Condensation-hardening composition

Abstract

A moisture-curable composition is shown and described herein. The moisture-curable composition includes a moisture-curable resin and a moisture scavenger selected from a cyanoalkylalkoxysilane. The inclusion of a cyanoalkylalkoxysilane in the moisture-curable composition has been found to effectively scavenge moisture and control the cure rate and viscosity increase of the composition.

Description

[Technical field]

[0001] The present invention relates to curable compositions, and in particular to condensation curable compositions, that contain a moisture scavenger to control the stability of the composition when exposed to moisture. [Background technology]

[0002] Silane-grafted polymers, resins, elastomers, adhesives, sealants, coatings, and the like often use moisture scavengers to stabilize these materials. In particular, moisture scavengers are typically included to provide a component that is more reactive with water than the silane-grafted material, stabilizing the composition and preventing the silane-grafted material from reacting too quickly and reacting with water prior to use. This allows the material to have a long shelf life, a longer pot life, and / or allows for better processing and application of the material. In moisture-curable polymer compositions, alkoxysilanes such as vinyltrimethoxysilane, methyltrimethoxysilane, phenyltrimethoxysilane, and propyltrimethoxysilane have been used as moisture scavengers. Although these materials are generally suitable as moisture scavengers, they may not provide the desired level of performance required for certain applications, and some of these materials may have safety concerns (toxicity, flammability, etc.) and are subject to regulations that will limit their use in the future. For example, vinyltrimethoxysilane is subject to regulation in some countries as a potential skin sensitizer, which may result in more restricted use of such materials in moisture curable compositions. Summary of the Invention

[0003] The following presents a summary of the disclosure to provide a basic understanding of some aspects. This summary is not intended to identify key or critical elements, nor is it intended to define any limitations to the embodiments or claims. Moreover, this summary may provide a simplified overview of some aspects, which may be described in more detail in other parts of the disclosure.

[0004] In one embodiment, a moisture-curable composition is provided, comprising a water-reactive polymer, such as a polymer containing hydrolyzable silyl groups, and a moisture scavenger selected from cyanoalkylalkoxysilanes.The inventors have surprisingly found that cyanoalkylalkoxysilanes can function as moisture scavenger materials.These materials also exhibit relatively low toxicity and flammability, making them suitable for use in many applications.

[0005] In another aspect, provided is a cured composition produced by contacting a moisture-curable composition with water.

[0006] In yet another aspect, provided is a moisture curable sealant, adhesive, or coating containing the moisture curable resin.

[0007] In still yet another embodiment, provided is a method of treating a substrate comprising applying the moisture-curable composition to a surface of the substrate.

[0008] In one embodiment, provided is a moisture-curable composition comprising: (a) a moisture-curable resin comprising a water-reactive polymer; and (b) a moisture scavenger selected from a cyanoalkylalkoxysilane.

[0009] In one embodiment, the cyanoalkylalkoxysilane has the formula: NC-R 1 -Si(R 2 )(R 3 )(R 4 ) wherein R 1 is selected from divalent hydrocarbon groups having 1 to 20 carbon atoms; R 2 , R 3 , and R 4 each independently represents a monovalent hydrocarbon of C1 to C30, a halide, or -OR 5 is selected from, where R 5 are independently selected from C1 to C30 monovalent hydrocarbons, with the proviso that R 2 , R 3 , and R 4 At least one of -OR 5 is selected from.

[0010] In one embodiment, R 1 is selected from C1 to C20 alkylene; R 2 , R 3 , and R 4 are each independently selected from C1-C20 alkyl, C4-C20 cycloalkyl, and C6-C30 aryl; and R 5 is independently selected from C1 to C20 alkyl.

[0011] In one embodiment, R 1 is selected from C1 to C20 alkylene; R 2 , R 3 , and R 4 each is selected from C1-C10 alkyl, and R 5 is selected from C1 to C10 alkyl.

[0012] In one embodiment, R 1 is selected from C1-C4 alkylene, and R 2 , R 3 , and R 4 Each of -OR 5 is selected from, where R 5 is independently selected from C1 to C4 alkyl.

[0013] In one embodiment of the moisture-curable composition according to any of the above embodiments, the cyanoalkylalkoxysilane is selected from 2-cyanoethyltrimethoxysilane, 2-cyanoethyltriethoxysilane, 2-cyanoethyltripropoxysilane, 2-cyanoethyldimethoxymethylsilane, 2-cyanoethyldimethoxyethylsilane, 2-cyanoethyldiethoxymethylsilane, 2-cyanoethyldiethoxyethylsilane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltripropoxysilane, 3-cyanopropyldimethoxymethylsilane, 3-cyanopropyldimethoxyethylsilane, 3-cyanodiethoxymethylsilane, 3-cyanopropyldiethoxyethylsilane, or a combination of two or more thereof.

[0014] In one embodiment of the moisture-curable composition according to any of the above embodiments, the cyanoalkylsiloxane is present in an amount of about 0.1% to about 20% by weight based on the total weight of the moisture-curable resin (a).

[0015] In one embodiment of the moisture-curable composition according to any of the above embodiments, the cyanoalkylsilane is present in an amount of about 0.5% to about 10% by weight based on the total weight of the moisture-curable resin (a).

[0016] In one embodiment of the moisture-curable composition according to any of the above embodiments, the moisture-curable resin comprises a hydrolyzable silyl group.

[0017] In one embodiment of the moisture-curable composition according to any of the above-mentioned embodiments, the moisture-curable resin (a) is selected from a silylated polyol; a silylated polyether; a silylated polyurethane; a silane-containing copolymer derived from the copolymerization of an ethylenically unsaturated silane selected from vinyl silane, allyl silane, methallyl silane, acryloxyalkyl silane, methacryloxyalkyl silane with an ethylenically unsaturated monomer selected from olefinic hydrocarbons, acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, ethylenically unsaturated dicarboxylic acids, and / or anhydrides of ethylenically unsaturated monomers, oligomers and / or polymers having ethylenic unsaturation; or a combination of two or more thereof.

[0018] In one embodiment of the moisture-curable composition according to any of the above embodiments, the moisture-curable resin (a) is selected from silylated polyurethanes.

[0019] In one embodiment, the silylated polyurethane has the formula: R z -[OC(O)NH-R 6 Si(R 7 ) x (OR 8 ) 3-x ] y wherein R z is the organic polymer part, and R 6 is an alkylene group of up to 12 carbon atoms, optionally containing one or more heteroatoms; R 7 are the same or different alkyl or aryl groups of up to 8 carbon atoms, R 8 are the same or different alkyl groups of up to 6 carbon atoms, x is 0, 1 or 2, and y is 1 to 6.

[0020] In one embodiment, R 1 is selected from C1 to C20 linear or branched divalent hydrocarbon groups; R 2 , R 3 , and R 4are each independently selected from C1 to C10 alkyl; 5 is selected from C1 to C10 alkyl.

[0021] In one embodiment, R 2 , R 3 , and R 4 Each of is C1 to C20 alkyl, C4 to C20 cycloalkyl, C6 to C30 aryl, or -OR 5 is selected from.

[0022] In one embodiment, R 1 is selected from C1 to C20 linear or branched divalent hydrocarbon groups, and R 2 , R 3 , and R 4 Each of -OR 5 is selected from, where R 5 is independently selected from C1 to C4 alkyl.

[0023] In one embodiment of the moisture-curable composition according to any of the above embodiments, the composition further comprises an additive selected from a pigment, a filler, a curing catalyst, a dye, a plasticizer, a thickener, a coupling agent, an extender, a solvent, a wetting agent, a tackifier, a crosslinking agent, a thermoplastic polymer, an adhesion promoter, a UV stabilizer, or a combination of two or more thereof.

[0024] In one embodiment of the moisture-curable composition according to any of the above embodiments, the composition further comprises a catalyst that catalyzes the reaction of the moisture-curable resin (a) with water under curing conditions.

[0025] In another aspect, provided is a cured composition produced by contacting a moisture-curable composition according to any of the above embodiments with water.

[0026] In yet another aspect, provided is a moisture-curable sealant, adhesive, or coating containing a moisture-curable resin composition according to any of the above-described embodiments.

[0027] Provided in still yet another aspect is a method of forming a hardened composition comprising contacting a composition according to any of the above embodiments with water.

[0028]

[0023] Provided in still yet another aspect is a method of treating a substrate comprising applying to a surface of the substrate a moisture-curable composition according to any of the above-described embodiments.

[0029] The following description and drawings disclose various exemplary aspects. Some improvements and novel aspects may be explicitly identified, while others may be apparent from the description and drawings. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0030] Reference will now be made to exemplary embodiments, examples of which are described in the following detailed description. As will be understood, other embodiments may be utilized, and structural and functional changes may be made. Furthermore, features of the various embodiments may be combined or varied. Thus, the following description is presented by way of example only, and is not intended to limit in any way the various alternatives and modifications that may be made to the illustrated embodiments. In this disclosure, numerous specific details are set forth to provide a thorough understanding of the disclosed subject matter. It should be understood that aspects of the present disclosure may be embodied in other embodiments that do not necessarily include all aspects set forth herein or elsewhere.

[0031] As used herein, the terms "example" and "exemplary" mean illustrative or illustrative. The terms "example" and "exemplary" do not indicate required or preferred aspects or embodiments. The term "or" is intended to be inclusive rather than exclusive, unless the context indicates otherwise. For example, the phrase "A uses B or C" includes any inclusive permutation (e.g., A uses B; A uses C; or A uses both B and C). As another matter, the articles "a" and "an" are generally intended to mean "one or more," unless the context indicates otherwise.

[0032] As used herein, the terms "polymer" and "resin" or "polymer resin" are used interchangeably.

[0033] The values ​​for each component range can be combined to form new unspecified ranges.

[0034] Provided is a composition comprising (a) a moisture-curable polymer and (b) a moisture scavenger, where the moisture scavenger is selected from (cyanoalkyl)alkoxysilanes. The (cyanoalkyl)alkoxysilanes have been found to be excellent moisture scavengers, providing comparable or better moisture scavenging action when compared to moisture scavengers such as traditional alkoxysilanes. One indicator of the effectiveness of the moisture scavenger is the viscosity of the composition when exposed to moisture. Exposure to moisture in a moisture-curable composition results in crosslinking, increasing the viscosity of the material. A suitable moisture scavenger has the effect of slowing down the increase in viscosity.

[0035] The moisture scavenger (b) is selected from cyanoalkylalkoxysilanes. In one embodiment, the cyanoalkylalkoxysilanes have the formula: NC-R 1 -Si(R 2 )(R 3 )(R 4 ) where R 1 is selected from divalent hydrocarbon groups having 1 to 20 carbon atoms; R 2 , R 3 , and R 4 each independently represents a monovalent hydrocarbon of C1 to C30, a halide, or -OR 5 is selected from, where R 5 is selected from C1 to C20 monovalent hydrocarbons, with the proviso that R 2 , R 3 , and R 4 At least one of the groups is a halide or -OR 5 is selected from.

[0036] The divalent hydrocarbon and the monovalent hydrocarbon can be selected from linear, branched, or cyclic hydrocarbons. Branched hydrocarbons generally contain three or more carbon atoms. Cyclic hydrocarbons generally contain four or more carbon atoms. Cyclic hydrocarbons may also contain one or more unsaturated C-C bonds, and in embodiments, may contain one or more aromatics. In one embodiment, the monovalent hydrocarbon is selected from alkyl, cycloalkyl, and aryl. In one embodiment, the divalent hydrocarbon is selected from alkylene. The alkylene may include cycloalkylene. The halide can be selected from chloride, bromide, or iodide.

[0037] In one embodiment, R 1 is selected from C1 to C20 alkylene; R 2 , R 3 , and R 4 are each independently selected from C1 to C20 alkyl, C4 to C20 cycloalkyl, and C6 to C30 aryl; and R 5 is selected from C1 to C20 alkyl.

[0038] Cycloalkyl can include groups with one or more cycloalkyl rings, which can be separated by bonds, linking groups, or fused together, and can optionally include one or more groups (e.g., alkyl, alcohol, etc.) attached to the rings. Aryl groups can include groups with one or more aromatic rings, where the groups with more than one ring can be joined by bonds, linking groups, or fused together, and can optionally include one or more groups (e.g., alkyl, alcohol, etc.) attached to the rings. C6-C30 aryl groups can include, for example, C7-C30 arylalkyl groups and C7-C30 alkylaryl groups.

[0039] In one embodiment, R 1 is selected from C1-C10 alkylene, C2-C8 alkylene, or C3-C6 alkylene; R 2 , R 3 , and R 4 each independently represents C1 to C10 alkyl, C3 to C8 alkyl, C4 to C6 alkyl, or -OR 5 is selected from, where R 5 is selected from C1-C10 alkyl, C2-C8 alkyl, or C3-C6 alkyl. 1 is selected from C2 alkylene; R 2 , R 3 , and R 4 are each C alkyl; and R 5 is a C1 alkyl.

[0040] In one embodiment, R 1 is selected from C1 to C20 alkylene, and R 2 , R 3 , and R 4 Each of -OR 5 is selected from, where R 5 is independently selected from C1-C20 alkyl, C4-C20 cycloalkyl, and C6-C30 aryl. 1is selected from C2-C4 alkylene, and R 2 , R 3 , and R 4 Each of -OR 5 is selected from, where R 5 is independently selected from C2 to C4 alkyl.

[0041] Examples of suitable cyanoalkylalkoxysilanes include, but are not limited to, cyanomethyltrimethoxysilane, cyanomethyltriethoxysilane, cyanomethyltripropoxysilane, 2-cyanoethyltrimethoxysilane, 2-cyanoethyltriethoxysilane, 2-cyanoethyltripropoxysilane, 2-cyanoethyldimethoxymethylsilane, 2-cyanoethyldimethoxyethylsilane, 2-cyanoethyldiethoxymethylsilane, 2-cyanoethyldiethoxyethylsilane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltripropoxysilane, 3-cyanopropyldimethoxymethylsilane, 3-cyanopropyldimethoxyethylsilane, 3-cyanopropyldiethoxymethylsilane, 3-cyanopropyldiethoxyethylsilane, and others, or combinations of two or more thereof.

[0042] The moisture scavenger is present in the composition in an amount of about 0.2% to about 2% by weight, about 0.5% to about 1.75% by weight, about 0.75% to about 1.5% by weight, or about 1% to about 1.25% by weight, based on the total weight of polymer (a).

[0043] The moisture-curable polymer (a) is not particularly limited and can be selected as desired for a particular purpose or intended use. A moisture-curable polymer is a polymer that undergoes hydrolysis and subsequent condensation when exposed to moisture to provide a resin with suitable properties for a particular purpose or intended use. In general, moisture-curable polymers are suitable for forming materials suitable for use in adhesives, sealants, coatings, and the like.

[0044] The basic structure, repeating units, or backbone of the polymer is generally not limited and can be selected as desired for a particular purpose or intended use. In one embodiment, the polymer is selected from polyepoxides, polyolefins, polyvinyl chlorides, polyesters, polyurethanes, polyamides, polyfluoroalkenes, polyethers, polyacrylic acids, polymethacrylic acids, and others that contain hydrolyzable functional groups that render the polymer reactive when exposed to moisture.

[0045] In one embodiment, the moisture-curable polymer is a polymer resin containing hydrolyzable silyl groups. These may also be called silylated polymers. Examples of suitable silylated polymers include, but are not limited to, silylated polyols, silylated polyethers, silylated polyurethane resins, and silane-containing copolymers derived from the copolymerization of one or more ethylenically unsaturated silanes, such as vinyl silanes, allyl silanes and methallyl silanes, acryloxyalkyl silanes, methacryloxyalkyl silanes, with one or more other ethylenically unsaturated monomers, such as olefinic hydrocarbons, acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, ethylenically unsaturated dicarboxylic acids and / or their anhydrides, oligomers and / or polymers having ethylenic unsaturation. In one embodiment, the moisture-curable polymer is selected from silylated polyurethane resins (SPUR). The moisture-curable polyurethane is not particularly limited and can be selected as desired for a particular purpose or intended use.

[0046] For silylated resins, the resins can be formed by reacting a suitable silane-functional material with a precursor resin. Such suitable precursor resins are generally known or can be determined by one skilled in the art. In one embodiment, suitable precursor resins include (i) polyether polyols, (ii) polyester polyols, (iii) hydroxy-terminated polybutadienes, (iv) hydroxy- and isocyanate-terminated polyurethane prepolymers derived from any of these, (v) isocyanate- and amine-terminated polyurethane polyurea (poly(urethane urea) or polyurethane urea) prepolymers and polyurea prepolymers derived from polyamines, and (vi) olefinically unsaturated polymers capable of hydrosilylation with hydridosilanes, such as polyolefins and polyethers with terminal olefinic unsaturation. The resins can be obtained by silylation of these and similar precursor resins in any manner known or to be discovered in the future. Some existing processes for obtaining silylated resins include, for example, the silylation of hydroxyl-terminated resins by reaction with isocyanate silanes, the silylation of isocyanate-terminated resins with silanes having functionality reactive towards isocyanates, such as mercapto or amino functionality, and the silylation of olefinically unsaturated resins by reaction with hydridosilanes (hydrosilanes) under hydrosilylation reaction conditions.

[0047] In one embodiment, the moisture curable resin is a silylated SPUR, such as, but not limited to, those described in U.S. Pat. No. 5,990,257, the entire contents of which are incorporated herein by reference in their entirety.

[0048] Isocyanate-terminated PUR prepolymers can be obtained by reacting one or more polyols, advantageously diols, with one or more polyisocyanates, advantageously diisocyanates, in such proportions that the resulting prepolymer is terminated with an isocyanate. When a diol is reacted with a diisocyanate, a molar excess of the diisocyanate is used.

[0049] Polyols that can be utilized for the preparation of isocyanate-terminated PUR prepolymers include polyether polyols, polyester polyols such as hydroxyl-terminated polycaprolactone, polyetherester polyols such as those obtained from the reaction of polyether polyols with ε-caprolactone, polyesterether polyols such as those obtained from the reaction of hydroxyl-terminated polycaprolactone with one or more alkylene oxides such as ethylene oxide and propylene oxide, hydroxyl-terminated polybutadiene, and others.

[0050] Specific suitable polyols that can be utilized for the preparation of isocyanate-terminated PUR prepolymers include poly(oxyalkylene) ether diols (i.e., polyether diols), particularly poly(oxyethylene) ether diols, poly(oxypropylene) ether diols and poly(oxyethylene-oxypropylene) ether diols, poly(oxyalkylene) ether triols, poly(tetramethylene) ether glycols, polyacetals, polyhydroxy polyacrylates, polyhydroxy polyester amides, polyhydroxy polythioethers, polycaprolactone diols and triols, and others. In one embodiment of the invention, the polyols used in the preparation of the isocyanate-terminated PUR prepolymers are poly(oxyethylene) ether diols having an equivalent weight of about 500 to about 25,000. In another embodiment of the invention, the polyols used in the preparation of the isocyanate-terminated PUR prepolymers are poly(oxypropylene) ether diols having an equivalent weight of about 1,000 to about 20,000. Mixtures of polyols of different structures, molecular weights, and / or functionality can also be used.

[0051] The polyether polyols can have a functionality of up to about 8, but preferably have a functionality of 2 to 4, and more preferably have a functionality of 2 (i.e., diols). Particularly suitable are polyether polyols prepared in the presence of double metal cyanide (DMC) catalysts, alkali metal hydroxide catalysts, or alkali metal alkoxide catalysts; see, for example, U.S. Patent Nos. 3,829,505, 3,941,849, 4,242,490, 4,335,188, 4,687,851, 4,985,491, 5,096,993, 5,100,997, 5,106,874, 5,116,931, 5,136,010, 5,185,420, and 5,266,681. The entire contents of each of these patents are incorporated herein by reference in their entirety. In one embodiment, the polyether polyol preferably has a number average molecular weight of about 1,000 to about 25,000, more preferably about 2,000 to about 20,000, and even more preferably about 4,000 to about 18,000. Examples of commercially available diols suitable for making isocyanate-terminated PUR prepolymers include ARCOL R-1819 (number average molecular weight 8,000), E-2204 (number average molecular weight 4,000), and ARCOL E-2211 (number average molecular weight 11,000).

[0052] Any of a number of polyisocyanates, advantageously diisocyanates and mixtures thereof, can be used to provide the isocyanate-terminated PUR prepolymer. In one embodiment, the polyisocyanate can be diphenylmethane diisocyanate ("MDI"), polymethylene polyphenylisocyanate ("PMDI"), paraphenylene diisocyanate, naphthylene diisocyanate, liquid carbodiimide-modified MDI and its derivatives, isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, toluene diisocyanate ("TDI"), particularly the 2,6-TDI isomer, as well as a variety of other aliphatic and aromatic polyisocyanates, and combinations thereof, that are well established in the art.

[0053] Silylation reactants for reacting with the isocyanate-terminated PUR prepolymers described above contain isocyanate-reactive functionality and at least one readily hydrolyzable and subsequently crosslinkable group, such as an alkoxy. Particularly useful silylation reactants have the general formula: XR 6 -Si(R 7 ) x (OR 8 ) 3-x where X is an active hydrogen-containing group reactive towards isocyanates, e.g., -SH or -NHR. 9 And this R 9 is H, a monovalent hydrocarbon radical of up to 8 carbon atoms, or -R 10 -Si(R 11 ) y (OR 12 ) 3-y and R 6 and R 10 each of which is the same or different divalent hydrocarbon radical of up to 12 carbon atoms, optionally containing one or more heteroatoms; R 7 and R 11 are the same or different monovalent hydrocarbon radicals of up to 8 carbon atoms, R 8 and R 12 are the same or different alkyl groups of up to 6 carbon atoms, and each of x and y is independently 0, 1 or 2.

[0054] Examples of silanes that can be used as reactants to silylate the resin include, but are not limited to, mercaptosilanes such as 2-mercaptoethyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 2-mercaptoethyltriethoxysilane, 3-mercaptopropyltriethoxysilane, 2-mercaptoethyltripropoxysilane, 2-mercaptoethyltrisec-butoxysilane, 3-mercaptopropyltri-t-butoxysilane, 3-mercaptopropyltriisoprop ... Mercaptopropyl methoxysilane, 2-mercaptoethyl tri-2'-ethylhexoxysilane, 2-mercaptoethyl dimethoxyethoxysilane, 3-mercaptopropyl methoxyethoxypropoxysilane, 3-mercaptopropyl dimethoxymethylsilane, 3-mercaptopropyl methoxydimethylsilane, 3-mercaptopropyl ethoxydimethylsilane, 3-mercaptopropyl diethoxymethylsilane, 3-mercaptopropyl cyclohexoxydimethylsilane, 4-mercaptobutyl trimethoxysilane, 3-mercapto-3-methylpropyl trimeth silane, 3-mercapto-3-methylpropyl-tripropoxysilane, 3-mercapto-3-ethylpropyl-dimethoxymethylsilane, 3-mercapto-2-methylpropyltrimethoxysilane, 3-mercapto-2-methylpropyldimethoxyphenylsilane, 3-mercaptocyclohexyl-trimethoxysilane, 12-mercaptododecyltrimethoxysilane, 12-mercaptododecyl-triethoxysilane, 18-mercaptooctadecyltrimethoxysilane, 18-mercaptooctadecylmethoxydimethylsilane, 2-mercapto to-2-methylethyl-tripropoxysilane, 2-mercapto-2-methylethyl-trioctoxysilane, 2-mercaptophenyltrimethoxysilane, 2-mercaptophenyltriethoxysilane, 2-mercaptotolyltrimethoxysilane, 2-mercaptotolyltriethoxysilane, 1-mercaptomethyltolyltrimethoxysilane, 1-mercaptomethyltolyltriethoxysilane, 2-mercaptoethylphenyltrimethoxysilane, 2-mercaptoethylphenyltriethoxysilane, 2-mercaptoethyltolyltrimethoxysilane,2-Mercaptoethyltolyltriethoxysilane, 3-mercaptopropylphenyltrimethoxysilane, and 3-mercaptopropylphenyltriethoxysilane, as well as aminosilanes such as 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 4-aminobutyltriethoxysilane, N-methyl-3-amino-2-methylpropyltrimethoxysilane, N-ethyl-3-amino-2-methylpropyltrimethoxysilane, N-ethyl-3-amino-2-methylpropyldiethoxymethylsilane, N-ethyl-3-amino-2-methylpropyltriethoxysilane, N-ethyl-3-amino-2-methylpropylmethyldimethoxysilane, N-butyl-3-amino-2-methylpropyltrimethoxysilane, 3-(N N-methyl-2-amino-1-methyl-1-ethoxy)-propyltrimethoxysilane, N-ethyl-4-amino-3,3-dimethyl-butyldimethoxymethylsilane, N-ethyl-4-amino-3,3-dimethylbutyltrimethoxysilane, N-(cyclohexyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, aminopropyltriethoxysilane, bis-(3-trimethoxysilyl-2-methylpropyl)amine, and N-(3'-trimethoxysilylpropyl)-3-amino-2-methylpropyltrimethoxysilane.

[0055] Catalysts are typically used to prepare isocyanate-terminated PUR prepolymers. Condensation catalysts are commonly used to prepare PUR. These catalysts may also catalyze the curing (hydrolysis and subsequent crosslinking) of the SPUR resin component of the moisture-curable composition. Suitable condensation catalysts include, but are not limited to, dialkyltin dicarboxylates such as dibutyltin dilaurate and dibutyltin acetate, tertiary amines, tin salts of carboxylic acids such as stannous octoate and stannous acetate, and others. In one embodiment of the invention, a dibutyltin dilaurate catalyst is used to prepare the PUR prepolymer. Other useful catalysts include zirconium- and bismuth-containing complexes such as K-KAT XC6212, K-KAT XC-A209, and K-KAT 348 available from King Industries, TYZOR available from Dorf Ketal, and others. 登録商標 Aluminum chelates, such as the KR type available from Kenrich Petrochemical Company, as well as other organometallic catalysts, such as those containing metals such as Zn, Co, Ni, Fe, and others.

[0056] In another embodiment, the moisture-curable SPUR resin can be obtained from a hydroxyl-terminated PUR prepolymer. The moisture-curable SPUR resin can be prepared by reacting a hydroxyl-terminated PUR prepolymer with an isocyanate silane, as described above. The hydroxyl-terminated PUR prepolymer can be obtained in substantially the same manner as described above for the preparation of an isocyanate-terminated PUR prepolymer, using substantially the same materials, namely, a polyol, a polyisocyanate, and optionally a catalyst (preferably a condensation catalyst). One major difference in these reactions is that the polyol and polyisocyanate are used in a ratio that results in a hydroxyl-terminated prepolymer. Thus, for example, in the case of a diol and a diisocyanate, the former is used in molar excess, thereby resulting in a hydroxyl-terminated hydroxyl-terminated PUR prepolymer.

[0057] Useful silylation reactants for hydroxyl-terminated SPUR resins are those that contain an isocyanate terminus and a readily hydrolyzable functionality, such as one to three alkoxy groups. Suitable silylation reactants have the general formula: OCN-R 6 -Si(R 7 ) x (OR 8 ) 3-x isocyanate silane, where R 6 is an alkylene group of up to 12 carbon atoms, optionally containing one or more heteroatoms; R 7 are the same or different alkyl or aryl groups of up to 8 carbon atoms, R 8 are the same or different alkyl groups of up to 6 carbon atoms, and x is 0, 1, or 2. 6 has 1 to 4 carbon atoms, R 8 are the same or different methyl, ethyl, propyl, or isopropyl groups, and x is 0.

[0058] Specific isocyanate silanes that can be used to react with the hydroxyl-terminated PUR prepolymer to provide the moisture-curable SPUR resin include, but are not limited to, isocyanate propyl trimethoxy silane, isocyanate isopropyl trimethoxy silane, isocyanate-n-butyl trimethoxy silane, isocyanate-t-butyl trimethoxy silane, isocyanate propyl triethoxy silane, isocyanate isopropyl triethoxy silane, isocyanate-n-butyl triethoxy silane, isocyanate-t-butyl triethoxy silane, and others.

[0059] The polymer, in various embodiments, has the general formula: R z -[OC(O)NH-R 6 Si(R 7 ) x (OR 8 ) 3-x ]y wherein R z is the organic polymer moiety, and R 6 , R 7 , and R 8 is as defined above, and y is 1 to 6. In one embodiment, the organic polymer segment is a polymer segment that includes at least one urethane group.

[0060] For practical applications, the moisture curable composition may optionally contain additives such as pigments, fillers, curing catalysts, dyes, plasticizers, thickeners, coupling agents, extenders, volatile organic solvents, wetting agents, tackifiers, crosslinking agents, thermoplastic polymers, and UV stabilizers. These additives may be used in any suitable amount as understood by those skilled in the art as useful for a particular purpose or intended application.

[0061] The catalyst (c) of the moisture curable composition can be any catalyst effective to promote the reaction between the moisture curable polymer (a) and the reactive modifier (b) when exposed to moisture. Suitable curing catalysts include, but are not limited to, organometallic catalysts, amine catalysts, and others. Preferably, the catalyst is selected from the group consisting of organotin compounds, zirconium complexes, aluminum chelates, titanium chelates, organozinc, organocobalt, organoferric, organonickel, and organobismuth, and mixtures thereof. The amine catalyst is selected from the group consisting of primary amines, secondary amines, tertiary amines, aminosilanes, and mixtures thereof. The catalyst can be a mixture of organometallic and amine catalysts.

[0062] Representative examples of catalysts include, but are not limited to, dibutyltin oxide, dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin diacetate, stannous octoate, stannous acetate, stannous oxide, morpholine, 3-aminopropyltrimethoxysilane, 2-(aminoethyl)-3-aminopropyltrimethoxysilane, tri-isopropylamine, bis-(2-dimethylaminoethyl)ether, and piperazine. Other useful catalysts include K-KAT, available from King Industries, Inc. TM XC6212, K-KAT TM 5218 and K-KAT TM Zirconium-, aluminum-, and bismuth-containing complexes, such as TYZOR 348, available from Dorfketal; 登録商標 Type and KR commercially available from Kenrich Petrochemical Company TM Titanium chelates such as type 1, commercially available from Momentive Performance Materials, Inc. TM Amines such as A-99 amine, and others.

[0063] The catalyst may be present in the moisture curable composition in an amount of from about 0.05% to about 5% by weight based on the combined weight of components (a), (b) and (c), preferably from about 0.1% to about 3% by weight based on the combined weight of components (a), (b) and (c), and most preferably from about 0.5% to about 2% by weight based on the combined weight of components (a), (b) and (c).

[0064] Typical fillers suitable for the moisture curable resin composition of the present application include, but are not limited to, ground, precipitated, and colloidal calcium carbonate, fumed silica, precipitated silica, silica gel, and reinforcing silicas such as hydrophobized silica and silica gel, for example, treated with compounds such as stearates or stearic acid; crushed and ground quartz, alumina, aluminum hydroxide, titanium hydroxide, diatomaceous earth, iron oxide, carbon black and graphite, or clays such as kaolin, bentonite, or montmorillonite, talc, mica, and others. In one embodiment of the present invention, the amount of filler is from 0.1% to about 90% by weight of the total composition. In yet another embodiment of the present invention, the amount of filler is from about 5% to about 60% by weight of the total composition. In yet another embodiment of the present invention, the amount of filler is from about 10% to about 40% by weight of the total composition. The filler may be a single type or may be a mixture of two or more types.

[0065] Plasticizers commonly used in the moisture curable resin composition of the present invention can also be used in the present invention to modify the properties of the filler to facilitate the use of high levels of filler. Exemplary plasticizers include phthalates, dipropylene and diethylene glycol dibenzoates, alkylsulfonate phenols, alkylphenanthrenes, alkyl / diaryl phosphates, and mixtures thereof, as well as others. The moisture curable resin composition of the present invention can include various thixotropic or non-sag agents. Various castor oils, fumed silica, treated clays, and polyamides are representative of this type of additive. Stabilizers that can be incorporated into the moisture curable resin composition of the present invention include, for example, hindered amines and dialkylhydroxyamines. Adhesion promoters, such as alkoxysilane adhesion promoters, are useful in the moisture curable composition of the present invention.

[0066] Examples of plasticizers suitable for the moisture curable compositions of the present application include, but are not limited to, phthalates, dipropylene and diethylene glycol dibenzoates and mixtures thereof, epoxidized soybean oil, and others. Dioctyl phthalate and diisodecyl phthalate are commercially available from Exxon Chemical Company under the trade names Jayflex DOP and JayFlex DIDP. Dibenzoates are available from Velsicol Chemical Company as Benzoflex 9-88, Benzoflex 9-88SG, Benzoflex 50, and Benzoflex 400. Epoxidized soybean oil is available from Hewton Chemical Company as Flexol EPO. Plasticizers can be present in the moisture curable composition at levels of 0 to 50 parts by weight, and preferably 5 to 15 parts by weight, per 100 parts by weight of the total composition.

[0067] Useful solvents include, but are not limited to, aromatic and aliphatic esters and ketones. In one embodiment, the solvent is present in an amount of about 0.1 to about 20 parts by weight, about 0.5 to about 5 parts by weight, or about 1 to about 3 parts by weight per 100 parts by weight of the total moisture curable composition of the present invention.

[0068] In one embodiment, the composition may further comprise an adhesion promoter. In one embodiment, the adhesion promoter may be a combination blend of n-2-aminoethyl-3-aminopropyltrimethoxysilane and 1,3,5-tris(trimethoxysilylpropyl)isocyanurate. Other adhesion promoters useful in the present invention include, but are not limited to, n-2-aminoethyl-3-aminopropyltriethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, bis-γ-trimethoxysilylpropyl)amine, N-phenyl-γ-aminopropyltrimethoxysilane, triaminofunctional trimethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropylmethyldiethoxysilane, methacryloxypropyltrimethoxysilane, methylaminopropyltrimethoxysilane, γ-glycidoxypropylethyldi ... propyltrimethoxysilane, gamma-glycidoxyethyltrimethoxysilane, beta-(3,4-epoxycyclohexyl)propyltrimethoxysilane, beta-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, isocyanatopropyltriethoxysilane, isocyanatopropylmethyldimethoxysilane, beta-cyanoethyltrimethoxysilane, gamma-acryloxypropyltrimethoxysilane, gamma-methacryloxypropylmethyldimethoxysilane, 4-amino-3,3-dimethylbutyltrimethoxysilane, and n-ethyl-3-trimethoxysilyl-2-methylpropanamine, and others.

[0069] The adhesion promoter may be added to the composition in the range of about 0.1% to about 20% by weight. In one embodiment of the invention, the adhesion promoter may range from about 0.3% to about 10% by weight of the total composition. In another embodiment of the invention, the adhesion promoter may range from about 0.5% to about 2% by weight of the total composition.

[0070] In another aspect, the present invention also relates to a cured composition prepared by curing the moisture-curable resin composition described above, as well as sealants, including hot melt sealants, primers, adhesives, including hot melt adhesives, and coatings containing such cured compositions. The cured composition of the present invention may be prepared by contacting the moisture-curable composition with water. As used herein, the term "water" means atmospheric moisture, steam, liquid water, ice, or water mixed with other organic compounds such as organic solvents, and preferably atmospheric moisture. An effective amount of water is an amount sufficient to react with the hydrolyzable silyl groups to effect curing of the composition. Illustratively, the cured composition includes a hot melt composition. As used herein, the term "hot melt composition" refers to a material that is solid at room temperature, melts when heated for application to a substrate, and solidifies again when cooled to form a strong bond between the solid material and the substrate. Hot melt compositions include, but are not limited to, hot melt sealants and hot melt adhesives.

[0071] In the above detailed description, the present technology has been described with reference to various aspects and embodiments. The technology may be further understood with reference to the following examples, which are intended to further illustrate, but not necessarily limit, aspects and embodiments of the present technology.

[0072] Working Example

[0073] Synthesis procedure of silane-grafted polymer A

[0074] A 1 L 4-neck round bottom flask was fitted with a mechanical stirrer, thermocouple, a dip leg for N2 sparging, and a condenser aligned with a Schlenk line. It was inerted with N2. The flask was charged with polyepoxydiol HMBT120 (500 grams). It was stirred overnight at 80°C while sparging with N2 under 40-50 mmHg pressure. The temperature was reduced to 70°C. Isophorone diisocyanate (IPDI, 5.1 grams) and dibutyltin dilaurate (DBTDL, 0.011 grams) were added, and the reaction mixture was stirred at 70-75°C. The viscosity of the reaction mixture was measured at 25°C with a Brookfield DV3THBCJ0 cone-plate viscometer and monitored until it reached approximately 30,000 cps. 3-Isocyanatopropyltrimethoxysilane (SILQUEST A-LINK35 silane, Momentive Performance Materials, Inc., 9.6 grams) was added with stirring. The reaction temperature was raised to 80-85°C and the viscosity was monitored again. When the viscosity reached 60,000-70,000 cps, methanol (0.4 grams) was added to quench the reaction. The mixture was stirred for an additional 10 minutes and cooled to give a viscous material (Silane-Grafted Polymer A).

[0075] Synthesis procedure of silane-grafted polymer B

[0076] A 1 L 4-neck round bottom flask was fitted with a mechanical stirrer, thermocouple, a dip leg for N2 sparging, and a condenser aligned with a Schlenk line. It was inerted using N2. The flask was charged with polyepoxydiol HMBT80 (500 grams). It was stirred overnight at 80°C while sparging with N2 under 40-50 mmHg pressure. Isophorone diisocyanate (IPDI, 4.2 grams) and dibutyltin dilaurate (DBTDL, 0.032 grams) were added, and the reaction mixture was stirred at about 80°C. The viscosity of the reaction mixture was monitored every 30 minutes until it remained constant at about 15,000 cps. 3-Isocyanatopropyltriethoxysilane (SILQUEST A-LINK25 silane, Momentive Performance Materials, Inc., 22.1 grams) was added with stirring. The reaction temperature was held at about 80°C, and the viscosity was again monitored. When the viscosity reached a constant level, ethanol (0.9 grams) was added to quench the reaction. The mixture was stirred for an additional 10 minutes and cooled to give a viscous material (Silane-grafted Polymer B).

[0077] Performance evaluation of moisture scavengers in silane-grafted polymers

[0078] The performance of the moisture scavenger was evaluated by monitoring the viscosity change of the silane-grafted polymer upon exposure to moisture. In the silane-grafted polymer, hydrolysis of the silane ends and subsequent intermolecular crosslinking upon exposure to air / moisture leads to an increase in viscosity. A small change in viscosity indicates good performance of the moisture scavenger added to the silane-grafted polymer.

[0079] A typical sample for performance testing was prepared as follows:

[0080] Silane-grafted polymer A or silane-grafted polymer B (10.0-50.0 grams) was placed in a plastic open-top container. Moisture scavenger material as shown in Table 1 was added to the container in an amount of 0.10-1.0 grams, which is 2.0% by weight based on polymer A or B, and mixed thoroughly with a speed mixer (FlackTek speed mixer, DAC600.2VAC-P). The samples were placed in a humidity chamber at 23°C and 50% relative humidity. The viscosity of the samples was measured periodically at intervals of 7 days. Viscosity was measured at 25°C with a Brookfield DV3THBCJ0 cone-plate viscometer. [Table 1]

[0081] Moisture scavengers S-3 and S-7 are scavengers of the present invention. Moisture scavengers S-1, S-2, S-4, S-5, and S-6 are known / conventional scavengers. Test results are summarized in Tables 2, 3, and 4. Test Examples C1-C10 are comparative examples. Test Examples E1-E3 correspond to examples according to aspects and embodiments of the technology of the present invention.

[0082] [Table 2]

[0083] [Table 3]

[0084] [Table 4]

[0085] Preparation procedure for sealant formulation

[0086] Masterbatch of sealant material without moisture scavengers:

[0087] Momentive's SPUR+1015 prepolymer (688.2 grams), BASF's Tinuvin 登録商標 213 UV absorber (6.9 grams), and Tinuvin from BASF 登録商標 765 Light Stabilizer (6.9 grams) was mixed in a Ross mixer at low vacuum for 10 minutes. Diisodecyl phthalate (DIDP, 543.0 grams), precipitated calcium carbonate (PCC, 990.0 grams), ground calcium carbonate (GCC, 660.0 grams), titanium dioxide (34.5 grams), and fumed silica (Cabot TS720, 34.5 grams) were then added stepwise and the mixture was mixed at high speed for 1-2 hours until the particles were well dispersed. It was cooled to room temperature to provide about 2900 grams of a master batch of sealant material.

[0088] Sealant formulations containing moisture scavengers

[0089] A master batch of the above sealant material (167.96 grams) was placed in a plastic cup. Momentive SILQUEST A-1120J silane (0.97 grams) was added and mixed under vacuum in a Speedmixer. It was then cooled to about 30°C. Catalyst Fomrez 登録商標 SUL-4 (dibutyltin dilaurate, 102 mg) and a candidate moisture scavenger (1.02 grams, selected from Table 1) were added to the mixture, which was mixed for an additional minute. Samples containing different moisture scavengers were prepared and tested in parallel. Their performance is shown in Table 5.

[0090] mechanical properties

[0091] The sealant formulations containing the moisture scavengers were cast into films and cured for 7 days in a humidity chamber at 23° C. and 50% relative humidity. Tensile properties were tested according to ASTM D412 and hardness was tested under ASTM C661. The test results are shown in Table 5.

[0092] Dry to touch time measurement

[0093] The sealant formulation containing the moisture scavenger was poured into an aluminum weighing pan and immediately placed in a humidity chamber. The tack-free time was assessed by using a wood block to contact the sample surface and lifting it off at intervals of several minutes. The tack-free time was determined when no more material was lifted by the wood block. The results are summarized in Table 5.

[0094] Extrusion speed measurement

[0095] The sealant formulation containing the moisture scavenger was packaged in a plastic cartridge. The initial extrusion rate was measured by extruding it through a ⅛ inch diameter nozzle. The cartridge was then tightly sealed / capped. It was aged at 50° C. for 2 weeks and the extrusion rate was measured again. It was then resealed and aged at 50° C. for another 2 weeks (4 weeks in total) and finally the final extrusion rate was measured. The extrusion rate was calculated by dividing the weight of the extruded material by the time. If the material was completely cured in the cartridge and could not be extruded, the resulting extrusion rate was zero. The results are summarized in Table 5. Examples C11 and C12 are comparative examples. Example E4 is an example of the present invention.

[0096] [Table 5]

[0097] The results in Table 2 show that the addition of any water scavenger helps to slow down the rate of viscosity increase. On the other hand, S-3 and S-1 perform equally well as water scavengers, with S-3 performing slightly better than S-1. However, they stabilize the silane-grafted polymer A more effectively than S-2 and S-4.

[0098] The moisture scavenger tests in Table 3 compare the performance of S-1, S-2, and S-3 in the ethoxysilane grafted polymer, Polymer B. This comparison also confirms that S-3 performs comparably to S-1 in applications such as stabilizing the polymer, and is an improvement over S-2. These experimental results also show that the methoxysilane moisture scavengers (S-1 / -2 / -3) are very effective in the ethoxysilane grafted polymer.

[0099] The ethoxy analogs of S-1, S-2, and S-3 are S-5, S-6, and S-7, respectively. The performance of these ethoxy moisture scavengers was also evaluated in ethoxysilane-grafted polymer B. Table 4 summarizes their performance as desiccants. Although moisture scavengers S-5, S-6, and S-7 are relatively less effective compared to their methoxy counterparts (in Table 3), they still have the effect of reducing the rate of viscosity change.

[0100] Based on the excellent stabilizing performance of S-1, S-2, and S-3 as moisture scavengers in the silane-grafted polymer, they were further evaluated in sealant formulations, which are shown in Table 5.

[0101] The results in Table 5 show that S-3 has the longest dry to touch time among those tested. This indicates strong water absorption performance in the formulation, which can lead to long pot life. This gives the formulator a lot of room to adjust the formulation and get the pot life in the desired range. As shown in Table 5, the two conventional scavengers (S-1 and S-2) and the scavenger S-3 of the present technology show similar performance in terms of mechanical properties and hardness of the corresponding sealant formulations.

[0102] The extrusion rate upon aging is one way to evaluate the shelf life of the sealant formulation. The tested silane materials were also tested as moisture scavengers to extend the shelf life of the sealant. The experimental data are shown in Table 5. S-1, S-2, and S-3 were able to provide reasonable flow, gunnability, and extrudability.

[0103] Performance testing has shown that the cyanoalkylalkoxysilanes of the present invention are equivalent or better moisture scavengers than conventional moisture scavengers. They are better desiccants than other silanes, such as propyltrimethoxysilane. On the other hand, cyanoalkylalkoxysilanes are not believed to be skin sensitizers or flammable materials compared to the more common trialkoxysilanes, and are therefore generally believed to be a more practical alternative.

[0104] The combination of these two advantages, their demonstrated effectiveness as moisture scavengers, and their safety profile, make cyanoalkylalkoxysilanes highly desirable moisture scavengers for polymers, elastomers, resins, adhesives, sealants, coatings, and filler treatments, and more.

[0105] The above description includes examples of the present specification. Of course, for purposes of describing the present specification, it is not possible to describe every conceivable combination of components or methodologies, but one skilled in the art may recognize that many further combinations and permutations of the present specification are possible. Therefore, the present specification is intended to embrace all such changes, modifications, and variations that are included within the spirit and scope of the appended claims. Furthermore, to the extent that the term "comprises" is used in the detailed description or claims, such term is intended to be inclusive in the same manner as "includes," as "comprises" is interpreted when used as a transitional term in the claims.

[0106] The above description identifies various, non-limiting embodiments of moisture-curable compositions that include cyanoalkylalkoxysilane moisture scavengers. Modifications may occur to those skilled in the art and those who may make and use the invention. The disclosed embodiments are for illustrative purposes only and are not intended to limit the scope of the invention or the subject matter described in the following claims.

Claims

1. 1. A moisture-curable composition comprising: (a) a moisture-curable resin comprising a polymer that is reactive with water; and (b) a moisture scavenger selected from cyanoalkylalkoxysilanes; A moisture-curable composition comprising:

2. Cyanoalkylalkoxysilanes have the formula: NC-R １ -Si(R ２ )(R ３ )(R ４ ) wherein R １ is selected from C1 to C20 divalent hydrocarbon groups; R ２ , R ３ , and R ４ are each independently a C1 to C30 monovalent hydrocarbon, a halide, or —OR ５ where R ５ are independently selected from C1 to C30 monovalent hydrocarbons, with the proviso that R ２ , R ３ , and R ４ At least one of is -OR ５ The moisture-curable composition of claim 1, wherein the moisture-curable composition is selected from the group consisting of:

3. R １ is selected from C1 to C20 alkylene; R ２ , R ３ , and R ４ are each independently selected from C1-C20 alkyl, C4-C20 cycloalkyl, and C6-C30 aryl; and R ５ 3. The moisture-curable composition of claim 2, wherein is independently selected from C1 to C20 alkyl.

4. R １ is selected from C1 to C20 alkylene; R ２ , R ３ , and R ４ each is selected from C1-C10 alkyl, and R ５ The moisture-curable composition of claim 2, wherein is selected from C1 to C10 alkyl.

5. R １ is selected from C1-C4 alkylene, and R ２ , R ３ , and R ４ Each of these is -OR ５ where R ５ 3. The moisture-curable composition of claim 2, wherein is independently selected from C1 to C4 alkyl.

6. 2. The moisture-curable composition of claim 1, wherein the cyanoalkylalkoxysilane is selected from 2-cyanoethyltrimethoxysilane, 2-cyanoethyltriethoxysilane, 2-cyanoethyltripropoxysilane, 2-cyanoethyldimethoxymethylsilane, 2-cyanoethyldimethoxyethylsilane, 2-cyanoethyldiethoxymethylsilane, 2-cyanoethyldiethoxyethylsilane, 3-cyanopropyltrimethoxysilane, 3-cyanopropyltriethoxysilane, 3-cyanopropyltripropoxysilane, 3-cyanopropyldimethoxymethylsilane, 3-cyanopropyldimethoxyethylsilane, 3-cyanodiethoxymethylsilane, 3-cyanopropyldiethoxyethylsilane, or a combination of two or more thereof.

7. 10. The moisture-curable composition of claim 1, wherein the cyanoalkylsiloxane is present in an amount of about 0.1% to about 20% by weight based on the total weight of the moisture-curable resin (a).

8. 10. The moisture-curable composition of claim 1, wherein the cyanoalkylsilane is present in an amount of about 0.5% to about 10% by weight based on the total weight of the moisture-curable resin (a).

9. 2. The moisture-curable composition of claim 1, wherein the moisture-curable resin contains a hydrolyzable silyl group.

10. 2. The moisture-curable composition of claim 1, wherein the moisture-curable resin (a) is selected from the group consisting of silylated polyols, silylated polyethers, silylated polyurethanes, silane-containing copolymers derived from copolymerization of an ethylenically unsaturated silane selected from vinyl silanes, allyl silanes, methallyl silanes, acryloxyalkyl silanes, and methacryloxyalkyl silanes with an ethylenically unsaturated monomer selected from olefinic hydrocarbons, acrylic acid, methacrylic acid, acrylic acid esters, methacrylic acid esters, and ethylenically unsaturated dicarboxylic acids, and / or anhydrides of ethylenically unsaturated monomers, oligomers and / or polymers having ethylenic unsaturation; and combinations of two or more thereof.

11. 3. The moisture-curable composition of claim 2, wherein the moisture-curable resin (a) is selected from silylated polyurethanes.

12. The silylated polyurethane has the formula: R ｚ -[OC(O)NH-R ６ Si(R ７ ) ｘ (OR ８ ) ３－ｘ ] ｙ wherein R ｚ is the organic polymer moiety, and R ６ is an alkylene group of up to 12 carbon atoms, optionally containing one or more heteroatoms; R ７ are the same or different alkyl or aryl groups of up to 8 carbon atoms, and R ８ 12. The moisture-curable composition of claim 11, wherein each of is the same or different alkyl group of up to 6 carbon atoms, x is 0, 1 or 2, and y is 1 to 6.

13. R １ is selected from C1 to C20 linear or branched divalent hydrocarbon groups; R ２ , R ３ , and R ４ are each independently selected from C1-C10 alkyl; ５ The moisture-curable composition of claim 11, wherein is selected from C1 to C10 alkyl.

14. R ２ , R ３ , and R ４ each of which is C1 to C20 alkyl, C4 to C20 cycloalkyl, C6 to C30 aryl, or —OR ５ The moisture-curable composition of claim 11 selected from:

15. R １ is selected from C1 to C20 straight or branched chain divalent hydrocarbon groups, and R ２ , R ３ , and R ４ Each of these is -OR ５ where R ５ 12. The moisture-curable composition of claim 11, wherein is independently selected from C1 to C4 alkyl.

16. 10. The moisture-curable composition of claim 1, wherein the composition further comprises an additive selected from a pigment, a filler, a curing catalyst, a dye, a plasticizer, a thickener, a coupling agent, an extender, a solvent, a wetting agent, a tackifier, a crosslinking agent, a thermoplastic polymer, an adhesion promoter, a UV stabilizer, or a combination of two or more thereof.

17. 10. The moisture-curable composition of claim 1, wherein the composition further comprises a catalyst that catalyzes the reaction of the moisture-curable resin (a) with water under curing conditions.

18. 18. A cured composition produced by contacting the moisture-curable composition of any of claims 1 to 17 with water.

19. A moisture-curable sealant, adhesive, or coating comprising the moisture-curable resin composition of any one of claims 1 to 17.

20. 18. A method of forming a cured composition comprising contacting the moisture-curable composition of any of claims 1 to 17 with water.

21. A method for treating a substrate, comprising applying the moisture-curable composition of any one of claims 1 to 17 to the surface of the substrate.