# US RE44,936 E1 · Aldehyde-functionalized polymers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US RE44,936 E1 - Document ID: USRE44936E1 - Status: Granted - Kind: E1 - Application number: 13/562,754 - Filed: 2012-07-31 - Granted: 2014-06-10 - Earliest claimed: 2004-01-26 - Assignees: Nalco Company - Applicants: Michael R. St. John; Angela P. Zagala - Inventors: Michael R. St. John; Angela P. Zagala - Web page: https://patentgrep.com/patent/USRE44936E1 ## Abstract A composition for enhancing the dewatering of a paper sheet on a paper machine and a method for using the composition is disclosed. The composition comprising one or more aldehyde-functionalized polymers comprising amino or amido groups wherein at least about 15 mole percent of the amino or amido groups are functionalized by reacting with one or more aldehydes and wherein the aldehyde functionalized polymers have a molecular weight of at least about 100,000. The method comprising adding the composition to the paper machine at a dosage of about 0.05 lb/ton to about 15 lb/ton, based on dry fiber. ## Claims ### Claim 1 A composition comprising: (i) one or more aldehyde-functionalized polymers comprising amino and/or amido groups wherein at least about 15 mole percent of the amino and/or amido groups are functionalized by reacting with one or more aldehydes and (ii) at least about 60 70 to 80 mole percent of the one or more aldehydes remain unreacted, wherein the amount of unreacted aldehyde is based on an amount used to functionalize the amino or amido groups. ### Claim 2 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymers are selected from the group consisting of: one or more aldehyde-functionalized polyamines; one or more aldehyde-functionalized polyamides; and combinations thereof. ### Claim 3 (depends on 2) The composition of claim 2, wherein the aldehyde-functionalized polyamide is selected from the group consisting of: an aldehyde-functionalized polymer comprising 100 mole percent of one or more nonionic monomers; an aldehyde-functionalized copolymer comprising about 5 to about 99 mole percent of one or more acrylamide monomers and about 95 mole percent to about 1 mole percent of one or more cationic, anionic, or zwitterionic monomers, or any mixture thereof; and any combinations of the foregoing. ### Claim 4 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized amphoteric polymer comprising up to about 40 mole percent of one or more cationic monomers and up to about 20 mole percent of one or more anionic monomers. ### Claim 5 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized amphoteric polymer comprising about 5 to about 10 mole percent of one or more cationic monomers and about 0.5 to about 4 mole percent of one or more anionic monomers. ### Claim 6 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized zwitterionic polymer comprising about 1 to about 95 mole percent of one or more zwitterionic monomers. ### Claim 7 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized zwitterionic polymer comprising about 1 to about 50 mole percent of one or more zwitterionic monomers. ### Claim 8 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized copolymer comprising about 50 to about 99 mole percent of one or more acrylamide monomers and about 50 to about 1 mole percent of one or more cationic monomers. ### Claim 9 (depends on 8) The composition of claim 8, wherein at least about 20 mole percent of the amide groups have reacted with aldehyde. ### Claim 10 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is a copolymer comprising about 50 to about 99 mole percent of one or more acrylamide monomers and about 50 to about 1 mole percent of one or more cationic monomers wherein the copolymer is functionalized with glyoxal. ### Claim 11 (depends on 10) The composition of claim 10, wherein the cationic monomer is a diallyl-N,N-disubstituted ammonium halide monomer. ### Claim 12 (depends on 11) The composition of claim 11, wherein about 20 to about 50 mole percent of the amide groups of the copolymer have reacted with glyoxal. ### Claim 13 (depends on 1) The composition of claim 1, wherein at least 60 mole percent of the one or more aldehydes remain unreacted. ### Claim 14 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer has a molecular weight of at least 100,000 g/mole. ### Claim 15 (depends on 1) The composition of claim 1, wherein the aldehyde-functionalized polymer is a copolymer comprising about 70 to about 99 mole percent of acrylamide and about 1 to about 30 mole percent of diallyldimethylammonium chloride. ### Claim 16 (depends on 1) The composition of claim 1, wherein about 20 to about 26 mole percent of the amino and/or amide groups of the copolymer have reacted with aldehyde. ### Claim 17 (depends on 1) The composition of claim 1, wherein the aldehydes are selected from the group consisting of: formaldehyde; paraformaldehyde; glyoxal; glutaraldehyde; and combinations thereof. ### Claim 18 (depends on 1) The composition of claim 1, wherein from about 15 mole percent to 23 mole percent of the amino and/or amido groups are functionalized. ### Claim 19 (depends on 1) The composition of claim 1, wherein from about 20 mole percent to 26 mole percent of the amino and/or amido groups are functionalized. ### Claim 20 (depends on 1) The composition of claim 1, wherein from about 22 mole percent to 30 mole percent of the amino and/or amido groups are functionalized. ### Claim 21 (depends on 1) The composition of claim 1, wherein from about 20 mole percent to about 50 mole percent of the amino and/or amido groups are functionalized. ### Claim 22 (depends on 1) The composition of claim 1, wherein from about 60 mole percent to 70 mole percent of the one or more aldehydes remain unreacted. ### Claim 23 (depends on 1) The composition of claim 1, wherein from about 70 mole percent to 80 mole percent of the one or more aldehydes remain unreacted. ### Claim 24 (depends on 1) A method of enhancing the dewatering of a paper sheet on a paper machine, the method comprising adding about 0.05 lb/ton to about 15 lb/ton, based on dry fiber, of the composition of claim 1 to the paper machine. ### Claim 25 (depends on 25) The method of claim 25 24, further comprising adding said composition to (i) wet end locations used for conventional wet end additives and/or (ii) at or prior to the press section. ### Claim 26 (depends on 24) The method of claim 24, further comprising spraying said composition onto the paper sheet prior to press dewatering. ### Claim 27 (depends on 24) The method of claim 24, wherein about 0.5 lb/ton to about 3 lb/ton, based on dry fiber, of said composition is added to the paper machine. ### Claim 28 (depends on 1) A method of enhancing a papermaking process, the method comprising adding the composition of claim 1 in the papermaking process. ### Claim 29 (depends on 28) The method of claim 28, further comprising adding said composition in the papermaking process at a wet end location. ### Claim 30 (depends on 28) The method of claim 28, further comprising adding said composition to a thin stock in the papermaking process. ### Claim 31 (depends on 28) The method of claim 28, further comprising adding said composition to a thick stock in the papermaking process. ### Claim 32 (depends on 28) The method of claim 28, further comprising adding said composition in the papermaking process after formation of a paper sheet. ### Claim 33 (depends on 28) The method of claim 28, further comprising adding said composition in the papermaking process prior to press dewatering. ### Claim 34 (depends on 28) The method of claim 28, further comprising adding about 0.05 lb/ton to about 15 lb/ton, based on dry fiber, of said composition in the papermaking process. ### Claim 35 A composition comprising one or more aldehyde-functionalized polymers comprising amino and/or amido groups, the amino and/or amido groups are functionalized by reacting with one or more aldehydes with the initial molar ratio of the aldehydes to amino and/or amido groups being 0.8 to 1.0, wherein at least about 70 to 80 mole percent of the one or more aldehydes remain unreacted and the amount of unreacted aldehyde is based on an amount used to functionalize the amino or amido groups. ### Claim 36 (depends on 35) The composition of claim 35, wherein the aldehyde-functionalized polymers are selected from the group consisting of: one or more aldehyde-functionalized polyamines; one or more aldehyde-functionalized polyamides; and combinations thereof. ### Claim 37 (depends on 35) The composition of claim 35, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized amphoteric polymer comprising up to about 40 mole percent of one or more cationic monomers and up to about 20 mole percent of one or more anionic monomers. ### Claim 38 (depends on 35) The composition of claim 35, wherein the aldehyde-functionalized polymer is an aldehyde-functionalized zwitterionic polymer comprising about 1 to about 95 mole percent of one or more zwitterionic monomers. ### Claim 39 (depends on 35) The composition of claim 35, wherein at least about 20 mole percent of the amino and/or amido groups have reacted with aldehyde. ### Claim 40 (depends on 35) The composition of claim 35, wherein the aldehyde-functionalized polymer has a molecular weight of at least 100,000 g/mole. ### Claim 41 (depends on 35) The composition of claim 35, wherein the aldehydes are selected from the group consisting of: formaldehyde; paraformaldehyde; glyoxal; glutaraldehyde; and combinations thereof. ### Claim 42 (depends on 35) The composition of claim 35, wherein from about 22 mole percent to 30 mole percent of the amino and/or amido groups are functionalized. ### Claim 43 (depends on 35) A method of enhancing the dewatering of a paper sheet on a paper machine, the method comprising adding about 0.05 lb/ton to about 15 lb/ton, based on dry fiber, of the composition of claim 35 to the paper machine. ### Claim 44 (depends on 43) The method of claim 43, further comprising adding said composition to (i) wet end locations used for conventional wet end additives and/or (ii) at or prior to the press section. ### Claim 45 (depends on 43) The method of claim 43, further comprising spraying said composition onto the paper sheet prior to press dewatering. ### Claim 46 (depends on 43) The method of claim 43, wherein about 0.5 lb/ton to about 3 lb/ton, based on dry fiber, of said composition is added to the paper machine. ### Claim 47 (depends on 35) A method of enhancing a papermaking process; the method comprising adding the composition of claim 35 in the papermaking process. ### Claim 48 (depends on 47) The method of claim 47, further comprising adding said composition in the papermaking process at a wet end location. ### Claim 49 (depends on 47) The method of claim 47, further comprising adding said composition to a thin stock in the papermaking process. ### Claim 50 (depends on 47) The method of claim 47, further comprising adding said composition to a thick stock in the papermaking process. ### Claim 51 (depends on 47) The method of claim 47, further comprising adding said composition in the papermaking process after formation of a paper sheet. ### Claim 52 (depends on 47) The method of claim 47, further comprising adding said composition in the papermaking process prior to press dewatering. ### Claim 53 A composition comprising: (i) one or more aldehyde-functionalized polymers comprising amino and/or amido groups wherein from 22 mole percent to 30 mole percent of the amino and/or amido groups are functionalized by reacting with one or more aldehydes and (ii) at least about 70 to 80 mole percent of the one or more aldehydes remain unreacted, wherein the amount of unreacted aldehyde is based on an amount used to functionalize the amino or amido groups.