RU2487865C2 - Способ получения изоцианата - Google Patents
Способ получения изоцианата Download PDFInfo
- Publication number
- RU2487865C2 RU2487865C2 RU2008144792/04A RU2008144792A RU2487865C2 RU 2487865 C2 RU2487865 C2 RU 2487865C2 RU 2008144792/04 A RU2008144792/04 A RU 2008144792/04A RU 2008144792 A RU2008144792 A RU 2008144792A RU 2487865 C2 RU2487865 C2 RU 2487865C2
- Authority
- RU
- Russia
- Prior art keywords
- amine
- phosgene
- reaction zone
- reaction
- bar
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000012948 isocyanate Substances 0.000 title claims abstract description 21
- 150000002513 isocyanates Chemical class 0.000 title abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012535 impurity Substances 0.000 claims abstract description 5
- -1 aliphatic isocyanate Chemical class 0.000 claims abstract description 4
- 150000003141 primary amines Chemical class 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 46
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-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
- 241001550224 Apha Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000796533 Arna Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 238000001736 differential pulse polarography Methods 0.000 description 2
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002156 mixing Methods 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
- 238000010992 reflux Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical class N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000013466 adhesive and sealant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000004246 zinc acetate 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 |
|---|---|---|---|
| US300007P | 2007-11-14 | 2007-11-14 | |
| US61/003,000 | 2007-11-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008144792A RU2008144792A (ru) | 2010-05-20 |
| RU2487865C2 true RU2487865C2 (ru) | 2013-07-20 |
Family
ID=40348488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008144792/04A RU2487865C2 (ru) | 2007-11-14 | 2008-11-13 | Способ получения изоцианата |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9382198B2 (https=) |
| EP (1) | EP2060560B1 (https=) |
| JP (2) | JP2009149614A (https=) |
| KR (1) | KR101602495B1 (https=) |
| CN (1) | CN101440046B (https=) |
| ES (1) | ES2582173T3 (https=) |
| HU (1) | HUE027861T2 (https=) |
| RU (1) | RU2487865C2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2028178A1 (de) * | 2007-08-22 | 2009-02-25 | Bayer MaterialScience AG | Herstellung von Isocyanaten mit niedrigen Chlorgehalten |
| DE102009032414A1 (de) * | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| JP5787908B2 (ja) * | 2010-03-18 | 2015-09-30 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | イソシアネートの生産方法 |
| DE102010019342A1 (de) * | 2010-05-05 | 2011-11-10 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| HUE025025T2 (en) * | 2011-03-31 | 2016-04-28 | Basf Se | Process for the preparation of isocyanates |
| CN103922969B (zh) * | 2014-04-10 | 2016-01-20 | 万华化学集团股份有限公司 | 一种制备颜色稳定的1,6-己二异氰酸酯的方法 |
| EP3129353B1 (de) * | 2014-04-11 | 2024-02-28 | Covestro Deutschland AG | Zusammensetzung zur herstellung transparenter polythiourethan-körper |
| WO2018050441A1 (de) * | 2016-09-14 | 2018-03-22 | Basf Se | Verfahren zur hydrierung eines gemisches in gegenwart eines farblosen amins |
| CN110387031B (zh) * | 2019-07-12 | 2021-06-29 | 万华化学集团股份有限公司 | 一种浅色异氰酸酯制备方法 |
| EP3939960A1 (de) | 2020-07-15 | 2022-01-19 | Covestro Deutschland AG | Verfahren zur gewinnung von diaminen aus wässrigen mischungen |
| EP4151619A1 (en) | 2021-09-20 | 2023-03-22 | Covestro Deutschland AG | Method for the removal of water from and transport of aliphatic diamines |
| EP4151618A1 (en) | 2021-09-20 | 2023-03-22 | Covestro Deutschland AG | Obtaining aliphatic amines from compositions |
| KR20250053185A (ko) | 2022-11-17 | 2025-04-21 | 완후아 케미컬 그룹 코., 엘티디 | 이소시아네이트 조성물과 이의 제조방법 및 용도 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041442A (en) * | 1963-01-07 | 1966-09-07 | Monsanto Co | Process for the purification of hexamethylenediamine |
| US3859323A (en) * | 1969-04-02 | 1975-01-07 | Allied Chem | Preparation of 4,4'-methylenebis (cyclohexylisocyanate) |
| US5484819A (en) * | 1991-12-10 | 1996-01-16 | Bayer Corporation | Process for preparing polyamines for lighter color polyisocyanate based foam |
| EP0866057A2 (de) * | 1997-03-19 | 1998-09-23 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Isocyanaten mit heller Farbe |
| RU2004137019A (ru) * | 2003-12-18 | 2006-05-27 | Байер МатириальСайенс АГ (DE) | Способ получения изоцианатов в газовой фазе |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017331A (en) * | 1959-04-15 | 1962-01-16 | Chemstrand Corp | Method for the purification of hexamethylenediamine |
| DE3714439A1 (de) * | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| DE4008074A1 (de) | 1990-03-14 | 1991-09-19 | Basf Ag | Verfahren zur qualitaetsverbesserung von rohen diaminodiphenylmethanen |
| US5133838A (en) * | 1991-02-28 | 1992-07-28 | E. I. Du Pont De Nemours And Company | Purification of 6-aminocapronitrile |
| US5312971A (en) * | 1992-07-23 | 1994-05-17 | Miles Inc. | Color reduction of polymethylene polyphenyl polyisocyanates |
| US5286760A (en) * | 1992-10-09 | 1994-02-15 | Miles, Inc. | Process for reducing impurity levels in methylene diphenyamines |
| US5942151A (en) * | 1997-11-20 | 1999-08-24 | Bayer Corporation | Polymeric MDI color |
| DE19812427A1 (de) * | 1998-03-20 | 1999-09-23 | Basf Ag | Verfahren zur Abtrennung eines Azepin-Derivats aus einer Mischung enthaltend ein Amin und ein Azepin-Derivat |
| DE19928741A1 (de) * | 1999-06-23 | 2000-12-28 | Basf Ag | Helle Isocyanate, Verfahren zu deren Herstellung und deren Verwendung |
| DE10025301A1 (de) | 2000-05-22 | 2001-11-29 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten mit Biuretstruktur |
| US6248926B1 (en) * | 2000-10-26 | 2001-06-19 | E. I. Du Pont De Nemours And Company | Recovery of hexamethylenediamine (HMD) with low polarographically reducible impurities (PRI) from mixtures of HMD, aminocapronitirle and PRI |
| DE10158160A1 (de) | 2001-11-28 | 2003-06-12 | Basf Ag | Herstellung von Isocyanaten in der Gasphase |
| DE10223827A1 (de) * | 2002-05-28 | 2003-12-11 | Basf Ag | Verfahren zur Reduzierung des Gehalts an einem ungesättigten Amin in einer Mischung enthaltend ein Aminonitril, ein Diamin, ein Dinitril oder deren Gemische |
| DE10235476A1 (de) * | 2002-08-02 | 2004-02-12 | Basf Ag | Integriertes Verfahren zur Herstellung von Isocyanaten |
| DE10245704A1 (de) | 2002-09-30 | 2004-04-01 | Bayer Ag | Verfahren zum Quenchen eines gasförmigen Reaktionsgemisches bei der Gasphasenphosgenierung von Diaminen |
| DE10260082A1 (de) * | 2002-12-19 | 2004-07-01 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Isocyanaten |
| DE10261187A1 (de) * | 2002-12-20 | 2004-07-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| US7060819B2 (en) * | 2003-09-15 | 2006-06-13 | Invista North America S.A.R.L. | Process for producing hexamethylenediamine and aminocapronitrile from adiponitrile, wherein the hexamethylenediamine contains less than 100 ppm tetrahydroazepine |
| US20070232827A1 (en) * | 2004-05-25 | 2007-10-04 | Basf Aktiengesellschaft | Isocyanate Production Method |
| DE102004030164A1 (de) * | 2004-06-22 | 2006-01-19 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| JP4938007B2 (ja) * | 2005-05-30 | 2012-05-23 | ハンツマン・インターナショナル・エルエルシー | ジフェニルメタン系ポリイソシアネートの製造法 |
| DE102006004047A1 (de) * | 2006-01-28 | 2007-08-02 | Bayer Materialscience Ag | Verfahren zur Herstellung von Di- und Polyaminen der Diphenylmethanreihe |
| US8030522B2 (en) * | 2006-06-07 | 2011-10-04 | Bayer Materialscience Llc | Process for the production of toluene diisocyanate |
-
2008
- 2008-11-03 ES ES08019172.9T patent/ES2582173T3/es active Active
- 2008-11-03 HU HUE08019172A patent/HUE027861T2/en unknown
- 2008-11-03 EP EP08019172.9A patent/EP2060560B1/en not_active Not-in-force
- 2008-11-12 US US12/291,774 patent/US9382198B2/en not_active Expired - Fee Related
- 2008-11-13 RU RU2008144792/04A patent/RU2487865C2/ru not_active IP Right Cessation
- 2008-11-13 JP JP2008291120A patent/JP2009149614A/ja active Pending
- 2008-11-13 KR KR1020080112546A patent/KR101602495B1/ko not_active Expired - Fee Related
- 2008-11-14 CN CN2008101842406A patent/CN101440046B/zh not_active Expired - Fee Related
-
2015
- 2015-02-06 JP JP2015022503A patent/JP2015110640A/ja active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041442A (en) * | 1963-01-07 | 1966-09-07 | Monsanto Co | Process for the purification of hexamethylenediamine |
| US3859323A (en) * | 1969-04-02 | 1975-01-07 | Allied Chem | Preparation of 4,4'-methylenebis (cyclohexylisocyanate) |
| US5484819A (en) * | 1991-12-10 | 1996-01-16 | Bayer Corporation | Process for preparing polyamines for lighter color polyisocyanate based foam |
| EP0866057A2 (de) * | 1997-03-19 | 1998-09-23 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Isocyanaten mit heller Farbe |
| RU2004137019A (ru) * | 2003-12-18 | 2006-05-27 | Байер МатириальСайенс АГ (DE) | Способ получения изоцианатов в газовой фазе |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101440046A (zh) | 2009-05-27 |
| ES2582173T3 (es) | 2016-09-09 |
| US9382198B2 (en) | 2016-07-05 |
| KR101602495B1 (ko) | 2016-03-10 |
| RU2008144792A (ru) | 2010-05-20 |
| JP2015110640A (ja) | 2015-06-18 |
| KR20090050002A (ko) | 2009-05-19 |
| HUE027861T2 (en) | 2016-11-28 |
| JP2009149614A (ja) | 2009-07-09 |
| US20090149671A1 (en) | 2009-06-11 |
| EP2060560B1 (en) | 2016-04-13 |
| CN101440046B (zh) | 2013-09-18 |
| EP2060560A1 (en) | 2009-05-20 |
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