JP6250682B2 - ポリカルボジイミドの精製方法 - Google Patents
ポリカルボジイミドの精製方法 Download PDFInfo
- Publication number
- JP6250682B2 JP6250682B2 JP2015532403A JP2015532403A JP6250682B2 JP 6250682 B2 JP6250682 B2 JP 6250682B2 JP 2015532403 A JP2015532403 A JP 2015532403A JP 2015532403 A JP2015532403 A JP 2015532403A JP 6250682 B2 JP6250682 B2 JP 6250682B2
- Authority
- JP
- Japan
- Prior art keywords
- polycarbodiimide
- diisocyanate
- carbodiimidization catalyst
- mixture
- entrainer
- 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
- 238000000034 method Methods 0.000 title claims description 92
- 238000000746 purification Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims description 176
- 239000000203 mixture Substances 0.000 claims description 149
- 125000005442 diisocyanate group Chemical group 0.000 claims description 112
- 238000004821 distillation Methods 0.000 claims description 92
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- 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 30
- 150000002430 hydrocarbons Chemical class 0.000 claims description 27
- 238000006116 polymerization reaction Methods 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 26
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 13
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 12
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 claims description 12
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 239000003431 cross linking reagent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
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- 238000004383 yellowing Methods 0.000 description 3
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- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 2
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 description 2
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 2
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07C267/00—Carbodiimides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6511—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38 compounds of group C08G18/3203
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP12185051 | 2012-09-19 | ||
| EP12185051.5 | 2012-09-19 | ||
| PCT/EP2013/069451 WO2014044742A1 (en) | 2012-09-19 | 2013-09-19 | Process for the purification of a polycarbodiimide |
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| JP2015531814A JP2015531814A (ja) | 2015-11-05 |
| JP2015531814A5 JP2015531814A5 (enExample) | 2016-11-10 |
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| EP (1) | EP2897934B1 (enExample) |
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|---|---|---|---|---|
| WO2014044743A1 (en) * | 2012-09-19 | 2014-03-27 | Basf Se | Process for producing polycarbodiimide |
| ES2833098T3 (es) | 2013-02-22 | 2021-06-14 | Basf Se | Procedimiento para la producción de preparaciones de poliuretano acuosas |
| CA3086223A1 (en) * | 2017-12-20 | 2019-06-27 | Lanxess Deutschland Gmbh | Method for producing carbodiimides |
| EP3868803A1 (de) * | 2020-02-18 | 2021-08-25 | Covestro Deutschland AG | Verfahren zur carbodiimidisierung |
| EP4667454A1 (de) | 2024-06-18 | 2025-12-24 | LANXESS Deutschland GmbH | Verfahren zur herstellung von tertiären araliphatischen carbodiimiden |
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| US5352400A (en) | 1992-04-29 | 1994-10-04 | E. I. Du Pont De Nemours And Company | Carbodiimides and processes therefor |
| DE4242504A1 (de) * | 1992-12-16 | 1994-06-23 | Rhein Chemie Rheinau Gmbh | Verfahren zur Herstellung von aromatischen Carbodiimiden |
| JP2598864B2 (ja) | 1993-01-14 | 1997-04-09 | 株式会社ワールドケミカル | 液体回収装置 |
| DE4302697A1 (de) | 1993-02-01 | 1994-08-04 | Bayer Ag | Verfahren zur Herstellung organischer Carbodiimide und ihre Verwendung als Kunststoff-Stabilisatoren |
| JP3258127B2 (ja) * | 1993-04-13 | 2002-02-18 | 三井化学株式会社 | ポリカルボジイミド及びその製造方法 |
| JP3845874B2 (ja) * | 1994-10-25 | 2006-11-15 | 東亞合成株式会社 | アクリル酸またはメタクリル酸エステルの製造方法 |
| JP3618890B2 (ja) * | 1996-03-14 | 2005-02-09 | 日清紡績株式会社 | ジシクロヘキシルカルボジイミドの製造方法 |
| US6184410B1 (en) | 1998-05-14 | 2001-02-06 | Basf Aktiengesellschaft | Carbodiimides based on 1,3-bis(1-methyl-1-isocyanatoethyl)benzene |
| NL1023817C2 (nl) | 2003-07-03 | 2005-01-04 | Stahl Int Bv | Werkwijze voor de bereiding van stabiele polycarbodiimide dispersies in water, welke geen organische oplosmiddelen bevatten en als vernettingsmiddel kunnen worden gebruikt. |
| JP5041794B2 (ja) * | 2006-12-07 | 2012-10-03 | 住化バイエルウレタン株式会社 | 変性ポリイソシアネートの製造方法 |
| EP2350228A1 (en) | 2008-10-29 | 2011-08-03 | Basf Se | A proppant |
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- 2013-09-19 US US14/429,151 patent/US9481641B2/en active Active
- 2013-09-19 JP JP2015532403A patent/JP6250682B2/ja not_active Expired - Fee Related
- 2013-09-19 BR BR112015006036A patent/BR112015006036A2/pt not_active Application Discontinuation
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Also Published As
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| CN104797554A (zh) | 2015-07-22 |
| CN104797554B (zh) | 2017-03-22 |
| JP2015531814A (ja) | 2015-11-05 |
| US20150225336A1 (en) | 2015-08-13 |
| EP2897934B1 (en) | 2016-12-28 |
| EP2897934A1 (en) | 2015-07-29 |
| US9481641B2 (en) | 2016-11-01 |
| BR112015006036A2 (pt) | 2017-07-04 |
| WO2014044742A1 (en) | 2014-03-27 |
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