Hexafluoropropene dimer-containing composition

Abstract

The present invention provides a hexafluoropropene dimer-containing composition as a novel mixture. Disclosed is a composition which contains hexafluoropropene dimers represented by C6F12, wherein: at least one of the hexafluoropropene dimers represented by C6F12 is a compound represented by formula (I); and the abundance ratio E / (E + Z) of the E-form among the E-form and the Z-form of the compound is more than 0.5.

Description

Composition containing hexafluoropropene dimer

[0001] The present invention relates to a hexafluoropropene dimer-containing composition, and to heat transfer fluids, foaming agents, lubricants, and cleaning agents containing the same.

[0002] Hexafluoropropene (HFP) dimers are known to be usable as heat transfer fluid compositions (Patent Document 1).

[0003] Because HFP dimers have a low global warming potential (GWP), they are attracting attention as a substitute for chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs).

[0004] Specification of Chinese Patent No. 115706279

[0005] In view of the circumstances described above, the object of this disclosure is to provide a novel hexafluoropropene dimer-containing composition as a mixture.

[0006] The inventors conducted extensive research to solve the above problems and found that by adjusting the geometric isomer ratio of the HFP dimer contained in the composition, they could provide a novel HFP dimer-containing composition as a mixture. Based on this finding, the inventors conducted further research and completed this disclosure.

[0007] In other words, this disclosure provides the following hexafluoropropene dimer-containing compositions, as well as heat transfer fluids, foaming agents, lubricants and cleaning agents containing the same. [Item 1] C ６ F １２ A composition comprising a hexafluoropropene dimer represented by C ６ F １２ A composition in which at least one of the hexafluoropropene dimers represented by is a compound represented by the following formula (I); and the ratio of the E-isomer to the Z-isomer of the compound, E / (E+Z), is greater than 0.5. [Clause 2] The composition according to Claim 1, wherein the E / (E+Z) of the compound represented by formula (I) is 0.8 to 1. [Clause 3] The composition according to Claim 1, wherein the E / (E+Z) of the compound represented by formula (I) is 0.965 to 1. [Clause 4] The composition according to any one of Claims 1 to 3, further comprising the compound represented by the following formula (II). [Section 5] The above C ６ F １２ The composition according to any one of claims 1 to 4, wherein the compound represented by formula (I) is contained in an amount of 80% by mass or more relative to the total amount of hexafluoropropene dimers represented by [Claim 6] C ６ F １２ [Claim 7] A heat transfer fluid comprising the composition according to any one of claims 1 to 5, wherein the compound represented by formula (I) is present in an amount of 95% by mass or more relative to the total amount of hexafluoropropene dimers represented by [Claim 7]. [Claim 8] A heat transfer device comprising a device and a mechanism for transferring heat from or to the device, comprising the heat transfer fluid according to claim 7. [Claim 9] A heat transfer method comprising the steps of preparing a device and transferring heat to or from the device using the heat transfer fluid according to claim 7 or claim 8. [Claim 10] A foaming agent comprising the composition according to any one of claims 1 to 6. [Claim 11] A lubricant comprising the composition according to any one of claims 1 to 6. [Claim 12] A cleaning agent comprising the composition according to any one of claims 1 to 6.

[0008] The composition according to the present disclosure as described above can provide a novel hexafluoropropene dimer-containing composition (hereinafter also simply referred to as "the composition") as a mixture.

[0009] In this specification, "contains" is a concept that encompasses all of the following: "contains," "consist essentially of," and "consist of." Furthermore, in this specification, when a numerical range is indicated as "A to B," it means A or greater and B or less.

[0010] (Hexafluoropropene dimer-containing composition) The composition of this disclosure is C６ F １２ and contains a compound represented by the above C ６ F １２ at least one of the compounds represented by is a compound represented by the following formula (I); the abundance ratio E / (E + Z) of the E-isomer among the E-isomer and Z-isomer of the above compound is more than 0.5.

[0011] The compound represented by the above formula (I) has geometric isomers (one E-isomer and one Z-isomer). The following formula (I-E) represents the E-isomer, and formula (I-Z) represents the Z-isomer.

[0012] The abundance ratio E / (E + Z) of the E-isomer among the E-isomer and Z-isomer of the compound represented by the above formula (I) contained in the composition of the present disclosure is more than 0.5 (that is, the abundance ratio of the E-isomer is larger than that of the Z-isomer), preferably 0.67 or more, more preferably 0.8 or more, still more preferably 0.91 or more, particularly more preferably 0.95 or more, and most preferably 0.965 or more. Since the compound represented by the above formula (I) is more stable in the E-isomer than in the Z-isomer, if E / (E + Z) is within the above range, decomposition during long-term use can be suppressed. In the present disclosure, the upper limit of E / (E + Z) of the compound represented by the above formula (I) is not particularly limited, but E / (E + Z) of the compound represented by the above formula (I) may be, for example, 1 or less.

[0013] Also, in the present disclosure, E / (E + Z) of the compound represented by the above formula (I) may be 1.

[0014] The composition of the present disclosure may contain a compound represented by C other than the compound represented by the above formula (I) ６ F[[ID=2৪]] １２ and as such a compound, known compounds represented by C ６ F １２ can be widely adopted without particular limitation. However, it is preferable that the compound represented by C ６ F １２ in this specification does not contain cycloalkane, and it is more preferably a hexafluoropropene (HFP) dimer.

[0015] C other than the compound represented by formula (I) ６ F １２ Examples of compounds represented by this formula include hexafluoropropene dimers, and more specifically, compounds represented by the following formula (II).

[0016]

[0017] In this specification, C other than the compound represented by formula (I) above. ６ F １２ The compounds represented by include both the E and Z geometric isomers unless otherwise specified.

[0018] C included in the composition of this disclosure ６ F １２ The compound represented by may include only the compound represented by formula (I) above, or it may be a mixture containing both formulas (I) and (II) above.

[0019] C ６ F １２ The content of the compound represented by formula (I) in the compound represented by the formula is as follows: ６ F １２ The total amount of HFP dimers represented by the formula is preferably 10% by mass or more, more preferably 50% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, particularly preferably 95% by mass or more, and particularly more preferably 98% by mass or more. The blending ratio of the compound represented by the above formula (I) is C ６ F １２With respect to the total amount of HFP dimer represented by mass% or less, 90 mass% or more and 100 mass% or less, 10 mass% or more and 98 mass% or less, 30 mass% or more and 98 mass% or less, 50 mass% or more and 98 mass% or less, 70 mass% or more and 98 mass% or less, 9 0 mass% or more and 98 mass% or less, 10 mass% or more and 96 mass% or less, 30 mass% or more and 96 mass% or less, 50 mass% or more and 96 mass% or less, 70 mass% or more and 96 mass% or less, 90 mass% or more9 6 mass% or less, 40 mass% or more and 95 mass% or less, 60 mass% or more and less than 95 mass%, 80 mass% or more and less than 95 mass%, 30 mass% or more and less than 85 mass%, 50 mass% or more and less than 85 mass%, 7 It may be 0% by mass or more and less than 85% by mass, 40% by mass or more and 80% by mass or less, 55% by mass or more and 80% by mass or less, 60% by mass or more and 75% by mass or less, 65% by mass or more and 70% by mass or less, 35% by mass or more and 60% by mass or less, 50% by mass or more and 60% by mass or less, 70% by mass or more and 90% by mass or less, 80% by mass or more and 100% by mass or less, 80% by mass or more and 95% by mass or less, 80% by mass or more and 90% by mass or less, 85% by mass or more and 100% by mass or less, 90% by mass or more and 100% by mass or less, or 85% by mass or more and 95% by mass or less, preferably 50% by mass or more and 100% by mass or less, preferably 60% by mass or more and 100% by mass or less, more preferably 80% by mass or more and 100% by mass or less, and even more preferably 95% by mass or more and 100% by mass or less.

[0020] Similarly, regarding the content of the compound represented by formula (II), C ６ F １２ The amount of HFP dimers represented by is preferably 1% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.2% by mass or less.

[0021] C contained in the composition ６ F １２The content of the compound represented by is preferably 20% by mass or more, more preferably 40% by mass or more, even more preferably 60% by mass or more, and particularly preferably 80% by mass or more, relative to the total composition. Also, C contained in the composition ６ F １２ The content of the compound represented by is preferably 99.9999% by mass or less of the total composition.

[0022] The compounds represented by formulas (I) and (II) above may be produced by conventional methods, for example, by the method described in Chinese Patent Application Publication No. 103787824, and are not limited thereto. They may also be obtained by dimerization using HFP as a raw material, and are not limited thereto; they may be obtained by employing a wide range of known methods.

[0023] The compositions disclosed herein include compounds other than those represented by formula (I) or (II), such as C ６ F １２ It may contain a compound represented by .

[0024] The compositions of this disclosure may contain hexafluoropropene trimers, and may contain, for example, one or more compounds represented by the following formulas (A) to (C).

[0025] The compositions of this disclosure may contain a hexafluoropropene tetramer.

[0026] The hexafluoropropene tetramer may contain 1,1,1,2,5,6,6,6-octafluoro-2,3,5-tris(trifluoromethyl)-4-(perfluoropropyl-2-yl)-3-hexene.

[0027] The compositions disclosed herein may further contain water. The water content is as follows: ６ F １２The amount of water is 0.0001 parts by mass or more, more preferably 0.0005 parts by mass or more, and even more preferably 0.001 parts by mass or more, per 100 parts by mass of the total amount of hexafluoropropene dimer represented by . By setting the concentration of water to 0.0001 parts by mass or more, the stability of the composition can be maintained and the charging of the composition can be suppressed.

[0028] Furthermore, the water content in the composition of this disclosure is as described above C ６ F １２ The amount of water is preferably 0.1 parts by mass or less, more preferably 0.05 parts by mass or less, even more preferably 0.01 parts by mass or less, particularly preferably 0.005 parts by mass or less, and most preferably 0.004 parts by mass or less, per 100 parts by mass of the total amount of hexafluoropropene dimer represented by . By setting the water content to 0.1 parts by mass or less, C ６ F １２ This can suppress the decomposition of the compound represented by [formula], and consequently, it can suppress the increase in fluoride ions and the rise in acidity. Furthermore, by reducing the water content to 0.004 parts by mass or less, rusting of the container can be suppressed.

[0029] In one embodiment, the water content is preferably 0.0001% by mass or more, more preferably 0.0005% by mass or more, and even more preferably 0.001% by mass or more, relative to the entire composition.

[0030] In one embodiment, the water content is preferably 0.1% by mass or less, more preferably 0.05% by mass or less, even more preferably 0.01% by mass or less, and particularly preferably 0.005 parts by mass or less, relative to the entire composition.

[0031] The compositions of this disclosure have improved dielectric strength by containing a predetermined amount of water. The dielectric strength of the compositions of this disclosure may preferably be 40 kV or more, preferably 50 kV or more, and more preferably 60 kV or more.

[0032] The compositions of this disclosure may further contain fluoride ions. The amount of fluoride ions in the composition is preferably 0.0000001% by mass or more, more preferably 0.000001% by mass or more, and even more preferably 0.00001% by mass or more, based on the total composition.

[0033] Furthermore, the amount of fluoride ions contained in the composition of this disclosure is preferably 5% by mass or less, more preferably 1% by mass or less, more preferably 0.1% by mass or less, more preferably 0.01% by mass or less, even more preferably 0.001% by mass or less, and particularly preferably 0.0001% by mass or less, relative to the entire composition.

[0034] Any known fluoride ion source can be widely used as the fluoride ion source, and there are no particular limitations. Specifically, examples include ions of hydrogen fluoride, sodium fluoride, sodium hydrogen fluoride, potassium fluoride, potassium hydrogen fluoride, lithium fluoride, cesium fluoride, calcium fluoride, magnesium fluoride, aluminum fluoride, zinc fluoride, silver fluoride, and iron fluoride. Only one of these may be included, or multiple types may be included. Preferably, the fluoride ion source is hydrogen fluoride.

[0035] The compositions of this disclosure are further C ６ HF １１ It may contain the compound represented by C. ６ HF １１ The content of the compound represented by the above C ６ F １２ The amount is 0.0001 parts by mass or more, more preferably 0.0005 parts by mass or more, and even more preferably 0.001 parts by mass or more, per 100 parts by mass of the total amount of hexafluoropropene dimer represented by . ６ HF １１ By setting the concentration of the compound represented by to 0.0001 parts by mass or more, C ６ F １２ The decomposition of the hexafluoropropene dimer represented by [formula] can be suppressed.

[0036] Furthermore, C contained in the composition of this disclosure ６ HF １１ The content of the compound represented by the above C ６ F １２ The amount of the hexafluoropropene dimer represented by is preferably 0.1 parts by mass or less, more preferably 0.05 parts by mass or less, and even more preferably 0.01 parts by mass or less, per 100 parts by mass of the total amount of the hexafluoropropene dimer represented by . ６ HF １１ By making the content of 0.1 parts by mass or less, C ６ F １２ The decomposition of the hexafluoropropene dimer represented by [formula] can be suppressed.

[0037] C ６ HF １１ Compounds represented by C include: ６ HF １１ A wide range of known methods represented by can be adopted, and there are no particular limitations. However, C in this specification ６ HF １１ The compound represented by preferably does not contain a cycloalkane, and more preferably is a compound in which one of the fluorine atoms of a hexafluoropropene (HFP) dimer is replaced by a hydrogen atom.

[0038] C ６ HF １１ Examples of specific structures of compounds represented by the formula are shown below.

[0039] In a preferred embodiment, the composition of the present disclosure is C ６ HF １１ The compound represented by includes at least one of the following:

[0040] In this specification, C ６ HF １１ The compounds represented by include both the E and Z geometric isomers unless otherwise specified.

[0041] C included in the composition of this disclosure ６ HF １１As the compound represented by [the formula], only one kind of the compounds represented by any of the above formulas may be included, or it may be a mixture containing two or more kinds.

[0042] In addition to the above, the composition of the present disclosure may also contain C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） [In the formula, m is an integer of 4 or more and 12 or less and other than 6. n is an integer of 4 or more and 12 or less.] may be included.

[0043] m is an integer of 4 or more, preferably an integer of 5 or more, and more preferably an integer of 6 or more. Also, n is an integer of 12 or less, preferably an integer of 11 or less, and more preferably an integer of 10 or less. However, m does not include 6.

[0044] n is an integer of 4 or more, preferably an integer of 5 or more, and more preferably an integer of 6 or more. Also, n is an integer of 12 or less, preferably an integer of 11 or less, and more preferably an integer of 10 or less. Furthermore, n is particularly preferably 6.

[0045] C ｍ F ２ｍ may be a chain compound or a cyclic compound which may have a substituted structure. The chain compound may be a so-called alkene, and may be linear or branched.

[0046] C ｎ F （２ｎ－２） may be a chain compound or a cyclic compound which may have a substituted structure. The chain compound may be a so-called diene or alkyne, and may be linear or branched.

[0047] Also, the content of C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） is preferably 0.0001% by mass or more based on the whole composition of the present disclosure.

[0048] On the other hand, C ｍ F ２ｍ and / or Cｎ F （２ｎ－２） The content of F is preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 1% by mass or less with respect to the whole composition of the present disclosure.

[0049] In one aspect, in the composition, C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） The content of is preferably 0.0001 part by mass or more, more preferably 0.01 part by mass or more, and still more preferably 0.1 part by mass or more with respect to 100 parts by mass in total of the compounds represented by C ６ F １２ In one aspect, in the composition, C

[0050] On the other hand, in the composition, C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） The content of is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and still more preferably 1 part by mass or less with respect to the total 100 parts by mass of the compounds represented by C ６ F １２ When C

[0051] Note that when a plurality of types of and / or are included, the above content means their total amount. ｍ F ２ｍ and / or C ｎ F （２ｎ－２） By setting the content of and / or within the above range, the decomposition of the HFP dimer represented by C

[0052] C ｍ F ２ｍ and / or C ｎ F （２ｎ－２） can be suppressed, and thus an increase in fluoride ions and an increase in acidity can be suppressed. ６ F １２ The composition of the present disclosure is C

[0053] The composition of the present disclosure is C ６ F １２The formula may include additional compounds different from the compound represented by [formula]. These additional compounds may be one or more types. Examples of additional compounds include perfluoropolyethers.

[0054] The perfluoropolyether is preferably of the general formula: RO-Rf １ Represented by -R', where R and R' are the same or different, and -C ｍ F ２ｍ＋１ A single-valued base represented by , where m is an integer from 1 to 8, and Rf １ is a divalent fluoropolyoxyalkylene group containing 2 to 20 repeating units, wherein the repeating units are: (i) -CFXO-, (wherein X is F or CF ３ (is); (ii) -CF ２ CFXO-(wherein X is F or CF) ３ (is); (iii) - CFXCF ２ O - (wherein X is F or CF) ３ (is); (iv) -CF ２ CF ２ CF ２ O-; or (v)-CF ２ CF ２ CF ２ CF ２ Represented by O-, or Rf １ (vi) - (CF ２ ) ｎ -CFY-O-(wherein n is an integer from 0 to 3, and Y is the general formula -ORf) ２ It is a monovalent group represented by Z, where Rf ２ is -CFXO-, -CF ２ CFXO-, -CF ２ CF ２ CF ２ O-, or -CF ２ CF ２ CF ２ CF ２ A divalent fluoropolyoxyalkylene group represented by O-, containing 2 to 20 repeating units, where each X is the same or different, F or CF ３ And Z is a monovalent C １－５It is a divalent group represented as a perfluoroalkyl group.

[0055] A specific example of a perfluoropolyether is the product GALDEN® "HT55" (manufactured by Solvay).

[0056] (Heat transfer fluid) This disclosure also relates to heat transfer fluid.

[0057] The heat transfer fluid of this disclosure comprises or consists of the compositions of this disclosure.

[0058] If the heat transfer fluid in this disclosure includes the perfluoropolyether described above, then these and C ６ F １２ Since the compounds represented by have similar properties as heat transfer fluids, the properties as heat transfer fluids remain basically unchanged regardless of their content ratio. Therefore, in this case, the heat transfer fluid of this disclosure is C ６ F １２ The compound represented by is preferably present in an amount of 40% to 99.9% by mass, more preferably 60% to 99.9% by mass, and even more preferably 80% to 99.9% by mass, relative to the total heat transfer fluid.

[0059] The heat transfer fluid of this disclosure may contain any additives other than those described above, as long as they do not impede its effects and purpose. Examples of such additives include stabilizers.

[0060] Stabilizers exert their functions as so-called acid acceptors or antioxidants by exhibiting stabilizing effects. Major stabilizing effects include preventing the decomposition of HFP dimers by capturing radicals generated in the system, and preventing further decomposition of HFP dimers by capturing acids generated in the system.

[0061] A wide range of known stabilizers can be used as such stabilizers. In particular, it is preferable to use one or more stabilizers selected from the group consisting of unsaturated alcohol-based stabilizers, nitro-based stabilizers, amine-based stabilizers, phenol-based stabilizers, and epoxy-based stabilizers, as these can effectively suppress the occurrence of metal corrosion caused by the composition.

[0062] A wide range of known unsaturated alcohol-based stabilizers can be used. For example, one or more selected from the group consisting of 3-buten-2-ol, 2-buten-1-ol, 4-propen-1-ol, 1-propen-3-ol, 2-methyl-3-buten-2-ol, 3-methyl-3-buten-2-ol, 3-methyl-2-buten-1-ol, 2-hexen-1-ol, 2,4-hexadiene-1-ol, and oleyl alcohol can be used.

[0063] As nitro-based stabilizers, a wide range of known substances can be used. Examples of aliphatic nitro compounds include nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. As aromatic nitro compounds, one or more selected from the group consisting of nitrobenzene, o-, m-, or p-dinitrobenzene, o-, m-, or p-nitrotoluene, dimethylnitrobenzene, m-nitroacetophenone, o-, m-, or p-nitrophenol, o-nitroanisole, m-nitroanisole, and p-nitroanisole can be used.

[0064] A wide range of known amine-based stabilizers can be used. For example, one or more selected from the group consisting of pentylamine, hexylamine, diisopropylamine, diisobutylamine, di-n-propylamine, diallylamine, triethylamine, N-methylaniline, pyridine, morpholine, N-methylmorpholine, triallylamine, allylamine, α-methylbenzylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, isopropylamine, dipropylamine, tripropylamine, butylamine, isobutylamine, dibutylamine, tributylamine, dibentilamine, tribentilamine, 2-ethylhexylamine, aniline, N,N-dimethylaniline, N,N-diethylaniline, ethylenediamine, propylenediamine, diethylenetriamine, tetraethylenepentamine, benzylamine, dibenzylamine, diphenylamine, and diethylhydroxylamine can be used.

[0065] A wide range of known phenolic stabilizers can be used. For example, one or more selected from the group consisting of 2,6-ditterybutyl-4-methylphenol, 3-cresol, phenol, 1,2-benzenediol, 2-isopropyl-5-methylphenol, and 2-methoxyphenol can be used.

[0066] A wide range of known epoxy stabilizers can be used. For example, one or more selected from the group consisting of butylene oxide, 1,2-propylene oxide, 1,2-butylene oxide, butyl glycidyl ether, diethylene glycol diglycidyl ether, and 1,2-epoxy-3-phenoxypropane can be used.

[0067] By using stabilizers with different stabilizing effects in combination, C can be controlled in various ways. ６ F １２For the reason that it more effectively prevents the decomposition of the compound represented by the above, it is preferable that the stabilizer consists of one or more selected from the group consisting of the epoxy-based stabilizer, unsaturated alcohol-based stabilizer, nitro-based stabilizer, and phenol-based stabilizer.

[0068] The above CC ６ F １２ From the viewpoint of effectively suppressing acid liberation from the compound represented by and inhibiting metal corrosion by the liquid composition, the stabilizer content relative to the total heat transfer fluid is preferably 0.0001% by mass or more, and more preferably 0.01% by mass or more. On the other hand, considering the need to avoid undesirable changes in the physical properties of the liquid composition due to excessive addition of stabilizers, the stabilizer content relative to the total heat transfer fluid is preferably 10% by mass or less, and more preferably 5% by mass or less.

[0069] The heat transfer fluids of this disclosure can be used to remove heat from or supply heat to various objects, and can be applied, for example, as a medium for immersion cooling such as single-phase immersion cooling and two-phase immersion cooling, as well as in applications such as chiller fluids and Rankine cycle working fluids.

[0070] In this disclosure, the objects to which heat is transferred include articles, devices, and atmospheres that are cooled, heated, or maintained at a temperature to be controlled. Examples of such objects to which heat is transferred include electrical components, mechanical components, and optical components, as well as processed products and assemblies thereof. Specific examples of objects to which heat is transferred in this disclosure, though not limited to these, include wafers used in the manufacture of semiconductor devices, microprocessors, power control semiconductors, electrical branch switches, power transformers, circuit boards, multi-chip modules, mounted and unmounted semiconductor devices, chemical reactors, nuclear reactors, fuel cells, lasers, and missile components.

[0071] The heat transfer fluids of this disclosure can be used in place of the heat transfer fluid currently in use in equipment designed to transfer heat using them.

[0072] The heat transfer fluids of this disclosure can be used as a drop-in, nearly drop-in, or retrofit replacement for existing heat transfer fluids. “Drop-in replacement” means replacement without any changes to the equipment. “Nearly drop-in replacement” means replacement with minimal changes to the equipment. “Retrofit replacement” means replacement with minimal changes to the equipment (without significant changes). Preferably, the heat transfer fluids of this disclosure can be used as a drop-in or nearly drop-in replacement for existing heat transfer fluids.

[0073] Whether a drop-in replacement, near-drop-in replacement, or retrofit replacement is possible can be determined by whether all of the following conditions are met: (i) The boiling point of the heat transfer fluid is at least about 80% of the boiling point of the heat transfer fluid before replacement, preferably at least about 85%. (ii) The freezing point of the heat transfer fluid is equal to or less than the freezing point of the heat transfer fluid before replacement. (iii) The kinematic viscosity of the heat transfer fluid is at least about 200% or less of the kinematic viscosity of the heat transfer fluid before replacement, preferably at least about 150% or less. (iv) The heat transfer fluid is compatible with the heat transfer fluid before replacement in any proportion.

[0074] By setting the boiling point of the heat transfer fluid of this disclosure to at least about 80% or more, preferably at least about 85% or more, of the boiling point of the heat transfer fluid before replacement, the occurrence of cavitation and leakage from the device can be suppressed. The upper limit of the boiling point of the heat transfer fluid is not particularly limited, but for example, it may be at least about 130% or less of the boiling point of the heat transfer fluid before replacement.

[0075] By setting the pour point of the heat transfer fluid of this disclosure to be equal to or lower than the pour point of the heat transfer fluid before replacement, it becomes possible to use it at temperatures below the conventional operating temperature, thereby widening the operating temperature range. The upper limit of the pour point of the heat transfer fluid is not particularly limited, but for example, it may be 30°C higher or lower than the pour point of the heat transfer fluid before replacement.

[0076] By setting the kinematic viscosity of the heat transfer fluid of this disclosure to at least about 200%, preferably at least about 150%, of the kinematic viscosity of the heat transfer fluid before replacement, it is possible to suppress an increase in power consumption or reduce power consumption. It is preferable, but not limited to, that the kinematic viscosity be compared at the operating temperature, and for example, it can be compared at any temperature between -20°C and -40°C, specifically at -20°C.

[0077] The heat transfer fluid of this disclosure is compatible with the heat transfer fluid before replacement in any proportion, which facilitates the replacement process.

[0078] Furthermore, the heat transfer fluids of this disclosure are more suitable for drop-in replacement, nearly drop-in replacement, or retrofit replacement if they satisfy the following conditions: (v) The heat transfer fluid of this disclosure has a dielectric constant of 120% or less of the heat transfer fluid before replacement. (vi) The heat transfer fluid of this disclosure has a dielectric strength of 90% or more of the heat transfer fluid before replacement. (vii) The heat transfer fluid of this disclosure has a specific heat of 90% or more of the heat transfer fluid before replacement. (viii) The heat transfer fluid of this disclosure has a thermal conductivity of 90% or more of the heat transfer fluid before replacement.

[0079] The heat transfer fluid of this disclosure can be suitably used as a substitute composition by setting its dielectric constant to 120% or less of the dielectric constant of the heat transfer fluid before replacement. The upper limit of the dielectric constant of the heat transfer fluid is not particularly limited, but for example, it may be 80% or more of the dielectric constant of the heat transfer fluid before replacement.

[0080] The heat transfer fluid disclosed herein can be suitably used as a replacement composition by setting its dielectric strength to 90% or more of the dielectric strength of the heat transfer fluid before replacement. The upper limit of the dielectric strength of the heat transfer fluid is not particularly limited, but for example, it may be 120% or less of the dielectric strength of the heat transfer fluid before replacement.

[0081] The heat transfer fluid of this disclosure can be suitably used as a substitute composition by setting its specific heat to 90% or more of the specific heat of the heat transfer fluid before replacement. The upper limit of the specific heat of the heat transfer fluid is not particularly limited, but for example, it may be 120% or less of the specific heat of the heat transfer fluid before replacement.

[0082] The heat transfer fluid of this disclosure can be suitably used as a substitute composition by setting its thermal conductivity to 90% or more of the thermal conductivity of the heat transfer fluid before replacement. There is no particular upper limit to the thermal conductivity of the heat transfer fluid, but for example, it may be 120% or less of the thermal conductivity of the heat transfer fluid before replacement.

[0083] The boiling point of the heat transfer fluid of this disclosure is preferably 40°C or higher, more preferably 45°C or higher. Furthermore, the upper limit of the boiling point of the heat transfer fluid of this disclosure is not particularly limited, but may be, for example, 80°C or lower, 70°C or lower, or 60°C or lower.

[0084] The pour point of the heat transfer fluid of this disclosure is preferably -80°C or lower, more preferably -90°C or lower, and even more preferably -100°C or lower. The lower limit of the pour point of the heat transfer fluid of this disclosure is not particularly limited, but may be, for example, -160°C or higher, or -140°C or higher.

[0085] The kinematic viscosity of the heat transfer fluid of this disclosure may be preferably 4.0 cSt or less, more preferably 3.0 cSt or less, even more preferably 2.0 cSt or less, and even more preferably 1.5 cSt or less at -20°C. Furthermore, the lower limit of the kinematic viscosity of the heat transfer fluid of this disclosure is not particularly limited, but may be, for example, 0.2 cSt or more.

[0086] The dielectric constant of the heat transfer fluid of this disclosure is preferably 3.0 or less, more preferably 2.5 or less, and even more preferably 2.0 or less. Furthermore, the lower limit of the dielectric constant of the heat transfer fluid of this disclosure is not particularly limited, but may be, for example, 1.1 or more.

[0087] The dielectric strength of the heat transfer fluid of this disclosure is preferably 40 kV or more, more preferably 50 kV or more, and even more preferably 50 kV or more. Furthermore, there is no particular upper limit to the dielectric strength of the heat transfer fluid of this disclosure, but it may be, for example, 150 kV or less, or 100 kV or less.

[0088] The specific heat of the heat transfer fluid of this disclosure may be preferably 800 J / kg·K or more, more preferably 900 J / kg·K or more, and even more preferably 1000 J / kg·K or more at 30°C. Furthermore, there is no particular upper limit to the specific heat of the heat transfer fluid of this disclosure, but it may be, for example, 2000 J / kg·K or less, or 1500 J / kg·K or less.

[0089] The thermal conductivity of the heat transfer fluid of this disclosure may be preferably 0.055 W / mK or higher, more preferably 0.060 W / mK or higher, at 30°C. Furthermore, there is no particular upper limit to the thermal conductivity of the heat transfer fluid of this disclosure, but it may be, for example, 0.090 W / mK or lower, or 0.080 W / mK or lower.

[0090] The boiling point of the heat transfer fluid in this disclosure is the temperature at which a peak originating from endothermic heating was observed when the temperature was increased from 25°C at a rate of 5°C / min using DSC (Suggestive Operational Calorimetry).

[0091] The pour point of the heat transfer fluid in this disclosure is the temperature at which a peak originating from endothermic heating is observed when the fluid is cooled to below its freezing point with liquid nitrogen using DSC, and then heated at a rate of 5°C / min.

[0092] The dielectric constant of the heat transfer fluid in this disclosure is the value observed at a frequency of 1 kHz under conditions of 25°C and 60% humidity, using the capacitance method.

[0093] The kinematic viscosity and density of the heat transfer fluids in this disclosure were measured using an Anton Paar SVM3001 kinematic viscometer.

[0094] The dielectric strength of the heat transfer fluid in this disclosure is the dielectric breakdown voltage when a liquid sample is immersed between spherical electrodes adjusted to a predetermined spacing and the voltage is increased at a constant rate. The measurement conditions are as follows: Electrode shape: Spherical (φ12.5 mm) Electrode spacing: 2.5 mm Voltage increase rate: 2 kV / sec Measurement atmosphere: Air (22°C, 57% RH)

[0095] The specific heat of the heat transfer fluid in this disclosure is obtained using a DSC under the following conditions: Measurement device: Perkin-Elmer differential scanning calorimeter DSC8500 Heating rate: 10°C / min Standard sample: Sapphire (-Al2O3) Atmosphere: Dry nitrogen stream Sample container: Sealed aluminum container

[0096] The thermal conductivity of the heat transfer fluid in this disclosure is a value obtained by the transient nanowire method.

[0097] The compatibility of the heat transfer fluids of this disclosure is determined by whether or not they become compatible when mixed with the solvent in question. Here, compatibility means that when the two are mixed, they become a uniform state, that is, the phases do not separate.

[0098] (Heat transfer device) The disclosure further discloses a heat transfer device comprising a device and a mechanism for transferring heat to or from the device, including the heat transfer fluid described above.

[0099] Examples of devices include computers, server computers, servers including blade servers; disk arrays / storage systems; storage area networks; network-connected storage; storage communication systems; workstations; routers; telecommunications infrastructure / switches; wired, optical and wireless communication equipment; cell processing equipment; printers; power supplies; displays; optical devices; measurement systems including handheld systems; and military electronic equipment.

[0100] In different terms, the device may be a component, workpiece, assembly, etc., that is cooled, heated, or maintained at a predetermined temperature or temperature range. Examples of such devices include electrical components, mechanical components, and optical components. Specifically, examples include, but are not limited to, microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, power distribution switches, power transformers, circuit boards, multi-chip modules, packaged or unpackaged semiconductor devices, lasers, chemical reactors, fuel cells, heat exchangers, and electrochemical cells. In some embodiments, the device may include a cooler, a heater, or a combination thereof.

[0101] Semiconductor elements are heat-generating elements mounted in devices, such as CPUs, GPUs, and SSDs. These semiconductor elements are composed of single elements such as silicon and germanium, and compound semiconductors such as gallium arsenide (GaAs), gallium phosphide (GaP), indium phosphide (InP), gallium nitride (GaN), and silicon carbide (SiC).

[0102] If the device is a server computer, one or more logic boards are located within its internal space. A logic board contains numerous heat-generating electronic components, including at least one processor such as a CPU or GPU. In addition, other heat-generating components of the computer may be used, such as chipsets; memory, graphics chips, network chips, RAM, power supplies, daughter cards; and storage drives such as solid-state drives and mechanical hard disks.

[0103] A heat transfer device is a device that uses the above-mentioned heat transfer fluid to transfer heat between itself and an object to be heated. Heat is exchanged (transferred) through thermal contact with the object to be heated. For example, removing heat from an object to be heated is called cooling, and supplying heat is called heating. Different mechanisms may be used depending on the case, but a single heat transfer device may be used to handle both cooling and heating.

[0104] There are no particular limitations on the heat transfer devices, and examples include pumps, valves, fluid confinement systems, pressure control systems, coolers, heat exchangers, heat sources, heat sinks, refrigeration systems, active temperature control systems, and passive temperature control systems.

[0105] More specifically, these include temperature-controlled wafer chucks in plasma-enhanced chemical vapor deposition (PECVD) tools, temperature-controlled test heads for die performance testing, temperature-controlled work areas in semiconductor process equipment, thermal shock test bath reservoirs, and constant temperature baths.

[0106] The heat transfer object that comes into thermal contact with the heat transfer device is an article, device, or atmosphere that is cooled, heated, or maintained at a temperature to be controlled. Examples of such heat transfer objects include electrical components, mechanical components, and optical components, as well as their processed products and assemblies. Specific examples of heat transfer objects in this disclosure include, but are not limited to, microprocessors, wafers used to manufacture semiconductor devices, power control semiconductors, electrical branch switches, power transformers, circuit boards, multi-chip modules, mounted and unmounted semiconductor devices, chemical reactors, nuclear reactors, fuel cells, lasers, and missile components.

[0107] When using the heat transfer apparatus of this disclosure, the temperature conditions for the heat transfer fluid of this disclosure are preferably -100 to 45°C, more preferably -90 to 45°C, and even more preferably -70 to 45°C. The heat transfer fluid of this disclosure has the advantage of exhibiting low kinematic viscosity even at low temperatures below -20°C, and especially low kinematic viscosity at -70 to -60°C, so the apparatus can be suitably used even in the above temperature range.

[0108] (Heat Transfer Method) The Disclosure further discloses a heat transfer method comprising the steps of preparing a device and transferring heat to or from the device using the heat transfer fluid described above. Here, heat can be transferred by positioning a heat transfer device in thermal contact with the device. When positioned in thermal contact with the device, the heat transfer device removes heat from the device, supplies heat to the device, or maintains the device at a selected temperature or temperature range. The direction of the heat flow (from or to the device) is determined by the relative temperature difference between the device and the heat transfer device.

[0109] (Foaming agents) This disclosure also relates to foaming agents.

[0110] The foaming agent of this disclosure comprises or consists of the composition of this disclosure.

[0111] The foaming agent in this disclosure is C ６ F １２ The compound may include additional compounds different from the compound represented by . The additional compounds may be one or more types. For example, C ６ F １２ Other examples include fluorine-substituted olefins, substituted or unsubstituted olefins other than fluorine-substituted olefins, halogenated hydrocarbons other than olefins, other organic compounds, or inorganic compounds.

[0112] C ６ F １２Other fluorine-substituted olefins may include, for example, hydrofluoroolefins or hydrochlorofluoroolefins having 1 to 30 carbon atoms, and specific examples include 1,3,3,3-tetrafluoropropene, 1,1,3,3-tetrafluoropropene, 1,2,3,3,3-pentafluoropropene, 1,1,1-trifluoropropene, 1,1,1,3,3-pentafluoropropene (HFO-1225zc), and 1,1,1,3,3,3-hexafluorobut-2-e Examples include octafluoro-2-butene, 1,1,2,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene, trans-1,2-dichloroethylene, 1-chloro-2,3,3,3-tetrafluoropropene, 2-chloro-1,3,3,3-tetrafluoropropene, 1-chloro-2,3,3,4,4,5,5-heptafluoropentene, 1,1-dichloro-2-fluoroethylene, and 1-chloro-3,3,3-trifluoropropene.

[0113] Other substituted or unsubstituted olefins besides fluorine-substituted olefins may include, for example, halogenated olefins having 1 to 30 carbon atoms, and specific examples include tetrachloroethylene, ethylene, propylene, and n-butene.

[0114] Examples of halogenated hydrocarbons other than olefins include difluoromethane, pentafluoroethane, 1,1,2,2-tetrafluoroethane, 1,1,1,2-tetrafluoroethane, difluoroethane, 1,1,1,2,3,3,3-heptafluoropropane, 1,1,1,3,3,3-hexafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluorobutane, trichlorofluoromethane, dichlorodifluoromethane, trichlorotrifluoroethane, dichlorohexafluoropropane, 2,2,3-3-tetrachlorohexafluorobutane, dichlorooctafluorobutane, dichloromethane, trichloroethane, octafluoropropane, and 1,1,1,2,2,3,3-heptafluoropropane.

[0115] Other organic compounds include, for example, hydrocarbons such as methane, ethane, propane, n-butane, isobutane, n-pentane, isopentane, neopentane, cyclopentane, n-hexane, isohexane, n-heptane, or n-octane, and CHF. ２ -O-CHF ２ CHF ２ -O-CH ２ F, CHF ２ -CF ２ -O-CH ３ ,CH ２ FO-CHF-CH ２ F, CHF ２ -CHF-O-CH ２ F, CF ３ -O-CHF-CH ３ CF ３ -CHF-O-CH ３ CHF ２ -O-CH ２ - CHF ２ CF ３ -O-CH ２ -CH ２ F, CF ３ -CH ２ -O-CH ２ F, CF ２ H-CF ２ -CF ２ -O-CH ３ CF ３ CF ２ CF ２ -O-CH ３ , C ４ H ９ -O-CF ３ , C ４ F ９ -O-C ２ H ５ Or C ３ F ７ -O-C ３ F ７Examples include hydrofluoroethers such as methanol, ethanol, propanol, isopropanol, alcohols such as 1-hexanol, 2-hexanol, 2-ethylhexanol, or 1-octanol, ethers such as dimethyl ether, methyl ethyl ether, diethyl ether, methyl propyl ether, methyl isopropyl ether, ethyl propyl ether, ethyl isopropyl ether, dipropyl ether, or diisopropyl ether, ketones such as methyl ethyl ketone, methyl isobutyl ketone, or perfluoroethyl isopropyl ketone, and organic acids such as methyl formate, ethyl formate, or formic acid.

[0116] Examples of inorganic compounds include water, nitrogen, oxygen, argon, and carbon dioxide.

[0117] The foaming agents of this disclosure may include the compounds listed above for any reason, such as for the purpose of being co-foaming agents or vapor pressure regulators, or as by-products during manufacturing.

[0118] C in the foaming agent of this disclosure ６ F １２ The content of the compound represented by may be any value depending on the intended use of the blowing agent in this disclosure. However, among the compounds listed above, GWP is C ６ F １２ A compound with a higher value than the compound represented by C ６ F １２ This also includes compounds that promote the decomposition of C in the foaming agent of this disclosure. ６ F １２ The content of the compound represented by is preferably 40% to 99% by mass, more preferably 60% to 99.9% by mass, and even more preferably 80% to 99.9% by mass, relative to the total foaming agent.

[0119] The foaming agent of this disclosure may contain a foam stabilizer (bubble stabilizer) for the purpose of improving foaming properties. Examples of foam stabilizers include polyoxyalkylene foam stabilizers such as polyoxyalkylene alkyl ethers, and surfactants such as silicone foam stabilizers such as octamethylcyclotetrasiloxane and organopolysiloxane. These foam stabilizers may be used alone or in combination of two or more.

[0120] From the viewpoint of improving foaming properties, the content of the foam stabilizer relative to the total foaming agent of this disclosure is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more. On the other hand, from the viewpoint of obtaining homogeneous foaming, the content of the foam stabilizer relative to the total foaming agent of this disclosure is preferably 10% by mass or less, and more preferably 5% by mass or less.

[0121] The blowing agent of this disclosure may contain a flame retardant for the purpose of improving flame retardancy. Examples of flame retardants include phosphate esters, phosphate-containing flame retardants, bromine-containing flame retardants, and metal hydroxides.

[0122] As the phosphate ester, it is preferable to use monophosphate esters, condensed phosphate esters, etc. For example, trimethyl phosphate, triethyl phosphate, tributyl phosphate, tri(2-ethylhexyl) phosphate, tributoxyethyl phosphate, triphenyl phosphate, tris(phenylphenyl) phosphate, trinaphthyl phosphate, cresyl diphenyl phosphate, xylenyl diphenyl phosphate, 2-methacryloyloxyethyl acid phosphate, diphenyl-2-methacryloyloxyethyl phosphate Examples include tyl phosphate, melamine phosphate, dimelamine phosphate, melamine pyrophosphate, triphenylphosphine oxide, tricresylphosphine oxide, diethyl phenylphosphonate, resylcinol bis(diphenyl phosphate), bisphenol A bis(diphenyl phosphate), trialkyl polyphosphate, resorcinol polyphenyl phosphate, resorcinol poly(di-2,6-xylyl) phosphate, hydroquinone poly(2,6-xylyl) phosphate, and condensates thereof.

[0123] Specific examples of phosphate-containing flame retardants include monophosphates and polyphosphates. Monophosphates are not particularly limited, but examples include ammonium salts such as ammonium phosphate, ammonium dihydrogen phosphate, and diammonium hydrogen phosphate; sodium salts such as monosodium phosphate, disodium phosphate, disodium phosphite, and sodium hypophosphite; potassium salts such as monopotassium phosphate, dipotassium phosphate, tripotassium phosphate, monopotassium phosphite, dipotassium phosphite, and potassium hypophosphite; lithium salts such as monolithium phosphate, dilithium phosphate, trilithium phosphate, monolithium phosphite, dilithium phosphite, and lithium hypophosphite; barium salts such as barium hydrogen phosphate and barium hypophosphite; magnesium salts such as magnesium monohydrogen phosphate, magnesium hydrogen phosphate, trimagnesium phosphate, and magnesium hypophosphite; calcium salts such as calcium dihydrogen phosphate, calcium hydrogen phosphate, tricalcium phosphate, and calcium hypophosphite; and zinc salts such as zinc phosphate, zinc phosphite, and zinc hypophosphite. Polyphosphates are not particularly limited, but examples include ammonium polyphosphate, piperazine polyphosphate, melamine polyphosphate, ammonium polyphosphate amide, and aluminum polyphosphate. One or more types of phosphate-containing flame retardants may be used.

[0124] From the viewpoint of improving flame retardancy, the flame retardant content relative to the total blowing agent of this disclosure is preferably 0.5% by mass or more, more preferably 2% by mass or more, and even more preferably 5% by mass or more. On the other hand, from the viewpoint of preventing foaming inhibition due to an excessive amount of flame retardant, the flame retardant content relative to the total blowing agent of this disclosure is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0125] There are no particular limitations on bromine-containing flame retardants as long as they are compounds that contain bromine in their molecular structure, but examples include aromatic brominated compounds. Specific examples of aromatic brominated compounds include monomer-based organic bromine compounds such as hexabromobenzene, pentabromotoluene, hexabromobiphenyl, decabromobiphenyl, hexabromocyclodecane, hexabromodiphenyl ether, bis(pentabromphenoxy)ethane, ethylene-bis(tetrabromophthalimide), and tetrabromobisphenol A; brominated polycarbonates such as copolymers of polycarbonate oligomers and bisphenol A; poly(brominated benzyl acrylate), brominated polyphenylene ether, brominated bisphenol A, cyanuryl chloride, and condensates of brominated phenols; brominated polystyrene such as brominated (polystyrene), poly(brominated styrene), and cross-linked brominated polystyrene. One or more types of bromine-containing flame retardants can be used.

[0126] Examples of metal hydroxides include aluminum hydroxide, magnesium hydroxide, calcium hydroxide, iron hydroxide, nickel hydroxide, zirconium hydroxide, zinc hydroxide, titanium hydroxide, copper hydroxide, tin hydroxide, and vanadium hydroxide. One or more types of metal hydroxides can be used.

[0127] The blowing agents of this disclosure may be used alone as physical blowing agents or in combination with known chemical blowing agents. Examples of the above chemical blowing agents include 4,4'-oxybis(benzenesulfonyl hydrazide), diphenylsulfon-3,3'-disulfonylhydrazide arylbis(sulfonyl hydrazide), p-toluenesulfonyl hydrazide, azodicarbonamide (ADCA), azobisformamide, azobisisobutyronitrile, p-toluenesulfonyl semicarbazide, 5-morpholyl-1,2,3,4-thiatriazole, N,N-dinitrosoterephthalamide, water, ammonium carbonate, ammonium bicarbonate, ammonium nitrite, ammonium borohydride, azides, etc. In addition to the above compounds, the above chemical blowing agents may also contain urea or the like as a blowing aid.

[0128] The blowing agent of this disclosure can be used in a variety of products in which a physical blowing agent may be used in the manufacturing process. A specific application is as a blowing agent used in the manufacture of rigid polyurethane foam. Conventionally, CFCs and HCFCs have been widely used as blowing agents for rigid polyurethane foam, and this is one area where the demand for alternative materials is increasing. The blowing agent of this disclosure can be suitably used as a substitute for CFCs and HCFCs as a blowing agent for rigid polyurethane foam.

[0129] (Lubricants) This disclosure also relates to lubricants.

[0130] The lubricants of the present disclosure comprise the compositions of the present disclosure. In a preferred embodiment, the lubricants of the present disclosure comprise the compositions of the present disclosure as diluent solvents for diluting the lubricant components.

[0131] The lubricant component may be in liquid, grease, or solid form. The lubricant component may be any of the known lubricants, such as mineral oil-based, synthetic oil-based, fluorine-based, or silicone-based lubricants. There may be one lubricant component or two or more.

[0132] As the mineral oil-based lubricant component, various commercially available lubricant components such as paraffin oil-based or naphthenic oil-based components may be used.

[0133] As components of the synthetic oil-based lubricant, alkylbenzene, poly(α-olefin), ester, polyol ester, polyalkylene glycol, polyvinyl ether, etc. may be used.

[0134] Specific examples of alkylbenzenes include n-octylbenzene, n-nonylbenzene, n-decylbenzene, n-undecylbenzene, n-dodecylbenzene, n-tridecylbenzene, 2-methyl-1-phenylheptane, 2-methyl-1-phenyloctane, 2-methyl-1-phenylnonane, 2-methyl-1-phenyldecane, 2-methyl-1-phenylundecane, 2-methyl-1-phenyldodecane, and 2-methyl-1-phenyltridecane.

[0135] Specific examples of esters include aromatic esters such as benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, and mixtures thereof, as well as dibasic acid esters, polyol esters, complex esters, and carbonate esters.

[0136] Examples of alcohols used as raw materials for polyol esters include polyhydric alcohols such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di(trimethylolpropane), tri(trimethylolpropane), pentaerythritol, di(pentaerythritol), and tri(pentaerythritol). Examples of carboxylic acids used as raw materials for polyol esters include valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, oleic acid, isopentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-ethylhexanoic acid, and 3,5,5-trimethylhexanoic acid.

[0137] Examples of polyalkylene glycols include compounds obtained by addition polymerization of alkylene oxides (e.g., ethylene oxide, propylene oxide, butylene oxide, etc.) with an alcohol having 1 to 18 carbon atoms (e.g., aliphatic alcohols such as methanol, ethanol, linear or branched propanol, linear or branched butanol, linear or branched pentanol, linear or branched hexanol, etc.).

[0138] Examples of polyvinyl ethers include polymethyl vinyl ether, polyethyl vinyl ether, poly-n-propyl vinyl ether, and polyisopropyl vinyl ether.

[0139] Examples of fluorine-based lubricant components include polytetrafluoroethylene (PTFE), tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer (PFA), tetrafluoroethylene-hexafluoropropylene copolymer (FEP), tetrafluoroethylene-ethylene copolymer (ETFE), polyvinylidene fluoride (PVDF), polychlorotrifluoroethylene (PCTFE), and perfluoropolyether.

[0140] Examples of silicone-based lubricant components include dimethyl silicone, methyl hydrogen silicone, methylphenyl silicone, cyclic dimethyl silicone, and modified silicone oil.

[0141] From the viewpoint of appropriately adjusting the thickness of the lubricant coating film, the content of the above-mentioned lubricant components is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass, and even more preferably 0.2 to 20% by mass, relative to the total lubricant of this disclosure.

[0142] The lubricants disclosed herein may be used depending on the application, C ６ F １２ The lubricant may contain additional compounds other than the compound represented by as other solvent components. The type of such solvent component is not particularly limited and may include various solvent components that are generally used as solvents or diluents for lubricants. When the lubricant of this disclosure contains other solvent components, from the viewpoint of compatibility with fluorine-based lubricant components or silicone-based lubricant components, and from the viewpoint of reducing the GWP of the lubricant, the other solvent component is preferably a hydrofluoroolefin, a hydrofluoroether, or a hydrofluorocarbon. Also from a similar viewpoint, C in the lubricant of this disclosure ６ F １２ The content of the compound represented by is preferably 40% to 99% by mass, more preferably 60% to 99.9% by mass, and even more preferably 80% to 99.9% by mass, relative to the total amount of solvent components.

[0143] The lubricant of this disclosure may contain other additives besides the solvent and lubricant components described above, depending on the application, as long as they do not impair the properties of the lubricant. Other additives may be various additives known in the art, such as antioxidants, wear inhibitors, rust inhibitors, thickeners, structural stabilizers, fluorescent agents, colorants, surfactants, etc., and one or more of these additives may be included.

[0144] The lubricant disclosed herein can be applied to any sliding parts such as metals, resins, and rubbers to prevent frictional heat and wear on the contact surface.

[0145] (Cleaning agents) This disclosure also relates to cleaning agents.

[0146] The cleaning agent of this disclosure comprises or consists of the composition of this disclosure.

[0147] The cleaning agent of this disclosure may contain the composition of this disclosure as a cleaning agent component, or as a solvent for the cleaning agent component, depending on the application. In either case, the composition of this disclosure is C ６ F １２ Additional compounds different from the compounds represented by may be included as detergent or solvent components. Examples of such additional detergent or solvent components include 1-bromo-2-methylpropane, trichlorofluoromethane, dichlorodifluoromethane, trichlorotrifluoroethane, 1,1,1,4,4,4-hexafluorobutane, 1,1,1,3,3-pentafluorobutane, 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane, 1,1,1,2,2,3,3,4,4-nonafluorohexane, 1,1, Halogenated hydrocarbons such as 2,2,3,3,4-heptafluorocyclopentane, 2,3,3,4,4,5,5-heptafluoro-1-pentene, 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene, 1-fluorooctane, 1-chloro-2,3,3,3-tetrafluoropropene, tetrachloroethylene, 1,1-dichloro-2-fluoroethylene, 1-chloro-3,3,3-trifluoropropene, and other halogenated olefins, CHF ２ -O-CHF ２ CHF ２ -O-CH ２ F, CHF ２ -CF ２ -O-CH ３ ,CH ２ FO-CHF-CH ２ F, CHF ２ -CHF-O-CH ２ F, CF ３ -O-CHF-CH ３ CF ３ -CHF-O-CH ３ CHF ２ -O-CH ２ - CHF ２ CF３ -O-CH ２ -CH ２ F, CF ３ -CH ２ -O-CH ２ F, CF ２ H-CF ２ -CF ２ -O-CH ３ CF ３ CF ２ CF ２ -O-CH ３ , C ４ H ９ -O-CF ３ , C ４ F ９ -O-C ２ H ５ Or C ３ F ７ -O-C ３ F ７ Examples include hydrofluoroethers such as n-hexane, isohexane, cyclohexane, ethylcyclohexane, methylcyclohexane, n-heptane, isoheptane, n-octane, isooctane, n-nonane, isononane, n-decane, isodecane, and other hydrocarbons; methanol, ethanol, propanol, isopropanol, 1-hexanol, 2-hexanol, 2-ethylhexanol, or 1-octanol, and other alcohols; ethers such as dimethyl ether, methyl ethyl ether, diethyl ether, methyl propyl ether, methyl isopropyl ether, ethyl propyl ether, ethyl isopropyl ether, dipropyl ether, or diisopropyl ether; ketones such as methyl ethyl ketone, methyl isobutyl ketone, or perfluoroethyl isopropyl ketone; or water.

[0148] C in the cleaning agent of this disclosure ６ F １２ The content of the compound represented by may be any value depending on the intended use of the detergent of this disclosure. However, among the compounds listed above, GWP is C ６ F １２ A compound with a higher value than the compound represented by C ６ F １２This also includes compounds that promote the decomposition of C in the detergent of this disclosure. ６ F １２ The content of the compound represented by is preferably 40% to 99% by mass, more preferably 60% to 99.9% by mass, and even more preferably 80% to 99.9% by mass, relative to the total detergent.

[0149] The cleaning agent of this disclosure may contain one or more stabilizers, additives, and other components, to the extent that it does not impair the performance as a cleaning agent. Examples of stabilizers that the cleaning agent of the present invention may contain include 1,2-butylene oxide, 2,3-butylene oxide, propylene oxide, pentene oxide, epichlorohydrin, butyl glycidyl ether, 2-ethylhexyl glycidyl ether, glycidyl acetate, glycidyl propionate, 1,2-epoxycyclopentane, styrene oxide, nitromethane, nitroethane, 1-nitropropane, 1,3-dioxolane, 1,4-dioxane, tetrahydrofuran, and the like. These may be used individually or in combination of two or more.

[0150] The additives may be various additives known in the art, such as water, ultraviolet absorbers, antioxidants, polymerization inhibitors, rust inhibitors, defoamers, surfactants, and chelating agents. These may be used individually or in combination of two or more.

[0151] Examples of UV absorbers include benzotriazole-based UV absorbers, benzophenone-based UV absorbers, and hindered amine-based UV absorbers.

[0152] Examples of antioxidants include phenolic antioxidants such as 2,6-di-t-butyl-4-methylphenol, triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], and 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], and amine-based antioxidants such as alkylated diphenylamine, tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, and N,N-di-sec-butyl-p-phenylenediamine.

[0153] Examples of rust inhibitors include cyclohexylamine, dicyclohexylamine, and N,N-bis(2-hydroxyethyl)-N-cyclohexylamine.

[0154] Examples of surfactants include higher alcohol ethylene oxide adducts, alkylphenol ethylene oxide adducts, fatty acid ethylene oxide adducts, higher alkylamine ethylene oxide adducts, fatty acid esters of sorbitol and sorbitan, sucrose fatty acid esters, silicone-based surfactants, and fluorine-based surfactants.

[0155] Other components that the detergents of this disclosure may contain include ethanol, methanol, 1-propanol, isopropyl alcohol, 1-butanol, methyl acetate, ethyl acetate, n-propyl acetate, amyl acetate, ethyl lactate, γ-butyrolactone, dimethyl carbonate, dimethyl oxalate, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether, limonene, pinene, myrcene, linalool, terpineol, and the like. The detergents of this disclosure may contain these components as fragrances or as impurities.

[0156] The cleaning agent of this disclosure can be suitably used as a cleaning agent for oil and grease stains adhering to various substrates. Specific types of stains include oil stains such as mineral oil, vegetable oil, animal oil, heavy oil, wax, silicone oil, and fluorine oil; stains derived from rosin-based flux; and resin stains such as urethane resin, epoxy resin, acrylic resin, silicone resin, ABS resin, polyamide resin, polyvinyl chloride resin, polyester resin, acrylic resin, and polylactic acid resin. The above-mentioned stain components are derived from, for example, cutting oil, press oil, drawing oil, heat treatment oil, rust-preventive oil, lubricating oil, metalworking oil, plastic working oil, grease, asphalt, water-soluble oil, solder, heat insulating material, coatings for electronic circuit boards, adhesives, etc., and can be used on various articles in which these may be used, such as glass, windows, substrates, displays, lenses, lighting fixtures, automobile parts, automobile interiors, industrial valves, gears, bearings, pump parts, pipes, building materials, paint filaments, etc.

[0157] Although embodiments of the present invention have been described above, the present invention is not limited in any way to these examples, and can be implemented in various forms without departing from the spirit of the invention.

[0158] The embodiments of the present invention will be described in more detail below based on examples, but the present invention is not limited to these.

[0159] (Preparation Example 1) An HFP dimer was obtained based on the method described in the Journal of Synthetic Organic Chemistry, Japan (1981), Vol. 39, pp. 51-62. The obtained HFP dimer was purified by distillation to remove impurities such as hexafluoropropene trimers. The obtained HFP dimer was washed with a 1% KOH aqueous solution. The fluoride ion concentration was less than 1 ppb by mass (below the detection limit). Furthermore, the purified HFP dimer was separated into the E-isomer of formula (I), the Z-isomer of formula (I), and the compound represented by (II) by rectification and preparative gas chromatography. Each of the separated HFP dimers was dehydrated using silica gel.

[0160] The compounds represented by the E-form of formula (I) and the Z-form of formula (I) obtained above were mixed in the proportions shown in Table 1 below to obtain a dimer mixture.

[0161] (Stability Test) The obtained heat-conducting fluid composition was placed in a stainless steel autoclave, sealed, and heated and held at the temperatures shown in Table 1 for 168 hours. The obtained heat-conducting fluid composition was also placed in a stainless steel autoclave, sealed, and heated and held at the temperatures shown in Table 1 for 336 hours.

[0162] (Measurement of the purity of the hexafluoropropene dimer) In the stability test, the purity of the hexafluoropropene dimer was measured by gas chromatography before and after 168 hours of heating and holding. The results obtained are shown in the "Post-test purity (1) (wt%)" column of Table 1. In addition, in the stability test, the purity of the hexafluoropropene dimer was measured by gas chromatography before and after 336 hours of heating and holding. The results obtained are shown in the "Post-test purity (2) (wt%)" column of Table 1.

[0163] From the results above, it was confirmed that Examples 1 to 14, where E / (E+Z) > 0.5, were stable and did not show any decrease in purity even after long-term storage at high temperatures.

Claims

1. C ６ F １２ A composition comprising a hexafluoropropene dimer represented by, wherein at least one of the hexafluoropropene dimers represented by ６ F １２ is a compound represented by the following formula (I); and the composition has a ratio E / (E + Z) of the E isomer to the Z isomer of the compound exceeding 0.

5.

2. The composition according to claim 1, wherein the E / (E+Z) of the compound represented by formula (I) is 0.8 to 1.

3. The composition according to claim 1, wherein the E / (E+Z) of the compound represented by formula (I) is 0.965 to 1.

4. The composition according to claim 1, further comprising a compound represented by the following formula (II).

5. Above C ６ F １２ The composition according to claim 1, wherein the compound represented by formula (I) is contained in an amount of 80% by mass or more relative to the total amount of hexafluoropropene dimers represented by the formula.

6. Above C ６ F １２ The composition according to claim 1, wherein the compound represented by formula (I) is contained in an amount of 95% by mass or more relative to the total amount of hexafluoropropene dimers represented by the formula.

7. A heat transfer fluid comprising the composition described in claim 1.

8. A heat transfer device comprising a device and a mechanism for transferring heat from or to the device, the heat transfer fluid described in claim 7.

9. A heat transfer method comprising the steps of preparing a device and transferring heat to or from the device using the heat transfer fluid described in claim 7.

10. A foaming agent comprising the composition described in claim 1.

11. A lubricant comprising the composition described in claim 1.

12. A detergent comprising the composition described in claim 1.

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