EP3520651B1 - Toothbrush bristles made of polyketone material, and toothbrush including same - Google Patents

Toothbrush bristles made of polyketone material, and toothbrush including same Download PDF

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Publication number
EP3520651B1
EP3520651B1 EP17856677.4A EP17856677A EP3520651B1 EP 3520651 B1 EP3520651 B1 EP 3520651B1 EP 17856677 A EP17856677 A EP 17856677A EP 3520651 B1 EP3520651 B1 EP 3520651B1
Authority
EP
European Patent Office
Prior art keywords
toothbrush
bristles
polyketone
toothbrush bristles
salt
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.)
Active
Application number
EP17856677.4A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP3520651A1 (en
EP3520651A4 (en
Inventor
Mi-Jeong Park
Won-Ho Ha
Kyung-Sub Lee
Jong-Hoon Lee
Hye-Ju YU
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LG H&H Co Ltd
Original Assignee
LG Household and Health Care Ltd
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Publication date
Application filed by LG Household and Health Care Ltd filed Critical LG Household and Health Care Ltd
Publication of EP3520651A1 publication Critical patent/EP3520651A1/en
Publication of EP3520651A4 publication Critical patent/EP3520651A4/en
Application granted granted Critical
Publication of EP3520651B1 publication Critical patent/EP3520651B1/en
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Classifications

    • AHUMAN NECESSITIES
    • A46BRUSHWARE
    • A46DMANUFACTURE OF BRUSHES
    • A46D1/00Bristles; Selection of materials for bristles
    • A46D1/02Bristles details
    • A46D1/0207Bristles characterised by the choice of material, e.g. metal
    • AHUMAN NECESSITIES
    • A46BRUSHWARE
    • A46BBRUSHES
    • A46B9/00Arrangements of the bristles in the brush body
    • A46B9/02Position or arrangement of bristles in relation to surface of the brush body, e.g. inclined, in rows, in groups
    • A46B9/04Arranged like in or for toothbrushes
    • AHUMAN NECESSITIES
    • A46BRUSHWARE
    • A46DMANUFACTURE OF BRUSHES
    • A46D1/00Bristles; Selection of materials for bristles
    • AHUMAN NECESSITIES
    • A46BRUSHWARE
    • A46DMANUFACTURE OF BRUSHES
    • A46D1/00Bristles; Selection of materials for bristles
    • A46D1/02Bristles details
    • A46D1/0276Bristles having pointed ends
    • 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
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/26Monocomponent 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
    • 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
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/28Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/30Monocomponent 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
    • 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
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/96Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from other synthetic polymers
    • 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
    • D06M13/10Treating 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
    • D06M13/12Aldehydes; Ketones
    • D06M13/123Polyaldehydes; Polyketones
    • AHUMAN NECESSITIES
    • A46BRUSHWARE
    • A46BBRUSHES
    • A46B2200/00Brushes characterized by their functions, uses or applications
    • A46B2200/10For human or animal care
    • A46B2200/1066Toothbrush for cleaning the teeth or dentures
    • DTEXTILES; PAPER
    • D10INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10BINDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2321/00Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D10B2321/02Fibres made from polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds polyolefins
    • DTEXTILES; PAPER
    • D10INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10BINDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
    • D10B2331/00Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products
    • D10B2331/06Fibres made from polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polycondensation products polyethers
    • D10B2331/061Fibres 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
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber

Definitions

  • the present disclosure relates to polyketone toothbrush bristles and a toothbrush including the same.
  • the present disclosure relates to toothbrush bristles of a polyketone material having high rigidity, high elasticity and excellent wear resistance and thus shows reduced bristle gap-widening and increased service life, and a toothbrush including the same.
  • a toothbrush is a tool used for cleaning an oral cavity including teeth and gingiva and includes a grip and toothbrush bristles, wherein the toothbrush bristles are generally made using an elastic synthetic resin.
  • toothbrush bristles have been made using a polyester polymer (e.g. polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), or the like).
  • PET polyethylene terephthalate
  • PTT polytrimethylene terephthalate
  • PBT polybutylene terephthalate
  • nylon has an advantage of suitable flexibility, it has high moisture absorbing property to provide a short service life, shows low strength, and thus is required to have a predetermined thickness or more.
  • polyester-based toothbrush bristles they have a disadvantage of low flexibility. Such conventional toothbrush bristles show a bristle gap-widening phenomenon even after 1 month to 3 months, and thus requires exchange.
  • the present inventors have conducted intensive studies to solve the bristle gap-widening problem of the existing nylon- and polyester (e.g. PBT)-based toothbrush bristles, particularly the problem of early bristle gap-widening and wearing caused by the thin ends of bristles in the case of fine bristles having a tapered shape.
  • PBT nylon- and polyester
  • toothbrush bristles having high rigidity, high elasticity and excellent wear resistance can be obtained by using a polyketone material.
  • the present disclosure is based on this finding.
  • the present disclosure is directed to providing toothbrush bristles including polyketone.
  • the present disclosure is also directed to providing a toothbrush including the toothbrush bristles.
  • toothbrush bristles including polyketone.
  • Toothbrush bristles are ultimately directed to maximizing a tooth-cleaning effect while minimizing damages upon the gingiva.
  • the tooth-cleaning effect is degraded.
  • the gingiva is damaged undesirably.
  • the present inventors have conducted intensive studies to solve the above-mentioned problem.
  • a polyketone resin is a novel type of resin developed recently, is synthesized from carbon monoxide and olefin, and has mechanical properties that belong to the category of high-performance plastics.
  • US Patent No. 4,843,144 discloses a linear alternate polymer synthesized from olefin, such as ethylene or propylene, with carbon monoxide.
  • the polyketone resin used therein has excellent impact resistance, high repulsion elasticity both at room temperature and low temperature and excellent creep characteristics.
  • the polyketone may have a basic structure including carbon monoxide and olefin.
  • the polyketone may be a hybrid polymer of carbon monoxide with ethylene or a terpolymer of carbon monoxide, ethylene and polyketone.
  • the polyketone ingredient is represented by the following chemical formula: wherein x:y is 1:10-10:1.
  • the polyketone polymer used for the toothbrush bristles according to the present disclosure may have a linear alternate structure, and may include carbon monoxide substantially per each unsaturated hydrocarbon molecule.
  • the ethylenic unsaturated hydrocarbon compound that may be used as a precursor of the polyketone polymer may have 1-20 carbon atoms, preferably 1-10 carbon atoms. More preferably, the ethylenic unsaturated hydrocarbon compound may be ethene or ⁇ -olefin (e.g. propene, 1-butene, isobutene, 1-hexene or 1-octene).
  • the polyketone resin may be obtained by liquid phase polymerization of carbon monoxide with olefin using an alcohol solvent in the presence of a catalyst composition including a palladium compound.
  • a catalyst composition including a palladium compound may be recovered through filtering and purification steps after the polymerization. The remaining catalyst composition is removed with a solvent, such as an alcohol or acetone.
  • the toothbrush bristles may include a polyketone material.
  • the toothbrush bristles may further include at least one water-insoluble polymer material selected from the group consisting of polypropylene, polyethylene, polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyurethane and nylon.
  • the toothbrush bristles according to the present disclosure may include a polyketone blend obtained by blending a linear alternate polymer containing carbon monoxide with at least one ethylenic unsaturated hydrocarbon and at least one water-insoluble polymer material described hereinabove.
  • the water-insoluble polymer material is one used for manufacturing conventional toothbrush bristles.
  • nylon has excellent heat resistance, elastic modulus and strength, but shows high moisture absorbability to cause a change in physical properties or dimension undesirably.
  • nylon is disadvantageous in that it undergoes a change in impact resistance when absorbing moisture. To solve this, it is possible to use a blend of nylon with polyketone as a material for the toothbrush bristles according to the present disclosure.
  • the polyketone blend may include 60-80 wt% of the linear alternate polyketone polymer and 20-40 wt% of at least one water-insoluble polymer as mentioned above.
  • polyketone and at least one water-insoluble polymer may be blended at a weight ratio of 9:1-7:3.
  • the polyketone blend may be prepared by melting each of the ingredients at high temperature, followed by compounding.
  • additional ingredients such as an antioxidant and UV stabilizer, may be further incorporated.
  • the toothbrush bristles may further include an ingredient favorable to the tooth health and selected from the group consisting of an anti-inflammatory and anti-bacterial agent, whitening agent, sensitive tooth-alleviating agent, anti-plaque agent, fragrance, bad breath-preventing agent, gingiva health-aid, tooth decay-preventing agent, oral cavity cleaner, xylitol, bamboo salt, bay salt, prepared salt, refined salt, pine salt, steamed salt, molten salt, processed salt and phosphate salt.
  • an ingredient favorable to the tooth health selected from the group consisting of an anti-inflammatory and anti-bacterial agent, whitening agent, sensitive tooth-alleviating agent, anti-plaque agent, fragrance, bad breath-preventing agent, gingiva health-aid, tooth decay-preventing agent, oral cavity cleaner, xylitol, bamboo salt, bay salt, prepared salt, refined salt, pine salt, steamed salt, molten salt, processed salt and phosphate salt.
  • toothbrush bristles further include the ingredients favorable to the tooth health as described above, such ingredients are released by tooth cleaning pressure and moisture upon tooth brushing, and act on the teeth or gingiva so that they may help effects of preventing various oral diseases, such as anti-bacterial, anti-inflammatory, anti-plaque and anti-sensitive effects.
  • toothbrush bristles according to the present disclosure may be provided in the form of fine bristles.
  • fine bristles In the case of fine bristles, they are soft and touch teeth everywhere to clean all corners of teeth, and particularly they show a high cleaning effect between teeth and the gingiva. On the contrary, in the case of general fine bristles, they are worn rapidly and end portions thereof are bent easily, and thus require exchange every 1-2 months. Therefore, it is required to conduct studies to improve the durability of toothbrush bristles, especially fine bristles.
  • the polyketone fine bristles according to the present disclosure has high rigidity, high elasticity and excellent wear resistance, and thus is advantageous in that they can be used for a period of use while maintaining the initial state.
  • the toothbrush bristles may be provided in the form of general bristles having the same diameter even at the end and round-shaped end portions, or in the form of needle-like fine bristles having tapered end portions.
  • bristles In the case of general bristles, they may have a diameter of 0.1-0.13 mm. In the case of fine bristles, they may be ultrafine bristles having a diameter of 0.02 mm or less, or 0.1 mm or less, at the end portions thereof.
  • the general bristles having a diameter of 0.1-0.13 mm may have at least three times larger number of bristles planted densely as compared to general bristles having a diameter of 0.16-0.20 mm, and thus show high elasticity and softness to provide a good cleaning effect to the gingiva and teeth and a high effect of massaging the gingiva. Thus, they can provide a tooth cleaning effect in combination with a gingiva massaging effect, which cannot be provided by general bristles.
  • fine bristles having a diameter of 0.02 mm or less at the end portions thereof they are thinner than the gap between the gingiva and teeth, and thus can clean plaque between the gingiva and teeth with ease and provide an effect of preventing gingivitis.
  • the toothbrush bristles according to the present disclosure may be obtained by forming fine bristles having a tapered shape and planting them in a toothbrush head in a 'V'-like shape.
  • the toothbrush bristles may be planted so that the length of planted bristles, which is the distance from the head top surface to the ends of bristles, may be 5-25 mm, but are not limited thereto.
  • the planted fine bristles may have a total length of 10-30 mm or 15-25 mm, a thickness of 0.01-0.1 mm and a planted portion length of 1-15 mm.
  • the height of fine bristles from the top surface of toothbrush head after planting may be 5-20 mm, but is not limited thereto.
  • the toothbrush bristles obtained by using polyketone according to the present disclosure have excellent elasticity and are suitable for removal of plaque on the severely indented tooth surfaces. Therefore, it is possible to remove plaque on the tooth surfaces and between teeth, where the conventional toothbrushes cannot function well.
  • the toothbrush bristles can also perform suitable massaging on the gingiva without irritation or bleeding. Therefore, it is possible to carry out tooth care continuously without a need for performing massage for the health of teeth and gingiva requiring additional time and labor.
  • a toothbrush including the polyketone toothbrush bristles.
  • the toothbrush according to the present disclosure may be provided in the form of a product including a toothbrush head made of an elastic member such as rubber or silicone so as to impart the effects of physical cleaning and gingiva massaging.
  • the toothbrush according to the present disclosure may include: a grip portion having a predetermined thickness and width and a toothbrush head portion linked thereto; polyketone toothbrush bristles formed on the top surface of the toothbrush head portion; and a tip provided in the toothbrush head portion.
  • the toothbrush according to the present disclosure may be provided with two or more types of toothbrush bristles made using different materials.
  • the toothbrush according to the present disclosure may include: a grip portion having a predetermined thickness and width and a toothbrush head portion linked thereto; the first toothbrush bristles fixed to one part of the head portion and the second toothbrush bristles fixed to the other part of the head portion, wherein the first toothbrush bristles include a polyketone material, and the second toothbrush bristles include at least one water-insoluble polymer material selected from the group consisting of polypropylene, polyethylene, polyethylene terephthalate, polybutylene terephthalate, polytrimethylene terephthalate, polyurethane and nylon.
  • toothbrush bristles and ingredients known to those skilled in the art may be applied to the toothbrush according to the present disclosure, except that the toothbrush bristles according to the present disclosure uses polyketone instead of conventional materials, such as nylon and PBT.
  • novel toothbrush bristles according to the present disclosure have higher rigidity and elasticity as compared to the conventional toothbrush bristles, are more helpful to tooth cleaning, show high wear resistance, and can be used for a long time.
  • tensile strength as the force upon the cutting of bristles, by which the rigidity of one strand of bristle could be evaluated, was determined. Then, evaluation was carried out by comparing the tensile strength of polyketone with that of the conventional material for toothbrush bristles, Nylon 612 or PBT.
  • both ends of one strand of toothbrush bristle were fixed by a fixing member and the strand was drawn along the axis of the specimen. Then, the force upon the cutting, i.e. tensile strength, was determined.
  • polyketone toothbrush bristles were planted to a toothbrush head to obtain a toothbrush. Then, the toothbrush was compared with toothbrushes using Nylon 612 and PBT in terms of elasticity loss.
  • the elasticity loss indicates durability (bristle gap-widening) during the use of a toothbrush. After carrying out reciprocating brushing 5000 times or 10000 times by using a brush machine, the gap-widening was determined according to the following mathematical Formula 1. As the value of elasticity loss is decreased, the difference of a gap in the bristles between before and after brushing is reduced, suggesting that the toothbrush bristles show lower gap-widening.
  • Elasticity loss % B ⁇ A ⁇ 100
  • Table 1 shows the results of tensile strength (Kgf) and elasticity loss (%) of each type of toothbrush bristle.
  • Kgf tensile strength
  • elasticity loss % of each type of toothbrush bristle.
  • polyketone toothbrush bristles show a tensile strength (kgf) 2.0 times higher than the tensile strength of nylon and 1.13 times higher than that of PBT (Table 1), which demonstrates that polyketone maintains high rigidity when it is applied to toothbrush bristles.
  • Polymers having high rigidity and excellent wear resistance like polyketone, include fluoro-resin (PTFE, PVDF), POM, PBT, PES, or the like.
  • fluoro-resin it is difficult to manufacture toothbrush bristles due to its high melting point.
  • POM it is not suitable for toothbrush bristles due to its brittleness.
  • PBT and PES are materials having sufficiently high rigidity and excellent wear resistance, like polyketone.
  • toothbrush bristles having a diameter of 0.18 mm were produced by using them in the same manner as the above-described example.
  • the end portions of bristles were planted without any separated processing for fine bristles to obtain toothbrush bristles.
  • the toothbrush bristles using three types of materials were evaluated by professional panels through a survey about gingiva irritation.
  • nylon toothbrush bristles and polyketone toothbrush bristles each having a diameter of 5 M (0.127 mm) were planted to provide test toothbrushes. Then, 20- to 40-aged 20 females and 20 males were allowed to use each toothbrush and compared the toothbrushes with each other. Before using a new toothbrush, the panels were allowed to have a quiescence of 3 days and to care their teeth as usual during the quiescence.
  • the polyketone bristles show high elasticity to provide a significantly higher effect of cleaning the tooth surface and interdental portion as compared to the nylon bristles.
  • Bacterial film coating on the artificial tooth surface was used after the tooth portion of a gnathostatic model was dipped in a colored polymer for about 10 seconds, taken out therefrom, dried in an isothermal-isohumidity chamber (25°C, 55%) maintaining a predetermined temperature and humidity for 60 minutes, and dried completely. Then, the toothbrushes, to which bristles having a diameter of 10 mils, 8 mils, 7 mils and 6 mils were planted, were used so that the section of bristles of the toothbrush and the narrower surface of the coated gnathostatic model were positioned horizontally with each other to cover the surfaces as much as possible during brushing.
  • a pressure of 300 g was applied to all types of toothbrushes and each toothbrush product was subjected to vertical brushing for 30 seconds alternately with horizontal brushing for 30 seconds, 8 times. Then, the area of the artificial tooth surface was measured before and after removing the bacterial film through a microscope and the rate of plaque removal was evaluated as a percent (%) value. The results are shown in FIG. 1 .
  • the top end/bottom end of one strand of toothbrush bristle were gripped to a universal test machine (UTM) with an interval of 1 cm and the top end was drawn at a rate of 200 mm/min to measure the force when the strand was cut.
  • UTM universal test machine
  • toothbrush bristles To evaluate elasticity (softness) of toothbrush bristles, one strand of toothbrush bristle was hang on a wire, which allows measurement of applied force at the point corresponding to 1/3 of the strand, and the force was measured.
  • polyketone (0.56 kgf) has a tensile strength improved by 40% as compared to nylon (0.40 kgf).

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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)
EP17856677.4A 2016-09-29 2017-09-25 Toothbrush bristles made of polyketone material, and toothbrush including same Active EP3520651B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR20160125903 2016-09-29
KR20170089694 2017-07-14
PCT/KR2017/010558 WO2018062791A1 (ko) 2016-09-29 2017-09-25 폴리케톤 소재 칫솔모와 이를 포함하는 칫솔

Publications (3)

Publication Number Publication Date
EP3520651A1 EP3520651A1 (en) 2019-08-07
EP3520651A4 EP3520651A4 (en) 2020-04-08
EP3520651B1 true EP3520651B1 (en) 2024-01-10

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EP17856677.4A Active EP3520651B1 (en) 2016-09-29 2017-09-25 Toothbrush bristles made of polyketone material, and toothbrush including same

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)

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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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KR101368490B1 (ko) * 2012-02-02 2014-03-10 비비씨 주식회사 칫솔모 및 그를 이용한 칫솔
KR101281635B1 (ko) * 2012-02-27 2013-07-03 비비씨 주식회사 내구성과 항균성 강화를 위해 제올라이트가 첨가된 블렌드 기법을 통한 칫솔모 및 그의 제조방법
KR101646037B1 (ko) * 2014-11-14 2016-08-12 주식회사 효성 폴리케톤 멀티필라멘트
KR101598359B1 (ko) * 2014-10-22 2016-03-14 비비씨 주식회사 생분해성 수지를 포함하는 칫솔모의 제조방법 및 이를 이용한 칫솔
CN105919275A (zh) * 2016-06-16 2016-09-07 朱群益 一种牙缝刷
DE202017002839U1 (de) * 2017-05-30 2018-08-31 Perlon Nextrusion Monofil GmbH Polyketonfasern, deren Herstellung und Verwendung

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JP2019530497A (ja) 2019-10-24
CN117223964A (zh) 2023-12-15
KR20180118591A (ko) 2018-10-31
EP3520651A1 (en) 2019-08-07
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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