WO2018062791A1 - 폴리케톤 소재 칫솔모와 이를 포함하는 칫솔 - Google Patents

폴리케톤 소재 칫솔모와 이를 포함하는 칫솔 Download PDF

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Publication number
WO2018062791A1
WO2018062791A1 PCT/KR2017/010558 KR2017010558W WO2018062791A1 WO 2018062791 A1 WO2018062791 A1 WO 2018062791A1 KR 2017010558 W KR2017010558 W KR 2017010558W WO 2018062791 A1 WO2018062791 A1 WO 2018062791A1
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WO
WIPO (PCT)
Prior art keywords
bristles
polyketone
bristle
toothbrush
salt
Prior art date
Application number
PCT/KR2017/010558
Other languages
English (en)
French (fr)
Korean (ko)
Inventor
박미정
하원호
이경섭
이종훈
유혜주
Original Assignee
주식회사 엘지생활건강
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.)
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Publication date
Application filed by 주식회사 엘지생활건강 filed Critical 주식회사 엘지생활건강
Priority to CN201780057212.5A priority Critical patent/CN109715009A/zh
Priority to EP17856677.4A priority patent/EP3520651B1/en
Priority to CN202311459770.8A priority patent/CN117223964A/zh
Priority to JP2019513742A priority patent/JP7199667B2/ja
Priority to US16/333,331 priority patent/US20190208901A1/en
Publication of WO2018062791A1 publication Critical patent/WO2018062791A1/ko

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Classifications

    • A—HUMAN NECESSITIES
    • A46—BRUSHWARE
    • A46D—MANUFACTURE OF BRUSHES
    • A46D1/00—Bristles; Selection of materials for bristles
    • A46D1/02—Bristles details
    • A46D1/0207—Bristles characterised by the choice of material, e.g. metal
    • A—HUMAN NECESSITIES
    • A46—BRUSHWARE
    • A46B—BRUSHES
    • A46B9/00—Arrangements of the bristles in the brush body
    • A46B9/02—Position or arrangement of bristles in relation to surface of the brush body, e.g. inclined, in rows, in groups
    • A46B9/04—Arranged like in or for toothbrushes
    • A—HUMAN NECESSITIES
    • A46—BRUSHWARE
    • A46D—MANUFACTURE OF BRUSHES
    • A46D1/00—Bristles; Selection of materials for bristles
    • A—HUMAN NECESSITIES
    • A46—BRUSHWARE
    • A46D—MANUFACTURE OF BRUSHES
    • A46D1/00—Bristles; Selection of materials for bristles
    • A46D1/02—Bristles details
    • A46D1/0276—Bristles having pointed ends
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/26—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from other polymers
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/30—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising olefins as the major constituent
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/96—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from other synthetic polymers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating 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 oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/123—Polyaldehydes; Polyketones
    • A—HUMAN NECESSITIES
    • A46—BRUSHWARE
    • A46B—BRUSHES
    • A46B2200/00—Brushes characterized by their functions, uses or applications
    • A46B2200/10—For human or animal care
    • A46B2200/1066—Toothbrush for cleaning the teeth or dentures
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2321/00—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D10B2321/02—Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds polyolefins
    • D—TEXTILES; PAPER
    • D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2331/00—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products
    • D10B2331/06—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyethers
    • D10B2331/061—Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyethers polyetherketones, polyetheretherketones, e.g. PEEK
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber

Definitions

  • the present invention relates to a polyketone bristle and a toothbrush comprising the same.
  • the present invention provides a bristle and a toothbrush including the bristles having reduced bridging properties and increased service life by producing bristles of a polyketone material having high rigidity, high elasticity and wear resistance.
  • Toothbrush is a tool used to clean the oral cavity including teeth and gums, and consists of a bag and bristles, among which the bristles are usually manufactured by using a synthetic resin having elasticity.
  • General bristles have been mainly made of nylon or polyester-based polymers (eg, polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT)).
  • PET polyethylene terephthalate
  • PTT polytrimethylene terephthalate
  • PBT polybutylene terephthalate
  • Nylon has the advantage of moderate flexibility, but the water absorption is short, the life is short, the strength is weak to have a thickness of a certain size or more, polyester-based bristle has the disadvantage of low flexibility.
  • Such conventional bristles have to be replaced with bristles when the bristles are shortened to 1 month and 3 months long.
  • the fine bristles made of polyester-based polymers such as PBT show a phenomenon that the bristles are getting thinner and wear faster because the tips of the bristles become thinner, which causes inconvenience of frequently replacing the toothbrush.
  • the present inventors have studied to solve the problem of the opening of the existing nylon and polyester-based bristles (PBT, etc.), and the problem of the bristles becoming faster and worn out due to the thin bristles, especially in the case of the bristles having thinner bristles.
  • the present invention has been completed by producing a bristle having excellent rigidity, high elasticity and wear resistance using a polyketone material.
  • an object of the present invention is to provide bristles including polyketone.
  • Another object of the present invention to provide a toothbrush comprising the bristles.
  • One aspect of the present invention is to provide bristles comprising polyketone.
  • the bristles are the ultimate goal of maximizing the cleaning power of the teeth while minimizing the damage to the gums.
  • the inventors of the present invention have found a surprising fact that when the polyketone resin is used in the bristles, the plaque is excellently removed due to its high strength and high elasticity, and at the same time there is little gum irritation.
  • Polyketone resin is a new resin developed in recent years, synthesized from carbon monoxide and olefins, the mechanical properties fall into the category of high performance plastics.
  • U.S. Patent No. 4,843,144 introduces linear alternating polymers synthesized from olefins such as ethylene and propylene and carbon monoxide.
  • the polyketone resin used in this patent has excellent impact resistance, high resilience at both room temperature and low temperature, and has excellent creep characteristics.
  • the polyketone may be one having a basic structure containing carbon monoxide and olefins.
  • the polyketone may be a hybrid polymer of carbon monoxide and ethylene or a terpolymer of carbon monoxide, ethylene and propylene.
  • polyketone component may be represented by the following formula:
  • x: y is 1:10 to 10: 1.
  • the polyketone polymer used for the bristles in the present invention may be a linear alternating structure, and may substantially include carbon monoxide per molecule of unsaturated hydrocarbons.
  • the ethylenically unsaturated hydrocarbon compound which can be used as a precursor of the polyketone polymer may have 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms. Even more preferably, the ethylenically unsaturated hydrocarbon compound is an ethene or ⁇ -olefin (eg propene, 1-butene, iso-butene, 1-hexene, 1-octene).
  • the polyketone resin may be prepared by a method of liquid-polymerizing carbon monoxide and olefin using an alcohol solvent in the presence of a catalyst composition containing a palladium compound.
  • a catalyst composition containing a palladium compound in the presence of a catalyst composition containing a palladium compound.
  • the polymer is recovered through polymerization and filtration and purification, and the remaining catalyst composition is removed with a solvent such as alcohol or acetone.
  • the bristles may be made of a polyketone material.
  • the bristles further comprise at least one water-insoluble polymeric material selected from the group consisting of polypropylene, polyethylene, polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyurethane and nylon components. It may be.
  • the bristles of the present invention may include a linear alternating polymer consisting of carbon monoxide and at least one ethylene unsaturated hydrocarbon and a polyketone blend prepared by blending one or more of the above water-insoluble high molecular materials. .
  • the water-insoluble polymer material is a material used when manufacturing the general bristles, of which nylon has excellent heat resistance, elastic modulus, and strength, but has a disadvantage of physical property change and dimensional change due to high water absorption.
  • nylon has excellent heat resistance, elastic modulus, and strength
  • a disadvantage of physical property change and dimensional change due to high water absorption there is a disadvantage in that the impact resistance change problem occurs when the moisture absorption, it is also possible to use a material of the bristle of the present invention by blending polyketone and nylon as a way to improve this.
  • polyketone blend it is possible to include 60 to 80% by weight of linear alternating polyketone polymer and 20 to 40% by weight of the at least one water insoluble polymer material.
  • the polyketone and at least one water insoluble polymer material may be mixed in a weight ratio of 9: 1 to 7: 3.
  • Polyketone blends can be prepared by melting each component at high temperature and then compounding, whereby it is also possible to mix antioxidants, UV stabilizers and other additional ingredients.
  • the bristle is an anti-inflammatory antibacterial agent, whitening agent, anti-irritant, tartar deterrent, flavoring agent, bad breath remover, gum health agent, tooth decay prevention agent, mouthwash, xylitol, bamboo salt, sun salt, preparation salt, tablet salt, pine salt It may further include a component useful for dental health selected from the group consisting of suicide, molten salt, processed salt and phosphate.
  • the toothbrush and the moisture during the brushing release the ingredients useful for dental health, and these ingredients act on the teeth or gums to prevent antibacterial, anti-inflammatory, anti-inflammatory and tartar
  • the vaccine will help prevent oral diseases.
  • the bristles of the present invention may be produced in the form of micro-hairs.
  • the polyketone fine bristle of the present invention has excellent wear resistance to high rigidity and high elasticity, the polyketone fine bristle has the advantage of being used while maintaining the initial state for the period of use.
  • the bristles are the same as the diameter of the bristle and the tip diameter, the tip is round round general hair form, or may be a needle-like fine hair form of tapered tapered width.
  • the diameter of the bristles may be 0.1 mm to 0.13 mm, and in the case of the micro hair form, the tip diameter may be ultra-fine hair having 0.02 mm or less or 0.01 mm or less.
  • the bristles of the bristles having a diameter of 0.1 mm to 0.13 mm have bristles more than three times more bristles than the general bristles having a diameter of 0.16 to 0.20 mm.
  • the gum massage effect is good, it can be a combination of two functions that can not be performed with a regular toothbrush and gum massage.
  • the fine bristles having a diameter of the bristle tip of 0.02 mm or less are thinner than the general gap between the teeth and the gums, so that the plaque between the teeth and the gums is easy to be cleaned and the gingivitis is prevented.
  • the bristles of the present invention may be prepared using a method of planting in fine "V" shape on the toothbrush head after pre-preparation of finer fine hairs having both ends.
  • the bristles to be planted may be 5 mm to 25 mm in length from the top of the head to the end of the bristles after being planted, but is not necessarily limited thereto.
  • the fine hair to be planted may have a total length of 10 to 30 mm or 15 to 25 mm, a thickness of 0.01 mm to 0.1 mm, a length of the hair transplanting part may be 1 mm to 15 mm, and after the planting, fine hair from the top of the toothbrush surface May have a height of 5 mm to 20 mm, but is not necessarily limited thereto.
  • the bristles prepared by using the polyketone of the present invention have excellent elasticity and are suitable for removing the plaque of the curved tooth surface, thereby effectively removing the plaque between the tooth surface and the interdental teeth, which were not easily removed with the existing toothbrushes.
  • Another aspect of the invention is to provide a toothbrush comprising the polyketone bristles described above.
  • the toothbrush of the present invention may be made of a product having a physical cleaning and gum massage effect upon brushing by making an elastic member such as rubber, silicone, and the like on a polyketone bristle.
  • the toothbrush of the present invention comprises a handle portion having a predetermined thickness and width and a toothbrush head portion connected thereto; Polyketone bristles formed on an upper surface of the toothbrush head; And it may be manufactured in the form having a tip provided on the toothbrush head.
  • the toothbrush of the present invention may be manufactured in the form of two or more bristles each made of a different material.
  • the toothbrush of the present invention comprises a handle portion having a predetermined thickness and width and a toothbrush head portion connected thereto; A first bristle is fixed to a portion of the head portion and a second bristle is fixed to another portion of the head portion, wherein the first bristle is made of a polyketone material, the second bristle is polypropylene, polyethylene, polyethylene tere It may be made of at least one water-insoluble polymer material selected from the group consisting of phthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyurethane and nylon components.
  • the bristle of the new material according to the present invention is high rigidity compared to the conventional bristle, excellent elasticity, more helpful for cleaning teeth, excellent wear resistance and can be used for a long time. It also has the advantage of being able to be used while maintaining its original state due to its reduced flakyness.
  • Figure 1 shows the result of measuring the interdental plaque removal rate by the bristle diameter.
  • Figure 2 is a photograph taken of each of the polyketone and nylon bristles immediately after brushing.
  • Resin powder made of bristles, made of nylon 612 (Dupont, Tynex), polybutylene terephthalate (PBT) (KOLON) or polyketone (Hyosung, M310U and M310U-like grades), respectively, and molded at the nozzle of the extrusion device. Extruded, cooled and dried by hot air to prepare bristles having a diameter of 0.18 mm in each material.
  • tensile strength which is the breaking force of the bristles to evaluate the rigidity of all the strands, was measured, and compared with the conventional bristle materials Nylon 612 and PBT.
  • both ends of the bristles were fixed with a fixing mechanism, and then pulled in the axial direction of the specimen to measure the force and tensile strength until failure.
  • polyketone bristles were planted in the toothbrush bar and manufactured with a toothbrush, and the elasticity loss degree of the toothbrush with nylon 612 and PBT bristles was compared.
  • Elasticity loss is to evaluate the durability (morphism) when using the toothbrush, and the degree of the gap after performing 5000 times of reciprocating brushing each 5000 times with a brush machine was measured in the same manner as in Equation 1. The smaller the value of elasticity loss, the smaller the gap between the before and after brushig.
  • tensile strength showed that polyketone bristles were 2.0 times higher than nylon and 1.13 times higher than PBT (Table 1), and it was confirmed that high rigidity properties were maintained even when manufactured with bristles.
  • toothbrushes with polyketone bristles showed 34% and 27% less elastic loss than nylon 612 and PBT at 5000 round trips, respectively, compared with 34% and 27% more polyketone compared to nylon 612 and PBT, respectively. That means it's done less well. Similarly, 10,000 round trips resulted in less than 31% and 12% less polyketones than nylon 612 and PBT, respectively.
  • Polymers with high stiffness and good abrasion resistance like polyketone include fluorine resins (PTFE, PVDF), POM, PBT, PES, etc.But fluorine resins are difficult to produce bristles due to their high melting point. Due to one property, bristles were not suitable.
  • PBT and PES are high strength materials such as polyketone and have excellent abrasion resistance. The material was used to produce bristles having a diameter of 0.18 mm in the same manner as in the manufacturing example above. It was planted without going through a toothbrush. Afterwards, panel evaluation was conducted through a questionnaire survey on the degree of gum irritation by professional panel with three toothbrushes.
  • the survey asked 20 women and 20 men in their 20s and 40s to use and compare experimental toothbrushes for 7 days each. Prior to using the new toothbrushes, they had a three-day rest period in between, and the teeth were taken care of as usual. The survey results are shown in Table 2 below (duplicate selections available).
  • Experimental toothbrushes were prepared by implanting nylon bristles and polyketone bristles with diameters of 5 M (0.127 mm) into 32 identical toothbrushes each having a diameter of 1.6 mm.
  • the toothbrushes were used for 20 women in their 20s and 40s and 20 men for 7 days. Prior to using the new toothbrushes, they had a three-day rest period in between, and the teeth were taken care of as usual.
  • the questionnaire consisted of questions to evaluate the elasticity and cleaning power of the toothbrush, and each of them was evaluated on a 5-point scale (higher satisfaction).
  • Toothbrushes with thin bristles have better interdental cleaning power, but bristles with thinner diameters, especially nylon bristles, which are most conventionally applied, have brittle brittleness, elasticity, and easy opening.
  • the surface of the artificial membrane was coated for 10 seconds in the colored polymer of the vertebral tooth, and then taken out and dried for 60 minutes in a constant temperature and humidity room (25 degrees, 55%) where the temperature and humidity were kept for a certain thickness. It was used after. Toothbrushes of 10 mils, 8 mils, 7 mils, and 6 mils in diameter were implanted so that the bristle section of the toothbrush and the buccal surface of the coated vertebrae were horizontally positioned to cover as much as possible during brushing stroke. 300 g of pressure was applied to all toothbrushes, and each product was carried out eight times with 30 sec of vertical stroke and 30 sec of horizontal stroke. After that, after measuring the area before and after the removal of the artificial membrane through the microscope, the plaque removal rate was evaluated as a percentage (%), and the results are shown in FIG. 1.
  • the width of the brush after measuring 5,000 round trips was measured on the toothbrush Brushing evaluator, and the shape of each of the polyketone and nylon bristles immediately after brushing was photographed.
  • the force was measured by applying a third point of the bristles to a wire capable of measuring the force.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Brushes (AREA)
  • Artificial Filaments (AREA)
PCT/KR2017/010558 2016-09-29 2017-09-25 폴리케톤 소재 칫솔모와 이를 포함하는 칫솔 WO2018062791A1 (ko)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201780057212.5A CN109715009A (zh) 2016-09-29 2017-09-25 聚酮材质的牙刷毛及包括该牙刷毛的牙刷
EP17856677.4A EP3520651B1 (en) 2016-09-29 2017-09-25 Toothbrush bristles made of polyketone material, and toothbrush including same
CN202311459770.8A CN117223964A (zh) 2016-09-29 2017-09-25 聚酮材质的牙刷毛及包括该牙刷毛的牙刷
JP2019513742A JP7199667B2 (ja) 2016-09-29 2017-09-25 ポリケトン素材歯ブラシ用毛及びそれを含む歯ブラシ
US16/333,331 US20190208901A1 (en) 2016-09-29 2017-09-25 Polyketone Bristles And Toothbrush Comprising The Bristles

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2016-0125903 2016-09-29
KR20160125903 2016-09-29
KR20170089694 2017-07-14
KR10-2017-0089694 2017-07-14

Publications (1)

Publication Number Publication Date
WO2018062791A1 true WO2018062791A1 (ko) 2018-04-05

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PCT/KR2017/010558 WO2018062791A1 (ko) 2016-09-29 2017-09-25 폴리케톤 소재 칫솔모와 이를 포함하는 칫솔

Country Status (7)

Country Link
US (1) US20190208901A1 (ja)
EP (1) EP3520651B1 (ja)
JP (1) JP7199667B2 (ja)
KR (2) KR101914177B1 (ja)
CN (2) CN117223964A (ja)
TW (1) TWI736680B (ja)
WO (1) WO2018062791A1 (ja)

Families Citing this family (2)

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Publication number Priority date Publication date Assignee Title
DE202017002839U1 (de) * 2017-05-30 2018-08-31 Perlon Nextrusion Monofil GmbH Polyketonfasern, deren Herstellung und Verwendung
KR102127595B1 (ko) * 2019-05-02 2020-06-29 조정희 친환경 섬유 원단 및 그 제조방법

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KR20110060431A (ko) * 2009-11-30 2011-06-08 김응완 항균 미백 칫솔모 및 그 제조방법
US20150017888A1 (en) * 2012-01-30 2015-01-15 Hahl Filaments GmbH Abrasive bristle, method for the manufacture thereof, brush with abrasive bristles and method for the surface treatment of a workpiece with a brush having abrasive bristles
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KR101914177B1 (ko) 2018-11-01
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JP2019530497A (ja) 2019-10-24
CN117223964A (zh) 2023-12-15
KR20180118591A (ko) 2018-10-31
EP3520651A1 (en) 2019-08-07
EP3520651B1 (en) 2024-01-10
US20190208901A1 (en) 2019-07-11
KR102308925B1 (ko) 2021-10-05
JP7199667B2 (ja) 2023-01-06
EP3520651A4 (en) 2020-04-08
CN109715009A (zh) 2019-05-03
TWI736680B (zh) 2021-08-21

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