ES2549980T3 - Preparación de poliisocianatos de tipo trimérico - Google Patents
Preparación de poliisocianatos de tipo trimérico Download PDFInfo
- Publication number
- ES2549980T3 ES2549980T3 ES09002902.6T ES09002902T ES2549980T3 ES 2549980 T3 ES2549980 T3 ES 2549980T3 ES 09002902 T ES09002902 T ES 09002902T ES 2549980 T3 ES2549980 T3 ES 2549980T3
- Authority
- ES
- Spain
- Prior art keywords
- phospholane
- mol
- phosphabiciclononano
- catalyst
- reaction
- 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.)
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- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 30
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000012948 isocyanate Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
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- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000011261 inert gas Substances 0.000 claims abstract description 7
- 239000012298 atmosphere Substances 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 230000008569 process Effects 0.000 abstract description 23
- -1 1-ethyl Chemical group 0.000 abstract description 10
- 150000001718 carbodiimides Chemical class 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 22
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- 150000001875 compounds Chemical class 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000009849 deactivation Effects 0.000 description 7
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
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- HUWKILZNNQBKKT-UHFFFAOYSA-N 1-butylphospholane Chemical compound CCCCP1CCCC1 HUWKILZNNQBKKT-UHFFFAOYSA-N 0.000 description 4
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
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- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- CDGZRUIQNOATAK-UHFFFAOYSA-N 1-methylphospholane Chemical compound CP1CCCC1 CDGZRUIQNOATAK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- 101100135363 Yarrowia lipolytica (strain CLIB 122 / E 150) RIM101 gene Proteins 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 2
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 description 1
- VKLNMSFSTCXMSB-UHFFFAOYSA-N 1,1-diisocyanatopentane Chemical compound CCCCC(N=C=O)N=C=O VKLNMSFSTCXMSB-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- VMOSOYFJISIDIQ-UHFFFAOYSA-N 1-butylphospholane Chemical compound C(CCC)P1CCCC1.C(CCC)P1CCCC1 VMOSOYFJISIDIQ-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
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- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
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- DTUNKRWZSJSVIH-UHFFFAOYSA-N 9-bicyclo[3.3.1]nonanyl-oxido-oxophosphanium Chemical class P(=O)(=O)C1C2CCCC1CCC2 DTUNKRWZSJSVIH-UHFFFAOYSA-N 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
- C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0255—Phosphorus containing compounds
- B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08004769 | 2008-03-14 | ||
| EP08004769A EP2100885A1 (de) | 2008-03-14 | 2008-03-14 | Herstellung von Polyisocyanaten vom Trimertyp |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2549980T3 true ES2549980T3 (es) | 2015-11-03 |
Family
ID=39531315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09002902.6T Active ES2549980T3 (es) | 2008-03-14 | 2009-02-28 | Preparación de poliisocianatos de tipo trimérico |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8097691B2 (enExample) |
| EP (2) | EP2100885A1 (enExample) |
| JP (1) | JP5478096B2 (enExample) |
| CN (1) | CN101531641B (enExample) |
| CA (1) | CA2658090A1 (enExample) |
| ES (1) | ES2549980T3 (enExample) |
| HU (1) | HUE026157T2 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011077573A1 (de) | 2011-06-15 | 2012-12-20 | Henkel Ag & Co. Kgaa | 2K-Polyurethan-Klebstoff mit aliphatischem Vernetzer |
| CN109970950A (zh) | 2011-11-30 | 2019-07-05 | 科思创德国股份有限公司 | 用于连续异氰酸酯改性的方法 |
| EP2700665B1 (de) * | 2012-08-23 | 2018-12-05 | Covestro Deutschland AG | Verfahren zur Trimerisierung cycloaliphatischer Diisocyanate |
| CN106604944B (zh) * | 2014-09-04 | 2019-03-15 | 旭化成株式会社 | 多异氰酸酯组合物、涂料组合物、涂膜及其制造方法、以及潮湿稳定化方法 |
| CA2980669C (en) * | 2015-04-21 | 2023-09-19 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
| US10717805B2 (en) * | 2015-04-21 | 2020-07-21 | Covestro Deutschland Ag | Process for producing polyisocyanurate plastics |
| CA2982261C (en) * | 2015-04-21 | 2023-09-26 | Covestro Deutschland Ag | Solids based on polyisocyanurate polymers produced under adiabatic conditions |
| US10597484B2 (en) * | 2015-04-21 | 2020-03-24 | Covestro Deutschland Ag | Polyisocyanurate plastics having high thermal stability |
| JP6568996B2 (ja) * | 2016-03-09 | 2019-08-28 | 旭化成株式会社 | ポリイソシアネート組成物、コーティング組成物、水系コーティング組成物、及びコーティング基材 |
| CN108499606B (zh) * | 2017-02-24 | 2020-11-20 | 万华化学集团股份有限公司 | 一种邻巯基芳基氮杂环卡宾金属配合物催化剂及其制备方法和用途 |
| CN106902872B (zh) * | 2017-03-29 | 2019-09-03 | 万华化学集团股份有限公司 | 一种异氰酸酯聚合催化剂及其制备方法，及其用于制备聚异氰酸酯的方法 |
| WO2020016119A1 (de) | 2018-07-16 | 2020-01-23 | Covestro Deutschland Ag | Verfahren zur oligomerisierung von isocyanaten mit polyedrischen silsesquioxan-katalysatoren |
| FR3095448B1 (fr) | 2019-04-26 | 2022-12-23 | Bostik Sa | Adhesif de lamination pour sterilisation |
| EP3741766B1 (de) | 2019-05-24 | 2022-08-31 | Covestro Intellectual Property GmbH & Co. KG | Neue katalysatoren für die synthese von oligomeren isocyanaten |
| CN110790895B (zh) * | 2019-11-08 | 2021-09-07 | 万华化学集团股份有限公司 | 一种脂肪族多异氰酸酯组合物、其制备方法及涂料组合物 |
| US20230211530A1 (en) * | 2020-07-02 | 2023-07-06 | Covestro Deutschland Ag | Coatings from polyisocyanurate coatings (rim) and their use in injection molding processes |
| CN111793182B (zh) * | 2020-07-15 | 2022-04-22 | 万华化学集团股份有限公司 | 一种多异氰酸酯组合物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2671082A (en) | 1951-09-25 | 1954-03-02 | Du Pont | Preparation of aromatic isocyanate dimers |
| US2853518A (en) | 1956-07-30 | 1958-09-23 | Du Pont | Chemical process |
| US2853473A (en) | 1956-08-27 | 1958-09-23 | Du Pont | Production of carbodiimides |
| GB856372A (en) | 1958-02-24 | 1960-12-14 | Ici Ltd | Derivatives of isocyanuric acid |
| NL276588A (enExample) | 1961-04-01 | |||
| GB1166316A (en) | 1966-02-02 | 1969-10-08 | Bayer Ag | Polymerization of Aromatic Polyisocyanates |
| DE1670720A1 (de) | 1966-07-21 | 1971-01-14 | Bayer Ag | Verfahren zur Herstellung von aliphatisch substituierten Uretdionen |
| DE1954093C3 (de) | 1968-11-15 | 1978-12-21 | Mobay Chemical Corp., Pittsburgh, Pa. (V.St.A.) | Verfahren zur Herstellung von polymeren organischen Isocyanaten |
| DE1934763A1 (de) | 1969-07-09 | 1971-01-28 | Veba Chemie Ag | Verfahren zur Herstellung von oligomerer Isocyanate |
| DE3432081A1 (de) | 1984-08-31 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von oligomeren polyisocyanaten und ihre verwendung bei der herstellung von polyurethankunststoffen |
| DE3437635A1 (de) | 1984-10-13 | 1986-04-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von uretdiongruppen aufweisenden verbindungen, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung bei der herstellung von polyurethankunststoffen |
| DE3809261A1 (de) * | 1988-03-19 | 1989-09-28 | Bayer Ag | Verfahren zur herstellung von uretdion- und isocyanuratgruppen aufweisenden polyisocyanatgemischen |
| DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| CA2264429A1 (en) | 1999-03-03 | 2000-09-03 | Allan James Robertson | Preparation of 9-hydrocarbyl-9-phosphabicyclononanes |
| DE10035013A1 (de) * | 2000-07-19 | 2002-01-31 | Bayer Ag | Verfahren zur Herstellung von Uretdionpolyisocyanaten mit verbesserter Monomerenstabilität |
| DE10254878A1 (de) | 2002-11-25 | 2004-06-03 | Bayer Ag | Herstellung uretdiongruppenhaltiger Polyisocyanate |
| DE10354544A1 (de) | 2003-11-21 | 2005-06-23 | Bayer Materialscience Ag | Herstellung uretdiongruppenhaltiger Polyisocyanate |
-
2008
- 2008-03-14 EP EP08004769A patent/EP2100885A1/de not_active Withdrawn
-
2009
- 2009-02-28 EP EP09002902.6A patent/EP2100886B1/de not_active Not-in-force
- 2009-02-28 HU HUE09002902A patent/HUE026157T2/en unknown
- 2009-02-28 ES ES09002902.6T patent/ES2549980T3/es active Active
- 2009-03-11 CA CA002658090A patent/CA2658090A1/en not_active Abandoned
- 2009-03-12 US US12/402,855 patent/US8097691B2/en not_active Expired - Fee Related
- 2009-03-13 JP JP2009060660A patent/JP5478096B2/ja not_active Expired - Fee Related
- 2009-03-13 CN CN200910128728.1A patent/CN101531641B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8097691B2 (en) | 2012-01-17 |
| HUE026157T2 (en) | 2016-05-30 |
| JP5478096B2 (ja) | 2014-04-23 |
| EP2100886B1 (de) | 2015-08-19 |
| EP2100886A3 (de) | 2011-08-31 |
| CN101531641A (zh) | 2009-09-16 |
| CN101531641B (zh) | 2015-04-08 |
| US20090234091A1 (en) | 2009-09-17 |
| CA2658090A1 (en) | 2009-09-14 |
| EP2100885A1 (de) | 2009-09-16 |
| JP2009221478A (ja) | 2009-10-01 |
| HK1137019A1 (en) | 2010-07-16 |
| EP2100886A2 (de) | 2009-09-16 |
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