WO2019180129A1 - Système catalytique pour dispersions d'uretdione - Google Patents

Système catalytique pour dispersions d'uretdione Download PDF

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Publication number
WO2019180129A1
WO2019180129A1 PCT/EP2019/057066 EP2019057066W WO2019180129A1 WO 2019180129 A1 WO2019180129 A1 WO 2019180129A1 EP 2019057066 W EP2019057066 W EP 2019057066W WO 2019180129 A1 WO2019180129 A1 WO 2019180129A1
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WO
WIPO (PCT)
Prior art keywords
acid
uretdione
catalyst system
group
catalyst
Prior art date
Application number
PCT/EP2019/057066
Other languages
German (de)
English (en)
Inventor
Saskia BEUCK
Sebastian Dörr
Hans-Josef Laas
Dorota Greszta-Franz
Nusret Yuva
Ralph-Georg BORN
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 US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/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 EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Priority to EP19711127.1A priority Critical patent/EP3768748A1/fr
Application filed by Covestro Deutschland Ag, Covestro Llc filed Critical Covestro Deutschland Ag
Priority to US17/040,063 priority patent/US20210024679A1/en
Priority to CN201980021559.3A priority patent/CN111868133A/zh
Publication of WO2019180129A1 publication Critical patent/WO2019180129A1/fr

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    • 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
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    • 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
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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
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    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
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    • C08G18/2072—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having at least three nitrogen atoms in the condensed ring system
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    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • 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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    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
    • C—CHEMISTRY; METALLURGY
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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
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    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
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    • C08G18/3225—Polyamines
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    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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    • C08G18/753—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
    • 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
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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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Definitions

  • the present invention relates to a catalyst system comprising
  • the present invention further relates to a kit, which comprises the catalyst system of the present invention and an aqueous uretdione dispersion having an acid value of from 1 to 100 mg KOH / g and further having at least one carboxyl group, a process for producing a polyurethane layer comprising the catalyst system of the present invention and said uretdione dispersion and the thereby obtained Polyurethane layer, as well as the use of the catalyst system for curing aqueous uretdione dispersions and / or for the production of paints or coatings.
  • EP 0 803 524 A1 describes amidines as catalysts in uretdione group-containing PU powder coating compositions.
  • the uretdione component and the OH-containing binder component are solid at room temperature. These are applied to the substrate by electrostatic powder spraying or vortex sintering, the curing temperatures being above 130 ° C. Their application as aqueous systems is not possible.
  • EP1526146 A1 describes a polyurethane powder coating composition.
  • the activity of the amidine catalysts decreases significantly in the presence of acids.
  • Epoxide group-terminated, uretdione-group-containing polyaddition compounds having a melting point of 40-130 ° C. are used.
  • the epoxide is anchored in the backbone, it is for example 2,3-epoxy-l-propanol and / or epoxidized soybean oil used.
  • a catalyst from the group of metal acetylacetonates, metal hydroxides, metal alcoholates, quaternary ammonium hydroxides, quaternary ammonium fluorides or quaternary ammonium carboxylates is used for curing.
  • the curing temperature is usually 120-160 ° C. Their application as aqueous systems is not possible.
  • WO 2009/095117 Al powder coating compositions which have a melting point of more than 40 ° C.
  • the catalyst used are quaternary ammonium salts or phosphonium salts.
  • the co-catalyst used is an epoxide compound of terephthalic acid diglycidyl ether and trimellitic triglycidyl ether (Araldit PT 912) or acetylacetonate. With these systems, no curing temperatures below 120 ° C are possible. Also, their use as aqueous systems is not possible.
  • Nonionic hydrophilicized dispersions have a permanent hydrophilicity, poor chemicals, and water resistance. Therefore, ionically hydrophilicized dispersions should be used. These are known to be anionic better than cationic. Typical anionic systems contain carboxyl groups to provide better dispersion. Catalysts that are sensitive to acids, including carboxyl groups, such as Na triazolate seemed therefore not suitable.
  • the object of the present invention was therefore to develop catalyst systems for the crosslinking of aqueous anionic polyurethane dispersions containing uretdione groups.
  • a cross-linking of the polymers should be possible.
  • the polymerization should preferably be able to take place below 100 ° C. (low-temperature crosslinking).
  • the catalyst systems should also be insensitive to acidic conditions.
  • the catalyst systems should contain no organometallic compounds.
  • a catalyst system comprising or consisting of
  • the present invention relates to:
  • Catalyst system comprising or consisting of
  • 1,2,3-triazole, 1,2,4-triazole and benzotriazole most preferably from the Na, Li and K salts of 1,2,3-triazole, 1,2,4-triazole and benzotriazole.
  • Catalyst system according to embodiment 1 or 2 characterized in that the at least one acid scavenger B) is selected from aliphatic or aromatic alcohols, diols, polyols, ethers and acids containing at least one epoxy group.
  • Catalyst system characterized in that A) to B) in a mass ratio of 1: 1 to 10: 1, preferably 2: 1 to 6: 1 and / or A) to C) in a mass ratio of 0.5: 1 to 5: 1, preferably 1: 1 to 2: 1 and / or B) to C) in a mass ratio of 1: 1 to 1:10, preferably 1: 1 to 1: 6 present.
  • a kit comprising the catalyst system according to any of embodiments 1 to 5 and separately therefrom an aqueous uretdione dispersion characterized by having an acid value of 1 to 100 mg KOH / g, preferably 2 to 50 mg KOH / g, stronger 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 of 2: 1 as a solvent and also having at least one carboxyl group.
  • kits according to embodiment 6 characterized in that the equivalent ratio of uretdione to hydroxy groups used is 0.5: 1 to 1: 0.5, preferably 0.75: 1 to 1: 0.75, most preferably 1: 1 ,
  • a process for producing a polyurethane layer comprising the steps
  • aqueous Uretdiondispersion having 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 the weight ratio 2: 1 as a solvent, and having at least one carboxyl group;
  • step iv) drying the mixture from step iii), preferably at room temperature and v) curing the mixture from step iv) with heat to 120 ° C, preferably up to 100 ° C, for up to 180 minutes, preferably up to 120 minutes.
  • Polyurethane layer in particular polyurethane film, obtainable by a method according to embodiment 8. 10.
  • molecular weights are determined by GPC (gel permeation chromatography) using polystyrene standards.
  • 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 acid scavenger B is to be understood as containing at least one type of acid scavenger, but contained in an arbitrary number of molecules in the composition.
  • two or more types of acid scavengers may be present in any arbitrary number, if the amounts are not defined.
  • a kit in the sense of the present invention is a system in which the catalyst system of the present invention and the aqueous carboxyl group-containing uretdione dispersion are spatially separated from each other.
  • the catalyst system comprises at least one compound A) selected from azoles, oxazoles, thiazoles, benzotriazole, benzimidazole, and benzoxazole and their salts.
  • the at least one compound A) is selected from pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole and benzotriazole and their salts.
  • the salts are preferably alkali metal, alkaline earth metal or ammonium salts.
  • the at least one compound A) selected from 1,2,3-triazole, 1,2,4-triazole and benzotriazole and their salts, more preferably from the alkali and alkaline earth salts of 1,2,3-triazole, 1 2,4-triazole and benzotriazole; most preferably from the Na, Li and K salts of 1,2,3-triazole, 1,2,4-triazole and benzotriazole, especially the sodium salts thereof.
  • the catalyst system comprises at least one acid scavenger B) containing at least one epoxy group.
  • the at least one acid scavenger B) is selected from aliphatic or aromatic alcohols, diols, polyols, ethers and acids containing at least one epoxy group, preferably selected from C 2-20 alcohols, C 2-20 diols, C 4- 50 polyols having at least 3 hydroxy groups, C 3-50 ethers and polyethers and C 3-20 acids containing at least one epoxy group.
  • glycidyl ethers such as butyl glycidyl ether, pentaerythritol tetraglycidyl ether, glycidyl isopropyl ether, 2-ethylhexyl glycidyl ether,
  • Polyethylene glycol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether or polyfunctional glycidyl ethers which are commercially available under the name HELOXY TM Modifier from Hexion.
  • the at least one acid scavenger B) preferably has a viscosity of from 5 to 500 mPas, more preferably from 50 to 250 mPas, most preferably from 100 to 200 mPas, measured at 25 ° C. according to DIN 53015: 2001-02.
  • the at least one acid scavenger B) has an epoxy equivalent (weight per epoxy group) of 120 to 650 g / eq, preferably 125 to 250 g / eq, measured according to DIN 16945: 1989-03.
  • the at least one acid scavenger B) has an epoxy value of from 20.0 to 35.0%, more preferably from 23.5 to 33.0%, most preferably from 26.5 to 32.5%, measured according to DIN 16945: 1989-03.
  • Suitable amidine catalysts C) in which the CN double bond is present as part of an open-chain molecule are, for example, N, N-dimethyl-N'-phenylformamidine or N, N, N'-trimethylformamidine, the preparation of which, for. In Chem. Ber. 98, 1078 (1965).
  • suitable amidines C) in which the CN double bond is part of a cyclic system may be mentioned here: in 1-position substituted 2-methyltetrahydropyrimidines, as described for.
  • Suitable catalysts C) in which the CN double bond is arranged exocyclically on a ring system are, for example, imines of N-alkyl-substituted lactams, such as 2-methylimino-1-methylpyrrolidone, the preparation of which, for. In Chem. Ber. 101, 3002 (1968).
  • Preferred as at least one component C) are bicyclic, N, N, N'-trisubstituted amidine-containing catalysts of the general formula (1)
  • n is an integer from 1 to 3, preferably 2.
  • Such bicyclic amidines is known and described, for example, in DE 1 545 855 A1 or EP 662 476 A1.
  • Particularly preferred catalysts C) are 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), in particular DBU.
  • no ammonium or phosphonium salts are included.
  • no organometallic catalysts and / or quaternary ammonium hydroxides, quaternary ammonium fluorides or quaternary ammonium carboxylates are contained.
  • no further catalysts are included.
  • the invention further relates to a kit in which an acidic aqueous uretdione dispersion and the catalyst system of the present invention are present separately.
  • Suitable uretdione dispersions are those generally known to those skilled in the art, with the proviso that they have 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 the weight ratio 2: 1 as solvent, and having at least one carboxyl group.
  • the aqueous uretdione dispersion according to the present invention has an equivalent ratio of uretdione to hydroxy groups of from 0.5: 1 to 1: 0.5, preferably from 0.75: 1 to 1: 0.75, most preferably 1 : 1 up.
  • Suitable aqueous polyurethane dispersions usually contain, in the same polymer molecule, the essential structural units (I) and (II) in which R is an aliphatic, cycloaliphatic, araliphatic or aromatic radical which is derived from a polyisocyanate selected from the group consisting of tetramethylene diisocyanate, cyclohexane-1,3- or 1,4-diisocyanate, pentamethylene diisocyanate (PDI),
  • TXDI Tetramethylxylylene diisocyanate
  • TDI tolylene diisocyanate
  • MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • R ' is an alkyne, preferably ethyl or methyl, more preferably methyl
  • X is a carboxylic acid (COOH) or carboxylate (COCT) radical
  • Y is NH 2
  • NHR "or OH, preferably OH and R" is an alkyne, preferably hexyl , Butyl, propyl, ethyl or methyl, more preferably methyl.
  • the dispersion which can be used in the present invention may contain both uretdione groups (acting as capped isocyanates) and hydroxyl groups in
  • Suitable uretdione dispersions can be prepared by the following process comprising the steps of:
  • a first step (I) an ionic uretdione group-containing, hydrophilicized, hydroxyl or isocyanate end-group-containing prepolymer by reaction of
  • BG further polyol component
  • M n molecular weight of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol
  • AG polyisocyanates
  • polyisocyanates (AG) having an NCO functionality of> 2 and
  • the implementation of the first two synthesis steps can be carried out in the reverse order or in a single reaction step. It is also possible to use the polyol component (BG) proportionally in the preparation of the prepolymer (I). It is likewise possible to use the compound (C) proportionally in the prepolymerization (II) of the uretdione group-containing polyisocyanate mixture.
  • an acid-functional compound (C) and a further polyisocyanate component (AG) are added simultaneously or in a further step.
  • the ratio of the isocyanate groups, including the uretdione groups, to all isocyanate-reactive groups is preferably from 0.5 to 5.0 to 1, more preferably from 0.6 to 2.0 to 1, especially from 0.8 to 1.5 to comply with 1.
  • Suitable polyisocyanate components are aliphatic, cycloaliphatic, araliphatic and / or aromatic isocyanates having an average functionality of from 2 to 5, preferably 2 and having an isocyanate content of from 0.5 to 60% by weight, preferably from 3 to 40% by weight.
  • % particularly preferably from 5 to 30 wt .-%, such as 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, Toluylene diisocyanate (TDI), diphenylmethane-2,4'- and / or 4,4'-diisocyanate (MDI), triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diiso
  • isophorone diisocyanate dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate or hexamethylene diisocyanate, in particular isophorone diisocyanate.
  • suitable polyisocyanate components are polyisocyanates prepared by modifying the di- and / or triisocyanates mentioned above with isocyanurate, iminooxadiazinetrione, urethane, allophanate, biuret and / or oxadiazinetrione structures, as described, for example, in J. Prakt. Chem. 336 (1994) 185-200 or DE-A 16 70 666 and EP-A 798 299 are described by way of example.
  • Suitable polyisocyanates are also the known prepolymers having terminal isocyanate groups, such as are obtainable in particular by reacting the abovementioned simple polyisocyanates, especially diisocyanates, with substoichiometric amounts of organic compounds having at least two isocyanate-reactive functional groups.
  • the ratio of isocyanate groups to NCO-reactive hydrogen atoms is 1.05: 1 to 10: 1, preferably 1.5: 1 to 4: 1, wherein the hydrogen atoms are preferably derived from hydroxyl groups.
  • the type and proportions of the starting materials used in the preparation of NCO prepolymers are selected so that the NCO prepolymers preferably have an average NCO functionality of 2 to 3 and a number average molecular weight of 300 to 10,000 g / mol, preferably 800 to 4000 g / mol.
  • Suitable components (A2 ') are polyisocyanates which contain at least one isocyanate group and at least one uretdione group. These are prepared, as described, for example, in WO 02/92657 A1 or WO 2004/005364 A1 by reaction of suitable starting isocyanates. 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 from which the uretdione-containing building blocks (A2 ') 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, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane,
  • Toluylene diisocyanate (TDI), diphenylmethane-2,4'- and / or 4,4'-diisocyanate (MDI), triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diisocyanate and any mixtures of such isocyanates.
  • TDI Toluylene diisocyanate
  • MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • triphenylmethane-4,4'-diisocyanate or naphthylene-l 5-diisocyanate and any mixtures of such isocyanates.
  • isophorone diisocyanate dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate or hexamethylene diisocyanate.
  • component (A2 ') may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • the polyol component (BG) 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 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 acid functional compounds (C) are hydroxy-functional carboxylic acids, preferably mono- and dihydroxycarboxylic acids, e.g. 2-hydroxyacetic acid, 3-hydroxypropanoic acid or 12-hydroxy-9-octadecanoic acid (ricinoleic acid).
  • Preferred carboxylic acids (C) are those in which the carboxyl group is hindered in its reactivity due to steric effects, e.g. Lactic acid.
  • Particularly preferred are 3-hydroxy-2,2-dimethylolpropanoic acid (hydroxypivalic acid) or dimethylolpropionic acid, most preferably exclusively dimethylolpropionic acid is used.
  • step (I) if component (BG) is used as a proportion in step (I), its proportion is at most 50% by weight, based on the sum of components (C) and (BG). Preferably, in step (I) only component (C) is used.
  • the polyol component (B2 ') is selected from the group of
  • linear, difunctional polyols having average molecular weights Mn of from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol,
  • Suitable polyol component (bl) are 2 to 6-hydric alcohols and / or mixtures thereof which have no ester groups. Typical examples are 1,2-ethanediol, 1,2-propanediol and 1,3-diol, 1,4-butanediol, 1,2 or 2,3, 1,6-hexanediol, 1,4-dihydroxycyclohexane, glycerol, Trimethylolethane, trimethylolpropane, pentaerythritol and sorbitol. Of course, as component (bl) it is also possible to use alcohols with ionic groups or groups convertible into ionic groups. Preference is given, for example, to 1,4- or 1,3-butanediol, 1,6-hexanediol or trimethylolpropane and mixtures thereof.
  • Suitable linear difunctional polyols (b2) are selected from the group of polyethers, polyesters and / or polycarbonates.
  • the polyol component (b2) contains at least one ester group-containing diol of molecular weight Mn from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, more 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 components may also be present which have a molecular weight below or above these limits. 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 e.g.
  • 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 having an average molecular weight of from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol, which are prepared in a manner known per se from a diol or diol mixture the type exemplified above as starter and e-caprolactone have been prepared.
  • the preferred starter molecule is 1,6-hexanediol.
  • Particularly preferred are those polycaprolactone diols which have been prepared by polymerization of e-caprolactone using 1,6-hexanediol as a starter.
  • linear polyol component (b2) it is also possible to use (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran.
  • polyethers having an average molecular weight Mn of from 500 to 2000 g / mol, such as e.g. Polyethylene 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.
  • Suitable mono-functional linear polyethers (b3) are, for example, (co) polyethers of ethylene oxide and / or propylene oxide. Preference is given to monoalcohol-initiated polyalkylene oxide polyethers of average molecular weight Mn of from 350 to 2500 g / mol with at least 70% of ethylene oxide units.
  • (co) polymers with more than 75% ethylene oxide units and a molecular weight Mn of 350 to 2500 g / mol, preferably from 500 to 1000 g / mol.
  • As starter molecules in the preparation of these polyether monofunctional alcohols having 1 to 6 carbon atoms are preferably used.
  • Suitable polyols (B3 ') are polyols having an OH functionality greater than or equal to 2, and with average molecular weights of 500 to 5000 g / mol, preferably from 500 to 3000 g / mol, particularly preferably from 500 to 2000 g / mol.
  • Preferred polyols (B3 ') are e.g. Polyether average molecular weight of 300 to 2000 g / mol and an average functionality of 2.5 to 4 OH groups / molecule. Also preferred are polyesters of average OH functionality of 2.5 to 4.0. Suitable diols and dicarboxylic acids for the polyesters are those mentioned under component (b2), but additionally contain tri- to hexafunctional short-chain polyols, e.g. Trimethylolpropane, pentaerythritol or sorbitol.
  • polyester polyols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid, as well as 1,4-butanediol and 1,6-hexanediol.
  • component (B3 ') are (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran average functionality of greater than or equal to 2, as well as polycarbonate polyols.
  • the carboxylic acid groups present in the polyurethanes of the invention are preferably at least 50%, more preferably 80% to 120%, particularly preferably 95 to 105% neutralized with suitable neutralizing agents (N) and then dispersed with deionized water.
  • the neutralization can take place before, during or after the dispersing or dissolving step. However, preference is given to neutralization before the addition of water.
  • Suitable neutralizing agents (N) 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.
  • Amines such as e.g. Triethylamine, diisopropylhexylamine, particularly preferred is dimethylethanolamine.
  • solvents may also be added to the reaction mixture if appropriate. Suitable are all known paint solvents such as N-methylpyrrolidone, methoxypropyl acetate, Proglyde DMM ® (Dow Chemicals), Shellsol ® (Shell AG) or xylene. Preferably, amounts of 0 to 10 wt .-%, preferably 0 to 5 wt .-%, are used. The solvent is preferably added during the polymerization.
  • auxiliaries and additives of the coating technology which are to be used, such as, for example, pigments, leveling agents or bubble-preventing additives, can also be added to the aqueous dispersions according to the invention.
  • suitable uretdione dispersions of the present invention are storage-stable, reactive aqueous uretdione-group-containing compositions which comprise a physical mixture dispersed in water and, if appropriate, organic solvents
  • At least one hardener containing uretdione groups based on aliphatic, (cyclo) aliphatic, araliphatic and / or aromatic polyisocyanates, which contains no chemically bonded hydrophilicizing groups;
  • (B12) at least one hydroxyl-containing polyol which contains at least one chemically bonded carboxylic acid group
  • the amount ratio of the components (Al l) and (Bl 2) is such that the molar ratio of the uretdione present NCO groups of the harder (Al l) to NCO-reactive groups of the polyol (B12) 0.5: 1 to 1: 0.5 and 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 of 2: 1 as a solvent.
  • Suitable polyisocyanates containing uretdione groups as starting compounds for the component (Al 1) are the polyisocyanates (A2 ') described above.
  • reaction of these uretdione group-carrying polyisocyanates to uretdione-containing hard (Al1) involves the reaction of the free NCO groups of the starting compounds (A2 ') with the polyol component (BG), optionally with the concomitant use of the polyol component (b2).
  • polyol component in the preparation of uretdione groups having curing agent (Al l) also low molecular weight ester-containing diols of a mean, calculated from functionality and hydroxyl number molecular weight of 134 to 349 g / mol, preferably 176 to 349 g / mol, are used.
  • ester-containing diols or mixtures of such diols 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 the preparation of 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 (Al l) and amino-functional compounds can be used.
  • suitable low molecular weight amino-functional compounds are aliphatic and cycloaliphatic amines and amino alcohols having primary and / or secondary bound amino groups, such as.
  • Diaminodicyclohexylmethane 4-aminocyclohexyl-4-amino-3-methylcyclohexylmethane, 4-amino-3,5-dimethylcyclohexyl-4-amino-3-methylcyclohexylmethane and 2- (4-aminocyclohexyl) -2- (4-amino-3-methylcyclohexyl )methane.
  • solvents may be used in the preparation of the uretdione group-containing hardeners (Al 1).
  • Suitable solvents for uretdione hardeners (Al l) are all liquid substances which do not react with other ingredients, eg. As acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, propylene glycol mono-n-butyl ether (Dowanol PnB, (Dow Chemicals)), ® Proglyde DMM (Dow Chemicals), methoxypropyl acetate and Dibasicester.
  • the uretdione group-containing hardener (Al l) are free from ionic or non-ionic hydrophilizing compounds.
  • ionically hydrophilizing compounds the person skilled in the art understands compounds which have at least one group capable of anion or cation formation.
  • 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 hardening agents (Al 1) are preferably free of anion-forming, 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,
  • uretdione-containing curing agents (Al 1) are preferably free from anion-containing compounds capable of forming anions, such as, for example, ⁇ , ⁇ -diaminovaleric acid, 2,4-diamino-toluenesulfonic acid and the like.
  • the uretdione group-containing hardeners (Al 1) are also preferably free of sulfonic acid groups capable of forming anions.
  • the uretdione hardening agents (Al 1) 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 hardeners (Al 1) are furthermore preferably free from nonionically hydrophilizing compounds, such as, for example, polyalkylene oxide polyether alcohols or polyalkylene oxide polyether amines.
  • the uretdione groups are hardeners (Al 1) preferably free of polyethylene oxide polyether or mixed polyalkylene oxide polyethers whose alkylene oxide units consist of at least 30 mol% of ethylene oxide units.
  • Preferred uretdione hardeners (Al 1) 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 C 2 N 2 O 2, molecular weight 84 g / mol).
  • the hardeners A (11) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • Suitable polyols (Bl 2) can be selected from polyester polyols, polyether polyols, polyurethane ether polyols, polyurethane ester polyols, polycaprolactone polyols,
  • Polyetheresterpolyole, polycarbonate polyols, poly (metha) acrylate 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.
  • Starting component for the polyols (B12) are those polyols, preferably diols, in question, which contain at least one carboxylic acid group, generally 1 to 3 carboxylic acid groups per molecule.
  • dihydroxycarboxylic acids such as a, a-dialkylolalkanoic acids, especially a, a dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-
  • Dihydroxysuccinic acid furthermore polyhydroxy acids, such as gluconic acid, or aminocarboxylic acids, such as, for example, a, W-diaminovaleric acid, 2,4-diamino-toluenesulfonic acid and the like. It is also possible to use mixtures of the compounds described above.
  • Starting component for the polyols (B12) is particularly preferred 2,2-dimethylolpropionic acid. Less preferred may also be monohydroxy-functional compounds having at least one carboxylic acid group, such as hydroxypivalic acid or hydroxydecanoic acid.
  • poly (metha) acrylate polyols are copolymers which contain monomer units with carboxylic acid or carboxylic anhydride groups, such as acrylic acid, methacrylic acid, ß-carboxyethyl acrylate, crotonic acid, fumaric acid, maleic acid (anhydride), ltaconic acid or monoalkyl esters of dibasic acids or anhydrides, for example maleic acid monoalkyl esters.
  • carboxylic acid or carboxylic anhydride groups such as acrylic acid, methacrylic acid, ß-carboxyethyl acrylate, crotonic acid, fumaric acid, maleic acid (anhydride), ltaconic acid or monoalkyl esters of dibasic acids or anhydrides, for example maleic acid monoalkyl esters.
  • acrylic acid or methacrylic acid copolymers Preference is given to acrylic acid or methacrylic acid copolymers.
  • Suitable polyols (B12) are polyols having an OH content greater than 1% by weight (calculated as OH group on solid content, molecular weight 17 g / mol) and with number-average molecular weights Mn from 500 to 20,000 g / mol, preferably from 500 to 10,000 g / mol, more preferably from 500 to 5,000 g / mol.
  • the preparation of the polyurethane resin used according to the invention is preferably carried out in such a way that a non-aqueous resin precursor of the polyol (B12) with at least one uretdione curing agent (Al l) 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 (B12) are preferably neutralized to at least 50%, more preferably 80% to 120%, particularly preferably 95 to 105% with suitable neutralizing agents (N) 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 (N) 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.
  • Amines such as e.g. Triethylamine, diisopropylhexylamine, particularly preferred is dimethylethanolamine.
  • solvents under (CI 3) are all liquid substances suitable that do not react with other ingredients. Preferred are acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, propylene glycol mono-n-butyl ether (Dowanol PnB), methoxypropyl acetate and dibasic ester.
  • the solvent used can then be removed by distillation.
  • leveling agents such as polysilicones or acrylates, light stabilizers, for.
  • sterically hindered amines, or other auxiliaries such as.
  • fillers and pigments such as titanium dioxide may be added in an amount of up to 50% by weight of the uretdione dispersion. Examples:
  • Pendulum hardness The pendulum hardness was measured on a glass plate according to DIN EN ISO 1522: 2007-04 and is determined by König.
  • the cured paints were tested for resistance to xylene, 1-methoxy-2-propyl acetate, ethyl acetate, acetone and water.
  • a piece of cotton wool soaked in the test substance was placed on the coating surface and covered with a watch glass. After the indicated exposure time, the cotton was removed, the exposed area was dried and examined immediately.
  • the evaluation of the softening or discoloration of the coating surface was carried out according to DIN EN ISO 4628-1: 2016-07.
  • the uretdione ring opening was characterized by a Bruker FT-fR spectrometer (Tensor II with platinum ATR (diamond crystal) unit) The spectra were recorded in a wavenumber range of (4000-400) cm 1. The maximum of the uretdione peak (approximately 1760 cm 1 ) was evaluated, and peak heights to comparative systems were compared to an initial value set to 100% (uretdione film without catalyst, dried at room temperature) The uretdione peak height of the films cured at 180 ° C. for 30 min set to 0%. Variations were determined relative to these 100 and 0% values (ratio formation).
  • the intensity of the spectrum depends on the occupation of the crystal surface. Since comparable measurements by sample preparation can not guarantee a comparable coverage of the crystal surface, a correction of this effect for the ratio formation by normalization of all spectra on the top of the CH- Stretching oscillation (wavenumber range) (3000-2800 cm 1 ) In the evaluation of the peak heights described above, a basic correction of the spectra is additionally performed.
  • the solids content (non-volatile content) was determined by heating a weighed sample at 125 ° C to constant weight. At constant weight, the solids content is calculated by weighing the sample back.
  • the NCO content was determined volumetrically according to DIN-EN ISO 11909.
  • the control of free NCO groups was carried out by IR spectroscopy (band at 2260 cm 1 ).
  • the indicated viscosities were determined by means of rotational viscometry according to DIN 53019: 2016-10 at 23 ° C. using a rotational viscometer with a shear rate of 40 l / s, Anton Paar Germany GmbH, Ostfildern, Germany.
  • the mean particle sizes (number average) of the polyurethane dispersions were determined after dilution with deionized water by laser correlation spectroscopy (instrument: Malvern Zetasizer 1000, Malver Inst. Limited, London, UK).
  • the zeta potential was measured by diluting one drop of the sample with 20 mL of demineralized water and homogenizing by stirring. Subsequently, the zeta potential was determined at 23 ° C in the Malvern Nanosizer ZS90 (Malvern Instruments,dorfberg, Germany).
  • the acid number of the respective dispersion was determined in accordance with DIN EN ISO 2114: 2002-06.
  • the solvent used was a mixture of acetone and ethanol (2: 1, by weight).
  • the unit of acid number is mg KOH per g of the sample analyzed.
  • Heloxy Modifier TP Polyfunctional glycidyl ether of trimethylolpropane, Hexion
  • Bayhydrol A2695 water-dilutable, OH-functional polyacrylate dispersion; about 41% in water / l-butoxy-2-propanol, neutralized with triethanolamine / dimethylethanolamine, 7.2% 1-butoxy-2-propanol, Fa. Covestro
  • Dowanol PnB Propylene glycol mono-n-butyl ether, Dow
  • Solvent Naphtha 100 an aromatic solvent, Azelis
  • DMPS Dimethylolpropionic acid
  • IPDI isophorone diisocyanate
  • DMAP 4-dimethylaminopyridine
  • the resulting white dispersion had the following properties:
  • Part 1 of Table 1 was weighed into a stirring apparatus under nitrogen and heated to 138 ° C. Thereafter, Part 2 was added uniformly at 138 ° C in 20 min. Subsequently, immediately part 3 and part 4 were added in parallel in 4 hrs. 30 Min. At 138 ° C evenly. After the addition, the reaction mixture was kept at 138 ° C for 30 min. Finally, Part 5 and Part 6 were added uniformly in 1 hr. 30 Min. At 138 ° C in parallel. After the addition, the reaction mixture was again held at 138 ° C for 1 hr. After cooling to 100 ° C, the reaction mixture was bottled. This gave a slightly yellowish, highly viscous polyacrylate solution.
  • Part 1 of Table 2 was weighed into a stirring apparatus under nitrogen and heated to 138 ° C. Thereafter, Part 2 was added uniformly at 138 ° C in 20 min. Subsequently, immediately part 3 and part 4 were added in parallel in 4 hrs. 30 Min. At 138 ° C evenly. After the addition, the reaction mixture was kept at 138 ° C for 30 min. Finally, Part 5 and Part 6 were added uniformly in 1 hr. 30 Min. At 138 ° C in parallel. After the addition, the reaction mixture was again held at 138 ° C for 1 hr. After cooling to 110 ° C, the reaction mixture was bottled. This gave a slightly yellowish, highly viscous polyacrylate solution.
  • Part 1 from Table 3 was weighed into a stirring apparatus under nitrogen and heated to 148 ° C. Thereafter, Part 2 was uniformly added at 128 ° C in 20 min. Subsequently, Part 3 and Part 4 were added in parallel at the same time in 6 hours at 148 ° C. After the addition, the reaction mixture was held at 148 ° C for 60 min. After the addition, the reaction mixture was again held at 148 ° C for 1 hr. After cooling to 80 ° C, the polyacrylate solution was bottled.
  • Part 1 of Table 4 was weighed into a stirring apparatus under nitrogen and heated to 144 ° C. Thereafter, part 2 was uniformly added at 144 ° C in 20 min. Subsequently, Part 3 and Part 4 were immediately added in parallel in 4 hrs. 30 Min. At 144 ° C evenly. After the addition, the reaction mixture was held at 144 ° C for 5 min. Finally, Part 5 and Part 6 were added uniformly in 1 hour 30 min. At 144 ° C dosed. After the addition, the reaction mixture was again held at 144 ° C for 1 hr. After cooling to 100 ° C, the reaction mixture was bottled. This gave a slightly yellowish, highly viscous polyacrylate solution.
  • the uretdione dispersion of Preparation Example 1 was dispersed in water and then mixed in a speed mixer (2000 rpm) with Bayhydrol A2695. Heloxy Modifier TP was added, then 1,2,4-Na triazolate (10% in water) and DBU (10% in water, freshly mixed) were added. The mixture was again mixed with a speed mixer (2000 rpm) and allowed to stand on the bench for 30 minutes for foam reduction.
  • the mixture was applied to glass or to a normalized coil test panel (Coil Coating black - CS 200570, Heinz Zanders für-Blech-Logiding) with a coating bar with a layer thickness of 150-180 ⁇ m (wet).
  • the plates were dried at room temperature for 5 minutes and then baked at 100 ° C for 30 minutes.
  • the films obtained were evaluated by application technology and an IR spectrum was recorded.
  • Example 4 Formulations and Comparative Formulations with Example Dispersion 1
  • the mixture was applied to glass or sheet with a coating knife having a layer thickness of 150-180 ⁇ m (wet).
  • the plates were dried at room temperature for 5 minutes and then baked at 100 ° C for 30 minutes.
  • the resulting coatings were evaluated by application technology and an IR spectrum was recorded.
  • the uretdione dispersion from Preparation Examples 3 ad was in a speed mixer (2000 rev / min) with the uretdione dispersion of Preparation Example 1, Heloxy Modifier TP, 1,2,4-Na triazolate (10% in water) and DBU (10% in water, freshly mixed). The mixture was allowed to stand for 30 minutes to reduce foam.
  • the mixture was applied to glass or sheet with a coating knife having a layer thickness of 150-180 ⁇ m (wet).
  • the plates were dried at room temperature for 5 minutes and then baked at 100 ° C for 30 minutes.
  • the resulting coatings were evaluated by application technology and recorded an IR spectrum.
  • the curing reaction can be monitored by observing the ring opening of the uretdione by IR spectroscopy.
  • IR uretdione peak With the combination of sodium triazolate, DBU and heloxy modifier TP, the IR uretdione peak has almost disappeared ( ⁇ 4% relative to the height of the uretdione peak of the dried starting material).
  • Pendulum hardness also increases with the effectiveness of the catalyst mixture.
  • the resistance to xylene, MPA, EA and acetone should be at least 1/1/2/4, the water resistance must be at least 1-2. Both resistances can only be obtained by the catalyst mixture.
  • an equimolar amount of uretdione to alcohol (entries 13 to 16) leads to much higher hardnesses and better resistances than an excess of alcohol (entries 9 to 12).

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  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

La présente invention concerne un système catalytique comprenant : A) au moins un composé choisi parmi les azoles, les oxazoles, les thiazoles, le benzotriazole, le benzimidazole, le benzoxazole et leurs sels ; B) au moins un piégeur d'acide contenant au moins un groupe époxy ; et C) au moins un catalyseur comprenant une structure amidine N,Ν,Ν'-trisubstituée ayant une teneur en groupes amidine de 12,0 à 47,0 % en poids, exprimé comme CN2 avec un poids moléculaire = 40. Un kit comprend le système catalytique de la présente invention et une dispersion aqueuse d'uretdione ayant un indice d'acide de 1 à 100 mg KOH/g et en outre au moins un groupe carboxyle. L'invention concerne également un procédé pour fabriquer une couche de polyuréthane avec le système catalytique selon la présente invention et ladite dispersion d'uretdione et la couche de polyuréthane ainsi obtenue, ainsi que l'utilisation du système catalytique pour le durcissement de dispersions d'uretdione aqueuses acides et/ou la fabrication de vernis ou de revêtements.
PCT/EP2019/057066 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione WO2019180129A1 (fr)

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EP19711127.1A EP3768748A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
CN201980021559.3A CN111868133A (zh) 2018-03-23 2019-03-21 脲二酮分散体的催化剂体系
US17/040,063 US20210024679A1 (en) 2018-03-23 2019-03-21 Catalyst system for uretdione dispersions

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US15/933,527 2018-03-23
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
US15/933,507 2018-03-23
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933,470 2018-03-23
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,570 2018-03-23
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,487 2018-03-23
US15/933,495 2018-03-23
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
EP18163621.8 2018-03-23
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
EP18163620.0 2018-03-23
US15/933,475 2018-03-23
EP18163625.9 2018-03-23
US15/933,553 2018-03-23
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,500 2018-03-23
EP18181876.6 2018-07-05
EP18181877.4 2018-07-05
EP18181877.4A EP3590988A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
US15/933,511 2018-08-23

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PCT/EP2019/057064 WO2019180127A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
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