CA2230148A1 - Process for the production of polyisocyanates having a biuret structure - Google Patents
Process for the production of polyisocyanates having a biuret structure Download PDFInfo
- Publication number
- CA2230148A1 CA2230148A1 CA002230148A CA2230148A CA2230148A1 CA 2230148 A1 CA2230148 A1 CA 2230148A1 CA 002230148 A CA002230148 A CA 002230148A CA 2230148 A CA2230148 A CA 2230148A CA 2230148 A1 CA2230148 A1 CA 2230148A1
- Authority
- CA
- Canada
- Prior art keywords
- organic
- temperature
- mixing chamber
- reaction mixture
- process according
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 10
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 150000004985 diamines Chemical class 0.000 claims abstract description 30
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 29
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical class C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 3
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic isocya-nates Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- NXBQNXVZAXYUBY-UHFFFAOYSA-N 2-oxopropyl acetate;zinc Chemical compound [Zn].CC(=O)COC(C)=O NXBQNXVZAXYUBY-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19707576A DE19707576C1 (de) | 1997-02-26 | 1997-02-26 | Verfahren zur Herstellung von Polyisocyanaten mit Biuretstruktur |
| DE19707576.2 | 1997-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2230148A1 true CA2230148A1 (en) | 1998-08-26 |
Family
ID=7821460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002230148A Abandoned CA2230148A1 (en) | 1997-02-26 | 1998-02-23 | Process for the production of polyisocyanates having a biuret structure |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5994491A (enExample) |
| EP (1) | EP0861829B1 (enExample) |
| JP (1) | JP4102471B2 (enExample) |
| KR (1) | KR100525684B1 (enExample) |
| BR (1) | BR9800208A (enExample) |
| CA (1) | CA2230148A1 (enExample) |
| DE (2) | DE19707576C1 (enExample) |
| ES (1) | ES2217447T3 (enExample) |
| MX (1) | MX9801513A (enExample) |
| TW (1) | TW555739B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4514293B2 (ja) * | 2000-07-13 | 2010-07-28 | 旭化成ケミカルズ株式会社 | ビウレット型ポリイソシアネート組成物及びその製造方法 |
| BR0212992A (pt) * | 2001-09-21 | 2004-09-21 | Du Pont | Processo para a preparação de poliisocianatos, composição dos mesmos, composição de revestimento, substrato revestido e substrato automotivo |
| US20080064829A1 (en) * | 2002-09-20 | 2008-03-13 | Adams Jerome T | Preparation and use of biuret-containing polyisocyanates as cross-linking agents for coatings |
| US6838542B1 (en) | 2003-07-24 | 2005-01-04 | Bayer Materialscience Llc | Stable liquid biuret modified and biuret allophanate modified diphenylmethane diisocyanates, prepolymers thereof, and processes for their preparation |
| US7378543B2 (en) * | 2003-07-24 | 2008-05-27 | Bayer Materialscience Llc | Stable liquid biuret modified and biuret allophanate modified toluene diisocyanates, prepolymers thereof, and processes for their preparation |
| US7772307B2 (en) * | 2003-08-27 | 2010-08-10 | Great Eastern Resins Industrial Co., Ltd. | Water dispersible polyisocyanate composition and its uses |
| DE10359627A1 (de) * | 2003-12-18 | 2005-07-21 | Bayer Materialscience Ag | Verfahren zur Herstellung von Diisocyanaten |
| JP2013534960A (ja) * | 2010-06-29 | 2013-09-09 | コンストラクション リサーチ アンド テクノロジー ゲーエムベーハー | チキソトロープ剤の製造法及びその使用 |
| EP2681189A1 (de) | 2011-03-03 | 2014-01-08 | Basf Se | Verfahren zur herstellung von biuretgruppenhaltigen polyisocyanaten |
| US8609887B2 (en) | 2011-03-03 | 2013-12-17 | Basf Se | Process for preparing polyisocyanates comprising biuret groups |
| JP7397865B2 (ja) | 2018-10-31 | 2023-12-13 | ダウ グローバル テクノロジーズ エルエルシー | 有機溶液からモノイソシアネートを除去するための方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3954825A (en) * | 1973-08-09 | 1976-05-04 | E. I. Du Pont De Nemours And Company | Biuret polyisocyanates |
| DE2803103A1 (de) * | 1978-01-25 | 1979-07-26 | Bayer Ag | Verfahren zur herstellung von biuret- und/oder harnstoffgruppen aufweisenden organischen polyisocyanaten |
| DE3114638A1 (de) * | 1981-04-10 | 1982-10-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von harnstoff- und/oder biuretgruppen aufweisenden aromatischen polyisocyanaten und ihre verwendung als isocyanatkomponente bei der herstellung von polyurethankunststoffen |
| DE3700209A1 (de) * | 1987-01-07 | 1988-07-21 | Bayer Ag | Verfahren zur herstellung von polyisocyanaten mit biuretstruktur |
-
1997
- 1997-02-26 DE DE19707576A patent/DE19707576C1/de not_active Expired - Fee Related
-
1998
- 1998-02-10 TW TW087101724A patent/TW555739B/zh active
- 1998-02-13 EP EP98102481A patent/EP0861829B1/de not_active Expired - Lifetime
- 1998-02-13 US US09/022,792 patent/US5994491A/en not_active Expired - Lifetime
- 1998-02-13 ES ES98102481T patent/ES2217447T3/es not_active Expired - Lifetime
- 1998-02-13 DE DE59811253T patent/DE59811253D1/de not_active Expired - Lifetime
- 1998-02-20 BR BR9800208A patent/BR9800208A/pt active Search and Examination
- 1998-02-23 CA CA002230148A patent/CA2230148A1/en not_active Abandoned
- 1998-02-24 JP JP05736298A patent/JP4102471B2/ja not_active Expired - Fee Related
- 1998-02-25 KR KR10-1998-0005913A patent/KR100525684B1/ko not_active Expired - Fee Related
- 1998-02-25 MX MX9801513A patent/MX9801513A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE19707576C1 (de) | 1998-04-16 |
| KR100525684B1 (ko) | 2005-12-21 |
| JPH10237037A (ja) | 1998-09-08 |
| DE59811253D1 (de) | 2004-06-03 |
| ES2217447T3 (es) | 2004-11-01 |
| EP0861829A3 (de) | 2002-08-07 |
| EP0861829B1 (de) | 2004-04-28 |
| BR9800208A (pt) | 1999-06-29 |
| EP0861829A2 (de) | 1998-09-02 |
| TW555739B (en) | 2003-10-01 |
| KR19980071684A (ko) | 1998-10-26 |
| MX9801513A (es) | 1998-11-30 |
| JP4102471B2 (ja) | 2008-06-18 |
| US5994491A (en) | 1999-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |