WO2020099685A1 - Composites polymères comprenant une matrice polyamide aliphatique et des fibres de verre ou de basalte encollées - Google Patents

Composites polymères comprenant une matrice polyamide aliphatique et des fibres de verre ou de basalte encollées Download PDF

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Publication number
WO2020099685A1
WO2020099685A1 PCT/EP2019/081698 EP2019081698W WO2020099685A1 WO 2020099685 A1 WO2020099685 A1 WO 2020099685A1 EP 2019081698 W EP2019081698 W EP 2019081698W WO 2020099685 A1 WO2020099685 A1 WO 2020099685A1
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WO
WIPO (PCT)
Prior art keywords
glass
polyamide
fibres
imide
sizing
Prior art date
Application number
PCT/EP2019/081698
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English (en)
Inventor
Gilles Orange
Yann GABET
Eliane Espuche
Olivier GAIN
Original Assignee
Rhodia Operations
Universite Claude Bernard Lyon 1
Universite Jean Monnet Saint-Etienne
Institut National Des Sciences Appliquees De Lyon
Le Centre National De La Recherche Scientifique
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 Rhodia Operations, Universite Claude Bernard Lyon 1, Universite Jean Monnet Saint-Etienne, Institut National Des Sciences Appliquees De Lyon, Le Centre National De La Recherche Scientifique filed Critical Rhodia Operations
Publication of WO2020099685A1 publication Critical patent/WO2020099685A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • C08J5/06—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials
    • C08J5/08—Reinforcing macromolecular compounds with loose or coherent fibrous material using pretreated fibrous materials glass fibres
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/1095—Coating to obtain coated fabrics
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/26—Macromolecular compounds or prepolymers
    • C03C25/32—Macromolecular compounds or prepolymers obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/26—Macromolecular compounds or prepolymers
    • C03C25/32—Macromolecular compounds or prepolymers obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C03C25/328—Polyamides
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/465—Coatings containing composite materials
    • C03C25/47—Coatings containing composite materials containing particles, fibres or flakes, e.g. in a continuous phase
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/08—Ingredients agglomerated by treatment with a binding agent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/70—Cleaning, e.g. for reuse
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • C08K7/04—Fibres or whiskers inorganic
    • C08K7/14—Glass

Definitions

  • Sizings usually contain as main component of the dry material a film forming agent, optionally with or without a coupling agent and further additives such as surfactants, defoaming agents, lubricants, and antistatics.
  • US 6,479,581 discloses aqueous solutions comprising a polyamide amic acid, a tertiary aliphatic amine and water to adjust a polyamide-amic acid content of from 0.5 to 15 wt% based on the total weight of the
  • thermoplastic polymers polymers having a high glass transition temperature
  • Non limitative examples of aliphatic diacids are notably oxalic acid
  • the aliphatic polyamide (PA) is nylon 66, i.e. the polyamide obtained by the polycondensation reaction between
  • a sizing system comprising a polyetherimide and/or a polyamide-imide and, optionally, silica nanoparticles and, optionally, further additives, e.g. coupling agents.
  • Basalt fibres are similar to glass fibres but have usually better physicomechanical properties compared to glass fibres.
  • Glass or basalt fibres are also not subject to any particular limitations and the skilled person will, based on his professional knowledge, select the best suitable type of glass or basalt fibre for the specific application intended.
  • Glass or basalt fibres may be be short (length below 1 mm), long (length exceeding 1 mm) or continuous and may be used e.g. as chopped fibres, as fibre strands, as fibre yarns or as endless fibres to give only some examples.
  • imide groups as such and/or in their corresponding amic acid form, are advantageously linked to an aromatic ring, as illustrated below:
  • the aromatic polyimide (P1) is an aromatic
  • the aromatic polyamide-imide can be notably manufactured by a process including the polycondensation reaction between (i) at least one acid monomer chosen from pyromellitic anhydride, bis(3,4- dicarboxyphenyl)ether dianhydride, trimellitic anhydride and trimellitic anhydride monoacid halides and (ii) at least one comonomer chosen from diamines and diisocyanates.
  • trimellitic anhydride monoacid halides trimellitic anhydride
  • a first class of aromatic polyetherimides consists of those wherein the
  • R 2 is selected from aromatic hydrocarbon radicals having from 6 to 20 carbon atoms and halogenated derivatives thereof, or alkyl substituted derivatives thereof, wherein the alkyl group contains 1 to 6 carbon atoms, alkylene and cycloalkylene radicals having from 2 to 20 carbon atoms and C 2 to Ce alkylene terminated polydiorganosiloxanes or a divalent radical of the formula (XVII) wherein R 3 and R 4 are as previously defined.
  • R1 b-3 may, for example, be prepared by effecting reaction in the presence of a dipolar aprotic solvent of a mixture of ingredients comprising, for instance,
  • n an integer from 1 to 6
  • n integer from 1 to 6
  • aromatic bis(ether anhydride)s of formula (XXXVI) include, for example,
  • the recurring units of the aromatic polyimide (P1 ) are recurring units (R1 ).
  • the sizing system may comprise a certain amount of other solvents than water in an amount being lower than the amount of water, i.e. water forms more than 50 wt% of the solvent content of the sizing system.
  • the sizing system is essentially free and particularly preferred free of solvents other than water.
  • Emulsions are mixtures of two or more liquids that are normally immisicible and are examples for colloids.
  • the sizing system may be in the form of an emulsion.
  • These agents may notably be selected from the family of surfactants and/or water soluble amphiphilic polymers.
  • an aqueous solution or emulsion comprising a polyamide-imide and/or a polyetherimide as described above (i.e. in the imide form or partly in the amic acid form) is deposited onto the surface of glass or basalt fibres (preferably glass fibres) and, optionally, the coated glass or basalt fibres (preferably glass fibres) are subjected to a heat treatment.
  • the aqueous solution or emulsion of the sizing system can e.g. be applied by dip-coating or spray coating or with a coating station comprising a roller contacting the fibres.
  • single filaments of glass or basalt fibres are pulled by a gathering shoe to create a multi-filament roving and the sizing deposition takes place prior to the strand assembly.
  • the sizing is picked-up by the fibres in the liquid state and after winding the fibres are dried and subjected to a heat treatment step in a hot oven at a temperature in the range from 100 to 300°C for a period of 12 to 24 hours.
  • the amount of coating deposited on the glass or basalt fibres embedded in the thermoplastic polyamide matrix using the sizing agent described hereinbefore is usually not exceeding 10 wt%, preferably not exceeding 5 wt% and even more preferably not exceeding 2.5 wt%, based on the weight of the glass or basalt fibres.
  • composite materials of the present invention comprising the glass or basalt fibres, preferably the glass fibres, coated with the sizing system disclosed herein show, in particular when such sizing system comprises silica nanoparticles, improved interfacial properties compared to
  • the sizing systems were applied by immersing the glass fibre substrate, cleaned as described above, for ten seconds in the aqueous solution of the PAI or PEI previously diluted in order to rech a content of non-volatile of 5% by weight and then manually withdrawing the fibres from the bath at a speed of approximately 10-15 cm/min.
  • the PEI sizing the coated fibres were heated to 110°C for 30 min and thereafter heated up to 280°C for 30 min.
  • For the PAI sizing the coated fibres were heated to 120°C for a period of 30 min, then heated to 180°C for 10 min and then to 280°C for ten minutes.
  • the interlaminar fracture toughness GIC is calculated thanks to the SBT method ( « simple beam theory ») with the following formula:

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Composite Materials (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Reinforced Plastic Materials (AREA)

Abstract

La présente invention concerne un matériau composite comprenant a) un polymère matriciel polyamide thermoplastique aliphatique et b) des fibres de verre ou de basalte incorporées dans ledit polymère matriciel a), les fibres de verre ou de basalte étant revêtues avec un système d'encollage comprenant un polyamide-imide et/ou un polyétherimide et, éventuellement, des nanoparticules de silice.
PCT/EP2019/081698 2018-11-16 2019-11-18 Composites polymères comprenant une matrice polyamide aliphatique et des fibres de verre ou de basalte encollées WO2020099685A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18306509 2018-11-16
EP18306509.3 2018-11-16

Publications (1)

Publication Number Publication Date
WO2020099685A1 true WO2020099685A1 (fr) 2020-05-22

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111808418A (zh) * 2020-07-23 2020-10-23 咸阳新德安新材料科技有限公司 一种注醇用柔性复合高压管材料及复合高压管
CN113979649A (zh) * 2021-12-07 2022-01-28 上海富晨化工有限公司 一种玄武岩纤维增强热固性树脂复合材料用纤维表面改性剂及其制备方法
CN115010383A (zh) * 2022-06-30 2022-09-06 天津斯坦利新型材料有限公司 具有至少两层涂覆层的玻璃纤维、制备方法及其应用
RU2793761C1 (ru) * 2022-03-18 2023-04-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированных стекловолокон и наполненный ими полиэфиримидный композит
WO2023052269A1 (fr) * 2021-10-01 2023-04-06 Cytec Industries Inc Compositions aqueuses exemptes de polyester et leur utilisation pour le collage de fibres de renforcement utilisées dans des composites

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CN108059364A (zh) * 2017-12-28 2018-05-22 安徽宏实光机电高科有限公司 一种玄武岩纤维用反应型浸润剂的制备方法

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CN108059364A (zh) * 2017-12-28 2018-05-22 安徽宏实光机电高科有限公司 一种玄武岩纤维用反应型浸润剂的制备方法

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111808418B (zh) * 2020-07-23 2023-04-07 咸阳新德安新材料科技有限公司 一种注醇用柔性复合高压管材料及复合高压管
CN111808418A (zh) * 2020-07-23 2020-10-23 咸阳新德安新材料科技有限公司 一种注醇用柔性复合高压管材料及复合高压管
WO2023052269A1 (fr) * 2021-10-01 2023-04-06 Cytec Industries Inc Compositions aqueuses exemptes de polyester et leur utilisation pour le collage de fibres de renforcement utilisées dans des composites
CN113979649A (zh) * 2021-12-07 2022-01-28 上海富晨化工有限公司 一种玄武岩纤维增强热固性树脂复合材料用纤维表面改性剂及其制备方法
RU2793855C1 (ru) * 2022-02-02 2023-04-07 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированного стекловолокна и полиэфиримидный композиционный материал
RU2793857C1 (ru) * 2022-02-02 2023-04-07 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированных стекловолокон и полиэфиримидные композиты на их основе
RU2793856C1 (ru) * 2022-02-02 2023-04-07 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированных стеклянных волокон и полиэфиримидный композит
RU2793761C1 (ru) * 2022-03-18 2023-04-05 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированных стекловолокон и наполненный ими полиэфиримидный композит
CN115010383A (zh) * 2022-06-30 2022-09-06 天津斯坦利新型材料有限公司 具有至少两层涂覆层的玻璃纤维、制备方法及其应用
CN115010383B (zh) * 2022-06-30 2023-12-15 天津斯坦利新型材料有限公司 具有至少两层涂覆层的玻璃纤维、制备方法及其应用
RU2811370C1 (ru) * 2023-03-09 2024-01-11 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова"(КБГУ) Способ получения аппретированного стекловолокна и полимерный композиционный материал на его основе
RU2816365C1 (ru) * 2023-03-09 2024-03-28 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированного стекловолокна и полимерный композиционный материал на его основе
RU2811289C1 (ru) * 2023-03-13 2024-01-11 Федеральное государственное бюджетное образовательное учреждение высшего образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" (КБГУ) Способ получения аппретированных стекловолокон и армированная полимерная композиция на их основе

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