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
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
  • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
  • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
  • B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
  • B23K35/02—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by mechanical features, e.g. shape
  • B23K35/0222—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by mechanical features, e.g. shape for use in soldering or brazing
  • B23K35/0244—Powders, particles or spheres; Preforms made therefrom
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
  • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
  • B23K35/00—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting
  • B23K35/22—Rods, electrodes, materials, or media, for use in soldering, welding, or cutting characterised by the composition or nature of the material
  • B23K35/36—Selection of non-metallic compositions, e.g. coatings or fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest
  • B23K35/3612—Selection of non-metallic compositions, e.g. coatings or fluxes; Selection of soldering or welding materials, conjoint with selection of non-metallic compositions, both selections being of interest with organic compounds as principal constituents
  • B23K35/3616—Halogen compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
  • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
  • C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
  • C07C225/06—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and acyclic
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
  • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
  • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
  • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
  • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
  • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D211/38—Halogen atoms or nitro radicals

Definitions

• This disclosure relates to apparatuses and methods that include nitrogen-containing fluoroketones as heat-transfer fluids.
• heat-transfer fluid which is inert, has a high dielectric strength, has low toxicity, good environmental properties, and good heat transfer properties over a wide temperature range.
• Other applications require precise temperature control and thus the heat-transfer fluid is required to be a single phase over the entire process temperature range and the heat-transfer fluid properties are required to be predictable, i.e., the composition remains relatively constant so that the viscosity, boiling point, etc. can be predicted so that a precise temperature can be maintained and so that the equipment can be appropriately designed.
• Perfluorocarbons perfluoropolyethers (PFPEs), and some hydrofluoroethers have been used for heat-transfer.
• Perfluorocarbons can have high dielectric strength and high resistivity. PFCs can be non-flammable and are generally mechanically compatible with materials of construction, exhibiting limited solvency. Additionally, PFCs generally exhibit low toxicity and good operator friendliness. PFCs can be manufactured in such a way as to yield a product that has a narrow molecular weight distribution. PFCs and PFPEs can exhibit one important disadvantage, however, and that is long environmental persistence which can give rise to high global warming potentials.
• Heat-transfer fluids for cooling electronics or electrical equipment include PFCs, PFPEs, silicone oils, and hydrocarbon oils. Each of these heat-transfer fluids has some disadvantage. PFCs and PFPEs may be environmentally persistent. Silicone oils and hydrocarbon oils are typically flammable.
• Perfluoroketone compounds comprise a class of commercially valuable chemical compounds that exhibit a wide range of properties.
• the compounds as a class are neutral and, in some cases, are surprisingly inert, thermally stable, and hydrolytically stable. Such properties have made them useful as heat transfer agents, as lubricants, and even as fire extinguishing agents.
• in-chain heteroatom refers to an atom other than carbon (for example, oxygen and nitrogen) that is bonded to carbon atoms in a carbon chain so as to form a carbon- heteroatom-carbon chain;
• device refers to an object or contrivance which is heated, cooled, or maintained at a predetermined temperature
• int refers to chemical compositions that are generally not chemically reactive under normal conditions of use
• mechanism refers to a system of parts or a mechanical appliance
• perfluoro- for example, in reference to a group or moiety, such as in the case of
• perfluoroalkylene or “perfluoroalkylcarbonyl” or “perfluorinated" means completely fluorinated such that, except as may be otherwise indicated, there are no carbon-bonded hydrogen atoms replaceable with fluorine;
• tertiary nitrogen refers to a nitrogen atom with three substituents other than hydrogen
• terminal refers to a moiety or chemical group that is at the end of a molecule or has only one group attached to it.
• a fluorochemical nitrogen-containing diketone compound includes a first terminal, branched perfluoroalkylcarbonyl group in which said perfiuoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms; at least one linear, branched, or cyclic perfluoroalkylene segment having 4 or more in-chain carbon or nitrogen atoms attached to the first terminal, branched perfluoroalkylcarbonyl group, said perfluoroalkylene segment containing one or more in-chain tertiary nitrogen atoms, and a second terminal, branched perfluoroalkylcarbonyl group in which said perfiuoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms , wherein the second perfluoroalkylcarbonyl group is attached to the perfluoroalky
• a fluorochemical nitrogen-containing monoketone compound comprises a first terminal, substituted or unsubstituted cyclic perfiuoroalkyl group in which said cyclic perfiuoroalkyl group contains a perfluoropiperazinyl, perfluoropiperidinyl, or perfluoropyrrolidinyl group which said groups may be , optionally, substituted with a perfiuoroalkyl group of 1 to 4 carbons or unsubstituted; a linear or branched perfluoroalkylene segment attached to the first terminal cyclic perfiuoroalkyl group which has from 1 to 4 carbon atoms and a second terminal, branched
• Rfi represents a perfluoroalkyl group of 3 to 10 carbon atoms that is branched or cyclic or a combination thereof
• Rf 2 is a linear or branched perfluorinated alkylene group of 1 to 4 carbons
• Rf 3 is a linear or branched perfluoroalkyl group of 1 to 4 carbons or -Rf 2 C(0)Rf5
• Rf 4 is F- or a linear or branched perfluoroalkyl group of 1 to 4 carbons
• Rf 5 is -CF(CF 3 ) 2 .
• Rfi can include at least one in-chain oxygen atom.
• an apparatus for heat transfer includes a device; and a mechanism for transferring heat to or from the device, the mechanism comprising a heat transfer fluid that includes a fluorochemical nitrogen-containing diketone compound comprising a first terminal, branched perfiuoroalkylcarbonyl group in which said perfluoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms; at least one linear, branched, or cyclic perfluoroalkylene segment having 4 or more in-chain carbon or nitrogen atoms attached to the first terminal, branched perfiuoroalkylcarbonyl group, said perfiuoroalkylene segment containing one or more in-chain tertiary nitrogen atoms, and a second terminal, branched perfiuoroalkylcarbonyl group in which said perfluoroalkyl group has from 3 to 10 in-chain carbon atoms which can include,
• perfluoropyrrolidinyl group which said groups may be, optionally, substituted with a perfiuoroalkyl group of 1-4 carbons or unsubstituted; a linear or branched
• perfiuoroalkylene segment attached to the first terminal cyclic perfiuoroalkyl group which has from 1 to 4 carbon atoms and a second terminal, branched
• the device can be an electronic component.
• the mechanism transfers heat to or from the device and includes a fluorochemical ketone.
• the apparatus can be used, for example for vapor phase soldering of electronic components.
• a method of transferring heat includes providing a device and transferring heat to or from the device using a mechanism, the mechanism comprising: a heat transfer fluid, wherein the heat transfer fluid includes a fluorochemical ketone compound that includes a first terminal, branched
• perfiuoroalkylcarbonyl group in which said perfiuoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms; at least one linear, branched, or cyclic perfiuoroalkylene segment having 4 or more in-chain carbon or nitrogen atoms attached to the first terminal, branched perfiuoroalkylcarbonyl group, said perfiuoroalkylene segment containing one or more in-chain tertiary nitrogen atoms, and a second terminal, branched perfiuoroalkylcarbonyl group in which said perfiuoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms, wherein the second perfiuoroalkylcarbonyl group is attached to the perfiuoroalkylene segment or, optionally a fluorochemical nitrogen-containing mono
• the provided nitrogen-containing fluorochemical mono- and diketones provide compounds that can be useful in heat transfer fluids.
• the provided fluorochemical ketones have surprisingly good thermal stability. They also have high dielectric strength, low electrical conductivity, chemical inertness, and good environmental properties.
• the provided fluorochemical ketones can also be useful in vapor phase soldering.
• Perfluoropolyethers While having the required thermal stability at the temperatures employed, also have as a drawback that they are very environmentally persistent with extremely long atmospheric lifetimes and concomitant high global warming potentials due to their high fluorine content. As such, there is a need for new materials which have a much shorter
• hydrofluoroethers have been disclosed as heat-transfer fluids. Exemplary hydrofluoroethers can be found in U. S. Pat. Appl. Ser. No. 12/263,661, entitled “Methods of Making Fluorinated Ethers, Fluorinated Ethers and Uses Thereof, filed November 3, 2008, and in U. S. Pat. Publ. Nos. 2007/0267464 (Vitcak et al.) and 2008/0139683 (Flynn et al), and U. S. Pat. Nos. 7,128,133 and 7,390,427 (Costello et al).
• Perf uorinated ketones of suitable structure having boiling points of at least 170°C, are believed to possess the required stability as well as the necessary short atmospheric lifetime and hence low global warming potential to make them viable candidates for these high temperature heat transfer applications.
• a low molecular weight ketone, C 2 F 5 COCF(CF 3 )2 is available as NOVEC 649 from 3M Company, St. Paul, MN and is photochemically active in the lower atmosphere and has an atmospheric lifetime of about 5 days.
• Higher molecular weight perfluorinated nitrogen-containing mono or diketones would be expected to have a similar absorption in the UV spectrum leading to a similar photochemical lifetime with only slight changes expected due to their structure.
• Provided nitrogen-containing fluorochemical ketones include a first terminal, branched
• perfluoroalkylcarbonyl group in which said perfluoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms; at least one linear, branched, or cyclic perf uoroalkylene segment having 4 or more in-chain carbon or nitrogen atoms attached to the first terminal, branched perfluoroalkylcarbonyl group, said perfluoroalkylene segment containing one or more in-chain tertiary nitrogen atoms, and a second terminal, branched perfluoroalkylcarbonyl group in which said perfluoroalkyl group has from 3 to 10 in-chain carbon atoms which can include, optionally, one or more in-chain oxygen atoms, wherein the second perfiuoroalkylcarbonyl group is attached to the perfiuoroalkylene segment or, optionally a fluorochemical nitrogen-containing monoketone compound that comprises a first terminal, substituted
• Branched perfiuoroalkylcarbonyl groups have perfiuoroalkyl groups that include 3 to 10 in-chain carbon atoms. Additionally, the alkyl moieties of the
• perfiuoroalkylcarbonyl groups can have branched perfiuoroalkylgroups having from 1 to 4 carbon atoms and can also include one or more in-chain oxygen groups.
• the provided nitrogen-containing fluorochemical ketones include one or two carbonyl groups.
• Provided fluorochemical nitrogen-containing diketones typically have terminal perfiuoroalkylcarbonyl groups on each end of a linear, branched or cyclic perfiuoroalkylene segment having 4 or more in-chain carbon or nitrogen atoms attached substantially between the two terminal perfiuoroalkyl carbonyl groups, said
• the provided diketones are symmetrical molecules of the A-B-A structure where A is the perfiuoroalkylcarbonyl group and B is the perfiuoroalkylene segment.
• Provided fluorochemical, nitrogen-containing monoketones have a
• perfiuoroalkyl group which contains a perfluoropiperazinyl, perfluoropiperidinyl, or perfluoropyrrolidinyl group which said groups may be, optionally, substituted with a perfiuoroalkyl group of 1 to 4 carbons.
• the provided nitrogen-containing fluorochemical ketones have a chemical structure comprising : RfiC(0)Rf 2 N(Rf 3 )-Rf 2 C(0)Rfi,
• Rfi represents a perfluoroalkyl group of 3 to 10 carbon atoms that is branched or cyclic or a combination thereof, that optionally contains at least one in-chain oxygen;
• Rf 2 is a linear or branched perfluorinated alkylene group of 1 to 4 carbons;
• Rf 3 is a linear or branched perfluoroalkyl group of 1 to 4 carbons or -Rf 2 C(0)Rf 5 ;
• Rf 4 is F- or a linear or branched perfluoroalkyl group of 1 to 4 carbons;
• Rf 5 is (CF 3 ) 2 CF-.
• Exemplary Rfi groups include
• the provided fluorochemical ketones comprise:
• an apparatus that requires heat transfer.
• the apparatus includes a device and a mechanism for transferring heat to or from the device using a heat-transfer fluid.
• Exemplary apparatuses include refrigeration systems, cooling systems, testing equipment, and machining equipment.
• Other examples include test heads used in automated test equipment for testing the performance of semiconductor dice; wafer chucks used to hold silicon wafers in ashers, steppers, etchers, PECVD tools; constant temperature baths, and thermal shock test baths.
• the provided apparatus can include a refrigerated transport vehicle, a heat pump, a supermarket food cooler, a commercial display case, a storage warehouse refrigeration system, a geothermal heating system, a solar heating system, an organic Rankine cycle device, and combinations thereof.
• the provided apparatus includes a device.
• the device is defined herein as a component, work-piece, assembly, etc. to be cooled, heated or maintained at a selected temperature.
• Such devices include electrical components, mechanical components and optical components.
• Examples of devices of the present invention include, but are not limited to microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, electrical distribution switch gear, power transformers, circuit boards, multi-chip modules, packaged and unpackaged semiconductor devices, lasers, chemical reactors, fuel cells, and electrochemical cells.
• the device can include a chiller, a heater, or a combination thereof.
• the device can include an electronic component to be soldered and solder.
• the heat required for soldering can be supplied by a vapor phase that has a temperature of greater than 170°C, greater than 200°C, greater than 230°C, or even greater.
• the present disclosure includes a mechanism for transferring heat.
• Heat is transferred by placing the heat transfer mechanism in thermal contact with the device.
• the heat transfer mechanism when placed in thermal contact with the device, removes heat from the device or provides heat to the device, or maintains the device at a selected temperature.
• the direction of heat flow is determined by the relative temperature difference between the device and the heat transfer mechanism.
• the heat transfer mechanism may include facilities for managing the heat-transfer fluid, including, but not limited to pumps, valves, fluid containment systems, pressure control systems, condensers, heat exchangers, heat sources, heat sinks, refrigeration systems, active temperature control systems, and passive temperature control systems.
• suitable heat transfer mechanisms include, but are not limited to, temperature controlled wafer chucks in PECVD tools, temperature controlled test heads for die performance testing, temperature controlled work zones within semiconductor process equipment, thermal shock test bath liquid reservoirs, and constant temperature baths.
• the upper desired operating temperature may be as high as 170°C, as high as 200°C, or even higher.
• the heat transfer mechanism includes the provided heat-transfer fluid.
• the provided heat transfer fluid can be represented by nitrogen-containing fluorochemical ketones having a chemical structure:
• Rfi represents a perfluoroalkyl group of 3 to 10 carbon atoms that is branched or cyclic or a combination thereof, that optionally contains at least one in-chain oxygen;
• Rf2. is a linear or branched perfluorinated alkylene group of 1 to 4 carbons;
• Rf 3 is a linear or branched perfluoroalkyl group of 1 to 4 carbons or -Rf2C(0)Rf 5 ;
• Rf 4 is F- or a linear or branched perfluoroalkyl group of 1 to 4 carbons;
• Rf 5 is (CF 3 ) 2 CF-.
• Rfi groups include (CF 3 ) 2 CF-, C 3 F 7 OCF(CF 3 )-, CF 3 OC 3 F 6 OCF(CF 3 )-, C 4 F 9 OCF(CF 3 )- and CF 3 OCF(CF 3 )-.
• the provided apparatuses and heat transfer fluids fulfill a market need for a high temperature heat transfer fluid.
• the provided nitrogen-containing fluorochemical ketones provide a stable, high temperature heat transfer fluid.
• the provided nitrogen-containing fluorochemical ketones provide a stable, high temperature heat transfer fluid that does not substantially change in purity as measured by gas
• the devices can include equipment that is used to test the performance of semiconductor dice.
• the dice are the individual "chips" that are cut from a wafer of semiconductor substrate.
• the dice come from the semiconductor foundry and must be checked to ensure they meet functionality requirements and processor speed requirements.
• the test is used to sort "known good dice” (KGD) from dice that do not meet the performance requirements. This testing is generally performed at temperatures ranging from about -80°C to about 100°C.
• the dice are tested one-by-one, and an individual die is held in a chuck.
• This chuck provides, as part of its design, provision for cooling the die.
• several dice are held in the chuck and are tested either sequentially or in parallel. In this situation, the chuck provides cooling for several dice during the test procedure.
• the dice are tested at very low temperatures. For example, complementary metal- oxide semiconductor (“CMOS”) devices in particular operate more quickly at lower temperatures. If a piece of automated testing equipment (ATE) employs CMOS devices "on board" as part of its permanent logic hardware, it may be advantageous to maintain the logic hardware at a low temperature.
• CMOS complementary metal- oxide semiconductor
• a heat-transfer fluid typically performs well at both low and high temperatures (i.e., typically has good heat transfer properties over a wide temperature range), is inert (i.e., is non-flammable, low in toxicity, non-chemically reactive), has high dielectric strength, has a low environmental impact, and has predictable heat-transfer properties over the entire operating temperature range.
• the devices can include etchers. Etchers can operate over temperatures ranging from about 70°C to about 150°C. Typically, during etching, a reactive plasma is used to anisotropically etch features into a semiconductor.
• the semiconductor can include a silicon wafer or include a II-VI or a III-V semiconductor.
• the semiconductor materials can include, for example, III-V semiconductor materials such as, for example, GaAs, InP, AlGaAs, GalnAsP, or GalnNAs.
• the provided process is useful for etching II- VI semiconductor materials such as, for example, materials that can include cadmium, magnesium, zinc, selenium, tellurium, and combinations thereof.
• An exemplary II-VI semiconductor material can include CdMgZnSe alloy.
• Other II-VI semiconductor materials such as CdZnSe, ZnSSe, ZnMgSSe, ZnSe, ZnTe, ZnSeTe, HgCdSe, and
• HgCdTe can also be etched using the provided process.
• the semiconductors to be processed are typically kept at a constant temperature. Therefore, the heat-transfer fluid that can have a single phase over the entire temperature range is typically used.
• the heat-transfer fluid typically has predictable performance over the entire range so that the temperature can be precisely maintained.
• the devices can include ashers that operate over temperatures ranging from about 40°C to about 150°C.
• Ashers are devices that can remove the photosensitive organic masks made of positive or negative photoresists. These masks are used during etching to provide a pattern on the etched semiconductor.
• the devices can include steppers that can operate over temperatures ranging from about 40°C to about 80°C. Steppers are an essential part of photolithography that is used in semiconductor manufacturing where reticules needed for manufacturing are produced. Reticules are tools that contain a pattern image that needs to be stepped and repeated using a stepper in order to expose the entire wafer or mask.
• Reticules are used to produce the patterns of light and shadow needed to expose the photosensitive mask.
• the film used in the steppers is typically maintained within a temperature window of +/- 0.2°C to maintain good performance of the finished reticule.
• the devices can include plasma enhanced chemical vapor deposition (PECVD) chambers that can operate over temperatures ranging from about 50°C to about 150°C.
• PECVD plasma enhanced chemical vapor deposition
• films of silicon oxide, silicon nitride, and silicon carbide can be grown on a wafer by the chemical reaction initiated in a reagent gas mixture containing silicon and at least any one of oxygen, nitrogen, or carbon.
• the chuck on which the wafer rests is kept at a uniform, constant temperature at each selected temperature.
• the devices can include electronic devices, such as processors, including microprocessors. As these electronic devices become more powerful, the amount of heat generated per unit time increases. Therefore, the mechanism of heat transfer plays an important role in processor performance.
• the heat-transfer fluid typically has good heat transfer performance, good electrical compatibility (even if used in "indirect contact” applications such as those employing cold plates), as well as low toxicity, low (or non-) flammability and low environmental impact. Good electrical compatibility requires the heat-transfer fluid candidate to exhibit high dielectric strength, high volume resistivity, and poor solvency for polar materials. Additionally, the heat- transfer fluid must exhibit good mechanical compatibility, that is, it must not affect typical materials of construction in an adverse manner.
• the provided device is defined herein as a component, work-piece, assembly, etc. to be cooled, heated or maintained at a selected temperature.
• Such devices include electrical components, mechanical components and optical components.
• Examples of devices of the present invention include, but are not limited to microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, electrical distribution switch gear, power transformers, circuit boards, multi-chip modules, packaged and unpackaged semiconductor devices, chemical reactors, fuel cells, and lasers.
• the provided apparatus includes a mechanism for transferring heat. Heat is transferred by placing the heat transfer mechanism in thermal contact with the device.
• the heat transfer mechanism when placed in thermal contact with the device, removes heat from the device or provides heat to the device, or maintains the device at a selected temperature.
• the direction of heat flow is determined by the relative temperature difference between the device and the heat transfer mechanism.
• the provided apparatus can also include refrigeration systems, cooling systems, testing equipment and machining equipment. In some embodiments, the provided apparatus can be a constant temperature bath or a thermal shock test bath.
• the heat transfer mechanism includes a provided heat-transfer fluid. Additionally, the heat transfer mechanism may include facilities for managing the heat-transfer fluid, including, but not limited to: pumps, valves, fluid containment systems, pressure control systems, condensers, heat exchangers, heat sources, heat sinks, refrigeration systems, active temperature control systems, and passive temperature control systems. Examples of suitable heat transfer mechanisms include, but are not limited to, temperature controlled wafer chucks in PECVD tools, temperature-controlled test heads for die performance testing, temperature controlled work zones within semiconductor process equipment, thermal shock test bath liquid reservoirs, and constant temperature baths. Constant temperature baths are typically operated over a broad temperature range. Therefore, desirable heat-transfer fluids preferably have a wide liquid range and good low- temperature heat transfer characteristics. A heat-transfer fluid having such properties allows a very wide operating range for the constant temperature bath. Typically, most testing fluids require fluid change-out for wide temperature extremes. Also, good temperature control is essential for accurately predicting physical properties of the heat- transfer fluids.
• a method of transferring heat includes providing a device and transferring heat to or from the device using a mechanism.
• the mechanism can include a heat transfer fluid such as the nitrogen-containing fluorochemical ketones disclosed herein.
• the provided method can include vapor phase soldering wherein the device is an electronic component to be soldered.
• solvents and reagents may be obtained from Aldrich Chemical Co. of Milwaukee, WI.
• NOVEC-7200 refers to ethyl perfluorobutyl ether and is available from 3M Company, St. Paul, MN.
• HFPO refers to hexafluoropropene oxide
• HFP refers to hexafluoropropene.
• Diglyme refers to diethylene glycol dimethyl ether.
• Example 1 Preparation of l, -(perfluoropiperazine-l,4-diyl)bis(l,l,3,4,4,4-hexafluoro-3- (trifluoromethyl)butan-2-one).
• (V) Preparation of Intermediate (4-ethoxycarbonylmethyl-piperazine- 1 -yl)acetic acid ethyl ester
• An overhead stirrer, water condensor, thermometer and addition funnel was equipped with an overhead stirrer, water condensor, thermometer and addition funnel and the apparatus placed under a nitrogen atmosphere using a glass tee on top of the condenser.
• Hexafiuoropropene (100 g 0.66 mol, MDA) was added as a gas to the reaction mixture.
• the reaction mixture was then stirred for 18 hours to allow for maximum reaction of the di-acid fluoride to react with the hexafiuoropropene.
• the reaction mix was cooled to room temperature and the salts were removed through vacuum filtration.
• the liquid was then transferred to a separatory funnel where the lower fiuorochemical phase was separated from the diglyme phase.
• the crude product was purified by fractional distillation using a concentric tube column. The final sample purity was 91.4% by GC- FID. The product mass was confirmed by GC/MS.
• This material was prepared by the electrochemical fluorination of
• CF 3 N(CF 2 CF 2 COF) 2 (240 g 0.636 mol), cesium fluoride (Aldrich, 77 g 0.51 mol), perfluoropropyl vinyl ether (Dyneon 618 g, 2.32 mol) and diglyme solvent (400 mL) were combined in a 2 L Parr pressure reactor. The reactor was sealed and heated to 65°C for 72 hours. After 72 hours, the mix was cooled and a sample was analyzed by GC-FID. GC- FID indicated conversion of 87%. The product mix was filtered from the cesium fluoride salts and transferred to a 1 L separatory funnel. The lower fluoroketone product phase was removed from the diglyme solvent.
• the distilled acid fluoride (75 g, 90% purity, 0.124 mol), cesium fluoride (6.21 g, 0.041 mol, Aldrich) and anhydrous diglyme (28 g, Aldrich) were added to a 600 mL Parr reactor, the reactor sealed and degassed under nitrogen and heated to 40°C.
• the product mass was confirmed by GC/MS.
• the IR of the ketone showed a carbonyl absorption at 1770 cm .
• the acid fluoride (126.5 g of about 90%> purity), cesium fluoride (18.2 g, 0.12 mol) and diglyme (50 g) were combined in a 600 mL Parr reactor, the reactor sealed and degassed under nitrogen and then heated to 40°C. Hexafluoropropylene (90 g, 0.6 mol, 3M) was added in several portions over five hours and then held for an additional 68 hours at 40°C. The reactor was then cooled, the excess hexafluoropropylene vented and the cesium fluoride solids filtered.
• the lower fluorochemical phase was separated from the solvent and this material (132 g) was placed in a 600 mL Parr reaction vessel along with cesium fluoride (10 g) and diglyme (27 g) and the reaction repeated with the addition of a large excess of HFP (210 g) as described. After workup as described the lower fluorochemical phase was analyzed and found to contain about 6.3% of the desired ketone by GC/MS. The ketone was distilled to a purity of 83% (bp > 218°C).
• the dimethyl ester was prepared by the addition of two moles of methyl acrylate to ethylamine in a procedure essentially as described in Example 2 for the addition methylamine with two moles of methyl methacrylate.
• This material was prepared by the electrochemical fluorination of

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