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CA2244486A1 - Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation - Google Patents

Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation

Info

Publication number
CA2244486A1
CA2244486A1 CA002244486A CA2244486A CA2244486A1 CA 2244486 A1 CA2244486 A1 CA 2244486A1 CA 002244486 A CA002244486 A CA 002244486A CA 2244486 A CA2244486 A CA 2244486A CA 2244486 A1 CA2244486 A1 CA 2244486A1
Authority
CA
Canada
Prior art keywords
preparation
polyisocyanates containing
iminooxadiazine dione
dione groups
polyisocyanates
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
Application number
CA002244486A
Other languages
French (fr)
Other versions
CA2244486C (en
Inventor
Frank Richter
Carl-Gerd Dieris
Harald Mertes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of CA2244486A1 publication Critical patent/CA2244486A1/en
Application granted granted Critical
Publication of CA2244486C publication Critical patent/CA2244486C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate 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
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • 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
    • C08G18/16—Catalysts
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention relates to a process for the preparation of polyisocyanates by oligomerizing isocyanates corresponding to formula I (OCN-CH2)X (I) wherein X represents the residue obtained by removing the OCN-CH2 group from a monomeric polyisocyanate, wherein the residue contains 3 to 20 carbon atoms and at least one NCO group, in the presence of hydrogen-polyfluoride oligomerization catalysts corresponding to formula II Mn+ n[F-((HF)m] (II) wherein M represents an n-valent cation and m is >= 0.1. The present invention is also directed to the polyisocyanates obtained by this process.
CA002244486A 1997-08-06 1998-08-03 Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation Expired - Fee Related CA2244486C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19734048.2 1997-08-06
DE19734048A DE19734048A1 (en) 1997-08-06 1997-08-06 Process for the preparation of polyisocyanates, polyisocyanates produced therewith and their use

Publications (2)

Publication Number Publication Date
CA2244486A1 true CA2244486A1 (en) 1999-02-06
CA2244486C CA2244486C (en) 2007-10-23

Family

ID=7838165

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002244486A Expired - Fee Related CA2244486C (en) 1997-08-06 1998-08-03 Polyisocyanates containing iminooxadiazine dione groups and a process for their preparation

Country Status (7)

Country Link
EP (1) EP0896009B1 (en)
JP (1) JP4106134B2 (en)
KR (1) KR100511245B1 (en)
AT (1) ATE268788T1 (en)
CA (1) CA2244486C (en)
DE (2) DE19734048A1 (en)
ES (1) ES2222536T3 (en)

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6107484A (en) * 1998-06-02 2000-08-22 Bayer Aktiengesellschaft Process for preparing polyisocyanates containing iminooxadiazinedione groups
US6191181B1 (en) 1998-11-20 2001-02-20 Bayer Aktiengesellschaft Urethane acrylates and their use in coating compositions
US6590098B2 (en) 2001-05-14 2003-07-08 Bayer Aktiengesellschaft Method of preparing aliphatic polyisocyanates with uretdione, isocyanurate and iminooxadiazindione structures
US7196134B2 (en) 2003-05-20 2007-03-27 Bayer Materialscience Ag High-solids binder combinations for scratch-resistant topcoats
US7834103B2 (en) 2005-10-21 2010-11-16 Asahi Kasei Chemicals Corporation Highly crosslinkable low-viscosity polyisocyanate composition and coating composition containing same
US8063144B2 (en) 2004-11-25 2011-11-22 Bayer Materialscience Ag Polyisocyanate mixtures, a process for their preparation and their use in coating compositions
CN102442959A (en) * 2010-08-03 2012-05-09 拜尔材料科学股份公司 Process for the preparation of polyisocyanates and their use
US8476362B2 (en) 2008-10-22 2013-07-02 Bayer Materialscience Ag Moisture-curing polyisocyanate mixtures
US9440937B2 (en) 2011-11-29 2016-09-13 Covestro Deutschland Ag Method for producing polyisocyanates and use thereof
US9567485B2 (en) 2012-07-09 2017-02-14 Covestro Deutschland Ag Coating method and hardener for polyurethane paint
US9790194B2 (en) 2011-11-30 2017-10-17 Covestro Deutschland Ag Process for continuous isocyanate modification
US9850338B2 (en) 2014-02-18 2017-12-26 Covestro Deutschland Ag Process for isocyanate modification using spirocyclic ammonium salts as catalyst
CN107531876A (en) * 2015-04-21 2018-01-02 科思创德国股份有限公司 Poly-isocyanurate plastics with high thermal stability
US9926402B2 (en) 2013-12-10 2018-03-27 Covestro Deutschland Ag Iminooxadiazinedione polyisocyanates
US9938369B2 (en) 2013-07-25 2018-04-10 Covestro Deutschland Ag Use of succinonitrile in the production of polyisocyanates comprising iminooxadiazinedione groups
US10131736B2 (en) 2014-02-18 2018-11-20 Covestro Deutschland Ag Method for isocyanate modification using catalysts with an NPN sequence
US10167358B2 (en) 2015-08-17 2019-01-01 Covestro Deutschland Ag Process for modifying isocyanates with use of cyclic ammonium salts as catalyst
EP3527602A1 (en) * 2018-02-15 2019-08-21 Asahi Kasei Kabushiki Kaisha Polyisocyanate composition, coating composition, method for producing coating film and coating film
US10544327B2 (en) 2015-09-09 2020-01-28 Covestro Deutschland Ag Scratch-resistant aqueous 2K PU coatings
US10590226B2 (en) 2015-04-21 2020-03-17 Covestro Deutschland Ag Solids based on polyisocyanurate polymers produced under adiabatic conditions
US10717805B2 (en) 2015-04-21 2020-07-21 Covestro Deutschland Ag Process for producing polyisocyanurate plastics
US10752723B2 (en) 2015-04-21 2020-08-25 Covestro Deutschland Ag Polyisocyanurate polymer 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
US10774239B2 (en) 2015-09-09 2020-09-15 Covestro Deutschland Ag Scratch-resistant two-component polyurethane coatings
US11286331B2 (en) 2015-04-21 2022-03-29 Covestro Deutschland Ag Hydrophilically modified polyisocyanurate plastic and process for production thereof
EP4015552A1 (en) * 2020-12-18 2022-06-22 Asahi Kasei Kabushiki Kaisha Polyisocyanate composition, water-based coating composition and coated substrate
US11613072B2 (en) 2016-11-14 2023-03-28 Covestro Deutschland Ag Dual-curing isocyanurate polymers
US11760828B2 (en) 2017-09-26 2023-09-19 Covestro Deutschland Ag Two-component system for elastic coatings
EP4166589A4 (en) * 2020-09-25 2024-03-06 Wanhua Chemical Group Co., Ltd Isocyanurate-containing polyisocyanate composition with stable chromaticity, and preparation method thereof

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DE10160305A1 (en) * 2001-12-07 2003-06-18 Degussa Catalysts and processes for the preparation of polyisocyanates containing isocyanurate groups and their use
DE10208395B4 (en) * 2002-02-27 2004-03-25 Ivoclar Vivadent Ag (Meth) acrylate substituted iminooxadiazinedione derivatives
DE10208396B4 (en) 2002-02-27 2006-05-18 Ivoclar Vivadent Ag Dental materials based on substituted iminooxadiazinedione derivatives
DE10336184A1 (en) * 2003-08-07 2005-02-24 Bayer Materialscience Ag New catalysts for selective isocyanate dimerization
DE10339912B4 (en) 2003-08-29 2016-07-21 Ivoclar Vivadent Ag Dental coating materials, their use and methods of coating a substrate surface
DE102004048871A1 (en) * 2004-10-07 2006-04-13 Bayer Materialscience Ag Process for the preparation of iminooxadiazinedione polyisocyanates
WO2006063745A1 (en) * 2004-12-13 2006-06-22 Basf Aktiengesellschaft Method for the production of low-yellowing (cyclo)aliphatic polyisocyanates
US8373004B2 (en) 2007-03-27 2013-02-12 Basf Se Method for producing colorless isocyanurates of diisocyanates
ES2400735T3 (en) 2007-11-28 2013-04-11 Basf Se Liquid Stabilizer Mix
US8119245B2 (en) 2008-02-05 2012-02-21 Bayer Materialscience Llc Dual-cure coating compositions based on polyaspartates polyisocyanates and acrylate-containing compounds
US20090226644A1 (en) 2008-03-05 2009-09-10 Wylie Amy S Gel coat compositions from acrylate-modified aspartates
JP5650119B2 (en) 2008-10-22 2015-01-07 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Method for producing colorless polyisocyanate
DE102009005712A1 (en) 2009-01-22 2010-07-29 Bayer Materialscience Ag Polyurethanvergussmassen
DE102009007194A1 (en) 2009-02-03 2010-08-05 Bayer Materialscience Ag Flexible coatings
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CA2844959C (en) 2011-08-19 2019-04-02 Ppg Europe Bv Coating composition and use thereof
DE102011115062A1 (en) 2011-10-07 2013-04-11 Dreve Prodimed Gmbh Blank for the removal of ear molds
CN105189597B (en) * 2013-03-22 2018-07-06 科思创德国股份有限公司 It is used to prepare the method for polyisocyanates and its catalytic component box
JP6329017B2 (en) * 2013-06-28 2018-05-23 旭化成株式会社 Polyisocyanate composition
EP3271432B1 (en) 2015-03-16 2019-07-31 Covestro Deutschland AG Polyisocyanate composition based on 1,5-pentamethylendiisocyanate
US9815739B2 (en) 2015-10-30 2017-11-14 Covestro Llc Polyisocyanurate based cement for wellbore fluid loss prevention
ES2927985T3 (en) 2016-08-09 2022-11-14 Covestro Intellectual Property Gmbh & Co Kg Silane-functional polymeric polyurethanes
WO2018073302A1 (en) 2016-10-18 2018-04-26 Covestro Deutschland Ag Coating of wires with catalytically crosslinked blocked polyisocyanates
CN109890865B (en) 2016-10-18 2021-12-07 科思创德国股份有限公司 Production of plastics by catalytic crosslinking of blocked polyisocyanates
ES2823248T3 (en) 2016-10-18 2021-05-06 Covestro Intellectual Property Gmbh & Co Kg Hard coatings with high chemical and mechanical stability
WO2018095869A1 (en) 2016-11-22 2018-05-31 Basf Se Method for producing trimeric isocyanates
WO2018153801A1 (en) 2017-02-22 2018-08-30 Covestro Deutschland Ag Method for modifying at least pentamethylene diisocyanate by means of spirocyclic ammonium salts as catalyst
EP3381962A1 (en) 2017-03-29 2018-10-03 Covestro Deutschland AG Generation of polyisocyanurate layers through separate application of isocyanate components and catalysts
EP3421516A1 (en) 2017-06-28 2019-01-02 Covestro Deutschland AG Coloured plastics based on crosslinked polyisocyanates
EP3444288A1 (en) 2017-08-15 2019-02-20 Covestro Deutschland AG Method for the preparation of polyisocyanates containing iminooxadiazindione groups using mixtures of catalysts
ES2981974T3 (en) 2017-11-14 2024-10-14 Covestro Deutschland Ag Semi-finished products based on dual cross-linking mechanism
CN111479842B (en) 2017-12-21 2023-09-05 科思创德国股份有限公司 Freeze-resistant aqueous coating based on polyisocyanates
CN111566140A (en) 2017-12-21 2020-08-21 科思创德国股份有限公司 Freeze-resistant adhesive based on polyisocyanates
WO2019157625A1 (en) 2018-02-13 2019-08-22 Covestro Deutschland Ag Aromatic polyisocyanates with a high solids content
CN113166364A (en) 2018-05-17 2021-07-23 科思创知识产权两合公司 Method for producing composite materials from polyethylene fibres having an ultrahigh molecular weight and crosslinked polyisocyanates
US11319402B2 (en) 2018-05-17 2022-05-03 Covestro Intellectual Property Gmbh & Co. Kg Method for producing a polyisocyanate polymer and a polyisocyanurate plastic
WO2020016119A1 (en) 2018-07-16 2020-01-23 Covestro Deutschland Ag Method for oligomerizing isocyanates by means of polyhedral silsesquioxane catalysts
WO2020079160A1 (en) 2018-10-19 2020-04-23 Covestro Deutschland Ag Anhydrously curing polyisocyanate-based adhesives
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KR20210132659A (en) 2019-02-27 2021-11-04 코베스트로 인텔렉쳐 프로퍼티 게엠베하 운트 콤파니 카게 Polyisocyanurate Materials as Electropotting Compounds
US11566145B2 (en) 2019-03-14 2023-01-31 Covestro Llc Polyurethane coating compositions and their use as gel coats
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CN114008102A (en) 2019-06-24 2022-02-01 巴斯夫欧洲公司 Water-emulsifiable isocyanates having improved properties
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EP3838939A1 (en) 2019-12-19 2021-06-23 Covestro Deutschland AG Catalyst component for the modification of isocyanates
EP3885385A1 (en) 2020-03-23 2021-09-29 Basf Se Process for modifying isocyanates with use of guanidinium salts as catalyst
EP4175820A1 (en) 2020-07-02 2023-05-10 Covestro Deutschland AG Coatings from polyisocyanurate coatings (rim) and their use in injection molding processes
EP3985044A1 (en) 2020-10-13 2022-04-20 Basf Se Process for modifying isocyanates
EP4301798A1 (en) 2021-03-02 2024-01-10 Basf Se Water-emulsifiable polyisocyanates with improved properties
US20240301154A1 (en) 2021-03-29 2024-09-12 Covestro Deutschland Ag Polyisocyanurate-prepregs and fiber composite components produced therefrom
EP4098678A1 (en) 2021-06-02 2022-12-07 Basf Se Process for modifying isocyanates with use of difluorosilicate salts as catalyst
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EP4433519A1 (en) 2021-11-16 2024-09-25 Basf Se Preparation of polyisocyanates containing iminooxadiazinedione groups and their use
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Cited By (36)

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Publication number Priority date Publication date Assignee Title
US6107484A (en) * 1998-06-02 2000-08-22 Bayer Aktiengesellschaft Process for preparing polyisocyanates containing iminooxadiazinedione groups
US6191181B1 (en) 1998-11-20 2001-02-20 Bayer Aktiengesellschaft Urethane acrylates and their use in coating compositions
US6590098B2 (en) 2001-05-14 2003-07-08 Bayer Aktiengesellschaft Method of preparing aliphatic polyisocyanates with uretdione, isocyanurate and iminooxadiazindione structures
US7196134B2 (en) 2003-05-20 2007-03-27 Bayer Materialscience Ag High-solids binder combinations for scratch-resistant topcoats
US8063144B2 (en) 2004-11-25 2011-11-22 Bayer Materialscience Ag Polyisocyanate mixtures, a process for their preparation and their use in coating compositions
US7834103B2 (en) 2005-10-21 2010-11-16 Asahi Kasei Chemicals Corporation Highly crosslinkable low-viscosity polyisocyanate composition and coating composition containing same
US8476362B2 (en) 2008-10-22 2013-07-02 Bayer Materialscience Ag Moisture-curing polyisocyanate mixtures
CN102442959B (en) * 2010-08-03 2016-07-27 科思创德国股份有限公司 The preparation method and its usage of polyisocyanates
US9458097B2 (en) 2010-08-03 2016-10-04 Covestro Deutschland Ag Process for the preparation of polyisocyanates and use thereof
CN102442959A (en) * 2010-08-03 2012-05-09 拜尔材料科学股份公司 Process for the preparation of polyisocyanates and their use
US9440937B2 (en) 2011-11-29 2016-09-13 Covestro Deutschland Ag Method for producing polyisocyanates and use thereof
US9790194B2 (en) 2011-11-30 2017-10-17 Covestro Deutschland Ag Process for continuous isocyanate modification
US9567485B2 (en) 2012-07-09 2017-02-14 Covestro Deutschland Ag Coating method and hardener for polyurethane paint
US9802223B2 (en) 2012-07-09 2017-10-31 Covestro Deutschland Ag Coating method and hardener for polyurethane paint
US9938369B2 (en) 2013-07-25 2018-04-10 Covestro Deutschland Ag Use of succinonitrile in the production of polyisocyanates comprising iminooxadiazinedione groups
US9926402B2 (en) 2013-12-10 2018-03-27 Covestro Deutschland Ag Iminooxadiazinedione polyisocyanates
US10131736B2 (en) 2014-02-18 2018-11-20 Covestro Deutschland Ag Method for isocyanate modification using catalysts with an NPN sequence
US9850338B2 (en) 2014-02-18 2017-12-26 Covestro Deutschland Ag Process for isocyanate modification using spirocyclic ammonium salts as catalyst
US11286331B2 (en) 2015-04-21 2022-03-29 Covestro Deutschland Ag Hydrophilically modified polyisocyanurate plastic and process for production thereof
US10752723B2 (en) 2015-04-21 2020-08-25 Covestro Deutschland Ag Polyisocyanurate polymer and process for the production of polyisocyanurate polymers
US11390707B2 (en) 2015-04-21 2022-07-19 Covestro Deutschland Ag Polyisocyanurate polymers and process for the production of polyisocyanurate polymers
CN107531876B (en) * 2015-04-21 2021-02-09 科思创德国股份有限公司 Polyisocyanurate plastics having high thermal stability
US10590226B2 (en) 2015-04-21 2020-03-17 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
US10717805B2 (en) 2015-04-21 2020-07-21 Covestro Deutschland Ag Process for producing polyisocyanurate plastics
US11286332B2 (en) 2015-04-21 2022-03-29 Covestro Deutschland Ag Hydrophobically modified polyisocyanurate plastic and method for production thereof
US10752724B2 (en) 2015-04-21 2020-08-25 Covestro Deutschland Ag Process for producing polyisocvanurate plastics having functionalized surfaces
CN107531876A (en) * 2015-04-21 2018-01-02 科思创德国股份有限公司 Poly-isocyanurate plastics with high thermal stability
US10167358B2 (en) 2015-08-17 2019-01-01 Covestro Deutschland Ag Process for modifying isocyanates with use of cyclic ammonium salts as catalyst
US10544327B2 (en) 2015-09-09 2020-01-28 Covestro Deutschland Ag Scratch-resistant aqueous 2K PU coatings
US10774239B2 (en) 2015-09-09 2020-09-15 Covestro Deutschland Ag Scratch-resistant two-component polyurethane coatings
US11613072B2 (en) 2016-11-14 2023-03-28 Covestro Deutschland Ag Dual-curing isocyanurate polymers
US11760828B2 (en) 2017-09-26 2023-09-19 Covestro Deutschland Ag Two-component system for elastic coatings
EP3527602A1 (en) * 2018-02-15 2019-08-21 Asahi Kasei Kabushiki Kaisha Polyisocyanate composition, coating composition, method for producing coating film and coating film
EP4166589A4 (en) * 2020-09-25 2024-03-06 Wanhua Chemical Group Co., Ltd Isocyanurate-containing polyisocyanate composition with stable chromaticity, and preparation method thereof
EP4015552A1 (en) * 2020-12-18 2022-06-22 Asahi Kasei Kabushiki Kaisha Polyisocyanate composition, water-based coating composition and coated substrate

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CA2244486C (en) 2007-10-23
KR100511245B1 (en) 2006-02-28
JPH11152320A (en) 1999-06-08
DE19734048A1 (en) 1999-02-11
ES2222536T3 (en) 2005-02-01
ATE268788T1 (en) 2004-06-15
DE59811531D1 (en) 2004-07-15
JP4106134B2 (en) 2008-06-25
EP0896009A1 (en) 1999-02-10
EP0896009B1 (en) 2004-06-09

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