B (OSRAM) |
| MX (1) | MX3344E (OSRAM) |
| NL (1) | NL172233C (OSRAM) |
| SU (1) | SU1036246A3 (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4294987A (en) * | 1979-12-31 | 1981-10-13 | The Upjohn Company | Process for preparing methylene dianilines |
| DE3323882A1 (de) * | 1982-10-09 | 1984-04-12 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen heissphosgenierung von aminen |
| US4554378A (en) * | 1983-02-22 | 1985-11-19 | The Dow Chemical Company | Process for preparing polyamines with ion exchange resin catalysts |
| EP0245244B1 (en) * | 1985-11-12 | 1992-03-11 | The Dow Chemical Company | A process for continuously preparing aromatic polyamines with ion exchange resin catalysts |
| US5241119A (en) * | 1986-10-22 | 1993-08-31 | Eniricerche S.P.A. | Process for the preparation of 4,4'-diaminodiphenyl-methane and its derivatives |
| US5097672A (en) * | 1988-11-18 | 1992-03-24 | Daikin Industries Ltd. | Spot air-conditioner |
| DE19707255A1 (de) * | 1997-02-24 | 1998-08-27 | Basf Ag | Verfahren zur Herstellung von aromatischen Polyamingemischen |
| CZ296966B6 (cs) * | 1997-02-24 | 2006-08-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg. | Farmaceutický prostredek |
| DE19711447A1 (de) * | 1997-03-19 | 1998-09-24 | Basf Ag | Verfahren zur Herstellung von Isocyanaten mit heller Farbe |
| IT1318437B1 (it) * | 2000-03-31 | 2003-08-25 | Eni Spa | Procedimento per la preparazione di miscele di metilendianilina e suoi omologhi superiori. |
| IT1318686B1 (it) * | 2000-09-07 | 2003-08-27 | Eni Spa | Procedimento per la sintesi di miscele di metilendianilina e suoiomologhi superiori con distribuzione controllata degli isomeri. |
| WO2003082803A1 (en) * | 2002-03-28 | 2003-10-09 | Huntsman International Llc | Process for the production of diaminodiphenylmethane and its higher homologues |
| US7238840B2 (en) * | 2002-03-28 | 2007-07-03 | Huntsman International Llc | Process for the production of diaminodiphenylmethane and its higher homologues |
| RU2330016C2 (ru) * | 2002-03-28 | 2008-07-27 | Хантсмэн Интернэшнл Ллс | Способ получения диаминодифенилметана и его высших гомологов |
| EP1960346B2 (en) * | 2005-12-08 | 2019-03-27 | Huntsman International Llc | Process for preparing diaminodiphenylmethanes |
| KR101199716B1 (ko) * | 2006-12-15 | 2012-11-08 | 다우 글로벌 테크놀로지스 엘엘씨 | 알데히드 및 케톤의 환원성 아민화 방법 |
| EP2014641A3 (en) * | 2007-06-06 | 2009-03-18 | Huntsman International Llc | Process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates |
| EP2039676A1 (en) | 2007-09-19 | 2009-03-25 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| EP2062869A1 (en) * | 2007-09-19 | 2009-05-27 | Huntsman International Llc | Process for the production of di-and polyamines of the diphenylmethane series |
| DE102008001492A1 (de) | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Diaminodiphenylalkanen |
| DE102008001469A1 (de) | 2008-04-30 | 2009-11-05 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Diaminodiphenylalkanen |
| DE102008002002A1 (de) | 2008-05-27 | 2009-12-03 | Evonik Degussa Gmbh | Chlor armes mehrstufiges Verfahren zur Herstellung von cycloaliphatischen Diisocyanaten |
| MX2011005962A (es) | 2008-12-22 | 2011-06-27 | Huntsman Int Llc | Proceso para la produccion de polifenil poliaminas puenteadas con metileno. |
| JP2017523159A (ja) | 2014-07-07 | 2017-08-17 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ジフェニルメタンシリーズのジアミンおよびポリアミンの製造方法 |
| US10538480B2 (en) | 2016-06-30 | 2020-01-21 | Covestro Deutschland Ag | Process for the production of di- and polyamines of the diphenylmethane series |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH177576A (de) * | 1934-06-09 | 1935-06-15 | Chem Ind Basel | Verfahren zur Herstellung eines neuen stickstoffhaltigen Kodensationsproduktes aus Anilin und Formaldehyd. |
| CH408038A (de) * | 1961-12-22 | 1966-02-28 | Bayer Ag | Verfahren zur Herstellung neuer aromatischer Aminoverbindungen |
| US3362979A (en) * | 1964-01-02 | 1968-01-09 | Jefferson Chem Co Inc | Mixtures of methylene-bridged polyphenyl polyisocyanates |
| BE667830A (OSRAM) * | 1964-08-24 | 1965-12-01 | ||
| DE1543611A1 (de) * | 1966-09-08 | 1969-07-31 | Bayer Ag | Verfahren zur Herstellung von Polyarylmethylenpolyaminen bzw. deren Gemischen |
| DE1643471A1 (de) * | 1966-12-19 | 1971-03-11 | Mobay Chemical Corp | Verfahren zur Herstellung von Aminobenzylaminen |
| FR1549769A (OSRAM) * | 1966-12-20 | 1968-12-13 | ||
| US3676497A (en) * | 1968-08-06 | 1972-07-11 | Upjohn Co | Process for preparing di(aminophenyl)-methanes |
| GB1223039A (en) * | 1968-12-20 | 1971-02-17 | Ici Ltd | Process for the manufacture of methylene bridged polyarylamines |
| US3857890A (en) * | 1969-07-25 | 1974-12-31 | Upjohn Co | Process for preparing methylene-di-anilines |
| US3860637A (en) * | 1971-01-26 | 1975-01-14 | Jefferson Chem Co Inc | Selective manufacture of 4,4{40 -isomer of diaminodiphenyl-methane |
| JPS4914746A (OSRAM) * | 1972-06-07 | 1974-02-08 | ||
| DD109615A1 (OSRAM) * | 1972-08-14 | 1974-11-12 | ||
| DE2426116B2 (de) * | 1973-06-01 | 1978-05-11 | Efim Freiburg Biller (Schweiz) | Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen |
-
1975
- 1975-07-24 US US05/598,794 patent/US4039580A/en not_active Expired - Lifetime
-
1976
- 1976-07-02 MX MX000916U patent/MX3344E/es unknown
- 1976-07-06 NL NLAANVRAGE7607443,A patent/NL172233C/xx not_active IP Right Cessation
- 1976-07-07 GB GB28264/76A patent/GB1501574A/en not_active Expired
- 1976-07-08 ES ES449690A patent/ES449690A1/es not_active Expired
- 1976-07-09 DE DE2631034A patent/DE2631034C3/de not_active Expired
- 1976-07-12 IT IT50374/76A patent/IT1066037B/it active
- 1976-07-22 BR BR7604755A patent/BR7604755A/pt unknown
- 1976-07-23 FR FR7622591A patent/FR2318903A1/fr active Granted
- 1976-07-23 SU SU762387956A patent/SU1036246A3/ru active
- 1976-07-23 JP JP51088066A patent/JPS5214754A/ja active Granted
- 1976-07-23 BE BE169185A patent/BE844461A/xx not_active IP Right Cessation
- 1976-07-23 DD DD194028A patent/DD126295A5/xx unknown
-
1977
- 1977-05-16 US US05/797,545 patent/US4092343A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL172233B (nl) | 1983-03-01 |
| BE844461A (fr) | 1977-01-24 |
| SU1036246A3 (ru) | 1983-08-15 |
| DE2631034A1 (de) | 1977-02-10 |
| JPS5214754A (en) | 1977-02-03 |
| NL172233C (nl) | 1983-08-01 |
| NL7607443A (nl) | 1977-01-26 |
| MX3344E (es) | 1980-10-01 |
| GB1501574A (en) | 1978-02-15 |
| DE2631034B2 (de) | 1980-01-31 |
| FR2318903A1 (fr) | 1977-02-18 |
| IT1066037B (it) | 1985-03-04 |
| ES449690A1 (es) | 1977-07-01 |
| FR2318903B1 (OSRAM) | 1981-12-18 |
| BR7604755A (pt) | 1977-08-02 |
| DD126295A5 (OSRAM) | 1977-07-06 |
| US4092343A (en) | 1978-05-30 |
| JPS5614104B2 (OSRAM) | 1981-04-02 |
| US4039580A (en) | 1977-08-02 |
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| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING., PAT.-ANW., 8000 MUENCHEN |
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| 8327 | Change in the person/name/address of the patent owner |
Owner name: THE DOW CHEMICAL CO. (EINE GES.N.D.GESETZEN D. STA |
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| 8328 | Change in the person/name/address of the agent |
Free format text: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZEL, W., DIPL.-ING. KOTTMANN, D., DIPL.-ING, PAT.-ANW., 8000 MUENCHEN |