WO1999029501A1 - Preparation de resines de polyester insature, a base d'empd - Google Patents

Preparation de resines de polyester insature, a base d'empd Download PDF

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Publication number
WO1999029501A1
WO1999029501A1 PCT/US1998/027286 US9827286W WO9929501A1 WO 1999029501 A1 WO1999029501 A1 WO 1999029501A1 US 9827286 W US9827286 W US 9827286W WO 9929501 A1 WO9929501 A1 WO 9929501A1
Authority
WO
WIPO (PCT)
Prior art keywords
empd
unsaturated polyester
polyester resins
preparation
resin
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/US1998/027286
Other languages
English (en)
Inventor
Dennis Joseph Golob
James Thomas Tanner, Iii
Larry Keith Johnson
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/US1998/027286 priority Critical patent/WO1999029501A1/fr
Publication of WO1999029501A1 publication Critical patent/WO1999029501A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/06—Unsaturated polyesters

Definitions

  • EMPD 1-ethyl-2-methyl-1 ,3-propanediol
  • EMPD is a glycol intermediate that can impart unique performance when used in unsaturated polyester resins. Its chemical structure brings the following properties to polyester resins and composites made from these resins: better resin processability, improved resin solubility, lower resin viscosity, improved chemical, water & stain resistance, better fiberglass wetting, lower styrene content, low profile surfaces, higher filler content and better mold filling.
  • WO 97/16401 describes reaction mixtures containing substituted hydrocarbon diols and their preparation and using in coatings.
  • the disclosure includes preparation of 2,2-disubstituted hydrocarbon diols and more specifically 2-ethyl-2-methyl-1 ,3-propanediol.
  • the application further described the polyesters derived from such diols and their utility in coatings, ink, sealant and adhesive composition.
  • WO 97/16473 describes polyesters and processes for preparing same.
  • the polyester are prepared from a diacids such as terephthalic acid or isophthalic acid and a diol, preferably, from 2,2-disubstituted 1 ,3- propanediol and more specifically 2-ethyl-2-methyl-1 ,3-propanediol.
  • the application further described curable coating, ink, sealant and adhesive compositions based on such polyesters.
  • the present invention relates to the use of EMPD to create unsaturated polyester resins similar to those based on propylene glycol (PG) and other commonly used glycols in unsaturated polyester resins without the processing and performance deficiencies normally associated with PG.
  • PG propylene glycol
  • Ethyl-2-methyl-1 ,3-propanediol may be used as a glycol and reacted with diacids such as isophthalic acid (PIA), phthalic anhydride (PA), terephthalic acid, adipic acid, maleic anhydride (MA), etc.
  • diacids such as isophthalic acid (PIA), phthalic anhydride (PA), terephthalic acid, adipic acid, maleic anhydride (MA), etc.
  • glycols that are typically used include neopentyl glycol, propylene glycol, ethylene glycol, diethylene glycol, triethylene glycol, 2-methyl-1 ,3-propanediol, 3-hydroxy-2,2-dimethylpropyl-3-hydroxy- 2,2-dimethylpropanoate, cyclohexanedimethanol, 2-butyl-2-ethyl-1 ,3- propanediol, 1 ,6-hexanediol, 2,2,4-trimethyl-1 ,3-pentanediol, etc.
  • EMPD resins made with isophthalic acid (PIA), phthalic anhydride (PA) and maleic anhydride (MA) are described below (Table 1 ).
  • the reactants were processed under a nitrogen blanket.
  • the first stage reactants were charged into two liter resin kettles equipped with heating mantle, agitator, nitrogen purge, temperature probe, packed distillation column, and total condenser.
  • the first stage contents of the kettle was heated to 210°C and held until an acid number of 13-17 was reached. This completed the first stage reaction and the kettle contents were cooled to 120°C.
  • the MA was added to the kettle and the temperature brought slowly to 210°C. The resins were held at 210°C until a neat resin ICI viscosity of 4.8-5.2 poise at 175°C. The resin was poured out hot into aluminum boats and allowed to harden.
  • the EMPD/PIA/MA resin was made into a 55% solids solution in styrene and 1/8 inch castings were prepared. The following physical data was obtained from these castings (Table 3). Table 3:1/8 inch Castin Ph sical Testin Results for EMPD/PIA/MA

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne l'utilisation d'EMPD pour la production de résine de polyester insaturé, similaire aux résines à base de propylèneglycol (PG) et d'autres glycols couramment utilisés dans les résines de polyester insaturé, mais ne présentant les insuffisances au traitement et les performance insuffisantes habituellement associées au PG.
PCT/US1998/027286 1998-12-22 1998-12-22 Preparation de resines de polyester insature, a base d'empd Ceased WO1999029501A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027286 WO1999029501A1 (fr) 1998-12-22 1998-12-22 Preparation de resines de polyester insature, a base d'empd

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1998/027286 WO1999029501A1 (fr) 1998-12-22 1998-12-22 Preparation de resines de polyester insature, a base d'empd

Publications (1)

Publication Number Publication Date
WO1999029501A1 true WO1999029501A1 (fr) 1999-06-17

Family

ID=22268533

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1998/027286 Ceased WO1999029501A1 (fr) 1998-12-22 1998-12-22 Preparation de resines de polyester insature, a base d'empd

Country Status (1)

Country Link
WO (1) WO1999029501A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5442023A (en) * 1994-06-30 1995-08-15 Union Carbide Chemicals & Plastics Technology Corporation Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5442023A (en) * 1994-06-30 1995-08-15 Union Carbide Chemicals & Plastics Technology Corporation Hindered-hydroxyl functional (meth)acrylate monomers containing di(meth)acrylates and compositions including same

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