# US 2019/0169314 A1 · Modified cellulose fibers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2019/0169314 A1 - Document ID: US20190169314A1 - Status: Published application - Kind: A1 - Application number: 15/757,700 - Filed: 2016-09-05 - Published: 2019-06-06 - Earliest claimed: 2015-09-07 - Assignees: Kao Corporation - Applicants: Kao Corporation - Inventors: Yutaka YOSHIDA; Shotaro SHIBATA; Yoshiaki KUMAMOTO; Takuma TSUBOI; Motoi KONISHI - Web page: https://patentgrep.com/patent/US20190169314A1 ## CPC - C08B 11/193: Mixed ethers, i.e. ethers with two or more different etherifying groups - C08L 1/284: {with hydroxylated hydrocarbon radicals} - C08L 7/00: Compositions of natural rubber - C08L 9/02: Copolymers with acrylonitrile - C08L 9/06: Copolymers with styrene - C08L 23/06: Polyethylene - C08L 25/06: Polystyrene - C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins - C08L 75/14: Polyurethanes having carbon-to-carbon unsaturated bonds - C08L 75/16: having terminal carbon-to-carbon unsaturated bonds - C08L 2205/08: containing additives to improve the compatibility between two polymers - C08L 2205/16: Fibres; Fibrils - 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) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) ## Abstract Modified cellulose fibers, wherein each of (A) one or more substituents selected from substituents represented by the following general formula (1) and substituents represented by the following general formula (2): —CH2—CH(OH)—R1 (1); —CH2—CH(OH)—CH2—(OA)n-O—R1 (2), wherein each R1 in the general formula (1) and the general formula (2) is independently a linear or branched alkyl group having 3 or more carbon atoms and 30 or less carbon atoms; n in the general formula (2) is a number of 0 or more and 50 or less; and A is a linear or branched, divalent saturated hydrocarbon group having 1 or more carbon atoms and 6 or less carbon atoms, and (B) a substituent represented by the following general formula (3): —CH2—CH(OH)—R2 (3), wherein R2 in the general formula (3) is an alkyl group having 1 or more carbon atoms and 2 or less carbon atoms, is independently bonded to cellulose fibers via an ether bond, wherein the modified cellulose fibers have a cellulose I crystal structure. The resin composition blended with the modified cellulose fibers of the present invention can be suitably used in various industrial applications such as daily sundries, household electric appliance parts, wrapping materials for household electric appliance parts and automobile parts. ## Claims ### Claim 1 Modified cellulose fibers, wherein each of (A) one or more substituents selected from substituents represented by the following general formula (1) and substituents represented by the following general formula (2): —CH2—CH(OH)—R1 (1) —CH2—CH(OH)—CH2—(OA)n-O—R1 (2) wherein each R1 in the general formula (1) and the general formula (2) is independently a linear or branched alkyl group having 3 or more carbon atoms and 30 or less carbon atoms; n in the general formula (2) is a number of 0 or more and 50 or less; and A is a linear or branched, divalent saturated hydrocarbon group having 1 or more carbon atoms and 6 or less carbon atoms, and (B) a substituent represented by the following general formula (3): —CH2—CH(OH)—R2 (3) wherein R2 in the general formula (3) is an alkyl group having 1 or more carbon atoms and 2 or less carbon atoms, is independently bonded to cellulose fibers via an ether bond, wherein the modified cellulose fibers have a cellulose I crystal structure. ### Claim 2 (depends on 1) The modified cellulose fibers according to claim 1, which are modified cellulose fibers represented by the following general formula (4): wherein R, which may be identical or different, is hydrogen, or (A) a substituent selected from substituents represented by the general formula (1) defined above and substituents represented by the general formula (2) defined above, or (b) a substituent represented by the general formula (3) defined above; and m is an integer of 20 or more and 3,000 or less, with proviso that a case where all R's are simultaneously hydrogens, a case where all are simultaneously substituents (A), and a case where all are simultaneously a substituent (B) are excluded. ### Claim 3 (depends on 1) The modified cellulose fibers according to claim 1, wherein the introduction ratio of the substituent or substituents selected from substituents represented by the general formula (1) and substituents represented by the general formula (2) is 0.001 mol or more and 1.5 mol or less, per mol of the anhydrous glucose unit. ### Claim 4 (depends on 1) The modified cellulose fibers according to claim 1, wherein n is a number of 0 or more and 20 or less, and A is a linear or branched, divalent saturated hydrocarbon group having 2 or more carbon atoms and 3 or less carbon atoms, in the substituent represented by the general formula (2). ### Claim 5 (depends on 1) The modified cellulose fibers according to claim 1, wherein the average fiber size is 5 μm or more. ### Claim 6 (depends on 1) The modified cellulose fibers according to claim 1, wherein the average fiber size is 5 Um or more and 100 μm or less. ### Claim 7 (depends on 1) The modified cellulose fibers according to claim 1, wherein the average fiber size is 1 nm or more and 500 nm or less. ### Claim 8 (depends on 1) The modified cellulose fibers according to claim 1, wherein the average fiber size is 3 nm or more and 300 nm or less. ### Claim 9 (depends on 1) The modified cellulose fibers according to claim 1, wherein R1 in the general formula (1) has the number of carbon atoms of 4 or more and 20 or less. ### Claim 10 (depends on 1) The modified cellulose fibers according to claim 1, wherein R1 in the general formula (2) has the number of carbon atoms of 4 or more and 20 or less. ### Claim 11 (depends on 1) The modified cellulose fibers according to claim 1, wherein A in the general formula (2) has the number of carbon atoms of 2 or more and 4 or less. ### Claim 12 (depends on 1) The modified cellulose fibers according to claim 1, wherein the introduction ratio of the substituent or substituents selected from substituents represented by the general formula (1) and substituents represented by the general formula (2) is 0.01 mol or more, per mol of the anhydrous glucose unit. ### Claim 13 (depends on 1) The modified cellulose fibers according to claim 1, wherein the crystallinity is 10% or more. ### Claim 14 (depends on 1) The modified cellulose fibers according to claim 1, wherein the crystallinity is 20% or more. ### Claim 15 A method for producing modified cellulose fibers, comprising introducing (b) a nonionic alkylene oxide compound having a total number of carbon atoms of 3 or more and 4 or less per molecule, and (a) one or more compounds selected from nonionic alkylene oxide compounds having a total number of carbon atoms of 5 or more and 32 or less per molecule and nonionic glycidyl ether compounds having a total number of carbon atoms of 5 or more and 100 or less per molecule to a cellulose-based raw material via an ether bond, in the presence of a base, concurrently or separately. ### Claim 16 (depends on 15) The method according to claim 15, wherein the method comprises the following steps II-1 and II-2: step II-1) introducing (b) a nonionic alkylene oxide compound having a total number of carbon atoms of 3 or more and 4 or less per molecule to a cellulose-based raw material via an ether bond, in the presence of a base, and step II-2) introducing (a) one or more compounds selected from nonionic alkylene oxide compounds having a total number of carbon atoms of 5 or more and 32 or less per molecule and nonionic glycidyl ether compounds having a total number of carbon atoms of 5 or more and 100 or less per molecule to cellulose fibers obtained in the step II-1 via an ether bond, in the presence of the base. ### Claim 17 (depends on 15) The method according to claim 15, wherein the base is one or more members selected from alkali metal hydroxides, alkaline earth metal hydroxides, primary to tertiary amines, quaternary ammonium salts, imidazoles and derivatives thereof, pyridine and derivatives thereof, and alkoxides. ### Claim 18 (depends on 15) The method according to claim 15, wherein the amount of the base is 0.01 equivalents or more and 10 equivalents or less, based on the anhydrous glucose unit in the cellulose-based raw material. ### Claim 19 (depends on 1) A resin composition comprising a thermoplastic resin or curable resin and modified cellulose fibers as defined in claim 1. ### Claim 20 (depends on 19) The resin composition according to claim 19, wherein the thermoplastic resin or curable resin is one or more resins selected from the group consisting of a thermoplastic resin, and a curable resin selected from an epoxy resin, a (meth)acrylic resin, a phenolic resin, an unsaturated polyester resin, a polyurethane resin, or a polyimide resin.