JP2012508303A - イソシアネートの三量化触媒系、前駆体配合物、イソシアネートの三量化方法、それから作製された硬質ポリイソシアヌレート／ポリウレタン発泡体、および該発泡体の作製方法 - Google Patents
イソシアネートの三量化触媒系、前駆体配合物、イソシアネートの三量化方法、それから作製された硬質ポリイソシアヌレート／ポリウレタン発泡体、および該発泡体の作製方法 Download PDFInfo
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- JP2012508303A JP2012508303A JP2011535728A JP2011535728A JP2012508303A JP 2012508303 A JP2012508303 A JP 2012508303A JP 2011535728 A JP2011535728 A JP 2011535728A JP 2011535728 A JP2011535728 A JP 2011535728A JP 2012508303 A JP2012508303 A JP 2012508303A
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- Prior art keywords
- trimerization
- optionally
- catalyst system
- isocyanate
- trimerization catalyst
- 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.)
- Ceased
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- 239000012948 isocyanate Substances 0.000 title claims abstract description 126
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 126
- 239000003054 catalyst Substances 0.000 title claims abstract description 123
- 238000005829 trimerization reaction Methods 0.000 title claims abstract description 121
- 239000006260 foam Substances 0.000 title claims abstract description 104
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 54
- 238000009472 formulation Methods 0.000 title claims abstract description 53
- 239000002243 precursor Substances 0.000 title claims abstract description 35
- 229920000582 polyisocyanurate Polymers 0.000 title claims description 62
- 239000011495 polyisocyanurate Substances 0.000 title claims description 62
- 229920005830 Polyurethane Foam Polymers 0.000 title description 3
- 239000011496 polyurethane foam Substances 0.000 title description 3
- -1 imidazolinium cation Chemical class 0.000 claims abstract description 58
- 150000003077 polyols Chemical class 0.000 claims abstract description 53
- 239000013638 trimer Substances 0.000 claims abstract description 44
- 229920005862 polyol Polymers 0.000 claims abstract description 40
- 150000001450 anions Chemical class 0.000 claims abstract description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims abstract description 21
- 230000004913 activation Effects 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000003063 flame retardant Substances 0.000 claims description 27
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 17
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- 125000003118 aryl group Chemical group 0.000 claims description 12
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- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005442 diisocyanate group Chemical group 0.000 claims description 10
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 6
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 3
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- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
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- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 claims description 3
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- PQGFDBPIIHVOKX-UHFFFAOYSA-O 2,3,4,5-tetrabutyl-1h-imidazol-3-ium Chemical compound CCCC[NH+]1C(CCCC)=NC(CCCC)=C1CCCC PQGFDBPIIHVOKX-UHFFFAOYSA-O 0.000 claims 1
- HADBBULLJCWBEI-UHFFFAOYSA-O 2,3,4,5-tetraethyl-1h-imidazol-3-ium Chemical compound CC[NH+]1C(CC)=NC(CC)=C1CC HADBBULLJCWBEI-UHFFFAOYSA-O 0.000 claims 1
- RZVBWHCDKFUXQQ-UHFFFAOYSA-N 2,3,4,5-tetraphenyl-1H-imidazol-3-ium acetate Chemical compound CC(=O)[O-].C1=CC=C(C=C1)C2=C([N+](=C(N2)C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5 RZVBWHCDKFUXQQ-UHFFFAOYSA-N 0.000 claims 1
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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 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 239000004604 Blowing Agent Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
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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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- 239000011541 reaction mixture Substances 0.000 description 6
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- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
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- JDBIDRXYAGVDQR-UHFFFAOYSA-N 1,3-ditert-butylimidazolidin-1-ium;acetate Chemical group CC([O-])=O.CC(C)(C)N1CC[NH+](C(C)(C)C)C1 JDBIDRXYAGVDQR-UHFFFAOYSA-N 0.000 description 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 4
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Classifications
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
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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
- C08G18/02—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
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1858—Catalysts containing secondary or tertiary amines or salts thereof having carbon-to-nitrogen double bonds
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and acids
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
-
- 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
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US11319608P | 2008-11-10 | 2008-11-10 | |
| US61/113,196 | 2008-11-10 | ||
| PCT/US2009/063733 WO2010054317A2 (en) | 2008-11-10 | 2009-11-09 | An isocyanate trimerisation catalyst system, a precursor formulation, a process for trimerising isocyanates, rigid polyisocyanurate/polyurethane foams made therefrom, and a process for making such foams |
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| JP2012508303A true JP2012508303A (ja) | 2012-04-05 |
| JP2012508303A5 JP2012508303A5 (https=) | 2012-12-27 |
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| ES (1) | ES2436013T3 (https=) |
| WO (1) | WO2010054317A2 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2012508302A (ja) * | 2008-11-10 | 2012-04-05 | ダウ グローバル テクノロジーズ エルエルシー | イソシアネートの三量化触媒系、前駆体配合物、イソシアネートの三量化方法、それから作製された硬質ポリイソシアヌレート／ポリウレタン発泡体、および該発泡体の作製方法 |
| US8709544B2 (en) * | 2009-11-23 | 2014-04-29 | Basf Se | Catalysts for polyurethane coating compounds |
| CN102432813B (zh) * | 2011-03-21 | 2014-04-30 | 江苏科泰绝热新材料有限公司 | 一种用离子液体催化制备pir材料的方法 |
| WO2013024108A1 (de) * | 2011-08-16 | 2013-02-21 | Bayer Intellectual Property Gmbh | Verfahren zur herstellung eines polyurethan-polyisocyanurat-hartschaums |
| EP2602023A1 (de) * | 2011-12-07 | 2013-06-12 | Basf Se | Katalysatorkombination zur Herstellung von Polyurethanschaumstoffformkörpern |
| EP2797994A2 (en) | 2011-12-30 | 2014-11-05 | Dow Global Technologies LLC | Foam composition with olefin block copolymer gel particles |
| CN104093759B (zh) * | 2012-02-08 | 2016-09-21 | 科思创德国股份有限公司 | 聚氨酯-聚异氰脲酸酯-硬质泡沫材料的制备方法 |
| CN105189595B (zh) | 2013-03-28 | 2018-03-02 | 陶氏环球技术有限责任公司 | 用于制备氨基甲酸酯‑异氰脲酸酯的方法 |
| AU2014318649B2 (en) | 2013-09-13 | 2017-09-07 | Dow Global Technologies Llc | Thixotropic polyol compositions containing dispersed urethane-modified polyisocyanurates |
| US10017599B2 (en) | 2013-09-13 | 2018-07-10 | Dow Global Technologies Llc | Polyisocyanate polyaddition polyol manufacturing process using stabilizers |
| RU2676285C1 (ru) * | 2013-12-16 | 2018-12-27 | Роквул Интернэшнл А/С | Композиты на основе вспененного полиизоцианурата, их получение и применение |
| EP2924058B1 (en) | 2014-03-28 | 2016-05-25 | Huntsman International Llc | Reinforced organic natural fiber composites |
| RU2707290C2 (ru) | 2014-04-03 | 2019-11-26 | Хантсмэн Интернэшнл Ллс | Катализатор тримеризации изоцианата для изготовления полиизоцианурат-содержащих пеноматериалов |
| EP3286241B1 (en) * | 2015-04-21 | 2020-04-15 | Covestro Deutschland AG | Process for producing polyisocyanurate plastics |
| WO2016170059A1 (en) * | 2015-04-21 | 2016-10-27 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
| US10752724B2 (en) * | 2015-04-21 | 2020-08-25 | Covestro Deutschland Ag | Process for producing polyisocvanurate plastics having functionalized surfaces |
| US10597484B2 (en) * | 2015-04-21 | 2020-03-24 | Covestro Deutschland Ag | Polyisocyanurate plastics having high thermal stability |
| EP3085720A1 (de) * | 2015-04-21 | 2016-10-26 | Covestro Deutschland AG | Hydrophil modifizierter polyisocyanuratkunststoff und verfahren zu dessen herstellung |
| CN107021920B (zh) * | 2016-08-12 | 2019-07-23 | 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 |
| WO2018087399A1 (de) * | 2016-11-14 | 2018-05-17 | Covestro Deutschland Ag | Beschichtungszusammensetzungen mit dualer härtung |
| WO2019014582A1 (en) * | 2017-07-13 | 2019-01-17 | Dow Global Technologies Llc | SILYLAMMONIUM SALTS AS LATENT POLYURETHANE CATALYSTS |
| EP3763792A1 (de) | 2019-07-11 | 2021-01-13 | Covestro Deutschland AG | Verfahren zur herstellung von isocyanuraten aus uretdionen |
| CN117120500A (zh) | 2021-04-14 | 2023-11-24 | 赢创运营有限公司 | 硬质聚氨酯或聚异氰脲酸酯泡沫的生产 |
| EP4282892A1 (de) * | 2022-05-25 | 2023-11-29 | Evonik Operations GmbH | Herstellung von polyurethanschaum unter verwendung von katalysatoren auf basis ionischer flüssigkeiten |
| WO2024038025A1 (de) * | 2022-08-16 | 2024-02-22 | Basf Se | Neue polyurethan-schaumkatalysatoren mit verbesserter lagerstabilität |
| CN120424305A (zh) | 2024-02-02 | 2025-08-05 | 赢创运营有限公司 | 聚氨酯或聚异氰脲酸酯泡沫的生产 |
| CN120424304A (zh) | 2024-02-02 | 2025-08-05 | 赢创运营有限公司 | 聚氨酯或聚异氰脲酸酯泡沫的生产 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005113626A2 (en) * | 2004-05-19 | 2005-12-01 | University Of Utah Research Foundation | Catalysts for the production of polyisocyanates |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335219A (en) * | 1981-04-06 | 1982-06-15 | The Dow Chemical Company | Process for reacting isocyanates in the presence of quaternary ammonium zwitterions |
| DE3227489A1 (de) * | 1982-07-23 | 1984-01-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen |
| DE3600764A1 (de) * | 1986-01-14 | 1987-07-16 | Bayer Ag | Waermehaertbare reaktionsharzgemische und ein verfahren zur herstellung von formkoerpern unter verwendung dieser gemische |
| GB2203159B (en) * | 1987-04-03 | 1990-12-12 | Asahi Chemical Ind | An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition |
| US5032623A (en) * | 1989-07-24 | 1991-07-16 | Foam Supplies, Inc. | Rigid foams using CHClF2 as a blowing agent |
| DE3930669A1 (de) * | 1989-09-14 | 1991-03-28 | Basf Ag | Verfahren zur herstellung von uretdiongruppen aufweisenden polyisocyanaten |
| US5260436A (en) * | 1992-09-21 | 1993-11-09 | Iowa State University Research Foundation, Inc. | Method for synthesis of triarylisocyanurates from aryl isocyanates using triazaprophosphatrane catalysts |
| ZA9810038B (en) * | 1997-11-04 | 2000-05-03 | Rhodia Chimie Sa | A catalyst and a method for the trimerization of isocyanates. |
| GB0008707D0 (en) * | 2000-04-07 | 2000-05-31 | Bp Chem Int Ltd | Imidazole carbenes |
| WO2005030824A1 (ja) * | 2003-09-29 | 2005-04-07 | Tosoh Corporation | 硬質ポリウレタンフォーム及びイソシアヌレート変性硬質ポリウレタンフォーム製造用触媒組成物及びそれを用いた原料配合組成物 |
| US8552077B2 (en) * | 2006-05-04 | 2013-10-08 | Air Products And Chemicals, Inc. | Trimer catalyst additives for improving foam processability |
| US8530534B2 (en) * | 2006-05-04 | 2013-09-10 | Air Products And Chemicals, Inc. | Trimerization catalysts from sterically hindered salts |
| US8148518B2 (en) * | 2007-02-14 | 2012-04-03 | Eastman Chemical Company | Cellulose esters and their production in carboxylated ionic liquids |
-
2009
- 2009-11-09 US US13/125,465 patent/US20110201709A1/en not_active Abandoned
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- 2009-11-09 JP JP2011535728A patent/JP2012508303A/ja not_active Ceased
- 2009-11-09 CN CN2009801539011A patent/CN102272181A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005113626A2 (en) * | 2004-05-19 | 2005-12-01 | University Of Utah Research Foundation | Catalysts for the production of polyisocyanates |
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| WO2010054317A3 (en) | 2010-12-02 |
| US20110201709A1 (en) | 2011-08-18 |
| ES2436013T3 (es) | 2013-12-26 |
| WO2010054317A8 (en) | 2010-07-01 |
| CN102272181A (zh) | 2011-12-07 |
| WO2010054317A2 (en) | 2010-05-14 |
| EP2346919B1 (en) | 2013-09-04 |
| EP2346919A2 (en) | 2011-07-27 |
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