# US 9,752,012 B2 · Carbon-fiber-precursor acrylic fiber bundle with oil composition adhering thereto, process for producing the same, oil composition for carbon-fiber-precursor acrylic fiber, and oil composition dispersion for carbon-fiber-precursor acrylic fiber > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,752,012 B2 - Document ID: US9752012B2 - Status: Granted - Kind: B2 - Application number: 14/002,263 - Filed: 2011-03-01 - Published: 2013-12-19 - Granted: 2017-09-05 - Earliest claimed: 2011-03-01 - Assignees: Mitsubishi Chemical Corporation - Applicants: Hiromi Aso - Inventors: Hiromi Aso - Web page: https://patentgrep.com/patent/US9752012B2 ## CPC - C08K 5/12: of cyclic polycarboxylic acids - B05D 3/0254: {After-treatment} - D01F 9/22: from polyacrylonitriles - D01F 11/06: of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds - D06M 13/224: Esters of carboxylic acids; Esters of carbonic acid - D06M 15/327: of unsaturated alcohols or esters thereof - D06M 15/6436: {containing amino groups} - D01F 6/18: from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide - D01F 6/38: comprising unsaturated nitriles as the major constituent - D06M 15/3568: {containing silicon} - D06M 2101/28: Acrylonitrile; Methacrylonitrile - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02) - 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 ## Abstract The present invention relates to a carbon-fiber-precursor acrylic fiber bundle with an oil composition adhering thereto, wherein the oil composition comprises an amino-modified silicone, an aromatic ester compound (1) having a structure represented by the following formula (1), and an aromatic ester compound (2) having a structure represented by the following formula (2), the amino-modified silicone, the aromatic ester compound (1), and the aromatic ester compound (2) meet the specific requirements, the process for producing the same, an oil composition carbon-fiber-precursor acrylic fiber, and an oil composition dispersion for carbon-fiber-precursor acrylic fiber. ## Claims ### Claim 1 A carbon-fiber-precursor acrylic fiber bundle with an oil composition adhering thereto, wherein: the oil composition comprises an amino-modified silicone, an aromatic ester compound (1) having a structure of formula (1): and an aromatic ester compound (2) having a structure of formula (2): an adhesion amount of the amino-modified silicone is from 0.01 to 0.2% by mass relative to a mass of the dry fiber, a total adhesion amount of the aromatic ester compound (1) and the aromatic ester compound (2) is from 0.4 to 1.2% by mass relative to the mass of the dry fiber, a ratio of the adhesion amounts of the aromatic ester compound (2) to the aromatic ester compound (1) is from 0.25 to 6.5, R1 and R2 are each independently a hydrocarbon group having 7 to 21 carbon atoms, m and n are each independently an integer of from 1 to 5, and R3, R4, and R5 are each independently a hydrocarbon group having 8 to 10 carbon atoms. ### Claim 2 (depends on 1) The fiber bundle according to claim 1, wherein the amino-modified silicone is an amino-modified silicone having a structure of formula (3): wherein o is an integer of from 5 to 300, and p is an integer of from 1 to 5. ### Claim 3 (depends on 1) The fiber bundle according to claim 1, wherein the amino-modified silicone has a kinematic viscosity of from 50 to 500 mm2/s at 25° C. ### Claim 4 (depends on 1) The fiber bundle according to claim 1, wherein a block copolymerization polyether comprising a propylene oxide unit and an ethylene oxide unit and having a structure of formula (4): H—OC2H4OxC3H6OyC2H4Oz—H (4) is further adhered in a quantity of from 5 to 70 parts by mass relative to 100 parts by mass representing a total adhesion amount of the aromatic ester compound (1), the aromatic ester compound (2), and the amino-modified silicone to the dry fiber, wherein x, y, and z are each independently an integer of from 1 to 200. ### Claim 5 (depends on 1) The fiber bundle according to claim 1, wherein the amino-modified silicone has a kinematic viscosity of from 50 to 300 mm2/s at 25° C. ### Claim 6 An oil composition comprising an amino-modified silicone, an aromatic ester compound (1) having a structure of formula (1): and an aromatic ester compound (2) having a structure of formula (2): wherein: a content of the amino-modified silicone is from 1 to 25 parts by mass relative to 100 parts by mass of a total quantity of the aromatic ester compound (1) and the aromatic ester compound (2), and a mass ratio of the aromatic ester compound (2) to the aromatic ester compound (1) is from 0.25 to 6.5, R1 and R2 are each independently a hydrocarbon group having 7 to 21 carbon atoms, m and n are each independently an integer of from 1 to 5, and R3, R4, and R5 are each independently a hydrocarbon group having 8 to 10 carbon atoms. ### Claim 7 (depends on 6) The oil composition according to claim 6, wherein the amino-modified silicone is an amino-modified silicone having a structure of formula (3): wherein o is an integer of from 5 to 300, and p is an integer of from 1 to 5. ### Claim 8 (depends on 6) The oil composition according to claim 6, wherein the amino-modified silicone has a kinematic viscosity of from 50 to 500 mm2/s at 25° C. ### Claim 9 (depends on 6) The oil composition according to claim 6, further comprising a block copolymerization polyether comprising a propylene oxide unit and an ethylene oxide unit and having a structure of formula (4): H—OC2H4OxC3H6OyC2H4Oz—H (4) in a quantity of from 10 to 50 parts by mass relative to 100 parts by mass of a total quantity of the amino-modified silicone, the aromatic ester compound (1), and the aromatic ester compound (2), wherein x, y, and z are each independently an integer of from 1 to 200. ### Claim 10 (depends on 6) An oil composition dispersion, wherein the oil composition according to claim 6 is dispersed in water or a solvent. ### Claim 11 (depends on 10) The oil composition dispersion according to claim 10, wherein the oil composition forms micelles with an average particle size of from 0.01 to 0.50 μm. ### Claim 12 (depends on 6) A process for producing a carbon-fiber-precursor acrylic fiber bundle with an oil composition adhering thereto, comprising: applying an oil composition dispersion obtained by dispersing the oil composition according to claim 6 in water or a solvent, forming micelles with an average particle size of from 0.01 to 0.50, to a carbon-fiber-precursor acrylic fiber bundle in a water-swelled state, and performing drying densification of the carbon-fiber-precursor acrylic fiber bundle. ### Claim 13 (depends on 6) The oil composition according to claim 6, wherein the amino-modified silicone has a kinematic viscosity of from 50 to 300 mm2/s at 25° C.