KR101829481B1 - 기체 상에서의 이소시아네이트의 제조 방법 - Google Patents
기체 상에서의 이소시아네이트의 제조 방법 Download PDFInfo
- Publication number
- KR101829481B1 KR101829481B1 KR1020127031740A KR20127031740A KR101829481B1 KR 101829481 B1 KR101829481 B1 KR 101829481B1 KR 1020127031740 A KR1020127031740 A KR 1020127031740A KR 20127031740 A KR20127031740 A KR 20127031740A KR 101829481 B1 KR101829481 B1 KR 101829481B1
- Authority
- KR
- South Korea
- Prior art keywords
- diluent
- amine
- oxygen
- reaction
- weight
- 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.)
- Active
Links
- 239000012948 isocyanate Substances 0.000 title claims description 32
- 150000002513 isocyanates Chemical class 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 103
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 97
- 239000003085 diluting agent Substances 0.000 claims abstract description 93
- 239000001301 oxygen Substances 0.000 claims abstract description 93
- 238000000034 method Methods 0.000 claims abstract description 53
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 91
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 64
- 238000009834 vaporization Methods 0.000 claims description 44
- 230000008016 vaporization Effects 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 239000007792 gaseous phase Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 15
- 239000007789 gas Substances 0.000 abstract description 44
- 230000007704 transition Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 25
- 238000004821 distillation Methods 0.000 description 24
- 239000011261 inert gas Substances 0.000 description 22
- 239000012071 phase Substances 0.000 description 22
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 229910052786 argon Inorganic materials 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 230000000171 quenching effect Effects 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010790 dilution Methods 0.000 description 7
- 239000012895 dilution Substances 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 7
- 239000013067 intermediate product Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002194 freeze distillation Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 238000010574 gas phase reaction Methods 0.000 description 4
- 229910052734 helium Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 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 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- QCDMSCUTQSXHCU-UHFFFAOYSA-N 1-(aminomethyl)cyclohexan-1-amine Chemical compound NCC1(N)CCCCC1 QCDMSCUTQSXHCU-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical class CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910001026 inconel Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- -1 only a few K Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010019342.9 | 2010-05-05 | ||
| DE201010019342 DE102010019342A1 (de) | 2010-05-05 | 2010-05-05 | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| PCT/EP2011/056848 WO2011138245A1 (de) | 2010-05-05 | 2011-04-29 | Verfahren zur herstellung von isocyanaten in der gasphase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20130061152A KR20130061152A (ko) | 2013-06-10 |
| KR101829481B1 true KR101829481B1 (ko) | 2018-02-14 |
Family
ID=44080245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127031740A Active KR101829481B1 (ko) | 2010-05-05 | 2011-04-29 | 기체 상에서의 이소시아네이트의 제조 방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9102594B2 (https=) |
| EP (1) | EP2566844B1 (https=) |
| JP (1) | JP5851488B2 (https=) |
| KR (1) | KR101829481B1 (https=) |
| CN (1) | CN103025709B (https=) |
| DE (1) | DE102010019342A1 (https=) |
| HU (1) | HUE032940T2 (https=) |
| RU (1) | RU2571826C2 (https=) |
| WO (1) | WO2011138245A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2559658A1 (en) * | 2011-08-19 | 2013-02-20 | Huntsman International LLC | A process to separate phosgene and hydrogen chloride from a fluid stream comprising phosgene and hydrogen chloride |
| EP3129353B1 (de) * | 2014-04-11 | 2024-02-28 | Covestro Deutschland AG | Zusammensetzung zur herstellung transparenter polythiourethan-körper |
| US20210060486A1 (en) * | 2020-11-11 | 2021-03-04 | Waga Energy | Facility For Producing Gaseous Biomethane By Purifying Biogas From Landfill Combining Membranes, Cryodistillation And Deoxo |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3714439A1 (de) | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| FR2697017B1 (fr) | 1992-10-16 | 1995-01-06 | Rhone Poulenc Chimie | Procédé de préparation de composés du type isocyanates aromatiques en phase gazeuse. |
| JP3201921B2 (ja) * | 1994-03-22 | 2001-08-27 | 三井化学株式会社 | 脂肪族ポリイソシアナートの製造方法 |
| US5523467A (en) * | 1994-03-22 | 1996-06-04 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of aliphatic polyisocyanates |
| DE19523385A1 (de) | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Herstellung von Triisocyanaten |
| US5872292A (en) | 1997-01-24 | 1999-02-16 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| JP3957396B2 (ja) * | 1998-04-28 | 2007-08-15 | 三井化学株式会社 | イソシアナート化合物の製造方法 |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| US7247658B2 (en) | 2003-07-08 | 2007-07-24 | Milliken & Company | Reduction of discoloration in white polyurethane foams |
| DE10335451A1 (de) | 2003-08-02 | 2005-03-10 | Bayer Materialscience Ag | Verfahren zur Entfernung von flüchtigen Verbindungen aus Stoffgemischen mittels Mikroverdampfer |
| DE10359627A1 (de) * | 2003-12-18 | 2005-07-21 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diisocyanaten |
| DE102005036870A1 (de) | 2005-08-02 | 2007-02-08 | Bayer Materialscience Ag | Verfahren zur Gasphasenphosgenierung |
| DE102005042392A1 (de) * | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102006022761A1 (de) * | 2006-05-16 | 2007-11-22 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102006058633A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102006058634A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| KR101572277B1 (ko) | 2007-08-30 | 2015-11-26 | 바스프 에스이 | 이소시아네이트의 제조 방법 |
| ES2582173T3 (es) * | 2007-11-14 | 2016-09-09 | Covestro Deutschland Ag | Preparación de isocianatos de color claro |
| HU227245B1 (en) * | 2007-12-17 | 2010-12-28 | Borsodchem Nyrt | Process for the preparation of polyirocyanates of the diphenylmethane series |
| CN101429138B (zh) * | 2008-12-18 | 2011-12-28 | 宁波万华聚氨酯有限公司 | 一种在气相中制备异氰酸酯的方法 |
| JP5416830B2 (ja) | 2009-04-24 | 2014-02-12 | ビーエーエスエフ ソシエタス・ヨーロピア | 色の安定なｍｄａとｍｄｉの製造方法 |
-
2010
- 2010-05-05 DE DE201010019342 patent/DE102010019342A1/de not_active Withdrawn
-
2011
- 2011-04-29 RU RU2012151871/04A patent/RU2571826C2/ru not_active IP Right Cessation
- 2011-04-29 US US13/696,195 patent/US9102594B2/en active Active
- 2011-04-29 WO PCT/EP2011/056848 patent/WO2011138245A1/de not_active Ceased
- 2011-04-29 KR KR1020127031740A patent/KR101829481B1/ko active Active
- 2011-04-29 EP EP11718339.2A patent/EP2566844B1/de active Active
- 2011-04-29 HU HUE11718339A patent/HUE032940T2/en unknown
- 2011-04-29 CN CN201180033335.8A patent/CN103025709B/zh active Active
- 2011-04-29 JP JP2013508443A patent/JP5851488B2/ja not_active Expired - Fee Related
-
2015
- 2015-07-02 US US14/790,478 patent/US9328064B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20130131377A1 (en) | 2013-05-23 |
| HUE032940T2 (en) | 2017-11-28 |
| DE102010019342A1 (de) | 2011-11-10 |
| US9328064B2 (en) | 2016-05-03 |
| EP2566844B1 (de) | 2017-03-15 |
| RU2012151871A (ru) | 2014-06-10 |
| US20150299111A1 (en) | 2015-10-22 |
| US9102594B2 (en) | 2015-08-11 |
| RU2571826C2 (ru) | 2015-12-20 |
| KR20130061152A (ko) | 2013-06-10 |
| WO2011138245A1 (de) | 2011-11-10 |
| CN103025709B (zh) | 2015-11-25 |
| CN103025709A (zh) | 2013-04-03 |
| EP2566844A1 (de) | 2013-03-13 |
| JP2013525463A (ja) | 2013-06-20 |
| JP5851488B2 (ja) | 2016-02-03 |
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