CA2352660A1 - Process for preparing a broad-compatibility, storage-stable, rheologically active urea urethane solution - Google Patents

Process for preparing a broad-compatibility, storage-stable, rheologically active urea urethane solution Download PDF

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Publication number
CA2352660A1
CA2352660A1 CA002352660A CA2352660A CA2352660A1 CA 2352660 A1 CA2352660 A1 CA 2352660A1 CA 002352660 A CA002352660 A CA 002352660A CA 2352660 A CA2352660 A CA 2352660A CA 2352660 A1 CA2352660 A1 CA 2352660A1
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CA
Canada
Prior art keywords
preparing
compatibility
broad
stable
storage
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
CA002352660A
Other languages
French (fr)
Other versions
CA2352660C (en
Inventor
Karlheinz Haubennestel
Ulrich Orth
Axel Woocker
Christoph Buchmann
Heribert Holtkamp
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.)
BYK Chemie GmbH
Original Assignee
BYK Chemie GmbH
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 BYK Chemie GmbH filed Critical BYK Chemie GmbH
Publication of CA2352660A1 publication Critical patent/CA2352660A1/en
Application granted granted Critical
Publication of CA2352660C publication Critical patent/CA2352660C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C08G18/06—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
    • C08G18/3225—Polyamines
    • 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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes
    • 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
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/284—Compounds containing ester groups, e.g. oxyalkylated monocarboxylic 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
    • C08G18/28—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
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/324—Polyamines aromatic containing only one aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/04—Thixotropic paints

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

The invention relates to a process for preparing a solution which comprises urea urethanes and is effective as a thixotropic agent, which involves reacting at least two structurally different monohydroxy compounds with an excess of toluylene diisocyanate to form monoisocyanate adducts, removing the unreacted portion of the toluylene diisocyanate, and reacting the resultant monoisocyanate adducts with diamines in an aprotic solvent in the presence of a lithium salt to form urea urethanes. The invention also relates to the use of the solution to receive thixotropic coating compositions.
CA002352660A 2000-08-16 2001-07-09 Process for preparing a broad-compatibility, storage-stable, rheologically active urea urethane solution Expired - Lifetime CA2352660C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10039837.5 2000-08-16
DE10039837A DE10039837C2 (en) 2000-08-16 2000-08-16 Process for the preparation of a storage-stable, rheologically effective urea urethane solution with broad compatibility

Publications (2)

Publication Number Publication Date
CA2352660A1 true CA2352660A1 (en) 2002-02-16
CA2352660C CA2352660C (en) 2008-10-21

Family

ID=7652494

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002352660A Expired - Lifetime CA2352660C (en) 2000-08-16 2001-07-09 Process for preparing a broad-compatibility, storage-stable, rheologically active urea urethane solution

Country Status (10)

Country Link
EP (1) EP1188779B1 (en)
JP (1) JP4942262B2 (en)
KR (1) KR100796040B1 (en)
CN (1) CN1204117C (en)
AT (1) ATE268790T1 (en)
CA (1) CA2352660C (en)
DE (2) DE10039837C2 (en)
DK (1) DK1188779T3 (en)
ES (1) ES2220631T3 (en)
TW (1) TWI226892B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8883942B2 (en) 2009-05-19 2014-11-11 Byk-Chemie Gmbh Terminally unsaturated, oxetane-based macromonomers, and methods for the production thereof
US8956452B2 (en) 2008-12-01 2015-02-17 Byk-Chemie Gmbh Method for producing rheologically effective urea urethanes in organic salts
US9617371B2 (en) 2009-09-08 2017-04-11 Byk-Chemie Gmbh Polyureas as rheology control agents
RU2621733C2 (en) * 2012-03-29 2017-06-07 Хантсмэн Интернэшнл Ллс Isocyanate-based prepolymer
US9796860B2 (en) 2014-04-15 2017-10-24 Byk-Chemie Gmbh Storage-stable urea preparations which are suitable as rheology control agents
WO2024008765A1 (en) * 2022-07-06 2024-01-11 Byk-Chemie Gmbh Composition comprising a cyclic amide

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DE10241853B3 (en) * 2002-09-09 2004-01-22 Byk-Chemie Gmbh Polymeric urea urethane as a rheology control agent and manufacturing process
WO2005005557A1 (en) * 2003-07-08 2005-01-20 Nuplex Resins B.V. Carbon-substituted methyl amine derivatives and their use as a rheology control agent
KR100482427B1 (en) * 2003-12-19 2005-04-14 박장원 Crosslinked foam which has inner-cavity structure, and process of forming thereof
US7220300B2 (en) * 2004-12-04 2007-05-22 Xerox Corporation Phase change inks containing bis(urea-urethane) compounds
US7144450B2 (en) * 2004-12-04 2006-12-05 Xerox Corporation Phase change inks containing trans-1,2-cyclohexane bis(urea-urethane) compounds
US7560587B2 (en) * 2004-12-04 2009-07-14 Xerox Corporation Bis[urea-urethane] compounds
WO2007105258A1 (en) * 2006-03-07 2007-09-20 The Yokohama Rubber Co., Ltd. Thixotropy-imparting agent, hardenable resin composition making use of the same and method of using the hardenable resin composition
DE102006010721B4 (en) * 2006-03-08 2010-04-15 Byk-Chemie Gmbh Biuret compounds for rheology control
KR100803024B1 (en) * 2006-07-25 2008-02-14 케이에스케미칼 주식회사 The preparing method of urethane-urea solution which is used as thixotropic agent in the paint
DE202008008419U1 (en) 2008-04-23 2009-06-04 Byk-Chemie Gmbh Stable dispersions of inorganic nanoparticles
DE102008029858A1 (en) 2008-04-23 2009-10-29 Byk-Chemie Gmbh Stable dispersions of inorganic nanoparticles
DE102008038488A1 (en) 2008-08-20 2010-02-25 Henkel Ag & Co. Kgaa Moisture-curing waterproof coating
JP5410595B2 (en) 2009-04-21 2014-02-05 ハンツマン・インターナショナル・エルエルシー Polyisocyanate composition
DE102009021912A1 (en) 2009-05-19 2010-12-02 Byk-Chemie Gmbh From oxetane-based macromonomers available polymers, processes for their preparation and their use as additives in coating materials and plastics
EP2528980B1 (en) 2010-01-28 2013-10-09 BYK-Chemie GmbH Coating preparation containing urea components and amide components
JP2014510808A (en) * 2011-02-22 2014-05-01 ビーエーエスエフ ソシエタス・ヨーロピア Rheological agents for radiation curable coating materials
EP2644632A1 (en) * 2012-03-29 2013-10-02 Huntsman International Llc Isocyanate-based prepolymer
JP6618802B2 (en) 2012-12-15 2019-12-11 ビイク−ヒエミー ゲゼルシャフト ミツト ベシユレンクテル ハフツングＢＹＫ−Ｃｈｅｍｉｅ ＧｍｂＨ Rheology control composition
JP6423000B2 (en) 2014-04-15 2018-11-14 ビイク−ヒエミー ゲゼルシャフト ミツト ベシユレンクテル ハフツングＢＹＫ−Ｃｈｅｍｉｅ ＧｍｂＨ Composition for rheology adjustment
WO2015158792A1 (en) 2014-04-15 2015-10-22 Byk-Chemie Gmbh Rheology control agents comprising an active substance combination
EP3328909B1 (en) 2015-07-27 2019-06-26 BYK-Chemie GmbH Urea urethanes for rheology control
KR101835720B1 (en) 2015-11-30 2018-03-08 케이에스케미칼 주식회사 Manufacturing method of thixotropic agent with shear thinning
EP3574029B1 (en) * 2017-01-30 2021-01-20 BYK-Chemie GmbH Urea-group- and/or urethane-group-containing amides as and in rheology control agents, their preparation and their use
EP3459985B1 (en) * 2017-09-22 2020-06-17 Cliq Swisstech Gmbh Urea urethanes (ii)
WO2018189297A1 (en) 2017-04-13 2018-10-18 Byk-Chemie Gmbh Polymer suitable as thickener
EP3428233A1 (en) 2017-07-13 2019-01-16 Sika Technology Ag Coating system with high surface roughness
WO2019096611A1 (en) * 2017-11-14 2019-05-23 Basf Se Process for preparing urea urethane polymer
CA3086715C (en) * 2017-12-21 2022-07-12 Byk-Chemie Gmbh Urea and urethane group containing anti-settling rheology control additive
KR102416797B1 (en) * 2017-12-21 2022-07-05 비와이케이-케미 게엠베하 Anti-sagging rheology control agent containing urea groups
KR102071950B1 (en) 2017-12-28 2020-01-31 낙우산업(주) Nanoclay to improve thickening and thixotropic behavior in natural paints and the preparing process the same
CN108070066B (en) * 2017-12-29 2020-11-27 陈鹏 Paint and ink anti-settling agent and preparation method thereof
CN112204067B (en) * 2018-03-27 2022-06-24 艾德凡斯化学公司 Thixotropic rheology modifier composition
JP7332251B2 (en) * 2018-06-28 2023-08-23 ホヤ レンズ タイランド リミテッド Polymerizable composition for optical members
EP3906268B1 (en) 2019-01-04 2022-11-23 Byk-Chemie GmbH Rheology control additive containing urea component
CN113840858B (en) 2019-03-14 2023-12-15 毕克化学有限公司 Rheology control additives containing cyclic amides
WO2022043175A1 (en) * 2020-08-24 2022-03-03 Basf Se Urea urethane compounds
US20240002582A1 (en) 2020-12-04 2024-01-04 Byk-Chemie Gmbh Rheology control agent
DE102021128685A1 (en) 2021-11-04 2023-05-04 Voco Gmbh Highly effective, silica-free, storage-stable dental etching gel

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8956452B2 (en) 2008-12-01 2015-02-17 Byk-Chemie Gmbh Method for producing rheologically effective urea urethanes in organic salts
US8883942B2 (en) 2009-05-19 2014-11-11 Byk-Chemie Gmbh Terminally unsaturated, oxetane-based macromonomers, and methods for the production thereof
US9617371B2 (en) 2009-09-08 2017-04-11 Byk-Chemie Gmbh Polyureas as rheology control agents
RU2621733C2 (en) * 2012-03-29 2017-06-07 Хантсмэн Интернэшнл Ллс Isocyanate-based prepolymer
US9796860B2 (en) 2014-04-15 2017-10-24 Byk-Chemie Gmbh Storage-stable urea preparations which are suitable as rheology control agents
WO2024008765A1 (en) * 2022-07-06 2024-01-11 Byk-Chemie Gmbh Composition comprising a cyclic amide

Also Published As

Publication number Publication date
DK1188779T3 (en) 2004-08-30
KR20020014680A (en) 2002-02-25
JP4942262B2 (en) 2012-05-30
ATE268790T1 (en) 2004-06-15
KR100796040B1 (en) 2008-01-21
DE50102521D1 (en) 2004-07-15
CN1338453A (en) 2002-03-06
DE10039837C2 (en) 2003-03-20
EP1188779B1 (en) 2004-06-09
CN1204117C (en) 2005-06-01
EP1188779A1 (en) 2002-03-20
JP2002105042A (en) 2002-04-10
ES2220631T3 (en) 2004-12-16
TWI226892B (en) 2005-01-21
DE10039837A1 (en) 2002-03-07
CA2352660C (en) 2008-10-21

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