DE3044389C2 - - Google Patents
Info
- Publication number
- DE3044389C2 DE3044389C2 DE3044389A DE3044389A DE3044389C2 DE 3044389 C2 DE3044389 C2 DE 3044389C2 DE 3044389 A DE3044389 A DE 3044389A DE 3044389 A DE3044389 A DE 3044389A DE 3044389 C2 DE3044389 C2 DE 3044389C2
- Authority
- DE
- Germany
- Prior art keywords
- aniline
- catalyst
- formaldehyde
- acid
- reaction
- 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 148
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 73
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 26
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical class NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000009833 condensation Methods 0.000 claims description 20
- 230000005494 condensation Effects 0.000 claims description 20
- 229920000768 polyamine Polymers 0.000 claims description 19
- 239000003377 acid catalyst Substances 0.000 claims description 17
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- -1 polymethylene Polymers 0.000 claims description 9
- 230000008707 rearrangement Effects 0.000 claims description 8
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000004927 clay Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000005909 Kieselgur Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 229960000892 attapulgite Drugs 0.000 claims description 2
- 229910052625 palygorskite Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 description 17
- 239000008346 aqueous phase Substances 0.000 description 16
- 239000000543 intermediate Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000011949 solid catalyst Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920000582 polyisocyanurate Polymers 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000007789 gas Substances 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- LEBICJHKTFJDJO-UHFFFAOYSA-N 1,2,3-triphenyltriazinane Chemical compound C1CCN(C=2C=CC=CC=2)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 LEBICJHKTFJDJO-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- SPJXZYLLLWOSLQ-UHFFFAOYSA-N 1-[(1-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CCCCC1(N)CC1(N)CCCCC1 SPJXZYLLLWOSLQ-UHFFFAOYSA-N 0.000 description 1
- ZEMCGIDMAMIJLF-UHFFFAOYSA-N 1-benzyl-2-phenylhydrazine Chemical class C=1C=CC=CC=1CNNC1=CC=CC=C1 ZEMCGIDMAMIJLF-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- LNWBFIVSTXCJJG-UHFFFAOYSA-N [diisocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)(N=C=O)C1=CC=CC=C1 LNWBFIVSTXCJJG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/108,522 US4294987A (en) | 1979-12-31 | 1979-12-31 | Process for preparing methylene dianilines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3044389A1 DE3044389A1 (de) | 1981-07-02 |
| DE3044389C2 true DE3044389C2 (OSRAM) | 1987-11-19 |
Family
ID=22322687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803044389 Granted DE3044389A1 (de) | 1979-12-31 | 1980-11-25 | Verfahren zur herstellung eines gemischs aus di(aminophenyl)methan und oligomeren polymethylenpolyphenylpolyaminen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4294987A (OSRAM) |
| JP (1) | JPS5827261B2 (OSRAM) |
| DE (1) | DE3044389A1 (OSRAM) |
| GB (1) | GB2066809B (OSRAM) |
| NL (1) | NL8006402A (OSRAM) |
| PT (1) | PT72135B (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0264744B1 (en) * | 1986-10-22 | 1992-12-23 | ENIRICERCHE S.p.A. | Process for the preparation of 4,4'-diaminodiphenylmethane and its derivatives |
| US5241119A (en) * | 1986-10-22 | 1993-08-31 | Eniricerche S.P.A. | Process for the preparation of 4,4'-diaminodiphenyl-methane and its derivatives |
| US4792624A (en) * | 1987-02-26 | 1988-12-20 | The Dow Chemical Company | Process for polymeric MDA, recycle of finished polymeric MDA |
| US4835319A (en) * | 1987-11-09 | 1989-05-30 | E. I. Du Pont De Nemours And Company | Process for the manufacture of 1,4-bis(4-phenoxybenzoyl)benzene with a zeolite catalyst |
| US6031136A (en) * | 1993-07-21 | 2000-02-29 | Bayer Corporation | Process for preparing methylene diphenylamines by partial neutralization of acidic methylene diphenylamines |
| CZ296966B6 (cs) | 1997-02-24 | 2006-08-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg. | Farmaceutický prostredek |
| DE19707255A1 (de) * | 1997-02-24 | 1998-08-27 | Basf Ag | Verfahren zur Herstellung von aromatischen Polyamingemischen |
| IT1312331B1 (it) * | 1999-05-27 | 2002-04-15 | Enichem Spa | Procedimento per la produzione di diamminodifenilmetano e suoiomologhi superiori. |
| 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. |
| US7238840B2 (en) * | 2002-03-28 | 2007-07-03 | Huntsman International Llc | Process for the production of diaminodiphenylmethane and its higher homologues |
| ATE536339T1 (de) * | 2007-06-12 | 2011-12-15 | Basf Se | Verfahren zur rückgewinnung von mineralsäuren bei der herstellung von diphenylmethandiamin |
| CN102399155B (zh) * | 2011-12-29 | 2014-03-26 | 河南省华鼎高分子合成树脂有限公司 | 4,4'-二氨基二苯基甲烷的制备方法 |
| KR20170031157A (ko) | 2014-07-07 | 2017-03-20 | 코베스트로 도이칠란트 아게 | 디페닐메탄 시리즈의 디아민 및 폴리아민의 제조 방법 |
| 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 |
|---|---|---|---|---|
| US3362979A (en) * | 1964-01-02 | 1968-01-09 | Jefferson Chem Co Inc | Mixtures of methylene-bridged polyphenyl polyisocyanates |
| US4071558A (en) * | 1967-09-28 | 1978-01-31 | Texaco Development Corporation | Aromatic polyamines and their preparation |
| US3676497A (en) * | 1968-08-06 | 1972-07-11 | Upjohn Co | Process for preparing di(aminophenyl)-methanes |
| GB1229695A (OSRAM) * | 1969-04-17 | 1971-04-28 | ||
| GB1277740A (en) * | 1969-07-11 | 1972-06-14 | Ici Ltd | Manufacture of methylene bridged polyarylamines |
| US3857890A (en) * | 1969-07-25 | 1974-12-31 | Upjohn Co | Process for preparing methylene-di-anilines |
| DE2127263A1 (de) * | 1971-06-02 | 1973-01-04 | Bayer Ag | Verfahren zur herstellung von aromatischen polyaminen |
| DE2238920C3 (de) * | 1972-08-08 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyaminen |
| DE2426116B2 (de) * | 1973-06-01 | 1978-05-11 | Efim Freiburg Biller (Schweiz) | Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen |
| US3971829A (en) * | 1974-11-18 | 1976-07-27 | Jefferson Chemical Company, Inc. | Preparation of methylene-bridged polyphenylpolyamine mixtures |
| DE2500573A1 (de) * | 1975-01-09 | 1976-07-15 | Bayer Ag | Verfahren zur herstellung von polyaminen |
| US4039581A (en) * | 1975-06-27 | 1977-08-02 | The Upjohn Company | Process for the preparation of di(amino phenyl)methanes |
| US4039580A (en) * | 1975-07-24 | 1977-08-02 | The Upjohn Company | Process for preparing di(aminophenyl)methanes |
| DE2557201A1 (de) * | 1975-12-18 | 1977-06-23 | Siemens Ag | Elektrisches bauelement, insbesondere trocken-elektrolytkondensator, und verfahren zu seiner herstellung |
-
1979
- 1979-12-31 US US06/108,522 patent/US4294987A/en not_active Expired - Lifetime
-
1980
- 1980-11-18 GB GB8036933A patent/GB2066809B/en not_active Expired
- 1980-11-24 NL NL8006402A patent/NL8006402A/nl not_active Application Discontinuation
- 1980-11-25 DE DE19803044389 patent/DE3044389A1/de active Granted
- 1980-12-02 PT PT72135A patent/PT72135B/pt unknown
- 1980-12-26 JP JP55189503A patent/JPS5827261B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5827261B2 (ja) | 1983-06-08 |
| PT72135B (en) | 1981-10-22 |
| JPS56120645A (en) | 1981-09-22 |
| PT72135A (en) | 1981-01-01 |
| US4294987A (en) | 1981-10-13 |
| GB2066809A (en) | 1981-07-15 |
| NL8006402A (nl) | 1981-08-03 |
| GB2066809B (en) | 1984-02-15 |
| DE3044389A1 (de) | 1981-07-02 |
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| DE3044389C2 (OSRAM) | ||
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8127 | New person/name/address of the applicant |
Owner name: THE DOW CHEMICAL CO. (EINE GES.N.D.GESETZEN D. STA |
|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |