CA1183145A - Continuous process for the production of organic isocyanates - Google Patents
Continuous process for the production of organic isocyanatesInfo
- Publication number
- CA1183145A CA1183145A CA000402393A CA402393A CA1183145A CA 1183145 A CA1183145 A CA 1183145A CA 000402393 A CA000402393 A CA 000402393A CA 402393 A CA402393 A CA 402393A CA 1183145 A CA1183145 A CA 1183145A
- Authority
- CA
- Canada
- Prior art keywords
- phosgene
- pressure
- solution
- mixing chamber
- amine
- 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
- 239000012948 isocyanate Substances 0.000 title claims abstract description 13
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- 238000010924 continuous production Methods 0.000 title claims abstract description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 49
- 150000001412 amines Chemical class 0.000 claims abstract description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 24
- 150000003141 primary amines Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000036647 reaction Effects 0.000 claims description 3
- 239000000306 component Substances 0.000 claims 2
- 239000005056 polyisocyanate Substances 0.000 abstract description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 201000006747 infectious mononucleosis Diseases 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 101150005851 NOS gene Proteins 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-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
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- ZZWIUWXGJRSQIR-UHFFFAOYSA-N 5-[(4-aminophenyl)methyl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC=C1CC1=CC=C(N)C=C1 ZZWIUWXGJRSQIR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CZEPJJXZASVXQF-ZETCQYMHSA-N ethyl (2s)-2,6-diaminohexanoate Chemical compound CCOC(=O)[C@@H](N)CCCCN CZEPJJXZASVXQF-ZETCQYMHSA-N 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- -1 lysine aminoethyl ester Chemical class 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical class CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material 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
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/10—Preparation of derivatives of isocyanic acid by reaction of amines with carbonyl halides, e.g. with phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3121036.8 | 1981-05-27 | ||
| DE19813121036 DE3121036A1 (de) | 1981-05-27 | 1981-05-27 | Verfahren zur kontinuierlicehn herstellung von organischen mono- oder polyisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1183145A true CA1183145A (en) | 1985-02-26 |
Family
ID=6133304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000402393A Expired CA1183145A (en) | 1981-05-27 | 1982-05-06 | Continuous process for the production of organic isocyanates |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4419295A (enExample) |
| EP (1) | EP0065727B1 (enExample) |
| JP (1) | JPS57200346A (enExample) |
| BR (1) | BR8203067A (enExample) |
| CA (1) | CA1183145A (enExample) |
| DD (1) | DD206782A5 (enExample) |
| DE (2) | DE3121036A1 (enExample) |
| ES (1) | ES512549A0 (enExample) |
| MX (1) | MX159880A (enExample) |
| SU (1) | SU1192613A3 (enExample) |
| UA (1) | UA7217A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3403204A1 (de) * | 1984-01-31 | 1985-08-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von organischen mono- und/oder polyisocyanaten |
| DE3717057A1 (de) * | 1987-05-21 | 1988-12-01 | Bayer Ag | Verfahren zur herstellung von isocyanaten |
| DE3717058A1 (de) * | 1987-05-21 | 1988-12-08 | Bayer Ag | Mischer zum vermischen mindestens zweier fliessfaehiger stoffe, insbesondere unter durchfuehrung bzw. einleitung einer reaktion waehrend der vermischung |
| JP2790513B2 (ja) * | 1989-02-23 | 1998-08-27 | 三井化学株式会社 | キシリレンジイソシアネートの製造方法 |
| DE4217019A1 (de) * | 1992-05-22 | 1993-11-25 | Bayer Ag | Verfahren zur Herstellung von aromatischen Diisocyanaten |
| DE4412327A1 (de) * | 1994-04-11 | 1995-10-12 | Bayer Ag | Verfahren zur Herstellung von Diisocyanaten |
| DE4443642A1 (de) * | 1994-12-08 | 1996-06-13 | Bayer Ag | Kontinuierliches Verfahren zur Herstellung von organischen Isocyanaten |
| DE19817691A1 (de) | 1998-04-21 | 1999-10-28 | Basf Ag | Verfahren zur Herstellung von Mischungen aus Diphenylmehandiisocyanaten und Polyphenylen-polymethylen-polyisocyanaten mit vermindertem Gehalt an chlorierten Nebenprodukten und verminderter Jodfarbzahl |
| ITMI20010860A1 (it) * | 2001-04-24 | 2002-10-24 | Enichem Spa | Procedimento per la produzione in continuo di poliisocianati |
| DE10222968A1 (de) * | 2002-05-23 | 2003-12-04 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| US20040008572A1 (en) * | 2002-07-09 | 2004-01-15 | Stuart Joseph Y. | Coaxial jet mixer nozzle with protruding centerbody and method for mixing two or more fluid components |
| DE10260094A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Isocyanaten |
| DE10260082A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10310888A1 (de) * | 2003-03-11 | 2004-09-23 | Basf Ag | Verfahren zur Herstellung von Polyisocyanaten |
| DE10349504A1 (de) * | 2003-10-23 | 2005-05-25 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| EP1758673A4 (en) * | 2004-06-09 | 2011-05-25 | Huntsman Int Llc | MIXING NOZZLE, PROCESS FOR MIXING AT LEAST TWO FLUIDS AND PROCESS FOR PRODUCING ISOCYANATES |
| DE102004032871A1 (de) * | 2004-07-07 | 2006-02-09 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyisocyanaten durch adiabate Phosgenierung von primären Aminen |
| US20060041166A1 (en) * | 2004-08-20 | 2006-02-23 | Stuart Joseph Y | Process for the continuous preparation of organic monoisocyanates and polyisocyanates |
| CN100366607C (zh) * | 2005-02-28 | 2008-02-06 | 北京金源化学集团有限公司 | 应用固体光气制备多异氰酸酯的方法 |
| US7547801B2 (en) * | 2006-06-26 | 2009-06-16 | Bayer Materialscience Llc | Process for the continuous preparation of isocyanates |
| CN101528678B (zh) * | 2006-10-26 | 2014-03-19 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| EP2014641A3 (en) * | 2007-06-06 | 2009-03-18 | Huntsman International Llc | Process for preparing mixtures of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates |
| HUP0700771A2 (en) * | 2007-11-30 | 2010-08-30 | Borsodchem Nyrt | Mixing device for mixing two liquids and process for the continuous preparation of organic mono-, di- or polysocianates |
| US20110228630A1 (en) * | 2010-03-16 | 2011-09-22 | Dow Global Technologies, Inc. | Reduced Transit Static Mixer Configuration |
| US20110230679A1 (en) * | 2010-03-16 | 2011-09-22 | Dow Global Technologies, Inc. | Reactive Static Mixer |
| PT3009185T (pt) | 2010-09-28 | 2017-11-14 | Dow Global Technologies Llc | Misturador estático de fluxo reativo com obstruções de fluxo cruzado |
| HUE031742T2 (en) | 2011-09-02 | 2017-07-28 | Basf Se | Process for the preparation of isocyanates |
| ES2658214T3 (es) | 2012-03-19 | 2018-03-08 | Covestro Deutschland Ag | Procedimiento para la preparación de isocianatos |
| CN104640840B (zh) | 2012-09-24 | 2018-03-02 | 科思创德国股份有限公司 | 通过二胺悬浮体的光气化制备二异氰酸酯的方法 |
| CN106458864B (zh) * | 2014-03-27 | 2020-08-11 | 科思创德国股份有限公司 | 运行气相光气化装置的方法 |
| HUE037053T2 (hu) * | 2014-03-27 | 2018-08-28 | Covestro Deutschland Ag | Eljárás izocianátok elõállítására |
| WO2015144681A1 (de) * | 2014-03-27 | 2015-10-01 | Bayer Material Science Ag | Verfahren zum betreiben einer gasphasenphosgenierungsanlage |
| WO2017001322A1 (de) | 2015-06-29 | 2017-01-05 | Covestro Deutschland Ag | Verfahren zur herstellung von polyisocyanaten |
| PT3313815T (pt) | 2015-06-29 | 2019-10-17 | Covestro Deutschland Ag | Método de preparação de cloreto de hidrogénio para reações químicas |
| WO2018114846A1 (de) | 2016-12-21 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung eines isocyanats |
| US11225546B2 (en) * | 2017-03-06 | 2022-01-18 | Dow Global Technologies Llc | Process for preparing isocyanates |
| KR102491064B1 (ko) * | 2017-04-10 | 2023-01-19 | 미쓰이 가가쿠 가부시키가이샤 | 자일릴렌 다이아이소사이아네이트 조성물, 자일릴렌 다이아이소사이아네이트 변성체 조성물, 이액형 수지 원료 및 수지 |
| HUE068310T2 (hu) | 2019-09-17 | 2024-12-28 | Covestro Deutschland Ag | Eljárás izocianátok elõállítására |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1792660U (de) | 1955-01-07 | 1959-07-30 | Voigt & Haeffner Ag | Installationsselbstschalter in sockel- oder elementform. |
| DE1146872B (de) | 1959-01-29 | 1963-04-11 | Bayer Ag | Verfahren zur Herstellung von organischen Isocyanaten |
| US3507626A (en) * | 1965-10-15 | 1970-04-21 | Mobay Chemical Corp | Venturi mixer |
| BE711392A (enExample) | 1968-02-28 | 1968-07-01 | Gnii Pi Azotnoj | |
| FR2119177A5 (enExample) * | 1970-12-23 | 1972-08-04 | Roure Bertrand Dupont Sa | |
| US3781320A (en) * | 1971-02-09 | 1973-12-25 | Du Pont | Process for manufacture of organic isocyanates |
| BE790461A (fr) | 1971-10-25 | 1973-02-15 | Quimco Gmbh | Procede de production d'isocyanates organiques |
| DD132340B1 (de) * | 1975-09-23 | 1983-06-08 | Hans Iben | Verfahren zur phosgenierung von aminen zu mono-,di-und polyisocyanaten |
| DE2803103A1 (de) * | 1978-01-25 | 1979-07-26 | Bayer Ag | Verfahren zur herstellung von biuret- und/oder harnstoffgruppen aufweisenden organischen polyisocyanaten |
| CA1137076A (en) | 1978-12-13 | 1982-12-07 | John R. Bauer | Fluid spray mixer - reactor system |
| US4289732A (en) * | 1978-12-13 | 1981-09-15 | The Upjohn Company | Apparatus for intimately admixing two chemically reactive liquid components |
-
1981
- 1981-05-27 DE DE19813121036 patent/DE3121036A1/de not_active Withdrawn
-
1982
- 1982-05-06 CA CA000402393A patent/CA1183145A/en not_active Expired
- 1982-05-15 DE DE8282104266T patent/DE3260452D1/de not_active Expired
- 1982-05-15 EP EP82104266A patent/EP0065727B1/de not_active Expired
- 1982-05-20 US US06/379,822 patent/US4419295A/en not_active Expired - Lifetime
- 1982-05-21 SU SU823441302A patent/SU1192613A3/ru active
- 1982-05-21 UA UA3441302A patent/UA7217A1/uk unknown
- 1982-05-24 DD DD82240117A patent/DD206782A5/de not_active IP Right Cessation
- 1982-05-24 MX MX192830A patent/MX159880A/es unknown
- 1982-05-26 JP JP57088169A patent/JPS57200346A/ja active Granted
- 1982-05-26 BR BR8203067A patent/BR8203067A/pt not_active IP Right Cessation
- 1982-05-26 ES ES512549A patent/ES512549A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4419295A (en) | 1983-12-06 |
| EP0065727A1 (de) | 1982-12-01 |
| DE3121036A1 (de) | 1982-12-16 |
| JPH0153664B2 (enExample) | 1989-11-15 |
| JPS57200346A (en) | 1982-12-08 |
| BR8203067A (pt) | 1983-05-10 |
| UA7217A1 (uk) | 1995-06-30 |
| DE3260452D1 (en) | 1984-08-30 |
| SU1192613A3 (ru) | 1985-11-15 |
| DD206782A5 (de) | 1984-02-08 |
| ES8304071A1 (es) | 1983-02-16 |
| MX159880A (es) | 1989-09-25 |
| EP0065727B1 (de) | 1984-07-25 |
| ES512549A0 (es) | 1983-02-16 |
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