CA2863145C - Fiber composite materials and methods of manufacturing same - Google Patents

Fiber composite materials and methods of manufacturing same Download PDF

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Publication number
CA2863145C
CA2863145C CA2863145A CA2863145A CA2863145C CA 2863145 C CA2863145 C CA 2863145C CA 2863145 A CA2863145 A CA 2863145A CA 2863145 A CA2863145 A CA 2863145A CA 2863145 C CA2863145 C CA 2863145C
Authority
CA
Canada
Prior art keywords
composition
mol
fiber
polyols
component polyurethane
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA2863145A
Other languages
English (en)
French (fr)
Other versions
CA2863145A1 (en
Inventor
Andreas Ferencz
Lothar Thiele
Tamara Schmidt
Konrad Becker
Wolfgang LUPP
Dustin ULLMANN
Oliver-Kei Okamoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of CA2863145A1 publication Critical patent/CA2863145A1/en
Application granted granted Critical
Publication of CA2863145C publication Critical patent/CA2863145C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • 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
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/0001—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor characterised by the choice of material
    • 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
    • B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
    • B29C45/17—Component parts, details or accessories; Auxiliary operations
    • B29C45/1701—Component parts, details or accessories; Auxiliary operations using a particular environment during moulding, e.g. moisture-free or dust-free
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
    • C08G18/2027—Heterocyclic amines; Salts thereof containing one heterocyclic ring having two nitrogen atoms in the ring
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
    • 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
    • C08K7/00—Use of ingredients characterised by shape
    • C08K7/02—Fibres or whiskers
    • 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
    • B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Mechanical Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Composite Materials (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Reinforced Plastic Materials (AREA)
CA2863145A 2012-02-28 2013-02-25 Fiber composite materials and methods of manufacturing same Expired - Fee Related CA2863145C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP12157299.4 2012-02-28
EP12157301 2012-02-28
EP12157299 2012-02-28
EP12157301.8 2012-02-28
PCT/EP2013/053699 WO2013127732A1 (de) 2012-02-28 2013-02-25 2k-polyurethansysteme mit phasentrennung

Publications (2)

Publication Number Publication Date
CA2863145A1 CA2863145A1 (en) 2013-09-06
CA2863145C true CA2863145C (en) 2021-03-16

Family

ID=47748639

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2863145A Expired - Fee Related CA2863145C (en) 2012-02-28 2013-02-25 Fiber composite materials and methods of manufacturing same
CA2863141A Active CA2863141C (en) 2012-02-28 2013-02-25 2k polyurethane systems with a high glass-transition temperature

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2863141A Active CA2863141C (en) 2012-02-28 2013-02-25 2k polyurethane systems with a high glass-transition temperature

Country Status (10)

Country Link
US (2) US10093766B2 (enExample)
EP (2) EP2820061B1 (enExample)
JP (3) JP2015510011A (enExample)
KR (2) KR102046197B1 (enExample)
CN (2) CN104136476B (enExample)
AU (1) AU2013225178B2 (enExample)
CA (2) CA2863145C (enExample)
ES (1) ES2885763T3 (enExample)
MX (2) MX365691B (enExample)
WO (2) WO2013127732A1 (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102011002809A1 (de) * 2011-01-18 2012-07-19 Henkel Ag & Co. Kgaa 2K-PU-Zusammensetzung mit verzögerter Vernetzung
JP2015510011A (ja) * 2012-02-28 2015-04-02 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co.KGaA 高いガラス転移温度を有する2kポリウレタン系
DE102014208353A1 (de) 2014-05-05 2015-11-05 Henkel Ag & Co. Kgaa Mehrphasige Polyurethan-Zusammensetzung mit reduzierter Schaumentwicklung
EP3002309B1 (en) * 2014-09-30 2017-01-11 Henkel AG & Co. KGaA Compositions comprising a fiber material and a thermoplastic binder
CN110114380B (zh) * 2016-12-28 2022-04-26 汉高股份有限及两合公司 双组分聚氨酯粘合剂
EP3533530A1 (en) 2018-03-01 2019-09-04 Henkel AG & Co. KGaA Process for the production of composite materials at low temperatures
PT2020102871B (pt) * 2018-11-22 2023-05-30 Formtap Interni Sist Automotivos S/A Processo de obtenção de compósitos termoestruturais

Family Cites Families (34)

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EP0013487B2 (en) 1978-12-11 1988-11-23 Imperial Chemical Industries Plc Modified diisocyanate compositions and polyurethanes thereof
DE3626223A1 (de) * 1986-08-02 1988-02-04 Henkel Kgaa Polyurethan-praepolymere auf basis oleochemischer polyole, ihre herstellung und verwendung
JPS63309510A (ja) * 1987-06-12 1988-12-16 Nippon Polyurethan Kogyo Kk ポリイソシアヌレ−ト複合体の製造法
DE8711301U1 (de) * 1987-08-20 1987-10-29 Pelzer, Helmut, 58313 Herdecke Faserverstärkter, hoch temperaturstabiler, plattenförmiger Werkstoff
US4800058A (en) 1987-08-24 1989-01-24 Arco Chemical Company Method for the preparation of rigid cast or transfer molded thermoset polyurethane modified polyisocyanurate compositions
US4743626A (en) 1987-09-14 1988-05-10 Basf Corporation Liquid carbodiimide-uretonimine modified polymethylene polyphenylene polyisocyanates and polyurethane foams made therefrom
ES2099240T3 (es) * 1991-05-03 1997-05-16 Ciba Geigy Ag Componente poliolico para la fabricacion de piezas moldeadas de poliuretano.
CA2188503A1 (en) * 1995-12-22 1997-06-23 Neil H. Nodelman Polyurethane resin transfer molding systems
CN1117111C (zh) * 1997-09-26 2003-08-06 陶氏环球技术公司 高使用温度的聚氨酯弹性体
DE19750820B4 (de) * 1997-11-17 2004-04-29 Höpner Lacke GmbH Beschichtungsstoff für mit Restrost behaftete Oberflächen
HK1042313A1 (zh) 1998-11-16 2002-08-09 亨茨曼国际有限公司 聚异氰脲酸酯组合物及复合材料
JP4031632B2 (ja) * 2001-10-31 2008-01-09 三菱重工業株式会社 繊維強化型プラスチックの製造方法
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DE10318740A1 (de) 2003-04-25 2004-11-11 Bayer Materialscience Ag Polyurethan-Formulierungen und ihre Verwendung
DE10356767A1 (de) * 2003-12-05 2005-07-07 Henkel Kgaa Platten und Formkörper auf Basis von Polyurethanbindemittel
DE102004033849A1 (de) 2004-07-13 2006-02-16 Bayer Materialscience Ag Verfahren zur Herstellung flüssiger, lagerstabiler Carbodiimid- und/oder Uretonimingruppen aufweisender organischer Isocyanate mit niedriger Farbzahl
US20060014890A1 (en) * 2004-07-14 2006-01-19 Zielinski David P Polyisocyanates with improved compatibility with high hydroxyl content polyols
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DE102006002158A1 (de) * 2006-01-17 2007-07-19 Bayer Materialscience Ag Verfahren zur Herstellung flüssiger, lagerstabiler Carboddimid- und/oder Uretonimingruppen aufweisender organischer Isocyanate
ITMI20061107A1 (it) * 2006-06-08 2007-12-09 Diab Int Ab Formulazioni per prodotti cellulari di polimero espanso basati su polivinl cloruro prodotti cellulari di polimero espanso migliorati basati su polivinil cloruro e processo per produrre detti prodotti cellulari di polimero espanso migliorati
US20080099141A1 (en) * 2006-10-26 2008-05-01 Ashland Inc. Method of producing flexible laminates
JP5041794B2 (ja) * 2006-12-07 2012-10-03 住化バイエルウレタン株式会社 変性ポリイソシアネートの製造方法
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DE102007062529A1 (de) * 2007-12-20 2009-06-25 Henkel Ag & Co. Kgaa 2K-PU-Klebstoff zum Verkleben von Faserformteilen
BRPI0907096A2 (pt) * 2008-01-29 2015-07-07 Basf Se Processos para preparar poliéter álcoois e para produzir poliuretanos, e, poliéter álcool
DE102008027914A1 (de) * 2008-06-12 2009-12-17 Henkel Ag & Co. Kgaa Vernetzende 2K-Isocyanat-Zusammensetzungen
CA2732421C (en) 2008-08-28 2016-05-17 Huntsman International Llc Mixture obtained by reacting polyol and anhydride and its use in polyisocyanates for making polyisocyanurates
KR101830203B1 (ko) * 2009-12-01 2018-02-20 바스프 에스이 폴리우레탄을 주성분으로 하는 인발성형 수지 시스템
DE102011002809A1 (de) * 2011-01-18 2012-07-19 Henkel Ag & Co. Kgaa 2K-PU-Zusammensetzung mit verzögerter Vernetzung
JP2015510011A (ja) * 2012-02-28 2015-04-02 ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェンHenkel AG & Co.KGaA 高いガラス転移温度を有する2kポリウレタン系
HUP1400402A2 (hu) * 2014-08-29 2016-03-29 Borsodchem Zrt Eljárás világos színû, stabilan tárolható uretonimin modifikált poliizocianát elõállítására
CN105447437B (zh) 2015-02-13 2017-05-03 比亚迪股份有限公司 指纹识别方法和装置

Also Published As

Publication number Publication date
MX365691B (es) 2019-06-11
AU2013225176B2 (en) 2016-01-28
WO2013127732A1 (de) 2013-09-06
KR102046197B1 (ko) 2019-11-18
EP2820060A1 (de) 2015-01-07
AU2013225178B2 (en) 2016-01-07
AU2013225176A1 (en) 2014-09-18
CA2863141C (en) 2021-08-17
US10131738B2 (en) 2018-11-20
US10093766B2 (en) 2018-10-09
CN104136476B (zh) 2017-04-19
MX365277B (es) 2019-05-29
US20140371391A1 (en) 2014-12-18
MX2014010290A (es) 2014-10-13
US20160362516A1 (en) 2016-12-15
KR20140127830A (ko) 2014-11-04
KR20140129304A (ko) 2014-11-06
CA2863141A1 (en) 2013-09-06
JP2015510011A (ja) 2015-04-02
AU2013225178A1 (en) 2014-09-18
CA2863145A1 (en) 2013-09-06
ES2885763T3 (es) 2021-12-15
EP2820061B1 (de) 2021-07-21
JP2019035088A (ja) 2019-03-07
WO2013127734A1 (de) 2013-09-06
MX2014010292A (es) 2014-10-13
CN104136476A (zh) 2014-11-05
CN104136477B (zh) 2016-06-29
CN104136477A (zh) 2014-11-05
JP6534260B2 (ja) 2019-06-26
EP2820061A1 (de) 2015-01-07
JP2015512979A (ja) 2015-04-30

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