EP0486651A1 - Preimpregne, procede de fabrication et application - Google Patents
Preimpregne, procede de fabrication et applicationInfo
- Publication number
- EP0486651A1 EP0486651A1 EP91910945A EP91910945A EP0486651A1 EP 0486651 A1 EP0486651 A1 EP 0486651A1 EP 91910945 A EP91910945 A EP 91910945A EP 91910945 A EP91910945 A EP 91910945A EP 0486651 A1 EP0486651 A1 EP 0486651A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- prepreg
- phenolic resin
- mixture
- phenol
- fibers
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 229920001568 phenolic resin Polymers 0.000 claims abstract description 17
- 239000002131 composite material Substances 0.000 claims abstract description 12
- 239000012783 reinforcing fiber Substances 0.000 claims abstract description 12
- 239000005011 phenolic resin Substances 0.000 claims abstract description 11
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003822 epoxy resin Substances 0.000 claims abstract description 6
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000004033 plastic Substances 0.000 claims abstract description 5
- 229920003023 plastic Polymers 0.000 claims abstract description 5
- 229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 3
- 239000004760 aramid Substances 0.000 claims abstract description 3
- 229920006231 aramid fiber Polymers 0.000 claims abstract description 3
- 239000004917 carbon fiber Substances 0.000 claims abstract description 3
- -1 elasticizers Substances 0.000 claims abstract description 3
- 239000000945 filler Substances 0.000 claims abstract description 3
- 239000003063 flame retardant Substances 0.000 claims abstract description 3
- 239000003365 glass fiber Substances 0.000 claims abstract description 3
- 239000000080 wetting agent Substances 0.000 claims abstract description 3
- 239000007858 starting material Substances 0.000 claims abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007859 condensation product Substances 0.000 claims description 7
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical group O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005470 impregnation Methods 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 239000005007 epoxy-phenolic resin Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 7
- 238000005452 bending Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000011089 mechanical engineering Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy 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
- C08J5/24—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
-
- 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]
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- 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
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- 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
Definitions
- the invention relates to a prepreg based on unidirectionally arranged reinforcements impregnated with durable plastics.
- Kung fibers such as glass fibers, carbon fibers, aramid fibers and the like.
- prepregs are produced by impregnating reinforcing fibers with 10 thermosetting plastics. These prepregs are preferably used to manufacture composite parts for aircraft and mechanical engineering and for the manufacture of sports articles. These composite parts are now subject to a number of requirements, such as high dynamic mechanical properties and high temperature and chemical resistance . It is known to use prepregs for such composite parts, the reinforcing fibers of which are impregnated with highly functional epoxy resins, whereby the desired temperature and chemical resistance may not be achieved, but the required dynamic mechanical properties such as sufficient toughness can be achieved in the finished composite parts.
- the invention is based on the object, a prepreg based on unidirectionally arranged, with thermoset plastic
- the prepreg according to the invention which is characterized in that its reinforcing fibers with a plastic mixture, an epoxy resin, a phenolic resin, optionally an accelerator and optionally additives such as fillers, flame retardants, elasticizers, wetting agents and the like ., are impregnated, the proportions of reinforcing fibers in the prepreg advantageously being 30-80% by weight, 70-20% by weight of epoxy-phenolic resin mixture and 0-30% by weight of additives.
- the prepreg according to the invention contains a phenol-formaldehyde condensation product in the molar ratio of phenol to formaldehyde in the resin mixture as phenolic resin from 1: 0.5 to 1: 0.9, but advantageously from 1: 0.6 to 1: 0 , 85.
- the invention is also based on the object of specifying a method for producing the prepreg according to the invention.
- a solvent in the range of 0-20% by weight is added to the epoxy-phenolic resin mixture before the impregnation process, this mixture being applied by means of a doctor blade to a continuously moving film in the form of a layer, into which then the tapered, endless reinforcing fibers are pressed in and thereby impregnated.
- a solvent-free epoxy resin-phenolic resin mixture is used for the impregnation, which is brought to an elevated temperature before the impregnation process in order to reduce the viscosity.
- This scrim advantageously runs through impregnated Reinforcing fibers additionally a heating device in which the epoxy resin-phenolic resin mixture is converted into the B state and the solvent which may be present is evaporated, and then, if appropriate, a calender. Furthermore, a phenol-formaldehyde condensation product with a molar ratio of phenol to formaldehyde of 1: 0.5 to 1: 0.9, advantageously from 1: 0.6 to 1: 0.85, is preferably used.
- the prepregs according to the invention are advantageously used for the production of hot-cured composite materials, the curing taking place, for example, in a closed form, but also in a state wound on a mandrel.
- the bending strength losses of the laminate A produced from the prepreg according to the invention are compared before and after a so-called high-pressure cooker test in comparison to the corresponding measured values on comparative products B, C and D.
- These are laminates which have been produced from prepregs which have been cured with nitrogen-containing compounds.
- the phenol-formaldehyde condensation product required for the preparation of the prepreg is produced in two stages, the first stage being phenol and formaldehyde in an aqueous solution in a molar ratio of phenol: formaldehyde in the range from about 1: 0.3 to 1: 0 , 7 are added, an acidic medium is established by adding a volatile acid and the whole is kept at an elevated temperature until the condensation reaction has ended, so that in a second stage the reaction product of the first stage is added a small part consists of phenol and otherwise predominantly dihydroxydiphenylmethane, formaldehyde is added in an amount so that the molar ratio in the first stage Phenol used
- the total amount of formaldehyde reacted in both stages is advantageously in the range from 1: 0.5 to 1: 0.9, advantageously 1: 0.6 to 1: 0.85, and the condensation reaction is continued at elevated temperature and ended, and that the condensation product is separated from the water and allowed to solidify outside the reaction kettle and com
- the resulting composite is passed through a heating zone, in which a temperature of 110 ° to 160 ° C prevails, whereby the desired B state of the impregnating resin is achieved.
- the prepreg is then passed through a calender and then cooled to room temperature in a cooling zone.
- test specimens for the High-pressure cooker test 15 layers of the prepregs produced as described are pressed into laminates and cured under a pressure of 7 bar at 170 ° C.
- the test specimens for the High-pressure cooker test For this purpose, the test specimens A, B, C and D are heated in an autoclave for one hour at 120 ° C./1.5 bar and then for two hours at 140 ° C./2.7 bar under steam.
- the flexural strength (MPa) of the test specimens was determined before and after the test.
- Hot-hardened composite materials with high permanent temperature and chemical resistance as well as composite parts for aircraft and mechanical engineering as well as for the manufacture of sporting goods are manufactured.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Composite Materials (AREA)
- Mechanical Engineering (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Préimprégné à base de fibres de renforcement, comme des fibres de verre, des fibres de carbone, des fibres d'aramide et similaires, disposées dans une seule direction et imprégnées par un mélange de matières plastiques duromères, dans lequel le mélange de matières plastiques contient une résine époxyde, une résine phénolique, le cas échéant un accélérateur et le cas échéant des additifs comme des charges, des retardateurs de flamme, des élastifiants, des agents mouillants et similaires. Ce préimprégné sert de matériau de départ pour des matériaux composites pressés à chaud ainsi que pour des éléments composites à constance thermique élevée et résistance élevée aux produits chimiques.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT1284/90 | 1990-06-13 | ||
AT0128490A AT396240B (de) | 1990-06-13 | 1990-06-13 | Prepreg verfahren zu seiner herstellung und seine verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0486651A1 true EP0486651A1 (fr) | 1992-05-27 |
Family
ID=3510559
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91910945A Withdrawn EP0486651A1 (fr) | 1990-06-13 | 1991-06-13 | Preimpregne, procede de fabrication et application |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0486651A1 (fr) |
JP (1) | JPH05501283A (fr) |
KR (1) | KR920702385A (fr) |
AT (1) | AT396240B (fr) |
WO (1) | WO1991019755A1 (fr) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59204678D1 (de) * | 1991-11-08 | 1996-01-25 | Ruetgerswerke Ag | Bindemittelsysteme auf Basis von Epoxydharz-Phenolharz-Kombinationen |
AT404240B (de) * | 1996-04-25 | 1998-09-25 | Isovolta | Laminat bestehend aus einer basis- und deckschicht sowie verfahren zur herstellung einer dekoroberfläche an diesem laminat |
GB2352249B (en) * | 1999-07-21 | 2004-04-14 | Rover Group | A method of manufacture of a glass fibre pre-preg for use in a polymer glazing application |
JP5762294B2 (ja) * | 2008-10-15 | 2015-08-12 | スリーエム イノベイティブ プロパティズ カンパニー | 一方向に整列した繊維を含む補強当て布 |
US20170087806A1 (en) | 2014-03-28 | 2017-03-30 | E I Du Pont De Nemours And Company | Fiber-reinforced composite laminate and articles made therefrom |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB888607A (en) * | 1958-06-18 | 1962-01-31 | Acoplast Kunststoff Verarbeitu | Improvements in and relating to the continuous production of profiled plastic sheets |
US3784659A (en) * | 1972-01-13 | 1974-01-08 | R Lupert | Method of producing continuous plastic shapes |
US3898113A (en) * | 1972-09-07 | 1975-08-05 | Gen Tire & Rubber Co | Method of making a continuous strand sheet molding compound |
JPS6037810B2 (ja) * | 1978-12-08 | 1985-08-28 | 東邦レーヨン株式会社 | ストランドプリプレグ組成物 |
GB2086444B (en) * | 1980-09-18 | 1985-01-23 | Sumitomo Chemical Co | Process for continuous production of prepreg sheets |
JPS59155044A (ja) * | 1983-02-23 | 1984-09-04 | 三井化学株式会社 | プリプレグおよび積層体 |
US4501787A (en) * | 1983-04-29 | 1985-02-26 | Westinghouse Electric Corp. | Flame retardant B-staged epoxy resin prepregs and laminates made therefrom |
US4599268A (en) * | 1984-04-16 | 1986-07-08 | International Business Machines Corporation | Product containing an epoxy composition |
DE3508600A1 (de) * | 1985-03-11 | 1986-09-11 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur herstellung von mit harz impraegnierten substraten zur verwendung bei der herstellung von laminaten fuer gedruckte schaltungen und danach hergestellte prepregs und laminate |
JPH02120330A (ja) * | 1988-10-28 | 1990-05-08 | Shin Kobe Electric Mach Co Ltd | 積層板の製造法 |
-
1990
- 1990-06-13 AT AT0128490A patent/AT396240B/de not_active IP Right Cessation
-
1991
- 1991-06-13 JP JP3510677A patent/JPH05501283A/ja active Pending
- 1991-06-13 KR KR1019920700320A patent/KR920702385A/ko not_active Application Discontinuation
- 1991-06-13 WO PCT/AT1991/000071 patent/WO1991019755A1/fr not_active Application Discontinuation
- 1991-06-13 EP EP91910945A patent/EP0486651A1/fr not_active Withdrawn
Non-Patent Citations (1)
Title |
---|
See references of WO9119755A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1991019755A1 (fr) | 1991-12-26 |
KR920702385A (ko) | 1992-09-03 |
JPH05501283A (ja) | 1993-03-11 |
AT396240B (de) | 1993-07-26 |
ATA128490A (de) | 1992-11-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE ES FR GB IT LI NL SE |
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17P | Request for examination filed |
Effective date: 19920521 |
|
17Q | First examination report despatched |
Effective date: 19950213 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 19960326 |