FR3087203B1 - Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation - Google Patents

Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation Download PDF

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Publication number
FR3087203B1
FR3087203B1 FR1859537A FR1859537A FR3087203B1 FR 3087203 B1 FR3087203 B1 FR 3087203B1 FR 1859537 A FR1859537 A FR 1859537A FR 1859537 A FR1859537 A FR 1859537A FR 3087203 B1 FR3087203 B1 FR 3087203B1
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France
Prior art keywords
meth
acrylic
composite
relates
polymeric
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Active
Application number
FR1859537A
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English (en)
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FR3087203A1 (fr
Inventor
Pierre Escale
Pierre Gerard
Dana Swan
Robert Barsotti
Nathan Bachman
Jing-Han Wang
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Arkema France SA
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Arkema France SA
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
Priority to FR1859537A priority Critical patent/FR3087203B1/fr
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to US17/284,828 priority patent/US20210388136A1/en
Priority to KR1020217010961A priority patent/KR20210076001A/ko
Priority to CN201980067683.3A priority patent/CN112805318A/zh
Priority to CA3114724A priority patent/CA3114724A1/fr
Priority to JP2021520560A priority patent/JP2022504940A/ja
Priority to PCT/EP2019/077996 priority patent/WO2020079015A1/fr
Priority to EP19789944.6A priority patent/EP3867302A1/fr
Priority to BR112021006662A priority patent/BR112021006662A2/pt
Publication of FR3087203A1 publication Critical patent/FR3087203A1/fr
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Publication of FR3087203B1 publication Critical patent/FR3087203B1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B15/00—Pretreatment of the material to be shaped, not covered by groups B29B7/00 - B29B13/00
    • B29B15/08—Pretreatment of the material to be shaped, not covered by groups B29B7/00 - B29B13/00 of reinforcements or fillers
    • B29B15/10—Coating or impregnating independently of the moulding or shaping step
    • B29B15/12—Coating or impregnating independently of the moulding or shaping step of reinforcements of indefinite length
    • B29B15/122—Coating or impregnating independently of the moulding or shaping step of reinforcements of indefinite length with a matrix in liquid form, e.g. as melt, solution or latex
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
    • B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
    • B29C70/28—Shaping operations therefor
    • B29C70/40—Shaping or impregnating by compression not applied
    • B29C70/50—Shaping or impregnating by compression not applied for producing articles of indefinite length, e.g. prepregs, sheet moulding compounds [SMC] or cross moulding compounds [XMC]
    • B29C70/52—Pultrusion, i.e. forming and compressing by continuously pulling through a die
    • B29C70/521—Pultrusion, i.e. forming and compressing by continuously pulling through a die and impregnating the reinforcement before the die
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/28—Oxygen or compounds releasing free oxygen
    • C08F4/32—Organic compounds
    • C08F4/34—Per-compounds with one peroxy-radical
    • 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
    • C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
    • C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
    • 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
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
    • C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
    • 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
    • C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
    • C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
    • B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
    • B29C70/28—Shaping operations therefor
    • B29C70/40—Shaping or impregnating by compression not applied
    • B29C70/50—Shaping or impregnating by compression not applied for producing articles of indefinite length, e.g. prepregs, sheet moulding compounds [SMC] or cross moulding compounds [XMC]
    • B29C70/52—Pultrusion, i.e. forming and compressing by continuously pulling through a die
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2033/00—Use of polymers of unsaturated acids or derivatives thereof as moulding material
    • B29K2033/04—Polymers of esters
    • B29K2033/12—Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
    • C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
    • 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
    • C08J2333/00—Characterised by the use 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; Derivatives of such polymers
    • C08J2333/04—Characterised by the use 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; Derivatives of such polymers esters
    • C08J2333/06—Characterised by the use 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; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
    • C08J2333/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
    • C08L2205/16—Fibres; Fibrils

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Composite Materials (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Reinforced Plastic Materials (AREA)
  • Moulding By Coating Moulds (AREA)

Abstract

La présente invention se rapporte à une composition (méth) acrylique appropriée pour des compositions polymères (méth) acryliques et des composites polymères (méth) acryliques, à son procédé de préparation et à son utilisation. En particulier la présente invention se rapporte à une composition (méth) acrylique qui est légèrement réticulée une fois polymérisée et qui est appropriée pour des composites (méth) acryliques et plus particulièrement pour des barres d'armature. Plus particulièrement la présente invention se rapporte à une composition (méth) acrylique appropriée pour des barres d'armature, à la préparation de telles compositions (méth) acryliques, à une barre d'armature composite la comprenant et à un procédé de préparation d'une telle barre d'armature composite. La présente invention se rapporte également à l'utilisation d'une telle composition (méth) acrylique et à l'utilisation de barres d'armature.
FR1859537A 2018-10-15 2018-10-15 Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation Active FR3087203B1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
FR1859537A FR3087203B1 (fr) 2018-10-15 2018-10-15 Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation
KR1020217010961A KR20210076001A (ko) 2018-10-15 2019-10-15 복합재용 (메트)아크릴 중합체 조성물, 이의 제조 방법 및 용도
CN201980067683.3A CN112805318A (zh) 2018-10-15 2019-10-15 用于复合材料的(甲基)丙烯酸系聚合物组合物、其制备方法和用途
CA3114724A CA3114724A1 (fr) 2018-10-15 2019-10-15 Compositions de polymere (meth)acrylique pour composite, son procede de preparation et son utilisation
US17/284,828 US20210388136A1 (en) 2018-10-15 2019-10-15 (meth) acrylic polymeric compositions for composite, its method of preparation and use
JP2021520560A JP2022504940A (ja) 2018-10-15 2019-10-15 複合材料のための（メタ）アクリルポリマー組成物、その調製方法および使用
PCT/EP2019/077996 WO2020079015A1 (fr) 2018-10-15 2019-10-15 Compositions de polymère (méth)acrylique pour composite, son procédé de préparation et son utilisation
EP19789944.6A EP3867302A1 (fr) 2018-10-15 2019-10-15 Compositions de polymère (méth)acrylique pour composite, son procédé de préparation et son utilisation
BR112021006662A BR112021006662A2 (pt) 2018-10-15 2019-10-15 composições poliméricas (met)acrílicas para compósito, seu método de preparação e uso

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1859537A FR3087203B1 (fr) 2018-10-15 2018-10-15 Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation

Publications (2)

Publication Number Publication Date
FR3087203A1 FR3087203A1 (fr) 2020-04-17
FR3087203B1 true FR3087203B1 (fr) 2022-01-21

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FR1859537A Active FR3087203B1 (fr) 2018-10-15 2018-10-15 Compositions polymeres (meth)acryliques pour composite, leur procede de preparation et leur utilisation

Country Status (9)

Country Link
US (1) US20210388136A1 (fr)
EP (1) EP3867302A1 (fr)
JP (1) JP2022504940A (fr)
KR (1) KR20210076001A (fr)
CN (1) CN112805318A (fr)
BR (1) BR112021006662A2 (fr)
CA (1) CA3114724A1 (fr)
FR (1) FR3087203B1 (fr)
WO (1) WO2020079015A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3117678B1 (fr) 2020-12-16 2024-02-23 Arkema France Article composite à base d’une matrice thermoplastique intégrant au moins un transducteur comprenant un polymère piézoélectrique
FR3130809A1 (fr) 2021-12-22 2023-06-23 Arkema France Composition (méth)acrylique pour composite, son procédé de préparation et son utilisation
FR3132523A1 (fr) * 2022-02-08 2023-08-11 Arkema France Composition (meth)acrylique, materiau composite polymérique obtenu a partir d’une telle composition, procede pour la production de ladite composition et dudit matériau et utilisations de ceux-ci
DE102022105682A1 (de) 2022-03-10 2023-09-14 Solidian Gmbh Verfahren zur Herstellung wenigstens eines teilgehärteten Bewehrungselements
FR3144139A1 (fr) * 2022-12-23 2024-06-28 Arkema France Composite thermoplastique et procédé pour la production de celui-ci pour le renforcement d’une structure.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH09111085A (ja) * 1995-10-13 1997-04-28 Mitsubishi Rayon Co Ltd 樹脂組成物、アクリル系プリミックス及びアクリル系人工大理石の製造方法
US6203911B1 (en) * 1998-06-17 2001-03-20 E. I. Du Pont De Nemours And Company Thermoset volatile monomer molding compositions
JP5486341B2 (ja) * 2010-02-23 2014-05-07 パナソニック株式会社 熱硬化型（メタ）アクリル系樹脂組成物とそれを用いたシートモールディングコンパウンド、バルクモールディングコンパウンドおよび成形品
FR2981652B1 (fr) 2011-10-21 2015-03-27 Arkema France Composites via la polymerisation in-situ de resines thermoplastiques methacryliques
FR2993581B1 (fr) 2012-07-18 2016-01-22 Arkema France Procede d'impregnation pour un substrat fibreux, sirop (meth)acrylique liquide pour le procede d'impregnation, son procede de polymerisation et produit structure obtenu a partir de celui-ci
CA2839915A1 (fr) 2014-01-17 2015-07-17 Borna Hajimiragha Barre d'armature en fibre de verre renforcee de polyester flexible
FR3030585B1 (fr) * 2014-12-22 2017-02-03 Arkema France Procede d'impregnation d'un substrat fibreux avec un melange (meth)acrylique, composition dudit melange, et materiau composite obtenu apres polymerisation dudit melange.
FR3064267B1 (fr) * 2017-03-27 2021-07-23 Arkema France Compose reticulant, son procede de synthese, composition liquide comprenant ledit compose reticulant, son procede de polymerisation, et materiau obtenu apres polymerisation de ladite composition

Also Published As

Publication number Publication date
EP3867302A1 (fr) 2021-08-25
US20210388136A1 (en) 2021-12-16
JP2022504940A (ja) 2022-01-13
FR3087203A1 (fr) 2020-04-17
WO2020079015A1 (fr) 2020-04-23
CA3114724A1 (fr) 2020-04-23
CN112805318A (zh) 2021-05-14
KR20210076001A (ko) 2021-06-23
BR112021006662A2 (pt) 2021-07-06

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