WO2009112515A1 - Fibre revêtue d'une composition d'apprêt - Google Patents

Fibre revêtue d'une composition d'apprêt Download PDF

Info

Publication number
WO2009112515A1
WO2009112515A1 PCT/EP2009/052847 EP2009052847W WO2009112515A1 WO 2009112515 A1 WO2009112515 A1 WO 2009112515A1 EP 2009052847 W EP2009052847 W EP 2009052847W WO 2009112515 A1 WO2009112515 A1 WO 2009112515A1
Authority
WO
WIPO (PCT)
Prior art keywords
sizing composition
anyone
fibre according
component
ethylene oxide
Prior art date
Application number
PCT/EP2009/052847
Other languages
English (en)
Inventor
Cristina Piccinelli
Johan Franz Gradus Antonius Jansen
Federica Galli
Martijn Marcus Gabriël ANTONISSE
Debora Genini
Ronald Leonardus Verleg
Original Assignee
Dsm Ip Assets B.V.
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 Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Publication of WO2009112515A1 publication Critical patent/WO2009112515A1/fr

Links

Classifications

    • 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
    • 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
    • C03C25/28—Macromolecular compounds or prepolymers obtained 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
    • C03C25/28—Macromolecular compounds or prepolymers obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C03C25/30—Polyolefins
    • 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
    • C03C25/323—Polyesters, e.g. alkyd resins
    • 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
    • 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
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/10—Epoxy resins modified by unsaturated 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
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/06—Unsaturated polyesters

Definitions

  • the deposition of sizing composition is very important as it makes it possible, on the one hand, to obtain the strands and, on the other hand, to use these strands effectively in making composites.
  • the size has the following usual functions: it protects the strand from abrasion, thus preventing them from breaking during their manufacture and possibly during their use; additionally, it allows the strands thus formed to be combined with organic and/or inorganic materials to be reinforced, especially making it easier for the strands to be wetted by and impregnated with these materials. In general, the size thus favours adhesion between the glass and the material to be reinforced, thereby making it possible to obtain composites having improved mechanical properties.
  • the sizing composition must provide the fibres with an outer film which is compatible with the resin they will reinforce.
  • Commonly applied sizing compositions are low viscosity aqueous sizing compositions comprising as sizing agent at least a compound having one or more epoxy functional groups such as bisphenol A diglycidyl ether or a novolac epoxy. See for example US-B-5779758, WO-A-2004/009507, US-B-7276282, US-A-2005/0214524.
  • a disadvantage of the use of such sizing compositions is that the adhesion between in particular an unsaturated polyester and/or vinyl ester resin matrix and glass fibres coated with such sizing compositions may be insufficient. In view of this, the industry continues to want improved fibre reinforcement for in particular an unsaturated polyester resin or vinyl ester resin matrix.
  • the object of the present invention is to increase the adhesion between in particular an unsaturated polyester or vinyl ester resin matrix and sized glass fibres.
  • the glass fibres are coated with a sizing composition
  • a sizing composition comprising 5-70 wt.% of a curable vinyl ester resin being the reaction product of component (a) being at least one component containing at least one glycidyl ether and component (b) being methacrylic acid and/or acrylic acid, 10-97 wt.% water and an ethylene oxide-propylene oxide copolymer as non-ionic emulsifier, wherein the wt.% is relative to the total sizing composition.
  • the vinyl ester resin in the sizing composition preferably has a molecular weight Mw of from 400 up to and including 10000.
  • any of the known components containing at least one glycidyl ether can be used in the preparation of the vinyl ester resin.
  • Components containing at least two glycidyl ethers are preferred.
  • Preferred components containing at least two glycidyl ether are bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, novolac glycidyl ethers or a mixture of at least two of these components. More preferred components are bisphenol A diglycidyl ether, preferably having a molecular weight Mw of from 360 up to and including 3000; novolac glycidyl ethers, preferably having a molecular weight Mw of from 1000 up to and including 10000; or a mixture thereof.
  • the sizing composition comprises water, preferably deionized water.
  • the amount of water in the sizing composition is at least 10 and at most 97 wt.%.
  • the amount of water in the sizing composition is at least 20 wt.%, more preferably at least 30 wt.%.
  • the amount of water in the sizing composition is at most 65 wt.%, more preferably at most 96 wt.% and even more preferably at most 95 wt.%.
  • the sizing composition comprises ethylene oxide-propylene oxide copolymer as non-ionic emulsifier.
  • the ethylene oxide-propylene oxide copolymer non- ionic emulsifier in the sizing composition preferably has a molecular weight Mw of from 5000 up to and including 50000.
  • the amount of ethylene oxide-propylene oxide copolymer in the sizing composition, relative to the total amount of vinyl ester resin in the sizing composition, is at least 0.1 wt.%, more preferably at least 0.5 wt.%.
  • the amount of ethylene oxide-propylene oxide copolymer in the sizing composition is at most 2.5 wt.%.
  • the reactive diluent is a methacrylate and/or styrene.
  • the amount of reactive solvent in the sizing composition is preferably lower than 20% by weight and more preferably lower than 5% by weight.
  • the peroxide is chosen from the group of organic peroxides.
  • suitable organic peroxides are: tertiary alkyl hydroperoxides (such as, for instance, t-butyl hydroperoxide), other hydroperoxides (such as, for instance, cumene hydroperoxide), the special class of hydroperoxides formed by the group of ketone peroxides (perketones, being an addition product of hydrogen peroxide and a ketone, such as, for instance, methyl ethyl ketone peroxide and acetylacetone peroxide), peroxyesters or peracids (such as, for instance, t-butyl peresters, benzoyl peroxide, peracetates and perbenzoates, lauryl peroxide, including (di)peroxyesters), perethers (such as, for instance, peroxy diethyl ether).
  • tertiary alkyl hydroperoxides such as, for instance, t
  • Emulsion A Synthesis resin A and emulsification
  • the sizing is used to produce vinyl ester resin sized glass fiber.
  • Preparation of reference sizing Neoxil 965 sizing
  • Neoxil 965 was used instead of 608g of VE emulsion B and 258g of Neoxil 965.
  • the sizing is used to produce Neoxil 965 sized glass fibre.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention porte sur une fibre de verre revêtue d'une composition d'apprêt, la composition d'apprêt comprenant 5-70 % en poids d'une résine d'ester vinylique durcissable qui est le produit de réaction d'un composant (a) qui est au moins un composant contenant au moins un éther de glycidyle et d'un composant (b) qui est l'acide méthacrylique et/ou l'acide acrylique, 10-97 % en poids d'eau et un copolymère d'oxyde éthylène-oxyde de propylène en tant qu'émulsifiant non ionique; le pourcentage en poids étant relatif à la composition d'apprêt totale.
PCT/EP2009/052847 2008-03-11 2009-03-11 Fibre revêtue d'une composition d'apprêt WO2009112515A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08004427.4 2008-03-11
EP08004427 2008-03-11

Publications (1)

Publication Number Publication Date
WO2009112515A1 true WO2009112515A1 (fr) 2009-09-17

Family

ID=39642660

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/052847 WO2009112515A1 (fr) 2008-03-11 2009-03-11 Fibre revêtue d'une composition d'apprêt

Country Status (1)

Country Link
WO (1) WO2009112515A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104356614A (zh) * 2014-11-14 2015-02-18 无锡中洁能源技术有限公司 一种基于乳液聚合法的pet聚酯的制备方法
CN112979185A (zh) * 2021-05-11 2021-06-18 山东墨匠新材料科技有限公司 一种玻璃纤维浸润剂及其制备方法
US11208564B2 (en) 2014-01-22 2021-12-28 Arkema France Impregnation process for a functional fibrous substrate, a liquid monomer syrup for the impregnation process, its method of polymerization and structured article obtained thereof
CN114853366A (zh) * 2022-05-30 2022-08-05 中海油天津化工研究设计院有限公司 一种海洋工程复合管道用玄武岩连续纤维浸润剂及其制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5114934A (ja) * 1974-07-30 1976-02-05 Saiden Kagaku Kk Ekijosetsuchakuryokukyokahifukusoseibutsu
US4487797A (en) * 1983-12-01 1984-12-11 Ppg Industries, Inc. Glass fibers to reinforce polymeric materials
JPS61227949A (ja) * 1985-03-29 1986-10-11 Nitto Electric Ind Co Ltd 光学ガラスフアイバ用被覆材料
WO1997042129A1 (fr) * 1996-05-08 1997-11-13 N.V. Owens-Corning S.A. Ensimage a haute solubilite pour fibres
JP2001172875A (ja) * 1999-12-17 2001-06-26 Nippon Electric Glass Co Ltd ガラス繊維及びそれを用いたガラス繊維強化プラスチック
EP1223016A2 (fr) * 1996-08-12 2002-07-17 Owens Corning Traitements chimiques de fibres et de fils composites enrobés pour le moulage d'articles composites thermoplastiques renforcés par des fibres
US20060078721A1 (en) * 2004-10-12 2006-04-13 Rau Robert B Resin compatible yarn binder and uses thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5114934A (ja) * 1974-07-30 1976-02-05 Saiden Kagaku Kk Ekijosetsuchakuryokukyokahifukusoseibutsu
US4487797A (en) * 1983-12-01 1984-12-11 Ppg Industries, Inc. Glass fibers to reinforce polymeric materials
JPS61227949A (ja) * 1985-03-29 1986-10-11 Nitto Electric Ind Co Ltd 光学ガラスフアイバ用被覆材料
WO1997042129A1 (fr) * 1996-05-08 1997-11-13 N.V. Owens-Corning S.A. Ensimage a haute solubilite pour fibres
EP1223016A2 (fr) * 1996-08-12 2002-07-17 Owens Corning Traitements chimiques de fibres et de fils composites enrobés pour le moulage d'articles composites thermoplastiques renforcés par des fibres
JP2001172875A (ja) * 1999-12-17 2001-06-26 Nippon Electric Glass Co Ltd ガラス繊維及びそれを用いたガラス繊維強化プラスチック
US20060078721A1 (en) * 2004-10-12 2006-04-13 Rau Robert B Resin compatible yarn binder and uses thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 197612, Derwent World Patents Index; AN 1976-21725X, XP002491661 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11208564B2 (en) 2014-01-22 2021-12-28 Arkema France Impregnation process for a functional fibrous substrate, a liquid monomer syrup for the impregnation process, its method of polymerization and structured article obtained thereof
CN104356614A (zh) * 2014-11-14 2015-02-18 无锡中洁能源技术有限公司 一种基于乳液聚合法的pet聚酯的制备方法
CN112979185A (zh) * 2021-05-11 2021-06-18 山东墨匠新材料科技有限公司 一种玻璃纤维浸润剂及其制备方法
CN114853366A (zh) * 2022-05-30 2022-08-05 中海油天津化工研究设计院有限公司 一种海洋工程复合管道用玄武岩连续纤维浸润剂及其制备方法

Similar Documents

Publication Publication Date Title
EP0741676B1 (fr) Compositions d'encollage de fibres de verre, fibres de verre encollees et procedes de renforcement de materiaux polymeres a l'aide de ces compositions
US6720072B1 (en) High-temperature resistant polymerizable metal oxide particles
US4341877A (en) Sizing composition and sized glass fibers and process
EP0146689B1 (fr) Fibres de verre pour renforcer des matières polymères
JP2005533738A (ja) ガラス繊維サイジング組成物、サイジングされたガラス繊維、およびポリオレフィン複合材
WO1993001051A1 (fr) Fibres de verre traitees chimiquement pour le renforcement de materiaux polymeres
CA2626117A1 (fr) Materiau composite renforce
JP5199366B2 (ja) ガラスストランド用の物理ゲルの形態であるサイジング組成物、得られたガラスストランドおよびそのストランドを含む複合材
WO2009112515A1 (fr) Fibre revêtue d'une composition d'apprêt
US10035284B2 (en) UV-curable glass fiber sizing compositions
WO2009055403A2 (fr) Composition aqueuse de liant ou de colle
SK28096A3 (en) Glass fibre size composition, manufacture method of sized glass fibres, sized glass fibres and composit materials gained by using this size composition
MXPA06012790A (es) Resina de vinilester de compuestos organicos volatiles bajos libre de adhesividad.
US5736246A (en) Reinforcing glass strands and composites resistant to corrosive media
JPH04103625A (ja) ガラス繊維サイズ
FI101629B (fi) Vinyyliesteri- tai polyesterihartsikoostumuksia lujitemuovikomposiitti matriiseja varten, menetelmä hartsikoostumusten stabiloimiseksi ja men etelmä niiden styreenipäästöjen alentamiseksi
WO2013135625A1 (fr) Compositions de résine thermodurcissable
KR100383253B1 (ko) F.r.p 절연봉 인발성형용 비닐에스테르 수지와 이를 이용한인발성형품의 제조방법
EP3177577B1 (fr) Composition d'ensimage de fibres de verre, fibres de verre encollées et composites de polyoléfines
WO1997043339A1 (fr) Resines ester vinyliques renforcees
CN117865510B (zh) 一种风电叶片用玻纤增强材料及其制备方法
CA1246775A (fr) Compositions de resine d'ester vinylique a faible protuberance de fibres
CN111691184A (zh) 一种缝编连续毡浸润剂的制备方法
JP2000344846A (ja) ラジカル硬化型難燃性樹脂組成物
WO2022238128A1 (fr) Compositions de diluant réactif à base de (méth)acrylate pour des résines polyester insaturées

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 09720822

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 09720822

Country of ref document: EP

Kind code of ref document: A1