# US 8,785,593 B2 · Polyamidoamine-epihalohydrin resins, method of manufacture, 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 8,785,593 B2 - Document ID: US8785593B2 - Status: Granted - Kind: B2 - Application number: 13/448,982 - Filed: 2012-04-17 - Published: 2012-10-25 - Granted: 2014-07-22 - Earliest claimed: 2011-04-21 - Assignees: Georgia-Pacific Chemicals LLC - Applicants: Karla D. Favors; Clay E. Ringold; Yuping Luo; Cornel Hagiopol - Inventors: Karla D. Favors; Clay E. Ringold; Yuping Luo; Cornel Hagiopol - Web page: https://patentgrep.com/patent/US8785593B2 ## CPC - C08G 73/0286: {Preparatory process from polyamidoamines and epihalohydrins} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract A novel process for producing a polyamidoamine-epihalohydrin resin composition comprises (a) reacting a polyamidoamine with epihalohydrin to obtain a reaction mixture comprising a polyamidoamine-epihalohydrin resin; (b) adding a first acid to the reaction mixture obtained in step (a) to obtain an acid treatment composition; (c) adding a base to the acid treatment composition in step (b) to obtain a base treatment composition; and (d) adding a second acid to the base treatment composition in step (c) to obtain a polyamidoamine-epihalohydrin resin composition; wherein the polyamidoamine-epihalohydrin resin composition obtained in step (d) has less than about 700 ppm of dihalopropanol (DHP) and 3-halopropanediol (HPD). ## Claims ### Claim 1 A process for producing a polyamidoamine-epihalohydrin resin composition, comprising: treating a polyamidoamine-epihalohydrin resin mixture containing halogenated epihalohydrin byproducts with formic acid to obtain a formic acid-treated resin mixture; treating the formic acid-treated resin mixture with a base to obtain a formic acid-base resin mixture; and adding a quenching acid to the formic acid-base resin mixture to obtain a polyamidoamine-epihalohydrin resin composition having less than 700 ppm of a combined amount of 1,3-dihalopropanol and 3-halopropanediol. ### Claim 2 (depends on 1) The process of claim 1, wherein the 1,3-dihalopropanol and the 3-halopropanediol are 1,3-dicloropropanol and 3-chloropropanediol, respectively. ### Claim 3 (depends on 1) The process of claim 1, wherein the polyamidoamine-epihalohydrin resin mixture has a solids content of about 10 wt % to about 50 wt %, based on the total weight of the mixture. ### Claim 4 (depends on 1) The process of claim 1, wherein the polyamidoamine-epihalohydrin resin mixture is prepared by reacting adipic acid with diethylenetriamine at a molar ratio of adipic acid to diethylenetriamine of less than 1.0:1.0. ### Claim 5 (depends on 1) The process of claim 1, further comprising treating the polyamidoamine-epihalohydrin resin mixture with a stabilizing acid prior to the treating with formic acid. ### Claim 6 (depends on 5) The process of claim 5, wherein the stabilizing acid is sulfuric acid. ### Claim 7 (depends on 1) The process of claim 1, wherein treating the polyamidoamine-epihalohydrin resin mixture comprises adding about 0.05 wt % to about 10.0 wt % of the formic acid, based on the total weight of the polyamidoamine-epihalohydrin resin mixture. ### Claim 8 (depends on 1) The process of claim 1, wherein the formic acid-treated treated resin mixture has a pH of about 2 to about 8. ### Claim 9 (depends on 1) The process of claim 1, wherein the formic acid-treated resin mixture has a solids content of about 10 wt % to about 35 wt %, based on the total weight of the formic acid-treated resin mixture. ### Claim 10 (depends on 1) The process of claim 1, wherein the base comprises diethanolamine. ### Claim 11 (depends on 1) The process of claim 1, wherein the base comprises sodium hydroxide and diethanolamine. ### Claim 12 (depends on 1) The process of claim 1, wherein the formic acid-base resin mixture has a pH of about 7 to about 11. ### Claim 13 (depends on 1) The process of claim 1, wherein the formic acid-base resin mixture has a pH of about 10 to about 11. ### Claim 14 (depends on 1) The process of claim 1, wherein the polyamidoamine-epihalohydrin resin composition has a pH of about 2 to about 4. ### Claim 15 (depends on 1) The process of claim 1, wherein the quenching acid is a combination of formic acid and sulfuric acid. ### Claim 16 (depends on 1) The process of claim 1, wherein the polyamidoamine-epihalohydrin resin composition has less than 500 ppm of the combined amount of the 1,3-dihalopropanol and the 3-halopropanediol. ### Claim 17 (depends on 16) The process of claim 16, wherein the 1,3-dihalopropanol and the 3-halopropanediol are 1,3-dicloropropanol and 3-chloropropanediol, respectively. ### Claim 18 (depends on 1) The process of claim 1, further comprising adding a stabilizing compound to the polyamidoamine-epihalohydrin resin composition in an amount of about 1% to about 15% by weight of solids of the polyamidoamine-epihalohydrin resin composition. ### Claim 19 A process for producing a polyamidoamine-epihalohydrin resin composition, comprising: treating a polyamidoamine-epihalohydrin resin mixture containing halogenated epichlorohydrin byproducts with formic acid to obtain a formic acid-treated resin mixture; treating the formic acid-treated resin mixture with an inorganic base and diethanolamine to obtain a formic acid-base resin mixture; and adding a quenching acid to the formic acid-base resin mixture to obtain a polyamidoamine-epihalohydrin resin composition having less than 500 ppm of a combined amount of 1,3-dihalopropanol and 3-halopropanediol. ### Claim 20 (depends on 19) The process of claim 19, the formic acid-base resin mixture has a pH of about 10 to about 11. ### Claim 21 (depends on 19) The process of claim 19, wherein the 1,3-dihalopropanol and the 3-halopropanediol are 1,3-dicloropropanol and 3-chloropropanediol, respectively. ### Claim 22 (depends on 1) The process of claim 1, wherein the quenching acid is added as a mixture comprising formic acid and sulfuric acid, and wherein the quenching acid has a molar ratio of formic acid to sulfuric acid of about 0.2:1 to about 1.5:1. ### Claim 23 (depends on 1) The process of claim 1, wherein the formic acid-treated resin mixture has a pH of about 2.5 to about 7.5, the formic acid-base resin mixture has a pH of about 7 to about 11, and the polyamidoamine-epihalohydrin resin composition has a pH of about 2 to about 4. ### Claim 24 (depends on 19) The process of claim 19, wherein the quenching acid is added as a mixture comprising formic acid and sulfuric acid, and wherein the quenching acid has a molar ratio of formic acid to sulfuric acid of about 0.2:1 to about 1.5:1. ### Claim 25 (depends on 19) The process of claim 19, wherein the formic acid-treated resin mixture has a pH of about 2.5 to about 7.5, the formic acid-base resin mixture has a pH of about 7 to about 11, and the polyamidoamine-epihalohydrin resin composition has a pH of about 2 to about 4.