USE OF SPECIFIC CATALYSTS FOR THE PREPARATION OF POLYURETHANE COATINGS

Abstract

The present invention relates to a compound for use as catalyst in the production of polyisocyanate polyaddition products, to the production thereof and to the use thereof as catalyst, preferably as thermolatent catalyst, for production of polyisocyanate polyaddition products. The invention further relates to a formulation and to a process for producing polyisocyanate polyaddition products, each using the compound of the invention, and to a polyisocyanate polyaddition product obtained or obtainable by said process. The invention finally relates to a coating composition for coating a substrate, comprising or consisting of the polyisocyanate polyaddition product of the invention.

Claims

1. A compound of the general formula (I) or (II): ##STR00005## where R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are independently hydrogen or are aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted or have heteroatoms; R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted or have heteroatoms; R.sub.6 and R.sub.7 are independently OH, SH, OR.sub.13, halogens, OC(O)R.sub.14, SR.sub.15, OC(S)R.sub.16, OS(O).sub.2OR.sub.17, OS(O).sub.2R.sub.18 or NR.sub.19R.sub.20, where R.sub.13 to R.sub.20 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted or have heteroatoms; V, W, X and Y are independently oxygen, sulfur, OC(O), OC(S), SC(O), SC(S), OS(O).sub.2O, OS(O).sub.2 or N(R.sub.21), where R.sub.21 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted or have heteroatoms; D.sub.1 and D.sub.2 are independently oxygen, sulfur or nitrogen; wherein in formula (I) at least one of the R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C do not bear the same radicals, and wherein formula (II) at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C and/or C and C do not bear the same radicals.

2. The compound of claim 1, wherein the at least one R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radical in formula (I) that is not hydrogen and the at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical.

3. The compound of claim 1, wherein R.sub.5 or R.sub.12 is a methyl, butyl or ethyl radical.

4. The compound of claim 1, wherein V, W, X and Y are oxygen or D.sub.1 and D.sub.2 are nitrogen.

5. The compound of claim 1, wherein R.sub.6 and R.sub.7 are identical.

6. The compound of formula (II) of claim 1, wherein at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted or have heteroatoms, and in that V, W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

7. The compound of formula (II) of claim 1, wherein R.sub.1 is a methyl radical, and the R.sub.2, R.sub.3, R.sub.4, Ra, R.sub.9, R.sub.10 and R.sub.11 radicals are hydrogen, or R.sub.1 and R.sub.2 are the same or different and are a methyl radical, and the R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 radicals are hydrogen, or R.sub.1 and R.sub.10 are the same or different and are a methyl radical, and the R.sub.2, R.sub.3, R.sub.4, Ra, R.sub.9 and R.sub.11 radicals are hydrogen, or R.sub.1, R.sub.2 and R.sub.10 are the same or different and are a methyl radical, and the R.sub.3, R.sub.4, Ra, R.sub.9 and R.sub.11 radicals are hydrogen, or R.sub.1, R.sub.2, R.sub.10 and R.sub.11 are the same or different and are a methyl radical, and the R.sub.3, R.sub.4, R.sub.8 and R.sub.9 radicals are hydrogen, and in that R.sub.5 and R.sub.12 are the same and are a methyl, butyl or ethyl radical, and W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

8. The compound of claim 1, wherein the compound is selected from the group 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, 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-4,12-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-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof.

9. (canceled)

10. A formulation for production of polyisocyanate polyaddition products, comprising the following components: a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate that is optionally substituted and/or has heteroatoms; b) at least one compound of claim 1 as catalyst; c) optionally further catalysts other than b); d) optionally auxiliaries and/or additives, where the ratio of the weight of tin from component b) and the weight of component a) is preferably not more than 1000 ppm when component a) is an aliphatic or (cyclo)aliphatic polyisocyanate, and is not more than 50 ppm when component a) is an aromatic polyisocyanate.

11. The formulation of claim 10, wherein the formulation contains 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); based on the total weight of the formulation.

12. A process for producing polyisocyanate polyaddition products by reaction of a composition: comprising the following components: A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate that is optionally substituted and/or has heteroatoms; B) at least one NCO-reactive compound; C) at least one compound of claim 1 as catalyst; D) optionally further catalysts other than C); E) optionally auxiliaries and/or additives, where the ratio of the weight of tin from component C) and the weight of component A) is preferably not more than 1000 ppm when component A) is an aliphatic or (cyclo)aliphatic polyisocyanate, and is not more than 50 ppm when component A) is an aromatic polyisocyanate.

13. The process of claim 12, wherein the composition contains 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); based on the total weight of the composition, and/or in that the reaction is effected at an isocyanate index of 80 to 150.

14-15. (canceled)

16. The compound of formula (II) of claim 1, wherein the at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is a methyl, ethyl, propyl, butyl, hexyl, or octyl or perfluoroalkyl radical, and R.sub.5 and R.sub.12 are the same and are a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl radical, and V, W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

17. The compound of formula (II) of claim 1, wherein the at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and R.sub.5 and R.sub.12 are the same and are a methyl, butyl or ethyl radical, and V, W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

18. The compound of claim 1, wherein the compound is selected from the group comprising 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-4,12-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-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.

19. The compound of claim 1, wherein the compound is selected from the group comprising 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-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.

20. The compound of claim 1, wherein the compound is selected from the group comprising 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.

Description

EMBODIMENTS

[0160] The present invention especially relates to the following embodiments:

[0161] In a first embodiment, the invention relates to a compound, especially a catalyst for production of polyisocyanate polyaddition products, having the general formula (I) or (II):

##STR00003##

where [0162] R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are independently hydrogen or are aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0163] R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0164] R.sub.6 and R.sub.7 are independently OH, SH, OR.sub.13, halogens, OC(O)R.sub.14, SR.sub.15, OC(S)R.sub.16, OS(O).sub.2OR.sub.12, OS(O).sub.2R.sub.18 or NR.sub.19R.sub.20, where R.sub.13 to R.sub.20 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0165] V, W, X and Y are independently oxygen, sulfur, OC(O), OC(S), SC(O), SC(S), OS(O).sub.2O, OS(O).sub.2 or N(R.sub.21), where R.sub.21 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0166] D.sub.1 and D.sub.2 are independently oxygen, sulfur or nitrogen;
characterized in that in formula (I) at least one of the R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C do not bear the same radicals, and in formula (II) at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C and/or C and C do not bear the same radicals.

[0167] In a second embodiment, the invention relates to a compound having the general formula (I) or (II) for use as catalyst in the production of polyisocyanate polyaddition products:

##STR00004##

where [0168] R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are independently hydrogen or are aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0169] R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0170] R.sub.6 and R.sub.7 are independently OH, SH, OR.sub.13, halogens, OC(O)R.sub.14, SR.sub.15, OC(S)R.sub.16, OS(O).sub.2OR.sub.17, OS(O).sub.2R.sub.18 or NR.sub.19R.sub.20, where R.sub.13 to R.sub.20 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0171] V, W, X and Y are independently oxygen, sulfur, OC(O), OC(S), SC(O), SC(S), OS(O).sub.2O, OS(O).sub.2 or N(R.sub.21), where R.sub.21 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0172] D.sub.1 and D.sub.2 are independently oxygen, sulfur or nitrogen;
characterized in that in formula (I) at least one of the R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C do not bear the same radicals, and in formula (II) at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C and/or C and C do not bear the same radicals.

[0173] In a third embodiment, the invention relates to a compound according to embodiment 1 or 2, characterized in that the at least one R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radical in formula (I) that is not hydrogen and the at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is aliphatic and is preferably a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical.

[0174] In a fourth embodiment, the invention relates to a compound according to any of the preceding embodiments, characterized in that R.sub.5 and/or R.sub.12 is a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl radical, preferably a methyl, butyl or ethyl radical.

[0175] In a fifth embodiment, the invention relates to a compound according to any of the preceding embodiments, characterized in that V, W, X and Y are oxygen and/or D.sub.1 and D.sub.2 are nitrogen.

[0176] In a sixth embodiment, the invention relates to a compound according to any of the preceding embodiments, characterized in that R.sub.6 and R.sub.7 are identical.

[0177] In a seventh embodiment, the invention relates to a compound of formula (II) according to embodiment 1, characterized in that the at least one R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radical in formula (II) that is not hydrogen is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, preferably a methyl radical, and in that R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms, are preferably the same and are a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl radical, and are more preferably the same and are a methyl, butyl or ethyl radical, and in that V, W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

[0178] In an eighth embodiment, the invention relates to a compound of formula (II) according to embodiment 1, characterized in that [0179] R.sub.1 is a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, preferably a methyl radical, and the R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 radicals are hydrogen, [0180] or [0181] R.sub.1 and R.sub.2 are the same or different and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, are preferably the same and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and are more preferably a methyl radical, and the R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 radicals are hydrogen, [0182] or [0183] R.sub.1 and R.sub.10 are the same or different and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, are preferably the same and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and are more preferably a methyl radical, and the R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9 and R.sub.11 radicals are hydrogen, [0184] or [0185] R.sub.1, R.sub.2 and R.sub.10 are the same or different and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, are preferably the same and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and are more preferably a methyl radical, and the R.sub.3, R.sub.4, R.sub.8, R.sub.9 and R.sub.11 radicals are hydrogen, [0186] or [0187] R.sub.1, R.sub.2, R.sub.10 and R.sub.11 are the same or different and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, are preferably the same and are a methyl, ethyl, propyl, butyl, hexyl, octyl or perfluoroalkyl radical, and are more preferably a methyl radical, and the R.sub.3, R.sub.4, R.sub.5 and R.sub.9 radicals are hydrogen, [0188] and [0189] in that R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms, are preferably the same and are a methyl, ethyl, propyl, butyl, pentyl, hexyl or octyl radical, and are more preferably the same and are a methyl, butyl or ethyl radical, [0190] and in that V, W, X and Y are oxygen and D.sub.1 and D.sub.2 are nitrogen.

[0191] In a ninth embodiment, the invention relates to a compound according to embodiment 1, characterized in that the compound is selected from the group comprising or consisting of [0192] 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, 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-4,12-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-dioctyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane or mixtures thereof, [0193] 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-4,12-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-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, [0194] 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-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, [0195] 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.

[0196] In a tenth embodiment, the invention relates to a process for producing a compound having the general formula (I) according to any of embodiments 1 to 9 by reaction of either [0197] a tin-containing compound of the R.sub.6R.sub.7SnZ.sub.2 type with [0198] a compound of the general formula (III):

HVC(R.sub.1;R.sub.2)CH.sub.2-D.sub.1(R.sub.5)CH.sub.2C(R.sub.3;R.sub.4)WH(III)

or [0199] a tin-containing compound of the SnZ.sub.4 type with [0200] a compound of the general formula (III); and

HVC(R.sub.1;R.sub.2)CH.sub.2-D.sub.1(R.sub.5)CH.sub.2C(R.sub.3;R.sub.4)WH(III) [0201] and then with compounds of the general formulae (IV) and (V):

R.sub.6-A(IV)

R.sub.7-A(V)

where [0202] R.sub.1, R.sub.2, R.sub.3, R.sub.4 are independently hydrogen or are aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0203] R.sub.5 is independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0204] R.sub.6 and R.sub.7 are independently OH, SH, OR.sub.13, halogens, OC(O)R.sub.14, SR.sub.15, OC(S)R.sub.16, OS(O).sub.2OR.sub.17, OS(O).sub.2R.sub.18 or NR.sub.19R.sub.20, where R.sub.13 to R.sub.20 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0205] V and W are independently oxygen, sulfur, OC(O), OC(S), SC(O), SC(S), OS(O).sub.2O, OS(O).sub.2 or N(R.sub.21), where R.sub.21 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0206] D.sub.1 is oxygen, sulfur or nitrogen; [0207] A is leaving groups, preferably OH, SH, N(R.sub.22)H or halogens, where R.sub.22 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0208] Z is halogens, alkoxides or mixtures thereof;
characterized in that at least one of the R.sub.1, R.sub.2, R.sub.3 or R.sub.4 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C do not bear the same radicals.

[0209] In an eleventh embodiment, the invention relates to a process according to embodiment 10, characterized in that [0210] the compound of the general formula (III) comprises or consists 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(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, 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 [0211] the compound of the general formula (IV) and/or of the general formula (V) comprises or consists of halogen, halides, alkoxides, carboxylates, peroxides, disulfides or mixtures thereof.

[0212] In a twelfth embodiment, the invention relates to a process according to embodiment 10 or 11, characterized in that the tin-containing compound of the SnZ.sub.4 type is selected from the group comprising or consisting of tin tetrachloride, tin tetrabromide, tin tetra-tert-alkoxide, especially tin tetra-tert-butoxide, and mixtures thereof.

[0213] In a thirteenth embodiment, the invention relates to a process according to any of embodiments 10 to 12, characterized in that the molar ratio of tin-containing compound to the sum total 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.

[0214] In a fourteenth embodiment, the invention relates to a process for producing a compound having the general formula (I) according to any of embodiments 1 to 9 by reaction of elemental tin or a tin-containing compound with [0215] a compound having the general formula (III); and

HVC(R.sub.1;R.sub.2)CH.sub.2-D.sub.1(R.sub.5)CH.sub.2C(R.sub.3;R.sub.4)WH(III) [0216] a compound having the general formula (IV);

HXC(R.sub.8;R.sub.9)CH.sub.2-D.sub.2(R.sub.12)CH.sub.2C(R.sub.10;R.sub.11)YH(VI);

where [0217] R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 are independently hydrogen or are aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0218] R.sub.5 and R.sub.12 are independently aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0219] V, W, X and Y are independently oxygen, sulfur, OC(O), OC(S), SC(O), SC(S), OS(O).sub.2O, OS(O).sub.2 or N(R.sub.21), where R.sub.21 is aliphatic, (cyclo)aliphatic or aromatic radicals that are optionally substituted and/or have heteroatoms; [0220] D.sub.1 and D.sub.2 are independently oxygen, sulfur or nitrogen;
characterized in that at least one of the R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.8, R.sub.9, R.sub.10 or R.sub.11 radicals is hydrogen and at least one of these radicals is not hydrogen, where the carbon atoms C and C and/or C and C do not bear the same radicals.

[0221] In a fifteenth embodiment, the invention relates to a process according to embodiment 14, characterized in that the compound of the general formula (III) and/or the compound of the general formula (VI) comprises or consists 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(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, 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, where it is preferable when the compound of the general formula (III) and the compound of the general formula (VI) are identical.

[0222] In a sixteenth embodiment, the invention relates to a process according to embodiment 14 or 15, characterized in that the tin-containing compound is selected from the group comprising or consisting of tin tetrachloride, tin tetrabromide, tin tetra-alkoxide, especially tin tetra-tert-butoxide, or mixtures thereof.

[0223] In a seventeenth embodiment, the invention relates to a process according to any of embodiments 14 and 16, characterized in that the molar ratio of elemental tin or tin-containing compound to the sum total of the compounds having the general formulae (III) and (VI) is from 1:1 to 1:4, preferably from 1:1 to 1:2.1.

[0224] In an eighteenth embodiment, the invention relates to the use of a compound as claimed in any of claims 1 to 9 as catalyst, preferably as thermolatent catalyst for production of polyisocyanate polyaddition products, especially polyurethanes, preferably polyurethane foams, polyurethane coatings, polyurethane paints or polyurethane adhesives.

[0225] In a nineteenth embodiment, the invention relates to a formulation for production of polyisocyanate polyaddition products, comprising or consisting of the following components: [0226] a) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate that is optionally substituted and/or has heteroatoms; [0227] b) at least one compound according to any of embodiments 1 to 9 as catalyst; [0228] c) optionally further catalysts other than b); [0229] d) optionally auxiliaries and/or additives,
where the ratio of the weight of tin from component b) and the weight of component a) is preferably not more than 1000 ppm when component a) is an aliphatic and/or (cyclo)aliphatic polyisocyanate, and is not more than 50 ppm when component a) is an aromatic polyisocyanate.

[0230] In a twentieth embodiment, the invention relates to a formulation according to embodiment 19, characterized in that the formulation contains [0231] 5% to 80% by weight of component a); [0232] 0.0001% to 2.0% by weight of component b); [0233] optionally 0.01% to 2.0% by weight of component c); [0234] optionally 5% to 50% by weight of component d);
based on the total weight of the formulation.

[0235] In a twenty-first embodiment, the invention relates to a process for producing polyisocyanate polyaddition products by reaction of a composition: [0236] comprising or consisting of at least one formulation according to embodiment 19 or 20 and at least one NCO-reactive compound, where the reaction is preferably effected at an isocyanate index of 80 to 150,
or [0237] comprising or consisting of the following components: [0238] A) at least one aliphatic, (cyclo)aliphatic or aromatic polyisocyanate that is optionally substituted and/or has heteroatoms; [0239] B) at least one NCO-reactive compound; [0240] C) at least one compound according to any of embodiments 1 to 9 as catalyst; [0241] D) optionally further catalysts other than C); [0242] E) optionally auxiliaries and/or additives, [0243] where the ratio of the weight of tin from component C) and the weight of component A) is preferably not more than 1000 ppm when component A) is an aliphatic and/or (cyclo)aliphatic polyisocyanate, and is not more than 50 ppm when component A) is an aromatic polyisocyanate.

[0244] In a twenty-second embodiment, the invention relates to a process according to embodiment 21, characterized in that the composition contains [0245] 5% to 80% by weight of component A); [0246] 5% to 80% by weight of component B); [0247] 0.0001% to 2.0% by weight of component C); [0248] optionally 0.01% to 2.0% by weight of component D); [0249] optionally 5% to 50% by weight of component E);
based on the total weight of the composition, and/or in that the reaction is effected at an isocyanate index of 80 to 150.

[0250] In a twenty-third embodiment, the invention relates to a polyisocyanate polyaddition product, obtained or obtainable by a process according to embodiment 21 or 22.

[0251] In a twenty-fourth embodiment, the invention relates to a coating composition for coating a substrate, comprising or consisting of at least one polyisocyanate polyaddition product according to embodiment 22, where the substrate is preferably a plastics part, a metal part or a shaped body made of wood.

Examples and Comparative Examples

[0252] The present invention will now be elucidated with reference to examples, but is not limited thereto.

[0253] In the examples, all percentages are to be understood as meaning percent by weight, unless otherwise stated. All reactions were carried out under an atmosphere of dry nitrogen. The preparation of the inventive catalysts and comparative catalysts listed in table 1, the synthesis of the ligands used for production thereof and the provision of the thermolatently catalyzed polyisocyanate curing agent formulations used is described in detail in WO 2021/249887 A1.

[0254] For better comparability of the activity of the activity of the catalysts to be used in accordance with the invention and the catalysts from the comparative examples, the amount of catalyst was reported as mg of Sn per kg of polyisocyanate curing agent (ppm), using, as polyisocyanate curing agent, the commercial product Desmodur ultra N 3300 (HC content 5 ppm) from Covestro AG, Leverkusen, D, NCO content 21.8%, and, as model compound for the isocyanate-reactive component (polyol), exactly one equivalent, based on the free isocyanate groups of the polyisocyanate curing agent, of triethylene glycol monoemthyl ether (product from Aldrich, Taufkirchen, Germany). Addition of 10% (based on Desmodur ultra N 3300) of n-butyl acetate ensured that, over the entire course of the reaction, samples of sufficiently low viscosity could be taken, which permit exact detection of the NCO content by titration according to DIN 53 185. The NCO content calculated at the start of the reaction without any NCOOH reaction is 11.1% and is normalized here to 100% as starting value. All titrated values are normalized thereto in table 2.

[0255] Comparative experiment 1 at a constant 30 C. shows the extremely slow decrease in the NCO content of the mixture in the uncatalyzed case (table 2, experiment 1). In order to enable comparison of the acceleration of the reaction at reaction temperature 50 C. (referred to in the real paint system as curing temperature), a series of experiments was additionally conducted, at first likewise without catalysis, firstly at a constant 30 C. (2 h) and then 50 C. (table 2, experiment 2). All comparative experiments 3 to 7 and the inventive examples (8 upward) were run according to the same regime: initially 2 h at 30 C. for assessment of thermolatency and then 50 C. for assessment of the reactivity at curing temperature.

TABLE-US-00001 TABLE 1 Overview of the catalysts used; 1-3 comparative, 4 upward inventive Catalyst IUPAC name.sup.1) 1 4,12-dibutyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane 2 4,12-dibutyl-2,6,10,14-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8- stannaspiro[7.7]pentadecane 3 4,12-dibutyl-2,2,6,6,10,10,14,14-octamethyl-1,7,9,15-tetraoxa-4,12-diaza-8- stannaspiro[7.7]pentadecane 4 4,12-dibutyl-2,2,10,10-tetramethyl-1,7,9,15-tetraoxa-4,12-diaza-8- stannaspiro[7.7]pentadecane 5 4,12-dibutyl-2,2,10-trimethyl-1,7,9,15-tetraoxa-4,12-diaza-8- stannaspiro[7.7]pentadecane 6 4,12-dibutyl-2,10-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane 7 4,12-dibutyl-2,2-dimethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane 8 4,12-dibutyl-2-methyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane 9 2,2,4,10,10,12-hexamethyl-1,7,9,15-tetraoxa-4,12-diaza-8-stannaspiro[7.7]pentadecane .sup.1)the IUPAC names were generated by the ChemDraw Professional Version 20.1.1125 program.

TABLE-US-00002 TABLE 2 Overview of the experiments conducted (examples 1-7: comparative examples, examples 8-15: inventive) NCO content of the mixture [% rel.] after [hh:mm] Ex. Cat. normalized to the calculated start value = 100% No. Cat. conc..sup.1) 00:30 1:00 1:30 2:00 2:10 2:20 2:30 3:00 4:00 6:00 1 none 0.sup.2) 100 99.9 99.8 99.6 99.6 99.5 99.5 99.4 99.4 99.2 2 none 0.sup.3) 100 100 99.7 99.6 99.5 98 97.5 96.2 92.3 85.3 3 Cat. 1 20.sup.3) 100 99.9 99.8 99.6 96.6 94.1 93.5 87.2 82.4 72.1 4 Cat. 1 60.sup.3) 100 98.2 97.4 97.2 91.8 90.5 89 82.6 56.9 37.2 5 Cat. 2 20.sup.3) 100 99.8 99.9 99.8 96.7 94.8 93.8 87 74.4 56.8 6 Cat. 2 60.sup.3) 99.8 97.9 96.2 95.9 88.8 86.4 85.9 82.6 56.9 22.3 7 Cat. 3 60.sup.3) 99.7 99.4 99.2 98.8 97.1 95.2 94.6 87.2 82.6 73.4 8 Cat. 4 20.sup.3) 99.6 98.5 97.2 96.8 87.4 85.1 81.1 77.7 54.1 18.9 9 Cat. 5 20.sup.3) 99.7 97.5 96.3 95.4 88.4 86.6 82.1 79.2 57.2 28.6 10 Cat. 6 20.sup.3) 99.7 97.8 96.2 95.7 88.8 86.4 85.2 81.2 59.1 32.1 11 Cat. 7 20.sup.3) 99.4 97.9 96.3 95.9 89.2 86.4 86.2 82 62.3 33.3 12 Cat. 8 20.sup.3) 99.5 98 96.5 95.9 94.8 93.2 88.8 83.3 65.5 48.9 13 Cat. 8 60.sup.3) 99.8 97.9 96.2 95.9 88.8 85.8 82 76.4 50.1 18.9 15 Cat. 9 20.sup.3) 99.5 98.4 97.0 96.6 87.2 84.9 80.0 76.2 48.1 16.7 .sup.1)Sn [ppm] based on polyisocyanate curing agent .sup.2)constant at 30 C. .sup.3)first 2 h at 30 C., then 50 C. - see text

[0256] As can be seen from the results shown in table 2, all systemsirrespective of whether they are inventive or notare sufficiently unreactive at 30 C. to be considered to be thermolatent. However, the systems of the invention with an unsymmetric ligand environment of the central atom at 50 C. display a much higher activity in some cases than is observed for the comparative systems based on catalysts 1-3. It is surprising in view of the very low reactivity of compound 3 and the moderate reactivity of compound 1 that compound 4, which is effectively a combination of the ligand environments of 1 and 3, is much more reactive than the two comparative catalysts. The person skilled in the art here would have expected reactivity between that of 1 and 3.

Examples 16-21: Experiment Series for Assessment of Color Stability

[0257] Catalysts 1, 2 and 4 according to table 1 were firstly dissolved in hexamethylene diisocyanate (HC content 25 ppm), choosing the catalyst concentration so as to result in each case in mixtures containing a uniform 0.1% tin (examples 16-18), and secondly blended as 10% solutions in n-butyl acetate (BA) with heating (50 C.) together with the Covestro Desmodur N 3900 polyisocyanate that contains iminooxadiazinedione groups (HC content 16 ppm) in such an amount as to result in a uniform 750 ppm of tin based on solvent-free Desmodur N 3900, which was then diluted to 90% solids by adding further butyl acetate (examples 19-21).

[0258] Hazen color number was measured by spectrophotometry according to DIN EN ISO 6271-2:2005-03 with a LICO 400 spectrophotometer from Lange, Germany.

[0259] These mixtures were stored at 50 C. under nitrogen, and the evolution of color was monitored; cf. table 3.

TABLE-US-00003 TABLE 3 Overview of the experiments conducted with regard to evolution of color of HDI (0.1% Sn) and Desmodur N 3900 (750 ppm of Sn based on polyisocyanate) (examples 16 and 17, and 19 and 20: comparative examples, examples 18 and 21: inventive) Example 16 17 18 19 20 21 Catalyst Days at 1 2 4 1 2 4 50 C. Hazen color number [Apha] 0 9 18 5 32 34 35 4 128 236 13 32 31 19 5 158 339 19 33 54 20 6 169 385 19 37 119 20 7 185 453 26 45 184 19 11 231 666 43 68 396 24 13 246 746 61 80 461 22 14 256 772 76 88 485 22 15 265 818 89 98 527 22 19 310 974 122 145 653 28 21 169 707 29 25 169 707 29 27 227 773 46 28 277 825 59

[0260] As can be seen, the inventive system based on catalyst 4 is distinctly superior to the structurally similar comparative systems (catalyst 2 is merely a positional isomer of 4!) with regard to the color stability of the isocyanate adducts as well.

Examples 22-27: Experiment Series for Assessment Of Color Stability

[0261] Catalysts 1, 2, 4 and 9 according to table 1 were firstly dissolved in bis(4-isocyanatocyclohexyl)methane (isomer mixture, Desmodur W product from Covestro, HC content <5 ppm, detection limit of the method chosen), choosing the catalyst concentration so as to result in each case in mixtures containing a uniform 0.1% tin (examples 22-25), and secondly catalysts 2 and 4 were blended as 10% solutions in n-butyl acetate (BA) with heating (50 C.) together with the Covestro Desmodur CQ U N 7300 polyisocyanate (HC content 12 ppm) in such an amount as to result in a uniform 750 ppm of tin based on solvent-free Desmodur CQ U N 7300, which was then diluted to 90% solids by adding further butyl acetate (examples 26-29).

[0262] Hazen color number was measured by spectrophotometry according to DIN EN ISO 6271-2:2005-03 with a LICO 400 spectrophotometer from Lange, Germany.

[0263] These mixtures were stored at 50 C. under nitrogen, and the evolution of color was monitored; cf. table 4.

TABLE-US-00004 TABLE 4 Overview of the experiments conducted with regard to evolution of color of Desmodur W (0.1% Sn) and Desmodur CQ U N 7300 (750 ppm of Sn based on polyisocyanate) (examples 22, 23 and 26: comparative examples, examples 24, 25 and 27: inventive) Example 22 23 24 25 26 27 Catalyst Days at 1 2 4 9 2 4 50 C. Hazen color number [Apha] 0 10 26 6 6 14 15 3 34 8 8 23 19 15 7 49 10 10 30 24 17 21 84 42 17 50 39 16 31 92 50 29 58 55 18 40 97 55 24 58 66 16 51 109 59 47 68 86 20 66 127 80 40 80 126 19 76 129 82 41 78 212 19 80 132 86 40 80 274 19 97 132 95 40 82 590 24 105 136 111 39 86 724 28 111 143 118 43 91 28 115 147 117 48 95 30 122 152 126 50 98 34 129 163 121 57 102 38 136 172 132 64 105 40 143 176 153 76 109 41 147 159 96 110 41 151 161 90 143 41 152 96 134 41 153 92 131 41 154 100 131 43 157 102 132 43 158 95 134 43 159 101 139 44 160 104 133 43 161 104 142 43 165 107 149 46 166 100 145 47 176 49 181 54

[0264] As can be seen, the products of the invention based on catalysts 4 and 9 are distinctly superior to the structurally similar comparative products (catalyst 2 is merely a positional isomer of 4!) with regard to the color stability of these isocyanate adducts as well. Without wishing to be bound to any theory, it seems to be plausible to assume that the lower residual halogen contents (detected by the HC content) of the isocyanates used here (comparing the results obtained with Desmodur W and HDI in particular) generally have a positive effect on color stability, and the catalysts used in accordance with the invention (4 and 9) again show distinctly better results than the comparative systems from the prior art (1 and 2).