WO2005082988A1 - Polyurethane thermoplastique contenant des nanotubes de carbone - Google Patents
Polyurethane thermoplastique contenant des nanotubes de carbone Download PDFInfo
- Publication number
- WO2005082988A1 WO2005082988A1 PCT/EP2005/002050 EP2005002050W WO2005082988A1 WO 2005082988 A1 WO2005082988 A1 WO 2005082988A1 EP 2005002050 W EP2005002050 W EP 2005002050W WO 2005082988 A1 WO2005082988 A1 WO 2005082988A1
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- WIPO (PCT)
- Prior art keywords
- tpu
- carbon nanotubes
- mwnt
- thermoplastic polyurethane
- ohm
- Prior art date
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- 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
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
Definitions
- the present invention relates to thermoplastic polyurethane containing carbon nanotubes.
- Thermoplastic polyurethanes also referred to below as TPU, preferably TPU elastomers are generally known, commercially available and generally consist of a soft phase made of higher molecular weight polyhydroxyl compounds, e.g. from polyester or polyether segments, and a hard phase from urethane groups, formed from low molecular chain extenders and polyisocyanates.
- the antistatic or conductive finishing of plastics is usually achieved through the use of conductive carbon blacks or metal powders. Antistatic can now be achieved with suitable salts in combination with moisture with the advantage of not obtaining black products.
- the mixing of inherently conductive polymers is very limited due to strong changes in the properties of the matrix polymer. Especially in thermoplastic polyurethane, each filler causes a deterioration in the elasticity, especially since a very high addition is necessary to achieve conductivity, even when using conductive metals. Furthermore, a previously prepared preparation of the above. Additives in the TPU changed after processing in such a way that the desired conductivity properties are often no longer present in the finished part.
- the object of the present invention was therefore to develop a TPU that is designed to be antistatic or conductive and also has very good mechanical and / or dynamic properties.
- thermoplastic polyurethanes mentioned at the beginning i.e. the addition of carbon nanotubes to TPU.
- the electrical conductivity of the TPU can be significantly improved without significantly changing the property profile of the polymer. This is particularly surprising in view of the very high, complex property level of TPU.
- the characteristics of surface smoothness, gloss and feel that are characteristic of TPU are retained when the nanoscale fillers are stored.
- the preferably conductive thermoplastic polyurethanes according to the invention are preferably used in preferably flexible conductor tracks, preferably conductive foils and / or in the electromagnetic shielding.
- Preferred for the TPU according to the invention are all applications with an antistatic finish, in particular extrusion or injection molded articles.
- the carbon nanotubes contained in the TPU according to the invention are generally known and are commercially available, for example, from Nanocyl SA, Namur, Belgium or Nanoledge, Jardin, France.
- the carbon nanotubes preferably have an outer diameter between 1 nm and 50 nm, preferably between 3 nm and 25 nm, particularly preferably between 5 nm and 15 nm, and a length between 1 ⁇ m and 100 ⁇ m, preferably between 1 ⁇ m and 50 ⁇ m, particularly preferably between 1 ⁇ m and 10 ⁇ m it can preferably be single-walled (single wall or also abbreviated as SWNT), double-walled (double wall) or preferably multi-walled (multi wall, also abbreviated as MWNT), the ends of which can be open or closed.
- the carbon nanotubes can be used as a pure substance or as a master batch containing in thermoplastic materials, preferably mixed homogeneously with the TPU
- Particularly suitable materials are so-called single-wall nanotubes (single-walled nanotubes) and / or multi-wall nanotubes (multi-walled carbon nanotubes), which also survive the processing conditions of the TPU without damage and maintain conductivity after processing.
- SWNT Single-walled carbon nanotubes
- thermoplastic polyurethane preferably contains between 0.5% by weight and 10% by weight, preferably between 1% by weight and 8% by weight, of the carbon nanotubes, in each case based on the total weight of the thermoplastic polyurethane.
- TPUs are obtained by reacting (a) isocyanates, preferably diisocyanates with (b) compounds reactive toward isocyanates, usually with a molecular weight (M w ) of 500 to 10,000, preferably 500 to 5000, particularly preferably 800 to 3000 and ( c) chain extenders with a molecular weight of 50 to 499 optionally prepared in the presence of (d) catalysts and / or (e) customary additives.
- M w molecular weight
- organic isocyanates for example tri-, tetra-, penta-, hexa-, hepta- and / or octamethylene diisocyanate, 2- Methyl-pentamethylene-diisocyanate-1, 5, 2-ethyl-butylene-diisocyanate-1, 4, pentamethylene-diisocyanate-1, 5, butylene-diisocyanate-1, 4, 1-isocyanato-3,3,5-trimethyl- 5-isocyanato-methyl-cyclohexane (isophorone diisocyanate, IPDI), 1,4- and / or 1,3-bis (isocyanatomethyl) cyclohexane (HXDI), 1,4-cyclohexane diisocyanate, 1-methyl-2,4 - and / or
- the generally known compounds which are reactive toward isocyanates can be used, for example polyesterols, polyetherols and / or polycarbonate diols, which are usually also summarized under the term "polyols", with molecular weights between 500 and 8000, preferably 600 to 6000, in particular 800 to less than 3000, and preferably an average functionality compared to isocyanates of 1.8 to 2.3, preferably 1.9 to 2.2, in particular 2.
- Polyether polyols are preferably used, for example those based on of generally known starter substances and customary alkylene oxides, for example ethylene oxide, propylene oxide and / or butylene oxide, preferably polyetherols based on 1,2-propylene oxide and ethylene oxide and in particular polyoxytetramethylene glycols.
- the polyetherols have the advantage that they have a higher hydrolysis stability than polyesterols.
- low-unsaturated polyetherols can also be used as polyetherols.
- low-unsaturated polyols are understood in particular to mean polyether alcohols with an unsaturated compound content of less than 0.02 meg / g, preferably less than 0.01 meg / g.
- Such polyether alcohols are usually produced by addition of alkylene oxides, in particular ethylene oxide, propylene oxide and mixtures thereof, onto the diols or triols described above in the presence of highly active catalysts.
- highly active catalysts are, for example, cesium hydroxide and multimetal cyanide catalysts, also referred to as DMC catalysts.
- DMC catalysts A frequently used DMC catalyst is zinc hexacyanocobaltate. After the reaction, the DMC catalyst can be left in the polyether alcohol; it is usually removed, for example by sedimentation or filtration.
- thermoplastic polyurethanes which are preferably partially crosslinked, e.g. by siloxane groups, biuret, allophanate and / or urethane structures and / or via covalent linkages which are achieved by UV or electron beam crosslinking of unsaturated compounds, e.g. Butadien Modellen.
- polybutadiene diols e.g. those with a molar mass of 500 to 10000 g / mol are preferably used 1000 to 5000 g / mol, in particular 2000 to 3000 g / mol.
- TPUs which have been produced using these polyols can be crosslinked by radiation after thermoplastic processing. This leads e.g. to a small drip when exposed to flame.
- dimer fatty acid diols and / or dimer fatty acid polyols e.g. Dimerfetttklarepolyestern.
- chain extenders for example diamines and / or alkanediols with 2 to 10 carbon atoms in the Alkylene radical, in particular 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol and / or di-, tri-, tetra-, penta-, hexa-, hepta-, octa-, nona- and / or decaalkylene glycols with 3 to 8 carbon atoms, preferably corresponding oligo- and / or polypropylene glycols, it also being possible to use mixtures of the chain extenders.
- chain extenders for example diamines and / or alkanediols with 2 to 10 carbon atoms in the Alkylene radical, in particular 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol and / or di-, tri-, tetra
- Components a) to c) are particularly preferably difunctional compounds, i.e. Diisocyanates (a), difunctional polyols, preferably polyetherols (b) and difunctional chain extenders, preferably diols.
- Suitable catalysts which in particular accelerate the reaction between the NCO groups of the diisocyanates (a) and the hydroxyl groups of the structural components (b) and (c) are the tertiary amines known and customary in the prior art, such as triethylamine, dimethylcyclohexylamine hexylamine, N-methylmorpholine, N, N'-dimethylpiperazine, 2- (dimethyiaminoethoxy) ethanol, diazabicyclo (2,2,2) octane and the like, and in particular organic metal compounds such as titanium esters, iron compounds such as iron (III ) - acetylacetonate, tin compounds, for example tin diacetate, tin dioctoate, tin dilaurate or the tin dialkyl salts of aliphatic carboxylic acids such as dibutyl tin diacetate, dibutyl tin dilaurate or the like.
- auxiliaries and / or additives (e) can also be added to the structural components (a) to (c).
- component (e) also includes hydrolysis stabilizers such as, for example, polymeric and low-molecular carbodiimides.
- the thermoplastic polyurethane preferably contains triazole and / or triazole derivative and antioxidants in an amount of 0.1 to 5% by weight, based on the total weight of the thermoplastic polyurethane.
- antioxidants are commercially available. Examples of antioxidants are sterically hindered phenols, aromatic amines, thiosynergists, organophosphorus compounds of trivalent phosphorus, and hindered
- Amine Light Stabilizers Examples of sterically hindered phenols are found in Plastics Additives Handbook, th edition 5, H. Zweifel, ed, Hanser Publishers, Kunststoff, 2001 ([1]), pp 98-107 and S. 116-121. Examples of aromatic amines can be found in [1] pp. 107-108. Examples of thiosynergists are given in [1], pp.104-105 and pp.112-113. Examples of phosphites can be found in [1],
- antioxidants are preferably suitable for use in the antioxidant mixture.
- the antioxidants in particular the phenolic antioxidants, have a molar mass of greater than 350 g / mol, particularly preferably of greater than 700 g / mol and a maximum molar mass of ⁇ 10,000 g / mol, preferably ⁇ 3000 g / mol.
- they preferably have a melting point of less than 180 ° C.
- Antioxidants which are amorphous or liquid are also preferably used. Mixtures of two or more antioxidants can also be used as component (i).
- inorganic and / or organic fillers can preferably be contained in the TPU, preferably calcium carbonate, talc, bentonites, hydrotalcites (eg intercalated), nanocompo- sits, conventional types of mica, for example generally known MICA, usually in an amount between 1 and 10% by weight, preferably between 1 and 6% by weight, based on the total weight of the thermoplastic polyurethane.
- TPU preferably calcium carbonate, talc, bentonites, hydrotalcites (eg intercalated), nanocompo- sits
- conventional types of mica for example generally known MICA
- MICA metal-like effect on the electrical values. This is particularly important for cables in order to achieve sufficient volume resistance.
- chain regulators usually with a molecular weight of 31 to 3000, can also be used.
- Such chain regulators are compounds which have only one functional group which is reactive toward isocyanates, e.g. monofunctional alcohols, monofunctional amines and / or monofunctional polyols.
- a flow behavior in particular with TPUs, can be specifically set.
- Chain regulators can generally be used in an amount of 0 to 5, preferably 0.1 to 1 part by weight, based on 100 parts by weight of component b), and by definition fall under component (c).
- the build-up components (b) and (c) can be varied in relatively wide molar ratios.
- Molar ratios of component (b) to chain extenders (c) to be used in total from 10: 1 to 1:10, in particular from 1: 1 to 1: 4 have proven successful, the hardness of the TPU increasing with increasing content of (c).
- the implementation for the production of the TPU can be with a key figure of 0.8 to 1.4: 1, preferably with a key figure from 0.9 to 1.2: 1, particularly preferably with a key figure of 1.05 to 1.2: 1 done.
- the characteristic number is defined by the ratio of the total isocyanate groups of component (a) used in the reaction to the groups reactive towards isocyanates, i.e. the active hydrogens, components (b) and optionally (c) and optionally monofunctional isocyanate-reactive components as chain terminators, such as Monoalcohols.
- the TPU can be produced continuously using the known processes, for example using reaction extruders or the belt process using one-shot or the prepolymer process, or batchwise using the known prepolymer process.
- the components (a), (b), (c) and optionally (d) and / or (e) coming into the reaction can be mixed with one another in succession or simultaneously, the reaction commencing immediately.
- the build-up components (a), (b), (c) and optionally (d) and / or (e) are introduced into the extruder individually or as a mixture, for example at temperatures from 100 to 280 ° C., preferably 140 to 250 ° C, and for reaction brought.
- the TPU obtained is usually extruded, cooled and granulated.
- the TPU can optionally be modified by assembly on an extruder. This configuration enables the TPU to be modified, for example, in terms of its melt index or its granulate shape, according to the requirements.
- TPUs produced according to the invention which are usually in the form of granules or in powder form, into injection molding and extrusion articles, e.g.
- injection molding and extrusion articles e.g.
- the desired foils, molded parts, rolls, fibers, cladding in automobiles, hoses, cable plugs, bellows, trailing cables, cable sheathing, seals, belts or damping elements are carried out according to customary methods, e.g. Injection molding or extrusion.
- Such injection molding and extrusion articles can also be made from compounds containing the TPU according to the invention and at least one further thermoplastic, in particular a polyethylene, polypropylene, polyester, polyether, polystyrene, polycarbonate, PVC, ABS, ASA, SAN, polyacrylonitrile, EVA, PBT, PET, polyoxymethylene.
- the TPU produced according to the invention can be used to produce the articles shown at the beginning.
- the carbon nanotubes can be incorporated into the thermoplastic polyurethane by generally known methods, for example by kneading the desired amount of the additive in batches in an internal mixer or continuously mixing it into the melt in an extruder.
- the addition during the TPU synthesis on a conveyor system or a reaction extruder via the raw materials (e.g. the polyol component) is also possible.
- the carbon nanotubes can be used in the form of a concentrate, preferably in at least one thermoplastic for mixing with the thermoplastic polyurethane.
- concentrates which preferably contain the carbon nanotubes in an amount between 10 and 30% by weight, based on the total weight of the concentrate, there are, for example Mixtures of carbon nanotubes in known thermoplastics in question, e.g. in polycarbonate, polyester, polycaprolactone or styrene copolymers.
- Thermoplastic polyurethane (Elastollan® 1185A, Elastogran GmbH, polyether-based) was made in a DACA micro compounder (DACA Instruments, Goleta, USA) with cleaned multi-walled carbon nanotubes (MWNT, very thin multi-wall straight and coiled nanotubes, purified, manufacturer Nanocyl SA, Belgium) at 210 ° C, a speed of 50 rpm for 5 min. Both materials were dried and pre-mixed in the preheated, rotating compounder.
- DACA micro compounder DACA micro compounder
- MWNT very thin multi-wall straight and coiled nanotubes
- the composite at the mixing speed was expressed through the nozzle with a diameter of 2 mm, and a strand obtained at 100 ° C
- Thermoplastic polyurethane (Elastollan® 1185A, polyether-based) and with cleaned multi-walled carbon nanotubes (MWNT, see Example 1) were used in a DACA micro compounder (DACA Instruments, Goleta, USA) at 210 ° C., a speed of 50 rpm and a masterbatch with 15% by weight MWNT was produced in a mixing time of 5 min.
- DACA micro compounder DACA micro compounder
- Both materials can be described as electrically conductive.
- Thermoplastic polyurethane (Elastollan® 1185A, polyether-based) was made with unpurified multi-walled carbon nanotubes (MWNT, very thin multi-wall straight and coiled nanotubes, crude, manufacturer Nanocyl SA, Belgium) using DACA- Micro compounder processed as in Example 1. The extruded strands were measured for their volume conductivity as described in Example 1. The following resistance values resulted:
- the TPU was ground at low temperatures in order to achieve an intensive premixing with the powdery MWNT.
- Mixtures with TPU were produced from the granulated masterbatch under the same conditions on a 300 g scale.
- the granules were then injection molded with an Engel ES200H injection molding machine into S2 injection molded bodies in accordance with DIN 53 504 and mechanically tested after tempering (100 ° C, 20 h) (ISO 527-2 / 5A / 20).
- pure TPU was subjected to the same extrusion and injection molding treatment.
- sections of annealed injection molded parts were pressed at 210 C to a disc with a thickness of approx. 0.35 mm using a Vogt press.
- the volume resistivity of strips of approx. 3 mm made from this was determined using a 4-point test apparatus (measuring distance between the gold contacts 20 mm) combined with a Keithley 6517A electrometer. The following mean values resulted from the measurement on 10 samples.
- MPa Modulus of elasticity
- MPa tensile strength
- MPa elongation at break
- Thermoplastic polyurethane (Elastollan® 1185A polyether-based) was produced in a DACA micro compounder (DACA Instruments, Goleta, USA) with a masterbatch based on polycarbonate with 15% by weight multi-walled carbon nanotubes (MWNT) by Hyperion Catalysis Inc. (Cambridge, USA) ) mixed so that the absolute MWNT contents were 1, 2, 3 and 5% by weight MWNT.
- the mixtures were made from pre-dried granule premixes at 210 ° C., a speed of 100 rpm and a mixing time of 5 minutes.
- the extruded strands were annealed as described in Example 1 and measured for electrical volume resistance. The following specific volume resistances were achieved:
- Thermoplastic polyurethane (Elastollan® C85 polyester-based) was produced in a DACA micro compounder (DACA Instruments, Goleta, USA) with a masterbatch based on polycarbonate with 15% by weight multi-walled carbon nanotubes (MWNT) by Hyperion Catalysis Inc. (Cambridge, USA) mixed analogously to Example 5.
- the extruded strands were annealed as described in Example 1 and measured for electrical volume resistance. The following specific volume resistances were achieved:
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Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102004010455A DE102004010455A1 (de) | 2004-03-01 | 2004-03-01 | Thermoplastische Polyurethane enthaltend Kohlenstoffnanoröhren |
DE102004010455.7 | 2004-03-01 |
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WO2005082988A1 true WO2005082988A1 (fr) | 2005-09-09 |
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PCT/EP2005/002050 WO2005082988A1 (fr) | 2004-03-01 | 2005-02-26 | Polyurethane thermoplastique contenant des nanotubes de carbone |
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WO (1) | WO2005082988A1 (fr) |
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WO2009030357A1 (fr) * | 2007-08-30 | 2009-03-12 | Bayer Materialscience Ag | Pièces moulées présentant des surfaces de qualité améliorée |
WO2009083584A2 (fr) * | 2007-12-31 | 2009-07-09 | Wolfgang Beck | Transmetteur thermique pour l'exploitation énergétique du rayonnement thermique et de la convection |
US20100130701A1 (en) * | 2007-07-05 | 2010-05-27 | Tamfelt Pmc Oy | Shoe press belt |
FR2961201A1 (fr) * | 2010-06-11 | 2011-12-16 | Snpe Materiaux Energetiques | Propergols solides composites aluminises a faible sensibilite aux decharges capacitives et chargement comprenant de tels propergols solides |
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CN103834051A (zh) * | 2014-03-21 | 2014-06-04 | 福州大学 | 一种阻隔抗静电tpu复合材料薄膜及其制备方法 |
WO2014198752A1 (fr) | 2013-06-14 | 2014-12-18 | Basf Se | Corps moulé pouvant être chauffé en polyuréthane thermoplastique électriquement conducteur |
CN105386152A (zh) * | 2015-12-29 | 2016-03-09 | 浙江华峰氨纶股份有限公司 | 一种具有耐拉伸疲劳性能的聚氨酯纤维的制备方法 |
CN108250726A (zh) * | 2018-01-15 | 2018-07-06 | 东莞市安拓普塑胶聚合物科技有限公司 | 一种具有电磁屏蔽功能的阻燃tpu电缆护套料及其制备方法 |
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CN108410160A (zh) * | 2018-01-15 | 2018-08-17 | 东莞市安拓普塑胶聚合物科技有限公司 | 一种具有电磁屏蔽功能的阻燃tpu电缆护套料及其制备方法 |
CN115141394A (zh) * | 2022-07-12 | 2022-10-04 | 中国人民解放军海军工程大学 | 一种利用碳纳米管介电微胶囊制备聚氨酯复合膜的方法 |
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DE102007039901A1 (de) * | 2007-08-23 | 2008-10-16 | Siemens Ag | Thermisches und elektrisches Kontaktmaterial mit mindestens zwei Materialbestandteilen und Verwendung des Kontaktmaterials |
DE102008038499A1 (de) * | 2008-08-20 | 2010-02-25 | Trelleborg Sealing Solutions Germany Gmbh | Kunststoffherstellungsverfahren |
DE102009012674A1 (de) | 2009-03-13 | 2010-09-16 | Bayer Materialscience Ag | Polyurethanmassen mit Kohlenstoffnanoröhrchen |
DE102009015333A1 (de) * | 2009-03-27 | 2010-09-30 | Bayer Materialscience Ag | Antistatische und elektrisch leitfähige Polyurethan-Formteile |
DE102011009469B4 (de) | 2011-01-21 | 2013-04-18 | Innovent E.V. | Verfahren zur Herstellung von polymerfunktionalisierten Kohlenstoffnanoröhren |
DE102012022482A1 (de) * | 2012-11-19 | 2014-05-22 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Polymerzusammensetzung mit verbesserter Langzeitstabilität, hieraus hergestellte Formteile sowie Verwendungszwecke |
DE102013005307A1 (de) | 2013-03-25 | 2014-09-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von organischen Oxyimiden als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffzusammensetzung und hieraus hergestelltem Formteil |
DE102014210214A1 (de) | 2014-05-28 | 2015-12-03 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von Oxyimid-enthaltenden Copolymeren oder Polymeren als Flammschutzmittel, Stabilisatoren, Rheologiemodifikatoren für Kunststoffe, Initiatoren für Polymerisations- und Pfropfprozesse, Vernetzungs- oder Kopplungsmittel sowie solche Copolymere oder Polymere enthaltende Kunststoffformmassen |
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WO2009030357A1 (fr) * | 2007-08-30 | 2009-03-12 | Bayer Materialscience Ag | Pièces moulées présentant des surfaces de qualité améliorée |
WO2009083584A2 (fr) * | 2007-12-31 | 2009-07-09 | Wolfgang Beck | Transmetteur thermique pour l'exploitation énergétique du rayonnement thermique et de la convection |
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