Rapid-curing, migration-free composition based on organic polymers containing silane groups

Abstract

The invention relates to a composition comprising at least one organic polymer that contains silane groups and at least one catalyst of formula (I). The composition is low in emissions and low-odor, has a good shelf-life, cures rapidly to form a mechanically high-quality, durable material with a very low propensity for migration-related defects such as exudation or dirt retention by the substrate. The composition is particularly suitable for use as an adhesive, sealant or coating.

Claims

1. A process for producing a composition comprising at least one organic polymer containing silane groups; and at least one catalyst of the formula (I), ##STR00009## wherein A is an aliphatic or cycloaliphatic or arylaliphatic hydrocarbyl radical which has 1 to 100 carbon atoms, optionally contains unsaturated moieties, optionally contains heteroatoms and optionally has amino groups or hydroxyl groups, or together with R.sup.1 is a divalent, optionally branched alkylene radical which has 4 to 12 carbon atoms and optionally contains a heteroatom, R.sup.1 is hydrogen or an alkyl or cycloalkyl or aralkyl radical having 1 to 8 carbon atoms, or together with A is a divalent, optionally branched alkylene radical which has 4 to 12 carbon atoms and optionally contains a heteroatom, and R.sup.2 and R.sup.5 are each independently an alkyl, cycloalkyl or aralkyl radical which has 1 to 18 carbon atoms and optionally contains heteroatoms, wherein A is a different radical from each of R.sup.2 and R.sup.5; wherein the catalyst of the formula (I) does not contain any nitrogen atom bonded directly to an aromatic ring or part of a heteroaromatic ring system, and the catalyst of the formula (I) is free of silane groups, and wherein the composition is free of carbodiimide, the process comprising preparing a catalyst of the formula (I), wherein at least one amine of the formula (II) is reacted with at least one carbodiimide of the formula (III), ##STR00010## adding the prepared catalyst to the at least one organic polymer containing silane groups or to a composition comprising the at least one organic polymer containing silane groups, wherein the adding is effected by preparing the catalyst in the presence of the at least one organic polymer containing silane groups.

2. The process as claimed in claim 1, wherein A is selected from the group consisting of n-hexyl, n-octyl, 2-ethylhexyl, n-decyl, lauryl, cyclohexyl, benzyl, 2-methoxyethyl, 3-methoxypropyl, polyoxyalkylene radical having oxyethylene and 1,2-oxypropylene units and a molecular weight in the range from about 180 to 600 g/mol, N-methyl-3-aminopropyl, N-(2-ethylhexyl)-3-aminopropyl, N-cyclohexyl-3-aminopropyl, 3-(N,N-dimethylamino)propyl, 2-aminopropyl, 3-aminopropyl, 3-aminopentyl, 5-amino-4-methylpentyl, 5-amino-2-methylpentyl, 6-aminohexyl, 6-amino-3,3(5),5-trimethylhexyl, 6-amino-2,2(4),4-trimethylhexyl, 8-aminooctyl, 10-aminodecyl, 12-aminododecyl, 3-aminomethyl-3,5,5-trimethylcyclohexyl, 3-amino-1,5,5-trimethylcyclo-hexylmethyl, 3-aminomethylcyclohexylmethyl, 4-aminomethylcyclohexyl-methyl, 3-aminomethylbenzyl, 5-amino-3-oxapentyl, -2-aminopropyl-polyoxypropylene radical having a molecular weight in the range from about 200 to 500 g/mol, 2-hydroxypropyl, 3-hydroxypropyl, 1,1-dimethyl-2-hydroxyethyl, and 5-hydroxy-3-oxapentyl.

3. The process as claimed in claim 1, wherein R.sup.1 is hydrogen.

4. The process as claimed in claim 1, wherein R.sup.2 and R.sup.5 are each independently ethyl, isopropyl, tert-butyl, 3-(dimethylamino)propyl or cyclohexyl.

5. The process as claimed in claim 1, wherein the organic polymer containing silane groups is a polyolefin containing silane groups or a polyester containing silane groups or a poly(meth)acrylate containing silane groups or a polyether containing silane groups or a mixed form of these polymers.

6. The process as claimed in claim 1, wherein at least one organotitanate is additionally present.

7. The process as claimed in claim 1, wherein the amine of the formula (II) is selected from the group consisting of n-hexylamine, n-octylamine, 2-ethylhexylamine, n-decylamine, laurylamine, cyclohexyl-amine, benzylamine, 2-methoxyethylamine, 3-methoxypropylamine, polyoxyalkyleneamine having oxyethylene and 1,2-oxypropylene units and a mean molecular weight in the range from 180 to 600 g/mol, N-methyl-1,3-propanediamine, N-(2-ethylhexyl)-1,3-propanediamine, N-cyclohexyl-1,3-propanediamine, N,N-dimethyl-1,3-propanediamine, 1,2-propanediamine, 1,3-propanediamine, 1,3-pentanediamine, 1,5-diamino-2-methylpentane, 1,6-hexanediamine, 2,2,4- and 2,4,4-trimethylhexa-methylenediamine, 1,8-octanediamine, 1,10-decanediamine, 1,12-dodecanediamine, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 1,3-bis(aminomethyl)benzene, bis(2-aminoethyl) ether, polyoxypropylene-diamine having a mean molecular weight in the range from about 220 to 500 g/mol, 1-amino-2-propanol, 3-amino-1-propanol, 2-amino-2-methyl-1-propanol, and 2-(2-aminoethoxy)ethanol.

8. The process as claimed in claim 1, wherein the carbodiimide of the formula (III) is selected from the group consisting of N,N-diisopropylcarbodiimide, N,N-di-tert-butylcarbodiimide, N,N-dicyclohexylcarbodiimide and N-ethyl-N-(3-dimethylaminopropyl)-carbodiimide.

9. A method for adhesively bonding, sealing, or coating a substrate, including the step of applying the composition produced in the process of claim 1 as an adhesive, sealant or coating to the substrate and exposing the composition to water.

10. A cured composition obtained from the composition produced in the process of claim 1 after it has been cured with water.

11. A method for catalytic crosslinking an organic polymer containing silane groups comprised in the composition produced in the process of claim 1, including exposing the composition to water.

12. A catalyst comprised of 1-(3-(N,N-dimethylamino)propyl)-2,3-dicyclohexylguanidine.

Description

EXAMPLES

(1) Adduced hereinafter are working examples which are intended to elucidate the invention described in detail. It will be appreciated that the invention is not restricted to these described working examples.

(2) Standard climatic conditions refer to a temperature of 231 C. and a relative air humidity of 505%.

(3) .sup.1H NMR spectra were measured on a spectrometer of the Bruker Ascend 400 type at 400.14 MHz; the chemical shifts are reported in ppm relative to tetramethylsilane (TMS). No distinction was made between true and pseudo-coupling patterns.

(4) Infrared spectra (FT-IR) were measured on a Nicolet iS5 FT-IR instrument from Thermo Scientific equipped with a horizontal ATR measurement unit with a diamond crystal. Liquid samples were applied undiluted as films; solid samples were dissolved in CH.sub.2Cl.sub.2. The absorption bands are reported in wavenumbers (cm.sup.1) (measurement window: 4000-650 cm.sup.1).

(5) Viscosities were measured on a thermostated Rheotec RC30 cone-plate viscometer (cone diameter 50 mm, cone angle 1, cone tip-plate distance 0.05 mm, shear rate 10 s.sup.1).

(6) The skin time (ST) was determined by applying a few grams of the composition to cardboard in a layer thickness of about 2 mm and measuring, under standard climatic conditions, the time until, when the surface of the composition was gently tapped by means of an LOPE pipette, no residues remained any longer on the pipette for the first time. The characteristics of the surface were tested by touch.

(7) The mechanical properties of tensile strength, elongation at break and modulus of elasticity (at 0-5% and at 0-50% elongation) were measured in accordance with DIN EN 53504 at a pulling speed of 200 win/min.

Preparation of Catalysts of the Formula (I)

Catalyst K-1: 1-(3-Triethoxysilylpropyl)-2,3-dicyclohexylguanidine

(8) In a round-bottom flask, 6.69 g of 3-aminopropyltriethoxysilane and 5.17 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 100 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 40 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 11.38 g of a colorless, low-odor oil.

(9) .sup.1H NMR (CDCl.sub.3): 0.5-0.75 (m, 2H, CH.sub.2Si), 1.1-1.4 (m, 21H), 1.55-2.0 (m, 10H), 2.95-3.1 (m, 2H, NCH.sup.Cy), 3.1-3.3 (m, 2H, CH.sub.2N), 3.85 (q, 6H, CH.sub.2O). FT-IR: 2972, 2924, 2851, 1641 (CN), 1496, 1447, 1389, 1363, 1326, 1297, 1237, 1165, 1101, 1074, 953, 888, 773.

Catalyst K-2: 1-(3-Trimethoxysilylpropyl)-2,3-dicyclohexylguanidine

(10) In a round-bottom flask, 6.42 g of 3-aminopropyltrimethoxysilane and 5.73 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 110 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 24 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 10.66 g of a pale yellow, low-odor oil.

(11) .sup.1H NMR (CDCl.sub.3): 0.5-0.75 (m, 2H, CH.sub.2Si), 1.1-1.4 (m, 12H), 1.55-2.0 (m, 10H), 2.95-3.1 (m, 2H, NCH.sup.Cy), 3.1-3.3 (m, 2H, CH.sub.2N), 3.55 (s, 9H, CH.sub.3O).

(12) FT-IR: 3405 (NH), 2923, 2849, 1639 (CN), 1498, 1448, 1327, 1305, 1237, 1189, 1081, 979, 889, 814, 787, 713.

Catalyst K-3: 1-(N-(3-Trimethoxysilylpropyl)-2-aminoethyl)-2,3-dicyclohexyl-guanidine

(13) In a round-bottom flask, 6.11 g of N-(2-aminoethyl)-3-aminopropyltrimethoxy-silane (Silquest A-1120, from Momentive) and 5.16 g of N,N-dicyclohexyl-carbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 25 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. This gave a colorless, low-odor oil.

(14) .sup.1H NMR (CDCl.sub.3): 0.6-0.7 (m, 2H, CH.sub.2Si), 1.0-1.5 (m, 10H), 1.55-2.0 (m, 12H), 2.60 (m, 2H, CH.sub.2N), 2.75 (m, 2H, CH.sub.2N), 2.9 (m, 1H, NCH.sup.Cy), 3.11 (m, 2H, CH.sub.2N), 3.23 (m, 1H, NCH.sup.Cy), 3.5-3.6 (br s, 9H, CH.sub.3O).

(15) FT-IR: 3233, 2924, 2839, 1637 (CN), 1605, 1538, 1448, 1409, 1364, 1330, 1269, 1257, 1189, 1079, 889, 813, 781.

Catalyst K-4: 1-(N-(3-Triethoxysilylpropyl)-2-aminoethyl)-2, 3-dicyclohexyl-guanidine

(16) In a round-bottom flask, 7.27 g of N-(2-aminoethyl)-3-aminopropyltriethoxy-silane (Geniosil GF-94, from Wacker Chemie) and 5.16 g of N, N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 12 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. This gave a colorless, low-odor oil.

(17) .sup.1H NMR (CDCl.sub.3): 0.6-0.7 (m, 2H, CH.sub.2Si), 1.05-1.45 (m, 19H), 1.55-2.1 (m, 12H), 2.60 (m, 2H, CH.sub.2N), 2.75 (m, 2H, CH.sub.2N), 2.9 (m, 1H, NCH.sup.Cy), 3.11 (m, 2H, CH.sub.2N), 3.23 (m, 1H, NCH.sup.Cy), 3.70-3.85 (m, 6H, OCH.sub.2CH.sub.3).

(18) FT-IR: 3232, 2972, 2924, 2851, 1640 (CN), 1605, 1544, 1448, 1389, 1344, 1269, 1257, 1165, 1101, 1074, 954, 889, 772, 671.

Catalyst K-5: 1-Hexyl-2,3-dicyclohexylguanidine

(19) In a round-bottom flask, 2.05 g of n-hexylamine and 3.68 g of N, N-dicyclo-hexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-1R spectroscopy. After 17 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 5.20 g of a colorless, low-odor oil.

(20) .sup.1H NMR (CDCl.sub.3): 0.9 (t, 3H, CH.sub.3CH.sub.2), 1.1-1.25 (m, 6H), 1.25-1.4 (m, 10H), 1.45-1.65 (m, 4H), 1.7-1.8 (m, 4H), 1.85-1.95 (m, 4H), 2.95-3.05 (m, 2H, CH.sub.2N), 3.1-3.3 (m, 2H, NCH.sup.Cy).

(21) FT-IR: 3305 (NH), 2952, 2850, 1636 (CN), 1495, 1448, 1361, 1322, 1253, 1147, 1112, 1031, 977, 888, 723.

Catalyst K-6: 1-Hexyl-2,3-diisopropylguanidine

(22) In a round-bottom flask, 2.93 g of n-hexylamine and 2.89 g of N, N-diisopropyl-carbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 4.5 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 4.96 g of a pale yellow, low-odor oil.

(23) FT-IR: 3304 (N-H), 2959, 2926, 2857, 1633 (CN), 1510, 1466, 1378, 1363, 1336, 1172, 1125, 723.

Catalyst K-7: 1-Benzyl-2,3-dicyclohexylguanidine

(24) In a round-bottom flask, 6.43 g of benzylamine and 10.32 g of N, N-dicyclo-hexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 70 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 15.67 g of a pale yellow, low-odor oil.

(25) .sup.1H NMR (CDCl.sub.3): 1.1-1.5 (m, 10H), 1.55-2.0 (m, 10H), 3.11 (m, 2H, NCH.sup.Cy), 3.6 (br s, 1H, NH), 4.31 (m, 2H, CH.sub.2Ph), 4.37 (br s, 1H, NH), 7.15-7.35 (m, 5H, Ph-H).

(26) FT-IR: 3432, 3270, 3060, 3025, 2923, 2849, 1633 (CN), 1493, 1448, 1335, 1328, 1253, 1236, 1188, 1146, 1112, 1072, 1028, 1002, 977, 888, 860, 802, 730, 696.

Catalyst K-8: 1-(2-Ethylhexyl)-2,3-dicyclohexylguanidine

(27) In a round-bottom flask, 7.76 g of 2-ethylhexylamine and 10.32 g of N, N-dicyclo-hexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 70 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 16.78 g of an orange-yellow, low-odor oil.

(28) .sup.1H NMR (CDCl.sub.3): 0.88 (m, 6H, CH.sub.3), 1.06-1.2 (m, 7H), 1.2-1.4 (m, 10H), 1.4-1.5 (m, 2H), 1.55-2.0 (m, 10H), 2.86-3.0 (m, 2H, CH.sub.2N), 3.0-3.2 (m, 2H, NCH.sup.Cy).

(29) FT-IR: 3440, 2954, 2923, 2851, 1644 (CN), 1493, 1448, 1361, 1335, 1255, 1236, 1188, 1145, 1090, 1050, 1027, 978, 927, 888, 845, 769, 726.

Catalyst K-9: 1-(5-Hydroxy-3-oxapentyl)-2,3-dicyclohexylguanidine

(30) In a round-bottom flask, 3.55 g of 2-(2-aminoethoxy)ethanol (Diglycolamine Agent, from Huntsman) and 6.81 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-1R spectroscopy. After 24 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 10.29 g of a pale yellow, low-odor oil.

(31) .sup.1H NMR (CDCl.sub.3): 1.05-1.3 and 1.3-1.45 (2m, 10H, CH.sub.2), 1.54-1.78 (m, 8H), 1.88-2.0 (m, 4H), 3.13 (t, 2H, CH.sub.2N), 3.69 (m, 4H, CH.sub.2O), 3.81 (t, 2H, OCH.sub.2CH.sub.2N).

(32) FT-1R: 3355(OH), 2922, 2849, 1617 (CN), 1520, 1447, 1340, 1257, 1240, 1117, 1066, 888, 717.

Catalyst K-10: 1-(3-Aminopropyl)-2,3-dicyclohexylguanidine

(33) In a round-bottom flask, 2.50 g of 1,3-diaminopropane and 6.89 g of N, N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 1 hour, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 9.36 g of a pale yellow, low-odor oil.

(34) .sup.1H NMR (CDCl.sub.3): 1.05-1.2 and 1.25-1.40 (2m, 10H), 1.54-1.78 (m, 10H), 1.88-2.0 (m, 4H), 2.73 (m, 2H), 3.12 (m, 2H), 3.22 (br s, 2H).

(35) FT-IR: 3371 (NH), 2921, 2849, 1627 (CN), 1502, 1447, 1324, 1238, 1147, 1111, 888, 713.

Catalyst K-11: 1-(3-Cyclohexylaminopropyl)-2,3-dicyclohexylguanidine

(36) In a round-bottom flask, 25.78 g of 3-(cyclohexylamino)propylamine (from BASF) and 30.95 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 48 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 54.4 g of a pale yellow, low-odor oil.

(37) FT-IR: 3283 (NH), 2921, 2849, 1634 (CN), 1493, 1447, 1343, 1322, 1256, 1145, 1111, 888, 713.

Catalyst K-12: 1-(3-Cyclohexylaminopropyl)-2,3-diisopropylguanidine

(38) In a round-bottom flask, 34.38 g of 3-(cyclohexylamino)propylamine (from BASF) and 25.24 g of N,N-diisopropylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-1R spectroscopy. After 2 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 56.50 g of a pale yellow, low-odor oil.

(39) FT-IR: 3292 (NH), 2960, 2924, 2852, 1633 (CN), 1505, 1448, 1361, 1329, 1176, 1125, 889, 714.

Catalyst K-13: 1-(6-Amino-2,2(4),4-trimethylhexyl)-2,3-dicyclohexylguanidine and 1-(6-amino-3,3(5),5-trimethylhexyl)-2,3-dicyclohexylguanidine

(40) In a round-bottom flask, 16.62 g of Vestamin TMD (mixture of 2,2,4- and 2,4,4-trimethyl-1,6-hexamethylenediamine, from Evonik) and 20.63 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 3 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 36.5 g of a pale yellow, low-odor oil.

(41) FT-IR: 3281 (NH), 2923, 2850, 1635 (CN), 1496, 1463, 1448, 1362, 1325, 1284, 1237, 1188, 1146, 1112, 1090, 1071, 1051, 1027, 977, 888, 860, 845, 804, 785, 714.

Catalyst K-14: 1-(5-Amino-2-methylpentyl)-2, 3-dicyclohexylguanidine and 1-(5-amino-4-methylpentyl)-2,3-dicyclohexylguanidine

(42) In a round-bottom flask, 12.20 g of 2-methylpentane-1,5-diamine (MPMD; from Invista) and 20.63 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-1R spectroscopy. After 3 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 32.3 g of a pale yellow, low-odor oil.

(43) FT-IR: 3304 (NH), 2922, 2849, 1636 (CN), 1495, 1462, 1447, 1361, 1324, 1285, 1237, 1188, 1145, 1112, 1071, 1051, 1027, 977, 926, 888, 859, 845, 802, 786, 715.

Catalyst K-15: 1-(3-(N,N-Dimethylamino)propyl)-2,3-dicyclohexylguanidine

(44) In a round-bottom flask, 6.64 g of 3-(N,N-dimethylamino)propylamine and 10.32 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 48 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 15.43 g of an orange-yellow, low-odor oil.

(45) .sup.1H NMR (CDCl.sub.3): 1.05-1.38 (m, 10H), 1.54-1.65 (m, 2H), 1.65-1.80 (m, 6H), 1.80-2.0 (m, 4H), 2.0 (s, 6H, NMe.sub.2), 2.30 (m, 2H, CH.sub.2NMe.sub.2), 3.06-3.25 (m, 4H).

(46) FT-1R: 3291, 2922, 2850, 2814, 1635 (CN), 1494, 1447, 1361, 1322, 1256, 1236, 1147, 1098, 1068, 1040, 996, 977, 888, 845, 785, 713.

Catalyst K-16: 1-(-Methoxy-polyoxypropylene-polyoxyethylene)-2, 3-dicyclohexylguanidine having a molecular weight of about 810 g/mol

(47) In a round-bottom flask, 14.32 g of polyoxypropylenemonoamine having a mean molecular weight of about 600 g/mol (Jeffamine M-600 from Huntsman, amine content about 1.7 meq/g) and 4.14 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 72 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. This gave 18.45 g of a pale yellow, colorless oil.

(48) FT-IR: 3367 (NH), 2969, 2926, 2854, 1640 (CN), 1449, 1372, 1342, 1297, 1255, 1100, 1014, 925, 889, 861, 715.

Catalyst K-17: 1,2,3-Tricyclohexylguanidine

(49) In a round-bottom flask, 7.99 g of cyclohexylamine and 15.83 g of N, N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 48 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. Thereafter, the reaction mixture was freed of the volatile constituents under reduced pressure. This gave 23.44 g of a low-odor brown solid.

(50) .sup.1H NMR (CDCl.sub.3): 1.05-1.38 (m, 16H), 1.54-1.65 (m, 4H), 1.65-1.80 (m, 6H), 1.8-2.0 (m, 6H), 3.06-3.25 (br s, 3H).

(51) FT-1R: 2923, 2851, 1643 (CN), 1491,1448, 1363, 1335, 1322, 1281, 1254, 1234, 1145, 1111, 978, 927, 846, 749, 720, 668.

Catalyst K-18: 1-(3-(3-(N,N-Dimethylamino)propyl)aminopropyl)-2, 3-dicyclohexylguanidine

(52) In a round-bottom flask, 9.40 g of N.sup.1-((3-dimethylamino)propyl)-1, 3-diaminopropane and 11.65 g of N,N-dicyclohexylcarbodiimide were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 3 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. This gave a yellow, low-odor oil.

(53) .sup.1H NMR (CDCl.sub.3): 1.05-1.38 (m, 10H), 1.54-1.70 (m, 10H), 1.80-2.0 (m, 4H), 2.21 (s, 6H, NMe.sub.2), 2.30 (m, 2H, CH.sub.2NMe.sub.2), 2.58-2.70 (m, 4H, CH.sub.2NH), 3.06-3.25 (m, 4H).

(54) FT-IR: 3270, 2922, 2850, 2813, 2784, 2763, 1633 (CN), 1495, 1447, 1359, 1335, 1321, 1257, 1237, 1097, 1041, 977, 888, 842, 785, 719.

Catalyst Ref-1: 1-Hexyl-2,3-bis(2,6-diisopropylphenyl)guanidine

(55) In a round-bottom flask, 1.20 g of n-hexylamine and 4.01 g of bis(2, 6-diisopropylphenyl)carbodiimide (Stabilisator 7000 from Raschig) were mixed and the mixture was heated to 120 C. while stirring. At regular intervals, the reaction mixture was examined by means of FT-IR spectroscopy. After 2 hours, the carbodiimide band at about 2120 cm.sup.1 had disappeared completely. This gave a yellow, low-odor oil.

(56) FT-1R: 3442, 3397, 2957, 2925, 2866, 1637 (CN), 1585, 1513, 1459, 1434, 1391, 1361, 1324, 1300, 1255, 1198, 1179, 1126, 1098, 1058, 1044, 956, 934, 895, 831, 804, 764, 699.

Catalyst Ref-2: 1-Phenyl-2,3-diisopropylguanidine

(57) In a test tube, 2.24 g of aniline and 2.52 g of N,N-diisopropylcarbodiimide (DIC) were mixed and the mixture was reacted in a microwave at a temperature of 220 C. and a pressure of 150 Pa for 10 minutes. The product obtained was recrystallized from a mixture of ethyl acetate and heptane in a ratio of 1:1. This gave 2.77 g of a white solid.

(58) .sup.1H NMR (CDCl.sub.3): 1.08 (d, 24H, CH.sub.3), 3.65 (m, 2H, CH aliph.), 6.75-6.80 (m, 2H, CH arom.), 6.82-6.88 (m, 1H, CH arom.), 7.14-7.20 (m, 2H, CH arom.).

(59) FT-1R: 3346, 3055, 2966, 2930, 2869, 1705, 1630 (CN), 1587, 1532, 1500, 1487, 1464, 1455, 1444, 1383, 1364, 1313, 1225, 1174, 1124, 1069, 1030, 996, 941, 898, 864, 831, 810, 755, 698.

Preparation of Polyethers Containing Silane Groups

Polymer STP-1

(60) With exclusion of moisture, 1000 g of Acclaim 12200 polyol (polyoxy-propylenediol having a low level of unsaturation, from Bayer; OH number 11.0 mg KOH/g), 43.6 g of isophorone diisocyanate (IPDI; Vestanat IPDI, from Evonik), 126.4 g of diisodecyl phthalate (DIDP) and 0.1 g of bismuth tris(neodecanoate) (10% by weight in DIDP) were heated up to 90 C. while stirring constantly and left at this temperature until the content of free isocyanate groups determined by titrimetry had reached a stable value of 0.63% by weight. Subsequently, 63.0 g of diethyl N-(3-trimethoxysilylpropyl)-aminosuccinate (adduct formed from 3-aminopropyltrimethoxysilane and diethyl maleate; prepared according to the details in U.S. Pat. No. 5,364,955) were mixed in and the mixture was stirred at 90 C. until it was no longer possible to detect any free isocyanate by means of FT-IR spectroscopy. The polyether containing trimethoxysilane groups thus obtained, having a silane equivalent weight of about 6880 g/eq (calculated from the amounts used), was cooled down to room temperature and stored with exclusion of moisture.

Polymer STP-2

(61) With exclusion of moisture, 1000 g of Acclaim 12200 polyol (polyoxy-propylenediol having a low level of unsaturation, from Bayer; OH number 11.0 mg KOH/g), 43.6 g of isophorone diisocyanate (IPDI; Vestanat IPDI, from Evonik), 126.4 g of diisodecyl phthalate (DIDP) and 0.1 g of bismuth tris(neodecanoate) (10% by weight in DIDP) were heated up to 90 C. while stirring constantly and left at this temperature until the content of free isocyanate groups determined by titrimetry had reached a stable value of 0.64% by weight. Subsequently, 70.6 g of diethyl N-(3-triethoxysilylpropyl)-aminosuccinate (adduct formed from 3-aminopropyltriethoxysilane and diethyl maleate) were mixed in and the mixture was stirred at 90 C. until it was no longer possible to detect any free isocyanate by means of FT-IR spectroscopy. The polyether containing triethoxysilane groups thus obtained, having a silane equivalent weight of about 6920 g/eq (calculated from the amounts used), was cooled down to room temperature and stored with exclusion of moisture.

Commercial Catalysts Used and Abbreviations Therefor

(62) DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene TMG 1,1,3,3-Tetramethylguanidine DHA N,N-Di-n-hexylacetamidine IBAY Tyzor IBAY, bis(ethylacetoacetato)diisobutoxytitanium(IV), from Dorf Ketal MTHP 2-Methyl-1,4,5,6-tetrahydropyrimidine TMTHP 2,5,5-Trimethyl-1,4,5,6-tetrahydropyrimidine DBTDL Dibutyltin(IV) dilaurate

Compositions Based on Polymers Containing Silane Groups

(63) Comparative examples are identified by (Ref) in tables 1 to 10.

Compositions B1 to B22 and Comparisons B23 to B31

(64) A composition composed of 96.5 g of polymer STP-1, 0.5 g of vinyltrimethoxy-silane and 3.0 g of 3-aminopropyltrimethoxysilane was mixed with various catalysts in the amounts specified according to table 1, and the mixture was tested for viscosity and skin time (ST) under standard climatic conditions, before and after storage. The skin time serves as a measure of the activity of the catalyst in relation to the crosslinking reaction of the silane groups, i.e. of the crosslinking rate; the change in viscosity and the skin time after storage are a measure of storage stability. In addition, the mixture applied, after 24 hours under standard climatic conditions, was tested as to whether the surface was dry as desired or whether a greasy film had formed, which is a sign of the exudation of the catalyst owing to pure compatibility with the cured polymer, and/or whether the surface was tacky, which is a sign of incomplete curing. In addition, the mixture was used to produce a film of thickness 2 mm, which was left to cure under standard climatic conditions for 7 days and tested for mechanical properties. The results are shown in tables 1 and 2. Comp. stands for composition.

(65) TABLE-US-00001 TABLE 1 Viscosity [Pa .Math. s] ST Comp. Catalyst Amount Concentration.sup.1 freshly stored.sup.2 increase freshly stored.sup.2 B1 K-1 0.41 g 1.0 19.8 23.6 19% 21 25 B2 K-2 0.37 g 1.0 20.2 22.3 10% 24 28 B3 K-1 0.21 g 0.5 23.6 28.0 19% 9 27 IBAY 0.22 g 0.5 B4 K-2 0.19 g 0.5 24.4 30.5 25% 12 18 IBAY 0.22 g 0.5 B5 K-3 0.80 g 1.9 27.2 32.4 19% 27 33 B6 K-4 0.87 g 1.9 26.8 34.1 27% 30 32 B7 K-5 0.56 g 1.9 37.6 37.7 0.3% 12 13 B8 K-5 0.15 g 0.5 48.0 50.6 5% 20 25 IBAY 0.22 g 0.5 B9 K-6 0.42 g 1.9 24.1 27.0 12% 15 18 B10 K-7 0.58 g 1.9 27.8 30.0 8% 20 19 B11 K-8 0.62 g 1.9 26.2 29.4 12% 16 17 B12 K-9 0.57 g 1.9 26.1 31.5 21% 13 16 B13 K-9 0.15 g 0.5 35.0 39.4 11.2% 21 28 IBAY 0.22 g 0.5 B14 K-10 0.51 g 1.9 21.4 28.4 33% 12 13 B15 K-11 0.66 g 1.9 24.1 27.3 13% 5 13 B16 K-12 0.52 g 1.9 22.8 28.0 23% 9 13 B17 K-13 0.67 g 1.9 28.4 39.9 41% 11 7 B18 K-14 0.59 g 1.9 27.7 40.1 45% 14 8 B19 K-15 0.56 g 1.9 24.3 25.7 6% 6 7 B20 K-15 0.15 g 0.5 50.9 52.0 2% 12 17 IBAY 0.22 g 0.5 B21 K-17.sup.3 0.57 g 1.9 26.0 27.2 4% 13 14 B22 K-18 0.67 g 1.9 21.8 26.9 23% 8 12 B23 DBU 0.28 g 1.9 27.2 36.9 36% 25 29 (Ref) B24 TMG 0.21 g 1.9 22.3 24.6 10% 65 75 (Ref) B25 DHA 0.42 g 1.9 24.8 32.6 31% 40 48 (Ref) B26 IBAY 0.87 g 2.0 24.8 30.2 22% 45 2 h (Ref) B27 DBU 0.07 g 0.5 24.9 28.1 13% 15 55 (Ref) IBAY 0.22 g 0.5 B28 TMG 0.06 g 0.5 23.2 25.0 8% 37 111 (Ref) IBAY 0.22 g 0.5 B29 24.8 28.9 17% 87 110 (Ref) B30 Ref-1 0.85 g 1.9 22.3 22.4 0% 95 100 (Ref) B31 Ref-2.sup.3 0.40 g 1.9 20.5 21.8 6% 108 107 (Ref) .sup.1mmol of amidine or guanidine groups or metal atoms per 100 g of polyether containing silane groups. .sup.2for 7 days at 60 C. in a closed container. .sup.3as a solution (20% by weight) in N-ethylpyrrolidone.

(66) TABLE-US-00002 TABLE 2 Elonga- Modulus of Surface Tensile tion elasticity Comp. after 24 h strength at break 0-5% 0-50% B1 dry 0.59 MPa 77% 1.18 MPa 0.77 MPa B2 dry 0.57 MPa 72% 1.17 MPa 0.78 MPa B3 dry 0.63 MPa 90% 1.13 MPa 0.75 MPa B4 dry 0.54 MPa 69% 1.17 MPa 0.76 MPa B5 dry 0.78 MPa 116% 1.11 MPa 0.80 MPa B6 dry 0.73 MPa 98% 1.08 MPa 0.81 MPa B7 dry 0.60 MPa 76% 1.18 MPa 0.81 MPa B8 dry 0.59 MPa 73% 1.26 MPa 0.81 MPa B9 dry 0.57 MPa 75% 1.14 MPa 0.76 MPa B10 dry 0.74 MPa 114% 0.98 MPa 0.76 MPa B11 dry 0.69 MPa 105% 1.08 MPa 0.76 MPa B12 dry 0.61 MPa 78% 1.05 MPa 0.75 MPa B13 dry 0.68 MPa 95% 1.17 MPa 0.80 MPa B14 dry 0.70 MPa 98% 1.04 MPa 0.78 MPa B15 dry 0.69 MPa 97% 1.07 MPa 0.78 MPa B16 dry 0.70 MPa 95% 1.04 MPa 0.79 MPa B17 dry 0.72 MPa 102% 1.23 MPa 0.79 MPa B18 dry 0.70 MPa 91% 1.20 MPa 0.81 MPa B19 dry 0.73 MPa 105% 1.11 MPa 0.78 MPa B20 dry 0.65 MPa 87% 1.24 MPa 0.81 MPa B21 dry 0.59 MPa 73% 1.19 MPa 0.81 MPa B22 dry 0.63 MPa 84% 1.23 MPa 0.81 MPa B23 (Ref) greasy 0.58 MPa 72% 1.16 MPa 0.77 MPa B24 (Ref) tacky 0.62 MPa 90% 1.19 MPa 0.75 MPa B25 (Ref) slightly tacky 0.63 MPa 82% 1.10 MPa 0.78 MPa B26 (Ref) tacky 0.59 MPa 91% 1.05 MPa 0.69 MPa B27 (Ref) slightly greasy 0.60 MPa 81% 1.11 MPa 0.76 MPa B28 (Ref) slightly tacky 0.69 MPa 100% 1.13 MPa 0.76 MPa B29 (Ref) dry 0.68 MPa 112% 1.02 MPa 0.69 MPa B30 (Ref) dry 0.59 MPa 79% 1.17 MPa 0.74 MPa B31 (Ref) dry 0.76 MPa 117% 0.79 MPa 0.75 MPa

Compositions B32 to B49 and Comparisons B50 to B56

(67) A composition composed of 95.9 g of polymer STP-2, 0.4 g of vinyltriethoxy-silane and 3.7 g of N-(2-aminoethyl)-3-aminopropyltriethoxysilane was blended with various catalysts in the amounts specified according to table 3 and the mixture was tested as described for composition B1 for viscosity, skin time (ST), surface characteristics and mechanical properties. The results are shown in tables 3 and 4. Comp. stands for composition.

(68) TABLE-US-00003 TABLE 3 Cata- Concen- Viscosity [Pa .Math. s] ST Comp. lyst Amount tration.sup.1 freshly stored.sup.2 increase freshly stored.sup.2 B32 K-1 1.56 g 3.8 46.2 50.4 9% 50 50 B33 K-2 1.41 g 3.8 48.0 53.8 12% 55 39 B34 K-1 0.62 g 1.5 40.3 48.0 19% 72 70 IBAY 0.82 g 1.9 B35 K-2 0.55 g 1.5 39.5 48.9 24% 70 50 IBAY 0.82 g 1.9 B36 K-3 1.56 g 3.8 30.4 33.6 10% 5 h 30 2 h 12 B37 K-4 1.72 g 3.8 31.5 34.6 10% 2 h 7 4 h 56 B38 K-5 1.15 g 3.8 35.1 38.5 10% 60 80 B39 K-5 0.58 g 1.9 50.1 54.5 9% 100 85 IBAY 0.79 g 1.6 B40 K-6 0.83 g 3.8 33.8 37.3 10% 65 60 B41 K-8 1.22 g 3.8 33.6 35.4 5% 128 100 B42 K-9 1.14 g 3.8 34.6 35.7 3% 90 70 643 K-9 0.58 g 1.9 49.8 59.9 20% 95 44 IBAY 0.79 g 1.6 B44 K-13 1.33 g 3.8 33.9 42.7 26% 92 40 B45 K-14 1.18 g 3.8 33.3 41.3 24% 81 35 B46 K-15 1.12 g 3.8 34.5 37.2 8% 56 36 B47 K-15 0.58 g 1.9 51.2 59.0 15% 50 50 IBAY 0.79 g 1.6 B48 K-16 2.94 g 3.8 32.9 35.4 8% 75 75 B49 K-17.sup.3 1.14 g 3.8 31.3 33.9 8% 77 66 B50 (Ref) DBU 0.55 g 3.8 48.8 58.1 19% 127 155 B51 (Ref) TMG 0.42 g 3.8 44.5 53.4 20% >12 h >12 h B52 (Ref) DHA 0.83 g 3.8 35.5 55.4 56% 5 h 30 4 h 15 B53 (Ref) MTHP 0.36 g 3.8 46.5 54.0 16% 120 110 B54 (Ref) TMTHP.sup.3 0.36 g 3.0 30.0 34.4 15% 3 h 40 3 h B55 (Ref) DBU 0.22 g 1.5 43.2 45.6 6% 3 h 20 3 h IBAY 0.82 g 1.9 B56 (Ref) TMG 0.17 g 1.5 38.2 42.8 12% >24 h >24 h IBAY 0.82 g 1.9 .sup.1mmol of amidine or guanidine groups or metal atoms per 100 g of polyether containing silane groups. .sup.2for 7 days at 60 C. in a closed container. .sup.3as a solution (20.0% by weight) in N-ethylpyrrolidone.

(69) TABLE-US-00004 TABLE 4 Modulus of Surface Tensile Elongation elasticity Comp. after 24 h strength at break 0-5% 0-50% B32 almost dry 0.64 MPa 170% 0.72 MPa 0.48 MPa B33 almost dry 0.66 MPa 176% 0.69 MPa 0.48 MPa B34 almost dry 0.58 MPa 138% 0.70 MPa 0.48 MPa B35 almost dry 0.59 MPa 140% 0.68 MPa 0.49 MPa B36 dry 0.62 MPa 147% 0.40 MPa 0.49 MPa B37 dry 0.62 MPa 125% 0.64 MPa 0.57 MPa B38 dry 0.54 MPa 97% 0.86 MPa 0.59 MPa B39 dry 0.62 MPa 112% 0.95 MPa 0.65 MPa B40 dry 0.66 MPa 125% 0.87 MPa 0.62 MPa B41 dry 0.60 MPa 111% 0.60 MPa 0.58 MPa B42 dry 0.63 MPa 115% 0.85 MPa 0.61 MPa B43 slightly 0.68 MPa 142% 0.76 MPa 0.60 MPa tacky B44 dry 0.63 MPa 115% 1.02 MPa 0.65 MPa B45 dry 0.58 MPa 96% 0.95 MPa 0.65 MPa B46 dry 0.62 MPa 117% 0.75 MPa 0.60 MPa B47 dry 0.65 MPa 121% 0.93 MPa 0.64 MPa B48 dry 0.63 MPa 141% 0.77 MPa 0.55 MPa B49 dry 0.61 MPa 112% 0.97 MPa 0.65 MPa B50 (Ref) greasy, tacky 0.55 MPa 152% 0.48 MPa 0.44 MPa B51 (Ref) very severely n.d. n.d. n.d. n.d. tacky B52 (Ref) severely 0.55 MPa 99% 0.92 MPa 0.57 MPa tacky B53 (Ref) greasy, tacky 0.53 MPa 165% 0.52 MPa 0.39 MPa B54 (Ref) greasy, tacky 0.45 MPa 80% 0.71 MPa 0.54 MPa B55 (Ref) slightly 0.66 MPa 145% 0.81 MPa 0.56 MPa greasy and tacky B56 (Ref) (liquid) n.d. n.d. n.d. n.d. n.d. = not determined or not measurable.

Compositions B57 to B61 and Comparison B62

(70) In a planetary mixer, 36.2 g of polymer STP-1, 60.2 g of ground chalk (Omyacarb 5 GU, from Omya), 1.2 g of thixotropic paste prepared as described below, 1.2 g of vinyltrimethoxysilane, 1.2 g of 3-aminopropyl-trimethoxysilane and various catalysts in the amounts specified according to table 5 were blended and the mixture was tested as described for composition B1 for viscosity, skin time (ST), surface characteristics and mechanical properties. The results are shown in table 5. Comp. stands for composition. The thixotropic paste was prepared by initially charging a vacuum mixer with 300 g of diisodecyl phthalate (Palatinol Z, from BASF) and 48 g of 4, 4-methylenediphenyl diisocyanate (Desmodur 44 MC L, from Bayer), gently heating the contents and then gradually adding 27 g of n-butylamine dropwise while stirring vigorously. The resultant paste was stirred under reduced pressure and with cooling for a further hour.

(71) TABLE-US-00005 TABLE 5 Modulus of elasticity Surface [MPa] Concen- after Tensile Elongation 0-5% Comp. Catalyst Amount tration.sup.1 ST 24 h strength at break 0-100% B57 K-2 0.31 g 0.8 11 dry 3.1 MPa 117% 6.2 3.0 B58 K-6 0.18 g 0.8 9 dry 2.8 MPa 136% 6.1 2.5 B59 K-13 0.29 g 0.8 20 dry 2.7 MPa 110% 6.3 2.5 B60 K-14 0.26 g 0.8 19 dry 2.8 MPa 120% 6.0 2.6 B61 K-15 0.25 g 0.8 9 dry 2.5 MPa 111% 6.2 3.7 B62 DBU 0.12 g 0.8 25 slightly 2.5 MPa 103% 6.1 2.8 (Ref) greasy 1mmol of amidine or guanidine groups per 100 g of composition.

Compositions B63 to B67 and Comparisons B68 and B69

(72) In a planetary mixer, 36.2 g of polymer STP-2, 60.2 g of ground chalk (Omyacarb 5 GU, from Omya), 1.2 g of thixotropic paste prepared as described for composition Z27, 1.2 g of vinyltriethoxysilane, 1.2 g of 3-minopropyltriethoxysilane and various catalysts in the amounts specified according to table 6 were blended and the mixture was tested as described for composition B1 for skin time (ST), surface characteristics and mechanical properties. The results are shown in table 6. Comp. stands for composition.

(73) TABLE-US-00006 TABLE 6 Modulus of elasticity Surface [MPa] Concen- after Tensile Elongation 0-5% Comp. Catalyst Amount tration.sup.1 ST 24 h strength at break 0-100% B63 K-1 1.11 g 2.6 48 dry 3.5 MPa 124% 5.7 3.1 B64 K-1 0.55 g 1.3 50 dry 2.3 MPa 165% 4.7 2.0 IBAY 0.59 g 1.3 B65 K-5 0.80 g 2.6 51 dry 2.7 MPa 145% 5.0 2.3 B66 K-6 0.59 g 2.6 52 dry 2.8 MPa 139% 5.0 2.4 B67 K-15 0.80 g 2.6 30 dry 2.5 MPa 158% 4.3 2.5 B68 DBU 0.40 g 2.6 83 greasy 2.5 MPa 155% 4.0 2.0 (Ref) B69 DBU 0.20 g 1.3 63 slightly 2.2 MPa 184% 3.6 1.8 (Ref) IBAY 0.59 g 1.3 greasy .sup.1mmol of amidine or guanidine groups or metal atoms per 100 g of polyether containing silane groups.

Composition B70 (In Situ Preparation of the Catalyst)

(74) A composition composed of 20.0 g of polymer STP-1 and 0.6 g of 3-amino-propyltrimethoxysilane, with exclusion of moisture, was blended with 0.95 g of a solution of N,N-dicyclohexylcarbodiimide (49.8% by weight in N-ethyl-pyrrolidone), and the mixture was dispensed into an internally coated aluminum tube and heated to 80 C. in an oven. After the time intervals specified in table 7, the mixture was tested for skin time (ST) under standard climatic conditions and for the conversion of the carbodiimide (via decrease in the intensity of the carbodiimide band at about 2120 cm.sup.1 in the FT-IR, intensity at the start=0% conversion, no band detectable any longer=100% conversion). The results are shown in table 7.

(75) TABLE-US-00007 TABLE 7 Carbodiimide Time ST conversion 0 h 115 0% 1 h 70 3% 2 h 40 14% 4 h 17 36% 5 h 13 48% 23 h 7 92%

Compositions B71 to B76 and Comparisons B77 to B79

(76) A composition composed of 98 g of MS Polymer S203H, a polyether containing silane groups (from Kaneka), and 2 g of 3-aminopropyltrimethoxy-silane was blended with various catalysts in the amounts specified according to table 8 and the mixture was tested as described for skin time (ST) and surface characteristics after 7 days under standard climatic conditions. The results are shown in table 8. Comp. stands for composition.

(77) TABLE-US-00008 TABLE 8 Surface Comp. Catalyst Amount Concentration.sup.1 ST after 7 d B71 K-1 10.26 g 24.0 3 h almost dry B72 DBTDL 1.52 g 2.4 50 dry K-1 1.71 g 4.0 B73 K-5 7.40 g 24.0 4 h 15 almost dry B74 DBTDL 0.76 g 1.2 63 dry K-5 3.71 g 12.0 B75 K-15 7.40 g 24.0 2 h 25 almost dry B76 DBTDL 0.76 g 1.2 75 dry K-15 3.70 g 12.0 B77 (Ref) DBU 3.65 g 24.0 >12 h greasy and tacky B78 (Ref) DBTDL 1.52 g 2.4 71 dry B79 (Ref) DBTDL 0.76 g 1.2 85 greasy DBU 1.83 g 12.0 and tacky .sup.1mmol of amidine or guanidine groups or metal atoms per 100 g of polyether containing silane groups.

Compositions B80 to B85 and Comparisons B86 to B89

(78) A composition composed of 96.5 g of TEGOPAC Bond 150, a polyether containing silane groups (from Evonik), 0.5 g of vinyltriethoxysilane and 3.0 g of 3-aminopropyltriethoxysilane was blended with various catalysts in the amounts specified according to table 9 and the mixture was tested as described for skin time (ST) and surface characteristics after 7 days under standard climatic conditions. The results are shown in table 9. Comp. stands for composition.

(79) TABLE-US-00009 TABLE 9 Surface Comp. Catalyst Amount Concentration.sup.1 ST after 7 d B80 K-1 6.19 g 15 56 almost dry B81 K-1 2.15 g 5 3 h almost dry IBAY 2.40 g 5 B82 K-5 4.61 g 15 81 almost dry B83 K5 1.54 g 5 105 dry IBAY 2.42g 5 B84 K-15 4.64 g 15 53 dry B85 K-15 1.54 g 5 63 dry IBAY 2.42 g 5 B86 (Ref) DBU 2.28 g 15 4 h 20 greasy B87 (Ref) DBTDL 0.79 g 1.25 1 h 45 dry B88 (Ref) IBAY 7.25 g 15 2 h soft and tacky B89 (Ref) DBU 4.93 g 5 3 h tacky IBAY 2.40 g 5 .sup.1mmol of amidine or guanidine groups or metal atoms per 100 g of polyether containing silane groups.

Compositions B90 to B95 and Comparisons B96 and B97

(80) A composition composed of 96.0 g of polyether containing silane groups, either GENIOSIL STP-E 15 (from Wacker) or Desmoseal S XP 2821 (from Bayer), 0.35 g of vinyltrimethoxysilane and 3.72 g of 3-aminopropyltrimethoxysilane was blended with various catalysts in the amounts specified according to table 10 and the mixture was tested as described for composition B1. The results are shown in table 10. Comp. stands for composition.

(81) TABLE-US-00010 TABLE 10 Modulus of Catalyst, Concen- Surface Tensile Elongation elasticity Comp. Polymer amount tration.sup.1 ST after 24 h strength at break 0-5% B90 E-15.sup.2 K-1, 1.9 18 dry 0.76 MPa 48% 1.91 MPa 0.81 g B91 E-15.sup.2 K-5 1.9 15 dry 0.72 MPa 44% 2.04 MPa 0.58 B92 E-15.sup.2 K-15 1.9 10 dry 0.85 MPa 59% 1.94 MPa 0.58 B93 2821.sup.3 K-1, 1.9 50 dry 0.96 MPa 31% 3.3 MPa 0.81 g B94 2821.sup.3 K-5 1.9 42 dry 0.82 MPa 28% 3.22 MPa 0.58 B95 2821.sup.3 K-15 1.9 32 dry 0.93 MPa 33% 3.21 MPa 0.58 B96 E-15.sup.2 DBU, 1.9 60 greasy 0.72 MPa 48% 1.84 MPa (Ref) 0.28 g B97 2821.sup.3 DBU, 1.9 55 dry 0.85 MPa 28% 3.20 MPa (Ref) 0.28 g .sup.1mmol of amidine or guanidine groups per 100 g of polyether containing silane groups. .sup.2GENIOSIL STP-E 15 (from Wacker) .sup.3Desmoseal S XP 2821 (from Bayer)