WO2006084592A1 - Macromonomeres polyetheramines a deux groupes hydroxyle primaires voisins et leur utilisation pour produire des polyurethannes - Google Patents

Macromonomeres polyetheramines a deux groupes hydroxyle primaires voisins et leur utilisation pour produire des polyurethannes Download PDF

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Publication number
WO2006084592A1
WO2006084592A1 PCT/EP2006/000754 EP2006000754W WO2006084592A1 WO 2006084592 A1 WO2006084592 A1 WO 2006084592A1 EP 2006000754 W EP2006000754 W EP 2006000754W WO 2006084592 A1 WO2006084592 A1 WO 2006084592A1
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formula
polyurethane
compounds
aliphatic
cycloaliphatic
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PCT/EP2006/000754
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German (de)
English (en)
Inventor
Klaus Pöllmann
Martin Glos
Jürgen MÜNTER
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Clariant Produkte (Deutschland) Gmbh
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    • 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
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • 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
    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
    • C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
    • C08G65/3255—Ammonia
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group

Definitions

  • the present invention relates to ⁇ - (alkoxy) - ⁇ -N, N-dihydroxyethylamino-polyalkylene glycols, and their use for the preparation of water-dispersible polyurethanes.
  • polyurethane systems Due to their high resistance and ease of application, polyurethane systems have opened up a broad field of application in the paint, coating, coating and textile industries. For environmental and occupational safety reasons, solvent-free, water-dispersed polyurethane systems have been developed in the recent past.
  • Aqueous polyurethane dispersions consist of polyurethane polymers or polyurethane-polyurea polymers which contain both urethane groups and urea groups and are accessible by polyaddition reactions of polyols, polyisocyanates and polyamines. From the polyols and the polyisocyanates polyurethane prepolymers are first prepared, which are then dispersed in the aqueous phase and chain extended with polyamines to form the polyurethane-polyurea polymers.
  • the polyurethane polymers must also contain a sufficient amount of hydrophilic groups, which ensure the stabilization in the aqueous phase. These hydrophilic groups are anionic, cationic or nonionic groups or a combination of the groups just mentioned.
  • the dispersion is stabilized in this case after neutralization of the carboxylic acid side groups by electrostatic repulsion of the carboxylate groups incorporated in the prepolymer.
  • aqueous polyurethane dispersions are also prepared by nonionic, hydrophilic, sterically stabilizing groups.
  • nonionic, hydrophilic, sterically stabilizing groups To achieve this steric stabilization of polyurethane dispersions, therefore, long, hydrophilic, non-isocyanate-reactive side chains are required, which, like DMPA, can be incorporated into the polyurethane prepolymer via two hydroxyl groups (DE-A-25 51 094).
  • Polyethers are particularly suitable
  • Step 1 Preparation of a hydroxymethyl-1,3-dioxolane from the trifunctional alcohol
  • Stage 2 Reaction of the alkaline hydroxymethyl-1, 3-dioxolane with a
  • Step 3 Reaction of the ⁇ -hydroxy- ⁇ - (1,3-dioxolano) -polyalkylene glycol with an alkyl halide or an alkyl monoisocyanate
  • Step 4 Acid-catalyzed cleavage of the 1,3-dioxolane ring to the diol.
  • a disadvantage of this process is that large amounts of alkali metal halides are obtained as by-products in the etherification in stage 3, which interfere with the further conversion to polyurethane prepolymers and are difficult to remove.
  • trihydroxy-functional polyalkylene glycols may be formed as by-products which may cause crosslinking and thus insolubility in the polyurethane prepolymer dispersion during the copolymerization into the polyurethane prepolymer dispersion (EP-A-0 43 966).
  • Object of the present invention was therefore to find a simple and inexpensive to produce ⁇ - (alkoxy) - ⁇ -dihydroxyalkyl-polyalkylene glycol, which does not have the above-mentioned disadvantages in the preparation and application.
  • Polyurethane prepolymer dispersions can be incorporated and ensure the stability of the aqueous prepolymer dispersions.
  • the invention thus relates to compounds of the formula 2
  • R 1 is H, methyl or ethyl
  • R 2 is C 1 -C 4 -alkyl
  • A is a C 2 to C 4 alkylene group
  • m is a number from 5 to 300
  • n is a number from 0 to 3.
  • Another object of the invention is a process for the preparation of polyurethane prepolymers by reacting compounds of formula 2 with a Polyisocyanate and optionally with further polyols or polyamines.
  • Another object of the invention is a process for the preparation of polyurethane polymers by reacting a) a compound of formula 2 with a polyisocyanate and optionally with other polyols or polyamines to a polyurethane prepolymer, and b) the resulting polyurethane prepolymer in aqueous Milieu reacted with a polyamine to a polyurethane polymer.
  • Another object of the invention are polyurethane prepolymers obtainable by the reaction of a compound of formula 2 with an isocyanate of the formula X (NCO) P , wherein p is a number from 2 to 4 and X is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical ,
  • Another object of the invention are polyurethane polymers obtainable by the reaction of a compound of formula 2 with an isocyanate of the formula X (NCO) P , wherein p is a number from 2 to 4 and X is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, and the subsequent reaction of the polyurethane prepolymer thus obtained in an aqueous medium with a polyamine of the formula Y (NH 2) q , in which Y is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, and q is a number from 2 to 4.
  • Another object of the invention is the use of the compounds of formula 2 for the preparation of polyurethane prepolymers by the compound of formula 2 with an isocyanate of the formula X (NCO) P , wherein p is a number from 2 to 4 and X is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical is reacted.
  • Another object of the invention is the use of the compounds of formula 2 for the preparation of Polyurethanpoiymeren by the compound of Formula 2 with an isocyanate of the formula X (NCO) P , wherein p is a number from 2 to 4 and X is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, is reacted, and the resulting polyurethane prepolymer in an aqueous medium with a polyamine of the formula Y (NH 2 ) q , wherein Y is an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical, and q is a number from 2 to 4.
  • the total number of alkoxy units is preferably between 10 and 200.
  • the alkoxy chain may be a homopolymer or block polymer chain having alternating blocks of various alkoxy units. It can also be a chain with a statistical sequence of the alkoxy units.
  • the alkoxy units are preferably either only ethoxy units, or a mixture of ethoxy and propoxy units.
  • - (AO) m -R 2 is an alkoxy of the formula b (CH (CH 3) - CH 2 - O) a - (O CH 2 - - CH 2) - wherein R * a is a number of 0 to 300, preferably 0 to 50 b, a number from 5 to 300, preferably 10 to 200 and R 2 has the meaning given above.
  • R 1 is hydrogen.
  • n 0 or 1. All embodiments have in common that preferably at least 50 mol% of the radicals (AO) are ethoxy radicals.
  • the compounds of the formula 2 are also referred to below as ⁇ -alkoxy polyetheramine diols.
  • the process for producing the ⁇ -alkoxy-polyether-amine diols and the preparation of polyurethane dispersions is thus described in greater detail below and illustrated by way of examples.
  • the ⁇ -alkoxy-polyether-amine diols can be prepared from commercially available ⁇ -amino- ⁇ -alkoxy polyalkylene glycols (DE-A-1643426), or ⁇ -amino- ⁇ -alkoxy polyalkylene glycols prepared specifically for this purpose are prepared from ⁇ -hydroxy- ⁇ - Alkoxypolyalkylenglykolen be prepared according to the process described in DE-A-1643426 by the ⁇ -hydroxy group is replaced by an amino group in an aminolysis reaction.
  • the ⁇ -alkoxy-Polyetheramindiole can also be prepared by other methods known in the literature, such as the addition of acrylonitrile to an alcohol, and subsequent reduction of the nitrile function to the amine. This amino group is then reacted without addition of an alkoxylation catalyst with exactly 2 moles of alkylene oxide to Dihydroxyethylaminooli.
  • the degree of water solubility defined by the cloud point according to DIN EN 1890, the ⁇ -alkoxy-Polyetheramindiole, and the degree of their hydrophilizing and dispersieren ⁇ den effect can be adjusted by the ratio and number of alkylene oxide units (AO) m , preferably from ethylene oxide to propylene oxide ,
  • the isocyanates of the formula X (NCO) P are preferably those in which X is an aliphatic hydrocarbon radical having 4 to 12 carbon atoms, a cycloaliphatic or aromatic hydrocarbon radical having 6 to 15 carbon atoms or an araliphatic 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 l -diisocyanato-diphenylmethane, 2,4'-diisocyanato-diphenylmethane, p-xylylene diisocyanate, tetramethylxylylene diisocyanate (TMXDI), the isomers of bis (4-isocyana
  • mixtures of these isocyanates are the mixtures of the respective structural isomers of diisocyanate toluene and diisocyanato-diphenylmethane; in particular, the mixture of 80 mol% 2,4-diisocyanatotoluene and 20 mol% 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, wherein the preferred mixing ratio of aliphatic to aromatic isocyanates 4: 1 to 1: 4.
  • polyurethanes can be used as compounds in addition to the aforementioned also isocyanates, in addition to the free isocyanate groups further blocked isocyanate groups, e.g. Wear uretdione groups.
  • the polyamines used for the reaction of the polyurethane prepolymers to the polyurethane polymers are those in which Y is an aliphatic hydrocarbon radical having 4 to 12 carbon atoms, a cycloaliphatic or aromatic hydrocarbon radical having 6 to 15
  • Preferred amines are polyfunctional amines of the molecular weight range from 32 to 500 g / mol, preferably from 60 to 300 g / mol, which contain at least two amino groups selected from the group of the primary and secondary amino groups.
  • diamines such as diaminoethane, diaminopropanes, diaminobutanes, diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane ⁇ sophorondiamin, IPDA), 4,4-diaminodicyclohexylmethane I, 1,4-diaminocyclohexane, aminoethylethanolamine, hydrazine, hydrazine hydrate or triamines such as diethyltriamine or 1, 8-diamino-4-aminomethyloctane.
  • diamines such as diaminoethane, diaminopropanes, diaminobutanes, diaminohexanes, piperazine, 2,5-dimethylpiperazine, amino-3-aminomethyl-3,5,5-trimethylcyclohexane ⁇ sophor
  • the amines may also be in blocked form, e.g. in the form of the corresponding ketimines (see, for example, CA-A 1 129 128), ketazines (see, for example, US-A 4,269,748) or amine salts (see US-A 4,292,226).
  • oxazolidines as used for example in US-A 4,192,937, are capped polyamines, which can be used for the preparation of the polyurethanes according to the invention for chain extension of the prepolymers. Preference is given to using mixtures of di- and triamines, particularly preferably mixtures of isophoronediamine (IPDA) and diethylenetriamine (DETA).
  • the described polyamines are also suitable for use in the reaction of the compound of formula 2 with a polyisocyanate.
  • diols are used in the reaction of the compounds of the formula 2 with polyisocyanates to give the polyurethane prepolymer, and in the preparation of the polyurethane polymers.
  • the diols are, in particular, polyester polyols, e.g. from Ulimann's Encyklopadie der ischen Chemie, 4th Edition, Volume 19, pp. 62 to 65 are known. Preference is given to using polyesterpolyols which are obtained by reacting dihydric alcohols with dibasic carboxylic acids. Instead of the free polycarboxylic acids, it is also possible to use the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols or mixtures thereof to prepare the polyesterpolyols.
  • the polycarboxylic acids may be aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic and optionally, e.g. by halogen atoms, substituted and / or unsaturated. Examples include:
  • dicarboxylic acids of the general formula HOOC- (CH 2 ) y -COOH, where y is a number from 1 to 20, preferably an even number from 2 to 20, for example succinic acid, adipic acid, sebacic acid and dodecanedicarboxylic acid.
  • polyhydric alcohols e.g. Ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,3-diol, butene-1,4-diol, butyne-1,4-diol, pentane-1,1-diol, neopentyl glycol, Bis (hydroxymethyl) cyclohexanes such as 1,4-bis (hydroxymethyl) cyclohexane, 2-methylpropane-1,3-diol, methylpentanediols, furthermore diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycols consideration.
  • Ethylene glycol propane-1,2-diol, propane-1,3-diol, butane-1,3-diol, butene-1,4-d
  • Alcohols of the general formula HO- (CH 2 ) X -OH are preferred, where x is a number from 1 to 20, preferably an even number from 2 to 20.
  • examples of these are ethylene glycol, butane-1, 4-diol, hexane-1, 6-diol, octane-1,8-diol and dodecane-1, 12-diol.
  • Further preferred is neopentyl glycol.
  • polycarbonate diols as can be obtained, for example, by reacting phosgene with an excess of the low molecular weight alcohols mentioned as synthesis components for the polyesterpolyols.
  • lactone-based polyesterdiols which are homopolymers or copolymers of lactones, preferably terminal hydroxyl-containing addition products of lactones onto suitable difunctional starter molecules.
  • Suitable lactones are preferably those which are derived from compounds of the general formula HO- (CHa) 2 -COOH, where z is a number from 1 to 20 and an H atom of a methylene unit by a Cr to C 4 alkyl may be substituted. Examples are e-caprolactone, ß-propiolactone, ⁇ -butyrolactone and / or methyl-e-caprolactone and mixtures thereof.
  • Suitable starter components are, for example, the low molecular weight dihydric alcohols mentioned above as the synthesis component for the polyesterpolyols.
  • the corresponding polymers of e-caprolactone are particularly preferred.
  • Lower polyester diols or polyether diols can also be used as starters for the preparation of the lactone polymers.
  • the polymers of lactones it is also possible to use the corresponding, chemically equivalent polycondensates of the hydroxycarboxylic acids corresponding to the lactones.
  • suitable monomers are polyether diols. They are in particular by polymerization of ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with itself, for example in the presence of BF 3 or by addition of these compounds, optionally in admixture or in succession, to starting components with reactive hydrogen atoms, such as alcohols or amines, eg Water, ethylene glycol, propane-1,2-diol, propane-1,3-diol, 1,2-bis (4-hydroxy-diphenyl) -propane or aniline available. Particularly preferred is polytetrahydrofuran having a molecular weight of 240 to 5000, and especially 500 to 4500.
  • polyhydroxyolefins preferably those having 2 terminal hydroxyl groups, e.g. ⁇ , - ⁇ -Dihydroxypolybutadien, ⁇ , - ⁇ -Dihydroxypoly- methacrylic ester or ⁇ x, - ⁇ -Dihydroxypolyacrylester as monomers.
  • Such compounds are known, for example, from EP-A-0 622 378.
  • Further suitable polyols are polyacetals, polysiloxanes and alkyd resins.
  • the total nitrogen content after the reaction was 1.6 wt .-%, corresponding to a molecular weight of 875 g / mol.
  • the proportion of tertiary amine was 99 wt .-%.
  • the product was characterized by 1 H-NMR.
  • the chain extension of the aqueous dispersed prepolymer was carried out with 7.1 g of ethylenediamine dissolved in 50 g of water.
  • the result was an orange translucent, low-viscosity and storage-stable polyurethane dispersion having a solids content of 30% by weight, a pH of 8.5 and an average particle diameter of 40 nm.

Abstract

L'invention concerne des composés de formule (II), dans laquelle R<SUP>1</SUP> représente H, méthyle ou éthyle, R<SUP>2</SUP> représente alkyle C<SUB>1</SUB> à C<SUB>4</SUB>, A représente un groupe alkylène C<SUB>2</SUB> à C<SUB>4</SUB>, m est un nombre compris entre 5 et 300 et n est un nombre compris entre 0 et 3. L'invention concerne également un procédé pour produire de tels composés, ainsi que leur utilisation dans la production de prépolymères de polyuréthanne.
PCT/EP2006/000754 2005-02-11 2006-01-28 Macromonomeres polyetheramines a deux groupes hydroxyle primaires voisins et leur utilisation pour produire des polyurethannes WO2006084592A1 (fr)

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DE200510006317 DE102005006317A1 (de) 2005-02-11 2005-02-11 Polyetheramin-Makromonomere mit zwei benachbarten primären Hydroxylgruppen und ihre Verwendung zur Herstellung von Polyurethanen
DE102005006317.9 2005-02-11

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Cited By (1)

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WO2008014844A1 (fr) * 2006-08-03 2008-02-07 Clariant Finance (Bvi) Limited Macromonomères de polyétheramine ayant deux groupes hydroxyle voisins et leur utilisation pour la fabrication de polyuréthannes

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Publication number Priority date Publication date Assignee Title
WO2008014844A1 (fr) * 2006-08-03 2008-02-07 Clariant Finance (Bvi) Limited Macromonomères de polyétheramine ayant deux groupes hydroxyle voisins et leur utilisation pour la fabrication de polyuréthannes
JP2010526155A (ja) * 2006-08-03 2010-07-29 クラリアント・ファイナンス・（ビーブイアイ）・リミテッド ２つの隣接する水酸基を有するポリエーテルアミンマクロモノマーおよびポリウレタンを製造するためのその使用

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