WO2002042348A3 - Polyols containing carboxyl groups and production thereof - Google Patents

Polyols containing carboxyl groups and production thereof Download PDF

Info

Publication number
WO2002042348A3
WO2002042348A3 PCT/US2001/044214 US0144214W WO0242348A3 WO 2002042348 A3 WO2002042348 A3 WO 2002042348A3 US 0144214 W US0144214 W US 0144214W WO 0242348 A3 WO0242348 A3 WO 0242348A3
Authority
WO
WIPO (PCT)
Prior art keywords
acid
carboxyl
containing polyol
directed
inorganic
Prior art date
Application number
PCT/US2001/044214
Other languages
French (fr)
Other versions
WO2002042348A2 (en
Inventor
Indulis Gruzins
Donald Farrell Mcelheney
Robert C Hire
Jerry Douglas Necessary
Joseph T Farrell
Original Assignee
Arch Chem 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 US09/723,263 external-priority patent/US6716913B1/en
Application filed by Arch Chem Inc filed Critical Arch Chem Inc
Priority to JP2002545062A priority Critical patent/JP2004514752A/en
Priority to AU2002217873A priority patent/AU2002217873A1/en
Priority to EP01997514A priority patent/EP1358244A4/en
Priority to KR10-2003-7007024A priority patent/KR20040027502A/en
Publication of WO2002042348A2 publication Critical patent/WO2002042348A2/en
Publication of WO2002042348A3 publication Critical patent/WO2002042348A3/en

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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • 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
    • C08G18/4887—Polyethers containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/40—Succinic acid esters
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
    • C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
    • C08G18/4241—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyethers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention is directed to a low viscosity carboxyl-containing polyol composition having a viscosity in the range of about 3,000-100,000 centipoise, and having an oligomer content of less than 30 mg KOH/g. Preferably, the carboxyl-containing polyol has one ester group per molecule. The carboxyl-containing polyol is suitable for use in preparing low viscosity polyurethane prepolymers. Also disclosed is a method of producing this carboxyl-containing polyol composition by reacting a low molecular weight triol with an acid anhydride in the presence of 25-500 ppm of an inorganic or organic acid catalyst. The organic or inorganic acid is preferably selected from the group consisting of hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, formic acid, proprionic acid, p-toluenesulfonic acid, oxalic acid, and combinations thereof. The present invention is also directed to methods of making the above carboxyl-containing polyols, as well as prepolymers and urethane polymers containing the above carboxyl-containing polyols.
PCT/US2001/044214 2000-11-27 2001-11-26 Polyols containing carboxyl groups and production thereof WO2002042348A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2002545062A JP2004514752A (en) 2000-11-27 2001-11-26 Polyol containing carboxyl group and method for producing the same
AU2002217873A AU2002217873A1 (en) 2000-11-27 2001-11-26 Polyols containing carboxyl groups and production thereof
EP01997514A EP1358244A4 (en) 2000-11-27 2001-11-26 Polyols containing carboxyl groups and production thereof
KR10-2003-7007024A KR20040027502A (en) 2000-11-27 2001-11-26 Polyols Containing Carboxyl Groups and Production Thereof

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US09/723,263 US6716913B1 (en) 2000-11-27 2000-11-27 Polyols containing grafted carboxyl groups and method of making same
US09/723,263 2000-11-27
US99648001A 2001-11-20 2001-11-20
US09/996,480 2001-11-20

Publications (2)

Publication Number Publication Date
WO2002042348A2 WO2002042348A2 (en) 2002-05-30
WO2002042348A3 true WO2002042348A3 (en) 2003-01-03

Family

ID=27110774

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/044214 WO2002042348A2 (en) 2000-11-27 2001-11-26 Polyols containing carboxyl groups and production thereof

Country Status (5)

Country Link
EP (1) EP1358244A4 (en)
JP (1) JP2004514752A (en)
KR (1) KR20040027502A (en)
AU (1) AU2002217873A1 (en)
WO (1) WO2002042348A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2183293B1 (en) * 2007-08-28 2015-09-09 Mankiewicz Gebr. & Co. Gmbh & Co Kg Coating composition for producing liquid films
JP6148069B2 (en) * 2013-05-23 2017-06-14 東栄化成株式会社 Method for producing aqueous urethane-modified (meth) acrylic resin dispersion
CN112358590A (en) * 2020-10-23 2021-02-12 国网福建省电力有限公司 Method for preparing aqueous polyurethane emulsion by using carboxyl polyether dihydric alcohol

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6103822A (en) * 1996-08-16 2000-08-15 Inolex Investment Corporation Polymeric acid functional polyols, polyurethanes and methods for making same

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3431223A (en) * 1966-06-10 1969-03-04 Upjohn Co Partial esters as polyols for polyurethane foams
BE795473A (en) * 1972-02-17 1973-08-16 Bayer Ag SYNTHETIC RESIN FOAMS WITH ACID GROUPS
DE2359613C3 (en) * 1973-11-30 1980-05-22 Bayer Ag, 5090 Leverkusen Liquid, solvent-free polyisocyanates containing aromatic carboxyl and / or carboxylate groups, processes for their preparation and their use
US4403091A (en) * 1982-09-28 1983-09-06 Ppg Industries, Inc. Ungelled hydroxy group-containing oligomers
DE3315381A1 (en) * 1983-04-28 1984-10-31 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING POLYESTER OR POLYETHER-POLYESTER POLYOLS
US4644047A (en) * 1984-06-20 1987-02-17 Stepan Company Self-compatibilizing phthalate-based polyester polyols
GB8524579D0 (en) * 1985-10-04 1985-11-06 Polyvinyl Chemicals Inc Coating compositions
DE3829588A1 (en) * 1988-09-01 1990-03-15 Wolff Walsrode Ag WATER-DISPERSIBLE ALLYLURETHANES AND THEIR USE FOR THE PRODUCTION OF VARNISHES
US5508340A (en) * 1993-03-10 1996-04-16 R. E. Hart Labs, Inc. Water-based, solvent-free or low voc, two-component polyurethane coatings
JP3276463B2 (en) * 1993-07-07 2002-04-22 三井化学株式会社 Manufacturing method of rigid polyurethane foam
EP0705858B1 (en) * 1994-10-07 1997-12-17 SYNTHOPOL CHEMIE Dr. rer. pol. Koch GmbH & CO. KG Novel polyesterpolyols and their use as a polyolcomponent in two-component polyurethane lacquers
KR0173522B1 (en) * 1995-12-20 1999-04-01 최근배 Method for preparing polyurethane prepolymer, method for preparing water-soluble polyurethane dispersion prepared from the prepolymer, and uses thereof
WO1997031964A1 (en) * 1996-02-29 1997-09-04 Synthopol Chemie Dr. Rer. Pol. Koch Gmbh & Co. Kg Novel polyester polyols and their use as the polyol component in two-component polyurethane paints
FI104553B (en) * 1997-05-07 2000-02-29 Fortum Oil & Gas Oy Process for the preparation and purification of complex esters

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6103822A (en) * 1996-08-16 2000-08-15 Inolex Investment Corporation Polymeric acid functional polyols, polyurethanes and methods for making same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP1358244A4 *

Also Published As

Publication number Publication date
AU2002217873A1 (en) 2002-06-03
KR20040027502A (en) 2004-04-01
EP1358244A4 (en) 2005-02-09
EP1358244A2 (en) 2003-11-05
WO2002042348A2 (en) 2002-05-30
JP2004514752A (en) 2004-05-20

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