TWI501944B - 在氣相中製備異氰酸酯之方法 - Google Patents
在氣相中製備異氰酸酯之方法 Download PDFInfo
- Publication number
- TWI501944B TWI501944B TW098142166A TW98142166A TWI501944B TW I501944 B TWI501944 B TW I501944B TW 098142166 A TW098142166 A TW 098142166A TW 98142166 A TW98142166 A TW 98142166A TW I501944 B TWI501944 B TW I501944B
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- TW
- Taiwan
- Prior art keywords
- reaction
- reaction space
- amine
- cross
- section
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 63
- 239000012948 isocyanate Substances 0.000 title claims description 37
- 230000008569 process Effects 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002513 isocyanates Chemical class 0.000 title description 29
- 238000006243 chemical reaction Methods 0.000 claims description 232
- 150000001412 amines Chemical class 0.000 claims description 63
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 55
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 51
- 125000003277 amino group Chemical group 0.000 claims description 51
- 238000002156 mixing Methods 0.000 claims description 39
- 239000011541 reaction mixture Substances 0.000 claims description 32
- -1 aromatic isocyanate Chemical class 0.000 claims description 21
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical group CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 description 45
- 238000010791 quenching Methods 0.000 description 16
- 230000000171 quenching effect Effects 0.000 description 15
- 238000001816 cooling Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 8
- 238000002309 gasification Methods 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- 230000008092 positive effect Effects 0.000 description 4
- 150000003142 primary aromatic amines Chemical class 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 238000005054 agglomeration Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OHOOTRXJVCLDRR-UHFFFAOYSA-N [Cl-].NC(N)NC(=[NH2+])N Chemical compound [Cl-].NC(N)NC(=[NH2+])N OHOOTRXJVCLDRR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010574 gas phase reaction Methods 0.000 description 2
- 238000009499 grossing Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical compound NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000112 cooling gas Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- LADVLFVCTCHOAI-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.CC1=CC=CC=C1 LADVLFVCTCHOAI-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
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 |
|---|---|---|---|
| DE102008061686A DE102008061686A1 (de) | 2008-12-11 | 2008-12-11 | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201035022A TW201035022A (en) | 2010-10-01 |
| TWI501944B true TWI501944B (zh) | 2015-10-01 |
Family
ID=41693159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098142166A TWI501944B (zh) | 2008-12-11 | 2009-12-10 | 在氣相中製備異氰酸酯之方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9024057B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2196455B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5574684B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR101673591B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN101747230B (cg-RX-API-DMAC10.html) |
| DE (1) | DE102008061686A1 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2394133T3 (cg-RX-API-DMAC10.html) |
| PL (1) | PL2196455T3 (cg-RX-API-DMAC10.html) |
| RU (1) | RU2528382C2 (cg-RX-API-DMAC10.html) |
| TW (1) | TWI501944B (cg-RX-API-DMAC10.html) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2658214T3 (es) | 2012-03-19 | 2018-03-08 | Covestro Deutschland Ag | Procedimiento para la preparación de isocianatos |
| US9932299B2 (en) | 2013-02-08 | 2018-04-03 | Covestro Deutschland Ag | Process for separating an isocyanate prepared by phosgenation of a primary amine in the gas phase from the gaseous crude product of the phosgenation |
| EP2829533A1 (de) | 2013-07-26 | 2015-01-28 | Bayer MaterialScience AG | Verfahren zur herstellung von isocyanaten |
| KR20160044473A (ko) | 2013-08-19 | 2016-04-25 | 코베스트로 도이칠란트 아게 | 이소시아네이트 제조로부터의 증류 잔류물로부터 유기 이소시아네이트를 수득하는 방법 |
| EP3160630B1 (de) | 2014-06-24 | 2022-08-31 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von chemischen produkten mit betriebsunterbrechungen |
| CN107667089B (zh) | 2015-06-12 | 2021-02-26 | 科思创德国股份有限公司 | 在气相中制备二异氰酸酯的方法 |
| WO2017009311A1 (de) | 2015-07-16 | 2017-01-19 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
| JP6913083B2 (ja) | 2015-09-30 | 2021-08-04 | 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 | イソシアネートの製造方法 |
| HUE055741T2 (hu) | 2016-08-17 | 2021-12-28 | Covestro Intellectual Property Gmbh & Co Kg | Eljárás és berendezés különféle vegyi termékek elõállítására |
| JP6932768B2 (ja) | 2016-09-01 | 2021-09-08 | 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 | イソシアネートの製造方法 |
| US11225546B2 (en) * | 2017-03-06 | 2022-01-18 | Dow Global Technologies Llc | Process for preparing isocyanates |
| WO2018224530A1 (de) | 2017-06-08 | 2018-12-13 | Covestro Deutschland Ag | Verfahren zur herstellung von isocyanaten |
| EP3634947B1 (de) | 2017-06-08 | 2022-09-07 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von isocyanaten in der gasphase |
| HUE056221T2 (hu) | 2017-07-03 | 2022-02-28 | Covestro Intellectual Property Gmbh & Co Kg | Termelõ berendezés kémiai termék elõállítására H-funkciós reagens és foszgén reagáltatásával és eljárás ennek üzemeltetésére |
| US10626084B2 (en) | 2018-08-03 | 2020-04-21 | Covestro Llc | Method for producing two isocyanates |
| US10851048B2 (en) * | 2018-11-13 | 2020-12-01 | Covestro Deutschland Ag | Process for preparing an isocyanate by partly adiabatically operated phosgenation of the corresponding amine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391683A (en) * | 1992-10-16 | 1995-02-21 | Rhone-Poulenc Chimie | Preparation of aromatic polyisocyanates |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATA50084A (de) | 1984-02-15 | 1986-06-15 | Lift Verkaufsgeraete Gmbh | Karteikastenartige vorrichtung zur aufnahme von steifen, flachen gegenstaenden |
| EP0275639B1 (en) | 1986-11-27 | 1992-07-15 | Beecham Group Plc | N-substituted cyclic amides, their preparation and pharmaceutical compositions containing them |
| DE3714439A1 (de) | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| DE4034840A1 (de) | 1990-11-02 | 1992-05-07 | Henkel Kgaa | Enzymatisches fluessigwaschmittel |
| DE4217019A1 (de) | 1992-05-22 | 1993-11-25 | Bayer Ag | Verfahren zur Herstellung von aromatischen Diisocyanaten |
| FR2723585B1 (fr) * | 1994-08-12 | 1996-09-27 | Rhone Poulenc Chimie | Procede de preparation de composes du type polyisocyanates aromatiques en phase gazeuse. |
| DE19523385A1 (de) | 1995-06-23 | 1997-01-09 | Bayer Ag | Verfahren zur Herstellung von Triisocyanaten |
| DE10133728A1 (de) * | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
| DE10133729A1 (de) | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
| DE10222023A1 (de) | 2002-05-17 | 2003-11-27 | Bayer Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10307141A1 (de) | 2003-02-20 | 2004-09-02 | Bayer Ag | Verfahren zur Herstellung von (Poly)isocyanaten in der Gasphase |
| DE10349504A1 (de) * | 2003-10-23 | 2005-05-25 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| 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 |
| US20070049482A1 (en) | 2005-08-11 | 2007-03-01 | Shin-Etsu Chemical Co., Ltd. | Synthetic quartz glass substrate for excimer lasers and making method |
| DE102005042392A1 (de) | 2005-09-06 | 2007-03-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102005042604A1 (de) | 2005-09-07 | 2007-03-08 | Basf Ag | Neutralisationsverfahren |
| WO2008055899A1 (de) * | 2006-11-07 | 2008-05-15 | Basf Se | Verfahren zur herstellung von isocyanaten |
| US20100056822A1 (en) * | 2006-11-07 | 2010-03-04 | Basf Se | Method for producing isocyanates |
| CN101583594B (zh) | 2006-11-07 | 2013-06-19 | 巴斯夫欧洲公司 | 生产异氰酸酯的方法 |
| DE102006058634A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102006058633A1 (de) * | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
-
2008
- 2008-12-11 DE DE102008061686A patent/DE102008061686A1/de not_active Withdrawn
-
2009
- 2009-11-28 ES ES09014815T patent/ES2394133T3/es active Active
- 2009-11-28 EP EP09014815A patent/EP2196455B1/de active Active
- 2009-11-28 PL PL09014815T patent/PL2196455T3/pl unknown
- 2009-12-02 JP JP2009274288A patent/JP5574684B2/ja not_active Expired - Fee Related
- 2009-12-07 US US12/632,117 patent/US9024057B2/en active Active
- 2009-12-10 RU RU2009145797/04A patent/RU2528382C2/ru not_active IP Right Cessation
- 2009-12-10 CN CN200910258555.5A patent/CN101747230B/zh active Active
- 2009-12-10 TW TW098142166A patent/TWI501944B/zh not_active IP Right Cessation
- 2009-12-10 KR KR1020090122317A patent/KR101673591B1/ko active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391683A (en) * | 1992-10-16 | 1995-02-21 | Rhone-Poulenc Chimie | Preparation of aromatic polyisocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| PL2196455T3 (pl) | 2013-02-28 |
| CN101747230B (zh) | 2014-04-09 |
| JP5574684B2 (ja) | 2014-08-20 |
| ES2394133T3 (es) | 2013-01-22 |
| KR101673591B1 (ko) | 2016-11-07 |
| CN101747230A (zh) | 2010-06-23 |
| EP2196455B1 (de) | 2012-09-26 |
| US9024057B2 (en) | 2015-05-05 |
| US20100152484A1 (en) | 2010-06-17 |
| DE102008061686A1 (de) | 2010-06-17 |
| RU2528382C2 (ru) | 2014-09-20 |
| RU2009145797A (ru) | 2011-06-20 |
| KR20100067626A (ko) | 2010-06-21 |
| EP2196455A1 (de) | 2010-06-16 |
| JP2010138171A (ja) | 2010-06-24 |
| TW201035022A (en) | 2010-10-01 |
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