# US 9,752,054 B2 · Liquid-applied waterproofing membrane for roofs comprising a trialdimine > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,752,054 B2 - Document ID: US9752054B2 - Status: Granted - Kind: B2 - Application number: 14/760,878 - Filed: 2014-01-21 - Published: 2015-12-10 - Granted: 2017-09-05 - Earliest claimed: 2013-01-22 - Assignees: Sika Technology AG - Applicants: Sika Technology AG - Inventors: Michael Byrne; Mark Gatrell; Alexander Coward; Urs Burckhardt - Web page: https://patentgrep.com/patent/US9752054B2 ## CPC - C09D 175/04: Polyurethanes - C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step - C08G 18/307: {Atmospheric humidity} - C08G 18/3256: {Reaction products of polyamines with aldehydes or ketones} - C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate} - C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates} - C09D 175/12: from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group - E04D 11/02: Build-up roofs, i.e. consisting of two or more layers bonded together in situ, at least one of the layers being of watertight composition (gravelling of flat roofs E04D7/00; venting or ventilation E04D13/17) - C08G 2190/00: Compositions for sealing or packing joints - 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) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - E04D: ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS (coverings of outer walls by plaster or other porous material E04F13/00) ## Abstract The present invention describes a one-part moisture-curing liquid-applied waterproofing membrane including a polyurethane polymer and both a trialdimine and a dialdimine as blocked amine hardeners in a specific ratio range. The membrane has a low odor, a long shelf life stability, a low viscosity at low solvent content, a sufficiently long open time to allow hand application and cures fast to a solid elastic material. The liquid-applied waterproofing membrane can be suitable for roofing applications, possessing high strength, high elongation and good durability under outdoor weathering conditions in a broad temperature range. ## Claims ### Claim 1 A one-part moisture-curing liquid-applied waterproofing membrane comprising: at least one isocyanate-functional polyurethane polymer; at least one trialdimine of the formula (I), wherein A is a trivalent hydrocarbyl moiety of molecular weight in the range of 380 to 5000 g/mol containing ether groups, R1 and R2 are the same or different C1 to C12 linear or branched alkyls, or are joined together to form a divalent linear or branched C4 to C12 hydrocarbyl moiety which is part of a 5- to 8-membered carbocyclic ring, R3 is hydrogen or a linear or branched C1 to C12 alkyl or arylalkyl or alkoxycarbonyl, and R4 and R5 are the same or different linear or branched C1 to C20 alkyl or cycloalkyl or aralkyl optionally containing ether groups, or are joined together to form a divalent linear or branched C4 to C12 hydrocarbyl moiety which is part of a 5- to 8-membered heterocyclic ring which, besides the nitrogen atom, may contain an ether or thioether or tertiary amino group; and at least one dialdimine; wherein the ratio between the number of the aldimino groups of the trialdimine and the number of aldimino groups of the dialdimine is in the range of 90/10 to 40/60. ### Claim 2 (depends on 1) The membrane according to claim 1, wherein the isocyanate-functional polymer is based on an aliphatic polyisocyanate. ### Claim 3 (depends on 1) The membrane according to claim 1, wherein the trialdimine of the formula (I) is N,N′,N″-tris(2,2-dimethyl-3-(N-morpholino)-propylidene)-polyoxypropylene triamine with an average molecular weight in the range of 860 to 5500 g/mol. ### Claim 4 (depends on 1) The membrane according to claim 1, wherein the dialdimine is a dialdimine of the formula (II), wherein G is a divalent hydrocarbyl moiety of molecular weight in the range of 28 to 400 g/mol, and R1, R2, R3, R4 and R5 are the same as in the formula (I). ### Claim 5 (depends on 4) The membrane according to claim 4, wherein the dialdimine of the formula (II) is selected from the group consisting of N,N′-bis(2,2-dimethyl-3-(N-morpholino)-propylidene)-hexamethylene-1,6-diamine and N,N′-bis(2,2-dimethyl-3-(N-morpholino)-propylidene)-3-aminomethyl-3,5,5-trimethylcyclohexylamine. ### Claim 6 (depends on 1) The membrane according to claim 1, wherein the dialdimine is a dialdimine of the formula (III), wherein G is a divalent hydrocarbyl moiety of a molecular weight in the range of 28 to 400 g/mol, R6 is a monovalent C6 to C20 hydrocarbyl moiety optionally containing ether, carbonyl or ester groups, and R1, R2 and R3 are the same as in the formula (I). ### Claim 7 (depends on 1) The membrane according to claim 1 further comprising: at least one ingredient selected from the group consisting of inorganic fillers and pigments, at least one ingredient selected from the group consisting of flame-retarding plasticizers and flame-retarding fillers, and at least one ingredient selected from the group consisting of catalysts, plasticizers, solvents and UV-stabilizers. ### Claim 8 (depends on 1) The membrane according to claim 1 containing from 15 to 70 weight-% isocyanate-functional polyurethane polymers; from 20 to 80 weight-% of fillers including inorganic fillers, flame-retarding fillers and pigments; from 5 to 30 weight-% of plasticizers including flame-retarding plasticizers; and at least one further ingredient selected from the group consisting of catalysts, solvents and UV-stabilizers. ### Claim 9 (depends on 1) The membrane according to claim 1 having a Brookfield viscosity in the range of 2000 to 15000 mPa·s at 20° C. ### Claim 10 (depends on 1) The membrane according to claim 1 containing 50 g VOC per liter or less. ### Claim 11 (depends on 1) A method for forming the membrane according to claim 1, the method comprising applying a composition in liquid state onto a substrate of a roof structure in a layer thickness in the range of 0.5 to 3 mm, and curing the composition to form the membrane according to claim 1. ### Claim 12 (depends on 1) Waterproofing system, consisting of: optionally a primer and/or an undercoat, one or more than one layer of the membrane according to claim 1, and optionally a top coat. ### Claim 13 (depends on 1, 12) The waterproofing system according to claim 12, wherein the one or more than one layer of the membrane according to claim 1 is in combination with a fibre reinforcement mesh. ### Claim 14 (depends on 1) Method of waterproofing a roof structure, comprising: applying a composition in liquid state onto a substrate of the roof structure in a layer thickness in the range of 0.5 to 3 mm, wherein the applying of the composition results in forming the membrane according to claim 1; contacting the membrane with a fibre reinforcement mesh within the open time of the membrane; exposing the membrane to moisture to thereby cure the membrane partially or fully to obtain an elastic coating, optionally applying a second layer of the membrane in a layer thickness in the range of 0.5 to 3 mm and curing it by exposure to moisture. ### Claim 15 (depends on 14) Waterproof roof structure, obtained by the method according to claim 14. ### Claim 16 A one-part moisture-curing liquid-applied waterproofing membrane comprising: at least one isocyanate-functional polyurethane polymer; at least one trialdimine of the formula (I), wherein A is a trivalent hydrocarbyl moiety of molecular weight in the range of 380 to 5000 g/mol containing ether groups, R1 and R2 are the same or different C1 to C12 linear or branched alkyls, or are joined together to form a divalent linear or branched C4 to C12 hydrocarbyl moiety which is part of a 5- to 8-membered carbocyclic ring, R3 is hydrogen or a linear or branched C1 to C12 alkyl or arylalkyl or alkoxycarbonyl, and R4 and R5 are the same or different linear or branched C1 to C20 alkyl or cycloalkyl or aralkyl optionally containing ether groups, or are joined together to form a divalent linear or branched C4 to C12 hydrocarbyl moiety which is part of a 5- to 8-membered heterocyclic ring which, besides the nitrogen atom, may contain an ether or thioether or tertiary amino group; and at least one dialdimine; wherein the ratio between the number of the aldimino groups of the trialdimine and the number of aldimino groups of the dialdimine is in the range of 90/10 to 40/60, wherein the at least one trialdimine of the formula (I) increases the cure speed of the one-part moisture-curing liquid-applied waterproofing membrane.