# US 10,118,983 B2 · Treated aldehyde-based resins containing polyamines and methods for making and using same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,118,983 B2 - Document ID: US10118983B2 - Status: Granted - Kind: B2 - Application number: 15/094,550 - Filed: 2016-04-08 - Published: 2016-10-13 - Granted: 2018-11-06 - Earliest claimed: 2015-04-10 - Assignees: Georgia-Pacific Chemicals LLC - Applicants: Georgia-Pacific Chemicals LLC - Inventors: Richard A. Rediger - Web page: https://patentgrep.com/patent/US10118983B2 ## CPC - C08G 8/28: Chemically modified polycondensates - C08G 14/06: and monomers containing hydrogen attached to nitrogen - C08L 61/14: Modified phenol-aldehyde condensates - C08L 61/34: Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20 - C09D 161/14: Modified phenol-aldehyde condensates - C09D 161/34: Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09D161/04, C09D161/18 and C09D161/20 - C09K 8/805: {Coated proppants} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract Treated aldehyde-based resins containing one or more polyamines and methods for making and same. The treated aldehyde-based resin can be or include an aldehyde-based resin and a polyamine. The polyamine can be or include one or more aromatic polyamines, one or more poly(C2-C5 alkylene) polyamines, or a mixture thereof. The treated aldehyde-based resin can include about 0.05 wt % to about 10 wt % of the polyamine, based on a solids weight of the aldehyde-based resin. ## Claims ### Claim 1 A treated aldehyde-based resin, comprising: an aldehyde-based resin; a polyamine comprising an aromatic polyamine, wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, or any mixture thereof, wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin; and an additive comprising a wax, a dibasic ester, or a mixture thereof. ### Claim 2 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin. ### Claim 3 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the treated aldehyde-based resin comprises about 0.05 wt % to 0.5 wt % of the polyamine, based on a solids weight of the aldehyde-based resin. ### Claim 4 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the aldehyde-based resin comprises a phenol-formaldehyde resin, a urea-formaldehyde resin, a melamine-formaldehyde resin, a resorcinol-formaldehyde resin, a melamine-urea-formaldehyde resin, a phenol-urea-formaldehyde resin, a phenol-melamine-formaldehyde resin, a phenol-resorcinol-formaldehyde resin, a copolymer thereof, or any mixture thereof. ### Claim 5 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the aldehyde-based resin comprises a phenol-formaldehyde novolac resin, a copolymer thereof, or a mixture thereof. ### Claim 6 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the aromatic polyamine comprises 1,4-diaminobenzene. ### Claim 7 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, or any mixture thereof. ### Claim 8 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the polyamine further comprises a poly(C2-C5 alkylene) polyamine, and wherein the poly(C2-C5 alkylene) polyamine comprises diethylenetriamine, dipropylenetriamine, dibutylenetriamine, an isomer thereof, or any mixture thereof. ### Claim 9 (depends on 1) The treated aldehyde-based resin of claim 1, wherein the additive comprises the mixture of the wax and the dibasic ester. ### Claim 10 A method for making a treated aldehyde-based resin, comprising: combining an aldehyde-based resin, a polyamine, and an additive to produce a mixture, wherein the polyamine comprises an aromatic polyamine, wherein the aromatic polyamine comprises 1,3-diaminobenzene, 1,4-diaminobenzene, 1,3-xylylenediamine, 1,4-xylylenediamine, 3,4′-diaminodiphenyl ether, 4,4′-diaminodiphenyl ether, an isomer thereof, and wherein the mixture comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin, and wherein the additive comprises a wax, a dibasic ester, or a mixture thereof; heating the mixture to a temperature of about 110° C. to about 200° C. to produce the treated aldehyde-based resin; and cooling the treated aldehyde-based resin to a temperature of less than 50° C. ### Claim 11 (depends on 10) The method of claim 10, wherein the mixture is heated to a temperature of about 120° C. to about 160° C. for about 10 minutes to about 60 minutes to produce the treated aldehyde-based resin, and wherein the treated aldehyde-based resin is cooled to a temperature of about 20° C. to about 30° C. to solidify the treated aldehyde-based resin. ### Claim 12 (depends on 10) The method of claim 10, further comprising: reacting formaldehyde and a reagent to produce the aldehyde-based resin, wherein the reagent comprises phenol, urea, or a mixture thereof; and adding the polyamine to the aldehyde-based resin to produce the mixture. ### Claim 13 A method for making a treated aldehyde-based resin, comprising: heating a solid aldehyde-based resin to a temperature of about 110° C. to about 200° C. to produce a molten aldehyde-based resin; combining the molten aldehyde-based resin and a polyamine to produce the treated aldehyde-based resin, wherein: the polyamine comprises an aromatic polyamine, a poly(C2-C5 alkylene) polyamine, or a mixture thereof, the treated aldehyde-based resin comprises about 0.05 wt % to about 10 wt % of the polyamine, based on a solids weight of the aldehyde-based resin, the polyamine is a solid when combined with the molten aldehyde-based resin, and the molten aldehyde-based resin and the polyamine are at a temperature of about 110° C. to about 200° C. when combined with one another; and cooling the treated aldehyde-based resin to a temperature of less than 50° C. ### Claim 14 (depends on 10) The method of claim 10, wherein the aldehyde-based resin comprises a phenol-formaldehyde resin, a urea-formaldehyde resin, or a mixture thereof, and wherein the mixture comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin. ### Claim 15 (depends on 10) The method of claim 10, wherein the aromatic polyamine comprises 1,4-diaminobenzene. ### Claim 16 (depends on 10) The method of claim 10, wherein the polyamine further comprises a poly(C2-C5 alkylene) polyamine, and wherein the poly(C2-C5 alkylene) polyamine comprises diethylenetriamine, dipropylenetriamine, dibutylenetriamine, an isomer thereof, or any mixture thereof. ### Claim 17 A method for making a treated aldehyde-based resin, comprising: combining formaldehyde and a reagent to produce a first mixture, wherein the reagent comprises phenol, urea, or a mixture thereof; heating the first mixture to produce an aldehyde-based resin; combining the aldehyde-based resin and an additive to produce a second mixture, wherein the additive comprises a wax, a dibasic ester, or a mixture thereof; combining the second mixture and a polyamine to produce a third mixture, wherein the polyamine comprises an aromatic polyamine, a poly(C2-C5 alkylene) polyamine, or a mixture thereof, and wherein the third mixture comprises about 0.05 wt % to 0.7 wt % of the polyamine, based on a solids weight of the aldehyde-based resin; heating the third mixture to a temperature of about 110° C. to about 200° C. for about 5 minutes to about 90 minutes to produce the treated aldehyde-based resin; and cooling the treated aldehyde-based resin to a temperature of less than 50° C. to solidify the treated aldehyde-based resin. ### Claim 18 (depends on 17) The method of claim 17, wherein the formaldehyde is added to the reagent to produce the first mixture, and wherein the polyamine is added to the second mixture to produce the third mixture. ### Claim 19 (depends on 17) The method of claim 17, wherein the first mixture is heated to a temperature of about 50° C. to about 100° C., and wherein the third mixture is heated to a temperature of about 110° C. to about 200° C. ### Claim 20 (depends on 17) The method of claim 17, wherein the third mixture is produced by adding the polyamine and an additional amount of formaldehyde to the second mixture, and wherein the third mixture comprises about 0.05 wt % to 0.6 wt % of the polyamine, based on a solids weight of the aldehyde-based resin.