WO2000046270A1 - Polyester with partially fluorinated side chains - Google Patents

Polyester with partially fluorinated side chains Download PDF

Info

Publication number
WO2000046270A1
WO2000046270A1 PCT/US2000/002714 US0002714W WO0046270A1 WO 2000046270 A1 WO2000046270 A1 WO 2000046270A1 US 0002714 W US0002714 W US 0002714W WO 0046270 A1 WO0046270 A1 WO 0046270A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
polyester
polyoxetane
repeating units
carbon atoms
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
Application number
PCT/US2000/002714
Other languages
English (en)
French (fr)
Inventor
Raymond J. Weinert
Edward N. Kresge
Robert E. Medsker
Daniel D. Woodland
Daniel C. Gottschalk
Joe A. Wright
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.)
Omnova Solutions Inc
Original Assignee
Omnova Solutions Inc
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
Priority claimed from US09/244,711 external-priority patent/US6423418B1/en
Application filed by Omnova Solutions Inc filed Critical Omnova Solutions Inc
Priority to AT00908454T priority Critical patent/ATE287912T1/de
Priority to EP20000908454 priority patent/EP1161479B1/en
Priority to JP2000597340A priority patent/JP4027601B2/ja
Priority to DE2000617717 priority patent/DE60017717T2/de
Priority to CA 2362215 priority patent/CA2362215A1/en
Publication of WO2000046270A1 publication Critical patent/WO2000046270A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
    • C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
    • C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • Y10T428/31794—Of cross-linked polyester

Definitions

  • the repeating units from said oxetane monomers desirably have the structure
  • the polyesters may be used in any traditional polyester ap- plication including as a molding material or a coating material.
  • the substrates When used as a coating material the substrates may be any material, which would benefit from a low surface energy, hydrophobic properties including stain resistance or dry-erase, and low coefficient of friction.
  • Examples of substrates that can be coated with coating compositions derived from these polyesters include cellulosic products (coated and uncoated paper, boardstock, cardboard, wood and paneling); fibers; synthetic polymers (including polyolefins, polyesters, polycarbonates, polystyrene, poly (methacrylates) and especially highly filled or highly plasticized ones which are more porous towards stains e.g. polyvinyl chloride); metals (requiring temporary or permanent protection from stains); and ceramics.
  • Table 1 results in high amounts of fluorine on the surface of the coating and the high amounts of fluorine are associated with low surface energy, good abrasion resistance, and easy cleaning.
  • Table I the XPS results for the first 100 angstroms of the top surface vary from about 14 to about 19 atomic percent.
  • Similar recipes wherein the polyoxetane had only hydroxyl end groups have resulted in about 7 to 9 atomic percent fluorine on the surface as determined by XPS. This is significant increase in the surface fluorine content without requiring additional fluorinated oxetane polymer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/US2000/002714 1999-02-04 2000-02-03 Polyester with partially fluorinated side chains Ceased WO2000046270A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AT00908454T ATE287912T1 (de) 1999-02-04 2000-02-03 Polyester mit teilweise fluorinierten seitengruppen
EP20000908454 EP1161479B1 (en) 1999-02-04 2000-02-03 Polyester with partially fluorinated side chains
JP2000597340A JP4027601B2 (ja) 1999-02-04 2000-02-03 部分的にフッ素化された側鎖を有するポリエステル
DE2000617717 DE60017717T2 (de) 1999-02-04 2000-02-03 Polyester mit teilweise fluorinierten seitengruppen
CA 2362215 CA2362215A1 (en) 1999-02-04 2000-02-03 Polyester with partially fluorinated side chains

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US09/244,711 1999-02-04
US09/244,711 US6423418B1 (en) 1998-03-05 1999-02-04 Easily cleanable polymer laminates
US09/384,464 US6383651B1 (en) 1998-03-05 1999-08-27 Polyester with partially fluorinated side chains
US09/384,464 1999-08-27

Publications (1)

Publication Number Publication Date
WO2000046270A1 true WO2000046270A1 (en) 2000-08-10

Family

ID=26936736

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/002714 Ceased WO2000046270A1 (en) 1999-02-04 2000-02-03 Polyester with partially fluorinated side chains

Country Status (8)

Country Link
US (1) US6383651B1 (https=)
EP (1) EP1161479B1 (https=)
JP (1) JP4027601B2 (https=)
AT (1) ATE287912T1 (https=)
CA (1) CA2362215A1 (https=)
DE (1) DE60017717T2 (https=)
ES (1) ES2235838T3 (https=)
WO (1) WO2000046270A1 (https=)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005871A1 (en) * 1999-07-16 2001-01-25 Aerojet-General Corporation Amorphous polyether glycols based on bis-substituted oxetane monomers
US6383651B1 (en) 1998-03-05 2002-05-07 Omnova Solutions Inc. Polyester with partially fluorinated side chains
WO2002036660A1 (en) * 2000-10-27 2002-05-10 Perstorp Specialty Chemicals Ab Novel branched oxetane polyester
US6465566B2 (en) 2000-07-06 2002-10-15 Omnova Solutions Inc. Anionic waterborne polyurethane dispersions containing polyfluorooxetanes
WO2002092660A3 (en) * 2001-05-14 2003-05-01 Omnova Soltions Inc Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups
US6579966B1 (en) 1998-03-05 2003-06-17 Omnova Solutions Inc. Cured polyesters containing fluorinated side chains
WO2003051959A1 (en) * 2001-12-13 2003-06-26 Omnova Solutions Inc. Oxetane block-containing copolymers
US6727344B2 (en) 1999-12-28 2004-04-27 Omnova Solutions Inc. Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer
US6927276B2 (en) 1999-12-28 2005-08-09 Omnova Solutions Inc. Monohydric polyfluorooxetane oligomers, polymers, and copolymers and coating containing the same
US7320829B2 (en) 1998-03-05 2008-01-22 Omnova Solutions Inc. Fluorinated polymer and amine resin compositions and products formed therefrom
US7846507B2 (en) 1998-03-05 2010-12-07 Omnova Solutions Inc. Method of making an easily cleanable polymer laminate

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US7727436B2 (en) * 1998-03-05 2010-06-01 Omnova Solutions Inc. Coating derived from polyesters crosslinked with melamine formaldehyde
US20020127420A1 (en) * 1998-03-05 2002-09-12 Weinert Raymond J. Two stage thermoformable fluorinated polyoxetane-polyester copolymers
US6673889B1 (en) * 1999-06-28 2004-01-06 Omnova Solutions Inc. Radiation curable coating containing polyfuorooxetane
WO2002000808A1 (en) * 2000-06-23 2002-01-03 General Electric Company Silicone pressure sensitive adhesive composition
US6660828B2 (en) * 2001-05-14 2003-12-09 Omnova Solutions Inc. Fluorinated short carbon atom side chain and polar group containing polymer, and flow, or leveling, or wetting agents thereof
US20040043248A1 (en) * 2002-08-30 2004-03-04 3M Innovative Properties Company Phosphorescent elecret films and methods of making the same
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US20040040652A1 (en) * 2002-08-30 2004-03-04 3M Innovative Properties Company Methods for electrostatically adhering an article to a substrate
US20040202820A1 (en) * 2002-08-30 2004-10-14 3M Innovative Properties Company Perforated electret articles and method of making the same
US20040043221A1 (en) * 2002-08-30 2004-03-04 3M Innovative Properties Company Method of adhering a film and articles therefrom
US20040109947A1 (en) * 2002-12-09 2004-06-10 Weinert Raymond J. Stain resistant coatings for flexible substrates, substrates coated therewith and related methods
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KR101117939B1 (ko) 2003-10-28 2012-02-29 사켐,인코포레이티드 세척액 및 에칭제 및 이의 사용 방법
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US7288514B2 (en) * 2005-04-14 2007-10-30 The Clorox Company Polymer-fluorosurfactant associative complexes
JP5506010B2 (ja) * 2006-03-17 2014-05-28 昭和電工株式会社 樹脂組成物
US7723279B2 (en) * 2006-08-23 2010-05-25 The Clorox Company Foamable compositions containing alcohol
US20100189809A1 (en) * 2006-08-23 2010-07-29 The Clorox Company Foamable Compositions Containing Alcohol
KR100801595B1 (ko) * 2006-11-09 2008-02-05 제일모직주식회사 탄소나노튜브 복합체 조성물 및 이를 이용한 투명 전도성필름
WO2009011694A1 (en) 2007-07-13 2009-01-22 Idea Paint Inc. Coatings having writable-erasable surfaces and methods of making the same
WO2009012479A1 (en) 2007-07-19 2009-01-22 Swagelok Company Coated seals
US7875672B2 (en) * 2007-08-24 2011-01-25 Perstorp France Two component waterborne polyurethane coatings for anti-graffiti application
US9056519B2 (en) * 2008-07-18 2015-06-16 Ideapaint, Inc. Ambient cure solvent-based coatings for writable-erasable surfaces
WO2010071887A1 (en) 2008-12-19 2010-06-24 Omnova Solutions Inc. Coating compositions with improved fluorosurfactants
CA3024534C (en) 2016-05-20 2024-02-20 Ideapaint, Inc. Dry-erase compositions and methods of making and using thereof
CN110770271B (zh) 2017-05-19 2023-04-18 埃特纳科技有限公司 官能化氟化单体的制备方法、氟化单体及用于制备其的组合物
US11859082B2 (en) 2020-12-31 2024-01-02 Rohm And Haas Electronic Materials Llc Polymers useful as surface leveling agents

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6579966B1 (en) 1998-03-05 2003-06-17 Omnova Solutions Inc. Cured polyesters containing fluorinated side chains
US6383651B1 (en) 1998-03-05 2002-05-07 Omnova Solutions Inc. Polyester with partially fluorinated side chains
US7320829B2 (en) 1998-03-05 2008-01-22 Omnova Solutions Inc. Fluorinated polymer and amine resin compositions and products formed therefrom
US6686051B1 (en) 1998-03-05 2004-02-03 Omnova Solutions Inc. Cured polyesters containing fluorinated side chains
US7846507B2 (en) 1998-03-05 2010-12-07 Omnova Solutions Inc. Method of making an easily cleanable polymer laminate
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US6727344B2 (en) 1999-12-28 2004-04-27 Omnova Solutions Inc. Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer
US6927276B2 (en) 1999-12-28 2005-08-09 Omnova Solutions Inc. Monohydric polyfluorooxetane oligomers, polymers, and copolymers and coating containing the same
US6962966B2 (en) 1999-12-28 2005-11-08 Omnova Solutions Inc. Monohydric polyfluorooxetane oligomers, polymers, and copolymers and coatings containing the same
US6972317B2 (en) 1999-12-28 2005-12-06 Omnova Solutions Inc. Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer
US6465566B2 (en) 2000-07-06 2002-10-15 Omnova Solutions Inc. Anionic waterborne polyurethane dispersions containing polyfluorooxetanes
WO2002036660A1 (en) * 2000-10-27 2002-05-10 Perstorp Specialty Chemicals Ab Novel branched oxetane polyester
WO2002092660A3 (en) * 2001-05-14 2003-05-01 Omnova Soltions Inc Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups
US7087710B2 (en) 2001-05-14 2006-08-08 Omnova Solutions Inc. Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups
US7022801B2 (en) 2001-05-14 2006-04-04 Omnova Solutions Inc. Polymeric surfactants derived from cyclic monomers having pendant fluorinated carbon groups
WO2003051959A1 (en) * 2001-12-13 2003-06-26 Omnova Solutions Inc. Oxetane block-containing copolymers

Also Published As

Publication number Publication date
JP4027601B2 (ja) 2007-12-26
EP1161479A1 (en) 2001-12-12
DE60017717D1 (de) 2005-03-03
DE60017717T2 (de) 2006-01-12
ES2235838T3 (es) 2005-07-16
EP1161479B1 (en) 2005-01-26
ATE287912T1 (de) 2005-02-15
CA2362215A1 (en) 2000-08-10
US6383651B1 (en) 2002-05-07
JP2003524677A (ja) 2003-08-19

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