EP1230294A1 - Feuille preimpregnee stable au stockage a base de matrices lipochimiques thermodurcissables - Google Patents

Feuille preimpregnee stable au stockage a base de matrices lipochimiques thermodurcissables

Info

Publication number
EP1230294A1
EP1230294A1 EP00981207A EP00981207A EP1230294A1 EP 1230294 A1 EP1230294 A1 EP 1230294A1 EP 00981207 A EP00981207 A EP 00981207A EP 00981207 A EP00981207 A EP 00981207A EP 1230294 A1 EP1230294 A1 EP 1230294A1
Authority
EP
European Patent Office
Prior art keywords
prepreg according
component
prepreg
oil
group
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Withdrawn
Application number
EP00981207A
Other languages
German (de)
English (en)
Inventor
Michael Skwiercz
Ralf Bemmann
Horst Sulzbach
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
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 Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1230294A1 publication Critical patent/EP1230294A1/fr
Withdrawn legal-status Critical Current

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
    • 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • 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
    • 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
    • C08J5/045—Reinforcing macromolecular compounds with loose or coherent fibrous material with vegetable or animal 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
    • C08J5/245—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using natural fibres
    • 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
    • C08L63/10—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
    • C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
    • C08J2363/10—Epoxy resins modified by unsaturated compounds

Definitions

  • the present application relates to storage-stable prepregs, a method for producing such prepregs, fiber composite materials produced from these prepregs and the use of such fiber composite materials.
  • Fiber composite materials consist at least of fibers and a matrix material.
  • the fibers serve to reinforce the material.
  • the fibers absorb tensile forces acting on the material in particular, the matrix fills voids between the fibers and envelops the fibers.
  • the matrix thus transmits in particular the shear forces that act on the composite material.
  • the matrix protects the coated fibers from external influences such.
  • Fiber composite materials are known, for example from glass fiber, metal fiber or carbon fiber reinforced synthetic plastics. In the past, these composite materials have proven themselves in many fields of application due to their high resilience, durability and reproducibility.
  • renewable raw materials are not exhausted, they can be regenerated at any time by growing suitable plants by photosynthesis.
  • Prepreg technology is regularly used in the production of fiber-resin composite materials.
  • Prepreg is understood to mean a semi-finished product pre-impregnated with thermoplastic or thermosetting material, which is further processed into the finished part in a further processing step.
  • fibers are impregnated with a resin matrix in suitable systems.
  • the prepregs can then either be processed directly after their production by curing to the desired finished parts or, and this is one of the advantages of this technique, first stored and then finished later if required. Since the prepregs themselves are usually in the form of mats, variable finished parts can be obtained from them, depending on requirements, for example.
  • thermosetting matrices With prepregs with thermosetting matrices, however, the problem arises that, due to the material properties of conventional thermosets, only very short storage times are possible (at most a few weeks, sometimes only a few minutes), since the material hardens quickly at normal temperature (21 ° C). If prepregs based on thermosets are to be stored for a longer period of time, the components need to be deep-frozen (up to - 30 ° C) on a regular basis.
  • thermosets are understood to mean both the raw materials prior to crosslinking (ie the reactive resins) and the cured reaction products.
  • the object on which the present invention was based was to produce prepregs based on thermosetting matrices which avoid the disadvantages mentioned above, in particular the short shelf life at normal temperature.
  • the production of the prepregs should continue to use predominantly to completely renewable raw materials.
  • a first subject of the present invention are prepregs which are stable at room temperature and contain a fiber material and a thermosetting matrix which contains (a) an epoxy and / or hydroxyl group-containing fatty substance with at least 12 carbon atoms, (b) a crosslinking agent and (c) a catalyst.
  • the prepregs according to the invention can contain synthetic fibers such as glass fibers, carbon fibers, metal fibers and the like, as well as natural fibers. Within the scope of the present invention, those prepregs are preferred which are produced at least partially, advantageously but completely, on the basis of natural fibers.
  • the proportion of natural fibers is preferably 50% by weight and larger, based on the weight of the fibers. Prepregs whose fibers s are composed of 100% by weight of natural fibers as defined below are particularly preferred.
  • These natural fibers can be used in the form of short fibers, yarns, rovings or preferably textile fabrics in the form of nonwovens, needled nonwovens, tangled nonwovens, woven fabrics, scrims or knitted fabrics.
  • natural fibers are preferably selected from flax, hemp, straw, wood wool, sisal, jute, coconut, ramie, bamboo, bast, cellulose, cotton or wool fibers, animal hair or fibers based on 0 chitin / chitosan or their combination.
  • those prepregs are preferred which completely or partially contain flax fibers as the fiber material.
  • the proportion by weight of fiber material is between 10 and 70% by weight, preferably 30 to 60% by weight and in particular 35 to 55% by weight
  • the fibers can be brought into contact with the matrix by all methods known to the person skilled in the art in order to obtain the prepregs according to the invention.
  • the fibers are preferably immersed in the matrix, but spray processes are also possible.
  • the thermoset matrix itself consists predominantly, preferably completely, of oleochemical raw materials. These are mixtures of (a) reactive, oxygen-containing fatty substances with (b) crosslinkers and (c) catalysts. It is preferred that the component mixtures from (a), (b) and (c) have a Brookfield viscosity, when applied to the fiber, of 600 to 1400 mPas, preferably 800 to 1200 mPas and in particular from 900 to 1100 mPas, measured with Spindle 5, 10 min- 1 . The viscosity values relate to the application temperature.
  • the matrix is applied to the fibers at temperatures of 40 to 80 ° C.
  • Compounds according to (a) are reactive, oxygen-containing fatty substances which can be characterized as follows, where at least 12 carbon atoms must be present in the molecule.
  • the upper limit for the carbon number is preferably 56, in particular 36, carbon atoms.
  • the compounds of reaction component (a) have at least one reactive oxygen-containing group, either the epoxy and / or the hydroxyl group in the molecule, which enables them to react with the crosslinking agents of group (b) and to form high molecular weight, solid agglomerates, which together with the fiber the fiber composite material has the desired physical properties, such as Tensile strength and flexural strength.
  • a group of component (a) are epoxidized triglycerides, such as z. B. can be obtained by reacting natural unsaturated fats and oils with formic acid and hydrogen peroxide.
  • suitable starting materials are preferably the natural fats and oils from rapeseed, sunflowers, soybeans, linseed, hemp, castor oil, coconuts, oil palms, oil palm kernels and oil trees, each of which contains triglycerides of unsaturated fatty acids in portions.
  • the most important representatives of the epoxidized fats and oils are the epoxidized soybean oil and the epoxidized rapeseed oil as well as the epoxidized linseed oil.
  • nucleophiles are alcohols such as. B. water methanol, ethanol, ethylene glycol, glycerol or trimethylolpropane, amines such as. B. ethanolamine, diethanolamine, triethanolamine, ethylenediamine, dipropylenetriamine or hexamethylenediamine or carboxylic acids such as acetic acid, dimer fatty acid, maleic acid, phthalic acid, terephthalic acid or a mixture of mono- and / or difunctional fatty acids with 6 to 30 carbon atoms.
  • alcohols such as. B. water methanol, ethanol, ethylene glycol, glycerol or trimethylolpropane
  • amines such as. B. ethanolamine, diethanolamine, triethanolamine, ethylenediamine, dipropylenetriamine or hexamethylenediamine or carboxylic acids such as acetic acid, dimer fatty acid, maleic acid, phthalic acid, terephthalic acid or a mixture
  • Nucleophiles for ring opening of the epoxidized fatty substances can also be fatty alcohols.
  • Suitable fatty alcohols are aliphatic, linear or branched primary alcohols with 6 to 22 carbon atoms. Typical examples are caprone alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, technical alcohol alcohol, aryl alcohol alcohol, arachyl alcohol, arachyl alcohol, arachyl alcohol, arachyl alcohol, arachyl alcohol, arachyl alcohol, alcohol alcohols in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsatur
  • nucleophiles for reaction with epoxidized triglycerides are propene, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane -, Heptadecanoic, Octadecanoic, Nonadecanoic, Eicosanoic, Docosanoic, Hexacosanoic and Triacontanoic acid and mixtures thereof.
  • crotonic acid, itaconic acid, maleic acid, fumaric acid or mixtures thereof are particularly preferred.
  • component (a) is, however, always the oxygen-containing derivatives.
  • R 1 represents a hydrogen atom or a methyl radical and R2 represents a hydrogen atom or represents an alkyl radical having 1 to 22 C atoms.
  • the salts of these compounds are also suitable.
  • Preferred compounds which fall under the general formula (I) are acrylic and methacrylic acid, and also their esters with fatty alcohols. Reaction products of linseed and / or soybean oil, which are mixed with acrylic and / or methacrylic acid, are preferred.
  • reaction components (a) is selected from reaction products of unsaturated fatty substances, preferably fatty acids or fatty acid esters, with anhydrides, preferably maleic anhydride.
  • Suitable unsaturated fatty acids are e.g. 10-undecanoic acid, laurolein, myristoleic, palmitolein, petroselin, petroseladein, oleic, eladic, ricinol, linoleic, linolaidic, gadoleinic, arachidonic, erucic, brassidic and clupanodonic acid and their mixtures.
  • Polyunsaturated acids are also suitable, e.g.
  • reaction products of triglycerides based on unsaturated fatty acids with the anhydrides are preferably used.
  • Reaction products of epoxidized triglycerides with anhydrides are also suitable components (a) for the production of matrices for storage-stable prepregs according to the invention.
  • Suitable anhydrides are preferably those which are prepared from cyclic polycarboxylic acids with two free carboxylic acid groups, for example cyclohexanedicarboxylic anhydride,
  • Cyclohexenedicarboxylic anhydride phthalic anhydride, trimellitic anhydride, hemimellitic anhydride, pyromellitic anhydride, 2,3-naphthalic anhydride, 1,2-cyclobutanoic dicarboxylic anhydride, 1,2-cyclopentanedicarboxylic anhydride,
  • Particularly suitable anhydrides are maleic anhydride, phthalic anhydride and trimellitic anhydride, and also derivatives of these anhydrides and mixtures.
  • the crosslinker (b) is an organic compound which has at least two reactive sites in the molecule which can react with the compounds according to (a). However, compounds with three, four or an even greater number of reactive sites in the molecule which are suitable for crosslinking are also suitable.
  • component (b) from the group selected from diallyl phthalates, dipropylene glycol diacrylate or diethylene glycol diacrylate are particularly suitable.
  • Reactive anhydrides are also suitable as component (b), here again preferably the maleic anhydride.
  • Catalysts (c) are added to the thermosetting matrices as initiators of the actual curing reaction.
  • These are preferably organic peroxide compounds, such as tert-butyl periso ⁇ anoate (TBPIN) or tert-butyl perethyl hexanoate (TBPEH).
  • Basic catalysts are also used, preferably organic aliphatic or aromatic amine compounds.
  • imidazoline derivatives preferably 1-methylimidazole, is particularly preferred.
  • Component (c) is contained in the matrices in amounts of from 0.01 to 10% by weight, preferably from 0.5 to 5% by weight and in particular from 1.0 to 3% by weight. Components (a) and (b) make up the remainder to 100% by weight of the matrix. It is preferred to select quantitative ratios of component (a) to (b) from 4: 1 to 1: 1. Component (a) is preferably contained in the matrix in excess of component (b). The quantitative ratio is then (a) / (b) from 80/20 to 60/40 and very preferably 70/30.
  • the matrices can also contain other auxiliaries and additives known to those skilled in the art of prepreg production, for example flame retardants, color pigments, UV absorbers and organic and inorganic fillers.
  • Another object of the invention relates to methods for producing a storage-stable prepreg by (I) a fiber material is brought into contact with a thermosetting matrix material at temperatures of 40 to 80 ° C in the presence of a catalyst and then (II) that with the matrix in
  • Contacted fiber material is cooled to temperatures of less than or equal to 30 ° C, which
  • Matrix material is selected from an epoxy and / or hydroxyl group-containing fatty substance with at least 12 carbon atoms, a crosslinking agent and a catalyst, and the matrix material in the
  • Temperatures in step (I) have a Brookfield viscosity of 600 to 1400 mPas.
  • the prepregs can be produced in all ways known to the person skilled in the art, a continuous procedure being preferred. Details can be found, for example, in Schlichting et al., Verbundwerkstoffe, Lexika-Verlag, Grafenau, 1978, pages 208 to 211.
  • the prepregs obtained in this way can be cured to the desired finished parts by curing at temperatures of> 80 ° C., preferably> 100 ° C.
  • a fiber composite material according to the invention is preferably obtained by curing the prepregs according to the invention at 100 to 250 ° C. Curing temperatures in the range from 120 to 180 ° C. and in particular from 130 to 160 ° C. are particularly preferred.
  • the curing time is usually short and is only a few minutes at temperatures around 150 ° C.
  • Another object of the invention relates to fiber composite materials that are produced as described above. Furthermore, the use of such fiber composites for the production of components for vehicle construction, aircraft construction, the construction industry, window construction, the furniture industry, the electrical industry, sports equipment, toys, machine and apparatus construction, the packaging industry, agriculture or security technology is claimed.
  • Linseed oil acrylate (a) was mixed with dipropylene glycol diacrylate as crosslinker (b) in a weight ratio of 70:30.
  • the mixture had a Brookfield viscosity of 1000 mPas (spindle 5; 10 min- 1 ) at 65 ° C.
  • 1% by weight of TBPEH and TBPIN were added to the mixture as free radical initiator (c) and the matrix was then applied to a flax fiber at 65 ° C.
  • the prepreg thus obtained was storable at temperatures ⁇ 30 ° C for 6 months.
  • the prepreg was cured at 150 ° C for 60 seconds and thus processed into a finished fiber composite workpiece.
  • Soybean oil acrylate (a) was mixed with diallyl phthalate (b) in a ratio of 70:30 to a matrix (Brookfield viscosity at 40 ° C 1000 mPas, spindle 5; 10 min- 1 ).
  • 1% by weight of TBPIN and TBPEH were added and the mixture was then applied to a flax fiber at 65 ° C.
  • the prepreg obtained in this way was storable for 6 months at temperatures of ⁇ 30 ° C and could then be easily processed into a finished component by curing (150 ° C, 60 seconds).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Reinforced Plastic Materials (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne des feuilles préimprégnées stables au stockage à température ambiante, à base de matrices lipochimiques thermodurcissables, obtenues par mise en contact d'une matière fibreuse contenant de préférence des fibres naturelles, avec une matière matricielle à des températures comprises entre 40 et 80 DEG C, en présence d'un catalyseur approprié. La matière fibreuse imprégnée de la matrice est refroidie à des températures de 30 DEG C et moins et la matière matricielle est sélectionnée dans le groupe comprenant un solide ayant au moins 12 atomes de C et contenant des groupes époxy et/ou hydroxyle, un agent réticulant, ainsi qu'un catalyseur. A des températures comprises entre 40 et 80 DEG C, la matière matricielle présente une viscosité Brookfield allant de 600 à 1400 mPas.
EP00981207A 1999-10-30 2000-10-21 Feuille preimpregnee stable au stockage a base de matrices lipochimiques thermodurcissables Withdrawn EP1230294A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19952364 1999-10-30
DE19952364A DE19952364A1 (de) 1999-10-30 1999-10-30 Lagerstabile Prepregs auf Basis duroplastischer, oleochemischer Matrices
PCT/EP2000/010394 WO2001032755A1 (fr) 1999-10-30 2000-10-21 Feuille preimpregnee stable au stockage a base de matrices lipochimiques thermodurcissables

Publications (1)

Publication Number Publication Date
EP1230294A1 true EP1230294A1 (fr) 2002-08-14

Family

ID=7927432

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00981207A Withdrawn EP1230294A1 (fr) 1999-10-30 2000-10-21 Feuille preimpregnee stable au stockage a base de matrices lipochimiques thermodurcissables

Country Status (7)

Country Link
EP (1) EP1230294A1 (fr)
JP (1) JP2003514048A (fr)
AR (1) AR026259A1 (fr)
AU (1) AU1853801A (fr)
CA (1) CA2389539A1 (fr)
DE (1) DE19952364A1 (fr)
WO (1) WO2001032755A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10148672A1 (de) * 2001-10-02 2003-04-24 Cognis Deutschland Gmbh Polyester
DE10154364A1 (de) * 2001-11-06 2003-05-15 Cognis Deutschland Gmbh Dämmstoff für Schallwellen
US8357643B2 (en) * 2004-08-10 2013-01-22 Battelle Memorial Institute Lubricants derived from plant and animal oils and fats
EP1919987A1 (fr) * 2005-08-16 2008-05-14 A B Composites Private Limited Composite thermodurcissable de fibres naturelles et son procede de fabrication
DE102006003762A1 (de) * 2006-01-25 2007-07-26 Dracowo Forschungs- Und Entwicklungs Gmbh Leinölepoxid-basierte Faserverbundwerkstoffe
ITMI20100101A1 (it) * 2010-01-27 2011-07-28 Consiglio Nazionale Ricerche Pannelli a base lignocellulosica a basso rilascio di formaldeide (classe e1)
DE102011001539A1 (de) * 2011-03-24 2012-09-27 Meyer Rohr + Schacht Gmbh Verbundwerkstoff
FR2973812A1 (fr) * 2011-04-06 2012-10-12 Fibres Rech Dev Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4119295C2 (de) * 1991-06-12 1994-12-01 Frische Gmbh Umweltsicherer Verbundwerkstoff aus Naturfasern bzw. -produkten und Kunststoffen des Typs Polyurethan-Polyester und/oder Polyurethan-Polyamid sowie Verfahren zu dessen Herstellung
CN1103791C (zh) * 1995-07-05 2003-03-26 空间分割系统预成形股份有限公司 聚合材料,其制造方法和应用
DE19644017A1 (de) * 1996-10-31 1998-05-07 Basf Ag Naturfaser-verstärkte Polyisocyanat-Polyaddidionsprodukte, Verfahren zu deren Herstellung und deren Verwendung
DE19930770A1 (de) * 1999-07-03 2001-01-04 Cognis Deutschland Gmbh Verfahren zur Herstellung von Faserverbundwerkstoffen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0132755A1 *

Also Published As

Publication number Publication date
AR026259A1 (es) 2003-02-05
AU1853801A (en) 2001-05-14
JP2003514048A (ja) 2003-04-15
CA2389539A1 (fr) 2001-05-10
WO2001032755A1 (fr) 2001-05-10
DE19952364A1 (de) 2001-07-19

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