# US 8,147,964 B2 · Benzylated polyalkylene polyamines and uses thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,147,964 B2 - Document ID: US8147964B2 - Status: Granted - Kind: B2 - Application number: 12/186,768 - Filed: 2008-08-06 - Published: 2009-01-22 - Granted: 2012-04-03 - Earliest claimed: 2007-02-07 - Assignees: Air Products and Chemicals, Inc. - Inventors: Gamini Ananda Vedage; Williams Rene Edouard Raymond; Michael Ian Cook; Robert Marjo Theodoor Rasing - Web page: https://patentgrep.com/patent/US8147964B2 ## CPC - C08G 59/4042: {Imines; Imides} - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - Y10T 428/31511: Of epoxy ether - Y10T 428/31529: Next to metal - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract The present invention provides curing agent compositions comprising benzylated polyalkylene polyamine compounds. Amine-epoxy compositions and articles produced from these amine-epoxy compositions are also disclosed. ## Claims ### Claim 1 A curing agent composition comprising (a) at least one benzylated polyalkylene polyamine having at least three nitrogen atoms, at least three active amine hydrogen atoms and at least one substituted or unsubstituted benzyl group and (b) at least one multifunctional amine having 3 or more active amine hydrogens; wherein the at least one benzylated polyalkylene polyamine comprises the reductive amination product of at least one substituted or unsubstituted benzaldehyde compound with at least one polyalkylene polyamine; and wherein the at least one multifunctional amine comprises at least one member selected from the group consisting of ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), propylenediamine, dipropylenetriamine, tripropylenetetramine, N-3-aminopropyl ethylenediamine (Am3), N,N′-bis(3-aminopropyl) ethylenediamine (Am4), N,N,N′-tris(3-aminopropyl) ethylenediamine (Am5); N-3-aminopropyl-1,3-diaminopropane, N,N′-bis(3-aminopropyl)-1,3-diaminopropane, N,N,N′-tris(3-aminopropyl)-1,3-diaminopropane, and any combination thereof. ### Claim 2 (depends on 1) The composition of claim 1, wherein the at least one polyalkylene polyamine compound is diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), dipropylenetriamine, tripropylenetetramine, or any combination thereof. ### Claim 3 (depends on 1) The composition of claim 1, wherein the at least one polyalkylene polyamine compound is diethylenetriamine (DETA), triethylenetetramine (TETA), or a mixture of diethylenetriamine (DETA) and triethylenetetramine (TETA). ### Claim 4 (depends on 1) The composition of claim 1, wherein the at least one polyalkylene polyamine compound comprises a mixture of diethylenetriamine (DETA) and triethylenetetramine (TETA). ### Claim 5 (depends on 1) The composition of claim 1, wherein the molar reactant ratio of the benzaldehyde compound to the at least one polyalkylene polyamine compound is in a range from about 0.8:1 to about 2:1. ### Claim 6 (depends on 1) The composition of claim 1, wherein the at least one benzylated polyalkylene polyamine has the formula: wherein RA is substituted or unsubstituted benzyl; RB, RC, RD, and RE are independently RA or a hydrogen atom; n is 1, 2, 3, 4, 5, 6, or 7, provided that the polyamine has at least three active amine hydrogen atoms. ### Claim 7 (depends on 6) The composition of claim 6 wherein RA is benzyl or vanillyl, RCis RA or a hydrogen atom; RB, RD, and RE are hydrogen atoms; and n is 1, 2, 3, or 4. ### Claim 8 (depends on 6) The composition of claim 6, wherein RA and RC are benzyl or vanillyl; RB, RD, and RE are hydrogen atoms; and n is 1 or 2. ### Claim 9 (depends on 1) The composition of claim 1 wherein the benzylated polyalkylene polyamine comprises at least 5 wt % dibenzylated polyamines. ### Claim 10 (depends on 1) The composition of claim 1, wherein the curing agent composition has an amine hydrogen equivalent weight (AHEW) based on 100% solids from about 50 to about 500. ### Claim 11 (depends on 1) The composition of claim 1, wherein the at least multifunctional amine is an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a Mannich base derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, a polyamide derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, or any combination thereof. ### Claim 12 (depends on 1) The composition of claim 1 wherein the benzylated polyalkylene polyamine comprises benzylated diethylenetriamine. ### Claim 13 (depends on 1) The composition of claim 1 wherein the benzylated polyalkylene polyamine comprises benzylated triethylenetetramine. ### Claim 14 A curing agent composition comprising (a) an amine-epoxide adduct and (b) at least one multifunctional amine having 3 or more active amine hydrogens; wherein the amine-epoxide adduct comprises a reaction product of a novolac epoxide resin and at least one benzylated polyalkylene polyamine having at least three nitrogen atoms, at least three active amine hydrogens and at least one substituted or unsubstituted benzyl group; wherein the at least one benzylated polyalkylene polyamine comprises the reductive amination product of at least one substituted or unsubstituted benzaldehyde compound with at least one polyalkylene polyamine; and wherein the at least one polyalkylene polyamine compound comprises at least one of diethylenetriamine and triethylenetetramine. ### Claim 15 An amine-epoxy composition comprising the reaction product of: A) a curing agent composition comprising the contact product of: at least one benzylated polyalkylene polyamine having at least three nitrogen atoms, at least three active amine hydrogen atoms and at least one substituted or unsubstituted benzyl group; and at least one multifunctional amine comprising at least one member selected from the group consisting of ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), propylenediamine, dipropylenetriamine, tripropylenetetramine, N-3-aminopropyl ethylenediamine (Am3), N,N′-bis(3-aminopropyl) ethylenediamine (Am4), N,N,N′-tris(3-aminopropyl) ethylenediamine (Am5); N-3-aminopropyl-113-diaminopropane, NIN′-bis(3-aminopropyl)-1,3-diaminopropane, N,N,N′-tris(3-aminopropyl)-1,3-diaminopropanel, and any combination thereof; and B) an epoxy composition comprising at least one multifunctional epoxy resin; wherein the at least one benzylated polyalkylene polyamine comprises the reductive amination product of at least one substituted or unsubstituted benzaldehyde compound with at least one polyalkylene polyamine. ### Claim 16 (depends on 15) The composition of claim 15, wherein the stoichiometric ratio of epoxy groups in the epoxy composition to amine hydrogens in the curing agent composition is in a range from about 1.3:1 to about 0.7:1. ### Claim 17 (depends on 15) An article of manufacture comprising the composition of claim 15. ### Claim 18 (depends on 17) The article of claim 17, wherein the article is an adhesive, a coating, a primer, a sealant, a curing compound, a construction product, a flooring product, or a composite product. ### Claim 19 (depends on 17) The article of claim 17, wherein the article is a coating, primer, sealant, or curing compound which is applied to a metal or cementitious substrate.