US20190203409A1 - Antibacterial regenerated cellulosic fibers and process of preparation thereof - Google Patents

Antibacterial regenerated cellulosic fibers and process of preparation thereof Download PDF

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Publication number
US20190203409A1
US20190203409A1 US16/333,887 US201716333887A US2019203409A1 US 20190203409 A1 US20190203409 A1 US 20190203409A1 US 201716333887 A US201716333887 A US 201716333887A US 2019203409 A1 US2019203409 A1 US 2019203409A1
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United States
Prior art keywords
ammonium chloride
antibacterial
regenerated cellulosic
fiber
dimethyl
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US16/333,887
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English (en)
Inventor
Vishvajit Chandrakant Juikar
Nilesh Guruling Waghmare
Sushant Dilip Murudkar
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Grasim Industries Ltd
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Grasim Industries Ltd
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Assigned to GRASIM INDUSTRIES LIMITED reassignment GRASIM INDUSTRIES LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: JUIKAR, VISHVAJIT CHANDRAKANT, MURUDKAR, SUSHANT DILIP, WAGHMARE, NILESH GURULING
Publication of US20190203409A1 publication Critical patent/US20190203409A1/en
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02Natural fibres, other than mineral fibres
    • D06M2101/04Vegetal fibres
    • D06M2101/06Vegetal fibres cellulosic

Definitions

  • the present disclosure provides antibacterial regenerated cellulosic fibers and a process for preparing the said antibacterial regenerated cellulosic fibers.
  • Cellulosic fibers are known for their good wearability. Cellulosic fibers are excellent in terms of sweat absorption because of their higher hydrophilicity as compared to other type of manmade fibers. Thus, cellulose fibers are suitable for use in outdoor clothes, sports clothes, shirts and undergarments that are in direct contact with the skin.
  • antibacterial cellulosic fibers and their products having anti-bacterial property, odor-preventing properties or destroying properties as well as deodorizing properties.
  • Such antibacterial cellulosic fibers should inhibit the inhabitation and proliferation of bacteria on fibers and be safe for human use while persistently maintaining antibacterial effects. Further, it is desirable that the antibacterial cellulosic fibers are made using approved chemicals (as per BPR or REACH).
  • the antibacterial regenerated cellulosic fiber comprises a quaternary ammonium compound in a concentration range of 0.05-1% w/w on the regenerated cellulosic fiber.
  • a process for preparing antibacterial regenerated cellulosic fibers comprises spinning a cellulosic solution through spinneret into a regeneration bath to obtain regenerated cellulosic fibers; washing the regenerated cellulosic fibers; treating the regenerated cellulosic fibers with a solution of quaternary ammonium compound having a concentration range of 0.1-1.5% w/w of regenerated cellulosic fibers to obtain treated regenerated cellulosic fibers; and drying the treated regenerated cellulosic fibers to obtain antibacterial regenerated cellulosic fibers.
  • the present disclosure provides antibacterial regenerated cellulosic fibers and a process for preparation thereof.
  • the antibacterial regenerated cellulosic fibers comprising a quaternary ammonium compound in a concentration range of 0.05-1% w/w on the regenerated cellulosic fiber.
  • the quaternary ammonium compound is selected from the group consisting of dodecyl dimethylammonium chloride (DDAC), C8-C18 alkyltrimethylammonium chlorides (such as trimethyloctylammonium chloride, decyltrimethylammonium chloride and hexadecyltrimethylammonium chloride), soyalkyltrimethylammonium chloride, dicocalkyl dimethyl ammonium chloride, alkyl-benzyldimethylammonium chlorides (such as benzyldimethylstearylammonium chloride, benzylalkyldimethylammonium chloride orcocalkyl(2,4-dichlorobenzyl) dimethylammonium chloride, Dimethyl Benzyl Ammonium Chloride, OctylDecyl Dimethyl Ammonium Chloride, Didecyl Dimethyl Ammonium Chloride, Dioctyl Dimethyl Ammonium Chlor
  • the antibacterial regenerated cellulosic fibers can be used to manufacture masks, scrubs, towels, doctor's coats, bath robes, pajamas, and uniforms for medical personnel; linens for use in hospitals; both sanitary and be perceived as sanitary; antibacterial finished socks required for foot ulcer prevention; antibacterial and antifungal finished socks and inner wear for military personnel; sportswear market comprising sport socks, gloves, sport bras, caps etc.; home textiles and furnishing; textiles; and antibacterial wipes etc.
  • the products obtained by utilization of the antibacterial regenerated cellulosic fibers have improved antibacterial properties; controlled odor and staining due to bacterial growth; antibacterial activity of more than 99% after at least 20 wash cycles.
  • Such products are obtained by environment friendly technology, as chemicals used in the process can be recycled in the process. Further, minimal amount of chemical is sufficient for antibacterial property. Additionally, the antibacterial regenerated cellulosic fibers retain antibacterial activity during downstream processing.
  • the antibacterial regenerated cellulosic fibers can be an antibacterial viscose staple fiber, antibacterial modal fiber or antibacterial lyocell fiber.
  • the antibacterial regenerated cellulosic fibers can be used for making woven, non-woven fabrics, fiber blends and fiber composites.
  • the present disclosure also provides a process for preparing antibacterial regenerated cellulosic fibers, the process comprising spinning a cellulosic solution through spinneret into a regeneration bath to obtain regenerated cellulosic fibers; washing the regenerated cellulosic fibers; treating the regenerated cellulosic fibers with a solution of quaternary ammonium compound having a concentration range of 0.1-1.5% w/w of regenerated cellulosic fibers to obtain treated regenerated cellulosic fibers; and drying the treated regenerated cellulosic fibers to obtain antibacterial regenerated cellulosic fibers.
  • present process provides a mechanism to open pores or striations on the surface of fibers to increase the surface area and infuse more active ingredients.
  • pathogens such as: gram-negative bacteria, gram-positive bacteria, mold, mildew, fungus, spores, and viruses, and not be washed away during repeated launderings and uses.
  • the regenerated cellulosic fibers are prepared by viscose process.
  • the viscose was prepared by treatment of pulp sheets (high alpha cellulose, viscose grade pulp) with caustic soda, shredding the resulting in alkali cellulose, xanthating the alkali cellulose and dissolving it in a caustic soda solution.
  • the viscose was then aged and spun by extrusion through orifices into a spinning bath containing sulfuric acid, sodium sulfate and zinc sulfate.
  • the spinning bath being maintained at a temperature of 30-50° C.
  • the filaments were withdrawn from the bath and passed over a first and second godets, then collected. After collecting the filaments, they were washed, desulfurized and bleached by conventional treatments.
  • the regenerated cellulosic fibres can also be prepared by Lyocell process, wherein the cellulose was dissolved in N-methylmorpholine (NMMO) under heated conditions, usually in the range of 90° C. to 130° C., and extruded from a multiplicity of fine apertured spinnerets into air.
  • NMMO N-methylmorpholine
  • the filaments of cellulose dope are continuously mechanically drawn in air by a factor in the range of about three to ten times to cause molecular orientation. They are then led into water, to regenerate the cellulosic fibres namely Lyocell.
  • extension of present invention to other cellulosic natural fibres such as cotton, Jute, hemp, flax etc., is conceivable for the person skilled in the art.
  • Viscose Staple Fiber (VSF) or Modal or Lyocell made using standard manufacturing process does not give durable antibacterial performance.
  • An antibacterial agent is used in Standard VSF or Modal or Lyocell manufacturing process to improve antibacterial performance of fiber.
  • a small amount of chemical DDAC i.e. 0.05-1% on weight of cellulose fiber
  • the resultant fiber was then evaluated for antibacterial performance in external biological laboratory as per standard test methods.
  • Triclosan did not demonstrate any antibacterial activity at 0.5% concentration to weight of cellulose, but DDAC shows 100% contact inhibition of bacteria in spite of lower concentration of 0.15%.
  • Viscose fiber treated with and without DDAC as an antibacterial agent Sr. No. Sample description Bacteria AATCC 100* JIS L-1902* C.E.-2.1 Viscose Fiber S. Aureus 97.7 2.07 K.pneumoniae 95 2.06 C.E.-2.2 Viscose Fiber-20 wash S. Aureus 0 1.79 K.pneumoniae 0 1.33 C.E.-2.3 Viscose Fiber --> Spunlaced to make S. Aureus 62.17 1.4 Nonwoven sheet K.pneumoniae 45.83 1.38 Ex.-2.1 Viscose fiber treated with 0.15% S.
  • Comparative example C.E.2.1-2.3 show less antibacterial activity and after 20 washes the activity is lost completely. Also, activity is considerably reduced during the process of making nonwoven spunlaced sheets. Similarly, in examples 2.1-2.7 which are treated with 0.05 to 1% DDAC on fiber surface, shows more than 99% bacterial kill and further this activity is retained after 20-30 wash cycles and even after spunlacing process.
  • Comparative example C.E.3.1-3.3 VSF fiber made by dope dyeing process i.e. dope dyed using black pigment
  • the activity is reduced after 5 washes and do not show any antibacterial activity after 20 washes.
  • example 3.1-3.3 which is sample prepared with addition of 0.15% DDAC on fiber surface, sample shows more that 99% bacterial kill and this activity is retained after 20 wash cycles.
  • dope dyed VSF fibers were treated with 0.1% and 0.2% DDAC and then spunlaced. These fibers were then tested for antibacterial activity as per ISO 20743 and it was found that addition of 0.1%-0.2% DDAC (EX-4.1 & EX-4.2) on fiber surface, sample pass the test but fiber without DDAC (C.E.-4) fail the test criteria as per ISO 20743.
  • Swatches of test and control specimens are inoculated with the organisms ( S. Aureus: 1.5 ⁇ 108 Cfu/ml and K. Pneumoniae: 1.5 ⁇ 108 Cfu/ml). After inoculation, the specimens are incubated for 18 hours. After incubation, the bacteria are eluted from the specimen swatches by shaking in known amounts of neutralizing solution.
  • A the number of bacteria recovered from the inoculated test specimen swatches incubated
  • C the number of bacteria recovered from the inoculated control specimen swatches Immediately after inoculation.
  • An antibacterial regenerated cellulosic fiber comprising a quaternary ammonium compound in a concentration range of 0.05-1% w/w on the regenerated cellulosic fiber is disclosed.
  • Such antibacterial regenerated cellulosic fiber(s) has an antibacterial activity of more than 99% after at least 20 wash cycles.
  • Such antibacterial regenerated cellulosic fiber(s) retain antibacterial activity during downstream processing.
  • Such antibacterial regenerated cellulosic fiber(s) is antibacterial viscose staple fiber, antibacterial modal fiber or antibacterial lyocell fiber.
  • Such antibacterial regenerated cellulosic fiber(s) is used for making woven, non-woven fabrics, fiber blends and fiber composites.
  • a process for preparing antibacterial regenerated cellulosic fibers comprises spinning a cellulosic solution through spinneret into a regeneration bath to obtain regenerated cellulosic fibers; washing the regenerated cellulosic fibers; treating the regenerated cellulosic fibers with a solution of quaternary ammonium compound having a concentration range of 0.1-1.5% w/w of regenerated cellulosic fibers to obtain treated regenerated cellulosic fibers; and drying the treated regenerated cellulosic fibers to obtain antibacterial regenerated cellulosic fibers.
  • Such process(s), wherein treatment of the regenerated cellulosic fibers with the solution of quaternary ammonium compound is carried out by spraying, padding, dipping, pouring or soaking.
  • quaternary ammonium compound is selected from the group consisting of dodecyl dimethyl ammonium chloride (DDAC), C8-C18 alkyl trimethyl ammonium chlorides (such as trimethyloctylammonium chloride, decyltrimethyl ammonium chloride and hexadecyltrimethyl ammonium chloride),
  • DDAC dodecyl dimethyl ammonium chloride
  • C8-C18 alkyl trimethyl ammonium chlorides such as trimethyloctylammonium chloride, decyltrimethyl ammonium chloride and hexadecyltrimethyl ammonium chloride

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Artificial Filaments (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US16/333,887 2016-09-19 2017-09-19 Antibacterial regenerated cellulosic fibers and process of preparation thereof Abandoned US20190203409A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN201621031892 2016-09-19
IN201621031892 2016-09-19
PCT/IB2017/055645 WO2018051308A1 (fr) 2016-09-19 2017-09-19 Fibres cellulosiques antibactériennes régénérées et leur procédé de préparation

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US (1) US20190203409A1 (fr)
EP (1) EP3516106A1 (fr)
CN (1) CN109983172A (fr)
WO (1) WO2018051308A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023216556A1 (fr) * 2022-05-10 2023-11-16 Suzhou J&K Ultrafine Materials Co., Ltd. Agent de finition antibactérien hydrophile, procédé de finition antibactérienne de tissu et tissu antibactérien

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113914098A (zh) * 2020-07-07 2022-01-11 中科鼎晟科技有限公司 一种抗菌材料及其制备方法和应用

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US5569724A (en) * 1994-01-28 1996-10-29 Bayer Aktiengesellschaft N-menthylol derivatives of polycondensation products, their preparation and use
US6376696B1 (en) * 1999-06-19 2002-04-23 Clariant Gmbh Antimicrobial siloxane quat formulations and their preparation and use
US20020188028A1 (en) * 1999-09-22 2002-12-12 Johnson B. Ron Anti-infective compositions, methods and systems for treating disordered tissue
WO2003032726A1 (fr) * 2001-10-12 2003-04-24 Kimberly-Clark Worldwide, Inc. Tissus traites avec une composition antimicrobienne
US20070048356A1 (en) * 2005-08-31 2007-03-01 Schorr Phillip A Antimicrobial treatment of nonwoven materials for infection control
US20090004474A1 (en) * 2007-06-29 2009-01-01 Weyerhaeuser Co. Lyocell fibers with anti-microbial activity
US20100049148A1 (en) * 2008-08-22 2010-02-25 Oleg Siniaguine Expansion Units for Attachment to Custom Patterned Wound Dressings and Custom Patterned Wound Dressings Adapted to Interface With Same
US20110220311A1 (en) * 2010-03-15 2011-09-15 Weyerhaeuser Nr Company Reduction of the adsorption of quaternary ammonium salts onto cellulosic fibers
US20120207805A1 (en) * 2011-02-11 2012-08-16 Kimberly-Clark Worldwide, Inc. Wipe for Use with a Germicidal Solution
GB2504666A (en) * 2012-07-23 2014-02-12 Clinisupplies Ltd Garments for sufferers of eczema, atopic dermatitis or psoriasis

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CN103668520B (zh) * 2013-12-04 2016-05-25 阜宁澳洋科技有限责任公司 一种抗菌再生纤维素纤维及其制备方法
CN105133320A (zh) * 2015-09-23 2015-12-09 芜湖环瑞汽车内饰件有限公司 一种轻质抗菌吸音棉及其制备方法

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US6376696B1 (en) * 1999-06-19 2002-04-23 Clariant Gmbh Antimicrobial siloxane quat formulations and their preparation and use
US20020188028A1 (en) * 1999-09-22 2002-12-12 Johnson B. Ron Anti-infective compositions, methods and systems for treating disordered tissue
WO2003032726A1 (fr) * 2001-10-12 2003-04-24 Kimberly-Clark Worldwide, Inc. Tissus traites avec une composition antimicrobienne
US20070048356A1 (en) * 2005-08-31 2007-03-01 Schorr Phillip A Antimicrobial treatment of nonwoven materials for infection control
US20090004474A1 (en) * 2007-06-29 2009-01-01 Weyerhaeuser Co. Lyocell fibers with anti-microbial activity
US20100049148A1 (en) * 2008-08-22 2010-02-25 Oleg Siniaguine Expansion Units for Attachment to Custom Patterned Wound Dressings and Custom Patterned Wound Dressings Adapted to Interface With Same
US20110220311A1 (en) * 2010-03-15 2011-09-15 Weyerhaeuser Nr Company Reduction of the adsorption of quaternary ammonium salts onto cellulosic fibers
US20120207805A1 (en) * 2011-02-11 2012-08-16 Kimberly-Clark Worldwide, Inc. Wipe for Use with a Germicidal Solution
GB2504666A (en) * 2012-07-23 2014-02-12 Clinisupplies Ltd Garments for sufferers of eczema, atopic dermatitis or psoriasis

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023216556A1 (fr) * 2022-05-10 2023-11-16 Suzhou J&K Ultrafine Materials Co., Ltd. Agent de finition antibactérien hydrophile, procédé de finition antibactérienne de tissu et tissu antibactérien

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EP3516106A1 (fr) 2019-07-31
WO2018051308A1 (fr) 2018-03-22
CN109983172A (zh) 2019-07-05

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