WO2000059989A1 - Substances composites a base de matieres premieres renouvelables - Google Patents

Substances composites a base de matieres premieres renouvelables Download PDF

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Publication number
WO2000059989A1
WO2000059989A1 PCT/EP2000/002532 EP0002532W WO0059989A1 WO 2000059989 A1 WO2000059989 A1 WO 2000059989A1 EP 0002532 W EP0002532 W EP 0002532W WO 0059989 A1 WO0059989 A1 WO 0059989A1
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WO
WIPO (PCT)
Prior art keywords
monomers
anhydride
composite materials
fibers
thermoplastics
Prior art date
Application number
PCT/EP2000/002532
Other languages
German (de)
English (en)
Inventor
Christian Priebe
Michael Skwiercz
Horst Sulzbach
Ralf Bemmann
Original Assignee
Cognis Deutschland Gmbh
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 filed Critical Cognis Deutschland Gmbh
Priority to AU41076/00A priority Critical patent/AU4107600A/en
Publication of WO2000059989A1 publication Critical patent/WO2000059989A1/fr

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Classifications

    • 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
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • 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
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • 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
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • C08J2377/12—Polyester-amides

Definitions

  • the invention relates to a composite material based on natural fibers and a matrix material and the use of such 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.
  • Natural fiber reinforced plastics are known per se; their advantages compared to glass fiber reinforced plastics are already described with regard to raw material basis, ecological balance, occupational safety, weight or thermal disposal, see e.g. B. Kohler, R .; Wedler, M .; Kessler, R .: “Do we use the potential of natural fibers?” In: Gülzower technical discussions “Natural fiber reinforced plastics” (Ed. horrisco, Gülzow 1995), pp. 95-100 or "Guideline for renewable raw materials, cultivation, processing, products” , 1st edition, Heidelberg: Müller, 1998, in particular chapter 8. A distinction can be made between thermoplastic and thermosetting systems with regard to the matrices used.
  • EP-A-687 711 describes a system with thermoplastic matrices based on renewable raw materials Fiber composite material made of biodegradable fibers and a matrix made of biodegradable material. Cellulose acetate, lignin, starch and starch derivatives are proposed as suitable thermoplastic materials for the matrix. In practical use, it can be seen that composites according to the disclosure of EP-A-687 711 have certain disadvantages in technical application. For example, starch-based matrix materials are not water-resistant and composites based on cellulose or biopoly are not acceptable due to the price
  • the present invention is therefore based on the object of providing composite materials based on thermoplastic materials, in which both the reinforcing agents and the matrix materials are essentially based on renewable raw materials. Furthermore, these materials are to be compared to both in practical use and in price known products improved
  • the present invention relates to composite materials based on natural fibers and a material that contains oleochemical thermoplastics with a melting point of less than 200 ° C., the thermoplastics being essentially composed of polyesters, polyamides and / or polyester amides based on renewable raw materials
  • Another object of the present invention is a method for producing components from the thermoplastics and natural fibers according to the invention
  • Another object of the present invention is the use of the composite materials according to the invention for the production of components for vehicle construction, i.e. automobile construction, rail vehicle construction, aircraft construction, the production of body parts and interior fittings.
  • the composite materials according to the invention can be used in the construction industry for insulation materials, sandwich elements and the like, in Window construction for the construction of window frames, door frames and doors are used, in the furniture industry for the production of panels, furniture parts and mobein, in the electrical / energy industry for the production of computers, household appliances, housings, air blowers or wind turbines in the field of leisure activities and in Sports can be made from the composite materials according to the invention, sports equipment, boats, gliders and Toys are manufactured, in mechanical engineering they can be used for the production of gearwheels or gear parts, in waste management for the production of waste containers In plant engineering containers, pumps, pipe elements can be produced from the composite materials according to the invention, in the packaging industry the materials according to the invention can be used for the production of Use bottles, hollow bodies, molded parts and technical packaging.
  • thermoplastics are polymeric, soft or hard materials at the operating temperature, which have a flow transition area above the operating temperature.DIN 7724 Part 2 limits the thermoplastics via the temperature curve of the shear modulus G from the other polymer classes, the elastomers and the thermosets Thermoplastics a variety of plastics, such as polyolefins, vinyl polymers or polyurethanes
  • thermoplastics which essentially contain those polymers which are available from selected polyesters, polyamides and polyester amides based on renewable raw materials. These thermoplastics have a melting point of less than 200 ° C. in order to be processed with the natural fibers To be particularly preferred are thermoplastics whose melting point is at 100 to 180 ° C. Oleochemical derivatives or fatty substances within the meaning of the present invention are natural, in particular vegetable or animal oils, and in particular their derivatives or secondary products by chemical reaction.
  • oils are in nature in the form of natural mixtures of different fatty acid glycol nests, for example in Palmol, Palmkernol, Palmstea ⁇ n, olive oil, Rubol, Koreanderol, sunflower oil, cotton oil, peanut oil, hemp oil, linseed oil, Lardol, Fischol, Fischtranol, pork lard or beef tallow Die Fe
  • t-acid components of the abovementioned natural triglycene are in particular the mono- or polyunsaturated acids palmitoleic, oil, elaidin, petroselinic, eruca, ricinol, hydroxymethoxysteanic, 12-hydroxystearic, linoleic, unioleic and gadoleic acids
  • further functional groups capable of crosslinking such as hydroxyl, mercapto, carboxyl, amino, acid anhydride or epoxy groups or else olefinic double bonds, can be introduced into
  • the composite materials according to the invention are produced on the basis of renewable raw materials.
  • the composite materials depending on the composition, can also have advantageous behavior In terms of biodegradation, however, this is not always an advantageous property, since depending on the use of the composite materials, in particular when components are used in the field of automobile construction, early rotting is undesirable.
  • composite materials which are only one Slow biodegradability is preferred. Biodegradability of such materials is understood to mean, for example, the proof that the corresponding material (which relates to any organic component in the material to a mass proportion of 1% by weight) is converted to C0 2 and / or biomass at least 60% by weight within 6 months.
  • a corresponding DIN is in preparation
  • the fatty acids (a) are unsaturated compounds of the general formula (I)
  • R 1 is a branched or unbranched olefinically unsaturated alkyl radical having 7 to 23 carbon atoms and 1 to 3 double bonds.
  • preferred unbranched mono- and polyunsaturated fatty acids are 10-undecenoic acid, laurolein, my ⁇ stolein, palmitolein, Petroselinic, petroseladeinic, oil, Eladm, ricinolic, linoleic, linolenic, linolaidic, gadolemic, arachidonic, erucic, brassidic and clupanodonic acids
  • thermoplastics in addition to the monocarboxylic acid of the formula (I), their derivatives, in particular their esters with C 1 to C 4 alcohols, ie methanol, ethanol, propanol and butanol, can also be used to prepare the thermoplastics according to the invention
  • Monomers (a) suitable which are prepared by ene reaction or Diels-Alder reaction of unsaturated anhydrides on isolated and / or conjugated double bonds with olefinically unsaturated C 2 2 fatty acids
  • Acid anhydrides are also suitable, such as maleic anhydride, succinic anhydride, citraconic anhydride, itaconic anhydride, phthalic anhydride, trimellitic anhydride, 4-cyclohexane-1, 2-dicarboxylic acid anhydride and naphthalene diacid, naphthalic dehydro-1, naphthalic dehydro-1, naphthalic dehydro-1, naphthalic dehydro-1, naphthalic dicarboxylic acid, naphthalic dicarboxylic acid, naphthalic dehydro-1, naphthalic dicarboxylic acid, naphthalic dicarboxylic acid, naphthalic dicarboxylic acid, naphthalic diacid anhydrides, and naphthalene dicarboxylic acid mixtures,
  • thermoplastics Another class (b) of monomer units for the production of thermoplastics are dicarboxylic acids. These are compounds of the general formula
  • R 2 is a saturated or unsaturated divalent alkyl or hydroxylalkyl radical with 1 to 20 C atoms.
  • Particularly preferred are aliphatic dicarboxylic acids with 2 to 18 C atoms in the molecule. Examples of such preferred aliphatic ⁇ , ⁇ -dicarboxylic acids are the oxalic, Malonic, amber, glutar-adipic, pimeline, cork, sube ⁇ n, azelaine, sebacic, undecandi, dodecanedic, brassyl and tetradecanic acid.
  • Unsaturated dicarboxylic acids are, for example, maine, fumaric, citraconic or mesaconic acid
  • Particularly advantageous thermoplastics contain azelaic acid as the monomer component.
  • Hydroxycarboxylic acids such as glycolic, lactic, almond, tartronic, apple, tartaric or citric acid, are particularly suitable as derivatives of dicarboxylic acid, with glycolic, lactic and tartaric acids being particularly preferred
  • Dimer fatty acids (c) are suitable as a third class of oleochemical raw materials.
  • the omegomerization of unsaturated fatty acids is a known electrocychic reaction about which, in review articles, for example, by A Behr in Fat Sei Technol 93, 340 (1991), G Spiteller in Fat Sei Technol 94 , 41 (1992) or P Daute et al in Fat Sei Technol 95, 91 (1993) is reported.
  • oligomerization occurs, an average of two to three fatty acids come together and form dimers or fibers, which predominantly have cycloaliphatic structures a so-called monomer fraction is obtained, in which there are unreacted starting materials and branched monomers which are formed in the course of the reaction by isomerization. In addition, there is of course also a fraction of higher oligomers, but this is generally not of major importance.
  • the ohgomerization can be thermal or in the presence of precious metal catalysate be carried out
  • the reaction is preferably carried out in the presence of clays such as, for example, montmorillonite [cf. Greases, soaps, paints. 72, 667 (1970)].
  • the regulation of the content of dimers and trimers and the extent of the monomer fraction can be controlled by the reaction conditions.
  • Technical mixtures can finally also be purified by distillation.
  • Technical unsaturated fatty acids with 12 to 22, preferably 16 to 18, carbon atoms are suitable as starting materials for the oligomerization.
  • Typical examples are palmoleic acid, oleic acid, elaidic acid, petroselinyl acid, linoleic acid, linolenic acid, conjuene fatty acid, elaeostearic acid, ricinoleic acid, gadoleic acid, erucic acid and their technical mixtures with saturated fatty acids.
  • Suitable technical mixtures are uncured split fatty acids of natural triglycerides with iodine numbers in the range from 40 to 140, such as palm fatty acid, tallow fatty acid, rapeseed oil fatty acid, sunflower fatty acid and the like. Split fatty acids with a high oleic acid content are preferred.
  • their esters preferably methyl esters, can also be dimerized in a manner known per se.
  • Dimer fatty acids which are particularly preferred for the purposes of the invention, are obtained by the oleigomerization of technical oleic acid and preferably have a dimer content of 50 to 99% by weight and a polymer content (including trimer content) of 1 to 50% by weight.
  • the monomer content can be 1 to 15% by weight and, if necessary, reduced by distillation.
  • Dimer fatty acids which are obtained by oil igomerization of technical oleic acid and have a dimer content of 70 to 85% by weight, a polymer content of 10 to 20% by weight and a monomer content of 5 to 15% by weight are particularly preferred.
  • The% by weight are based on the total amount of dimer fatty acid.
  • dimer fatty acids their derivatives, in particular dimer diamines, can also be used to produce the thermoplastics according to the invention.
  • dimer diamines these are amino fatty substances based on dimer and / or trimer acids that have been reacted with low molecular weight polyamines.
  • Dimer diols can be used further as derivatives of Dimerfettsauren, as sold for example under the trade name Sovermol 908 ® by the applicant.
  • the last class of suitable monomers are the polyols and their derivatives (d). These are compounds with at least two carbon atoms and two hydroxyl groups in the molecule.
  • Suitable polyols are glycol, glycerin and Glycennmono-, di and -trifettsaureester, especially Glyce ⁇ monoester with C 8 -C 2 fatty acids, and their di- and polymers, especially Polyglyce ⁇ ne come according to DE-A-36 36 086 Diglyce ⁇ n, T ⁇ glyce ⁇ n and linear or branched Tetraglycenn as well as technical Polyglycine mixtures, such as those produced by condensing Glycenn at elevated temperature and reduced pressure in the presence of alkaline catalysts with exclusion of air and subsequent removal of the catalyst with the aid of ion exchangers, are considered.
  • Preferred polyglycines in the sense of the invention are those which contain the glycerol ethers from diglycene to heptaglycne and up to 20% by weight of monomeric glycine and, above all, may have hydroxyl numbers in the range from 900 to 1200
  • the preparation of the material is carried out in a manner known per se by polymerizing the monomers. Both homopolymers and copolymers or terpolymers can be used. Material materials based on purely oleochemical monomers are preferred. However, other monomers, such as aliphatic diamines, can also be condensed are known alkyl derivatives with 4 to 22 carbon atoms which have two amino groups -NH 2 in the molecule.
  • diamines examples include ethylenediamine or 1,2-diminopropane, 1,3-diminopropane, 1,6 diammohexane, 1, 8-D ⁇ am ⁇ nooctan, 1, 9-D ⁇ am ⁇ nononan or 1, 12-D ⁇ am ⁇ nododecan
  • Aromatic diamines for example 4,4-D ⁇ am ⁇ nod ⁇ phenylbutan or Diaminobenzen are suitable
  • thermoplastic materials contained in the composite materials according to the invention essentially consist, ie at least 50% by weight, of monomers (a) to (c). Depending on the monomers selected, polyesters, polyamides or polyester amides are formed.
  • Thermoplastic materials are also expressly used in the context of the present application
  • Basis of polycarbonates comprises the polycarbonates are polyesters, which preferably! can be formed by reacting phosgene with oleochemically based dimer alcohols, fatty acid monoglycides or ricinole fatty acid ethylene glycol diesters
  • the material can be made up of up to 100% by weight from these monomers.
  • monomers other than (a) to (d) can also be condensed in, their proportion then being less than 50% by weight, preferably in the range of 5 to 40 % By weight and preferably in the range from 10 to 30% by weight.
  • Particularly preferred are those thermoplastic matrix materials which are obtained predominantly or completely by condensation of dimer fatty acids or derivatives (c) with dicarboxylic acids or their derivatives (b).
  • Thermoplastics which are predominantly or completely composed of dicarboxylic acids (monomers of group (b)) and polyols, in particular ethylene glycol (monomers of group (d)), are also preferred.
  • auxiliaries can be added to the composite materials, these include flame retardants, color pigments, UV absorbers and organic and / or inorganic fillers.
  • natural fibers are preferably used according to the invention.
  • These natural fibers can be in the form of short fibers, yarns, rovings or, preferably, textile fabrics in the form of nonwovens, needled nonwovens, random nonwovens, woven fabrics, scrims or knitted fabrics. It can contain cellulose fibers such as flax, hemp, straw, wood wool, sisal, jute, coconut, ramie, bamboo, bast or cotton fibers or wool fibers, animal hair or fibers based on chitin / chitosan and Combinations of the fibers mentioned above can be used.
  • the fiber composite materials according to the invention can be processed to shaped articles by all known production technologies. It is common to all these known production technologies for molded articles that the starting materials fiber and matrix are brought together to form a molding compound which solidifies on, in or between solid molding tools to form a composite. In this process, the fiber starting material is introduced into a melted matrix mass of the thermoplastic and completely wetted and coated with it by means of a compression process. The type of fiber material to be introduced therefore largely determines the manufacturing process to be used. So z. B. no reinforcing material in the form of fabric can be used in an extrusion process. Short fibers, on the other hand, are very suitable for extrusion processes or spray applications of matrix / fiber mixtures.
  • the choice of the suitable matrix material depends on the type of fiber, the fiber pre-product and last but not least on the setting speed and the area size.
  • the impregnation of the fiber and the hardness cycle of the matrix determine both the quality of the bond and the connection of the layers to one another, especially that of the interlaminar strength.
  • Examples of manufacturing technologies which can be used according to the invention include the pultrusion process, production using the winding technique, pressing technique, vacuum technique, differential pressure-resin transfer molding (DP-RTM), resin transfer molding (RTM), prepreg technology.
  • thermoplastics Manufacture of thermoplastics. For the work-up, the reaction product was poured out and broken after cooling.
  • dimer fatty acid (Empol ® 1061) were reacted with 107.2 g of azelaic acid and 132.2 g of 1, 6-diaminohexane under a nitrogen atmosphere at 180 ° C. for five hours in a steel double-jacket reactor. The water formed was distilled off.
  • dimer fatty acid (Empol ® 1061) were reacted with 107.2 g of azelaic acid and 644.5 g of dimer diamine (Versamine 552) under nitrogen atmosphere at 180 ° C for five hours in a Stahldoppelmanteireaktor to the reaction. The water formed was distilled off.
  • Composites were in each case produced from the thermoplastics according to Examples 1, 2 and 4, in that tangled nonwovens made of flax with a mass of 200 g / m 2 were enclosed in the soft thermoplastics at 200 ° C. and the material was subsequently pressed.
  • the composite materials according to the invention have homogeneously bonded flax layers and show improved tensile strength values compared to the comparative examples. Table 1

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nonwoven Fabrics (AREA)

Abstract

L'invention concerne une substance composite fibreuse à base de fibres naturelles et d'une matière matricielle contenant des matières thermoplastiques oléochimiques dont le point de fusion est inférieur à 200 °C. Lesdites matières thermoplastiques oléochimiques sont constituées essentiellement de polyesters, de polyamides et/ou de polyamides d'esters à base de matières premières renouvelables.
PCT/EP2000/002532 1999-04-01 2000-03-22 Substances composites a base de matieres premieres renouvelables WO2000059989A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU41076/00A AU4107600A (en) 1999-04-01 2000-03-22 Composite substances based on renewable raw materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1999114925 DE19914925A1 (de) 1999-04-01 1999-04-01 Verbundwerkstoffe
DE19914925.9 1999-04-01

Publications (1)

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WO2000059989A1 true WO2000059989A1 (fr) 2000-10-12

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AU (1) AU4107600A (fr)
DE (1) DE19914925A1 (fr)
WO (1) WO2000059989A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009112369A1 (fr) * 2008-03-13 2009-09-17 Ems-Patent Ag Élastomère de polyamide
WO2010058140A1 (fr) * 2008-11-21 2010-05-27 Arkema France Compositions de polyamide et de renforts bioressources a proprietes mecaniques ameliorees
EP2415838A1 (fr) * 2010-08-06 2012-02-08 Henkel AG & Co. KGaA Matériau composite contenant des fibres naturelles
CN107254778A (zh) * 2017-07-25 2017-10-17 安徽亚源印染有限公司 一种抗菌耐污的亚麻人造棉弹力面料

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008012096B4 (de) * 2008-02-29 2010-01-14 Rittal Gmbh & Co. Kg Schaltschrank oder Rack
FR2966171B1 (fr) * 2010-10-18 2013-12-27 Univ Nancy 1 Henri Poincare Materiau souple a base de fibres et de resines naturelles

Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0518338A1 (fr) * 1991-06-12 1992-12-16 Dr. Frische GmbH Compound compatible avec l'environnement
EP0687711A2 (fr) * 1994-06-16 1995-12-20 DEUTSCHE FORSCHUNGSANSTALT FÜR LUFT- UND RAUMFAHRT e.V. Matériau composite fibreux et procédé pour le produire
DE19705280C1 (de) * 1997-02-12 1998-03-05 Daimler Benz Ag Faserverstärktes Kunststoff-Formteil und Verfahren zu dessen Herstellung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0518338A1 (fr) * 1991-06-12 1992-12-16 Dr. Frische GmbH Compound compatible avec l'environnement
EP0687711A2 (fr) * 1994-06-16 1995-12-20 DEUTSCHE FORSCHUNGSANSTALT FÜR LUFT- UND RAUMFAHRT e.V. Matériau composite fibreux et procédé pour le produire
DE19705280C1 (de) * 1997-02-12 1998-03-05 Daimler Benz Ag Faserverstärktes Kunststoff-Formteil und Verfahren zu dessen Herstellung

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009112369A1 (fr) * 2008-03-13 2009-09-17 Ems-Patent Ag Élastomère de polyamide
WO2010058140A1 (fr) * 2008-11-21 2010-05-27 Arkema France Compositions de polyamide et de renforts bioressources a proprietes mecaniques ameliorees
FR2938847A1 (fr) * 2008-11-21 2010-05-28 Arkema France Compositions de polyamide et de renforts bioressources a proprietes mecaniques ameliorees
CN102282199A (zh) * 2008-11-21 2011-12-14 阿克马法国公司 具有改善的机械性能的聚酰胺与生物资源增强材料的组合物
US10358527B2 (en) 2008-11-21 2019-07-23 Arkema France Polyamide and bioresourced reinforcement compositions having improved mechanical properties
EP2415838A1 (fr) * 2010-08-06 2012-02-08 Henkel AG & Co. KGaA Matériau composite contenant des fibres naturelles
WO2012016799A1 (fr) 2010-08-06 2012-02-09 Henkel Ag & Co. Kgaa Matériau composite contenant des fibres naturelles
CN103052686A (zh) * 2010-08-06 2013-04-17 汉高股份有限及两合公司 含有天然纤维的复合材料
US8969440B2 (en) 2010-08-06 2015-03-03 Henkel Ag & Co. Kgaa Composite material containing natural fibers
KR101838768B1 (ko) * 2010-08-06 2018-03-14 헨켈 아게 운트 코. 카게아아 천연 섬유를 함유하는 복합 재료
CN107254778A (zh) * 2017-07-25 2017-10-17 安徽亚源印染有限公司 一种抗菌耐污的亚麻人造棉弹力面料

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AR023232A1 (es) 2002-09-04
DE19914925A1 (de) 2000-10-05
AU4107600A (en) 2000-10-23

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