WO2006062610A2 - Phase change material (pcm) compositions for thermal management - Google Patents
Phase change material (pcm) compositions for thermal management Download PDFInfo
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- WO2006062610A2 WO2006062610A2 PCT/US2005/038747 US2005038747W WO2006062610A2 WO 2006062610 A2 WO2006062610 A2 WO 2006062610A2 US 2005038747 W US2005038747 W US 2005038747W WO 2006062610 A2 WO2006062610 A2 WO 2006062610A2
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- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
- C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials
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Definitions
- PCM Phase Change Material
- the present invention relates to Phase Change Material (PCM) compositions for the thermal management in different applications like for example in building, automotive, packaging, garments and footwear.
- PCM Phase Change Material
- the present invention also relates to sheets and molded parts comprising the above PCM composition.
- PCM materials are highly-productive thermal storage media which are capable of absorbing and releasing high amounts of latent heat during melting and crystallization, respectively. During such phase changes, the temperature of the PCM materials remains nearly constant and so does the space surrounding the PCMs, the heat flowing through the PCM being "entrapped" within the PCM itself. Paraffin waxes are known to be particularly efficient as PCMs.
- Figure 1 shows a temperature profile simulation of the inside surface of three building wall structures (wood timber frames) during a typical summer day (latitude 45°; azimuth 180°; air T min 15°C; air T max 35 0 C).
- Such three wall structures comprise an external layer (wood siding, thickness 20 mm), a stone wool layer (thickness 250 mm) adjacent to such external layer and an internal gypsum board (thickness 10 mm).
- the first wall structure (W1) does not include PCM
- the second and third wall %tfuct ⁇ tes '1 (W2;W3 ' ) '1 furth ⁇ r 1 ' ' comprise a PCM composition layer positioned between the stone wool layer and the gypsum board layer, the PCM composition layers consisting of 7.15 wt% of PCM and 92.85 wt% of an hypothetical polymer and 45 wt% of PCM and 55 wt% of an hypothetical polymer, respectively.
- the PCM considered for this simulation is commercially available from Rubitherm under the trade name Rubitherm® RT20 (melting point 22°C).
- Figure 1 shows that the variation of the inside wall temperature during the day is reduced with increasing PCM amount in the wall structure or, in other words, that the heat management performance of the wall structure increases with increasing amount of PCM included therein.
- WO 2004/044345 discloses a wall covering assembly comprising phase change materials like crystalline alkyl hydrocarbons as a thermal storage mean.
- the assembly comprises 1 ) a cover layer of fabric or paper covered by a vinyl coating; 2) an intermediate layer made of an acrylic coating compound which contains finely divided PCM and a rear layer made of a liquid ceramic compound facing the wall during use.
- the capacity of the acrylic coating to incorporate PCM is limited due to the polarity and the elevated crystallinity degree of the acrylic material itself, so that the heat storage capacity of the overall assembly is limited to a certain extent.
- US 5,053,446 discloses a composite useful in thermal energy storage, said composite being a polyolefin matrix having a PCM (for example a crystalline alkyl hydrocarbon) incorporated therein.
- the polyolefin matrix is crystalline and must be thermally form stable up to temperatures of 150 - 180 0 C. This is due to the fact that the PCM imbibition of the matrix must take place at temperatures up to the above values in order to enable the PCM material itself to penetrate into the narrow spaces of the crystalline matrix.
- the thermal stability is usually achieved by reticulating the polyolefin prior to the imbibition process. This is an additional step for the preparation of the composite material, which additional step renders the overall manufacturing process more complicated and expensive.
- the problem at the root of the present invention is therefore to provide a PCM composition for the thermal management in different applications like for example in building, automotive, garments and footwear, which PCM composition can overcome the problems mentioned above.
- a PCM composition comprising: a) from 20 to 80 wt% of a PCM; and b) from 20 to 80 wt% of one or more polymers chosen from the group consisting of: b1) Very Low Density Polyethylene (VLDPE) having a density equal or lower than 0.910 g/cm 3 measured according to ASTM 792; b2) Ethylene Propylene Rubber (EPR) having a density equal or lower than 0.900 g/cm 3 measured according to ASTM 792; b3) Styrene Ethylene Butadiene Styrene (SEBS) copolymers; and b4) Styrene Butadiene Styrene (SBS) copolymers; the weight percentages being based on the total weight of the composition.
- VLDPE Very Low Density Polyethylene
- EPR Ethylene Propylene Rubber
- SEBS Styrene Ethylene Butadiene Styrene
- SBS Styrene Butadiene
- Figure 1 is a temperature profile simulation of the inside surface of three building wall structures (wood timber frames) during a typical summer day (latitude 45°; azimuth 180°; air T min 15°C; air T max 35 0 C).
- the polymers used in the present invention have low polarity and crystallinity.
- the low polarity degree of the polymer is important to enable compatibility between the polymer itself and a PCM of non-polar nature.
- the polymer matrices used in the present invention have sufficient absorption capacity to incorporate and retain high amounts of PCM, even at temperatures which are above or below the melting point of the PCM itself.
- the capacity of the above polymers to efficiently retain the PCM within their own matrix confers to the composition of the present invention an excellent heat management performance over long periods of time.
- the one or more polymers can be chosen among all types of SEBSs and SBSs copolymers which are well known to be amorphous and which typically have densities varying between 0.900 and 1.1 g/cm 3 .
- the PCM composition includes EPRs which are chosen among Ethylene Propylene Diene Methylene (EPDM), Ethylene Propylene Methylene (EPM) and mixtures thereof.
- EPRs which are chosen among Ethylene Propylene Diene Methylene (EPDM), Ethylene Propylene Methylene (EPM) and mixtures thereof.
- the sole polymer used in the PCM composition of the present invention is VLDPE having a density equal or lower than 0.910 g/cm 3 .
- the PCM composition of the present invention comprises from 30 to 50 wt% and still more preferably about 40 wt% of the one or more polymers, the weight percentages being based on the total weight of the PCM composition.
- the PCM is chosen among one or more alkyl hydrocarbons (paraffin waxes).
- Paraffin waxes are saturated hydrocarbon mixtures and generally consist of a mixture of mostly straight-chain n-alkanes with the chemical formula CH3-(CH2)n-CH3.
- the crystallization of the -(CH2)n- chain releases a large amount of the latent heat. Both the melting point and the heat of fusion increase with increasing chain length. Therefore, it is possible to select the paraffin waxes, which are products of petroleum refining, in such a way that the phase change temperature range matches with the temperature of the operation system to which the PCM is applied.
- the PCM composition of the present invention includes from 50 to 70 wt% of PCM, preferably 60 wt%, the weight percentages being based on the total weight of the PCM composition.
- the PCM composition of the present invention further comprises from 10 to 40 wt% of an inert powder having an absorption capacity of at least 50 wt% and preferably of at least 120 wt%, the weight percentages being based on the dried mass of the inert powder itself. The use of the inert powder further improves retention of the PCM within the polymeric matrix.
- the inert powder used in the PCM composition of the present invention is silicate, one or more flame retardant fillers and mixtures thereof.
- the one or more flame retardant fillers are advantageously chosen among aluminum trihydrate, magnesium hydroxide, melamine pyrophosphate, melamine cyanurate, one or more brominated fillers and mixtures thereof.
- the one or more polymers of the PCM composition are grafted with 0.2 to 3 wt% of a carboxylic acid or carboxylic acid anhydride functionality, the weight percentages being based on the total weight of the one or more polymers. While this small quantity of carboxylic acid or carboxylic acid anhydride does not affect the overall polarity of the polymer matrix, it is desirable to have such functionality in such amount if the PCM composition is used in combination with, for example, aluminum foils since the carboxylic acid or carboxylic acid anhydride functionality strongly improves adhesion of the PCM composition to metal surfaces.
- the polymer matrix of the PCM composition according to the present invention may be cross-linked after the PCM has been incorporated into it by means of any conventional method known in the art like for example by using cross-linking agents based on silane and/or peroxide groups. During this process, it is important to avoid that cross- linking of the PCM takes place. This is possible, for example, by grafting silane groups onto the polymer molecules prior to incorporating the PCM. Such grafting can occur by means of conventional techniques, such as by extruding the polymer at temperatures above 150 0 C after adding 0.2 to 2 wt-% of vinyl-tri-methoxy-silane or vinyl-tri-ethoxy-silane together with 0.05 to 0.5 wt-% peroxide.
- the PCM can then be incorporated into the silane grafted polymer and the resulting blend can be cross-linked, in presence of water or water moisture, by using catalysts like di-butyl-tin-laureate.
- catalysts like di-butyl-tin-laureate.
- the PCM composition of the invention may further comprise conventional additives such as antioxidants and UV filters. These additives may be present in the composition in amounts and in forms well known in the art.
- the PCM composition according to the present invention can be produced by soaking the different components all together at temperatures which are slightly above the melting point of the PCM but below the melting point of the one or more polymers. Soaking is a natural absorption of the molten PCM by the polymer matrix.
- the components are mixed together in a tumble blender during a certain period of time which can vary in function of the rotational speed of the tumble blender itself. Typical periods of time are around eight (8) hours.
- PCM composition of the present invention is by melt blend extrusion whereby the components are blended at temperatures above the melting point of both the one or more polymers and the PCM, the thus obtained mixture being subsequently extruded into granules or directly into sheets or any other suitable form.
- Sheets made with the PCM composition described above are also an object of the present invention.
- Preferably such sheets have a thickness varying between 0.5 and 10 mm and can be manufactured either directly by melt blend extrusion as described above, or alternatively by preparing the PCM composition which is subsequently processed by means of any conventional technology such as extrusion, calendering and hot lamination.
- Another object of the present invention is a multilayer structure comprising at least one sheet (A) of the above PCM composition, which is adjacent to at least one layer (B).
- sheet (A) is positioned between two layers (B1 ,B2).
- One of the functions of the at least one layer (B), or preferably of two layers (B1 ,B2) is to help keep the PCM material of the sheet (A) within the polymer matrix, thus enabling to maintain the heat management performance of the PCM sheet (A) at a high level over a long period of time.
- undesired grease stains on the surfaces adjacent to the PCM composition are hereby avoided.
- the multilayer structure comprises in the following sequence: a) at least one sheet (A); b) at least one layer (B) positioned adjacent to the at least one sheet (A); c) one or more additional layers (C) positioned adjacent to the at least one layer (B).
- the multilayer structure further comprises one or more additional layers (C) positioned adjacent and externally to one or more of the layers (B 1 , B2).
- the at least one layer (B) and the one or more additional layers (C) can also have the function of conferring to the overall multilayer structure improved fire retardancy and heat conductivity so that heat is easily conveyed through such at least one layer to the PCM composition and vice versa.
- the at least one layer (B) and the one or more additional layers (C) can be made of aluminum. It is also possible to use polyester vacuum coated on one side with aluminum, the aluminated side facing the PCM sheet (A), in order to achieve optimum adhesion. The use of aluminated polyester also confers to the overall PCM multilayer structure an excellent mechanical strength as well as an excellent elasticity.
- the at least one layer (B) and the one or more additional layers (C) can be made of other materials instead of (or in addition to) the above mentioned aluminum and/or polyester vacuum coated material, according to the specific use and application.
- Such materials can be independently chosen from one or more of flame retardant polymer compositions (polymers filled with flame retardant inorganic fillers like aluminum trihydrate, magnesium hydroxide, calcium carbonate, brominated fillers and melamine pyrophosphate), plaster (plaster boards and panels, gypsum boards), rock-wool insulation, glass-wool insulation, foamed polystyrene and other materials conventionally used in the construction industry.
- the at feastof ⁇ e layer (B) and the one or more additional layers (C) may have a thickness varying from 5 ⁇ m up to 20 cm in accordance with the materials used.
- Aluminum layers for example, will have thicknesses typically varying from 5 to 500 ⁇ m, preferably from 20 to 80 ⁇ m and, still more preferably, of about 50 ⁇ m.
- the multilayer structure of the present invention can be manufactured by conventional methods. This includes extrusion coating the PCM material onto the at least one layer (B), extrusion laminating the PCM material between two of such layers (B1 , B2), and co-extruding the PCM material with the at least one layer (B) if the material of such at least one layer (B) makes it possible (for example if the at least one layer is made of a flame retardant composition).
- An additional aspect of the present invention relates to a molded part made of a PCM composition as described above.
- Such molded part can be manufactured by any process suitable for transforming thermoplastic materials including injection molding, blow molding, thermoforming and rotomolding.
- the PCM composition of the present invention can be used in several applications where thermal management is needed. While temperature management inside buildings is one of the most relevant applications, the PCM composition of the present invention may also be used in automotive applications (for example in the ceiling, seats and tires of vehicles); air filters in air ducts; transportation applications; food packaging (to keep food chilled or warm); medical packaging; woven and nonwoven fabrics for garments and sport wear; footwear; tree wraps, hand grips (in tools, sporting goods and vehicles); bedding; carpets; wood composites; electric cables and plastic tubes for hot media including water.
- automotive applications for example in the ceiling, seats and tires of vehicles
- air filters in air ducts transportation applications
- food packaging to keep food chilled or warm
- medical packaging to woven and nonwoven fabrics for garments and sport wear
- footwear tree wraps, hand grips (in tools, sporting goods and vehicles)
- bedding carpets
- wood composites electric cables and plastic tubes for hot media including water.
- Example 1 55 g of paraffinic wax (PCM) commercially available from Rubitherm under the trade name Rubitherm® RT20 (melting point 22 0 C) and 45 g of granules of VLDPE (density 0.863 g/cm 3 ) grafted with 0.5 wt% of maleic anhydride, commercially available from E. I. du Pont de Nemours and Company under the trade name Fusabond® 493 D, were simultaneously introduced into an one liter tumble blender. Blending was carried out during eight (8) hours at 25°C in order to enable sufficient time for maximal incorporation of the liquid paraffinic wax into the polymer matrix (soaking).
- PCM paraffinic wax
- the granules soaked with the paraffinic wax were taken out of the blender and filtered in order to remove rests of liquid paraffin wax from their external surface. The difference in the granules weight before and after soaking was measured, thus allowing to calculate the weight percentage of wax absorbed by the polymer matrix.
- Slabs were compression molded using the PCM composition obtained above.
- the granules were placed in a frame (thickness of 2 mm) between 2 steel slabs and the whole system was subsequently pressed at a jaw temperature of 100 0 C and at a pressure of 1 bar during the first minute and of 80 bars during the subsequent 2 minutes.
- the jaws were then cooled down to 25 0 C during a period of 4 minutes always under a pressure of 80 bars. The pressure was eventually released and the produced polymer slabs removed from the frame.
- Example 1 was repeated using granules of ethylene methyl acrylate, comprising 25 wt% of methyl acrylate, commercially available from E .I. du Pont de Nemours and Company under the trade name Elvaloy® AC 1125. No slabs were made with the PCM composition obtained under this Example 2.
- Example 1 was repeated using granules of VLDPE (density 0.863 g/cm 3 ), commercially available from Dow Chemicals under the trade name Engage® 8180. No slabs were made with the PCM composition obtained under this Example 3. The results are shown in Table 2.
- Example 1 was repeated using granules of HDPE (density 0.965 g/cm 3 ), commercially available from E. I. du Pont de Nemours and Company under the name DuPontTM 6611. No slabs were made with the PCM composition obtained under this Example 4. The results are shown in Table 2.
- Example 5 (comparative) Example 1 was repeated using granules of HDPE (density 0.965 g/cm 3 ), commercially available from E. I. du Pont de Nemours and Company under the name DuPontTM 6611. Blending was carried out during eight (8) hours at 18O 0 C.
- HDPE density 0.965 g/cm 3
- Table 2 shows that the polymer matrices according to the present invention (Examples 1 and 3) can absorb the whole amount of PCM (55 g PCM per 45 g polymer) at 25 0 C while polymers having high degrees of polarity (Example 2) or high degrees of crystallinity (Example 4) can absorb PCM only to a limited extent.
- PCM polymer having high degrees of polarity
- Example 4 polymers having high degrees of crystallinity
- Slabs obtained by molding the PCM compositions according to the present invention are very flexible and show excellent mechanical properties.
- Example 5 shows that slabs prepared with PCM compositions based on crystalline polymers (HDPE) are very brittle. Therefore, from a mechanical point of view, such compositions are not suitable in the thermal management applications described above even if their PCM content is quite high.
- HDPE crystalline polymers
- VLDPE density 0.863 g/cm 3
- Engage® 8180 a mix of vinyl-tri- methoxy-silane and peroxide catalyst
- PCM paraffinic wax
- Rubitherm® RT20 melting point 22°C
- di-butyl-tin- laureate 0.03 g of di-butyl-tin- laureate and 45 g of the VLDPE based blend obtained above, were simultaneously introduced into an one liter tumble blender. Blending was carried out during eight (8) hours at 25°C in order to enable sufficient time for maximal incorporation of the liquid paraffinic wax and di-butyl-tin- laureate into the polymer matrix (soaking). The granules soaked with the paraffinic wax and di-butyl-tin-laureate were taken out of the blender.
- PCM paraffinic wax
- Slabs were compression molded using the PCM composition obtained in this Example 6 as well as the one obtained in Example 3.
- the granules were placed in a frame (thickness of 2 mm) between 2 steel plates and the whole system was subsequently pressed at a jaw temperature of 150 0 C and at a pressure of 1 bar during the first minute and of 80 bars during the subsequent 2 minutes.
- the jaws were then cooled down to 25°C during a period of 4 minutes always under a pressure of 80 bars.
- the pressure was eventually released and the produced polymer slabs removed from the frame.
- the slabs were then immerged in water during 4 hours and dumble bar samples were cut out from these slabs, according to method DIN 53504 S2.
- Table 3 shows that the cross-linked composition obtained in Example 6 has a significantly improved resistance to heat deformation if compared to the same uncross-l inked composition (Example 3).
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Abstract
Description
Claims
Priority Applications (6)
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CA2588304A CA2588304C (en) | 2004-12-09 | 2005-10-26 | Phase change material (pcm) compositions for thermal management |
AT05812787T ATE541022T1 (en) | 2004-12-09 | 2005-10-26 | LATERENT HEAT STORAGE MATERIALS (PCM) FOR THERMAL MANAGEMENT |
EP05812787A EP1838802B1 (en) | 2004-12-09 | 2005-10-26 | Phase change material (pcm) compositions for thermal management |
ES05812787T ES2379637T3 (en) | 2004-12-09 | 2005-10-26 | Compositions of phase change materials (MCF) for thermal management |
JP2007545461A JP5204491B2 (en) | 2004-12-09 | 2005-10-26 | Phase change material (PCM) composition for temperature control |
CN2005800479903A CN101115817B (en) | 2004-12-09 | 2005-10-26 | Phase change material (pcm) compositions for thermal management |
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US63459204P | 2004-12-09 | 2004-12-09 | |
US60/634,592 | 2004-12-09 |
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US (2) | US20060124892A1 (en) |
EP (2) | EP1838802B1 (en) |
JP (1) | JP5204491B2 (en) |
CN (1) | CN101115817B (en) |
AT (1) | ATE541022T1 (en) |
CA (1) | CA2588304C (en) |
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2005
- 2005-10-26 CA CA2588304A patent/CA2588304C/en not_active Expired - Fee Related
- 2005-10-26 WO PCT/US2005/038747 patent/WO2006062610A2/en active Application Filing
- 2005-10-26 AT AT05812787T patent/ATE541022T1/en active
- 2005-10-26 EP EP05812787A patent/EP1838802B1/en not_active Not-in-force
- 2005-10-26 ES ES05812787T patent/ES2379637T3/en active Active
- 2005-10-26 EP EP10184154A patent/EP2261297A2/en not_active Withdrawn
- 2005-10-26 US US11/258,779 patent/US20060124892A1/en not_active Abandoned
- 2005-10-26 CN CN2005800479903A patent/CN101115817B/en not_active Expired - Fee Related
- 2005-10-26 JP JP2007545461A patent/JP5204491B2/en not_active Expired - Fee Related
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2011
- 2011-06-20 US US13/164,239 patent/US8333903B2/en not_active Expired - Fee Related
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EP1881026A2 (en) * | 2006-07-19 | 2008-01-23 | Continental Aktiengesellschaft | Rubber composition |
EP1881026A3 (en) * | 2006-07-19 | 2010-01-06 | Continental Aktiengesellschaft | Rubber composition |
JP2011515551A (en) * | 2008-03-26 | 2011-05-19 | ルビテルム・テクノロジーズ・ゲーエムベーハー | Method for producing phase change material polymer composite |
WO2011014636A1 (en) | 2009-07-30 | 2011-02-03 | E. I. Du Pont De Nemours And Company | Thermal insulation unit |
WO2011089061A1 (en) | 2010-01-19 | 2011-07-28 | Huntsman International Llc | Materials comprising a matrix and process for preparing them |
WO2011143278A1 (en) | 2010-05-13 | 2011-11-17 | E. I. Du Pont De Nemours And Company | Phase change material compositions |
US8308861B2 (en) | 2010-05-13 | 2012-11-13 | E I Du Pont De Nemours And Company | Phase change material compositions |
DE102012110330A1 (en) * | 2012-10-29 | 2014-04-30 | STS Textiles GmbH & Co. KG | Textile fabric useful as a mat with defined outlines, comprises a latent heat accumulator comprising a monofilament made of a phase change material, and does not comprise outer shell or other structuring material |
DE102012110330B4 (en) * | 2012-10-29 | 2014-07-24 | STS Textiles GmbH & Co. KG | Textile fabric with a latent heat storage |
US10435606B2 (en) | 2014-05-01 | 2019-10-08 | Performance Materials Na, Inc. | Cables made of phase change material |
WO2015168096A1 (en) | 2014-05-01 | 2015-11-05 | E. I. Du Pont De Nemours And Company | Cables made of phase change material |
WO2016165999A1 (en) | 2015-04-13 | 2016-10-20 | Hutchinson | Heat storage material |
US11180625B2 (en) | 2015-04-13 | 2021-11-23 | Hutchinson | Thermally and/or electrically conductive materials and method for the production thereof |
US11326083B2 (en) | 2015-04-13 | 2022-05-10 | Hutchinson | Heat storage matertal |
WO2017079018A1 (en) | 2015-11-03 | 2017-05-11 | E. I. Du Pont De Nemours And Company | Cables made of phase change material |
DE102016209098A1 (en) * | 2016-05-25 | 2017-11-30 | Leibniz-Institut Für Polymerforschung Dresden E.V. | RUBBER OR ELASTOMER COMPOSITIONS AND METHOD FOR THE PRODUCTION THEREOF |
US10435543B2 (en) | 2016-05-25 | 2019-10-08 | Leibniz-Institut Fuer Polymerforschung Dresden E.V. | Rubber or elastomer compositions and processes for their manufacturing |
WO2017214398A1 (en) | 2016-06-09 | 2017-12-14 | E. I. Du Pont De Nemours And Company | Heat storage cable including closing system |
EP3878922A1 (en) | 2016-06-09 | 2021-09-15 | E. I. du Pont de Nemours and Company | Heat storage cable including closing system |
WO2018204298A2 (en) | 2017-05-01 | 2018-11-08 | E. I. Du Pont De Nemours And Company | Composition and methods for coaxial devices including a phase change material |
KR20200078178A (en) | 2018-12-21 | 2020-07-01 | 한국화학연구원 | Composition comprising phase change material and method for producing thereof |
Also Published As
Publication number | Publication date |
---|---|
US20060124892A1 (en) | 2006-06-15 |
CA2588304A1 (en) | 2006-06-15 |
WO2006062610A3 (en) | 2007-02-08 |
JP5204491B2 (en) | 2013-06-05 |
CN101115817A (en) | 2008-01-30 |
US8333903B2 (en) | 2012-12-18 |
EP1838802A2 (en) | 2007-10-03 |
ES2379637T3 (en) | 2012-04-30 |
CN101115817B (en) | 2013-09-18 |
CA2588304C (en) | 2012-12-18 |
EP2261297A2 (en) | 2010-12-15 |
EP1838802B1 (en) | 2012-01-11 |
JP2008523204A (en) | 2008-07-03 |
ATE541022T1 (en) | 2012-01-15 |
US20110248208A1 (en) | 2011-10-13 |
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