# US 12,180,615 B2 · Method for producing micronized hydrophobically modified cellulose fiber > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,180,615 B2 - Document ID: US12180615B2 - Status: Granted - Kind: B2 - Application number: 16/958,369 - Filed: 2018-12-21 - Published: 2021-03-25 - Granted: 2024-12-31 - Earliest claimed: 2017-12-27 - Assignees: Kao Corporation - Applicants: Kao Corporation - Inventors: Shunsuke Fukui; Yutaka Yoshida; Kyohei Yamato; Ryohta Yamamoto - Web page: https://patentgrep.com/patent/US12180615B2 ## CPC - D01F 2/00: Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof - D06M 13/17: Polyoxyalkyleneglycol ethers - C08B 15/04: Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide - C08B 15/06: containing nitrogen {, e.g. carbamates} - C08K 7/02: Fibres or whiskers - C08L 1/04: Oxycellulose; Hydrocellulose {, e.g. microcrystalline cellulose} - C08L 1/08: Cellulose derivatives - C08L 21/00: Compositions of unspecified rubbers - C08L 87/00: Compositions of unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds - D01F 11/02: of cellulose, cellulose derivatives, or proteins - D06M 13/325: Amines - D06M 15/53: Polyethers (polyacetals D06M15/39) - D06M 2101/06: cellulosic - D06M 2200/12: Hydrophobic properties - D06M 2400/01: Creating covalent bondings between the treating agent and the fibre - D10B 2201/20: Cellulose-derived artificial fibres - D01F: CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS - D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS - 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) - 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) - D10B: INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES ## Abstract The present invention relates to a method for producing fine hydrophobically modified cellulose fibers wherein anionic group-containing anionically modified cellulose fibers are bound to a modifying group, the method including subjecting hydrophobically modified cellulose fibers having an average fiber length of 1 μm or more and 1,000 μm or less to a finely pulverizing treatment in an organic solvent. The fine hydrophobically modified cellulose fibers obtained by the method for production of the present invention can be suitably used in various resin manufactured articles for daily sundries, household electric appliance parts, wrapping materials for household electric appliance parts, and various industrial applications such as automobile parts. ## Claims ### Claim 1 A method for producing fine hydrophobically modified cellulose fibers having an average fiber length of 1 μm or more and 1,000 μm or less comprising anionic group-containing anionically modified cellulose fibers bound to a modifying group, the method comprising: subjecting anionically modified cellulose fibers to a fiber shortening treatment, subsequently introducing the anionically modified cellulose fibers to a modifying group to produce hydrophobically modified cellulose fibers comprising anionic group-containing anionically modified cellulose fibers, and thereafter subjecting the hydrophobically modified cellulose fibers to a finely pulverizing treatment in an organic solvent to produce the fine hydrophobically modified cellulose fibers; wherein the fiber shortening treatment is a hydrothermal decomposition treatment. ### Claim 2 (depends on 1) The method for production according to claim 1, wherein the average fiber length of the hydrophobically modified cellulose fibers is 5 μm or more and 500 μm or less. ### Claim 3 (depends on 1) The method for production according to claim 1, wherein the average fiber diameter of the hydrophobically modified cellulose fibers is 1 μm or more and 300 μm or less. ### Claim 4 (depends on 1) The method for production according to claim 1, wherein the anionic group comprises one or more groups selected from the group consisting of a carboxy group, a sulfonate group, and a phosphate group. ### Claim 5 (depends on 1) The method for production according to claim 1, wherein the anionic group is a carboxy group. ### Claim 6 (depends on 1) The method for production according to claim 1, wherein the step of introducing the anioninically modified cellulose fibers to the modifying group includes bonding the anionic group-containing anionically modified cellulose fibers to a compound having the modifying group at the anionic group via ionic bonding and/or a covalent bonding. ### Claim 7 (depends on 6) The method for production according to claim 6, wherein the compound having a modifying group is one or more amines selected from the group consisting of the amines represented by the following general formulas (1) to (3): NH2—R1 (1) NH—R2R2′ (2) N—R3R3′R3″ (3) wherein R1 in the general formula (1) is a linear or branched, saturated or unsaturated hydrocarbon group having 6 or more carbon atoms and 30 or less carbon atoms; each of R2 and R2′ in the general formula (2), which may be identical or different, is a linear or branched, saturated or unsaturated hydrocarbon group in which a total number of carbon atoms of R2 and R2′ is 8 or more and 40 or less; and each of R3, R3′ and R3″ in the general formula (3), which may be identical or different, is a linear or branched, saturated or unsaturated hydrocarbon group in which a total number of carbon atoms of R3, R3′ and R3″ is 9 or more and 50 or less. ### Claim 8 (depends on 6) The method for production according to claim 6, wherein the compound having a modifying group is one or more amines selected from the group consisting of primary amines, secondary amines, and tertiary amines. ### Claim 9 (depends on 1) The method for production according to claim 1, wherein a total mass of the modifying group in the hydrophobically modified cellulose fibers, based on 100 parts by mass of the amount of the cellulose fibers, is 1 part by mass or more and 200 parts by mass or less. ### Claim 10 (depends on 1) The method for production according to claim 1, wherein the organic solvent comprises one or more organic solvents selected from the group consisting of N,N-dimethylformamide, dimethyl sulfoxide, N,N-dimethylacetamide, N-methylpyrrolidone, tetrahydrofuran (THF), a diester obtained from succinic acid and triethylene glycol monomethyl ether, dichloromethane, chloroform, toluene, acetic acid, methanol, ethanol, benzyl alcohol, n-propanol, 2-propanol, ethylene glycol, propylene glycol, t-butyl alcohol, cyclohexanone, acetonitrile, silicone oil, 1,3-dioxolane, methyl acetate, ethyl acetate, butyl acetate, acetone, and methyl ethyl ketone. ### Claim 11 A method for producing a dispersion of fine hydrophobically modified cellulose fibers having an average fiber length of 1 μm or more and 1,000 μm or less comprising anionic group-containing anionically modified cellulose fibers bound to a modifying group, the method comprising: subjecting anionically modified cellulose fibers to a fiber shortening treatment, subsequently introducing the anionically modified cellulose fibers to a modifying group to produce hydrophobically modified cellulose fibers comprising anionic group-containing anionically modified cellulose fibers, and thereafter subjecting the hydrophobically modified cellulose fibers to a finely pulverizing treatment in an organic solvent to produce the fine hydrophobically modified cellulose fibers; wherein the fiber shortening treatment is a hydrothermal decomposition treatment. ### Claim 12 (depends on 1) A method for producing a resin composition comprising: mixing fine hydrophobically modified cellulose fibers having an average fiber length of 1 μm or more and 1,000 μm or less produced by a method for production as defined in claim 1 with a resin. ### Claim 13 (depends on 12) A method for producing a resin molded article comprising molding a resin composition produced by a method for producing a resin composition as defined in claim 12. ### Claim 14 (depends on 1) A resin composition obtained by mixing: fine hydrophobically modified cellulose fibers produced by a method for production as defined in claim 1 with a resin. ### Claim 15 (depends on 14) A resin molded article comprising a resin composition as defined in claim 14 molded therewith. ### Claim 16 (depends on 11) A method for producing a resin composition comprising: mixing a dispersion of fine hydrophobically modified cellulose fibers wherein anionic group-containing anionically modified cellulose fibers are bound to a modifying group, with a resin; and wherein the dispersion of fine hydrophobically modified cellulose fibers are produced by a method as defined in claim 11.