Use of certain catalysts for the preparation of polyurethane coatings

Abstract

The present invention relates to compounds for use as catalysts in the preparation of polyisocyanate polyaddition products, their preparation and their use as catalysts, preferably as thermally latent catalysts, for the preparation of polyisocyanate polyaddition products.The present invention also relates to formulations and methods for the preparation of polyisocyanate polyaddition products, using the compounds claimed respectively, as well as to the polyisocyanate polyaddition products obtained or obtainable by said methods.Finally, the present invention relates to coating agents for coating substrates, comprising or consisting of the claimed polyisocyanate polyaddition products.

Description

[Technical field]

[0001] The present invention relates to compounds for use as catalysts in the preparation of polyisocyanate polyaddition products, their preparation and their use as catalysts, preferably as thermally latent catalysts, for the preparation of polyisocyanate polyaddition products.The present invention further relates to formulations and methods for the preparation of polyisocyanate polyaddition products, respectively, using the compounds of the present invention, as well as polyisocyanate polyaddition products obtained or obtainable by said methods.Finally, the present invention relates to coating compositions for coating substrates, comprising or consisting of the polyisocyanate polyaddition products of the present invention. [Background technology]

[0002] prior art Polyurethane coatings have been known for a long time and are used in many fields. They are generally produced from a polyisocyanate component and a hydroxyl component by mixing immediately before application (two-component (2K) technology). Lightfast coatings generally use a polyisocyanate component based on aliphatic polyisocyanates, which react rather slowly with the hydroxyl component compared to products with aromatically bound isocyanate groups. The reaction must therefore be catalyzed in most cases. Furthermore, if possible, the mixture is heated to further accelerate the reaction. Organotin compounds, in particular dibutyltin dilaurate (DBTL), have been found useful here as catalysts. These have the general disadvantage of an unfavourable ecological profile and, among other things, the substance class of organotin compounds has already been completely banned from marine paints, where they were added as biocides.

[0003] A general disadvantage of 2K technology is that the reaction between NCO and OH groups proceeds slowly already at room temperature, which means that there is only a narrow time window available for processing the formulated mixture of such a 2K system, called the pot life, which is further shortened by the presence of catalysts.

[0004] Therefore, there have been many attempts to develop catalysts, known as latent catalysts, which do not significantly promote the crosslinking reaction during preparation of the 2K mixture, but significantly promote it after application.

[0005] A particularly promising technology is thermally latent catalysis using inorganic tin compounds, as described, for example, in WO2011 / 051247A1. One drawback of thermally latent catalyst systems identified in the prior art is that the catalyst requirements are very high and the stability of the polyisocyanate curing agent may be insufficient, for example, in terms of yellowing and / or viscosity increase, which is usually accompanied by a reduction in the isocyanate content (NCO reduction).

[0006] This effect occurs in particular in the case of polyisocyanates containing iminooxadiazinedione groups, which can be obtained, for example, according to the teachings of EP 798299 B1, EP 3337836 A1 or EP 3107948 A1, so that it has hitherto been practically impossible to modify this substance class with thermally latent catalysts. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2011 / 051247 [Patent Document 2] European Patent Publication No. 798299 [Patent Document 3] European Patent Application Publication No. 3337836 [Patent Document 4] European Patent Application Publication No. 3107948 Summary of the Invention [Problem to be solved by the invention]

[0008] Object of the invention The object of the present invention was therefore to provide compounds for use as catalysts in the production of polyisocyanate polyaddition products. In particular, the compounds had a long pot life and sufficient hardness of the products produced, had a relatively low catalyst loading or allowed a higher reactivity at the same catalyst loading, even though the other property profiles remained unchanged or were even improved. Furthermore, the compounds allowed a reduction in the yellowing tendency and / or viscosity increase / NCO of the products at least to the same extent as existing prior art systems. The pot life is the time at which the viscosity of the formulated paint formulation increases to an unacceptable extent. It is indirectly determined, for example, by doubling the flow time of the formulated paint formulation in a DIN4 cup. These improved catalyst systems were likewise very substantially free of toxic components, such as cadmium, mercury, lead and / or organotin compounds, and could be produced from cheap and industrially readily available reactants. Organotin compounds are by definition understood to mean species having at least one Sn-C bond in the molecule. [Means for solving the problem]

[0009] Achieving purpose These objects have surprisingly been achieved by compounds having the general formula (I) or (II) for use as catalysts in the preparation of polyisocyanate polyaddition products: [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; In formula (I), at least one of the R1, R2, R3 or R4 groups is hydrogen and at least one of these groups is not hydrogen, where the carbon atoms C' and C'' do not have the same group, and in formula (II), R1, R2, R3, R4, R8, R9, R 10 or R 11 At least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not have the same groups.

[0010] Furthermore, the present invention provides a method for producing a Tin-containing compounds of the R6R7SnZ2 type Compounds of general formula (III): [ka] or Tin-containing compounds of the SnZ4 type, a compound of general formula (III); [ka] React one of the following: Then, compounds of general formula (IV) and (V): [ka] [During the ceremony, R1, R2, R3, R4 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V and W are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 is oxygen, sulfur or nitrogen; A is a leaving group, preferably -OH, -SH, N(R 22 ) H- or halogen, where R22 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; Z is a halogen, an alkoxide or a mixture thereof; At least one of the R1, R2, R3 or R4 groups is hydrogen, and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' do not carry the same group. The present invention relates to a process for the preparation of the compounds of the present invention having general formula (I) by reacting

[0011] The present invention also relates to a method for producing a tin-containing tin alloy comprising the steps of: a compound having the general formula (III); [ka] and, a compound having the general formula (IV); [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; R1, R2, R3, R4, R8, R9, R10 or R 11 at least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not bear the same groups. The present invention relates to a process for preparing the compounds of the present invention having the general formula (II) by the reaction of:

[0012] The present invention further relates to the use of the compounds of the invention as catalysts, preferably as thermally latent catalysts, for the production of polyisocyanate polyaddition products, in particular polyurethanes, preferably polyurethane foams, polyurethane coatings, polyurethane paints or polyurethane adhesives.

[0013] Further, the present invention relates to a composition comprising the following components: a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; b) at least one compound of the invention as a catalyst; c) optionally a further catalyst other than b); d) Optionally, auxiliaries and / or additives The present invention relates to a formulation for the preparation of polyisocyanate polyaddition products, comprising or consisting of: Here, the ratio of the weight of tin from component b) to the weight of component a) is preferably not more than 1000 ppm when component a) is an aliphatic and / or (cyclo)aliphatic polyisocyanate and not more than 50 ppm when component a) is an aromatic polyisocyanate.

[0014] The present invention also provides: A composition comprising or consisting of at least one formulation according to claim 16 and at least one NCO-reactive compound, wherein the reaction is preferably carried out at an isocyanate index of 80 to 150; or A composition comprising or consisting of the following components: A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; B) at least one NCO-reactive compound; C) at least one compound of the invention as a catalyst; D) optionally, a further catalyst other than C); E) Optionally, auxiliaries and / or additives wherein the ratio of the weight of tin from component C) to the weight of component A) is preferably not more than 1000 ppm when component A) is an aliphatic and / or (cyclo)aliphatic polyisocyanate and not more than 50 ppm when component A) is an aromatic polyisocyanate; The present invention relates to a method for producing a polyisocyanate polyaddition product by the reaction of

[0015] The present invention further relates to polyisocyanate polyaddition products obtained or obtainable by the aforementioned process of the invention.

[0016] The present invention finally relates to a coating composition for coating a substrate, comprising or consisting of at least one polyisocyanate polyaddition product according to the invention, where the substrate is preferably a plastic part, a metal part or a wooden molding. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] Compounds of the Invention The present invention provides a compound of general formula (I) or (II) for use as a catalyst in the preparation of polyisocyanate polyaddition products: [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; In formula (I), at least one of the R1, R2, R3 or R4 groups is hydrogen and at least one of these groups is not hydrogen, where the carbon atoms C' and C'' do not have the same group, and in formula (II), R1, R2, R3, R4, R8, R9, R 10 or R 11 At least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not have the same groups.

[0018] Preferably, at least one R1, R2, R3 or R4 group in formula (I) is not hydrogen, and at least one R1, R2, R3, R4, R8, R9, R 10 or R 11 The group is aliphatic and is preferably a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group.

[0019] R5 and / or R 12 It is also preferred that is a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl group, more preferably a methyl, butyl or ethyl group.

[0020] V, W, X and Y are preferably oxygen and / or D1 and D2 are nitrogen.

[0021] Furthermore, it is preferred that R6 and R7 are the same.

[0022] In a preferred embodiment, the compound of formula (II) is a compound having at least one of R, R, R, R, R, R, R, R in formula (II) which is not hydrogen. 10 or R 11 R5 and R6 are each a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, preferably a methyl group; 12 are independently optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic groups, preferably the same groups and being methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl groups, more preferably the same groups and being methyl, butyl or ethyl groups; V, W, X and Y are oxygen; and D1 and D2 are nitrogen.

[0023] In a preferred embodiment, the compound of formula (II) is R1 is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, preferably a methyl group; R2, R3, R4, R8, R9, R 10 and R 11 The group is hydrogen; or R1 and R2 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably a methyl group; R3, R4, R8, R9, R 10 and R 11 The group is hydrogen; or R1 and R 10 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are a methyl group; R, R, R, R, R and R 11 The group is hydrogen; or R1, R2 and R 10 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are a methyl group; R, R, R, R and R 11 The group is hydrogen; or R1, R2, R 10 and R 11are the same or different radicals and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same radicals and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are methyl groups, and the R3, R4, R8 and R9 radicals are hydrogen, and R5 and R 12 are independently optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic groups, preferably the same groups and are methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl groups, more preferably the same groups and are methyl, butyl or ethyl groups, and V, W, X and Y are oxygen, and D1 and D2 are nitrogen.

[0024] In a preferred embodiment, the compound of the invention is 2,2-dichloro-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dibromo-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dimethoxy-4,6-dimethyl-1,3,6,2-dioxazastannocane, 4,6-dimethyl-1,3,6,2-dioxazastannocane-2,2-diyl dibenzoate, 6-ethyl-4-methyl-1,3,6,2-dioxazastannocane-2,2-diyl dibenzoate, 6-butyl-4-methyl-1,3,6,2-dioxazastannocane-2,2- Diyl dibenzoate, 2,4,12-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,4,10,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,10,12-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane stannaspiro[7.7]pentadecane, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,10,10,12-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, ,12,14-nonamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl -2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2-dimethyl-1,7,9, 15-Tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane ro[7.7]pentadecane, 4,12-dibutyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,10-bis(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4 ,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. Preferably, 2,4,12-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,4,10,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,10,12-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8 -Stannaspiro[7.7]pentadecane, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,10,10,12-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4 ,6,6,10,10,12,14-nonamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,1 2-Diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4, 12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-di Aza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. More preferably, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, or mixtures thereof; Most preferably, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. or is selected from the group consisting of:

[0025] The compounds of the present invention can be used as catalysts, more preferably as thermally latent catalysts, for the production of polyisocyanate polyaddition products, especially polyurethanes, preferably polyurethane foams, polyurethane coatings, polyurethane paints or polyurethane adhesives. As thermally latent catalysts, the compounds of the present invention exert their activity preferably by increasing the temperature, for example to 60-100°C.

[0026] Method for producing the compounds of the present invention Compounds having the general formula (I): The compounds of the present invention having the general formula (I) Tin-containing compounds of the R6R7SnZ2 type Compounds of general formula (III): [ka] or Tin-containing compounds of the SnZ4 type and a compound of general formula (III); [ka] Either reaction, then with compounds of general formula (IV) and (V): [ka] [During the ceremony, R1, R2, R3, R4 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V and W are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 is oxygen, sulfur or nitrogen; A is a leaving group, preferably -OH, -SH, N(R 22 ) H- or halogen, where R 22 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; Z is a halogen, an alkoxide or a mixture thereof; at least one of the R1, R2, R3 or R4 groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' do not bear the same group; Reaction of It can be prepared by

[0027] Here, it is preferred that The compound of general formula (III) is 2,2'-(methylazanediyl)bis(ethan-1-ol), 2,2'-(ethylazanediyl)bis(ethan-1-ol), 2,2'-(butylazanediyl)bis(ethan-1-ol), 1-((2-hydroxyethyl)(methyl)amino)propan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)propan-2-ol, 1-(butyl(2-hydroxyethyl)amino)propan-2-ol, 1,1'-(methylazanediyl)bis(propan-2-ol), 1,1'-(ethylazanediyl)bis(propan-2-ol), 1,1'-(butylazanediyl)bis(propan-2-ol, 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, and / or comprising or consisting of 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol or mixtures thereof, preferably 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol or mixtures thereof; and / or The compounds of general formula (IV) and / or general formula (V) comprise or consist of halogens, halides, alkoxides, carboxylates, peroxides, disulfides or mixtures thereof.

[0028] The tin-containing compound of the SnZ4 type preferably comprises or is selected from the group consisting of tin tetrachloride, tin tetrabromide, tin tetra-tert-alkoxide, especially tin tetra-tert-butoxide, or mixtures thereof. It is also preferred that the molar ratio of the tin-containing compound to the sum of the compounds having the general formulae (III), (IV) and (V) is from 1:1 to 1:4, preferably from 1:1 to 1:2.1.

[0029] Preferably, Z in tin-containing compounds of the type R6R7SnZ2 is a halogen, such as chlorine (R6R7SnCl2).

[0030] Compounds having the general formula (II): The compounds of the present invention having the general formula (II) are those which are compounded with elemental tin or a tin-containing compound. a compound having the general formula (III); [ka] and a compound having the general formula (IV); [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; R1, R2, R3, R4, R8, R9, R 10 or R 11 at least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not bear the same groups. It can be produced by the reaction of

[0031] The compound of general formula (III) and / or the compound of general formula (VI) may be 2,2'-(methylazanediyl)bis(ethan-1-ol), 2,2'-(ethylazanediyl)bis(ethan-1-ol), 2,2'-(butylazanediyl)bis(ethan-1-ol), 1-((2-hydroxyethyl)(methyl)amino)propan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)propan-2-ol, 1-(butyl(2-hydroxyethyl)amino)propan-2-ol, 1,1'-(methylazanediyl)bis(propan-2-ol), 1,1'-(ethylazanediyl)bis(propan-2-ol), 1,1'-(butylazanediyl)bis(propan-2-ol), 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. The compound of formula (III) and (VI) may be the same or different. For example, in the case of alkanolamines, these can be, for example, the respective groups (R1, R2, R3, R4 or R8, R9, R 10 , R 11 The corresponding epoxides geminally substituted by HNR or HNR can be prepared by methods known to those skilled in the art using the general formula HNR or HNR 12and, in a sequential manner, optionally a compound of the formula R5N(H)CH2C(R1,R2)OH or R 12 It can be obtained by reaction with isolation of the NH-functional intermediate N(H)CH2C(R8,R9)OH.

[0032] Tin-containing compounds suitable according to the invention are generally tin(IV)-containing compounds. In a further embodiment of the method of the invention, it is also possible to use Sn(II) compounds. In this case, an oxidation treatment of the obtained Sn(II) complex follows. Apparatus suitable for this purpose are known per se to the person skilled in the art. The tin-containing compound is more preferably selected from the group comprising or consisting of tin tetrachloride, tin tetrabromide, tin tetraalkoxides, in particular tin tetra-tert-butoxide, or mixtures thereof. According to the invention, it is very particularly preferred to use tin tetra-tert-butoxide or tin tetrachloride. Furthermore, it is preferred that the molar ratio of elemental tin or tin-containing compounds to the sum of compounds having the general formulae (III) and (VI) is 1:1 to 1:4, preferably 1:1 to 1:2.1.

[0033] It is also possible to use elemental tin (tin powder) to prepare compounds having the general formula (II), in particular tin(IV) alkoxides. The preparation of tin(IV) alkoxides starting from elemental tin is described, for example, in DE102010012237A1.

[0034] The compounds having the general formulae (III) and (VI) are preferably provided or initially charged in a suitable reactor (such as, for example, a stirred reactor equipped with suitable devices for the addition of the reaction components), optionally in a solvent, at a suitable temperature. Suitable solvents are, for example, selected from the group consisting of alcohols, preferably methanol, ethanol, propanol, in particular isopropanol, or mixtures thereof, ethers, preferably diethyl ether, tetrahydrofuran, tert-butyl methyl ether, or mixtures thereof, halogenated solvents, preferably dichloromethane, chloroform, or mixtures thereof, aromatic solvents, preferably toluene, and mixtures thereof. The process of the present invention is preferably carried out in a temperature range of from -30 to +150°C, more preferably from -10 to 100°C, most preferably from -10°C to room temperature. It is further preferred if the process of the present invention is carried out under an inert atmosphere, for example under nitrogen. In addition to the compounds having the general formulae (III) and (VI), further components may optionally be included in the initial charge. These are, for example, selected from auxiliary bases, such as alkoxides, and mixtures containing these.

[0035] More preferably, the compounds having general formulae (III) and (VI) are the same and are reacted with a tin-containing compound to obtain the catalyst of general formula (II).

[0036] In a particularly preferred embodiment of the process of the present invention, the at least one tin-containing compound is initially charged to a suitable reactor, and the compound of general formula (III) and the compound of general formula (VI) are added in diluted form.

[0037] The resulting reaction solution can be worked up by methods known to those skilled in the art, such as filtration, distillative removal of the solvent, crystallization, and the like.

[0038] Formulations for the preparation of polyisocyanate polyaddition products The present invention also relates to a method for producing a composition comprising the following components: a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; b) at least one compound of the invention as a catalyst; c) optionally a further catalyst other than b); d) optionally auxiliaries and / or additives; (wherein the ratio of the weight of tin from component b) to the weight of component a) is preferably not more than 1000 ppm when component a) is an aliphatic and / or (cyclo)aliphatic polyisocyanate, and not more than 50 ppm when component a) is an aromatic polyisocyanate) The present invention relates to a formulation for the preparation of polyisocyanate polyaddition products, comprising or consisting of:

[0039] The formulation preferably comprises, based on the total weight of the formulation: 5% to 80% by weight of component a); 0.0001% to 2.0% by weight of component b); optionally, 0.01% to 2.0% by weight of component c); optionally, 5% to 50% by weight of component d); Contains:

[0040] Method for producing polyisocyanate polyaddition products The compounds of the present invention can be used for the preparation of polyisocyanate polyaddition products. A composition comprising or consisting of at least one compound according to claim 16 or 17 and at least one NCO-reactive compound, the reaction being preferably carried out at an isocyanate index of 80 to 150. or Ingredients include: A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; B) at least one NCO-reactive compound; C) at least one compound of the invention as a catalyst; D) optionally, a further catalyst other than C); E) optionally auxiliaries and / or additives; (wherein the ratio of the weight of tin from component C) to the weight of component A) is preferably not more than 1000 ppm when component A) is an aliphatic and / or (cyclo)aliphatic polyisocyanate, and not more than 50 ppm when component A) is an aromatic polyisocyanate) A composition comprising or consisting of The present invention provides a method for producing a polyisocyanate polyaddition product by converting

[0041] The composition preferably comprises, based on the total weight of the composition: 5% to 80% by weight of component A); 5% to 80% by weight of component B); 0.0001% to 2.0% by weight of component C); optionally, 0.01% to 2.0% by weight of component D); optionally, 5% to 50% by weight of component E); and / or the reaction is carried out at an isocyanate index of 80 to 150.

[0042] The above method results in / can result in a polyisocyanate polyaddition product.

[0043] Isocyanate index (also known as index or NCO / OH index) is understood to mean the quotient of the amount of substance [mol] of isocyanate groups actually used and the amount of substance [mol] of isocyanate-reactive groups actually used, multiplied by 100. In other words, the index indicates the percentage ratio of the amount of isocyanate actually used to the stoichiometric amount of isocyanate, i.e. the amount calculated for the conversion of OH equivalents. An equivalent of NCO groups and NCO-reactive hydrogen atoms corresponds to an NCO / OH index of 100.

number

[0044] The polyisocyanate polyaddition products are preferably polyurethanes. The individual components of the polyisocyanate polyaddition products of the invention, in particular polyurethanes, are described in detail below.

[0045] Aliphatic, (cyclo)aliphatic or aromatic polyisocyanates a) or A) (hereinafter also referred to as polyisocyanate components) suitable for the preparation of optionally substituted and / or heteroatom-containing polyisocyanate polyaddition products and / or formulations are organic polyisocyanates having at least two isocyanate groups per molecule known per se to the person skilled in the art, and mixtures thereof. Examples of polyisocyanates of this type are diisocyanates or triisocyanates, such as butane diisocyanate, pentane diisocyanate (pentamethylene diisocyanate, PDI), hexane diisocyanate (hexamethylene diisocyanate, HDI), 4,4'-methylenebis(cyclohexylisocyanate) (HDI ... 12 MDI), 3,5,5-trimethyl-1-isocyanato-3-isocyanatomethylcyclohexane (isophorone diisocyanate, IPDI), 1,3- and 1,4-bis(isocyanatomethyl)cyclohexane (H6XDI), naphthalene 1,5-diisocyanate, diisocyanatodiphenylmethane (2,2'-, 2,4'- and 4,4'-MDI or mixtures thereof), diisocyanatomethylbenzene (tolylene 2,4- and 2,6-diisocyanate, TDI) and technical mixtures of the two isomers, as well as 1,3-bis(isocyanatomethyl)benzene (XDI), 3,3'-dimethyl-4,4'-biphenyl diisocyanate (TODI), paraphenylene 1,4-diisocyanate (PPDI) and cyclohexyl diisocyanate (CHDI), and the higher molecular weight oligomers obtained from the above individually or as mixtures and having biuret, uretdione, isocyanurate, iminooxadiazinedione, allophanate, urethane and carbodiimide / uretonimine structural units. The use of polyisocyanates based on aliphatic and cycloaliphatic diisocyanates is highly preferred.

[0046] The polyisocyanate components a) and / or A) can be present in a suitable solvent. Suitable solvents are those that have sufficient solubility for the polyisocyanate components and do not contain groups reactive with isocyanates. Examples of such solvents are acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, methyl isoamyl ketone, diisobutyl ketone, ethyl acetate, n-butyl acetate, ethylene glycol diacetate, butyrolactone, diethyl carbonate, propylene carbonate, ethylene carbonate, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, methylal, ethylal, butyral, 1,3-dioxolane, glycerol formal, benzene, toluene, n-hexane, cyclohexane, solvent naphtha, 2-methoxypropyl acetate (MPA) and mixtures thereof.

[0047] The isocyanate component may be optionally supplemented with customary auxiliaries and additives, such as rheology improvers (e.g. ethylene carbonate, propylene carbonate, dibasic acid esters, citrate esters), stabilizers (e.g. Brönsted and Lewis acids, such as hydrochloric acid, phosphoric acid, benzoyl chloride, organic mineral acids, such as dibutyl phosphate, adipic acid, malic acid, succinic acid, pyruvic acid or citric acid), UV stabilizers (e.g. 2,6-dibutyl-4-methylphenol), hydrolysis stabilizers (e.g. sterically hindered carbodiimides), emulsifiers and catalysts (e.g. For example, trialkylamines, diazabicyclooctanes, tin dioctoates, dibutyltin dilaurate, N-alkylmorpholines, lead octoates, tin octoates, calcium octoates, magnesium octoates, the corresponding naphthenates and p-nitrophenoxides and / or mercuric phenyl neodecanoates) and fillers (e.g. chalk), dyes (thus having Zerewitinoff active hydrogen atoms) and / or color pigments which can be incorporated into the polyurethane / polyurea formed at a later stage.

[0048] The NCO-reactive compounds B) used are preferably known to those skilled in the art and can be any of the compounds having an average OH or NH functionality of at least 1.5. They can be, for example, low molecular weight diols (e.g. 1,2-ethanediol, 1,3- or 1,2-propanediol, 1,4-butanediol), triols (e.g. glycerol, trimethylolpropane) and tetraols (e.g. pentaerythritol), short-chain polyamines, and higher molecular weight polyhydroxyl compounds, such as polyether polyols, polyester polyols, polycarbonate polyols, polysiloxane polyols, polyamines and polyether polyamines and polybutadiene polyols.

[0049] Polyether polyols can be obtained in a manner known per se by alkoxylation of suitable starter molecules under base catalysis or using double metal cyanide compounds (DMC compounds). Examples of starter molecules suitable for the preparation of polyether polyols are simple low molecular weight polyols, water, organic polyamines having at least two NH bonds, or any mixture of such starter molecules. Preferred starter molecules for the preparation of polyether polyols by alkoxylation, in particular by the DMC method, are in particular simple polyols, such as ethylene glycol, propylene 1,3-glycol and butane-1,4-diol, hexane-1,6-diol, neopentyl glycol, 2-ethylhexane-1,3-diol, glycerol, trimethylolpropane, pentaerythritol, and low molecular weight, hydroxyl group-containing esters of such polyols with dicarboxylic acids of the type specified below by way of example, or low molecular weight ethoxylation or propoxylation products of such simple polyols, or any desired mixture of such modified or unmodified alcohols. Suitable alkylene oxides for the alkoxylation are in particular ethylene oxide and / or propylene oxide, which can be used for the alkoxylation in any order or in a mixture.

[0050] The polyester polyols are prepared by the synthesis of low molecular weight polycarboxylic acid derivatives, such as succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetrachlorophthalic anhydride, endomethylenetetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid, dimeric fatty acid, trimeric fatty acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, citric acid or trimellitic acid, and low molecular weight polyols, such as ethylene glycol, diethylene glycol, neopentane, ethylene glycol ... Polyester polyols can be prepared in a known manner by polycondensation with cyclic carboxylic acid esters such as ε-caprolactone, ethylene glycol, hexanediol, butanediol, propylene glycol, glycerol, trimethylolpropane, 1,4-hydroxymethylcyclohexane, 2-methyl-1,3-propanediol, butane-1,2,4-triol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, dibutylene glycol and polybutylene glycol, or by ring-opening polymerization of cyclic carboxylic acid esters such as ε-caprolactone. It is also possible to polycondense hydroxycarboxylic acid derivatives, such as lactic acid, cinnamic acid or ω-hydroxycaproic acid, to obtain polyester polyols. However, it is also possible to use polyester polyols of oleochemical origin. Such polyester polyols can be prepared, for example, by complete ring opening of epoxidized triglycerides of a fat mixture containing at least partially olefinically unsaturated fatty acids with one or more alcohols having 1 to 12 carbon atoms, followed by partial transesterification of the triglyceride derivatives to alkyl ester polyols having 1 to 12 carbon atoms in the alkyl group.

[0051] The preparation of suitable polyacrylate polyols is known per se to those skilled in the art. They are obtained by free radical polymerization of olefinically unsaturated monomers having hydroxyl groups or by free radical copolymerization of the olefinically unsaturated monomers having hydroxyl groups with optionally different olefinically unsaturated monomers, such as ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, isobornyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, styrene, acrylic acid, acrylonitrile, and / or methacrylonitrile. Suitable olefinically unsaturated monomers having hydroxyl groups are in particular 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, hydroxypropyl acrylate isomer mixtures obtained by addition of propylene oxide to acrylic acid, and hydroxypropyl methacrylate isomer mixtures obtained by addition of propylene oxide to methacrylic acid. Suitable free radical initiators are those from the group of the azo compounds, such as azoisobutyronitrile (AIBN), or those from the group of the peroxides, such as di-tert-butyl peroxide.

[0052] Component B) preferably comprises higher molecular weight polyhydroxy compounds, for example with a molecular weight of 500 to 10 000 g / mol, preferably 1000 to 10 000 g / mol.

[0053] Component B) may be present in a suitable solvent. Suitable solvents are those which exhibit sufficient solubility for the components. Examples of such solvents are acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, methyl isoamyl ketone, diisobutyl ketone, ethyl acetate, n-butyl acetate, ethylene glycol diacetate, butyrolactone, diethyl carbonate, propylene carbonate, ethylene carbonate, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, methylal, ethylal, butyral, 1,3-dioxolane, glycerol formal, benzene, toluene, n-hexane, cyclohexane, solvent naphtha, 2-methoxypropyl acetate (MPA) and mixtures thereof. Furthermore, the solvent may also have groups which are reactive towards isocyanates. Examples of such reactive solvents are those in which the average functionality of the groups reactive towards isocyanates is at least 1.8. These may be, for example, low molecular weight diols (e.g. ethane-1,2-diol, propane-1,3- or -1,2-diol, butane-1,4-diol), triols (e.g. glycerol, trimethylolpropane), but also low molecular weight diamines, for example polyaspartic acid esters.

[0054] To obtain the inventive polyisocyanate polyaddition products and / or the inventive formulations, at least one inventive compound as catalyst is used as component b) or C).

[0055] The statements made with regard to the catalysts of the invention, particularly with regard to the preferred embodiments, are applicable here as well. The catalysts of the invention can be added to the reaction mixture dissolved in a solvent and / or pre-dissolved in a polyisocyanate via an NCO-reactive compound (polyol).

[0056] The polyisocyanate polyaddition products of the invention or the formulations of the invention can be further obtained by optional use of further catalysts and / or activators other than components D) or c) and C) or b), in particular acids, amines, sterically hindered phenols, phosphites, etc. These are known per se to the skilled artisan and are described, for example, in WO2014 / 048879A1. Furthermore, the catalysts of the invention can be combined with further catalysts / activators known from the prior art, for example titanium, zirconium, bismuth, tin(II) and / or iron catalysts can be used, as described, for example, in WO2005 / 058996. It is also possible to add amines or amidines. Furthermore, in the polyisocyanate polyaddition reaction, it is also possible to add acidic compounds, for example 2-ethylhexanoic acid, or alcohols, in order to control the reaction.

[0057] The polyisocyanate polyaddition products of the invention and / or the formulations of the invention can further be obtained by the optional use of components E) or d): fillers, pigments, additives, thickeners, defoamers and / or other auxiliaries and additives. Substances particularly suitable as components E) / d) are selected from the group consisting of customary rheology improvers, stabilizers, UV stabilizers, hydrolysis stabilizers, emulsifiers, fillers, optionally incorporable dyes, i.e. dyes with Zerewitinoff active hydrogen atoms, color pigments and mixtures thereof. Preferred auxiliaries and additives in the preparation of polyisocyanate polyaddition products are blowing agents, fillers, chalk, carbon black or zeolites, flame retardants, dye pastes, water, antibacterial agents, flow improvers, thixotropic agents, surface modifiers and retarders. Other auxiliaries and additives include defoamers, emulsifiers, foam stabilizers and cell regulators. A review is given in G. Oertel, Polyurethane Handbook, Part 2, Carl Hanser Verlag, Munich, 1994, Ch. 3.4.

[0058] Coating Composition The polyisocyanate polyaddition products of the present invention can be used in a wide variety of different applications. In particular, the present invention provides a coating composition for coating a substrate, which comprises or consists of at least one polyisocyanate polyaddition product of the present invention, wherein the substrate is preferably a plastic part, a metal part or a wooden molding.

[0059] The system of the invention, composed of the above-mentioned components, can generally be applied to the substrate to be coated in solid form by any method known to those skilled in the art, such as from solution or melt, and in the case of powder coatings, painting, rolling, pouring, spraying, dipping, fluidized bed processes or electrostatic spraying, etc. Examples of suitable substrates are materials such as metal, wood, plastic or ceramic.

[0060] Embodiments: The present invention relates in particular to the following embodiments: In a first embodiment, the present invention relates to compounds having the general formula (I) or (II), in particular catalysts for the preparation of polyisocyanate polyaddition products: [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; In formula (I), at least one of the R1, R2, R3 or R4 groups is hydrogen and at least one of these groups is not hydrogen, where the carbon atoms C' and C'' do not have the same group, and in formula (II), R1, R2, R3, R4, R8, R9, R 10 or R 11 At least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not have the same groups.

[0061] In a second embodiment, the present invention relates to a compound having the general formula (I) or (II) for use as a catalyst in the preparation of polyisocyanate polyaddition products: [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; In formula (I), at least one of the R1, R2, R3 or R4 groups is hydrogen and at least one of these groups is not hydrogen, where the carbon atoms C' and C'' do not have the same group, and in formula (II), R1, R2, R3, R4, R8, R9, R 10 or R 11 At least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not have the same groups.

[0062] In a third embodiment, the present invention provides a compound having at least one R1, R2, R3 or R4 group in formula (I) which is not hydrogen, and at least one R1, R2, R3, R4, R8, R9, R 10 or R 11It relates to compounds according to embodiment 1 or 2, characterized in that the radical is an aliphatic, preferably a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical.

[0063] In a fourth embodiment, the present invention provides a compound comprising R5 and / or R 12 is a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl group, preferably a methyl, butyl or ethyl group.

[0064] In a fifth embodiment, the invention relates to a compound according to any of the previous embodiments, characterized in that V, W, X and Y are oxygen and / or D1 and D2 are nitrogen.

[0065] In a sixth embodiment, the invention relates to a compound according to any of the previous embodiments, characterized in that R6 and R7 are identical.

[0066] In a seventh embodiment, the present invention relates to a compound having at least one of R, R, R, R, R, R, R, R in formula (II) which is not hydrogen. 10 or R 11 R5 and R6 are each a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, preferably a methyl group; 12 are independently optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic groups, preferably the same groups and are methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl groups, more preferably the same groups and are methyl, butyl or ethyl groups; and V, W, X and Y are oxygen; and D1 and D2 are nitrogen.

[0067] In an eighth embodiment, the present invention provides a method for producing a composition comprising: R1 is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, preferably a methyl group; R2, R3, R4, R8, R9, R 10 and R 11 The group is hydrogen; or R1 and R2 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably a methyl group; R3, R4, R8, R9, R 10 and R 11 The group is hydrogen; or R1 and R 10 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are a methyl group; R, R, R, R, R and R 11 The group is hydrogen; or R1, R2 and R 10 are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are a methyl group; R, R, R, R and R 11 The group is hydrogen; or R1, R2, R 10 and R 11are the same or different radicals and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, preferably are the same radicals and are methyl, ethyl, propyl, butyl, hexyl, octyl or a perfluoroalkyl group, more preferably are methyl groups, and the R3, R4, R8 and R9 radicals are hydrogen, and R5 and R 12 are independently optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic groups, preferably the same groups and are methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl groups, more preferably the same groups and are methyl, butyl or ethyl groups, and compounds of formula (II) according to embodiment 1, characterized in that V, W, X and Y are oxygen, and D1 and D2 are nitrogen.

[0068] In a ninth embodiment, the present invention relates to a compound comprising: 2,2-dichloro-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dibromo-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dimethoxy-4,6-dimethyl-1,3,6,2-dioxazastannocane, 4,6-dimethyl-1,3,6,2-dioxazastannocane-2,2-diyl dibenzoate, 6-ethyl-4-methyl-1,3,6,2-dioxazastannocane-2,2-diyl dibenzoate, 6-butyl-4-methyl-1,3,6,2-dioxazastannocane-2,2- Diyl dibenzoate, 2,4,12-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,4,10,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,10,12-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane stannaspiro[7.7]pentadecane, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,10,10,12-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, ,12,14-nonamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl -2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2-dimethyl-1,7,9, 15-Tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane ro[7.7]pentadecane, 4,12-dibutyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,10-bis(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4 ,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. Preferably, 2,4,12-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,4,10,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,10,12-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8 -Stannaspiro[7.7]pentadecane, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,10,10,12-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4 ,6,6,10,10,12,14-nonamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,1 2-Diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4, 12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-di Aza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. More preferably, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, or mixtures thereof; Most preferably, 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof. The compound according to embodiment 1, characterized in that it comprises or is selected from the group consisting of:

[0069] In a tenth embodiment, the present invention provides a method for producing a composition comprising the steps of: Tin-containing compounds of the R6R7SnZ2 type Compounds of general formula (III): [ka] or Tin-containing compounds of the SnZ4 type and a compound of general formula (III); [ka] Either reaction, then with compounds of general formula (IV) and (V): [ka] [During the ceremony, R1, R2, R3, R4 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R6 and R7 are independently -OH, -SH, -OR 13 , halogen, -OC(=O)R 14 , -SR 15 , -OC(=S)R 16 , -OS(=O)2OR 17 , -OS(=O)2R 18 or -NR 19 R 20 where R 13 ~R 20 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V and W are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 is oxygen, sulfur or nitrogen; A is a leaving group, preferably -OH, -SH, N(R 22 ) H- or halogen, where R 22 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; Z is a halogen, an alkoxide or a mixture thereof; At least one of the R1, R2, R3 or R4 groups is hydrogen, and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' do not carry the same group. The present invention relates to a process for the preparation of a compound having general formula (I) according to any one of the embodiments 1 to 9, by the reaction:

[0070] In an eleventh embodiment, the present invention provides a method for producing a composition comprising the steps of: The compound of general formula (III) is 2,2'-(methylazanediyl)bis(ethan-1-ol), 2,2'-(ethylazanediyl)bis(ethan-1-ol), 2,2'-(butylazanediyl)bis(ethan-1-ol), 1-((2-hydroxyethyl)(methyl)amino)propan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)propan-2-ol, 1-(butyl(2-hydroxyethyl)amino)propan-2-ol, 1,1'-(methylazanediyl)bis(propan-2-ol), 1,1'-(ethylazanediyl)bis(propan-2-ol), 1,1'-(butylazanediyl)bis(propan-2-ol, 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, and / or comprising or consisting of 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol or mixtures thereof, preferably 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol or mixtures thereof; and / or The compounds of general formula (IV) and / or general formula (V) contain or consist of halogens, halides, alkoxides, carboxylates, peroxides, disulfides or mixtures thereof. 11. The method according to embodiment 10,

[0071] In a twelfth embodiment, the present invention relates to a process according to embodiment 10 or 11, characterized in that the tin-containing compound of the SnZ4 type comprises or is selected from the group consisting of tin tetrachloride, tin tetrabromide, tin tetra-tert-alkoxides, in particular tin tetra-tert-butoxide, and mixtures thereof.

[0072] In a thirteenth embodiment, the present invention relates to the process according to any of the tenth to twelfth embodiments, characterized in that the molar ratio of the tin-containing compound to the sum of the compounds having the general formulae (III), (IV) and (V) is from 1:1 to 1:4, preferably from 1:1 to 1:2.1.

[0073] In a fourteenth embodiment, the present invention relates to a method for producing a tin-containing tin alloy comprising the steps of: a compound having the general formula (III); [ka] and a compound having the general formula (IV); [ka] [During the ceremony, R1, R2, R3, R4, R8, R9, R 10 and R 11 are independently hydrogen or an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; R5 and R 12 is independently an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; V, W, X and Y are independently oxygen, sulfur, -OC(=O)-, -OC(=S)-, -SC(=O)-, -SC(=S)-, -OS(=O)2O-, -OS(=O)2- or -N(R 21 )-, where R 21 is an optionally substituted and / or heteroatom-containing aliphatic, (cyclo)aliphatic or aromatic group; D1 and D2 are independently oxygen, sulfur or nitrogen; R1, R2, R3, R4, R8, R9, R 10 or R 11at least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not bear the same groups. The present invention relates to a method for producing a compound having general formula (I) according to any one of the embodiments 1 to 9, by the reaction of:

[0074] In a fifteenth embodiment, the present invention relates to a compound of general formula (III) and / or a compound of general formula (VI) which is selected from the group consisting of 2,2'-(methylazanediyl)bis(ethan-1-ol), 2,2'-(ethylazanediyl)bis(ethan-1-ol), 2,2'-(butylazanediyl)bis(ethan-1-ol, 1-((2-hydroxyethyl)(methyl)amino)propan-2-ol, 1-(ethyl ... 1-(ethyl)amino)propan-2-ol, 1-(butyl(2-hydroxyethyl)amino)propan-2-ol, 1,1'-(methylazanediyl)bis(propan-2-ol), 1,1'-(ethylazanediyl)bis(propan-2-ol), 1,1'-(butylazanediyl)bis(propan-2-ol), 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, 1-( 15. The process according to embodiment 14, characterized in that the compound of general formula (III) and the compound of general formula (VI) are preferably identical, and further comprising or consisting of 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol, 1-(butyl(2-hydroxypropyl)amino)-2-methylpropan-2-ol or mixtures thereof, preferably 1-((2-hydroxyethyl)(methyl)amino)-2-methylpropan-2-ol, 1-(ethyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol and 1-(butyl(2-hydroxyethyl)amino)-2-methylpropan-2-ol or mixtures thereof,

[0075] In a sixteenth embodiment, the present invention relates to the process according to embodiment 14 or 15, characterized in that the tin-containing compound comprises or is selected from the group consisting of tin tetrachloride, tin tetrabromide, tin tetraalkoxides, in particular tin tetra-tert-butoxide, or mixtures thereof.

[0076] In a seventeenth embodiment, the present invention relates to a process according to any of the fourteenth and sixteenth embodiments, characterized in that the molar ratio of elemental tin or tin-containing compound to the sum of compounds having the general formulae (III) and (VI) is from 1:1 to 1:4, preferably from 1:1 to 1:2.1.

[0077] In an eighteenth embodiment, the present invention relates to the use of a compound according to any of claims 1 to 9 as catalyst, preferably as thermally latent catalyst, for the production of polyisocyanate polyaddition products, in particular polyurethanes, preferably polyurethane foams, polyurethane coatings, polyurethane paints or polyurethane adhesives.

[0078] In a nineteenth embodiment, the present invention provides a composition comprising the following components: a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; b) at least one compound according to embodiments 1 to 9 as a catalyst; c) optionally a further catalyst other than b); d) Optionally, auxiliaries and / or additives [wherein the ratio of the weight of tin from component b) to the weight of component a) is preferably not more than 1000 ppm when component a) is an aliphatic and / or (cyclo)aliphatic polyisocyanate and not more than 50 ppm when component a) is an aromatic polyisocyanate] The present invention relates to a formulation for the preparation of polyisocyanate polyaddition products, comprising or consisting of:

[0079] In a twentieth embodiment, the present invention relates to a composition comprising, based on the total weight of the composition, 5% to 80% by weight of component a); 0.0001% to 2.0% by weight of component b); optionally, 0.01% to 2.0% by weight of component c); optionally, 5% to 50% by weight of component d); 19. The formulation according to embodiment 19, characterized in that it contains

[0080] In a twenty-first embodiment, the present invention provides a method for the preparation of a composition comprising: A composition comprising or consisting of at least one compound according to embodiment 19 or 20 and at least one NCO-reactive compound, wherein the reaction is preferably carried out at an isocyanate index of 80 to 150. or A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate, which may be substituted and / or which contains heteroatoms; B) at least one NCO-reactive compound; C) at least one compound according to embodiments 1 to 9 as a catalyst; D) optionally, a further catalyst other than C); E) Optionally, auxiliaries and / or additives [wherein the ratio of the weight of tin from component C) to the weight of component A) is preferably not more than 1000 ppm when component A) is an aliphatic and / or (cyclo)aliphatic polyisocyanate and not more than 50 ppm when component A) is an aromatic polyisocyanate] A composition comprising or consisting of The present invention relates to a method for producing a polyisocyanate polyaddition product by reacting a composition comprising:

[0081] In a twenty-second embodiment, the present invention relates to a composition comprising, based on the total weight of the composition: 5% to 80% by weight of component A); 5% to 80% by weight of component B); 0.0001% to 2.0% by weight of component C); optionally, 0.01% to 2.0% by weight of component D); optionally, 5% to 50% by weight of component E); and / or the reaction is carried out with an isocyanate index of 80 to 150.

[0082] In a twenty-third embodiment, the present invention relates to a polyisocyanate polyaddition product obtained or obtainable by the process according to embodiment 21 or 22.

[0083] In a twenty-fourth embodiment, the present invention relates to a coating composition for coating a substrate, comprising or consisting of at least one polyisocyanate polyaddition product according to embodiment twenty-two, the substrate being preferably a plastic part, a metal part or a wooden molding. EXAMPLES

[0084] Examples and Comparative Examples: The present invention will be described below with reference to examples, but the present invention is not limited to these.

[0085] In the examples, all percentages should be understood to mean weight percent unless otherwise specified. All reactions were carried out under a dry nitrogen atmosphere. The preparation of the catalysts of the present invention and comparative catalysts listed in Table 1, the synthesis of the ligands used in their preparation, and the provision of the thermally latent catalyzed polyisocyanate curing agent formulations used are described in detail in WO2021 / 249887A1.

[0086] In order to better compare the activity of the catalysts used according to the invention and those from comparative examples, the amount of catalyst is reported as mg of Sn (ppm) per kg of polyisocyanate hardener, using the commercial product Desmodur ultra N 3300 (HC content 5 ppm) (from Covestro AG, Leverkusen, D, NCO content 21.8%) as polyisocyanate hardener and exactly 1 equivalent of triethylene glycol monomethyl ether (product from Aldrich, Taufkirchen, Germany) based on the free isocyanate groups of the polyisocyanate hardener as model compound. The addition of 10% (based on Desmodur ultra N3300) n-butyl acetate ensured that samples of sufficiently low viscosity could be taken over the entire course of the reaction, allowing accurate detection of the NCO content by titration according to DIN 53185. The calculated NCO content at the start of the reaction without NCO-OH reaction was 11.1%, which is normalized here to 100% as the starting value, and all titration values ​​are normalized thereto in Table 2.

[0087] Comparative experiment 1 at constant 30° C. shows the extremely slow decrease of the NCO content of the mixture in the absence of catalysis (Table 2, experiment 1). To allow a comparison of the acceleration of the reaction at the reaction temperature 50° C. (called the "curing temperature" in the actual coating system), a series of experiments was additionally carried out, first at a constant 30° C. (2 h) and then at 50° C., also without catalysis (Table 2, experiment 2). All comparative experiments 3 to 7 and the examples of the invention (8 and above) were carried out according to the same regime: first at 30° C. for 2 h for the evaluation of the thermal latency and then at 50° C. for the evaluation of the reactivity at the "curing temperature".

[0088] Table 1 Summary of catalysts used: 1 to 3 are comparative examples, 4 and above are the present invention [Table 1]

[0089] Table 2 Overview of the experiment (Examples 1 to 7: Comparative Examples, Examples 8-15: The present invention ) [Table 2]

[0090] As can be seen from the results in Table 2, all systems, whether they are inventive or not, are not fully reactive at 30 °C, which is considered to be thermally latent. However, the inventive systems with the "asymmetric" ligand environment of the central atom at 50 °C show in some cases much higher activity than observed in the comparative systems based on catalysts 1-3. Considering the very low reactivity of compound 3 and the moderate reactivity of compound 1, it is surprising that compound 4, which is essentially a "combination" of the ligand environments of 1 and 3, is much more reactive than the two comparative catalysts. Here, one skilled in the art would have expected a reactivity between 1 and 3.

[0091] Examples 16-21: Experimental series for evaluation of color stability Catalysts 1, 2 and 4 from Table 1 were first dissolved in hexamethylene diisocyanate (HC content 25 ppm), the catalyst concentration selected to give a homogeneous mixture containing 0.1% tin (Examples 16-18), then mixed as a 10% solution in n-butyl acetate (BA) with Covestro Desmodur N3900 polyisocyanate containing iminooxadiazinedione groups (HC content 16 ppm) in an amount to give a homogeneous 750 ppm tin based on the solvent-free Desmodur N 3900 with heating (50°C), then further diluted to 90% solids with the addition of butyl acetate (Examples 19-21).

[0092] The Hazen colour index was determined spectrophotometrically according to DIN EN ISO 6271-2:2005-03 using a LICO 400 spectrophotometer (Lange, Germany).

[0093] These mixtures were stored under nitrogen at 50° C. and monitored for color development (see Table 3).

[0094] Table 3 Summary of experiments carried out on the colour development of HDI (0.1% Sn) and Desmodur N 3900 (750 ppm Sn based on polyisocyanate) (Examples 16, 17, 19 and 20: Comparative Examples, Examples 18 and 21: The present invention ) [Table 3]

[0095] As can be seen, the inventive system based on catalyst 4 is also clearly superior to the structurally similar comparison system (catalyst 2 is simply a positional isomer of 4!) in terms of color stability of the isocyanate adduct.

[0096] Examples 22-27: Experimental series for evaluation of color stability Catalysts 1, 2, 4 and 9 according to Table 1 were first dissolved in bis(4-isocyanatocyclohexyl)methane (isomer mixture, Desmodur W product from Covestro, HC content <5 ppm, detection limit of the selected method), the catalyst concentration being selected in each case to obtain a homogeneous mixture containing 0.1% tin (Examples 22-25), then catalysts 2 and 4 were mixed with Covestro Desmodur CQ N 7300 polyisocyanate (HC content 12 ppm) as a 10% solution in n-butyl acetate (BA) in an amount such that a homogeneous 750 ppm of tin was obtained based on the solvent-free Desmodur CQ UN 7300, with heating (50° C.), then diluted to 90% solids by further addition of butyl acetate (Examples 26-29).

[0097] The Hazen colour index was determined spectrophotometrically according to DIN EN ISO 6271-2:2005-03 using a LICO 400 spectrophotometer (Lange, Germany).

[0098] These mixtures were stored under nitrogen at 50° C. and monitored for color development (see Table 4).

[0099] Table 4 Summary of experiments carried out on the colour development of Desmodur W (0.1% Sn) and Desmodur CQ UN 7300 (750 ppm Sn based on polyisocyanate) (Examples 22, 23 and 26: Comparative Examples, Examples 24, 25 and 27: The present invention ) [Table 4]

[0100] As can be seen, the inventive products based on catalysts 4 and 9 are clearly superior to the structurally similar comparative products (catalyst 2 is simply a positional isomer of 4!) also in terms of the color stability of their isocyanate adducts. Without wishing to be bound by any theory, it seems reasonable to assume that the lower residual halogen content (detected by the HC content) of the isocyanates used here (compare in particular the results obtained with Desmodur W and HDI) generally has a positive effect on color stability, and that the catalysts used according to the invention (4 and 9) also show clearly better results than the comparative systems from the prior art (1 and 2).

Claims

1. Compounds of general formula (I) or (II) for use as catalysts in the preparation of polyisocyanate polyaddition products: 【Chemistry 1】 [During the ceremony, R １ , R ２ , R ３ , R ４ , R ８ , R ９ , R １０ and R １１ are independently hydrogen or an aliphatic, (cyclo)aliphatic or aromatic group; R ５ and R １２ are independently an aliphatic, (cyclo)aliphatic, or aromatic group; R ６ and R ７ are independently —OH, —SH, —OR １３ , halogen, —OC(═O)R １４ , -SR １５ , -OC(=S)R １６ , -OS(=O) ２ OR １７ , -OS(=O) ２ R １８ or -NR １９ R ２０ where R １３ ~R ２０ are independently an aliphatic, (cyclo)aliphatic, or aromatic group; V, W, X, and Y are independently oxygen, sulfur, —OC(═O)—, —OC(═S)—, —SC(═O)—, —SC(═S)—, or —OS(═O) ２ O-, -OS (=O) ２ - or -N(R ２１ )—, where R ２１ is an aliphatic, (cyclo)aliphatic or aromatic group; D １ and D ２ are independently oxygen, sulfur, or nitrogen; In formula (I), R １ , R ２ , R ３ or R ４ At least one of the groups is hydrogen and at least one of the groups is not hydrogen, wherein the carbon atoms C′ and C″ do not have the same group, and in formula (II), R １ , R ２ , R ３ , R ４ , R ８ , R ９ , R １０ or R １１ At least one of the groups is hydrogen and at least one of these groups is not hydrogen, wherein the carbon atoms C' and C'' and / or C''' and C'''' do not have the same group.

2. At least one R in formula (I) that is not hydrogen １ , R ２ , R ３ or R ４ group, and at least one R in formula (II) that is not hydrogen １ , R ２ , R ３ , R ４ , R ８ , R ９ , R １０ or R １１ 2. The compound according to claim 1, characterized in that the group is aliphatic.

3. R ５ and / or R １２ 3. The compound according to claim 1, wherein is a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl group.

4. V, W, X and Y are oxygen, and / or D １ and D ２ 3. The compound according to claim 1 or 2, characterized in that is nitrogen.

5. R ６ and R ７ The compound according to claim 1 or 2, characterized in that:

6. At least one R in formula (II) is not hydrogen １ , R ２ , R ３ , R ４ , R ８ , R ９ , R １０ or R １１ the radical is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, And R ５ and R １２ are independently an aliphatic, (cyclo)aliphatic or aromatic group, and V, W, X and Y are oxygen; D １ and D ２ 2. The compound of formula (II) according to claim 1, characterized in that is nitrogen.

7. R １ is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl group, and R ２ , R ３ , R ４ , R ８ , R ９ , R １０ and R １１ The group is hydrogen, or R １ and R ２ are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl groups, and R ３ , R ４ , R ８ , R ９ , R １０ and R １１ The group is hydrogen, or R １ and R １０ are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl groups, and R ２ , R ３ , R ４ , R ８ , R ９ and R １１ The group is hydrogen, or R １ , R ２ and R １０ are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl groups, and R ３ , R ４ , R ８ , R ９ and R １１ The group is hydrogen, or R １ , R ２ , R １０ and R １１ are the same or different groups and are methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl groups, R ３ , R ４ , R ８ and R ９ The group is hydrogen, and R ５ and R １２ are independently an aliphatic, (cyclo)aliphatic or aromatic group; and V, W, X and Y are oxygen, and D １ and D ２ 2. The compound of formula (II) according to claim 1, characterized in that is nitrogen.

8. The compound is 2,2-dichloro-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dibromo-4,6-dimethyl-1,3,6,2-dioxazastannocane, 2,2-dimethoxy-4,6-dimethyl-1,3,6,2-dioxazastannocane, 4,6-dimethyl-1,3,6,2-dioxazastannocane-2,2-diyldibenzoate, 6-ethyl-4-methyl-1,3,6,2-dioxazastannocane-2,2-diyldibenzoate, 6-butyl-4-methyl-1,3,6,2-dioxazastannocane-2,2-diyldibenzoate 2,4,12-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,4,10,12-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,10,12-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,10,10,12-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 2,2,4,6,6,10,10,12,14-nonamethyl-1,7, 9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa -4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-diethyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2, 10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,10,10-pentamethyl-1,7,9,15-tetraoxa-4,12-diaza- 8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,2,6,6,10,10,14-heptamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2-(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dibutyl-2,10-bis(trifluoromethyl)-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipropyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dipentyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[ 7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dihexyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, 4,12-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane, or mixtures thereof.

9. 3. Use of a compound according to claim 1 or 2 as a catalyst.

10. Ingredients: a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate; b) at least one compound according to claim 1 or 2 as a catalyst; 1. A formulation for producing polyisocyanate polyaddition products, comprising or consisting of:

11. The formulation comprises, based on the total weight of the formulation: 5% to 80% by weight of component a); 0.0001% to 2.0% by weight of component b); 11. The formulation according to claim 10, characterized in that it contains:

12. The following ingredients: A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate; B) at least one NCO-reactive compound; C) at least one compound according to claim 1 or 2 as a catalyst; 1. A method for producing a polyisocyanate polyaddition product by reacting a composition comprising or consisting of:

13. The composition comprises, based on the total weight of the composition: 5% to 80% by weight of component A); 5% to 80% by weight of component B); 0.0001% to 2.0% by weight of component C); and / or the reaction is carried out at an isocyanate index of 80 to 150.

14. 13. A polyisocyanate polyaddition product obtained or obtainable by the process according to claim 12.

15. 15. A coating composition for coating a substrate, comprising or consisting of at least one polyisocyanate polyaddition product according to claim 14.

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