EP1723189A1

EP1723189A1 - Polyurethane compositions that can be cured at low temperatures and contain uretdione groups

Info

Publication number: EP1723189A1
Application number: EP05701506A
Authority: EP
Inventors: Emmanouil Spyrou
Original assignee: Degussa GmbH
Current assignee: Evonik Operations GmbH
Priority date: 2004-03-06
Filing date: 2005-01-13
Publication date: 2006-11-22
Also published as: WO2005085315A1; CN1878817A; US20070266897A1; DE102004011005A1

Abstract

The invention relates to polyurethane compositions that can be cured at low temperatures and contain uretdione groups.

Description

Low temperature curable. uretdiongπippenhaltige

Polyurethanzusammensetzungcn

The invention relates to uretdione group-containing polyurethane compositions which cure at low stoving temperatures, to processes for the production of such compositions and to their use for the production of plastics, in particular paint coatings and adhesives.

Externally or internally blocked polyisocyanates represent valuable crosslinkers for thermally crosslinkable polyurethane (PUR) lacquer and lubricant compositions.

For example, B. DE-OS 27 35 497 PUR paints with excellent weather and heat stability. The crosslinkers, the preparation of which is described in DE-OS 27 12 931, consist of isophorone diisocyanate containing ε-caprolactam blocked isocyanurate groups. Polyisocyanates containing urethane, biuret or urea groups are also known, the isocyanate groups of which are also blocked

The disadvantage of these externally blocked systems is that the blocking agent is split off during the mechanical crosslinking reaction. Since the blocking agent can thus emit into the environment, special precautions must be taken for cleaning the exhaust air and / or recovering the blocking agent for ecological and occupational hygiene reasons. In addition, the networkers have a low reactivity. Curing temperatures above 170 ° C are required.

DE-OS 30 30 539 and DE-OS 30 30 572 describe ner processes for the preparation of polyaddition compounds containing uretdione groups, the terminal isocyanate groups of which are irreversibly blocked with monoalcohols or monoamines. The chain-breaking components of the network are particularly disadvantageous, which lead to low network densities of the PU lacquer coatings and thus to moderate resistance to solvents.

Hydroxylgrappente_-t - are ined, uretdione group-containing polyaddition compounds Subject of EP 669 353. Because of their functionality of two, they have an improved resistance to solvents. A common feature of the compositions based on these polyisocyanates containing uretdione groups is that they do not emit any volatile compounds during the curing reaction. However, the baking temperatures are at a high level with at least 180 ° C.

EP 803 524 describes the use of amidines as catalysts in PUR-L ιck compositions. Although these catalysts lower the curing temperature, they show considerable yellowing, which is generally undesirable in the coating area. The cause of this yellowing is probably the reactive nitrogen atoms in the amidines. These can react with atmospheric oxygen to form N-oxides, which are responsible for the discoloration

EP 803 524 also mentions other catalysts which have hitherto been used for this purpose, but without showing any particular effect on the curing temperature. These include the organometallic catalysts known from polyurethane chemistry, such as. B. dibutyltin dilaurate (DBTL), or tertiary amines, such as. B. 1,4-diazabicylco [2.2.2] octane (DABCO).

It was therefore the task of the present invention to find highly reactive uretdione group-containing polyurethane compositions which can be cured even at very low temperatures and which are particularly suitable for the production of plastics and of high-gloss or matt, light and weather-resistant, highly reactive lacquer and Hebstoffiiis-i -settings are suitable.

Surprisingly, it was found that certain catalysts accelerate the cleavage of uretdione groups to such an extent that the curing temperature of polyurethane additives can be considerably reduced when using uretdione-containing hardeners

Conventional uretdione-containing polyurethane compositions can only be cured under normal conditions (DBTL catalysis) from 180 ° C. With the help of the invention Low-temperature curing polyurethane --- not only energy and (curing) time can be saved at a curing temperature of 100 - 160 ° C, but also many temperature-sensitive substrates can be coated or bonded, which at 180 ° C would show undesirable signs of yellowing, decomposition and / or embrittlement. In addition to metal, glass, wood, leather, plastics and MDF boards, certain aluminum substrates are also suitable. In the latter case, too high a temperature load sometimes leads to an undesirable change in the crystal structure.

The present invention essentially relates to highly reactive uretdione group-containing polyurethane solutions

A) at least one hardener containing uretdione, based on aromatic, aliphatic, (cyclo) aliphatic or cycloaliphatic polyisocyanates and compounds containing hydroxyl groups, with a free NCO content of mine 5% by weight and a uretdione content of 1 - 18% by weight, B ) optionally a polymer containing hydroxyl groups or amine groups with an OH number between 20 and 500 mg KOH / gram or a comparable amine content,

C) at least one catalyst of the formula [PR ¹ RR ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ^{4. At the} same time or independently of one another, alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, each linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of cycles, bicycls or tricycls and the bridging atoms can also be heteroatoms in addition to carbon, with 1 to 18 carbon atoms and each radical R ¹ - R ⁴ additionally one or may have more alcohol, arnino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO is synonymous with R ⁶ with alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, linear or branched, with 1 - 18 carbon atoms, which additionally contain one or more alcohol, amino, ester, keto, thio, acid, urethane -, urea, allophanate groups, double bonds, triple bin dung or halogen atoms, so that the proportion of the catalyst under C) 0.001 - 5 wt .-% of the total amount of components A) and B), and wherein the catalysts C) can be surrounded by an inert shell and thus encapsulated, and

D) optionally at least one compound reactive towards acid groups with a weight fraction, based on the total formulation, of 0.1 to 10%, E) optionally at least one acid in monomeric or polymeric form in a weight fraction, based on the overall formulation, of 0.1 until 10 %,

F) optionally solvent,

G) optionally auxiliaries and additives.

Another object of the invention is a method for producing the polyurethane compositions.

The invention also relates to the use of the polyurethane-J compositions according to the invention for the production of liquid and powdery lacquer coatings on metal, plastic, glass, wood or leather substrates or other heat-resistant substrates.

The invention also relates to the use of the polyurethane compositions according to the invention as oleic compositions for bonding metal, plastic, glass, wood or leather substrates or other heat-resistant substrates.

The invention also relates to melamine coating compositions, in particular for automobile bodies, motorcycles and bicycles, building parts and household appliances, wood coating compositions, glass coating compositions, leather coating compositions and plastic coating compositions.

Polyisocyanates containing uretdione groups are well known and are described, for example, in US 4,476,054, US 4,912,210, US 4,929,724 and EP 417 603. A comprehensive one

Overview of industrially relevant processes for the dimerization of isocyanates Uretdione Hefert das J. Prakt. Chem. 336 (1994) 185-200. In general, the conversion of isocyanates to uretdiones takes place in the presence of soluble dimerization catalysts such as. B. Dia - syla --- tinopyridines, trialkylphosphines, phosphorous acid triamides or imidazoles. The reaction - optionally carried out in solvents, but preferably carried out in the absence of solvents - is stopped when a desired conversion is reached by adding catalyst poisons. Excess monomeric isocyanate is then separated off by short-path evaporation. If the catalyst is volatile enough, the reaction mixture can be freed from the catalyst in the course of the monomer separation. In this case, the addition of catalyst poisons is not necessary. In principle, a wide range of isocyanates is suitable for the production of polyisocyanates containing uretdione groups. According to the invention, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), 2-methylpentane diisocyanate (MPDI), 2,2,4-trimethylhexamethylene diisocyanate1,4,4-trime yl-hexamethylene diisocyanate (TMDI), norbornane diisocyanate (NBDI) , Methylene diphenyl diisocyanate (MDI), toluidine diisocyanate (TDI) and tetramethyl-xylylene diisocyanate (TMXDI) are preferably used. IPDI and HDI are very particularly preferred.

The conversion of these polyisocyanates containing uretdione groups to hardeners A) containing uretdione groups involves the reaction of the free NCO groups with hydroxyl-containing monomers or polymers, such as, for. B. polyesters, polythioethers, polyethers, polycaprolactams, polyepoxides, polyesteramides, polyurethanes or low molecular weight di-, tri- and / or tetraalcohols as chain extenders and optionally monoamines and / or monoalcohols as chain terminators and has already been described frequently (EP 669 353, EP 669 354 , DE 3030 572, EP 639 598 or EP 803 524). Preferred hardener A) containing uretdione groups have a free NCO content of less than 5% by weight and a uretdione group content of 6 to 18% by weight (calculated as C ₂ N ₂ O ₂ , molecular weight 84). Polyesters with an OH number of 30 to 150 mg KOH / g and an average molecular weight of 500 to 6000 g / mol as well as monomeric dialcohols, such as, for. B. ethylene glycol, propanediol (1,2) and - (1,3), 2,2-dimethylpropane (1,3), butanediol (1,4), hexanediol (1,6), 2-methylpentanediol -l, 5, 2,2,4- trimethylhexanediol- (l, 6), 2,4,4-trimethylhexanediol- (l, 6), heptanediol- (l, 7), dodecanediol- (1,12), octadec-9-en-l, 12-diol, thiodiglycol, octadecanediol- (l, 18), 2,4-dimethyl-2-propylheptanediol- (l, 3), diethylene glycol, Triethylene glycol, tetraethylene glycol, trans and cis 1,4-cyclo-hexanedimethanol, used.

In addition to the uretdione groups, the hardeners can also have isocyanurate, biuret, allophanate, urethane and / or urea structures.

As the hydroxyl group or imine group-containing polymers B), preference is given to using polyesters, polyethers, polyacrylates, polyurethanes, polyimidamines, polyethers and / or polycarbonates with an OH number of 20-500 (in mg KOH / gram) or a comparable amine content , Polyesters with an OH number of 30-150, an average molecular weight of 500-6000 g / mol are particularly preferred. Such binders have been described, for example, in EP 669 354 and EP 254 152. Mixtures of the abovementioned polymers can of course also be used.

The invention also relates to the use of at least one catalyst of the formula [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, A-koxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , below Formation of cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1 to 18 carbon atoms and each radical R ¹ - R ⁴ additionally also one or more alcohol, amino, ester, keto, Thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl , linear or branched, with 1 - 18 carbon atoms, which can additionally have one or more alcohol, amino, ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms , these catalysts m it is surrounded by an inert shell and can therefore be encapsulated, in polyurethane compositions, as well as the catalysts themselves.

The catalysts C) of the invention satisfy the formula [PR ¹ R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another are alkyl, aryl, aralkyl, heteroaryl, Alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of cycles, bicycles or tricyclics and the bridging atoms in addition to carbon can also be heteroatoms, with 1 to 18 carbon atoms and each radical R ¹ - R ^{4 can} additionally have one or more alcohol, amino, ester, keto, thio, urethane, urea, AHophanatgruppen, double bonds, triple bonds or halogen atoms, and R ⁵ either OH, F, or R ⁶ With R ^6, COO means synonymously with alkyl, aryl, aralkyl, heteroaryl, A-koxya-kyl residues, linear or branched, with 1-18 carbon atoms, which additionally contain one or more alcohol, amino, ester, May have keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, these catalysts being able to be surrounded by an inert shell and thus encapsulated.

Examples of such catalysts under C) are tetrabutylphosphonium acetate, tetrabutylphosphonium benzotriazolate, tetrabutylphosphonium hydroxide, ethyltriphenylphosphonium acetate, tetraphenylphosphonium phenolate, trihexyltetradecylphosphonium fluoronutanoate and tetrabecylphosphonium decanoate

Of course, mixtures of such catalysts can also be used. Teträbutylphosphonium hydroxide is particularly preferably used. They are present in an amount of 0.001-5% by weight, preferably 0.01-3% by weight, particularly preferably 0.5-1.5% by weight, based on components A) and B) the paint or Öebsto --- -saπ-mencement included. The catalysts can contain water of crystallization, which is not taken into account when calculating the amount of catalyst used, i. H. the amount of water is calculated. A variant according to the invention includes the polymeric attachment of such catalysts C) to the hardener A) or to the hydroxyl-containing polymers B). So z. B. free alcohol, thio or amino groups of the phosphonium salts with acid, isocyanate, or glycidyl groups of the hardener A) or hydroxyl-containing polymers B) are implemented in order to integrate the catalysts C) into the polymeric composite.

It should be noted in this connection that the activity of these catalysts in Presence of acids decreases significantly. The conventional reaction partners of the hardeners containing uretdione include hydroxyl-containing polyesters. Because of the way polyester is made, they sometimes carry acid groups to a small extent. In the presence of such polyesters bearing acid groups, it is advisable either to use the catalysts mentioned in excess, based on the acid groups, or to add reactive compounds which are able to scavenge acid groups. Both monofunctional and multifunctional compounds can be used for this.

Reactive acid-repellant compounds D) are generally known in paint chemistry. For example, epoxy compounds, carbodiiπ-ide, Hy <_- coxya-kylatr-ide or 2-oxazolines, but also inorganic salts such as hydroxides, hydrogen carbonates or carbonates react with acid groups at elevated temperatures. Possible z. B. triglyddyl ether isocyanurate (TGIC), EPIKOTE 828 (diglycidyl ether based on bisphenol A, Schell), versatic acid glycidyl ester, ethylhexylglycidyl ether, butylglycidyl ether, POLYPOX R 16 (pentaerythritol traglycidyl ether, UPox type V3), and with other EPYP type AGP epoxy groups VESTON EPX type AGEST and EPAP type AGEST (EPON AG) VEGON type EPYPOT AG with EPAP type AGEST as well as Polypox RX (EPPC AG) VESTON epoxy groups, as well as other Polypox RX (AG) epoxy groups AG), but also phenylenebisoxazoline, 2-methyl-2-oxazoline, 2-hydroxyethyl-2-oxazoline, 2-hydroxypropyl-2-oxazoline, 5-hydroxypentyl-2-oxazoHn, sodium carbonate and calcium carbonate. Mixtures of such substances are of course also possible. These reactive compounds can be used in proportions by weight of 0.1 to 10%, preferably 0.5 to 3%, based on the overall formulation.

Acids that are mentioned under E) are all substances, solid or liquid, organic or inorganic, monomeric or polymeric, which have the properties of a Brönstedt or a Lewis acid. Examples include: sulfuric acid, acetic acid, benzoic acid, malonic acid, terephthalic acid, but also copolyesters or copolyamides with an acid number of at least 20.

Suitable solvents under F) are all liquid substances that do not react with other ingredients, e.g. B. acetone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, methoxypropyl acetate and Dϊbasicester.

For the polymethane compositions, the additives G), such as leveling agents, e.g. B. PolysiUcone or acrylates, light stabilizers such. B. sterically hindered A ine, or other auxiliaries such as z. B. have been described in EP 669 353, are added in a total amount of 0.05 to 5 wt .-%. Fuels and pigments such as B. Titanium dioxide can be added in an amount of up to 50% by weight of the total?

Additional catalysts, as are already known in polyurethane chemistry, can optionally be included. These are mainly meta-inorganic catalysts, such as. B. dibutyltin dilaurate, or tertiary amines, such as. B. 1,4-diazabicylco [2,2,2-octane, in amounts of 0.001-1% by weight.

The homogenization of all components for the preparation of the polyurethane composition according to the invention can be carried out in suitable units, such as, for. B. heated stirred kettles, kneaders, or extruders, temperature limits of 120 to 130 ° C should not be exceeded. The homogeneous mixture of constituents can be either solid or liquid, depending on the starting substances or the use of solvents. The well-mixed mass is applied to the substrate by suitable application (e.g. rolling, spraying). In the case of solid formulations, the application of ready-to-spray powders to suitable substrates can be carried out by the known processes, such as, for. B. by electrostatic powder spraying, fluidized bed sintering, or electrostatic fluidized bed sintering. After the application, the coated workpieces are cured for 4 to 60 minutes at a temperature of 60 to 220 ° C, preferably 6 to 30 minutes at 80 to 160 ° C.

The subject matter of the invention is explained in more detail below with the aid of examples. Examples:

Mp: melting point; T _G : glass transition point;

General production of Polymeth-u compositions The comminuted starting materials - hardener and catalyst - are mixed intimately in a pan mill and then homogenized in the extruder up to a maximum of 130 ° C. After cooling, the extrudate is broken and ground with a pin mill to a grain size <100 μm.

Polyurethane - us unmeasurement A 95.25 parts of VESTAGON BF 1540 and 4.75 parts of TPAH were homogenized, broken and ground in an extruder at 120 ° C. as described.

Lacquer compositions (details in% by weight): Example 1 is based on the polyurethane composition A

* Comparative example not according to the invention

The polyurethane compositions were dissolved in the solvent at room temperature with stirring, then knife-coated onto steel sheet (Bonder 901) and, after briefly venting the solvent, cured in a forced-air oven at 150 ° C. for 30 minutes (Dry layer thickness 25 - 30 μm).

The MEK test (double strokes) reflects the solvent resistance (methyl ethyl ketone) of the coating, while the pendulum hardness provides information about the hardness of the coating. Both depend on the crosslinking of the coating. Obviously sufficient crosslinking has taken place in Example 1 according to the invention, but not in Comparative Example 1.

Claims

claims:

1. Highly reactive uretdione group-containing urethane groups - usa ---- compositions essentially containing A) at least one hardener containing uretdione, based on aromatic, aliphatic, (cyclo) ahatic or cyclophilic polyisocyanates and hydroxyl-containing compounds, with a free NCO content of less than 5% by weight .-% and a uretdione content of 1 - 18 wt .-%, B) optionally a hydroxyl-containing or amine-containing polymer with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least one catalyst of the formula [PR ^J R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or with other radicals R ^J - R ⁴ bridged, with the formation of cycles, bicycles or tricycles and the bridging atoms can be heteroatoms in addition to carbon, with 1-18 carbon atoms and each radical R ¹ - R ^{4 can} additionally have one or more alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ⁵ can either contain OH , F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, alkoxyalky radicals, linear or branched, with 1 - 18 carbon atoms, which additionally contain one or more alcohol, amino , Ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, so that the proportion of the catalyst under C) 0.001 - 5 wt .-% of the total amount of components A) and B).

2. Polyuretl - a - c-α] composition according to claim 1, characterized in that D) that at least one compound reactive towards acid groups with a The proportion by weight, based on the total formulation, of 0.1 to 10% by weight and / or E) that at least one acid in monomeric or polymeric form in a proportion by weight, based on the total formulation, of 0.1 to 10% is.

3. Polyurethane-ms-tn-menseteung according to claim 1 or 2, characterized in that solvent F) and / or hooves and additives are included

4. Polyurethane_-xιs compositions according to at least one of claims 1 to 3, characterized in that uretdione-containing hardener A) based on isophorone diisocyanate (DPDI), hexamethylene diisocyanate (HDI), 2-methylpentadnsocyanate (MPDI), 2,2,4-trimethyl hex-ιmethylenediisocyanana1 2,4,4-trimethyl-hexamethylene diisocyanate (TMDI), norbornane diisocyanate (NBDI), methylene diphenyl diisocyanate (MDI), toluidine diisocyanate (TDI) and tetramethyl-xylylene diisocyanate (TMXDI), also in or in mixtures

5. polyurethane-ιan - compositions according to claim 4, characterized in that uretdione-containing hardeners based on IPDI and / or HDI are included

6. Polyurethane u-compositions according to at least one of claims 1 to 5, characterized in that uretdione-containing hardener A) based on hydroxyl-containing polyesters, polythioethers, polyethers, polycaprolactams, polyepoxides, polyesteramides, polyurethanes, low molecular weight di-, tri- and / or Tetraalcohols, monoamines and / or monoalcohols, alone or in mixtures, are contained

7. Polyurethan_αιsa ---- mensungen according to claim 6, characterized in that polyester and / or monomeric dialcohols are included

8. Polyurethane compositions according to at least one of claims 1 to 7, characterized in that the hydroxyl-containing polymers B) are polyesters, polyethers, polyacrylates, polyurethanes and polycarbonates, all or in mixtures

9. polyurethane compositions according to claim 8, characterized in that polyesters with an OH number of 30 to 150 mg KOH / g and an average molecular weight of 500 to 6000 g mol are contained

10. Polyure1han - us-unmensungen according to at least one of claims 1 to 9, characterized in that catalysts C), selected from tetrabutylphosphonium acetate, tetrabutylphosphonium benzotriazolate, tetrabutylphosphonium hydroxide, are ethyltriphenylphosphonium acetate, tetraphenylphosphoniumphosphonium phosphonium phosphonium phosphonium phosphonium phosphonium fluoride, naphthenophosphonium phosphonium phosphonium fluoride

11. Polyurethane --- compositions according to at least one of claims 1 to 10, characterized in that the catalyst C) contains tributylphosphonium hydroxide.

12. Polyurethane --- Zusan_ιmenset - ungen according to at least one of claims 1 to 11, characterized in that epoxy compounds, carbodiimides, hydroxyalkylamides, basic salts and / or 2-oxazolines are included as component D)

13. Polyurethane --_ compositions according to claim 12, characterized in that triglycidyl ether isocyanurate, EPIKOTE ^® 828, versatic acid glycidyl ester, vestagon EP HA 320, phenylene bisoxazoline, 2-methyl-2-oxazoline, 2-hydroxyethyl-2-oxazoline, 2-hydroxypropyl-2-oxazoline and / or 5-hydroxypentyl-2-oxazoline, sodium carbonate or calcium carbonate, alone or in Mixtures are included

14. Polyurethane compositions according to at least one of claims 1 to 13, characterized in that the acid E) contains sulfuric acid, acetic acid, benzoic acid, malonic acid, terephthalic acid, but also copolyesters or copolyamides with an acid number of at least 20

15. A process for the preparation of highly reactive uretdione groups containing polyure1ha ---- πιsa ---- compositions, essentially containing A) at least one uretdione-containing hardener, based on aromatic, afiphatic, (cyclo) aphatic or cycloophatic polyisocyanates and compounds containing hydroxyl groups, with a free NCO content of less than 5% by weight and a uretdione content of 1 to 18% by weight, B) optionally a polymer containing hydroxyl groups and / or amine groups with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least one catalyst of the formula [PR ^J R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, each linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms k , with 1 - 18 carbon atoms and each radical R ¹ - R ⁴ additionally have one or more alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms can, and R ^{5 is} either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, A-koxyalkyl residues, linear or branched, with 1 - 18 carbon atoms, which additionally HCH one or more alcohol, aniino, ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, May have triple bonds or halogen atoms, so that the proportion of the catalyst under C) is 0.001-5% by weight of the total amount of components A) and B), by homogenization.

16. Use of at least one catalyst of the formula, [PR ¹ R ² R ³ R] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R * - R ⁴ , with the formation of cycles, bicycls or tricycles and the bridging atoms can also be heteroatoms in addition to carbon, with 1 - 18 carbon atoms and each radical R ¹ - R ⁴ additionally one or more alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ^{6 is} COO with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, A-koxyalkyl radicals, linear or branched, with 1 - 18 carbon atoms, which additionally contain one or more alcohol, amino, ester, keto, thio, acid -, urethane, urea, AHophanatgruppen, double bonds, three can have fencing bonds or halogen atoms, in polyurelha ---- αιsa nm settlements.

17. Use according to spoke 16, characterized in that compounds selected from tetrabutylphosphonium acetate, tetrabutylphosphonium benzotriacolate, tetrabutylphosphonium hydroxide, ethyltriphenylphosphonium acetate, tetraphenylphosphoniumphenolate, trihexyltetradecylphosphonium or tetronium phosphonium or tetronium decanoate are used.

18. Catalyst for accelerating the curing of polyurethane compositions, essentially containing a uretdione-containing hardener and a hydroxyl-containing polymer, of the formula [PR ^J R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^' , where R ¹ - R ⁴ simultaneously or independently of one another Alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, each linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of Cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1-18 carbon atoms and each radical R ¹ - R ⁴ additionally also one or more alcohol, amino, ester, keto, thio, urethane -, Urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, hnear or branched , with 1 - 18 carbon atoms, which can additionally have one or more alcohol, amino, ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms,

19. Catalyst according spoke 18, selected from tetrabutylphosphonium acetate, tetrabutylphosphonium benzotriacolate, tetrabutylphosphonium hydroxide, ethyltriphenylphosphonium acetate, tetraphenylphosphoniumphenolate, trihexyltetradecylphosphonium decanoate and / or tetrabutonium fluoride

20. A catalyst according to claim 19, consisting of tetiabutylphosphonium hydroxide

21. Use of polyurethane compositions essentially containing A) at least one uretdione-containing hardener, based on aromatic, aliphatic, (cyclo) ahphatic or cyclophosphate polyisocyanates and compounds containing hydroxyl groups, with a free NCO content of 5% by weight and a uretdione content of 1-18% by weight, B) optionally a polymer containing hydroxyl groups and / or amine groups with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least one catalyst of the formula | TR ¹ R ² R ³ RY [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1 to 18 carbon atoms and each radical R ¹ - R ⁴ additionally one or more Alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl -, Aryl, aralkyl, heteroaryl, A-koxyalkyl radicals, linear or branched, with 1-18 carbon atoms, which additionally contain one or more alcohol, amino, ester, keto, thio, acid, urethane -, Urea, allophanate groups, double bonds, triple bonds or halogen atoms, so that the proportion of the catalyst under C) is 0.001 - 5 wt .-% of the total amount of components A) and B) for the production of liquid and powdered lacquer and adhesive compositions.

22. Use according to claim 21, characterized in that starting compounds according to at least one of claims 2 to 14 are included

23. Use according to spoke 21 or 22 for the production of liquid and powdery lacquer and coating compositions for metal, plastic, wood, glass, leather or other heat-resistant substrates.

24. MetaHbeswichtungs - us-ιn-formulations, essentially containing a polyurethane-imung from A) at least one uretdione-containing hardener, based on aromatic, aliphatic, (cyclo) aphatic or cycloophatic - polyisocyanates and hydroxyl-containing compounds, with a free NCO Content of Meiner 5 wt .-% and a uretdione content of 1 - 18 wt .-%, B) optionally a hydroxyl-containing or amine-containing polymer with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least a catalyst of the formula [PR ^J R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, Alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R * - R ⁴ , with the formation of cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1-18 carbon atoms and each radical R ¹ - R ^{4 can} additionally have one or more alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ^{5 means} either OH, F or R ⁶ COO with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl residues, linear or branched, with 1 - 18 carbon atoms, which additionally contain one or more alcohol, amino, ester, keto, thio, May have acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, so that the proportion of the catalyst under C) is 0.001-5% by weight of the total amount of components A) and B).

25. Wood coating composition, essentially comprising a polyuret-a-dack composition from A) at least one uretdione-containing hardener, based on aromatic, aliphatic, (cyclo) aliphatic or cyclophthalic polyisocyanates and hydroxyl-containing compounds, with a free NCO content of mine 5% by weight and a uretdione content of 1 to 18% by weight, B) optionally a polymer containing hydroxyl groups or amine groups with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least one catalyst of the formula ppR ¹ R ² R ³ RY [R ⁵ ] ^' , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or with other radicals R ¹ - R ^{4 is} bridged, with the formation of cycles, bicycles or tricycles, and the bridging atoms can also be heteroatoms in addition to carbon, with 1 to 18 carbon atoms mean and each radical R ¹ - R ⁴ additionally also one or more alcohol, amino, ester, keto, thio, urethane, urea, AHophanat groups, May have double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO with R ^{6 is} synonymous with alkyl, aryl, aralkyl, heteroaryl, A-koxyalkyl radicals, linear or branched, with 1-18 Carbon atoms, which additionally have one or more alcohol, amino, ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, so that the proportion of the catalyst under C ) 0.001 - 5 wt .-% of the total amount of components A) and B).

26. l_ ^ derbescMch1ungs - compositions, essentially containing a polyurethane-ιmlack - usan - set from A) at least one uretdione-containing hardener, based on aromatic, aliphatic, (cyclo) aphatic or cycloophatic polyisocyanates and hydroxyl-containing compounds, with a free NCO content of mine 5% by weight and a uretdione content of 1 - 18% by weight, B) optionally a polymer containing hydroxyl groups or amine groups with an OH number between 20 and 500 mg KOH / gram or an equivalent A content, C) at least one catalyst of the formula [PR ¹ R ² R ³ R ⁴ ] ⁺ [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , with the formation of cycles, bicycles or tricycles and the bridging atoms can also be heteroatoms in addition to carbon, with 1-18 carbons mean atoms and each radical R ¹ - R ^{4 can} additionally have one or more alcohol, amino, ester, keto, thio, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms, and R ⁵ either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, linear or branched, with 1-18 carbon atoms, which additionally contain one or more alcohol, amino, Ester, keto, thio, acid, urethane, urea, AHophanatgruppen, double bonds, May have triple bonds or halogen atoms, so that the proportion of the catalyst under C) is 0.001-5% by weight of the total amount of components A) and B).

27. Plastic - coating ιsaπ - meιιse1 - quantities, essentially containing a polyurctl-an-_usa ---- composition from A) at least one uretdione-containing hardener, based on aromatic, aliphatic, (cyclo) aphatic or cycloophatic polyisocyanates and hydroxyl-containing compounds, with a free NCO content of mine 5% by weight and a uretdione content of 1 - 18% by weight, B) optionally a hydroxyl-containing or amine-containing polymer with an OH number between 20 and 500 mg KOH / gram or an equivalent amine content, C) at least one catalyst of the formula [R ⁵ ] ^" , where R ¹ - R ⁴ simultaneously or independently of one another alkyl, aryl, aralkyl, heteroaryl, alkoxyalkyl radicals, in each case linear or branched, unbridged or bridged with other radicals R ¹ - R ⁴ , under Formation of cycles, bicycles or tricycles and the bridging atoms in addition to carbon can also be heteroatoms, with 1 to 18 carbon atoms and each radical R ¹ - R ⁴ additionally also one or more alcohol, amino, ester, keto, thio , Urethane, urea, AHophanatgruppen, double bonds, triple bonds or halogen atoms, and R ^{5 is} either OH, F, or R ⁶ COO means with R ⁶ synonymous with alkyl, aryl, aralkyl, heteroaryl, A-koxyalkyl radicals , linear or branched, with 1-18 carbon atoms, which may additionally have one or more alcohol, amino, ester, keto, thio, acid, urethane, urea, allophanate groups, double bonds, triple bonds or halogen atoms so the share of the kata analyzer under C) 0.001 - 5 wt .-% of the total amount of components A) and B).

28. Metal coating according to spoke 24 for car bodies, motorbikes and bicycles, building parts and household appliances.

29. Coating compositions according to one of claims 24 to 28, characterized in that at least one of components D) to G) is contained.

30. Coating compositions according to one of claims 24 to 29, characterized in that they contain compounds according to at least one of claims 2 to 14.