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WO1999060046A1 - Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables - Google Patents

Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables Download PDF

Info

Publication number
WO1999060046A1
WO1999060046A1 PCT/US1998/027921 US9827921W WO9960046A1 WO 1999060046 A1 WO1999060046 A1 WO 1999060046A1 US 9827921 W US9827921 W US 9827921W WO 9960046 A1 WO9960046 A1 WO 9960046A1
Authority
WO
WIPO (PCT)
Prior art keywords
functionality
carboxylic acid
acid
glycol
polyester
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/US1998/027921
Other languages
English (en)
Inventor
Travis Eugene Jones
Stacey James Marsh
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.)
Eastman Chemical Co
Original Assignee
Eastman Chemical 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 Chemical Co filed Critical Eastman Chemical Co
Priority to PCT/US1998/027921 priority Critical patent/WO1999060046A1/fr
Publication of WO1999060046A1 publication Critical patent/WO1999060046A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C09D175/06—Polyurethanes from polyesters
    • 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
    • C08G18/28—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
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic 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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • 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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • 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

Definitions

  • This invention concerns the use of trimellitic anhydride (TMA) and/or dimethylolpropionic acid (DMPA) in concert with polyols and chain extending diacids and glycols at temperatures at or below 180°C to produce acid-functional polyesters with high hydroxyl functionality for waterbome applications (Table 1 and Table 4) .
  • TMA and/or DMPA provide chain-extension and pendant acid groups while polyols provide branching to the polyester. This allows for formulation of highly branched polyesters with reduced propensity for gelation during polymerization.
  • These polyesters are suitable for use with crosslinkers that are capable of reacting with hydroxyls such as isocyanates and melamines .
  • HHTA hexahydro- trimellitic anhydride
  • TMA trimethylolpropane
  • glycerol trimethylolethane
  • di-trimethylolpropane pentaerythritol
  • Glycols and diacids that are hydrophobic and non-polar provide TMA and/or DMPA containing polyesters with excellent hydrolytic stability (Table 3) .
  • hydrophobic, non-polar monomers include, but are not limited to, dodecanedioic acid (DDDA) , 1 , 4-cyclohexanedicarboxylic acid (1,4-CHDA), 1, 3-cyclohexanedicarboxylic acid (1,3-CHDA), hexahydrophthalic anhydride (HHPA) , tetrahydrophthalic anhydride (THPA) , 3-hydroxy-2 , 2-dimethylpropyl 3-hydroxy-2 , 2-dimethylpropanoate (HPHP) , 2-butyl-2-ethyl-l, 3-propanediol (BEPD) , 2,2,4- trimethyl-l,3-pentanediol ( TMPD glycol) , 2 , 2-diethyl-l , 3- propane
  • Stage 2 maximum reaction temperature is 180°C.
  • polyester resins were dispersed in water (Table 6) and tested for hydrolysis resistance at 52°C. Acid number and pH drift were measured every two weeks .
  • the resins were tested in coating formulations (Table 7) .
  • the coatings were stored at 50°C and samples taken at two and six weeks of aging. Various cure-film tests were performed.
  • the resins have acceptable storage stability in water as well as acceptable film properties before and after aging.
  • Resins of the invention are useful in coatings exposed to natural weather conditions.
  • the resins may also be used in zero to low VOC systems when combined with a neutralizing agent such as ammonia.
  • Resins of the invention may also be formulated over a wide range of viscosity profiles.
  • Resins of the invention may also be blended with water-reducible resins known in the art, such as acrylic resins, to
  • Glycol variable TMPD glycol, BEPD, or CHDM Table 2 Camile System Startup & Shutdown Conditions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Paints Or Removers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

Cette invention a trait à une résine polyester, résistant à la gélification, stable du point de vue hydrolytique et dotée de fonctionnalités hydroxy et acide carboxylique élevées. Elle concerne également une composition d'enduit aqueux obtenue à l'aide de cette résine. Elle porte, du surcroît, sur un procédé de préparation de ces compositions d'enduit aqueux.
PCT/US1998/027921 1998-12-30 1998-12-30 Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables Ceased WO1999060046A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027921 WO1999060046A1 (fr) 1998-12-30 1998-12-30 Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027921 WO1999060046A1 (fr) 1998-12-30 1998-12-30 Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables

Publications (1)

Publication Number Publication Date
WO1999060046A1 true WO1999060046A1 (fr) 1999-11-25

Family

ID=22268590

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/027921 Ceased WO1999060046A1 (fr) 1998-12-30 1998-12-30 Resines polyester resistantes a la gelification, stables du point de vue hydrolytique a fonctionnalites hydroxy et acide carboxylique elevees pour enduits aqueux a base d'isocyanate reticulables

Country Status (1)

Country Link
WO (1) WO1999060046A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1261650A4 (fr) * 2000-01-18 2003-04-02 Accurez Corp Resines polyesteres reductibles dans l'eau et revetements urethane produits a partir de ces resines
US7199194B2 (en) * 2002-02-20 2007-04-03 E. I. Du Pont De Nemours And Company Two component coating compositions containing highly branched copolyester polyol
CN110358047A (zh) * 2017-02-14 2019-10-22 广东博海化工科技有限公司 一种环保型耐温转移涂料用水性聚氨酯涂料及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4116902A (en) * 1977-10-05 1978-09-26 International Minerals & Chemical Corp. Polyurethane-modified alkyd resin
US4172822A (en) * 1977-06-06 1979-10-30 Herberts Gesellschaft Mit Beschrankter Haftung Aqueous coating compositions containing polyester containing carboxyl groups
US5306567A (en) * 1992-11-27 1994-04-26 Eastman Kodak Company Thermosetting coating compositions
EP0612779A2 (fr) * 1993-02-26 1994-08-31 Hoechst Aktiengesellschaft Polyesters modifiés par l'acide et leur utilisation dans des vernis au four

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4172822A (en) * 1977-06-06 1979-10-30 Herberts Gesellschaft Mit Beschrankter Haftung Aqueous coating compositions containing polyester containing carboxyl groups
US4116902A (en) * 1977-10-05 1978-09-26 International Minerals & Chemical Corp. Polyurethane-modified alkyd resin
US5306567A (en) * 1992-11-27 1994-04-26 Eastman Kodak Company Thermosetting coating compositions
EP0612779A2 (fr) * 1993-02-26 1994-08-31 Hoechst Aktiengesellschaft Polyesters modifiés par l'acide et leur utilisation dans des vernis au four

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1261650A4 (fr) * 2000-01-18 2003-04-02 Accurez Corp Resines polyesteres reductibles dans l'eau et revetements urethane produits a partir de ces resines
US7199194B2 (en) * 2002-02-20 2007-04-03 E. I. Du Pont De Nemours And Company Two component coating compositions containing highly branched copolyester polyol
CN110358047A (zh) * 2017-02-14 2019-10-22 广东博海化工科技有限公司 一种环保型耐温转移涂料用水性聚氨酯涂料及其制备方法
CN110358046A (zh) * 2017-02-14 2019-10-22 广东博海化工科技有限公司 一种成膜性好的耐温转移涂料用水性聚氨酯乳液及其制备方法
CN110358048A (zh) * 2017-02-14 2019-10-22 广东博海化工科技有限公司 一种耐温转移涂料用水性聚氨酯乳液的制备方法

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