DE19609617A1 - One- or two-component polyurethane coating materials - Google Patents

Abstract

One- or two-component polyurethane coating materials (PUCM), contg. at least one component which is reactive towards polyisocyanates, contain a cpd. (A) with a NCO gp., a urethane, thiourethane or urea gp. and two capped gps. which are reactive towards isocyanate. Also claimed are (i) addition prods. of 1 mole di-isocyanate and 1 mole of a dioxolane or dioxan cpd., and (ii) substrates coated with PUCM. Cpd. (A) is the addition prod. of 1 mole di-isocyanate and 1 mole of a cpd. of formula (I), in which R<1>, R<2> = H or 1-10C alkyl; X, Y = O, S or NR<6>; R<3> = 1-5C alkylene, and the heterocyclic ring may be substd. with other gps. R<4> and R<5>, where one of the gps. R<4>, R<5> or R<6> is or contains a NCO-reactive gp. such as OH, SH or prim. or sec. amino, and the others (if present) contain no NCO-reactive gps. Pref. (I) are dioxolanes of formula (II), dioxans of formula (III) or oxazolidine derivs. of formula (IV), in which R<8>, R<9>, R<10> = H or 1-10C alkyl; R<7> = 1-30C aliphatic or aromatic residue substd. with a NCO-reactive gp. such as OH, SH or prim. or sec. amino, and opt. contg. ether gps. in the aliphatic type. 1-100 wt% of the reactive component in the PUCM consists of cpds. (A).

Description

The invention relates to one-component and two-component poly urethane coating compositions containing at least one with poly Isocyanate reactive component, characterized records that the reactive component is a ver bond A) with an isocyanate group, a urethane, thiourethane or urea group and with two capped with isocyanate reak capable groups.

Polyurethane coating compositions generally contain a poly isocyanate and an isocyanate-reactive component, e.g. B. a polyol. To set the necessary processing viscos The coating compositions usually contain an organic solvent. However, the lowest possible is desired Solvent requirements. To achieve this, the Beschich already without solvent or with low solvents quantities, d. H. high solids content, the lowest possible Have viscosity. This effect can e.g. B. thereby achieved be that so-called reactive thinners are added, which the Reduce viscosity and then react in the system.

From EP-A-403 921 z. B. polyaspartic acid derivatives as Reactive thinner known. These compounds contain secondary ones Amino groups, which with the isocyanate groups of the polyisocyanates react to urea groups. A disadvantage of the previously known ten reactive diluents is in particular that the content of poly Isocyanate in the coating mass must be increased to the necessary complete turnover with the reactive diluents to reach. The cost of the coating mass depends significantly from the polyisocyanate as a component of value.

From GB 14 63 944 are addition products of oxazolidinderi vaten and diisocyanates known as such.

The object of the present inventions was therefore polyurethane coating compositions which have a high solids content have low viscosity. The object of the invention was also Reactive components or reactive thinners for two-component Polyurethane coatings.  

Accordingly, the polyurethane coating defined at the outset masses found. Suitable reactive components were also used or reactive thinner for one-component and two-component Polyurethane coating compositions found.

The further statements relate to preferred embodiments the invention.

Compound A) is preferably a lower one molecular compound with a molecular weight below 2000 g / mol, ins especially below 1000 g / mol and particularly preferably below 500 g / mol.

A preferred compound A) is the addition product of 1 mol Diisocyanate and 1 mole of a compound with the general Structural formula

wherein R¹ and R² independently represent an H atom or a C₁ to C₁₀ alkyl group, X and Y are independently are an oxygen atom, a sulfur atom or a group N-R⁶, R³ represents a C₁-C₅ alkylene group and with X, Y and R³ heterocyclic ring formed by further radicals, R⁴ and R⁵ sub can be substituted, whereby one of the radicals R⁴, R⁵ and R⁶ is a group reactive with isocyanate or one with iso cyanate reactive group, e.g. B. a mercapto group, a Hydroxyl group, contains a primary or secondary amino group and the other radicals R⁴, R⁵ and R⁶ none react with isocyanate capable group included.

R¹ and R² are preferably an H atom or a C₁-C₄ alkyl group.

R⁴, R⁵ and R⁶, insofar as they do not contain an isocyanate-reactive group hold, are preferably an aromatic, especially ali phatic group with up to 20 carbon atoms; particularly preferred they represent a C₁-C₈ alkyl group.  

In the group R⁴, R⁵, R⁶, which is reactive with isocyanate Group, e.g. B. a hydroxyl group, a mercapto group, a contains primary or secondary amino group preferably an aromatic group with 5 to 10 carbon atoms or an alipha, optionally interrupted by ether groups table group with 1 to 20 carbon atoms, which is characterized by a hydroxyl group, mercapto group or a primary amino group, substi tuiert, or contains a secondary amino group. Suitable are compounds I which, apart from the rest with the group reactive towards isocyanate, no further Contain radicals R⁴, R⁵ or R⁶. It is essential that the connection of formula I only one free, d. H. not blocked and therefore contains isocyanate reactive group.

The compound A) as an addition product of a diisocyanate with the Compound I then contains exactly one urethane group (implementation a hydroxyl group with isocyanate), a thiourethane group (Reaction of a mercapto group with an isocyanate) or a Urea group (implementation of a primary or secondary amino group with isocyanate), exactly one isocyanate group and exactly two blocked groups reactive with isocyanate.

Apart from the isocyanate groups, the diisocyanates exist preferably exclusively from carbon and hydrogen.

Straight-chain or branched C₄-C₁₄ alkylenediiso may be mentioned cyanates, e.g. B. tetramethylene diisocyanate, hexamethylene diisocyanate (1,6-diisocyanatohexane), octamethylene diisocyanate, Decamethylene diisocyanate, dodecamethylene diisocyanate, tetra decamethylene diisocyanate, trimethylhexane diisocyanate or tetra methylhexane diisocyanate, cycloaliphatic diisocyanates such as 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4'-di (isocyanatocyclohe xyl) methane, 1-isocyanato-3,3,5-trimethyl-5- (isocyanato methyl) cyclohexane (isophorone diisocyanate) or 2,4- or 2,6-diisocyanato-1-methylcyclohexane, aromatic diisocyanates such as 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 1,4-diisocyanato benzene, 4,4, - and 2,4'-diisocyanatodiphenylmethane, p-xylylene diisocyanate, and 1,5-naphthylene diisocyanate or the aromatic substituted isocyanates such as tetramethylxylylene diisocyanate and Isopropenyldimethyltoluenediisocyanate.

Preferred compounds A) are e.g. B. the addition products of the above diisocyanates, especially hexamethylene diisocyanate, isophorone diisocyanate, 4,4, -di (isocyanatocyclohexyl) methane, tetra methylxylylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate or mixtures of these Isocyanates
Dioxolanes of the formula

Dioxanes of the formula

or
Oxazolidine derivatives of the formula

in which
R⁸, R⁹ and R¹⁰ independently of one another represent an H atom or a C₁-C₁₀ alkyl group, preferably a C₁-C₄ alkyl group, R⁸ and R⁹ particularly preferably represent an H atom or a methyl group and R¹⁰ particularly preferably an ethyl group and R⁷ the meaning of an aliphatic or aromatic radical having 1 to 30 carbon atoms, preferably an aromatic group having 5 to 10 carbon atoms and an aliphatic group having 1 to 20 carbon atoms, which may be interrupted by ether groups, which is imperative by a hydroxyl group, mercapto group or a primary amino group is substituted or necessarily contains a secondary amino group.

R⁷ particularly preferably represents a C₁-C₈ branched or linear hydrocarbon chain through a hydroxyl group or a primary amino group is substituted.  

The two-component polyurethane coating according to the invention Compound A) can be the only compound to react with isocyanate reactive component because the compound A) in addition to one isocyanate group, two blocked with isocyanate reak tive groups (groups X and Y in formula I) contains.

The blocking agents are removed from compound A) in the later use free by exposure to air humidity set so that the previously blocked groups are then in their reactive form, as hydroxyl, mercapto or primary or secondary amino group are present.

The polyurethane coating composition of the invention can in addition Compounds A) further reactive with isocyanate components (hereinafter referred to as reactive components) contain.

The proportion of the compounds A) is preferably 1 to 100% by weight, based on the reactive components.

The one that can be achieved by connections A) is particularly high Lowering the viscosity of the coating composition at a content from 5 to 100, particularly preferably 20 to 100 wt .-% and whole particularly preferably 50 to 100% by weight of the compounds A), based on the total amount of reactive components.

As further reactive components such. B. hydroxy functional Polymers (radical polymerized), polycondensates or poly called adducts.

The hydroxy-functional polymers are e.g. B. to polymers with a hydroxyl group content of 0.1 to 20, preferably 0.5 to 10 wt .-%. The number average molecular weight M _{n of} the polymers is preferably 1000 to 100,000, particularly preferably 2000 to 10,000. The polymers are preferably those which are more than 50% by weight of C₁-C₂₀-alkyl (meth) acrylate , Vinyl aromatics with up to 20 carbon atoms, vinyl esters of up to 20 carbon atoms containing carboxylic acids, vinyl halides, non-aromatic hydrocarbons with 4 to 8 carbon atoms and 1 or 2 double bonds, unsaturated nitriles and mixtures thereof. The polymers are particularly preferably made up of more than 60% by weight of C₁-C₁ Alkyl alkyl (meth) acrylates, styrene or mixtures thereof.

In addition, the polymers contain hydroxy functional Monomers corresponding to the above hydroxyl group content and optionally further monomers, e.g. B. ethylenically unsaturated  Acids, especially carboxylic acids, acid anhydrides or acid amide.

Other reactive components are e.g. B. polyesterols, as by Condensation of polycarboxylic acids, especially dicarboxylic acids with polyols, especially diols are available.

Polyetherols are also suitable as reactive components, by adding ethylene oxide, propylene oxide or butylene oxide be made from H-active components. Likewise, poly condensates from butanediol suitable.

The reactive components can of course also be Act compounds with primary or secondary amino groups.

May be mentioned for. B. so-called Jeffamine, d. H. with amino groups terminated polyetherols, or oxazolidines.

In the case of one-component polyurethane coating compositions, one of them Reaction partners (isocyanate or Ver bond) completely in blocked, d. H. non-reactive form, in front.

The one-component polyurethane coating according to the invention therefore contain only reactive components with blocking ten isocyanate-reactive groups. In addition to the ver bindings A can also block other reactive components ten isocyanate-reactive groups are used, e.g. B. Aldimine, Ketimine, Oxazolidine.

In general, contain the one-component according to the invention Polyurethane coating compositions 50 to 100 wt .-%, preferably 70 up to 100% by weight and particularly preferably exclusively Ver bonds A) as a reactive component with blocked, opposite Isocyanate reactive groups.

Mixing the polyisocyanates with the reactive components briefly before processing, not applicable.

The one-component polyurethane coating compositions contain poly isocyanates and the reactive component with blocked, opposite Isocyanate reactive groups and are stable on storage.

Two-component polyurethane coating compositions included at least one of the above reactive components free isocyanate-reactive groups. This reactive component is generally processed shortly before processing  other polyisocyanates and compounds A) mixed (therefore 2 components).

The polyurethane coating compositions according to the invention contain in addition to the reactive components, as already mentioned above remove at least one reactive with these reactive components Compatible component, especially polyisocyanates.

As polyisocyanate z. B. conventional diisocyanates and / or usual higher functional polyisocyanates with an average ler NCO functionality from 2.0 to 4.5. These components can be present alone or in a mixture.

Examples of common diisocyanates are aliphatic diisocyanates such as tetramethylene diisocyanate, hexamethylene diisocyanate (1,6-diiso cyanatohexane), octamethylene diisocyanate, decamethylene diisocyanate, Dodecamethylene diisocyanate, tetradecamethylene diisocyanate, Tetramethylxylylene diisocyanate, trimethylhexane diisocyanate or Tetramethylhexane diisocyanate, cycloaliphatic diisocyanates such as 1,4-, 1,3- or 1,2-diisocyanatocyclohexane, 4,4'-di (isocyanato cyclohexyl) methane, 1-isocyanato-3,3,5-trimethyl-5- (isocyanato methyl) cyclohexane (isophorone diisocyanate) or 2,4-, or 2,6-diisocyanato-1-methylcyclohexane and aromatic diiso cyanates such as 2,4- or 2,6-tolylene diisocyanate, p-xylylene diiso cyanate, 2,4'- or 4,4'-diisocyanatodiphenylmethane, 1,3- or 1,4-phenylene diisocyanate, 1-chloro-2,4-phenylene diisocyanate, 1,5-naphthylene diisocyanate, tetramethylxylylene diisocyanate, Diphenylene-4,4'-diisocyanate, 4,4'-diisocyanato-3,3'-dimethyldi phenyl, 3-methyldiphenylmethane-4,4'-diisocyanate or diphenyl ether 4,4'-diisocyanate. Mixtures of the above can also be used Diisocyanates are present. Hexamethylene diisocyanate is preferred and isophorone diisocyanate, and 2,4- and 2,6-tolylene diisocyanate and 2,4'- and 4,4'-diphenylmethane diisocyanate.

The usual higher functional polyisocyanates are suitable for for example triisocyanates such as 2,4,6-triisocyanatotoluene or 2,4,4'-triisocyanatodiphenyl ether or the mixtures of di-, tri- and higher polyisocyanates by phosgenation of ent speaking aniline / formaldehyde condensates are obtained and Represent polyphenyl polyisocyanates having methylene bridges.

Common aliphatic higher functions are of particular interest nelle polyisocyanates of the following groups:

• (a) Isocyanurate group-containing polyisocyanates from alipha tables and / or cycloaliphatic diisocyanates. Especially the corresponding isocyanato iso are preferred  cyanurate based on hexamethylene diisocyanate and iso phorone diisocyanate. The present isocyanurates are concerned it is in particular simple tris-isocyanatoalkyl or Tris-isocyanatocycloalkyl-isocyanurates, which are cyclic Represent trimers of diisocyanates, or mixtures with their higher, more than one isocyanurate ring Homologues. The isocyanato isocyanurates generally have an NCO content of 10 to 30 wt .-%, in particular 15 to 25 wt .-%, and an average NCO functionality of 2.6 to 4.5.
• (b) Diisocyanates containing uretdione groups with aromatic, ali phatic and / or cycloaliphatic isocyanate groups, preferably of hexamethylene diisocyanate or iso derived from phorone diisocyanate. With uretdione diisocyanates han cyclic dimerization products from Diiso cyanates.
• (c) Biuret group-containing polyisocyanates with aliphatic bound isocyanate groups, especially tris (6-isocyanato hexyl) biuret or its mixtures with its higher homo lied. These biuret groups have polyisocyanates generally an NCO content of 10 to 30 wt .-%, ins particular from 18 to 25% by weight and an average NCO Functionality from 3 to 4.5.
• (d) Polyiso containing urethane and / or allophanate groups cyanates with aliphatic or cycloaliphatic bound Isocyanate groups, as for example by reacting excess amounts of hexamethylene diisocyanate or iso phorone diisocyanate with polyhydric alcohols such as trimethylol propane, glycerin, 1,2-dihydroxypropane or mixtures thereof can be obtained. This urethane and / or allophanate have in general polyisocyanates an NCO content of 12 to 20% by weight and an average NCO Functionality from 2.5 to 3.
• (e) Polyisocyanates containing oxadiazinetrione groups, preferably example of hexamethylene diisocyanate or isophorone diisocyanate derived. Such poly containing oxadiazinetrione groups Isocyanates can be produced from diisocyanate and carbon dioxide.
• (f) Carbodiimide or uretonimine modified polyisocyanates.

The isocyanate groups of the above polyisocyanates a) -f) can also be partially implemented with monoalcohols.  

Aliphatic and cycloaliphatic polyisocyanates are special prefers. Hexamethylene diisocyanate is very particularly preferred and isophorone diisocyanate and in particular their isocyanurates and Biurete.

The coating compositions of the invention contain the polyiso cyanate and the reactive component (i.e. compound A and given if necessary, further compounds reactive with isocyanate) in general mean in such quantities that, based on 1 mole, total handener isocyanate groups, 0.8 to 1.2 moles with isocyanate reak groups, both free and blocked groups are available. The molar ratio is particularly preferably approximately 1: 1.

The polyisocyanates in both the one-component and two component systems can, however, completely or partially others reactive with the reactive component or components Connections to be replaced. Consider z. B. polyepoxides, Compounds with acid anhydride groups or N-methylol groups or compounds containing etherified N-methylol groups, e.g. B. Urea or melamine resins, which with the groups X and Y of Compound A) can react.

The coating compositions of the invention can still organic solvents, e.g. B. xylene, butyl acetate, methyl isobutyl contain ketone, methoxypropyl acetate, N-methylpyrrolidone. With Solvent is used for processing, i.e. H. for application on sub strate desired low viscosity of the coating composition posed. Connection A) makes this much less Solvent needed, d. H. the desired lower viscosity is achieved with higher detentions.

The coating compositions can of course, further, in the Coating technology common additives, e.g. B. pigments, Contain fillers, leveling agents, etc.

You can also use catalysts for urethane formation, e.g. B. Dibutyltin dilaurate.

To produce the coating compositions of the invention the individual components ver together in a known manner to be mixed. The compounds A) and optionally further Reactive components with blocked isocyanate-reactive Groups can work with the polyisocyanates long before processing can be mixed (1-component system). Reactive components with free, with Isocyanate-reactive groups become the isocyanate in general added shortly before processing (2-component systems). With ransom  The desired viscosity can be set using the medium. The Be Layering compound can be sprayed, poured, Rolls, brushes, etc., are applied to substrates. The coating composition is particularly suitable for substrates such as metallic substrates, wood or wood-based materials, plastics Etc.

Under the influence of humidity, the blocked with Isocyanate-reactive groups of compound A) are released. After that the reaction of the compounds A) takes place with the polyisocyanates at room temperature in a known manner.

The coatings obtained have very good mechanical properties high hardness, flexibility and Chemical resistance.

Examples

The hydroxy-functional starting compounds (structure formulas (1) to (5) for the compounds A) are in Table 1 listed and are in accordance with the specified work regulations (AV) manufactured or purchased from the specified company.

Acetone-capped glycerin

masked trimethylol propane

ethoxylated with 3 moles of ethylene oxide masked glycerin

propoxylated with 2 moles of propylene oxide masked glycerin

Oxazolidines

Table 1

Hydroxy-functional starting compounds

AV 1 Preparation of the masked trimethylolpropane derivatives

250 g of trimethylolpropane are mixed with 750 ml of petroleum ether (Boiling range 30-75 ° C), 750 ml of the corresponding ketone and 0.15 g of p-toluenesulfonic acid monohydrate heated under reflux for 24 h. The resulting product is then removed using a water separator Water of reaction circled. The solution is cooled, 0.5 g Sodium methoxide added and stirred for 1 h at room temperature. The solution is filtered, the solvent on a rotary ver steamer removed and the residue distilled in vacuo.

2b: educ. 78% of theory Theor., Siedep. 71-72 ° C (0.5 mbar)
2c: educ. 84% of theory Theor., Siedep. 89 ° C (0.3 mbar)
2d: training 83% of theory Theor., Siedep. 96 ° C (0.3 mbar)

AV 2 Preparation of the alkoxylated isopropylidene glycerol derivatives

In a 5 l reactor, suitable for the production of polyetherols, 1060 g (8 mol) of isopropylidene glycerol (1) are introduced, 4 g Potassium tert-butoxide added and heated to 110 ° C. At this Temperature becomes 24 mol ethylene oxide or 16 mol propylene oxide admitted. The reaction is continued until the pressure is constant. A vacuum is then applied for 30 min. After Entmono merization is aerated with nitrogen, cooled to 50 ° C and drained the product. Refurbishment to remove the Alkali is made by adding 3% by weight of a Mg silicate (Ambusol, cation exchanger) and heat to 100 ° C for 2 h. The  Silicate is filtered off and the end product with 0.15% by weight. 2,6-di-tert-butyl-p-cresol (Kerobit TBK) stabilized.

3: OH number = 216 mg KOH / g.
4: OH number = 219 mg KOH / g.

Preparation of the compounds A)

Compounds A were obtained by reacting the above Hydroxy-functional starting compounds with diisocyanates according to the working instructions AV 3, AV 4 and AV 5. The Compounds obtained are according to the starting components named, e.g. B. IPDI-1 for connection A) from IPDI and 1 and are in Table 2 listed.  

Table 2

Compounds A (Monourethane)

AV 3 Monourethane from IPDI, IPCI or BEPDI

The aliphatic diisocyanate and 200 ppm dibutyltin dilaurate who the submitted under nitrogen blanket, to 80 ° C, at IPCI 50 ° C, heated and the OH component at this temperature within Added dropwise for 30 min. Then allowed to 60 min at 80 ° C (IPCI 50 ° C) after-react. The molar ratio between isocyanate and OH component is 1: 1, as a by-product occurs next to the monomeric isocyanate (3-6%) the diurethane. The yields Monourethane are naturally lower due to the 1: 1 driving style than that of HDI products.

AV 4 Monourethane from HDI

1680 g HDI (10 mol) and 0.84 g dibutyltin dilaurate (500 ppm rel. HDI) are placed under a nitrogen blanket and at 50 ° C warms. At this temperature, 2 mol of the are within 30 min OH component added dropwise. The mixture is left to react at 50 ° C. for 30 minutes. The product is then distilled on a thin layer evaporator at 165 ° C (oil temperature) and 2.5 mbar of monomeric HDI exempted. The residual monomer content of the end product is below 0.2%. Characteristic of this "under-shot driving style" is the high yield of monourethane (<85%).

AV 5 Monourethanes from the aromatic diisocyanates TDI and MDI

The aromatic diisocyanate is pre-blanketed with nitrogen sets, heated to 80 ° C and the OH component at this Temperature added dropwise within 30 min. Then you leave React for 60 min at 80 ° C. The molar ratio between Iso cyanate and OH component is 1: 1, occurs as a by-product in addition to the monomeric isocyanate (TDI 4%, because it is more selective due to un different reactive NCO groups, MDI 13%) on the diurethane.

Production and testing of clearcoats with compounds A 2-component system

The compounds A) were with the hydroxifunctional vinyl polymer Lumitol® H 136, BASF and the polyisocyanate Basonat® HI 100, BASF in equimolar amounts of the isocyanate groups to isocyanate reactive (blocked and unblocked)  Groups mixed according to Table 3 and to accelerate the Cured with dibutyltin dilaurate (DBTL, Merck) catalyzed.

For comparison, no compound A) was used in clear coat 1 and in clear coat 2 a bisoxazolidine as commercially available Reactive thinner used. Attitude to an appli cation viscosity of 20 s (DIN 53 211 cup 4 mm outlet nozzle) was done with butyl acetate. The fixed salaries were after DIN V 53 216 1st part determined.

Coatings were made on glass plates with a film drawing frame applied with a wet film thickness of 200 microns. The so obtained Clear varnishes were cured for 7 days in a standard atmosphere. The resulting hardness of the paints was measured by means of pendulum damping measurement according to König (DIN 53 157).

The coating properties obtained are summarized in Table 3 composed.

The clearcoats of the invention have a viscosity of 20 s very high fixed contents. For an equimolar turnover with Polyisocyanate are comparatively small amounts of polyiso cyanate necessary. The coatings obtained have good mecha African properties, e.g. B. high hardness.

1-component system

Compounds A) from Table 2 were according to the stoichio mixed with Basonat® HI 100 or Basonat®P LR 8901 and to accelerate curing before application with 0.1% (f.a.f) Dibutyltin dilaurate (DBTL, Merck) catalyzed. The Mixtures did not contain any compounds or polymers free isocyanate-reactive groups. The reaction of the Isocyanate groups later occur exclusively with the masked, groups reactive toward isocyanate. The setting on an application viscosity of 20 s (DIN 53 211 cup 4 mm Outlet nozzle) was carried out with butyl acetate. The paint solids were determined according to DIN V 53 216 1st part, the VOC values from mass / Volume ratios calculated.

The paint solids are summarized in Table 4.

Table 4

1-component clear coats

From the compounds A can be selected by a suitable choice System partners produce one-component paints that cover the entire Property range (from tough elastic - paint no. 31 - up to brittle / hard coatings - paint no. 33 -) cover. The income  Component paints are stable for months and stand out moreover due to very high paint solids or very low Solvent content (VOC = volatile organic compounds).

Claims (9)

1. One-component or two-component polyurethane coating compositions comprising at least one reactive component reactive with polyisocyanates, characterized in that the reactive component is a compound A) having an isocyanate group, a urethane, thiourethane or urea group and two capped, capable of reacting with isocyanate Groups. 2. One-component or two-component polyurethane coating compositions according to claim 1, characterized in that compound A) is the addition product of 1 mol of a compound having the general structural formula and one mole of diisocyanate, where R¹ and R² independently represent an H atom or a C₁-C₁₀ alkyl group, X and Y independently represent an oxygen atom, a sulfur atom or a group N-R⁶, R³ represents a C₁ -C₅-alkylene group and the heterocyclic ring can be substituted by further radicals R⁴ and R⁵, where a radical R⁴, R⁵ or R⁶ is an isocyanate-reactive group, for. B. carries a hydroxyl group, mercapto group, primary or secondary amino group or is such a group and the other radicals R⁴, R⁵ or R⁶, if present at all, contain no isocyanate-reactive group. 3. One-component or two-component polyurethane coating compositions according to claim 1 or 2, characterized in that it is in the connection of structural formula I.
Dioxolanes of the formula Dioxanes of the formula or
Oxazolidine derivatives of the formula where R⁸, R⁹ and R¹⁰ independently represent an H atom or a C₁-C₁₀ alkyl group and R⁷ represents an aliphatic or aromatic radical of 1 to 30 carbon atoms which may contain ether groups in the case of the aliphatic radical, and mandatory through a group reactive with isocyanate, e.g. B. a hydroxyl, mercapto or primary or secondary amino group is substituted. 4. addition product of one mole of diisocyanate and one mole of Dioxolans of structural formula II. 5. addition product of one mole of diisocyanate and one mole of Dioxane of the formula III. 6. One-component or two-component polyurethane coating tion masses, according to one of claims 1 to 3, characterized ge indicates that it is 1 to 100 wt .-% of the reactive component is compounds A). 7. Use of the compound A) according to one of claims 1 to 3 as a reactive thinner for two-component polyurethane layering compounds.   8. Use of the compound A) according to any one of claims 1 to 3 in one-component polyurethane coating materials as a reak active component for polyisocyanates. 9. With one-component or two-component polyurethane coating Coating compositions coated according to one of claims 1 to 3 Substrates.