WO2021229909A1 - 繊維処理剤、繊維処理組成物、繊維加工品および繊維処理剤の製造方法 - Google Patents

繊維処理剤、繊維処理組成物、繊維加工品および繊維処理剤の製造方法 Download PDF

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Publication number
WO2021229909A1
WO2021229909A1 PCT/JP2021/009864 JP2021009864W WO2021229909A1 WO 2021229909 A1 WO2021229909 A1 WO 2021229909A1 JP 2021009864 W JP2021009864 W JP 2021009864W WO 2021229909 A1 WO2021229909 A1 WO 2021229909A1
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WO
WIPO (PCT)
Prior art keywords
fiber treatment
mass
treatment agent
fiber
content
Prior art date
Application number
PCT/JP2021/009864
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
一成 深瀬
直樹 村田
卓也 葛谷
康宏 中川
Original Assignee
昭和電工株式会社
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 昭和電工株式会社 filed Critical 昭和電工株式会社
Priority to JP2022522532A priority Critical patent/JPWO2021229909A1/ja
Priority to CN202180034512.8A priority patent/CN115552069B/zh
Publication of WO2021229909A1 publication Critical patent/WO2021229909A1/ja

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/44Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04Homopolymers or copolymers of esters
    • C08L33/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • D06M13/11Compounds containing epoxy groups or precursors 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
    • D06M15/19Treating 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

Definitions

  • the present invention has been made in view of the above circumstances, and is a fiber treatment having an aqueous medium as a dispersion medium, having excellent storage stability, and having a high effect of improving the strength of the fiber by mixing with a curing agent. It is an object of the present invention to provide a fiber treatment agent from which a composition can be obtained, and a method for producing the same. Further, the present invention contains the fiber treatment agent and the curing agent of the present invention, has good viscosity stability, and can obtain a high-strength processed fiber product by adhering to the fiber and curing the fiber. The purpose is to provide goods. Another object of the present invention is to provide a high-strength processed fiber product in which a cured product of the fiber treatment composition of the present invention is attached to the fiber.
  • the content of the carboxy group in the total mass of the copolymer (X) and the polyepoxy compound (Y) is 0.10 ⁇ 10 -4 mol / g or more, [1] to [ 7]
  • the content of the epoxy group in the total mass of the copolymer (X) and the polyepoxy compound (Y) is 0.50 ⁇ 10 -4 mol / g or more, [1] to [ 8]
  • (meth) acrylate is meant acrylate or methacrylate.
  • (Meta) Acrylic means acrylic or methacryl.
  • the "ethylenically unsaturated bond” means a double bond between adjacent carbon atoms, excluding the carbon atoms forming an aromatic ring.
  • the "weight average molecular weight” is a standard polystyrene-equivalent value measured by gel permeation chromatography (GPC).
  • the polyepoxy compound (Y) is a hydrophobic compound such as a bisphenol type epoxy compound, a hydrogenated bisphenol type epoxy compound, or a phenol novolac type epoxy compound
  • the ratio of the structural unit (a1) to the structural unit (a) is , 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less. This is because the inclusion of the structural unit (a2) derived from the (meth) acrylic acid ester (A2) improves the affinity between the copolymer (X) and the polyepoxy compound (Y).
  • Examples of the other monomer (C) include ethylenically unsaturated aromatic compounds, saturated aliphatic vinyl ester compounds, conjugated diene compounds, maleimide compounds, vinyl ether compounds, allyl ether compounds, and dialkyl esters of unsaturated dicarboxylic acids.
  • Examples include vinyl compounds having a cyano group.
  • dialkyl ester of unsaturated dicarboxylic acid examples include dialkyl esters such as maleic acid, fumaric acid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride, itaconic anhydride, citraconic anhydride and tetrahydrophthalic anhydride. ..
  • dialkyl ester of these unsaturated dicarboxylic acids only one kind may be used, or two or more kinds may be used in combination.
  • R is an alkyl group.
  • the fiber treatment agent ( ⁇ ) of the present embodiment is, for example, as a raw material for a monomer (that is, a copolymer (X)) containing a (meth) acrylic acid ester (A) and an ethylenically unsaturated carboxylic acid (B).
  • the monomer (monomer) to be used) can be produced by a method of emulsion polymerization in the aqueous medium (Z) in the presence of the polyepoxy compound (Y).
  • a polymerization initiator can be appropriately selected and used as needed.
  • a surfactant may be used.
  • each component including a monomer used as a raw material of the copolymer (X) may be collectively charged into a reaction vessel and emulsion-polymerized, or each of them may be emulsion-polymerized.
  • Emulsion polymerization may be carried out while continuously supplying the components into the reaction vessel.
  • a monomer used as a raw material for the copolymer (X), a polyepoxy compound (Y), a surfactant, and an aqueous medium (Z) are mixed to form an emulsion, and then the emulsion and a polymerization initiator. And may be mixed and polymerized.
  • the emulsion polymerization reaction is preferably carried out while stirring the raw materials in the reaction vessel using a known method.
  • the non-volatile content concentration of the fiber treatment agent ( ⁇ ) is preferably 15 to 65% by mass, more preferably 20 to 60% by mass, and even more preferably 30 to 55% by mass.
  • the non-volatile content concentration may be 35 to 50% by mass, or 40 to 48% by mass.
  • the non-volatile content concentration of the fiber treatment agent ( ⁇ ) is determined by a step of mixing the fiber treatment agent ( ⁇ ), the curing agent ( ⁇ ), the curing accelerator ( ⁇ ), etc., which will be described later, and / or applying the fiber treatment composition. It can be appropriately determined in consideration of workability in the process.
  • the non-volatile content concentration of the fiber treatment agent ( ⁇ ) can be appropriately adjusted by, for example, a method of adjusting the content of the aqueous medium (Z) in the fiber treatment agent ( ⁇ ).
  • the content of the epoxy group in the total mass of the copolymer (X) and the polyepoxy compound (Y) may be 15 ⁇ 10 -4 mol / g or less, and 12 ⁇ 10 -4 mol / g or less. May be.
  • the curing agent ( ⁇ ) a commercially available one may be used.
  • examples of commercially available curing agents include ADEKA HANDNER EH-8051 (polyamine) (manufactured by ADEKA Co., Ltd.); Fujicure FXI-919; tomide TXH-674-B and TXS-53-C (manufactured by T & K TOKA Co., Ltd.); Examples include Jamaicacid BTW (manufactured by Shin Nihon Rika Co., Ltd.); and Karenz MT BD-1 (manufactured by Showa Denko KK).
  • the fiber treatment agent ( ⁇ ) of the present embodiment is excellent in productivity because it does not need to use large equipment at the time of manufacturing and does not need to have a complicated manufacturing process.
  • the fiber treatment composition of the present embodiment contains the fiber treatment agent ( ⁇ ) of the present embodiment and a predetermined amount of a curing agent ( ⁇ ) composed of a compound having a functional group (F) reactive with an epoxy group. .. Therefore, the fiber treatment composition of the present embodiment has good viscosity stability. Therefore, the fiber treatment composition of the present embodiment can be easily applied to the fiber, the work of adhering the fiber treatment composition to the fiber can be efficiently performed, and the adhesion amount can be easily adjusted with high accuracy. Can be done. Further, the fiber treatment composition of the present embodiment is obtained by adhering it to the fiber and curing it to obtain a high-strength processed fiber product.
  • the amount N 1 [mol / g] of the epoxy group of the fiber treatment agent ( ⁇ ) was measured by the method shown below. Excess hydrogen chloride was added to the total amount of epoxy groups contained in the component (raw material) used for the synthesis of the fiber treatment agent ( ⁇ ), and the mixture was reacted with the epoxy groups. Next, the amount of remaining hydrogen chloride was confirmed by titrating unreacted hydrogen chloride with potassium hydroxide.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2021/009864 2020-05-13 2021-03-11 繊維処理剤、繊維処理組成物、繊維加工品および繊維処理剤の製造方法 WO2021229909A1 (ja)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2022522532A JPWO2021229909A1 (zh) 2020-05-13 2021-03-11
CN202180034512.8A CN115552069B (zh) 2020-05-13 2021-03-11 纤维处理剂、纤维处理组合物、纤维加工品及纤维处理剂的制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020084744 2020-05-13
JP2020-084744 2020-05-13

Publications (1)

Publication Number Publication Date
WO2021229909A1 true WO2021229909A1 (ja) 2021-11-18

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PCT/JP2021/009864 WO2021229909A1 (ja) 2020-05-13 2021-03-11 繊維処理剤、繊維処理組成物、繊維加工品および繊維処理剤の製造方法

Country Status (4)

Country Link
JP (1) JPWO2021229909A1 (zh)
CN (1) CN115552069B (zh)
TW (1) TW202206477A (zh)
WO (1) WO2021229909A1 (zh)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49106586A (zh) * 1973-02-08 1974-10-09
JPH08231616A (ja) * 1994-12-27 1996-09-10 Asahi Chem Ind Co Ltd 硬化性水性樹脂組成物
JPH10237764A (ja) * 1996-12-16 1998-09-08 Takeda Chem Ind Ltd バッキング用遅燃性樹脂水性組成物
JP2002173871A (ja) * 2000-12-06 2002-06-21 Nippon Carbide Ind Co Inc 繊維加工用架橋型樹脂水性分散液。
JP2002194035A (ja) * 2000-12-26 2002-07-10 Nippon Nsc Ltd エポキシ樹脂水分散体の製造方法及びそれを用いて製造されるエポキシ樹脂水分散体
JP2003119657A (ja) * 2001-10-15 2003-04-23 Nippon Shokubai Co Ltd 積層板用不織布用水性バインダー及びそれにより形成されてなる積層板用不織布、プリント配線板及び絶縁板
WO2020100790A1 (ja) * 2018-11-13 2020-05-22 昭和電工株式会社 水性樹脂エマルジョン及びその製造方法、並びに水性樹脂組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS49106586A (zh) * 1973-02-08 1974-10-09
JPH08231616A (ja) * 1994-12-27 1996-09-10 Asahi Chem Ind Co Ltd 硬化性水性樹脂組成物
JPH10237764A (ja) * 1996-12-16 1998-09-08 Takeda Chem Ind Ltd バッキング用遅燃性樹脂水性組成物
JP2002173871A (ja) * 2000-12-06 2002-06-21 Nippon Carbide Ind Co Inc 繊維加工用架橋型樹脂水性分散液。
JP2002194035A (ja) * 2000-12-26 2002-07-10 Nippon Nsc Ltd エポキシ樹脂水分散体の製造方法及びそれを用いて製造されるエポキシ樹脂水分散体
JP2003119657A (ja) * 2001-10-15 2003-04-23 Nippon Shokubai Co Ltd 積層板用不織布用水性バインダー及びそれにより形成されてなる積層板用不織布、プリント配線板及び絶縁板
WO2020100790A1 (ja) * 2018-11-13 2020-05-22 昭和電工株式会社 水性樹脂エマルジョン及びその製造方法、並びに水性樹脂組成物

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Publication number Publication date
CN115552069A (zh) 2022-12-30
TW202206477A (zh) 2022-02-16
JPWO2021229909A1 (zh) 2021-11-18
CN115552069B (zh) 2024-04-26

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