WO2007124263A3 - Method of making urethane based fluorinated monomers - Google Patents

Method of making urethane based fluorinated monomers Download PDF

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Publication number
WO2007124263A3
WO2007124263A3 PCT/US2007/066228 US2007066228W WO2007124263A3 WO 2007124263 A3 WO2007124263 A3 WO 2007124263A3 US 2007066228 W US2007066228 W US 2007066228W WO 2007124263 A3 WO2007124263 A3 WO 2007124263A3
Authority
WO
WIPO (PCT)
Prior art keywords
fluorinated
urethane based
reacting
organic solvent
isocyanate
Prior art date
Application number
PCT/US2007/066228
Other languages
French (fr)
Other versions
WO2007124263A2 (en
Inventor
Frans Audenaert
Bernd Kuehneweg
Original Assignee
3M Innovative Properties Co
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 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to EP07797213A priority Critical patent/EP2004716A4/en
Priority to CA002649222A priority patent/CA2649222A1/en
Publication of WO2007124263A2 publication Critical patent/WO2007124263A2/en
Publication of WO2007124263A3 publication Critical patent/WO2007124263A3/en

Links

Classifications

    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
    • 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
    • C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester 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
    • C08G18/70—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
    • 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
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates

Abstract

Method of preparing urethane based fluorinated monomers comprising (i) reacting a fluorinated alcohol and an isocyanate functional non-fluorinated monomer or (ii) reacting in one or two steps a fluorinated alcohol, a polyisocyanate and an isocyanate reactive non-fluorinated monomer, wherein reactions (i) and (ii) are carried out in the presence of one or more reactive diluents, the reactive diluents having an ethylenically unsaturated group and being free of isocyanate reactive groups. The method does not require an inert organic solvent as a reaction medium, thus excluding volatile organic compounds (VOC's). The resulting compositions can be readily and conveniently used to prepare radiation curable coating compositions without the need to remove organic solvent from the composition.
PCT/US2007/066228 2006-04-13 2007-04-09 Method of making urethane based fluorinated monomers WO2007124263A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP07797213A EP2004716A4 (en) 2006-04-13 2007-04-09 Method of making urethane based fluorinated monomers
CA002649222A CA2649222A1 (en) 2006-04-13 2007-04-09 Method of making urethane based fluorinated monomers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/279,653 2006-04-13
US11/279,653 US20070244289A1 (en) 2006-04-13 2006-04-13 Method of making urethane based fluorinated monomers

Publications (2)

Publication Number Publication Date
WO2007124263A2 WO2007124263A2 (en) 2007-11-01
WO2007124263A3 true WO2007124263A3 (en) 2007-12-21

Family

ID=38605664

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/066228 WO2007124263A2 (en) 2006-04-13 2007-04-09 Method of making urethane based fluorinated monomers

Country Status (4)

Country Link
US (1) US20070244289A1 (en)
EP (1) EP2004716A4 (en)
CA (1) CA2649222A1 (en)
WO (1) WO2007124263A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110186790A1 (en) * 2009-07-23 2011-08-04 E. I. Du Pont De Nemours And Company Fluorinated hybrid compositions
EP2353736A1 (en) 2010-01-29 2011-08-10 3M Innovative Properties Company Continuous process for forming a multilayer film and multilayer film prepared by such method
US8170441B2 (en) * 2010-02-26 2012-05-01 Eastman Kodak Company Cleaning blade for electrostatographic apparatus
US8594528B2 (en) 2011-05-27 2013-11-26 Eastman Kodak Company Electrostatographic cleaning blade member and apparatus
US10030334B2 (en) 2012-04-24 2018-07-24 3M Innovative Properties Company Fluorochemical compounds, compositions, articles, and methods
EP3197865A1 (en) * 2014-09-26 2017-08-02 The Chemours Company FC, LLC Sulfonated fluorinated, non-fluorinated or partially fluorinated urethanes
JP6547384B2 (en) * 2015-04-17 2019-07-24 ダイキン工業株式会社 Surface treatment composition
CN112608445B (en) * 2020-12-04 2022-07-12 上海应用技术大学 Ultraviolet light curing resin and preparation method thereof

Citations (4)

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Publication number Priority date Publication date Assignee Title
US4960543A (en) * 1987-12-29 1990-10-02 Hoechst Aktiengesellschaft Urethane made from aliphatic fluorinated alcohols, isocyanates and substituted aromatic compounds, a process for their preparation, and their use
US6239247B1 (en) * 1997-05-14 2001-05-29 3M Innovative Properties Company Fluorochemical composition comprising a urethane having a fluorochemical oligomer and a hydrophilic segment to impart stain release properties to a substrate
WO2004067499A1 (en) * 2003-01-31 2004-08-12 Daikin Industries, Ltd. Fluorinated urethane compound and use thereof
US6790924B2 (en) * 2001-02-22 2004-09-14 E. I. Du Pont De Nemours And Company Method for protection of stone with fluorinated urethane

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US4960543A (en) * 1987-12-29 1990-10-02 Hoechst Aktiengesellschaft Urethane made from aliphatic fluorinated alcohols, isocyanates and substituted aromatic compounds, a process for their preparation, and their use
US6239247B1 (en) * 1997-05-14 2001-05-29 3M Innovative Properties Company Fluorochemical composition comprising a urethane having a fluorochemical oligomer and a hydrophilic segment to impart stain release properties to a substrate
US6790924B2 (en) * 2001-02-22 2004-09-14 E. I. Du Pont De Nemours And Company Method for protection of stone with fluorinated urethane
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Non-Patent Citations (1)

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Title
See also references of EP2004716A4 *

Also Published As

Publication number Publication date
EP2004716A2 (en) 2008-12-24
EP2004716A4 (en) 2012-06-06
US20070244289A1 (en) 2007-10-18
WO2007124263A2 (en) 2007-11-01
CA2649222A1 (en) 2007-11-01

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