MXPA99009361A - Compounds curable by humidity containing isocyanate and alcoxisil groups - Google Patents

Abstract

The present invention relates to moisture curable compounds which a) have an aliphatically bound (cyclo) isocyanate group content (calculated as NCO, PM 42) of 0.2 to 30% by weight and a content of alkoxysilane groups (calculated as Si, MW 28) from 0.2 to 4.5% by weight, b) optionally contain repeating units of ethylene oxide and C) have an equivalent ratio of isocyanate groups (cyclo) aliphatically bound to alkoxy groups, which are attached to Yes, from 1.0: 0.05 to 1.0: 1.4, where the above percentages are based on the weight of moisture-curable compounds and where the alkoxysilane groups are incorporated as reaction products of polyisocyanates with compounds amino acids corresponding to formula I (See Formula). The present invention also relates to coating, adhesive or sealant compositions containing these moisture curable compounds as they bind

Description

CURABLE COMPOUNDS FOR HUMIDITY CONTAINING ISOCYANATE AND ALCOHOLISILANE GROUPS BACKGROUND OF THE INVENTION Field of the Invention The present invention relates to curable compounds - by moisture containing aliphatically bound isocyanate (cyclo) groups and alkoxysilane groups incorporated through aspartate groups, which can be cured in the presence of moisture for form coatings, adhesives and sealants. DESCRIPTION OF THE PRIOR ART It is known that polyisocyanate resins are curable in the presence of atmospheric moisture to form polyurea coatings. During the curing mechanism, an isocyanate group reacts with moisture to form an amino group, which then reacts with another isocyanate group to form a urea. One of the disadvantages of these resins curable by moisture is that the curing mechanism is relatively slow. It has been suggested in US Pat. 3,420,800 and 3,567,692 that the speed of moisture curable polyisocyanates can be increased by incorporating aldimines or ketimines. It is said that the reaction of moisture with an aldimine or ketimine to form the corresponding amine is faster than the reaction of moisture with an isocyanate group to form an amine. A drawback of the use of aldimines and ketimines to accelerate the curing of polyisocyanates is that it requires the preparation of an additional component and requires some type of dosing equipment to ensure that the two components are mixed in the proper proportions.

It is an object of the present invention to increase the curing speed of the curable polyisocyanates by moisture without the need for a co-reactant. This object can be achieved with the poly-socianates according to the present invention, which have been modified to contain alkoxysilanesilane groups incorporated through aspartate groups. The faster curing speeds obtained according to the present invention are surprising since the alkoxysilane groups, which are also curable in the presence of moisture, cure more slowly than the polyisocyanates. However, when both isocyanate groups and alkoxysilane groups are present, a faster curing speed is obtained. The copending application, USA Serial No. 09 / 058,072, discloses water-dispersible compounds containing isocyanate and alkoxysilane groups. The water-dispersible compounds should be prepared from a polyisocyanate component having a minimum average functionality of 2.4 and converted into water-dispersible by the use of ionic or non-ionic hydrophilic groups. The copending application, USA Serial No. 08 / 992,163, describes the preparation of polyurethane-urea dispersions containing alkoxysilane groups incorporated through aspartate groups. However, since the resulting polyurethane dispersions are dispersed in water, they do not contain unreacted isocyanate groups. SUMMARY OF THE INVENTION The present invention relates to moisture curable compounds that a) have an aliphatically bound (cyclo) isocyanate group content (calculated as NCO, PM 42) of 0.2 to 30% by weight and a contained in alkoxysilane groups (calculated as Si, MW 28) of 0.2 to 4.5% by weight, b) optionally contain repeating units of ethylene oxide and c) have an equivalent ratio of isocyanate groups (cyclo) aliphatically bound to alkoxy groups, which are attached to Si, from 1.0: 0.05 to 1.0: 1.4, where the above percentages are based on the weight of the curable compounds by moisture and where the alkoxysilane groups they are incorporated as the reaction products of polyisocyanates with amino compounds corresponding to the formula I COOR2 Z-CHR3-CR4-NH-Y-SÍ- (X) (I) wherein X represents identical or different organic groups which are inert to the groups isocyanate below 100 C, provided that at least one of this s groups is an alkoxy group, Y represents a linear or branched alkylene radical containing from 1 to 8 carbon atoms, Z represents COOR? or an aromatic ring, Ri and R2 are identical or different and represent organic groups which are inert to the isocyanate groups at a temperature of 100 ° C or less and R3 and R4 are identical or different and represent hydrogen or organic groups which are inert to the isocyanate groups at a temperature of 100 ° C or less. The present invention also relates to coating, adhesive or sealant compositions containing these moisture curable compounds as binders. DETAILED DESCRIPTION OF THE INVENTION The compounds according to the present invention are based on the reaction products of polyisocyanates containing (cyclo) aliphatically bound isocyanate groups, compounds containing alkoxysilane groups and aspartate groups and, optionally, compounds containing oxide units. of ethylene and isocyanate-reactive groups, preferably hydroxy groups. The alkoxysilane groups are incorporated in the form of urea groups, while the hydrophilic groups are incorporated, in general, in the form of urethane groups. The moisture-curable compounds have "a) a content of alkoxysilane groups (calculated as Si, MW 28) of 0.2 to 4.5% by weight, preferably 0.2 to 4%, and more preferably 0 5 to 3.5%, b) a content of aliphatically bound isocyanate (cycloalkyl) groups (calculated as NCO, PM 42) of 0.2 to 30% by weight, preferably 0.5 to 20% by weight, weight and, more preferably, from 1.0 to 15% by weight, and c) optionally, a content of ethylene oxide groups (calculated as CH2-CH2-0, MW 44) from 5 to 35% by weight, preferably from 5 to 30% by weight and, more preferably, from 10 to 25% by weight, where the above percentages are based on the weight of moisture-curable compounds, such as suitable compounds containing alkoxysilane groups and amino groups, which can be used to prepare compounds curable by moisture include those corresponding to formula I where X represents identical or different organic groups that are ineffective. ions to the isocyanate groups below 100 ° C, provided that at least one of these groups is an alkoxy group, preferably alkyl or alkoxy groups having 1 to 4 carbon atoms and, more preferably, alkoxy groups; Y represents a linear or branched alkylene radical containing from 1 to 8 carbon atoms, preferably a linear radical containing from 2 to 4 carbon atoms or a branched radical containing from 5 to 6 carbon atoms, more preferably a linear radical which contains 3 carbon atoms; Z represents COORi or an aromatic ring, preferably COOR; Rx and R2 are identical or different and represent organic groups which are inert to the isocyanate groups at a temperature of 100 ° C or less, preferably alkyl groups having from 1 to 9 carbon atoms, more preferably methyl, ethyl or butyl groups, and R3 and R4 are identical or different and represent hydrogen or organic groups which are inert to the isocyanate groups at a temperature of 100 ° C, preferably hydrogen. Especially preferred are compounds wherein X represents methoxy, ethoxy or propoxy groups, more preferably methoxy or ethoxy groups and, more preferably, methoxy groups.

The compounds of formula I are prepared by reaction of aminoalkylalkoxysilanes corresponding to formula II H2N-Y-Si- (X) 3 (II) with esters of maleic, fumaric or cinnamic acid corresponding to formula III Z-CR3 = CR4- COOR2 (III) Examples of suitable aminoalkylalkoxysilanes of formula II include 2-aminoethyldimethylmethoxysilane, 6-aminohexyl-taxyoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxy-silane, 3-aminopropyl-1-methylethioxysilane, 5-aminopenti-1-trimethoxysilane, 5-aminopentyltriethoxysilane, 3- amino-propyltriisopropoxy silane and 4-amino-3, 3-dimethylbutyl-dimethoxymethylsilane. 4-Amino-3, 3-dimethyl-butyldimethoxymethylsilane is preferred and 3-aminopropyltrimethoxysilane and 3-aminopropyltriethoxysilane are especially preferred. Examples of optionally substituted esters of maleic, fumaric or cinnamic acid for use in the preparation of polyaspartates include dimethyl, diethyl, dibutyl (eg, di-n-butyl), diamyl, di-2-ethylhexyl esters and mixed esters based on the mixture of these and / or other alkyl groups of maleic acid and fumaric acid; the methyl, ethyl and butyl esters of cinnamic acid, and the corresponding esters of maleic, fumaric and cinnamic acid substituted by methyl in the 2 and / or 3 position. The dimethyl, diethyl and dibutyl esters of maleic acid are preferred. they especially prefer diethyl and dibutyl esters. The reaction of primary amines with esters of maleic, fumaric or cinnamic acid to form the aspartates of formula I is known and is described, for example, in US Pat. 5,364,955, incorporated herein by reference. The preparation of the aspartates can be carried out, for example, at a temperature of from 0 to 100 ° C using the starting materials in proportions such that at least 1, preferably 1, olefinic double bond is present for each amino group primary. The excess of the starting materials can be removed by distillation after the reaction. The reaction can be carried out with or without a solvent, but the use of solvent is less preferred. If a solvent is used, dioxane is an example of a suitable solvent. The compounds of formula I are colorless to light yellow. They can react with polyisocyanate compound to form the compounds containing urea and alkoxysilane groups without further purification. Suitable polyisocyanates for preparing the compounds containing urea and alkoxysilane groups are selected from monomeric diisocyanates, polyisocyanate adducts and NCO prepolymers. The polyisocyanates contain linked (cyclo) aliphatic isocyanate groups and have an average functionality of from 1.5 to 6. The monomeric diisocyanates and adducts of polyisocyanates preferably have an average functionality of from 1.8 to 6, more preferably from 2 to 6 and, more preferably, from 2 to 4. The NCO prepolymers preferably have an average functionality of 1.5 to 4.5, more preferably 1.7 to 3.5 and, more preferably, 1.8 to 3. ,2. Suitable monomeric diisocyanates can be represented by the formula R (NCO) 2 where R represents an organic group obtained by removing the aliphatic and / or cycloaliphatically isocyanate groups attached from an organic diisocyanate having a molecular weight of about 112 to 1,000, preferably about 140 a_400. Preferred diisocyanates for the process according to the invention are those in which R represents a divalent aliphatic hydrocarbon group having from 4 to 40, preferably from 4 to 18 carbon atoms, a divalent cycloaliphatic hydrocarbon group having from 5 to 15 carbon atoms or a divalent araliphatic hydrocarbon group having from 7 to 15 carbon atoms Examples of suitable organic diisocyanates include 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, diisocyanate 2,2,4-trimethyl-1, 6-hexamethylene, 1,2-dodecamethylene diisocyanate, cyclohexane-1, 3-, and 1,4-diisocyanate, 1-isocyanato-2-isocyanatomethylcyclopentane, 1- isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane (isophorone diisocyanate or DIIF), bis (4-isocyanatocyclohexyl) methane, di-2,4-diisocyanate-dicyclohexylmethane, 1,3- and 1 , 4-bis (isocyanatomethyl) cyclohexane, bis (4-isocyanato-3-methylcyclo- hexyl) methane, di, a, a, a ', a'-tetramethyl-1, 3- and / or -1, 4-xylylene, 1-isocyanato-1-methyl-4 (3) -isocyanato-methylcyclohexane, diisocyanate of 2,4- and / or 2,6-hexahydro-drotoluylene and mixtures thereof. Polyisocyanates containing 3 or isocyanate groups, such as 4-isocyanatomethyl-1, 8-octamethylene diisocyanate can also be used. Preferred organic diisocyanates include 1,6-hexamethylene diisocyanate, l-isocyanato-3-isocyanatomethyl-3,5,5-trimethylcyclohexane (isophorone diisocyanate or DIIF), bis (4-isocyanatocyclohexyl) methane and 1- isocyanat-1. -methyl-4 (3) -isocyanatomethyl-cyclohexane.

According to the present invention, the polyisocyanate component is preferably in the form of an adduct of polyisocyanates. Suitable polyisocyanate adducts are those containing isocyanurate, uretdione, biuret, urethane, allophanate, carbodiimide and / or oxadiazinetrione groups. The polyisocyanate adducts, which preferably have an NCO content of 5 to 30% by weight, include: 1) Polyisocyanates containing isocyanurate groups, which can be prepared according to DE-PS 2,616,416, EP-OS 3,765, EP-OS 10,589, EP-OS 47. 452, US-PS 4,288,586 and US-PS 4,324,879. The isocyanato isocyanurates generally have an average NCO functionality of from 3 to 3.5 and an NCO content of 5 to 30%, preferably from 10 to 25% and, more preferably, from 15 to 25%. % by weight. 2) uretdione diisocyanates, which can be prepared by oligomerization of a portion of the isocyanate groups of a diisocyanate in the presence of a suitable catalyst, for example a trialkyl phosphine catalyst, and which can be used in admixture with other aliphatic polyisocyanates and / or cycloaliphatics, particularly the polyisocyanates containing isocyanurate groups indicated in (1) above. 3) Polyisocyanates containing biuret groups, which can be prepared according to the procedures described in US Pat. Nos. 3,124,605, 3,358,010, 3,644,490, 3,862,973, 3,906,126, 3,903,127, 4,051,165, 4,147,714 or 4,220,749 using co-reactants such as water, tertiary alcohols, monoamines. primary and secondary and primary and / or secondary diamines. These polyisocyanates preferably have an NCO content of 18 to 22% by weight and an average NCO functionality of 3 to 3.5. Polyisocyanates containing urethane groups, which can be prepared according to the process described in US Pat. No. 3,183,112 for reaction of excess quantities of polii¬ socianates, preferably diisocyanates, with low molecular weight glycols and polyols having molecular weights of less than 400, such as trimethylolpropane, glycerin, 1,2-dihydroxypropane and mixtures thereof. The polyisocyc¬ ions containing urethane groups have a more preferred NCO content of 12 to 20% by weight and (average) NCO functionality of 2.5 to 3. Polyisocyanates containing allophanate groups, Which can be prepared according to the procedures described in U.S. Pat. No. 3,769,318, 4,160,080 and 4,177,342. The polyisocyanates containing allophanate groups have a more preferred NCO content of 12 to 21% by weight and a (average) NCO functionality of 2 to 4.5. 6) Polyisocyanates containing isocyanurate and allophanate groups, which can be prepared according to the procedures set forth in the Patents te US 5,124,427, 5,208,334 and 5,235,018, the descriptions of which are incorporated herein by reference, preferably polyisocyanates containing these groups in a proportion of monoisocyanurate groups to monoalphanate groups of about 10: 1 to 1:10, preferably about 5: 1 to 1: 7. 7) Polyisocyanates containing iminooxadiazinedione groups and, optionally, isocyanurate, which can be prepared in the presence of special fluorine-containing catalysts, as described in DE-A 19611849. These polyisocyanates generally have an average NCO functionality of 3 to 3, 5 and an NCO content of 5 to 30%, preferably 10 to 25% and, more preferably, 15 to 25% by weight. 8) Polyisocyanates containing carbodiimide groups, which can be prepared by oligomerization of di- or polyisocyanates in the presence of known carbodiimidation catalysts, as described in DE-PS 1,092,007, US-PS 3,152,162 and DE- OS 2,504,400, 2,537,685 and "2,552,350,9) polyisocyanates containing oxadiazinetrione groups and containing the reaction product of two moles of a diisocyanate and one mole of carbon dioxide are preferred polyisocyanate adducts. polyisocyanates that contain isocyanurate groups, uretdione, biuret, iminooxadiazinadione and / or allophanate. The NCO prepolymers, which can also be used as the polyisocyanate component according to the present invention, are prepared with the monomeric polyisocyanates or polyisocyanate adducts previously described, preferably monomeric diisocyanates, and organic compounds containing at least two isocyanate-reactive groups, preferably at least two hydroxy groups. These organic compounds include high molecular weight compounds, having molecular weights of from 500 to about 10,000, preferably from 800 to about 8,000, and more preferably from 1,800 to 8,000, and, optionally, low molecular weight compounds, having molecular weights less than 500. The molecular weights are number average molecular weights (Mn) and are determined by analysis of final groups (number of OH and / or NH). The products obtained by reacting polyisocyanates exclusively with low molecular weight compounds are adducts of polyisocyanates containing urethane groups and are not considered as NCO prepolymers. Examples of the high molecular weight compounds are polyester polyols, polyether polyols, polyhydroxypolycarbonates, polyhydroxypolyacetals, polyhydroxy polyacrylates, polyhydroxypolyester amides and polyhydroxypolythioethers. Polyester polyols, polyether polyols and polyhydroxypolycarbonates, especially polyether polyols, are preferred. Examples of suitable high molecular weight polyhydroxy compounds include polyester polyols prepared with low molecular weight alcohols and polybasic carboxylic acids, such as adipic acid, sebacic acid, phthalic acid, isophthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, the anhydrides of these acids and mixtures of these acids and / or acid anhydrides. Polylactones having hydroxyl groups, particularly poly-caprolactone, are also suitable for producing the prepolymers. Also suitable for preparing the prepolymers are polyether polyols, which can be obtained in a known manner by alkoxylation of suitable starter molecules. Examples of suitable starter molecules include polyols, water, organic polyamines having at least two N-H bonds and mixtures thereof. The alkylene oxides suitable for the alkoxylation reaction are preferably ethylene oxide and / or propylene oxide, which can be used in sequence or as a mixture. Other suitable polyols include polycarbonates having hydroxyl groups, which can be produced by the reaction of diols with phosgene or diaryl carbonates, such as diphenyl carbonate. Other details concerning the low molecular weight compounds and the starting materials and methods for preparing the high molecular weight polyhydroxy compounds are described in US Pat. 4. 701,480, incorporated herein by reference. Other examples include the known high molecular weight amine functional compounds, which can be prepared by converting the terminal hydroxy groups of the previously described polyols to amino groups, and the high molecular weight polyaspartates and polyaldimines described in US Pat. 5,243,012 and 5,466,771, respectively, incorporated herein by reference. - - - These NCO prepolymers have an isocyanate content of from 0.3 to 35% by weight, more preferably from 0.6 to 25% by weight and, more preferably, from 1.2 to 20% by weight. % in weigh. The NCO prepolymers are produced by reacting the diisocyanates with the polyol component at a temperature of from 40 to 120 ° C, preferably from 50 to 100 ° C, at an NCO / OH equivalent ratio of 1.3: 1 to 20: 1, preferably 1.4: 1 to 10: 1. If prolongation of the chain by means of urethane groups is desired during the preparation of the isocyanate prepolymers, an equivalent NCO / OH ratio of 1.3: 1 to 2: 1 is selected. If prolongation of the chain is not desired, an excess of diisocyanate, corresponding to an NCO / OH equivalent ratio of 4: 1 to 20: 1, preferably 5: 1 to 10: 1, is preferably used. The excess diisocyanate can optionally be removed by thin layer distillation when the reaction is complete. According to the present invention, the NCO prepolymers also include NCO semi-prepolymers containing unreacted starting polyisocyanates in addition to the prepolymers containing urethane groups. Suitable compounds containing ethylene oxide units, which may optionally be incorporated into the moisture curable compounds according to the present invention, include compounds that contain lateral or terminal ethylene oxide units. Suitable compounds for incorporating side or terminal hydrophilic ethylene oxide units are known and described in US Pat. 3,905,929, 3,920,598 and 4,190,566 (the descriptions of which are incorporated herein by reference). Preferred hydrophilic components are monohydroxypolyethers having terminal hydrophilic chains containing ethylene oxide units. These hydrophilic components can be produced as described in the preceding patents by alkoxylation of a monofunctional initiator, such as methanol or n-butanol, using ethylene oxide and, optionally, another alkylene oxide, for example propylene oxide. The moisture curable compounds according to the invention are prepared by reacting the polyisocyanate component with the amino-functional silanes in an amount such that the moisture curable compounds contain isocyanate groups and alkoxy groups, which are bonded to Si, in an equivalent ratio of 1.0: 0.05 to 1.0: 1.4, preferably 1.0: 0.05 to 1.0: 1.2 and, more preferably, 1.0: 0.1 to 1.0: 1.0 Compounds containing repeating units of "ethylene oxide" react with the polyisocyanates in amounts sufficient to provide the amount of ethylene oxide units previously indicated. In one embodiment of the present invention, the moisture curable compounds do not contain enough ethylene oxide units to be stably dispersed in water. Compounds which can not be stably dispersed in water are those which do not remain mixed in the water, either in the form of an oil-in-water emulsion or a water-in-oil emulsion, without sedimentation, coagulation or separation. The reaction is preferably carried out by increasingly adding the isocyanate-reactive compound to the polyisocyanate. The silane aspartate and the optional compound containing ethylene oxide groups can be added sequentially or in a mixture. When present, the compound containing ethylene oxide units is first added, followed by the silane aspartate. "The compounds according to the invention can also be prepared by mixing different types of compounds, provided that they satisfy the preceding guidelines as regards the amounts of hydrophilic groups, alkoxysilane groups and isocyanate groups. For example, "" compounds containing alkoxysilane groups, but free of isocyanate groups, and / or compounds containing isocyanate groups, but not containing alkoxysilane groups, may be present as a portion of the compounds according to the invention. The reaction to form the urea moieties is conducted at a temperature of from 10 to 100 ° C, preferably from 20 to 80 ° C and, more preferably, from 20 to 50 ° C, while the reaction with the compounds contain ethylene oxide units is conducted at a temperature of 20 to 150 ° C, preferably 50 to 120 ° C and, more preferably, 60 to 100 ° C. - According to the present invention, the special type of urea groups formed by the reaction of the amino-functional compounds containing alkoxysilane groups and aspartate groups with the polyisocyanate component can be converted to hydantoin groups in a known manner, by slowing the compounds to high temperatures, possibly in the presence of a catalyst. Therefore, the term "urea groups" is also intended to include other compounds containing the group N-CO-N, such as hydan-toine groups. The formation of hydantoin groups is not preferred according to the present invention, since this reaction also gives rise to the formation of a monoalcohol, which will react with the isocyanate groups without chain extension. For this reason, it is preferred to form the urea groups at low temperatures to avoid the formation of hydantoin groups. However, since the hydantoin groups can also be formed under ambient conditions during storage, it is preferred to use the products of the invention shortly after their preparation. The compounds of the present invention are suitable for use in coating compositions, adhesives or one-component sealants, which can be cured in the presence of atmospheric moisture. The compositions cure by a double curing mechanism, i.e., 1) by reaction of the isocyanate groups with moisture and 2) by "polycondensation of silane" from the hydrolysis of alkoxysilane groups to form Si -OH groups and their subsequent reaction with Si-OH or Si-OR groups to form siloxane groups (Si-O-Si) and 3) possibly, by reaction of the isocyanate groups with Si-OH groups. Acidic or basic catalysts can be used to promote the curing reaction Examples include acids, such as paratoluenesulfonic acid; -metallic salts, such as dibutyltin dilaurate; tertiary amines, such as triethylamine or triethylene diamine, and mixtures of these catalysts. The basic aminoalkyltrialkoxysilanes of low molecular weight, such as those represented by formula II, also accelerate the hardening of the compounds according to the invention. The one-component compositions can generally be solvent-free or contain up to 70%, preferably up to 60%, of organic solvents, based on the weight of the composition of a component, depending on the particular application. Suitable organic solvents include those known from the chemistry of polyurethanes. The compositions may also contain known additives, such as leveling agents, wetting agents, flow control agents, antiscratching agents, anti-foaming agents, fillers (such as silica, aluminum silicates and high-boiling waxes). , viscosity regulators, plasticizers, pigments, dyes, UV absorbents and stabilizers against thermal and oxidative degradation. The one-component compositions can be applied to any desired substrate, such as wood, plastic, leather, paper, textiles, glass, ceramics, plaster, masonry, metals and concrete, and can be applied by standard methods, such as spray coating. , coating by extension, flood coating, casting, dip coating, roller coating, etc. The coating compositions can be clear or pigmented lacquers.The one component compositions can be cured at room temperature or elevated temperatures. Moisture-curable resins are cured at room temperature The invention is further illustrated, but without intending to limit it, by the following examples, in which all parts and percentages are by weight, unless otherwise indicated. Polyisocyanate resin 1 (Comparison) A polyisocyanate containing isocyanurate groups prepared from 1,6-hexamethylene diisocyanate and having an isocyanate content of 21.6%, a monomeric diisocyanate content of < 0.2% and a viscosity at 20 ° C of 3,000 mPa. s (available from Bayer Corporation as Desmodur N 3300). Polyether 1 A polyethylene oxide monool prepared by ethoxylation of methanol and having a molecular weight of 550 (available from Union Carbide as Carbowax 550).

Silane Aspartate 1 - N- (3-trimethoxysilylpropyl) aspartic acid diethyl ester 1,438 parts (8.27 equiv.) Of 3-ammopropyltrimethoxysilane were added to a 5-liter flask equipped with stirrer, thermocouple, nitrogen inlet and funnel. addition with condenser. 1,423.2 parts (8.27 equiv.) Of diethyl maleate were added dropwise over a period of 2 hours. The reactor temperature was maintained at 25 ° C during the addition. The reactor was maintained at 25 ° C for a further 5 hours, at which time the product was poured into glass containers and sealed under a blanket of nitrogen. After one week, the unsaturation number was 0.6, indicating that the reaction had been completed at -99%. The product, N- (3-trimethoxysilylpropyl) aspartic acid diethyl ester, had a viscosity of 11 mPa.s at 25 ° C. Polyisocyanate resin 2 containing silane aspartate groups 514 parts (1.46 equiv.) Of poly-socianate 1 and 200 parts of n-butyl acetate were added at room temperature to a 2 liter flask equipped with stirrer, nitrogen, heater and temperature controller. 285 parts (1.46 equiv.) Of silane aspartate 1 were added by dripping as quickly as possible over a period of thirty minutes, to keep the reaction temperature below 30 ° C. The reaction was maintained at 30 C for 4 hours, until no isocyanate group remained, as determined by IR spectroscopy. After cooling, the resulting product had a viscosity of 1250 mPa.s at 25 ° C. Polyisocyanate 3 containing ethylene oxide groups (Comparison) 82.5 parts (0.15 equiv.) Of polyether 1, which had been melted at 60 ° C, were added to a 500 ml flask equipped with stirrer, nitrogen inlet , heater and temperature controller. 195 parts (1 equiv.) Of polyisocyanate 1 were then added. The reaction flask was heated and maintained at 60 ° C for 16.5 hours, until the NCO content was 12.65% (theoretical NCO 12.88. %). The resulting product had a viscosity of 2,644 mPa.s at 25 ° C. Polyisocyanate 4 containing silane aspartate and ethylene oxide groups 82.5 parts (0.15 equiv.) Of polyether 1, which had been melted at 60 ° C, were added to a 500 ml flask equipped with stirrer, inlet nitrogen, heater and temperature controller. 195 parts (1 equiv.) Of polyisocyanate 1 were then added. The reaction flask was heated and maintained at 60 ° C for 13 hours until the NCO content was 12.65% (theoretical NCO 12.88%) . The reaction mixture was cooled to 35 ° C. 31.1 parts (0.85 equiv.) Of silane aspartate 1 were added and the reaction mixture produced an exotherm at 43 ° C. The reaction was heated and maintained at 60 ° C. for two hours. it had an NCO content of 10.18% (theoretical NCO 10.41%) and a viscosity of 4532 mPa.s at 25 ° C. Polyisocyanate 5 containing silane aspartate and ethylene oxide groups were added. , 15 equiv.) Of polyether 1, which had been melted at 60 ° C, to a 500 ml flask equipped with stirrer, nitrogen inlet, heater and temperature controller, 195 parts (1 equiv.) Of polyisocyanate were then added. 1. The reaction flask was heated and maintained at 60 ° C for 12.5 hours until the NCO content was 12.63% (theoretical NCO 12.88%). The reaction mixture was cooled to 35 ° C. C. 100.6 parts (0.275 equiv.) Of silane aspartate 1 were added and the reaction mixture produced an exotherm at 43 ° C. The reaction was heated and maintained at 100 ° C. 60 C for two hours The resulting product had an NCO content of 5.97% (theoretical NCO 6.38%) and a viscosity of 13,500 mPa.s at 25 ° C. Preparation of films with the polyisocyanate resins 1 and 2 Coating compositions were prepared by mixing the polyisocyanate resins 1 and / or 2 with the catalysts and solvents indicated in the following table. The compositions, which had solids content of 80%, were applied to glass plates with a 3 mil bar. The drying times were determined with a Gardner Drying Time Meter as described in the Pacific Scientific DG-9600 and DG-9300 Instruction Manuals. The compositions and drying times are indicated in Table 1. "Table 1 Preparation of films with the polyisocyanate resins 3. 4 and 5 20 g of each of the polyisocyanate resins 3, 4 and 5 were mixed with 0.02 g of triethylenediamine catalyst (Dabco 33LV, Air Products), , 02 g of dibutyltin acetoacetonate catalyst and 5 g of n-butyl acetate solvent The resulting compositions were applied to glass plates with a 3-mil bar The drying times were determined with a Drying Time Meter Gardner as described in the Pacific Scientific Instructions Manuals DG-9600 and DG-9300. Table 2 shows the drying times Table 2 Polyisocyanate resin Gardner drying times, minutes Although the invention has been described in detail in the foregoing for illustrative purposes, it is to be understood that said detail has only that purpose and that those skilled in the art can make variations therein without departing from the spirit and scope of the invention, except in what may be limited by the claims.

Claims (9)

1. CLAIMS 1. A moisture curable compound that a) has an aliphatically bound (cyclo) isocyanate group content (calculated as NCO, PM 42) of 0.2 to 30% by weight and a content of alkoxysilane groups (calculated as Si). , MW 28) from 0.2 to 4.5% by weight, b) optionally contains repeating units of ethylene oxide and c) has an equivalent ratio of isocyanate groups (cyclo) aliphatically bound to alkoxy groups, which are attached to Si, from 1.0: 0.05 to 1.0: 1.4, where the above percentages are based on the weight of the moisture curable compound and where the alkoxysilane groups are incorporated as the reaction product of a polyisocyanate with an amino compound corresponding to the formula I C00R2 Z-CHR3-CR4-NH-Y-YES- (X) 3 (I) where X represents identical or different organic groups which are inert to the isocyanate groups below 100 ° C, provided that the less one of these groups is an alkoxy group, represents a linear or branched alkylene radical ficate containing 1 to 8 carbon atoms,
2. Z represents COORi or an aromatic ring, i and 2 are identical or different and represent organic groups that are inert to the isocyanate groups at a temperature of 100 ° C or less and R3 and R4 are identical or different and represent hydrogen or organic groups which are inert to the isocyanate groups at a temperature of 100 ° C or less. 2. The moisture curable compound of Claim 1, wherein X represents identical or different alkyl or alkoxy groups having 1 to 4 carbon atoms, Y represents a linear radical containing from 2"to 4 carbon atoms or a branched radical containing from 5 to 6 carbon atoms, Z represents COORi, Rx and R2"are" identical or different and represent alkyl groups having from 1 to 9 carbon atoms and R3 and R represent hydrogen. moisture curable compound of Claim 1, wherein X represents identical or different alkoxy groups having 1 to 4 carbon atoms, Y represents a linear radical containing from 2 to 4 carbon atoms or a branched radical containing 5 to 4 carbon atoms. to 6 carbon atoms, Z "" represents COORi, Ri and R2 are identical or different and represent methyl, ethyl or butyl and R3 and R4 represent hydrogen 4. The moisture curable compound of Claim 1, where the groups alcox isilanes are incorporated as the reaction product of a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and / or uretdione groups with an amino compound. 5. The moisture curable compound of Claim 2, wherein the alkoxysilane groups are incorporated as the reaction product of a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and / or uretdione groups with an amino compound. 6. The compound curable by the moisture of the
3. Claim 3, wherein the alkoxysilane groups are incorporated as the reaction product of a polyisocyanate adduct containing isocyanurate groups, biuret groups, allophanate groups and / or uretdione groups with an amino compound. 7. The compound curable by the moisture of the
4. Claim 1, wherein the alkoxysilane groups are incorporated as the reaction product of an NCO prepolymer with an amino compound. 8. The moisture curable compound of Claim 2, wherein the alkoxysilane groups are incorporated as the reaction product of an NCO prepolymer with an amino compound. 9. The moisture curable compound of Claim 3, wherein the alkoxysilane groups are incorporated as the reaction product of an NCO prepolymer with an amino compound. 10. The moisture curable compound of Claim 1, wherein said moisture curable compound can not be stably dispersed in water. 11. The compound curable by the moisture of the
5. Claim 2, wherein said moisture curable compound can not be stably dispersed in water. 12. The moisture curable compound of Claim 3, wherein said moisture curable compound can not be stably dispersed in water. 13. The moisture curable compound of Claim 4, wherein said moisture curable compound can not be stably dispersed in water. 14. The moisture curable compound of Claim 5, wherein said moisture curable compound can not be stably dispersed in water. 15. The compound curable by the moisture of the
6. Claim 6, wherein said moisture curable compound can not be stably dispersed in water. 16. The moisture curable compound of
7. Claim 7, wherein said moisture curable compound can not be stably dispersed in water. 17. The moisture curable compound of
8. Claim 8, wherein said moisture curable compound can not be stably dispersed in water. 18. The moisture curable compound of
9. Claim 9, wherein said moisture curable compound can not be stably dispersed in water. 19. A one-component coating, adhesive or sealant composition wherein the binder consists of a moisture curable compound of Claim 1.