JP3869494B2 - トリイソシアネートの製造方法 - Google Patents
トリイソシアネートの製造方法 Download PDFInfo
- Publication number
- JP3869494B2 JP3869494B2 JP17979596A JP17979596A JP3869494B2 JP 3869494 B2 JP3869494 B2 JP 3869494B2 JP 17979596 A JP17979596 A JP 17979596A JP 17979596 A JP17979596 A JP 17979596A JP 3869494 B2 JP3869494 B2 JP 3869494B2
- Authority
- JP
- Japan
- Prior art keywords
- triisocyanate
- triamine
- temperature
- reaction chamber
- solvent
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 239000011261 inert gas Substances 0.000 claims description 10
- 239000012442 inert solvent Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical group NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- FUIFPVKJGLFULI-UHFFFAOYSA-N [3,5-bis(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CC(CN)CC(CN)C1 FUIFPVKJGLFULI-UHFFFAOYSA-N 0.000 claims description 2
- DQWFTGPZPKZMAB-UHFFFAOYSA-N undecane-1,6,11-triamine Chemical compound NCCCCCC(N)CCCCCN DQWFTGPZPKZMAB-UHFFFAOYSA-N 0.000 claims description 2
- ORXJAHKNMXPUIS-UHFFFAOYSA-N 4-(3-aminopropyl)heptane-1,7-diamine Chemical compound NCCCC(CCCN)CCCN ORXJAHKNMXPUIS-UHFFFAOYSA-N 0.000 claims 1
- XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000008246 gaseous mixture 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- JKGFFBTZLGLPHB-UHFFFAOYSA-N 2-methylcyclohexane-1,1,2-triamine Chemical class CC1(N)CCCCC1(N)N JKGFFBTZLGLPHB-UHFFFAOYSA-N 0.000 description 1
- CKUKPNSCLYHVHU-UHFFFAOYSA-N 3-(aminomethyl)hexane-1,6-diamine Chemical compound NCCCC(CN)CCN CKUKPNSCLYHVHU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XKNMBLOUCCIBMS-UHFFFAOYSA-N [2,2-bis(aminomethyl)cyclohexyl]methanamine Chemical class NCC1CCCCC1(CN)CN XKNMBLOUCCIBMS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 aliphatic diamines Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000012808 vapor phase Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C263/00—Preparation of derivatives of isocyanic acid
- C07C263/18—Separation; Purification; Stabilisation; Use of additives
- C07C263/20—Separation; Purification
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 |
|---|---|---|---|
| DE19523385A DE19523385A1 (de) | 1995-06-23 | 1995-06-23 | Verfahren zur Herstellung von Triisocyanaten |
| DE19523385.9 | 1995-06-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH0912525A JPH0912525A (ja) | 1997-01-14 |
| JPH0912525A5 JPH0912525A5 (enExample) | 2004-07-15 |
| JP3869494B2 true JP3869494B2 (ja) | 2007-01-17 |
Family
ID=7765390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17979596A Expired - Fee Related JP3869494B2 (ja) | 1995-06-23 | 1996-06-21 | トリイソシアネートの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5633396A (enExample) |
| EP (1) | EP0749958B1 (enExample) |
| JP (1) | JP3869494B2 (enExample) |
| CA (1) | CA2179344A1 (enExample) |
| DE (2) | DE19523385A1 (enExample) |
| ES (1) | ES2139279T3 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020123644A1 (en) * | 1997-01-16 | 2002-09-05 | Mitsumasa Kitai | Aliphatic triisocyanate compound, process for producing the same, and polyurethane resin made from the compound |
| DE19800529A1 (de) | 1998-01-09 | 1999-07-15 | Bayer Ag | Verfahren zur Phosgenierung von Aminen in der Gasphase unter Einsatz von Mikrostrukturmischern |
| AU2001252127A1 (en) * | 2000-02-16 | 2001-08-27 | Basf Aktiengesellschaft | Polyisocyanates as coating components for coating means rich in solids |
| 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 |
| DE10158160A1 (de) | 2001-11-28 | 2003-06-12 | Basf Ag | Herstellung von Isocyanaten in der Gasphase |
| DE10161384A1 (de) * | 2001-12-14 | 2003-06-18 | Bayer Ag | Verbessertes Verfahren für die Herstellung von (/Poly)-isocyanaten in der Gasphase |
| JPWO2004022527A1 (ja) * | 2002-09-09 | 2005-12-22 | 協和発酵ケミカル株式会社 | リジンエステルトリイソシアネート及びその製造法 |
| 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 |
| 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 |
| DE102004030164A1 (de) | 2004-06-22 | 2006-01-19 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102005037328A1 (de) | 2005-08-04 | 2007-02-08 | Basf Ag | Verfahren zur Herstellung von Isocyanaten |
| ATE496881T1 (de) | 2006-02-15 | 2011-02-15 | Ge Healthcare As | Kontrastmittel |
| US7547801B2 (en) * | 2006-06-26 | 2009-06-16 | Bayer Materialscience Llc | Process for the continuous preparation of isocyanates |
| JP2010508374A (ja) | 2006-11-07 | 2010-03-18 | ビーエーエスエフ ソシエタス・ヨーロピア | イソシアネートの製造方法 |
| DE102006058633A1 (de) | 2006-12-13 | 2008-06-19 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| CN102850239B (zh) * | 2007-01-17 | 2014-07-02 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| WO2009037179A1 (de) | 2007-09-19 | 2009-03-26 | Basf Se | Verfahren zur herstellung von isocyanaten |
| DE102007056511A1 (de) | 2007-11-22 | 2009-05-28 | Bayer Materialscience Ag | Verfahren zur Herstellung aromatischer Diisocyanate in der Gasphase |
| CN102245565B (zh) * | 2008-10-15 | 2014-12-31 | 巴斯夫欧洲公司 | 制备异氰酸酯的方法 |
| DE102008061686A1 (de) | 2008-12-11 | 2010-06-17 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102008063728A1 (de) | 2008-12-18 | 2010-06-24 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102009032413A1 (de) | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten |
| DE102009032414A1 (de) | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| DE102009033639A1 (de) | 2009-07-17 | 2011-01-20 | Bayer Materialscience Ag | Verfahen zur Herstellung von Isocyanaten in der Gasphase |
| IN2012DN03890A (enExample) | 2009-11-03 | 2015-09-04 | Bayer Materialscience Ag | |
| EP2497084B1 (de) | 2009-11-03 | 2013-12-25 | Bayer Intellectual Property GmbH | Auswahlverfahren für additive in photopolymeren |
| ES2522840T3 (es) | 2010-03-18 | 2014-11-18 | Basf Se | Procedimiento para la preparación de isocianatos |
| US8981145B2 (en) | 2010-03-18 | 2015-03-17 | Basf Se | Process for preparing isocyanates |
| DE102010019342A1 (de) | 2010-05-05 | 2011-11-10 | Bayer Materialscience Ag | Verfahren zur Herstellung von Isocyanaten in der Gasphase |
| PL214498B1 (pl) | 2010-12-10 | 2013-08-30 | Inst Chemii Przemyslowej Im Prof Ignacego Moscickiego | Sposób wydzielania produktów reakcji fosgenowania toluilenodiaminy (TDA) w fazie gazowej przy wytwarzaniu toluilenodiizocyjanianu (TDI) |
| PL393216A1 (pl) | 2010-12-10 | 2012-06-18 | Zakłady Chemiczne Zachem Spółka Akcyjna | Sposób otrzymywania toluilenodiizocyjanianu (TDI) poprzez prowadzenia reakcji fosgenowania toluilenodiaminy (TDA) w fazie gazowej oraz urządzenie do otrzymywania toluilenodiizocyjanianu (TDI) poprzez prowadzenie reakcji fosgenowania toluilenodiaminy (TDA) w fazie gazowej |
| HUE034207T2 (hu) | 2013-02-08 | 2018-01-29 | Covestro Deutschland Ag | Eljárás primer amin foszfogenálásával gázfázisban elõállított izocianát elválasztására a foszfogenálás gáz halmazállapotú nyerstermékétõl |
| EP2829533A1 (de) | 2013-07-26 | 2015-01-28 | Bayer MaterialScience AG | Verfahren zur herstellung von isocyanaten |
| US9266824B2 (en) | 2014-01-13 | 2016-02-23 | Warsaw Orthopedic, Inc. | Methods and compositions for making an amino acid triisocyanate |
| EP3307708B1 (de) | 2015-06-12 | 2021-12-01 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von diisocyanaten in der gasphase |
| JP6804512B2 (ja) | 2015-07-16 | 2020-12-23 | 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 |
| WO2018002916A1 (en) | 2016-06-26 | 2018-01-04 | Technion Research & Development Foundation Limited | Hhh |
| CN110546135B (zh) | 2017-05-15 | 2021-12-14 | 旭化成株式会社 | 异氰酸酯的制造方法 |
| EP3634947B1 (de) | 2017-06-08 | 2022-09-07 | Covestro Intellectual Property GmbH & Co. KG | Verfahren zur herstellung von isocyanaten in der gasphase |
| CN110914236B (zh) | 2017-06-08 | 2023-01-31 | 科思创德国股份有限公司 | 制备异氰酸酯的方法 |
| EP3524591A1 (en) | 2018-02-13 | 2019-08-14 | Covestro Deutschland AG | Process for the preparation of isocyanates |
| CN112020493B (zh) | 2018-05-15 | 2023-04-21 | 旭化成株式会社 | 氨基甲酸酯的制造方法和异氰酸酯的制造方法 |
| US10626084B2 (en) | 2018-08-03 | 2020-04-21 | Covestro Llc | Method for producing two isocyanates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127341A (en) * | 1980-03-11 | 1981-10-06 | Asahi Chem Ind Co Ltd | New aliphatic triisocyanate, its preparation and nonyellowing polyurethane resin hardener composed thereof |
| JPS60233044A (ja) * | 1984-05-04 | 1985-11-19 | Asahi Chem Ind Co Ltd | ポリイソシアネ−トの製造方法 |
| JPS60233043A (ja) * | 1984-05-04 | 1985-11-19 | Asahi Chem Ind Co Ltd | ポリイソシアネ−トの製法 |
| DE3714439A1 (de) * | 1987-04-30 | 1988-11-10 | Bayer Ag | Verfahren zur herstellung von (cyclo)aliphatischen diisocyanaten |
| JP2986888B2 (ja) * | 1989-10-23 | 1999-12-06 | 三井化学株式会社 | 脂肪族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 |
| US5523467A (en) * | 1994-03-22 | 1996-06-04 | Mitsui Toatsu Chemicals, Inc. | Process for the preparation of aliphatic polyisocyanates |
| DE4412327A1 (de) * | 1994-04-11 | 1995-10-12 | Bayer Ag | Verfahren zur Herstellung von Diisocyanaten |
-
1995
- 1995-06-23 DE DE19523385A patent/DE19523385A1/de not_active Withdrawn
-
1996
- 1996-06-11 DE DE59603399T patent/DE59603399D1/de not_active Expired - Lifetime
- 1996-06-11 EP EP96109316A patent/EP0749958B1/de not_active Expired - Lifetime
- 1996-06-11 ES ES96109316T patent/ES2139279T3/es not_active Expired - Lifetime
- 1996-06-17 US US08/666,725 patent/US5633396A/en not_active Expired - Lifetime
- 1996-06-18 CA CA002179344A patent/CA2179344A1/en not_active Abandoned
- 1996-06-21 JP JP17979596A patent/JP3869494B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0912525A (ja) | 1997-01-14 |
| ES2139279T3 (es) | 2000-02-01 |
| EP0749958A1 (de) | 1996-12-27 |
| US5633396A (en) | 1997-05-27 |
| DE59603399D1 (de) | 1999-11-25 |
| EP0749958B1 (de) | 1999-10-20 |
| CA2179344A1 (en) | 1996-12-24 |
| DE19523385A1 (de) | 1997-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3869494B2 (ja) | トリイソシアネートの製造方法 | |
| US4847408A (en) | Process for the preparation of (cyclo)aliphatic diisocyanates | |
| US5516935A (en) | Process for the production of diisocyanates | |
| KR101433943B1 (ko) | 이소시아네이트의 기상 제조 방법 | |
| EP1275640B1 (de) | Verfahren zur Herstellung von (cyclo)aliphatischen Isocyanaten | |
| US5449818A (en) | Process for the preparation of aromatic diisocyanates | |
| JP5576390B2 (ja) | イソシアネートの製造方法 | |
| EP1935876B1 (de) | Verfahren zur Herstellung von Isocyanaten in der Gasphase | |
| JP5699128B2 (ja) | イソシアネートの製造方法 | |
| JPH0912525A5 (enExample) | ||
| CN106715384B (zh) | 在气相中制备1,5-戊二异氰酸酯的方法 | |
| US8378140B2 (en) | Processes for preparing low-chlorine isocyanates | |
| KR20090104866A (ko) | 이소시아네이트의 제조 방법 | |
| KR20110097790A (ko) | 이소시아네이트의 제조 방법 | |
| KR101564097B1 (ko) | 기체상의 방향족 디이소시아네이트의 제조 방법 | |
| CN103025709B (zh) | 用于在气相中制备异氰酸酯的方法 | |
| US9029594B2 (en) | Separation of ammonium chloride from the gas phase of an isocyanate production process |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20060907 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20060919 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20061013 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20091020 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20101020 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20111020 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121020 Year of fee payment: 6 |
|
| LAPS | Cancellation because of no payment of annual fees |