# US 9,040,681 B2 · Method for producing cationized cellulose and method for producing cationized hydroxyalkyl cellulose > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,040,681 B2 - Document ID: US9040681B2 - Status: Granted - Kind: B2 - Application number: 13/581,760 - Filed: 2011-02-28 - Published: 2013-01-03 - Granted: 2015-05-26 - Earliest claimed: 2010-03-02 - Assignees: Kao Corporation - Applicants: Akiyoshi Kimura; Keiichiro Tomioka; Toru Nishioka; Kohei Nakanishi - Inventors: Akiyoshi Kimura; Keiichiro Tomioka; Toru Nishioka; Kohei Nakanishi - Web page: https://patentgrep.com/patent/US9040681B2 ## CPC - C08B 11/08: with hydroxylated hydrocarbon radicals; Esters, ethers, or acetals thereof - C08B 1/06: Rendering cellulose suitable for etherification {(etherification per se C08B11/00)} - C08B 11/145: with basic nitrogen, e.g. aminoalkyl ethers - C08B 11/20: Post-etherification treatments of chemical or physical type, {e.g. mixed etherification in two steps}, including purification - C08B: POLYSACCHARIDES; DERIVATIVES THEREOF (polysaccharides containing less than six saccharide radicals attached to each other by glycosidic linkages C07H; fermentation or enzyme-using processes C12P19/00; sugar industry C13; production of cellulose D21) ## Abstract A production method of a cationized cellulose or a cationized hydroxyalkylcellulose, including step 1 for adding a cationizing agent to cellulose and mechanically decrystallizing the cellulose and step 2 for adding a basic compound to the mixture obtained in step 1 and mechanically decrystallizing the cellulose, or a production method of a cationized cellulose or a cationized hydroxyalkylcellulose, including a step 3 for adding a basic compound to cellulose and mechanically decrystallizing the cellulose and step 4 for adding a cationizing agent to the mixture obtained in step 3 and mechanically decrystallizing the cellulose. The cellulose and the cationizing agent are allowed to react with each other in step 2 or step 4. ## Claims ### Claim 1 A method of producing a cationized cellulose, the method comprising: first, adding a cationizing agent represented by formula (1): wherein each of R1 to R3 is independently a hydrocarbon group having 1 to 3 carbon atoms and X− is an anionic atom or group, to a cellulose and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P1) in crystallinity from said first adding is represented by calculation formula (1): P1=crystallinity (%) of cellulose before starting said first adding−crystallinity (%) of cellulose after completing said first adding (1) reaches 1 to 60%, thereby obtaining a mixture, and second, adding a basic compound to the mixture obtained from said first adding in an amount of 0.01 to 1 equiv per one mole of anhydroglucose unit of the cellulose in the mixture and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P2) in crystallinity from said second adding is represented by calculation formula (2): P2=crystallinity (%) of cellulose before starting said second adding−crystallinity (%) of cationized cellulose after completing said second adding (2) reaches 1 to 80%, wherein the cellulose is allowed to react with a cationizing agent represented by formula (1) during said second adding. ### Claim 2 (depends on 1) The method according to claim 1, wherein the mechanical decrystallization carried out in at least one of said first adding and said second adding is conducted in the presence of water in an amount of 5 to 50% by mass of the cellulose present during said first adding. ### Claim 3 (depends on 1) The method according to claim 1, wherein the mechanical decrystallization carried out in at least one of said first adding and said second adding is conducted in the presence of a polyether. ### Claim 4 (depends on 1) The method according to claim 1, further comprising aging a reaction mixture obtained through said first adding and second adding at 20 to 200° C. ### Claim 5 (depends on 4) The method according to claim 4, wherein the aging is conducted in the presence of water in an amount of 5 to 100% by mass of the cellulose present during said first adding. ### Claim 6 (depends on 4) The method according to claim 4, wherein the aging is conducted for 0.1 to 72 h. ### Claim 7 (depends on 1) The method according to claim 1, wherein a content of water solubles in the cationized cellulose is at least 31%, and wherein an average degree of polymerization in the cationized cellulose is at least 809. ### Claim 8 (depends on 1) The method according to claim 1, wherein, during adding the cationizing agent to the cellulose, the cellulose has an average degree of polymerization of from 1000 to 3000. ### Claim 9 A method of producing a cationized cellulose, the method comprising: first, adding a basic compound to a cellulose in an amount of 0.01 to 1 equiv per one mole of anhydroglucose unit of the cellulose and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P3) in crystallinity from said first adding is represented by calculation formula (3): P3=crystallinity (%) of cellulose before starting said first adding−crystallinity (%) of cellulose after completing said first adding (3) reaches 1 to 60%, thereby obtaining a mixture, and second, adding a cationizing agent represented by formula (1): wherein each of R1 to R3 is independently a hydrocarbon group having 1 to 3 carbon atoms and X− is an anionic atom or group, to the mixture obtained from said first adding and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P4) in crystallinity from said second adding represented by calculation formula (4): P4=crystallinity (%) of cellulose before starting said second adding−crystallinity (%) of cationized cellulose after completing said second adding (4) reaches 1 to 80%, wherein the cellulose is allowed to react with a cationizing agent represented by formula (1) during said second adding. ### Claim 10 (depends on 9) The method according to claim 9, wherein the mechanical decrystallization of at least one of said first adding and said second adding is conducted in the presence of water in an amount of 5 to 50% by mass of the cellulose present during said first adding. ### Claim 11 (depends on 9) The method according to claim 9, wherein the mechanical decrystallization carried out in at least one of said first adding and said second adding is conducted in the presence of a polyether. ### Claim 12 (depends on 9) The method according to claim 9, further comprising aging a reaction mixture obtained through said first adding and said second adding at 20 to 200° C. ### Claim 13 (depends on 12) The method according to claim 12, wherein the aging is conducted in the presence of water in an amount of 5 to 100% by mass of the cellulose present during said first adding. ### Claim 14 (depends on 12) The method according to claim 12, wherein the aging is conducted for 0.1 to 72 h. ### Claim 15 (depends on 9) The method according to claim 9, wherein a content of water solubles in the cationized cellulose is at least 31%, and wherein an average degree of polymerization in the cationized cellulose is at least 809. ### Claim 16 (depends on 9) The method according to claim 9, wherein, during adding the basic compound to the cellulose, the cellulose has an average degree of polymerization of from 1000 to 3000. ### Claim 17 A method of producing a cationized hydroxyalkylcellulose, the method comprising: first, adding a cationizing agent represented by formula (1): wherein each of R1 to R3 is independently a hydrocarbon group having 1 to 3 carbon atoms and X− is an anionic atom or group, to a cellulose and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P1) in crystallinity from said first adding is represented by calculation formula (1): P1=crystallinity (%) of cellulose before starting said first adding−crystallinity (%) of cellulose after completing said first adding (1) reaches 1 to 60%, thereby obtaining a mixture, second, adding a basic compound to the mixture obtained from said first adding in an amount of 0.01 to 1 equiv per one mole of anhydroglucose unit of the cellulose in the mixture and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P2) in crystallinity from said second adding represented by calculation formula (2): P2=crystallinity (%) of cellulose before starting said second adding−crystallinity (%) of cationized cellulose after completing said second adding (2) reaches 1 to 80%, thereby producing a cationized cellulose; and reacting the cationized cellulose with an alkylene oxide having from 2 to 4 carbon atoms, wherein the cellulose is allowed to react with a cationizing agent represented by formula (1) during said second adding. ### Claim 18 A method of producing a cationized hydroxyalkylcellulose, the method comprising: first, adding a basic compound to a cellulose in an amount of 0.01 to 1 equiv per one mole of anhydroglucose unit of the cellulose and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P3) in crystallinity from the first adding represented by calculation formula (3): P3=crystallinity (%) of cellulose before starting said first adding−crystallinity (%) of cellulose after completing said first adding (3) reaches 1 to 60%, thereby obtaining a mixture, and second, adding a cationizing agent represented by formula (1): wherein each of R1 to R3 is independently a hydrocarbon group having 1 to 3 carbon atoms and X− is an anionic atom or group, to the mixture obtained from said first adding and mechanically decrystallizing the cellulose with a tank-drive media mill such that a reduction (P4) in crystallinity from said second adding is represented by calculation formula (4): P4=crystallinity (%) of cellulose before starting said second adding−crystallinity (%) of cationized cellulose after completing said second adding (4) reaches 1 to 80%, thereby producing a cationized cellulose; and reacting the cationized cellulose with an alkylene oxide having from 2 to 4 carbon atoms, wherein the cellulose is allowed to react with a cationizing agent represented by formula (1) during said second adding.