FR3060577B1 - Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition - Google Patents

Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition Download PDF

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Publication number
FR3060577B1
FR3060577B1 FR1663063A FR1663063A FR3060577B1 FR 3060577 B1 FR3060577 B1 FR 3060577B1 FR 1663063 A FR1663063 A FR 1663063A FR 1663063 A FR1663063 A FR 1663063A FR 3060577 B1 FR3060577 B1 FR 3060577B1
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France
Prior art keywords
liquid composition
composition
invention further
further relates
polymerization
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FR1663063A
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FR3060577A1 (fr
Inventor
Pierre Gerard
Pierre Escale
Alexander Zoller
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Arkema France SA
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Arkema France SA
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Publication date
Priority to FR1663063A priority Critical patent/FR3060577B1/fr
Application filed by Arkema France SA filed Critical Arkema France SA
Priority to CN201780079149.5A priority patent/CN110088388B/zh
Priority to KR1020197017704A priority patent/KR102559703B1/ko
Priority to US16/468,003 priority patent/US11459416B2/en
Priority to PCT/EP2017/084201 priority patent/WO2018115342A1/fr
Priority to CA3044608A priority patent/CA3044608A1/fr
Priority to BR112019011102-6A priority patent/BR112019011102B1/pt
Priority to JP2019533527A priority patent/JP2020502349A/ja
Priority to MX2019006506A priority patent/MX2019006506A/es
Priority to EP17818172.3A priority patent/EP3559335A1/fr
Publication of FR3060577A1 publication Critical patent/FR3060577A1/fr
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Publication of FR3060577B1 publication Critical patent/FR3060577B1/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
    • 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
    • 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
    • B29C70/06—Fibrous reinforcements only
    • 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
    • B29C70/42—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles
    • B29C70/46—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles using matched moulds, e.g. for deforming sheet moulding compounds [SMC] or prepregs
    • B29C70/48—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles using matched moulds, e.g. for deforming sheet moulding compounds [SMC] or prepregs and impregnating the reinforcements in the closed mould, e.g. resin transfer moulding [RTM], e.g. by vacuum
    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • 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
    • C08F4/38—Mixtures of peroxy-compounds
    • 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
    • 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
    • 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
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides
    • 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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Composite Materials (AREA)
  • Mechanical Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
  • Reinforced Plastic Materials (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

La présente invention concerne une composition liquide comprenant un monomère, un polymère (méth) acrylique et au moins deux initiateurs. En particulier, la présente invention concerne une composition liquide comprenant un monomère, un polymère (méth) acrylique et au moins deux initiateurs qui ont des temps de demi-vie différents. Cette composition liquide peut être utilisée sous la forme d'un sirop et en particulier, sous la forme d'un sirop pour l'imprégnation de fibres ou de matériau fibreux. L'invention concerne en outre un matériau thermoplastique obtenu après polymérisation de la composition liquide. L'invention concerne en outre un procédé de fabrication d'une telle composition liquide. L'invention concerne en outre un procédé d'imprégnation d'un substrat fibreux de fibres longues avec ladite composition liquide. L'invention concerne en outre un substrat fibreux imprégné avec ladite composition liquide qui est utile pour fabriquer des pièces composites. La présente invention concerne en outre un procédé de fabrication de pièces mécaniques ou d'éléments structuraux constitués de matériau composite et des pièces mécaniques ou des éléments structuraux constitués de matériau composite obtenus par un procédé utilisant une telle composition liquide.
FR1663063A 2016-12-21 2016-12-21 Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition Active FR3060577B1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
FR1663063A FR3060577B1 (fr) 2016-12-21 2016-12-21 Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition
MX2019006506A MX2019006506A (es) 2016-12-21 2017-12-21 Composicion liquida que comprende dos iniciadores, su proceso de polimerizacion, uso y material o composicion obtenida despues polimerizacion de la composicion.
US16/468,003 US11459416B2 (en) 2016-12-21 2017-12-21 Liquid composition comprising two initiators, its process of polymerization, use and material or composition obtained following polymerization of composition
PCT/EP2017/084201 WO2018115342A1 (fr) 2016-12-21 2017-12-21 Composition liquide comportant deux initiateurs, son processus de polymérisation, son utilisation et matériau ou composition obtenu(e) suite à la polymérisation de la composition
CA3044608A CA3044608A1 (fr) 2016-12-21 2017-12-21 Composition liquide comportant deux initiateurs, son processus de polymerisation, son utilisation et materiau ou composition obtenu(e) suite a la polymerisation de la composition
BR112019011102-6A BR112019011102B1 (pt) 2016-12-21 2017-12-21 Composição líquida compreendendo dois iniciadores, seu processo de polimerização, uso e material ou composição obtida seguindo a polimerização de composição
CN201780079149.5A CN110088388B (zh) 2016-12-21 2017-12-21 包含两种引发剂的液体组合物、其聚合方法、用途以及在组合物聚合后获得的材料或组合物
KR1020197017704A KR102559703B1 (ko) 2016-12-21 2017-12-21 2 종의 개시제를 포함하는 액체 조성물, 이의 중합 방법, 용도 및 조성물의 중합 후에 수득되는 재료 또는 조성물
EP17818172.3A EP3559335A1 (fr) 2016-12-21 2017-12-21 Composition liquide comportant deux initiateurs, son processus de polymérisation, son utilisation et matériau ou composition obtenu(e) suite à la polymérisation de la composition
JP2019533527A JP2020502349A (ja) 2016-12-21 2017-12-21 二つの開始剤を含む液体組成物、その重合方法、使用及び材料、又は組成物の重合後に得られる組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1663063 2016-12-21
FR1663063A FR3060577B1 (fr) 2016-12-21 2016-12-21 Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition

Publications (2)

Publication Number Publication Date
FR3060577A1 FR3060577A1 (fr) 2018-06-22
FR3060577B1 true FR3060577B1 (fr) 2020-11-06

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FR1663063A Active FR3060577B1 (fr) 2016-12-21 2016-12-21 Composition liquide comprenant deux initiateurs, son procede de polymerisation, utilisation et materiau ou composition obtenu apres polymerisation de la composition

Country Status (10)

Country Link
US (1) US11459416B2 (fr)
EP (1) EP3559335A1 (fr)
JP (1) JP2020502349A (fr)
KR (1) KR102559703B1 (fr)
CN (1) CN110088388B (fr)
BR (1) BR112019011102B1 (fr)
CA (1) CA3044608A1 (fr)
FR (1) FR3060577B1 (fr)
MX (1) MX2019006506A (fr)
WO (1) WO2018115342A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3082845B1 (fr) * 2018-06-21 2021-01-15 Arkema France Composition liquide comprenant trois initiateurs, son procede de polymerisation, son utilisation et materiau obtenu apres polymerisation de la composition
FR3093727B1 (fr) * 2019-03-11 2021-10-22 Arkema France Composition liquide comprenant un composé de cire, son procédé de polymérisation, utilisation et matériau ou composition obtenus suite à la polymérisation de la composition
FR3110169B1 (fr) * 2020-05-15 2022-08-26 Arkema France Composition comprenant au moins deux peroxydes organiques pour la polymérisation de monomères éthyléniquement insaturés
CN111718439A (zh) * 2020-06-19 2020-09-29 宁波南大光电材料有限公司 甲基丙烯酸树脂及其制备方法和应用
CN111875729B (zh) * 2020-07-08 2022-10-11 中国航发北京航空材料研究院 成型碳纤维复合材料的甲基丙烯酸甲酯树脂原位聚合体系
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.

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JPS6045209B2 (ja) * 1976-07-20 1985-10-08 住友化学工業株式会社 連続重合方法
US4211741A (en) 1977-04-07 1980-07-08 Sunlite Plastics, Inc. Extrusion process for laminated medical-surgical tubing
US4328329A (en) * 1980-12-11 1982-05-04 E. I. Du Pont De Nemours And Company Process for polymerizing methyl methacrylate syrup using a dual initiator system
US4588798A (en) * 1985-02-01 1986-05-13 E. I. Du Pont De Nemours And Company Process for preparing acrylic polymer sheets using a dual peroxide initiator system
US4605717A (en) * 1985-06-21 1986-08-12 E. I. Du Pont De Nemours And Company Preparation of acrylic polymer sheets using a ternary peroxide initiator system
JPS62109004A (ja) * 1985-11-08 1987-05-20 Hitachi Ltd プラスチツク光フアイバ、その製法及び樹脂
JP2567726B2 (ja) * 1990-09-04 1996-12-25 三菱レイヨン株式会社 メタクリル樹脂板の製造方法
JP4270480B2 (ja) * 1999-04-30 2009-06-03 綜研化学株式会社 アクリル系重合体の製造法
US8378044B2 (en) * 2008-05-09 2013-02-19 Kyoto University Living radical polymerization method using alcohol as catalyst
CN101683244B (zh) * 2008-09-27 2012-05-30 上海杰事杰新材料(集团)股份有限公司 一种可回收全热塑性卫浴制品及其制备方法
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
FR3005057B1 (fr) 2013-04-25 2015-05-15 Arkema France Sirop liquide (meth)acrylique, son procede de polymerisation, son utilisation et objet moule obtenu a partir de celui-ci
FR3016642B1 (fr) 2014-01-22 2020-02-21 Arkema France Procede d'impregnation pour un substrat fibreux, sirop monomere liquide pour le procede d'impregnation, sa methode de polymerisation et article structurel obtenu
CA3137959A1 (fr) * 2019-04-26 2020-10-29 3V Sigma Usa Inc. Compositions polymeres de gel rapide, systemes et procedes

Also Published As

Publication number Publication date
US11459416B2 (en) 2022-10-04
BR112019011102A2 (pt) 2019-10-08
KR20190091287A (ko) 2019-08-05
MX2019006506A (es) 2019-08-21
BR112019011102B1 (pt) 2023-10-17
CN110088388A (zh) 2019-08-02
US20200010639A1 (en) 2020-01-09
WO2018115342A1 (fr) 2018-06-28
FR3060577A1 (fr) 2018-06-22
EP3559335A1 (fr) 2019-10-30
JP2020502349A (ja) 2020-01-23
CN110088388B (zh) 2023-04-18
KR102559703B1 (ko) 2023-07-25
CA3044608A1 (fr) 2018-06-28

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