WO2023027910A1 - Dry spinning of cellulose acetate fiber - Google Patents

Dry spinning of cellulose acetate fiber Download PDF

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Publication number
WO2023027910A1
WO2023027910A1 PCT/US2022/040390 US2022040390W WO2023027910A1 WO 2023027910 A1 WO2023027910 A1 WO 2023027910A1 US 2022040390 W US2022040390 W US 2022040390W WO 2023027910 A1 WO2023027910 A1 WO 2023027910A1
Authority
WO
WIPO (PCT)
Prior art keywords
cellulose ester
dope
weight
fibers
cellulose
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2022/040390
Other languages
English (en)
French (fr)
Inventor
Marcus David Shelby
Mark Edward Stewart
James Collins Maine
Tanner Storm DORTON
John Michael Allen
Yong Li
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Chemical Co
Original Assignee
Eastman Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Chemical Co filed Critical Eastman Chemical Co
Priority to CN202280058133.7A priority Critical patent/CN117916413A/zh
Priority to KR1020247009888A priority patent/KR20240044539A/ko
Priority to EP22765326.8A priority patent/EP4392601A1/en
Priority to JP2024513067A priority patent/JP2024531481A/ja
Priority to US18/688,461 priority patent/US20250011975A1/en
Publication of WO2023027910A1 publication Critical patent/WO2023027910A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/24Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
    • D01F2/28Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate
    • D01F2/30Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives from organic cellulose esters or ethers, e.g. cellulose acetate by the dry spinning process
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01DMECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D1/00Treatment of filament-forming or like material
    • D01D1/02Preparation of spinning solutions
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01DMECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00Formation of filaments, threads, or the like
    • D01D5/04Dry spinning methods
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00General methods for the manufacture of artificial filaments or the like
    • D01F1/02Addition of substances to the spinning solution or to the melt
    • D01F1/10Other agents for modifying properties
    • DTEXTILES; PAPER
    • D02YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
    • D02GCRIMPING OR CURLING FIBRES, FILAMENTS, THREADS, OR YARNS; YARNS OR THREADS
    • D02G3/00Yarns or threads, e.g. fancy yarns; Processes or apparatus for the production thereof, not otherwise provided for
    • D02G3/02Yarns or threads characterised by the material or by the materials from which they are made
    • DTEXTILES; PAPER
    • D03WEAVING
    • D03DWOVEN FABRICS; METHODS OF WEAVING; LOOMS
    • D03D15/00Woven fabrics characterised by the material, structure or properties of the fibres, filaments, yarns, threads or other warp or weft elements used
    • D03D15/20Woven fabrics characterised by the material, structure or properties of the fibres, filaments, yarns, threads or other warp or weft elements used characterised by the material of the fibres or filaments constituting the yarns or threads
    • D03D15/208Woven fabrics characterised by the material, structure or properties of the fibres, filaments, yarns, threads or other warp or weft elements used characterised by the material of the fibres or filaments constituting the yarns or threads cellulose-based
    • D03D15/225Woven fabrics characterised by the material, structure or properties of the fibres, filaments, yarns, threads or other warp or weft elements used characterised by the material of the fibres or filaments constituting the yarns or threads cellulose-based artificial, e.g. viscose
    • DTEXTILES; PAPER
    • D04BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04BKNITTING
    • D04B1/00Weft knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes
    • D04B1/14Other fabrics or articles characterised primarily by the use of particular thread materials
    • D04B1/16Other fabrics or articles characterised primarily by the use of particular thread materials synthetic threads
    • DTEXTILES; PAPER
    • D04BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04BKNITTING
    • D04B21/00Warp knitting processes for the production of fabrics or articles not dependent on the use of particular machines; Fabrics or articles defined by such processes
    • D04B21/14Fabrics characterised by the incorporation by knitting, in one or more thread, fleece, or fabric layers, of reinforcing, binding, or decorative threads; Fabrics incorporating small auxiliary elements, e.g. for decorative purposes
    • D04B21/16Fabrics characterised by the incorporation by knitting, in one or more thread, fleece, or fabric layers, of reinforcing, binding, or decorative threads; Fabrics incorporating small auxiliary elements, e.g. for decorative purposes incorporating synthetic threads
    • DTEXTILES; PAPER
    • D04BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04HMAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
    • D04H1/00Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
    • D04H1/40Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
    • D04H1/42Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
    • D04H1/425Cellulose series
    • DTEXTILES; PAPER
    • D10INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10BINDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2201/00Cellulose-based fibres, e.g. vegetable fibres
    • D10B2201/20Cellulose-derived artificial fibres
    • D10B2201/28Cellulose esters or ethers, e.g. cellulose acetate

Definitions

  • the present application is generally related to the spinning of fibers. More particularly, the present application is generally related to the dry spinning of cellulose esters into fibers.
  • the cellulose ester dope comprises not more than 50% by weight acetone, based on the total weight of the cellulose ester dope;
  • the disclosure further provides a yarn, article, woven article, nonwoven article, staple fiber, and/or knitted textile comprising the cellulose ester fiber formed according to one or both of the above processes.
  • At least one cellulose ester and at least one dissolution solvent may be introduced into a dope mixer so as to form the cellulose ester dope.
  • the dope mixer can comprise any conventional device capable of mixing the cellulose ester and the dissolution solvent.
  • Exemplary dope mixers can include a continuous stirred tank reactor (“CSTR”). While in the dope mixer, the cellulose ester and solvent can be subjected to temperature and mixing conditions that facilitate the dissolution of the cellulose ester into the dissolution solvent, thereby forming the cellulose ester dope.
  • the cellulose ester dope can comprise a solids content in the range of 15% to 35%, 16% to 34%, 17% to 33%, 17% to 22%, 18% to 32%, 19% to 31 %, 20% to 31 %, 21 % to 30%, 22% to 29%, or 23% to 28% by weight, based on the total weight of the dope.
  • the cellulose ester can comprise a hemicellulose content of at least 0.25%, at least 0.5%, at least 1%, at least 2%, at least 3%, at least 4%, at least 5%, at least 6%, or at least 7% by weight. Additionally or alternatively, in one embodiment or in combination with any other mentioned embodiments, the cellulose ester can comprise a hemicellulose content of not more than 10%, not more than 9%, not more than 8%, not more than 7%, not more than 6%, not more than 5%, not more than 4%, not more than 3%, not more than 2%, or not more than 1% by weight.
  • the cellulose ester is present in the dope at a level of at least 35%, at least 40%, at least 55%, at least 65%, at least 75%, at least 85%, at least 95%, at least 98%, or 100% by weight, based on total solids in the dope.
  • the cellulose ester is present in the dope from 35% to 100%, from 45% to 100%, from 55% to 100%, from 55% to 98%, from 65% to 98%, or from 75% to 98%, based on total solids in the dope.
  • the combined weight of any polyurethanes, polyolefins, nylons, polyesters, and/or polyurethaneureas that might be present in cellulose ester dope is not more than 65%, not more than 60% by weight, not more than 55%, not more than 50%, not more than 45%, not more than 40%, not more than 35%, not more than 30%, not more than 25%, not more than 20%, not more than 15%, not more than 10%, not more than 5%, not more than 4%, not more than 3%, not more than 2%, not more than 1%, or 0% by weight, based on the total solids in the cellulose ester dope.
  • any polyurethanes that might be present in the cellulose ester dope is not present at a level of more than 10%, not more than 9%, not more than 8%, not more than 7%, not more than 6%, not more than 5%, not more than 4%, not more than 3%, not more than 2%, not more than 1%, or 0% by weight, based on the total solids in the cellulose ester dope.
  • the dope is prepared by first slurrying the cellulose ester, solvent, and any other components and then cooling to very low temperatures.
  • this temperature is at least -100°C, at least -75°C, at least -70°C, at least -65°C, at least -60°C, at least -55°C, or at least -50°C and/or not more than 5°C, not more than 4°C, not more than 3°C, not more than 2°C, not more than 1 °C, not more than 0°C, not more than -5°C, or not more than -10°C and storing at one of the foregoing temperatures of at least 1 hour, at least 2 hours, at least 3 hours, at least 4 hours, at least 5 hours, at least 6 hours, at least 7 hours, at least 8 hours, at least 9 hours, or at least 10 hours and/or not more than 48 hours, not more than 36 hours, not more than 30 hours
  • the cellulose ester dope can be spun at a rate of 10 to 1000 m/min through spinneret holes having a design known in the art (e.g., having a hole area equivalent to a circular diameter of 20 to 200 microns).
  • the spinneret may be maintained at a temperature of at least 75°C, at least 80°C, at least 85°C, at least 90°C, at least 95°C, or at least 100°C and/or not more than 175°C, not more than 170°C, not more than 165°C, not more than 160°C, not more than 155°C, or not more than 150°C.
  • the head of the spinneret may be maintained at a temperature in the range of 75°C to 175°C, 85°C to 165°C, 95°C to 160°C, or 100°C to 150°C.
  • the fibers are extruded through the spinneret into a vertical spinning cabinet, which may have walls that are nominally 150°C to 240°C and which may contain gases inside the cabinet that are nominally 200- 500°C, where the solvent is flashed off or evaporated.
  • the resulting cellulose ester fibers can comprise at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%, at least 99%, or at least 99.9% by weight of the cellulose ester, based on the total weight of the fiber.
  • the cellulose ester fiber can be formed entirely from the cellulose ester.
  • a typical spinning cabinet for spandex fibers may have more than 30 ends (or yarns), for cellulose esters, it is desirable to have no more than 30 ends per cabinet, no more than 25 per cabinet, no more than 20 per cabinet, no more than 15 per cabinet, no more than 10 per cabinet, no more than 8 per cabinet, no more than 6 per cabinet, no more than 4 per cabinet.
  • the reduction in the number of ends in a vertical spinning cabinet will allow sufficient solvent evaporation at lower temperature which is beneficial for preventing discoloration of fibers.
  • the cellulose ester fibers prefferably be drawn no more than 2x, no more than 1 ,8x, no more than 1 ,6x, no more than 1 ,4x, no more than 1 ,2x.
  • draw ratio is defined as the ratio of the fiber speed at the exit of the vertical spinning cabinet over the speed of the fiber at the exit of the spinneret holes.
  • the cellulose ester fibers and/or the yarn produced therefrom may exhibit a tenacity of at least 0.2 g/denier, at least 0.3 g/denier, at least 0.4 g/denier, at least 0.5 g/denier, at least 0.6 g/denier, at least 0.7 g/denier, at least 0.8 g/denier, at least 0.9 g/denier, at least 1 g/denier, at least 1 .1 g/denier, at least 1 .2 g/denier, at least 1 .3 g/denier, at least 1 .4 g/denier, at least 1 .5 g/denier, at least 1 .6 g/denier, at least 1 .7 g/denier, at least 1 .8 g/denier, at least 1 .9 g/denier, or at least 2 g/denier, and/or not more than 3.
  • Elongation also known as elongation at break, is expressed as a percentage and it is indicative of how much a yarn or filament will stretch before it breaks.
  • the cellulose ester fibers and/or the yarn produced therefrom may exhibit an elongation at break of at least 10%, at leastl 5%, at least 16%, at least 17%, at least 18%, at least 19%, at least 20%, at least 21%, at least 22%, at least 23%, at least 24%, at least 25%, at least 26%, at least 27%, at least 28%, at least 29%, or at least 30% as measured according to ASTM D22556.
  • the cellulose ester fibers and/or the yarn produced therefrom may exhibit a silk factor of at least 5.0, at least 6.0, at least 7.0, or at least 7.6, where elongation is defined as a percentage and tenacity is in grams/denier.
  • the crimp amplitude of the fibers when crimped, may vary and can, for example, be at least 0.85, 0.90, 0.93, 0.96, 0.98, 1 .00, or 1 .04 mm. Additionally or alternatively, in one embodiment or in combination with any other mentioned embodiments, the crimp amplitude of the fibers can be up to 1 .75, up to 1 .70, up to 1 .65, up to 1 .55, up to 1 .35, up to 1 .28, up to 1 .24, up to 1 .15, up to 1 .10, up to 1 .03, or up to 0.98 mm.
  • Crimp amplitude and crimp ratio are measured according to the procedure outlined in U.S. Pat. App. Pub. No. 2020/0299822, which is incorporated herein by reference to the extent not inconsistent with the present disclosure.
  • the cellulose ester fibers can include at least one plasticizer or, in the alternative, no plasticizer.
  • the cellulose ester fibers may comprise less than 30, less than 12, less than 10, less than 9, less than 8, less than 7, less than 6, less than 5, less than 4, less than 3, less than 2, less than 1 , less than 0.5 weight percent of at least one plasticizer, based on the total weight of the cellulose ester fiber.
  • the plasticizer may be incorporated into the fiber itself by spinning a dope containing a plasticizer, contained in a flake used to make the dope, and/or the plasticizer may be applied to the surface of the fiber or filament by any of the methods used to apply a finish. If desired, the plasticizer can be contained in the finish formulation.
  • the cellulose ester fibers and/or the yarns formed therefrom can exhibit a weight loss of at least 5%, at least 10%, at least 15%, or at least 20% after burial in soil for 60 days and/or a weight loss of at least 15%, at least 20%, at least 25%, at least 30%, or at least 35% after 15 days of exposure in a composter.
  • the rate of degradation may vary depending on the particular end use of the fibers. Exemplary test conditions are provided in U.S. Pat. Nos. 5,870,988 and 6,571 ,802, incorporated herein by reference. [0078]
  • the cellulose ester fibers and/or the yarns formed therefrom can be compostable.
  • the cellulose ester fibers and/or the yarns formed therefrom can exhibit a biodegradation of at least 70 percent in a period of not more than 49, not more than 48, not more than 47, not more than 46, not more than 45, not more than 44, not more than 43, not more than 42, not more than 41 , not more than 40, not more than 39, not more than 38, or not more than 37 days when tested under these conditions, also called “home composting conditions.” These conditions may not be aqueous or anaerobic.
  • the denier per filament (weight in g of 9000 m fiber length), or “DPF,” of the cellulose ester fibers may be within a range of 0.5 to less than 20.
  • the particular method for measurement is not limited and include the ASTM 1577-07 method using the FAVIMAT vibroscope procedure if filaments can be obtained from which the staple fibers are cut, a microbalance weight measurement of a sample of known length, or a width analysis using any convenient optical microscopy or analyzer.
  • the DPF can also be correlated to the maximum width of a fiber.
  • the cellulose ester fibers may be formed into a nonwoven article, such as a nonwoven textile.
  • exemplary nonwoven articles can include wet-laid nonwoven articles, air-laid non-woven articles, carded articles, and/or dry-laid non-woven articles.
  • the end products described herein, including the staple fibers, yarns, nonwoven articles, knitted articles, and the woven articles, may comprise at least 0.25, at least 0.5, at least 0.75, at least 1 , at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 12, at least 15, at least 18, at least 20, at least 25, at least 30, at least 35, at least 40, at least 45, at least 50, at least 55, at least 60, at least 65, at least 70, at least 75, at least 80, at least 85, at least 90, at least 95, at least 99, or at least 99.9 weight percent of one or more cellulose ester fibers, based on the total weight of the article.
  • the end products described herein may comprise not more than 99, not more than 95, not more than 90, not more than 85, not more than 80, not more than 75, not more than 70, not more than 65, not more than 60, not more than 55, not more than 50, not more than 45, not more than 40, not more than 35, not more than 30, not more than 25, not more than 20, not more than 15, not more than 10, not more than 9, not more than 8, not more than 7, not more than 6, or not more than 5 weight percent of one or more cellulose ester fibers, based on the total weight of the article.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Artificial Filaments (AREA)
PCT/US2022/040390 2021-08-26 2022-08-16 Dry spinning of cellulose acetate fiber Ceased WO2023027910A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN202280058133.7A CN117916413A (zh) 2021-08-26 2022-08-16 乙酸纤维素纤维的干纺
KR1020247009888A KR20240044539A (ko) 2021-08-26 2022-08-16 셀룰로오스 아세테이트 섬유의 건식 스피닝
EP22765326.8A EP4392601A1 (en) 2021-08-26 2022-08-16 Dry spinning of cellulose acetate fiber
JP2024513067A JP2024531481A (ja) 2021-08-26 2022-08-16 酢酸セルロース繊維の乾式紡糸
US18/688,461 US20250011975A1 (en) 2021-08-26 2022-08-16 Dry spinning of cellulose acetate fiber

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163260580P 2021-08-26 2021-08-26
US63/260,580 2021-08-26

Publications (1)

Publication Number Publication Date
WO2023027910A1 true WO2023027910A1 (en) 2023-03-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2022/040390 Ceased WO2023027910A1 (en) 2021-08-26 2022-08-16 Dry spinning of cellulose acetate fiber

Country Status (6)

Country Link
US (1) US20250011975A1 (https=)
EP (1) EP4392601A1 (https=)
JP (1) JP2024531481A (https=)
KR (1) KR20240044539A (https=)
CN (1) CN117916413A (https=)
WO (1) WO2023027910A1 (https=)

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WO2024205978A1 (en) * 2023-03-29 2024-10-03 Eastman Chemical Company Blended cellulose acetate fiber and process for the making thereof
WO2024229055A3 (en) * 2023-05-04 2025-02-06 Eastman Chemical Company Methods of converting assets to increase cellulosic yarn production

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