WO2011009766A1 - Polyesters à haute fonctionnalité, fortement ou très fortement ramifiés, ainsi que leur fabrication et leur utilisation - Google Patents

Polyesters à haute fonctionnalité, fortement ou très fortement ramifiés, ainsi que leur fabrication et leur utilisation Download PDF

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Publication number
WO2011009766A1
WO2011009766A1 PCT/EP2010/060045 EP2010060045W WO2011009766A1 WO 2011009766 A1 WO2011009766 A1 WO 2011009766A1 EP 2010060045 W EP2010060045 W EP 2010060045W WO 2011009766 A1 WO2011009766 A1 WO 2011009766A1
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WO
WIPO (PCT)
Prior art keywords
acid
groups
hydroxymethyl
mol
reaction
Prior art date
Application number
PCT/EP2010/060045
Other languages
German (de)
English (en)
Inventor
Monika Haberecht
Bernd Bruchmann
Darijo Mijolovic
Angelika Maria Steinbrecher
Oihana Elizalde
Original Assignee
Basf Se
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 Basf Se filed Critical Basf Se
Priority to EP10170358A priority Critical patent/EP2277934A1/fr
Publication of WO2011009766A1 publication Critical patent/WO2011009766A1/fr

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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
    • C08G63/02—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
    • C08G63/137—Acids or hydroxy compounds containing cycloaliphatic 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
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive 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
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/005—Hyperbranched macromolecules

Definitions

  • a monocarboxylic acid F wherein the ratio of the reactive groups in the reaction mixture is selected such that a molar ratio of OH groups to carboxy groups or derivatives thereof is from 5: 1 to 1: 5, preferably from 4: 1 to 1: 4, more preferably from 3: 1 to 1: 3 and most preferably from 2: 1 to 1: 2 sets, and the proportion of hydroxy groups in ß, ß, ß ', ß'-tetra (hydroxymethyl) cycloalkanol based to the sum of the hydroxy groups in the components ß, ß, ß ', ß'- tetra (hydroxymethyl) cycloalkanol, (B2) and (C x ) is 10 to 100 mol%, with the proviso that
  • aromatic dicarboxylic acids such as, for example, phthalic acid, isophthalic acid or terephthalic acid.
  • unsaturated dicarboxylic acids such as maleic acid, fumaric acid, itaconic acid, mescaconic acid, glutaconic acid or citraconic acid.
  • the dicarboxylic acids mentioned can also be substituted by one or more radicals selected from
  • extraction and washing processes and apparatuses known per se can be used, e.g. those described in Ullmann's Encyclopedia of Industrial Chemistry, 6th ed, 1999 Electronic Release, Chapter: Liquid - Liquid Extraction - Apparatus.
  • these can be one-stage or multistage, preferably single-stage extractions, and those in cocurrent or countercurrent mode, preferably countercurrent mode.
  • an inert gas under the reaction conditions may be introduced into the distillation apparatus, for example, 0.1 to 1, preferably 0,2 - 0,8 and more preferably from 0.3 to 0.7 m 3 oxygen containing gas per m 3 reaction mixture and per hour.
  • solvent stripping may be carried out.
  • the product which may still contain small amounts of solvent or low-boiling impurities, heated to 50 - 150 0 C, preferably 80 - 150 0 C and removed the remaining amounts of solvent with a suitable gas in a suitable apparatus. If necessary, a vacuum can also be applied to assist.
  • the isocyanate groups of the di- or polyisocyanates may also be present in capped form.
  • Suitable capping agents for NCO groups are e.g. Oximes, phenols, imidazoles, pyrazoles, pyrazolinones, triazoles, diketopiperazines, caprolactam, malonic acid esters or compounds as mentioned in the publications of Z.W. Wicks, Prog. Org. Coat. 3 (1975) 73-99 and Prog. Org. Coat 9 (1981), 3-28, by DA Wicks and Z.W. Wicks, Prog. Org. Coat. 36 (1999), 148-172 and Prog. Org. Coat. 41 (2001), 1-83 and in Houben-Weyl, Methods of Organic Chemistry, Vol. XIV / 2, 61 ff. Georg Thieme Verlag, Stuttgart 1,963th
  • Suitable examples include epoxidized olefins, glycidyl esters (eg glycidyl (meth) acrylate) of saturated or unsaturated carboxylic acids or glycidyl ethers of aliphatic or aromatic polyols. Such products are commercially available in large numbers. Polyglycidyl compounds of the bisphenol A, F or B type and glycidyl ethers of polyhydric alcohols, for example of butanediol, of 1,6-hexanediol, of glycerol and of pentaerythritol, are particularly preferred. Examples of such polyepoxide compounds are Epikote® 812 (epoxy value: approx.
  • Suitable urea resins are those which are obtainable by reacting ureas with aldehydes and can be modified if appropriate.
  • ureas urea, N-substituted or N, N'-disubstituted ureas are suitable, e.g.
  • N-methylurea N-phenylurea, N, N'-dimethylurea, hexamethylenediurea, N, N'-diphenylurea, 1,2-ethylenediurea, 1,3-propylenediurea, diethylenetriurea, dipropylenetriurea, 2-hydroxypropylenediurea, 2- imidazolidinone (ethyleneurea), 2-oxohexahydropyrimidine (propyleneurea) or 2-oxo-5-hydroxyhexahydropyrimidine (5-hydroxypropyleneurea).
  • Urea resins may optionally be partially or fully modified, e.g. by reaction with mono- od.
  • Polyfunctional alcohols, ammonia or amines (cationically modified urea resins) or with (hydrogen) sulfites (anionic modified urea resins), particularly suitable are the alcohol-modified urea resins.
  • the waterborne basecoats have, for example, solids contents of 10 to 50% by weight; for effect waterborne basecoats, for example, they are preferably 15 to 30% by weight; for unicolour waterborne basecoats, they are preferably higher, for example 20 to 45% by weight.
  • a functionalization of hydroxyl-containing polyesters according to the invention with saturated or unsaturated, aliphatic, cycloaliphatic, araliphatic or aromatic monocarboxylic acids F may preferably be carried out subsequently, ie after completion of the actual reaction of the components A2, B2, C x and / or D y in a separate step.
  • Suitable saturated monocarboxylic acids F may comprise 1 to 30 carbon atoms, preferably 2 to 30, particularly preferably 4 to 25, very particularly preferably 6 to 20 and in particular 8 to 20 carbon atoms.
  • a reaction in the sense of a transesterification can be carried out, for example, in the presence of at least one transesterification catalyst, for example metal chelate compounds of, for example, As hafnium, titanium, zirconium or calcium, alkali metal and Magnesiumalkohola- te, organic tin compounds or calcium and lithium compounds, for example, oxides, hydroxides, carbonates or halides, but preferably titanium, magnesium or aluminum.
  • a transesterification catalyst for example metal chelate compounds of, for example, As hafnium, titanium, zirconium or calcium, alkali metal and Magnesiumalkohola- te, organic tin compounds or calcium and lithium compounds, for example, oxides, hydroxides, carbonates or halides, but preferably titanium, magnesium or aluminum.
  • esters of ⁇ , ⁇ -unsaturated carboxylic acids with the polyesters according to the invention can be used, for example, in radiation-curable coating compositions.
  • Hydroxy-containing high-functionality, high or hyperbranched polyesters can be obtained, for example, by addition of molecules containing isocyanate groups be modified.
  • polyesters containing urethane groups can be obtained by reaction with alkyl or aryl isocyanates.
  • the polymer according to the invention was obtained in the form of a pale yellow solid.
  • the polymer according to the invention was obtained in the form of a pale yellow solid.
  • a hopper filled with approx. 60-8Og of sand and equipped with wheels is pulled over a lacquer-coated glass plate at a constant feed rate.
  • the feed rate is 1 cm / h.
  • Sand drying is the period of time between the beginning of the test and the last permanent adhesion of the grains of sand.
  • the through-drying is determined as the time in which the wheels of the funnel still leave a trace in the paint.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention porte sur des polyesters hautement fonctionnels, construits d'une manière ciblée, à forte ou très forte ramification, qui contiennent, incorporés en tant que composants de construction, un ß,ß,ß',ß'-tétra(hydroxyméthyl)cycloalkanol. L'invention porte également sur un procédé de fabrication de ces polyesters ainsi que sur leur utilisation.
PCT/EP2010/060045 2009-07-24 2010-07-13 Polyesters à haute fonctionnalité, fortement ou très fortement ramifiés, ainsi que leur fabrication et leur utilisation WO2011009766A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP10170358A EP2277934A1 (fr) 2009-07-24 2010-07-22 Utilisation de polycarbonates hautement fonctionnels, hautement ramifies ou hyper ramifies

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09166368.2 2009-07-24
EP09166368 2009-07-24

Publications (1)

Publication Number Publication Date
WO2011009766A1 true WO2011009766A1 (fr) 2011-01-27

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8664427B2 (en) 2009-10-16 2014-03-04 Basf Se Process for preparing highly branched polyhydroxybenzoic acid alkoxylates
CN114350070A (zh) * 2022-03-03 2022-04-15 安徽海铭塑业有限公司 一种载银抗菌母粒及其应用
CN114957630A (zh) * 2022-05-24 2022-08-30 珠海金发生物材料有限公司 一种半芳香族聚酯及其制备方法和应用

Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1047429B (de) * 1957-03-29 1958-12-24 Basf Ag Verfahren zur Herstellung von harzartigen Polyestern der Terephthalsaeure
DE1770043A1 (de) * 1968-03-23 1971-09-23 Hoechst Ag Thermoplastische Polyester enthaltende Formmassen
DE2223136A1 (de) 1972-05-12 1973-11-22 Basf Ag Verfahren zur herstellung von hydroxyalkylcycloalkanolen
US4209411A (en) * 1979-03-23 1980-06-24 Exxon Research & Engineering Co. Methylol polyesters of C12 -C22 hydrocarbon substituted succinic anhydride or acid, their preparation and use as additives for lubricants and fuels
US5039760A (en) 1989-02-07 1991-08-13 Polyplastics Co., Ltd. Polyester resin composition
WO1993017060A1 (fr) 1992-02-26 1993-09-02 Perstorp Ab Macromolecule dendritique, procede d'elaboration et utilisation
DE4319671A1 (de) 1993-06-14 1994-12-15 Basf Ag Verfahren zur Herstellung von Polyisobutylbernsteinsäureanhydriden
DE4319672A1 (de) 1993-06-14 1994-12-15 Basf Ag Verfahren zur Herstellung von Polyisobutylbernsteinsäureanhydriden
DE19519042A1 (de) 1995-05-24 1996-11-28 Basf Ag Herstellung von Polyalkenylbernsteinsäure-Derivaten und ihre Verwendung als Kraft- und Schmierstoffadditive
EP0799279A1 (fr) 1994-12-21 1997-10-08 Perstorp Ab Produit thermodurcissable
US5770650A (en) 1995-10-06 1998-06-23 Basf Corporation Curable compositions for coatings
EP1109775A1 (fr) 1998-09-05 2001-06-27 BASF Coatings AG Composes hyperramifies dotes d'un groupe central tetrafonctionnel et leur utilisation
DE10163163A1 (de) 2001-12-20 2003-07-03 Basf Ag Verfahren zur Herstellung hochfunktioneller, Hyperverzweigter Polyester durch enzymatische Veresterung
DE10219508A1 (de) 2002-04-30 2003-11-13 Basf Ag Verfahren zur Herstellung hochfunktioneller, hyperverzweigter Polyester
WO2005118677A1 (fr) 2004-06-01 2005-12-15 Basf Aktiengesellschaft Polyesters hautement fonctionnels, hautement ramifies ou hyper ramifies, leur production et leur utilisation
WO2007134736A2 (fr) 2006-05-19 2007-11-29 Basf Coatings Ag Laque en poudre comprenant des polycarbonates de fonctionnalité élevée, hautement ou hyper-ramifiés
WO2008009516A2 (fr) 2006-07-20 2008-01-24 Basf Se Laques à base aqueuse renfermant des polycarbonates hautement ou hyper-ramifiés hautement fonctionnels

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1047429B (de) * 1957-03-29 1958-12-24 Basf Ag Verfahren zur Herstellung von harzartigen Polyestern der Terephthalsaeure
DE1770043A1 (de) * 1968-03-23 1971-09-23 Hoechst Ag Thermoplastische Polyester enthaltende Formmassen
DE2223136A1 (de) 1972-05-12 1973-11-22 Basf Ag Verfahren zur herstellung von hydroxyalkylcycloalkanolen
US4209411A (en) * 1979-03-23 1980-06-24 Exxon Research & Engineering Co. Methylol polyesters of C12 -C22 hydrocarbon substituted succinic anhydride or acid, their preparation and use as additives for lubricants and fuels
US5039760A (en) 1989-02-07 1991-08-13 Polyplastics Co., Ltd. Polyester resin composition
EP0630389A1 (fr) 1992-02-26 1994-12-28 Perstorp Ab Macromolecule dendritique, procede d'elaboration et utilisation
WO1993017060A1 (fr) 1992-02-26 1993-09-02 Perstorp Ab Macromolecule dendritique, procede d'elaboration et utilisation
DE4319671A1 (de) 1993-06-14 1994-12-15 Basf Ag Verfahren zur Herstellung von Polyisobutylbernsteinsäureanhydriden
DE4319672A1 (de) 1993-06-14 1994-12-15 Basf Ag Verfahren zur Herstellung von Polyisobutylbernsteinsäureanhydriden
EP0799279A1 (fr) 1994-12-21 1997-10-08 Perstorp Ab Produit thermodurcissable
DE19519042A1 (de) 1995-05-24 1996-11-28 Basf Ag Herstellung von Polyalkenylbernsteinsäure-Derivaten und ihre Verwendung als Kraft- und Schmierstoffadditive
US5770650A (en) 1995-10-06 1998-06-23 Basf Corporation Curable compositions for coatings
EP1109775A1 (fr) 1998-09-05 2001-06-27 BASF Coatings AG Composes hyperramifies dotes d'un groupe central tetrafonctionnel et leur utilisation
DE10163163A1 (de) 2001-12-20 2003-07-03 Basf Ag Verfahren zur Herstellung hochfunktioneller, Hyperverzweigter Polyester durch enzymatische Veresterung
DE10219508A1 (de) 2002-04-30 2003-11-13 Basf Ag Verfahren zur Herstellung hochfunktioneller, hyperverzweigter Polyester
WO2005118677A1 (fr) 2004-06-01 2005-12-15 Basf Aktiengesellschaft Polyesters hautement fonctionnels, hautement ramifies ou hyper ramifies, leur production et leur utilisation
WO2007134736A2 (fr) 2006-05-19 2007-11-29 Basf Coatings Ag Laque en poudre comprenant des polycarbonates de fonctionnalité élevée, hautement ou hyper-ramifiés
WO2008009516A2 (fr) 2006-07-20 2008-01-24 Basf Se Laques à base aqueuse renfermant des polycarbonates hautement ou hyper-ramifiés hautement fonctionnels

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
D.A. WICKS; Z.W. WICKS, PROG. ORG. COAT., vol. 36, 1999, pages 148 - 172
H. FREY ET AL., ACTA POLYM., vol. 48, 1997, pages 30 - 35
H. FREY ET AL., CHEMISTRY - A EUROPEAN JOURNAL, vol. 6, no. 14, 2000, pages 2499
P.J. FLORY, J. AM. CHEM. SOC., vol. 74, 1952, pages 2718
PLAST. MASSY, 1963, pages 18 - 20
PROG. ORG. COAT, vol. 9, 1981, pages 3 - 28
PROG. ORG. COAT., vol. 41, 2001, pages 1 - 83
Z.W. WICKS, PROG. ORG. COAT., vol. 3, 1975, pages 73 - 99

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8664427B2 (en) 2009-10-16 2014-03-04 Basf Se Process for preparing highly branched polyhydroxybenzoic acid alkoxylates
CN114350070A (zh) * 2022-03-03 2022-04-15 安徽海铭塑业有限公司 一种载银抗菌母粒及其应用
CN114350070B (zh) * 2022-03-03 2023-09-12 安徽海铭塑业有限公司 一种载银抗菌母粒及其应用
CN114957630A (zh) * 2022-05-24 2022-08-30 珠海金发生物材料有限公司 一种半芳香族聚酯及其制备方法和应用

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