WO2008077118B1 - An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions - Google Patents

An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions

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Publication number
WO2008077118B1
WO2008077118B1 PCT/US2007/088194 US2007088194W WO2008077118B1 WO 2008077118 B1 WO2008077118 B1 WO 2008077118B1 US 2007088194 W US2007088194 W US 2007088194W WO 2008077118 B1 WO2008077118 B1 WO 2008077118B1
Authority
WO
WIPO (PCT)
Prior art keywords
solid content
stream
ultra
high solid
polyurethane dispersion
Prior art date
Application number
PCT/US2007/088194
Other languages
French (fr)
Other versions
WO2008077118A3 (en
WO2008077118A2 (en
Inventor
Bedri Erdem
Debkumar Bhattacharjee
Original Assignee
Dow Global Technologies Inc
Bedri Erdem
Debkumar Bhattacharjee
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 Dow Global Technologies Inc, Bedri Erdem, Debkumar Bhattacharjee filed Critical Dow Global Technologies Inc
Priority to AT07865887T priority Critical patent/ATE517933T1/en
Priority to MX2009006624A priority patent/MX2009006624A/en
Priority to US12/519,831 priority patent/US8821983B2/en
Priority to EP07865887A priority patent/EP2094756B1/en
Priority to CA002672604A priority patent/CA2672604A1/en
Priority to CN2007800513918A priority patent/CN101605831B/en
Priority to BRPI0719419A priority patent/BRPI0719419B8/en
Priority to JP2009543194A priority patent/JP2010513701A/en
Publication of WO2008077118A2 publication Critical patent/WO2008077118A2/en
Publication of WO2008077118A3 publication Critical patent/WO2008077118A3/en
Publication of WO2008077118B1 publication Critical patent/WO2008077118B1/en

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • C08G18/10Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12Prepolymer 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
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805Compounds having only one group containing active hydrogen
    • C08G18/2815Monohydroxy compounds
    • C08G18/283Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/302Water
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/32Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225Polyamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/4009Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/42Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
    • C08G18/4269Lactones
    • C08G18/4277Caprolactone and/or substituted caprolactone
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4804Two or more polyethers of different physical or chemical nature
    • C08G18/4808Mixtures of two or more polyetherdiols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4833Polyethers containing oxyethylene units
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/48Polyethers
    • C08G18/4833Polyethers containing oxyethylene units
    • C08G18/4837Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/62Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00Compositions for sealing or packing joints
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2270/00Compositions for creating interpenetrating networks

Abstract

The instant invention is an ultra-high solid content polyurethane dispersion, and a continuous process for producing ultra-high solid content polyurethane dispersions. The ultra-high solid content polyurethane dispersion includes the reaction product of: (1) a first component, wherein the first component is a first polyurethane prepolymer or a first polyurethane prepolymer emulsion; (2) a second component, wherein the second component is a second polyurethane prepolymer, a second polyurethane prepolymer emulsion, a low solid content polyurethane dispersion, a seed latex, or combinations thereof; (3) and a chain extender. The ultra-high solid content polyurethane dispersion has a solid content of at least 60 percent by weight of the solid, based on the total weight of the ultra-high solid content polyurethane dispersion, and a viscosity in the range of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer. The method for producing a high-solid content polyurethane dispersion includes the following steps: (1) providing a first stream, wherein said first stream comprising a first polyurethane prepolymer or a first polyurethane prepolymer emulsion; (2) providing a second stream, wherein said second stream being a media phase selected from the group consisting of a second polyurethane prepolymer, a second polyurethane prepolymer emulsion, a polyurethane prepolymer dispersion, a seed latex emulsion, or combinations thereof; (3) continuously merging said first stream with said second stream in the presence of a chain extender; and (4) thereby forming a polyurethane dispersion having a solid content of at least 60 percent by weight of the solid, based on the total weight of the ultra-high solid content polyurethane dispersion, and a viscosity in the range of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer.

Claims

AMENDED CLAIMS received by the International Bureau on 20 October 2008 (20.10.2008)WE CLAIM:
1. A continuous process for producing an ultra-high solid content polyurethane dispersion comprising the steps of: providing a first stream, wherein said first stream comprises a first polyurethane prepolymer or a first polyurethane prepolymer emulsion; providing a second stream, wherein said second stream is a media phase selected from the group consisting of a second polyurethane prepolymer, a second polyurethane prepolymer emulsion, a low solid content polyurethane dispersion, a seed latex, and combinations thereof ; continuously merging said first stream with said second stream in the presence of a chain extender; thereby forming said ultra-high solid content polyurethane dispersion, wherein said ultra-high solid content polyurethane dispersion having at least a solid content of at least 60 percent by weight of said solid, based on the total weight of said ultra-high solid content polyurethane dispersion, and a viscosity of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer.
2. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 1, wherein said first stream comprises first polymer resins and said second stream comprises second polymer resins, and wherein said first polymer resin and said second polymer resin have a volume average particle size ratio in the range of 1 :5 to 1 :2.
3. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 2, wherein said first polymer resin and said second polymer resin have a volume average particle size ratio in the range of about 1 :3.
4. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 1, wherein said first stream comprises first polymer resins and said second stream comprises second polymer resins, and wherein
42 said ultra-high solid content polyurethane dispersion comprises 20 to 40 percent by weight of said first polymer resins having a particle size in the range of 0.04 micron to 5.0 micron, and 60 to 80 percent by weight of said second polymer resins having a particle size in the range of 0.05 micron to 5.0 micron, based on the total weight of said first polymer resin and said second polymer resin.
5. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 1, wherein said seed latex is selected from the group consisting of a dispersion, emulsion, and latex of olefins, epoxies, silicon, styrene, acrylate, butadiene, isoprene, vinyl acetate, copolymers thereof, and blends thereof.
6. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 1, wherein said seed latex is an oil phase emulsified in water.
7. A continuous process for producing an ultra-high solid content polyurethane dispersion comprising the steps of: providing a first stream, wherein said first stream is a first polyurethane prepolymer stream; providing a second stream, wherein said second stream is a media phase; continuously merging said first and said second stream together in the presence of a surfactant at a temperature in the range of 100C to 7O0C, wherein the ratio of said second stream to first stream being in the range of 0.1 to 0.6, and wherein said surfactant being present in a concentration range of 0.1 to 3.0 percent, based on the total weight of said first stream, said second stream, and said surfactant; thereby forming said ultra-high solid content polyurethane dispersion, wherein said ultra-high solid content polyurethane dispersion having at least a solid content of at least 60 percent by weight of said solid, based on the total weight of said ultra-high solid content polyurethane dispersion, and a viscosity of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer.
43
8. An ultra high solid content polyurethane dispersion prepared according to the continuous process of either Claim 1 or Claim 7.
9. The ultra-high solid content polyurethane dispersion according to Claim 8, wherein said ultra high solid content polyurethane dispersion further comprises an inorganic filler.
10. The continuous process for producing an ultra-high solid content polyurethane dispersion according to either Claim 1 or Claim 7, wherein said first or second polyurethane prepolymer is a reaction product of at least one polyisocyanate and at least one polyol.
11. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 10, wherein said polyisocyanate is aromatic or aliphatic.
12. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 11, wherein said polyol is selected from the group consisting of polyether, polyester, polycarbonate, natural seed oil polyol, and combinations thereof.
13. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 12, wherein said first or second polyurethane prepolymer is ionic or non-ionic.
14. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 8, wherein said first or second polyurethane prepolymer is isocyanate terminated or hydroxyl terminated.
44
15. The continuous process for producing an ultra-high solid content polyurethane dispersion according to Claim 8, wherein said first or second polyurethane prepolymer is isocyanate terminated or hydroxy! terminated.
16. A method for producing an article comprising the steps of: providing a first stream, wherein said first stream comprises a first polyurethane prepolymer or a first polyurethane prepolymer emulsion; providing a second stream, wherein second stream is a media phase selected from the group consisting of a second polyurethane prepolymer, a second polyurethane prepolymer emulsion, a polyurethane dispersion, a seed latex emulsion, or combinations thereof; continuously merging the first stream with the second stream optionally in the presence of a chain extender; (4) thereby forming a polyurethane dispersion having a solid content of at least 60 percent by weight of the solid, based on the total weight of the ultra-high solid content polyurethane dispersion, and a viscosity of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer; applying the dispersion to a substrate drying the dispersion; and thereby forming the article.
17. A method for producing an article comprising the steps of: providing a first stream, wherein said first stream comprises a first polyurethane prepolymer or a first polyurethane prepolymer emulsion; providing a second stream, wherein second stream is a media phase selected from the group consisting of a second polyurethane prepolymer, a second polyurethane prepolymer emulsion, a polyurethane dispersion, a seed latex emulsion, or combinations thereof; continuously merging the first stream with the second stream optionally in the presence of a chain extender; (4) thereby forming a polyurethane dispersion having a solid content of at least 60 percent by weight of the solid, based on the total weight of the ultra-high solid content polyurethane dispersion, and a viscosity of less than 5000 cps at 20 rpm at 21° C using spindle #4 with Brookfield viscometer; frothing the dispersion; thereby forming a foam; drying the foam; and thereby forming the article.
18. An article produced according to the method of either Claim 16 or Claim 17.
46
PCT/US2007/088194 2006-12-19 2007-12-19 An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions WO2008077118A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AT07865887T ATE517933T1 (en) 2006-12-19 2007-12-19 ULTRA HIGH SOLIDS POLYURETHANE DISPERSION AND CONTINUOUS PROCESS FOR PRODUCING ULTRA HIGH SOLIDS POLYURETHANE DISPERSIONS
MX2009006624A MX2009006624A (en) 2006-12-19 2007-12-19 An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions.
US12/519,831 US8821983B2 (en) 2006-12-19 2007-12-19 Ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions
EP07865887A EP2094756B1 (en) 2006-12-19 2007-12-19 An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions
CA002672604A CA2672604A1 (en) 2006-12-19 2007-12-19 An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions
CN2007800513918A CN101605831B (en) 2006-12-19 2007-12-19 Ultra-high solid content polyurethane dispersion and continuous process for producing ultra-high solid content polyurethane dispersions
BRPI0719419A BRPI0719419B8 (en) 2006-12-19 2007-12-19 continuous process for producing an ultra-high solids aqueous polyurethane dispersion and method for producing an article
JP2009543194A JP2010513701A (en) 2006-12-19 2007-12-19 Polyurethane dispersion with ultra-high solid content and continuous process for producing polyurethane dispersion with ultra-high solid content

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US87565606P 2006-12-19 2006-12-19
US60/875,656 2006-12-19

Publications (3)

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WO2008077118A2 WO2008077118A2 (en) 2008-06-26
WO2008077118A3 WO2008077118A3 (en) 2008-10-16
WO2008077118B1 true WO2008077118B1 (en) 2008-11-27

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PCT/US2007/088197 WO2008077120A1 (en) 2006-12-19 2007-12-19 Composition comprising polyurethane dispersion having high solids content
PCT/US2007/088194 WO2008077118A2 (en) 2006-12-19 2007-12-19 An ultra-high solid content polyurethane dispersion and a continuous process for producing ultra-high solid content polyurethane dispersions

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US (2) US8821983B2 (en)
EP (2) EP2094756B1 (en)
JP (2) JP2010513702A (en)
KR (2) KR101467594B1 (en)
CN (2) CN101432327A (en)
AT (2) ATE499394T1 (en)
BR (2) BRPI0719419B8 (en)
CA (2) CA2643426A1 (en)
DE (1) DE602007012665D1 (en)
DK (1) DK1991597T3 (en)
MX (2) MX2008013124A (en)
RU (2) RU2009127752A (en)
TW (2) TW200838891A (en)
WO (2) WO2008077120A1 (en)
ZA (1) ZA200807314B (en)

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