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WO2001032740A1 - Resines polyester a fonction acide et a fonction epoxy - Google Patents

Resines polyester a fonction acide et a fonction epoxy Download PDF

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Publication number
WO2001032740A1
WO2001032740A1 PCT/EP2000/010916 EP0010916W WO0132740A1 WO 2001032740 A1 WO2001032740 A1 WO 2001032740A1 EP 0010916 W EP0010916 W EP 0010916W WO 0132740 A1 WO0132740 A1 WO 0132740A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
group
functional polyester
carboxyl
polyester resins
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/EP2000/010916
Other languages
English (en)
Inventor
Ronald Petrus Clemens Van Gaalen
Petrus Gerardus Kooijmans
Leo Wim Van Noort
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.)
Shell Internationale Research Maatschappij BV
Resolution Research Nederland BV
Original Assignee
Shell Internationale Research Maatschappij BV
Resolution Research Nederland BV
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 Shell Internationale Research Maatschappij BV, Resolution Research Nederland BV filed Critical Shell Internationale Research Maatschappij BV
Priority to AU18557/01A priority Critical patent/AU1855701A/en
Publication of WO2001032740A1 publication Critical patent/WO2001032740A1/fr
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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
    • 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
    • C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
    • C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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

  • the high level of hydrolizable chlorine is reflected in example 2 of EP-A-447,360 which relates to the glycidation of the 2:1 adduct of hexahydrophthalic anhydride and dimethylolpropionic acid.
  • the product obtained has a chlorine content of 1.5%.
  • Such a high level of residual chlorine is generally undesirable in coating compositions.
  • the triglycidylesters reported in EP-A-447,360 are liquid, they can not be applied in powder coating compositions .
  • X+Y+2Z+3Q+P:X:Y:Z:Q wherein X ranges from 1 to 8, Y ranges from 0 to 8, Z ranges from 0 to 4 and Q ranges from 0 to 3 and wherein p ranges from 1 to 5, and preferably 1-3 and is most preferably equal to 1, at a temperature of from 100 to 240 °C, and preferably fr :o ⁇ m 180 to 210 °C if any compound C is present, until essentially all the hydroxyl groups as initially present in the reaction mixture have been reacted.
  • the invention provides carboxyl functional polyester resins obtainable by reaction of: a) at least a compound of the formula
  • Ai: (C+A 2 ) :B:D:E 1 :E 2 being, (X+Y+l) : Y : 2 :X : Q: P, wherein X ranges from 0 to 8, Y ranges from 1 to 8, Q ranges from 0 to 3 and wherein P ranges from 0 to 3, at a temperature of from 100 to 240 °C, until essentially all the hydroxyl groups as initially present in the reaction mixture have been reacted.
  • the temperature of the condensation reaction is in the range of from 180 to 210 °C if any compound D is present.
  • R3, R4 and R5 are alkyl groups, having together from 5 to 13 carbon atoms, and preferably from 9 to 11 carbon atoms. More preferably the component A2 comprises CARDURA E10 monoglycidyl esters (CARDURA is a trade mark) .
  • Suitable compounds A for use in the process of the present invention are difunctional acids, for example dodecanedioic acid, cyclobutanedicarboxylic acid, suberic acid, succinic acid, glutaric acid, azelaic acid, 1, 4-cyclohexanedicarboxylic acid and 1, 3-cyclohexane- dicarboxylic acid or combinations thereof; of which the cyclohexanedicarboxylic acids being preferred and 1,4-cyclohexane dicarboxylic acid being the most preferred.
  • difunctional acids for example dodecanedioic acid, cyclobutanedicarboxylic acid, suberic acid, succinic acid, glutaric acid, azelaic acid, 1, 4-cyclohexanedicarboxylic acid and 1, 3-cyclohexane- dicarboxylic acid or combinations thereof; of which the cyclohexanedicarboxylic acids being preferred and 1,4-cyclohexane dicar
  • the amount of cross-linking compound used in the coating compositions of the invention will normally be such so as to provide about equal amounts of reactive groups of the cross-linking compound and of the carboxyl groups present in the carboxyl functional polyester resin or of the epoxy groups present in the polyglycidylester resin.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (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)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne des résines polyester à fonction carboxylique que l'on obtient par la réaction de: a) au moins un acide aliphatique ou cycloaliphatique dicarboxylique (A1), mélangé avec une quantité molaire plus petite d'esters monoglycidyles d'acides carboxyles α, et à branches α (A2); b) au moins un composé B comprenant un groupe hydroxyle primaire ou secondaire et un groupe carboxyle aliphatique tertiaire, de préférence un acide hydroxypivalique; c) éventuellement un composé diol C; d) éventuellement un composé acide dihydroxymonocarboxylique D, comprenant un groupe carboxylique aliphatique tertiaire et deux groupes hydroxyles aliphatiques; et e) éventuellement un trihydroxyalkane (E1) ou un tétrahydroxyalkane (E2). Cette invention concerne aussi des résines polyester à fonction glycidyle dérivée de celles-ci, des compositions de revêtement comprenant ces résines polyester à fonction carboxyle et/ou ces résines polyester à fonction glycidyle, et des adduits intermédiaires préparés à partir de A1 et de A2.
PCT/EP2000/010916 1999-11-04 2000-11-02 Resines polyester a fonction acide et a fonction epoxy Ceased WO2001032740A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18557/01A AU1855701A (en) 1999-11-04 2000-11-02 Acid functional and epoxy functional polyester resins

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99203655.8 1999-11-04
EP99203655 1999-11-04

Publications (1)

Publication Number Publication Date
WO2001032740A1 true WO2001032740A1 (fr) 2001-05-10

Family

ID=8240827

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/010916 Ceased WO2001032740A1 (fr) 1999-11-04 2000-11-02 Resines polyester a fonction acide et a fonction epoxy

Country Status (3)

Country Link
JP (1) JP2001131270A (fr)
AU (1) AU1855701A (fr)
WO (1) WO2001032740A1 (fr)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045391A (en) * 1975-02-25 1977-08-30 Deutsche Texaco Aktiengesellschaft Process for preparing low viscosity fatty acid-modified polyesters
JPH0488096A (ja) * 1990-07-30 1992-03-19 Sanken Kako Kk 冷凍機用潤滑油
JPH08165452A (ja) * 1994-12-15 1996-06-25 Nippon Paint Co Ltd 上塗塗料組成物及び塗膜形成方法
WO1998023661A1 (fr) * 1996-11-25 1998-06-04 Shell Internationale Research Maatschappij B.V. Resines polyester a fonctionnalite acide et a fonctionnalite epoxy
WO1998024828A1 (fr) * 1996-12-02 1998-06-11 Shell Internationale Research Maatschappij B.V. Resines de polyester a fonctionnalite acide ou a fonctionnalite epoxy
WO1998042768A2 (fr) * 1997-03-25 1998-10-01 Shell Internationale Research Maatschappij B.V. Resines polyester a fonctions acide et epoxy
WO1999051659A1 (fr) * 1998-04-07 1999-10-14 Shell Internationale Research Maatschappij B.V. Compositions basse viscosite a base de resines polyester a fonctionnalite epoxy

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4045391A (en) * 1975-02-25 1977-08-30 Deutsche Texaco Aktiengesellschaft Process for preparing low viscosity fatty acid-modified polyesters
JPH0488096A (ja) * 1990-07-30 1992-03-19 Sanken Kako Kk 冷凍機用潤滑油
JPH08165452A (ja) * 1994-12-15 1996-06-25 Nippon Paint Co Ltd 上塗塗料組成物及び塗膜形成方法
WO1998023661A1 (fr) * 1996-11-25 1998-06-04 Shell Internationale Research Maatschappij B.V. Resines polyester a fonctionnalite acide et a fonctionnalite epoxy
WO1998024828A1 (fr) * 1996-12-02 1998-06-11 Shell Internationale Research Maatschappij B.V. Resines de polyester a fonctionnalite acide ou a fonctionnalite epoxy
WO1998042768A2 (fr) * 1997-03-25 1998-10-01 Shell Internationale Research Maatschappij B.V. Resines polyester a fonctions acide et epoxy
WO1999051659A1 (fr) * 1998-04-07 1999-10-14 Shell Internationale Research Maatschappij B.V. Compositions basse viscosite a base de resines polyester a fonctionnalite epoxy

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002161949, retrieved from STN Database accession no. 117:134337/DN, HCAPLUS *
DATABASE CHEMABS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002161950, retrieved from STN Database accession no. 125:198678/DN, HCAPLUS *
UPASIRI SAMARAWEERA ET AL: "ENHANCED REACTIVITY OF MELAMINE-FORMALDEHYDE RESINS BY FRACTIONATION. CROSSLINKING AT AMBIENT TEMPERATURE", JOURNAL OF APPLIED POLYMER SCIENCE,US,JOHN WILEY AND SONS INC. NEW YORK, vol. 45, no. 11, 15 August 1992 (1992-08-15), pages 1903 - 1909, XP000292406, ISSN: 0021-8995 *

Also Published As

Publication number Publication date
AU1855701A (en) 2001-05-14
JP2001131270A (ja) 2001-05-15

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