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EP2307472A1 - Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères - Google Patents

Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères

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Publication number
EP2307472A1
EP2307472A1 EP09780850A EP09780850A EP2307472A1 EP 2307472 A1 EP2307472 A1 EP 2307472A1 EP 09780850 A EP09780850 A EP 09780850A EP 09780850 A EP09780850 A EP 09780850A EP 2307472 A1 EP2307472 A1 EP 2307472A1
Authority
EP
European Patent Office
Prior art keywords
polymer according
polymer
polymers
preparation
compounds
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.)
Withdrawn
Application number
EP09780850A
Other languages
German (de)
English (en)
Inventor
Darijo Mijolovic
Sebastien Garnier
Qiang MIAO
Maria Guixa Guardia
Gerd-Dieter Tebben
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.)
BASF SE
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 EP09780850A priority Critical patent/EP2307472A1/fr
Publication of EP2307472A1 publication Critical patent/EP2307472A1/fr
Withdrawn legal-status Critical Current

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    • 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
    • C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • 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
    • 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
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
    • C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
    • 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
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
    • C08G18/4219—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from aromatic 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
    • 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
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08—Lactones or lactides
    • 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
    • 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
    • C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/916—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
    • C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
    • C08G69/14—Lactams
    • 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
    • C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • 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
    • C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates

Definitions

  • the invention relates to a polymer which is obtainable by polycondensation or polyadduct formation of monomeric compounds, wherein as a monomeric compound
  • Diols are used for the preparation of polymers, e.g. Polyesters or polyurethanes needed.
  • polymers e.g. Polyesters or polyurethanes needed.
  • EP-A 562 578 z the use of various cyclohexanediols such as 1,4-cyclohexanedimethanol or 1,4-cyclohexanediethanol for the preparation of polyesters has been described.
  • the viscosity is important, be it as melt viscosity (100% systems) or as solution viscosity (polymer solutions).
  • the coatings produced are said to have good mechanical properties for coating applications, such as impact resistance and elasticity, high scratch and impact resistance, good resistance to water, solvents, grease and chemicals and environmental influences, and to have a high gloss.
  • the object of the present invention was to provide such polymers.
  • R is a linear or branched alkyl radical having 1 to 20 carbon atoms.
  • the polymer according to the invention is characterized in that are used as the monomeric compound or its alkoxylated derivatives of formula I those in which R is methyl or 3-methyl-butyl.
  • the polymer according to the invention is advantageous, characterized in that the compounds of the formula I are obtainable by reacting 3-methyl-2-alkylbutanal with formaldehyde in an Aldol Cannizarro reaction or by aldol reaction and subsequent hydrogenation.
  • the polymer according to the invention is characterized in that it is a polyester.
  • the polymer according to the invention is characterized in that it is a polycarbonate diol which is obtainable by reacting dialkyl carbonates or cyclic carbonates with diols with elimination of alcohol.
  • the polymer according to the invention is advantageously characterized in that it is a polyurethane.
  • the polymer according to the invention is characterized in that it is a polyadduct obtainable by ring-opening polymerization of lactones or lactams
  • Another object of the invention is the use of the polymer according to the invention for the preparation of a thermoplastic composition.
  • Another object of the invention is a thermoplastic composition containing a polymer according to the invention and / or repeat units of the polymer according to the invention. Another object of the invention is the use of the thermoplastic compositions according to the invention for the production of moldings.
  • Another object of the invention is the use of the polymer according to the invention for the preparation of coating compositions, sealants or adhesives.
  • Another object of the invention are coating compositions, sealants or adhesives containing repeating units of the polymer of the invention.
  • the coating compositions, sealants or adhesives of the invention are characterized in that they are aqueous compositions.
  • Another object of the invention is the use of the polymer according to the invention for the preparation of powder coatings.
  • Another object of the invention is a powder coating containing repeating units of the polymer according to the invention.
  • Another object of the invention is the use of the polymer according to the invention for the preparation of radiation-curable coating compositions.
  • Another object of the invention is a radiation-curable coating compositions containing repeating units of the polymer according to the invention.
  • R is a linear or branched alkyl radical having 1 to 10 carbon atoms.
  • R is selected from the group of methyl, ethyl, propyl, isopropyl, n-butyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, tert-butyl. Particularly preferred are methyl or 3-methyl-butyl.
  • the alkoxylated derivatives of the compound of general formula I are products of the reaction with one or a mixture of alkylene oxides.
  • alkylene oxides are ethylene, propylene, n-butylene, isobutylene, styrene or cyclohexene oxide.
  • the above diols are ethoxylated and propoxylated.
  • the alkoxylation products are obtainable in a known manner by reacting the above alcohols with alkylene oxides, in particular ethylene oxide or propylene oxide.
  • the degree of alkoxylation per hydroxyl group is preferably 0 to 20, in particular 0 to 10, ie 1 mol of hydroxyl group may preferably be alkoxylated with up to 20 mol, in particular 10 mol, of alkylene oxides.
  • the compounds of formula I are not alkoxylated.
  • the compounds of formula I are obtained by a Cannizzaro reaction of the corresponding 3-methyl-2-alkylbutanals with formaldehyde.
  • the process for preparing such 1, 3-propanediol derivatives is already known and described in GB 1009915 or US 3975450.
  • the 1,3-propanediols can alternatively be obtained by aldol reaction of the corresponding 3-methyl-2-alkylbutanals with formaldehyde to give the corresponding 2-hydroxymethyl-3-methyl-2-alkylbutanals and subsequent hydrogenation of the last.
  • the aldol reaction is described, for example, in WO 01/51438, WO 97/17313 or WO 98/29374.
  • the hydrogenation can be carried out analogously to the disclosure of EP-A 44412 or EP-A 44444.
  • 2-isopropyl-2 (3-methylbutyl) -1,3-propanediol the corresponding 3-methyl-2-alkylbutanal is prepared by homoaldol condensation of i-valeraldehyde and subsequent selective hydrogenation of the double bond, as described in EP-A 487035 (Pages 2 to 5).
  • the polymers are obtainable by polycondensation or polyadduct formation of monomeric compounds with concomitant use of one or more compounds of the formula I; the polymers may, if desired, be chemically modified by other or further reactions, e.g. functionalized or networked.
  • Preferred polycondensates are polyesters, which are obtainable by reacting di- or polyols with di- or polycarboxylic acids, which can also be used in the form of reactive derivatives, such as anhydrides or esters.
  • polyester is to be understood below as meaning a polymer which contains more than 50% by weight, more preferably more than 70% by weight and in particular more than 90% by weight, of synthesis components selected from among diols, polyols , Dicarboxylic acids and polycarboxylic acids. Also mentioned are polycarbonate diols which are obtainable by reacting dialkyl carbonates or cyclic carbonates with diols with elimination of alcohols.
  • Polyurethane in particular is called polyadduct.
  • polyurethanes may also contain repeating units of polymers according to the invention.
  • polyurethane is to be understood in the following to mean a polymer which contains more than 50% by weight, more preferably more than 70% by weight, in particular more than 90% by weight, of synthesis components selected from diisocyanates , Polyisocyanates, diols and polyols.
  • All these polymers have in common that they are composed essentially of diols and compounds reactive with these diols, such as di- or polycarboxylic acids (polyesters) or di- or polyisocyanates (polyurethanes).
  • Preferred polymers are polyesters and polyurethanes, particularly preferred are polyesters.
  • the polymers according to the invention preferably have the following content of the monomer building blocks of the compounds of the formula I or its alkoxylated derivatives.
  • the following weights for the content of the compounds of the formula I or their alkoxylated derivatives in the polymer refer to the units of the polymers which are different from Derive compounds of the formula I or their alkoxylated compounds. For polyadducts, the weight of these units unchanged corresponds to the compound of the formula I or its alkoxylated derivatives; in the case of polycondensates, the weight of these units is reduced by the hydrogen atoms of the hydroxyl groups.
  • Preferred polymers comprise at least 0.5, more preferably at least 2, most preferably at least 5 and in particular at least 10% by weight and in a particular embodiment at least 20% by weight of compounds of the formula I or their alkoxylated derivatives , Since the concomitant use of other reactive with the diols compounds is mandatory, the polymers are generally not more than 90 wt .-%, in particular not more than 60 wt .-% or not more than 50 wt .-% of the compounds of the formula I or their alkoxylated derivatives.
  • the polymers may also contain other diols or polyols as structural components. In a preferred embodiment is at least 10 wt .-%, more preferably at least 25 wt .-% and most preferably at least 50 wt .-% of the diols and polyols, of which the polymers are made, the compounds of formula I. or their alkoxylated derivatives.
  • At least 70% by weight or at least 90% by weight of the diols and polyols of which the polymers consist can be the compounds of the formula I or their alkoxylated derivatives.
  • 100% by weight of all the diols and polyols of which the polymers consist can be the compounds of formula I or their alkoxylated derivatives.
  • polyesters may contain further diols or polyols as synthesis components.
  • diols are e.g. Ethylene glycol, propylene glycol, and their more highly condensed species, e.g. such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., butanediol, pentanediol, hexanediol, neopentyl glycol, alkoxylated phenolic compounds, such as ethoxylated or propoxylated bisphenols, cyclohexanedi methanol mentioned.
  • Ethylene glycol, propylene glycol, and their more highly condensed species e.g. such as diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, etc., butanediol, pentanediol, hexanediol, neopentyl glycol, alkoxylated phenolic compounds, such as ethoxy
  • polystyrene resin examples include glycerol, trimethylolpropane, butanetriol, trimethylolethane, pentaerythritol, neopentyl glycol, ditrimethylolpropane, dipentaerythritol, sorbitol, mannitol.
  • glycerol trimethylolpropane
  • butanetriol trimethylolethane
  • pentaerythritol neopentyl glycol
  • ditrimethylolpropane dipentaerythritol
  • sorbitol mannitol
  • the above diols or polyols may be alkoxylated, in particular ethoxy- and propoxylated.
  • the alkoxylation products can be obtained in a known manner by reacting the above alcohols with alkylene oxides, in particular ethylene oxide or propylene oxide.
  • the degree of alkoxylation per hydroxyl group is 0 to 20, i. 1 mol of hydroxyl group may preferably be alkoxylated with up to 20 mol of alkylene oxides.
  • the polyesters also contain dicarboxylic acids or polycarboxylic acids as constituent components.
  • Dicarboxylic acids or polycarboxylic acids can also be used in the preparation of the polyesters in the form of their reactive derivatives, for example as anhydrides or esters.
  • Suitable dicarboxylic acids are succinic acid, glutaric acid, adipic acid, sebacic acid, isophthalic acid, terephthalic acid, their isomers and hydrogenation products, such as tetrahydrophthalic acid.
  • maleic acid and fumaric acid for unsaturated polyesters.
  • Polyesters may also contain monoalcohols or monocarboxylic acids as a constituent; By concomitant use of such compounds, the molecular weight can be adjusted or limited.
  • the polyesters may contain special functional groups.
  • Water-soluble or water-dispersible polyesters contain the necessary amount of hydrophilic groups, e.g. Carboxyl phenomenon or Carboxylat phenomenon to achieve a water solubility or water dispersibility.
  • Crosslinkable polyesters e.g. for powder coatings contain functional groups which undergo a crosslinking reaction with the crosslinking agent used. They may also be carboxylic acid groups if crosslinking with hydroxyl-containing compounds, e.g. Hydroxyalkylamiden is intended.
  • the functional groups may also be ethylenically unsaturated groups, e.g. by modification of the polyester with unsaturated dicarboxylic acids (maleic acid) or reaction with (meth) acrylic acid.
  • Such polyesters are thermally or chemically crosslinkable or radiation-curable.
  • Unsaturated polyesters can be 0 alkyl acrylates, Dialkylacrylaten, z with simple or multi-ethylenically unsaturated, radically polymerizable compounds such as styrene, C r Ci.
  • B. the diacrylate of ethanediol or butanediol are copolymerized.
  • the unsaturated polyester may be used in admixture with the ethylenically unsaturated monomers, such as. As described in WO 00/23495 and EP 1 131372.
  • the above ethylenically unsaturated compounds simultaneously serve as solvents (reactive diluents), so that the mixture is preferably present as a solution of the polyesters in these compounds.
  • the mixture may, for. B. as a coating or impregnating agent, in particular for the production of laminates.
  • the curing can be effected thermally or photochemically, in both cases optionally also with the addition of an initiator
  • Polyurethanes contain diisocyanates or polyisocyanates as essential constituent components.
  • diisocyanates X (NCO) 2 wherein X is an aliphatic hydrocarbon radical having 4 to 15 carbon atoms, a cycloaliphatic or aromatic hydrocarbon radical having 6 to 15 carbon atoms or an arabiphatic hydrocarbon radical having 7 to 15 carbon atoms.
  • diisocyanates examples include tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, 1,4-diisocyanatocyclohexane, 1-isocyanato-3,5,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 2,2-bis (4-isocyanatocyclohexyl) propane , Trimethylhexane diisocyanate, 1,4-diisocyanatobenzene, 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4'-diisocyanato-diphenylmethane, 2,4'-diisocyanato-diphenylmethane, p-xylylene diisocyanate, tetramethylxylylene diisocyanate (TMXDI), the isomers of bis (4-isocyanato
  • Such diisocyanates are available commercially.
  • mixtures of these isocyanates are the mixtures of the respective structural isomers of diisocyanatotoluene and diisocyanatodiphenylmethane; in particular, the mixture of 80 mol% of 2,4-diisocyanatotoluene and 20 mol% of 2,6-diisocyanatotoluene is suitable.
  • mixtures of aromatic isocyanates such as 2,4-diisocyanatotoluene and / or 2,6-diisocyanatotoluene with aliphatic or cycloaliphatic isocyanates such as hexamethylene diisocyanate or IPDI are particularly advantageous, the preferred mixing ratio of aliphatic to aromatic isocyanates being 4: 1 to 1: 4 is.
  • compounds of the general formula I are used according to the invention as pure substances or as mixtures of compounds of the general formula I or in admixture with other diols or polyols.
  • polymers of the invention it is also possible to use polymers of the invention as diols or polyols.
  • polyester diols or polyols are preferably also used as diols or polyols.
  • polyesterols are obtained beforehand by reacting di- or polyols with di- or polycarboxylic acids (see above description of the polyesters).
  • the compounds of the general formula I or mixtures of compounds of the general formula I may be present in the polyurethanes in the form of such polyesterols.
  • diols, polyols the above genierenden come into consideration, either as structural components which are reacted directly with the di- or polyisocyanates, either as part of the polyesterols.
  • Suitable dicarboxylic acids or polycarboxylic acids for the polyester radicals are also those mentioned above.
  • the polyurethanes may also contain monoalcohols or monoisocyanates as constituents; By concomitant use of such compounds, the molecular weight can be adjusted or limited.
  • the polyurethanes may contain special functional groups.
  • Water-soluble or water-dispersible polyurethanes contain the necessary amount of hydrophilic groups, for example carboxyl groups or carboxylate groups, in order to achieve water solubility or water dispersibility.
  • a suitable synthesis component is, for example, dimethylolpropionic acid.
  • Crosslinkable polyurethanes contain functional groups which undergo a crosslinking reaction with the crosslinking agent used.
  • the polyurethanes In addition to urethane groups in particular, other functional groups, for example urea groups, which are formed by reaction of the di- or polyisocyanates with amino compounds.
  • the polymers may, if desired, be incorporated at or more particularly at a later time, e.g. in use, chemically modified by other or further reactions, e.g. functionalized or networked.
  • the polymers may contain crosslinking groups which, once the necessary conditions are present, undergo a crosslinking reaction.
  • the polymers may in particular also be used in admixture with crosslinkers which undergo a crosslinking reaction with the polymer at the desired time under the necessary conditions (in particular at elevated temperature).
  • the crosslinker is added just before the later use
  • the crosslinker can be added to the system early (latent crosslinker), the crosslinking occurs only at the later set conditions, e.g. in the removal of solvent and / or temperature increase.
  • Typical crosslinkers are e.g. Isocyanates, epoxides, acid anhydrides or in the case of polymers having free-radically polymerizable ethylenically unsaturated groups, also ethylenically unsaturated monomers such as styrene.
  • the polymers are useful as a component of thermoplastic compositions.
  • the polymers e.g. Polyesters or polyurethanes preferably have a sufficiently high molecular weight to have thermoplastic properties.
  • Thermoplastic compositions are generally used to make molded articles using conventional methods such as injection molding, extrusion or blow molding.
  • the polymers are suitable as a constituent of coating compositions, sealants or adhesives.
  • the coating compositions, sealants or adhesives preferably contain the polymers according to the invention as binders. They may contain further binders and other additives, for example antioxidants, stabilizers, dyes, pigments, leveling agents, thickeners or wetting aids.
  • the coating compositions, sealants or adhesives may be aqueous or solvent-containing compositions. Preference is given to aqueous compositions.
  • Such compositions preferably contain the binders according to the invention in the form of solutions or dispersions in water or organic solvents or mixtures thereof. If necessary, the polymers contain additional functional groups which cause solubility or dispersibility in water or organic solvents, preferably in water (see above).
  • the coating compositions, sealants or adhesives may also be masses which are substantially free of water or organic solvents (so-called 100% systems).
  • Such compositions generally contain less than 10 parts by weight of water or other organic solvents (boiling point less than 150 0 C, at 1 bar), per 100 parts by weight of the masses. More preferably, they contain less than 2 parts by weight, most preferably less than 1 part by weight, or less than 0.5 parts by weight of water or other organic solvents (boiling point less than 150 0 C, at 1 bar), to 100 parts by weight of the masses.
  • These may be masses which are still free-flowing at room temperature or masses containing e.g. present as a powder and are processed only at elevated temperatures.
  • compositions in particular coating compositions, may be radiation-curable or used as radiation-curable compositions or coating compositions.
  • they preferably contain a radiation-curable polymer according to the invention, in particular a radiation-curable polyester (see above).
  • Radiation curing can be performed with high energy radiation, e.g. Electron radiation or UV light; when using UV light, a photoinitiator may preferably be added to the polymers.
  • a preferred use in the context of the present invention is the use of the polymers according to the invention as or in powder coatings.
  • polyesters are used as powder coating, which are crosslinkable.
  • the powder coating is prepared by mixing and melting the polyester, crosslinker and other additives, e.g. Pigments and leveling agents produced at high temperatures. The mixture can be powdered by subsequent extrusion and processing of the extrudate.
  • the powder coating can in the usual way, for example, electrostatically, to the desired substrates; For example, those with metal, plastic or wood surfaces, are coated.
  • the polymers according to the invention have a low viscosity, both a low melt viscosity (100% systems) or a low solution viscosity (polymer solutions).
  • the low viscosity allows easy handling, causes good coating properties and allows higher solids content in solutions or dispersions or lower binder levels in pigment-containing masses.
  • the polymers according to the invention are in particular also very resistant to hydrolysis.
  • the polymers according to the invention When used in coating compositions, sealants and adhesives, the polymers according to the invention have good mechanical properties; in particular the coating compositions, e.g. Powder Coatings; have a high impact resistance, good elasticity and a good shine.
  • the coating compositions e.g. Powder Coatings
  • the combined organic phases were freed of methanol and amyl alcohol under reduced pressure.
  • the crude distillation of the product was carried out via a distillation bridge (109-135 0 C at 4 mbar).
  • the purifying distillation was carried out in a packed column (108-106 0 C at 4 mbar).
  • the product was obtained with a purity of 98% as a solid and in 92% yield.
  • the organic phase (1993 g, 82% yield) contained by GC-FI%: 5% methanol, 85% 2-isopropyl-5-methyl-2-hexenal, 5% 2-isopropyl-5-methyl-1, 3 hexanediol, among others.
  • GC-FI% 5% methanol, 85% 2-isopropyl-5-methyl-2-hexenal, 5% 2-isopropyl-5-methyl-1, 3 hexanediol, among others.
  • the organic phase from the aldol condensation (1700 g) was hydrogenated with 1, 5% Pd / C (25.5 g, 10%) in an autoclave at 20 bar and 80 0 C for 5 h.
  • the composition of the effluent was GC-FI%: 6% methanol, 1.8% 2-isopropyl-5-methyl-2-hexenal, 70% 2-isopropyl-5-methyl-2-hexanal, 4% 2- isopropyl-5-methyl-2-hexenol, 5% 2-isopropyl-5-methyl-1,3-hexanediol, among others. (Yield of hydrogenation: 81%)
  • the combined organic phases were freed of methanol and amyl alcohol under reduced pressure.
  • the crude distillation of the product was carried out via a distillation bridge (124-165 0 C at 2 mbar).
  • the purifying distillation was carried out in a packed column (bottom temperature 180-178 0 C, head temperature 126-129 0 C at 2.5 mbar).
  • the product was obtained with a purity of 95% as a colorless liquid and 69% yield.
  • the structure was determined by GC, GC-MS and NMR ( 1 H, 13 C).
  • ADS adipic acid
  • D polydispersity index (M w / M n )
  • IMBPD 2-isopropyl-2- (3-methyl-butyl) -propane-1,3-diol
  • NPG neopentyl glycol
  • T 9 glass transition temperature
  • TMP trimethylolpropane
  • TMSA trimellitic anhydride
  • TPS terephthalic acid
  • ⁇ -i melt viscosity r
  • 2 solution viscosity
  • the determination of the solution viscosity r 2 of the polyesters is carried out with a cone-plate viscometer at room temperature in a rotary mode.
  • the solutions consist of 70% polyester and 30% solvent (mixture Solvesso 100 TM / Solvenon PM TM 5/1).
  • the Tg of the polyester is determined by DSC according to ASTM D3418.
  • Step II Preparation of COOH Group-Containing Polymer P1
  • the oligomer synthesized above is cooled to 180 ° C before adding 132.8 g of IPS (0.80 mol).
  • the temperature is raised to 230 0 C, and it is further condensed under these conditions until the polymer has an SZ of 30 to 40 mg KOH / g.
  • the water resulting from the polymerization can end up be pulled through the reaction by a slight vacuum to reach the desired SZ.
  • P1 has a glass transition temperature T 9 of 72 0 C and a melt viscosity ⁇ i of 194 Pa * s at 160 0 C.
  • inventive polymers P1, P3, P4 and P6 have a significantly lower melt viscosity than the corresponding comparative polymers P2, P5 and P7 comparable SZ and M n .
  • the reaction mixture is gradually heated to 230 0 C within 3 to 5 h with stirring and nitrogen flow, and further stirred at 230 0 C until the polyester P8 has a SZ of 10 to 15 mg KOH / g.
  • a branched amorphous OH-group-containing polyester P8 is obtained whose SZ is 12 mg KOH / g.
  • P8 has an OHN of 100 mg KOH / g and a glass transition temperature T 9 of 26 0 C.
  • P8 has a melt viscosity ⁇ i of 2.9 Pa * s at 160 0 C.
  • the solution viscosity n, 2 of the polyester P8 at room temperature (P8 solution with 70% nFA and a mixture Solvesso 100 TM / Solvenon PM TM 5/1 as solvent) is 29.8 Pa * s (see Table 2).
  • the polymers P8 and P9 according to the invention have a significantly lower melt viscosity and a significantly lower solution viscosity than the comparative polymer P10.
  • Stage I Preparation of the OH Group-Containing Oligomer 170.5 g IMPD (1.29 mol), 302.2 g NPG (2.91 mol), 401, 9 g IPS (2.42 mol) and 0.5 Catalyst DBZO are placed in a 2L four-necked flask equipped with thermometer, inert gas inlet, stirrer and reflux condenser. By passing a nitrogen stream and under reflux, the reactant mixture is heated to 160 0 C quickly. Water is distilled off continuously.
  • reaction mixture is gradually heated to 220 0 C within 3 to 5 h with stirring and nitrogen flow, and stirred at 220 0 C until the reaction mixture has an SZ of 10 to 15 mg KOH / g.
  • the SZ of the oligomer is 14 mg KOH / g.
  • a 20% aqueous colloidal solution of P11 is prepared, brought to pH 8 with N, N-dimethylethanolamine and stored at 45 0 C. The time interval until the colloidal solution precipitates is taken as a measure of the hydrolysis resistance of the polyester (see Table 4).
  • the inventive polymers P1 1 and P12 have a significantly lower melt viscosity than the comparative polymer P13.
  • the inventive polymers P1 1 and P12 are more resistant to hydrolysis than the comparative polymer P13.
  • the polyester resin Uralac P-862 T 9 58.0 0 C, SZ 35 mg KOH / g of DSM Resins BV is used.
  • a reference binder the polyester resin Uralac P-862 (T 9 58.0 0 C, SZ 35 mg KOH / g) of DSM Resins BV is used.
  • 570.0 g of powder polyester P3, P4, P5, P6, P7 or REF are each treated with 30.0 g of commercial primer Primid® XL-552 (hydroxyalkylamide EMS), 300.0 g of Kronos® 2160 titanium dioxide pigment (Kronos), 9.0 g of Resiflow® PV5 leveling agent (Worlee Chemie GmbH) and 2.5 g of benzoin in a laboratory universal mixer (MIT mixing technology GmbH) are mixed, melted, and then in a twin-screw extruder (MP 19, APV) at 80 -. 100 0 C extruded. The resulting extrudate is then roughly crushed, ground and sieve
  • the powder coatings are applied electrostatically to steel test panels (Q-Panel R-36) and at 160 0 C for 15 min. long burned. In this case, layer thicknesses of 60 microns to 80 microns are desired.
  • the resulting coatings are subjected to the following tests:
  • the powder coatings of the invention have very good performance properties. PL3 is less prone to yellowing than PL5; PL4 is highly glossy and has better mechanical properties than PL5.
  • the powder coating PL6 according to the invention has good performance properties, with advantage over PL7 in yellowing and appearance.
  • the high-solids paints 1K-PL8 and 1K-PL9 according to the invention show a very good property profile.
  • IMPD and IMBPD show an advantage over NPG in the mechanical properties of the film, as well as in acid resistance.
  • 70% polyester P8, P9 and P10 solutions are prepared in butyl acetate.
  • 70 g of the 70% polyester solutions are each treated with 1 g of solution (10% strength in butyl acetate) of the leveling agent Baysilon® OL17 (polyether from Borchers GmbH), 1 g of catalyst dibutyltin dilaurate solution (5% strength in butyl acetate) , 3 g of methoxypropyl acetate, 20 g of commercial hardener Basonat® HL 190 BS (90% strength, polyisocyanate from BASF) and 5 g of butyl acetate.
  • Baysilon® OL17 polyether from Borchers GmbH
  • catalyst dibutyltin dilaurate solution 5% strength in butyl acetate
  • methoxypropyl acetate 20 g of commercial hardener Basonat® HL 190 BS (90% strength, polyisocyanate from BASF) and 5 g of butyl a
  • the resulting solutions (nFA 67%) are applied to glass plates and steel test panels by means of box doctor. In this case, layer thicknesses of 40 microns to 50 microns are desired. Afterwards the coated th test sheets at 80 0 C for 30 min. long burned. The resulting coatings are subjected to the following tests:
  • the high-solids paints 2K-PL8 and 2K-PL9 according to the invention show a very good property profile.
  • the mechanical properties as well as the resistance to hydrolysis are significantly better than the paint 2K-PL10 based on NPG only.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Sealing Material Composition (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un polymère susceptible d'être obtenu par polycondensation ou polyaddition de composés monomères, caractérisé par le fait que, comme monomères, le composé 2-isopropyl-2-alkyl-1,3-propandiol de la formule (I) ou ses dérivés alcoxylés est (sont) utilisé(s) comme comonomère(s).
EP09780850A 2008-07-23 2009-07-21 Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères Withdrawn EP2307472A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09780850A EP2307472A1 (fr) 2008-07-23 2009-07-21 Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08160996 2008-07-23
EP09780850A EP2307472A1 (fr) 2008-07-23 2009-07-21 Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères
PCT/EP2009/059326 WO2010010075A1 (fr) 2008-07-23 2009-07-21 Utilisation de 2-isopropyl-2-alkyl-1,3-propandiols pour la fabrication de polymères

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JP (1) JP2011528745A (fr)
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WO (1) WO2010010075A1 (fr)

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KR20110053969A (ko) 2011-05-24
CN102105503A (zh) 2011-06-22
WO2010010075A1 (fr) 2010-01-28
TW201012843A (en) 2010-04-01
CN102105503B (zh) 2014-03-19
US8530570B2 (en) 2013-09-10
US20110124809A1 (en) 2011-05-26
US20130253132A1 (en) 2013-09-26
JP2011528745A (ja) 2011-11-24

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