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WO2019180127A1 - Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation - Google Patents

Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation Download PDF

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Publication number
WO2019180127A1
WO2019180127A1 PCT/EP2019/057064 EP2019057064W WO2019180127A1 WO 2019180127 A1 WO2019180127 A1 WO 2019180127A1 EP 2019057064 W EP2019057064 W EP 2019057064W WO 2019180127 A1 WO2019180127 A1 WO 2019180127A1
Authority
WO
WIPO (PCT)
Prior art keywords
uretdione
acid
group
diisocyanate
groups
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/EP2019/057064
Other languages
German (de)
English (en)
Inventor
Dorota Greszta-Franz
Saskia BEUCK
Sebastian Dörr
Hans-Josef Laas
Nusret Yuva
Heinz-Dietmar Gewiss
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.)
Covestro Deutschland AG
Covestro LLC
Original Assignee
Covestro Deutschland AG
Covestro LLC
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
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Application filed by Covestro Deutschland AG, Covestro LLC filed Critical Covestro Deutschland AG
Priority to CN201980021445.9A priority Critical patent/CN111886272B/zh
Priority to EP19711125.5A priority patent/EP3768749A1/fr
Priority to US17/040,071 priority patent/US20210024680A1/en
Publication of WO2019180127A1 publication Critical patent/WO2019180127A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • 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
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    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2036—Heterocyclic amines; Salts thereof containing one heterocyclic ring having at least three nitrogen atoms in the ring
    • C—CHEMISTRY; METALLURGY
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    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
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    • C08G18/2805—Compounds having only one group containing active hydrogen
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    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/325—Polyamines containing secondary or tertiary amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/3253—Polyamines being in latent form
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    • 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
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    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
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    • C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
    • C—CHEMISTRY; METALLURGY
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    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
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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
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates to aqueous uretdione group-containing compositions comprising or consisting of
  • At least one hardener containing uretdione groups based on aliphatic, cycloaliphatic, araliphatic and / or aromatic polyisocyanates, which contains no chemically bonded hydrophilizing groups;
  • the quantitative ratio of components (A) and (B) is such that the molar ratio of the uretdione present NCO groups of the harder (A) to NCO-reactive groups of the polyol (B) 3: 0.5 to 0 , 5: 3 and wherein A and B are present as a physical mixture.
  • the invention relates to a process for producing a polyurethane layer using the aqueous uretdione group-containing composition of the present invention, the polyurethane layer obtained therefrom, and a substrate coated or adhered to this polyurethane layer.
  • aqueous coating systems are already available for many applications, they often can not achieve the high quality level of conventional, solvent-borne coatings in terms of resistance to solvents and chemicals or even elasticity and mechanical stress.
  • no polyurethane-based coating agents to be processed from an aqueous phase have hitherto become known which sufficiently satisfy the high requirements in practice.
  • aqueous uretdione-containing dispersion coatings can be prepared by combining a solid uretdione compound with a molten water-dispersible resin, salting the water-dispersible resin if necessary, and dispersing the resin composition in water.
  • the molten water-dispersible resin may have a functionality reactive with the uretdione compound, or the coating composition may contain another water-dispersible resin having a uretdione compound-reactive functionality.
  • an epoxy resin was used. It is well known that the epoxy varnishes are inferior in most properties to polyurethane varnishes.
  • EP 1687354 A1 it is also necessary for the preparation of these dispersion coatings to use an additional emulsifier, which further impairs the coating properties of the dispersion coatings.
  • the production method described in EP 1687354 A1 is associated with a very high thermal load for the uretdione groups, which in practice would most likely lead to a loss of the uretdione groups.
  • the dispersions described in EP 1687354 Al were applied immediately after preparation. There is no information in EP 1687354 Al about the stability of these dispersions.
  • water-dispersible hydrophilic uretdione-containing polyisocyanates can be found, for example, in DE 2538484 A1 and DE 10 2005 036 654 A1.
  • a hydrophilizing group ie, a carboxyl group
  • DE 2538484 A nor DE 10 2005 036 654 Al give information on the stability of these dispersions.
  • no physical Mixtures of a specific uretdione hardener and a specific polyol are present.
  • US 2015232609A1 discloses water-dispersible hydrophilic uretdione-containing polyisocyanates obtainable by reacting a uretdione group-bearing prepolymer with an emulsifier comprising an ionogenic group, the ionic group having either a pKa> 8 or a pKb> 8 in water at room temperature.
  • Such uretdione-containing reaction products showed an improved storage stability of 8 weeks at room temperature, but this is still insufficient for practical applications in industry, where in many cases long transport distances must be expected.
  • the present invention particularly relates to:
  • Aqueous uretdione group-containing compositions comprising or consisting of
  • At least one hardener containing uretdione groups based on aliphatic, cycloaliphatic, araliphatic and / or aromatic polyisocyanates, preferably based on aliphatic, cycloaliphatic, and / or araliphatic polyisocyanates, particularly preferably based on aliphatic and / or cycloaliphatic polyisocyanates, which does not chemically bound hydrophilicizing groups;
  • the quantitative ratio of the components (A) and (B) is such that the molar ratio of the uretdione NCO groups of the harder (A) to NCO-reactive groups of the polyol (B) is 3.0: 0, 5 to 0.5: 3.0, preferably from 2.5: 1.0 to 1.0: 2.5; more preferably 2.0: 2.0 to 1.0 to 1.0: 2.0 and wherein (A) and (B) exist as a physical mixture.
  • Aqueous uretdione group-containing composition characterized in that the at least one uretdione group-containing curing agent (A) by reacting monomeric isocyanates comprising or consisting of at least one monomeric isocyanate selected from tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), l-isocyanato 3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, tolylene diisocyanate (TDI), diphenylmethane-2, 4'- and / or 4,
  • Aqueous uretdione group-containing composition according to aspect 1 or 2 characterized in that
  • uretdione group-containing hardener (A) hydroxyl-containing monomers and / or polymers are used as feedstocks for the at least one uretdione group-containing hardener (A) hydroxyl-containing monomers and / or polymers.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one uretdione group-containing curing agent (A) has a free NCO content of less than 5 wt .-% and a content of uretdione groups from 1 to 18 wt .-% (calculated as C2N2O2, molecular weight 84 g / mol).
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the aqueous composition has an acid number of 1 to 100 mg KOH / g, preferably 2 to 50 mg KOH / g, more preferably 5 to 30 mg KOH / g, preferably measured according to DIN EN ISO 2114: 2002-06 with acetone and ethanol in a weight ratio 2: 1 as a solvent, and calculated on solids content.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one hydroxyl-containing polyol (B) by reacting hydroxy or aminocarboxylic acids comprising or consisting of at least one carboxylic acid selected from 2,2-dimethylolacetic acid, 2,2-dimethylol butyric acid, 2,2-dimethylolpentanoic acid, dihydroxysuccinic acid, a, W-diaminovaleric acid or mixtures thereof, preferably from dimethylolpropionic acid or hydroxypivalic acid.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one hydroxy group-containing polyol (B) has an OH content greater than 1% by weight, calculated as OH group to solids content, molecular weight 17 g / mol, and a number average molecular weight Mn of 500 to 20,000 g / mol.
  • the solvent is selected from acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 or Solvesso 150,
  • Aqueous uretdione dispersion according to one of the preceding aspects, characterized in that
  • auxiliaries and additives are selected from the group of flow control agents, for example polysilicones or acrylates, light stabilizers, for example sterically hindered amines, catalysts, for example tin (II) 2-ethylhexanoate or dibutyltin dilaurate, fillers and pigments, for example titanium dioxide, or Mixtures thereof.
  • flow control agents for example polysilicones or acrylates
  • light stabilizers for example sterically hindered amines
  • catalysts for example tin (II) 2-ethylhexanoate or dibutyltin dilaurate
  • fillers and pigments for example titanium dioxide, or Mixtures thereof.
  • pigments for example titanium dioxide, or Mixtures thereof.
  • step iii) curing the mixture from step iii) with heat from 40 ° C to 180 ° C for up to 180 minutes.
  • Harder (A) containing at least one hydroxy group-containing polyol (B) was obtained in the absence of water and subsequent dispersion with water. 13.
  • the average molecular weight is defined according to this invention as the number average molecular weight Mn, unless explicitly stated otherwise.
  • Mn is determined by gel permeation chromatography (GPC) at 23 ° C in tetrahydrofuran as a solvent. The measurement is carried out as described in DIN 55672-1: 2016-03: "Gel Permeation Chromatography, Part 1 - Tetrahydrofuran as Eluent” (SECURITY GPC system from PSS Polymer Service, flow rate 1.0 ml.
  • percentages by weight in the present invention refer to the total weight of the particular system or the total weight of the particular component.
  • a copolymer may contain a given monomer in weight percent, in which case the weight percentages would be based on the total weight of the copolymer.
  • At least one refers to the nature of the compounds rather than individual molecules.
  • at least one polyol is to be understood as containing at least one type of polyol, but contained in an arbitrary number of molecules in the composition.
  • two or more types of polyols may be present in any arbitrary number, if the amounts are not defined.
  • the aqueous uretdione group-containing composition is substantially free of another co-emulsifier (in addition to component (B)).
  • the term "substantially free of” according to the present invention is defined as preferably less than 1 wt%, more preferably less than 0.25 wt%, even more preferably less than 0.1 wt%. , most preferably less than 0.01 wt .-% or no fraction of the respective compound, each based on the total weight of the aqueous uretdione groups-containing composition.
  • the aqueous uretdione group-containing composition of the present invention is preferably a polyurethane-based composition.
  • Suitable polyisocyanates containing uretdione groups as starting compounds for component (A) are polyisocyanates containing at least one isocyanate group and at least one Uretdion group included. These are prepared, as described, for example, in WO 02/92657 A1 or WO 2004/005364 A1 by reaction of suitable starting isocyanates (al). Here, under catalysis, for example with triazolates or 4-dimethylaminopyridine (DMAP) as catalysts, some of the isocyanate groups are converted into uretdione groups.
  • DMAP 4-dimethylaminopyridine
  • isocyanates (a1) from which the uretdione-containing building blocks are synthesized are tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), 1-isocyanato-3,3,5 trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane-2,4'- and / or 4,4'-diisocyanate,
  • TXDI Tetramethylxylylene diisocyanate
  • TDI Triisocyanatononan
  • MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • MDI triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diisocyanate and any Mixtures of such isocyanates.
  • component (A) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • reaction of these uretdione group-carrying polyisocyanates to uretdione-containing hard (A) involves the reaction of the free NCO groups of the abovementioned polyisocyanates with a polyol component (bl), optionally with the concomitant use of the polyol component (b2).
  • the polyol component (bl) preferably has a hydroxyl group functionality of> 2 and a molecular weight M n of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol.
  • the polyol component (bl) preferably contains 2- to 6-valent polyol components of molecular weight Mn of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol.
  • Preferred polyol components (bl) are, for example, 1,4- and / or 1,3-butanediol, 1,6-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane, polyester and / or polyether polyols of the middle one Molar weight M n of less than or equal to 500 g / mol.
  • Suitable linear difunctional polyols (b2) are selected from the group of polyethers, polyesters, polycaprolactone diols and / or polycarbonates.
  • the polyol component (b2) contains at least one diol containing ester groups of molecular weight Mn from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol. It is the average, calculated from the hydroxyl number molecular weight.
  • the ester diols are mixtures in which, in minor amounts, individual constituents may also be present which are lower or higher having these limits lying molecular weight.
  • These are the polyester diols known per se, which are built up from diols and dicarboxylic acids.
  • Suitable diols are, for example, 1,4-dimethylolcyclohexane, 1,4- or 1,3-butanediol, 1,6-hexanediol, neopentyl glycol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane and also pentaerythritol or mixtures thereof diols.
  • Suitable dicarboxylic acids are, for example, aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid, cycloaliphatic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid or its anhydrides and aliphatic dicarboxylic acids which are preferably used, such as succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid or their anhydrides.
  • aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid
  • cycloaliphatic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid or its anhydrides
  • aliphatic dicarboxylic acids which are preferably used, such as succinic acid,
  • Polyester diols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid are preferably used as component (b2).
  • preferred diols for example, 1,4- or 1,3-butanediol, 1,6-hexanediol or trimethylolpropane and mixtures thereof are used.
  • component (b2) are polycaprolactone diols of average molecular weight from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol, which in a conventional manner from a diol or diol mixture the type exemplified above as starter, and lactones such as .beta.-propiolactone, g-butyrolactone, g- and d-valerolactone, e-caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any mixtures of such lactones have been produced.
  • lactones such as .beta.-propiolactone, g-butyrolactone, g- and d-valerolactone, e-caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any mixtures of such lactones have been produced.
  • Particularly preferred are those polycaprolactone dio
  • linear polyol component (b2) it is also possible to use (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran, which consist of less than 30 mol% of ethylene oxide units.
  • polyethers having an average molecular weight Mn of from 500 to 2000 g / mol such as e.g. Polypropylene oxides or polytetrahydrofurandiols.
  • hydroxyl-containing polycarbonates preferably average molecular weight Mn of from 400 to 4000 g / mol, preferably from 400 to 2000 g / mol, for example hexanediol polycarbonate and polyestercarbonates.
  • diol component (b2) in the preparation of the curing agent (A) containing uretdione groups it is also possible to use diols having an average molecular weight, calculated from functionality and hydroxyl number, of 134 to 349 g / mol, preferably 176 to, low molecular weight ester groups 349 g / mol, are used. These are, for example, the per se known, ester-containing diols or mixtures of such diols, as they are, for. B. by reacting alcohols with minor amounts of dicarboxylic acids, corresponding dicarboxylic anhydrides, corresponding dicarboxylic acid esters of lower alcohols or lactones.
  • Suitable acids are succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic acid, maleic acid, maleic anhydride, terephthalic acid dimethyl ester and terephthalic acid bis-glycol ester.
  • Suitable lactones for preparing these ester diols are, for example, ⁇ -propiolactone, g-butyrolactone, g- and d-valerolactone, ⁇ -caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any desired mixtures of such lactones.
  • uretdione groups having curing agent (A) and amino-functional compounds can be used.
  • suitable low molecular weight amino-functional compounds are aliphatic and cy cloaliphatic amines and amino alcohols with primary and / or secondary bound amino groups, such as. B.
  • cyclohexylamine 2-methyl-l, 5-pentanediamine, diethanolamine, monoethanolamine, propylamine, butylamine, dibutylamine, hexylamine, monoisopropanolamine, diisopropanolamine, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, isophoronediamine, diethylenetriamine, ethanolamine, Aminoethylethanolamine, diaminocyclohexane, hexamethylenediamine, methyliminobispropylamine, iminobispropylamine, bis (aminopropyl) piperazine, aminoethylpiperazine, 1,2-diaminocyclohexane, triethylenetetramine, tetraethylenepentamine, bis (4-amino-cyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane
  • solvents may be used in the preparation of the curing agent (A) containing uretdione groups.
  • Suitable solvents for uretdione curing agents (A) are all liquid substances which do not react with other ingredients, eg. Acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
  • the uretdione group-containing hardeners (A) are substantially free of ionic or non-ionic, chemically-bonded hydrophilicizing groups.
  • ionic hydrophilizing groups those skilled in the art will understand groups having an ability to form anions or cations.
  • Groups capable of anion or cation formation are those which can be converted by chemical reaction into an anionic or cationic group, in particular by neutralization.
  • the uretdione group-containing curing agents (A) are preferably free of anionic-capable, carboxyl-containing polyols or diols, e.g. Dihydroxycarboxylic acids, such as ⁇ , ⁇ -dialkylolalkanoic acids, in particular ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid,
  • Dihydroxycarboxylic acids such as ⁇ , ⁇ -dialkylolalkanoic acids, in particular ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid,
  • the hardeners (A) containing uretdione groups are preferably free from amino-containing compounds capable of anion formation such as, for example, ⁇ , W-diaminovaleric acid or 2,4-diamino-toluene-sulphonic acid.
  • the uretdione group-containing hardeners (A) are also preferably free of sulfonic acid groups capable of forming anions.
  • uretdione hardening agents (A) are preferably free of cation-forming compounds from the group of tertiary amino or ammonium compounds, e.g. Tris (hydroxyalkyl) amines, N, N'-bis (hydroxyalkyl) alkylamines, N-hydroxyalkyldialkylamines, trisaminoalkylamines, N, N'-bisaminoalkylalkylamines, N-aminoalkyldialkylamines, and mixtures thereof.
  • Tris (hydroxyalkyl) amines e.g. Tris (hydroxyalkyl) amines, N, N'-bis (hydroxyalkyl) alkylamines, N-hydroxyalkyldialkylamines, trisaminoalkylamines, N, N'-bisaminoalkylalkylamines, N-aminoalkyldialkylamines, and mixtures thereof.
  • the uretdione group-containing curing agents (A) are furthermore preferably free from nonionically hydrophilizing compounds, such as, for example, polyalkylene oxide polyether alcohols or polyalkylene oxide polyetheramines.
  • the hardeners (A) containing uretdione groups are preferably free of polyethylene oxide polyethers or mixed polyalkylene oxide polyethers whose alkylene oxide units consist of at least 30 mol% of ethylene oxide units.
  • Preferred uretdione hardeners (A) have a free NCO content of less than 5% by weight and a content of uretdione groups of 1 to 18% by weight (calculated as C2N2O2, molecular weight 84 g / mol).
  • the hardeners (A) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • the composition also contains at least one hydroxyl-containing polyol which contains at least one chemically bonded carboxylic acid group (component (B)).
  • Suitable polyols (B) may be selected from polyester polyols, polyether polyols, polyurethane ether polyols, polyurethane ester polyols, polycaprolactone polyols,
  • Polyetheresterpolyolen, polycarbonate polyols, C2-io-hydrocarbon having at least two hydroxyl groups or mixtures thereof are selected, as long as such polyols have at least one chemically bonded carboxylic acid groups.
  • the suitable polyols (B) are preferably from the group of polyurethane ether polyols, polyurethane ester polyols,
  • Polycaprolactone polyols or polycarbonate polyols Particularly preferred are polyurethane ester polyols (B) prepared from 5 to 80 wt .-%, preferably 10 to 60 wt .-% of isocyanates (al),
  • At least one chemically bonded carboxylic acid group-containing starting component (b3) for the polyols (B) are suitable such polyols, preferably diols, containing at least one carboxylic acid group, generally 1 to 3 carboxylic acid groups per molecule.
  • dihydroxycarboxylic acids such as ⁇ , ⁇ -dialkylolalkanoic acids, especially ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethyloleacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid, dihydroxysuccinic acid, furthermore polyhydroxy acids, such as Gluconic acid, or aminocarboxylic acids such as a, W-diaminovaleric acid, and 2,4-diamino-toluene-sulfonic acid. It is also possible to use mixtures of the compounds described above.
  • At least one chemically bonded carboxylic acid group-containing starting component (b3) for the polyols (B) is particularly preferred 2,2-dimethylolpropionic acid.
  • monohydroxy-functional compounds which have at least one carboxylic acid group, for example hydroxypivalic acid or hydroxydecanoic acid.
  • Suitable polyols (B) are polyols which preferably have an OH content of more than 1% by weight (calculated as OH group on solid content, molecular weight 17 g / mol) and preferably a number average Molecular weight Mn of 500 to 20,000 g / mol, preferably from 500 to 10,000 g / mol, particularly preferably from 500 to 5000 g / mol.
  • the preparation of the polyurethane resin used according to the invention is preferably carried out by reacting a non-aqueous resin precursor of the polyol (B) with at least one uretdione curing agent (A) based on aliphatic, (cyclo) aliphatic, araliphatic and / or aromatic polyisocyanates, which contains no chemically bound hydrophilizing groups, homogeneously mixed in a nonaqueous system.
  • the carboxylic acid groups present in the polyol (B) are preferably neutralized to at least 50%, more preferably 80% to 120%, particularly preferably 95 to 105% with suitable neutralizing agents and then dispersed with deionized water.
  • the neutralization may be carried out before, during or after the dispersing step. However, preference is given to neutralization before the addition of water.
  • Suitable neutralizing agents are, for example, triethylamine, dimethylaminoethanol, dimethylcyclohexylamine, triethanolamine, methyldiethanolamine, diisopropanolamine, ethyldiisopropylamine, diisopropylcyclohexylamine, N-methylmorpholine, 2-amino-2-methyl-1-propanol, ammonia or other customary neutralizing agents or neutralization mixtures thereof. Preference is given to tert. Amines such as e.g. Triethylamine, diisopropylhexylamine, particularly preferred is dimethylethanolamine.
  • the neutralizing agents are to be counted among the group of auxiliary additives (D).
  • solvents under (C) all liquid substances are suitable which do not react with other ingredients.
  • Preferred are acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
  • the solvent used can then be removed by distillation.
  • customary additives such as leveling agents, for.
  • leveling agents for.
  • polysilicones or acrylates light stabilizers, for.
  • sterically hindered amines, catalysts for example, tin (II) 2-ethylhexyloctoate or dibutyltin dilaurate or other auxiliaries, as described, for.
  • tin (II) 2-ethylhexyloctoate or dibutyltin dilaurate or other auxiliaries as described, for.
  • fillers and pigments such as titanium dioxide may be added in an amount of up to 50% by weight of the aqueous composition.
  • the aqueous uretdione group-containing compositions contains or consists of
  • Polyester 1 an aliphatic polyester prepared from 1419 g of trimethylolpropane, 4773 g of neopentyl glycol, 3093 g of adipic acid, 4101 g of isophthalic acid and 267 g of 1,2-propylene glycol having an acid number ⁇ 3 mg KOH / g and an OH number of 181 mg KOH / G.
  • the NCO contents were determined titrimetrically in accordance with DIN EN ISO 11909: 2007-05.
  • the determination of the average particle size (MTG) was carried out with a Zetasizer Nano Fa.
  • pH value determination was carried out with a pH meter according to DIN ISO 976: 2008-07 diluted 1: 4 with distilled water.
  • the residual monomer contents were measured according to DIN EN ISO 10283 by gas chromatography with an internal standard.
  • the pendulum hardness was measured on a standardized coil test panel (Coil Coating black - CS 200570, Heinz Zanders für-Blech-Logiding) according to DIN EN ISO 1522: 2007-04 with a König pendulum.
  • Part 1 from Table 1 was weighed into a stirring apparatus under nitrogen and homogenized for 1 hour at 60 ° C. Thereafter, Part 2 was added at 55 ° C so that by the exothermic reflux has arisen. The reaction mixture was refluxed until the NCO content dropped below 0.05%. Subsequently, the reaction mixture was cooled to 50 ° C, Part 3 was added and stirred for 1 hr. At 50 ° C. Thereafter, part 4 was added and stirred for 30 min. Finally, part 5 was stirred in 15 minutes and acetone distilled off in vacuo.
  • the dispersion remained stable for 14 months at 23 ° C.
  • Example 2 was prepared as Example 1, except that 718 g of crosslinker 1 solution and 38 g of dimethylethanolamine were used.
  • the dispersion thus obtained has the following characteristics:
  • the dispersion remained stable for 14 months at 23 ° C.
  • Example 3 was prepared as Example 1, except that the following quantity framework from Table 2 was used: TABLE 2
  • the dispersion remained stable at 23 ° C for 10 months.
  • IPDI isophorone diisocyanate
  • DMAP 4-dimethylaminopyridine
  • the dispersions were mixed in a speed mixer at 2000 rpm for 1 minute and applied to a coil plate with a doctor blade having a layer thickness of 180 ⁇ m (wet).
  • the plates with the applied wet paints were aerated for 5 min at room temperature and then baked for 30 min at 180 ° C and stored for 4 days at room temperature.
  • the stored films were evaluated by application technology (Table 4). Table 4
  • the uretdione-containing dispersions according to the invention give hard and stable coatings.

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Abstract

La présente invention concerne des compositions aqueuses contenant des groupes uretdione comprenant ou constituées de (A) au moins un durcisseur contenant des groupes uretdione, à base de polyisocyanates aliphatiques, cycloaliphatiques, araliphatiques et/ou aromatiques qui ne contient aucun groupe hydrophilisant chimiquement lié ; (B) au moins un polyol contenant des groupes hydroxyle qui contient au moins un groupe acide carboxylique chimiquement lié ; (C) le cas échéant, des solvants ; et (D) le cas échéant, des substances auxiliaires et des additifs ; la proportion des composants (A) et (B) étant mesurée de telle sorte que le rapport molaire entre les groupes NCO du durcisseur (A) présents sous forme d'uretdione et les groupes réactifs au NCO du polyol (B) s'élève de 3,0 : 0,5 à 0,5 : 3,0 et de telle sorte que A et B soient présents sous forme de mélange physique. L'invention concerne en outre un procédé pour préparer une couche de polyuréthane en utilisant la composition aqueuse contenant des groupes uretdione selon la présente invention, la couche de polyuréthane ainsi obtenue et un substrat qui est recouvert de cette couche de polyuréthane ou bien collé à celle-ci.
PCT/EP2019/057064 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation Ceased WO2019180127A1 (fr)

Priority Applications (3)

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CN201980021445.9A CN111886272B (zh) 2018-03-23 2019-03-21 含脲二酮基团的水性组合物及其制备方法
US17/040,071 US20210024680A1 (en) 2018-03-23 2019-03-21 Aqueous uretdione group-containing compositions and method for producing same
EP19711125.5A EP3768749A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation

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US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
US15/933,487 2018-03-23
EP18163620.0 2018-03-23
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
US15/933,500 2018-03-23
US15/933,527 2018-03-23
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
EP18163621.8 2018-03-23
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
EP18163625.9 2018-03-23
US15/933,570 2018-03-23
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,553 2018-03-23
US15/933,470 2018-03-23
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
US15/933,475 2018-03-23
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,511 2018-03-23
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,507 2018-03-23
US15/933,495 2018-03-23
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
EP18181877.4 2018-07-05
EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181877.4A EP3590988A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181876.6 2018-07-05

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PCT/EP2019/057069 Ceased WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
PCT/EP2019/057066 Ceased WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
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PCT/US2019/023292 Ceased WO2019183305A1 (fr) 2018-03-23 2019-03-21 Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche
PCT/US2019/023314 Ceased WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
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PCT/EP2019/057069 Ceased WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
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PCT/US2019/023299 Ceased WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
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Publication number Priority date Publication date Assignee Title
CN110698622A (zh) * 2019-10-12 2020-01-17 北京长润化工有限公司 酮亚胺潜伏固化剂和具有其的反应型聚氨酯热熔胶及应用
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CN116063975B (zh) * 2021-11-02 2025-07-29 浙江华峰合成树脂有限公司 一种聚氨酯胶黏剂及其制备和应用
CN116410442A (zh) * 2021-12-31 2023-07-11 万华化学集团股份有限公司 一种存储稳定的多异氰酸酯组合物

Citations (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2456469A1 (de) 1974-11-29 1976-08-12 Bayer Ag Verfahren zur herstellung von in wasser loeslichen bzw. dispergierbaren blockierten polyisocyanaten
DE2538484A1 (de) 1975-08-29 1977-03-10 Veba Chemie Ag Thermisch vernetzbare waessrige polyurethandispersionen
DE2814815A1 (de) 1977-04-07 1978-10-19 Grace W R & Co Waessrige urethandispersionen und codispersionen
EP0012348A1 (fr) 1978-12-14 1980-06-25 Bayer Ag Un liant contenant un polyisocyanate et un composé polyhydroxylé comme agent de revêtement applicable à partir d'une phase aqueuse
US4496684A (en) 1984-06-01 1985-01-29 Olin Corporation Uretdione group-containing polyurethane oligomers and aqueous dispersions thereof
EP0424697A2 (fr) 1989-10-03 1991-05-02 Asahi Glass Company Ltd. Composition de polyuréthane aqueuse et son utilisation
DE4001783A1 (de) 1990-01-23 1991-07-25 Bayer Ag Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung als bindemittel fuer ueberzugsmittel oder als reaktionspartner fuer gegenueber isocyanatgruppen oder carboxylgruppen reaktionsfaehige verbindungen
EP0576952A2 (fr) 1992-07-03 1994-01-05 Bayer Ag Compositions dispersables de polyisocyanates solubles dans l'eau et leur utilisation dans des vernis au four
EP0669353A1 (fr) 1994-02-28 1995-08-30 Hüls Aktiengesellschaft Produits de polyaddition contenant des groupes hydroxy- et uretdione, procédé de leur préparation et leur utilisation pour la préparation de vernis en poudre de polyuréthane à haute réactivité ne relâchant pas de produits de décomposition et vernis en poudre de polyuréthane obtenus par ce procédé
EP0818482A1 (fr) * 1996-07-13 1998-01-14 Hüls Aktiengesellschaft Adhésifs à un composant à partir de polyuréthanes, un procédé pour leur préparation ainsi que leur utilisation
WO2002092657A1 (fr) 2001-05-14 2002-11-21 Bayer Aktiengesellschaft Procede de dimerisation de diisocyanate d'isophorone
WO2004005364A1 (fr) 2002-07-04 2004-01-15 Bayer Materialscience Ag Isocyanates presentant des groupes uretdione
EP1687354A1 (fr) 2003-11-25 2006-08-09 Basf Corporation Procede de fabrication de revetement aqueux a reticulant solide
DE102005036654A1 (de) 2005-08-04 2007-02-15 Bayer Materialscience Ag Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur
US20120252926A1 (en) * 2011-03-30 2012-10-04 Basf Se Latently reactive polyurethane dispersion with activatable crosslinking
DE102012218081A1 (de) * 2012-10-04 2014-04-10 Evonik Industries Ag Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität

Family Cites Families (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169945A (en) 1956-04-13 1965-02-16 Union Carbide Corp Lactone polyesters
DE1078568B (de) 1957-08-30 1960-03-31 Basf Ag Verfahren zur Herstellung von Carbonsaeureamidinen
NL265610A (fr) 1960-10-14
DE2312391A1 (de) * 1973-03-13 1974-09-19 Bayer Ag Pulverfoermige, vernetzbare ueberzugsmittel
DE3030572A1 (de) * 1980-08-13 1982-03-18 Chemische Werke Hüls AG, 4370 Marl Verfahren zur herstellung von uretdiongruppenhaltigen polyadditionsprodukten sowie die danach hergestellten produkte
JPS63284273A (ja) * 1987-05-15 1988-11-21 Dainippon Ink & Chem Inc 粉体塗料用樹脂組成物
CA2047635C (fr) * 1990-07-30 2003-09-30 Terry A. Potter Revetement de polyurethanne a deux elements en dispersion aqueuse
DE4136618A1 (de) * 1991-11-07 1993-05-13 Bayer Ag Wasserdispergierbare polyisocyanatgemische
DE4322242A1 (de) * 1993-07-03 1995-01-12 Basf Lacke & Farben Wäßriges Zweikomponenten-Polyurethan-Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung in Verfahren zur Hestellung einer Mehrschichtlackierung
CA2134009C (fr) 1993-11-11 2005-03-08 Oleg Werbitzky Amidines bicycliques, methode pour leur obtention et leur utilisation comme catalyseur
US5795950A (en) * 1994-05-20 1998-08-18 Asahi Kasei Kogyo Kabushiki Kaisha Straight chain crystalline polyuretdione
DE69531847T2 (de) * 1994-06-06 2004-08-05 Basf Corp. Aldimin und Isocyanat enthaltende Beschichtungszusammensetzungen sowie Verfahren zu deren Herstellung
US5523376A (en) * 1994-12-21 1996-06-04 Bayer Corporation Coating compositions based on aldimines and polyisocyanates containing uretdione groups
CA2245730C (fr) * 1996-02-17 2006-01-03 Imperial Chemical Industries Plc Composition de revetement
DE19611849A1 (de) 1996-03-26 1997-10-02 Bayer Ag Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung
DE19616496A1 (de) 1996-04-25 1997-10-30 Bayer Ag Abspaltfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur
DE19628328A1 (de) * 1996-07-13 1998-01-15 Huels Chemische Werke Ag Wärmehärtender abspalt- und lösemittelfreier Einkomponenten-Klebstoff auf Basis von Polyurethanen sowie deren Verwendung
US5977285A (en) * 1997-08-07 1999-11-02 Akzo Nobel N.V. Sprayable coating compositions comprising oxazolidines, isocyanates and hydroxyl or amine functional resins
US5814689A (en) * 1997-08-29 1998-09-29 Arco Chemical Technology, L.P. Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings
JPH11279450A (ja) * 1998-02-02 1999-10-12 Asahi Chem Ind Co Ltd 粉体塗料用組成物
DE19814061A1 (de) 1998-03-30 1999-10-07 Bayer Ag Copolymerisatdispersionen, Bindemittelkombinationen auf Basis der Copolymerisatdispersionen, ein Verfahren zu deren Herstellung und deren Verwendung
DE19854405B4 (de) * 1998-11-25 2016-05-04 Basf Se Kompakte Kaschierung auf der Basis von Polyisocyanat-Polyadditionsprodukten
GB9828446D0 (en) * 1998-12-24 1999-02-17 Ici Plc Coating composition
DE19903391A1 (de) 1999-01-29 2000-08-03 Bayer Ag Wäßriges Überzugsmittel, Verfahren zu seiner Herstellung und seine Verwendung
DE19929064A1 (de) * 1999-06-25 2000-12-28 Bayer Ag Verfahren zur Herstellung Uretdiongruppen aufweisender Polyadditionsverbindungen
DE69901260T2 (de) * 1999-12-07 2002-08-14 Chinese Petroleum Corp., Taipeh/T'ai-Pei Uretedionderivat, es enthaltende härtbare Harzzusammensetzung und Verfahren zu seiner Herstellung
ES2257369T3 (es) * 2000-10-13 2006-08-01 Tosoh Corporation Catalizador para la preparacion de una composicion sellante de dos componentes a base de poliuretano.
DE10234792A1 (de) * 2002-07-31 2004-02-12 Basf Coatings Ag Strukturviskose Klarlack-Slurry, Verfahren zu ihrer Herstellung und ihre Verwendung
ITVA20020064A1 (it) * 2002-12-02 2004-06-03 Lamberti Spa Dispersioni acquose stabili di poliisocianati bloccati non ionici.
JP4143825B2 (ja) * 2003-01-28 2008-09-03 三菱瓦斯化学株式会社 ポリイソシアネート化合物、その製造方法、重付加組成物、および粉体塗料
DE10320267A1 (de) * 2003-05-03 2004-11-18 Degussa Ag Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen
DE10347902A1 (de) * 2003-10-15 2005-05-19 Degussa Ag Feste uretdiongruppenhaltige Polyadditionsverbindungen
DE10347901A1 (de) * 2003-10-15 2005-05-19 Degussa Ag Polyurethan-Pulverlackbeschichtungen, welche feste uretdiongruppenhaltige Polyadditionsverbindungen enthalten, und ein Verfahren zu ihrer Herstellung
DE10348966A1 (de) 2003-10-22 2005-06-02 Degussa Ag Hochreaktive Polyurethan-Pulverlackzusammensetzungen auf Basis epoxidgruppenterminierter, uretdiongruppenhaltiger Polyadditionsverbindungen
DE102004012903A1 (de) * 2004-03-17 2005-10-06 Bayer Materialscience Ag Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
DE102004020429A1 (de) * 2004-04-27 2005-11-24 Degussa Ag Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten
DE102004020451A1 (de) * 2004-04-27 2005-12-01 Degussa Ag Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten
US7485729B2 (en) * 2004-08-12 2009-02-03 King Industries, Inc. Organometallic compositions and coating compositions
US20060036007A1 (en) * 2004-08-12 2006-02-16 King Industries, Inc. Organometallic compositions and coating compositions
DE102004043540A1 (de) * 2004-09-09 2006-03-30 Bayer Materialscience Ag Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
DE102004043538A1 (de) * 2004-09-09 2006-03-16 Bayer Materialscience Ag Herstellung von neuen strahlenhärtenden Bindemitteln
DE102004048773A1 (de) * 2004-10-07 2006-04-13 Degussa Ag Hydroxylterminierte uretdiongruppenhaltige Polyurethanverbindungen
DE102004049592A1 (de) * 2004-10-12 2006-05-04 Bayer Materialscience Ag Mit Soft-Touch-Lack beschichtete, verformbare Kunststoffverbundfolien und Kunststoffverbundelemente sowie deren Herstellung
US7135505B2 (en) * 2004-10-25 2006-11-14 Bayer Materialscience Llc Radiation curable coatings based on uretdione polyisocyanates
ATE409711T1 (de) * 2004-12-15 2008-10-15 Akzo Nobel Coatings Int Bv Thiolfunktionelle verbindungen enthaltende wässrige beschichtungszusammensetzung
DE102004062588A1 (de) * 2004-12-24 2006-07-06 Degussa Ag Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan
DE102005013401A1 (de) * 2005-03-23 2006-09-28 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
DE102005013329A1 (de) * 2005-03-23 2006-11-16 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
DE102005019430A1 (de) * 2005-04-25 2006-10-26 Bayer Materialscience Ag N-Methylpyrrolidon-freie Polyurethan-Dispersionen auf Basis von Dimethylolpropionsäure
DE102005049916A1 (de) * 2005-10-17 2007-04-19 Degussa Gmbh Lagerstabile, reaktive Pulverlackzusammensetzungen mit kristallinen Bestandteilen
DE102005053678A1 (de) * 2005-11-10 2007-05-16 Bayer Materialscience Ag Hydrophile Polyisocyanatgemische
DE102005060828A1 (de) * 2005-12-20 2007-06-28 Bayer Materialscience Ag Verfahren zur Herstellung von Polyadditionsverbindungen
DE102006042494A1 (de) * 2006-09-07 2008-03-27 Evonik Degussa Gmbh Bei niedriger Temperatur härtbare, uretdiongruppenhaltige Polyurethanzusammensetzungen mit quartären Ammoniumhalogeniden
DE102006046368A1 (de) * 2006-09-29 2008-04-03 Construction Research & Technology Gmbh Funktionalisiertes Polyurethanharz, Verfahren zu seiner Herstellung sowie dessen Verwendung
DE102007040239A1 (de) * 2007-08-25 2009-05-07 Bayer Materialscience Ag Verfahren zur Herstellung von niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen
DE102008007386A1 (de) 2008-02-01 2009-08-06 Evonik Degussa Gmbh Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend
CN101977954B (zh) * 2008-03-20 2013-03-27 巴斯夫欧洲公司 用于在低模塑温度下制备聚氨酯夹层部件的聚氨酯体系
EP2110396A1 (fr) * 2008-04-18 2009-10-21 Bayer MaterialScience AG Systèmes 1K-PUR en polyuréthanes aqueux ou solubles dans l'eau
EP2110395A1 (fr) * 2008-04-18 2009-10-21 Bayer MaterialScience AG Solutions de polyuréthane aqueuses pour systèmes de polyuréthane
DE102008002703A1 (de) * 2008-06-27 2009-12-31 Evonik Degussa Gmbh Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten
DE102008040967A1 (de) * 2008-08-04 2010-02-11 Leibniz-Institut Für Polymerforschung Dresden E.V. Werkstoff-Kunststoff-Verbunde und Verfahren zu ihrer Herstellung
DE102009008950A1 (de) * 2009-02-13 2010-08-19 Bayer Materialscience Ag Wässrige Beschichtungssysteme auf Basis physikalisch trocknender Urethanacrylate
DK2236533T3 (da) * 2009-03-31 2012-02-20 Sika Technology Ag Varmehærdende eller varmeaktiverbar sammensætning indeholdende et overfladeaktiveret polyisocyanat
US20110045219A1 (en) * 2009-08-18 2011-02-24 Bayer Materialscience Llc Coating compositions for glass substrates
US9080074B2 (en) * 2010-03-19 2015-07-14 Bayer Materialscience Llc Low temperature curing polyuretdione compositions
CN102311700A (zh) * 2010-06-29 2012-01-11 拜耳材料科技(中国)有限公司 脂肪族聚脲涂料、制备方法及其应用
CN103314043B (zh) * 2010-09-07 2015-07-08 拜耳知识产权有限责任公司 发泡耐光聚氨酯成型件
CN103314025B (zh) * 2010-10-29 2016-08-10 路博润高级材料公司 水性阳离子聚氨酯分散体
WO2012078331A1 (fr) * 2010-12-08 2012-06-14 Dow Global Technologies Llc Adhésif de polyuréthane à deux composants pour coller des matières plastiques renforcées de fibres
EP2465886A1 (fr) * 2010-12-16 2012-06-20 Bayer MaterialScience AG Produits de polyaddition de polyisocyanate, leur procédé de fabrication et d'utilisation
EP2683767A1 (fr) * 2011-03-06 2014-01-15 King Industries, Inc. Compositions d'un complexe métal amidine et d'un second composé, compositions de revêtement les comprenant
EP2758443B1 (fr) * 2011-09-21 2019-02-27 Dow Global Technologies LLC Polyuréthanes obtenus à l'aide de mélanges de composés amines tertiaires et d'acides de lewis comme catalyseurs
CN103842095B (zh) * 2011-09-30 2017-08-15 关西涂料株式会社 形成涂膜的方法和涂装的物品
WO2014016294A1 (fr) * 2012-07-26 2014-01-30 Bayer Materialscience Ag Dispersion aqueuse de polyuréthane comprenant un polyester d'acide téréphtalique
US9175117B2 (en) * 2013-03-15 2015-11-03 Covestro Llc Dual cure composite resins containing uretdione and unsaturated sites
CN104130686B (zh) * 2013-04-30 2017-09-19 旭化成株式会社 多异氰酸酯组合物及涂料组合物
EP2801587A1 (fr) * 2013-05-07 2014-11-12 Rhein Chemie Rheinau GmbH Compositions, leur fabrication et leur utilisation pour la fabrication de polyamides de fonte
US9206320B1 (en) * 2013-07-18 2015-12-08 Hentzen Coatings, Inc. Matte-appearance powder coating compositions with chemical agent resistance
AU2014356702B2 (en) * 2013-11-29 2018-03-15 Basf Se Polyurethane system with long pot life and rapid hardening
DE102014209183A1 (de) * 2014-05-15 2015-11-19 Evonik Degussa Gmbh Reaktive Zusammensetzung aus einer Uretdiongruppen haltigen Dispersion und Polyaminen
DE102014214130A1 (de) * 2014-07-21 2016-01-21 Evonik Degussa Gmbh Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten
EP2979851A1 (fr) * 2014-07-28 2016-02-03 Evonik Degussa GmbH Fabrication efficace de demi-produits et composants composites dans le cadre du procédé de pressage à froid utilisant des (méth)acrylates hydroxyfonctionnalisés réticulés par duroplastie à l'aide d'isocyanates ou d'uretdions
PL2990398T3 (pl) * 2014-08-29 2019-06-28 Covestro Deutschland Ag Hydrofilne estry kwasu poliasparginowego
EP2993202A1 (fr) * 2014-09-08 2016-03-09 Evonik Degussa GmbH Demi-produits composites et pièces moulées en étant constituées ainsi que pièces moulées directement fabriquées à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdions réticulés par duroplastie
EP3026071A1 (fr) * 2014-11-26 2016-06-01 Henkel AG & Co. KGaA Dispersions de polyuréthane stabilisées
DK3303437T3 (da) * 2015-05-29 2020-03-16 Basf Se Polyurethan-polyisocyanurat-harpiks til fiber-kompositmaterialer med lang åben klæbetid
WO2017154963A1 (fr) * 2016-03-09 2017-09-14 旭化成株式会社 Composition de polyisocyanate, composition de revêtement, composition de revêtement à base d'eau, et base revêtue

Patent Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2456469A1 (de) 1974-11-29 1976-08-12 Bayer Ag Verfahren zur herstellung von in wasser loeslichen bzw. dispergierbaren blockierten polyisocyanaten
DE2538484A1 (de) 1975-08-29 1977-03-10 Veba Chemie Ag Thermisch vernetzbare waessrige polyurethandispersionen
DE2814815A1 (de) 1977-04-07 1978-10-19 Grace W R & Co Waessrige urethandispersionen und codispersionen
EP0012348A1 (fr) 1978-12-14 1980-06-25 Bayer Ag Un liant contenant un polyisocyanate et un composé polyhydroxylé comme agent de revêtement applicable à partir d'une phase aqueuse
US4496684A (en) 1984-06-01 1985-01-29 Olin Corporation Uretdione group-containing polyurethane oligomers and aqueous dispersions thereof
EP0424697A2 (fr) 1989-10-03 1991-05-02 Asahi Glass Company Ltd. Composition de polyuréthane aqueuse et son utilisation
DE4001783A1 (de) 1990-01-23 1991-07-25 Bayer Ag Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung als bindemittel fuer ueberzugsmittel oder als reaktionspartner fuer gegenueber isocyanatgruppen oder carboxylgruppen reaktionsfaehige verbindungen
EP0576952A2 (fr) 1992-07-03 1994-01-05 Bayer Ag Compositions dispersables de polyisocyanates solubles dans l'eau et leur utilisation dans des vernis au four
EP0669353A1 (fr) 1994-02-28 1995-08-30 Hüls Aktiengesellschaft Produits de polyaddition contenant des groupes hydroxy- et uretdione, procédé de leur préparation et leur utilisation pour la préparation de vernis en poudre de polyuréthane à haute réactivité ne relâchant pas de produits de décomposition et vernis en poudre de polyuréthane obtenus par ce procédé
EP0818482A1 (fr) * 1996-07-13 1998-01-14 Hüls Aktiengesellschaft Adhésifs à un composant à partir de polyuréthanes, un procédé pour leur préparation ainsi que leur utilisation
WO2002092657A1 (fr) 2001-05-14 2002-11-21 Bayer Aktiengesellschaft Procede de dimerisation de diisocyanate d'isophorone
WO2004005364A1 (fr) 2002-07-04 2004-01-15 Bayer Materialscience Ag Isocyanates presentant des groupes uretdione
EP1687354A1 (fr) 2003-11-25 2006-08-09 Basf Corporation Procede de fabrication de revetement aqueux a reticulant solide
DE102005036654A1 (de) 2005-08-04 2007-02-15 Bayer Materialscience Ag Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur
US20120252926A1 (en) * 2011-03-30 2012-10-04 Basf Se Latently reactive polyurethane dispersion with activatable crosslinking
DE102012218081A1 (de) * 2012-10-04 2014-04-10 Evonik Industries Ag Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität
US20150232609A1 (en) 2012-10-04 2015-08-20 Evonik Industries Ag Innovative hydrophilic polyisocyanates with improved storage stability

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