CA2130603A1 - Improvement of water-dispersible poly (urethane-urea) compositions - Google Patents

Improvement of water-dispersible poly (urethane-urea) compositions

Info

Publication number
CA2130603A1
CA2130603A1 CA2130603A CA2130603A CA2130603A1 CA 2130603 A1 CA2130603 A1 CA 2130603A1 CA 2130603 A CA2130603 A CA 2130603A CA 2130603 A CA2130603 A CA 2130603A CA 2130603 A1 CA2130603 A1 CA 2130603A1
Authority
CA
Canada
Prior art keywords
urethane
urea
poly
water
prepolymer
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
CA2130603A
Other languages
French (fr)
Other versions
CA2130603C (en
Inventor
Urvee Y. Treasurer
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.)
Sherwin Williams Co
Original Assignee
Eastman Kodak 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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of CA2130603A1 publication Critical patent/CA2130603A1/en
Application granted granted Critical
Publication of CA2130603C publication Critical patent/CA2130603C/en
Anticipated expiration legal-status Critical
Expired - Fee Related 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
    • 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
    • C08G18/36—Hydroxylated esters of higher fatty 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids

Abstract

Water dispersible, one component, self crosslinkable poly(urethane-urea) composition that is stable and capable of curing at room temperature is prepared by forming a prepolymer comprising an alcoholized drying oil; a diisocyanate, a polyalkylene ether polyol, and a dihydroxy containing alkanoic acid polyol; neutralizing the prepolymer; contacting the neutralized prepolymer with water and diamine wherein the alcoholized drying oil has a sufficient content of monoglycerides to allow for chain extension in step (C) and the poly(urethane-urea) self-crosslinks upon drying. The waterborne poly(urethane-urea) composition exhibits good chemical resistance, adhesion, abrasion, and high gloss properties when used as a coating.
CA002130603A 1993-08-31 1994-08-22 Improvement of water-dispersible poly (urethane-urea) compositions Expired - Fee Related CA2130603C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/115,280 US5504145A (en) 1993-08-31 1993-08-31 Water-dispersible poly(urethane-urea) compositions
US08/115,280 1993-08-31

Publications (2)

Publication Number Publication Date
CA2130603A1 true CA2130603A1 (en) 1995-03-01
CA2130603C CA2130603C (en) 1999-11-02

Family

ID=22360348

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002130603A Expired - Fee Related CA2130603C (en) 1993-08-31 1994-08-22 Improvement of water-dispersible poly (urethane-urea) compositions

Country Status (6)

Country Link
US (1) US5504145A (en)
EP (1) EP0640632B1 (en)
AU (1) AU683670B2 (en)
CA (1) CA2130603C (en)
ES (1) ES2155076T3 (en)
NZ (1) NZ264337A (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5895806A (en) * 1996-05-06 1999-04-20 Uniroyal Chemical Company, Inc. Polyurethane composition useful for coating cylindrical parts
US5672653A (en) * 1996-05-13 1997-09-30 Elf Atochem North America, Inc. Anionic waterborne polyurethane dispersions
US20020058774A1 (en) 2000-09-06 2002-05-16 Kurth Thomas M. Transesterified polyol having selectable and increased functionality and urethane material products formed using the polyol
US8575226B2 (en) 1998-09-17 2013-11-05 Rhino Linings Corporation Vegetable oil-based coating and method for application
DE19858554A1 (en) * 1998-12-18 2000-06-21 Sueddeutsche Kalkstickstoff Self crosslinking hybrid polymer dispersion, for binder, e.g. in coating or sealing materials, contains fatty acid modified polyurethane
AT409134B (en) * 1999-02-04 2002-05-27 Solutia Austria Gmbh OXYDATIVE DRYING POLYURETHANE DISPERSIONS
DE19930961A1 (en) * 1999-07-05 2001-01-11 Bayer Ag Polyurethane dispersions
WO2002036654A2 (en) * 2000-10-30 2002-05-10 Crompton Corporation Anionic polyurethane dispersion
US7462679B1 (en) * 2002-11-27 2008-12-09 Han Xiong Xiao Process for preparing functionalized oils; adhesives and coatings and interpenetrating polymer networks prepared from the functionalized oils
US7071248B2 (en) * 2003-01-21 2006-07-04 Ashland Licensing And Intellectual Property, Llc Adhesive additives and adhesive compositions containing an adhesive additive
BRPI0408909B1 (en) 2003-04-02 2016-08-02 Valspar Sourcing Inc method for forming a dispersion, composition, method for coating an article, and, article
EP1819789B1 (en) 2004-10-20 2011-06-15 Valspar Sourcing, Inc. Coating compositions for cans and methods of coating
US7858698B2 (en) * 2006-02-16 2010-12-28 A-Line Products Corporation Compositions containing functionalized oils and polyolefins
WO2007131959A1 (en) * 2006-05-12 2007-11-22 Nuplex Resins B.V. Aqueous dispersion of an auto-oxidatively drying polyurethane
KR100764104B1 (en) * 2006-06-07 2007-10-05 구자은 Manufacturing method for water-dispersed polyisocynate
US8076001B2 (en) * 2008-09-02 2011-12-13 Ppg Industries Ohio, Inc Crosslinked coatings comprising lactide
US8614286B2 (en) 2008-09-02 2013-12-24 Ppg Industries Ohio, Inc. Biomass derived radiation curable liquid coatings
US20100055471A1 (en) * 2008-09-02 2010-03-04 Ppg Industries Ohio, Inc. Waterborne polyurethane dispersion comprising biomass derived polyol and coatings comprising same
US9650540B2 (en) 2008-09-02 2017-05-16 Ppg Industries Ohio, Inc. Radiation curable coating compositions comprising a lactide reaction product
EP2416962B1 (en) 2009-04-09 2016-08-10 Valspar Sourcing, Inc. Polymer having unsaturated cycloaliphatic functionality and coating compositions formed therefrom
EP3208289A1 (en) 2009-07-17 2017-08-23 Valspar Sourcing, Inc. Coating composition and articles coated therewith
BR112012006030A2 (en) 2009-09-18 2016-03-22 Valspar Sourcing Inc method coated article and composition
DE102010009896A1 (en) 2010-03-02 2011-09-08 Bayer Materialscience Ag Aqueous polyurethane dispersions
EP2409999A1 (en) 2010-07-24 2012-01-25 Cytec Austria GmbH Polyurethane dispersions, a process of making, and a method of use thereof
ES2545993T3 (en) 2010-10-20 2015-09-17 Basf Coatings Gmbh Transparent scratch-resistant touch-up coating
EP4019565A1 (en) * 2011-01-27 2022-06-29 Vertellus Holdings LLC High molecular weight castor-oil-based polyols and uses thereof
US20150353771A1 (en) 2014-06-10 2015-12-10 Bayer Materialscience Llc Coating compositions with an aqueous dispersion containing a polyurethane and an acid reactive crosslinking agent
US10428172B2 (en) 2016-04-29 2019-10-01 H.B. Fuller Company Reactive polyurethane adhesive composition, polyurethane prepolymer, and flexible laminates including the same

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2634279A (en) * 1949-07-16 1953-04-07 Eastman Kodak Co Preparation of monoglycerides
US2634234A (en) * 1949-07-16 1953-04-07 Eastman Kodak Co Production of monoesters of polyhydric alcohols
US2634278A (en) * 1949-07-16 1953-04-07 Eastman Kodak Co Process for substantially complete conversion of fatty material to partial ester
DE1966836A1 (en) * 1968-10-08 1974-07-04 Reichhold Albert Chemie Ag Water dilutable polyurethanes - for use as coating resins curing by oxidative drying
US3640924A (en) * 1968-12-20 1972-02-08 American Cyanamid Co Textile adhesive from polyurethane containing carboxylate groups
DE1966827A1 (en) * 1969-09-25 1974-06-27 Reichhold Albert Chemie Ag Water-miscible oil-modified polyurethane resin prodn - from excess diisocyanate and hydroxy ester with drying oil in unsatd fatty acid component, for improved drying
US3808162A (en) * 1972-10-10 1974-04-30 Minnesota Mining & Mfg Preparation of urethanes and catalysts therefor
US4056493A (en) * 1972-12-29 1977-11-01 Ford Motor Company Trimellitic anhydride modified urethane electrocoating resins
US4046729A (en) * 1975-06-02 1977-09-06 Ppg Industries, Inc. Water-reduced urethane coating compositions
US4277380A (en) * 1979-03-29 1981-07-07 Textron, Inc. Water-dispersible urethane polymers and aqueous polymer dispersions
JPS5785815A (en) * 1980-11-14 1982-05-28 Dainippon Ink & Chem Inc Water-dispersible resin for paint
DE3526016A1 (en) * 1985-07-20 1987-01-22 Huels Chemische Werke Ag STORAGE-STABLE, RADIATION-HARDENABLE, NCO-FREE, AQUEOUS EMULSIONS
DE3704350A1 (en) * 1987-02-12 1988-08-25 Henkel Kgaa WATER-DISCOVERABLE COATING AGENTS
US4912154A (en) * 1988-12-30 1990-03-27 The Sherwin-Williams Company Water-dispersible air-drying coatings containing 2-oxazoline groups
US5104737A (en) * 1988-12-30 1992-04-14 The Sherwin-Williams Company Water-dispersable air-drying coatings
US5039732A (en) * 1988-12-30 1991-08-13 The Sherwin-Williams Company Water-dispersable air-drying coatings
DE4011376A1 (en) * 1990-04-07 1991-10-10 Basf Lacke & Farben OXIDATIVELY CROSSLINKING URETHANE RESIN
US5095069A (en) * 1990-08-30 1992-03-10 Ppg Industries, Inc. Internally-curable water-based polyurethanes

Also Published As

Publication number Publication date
NZ264337A (en) 1996-09-25
US5504145A (en) 1996-04-02
EP0640632A1 (en) 1995-03-01
CA2130603C (en) 1999-11-02
AU7155694A (en) 1995-03-16
EP0640632B1 (en) 2001-02-28
ES2155076T3 (en) 2001-05-01
AU683670B2 (en) 1997-11-20

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