JP2014205854A5 - - Google Patents
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- Publication number
- JP2014205854A5 JP2014205854A5 JP2014142501A JP2014142501A JP2014205854A5 JP 2014205854 A5 JP2014205854 A5 JP 2014205854A5 JP 2014142501 A JP2014142501 A JP 2014142501A JP 2014142501 A JP2014142501 A JP 2014142501A JP 2014205854 A5 JP2014205854 A5 JP 2014205854A5
- Authority
- JP
- Japan
- Prior art keywords
- diisocyanate
- reactor
- group
- isocyanate
- conversion step
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims description 63
- 239000012948 isocyanate Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000002513 isocyanates Chemical class 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 8
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 6
- 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 claims description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000006384 oligomerization reaction Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000013638 trimer Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- -1 aromatic isocyanates Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000005056 polyisocyanate Substances 0.000 claims description 3
- 229920001228 polyisocyanate Polymers 0.000 claims description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims description 3
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 claims description 2
- NGKKXKRXUOBKGI-UHFFFAOYSA-N 1,2,9-triisocyanatononane Chemical compound O=C=NCCCCCCCC(N=C=O)CN=C=O NGKKXKRXUOBKGI-UHFFFAOYSA-N 0.000 claims description 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 2
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 claims description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 claims description 2
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 claims description 2
- GNDOBZLRZOCGAS-JTQLQIEISA-N 2-isocyanatoethyl (2s)-2,6-diisocyanatohexanoate Chemical compound O=C=NCCCC[C@H](N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-JTQLQIEISA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 2
- RZBQQMOPDAXLOS-UHFFFAOYSA-N CC1=CC=C(N=C=O)C=C1N=C=O.O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O.O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O RZBQQMOPDAXLOS-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 1
- MTKLMAGWSTVQPY-UHFFFAOYSA-N N(=C=O)C1(C2CCC1(CC2)C)N=C=O Chemical compound N(=C=O)C1(C2CCC1(CC2)C)N=C=O MTKLMAGWSTVQPY-UHFFFAOYSA-N 0.000 claims 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0852233A FR2929612B1 (fr) | 2008-04-03 | 2008-04-03 | Procede d'oligomerisation des isocyanates en continu |
| FR0852233 | 2008-04-03 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011502424A Division JP2011517454A (ja) | 2008-04-03 | 2009-04-02 | イソシアネートの連続的オリゴマー化の方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014205854A JP2014205854A (ja) | 2014-10-30 |
| JP2014205854A5 true JP2014205854A5 (enExample) | 2016-01-28 |
| JP5941106B2 JP5941106B2 (ja) | 2016-06-29 |
Family
ID=40032531
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011502424A Withdrawn JP2011517454A (ja) | 2008-04-03 | 2009-04-02 | イソシアネートの連続的オリゴマー化の方法 |
| JP2014142501A Active JP5941106B2 (ja) | 2008-04-03 | 2014-07-10 | イソシアネートの連続的オリゴマー化の方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011502424A Withdrawn JP2011517454A (ja) | 2008-04-03 | 2009-04-02 | イソシアネートの連続的オリゴマー化の方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8378139B2 (enExample) |
| EP (1) | EP2271684B8 (enExample) |
| JP (2) | JP2011517454A (enExample) |
| CN (1) | CN102015802B (enExample) |
| BR (1) | BRPI0906533B1 (enExample) |
| FR (1) | FR2929612B1 (enExample) |
| HU (1) | HUE046011T2 (enExample) |
| PL (1) | PL2271684T3 (enExample) |
| WO (1) | WO2009136032A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2649097T3 (es) | 2011-11-30 | 2018-01-10 | Covestro Deutschland Ag | Procedimiento para la modificación continua de isocianato |
| CN103435778A (zh) * | 2013-08-27 | 2013-12-11 | 华南理工大学 | 一种六亚甲基二异氰酸酯三聚体固化剂的制备方法 |
| CN106062026B (zh) * | 2014-03-04 | 2019-05-17 | 三井化学株式会社 | 异氰脲酸酯组合物 |
| US10167358B2 (en) * | 2015-08-17 | 2019-01-01 | Covestro Deutschland Ag | Process for modifying isocyanates with use of cyclic ammonium salts as catalyst |
| CN108822276B (zh) * | 2018-05-29 | 2021-01-19 | 武汉理工大学 | 一种pvc/pet复合膜胶黏剂的制备方法 |
| CN109651279B (zh) * | 2018-11-19 | 2020-11-24 | 万华化学（宁波）有限公司 | 一种低色度、储存稳定的脂肪族多异氰酸酯的制备方法 |
| CN114874129B (zh) * | 2022-06-14 | 2024-06-14 | 贵州民族大学 | 一种可低温高效解封的封闭型异氰酸酯的制备方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI830714A7 (fi) * | 1982-03-03 | 1983-09-04 | Castle & Cooke Techniculture | Apparatur, process och foerfarande foer kontinuerlig polymerisation |
| AU5949390A (en) * | 1989-06-27 | 1991-01-17 | Dow Chemical Company, The | Melt polymerization process for making polyurethanes |
| JP3242697B2 (ja) * | 1991-06-19 | 2001-12-25 | 三井化学株式会社 | ウレタン化反応方法 |
| WO1994015985A1 (en) * | 1992-12-31 | 1994-07-21 | The Dow Chemical Company | Thermoplastic polyurethanes and a process for their preparation |
| JP3996214B2 (ja) * | 1994-07-21 | 2007-10-24 | 三井化学ポリウレタン株式会社 | イソシアヌレート化及び／又はアロファネート化方法、並びにイソシアヌレート基及び／又はアロファネート基含有ポリイソシアネートの製造法 |
| ZA9810038B (en) * | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
| DE19758050A1 (de) * | 1997-12-29 | 1999-07-01 | Huels Chemische Werke Ag | Verfahren zur Herstellung eines farbreduzierten isocyanatgruppenhaltigen Polyisocyanats auf Basis von 1-Isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexan (IPDI) |
| US6534617B1 (en) * | 1998-12-02 | 2003-03-18 | Kraton Polymers U.S. Llc | Extruder process for making thermoplastic polyurethanes |
| US6258310B1 (en) * | 1999-03-18 | 2001-07-10 | Basf Corporation | Cross-linking thermoplastic polyurethane |
| US6100360A (en) * | 1999-05-19 | 2000-08-08 | Acelon Chemicals & Fiber Corporation | Process for preparing a polyurethane elastic fiber |
| FR2804112B1 (fr) * | 2000-01-20 | 2004-04-30 | Rhodia Chimie Sa | Procede d'obtention de cyclotrimeres d'isocyanate(s) ramifie(s) faiblement colore(s) et composition en decoulant |
| CN100341860C (zh) * | 2000-01-20 | 2007-10-10 | 罗狄亚化学公司 | 制备轻度着色的支化多异氰酸酯的方法及所得到的组合物 |
| US6921518B2 (en) * | 2000-01-25 | 2005-07-26 | Meggitt (Uk) Limited | Chemical reactor |
| ATE285842T1 (de) * | 2000-01-25 | 2005-01-15 | Meggitt Uk Ltd | Chemischer reaktor mit wärmeaustauscher |
| FR2823995B1 (fr) * | 2001-04-25 | 2008-06-06 | Alfa Laval Vicarb | Dispositif perfectionne d'echange et/ou de reaction entre fluides |
| DE10131525A1 (de) * | 2001-07-02 | 2003-01-16 | Degussa | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat |
| DE10159803A1 (de) * | 2001-12-05 | 2003-07-03 | Degussa | Katalysatoren und Verfahren zur Herstellung von Isocyanuratgruppen enthaltenden Polyisocyanaten und deren Verwendung |
| SE524540C2 (sv) * | 2002-11-18 | 2004-08-24 | Alfa Laval Corp Ab | Flödesstyrande insats i en reaktorkammare samt reaktor försedd med insatsen |
| DE10309432A1 (de) * | 2003-03-05 | 2004-09-16 | Degussa Ag | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten auf Basis von Isophorondiisocyanat |
| DE502005004848D1 (de) * | 2004-12-13 | 2008-09-04 | Basf Se | Ilen biuretgruppenhaltigen polyisocyanaten |
| WO2006063749A1 (de) * | 2004-12-13 | 2006-06-22 | Basf Aktiengesellschaft | Verfahren zur herstellung von polyisocyanaten |
| FR2880967A1 (fr) * | 2005-01-14 | 2006-07-21 | Alfa Laval Vicarb Sa | Optimisation d'une reaction chimique dans un reacteur ouvert du type a plaques |
| US7795359B2 (en) * | 2005-03-04 | 2010-09-14 | Novartis Ag | Continuous process for production of polymeric materials |
-
2008
- 2008-04-03 FR FR0852233A patent/FR2929612B1/fr active Active
-
2009
- 2009-04-02 US US12/936,342 patent/US8378139B2/en active Active
- 2009-04-02 BR BRPI0906533-4A patent/BRPI0906533B1/pt active IP Right Grant
- 2009-04-02 EP EP09742230.7A patent/EP2271684B8/fr active Active
- 2009-04-02 HU HUE09742230A patent/HUE046011T2/hu unknown
- 2009-04-02 PL PL09742230T patent/PL2271684T3/pl unknown
- 2009-04-02 WO PCT/FR2009/050562 patent/WO2009136032A1/fr not_active Ceased
- 2009-04-02 CN CN200980112435.2A patent/CN102015802B/zh active Active
- 2009-04-02 JP JP2011502424A patent/JP2011517454A/ja not_active Withdrawn
-
2014
- 2014-07-10 JP JP2014142501A patent/JP5941106B2/ja active Active
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