# US 11,078,332 B2 · Carbohydrate polyamine binders and materials made therewith > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,078,332 B2 - Document ID: US11078332B2 - Status: Granted - Kind: B2 - Application number: 16/867,526 - Filed: 2020-05-05 - Published: 2020-10-22 - Granted: 2021-08-03 - Earliest claimed: 2010-05-07 - Assignees: Knauf Insulation, Inc.; Knauf Insulation SPRL - Applicants: Knauf Insulation Sprl; Knauf Insulation, Inc. - Inventors: Charles Fitch Appley; Carl Hampson; Gert R. Mueller; Benedicte Pacorel - Web page: https://patentgrep.com/patent/US11078332B2 ## CPC - C08G 73/02: Polyamines - C08G 12/00: Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen (aminophenols C08G8/16) - C08G 14/00: Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 - C08G 16/00: Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 (with polynitriles C08G69/38) - C08K 7/14: Glass - C08L 97/02: Lignocellulosic material, e.g. wood, straw or bagasse {(manufacture of articles made from lignocellulosic material by dry processes B27N)} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract A binder comprising the products of a carbohydrate reactant and polyamine is disclosed. The binder is useful for consolidating loosely assembled matter, such as fibers. Uncured fibrous products comprising fibers in contact with a carbohydrate reactant and a polyamine are also disclosed. The binder composition may be cured to yield a fibrous product comprising fibers bound by a cross-linked polymer. Further disclosed are methods for binding fibers with the carbohydrate reactant and polyamine based binder. ## Claims ### Claim 1 A method of making a collection of matter bound with a cured, thermoset, polymeric binder comprising: preparing an aqueous binder solution, said preparing comprising mixing reactants for producing the cured, thermoset, polymeric binder, wherein the reactants include a) a reducing sugar reactant comprising at least one of dextrose and fructose and b) 1,6-diaminohexane; subsequently disposing the binder solution onto a collection of matter; subsequently drying the binder solution to form an uncured binder and thermally curing the uncured binder to form the collection of matter bound with the cured, thermoset, polymeric binder. ### Claim 2 (depends on 1) The method of claim 1, in which the cured, thermoset, polymeric binder is formaldehyde free. ### Claim 3 (depends on 1) The method of claim 1, in which neither formaldehyde nor phenol is used as a reagent. ### Claim 4 (depends on 1) The method of claim 1, wherein the collection of matter comprises matter selected from the group consisting of glass fibers, mineral fibers, aramid fibers, ceramic fibers, metal fibers, carbon fibers, polyimide fibers, polyester fibers, rayon fibers, cellulosic fibers, wood shavings, sawdust, wood pulp, ground wood, jute, flax, hemp, straw, particulates, coal particulates and sand particulates. ### Claim 5 (depends on 1) The method of claim 1, wherein the collection of matter comprises glass fibers present in the range from 70% to 99% by weight. ### Claim 6 (depends on 1) The method of claim 1, wherein a weight ratio of the reducing sugar reactant to 1,6-diaminohexane is in the range of 2:1 to 10:1. ### Claim 7 (depends on 1) The method of claim 1, wherein a weight ratio of the reducing sugar reactant to 1,6-diaminohexane is in the range of 3:1 to 6:1. ### Claim 8 (depends on 1) The method of claim 1, wherein the collection of matter is a mineral fiber insulation product. ### Claim 9 (depends on 1) The method of claim 1, wherein the reducing sugar reactant comprises dextrose and fructose provided by high fructose corn syrup. ### Claim 10 (depends on 1) The method of claim 1, wherein the reactants consist essentially of dextrose, fructose and 1,6-diaminohexane. ### Claim 11 (depends on 1) The method of claim 1, wherein the collection of matter and the cured, thermoset, polymeric binder further comprises a material selected from the group consisting of a silicon-containing compound, gamma-aminopropyltriethoxysilane, gamma-glycidoxypropyltrimethoxysilane, aminoethylaminopropyltrimethoxysilane, an aminofunctional oligomeric silane, an aminofunctional oligomeric siloxane and mixtures thereof. ### Claim 12 A method of making a composite wood board comprising a collection of matter comprising cellulosic fibers bound with a cured, thermoset, polymeric binder comprising: preparing an aqueous binder solution, said preparing comprising mixing reactants for producing the cured, thermoset, polymeric binder, wherein the reactants include a) a reducing sugar reactant comprising at least one of dextrose and fructose and b) 1,6-diaminohexane; subsequently disposing the binder solution onto a collection of matter comprising cellulosic fibers; subsequently drying the binder solution to form an uncured binder and thermally curing the uncured binder to form the composite wood board bound with the cured, thermoset, polymeric binder; wherein the composite wood board is selected from the group consisting of: a composite wood board having a modulus of elasticity (MOE) of at least 1800 N/mm2; a composite wood board having a bending strength (MOR) of at least 18 N/mm2; a composite wood board having an internal bond strength (TB) of at least 0.28 N/mm2; a composite wood board which swells less than or equal to 12%, as measured by a change in thickness, after 24 hours in water at 20° C.; a composite wood board having a water absorption after 24 hours in water at 20° C. of less than or equal to 40%; a composite wood board comprising a wax; an orientated strandboard; and a medium density fiberboard. ### Claim 13 (depends on 12) The method of claim 12, wherein a weight ratio of the reducing sugar reactant to 1,6-diaminohexane is in the range of 2:1 to 10:1. ### Claim 14 (depends on 12) The method of claim 12, wherein a weight ratio of the reducing sugar reactant to 1,6-diaminohexane is in the range of 3:1 to 6:1. ### Claim 15 (depends on 12) The method of claim 12, wherein the reducing sugar reactant comprises dextrose and fructose. ### Claim 16 (depends on 12) The method of claim 12, wherein the reducing sugar reactant comprises dextrose and fructose provided by high fructose corn syrup. ### Claim 17 (depends on 12) The method of claim 12, wherein the reactants consist essentially of dextrose, fructose and 1,6-diaminohexane. ### Claim 18 (depends on 12) The method of claim 12, wherein the cellulosic fibers comprise matter selected from the group consisting of wood shavings, sawdust, wood pulp, ground wood, jute, flax, hemp and straw. ### Claim 19 (depends on 12) The method of claim 12, wherein the composite wood board is a wood particle board. ### Claim 20 (depends on 12) The method of claim 12, wherein the composite wood board has from 8% to 18% by dry weight of the binder.