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

Definitions

• the present invention relates to a composition for a cooling/heating transfer medium liquid and a method for producing the same.
• a circulating thermostatic device that maintains a controlled object at a preset temperature by circulating a temperature-controlled circulating fluid through the controlled object, such as various devices or processes, that require temperature control.
• Fluorine-based inert liquids are colorless, transparent, odorless, inert, and non-flammable liquids that have a completely fluorinated structure, and are often used as cooling or heating medium liquids.
• PFAS perfluoroalkyl substances and polyfluoroalkyl compounds
• Patent Document 1 discloses a circulating oil for hydrocarbon refrigerants and a refrigerant composition.
• the circulating oil for hydrocarbon refrigerants and the refrigerant composition described in Patent Document 1 have a low global warming potential and an ozone depletion potential of zero, and are therefore considered suitable for use as an alternative to PFAS, particularly as a refrigerant for freezers.
• Patent Documents 2 and 3 also disclose that the internal temperature of a circulating thermostatic bath can be controlled over a wide temperature range by using silicone oil alone as a cooling and heating medium liquid.
• these cooling and heating medium liquids are used in closed circulating thermostatic baths.
• the cooling and heating medium liquids described in Patent Documents 1 to 3 are used in a circulating thermostatic bath that is partially or entirely an open system, there is a risk that water due to condensation, liquid samples, dust, etc. may get mixed into the circulating liquid through gaps in the circulating thermostatic bath.
• the mixed substances do not float near the liquid surface but dissolve or sink, making it necessary to replace the liquid with a new cooling and heating medium liquid within a short period of time, and it cannot be used continuously for long periods of time.
• the present invention aims to provide a composition for a cooling/heating transfer medium liquid that can be used continuously for long periods of time even in an open circulating thermostatic bath, and a method for producing the same.
• a composition for a cooling/heating transfer medium liquid comprising: (A) an ester compound which is in a liquid state at room temperature and has a melting point of -15°C or lower, a boiling point of 100°C or higher, and a specific gravity of 1.00 or higher; and (B) a hydrophobized cellulose.
• composition for cooling/heating transfer liquid according to ⁇ 3> wherein R 10 in the formula (3) is each independently a linear or branched alkyl group having 2 to 5 carbon atoms which may have a substituent.
• composition for a cooling/heating transfer medium liquid according to any one of ⁇ 1> to ⁇ 5>, wherein the hydrophobized cellulose contains alkyl cellulose.
• composition for a cooling/heating transfer liquid according to ⁇ 6> wherein the hydrophobized cellulose contains an alkyl cellulose represented by the following formula (5):
• R 20 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and n represents an integer of 50 to 1500, with the proviso that at least one of the 3n R 20 represents an alkyl group.
• composition for a cooling/heating transfer medium liquid according to any one of ⁇ 1> to ⁇ 7>, wherein the content of the hydrophobized cellulose is 0.1 to 10.0% by mass.
• composition for a cooling/heating transfer liquid according to any one of ⁇ 1> to ⁇ 8>, further comprising an additive having a density of more than 1.0 g cm ⁇ 3 .
• a method for producing a composition for a cooling/heating transfer liquid comprising the steps of:
• the present invention provides a composition for a cooling/heating medium liquid that can be used continuously for a long period of time even in an open circulating thermostatic bath, and a method for producing the same.
• the cooling/heating transfer liquid composition according to this embodiment contains (A) an ester compound that is liquid at room temperature and has a melting point of ⁇ 15° C. or lower, a boiling point of 100° C. or higher, and a specific gravity of 1.00 or higher (hereinafter also referred to as “component (A)”), and (B) a hydrophobized cellulose (hereinafter also referred to as “component (B)”).
• component (A) an ester compound that is liquid at room temperature and has a melting point of ⁇ 15° C. or lower, a boiling point of 100° C. or higher, and a specific gravity of 1.00 or higher
• component (B) a hydrophobized cellulose
• cooling/heating transfer liquid composition of this embodiment when a cooling/heating transfer liquid composition is used in an open circulating thermostatic bath, there is a risk that water due to condensation, liquid samples, dust, etc. may get into the circulating liquid through gaps in the circulating thermostatic bath.
• the contaminants do not dissolve or settle in the cooling/heating transfer liquid composition, but float near the liquid surface, making it easy to remove the contaminants. For this reason, the cooling/heating transfer liquid composition of this embodiment can be used continuously for long periods of time even in an open circulating thermostatic bath.
• the cooling/heating transfer medium composition according to this embodiment is not particularly limited as long as it is composed of components (A) and (B), but from the viewpoint of use as a cooling/heating transfer medium liquid for circulating thermostatic baths in a wide range of fields, it is preferable that the composition is a transparent liquid. Being a transparent liquid is preferable in that it can be installed not only in industrial applications but also in equipment in the optical field.
• the specific gravity of the cooling/heating transfer liquid composition according to this embodiment is preferably 1.00 to 1.20, and more preferably 1.01 to 1.10.
• the specific gravity can be measured at 25°C using a density specific gravity meter.
• the viscosity of the cooling/heating transfer medium composition according to this embodiment is preferably 10 to 5,000 mPa ⁇ s, more preferably 40 to 500 mPa ⁇ s, and even more preferably 50 to 150 mPa ⁇ s.
• the viscosity can be measured at 25°C using a rheometer with a cone plate having a diameter of 50 mm and an angle of 2°.
• components in contact with the cooling/heating medium liquid may deteriorate due to the migration of the cooling/heating medium liquid composition.
• various resins such as polystyrene (PS) resin, polycarbonate (PC) resin, polyethylene (PE) resin, polypropylene (PP) resin, acrylonitrile-styrene copolymer (AS) resin, acrylonitrile-butadiene-styrene copolymer (ABS) resin, polyurethane (PU) resin, acrylic resin, and polyester resin are often used for the components of the circulating thermostatic bath. Most of these exhibit chemical migration. This migration may cause the components to swell and deteriorate. To prevent this problem, it is more preferable to use a compound with low migration to resin in the cooling/heating medium liquid composition.
• cooling/heating transfer liquid composition according to this embodiment will be described in detail below. Each of the following components may be used alone or in combination of two or more.
• the ester compound as component (A) (hereinafter also referred to as the "specific ester compound”) has a melting point of -15°C or lower, a boiling point of 100°C or higher, and a specific gravity of 1.00 or higher. In other words, the specific ester compound is liquid in the range of more than -15°C and less than 100°C.
• the molecular weight of the specific ester compound is not particularly limited, but is, for example, 50 to 1000, and preferably 200 to 600.
• the molecular weight may be 250 to 500.
• the specific ester compound preferably has a bulky structure, and a bulky structure can be easily achieved by setting the molecular weight below a certain level.
• the molecular weight of the specific ester compound can be calculated from its structural formula, or can be measured by gel permeation chromatography (GPC).
• the melting point of the specific ester compound may be -20°C or lower, or -40°C or lower.
• the lower limit of the melting point is not particularly limited, but in one example it is -100°C or higher, and in another example it is -80°C or higher.
• the melting point can be measured by a differential scanning calorimeter at 1 atmosphere.
• the boiling point of the specific ester compound may be 150°C or higher, or 200°C or higher. There is no particular upper limit for this boiling point, but in one example it is 500°C or lower, and in another example it is 300°C or lower.
• the boiling point can be measured at 1 atmosphere by the equilibrium reflux boiling point method described in JIS K 2233.
• the specific gravity of the specific ester compound is preferably 1.00 to 1.30, more preferably 1.01 to 1.20, and even more preferably 1.02 to 1.10. By making the specific gravity of the specific ester compound greater than 1.00, it is possible to enhance the effect of suppressing the settling of impurities when they are mixed into the cooling/heating transfer medium composition.
• the specific gravity can be measured at 25°C using a density specific gravity meter.
• the specific ester compound is preferably a bulky compound in order to suppress migration to the resin member described above.
• An example of the specific ester compound is a compound represented by the following formula (1).
• R 1 represents a linear or branched alkyl group having 1 to 15 carbon atoms which may have a substituent.
• the linear or branched alkyl group having 1 to 15 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-pentyl group, a 2-methylbutyl group, an n-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, an n-heptyl group, a 2-methylhexyl group, a 3-methylhexyl group, a 2,3-dimethylpentyl group, a 2-ethylpentyl group, an n-octyl group, a 2-methylh
• a linear or branched alkyl group having 1 to 10 carbon atoms is preferred, a linear or branched alkyl group having 2 to 5 carbon atoms is more preferred, and an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group are even more preferred.
• the substituent that the alkyl group represented by R 1 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, an aryl group, and a halogen atom.
• the alkyl portion of the alkoxy group include the above-mentioned alkyl groups having 1 to 6 carbon atoms.
• the aryl group include a phenyl group.
• the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
• a represents an integer of 2 to 5, preferably an integer of 2 to 4, and more preferably 2 or 3.
• the structures in parentheses followed by a may be the same or different.
• R2 represents a (a+b)-valent hydrocarbon group having 1 to 10 carbon atoms, and is preferably a divalent to tetravalent hydrocarbon group.
• Examples of the (a+b)-valent hydrocarbon group having 1 to 10 carbon atoms include groups obtained by removing 2 to 4 hydrogen atoms from a hydrocarbon compound such as propane, cyclohexane, and cyclohexene; groups obtained by removing 2 to 4 hydrogen atoms from an aromatic compound such as benzene; and the like.
• R3 represents a hydroxy group or an acyloxy group having 2 to 6 carbon atoms which may have a substituent.
• the acyloxy group having 2 to 6 carbon atoms include an acetyloxy group, a propanoyloxy group, a butyryloxy group, and a pentanoyloxy group. Among these, an acetyloxy group is preferable.
• the substituent that the acyloxy group represented by R3 may have include a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, and a halogen atom.
• b 0 or 1.
• the specific ester compound may also be a compound represented by the following formula (2):
• each Q independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, a linear or branched alkenyl group having 2 to 3 carbon atoms, or a linear or branched alkoxy group having 1 to 6 carbon atoms.
• Two Qs may be bonded to each other to form an alkylene group or an alkenylene group.
• alkenyl groups having 2 to 3 carbon atoms include vinyl groups, allyl groups, and isopropenyl groups.
• m represents an integer from 0 to 5
• k represents an integer from 0 to 2.
• the m k's may be the same or different.
• each X independently represents a group represented by the following formula (2-1):
• R4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 15 carbon atoms which may have a substituent.
• Examples of the linear or branched alkyl group having 1 to 15 carbon atoms include the same groups as R1 in the above formula (1).
• Examples of the substituent that the alkyl group represented by R4 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, an aryl group, a halogen atom, etc.
• Y represents a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 3 carbon atoms which may have a substituent, a linear or branched alkoxy group having 1 to 6 carbon atoms which may have a substituent, or an acyloxy group having 2 to 6 carbon atoms which may have a substituent.
• substituents that the alkyl group, alkoxy group, or acyloxy group represented by Y may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, etc.
• the compound represented by formula (2) above may be one produced by a known method or one that is commercially available, and there is no particular restriction on this.
• methods for producing the compound represented by formula (2) above include a method in which a specific acid component and an alcohol component are subjected to an esterification reaction or transesterification reaction in the absence or presence of a catalyst, preferably in an inert gas atmosphere such as nitrogen.
• a preferred example of the specific ester compound is the compound represented by the following formula (3) (citric acid derivative).
• R 10 each independently represents a linear or branched alkyl group having 1 to 15 carbon atoms which may have a substituent.
• the linear or branched alkyl group having 1 to 15 carbon atoms include the same groups as R 1 in the above formula (1). Among them, a linear or branched alkyl group having 1 to 10 carbon atoms is preferred, a linear or branched alkyl group having 2 to 5 carbon atoms is more preferred, and an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group are more preferred.
• the substituent that the alkyl group represented by R 10 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, an aryl group, a halogen atom, and the like.
• R 12 represents a linear or branched alkyl group having 1 to 5 carbon atoms which may have a substituent.
• substituent that the alkyl group represented by R 12 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, and the like.
• R 10 is a butyl group which may have a substituent
• R 11 is a group represented by —C( ⁇ O)R 12 are preferred.
• Specific examples of the compound represented by the above formula (3) include citric acid esters such as trimethyl citrate, triethyl citrate, tripropyl citrate, triisopropyl citrate, and tributyl citrate; and acetyl citrate esters such as acetyl trimethyl citrate, acetyl triethyl citrate, acetyl tripropyl citrate, acetyl triisopropyl citrate, and acetyl tributyl citrate.
• citric acid esters such as trimethyl citrate, triethyl citrate, tripropyl citrate, triisopropyl citrate, and tributyl citrate
• acetyl citrate esters such as acetyl trimethyl citrate, acetyl triethyl citrate, acetyl tripropyl citrate, acetyl triisopropyl citrate, and acetyl tributyl citrate.
• ring A represents a cyclohexane ring, a cyclohexene ring, or a benzene ring.
• Ring A is preferably a cyclohexene ring or a benzene ring.
• R 13 each independently represents a linear or branched alkyl group having 1 to 15 carbon atoms which may have a substituent.
• Examples of the linear or branched alkyl group having 1 to 15 carbon atoms include the same groups as R 1 in the above formula (1). Among them, a linear or branched alkyl group having 1 to 10 carbon atoms is preferred, a linear or branched alkyl group having 2 to 5 carbon atoms is more preferred, and an ethyl group, an n-propyl group, an n-butyl group, and a tert-butyl group are more preferred.
• Examples of the substituent that the alkyl group represented by R 13 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, an aryl group, a halogen atom, and the like. It is preferable that the two R 13 have the same structure.
• cyclohexene dicarboxylates such as diethyl cis-4-cyclohexene-1,2-dicarboxylate, dibutyl cis-4-cyclohexene-1,2-dicarboxylate, diheptyl cis-4-cyclohexene-1,2-dicarboxylate, butyl benzyl cis-4-cyclohexene-1,2-dicarboxylate, diisodecyl cis-4-cyclohexene-1,2-dicarboxylate, and diisodecyl 2-cyclohexene-1,4-dicarboxylate; and phthalate esters such as diethyl phthalate, dibutyl phthalate, diheptyl phthalate, dioctyl phthalate, di-2-ethylhexyl phthalate, diisononyl phthalate, diisodecyl
• aliphatic dibasic acid esters such as diisononyl adipate, di-2-ethylhexyl sebacate, and diisononyl sebacate
• isophthalic acid esters such as bis(2-ethylhexyl) isophthalate
• terephthalic acid esters such as bis(2-ethylhexyl) terephthalate
• trimellitic acid esters such as tri-2-ethylhexyl trimellitate, triisononyl trimellitate, and triisodecyl trimellitate
• pyromellitic acid esters such as tetra-2-ethylhexyl pyromellitate.
• the content of the specific ester compound in the cooling/heating transfer liquid composition according to this embodiment is preferably 60 to 99.9% by mass, and more preferably 80 to 99.9% by mass.
• the hydrophobized cellulose as component (B) is obtained by introducing hydrophobic groups such as alkyl groups to the hydroxy groups of cellulose, which is a natural polymer, and serves to facilitate separation of the specific ester compound into an organic phase and an aqueous phase.
• alkyl cellulose is preferred from the viewpoint of transparency when dissolved in a specific ester compound.
• alkyl cellulose refers to modified cellulose in which at least a portion of the hydroxyl groups of cellulose, a natural polymer, has been alkyl-etherified.
• the hydrophobized cellulose is preferably an alkyl cellulose represented by the following formula (5):
• R 20 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent.
• the linear or branched alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-pentyl group, a 2-methylbutyl group, an n-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 2,3-dimethylbutyl group, and a 2-ethylbutyl group.
• the substituent that the alkyl group represented by R 20 may have include a linear or branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, and the like.
• n is an integer between 50 and 1500.
• the alkyl cellulose represented by the formula (5) at least one of the 3n R 20 represents an alkyl group.
• the degree of modification which is the proportion of the alkyl groups among the 3n R 20 , is preferably 30 to 80%, more preferably 50 to 60%.
• alkyl celluloses represented by the above formula (5) methyl cellulose, ethyl cellulose, propyl cellulose, and butyl cellulose are preferred, and ethyl cellulose is more preferred.
• the molecular weight of alkyl cellulose affects its solubility in specific ester compounds and its viscosity in solution. From the standpoint of solubility in specific ester compounds, the mass average molecular weight of alkyl cellulose is preferably 10,000 to 300,000, and more preferably 10,000 to 100,000.
• the content of hydrophobized cellulose in the cooling/heating transfer liquid composition according to this embodiment is preferably 0.1 to 10.0% by mass. From the viewpoint of obtaining an appropriate viscosity during dissolution, in the case of alkyl cellulose with a mass average molecular weight of 10,000 to 100,000, the content is preferably 0.1 to 7.0% by mass, and more preferably 0.3 to 3.0% by mass. In addition, in the case of alkyl cellulose with a mass average molecular weight of 100,000 to 300,000, the content is preferably 0.1 to 1.0% by mass.
• the cooling/heating transfer liquid composition according to this embodiment may further contain an additive having a density of more than 1.0 g ⁇ cm ⁇ 3 , in addition to the above-mentioned components (A) and (B).
• Such additives can be high-density polymers having many oxygen atoms or nitrogen atoms in the molecular structure, inorganic fine particles, etc.
• examples of the above-mentioned polymers include polylactic acid, polymethyl methacrylate, polyvinyl chloride resin, etc.
• examples of inorganic fine particles include particles made of metal oxides such as titania and zirconia. For example, it is preferable to uniformly disperse nano-sized inorganic fine particles in the cooling/heating transfer medium liquid composition.
• the content is preferably 0.1 to 40 mass %, and more preferably 10 to 30 mass %.
• the method for producing a cooling/heating transfer liquid composition includes the steps of mixing an ester compound that is liquid at room temperature with a powdered hydrophobized cellulose to prepare a mixture, maintaining the mixture at a temperature range of 30 to 300° C. and below the boiling point of the ester compound to cause it to swell, and crushing and defibrating the mixture after the swelling.
• the ester compound that is liquid at room temperature is the above-mentioned component (A)
• the powdered hydrophobized cellulose is the above-mentioned component (B).
• the order in which components (A) and (B) are mixed is not particularly limited.
• it may be a method of adding liquid component (A) to powdered component (B), or a method of adding powdered component (B) to liquid component (A).
• the former method is effective when mixing on a small scale, and the latter method is effective when mixing on a medium or large scale.
• components (A) and (B) are placed in a container and heated in an incubator for 1-2 days to transfer component (A) into component (B) and allow component (B) to swell sufficiently.
• the heating temperature is in the range of 30-300°C and below the boiling point of component (A), and in order to prevent hydrolysis of component (A), it is preferably in the range of 30-80°C, and more preferably in the range of 30-50°C.
• the swollen mixture can be crushed and defibrated by a known method.
• a stirring blade with blades such as anchor blades connected to a stirrer such as a homogenizer or a three-one motor, and stir at a rotation speed of 300 rpm or more at the heating temperature mentioned above.
• the method for producing a cooling/heating transfer liquid composition according to this embodiment may further include a step of adding an additive having a density greater than 1.0 g ⁇ cm ⁇ 3 to the mixture after crushing and defibrating.
• ester compounds 4-Cyclohexene-1,2-dicarboxylate bis(2-ethylhexyl); manufactured by Tokyo Chemical Industry Co., Ltd., molecular weight: 394.60, specific gravity: 0.97, melting point: -60°C, boiling point: 460°C Bis(2-ethylhexyl) adipate; manufactured by Tokyo Chemical Industry Co., Ltd.; molecular weight: 370.57; specific gravity: 0.92; melting point: ⁇ -60°C; boiling point: 210°C Dibutyl adipate; manufactured by Tokyo Chemical Industry Co., Ltd., molecular weight: 258.36, specific gravity: 0.96, melting point: -32°C, boiling point: 305°C
• Example 1 First, 0.5 parts by mass of ethyl cellulose (10 cP) and 99.5 parts by mass of triethyl citrate were added to a 50 cc screw cap at room temperature (25° C.) and heated in an incubator at 40° C. for 1 day. Next, the mixture was stirred with an ultrasonic homogenizer for 3 minutes to obtain a test composition.
• test composition was vigorously shaken with water, and then left to stand at 25°C.
• the state of the mixture was visually observed, and the time until separation into an organic phase and an aqueous phase was evaluated on the following four levels. Specifically, an investigation was conducted on the separation of an organic phase (test composition) and an aqueous phase (ion-exchanged water) that had been manually mixed for 1 minute due to the difference in specific gravity.
• a sample bottle with a capacity of 50 mL was prepared, and the test composition and ion-exchanged water were added thereto. After being manually shaken for 1 minute, the bottle was left to stand to separate into an organic phase and an aqueous phase.
• Viscosity Measurement The viscosity of the obtained test composition was measured under the following conditions: The sample was not diluted, and about 1.0 g was placed on the sample stage with a dropper and used for the measurement. Apparatus: Rheometer MCR302 (manufactured by Anton Paar) Measurement tool: cone plate 2°, 50mm ⁇ Measurement time: 100 [s] Shear rate: 0.01 ⁇ 100 [1/s] Temperature: constant at 24°C Gap: 1.0 mm
• Example 2 A test composition was obtained in the same manner as in Example 1, except that tributyl citrate was used instead of triethyl citrate. The obtained test composition was then subjected to the evaluations (I) to (VI) above. The results are shown in Table 1.
• Example 3 A test composition was obtained according to the same procedure as in Example 1, except that acetyl triethyl citrate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. Then, the above evaluations (I) to (VI) were carried out on the obtained test composition. The results are shown in Table 1.
• Example 4 A test composition was obtained according to the same procedure as in Example 1, except that acetyl tributyl citrate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. Then, the above evaluations (I) to (VI) were carried out on the obtained test composition. The results are shown in Table 1.
• Example 5 A test composition was obtained according to the same procedure as in Example 4, except that the amount of acetyl tributyl citrate used was changed from 99.5 parts by mass to 99.0 parts by mass, and the amount of ethyl cellulose (10 cP) used was changed from 0.5 parts by mass to 1.0 parts by mass. At that time, the ethyl cellulose (10 cP) was completely dissolved. Then, the above evaluations (I) to (VI) were carried out on the obtained test composition. The results are shown in Table 1.
• Example 6 A test composition was obtained in the same manner as in Example 4, except that the amount of acetyl tributyl citrate used was changed from 99.5 parts by mass to 95.0 parts by mass, and the amount of ethyl cellulose (10 cP) used was changed from 0.5 parts by mass to 5.0 parts by mass. The obtained test composition was then evaluated in the above items (I) to (VI). The results are shown in Table 1.
• Example 7 A test composition was obtained in the same manner as in Example 4, except that ethyl cellulose (45 cP) was used instead of ethyl cellulose (10 cP). The obtained test composition was then subjected to the above evaluations (I) to (VI). The results are shown in Table 1.
• Example 8 A test composition was obtained in the same manner as in Example 4, except that ethyl cellulose (100 cP) was used instead of ethyl cellulose (10 cP). The obtained test composition was then subjected to the above evaluations (I) to (VI). The results are shown in Table 1.
• Example 9 A test composition was obtained in the same manner as in Example 1, except that diethyl phthalate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. The obtained test composition was then subjected to the above evaluations (I) to (VI). The results are shown in Table 1.
• Example 10 A test composition was obtained in the same manner as in Example 1, except that diethyl cis-4-cyclohexene-1,2-dicarboxylate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. Then, the above evaluations (I) to (VI) were carried out on the obtained test composition. The results are shown in Table 1.
• Example 2 A test composition was obtained in the same manner as in Example 1, except that bis(2-ethylhexyl) 4-cyclohexene-1,2-dicarboxylate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. Then, the above evaluations (I) to (VI) were carried out on the obtained test composition. The results are shown in Table 1.
• Example 3 A test composition was obtained in the same manner as in Example 1, except that bis(2-ethylhexyl) adipate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. The obtained test composition was then subjected to the above evaluations (I) to (VI). The results are shown in Table 1.
• Example 4 A test composition was obtained in the same manner as in Example 1, except that dibutyl adipate was used instead of triethyl citrate. At that time, the ethyl cellulose (10 cP) was completely dissolved. The obtained test composition was then subjected to the above evaluations (I) to (VI). The results are shown in Table 1.
• test compositions of Comparative Examples 1 to 4 were mixed with water and vigorously shaken, it took 2 to 3 days for them to separate into an organic layer and an aqueous phase, whereas the test compositions of Examples 1 to 10 separated into an organic layer and an aqueous phase within a few minutes to a few hours. Therefore, the test compositions of Examples 1 to 10 can be suitably used as a cooling/heating medium liquid composition for an open circulating thermostatic bath. The test compositions of Examples 1 to 10 also had excellent transparency.
• ethyl cellulose (10 cP) was higher when acetyl triethyl citrate or acetyl tributyl citrate was used (Examples 3 and 4) than when triethyl citrate, tributyl citrate, diethyl phthalate, or diethyl cis-4-cyclohexene-1,2-dicarboxylate was used (Examples 1, 2, 9, and 10).
• Example 4 when acetyl tributyl citrate was used (Example 4), a more stable and transparent composition was obtained at room temperature (25°C) than when acetyl triethyl citrate was used (Example 3). This is thought to be because the combined use of acetyl tributyl citrate and ethyl cellulose can better suppress foaming at room temperature (25°C).

Landscapes

• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Physics & Mathematics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Combustion & Propulsion (AREA)
• Thermal Sciences (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Polysaccharides And Polysaccharide Derivatives (AREA)
• Compositions Of Macromolecular Compounds (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

Family

ID=91195679

Family Applications (1)

Country Status (3)

Citations (6)

• 2023
  • 2023-11-17 WO PCT/JP2023/041477 patent/WO2024111522A1/ja not_active Ceased
  • 2023-11-17 JP JP2024560124A patent/JPWO2024111522A1/ja active Pending
  • 2023-11-22 TW TW112145081A patent/TW202440870A/zh unknown

Patent Citations (6)

Also Published As

Similar Documents

Legal Events