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US20050246840A1 - Fiber processing agent and fiber processed with the fiber processing agent - Google Patents

Fiber processing agent and fiber processed with the fiber processing agent Download PDF

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Publication number
US20050246840A1
US20050246840A1 US10/518,541 US51854105A US2005246840A1 US 20050246840 A1 US20050246840 A1 US 20050246840A1 US 51854105 A US51854105 A US 51854105A US 2005246840 A1 US2005246840 A1 US 2005246840A1
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US
United States
Prior art keywords
fiber
processing agent
group
fiber processing
component
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.)
Abandoned
Application number
US10/518,541
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English (en)
Inventor
Masahiro Sano
Tomoyuki Kanemitsu
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.)
Idemitsu Technofine Co Ltd
Original Assignee
Idemitsu Technofine Co Ltd
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 Idemitsu Technofine Co Ltd filed Critical Idemitsu Technofine Co Ltd
Assigned to IDEMITSU TECHNOFINE CO., LTD. reassignment IDEMITSU TECHNOFINE CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KANEMITSU, TOMOYUKI, SANO, MASAHIRO
Publication of US20050246840A1 publication Critical patent/US20050246840A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • 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
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/15Proteins or derivatives thereof
    • 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
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material

Definitions

  • the present invention relates to a fiber processing agent and fiber processed with the fiber processing agent.
  • the fiber as a material for producing the products is required to have various characteristics for satisfying needs in each field of application.
  • the required characteristics include, for instance, moisture retention, water-absorbing property, moisture-absorbing property, antistatic property.
  • the fibers as described above include, but not limited to: synthetic fiber such as nylon, polyester, acryl and polyurethane; natural fibers such as cotton, linen, wool; and compound fibers prepared with the synthetic and natural fibers.
  • the fibers are subjected to processing with a specific fiber processing agent for improving the properties described above, or for adding any other specific property other than those described above.
  • the eggshell membrane has, in addition to the capability of improving the properties described above, the wound-treating property of promoting cure of a wound when applied to a surface of wounded skin, and there has been known the use of the eggshell membrane as a sheet material prepared by mixing powder of eggshell membrane in a fiber material and forming the mixture into a thin sheet so that the sheet material can easily be applied to a surface of wounded skin.
  • the sheet material prepared by the method is used only once as a disposable material, the characteristics such as the wound-treating property is provided, and thus there occurs no problem.
  • An object of the present invention is to provide a fiber processing agent having excellent durability and capable of continuously providing moisture retention property, water-absorbing property, moisture-absorbing property, antistatic property and wound-treating property, as well as fibers processed with this fiber processing agent.
  • the fiber processing agent according to the present invention is used for processing a surface of fiber, and contains soluble eggshell membrane and a reactive organic compound having a reactive group.
  • the soluble eggshell membrane indicates an eggshell membrane of a bird's egg (represented by a hen's egg) which is chemically-processed with an agent such as an acid, an alkali, an oxidizing agent, or a reducing agent into the water-soluble state.
  • an agent such as an acid, an alkali, an oxidizing agent, or a reducing agent into the water-soluble state.
  • eggs of goose, quail, ostrich, and the like may be used as materials for the eggshell membrane according to the present invention.
  • Representative reducing agents which may be used in the chemical processing according to the preset invention include thioglycolic acid, thiopropionic acid, and 2-melcaptoethanole.
  • an aqueous solution of the soluble eggshell membrane is prepared, and then any method may be used for preparing the fiber processing agent.
  • any method may be used for preparing the fiber processing agent.
  • 10 to 32 weight portions of the aqueous solution of thioglycolic acid (14.3 mol with the concentration of 100% in the liquid phase) or thiopropionic acid (11.3 mol with the concentration of 100% in the liquid phase), or a mixture thereof with the concentration of 1 mol/litter or more is added to one weight portion of the eggshell membrane.
  • the mixture solution is heated to a temperature in the range from 50 to 70° C., and is kept under the temperature for five to several tens hours until the eggshell membrane is completely dissolved. Then the reducing agent used in the reaction is removed to obtain an aqueous solution.
  • acetone is added to the solution above to precipitate the eggshell membrane having been processed into the soluble state and dissolved therein, the solution (reducing agent) is removed, and then the precipitate is washed with acetone once or twice, and then water is added to the precipitate to obtain an aqueous solution.
  • the reducing agent solution with the eggshell membrane dissolved therein is processed into the acidic state with hydrochloric acid for preventing oxidization, and then the solution is dialyzed through water to remove the reducing agent.
  • the pH is adjusted to the alkaline side in the range from about 9 to 10 for strengthening the reducing capability, and is heated for five to several tens hours at a temperature in the range from 50 to 70° C.
  • the processing is terminated within a prespecified period of time, and then impurities are removed by centrifugation, and the remaining solution is dialyzed through water, or the dissolved eggshell membrane is precipitated with acetone, and the precipitated eggshell membrane is dissolved, for instance, in water to obtain an aqueous solution of soluble eggshell membrane.
  • the soluble eggshell membrane is prepared by dissolving the eggshell membrane with alkali, an aqueous solution of 1 to N (specified value) sodium hydroxide or that further containing alcohol (with the alcohol density of 50 to 70%) is added to one weight portion of eggshell membrane, the mixture solution is heated for 3 to 6 hours at a temperature in the range from 40 to 60° C., and then is dialyzed through water for neutralization.
  • 1 to N specified value
  • alcohol with the soluble eggshell membrane is prepared by dissolving the eggshell membrane with alkali, an aqueous solution of 1 to N (specified value) sodium hydroxide or that further containing alcohol (with the alcohol density of 50 to 70%) is added to one weight portion of eggshell membrane, the mixture solution is heated for 3 to 6 hours at a temperature in the range from 40 to 60° C., and then is dialyzed through water for neutralization.
  • the reactive organic agent preferably contains one or more selected from the group consisting of (component 1) a hydrophilic compound having a polymerizable vinyl group in the molecule, (component 2) a monomer containing any of a hydroxyl group, a carboxylic group, an amino group, a sulfonic group, and a phosphate group, (component 3) a hydrophilic compound having an epoxy group, and (component 4) a compound having an aziridine group.
  • component 1 a hydrophilic compound having a polymerizable vinyl group in the molecule
  • component 2 a monomer containing any of a hydroxyl group, a carboxylic group, an amino group, a sulfonic group, and a phosphate group
  • component 3 a hydrophilic compound having an epoxy group
  • component 4 a compound having an aziridine group.
  • the (component 1) above is any of polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, bisphenol A polyethylene glycol diacrylate, bisphenol A polyethylene glycol dimethacrylate, bisphenol S polyethylene glycol dimethacrylate, and the like.
  • the (component 2) is any of acrylic acid, methacrylic acid, maleic acid, itaconic acid, acrylamide, metahcrylamide, vinyl sulfonic acid, hydroxylpropyl methacrylate, and the like.
  • the (component 3) is polyethylene glycoldiglycidyl ether or the like.
  • the (component 4) is, for instance, a compound having the following formula:
  • the aqueous solution of soluble eggshell membrane described above and the reactive organic compound are mixed with each other to prepare the fiber processing agent.
  • soluble eggshell membrane and the reactive organic compound such materials as fibroin, sericin, and chitosan may be blended therein.
  • the material or materials are blended therein, the moisture-absorbing property is improved.
  • the present invention because a reactive organic compound having a reactive group is contained therein, even when the fiber processed with the agent is used for a long period of time, the eggshell membrane is never removed. Therefore, the various properties of the eggshell membrane are maintained, so that a fiber processing agent with excellent durability and also continuously providing the moisture retention property, water-absorbing property, moisture-absorbing property, antistatic property, and wound-treating property can be obtained.
  • the soluble eggshell membrane is contained in the range from 0.1 to 10% by weight relative to the total weight of the fiber processing agent and the reactive organic compound in the range from 1 to 20% by weight. More preferably, the soluble eggshell membrane is contained in the range from 0.2 to 5% by weight and the reactive organic compound in the range from 2 to 10% by weight.
  • the concentration of the soluble eggshell membrane is less than 0.1% by weight and that of the reactive organic compound is less than 1% by weight, effects of the moisture retention property and the like are insufficient.
  • the concentration of the soluble eggshell membrane is more than 10% by weight and that of the reactive organic compound is more than 20% by weight, the fiber processed with the agent may become stiff.
  • the fiber processing agent according to the present invention may have also the composition as described below.
  • the fiber processing agent according to the present invention is used for processing a surface of fiber, and contains a soluble eggshell membrane and an organic compound having the adhesiveness.
  • the soluble eggshell membrane is described as that contained in the fiber processing agent according to the present invention above, so that description thereof is omitted herefrom.
  • a reactive organic compound having a reactive group may be used as the organic compound having the adhesiveness described above.
  • the fiber processing agent according to the present invention preferably contains one or more selected from the group consisting of (component 1) a hydrophilic compound having a polymerizable vinyl group in the molecule, (component 2) a monomer containing any of a hydroxyl group, a carboxylic group, an amino group, a sulfonic group, and a phosphate group, (component 3) a hydrophilic compound having an epoxy group, (component 4) a compound having an aziridine group, and (component 5) a compound having an isocyanate group or a precursor thereof.
  • component 1 a hydrophilic compound having a polymerizable vinyl group in the molecule
  • component 2 a monomer containing any of a hydroxyl group, a carboxylic group, an amino group, a sulfonic group, and a phosphate group
  • component 3 a hydrophilic compound having an epoxy group
  • component 4) a compound having an aziridine group
  • component 5) a compound having an is
  • Examples of the (component 1) to (component 4) contained in the reactive organic compound are the same as the (component 1) to (component 4) described as those contained in the fiber processing agent according to the present invention above, so that descriptions thereof are omitted herefrom.
  • Examples of the (component 5) containing an isocyanate group are, for instance, hexamethylene diisocyanate and 1,3,5-trisocyanate-n-pentane expressed by the chemical formulas (1) and (ii) respectively:
  • Examples of the (component 5) containing a precursor of an isocyanate group are, for instance, a precursor of hexamethylene diisocyanate and a precursor of 1,3,5-triisocyanate-n-pentane.
  • the precursor of hexamethylene diisocyanate are, for instance, 1, 6-di(methylcarbamoyl)-n-hexane and 1,6,-di(phenylcarbamoyl)-n-hexane expressed by the chemical formulas (iii) and (iv) respectively.
  • the precursor of 1,3,5-trisocyanate-n-pentane is, for instance, the compound expressed by the chemical formula (v) below:
  • any of lipophilic compounds such as wax or silicone and/or high molecular compounds such as ether, acryl, urethane, and those having an amide or ester group and the like may be used.
  • the organic compounds having the adhesiveness are those not reactive but having an appropriate degree of lipophilicity or hydrophilicity and adhere to a surface of fiber, and are used as a softening agent, a smoothing agent, an antistatic agent and the like. More specifically, the lipophilic compounds are, for instance, wax, silicone, neutral fat, mineral oil, and animal wax.
  • the high molecule compounds are, for instance, polyethylene glycol (di)alkylate, polyvalent alcohol ester, polyalkyl amide, polyacrylate.
  • the lipophilic compounds and/or high molecular compounds adhere to a surface of fiber, and elution of the eggshell membrane protein contained in the fiber to outside of the fiber can be prevented. Because of the characteristics, removal of the eggshell membrane can be prevented even when the fiber having been subjected to processing with the agent is used for a long period of time.
  • the fiber according to the present invention is characterized that the fiber is subjected to the fiber processing agent according to the present invention.
  • the fibers which can be processed with the fiber processing agent according to the present invention, are, for instance, synthetic fibers such as nylon, polyester, acryl, and polyurethane; natural fibers such as cotton, linen, and wool; and compound fibers thereof.
  • the immersing method includes, for instance, the room-temperature static method, and heating and agitating method.
  • the padding method includes, for instance, the pad dry method, and pad steam method. Any methods listed above may be employed in a case of the reactive organic compound. In a case of a not-reactive compound, it is preferable to employ the pad dry method.
  • the fibers are subjected to processing with the fiber processing agent, the fibers have excellent durability and can continuously show the moisture retention property, water-absorbing property, moisture-absorbing property, antistatic property, and wound-treating property.
  • an aqueous solution of the soluble eggshell membranes was prepared. Hen's eggs each with a shell was broken to remove the egg mixture, and the obtained eggshells each with an eggshell membrane were put in clear water to manually remove the eggshell, and then the eggshell membrane were immersed for one hour in a 1% hydrochloric acid aqueous solution to dissolve fine eggshell pieces deposited on the eggshell membranes, and then the eggshell membranes were washed with water and naturally dried to obtain the eggshell membranes.
  • the aqueous solution with eggshell membranes dissolved therein was dialyzed through water acidified with hydrochloric acid to remove thioglycolic acid, thus the aqueous solution of the soluble eggshell membranes being obtained.
  • the fiber processing agent prepared as described above was impregnated in the taffeta cloth containing 100% polyester (with the apparent specific gravity of 120 g/m 2 ), and the cloth was wrung with a mangle to the agent content of 70%. Then the cloth was heated with steam for 10 minutes at a temperature of 105° C., and then washed with hot water (for 10 minutes at a temperature of 40° C.), dried and thermally set.
  • the taffeta cloth obtained according to the same procedure as that in Example 1 was washed with an automatic washing machine 10 times, and in each washing cycle the cloth was washed once and rinsed twice for 15 minutes.
  • the aqueous solution of soluble eggshell membrane was blended with the Light Silicone PS-1000 (produced by KOEISHA CHEMCIAL Co. Ltd.) which is an organic compound with the adhesiveness to prepare the fiber processing agent according to a second aspect of the present invention.
  • the aqueous solution of soluble eggshell membrane used for preparing the fiber processing agent was prepared according to the same procedure as that described in Example 1. Solid phase of the soluble eggshell membrane 10.0% by weight Light Silicone PS-1000 10.0% by weight Water 80.0% by weight
  • the fiber processing agent prepared as described above was impregnated in the taffeta cloth containing 100% polyester (with the apparent specific gravity of 120 g/m 2 ), and the cloth was wrung with a mangle to the agent content of 70%. Then the cloth was dried within a hot air drier for 5 minutes at a temperature of 150° C., and then washed with an automatic washing machine in the same way as that employed in Example 2, namely 10 times and in each washing cycle the cloth was washed once and rinsed twice for 15 minutes.
  • the fiber processing agent employed in this comparative example was different from that employed in Example 1 only in the point that the fiber processing agent contained only the soluble eggshell membrane. Concentrations of the components of the fiber processing agent are as shown below: Solid phase of the soluble eggshell membrane 5% by weight Water 95% by weight
  • the cloth was washed 10 times like in Example 2.
  • the taffeta cloth was prepared with the fiber processing agent prepared by blending the components as shown below and according to the same procedure as that described in Example 3. Solid phase of the soluble eggshell membrane 10.0% by weight Water 90.0% by weight
  • the taffeta cloth was prepared with the fiber processing agent prepared by blending the components as shown below and according to the same procedure as that described in Reference Example 3.
  • Light Silicone PS-100 10.0% by weight Water 90.0% by weight
  • the moisture-absorbing property, a water-absorbing rate, and friction-charged electrostatic potential were measured. Further for the taffeta cloths according to the second aspect of the present invention in Example 3, Comparative Example 3, and Reference Example 1, the water-absorbing rate and friction-charged electrostatic potential were measured. Measurement of the moisture-absorbing property was performed by placing a sample of the processed taffeta cloth for 12 hours in the atmospheric air with the relative humidity of 30% at a temperature of 23° C. for moisture control and measuring a change in the weight under the atmospheric air with the relative humidity of 80% at the temperature of 30° C.
  • Example 1 The water-absorbing rate was measured by the JIS L 1096-A method. Further the friction-charged electrostatic potential was measured by the JIS L 1094-B method. A result of the assessment is shown in Table 1. TABLE 1 Moisture Friction-charged Absorbing Water Absorbing electrostatic property rate potential [V] Example 1 2.1 1 sec. or below 200 Example 2 2.0 1 sec. or below 400 Com. Example 1 0.1 No absorption in 5 4800 minutes or more Com. Example 2 0.2 No absorption in 5 4500 minutes or more Example 3 — 1 to 5 sec 1400 Com. Example 3 — No absorption in 5 4200 minutes or more Ref. Example 1 — 2 to 5 minutes 2800
  • Example 1 From the result of the Assessment Method 1 above, it is understood that the moisture-absorbing property and water-absorbing rate in Example 1 are higher as compared to those in Comparative Example 1 and the friction-charged electrostatic potential in Example 1 is smaller as compared to that in Comparative Example, which indicates that Example 1 is superior to Comparative Example 1 in all aspects. From this result, it is understood that the fiber processed with the fiber processing agent according to the present invention (containing a reactive organic compound) was improved in the water-absorbing property, moisture-absorbing property, and antistatic property.
  • Example 2 shows the higher moisture-absorbing property and water-absorbing rate and smaller friction-charged electrostatic potential as compared to Comparative Example 2, which suggests that Example 2 is superior to Comparative Example 2 in all aspects. Therefore it is understood that the fiber processed with the fiber processing agent according to the present invention (containing a reactive organic compound) does not lose the effects provided by the fiber processing agent even after washed repeatedly and has excellent durability.
  • the moisture-absorbing property is 20%
  • the water-absorbing rate is not more than one second
  • the friction-charged electrostatic potential is 500 V in the initial state before washing. Comparison of the initial state to the state after washing suggests that the fiber processing agent containing only the soluble eggshell membrane like that in the conventional technology does not improve the durability.
  • Example 3 shows the higher water-absorbing rate and smaller friction-charged electrostatic potential as compared to Comparative Example 3, and that Example 3 is superior to Comparative Example 3 in all aspects. Also comparison of Example 3 to Reference Example 1 suggests the same conclusion. For the reasons as described above, it is understood that the fiber processed with the fiber processing agent according to the present invention (containing an organic compound having the adhesiveness) is improved in the water-absorbing property and the antistatic property.
  • Example 1 From a result of assessment according to the Assessment Method 2, it is understood that the conductance in Example 1 is larger as compared to that in Comparative Example 1. A larger value of this conductance indicates improved conductivity of human skin, which indicates that the roughed skin is being cured and the moisture retention of the skin is being improved.
  • the present invention provides a fiber processing agent capable of improving the various properties such as moisture retention, water-absorbing property, moisture-absorbing property, and antistatic property, and also provides fibers and fiber products improved in the properties as described above.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US10/518,541 2002-07-05 2003-07-07 Fiber processing agent and fiber processed with the fiber processing agent Abandoned US20050246840A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002196880 2002-07-05
JP2002-196880 2002-07-05
PCT/JP2003/008591 WO2004005607A1 (ja) 2002-07-05 2003-07-07 繊維処理剤およびこの繊維処理剤により処理された繊維

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US20050246840A1 true US20050246840A1 (en) 2005-11-10

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US (1) US20050246840A1 (ja)
EP (1) EP1541748A4 (ja)
CN (1) CN100402735C (ja)
AU (1) AU2003281313A1 (ja)
WO (1) WO2004005607A1 (ja)

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US20090031691A1 (en) * 2007-07-30 2009-02-05 Takeharu Tajima Fiber, fiber assembly, and fiber producing method
US10932952B2 (en) 2015-11-11 2021-03-02 Biovotec As Dry biocompatible disintegratable films for delivering particulate egg shell membrane to a wound
US11045578B2 (en) 2015-06-24 2021-06-29 Biovotec As Tissue engineering scaffolds comprising particulate egg shell membrane
US11992508B2 (en) 2014-10-28 2024-05-28 Biovotec As Micronized eggshell membrane particles and the use thereof to promote the healing of wounds

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JP4387806B2 (ja) * 2004-01-07 2009-12-24 出光テクノファイン株式会社 繊維処理液、改質繊維布帛およびその製造方法
CN101487189B (zh) * 2008-11-03 2011-02-16 浙江理工大学 一种脆弱丝绸的蚕丝蛋白加固方法
WO2011019738A1 (en) 2009-08-10 2011-02-17 Galenea Corporation Compounds and methods of use thereof
CN102352562A (zh) * 2011-07-29 2012-02-15 苏州卡奇特纺织有限公司 一种毛晴织物用抗静电剂
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JP2013129938A (ja) * 2011-12-21 2013-07-04 Komatsu Seiren Co Ltd 機能性繊維布帛及びその製造方法
CN102766939A (zh) * 2012-06-27 2012-11-07 吴江亚太化纺有限公司 一种聚酰胺66bcf地毯丝
CN103726323A (zh) * 2012-10-16 2014-04-16 东丽纤维研究所(中国)有限公司 一种耐久抗静电涤纶纺织品
CN105544213B (zh) * 2016-01-21 2018-05-15 苏州印丝特纺织数码科技有限公司 一种鸡蛋壳改性的聚丙烯浆料及其制备方法
CN116926952B (zh) * 2023-07-04 2025-06-03 江南大学 浸渍蛋壳膜的柔性棉织物基压电传感器制备方法及其应用

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US20090031691A1 (en) * 2007-07-30 2009-02-05 Takeharu Tajima Fiber, fiber assembly, and fiber producing method
US7767297B2 (en) * 2007-07-30 2010-08-03 Idemitsu Technofine Co., Ltd. Fiber, fiber assembly, and fiber producing method
US11992508B2 (en) 2014-10-28 2024-05-28 Biovotec As Micronized eggshell membrane particles and the use thereof to promote the healing of wounds
US12390495B2 (en) 2014-10-28 2025-08-19 Biovotec As Micronized eggshell membrane particles and the use thereof to promote the healing of wounds
US11045578B2 (en) 2015-06-24 2021-06-29 Biovotec As Tissue engineering scaffolds comprising particulate egg shell membrane
US10932952B2 (en) 2015-11-11 2021-03-02 Biovotec As Dry biocompatible disintegratable films for delivering particulate egg shell membrane to a wound

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CN1665979A (zh) 2005-09-07
EP1541748A4 (en) 2008-02-20
WO2004005607A1 (ja) 2004-01-15
AU2003281313A1 (en) 2004-01-23
CN100402735C (zh) 2008-07-16

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