WO2014001081A1 - Siloxan-mischungen - Google Patents
Siloxan-mischungen Download PDFInfo
- Publication number
- WO2014001081A1 WO2014001081A1 PCT/EP2013/062037 EP2013062037W WO2014001081A1 WO 2014001081 A1 WO2014001081 A1 WO 2014001081A1 EP 2013062037 W EP2013062037 W EP 2013062037W WO 2014001081 A1 WO2014001081 A1 WO 2014001081A1
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- WIPO (PCT)
- Prior art keywords
- mass
- zero
- sio
- general formula
- methylpolysiloxanes
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 91
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title description 29
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000012530 fluid Substances 0.000 claims abstract description 10
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims abstract description 3
- 230000000704 physical effect Effects 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract description 2
- -1 siloxanes Chemical class 0.000 description 14
- 238000000034 method Methods 0.000 description 11
- 229910004298 SiO 2 Inorganic materials 0.000 description 8
- 229920002545 silicone oil Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 6
- 239000013529 heat transfer fluid Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000008646 thermal stress Effects 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229920004488 WACKER® AK 5 SILICONE FLUID Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002902 bimodal effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- 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
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24S—SOLAR HEAT COLLECTORS; SOLAR HEAT SYSTEMS
- F24S80/00—Details, accessories or component parts of solar heat collectors not provided for in groups F24S10/00-F24S70/00
- F24S80/20—Working fluids specially adapted for solar heat collectors
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/40—Solar thermal energy, e.g. solar towers
Definitions
- the present invention relates to mixtures of siloxanes and their use as heat transfer fluid.
- Organosiloxanes and organopolysiloxanes are frequently used as heat transfer fluids because of their high thermal stability, their wide fluid range and the low temperature dependence of their viscosity Particularly in the range of very low (below -50 ° C.) or very high temperatures (200 ⁇ 400 ° C.), they are superior to organic heat transfer fluids or the only nonionic heat transfer fluid that can be used
- siloxanes predestine them for use as high-temperature heat transfer fluids, for example in solar thermal power plants, especially in those with parabolic trough and Fresnel technology, where the heat transfer fluid is exposed for years to high thermal stress up to 400 ° C and strong temperature fluctuations.
- the Use of silicone oils in solar thermal devices is described in DE 2754705 A1, US 4122109 and US 4193885.
- composition 'of siloxane mixtures is by rearrangement approximately processes depending on the temperature and thus to reach a state of equilibrium at the selected temperature and time dependent.
- achieving equilibrium for example at 400 ° C, may take several days.
- the physical properties change as well. This can lead to that important operating parameters of a siloxane mixture with an operated as a heat transfer fluid device / for example, the vapor pressure or significantly change with time the viscosity. This is disadvantageous since it may require additional control and regulation effort or even additional expenditure in the construction of the device, or the device may be limited or not usable in this period of time.
- the object of the invention is therefore to provide siloxanes which have temporally approximately constant physical properties after reaching a certain temperature in order to avoid the disadvantages mentioned.
- siloxane mixtures can have temporally approximately constant physical properties under thermal stress at a constant temperature, although their chemical composition changes over time to equilibrium.
- the composition of these siloxane mixtures must not speak of equilibrium composition at this temperature ent ⁇ surprisingly,
- the invention provides mixtures of methylpolysiloxanes containing at least two methylpolysiloxanes selected from linear compounds of the general formula I.
- x has values greater than or equal to zero and the one with the
- Molar arithmetic mean of x over all linear methylpolysiloxanes is between 3 and 20,
- y has values greater than or equal to 3 and the arithmetic mean of y over all cyclic methylpolysiloxanes weighted by the molar proportions is between 3 and 6,
- the number ratio of Me 3 Si chain end groups in the compounds of general formula I to the sum of Me 2 SiO units in the compounds of general formulas I and II is at least 1: 2 and at most 1:10,
- the sum of the proportions of all cyclic methylpolysiloxanes of the general formula 11 is at least 10% by mass and at most 40% by mass
- the mixture is liquid at 25 ° C and has a viscosity of less than 100 mPa * s.
- the composition of the mixture is chosen so that at least one of the physical properties density, vapor pressure, viscosity, heat capacity or thermal conductivity during thermal stress of the mixture at a constant temperature remains approximately constant over time.
- the composition of the mixture if the desired physical properties of all components of the mixture are known to be temperature-dependent, can be determined by calculation or also empirically. The case that the composition of the Mi ⁇ research the equilibrium mixture corresponding to at the selected temperature, is trivial.
- the invention is based on the fact that mixtures of composition other than the equilibrium composition can have the physical properties of the equilibrium mixture at the selected temperature.
- the siloxane mixtures according to the invention have the advantage that at least one physical property selected from density, vapor pressure, viscosity, heat capacity or thermal conductivity can be kept constant over time, even though the chemical composition of the siloxane mixture still changes until equilibrium is reached, In designing and operating the solar thermal device, therefore, no consideration needs to be given to any changes in the selected physical properties,
- variable x preferably assumes values between zero and 100, particularly preferably between zero and 70, very particularly preferably between zero and 40.
- the weighted arithmetic mean value of x over all linear methylpolysiloxanes is preferably between 4 and 15, more preferably between 5 and 10, in each case including the stated limit values.
- variable y preferably has values between 3 and 100, particularly preferably between 3 and 70, very particularly preferably between 3 and 40.
- the weighted arithmetic mean of y over all cyclic methylpolysiloxanes is preferably between 3.5 and 5.5, more preferably between 4 and 5, in particular between 4 and 4.5, in each case including the stated limit values.
- the number ratio of the Me 3 Si-chain end groups in the general formula I to the sum of Me 2 SiO- Einhei s in the ERAL ⁇ NEN formulas I and II is preferably at least 1: 2.5 and not more than 1: 8, more preferably at least 1: 3 and at most 1: 6,
- % for X 29 and 30 each between 0.1 and 6 mass%, for X 31 to 34 each between zero and 3 mass%, for X a 35 to 40 each between zero and 1.5 mass%, for X 41 to 70 each between zero and 0.5 mass%, and for x greater than 70 each between zero and 0.1 mass%, and independently particularly preferred
- the sum of the proportions of all cyclic methylpolysiloxanes of the general formula II is at least 12.5 mass% and at most 35 mass%, in particular at least 15 mass% and at most 30 mass%.
- the viscosity of the siloxane mixtures according to the invention at 25 ° C. preferably has values below 50 mPa * s, more preferably below 20 mPa * s, very particularly preferably below 10 mPa * s,
- the siloxane mixtures according to the invention can be present in a monomodal, bimodal or multimodal molecular weight distribution; at the same time, the molecular weight distribution can be narrow or broad.
- the siloxane mixtures according to the invention preferably have a bimodal, trimodal or tetramodal molecular weight distribution.
- the siloxane mixtures according to the invention preferably contain less than 1000 ppm of water, more preferably less than 500 ppm of water, most preferably less than 200 ppm of water, in each case based on the mass,
- the mixtures according to the invention consist of methylpolysiloxanes
- the mixtures have a trimodal molecular weight distribution and at 25 ° C have a viscosity of less than 10 mPa * s, preferably the physical properties selected from density, vapor pressure, viscosity, heat capacity and thermal conductivity of the mixture, in particular all these properties after reaching a constant temperature between 300 ° C.
- Siloxane mixtures according to the invention can be prepared by preparing pure siloxanes of the general formulas I or II or mixtures of such siloxanes in any order, mixing them and metering them together, if appropriate also multiply-repeating, also alternately or simultaneously. By suitable methods, for example distillation, siloxanes or slixxane mixtures can also be removed again.
- the composition of the siloxane mixture according to the invention is controlled by the amounts of siloxanes of general formulas I and II used or removed.
- the process can be carried out at room temperature and ambient pressure, but also at elevated or reduced temperature and elevated or reduced pressure.
- Siloxane mixtures according to the invention can furthermore be prepared by hydrolyzing or cohydrolyzing suitable chlorosilanes, alkoxysilanes or mixtures of chlorosilanes or alkoxysilanes and subsequently liberating them from by-products such as chlorine hydrogen or alcohols and optionally from excess water.
- further siloxane can be added to the resulting siloxane mixture or removed by suitable methods, for example distillation.
- the process can be carried out at room temperature and ambient pressure, but also at elevated or reduced temperature and elevated or reduced pressure.
- the composition of the siloxane mixture according to the invention is controlled by the ratio of the used and optionally again removed amounts of silanes or siloxanes.
- Siloxane mixtures according to the invention can also be prepared by adding pure siloxanes of the general formulas I or II or any mixtures of such siloxanes are heated to temperatures at which the said rearrangement processes take place, so that siloxane mixtures having a different composition are obtained.
- This composition may or may not be equivalent to the equilibrium composition at that temperature.
- the heating may take place in an open or closed system, preferably under a protective gas atmosphere. The process can be carried out at ambient pressure, but also elevated or reduced pressure. The heating may occur uncatalyzed or in the presence of a homogeneous or heterogeneous catalyst, for example an acid or base.
- the catalyst may then be deactivated or removed from the siloxane mixture, for example by distillation or filtration, but need not.
- siloxanes or siloxane mixtures can be removed again.
- the composition of the siloxane mixture according to the invention is characterized by the ratio of the amounts of siloxanes of the general formulas I and II which are used and optionally again removed, the temperature and
- Type ⁇ open or closed system Type ⁇ open or closed system
- the three methods described above can also be combined; they can optionally be carried out in the presence of one or more solvents. Preferably, no solvent is used.
- the silanes, silane mixtures, siloxanes and siloxane mixtures used are either standard products of the silicone industry or can be prepared by literature-known synthesis processes.
- the siloxane mixtures according to the invention may contain dissolved or suspended or emulsified additives to their Increase stability or influence their physical properties.
- Dissolved metal compounds for example iron carboxylates, as radical scavengers and oxidation inhibitors can increase the durability of a heat carrier.
- Suspended additives for example carbon or iron oxide, can improve physical properties of a heat carrier, for example heat capacity or thermal conductivity, preferably the sum of the proportions of all methylpolysiloxanes of the general formulas I or II is at least 95% by mass, especially at least 98% by mass, in particular at least 99.5% by mass, based on the total mixture.
- He indungsvelen siloxane mixtures can be used as heat transfer fluids, preferably as high tempera ture ⁇ heat transfer in solar devices, particularly in parabolic trough and Fresnel power plants. They can furthermore be used as heat transfer fluids in the chemical industry and the metal industry, as heat transfer fluids for low temperatures and as working fluids in heat engines, in particular solar thermal.
- the siloxane mixtures are preferably used at temperatures of 200 ° C to 550 ° C, more preferably 300 ° C to 500 ° C, in particular 350 ° C to 450 ° C, at temperatures above 200 ° C, the use of a A protective gas atmosphere is preferred in order to prevent oxidative decomposition.
- Me 3 SiO- (Me 2 SiO) u -SiMe 3, 5, 1% Me 3 SiO- (Me 2 SiO) SiMe 3 a2, 19.0% Me 3 SiO- (Me 2 SLO) x -SiMe 3 x> 12, 0.12% cyclic Methypolysi- loxanes of the general formula II with y 5 to 12; Viscosity 5.4 mPa * s) are heated in an autoclave with pressure transducer for 1 week at 405 ° C internal temperature.
- the recorded steam ⁇ pressure-time curve in Table 1 shows that only after ⁇ 5 days, an approximately constant pressure of ⁇ 16 bar is reached.
- the silicone oil has the following composition (in each case GC area%):
- Me 3 SiO- (Me 2 SiO) 3 SiMe X2, 20.2% Me 3 SiO- (Me 2 SiO) x SiMe ⁇ 3 with x> 12, 1.8% (Me 2 SiO) 3 / 10.1 % (Me 2 SiO) 4 , 3.6% (Me 2 SiO) s , 0.9% (Me 2 SiO) 6 , 0.3% (e 2 SiO) 7 , 0.3% (Me 2 SiO) y with y>7; weighted arithmetic mean of x 7.6 ( 29 Si NMR); Viscosity 4.6 mPa * s.
- Me 3 SiO- (Me 2 SiO) u-SiMe 3 , 4.1% Me 3 SiO- (Me 2 SiO) i 2 -SiMe 3 , 15.2% Me 3 SiO- (Me 2 SiO) x -SiMe 3 with ⁇ > 12, 16.0% (Me 2 SiO) 4 , 0.10% cyclic methypolysiloxanes of the general formula II where y 5 to 12; Viscosity 4.6 mPa * s) are in an autoclave with
- the silicone oil has the following composition (in each case GC area%):
- Me 3 SiO- (Me 2 SiO) 8 -SiMe 3 5.1% Me 3 SiO- (Me 2 SiO) 9 -SiMe 3 , 4.4%
- Me 3 SiO- (Me 2 SiO) 12 -SiMe 3 , 21.7% Me 3 SiO- (Me 2 SiO) x -SiMe 3 with x> 12, 1.9% (Me 2 SiO) 3 , 11.7 % (Me 2 SiO) 4 , 4.3% (Me 2 SiO) 5 , 1.1% (Me 2 SiO) 6 , 0.3% (Me 2 SiO) 7 , 0.3% (Me 2 SiO) y with y>7; weighted arithmetic mean of x 8.6 ( 2S Si NMR); Viscosity 4.8 mPa * s. Table 1
- Example 2 in comparison with Example 1 demonstrates the present invention: a suitably selected siloxane mixture exhibits a temporally nearly constant physical property (in this case the vapor pressure) at a constant temperature, although the chemical composition varies over time,
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- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Sustainable Energy (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020147036581A KR101656169B1 (ko) | 2012-06-29 | 2013-06-11 | 실록산 혼합물 |
EP13727924.6A EP2867323B1 (de) | 2012-06-29 | 2013-06-11 | Siloxan-mischungen |
US14/409,341 US9862869B2 (en) | 2012-06-29 | 2013-06-11 | Siloxane mixtures |
CN201380034945.9A CN104395426B (zh) | 2012-06-29 | 2013-06-11 | 硅氧烷混合物 |
JP2015518955A JP6049873B2 (ja) | 2012-06-29 | 2013-06-11 | シロキサン混合物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102012211258.8A DE102012211258A1 (de) | 2012-06-29 | 2012-06-29 | Siloxan-Mischungen |
DE102012211258.8 | 2012-06-29 |
Publications (1)
Publication Number | Publication Date |
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WO2014001081A1 true WO2014001081A1 (de) | 2014-01-03 |
Family
ID=48579107
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2013/062037 WO2014001081A1 (de) | 2012-06-29 | 2013-06-11 | Siloxan-mischungen |
Country Status (7)
Country | Link |
---|---|
US (1) | US9862869B2 (de) |
EP (1) | EP2867323B1 (de) |
JP (1) | JP6049873B2 (de) |
KR (1) | KR101656169B1 (de) |
CN (1) | CN104395426B (de) |
DE (1) | DE102012211258A1 (de) |
WO (1) | WO2014001081A1 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106414656A (zh) * | 2014-05-21 | 2017-02-15 | 瓦克化学股份公司 | 用于运行使用硅氧烷高温流体的系统的方法 |
WO2019072403A1 (de) | 2017-10-13 | 2019-04-18 | Wacker Chemie Ag | Mischungen von md-methylpolysiloxanen als wärmeträgerfluid |
WO2021098940A1 (de) | 2019-11-18 | 2021-05-27 | Wacker Chemie Ag | Methylpolysiloxanmischungen als wärmeträgerfluid |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102015202158A1 (de) | 2015-02-06 | 2016-08-11 | Technische Universität München | Verzweigte Organosiloxane als Wärmeträgerflüssigkeit |
ES2775750T3 (es) * | 2017-08-11 | 2020-07-28 | Wacker Chemie Ag | Procesos cíclicos con siloxanos supercríticos |
KR20210003200A (ko) * | 2018-05-02 | 2021-01-11 | 하이실랩스 에스에이에스 | 수소 운반체 화합물의 제조 및 재생 방법 |
WO2021180308A1 (de) * | 2020-03-10 | 2021-09-16 | Wacker Chemie Ag | Verfahren zur aufarbeitung von (m/d/t)-methylpolysiloxan-mischungen aus wärmeträgeranwendungen |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2754705A1 (de) | 1976-12-09 | 1978-06-22 | Dow Corning | Sonnenenergiesammelsystem |
US4122109A (en) | 1977-08-02 | 1978-10-24 | Dow Corning Corporation | Method for preparing a thermal-stability additive and a thermally stabilized methylpolysiloxane and compositions therefrom |
US4193885A (en) | 1977-08-02 | 1980-03-18 | Dow Corning Corporation | Method for preparing a thermal-stability additive and a thermally stabilized methylpolysiloxane and compositions therefrom |
DE3839333A1 (de) * | 1988-11-22 | 1990-05-23 | Bayer Ag | Kaeltetraegeroel auf siloxanbasis |
EP1473346B1 (de) | 2003-04-28 | 2006-05-24 | Shin-Etsu Chemical Company, Ltd. | Dimethylpolysiloxan -Zusammensetzung |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH153046A (de) | 1930-02-12 | 1932-02-29 | Siemens Ag | Selbstverkäufer mit Gebühreneinzugsvorrichtung. |
US3694405A (en) * | 1970-10-21 | 1972-09-26 | Union Carbide Corp | Rearrangement of organosiloxanes using macroreticular sulfonic acid cation exchange resin |
US4222952A (en) * | 1979-06-25 | 1980-09-16 | Union Carbide Corporation | Siloxane bond rearrangement effected by solid perfluorinated polymers containing pendant sulfonic acid groups |
US4593114A (en) * | 1984-09-13 | 1986-06-03 | Union Carbide Corporation | Direct process for preparing dimethylsiloxanes |
GB2397691B (en) | 2003-01-24 | 2005-08-10 | Leica Microsys Lithography Ltd | Cooling of a device for influencing an electron beam |
JP4493007B2 (ja) * | 2003-04-28 | 2010-06-30 | 信越化学工業株式会社 | ジメチルポリシロキサン組成物 |
-
2012
- 2012-06-29 DE DE102012211258.8A patent/DE102012211258A1/de not_active Withdrawn
-
2013
- 2013-06-11 CN CN201380034945.9A patent/CN104395426B/zh active Active
- 2013-06-11 US US14/409,341 patent/US9862869B2/en active Active
- 2013-06-11 EP EP13727924.6A patent/EP2867323B1/de not_active Revoked
- 2013-06-11 KR KR1020147036581A patent/KR101656169B1/ko active IP Right Grant
- 2013-06-11 WO PCT/EP2013/062037 patent/WO2014001081A1/de active Application Filing
- 2013-06-11 JP JP2015518955A patent/JP6049873B2/ja active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2754705A1 (de) | 1976-12-09 | 1978-06-22 | Dow Corning | Sonnenenergiesammelsystem |
US4122109A (en) | 1977-08-02 | 1978-10-24 | Dow Corning Corporation | Method for preparing a thermal-stability additive and a thermally stabilized methylpolysiloxane and compositions therefrom |
US4193885A (en) | 1977-08-02 | 1980-03-18 | Dow Corning Corporation | Method for preparing a thermal-stability additive and a thermally stabilized methylpolysiloxane and compositions therefrom |
DE3839333A1 (de) * | 1988-11-22 | 1990-05-23 | Bayer Ag | Kaeltetraegeroel auf siloxanbasis |
EP1473346B1 (de) | 2003-04-28 | 2006-05-24 | Shin-Etsu Chemical Company, Ltd. | Dimethylpolysiloxan -Zusammensetzung |
Non-Patent Citations (1)
Title |
---|
"SYLTHERM 800 Heat Transfer Fluid Product Technical Data", October 1997, DER FIRMA THE DOW CHEMICAL COMPANY |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106414656A (zh) * | 2014-05-21 | 2017-02-15 | 瓦克化学股份公司 | 用于运行使用硅氧烷高温流体的系统的方法 |
CN106414656B (zh) * | 2014-05-21 | 2019-05-28 | 瓦克化学股份公司 | 用于运行使用硅氧烷高温流体的系统的方法 |
WO2019072403A1 (de) | 2017-10-13 | 2019-04-18 | Wacker Chemie Ag | Mischungen von md-methylpolysiloxanen als wärmeträgerfluid |
WO2021098940A1 (de) | 2019-11-18 | 2021-05-27 | Wacker Chemie Ag | Methylpolysiloxanmischungen als wärmeträgerfluid |
Also Published As
Publication number | Publication date |
---|---|
US20150175868A1 (en) | 2015-06-25 |
EP2867323A1 (de) | 2015-05-06 |
EP2867323B1 (de) | 2016-08-10 |
KR20150022910A (ko) | 2015-03-04 |
US9862869B2 (en) | 2018-01-09 |
KR101656169B1 (ko) | 2016-09-08 |
JP6049873B2 (ja) | 2016-12-21 |
CN104395426B (zh) | 2017-03-01 |
JP2015531003A (ja) | 2015-10-29 |
DE102012211258A1 (de) | 2014-01-02 |
CN104395426A (zh) | 2015-03-04 |
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