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  Aspartic ester functional compoundsUSPTO Application #: 20060011295Title: Aspartic ester functional compounds Abstract: A functional aspartate prepared by A) reacting an aziridine with a Michael-acceptor molecule to form an aziridinyl aspartate, and B) reacting the aziridinyl aspartate with an active hydrogen containing compound to form the functional aspartate. The functional aspartate can be used in adhesive, sealant or coating compositions that also include an isocyanate functional material. The composition can be used in a method of bonding a first substrate to a second substrate that includes applying a coating of the above-identified adhesive composition to at least one surface of the first substrate or the second substrate, and contacting a surface of the first substrate with a surface of the second substrate, where at least on of the contacting surfaces has the coating applied thereto. The composition can also be used to coat substrates. (end of abstract) Agent: Bayer Material Science LLC - Pittsburgh, PA, US Inventors: Karsten Danielmeier, Douglas A. Wicks, Karen Marie Henderson, Evan Randall Minnich, John J. McLafferty, Stephanie A. Strazisar, Kurt C. Frisch USPTO Applicaton #: 20060011295 - Class: 156330900 (USPTO) The Patent Description & Claims data below is from USPTO Patent Application 20060011295. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE INVENTION [0001] The present invention relates to functional aspartic ester compounds and their use in adhesive, sealant, and coating compositions. BACKGROUND ART [0002] Aspartic esters represent a unique class of reactants in adhesive, coating, and sealant formulations. Their reactivity typically lies between slow classical polyols and faster reacting primary and secondary amines. [0003] U.S. Pat. Nos. 5,412,056, 5,623,045, 5,126,170, and 5,821,326 disclose coating compositions in which the binding agent is a two-component system containing a polyisocyanate component and an isocyanate-reactive component. The latter component includes at least one aspartic acid diester group formed by reacting an amine with a maleic or fumaric diester. [0004] EP 0 667 362 A1 discloses coating compositions including a polyisocyanate component, a component that includes at least one aspartic acid diester group formed by reacting an amine with a maleic or fumaric diester, and a water-adsorbing zeolite. [0005] Adhesives are commonly used to join or fasten two or more adherends. Adherends are considered as being any two or more materials, or pieces of material that are being joined together, including wood, metals, plastics, paper, ceramics, stone, glass, concrete, etc. Adhesives used for these purposes are based on a wide range of technologies, including elastomer/solvent/resin mixtures, epoxies, latexes, polyurethanes, silicones, cyanoacrylates, acrylics, hot melts, and others. Such adhesives can have one or more drawback, such as they may contain solvents which are toxic and often flammable, they can be incompatible with one or more classes of adherends, they can have undesirably long cure times and in many cases the bonds they form of are of insufficient strength. [0006] It is often desirable for coatings applied to substrates to provide a desirable appearance, in many cases by applying multiple coating layers, the last of which can be a pigmented or unpigmented topcoat. Unfortunately, as the article containing the coated substrate ages, scratches that occur through normal "wear and tear", tend to deteriorate the appearance of the coated surface of the substrate, [0007] A sealant is typically a thin film, often containing a plastic, that is applied onto one or more surfaces on one or more substrates to prevent passage of a liquid or gas through the film. The sealant can be used to prevent exposure of the substrate or is often additionally used to prevent exposure via defects in a substrate or between gaps that can exist between substrates. [0008] Oftentimes, high molecular weight compounds containing aspartic esters are desired for various adhesive, coating and sealant applications. However, the corresponding precursors often react very slowly leading to undesirably long processing times, poor conversion to the desired product, and/or impure products. [0009] Additionally, desired functionality and/or molecular architectures in the aspartic ester materials may not be achievable using the established amine--maleic/fumaric ester synthetic pathway. This limits the possible aspartic ester containing materials available for formulation. [0010] U.S. Pat. No. 2,569,200 discloses polyvalent alkylene imine esters and methods for preparing them. [0011] There is an established need in the art for alternative synthetic pathways that can provide a wider range of molecular architectures and functional groups for aspartic ester containing compounds that can be made efficiently. SUMMARY OF THE INVENTION [0012] The present invention is directed to functional dialkyl aspartic esters (aspartates) according to the formula: where [0013] R.sup.1 and R.sup.2 are independently C.sub.1-C.sub.8 linear, branched or cyclic alkyl, [0014] each occurrence of R.sup.3 is independently selected from H, C.sub.1-C.sub.20 linear, branched, or cyclic alkyl, aryl, alkaryl or aralkyl, [0015] Y is a linking group selected from the group consisting of --O--, --S--, --NR.sup.5--, [0016] --O--P(O).sub.2--O--, --P(O).sub.2--O--, --S(O).sub.2--O--, [0017] and a group resulting from the removal of an acidic hydrogen from a carbon that is positioned adjacent to one or more electron withdrawing groups according to one of the formulas [0018] where [0019] R.sup.5 is H or C.sub.1-C.sub.3 linear or branched alkyl, [0020] W.sup.1 is an electron withdrawing group selected from the group consisting of nitrile, R.sup.11--CO--, nitro, carboxylic acids and their corresponding salts, C.sub.1-C.sub.24 linear, branched or cyclic alkyl, alkenyl, aryl, alkaryl, or aralkyl esters of carboxylic acids, and C.sub.1-C.sub.24 linear, branched or cyclic alkyl sulfonyl, [0021] W.sup.2 is a ketone, [0022] R.sup.11 is selected from H. --OH, C.sub.1-C.sub.24 linear, branched or cyclic alkyl, aryl, alkaryl, or aralkyl, which may contain one or more hetero atoms selected from O, S, and/or N, [0023] R.sup.12 is C.sub.1-C.sub.24 linear, branched or cyclic alkylene, arylene, alkarylene, or aralkylene, which may contain one or more hetero atoms selected from O, S, and/or N, and [0024] R.sup.4 is a linking group selected from the group consisting of [0025] C.sub.1-C.sub.24 linear, branched or cyclic alkylene, arylene, alkarylene, or aralkylene, [0026] --(--[CHR.sup.7--].sub.n--O-)p-R.sup.8--, where R.sup.7 is C.sub.1-C.sub.3 linear or branched alkyl or aklylol, [0027] n is 1 to 4, and [0028] p is 1 to 1,000, [0029] where q is 1 to 1,000, and each occurrence of R.sup.8 is independently selected from C.sub.1-C.sub.24 linear, branched or cyclic alkylene, alkenylene, arylene, alkarylene, or aralkylene, optionally including substituent hydroxyl, carboxylic acid, or C.sub.1-C.sub.8 linear, branched or cyclic carboxylic acid ester groups, [0030] where r is 1 to 10,000, [0031] R.sup.9 is C.sub.1-C.sub.3 linear or branched alkyl, [0032] X is --OR.sup.10 or --NR.sup.5.sub.2, where R.sup.5 is as defined above, [0033] R.sup.10 is H or C.sub.1-C.sub.24 linear, branched or cyclic alkyl, aryl, alkaryl, and aralkyl, [0034] and combinations thereof, and [0035] Z is selected from --H, --OR.sup.10, --R.sup.4--OR.sup.10, --NR.sup.5.sub.2, --R.sup.4--NR.sup.5.sub.2, --SH, --R.sup.4--SH, [0036] The present invention is also directed to a method of preparing a functional aspartate and the functional aspartate resulting from the method. The method includes [0037] A) reacting an aziridine with a Michael-acceptor molecule to form an aziridinyl aspartate, and [0038] B) reacting the aziridinyl aspartate with an active hydrogen containing compound to form the functional aspartate. [0039] The present invention is further directed to adhesive, sealant or coating compositions that include [0040] i) the above described functional aspartates, and [0041] ii) an isocyanate functional material. DETAILED DESCRIPTION OF THE INVENTION [0042] Other than in the operating examples, or where otherwise indicated, all numbers or expressions referring to quantities of ingredients, reaction conditions, etc., used in the specification and claims are to be understood as modified in all instances by the term "about." Various numerical ranges are disclosed in this patent application. Because these ranges are continuous, they include every value between the minimum and maximum values. Unless expressly indicated otherwise, the various numerical ranges specified in this application are approximations. [0043] As used herein the term "alkyl" refers to a monovalent radical of an aliphatic hydrocarbon chain of general formula C.sub.sH.sub.2s+1, where s is the number of carbon atoms, or ranges therefore, as specified. The term "substituted alkyl" refers to an alkyl group, where one or more hydrogens are replaced with a non-carbon atom or group, non-limiting examples of such atoms or groups include halides, amines, alcohols, oxygen (such as ketone or aldehyde groups), and thiols. [0044] As used herein the terms "cyclic alkyl" or "cycloalkyl" refer to a monovalent radical of an aliphatic hydrocarbon chain that forms a ring of general formula C.sub.sH.sub.2s-1, where s is the number of carbon atoms, or ranges therefore, as specified. The term "substituted cycloalkyl" refers to a cycloalkyl group, containing one or more hetero atoms, non-limiting examples being --O--, --NR--, and --S-- in the ring structure, and/or where one or more hydrogens are replaced with a non-carbon atom or group, non-limiting examples of such atoms or groups include halides, amines, alcohols, oxygen (such as ketone or aldehyde groups), and thiols. R represents an alkyl group of from 1 to 24 carbon atoms. [0045] As used herein, the term "aryl" refers to a monovalent radical of an aromatic hydrocarbon. Aromatic hydrocarbons include those carbon based cyclic compounds containing conjugated double bonds where 4t+2 electrons are included in the resulting cyclic conjugated pi-orbital system, where t is an integer of at least 1. As used herein, aryl groups can include single aromatic ring structures, one or more fused aromatic ring structures, covalently connected aromatic ring structures, any or all of which can include heteroatoms. Non-limiting examples of such heteroatoms that can be included in aromatic ring structures include O, N, and S. [0046] As used herein, the term "alkylene" refers to acyclic or cyclic divalent hydrocarbons having a carbon chain length of from C.sub.1 (in the case of acyclic) or C.sub.4 (in the case of cyclic) to C.sub.25, typically C.sub.2 to C.sub.12, which may be substituted or unsubstituted, and which may include substituents. As a non-limiting example, the alkylene groups can be lower alkyl radicals having from 1 to 12 carbon atoms. As a non-limiting illustration, "propylene" is are intended to include both n-propylene and isopropylene groups; and, likewise, "butylene" is intended to include both n-butylene, isobutylene, and t-butylene groups. [0047] As used herein, the term "(meth)acrylic" and "(meth)acrylate" are meant to include the corresponding derivatives of acrylic acid and methacrylic acid, without limitation. Continue reading... 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