Use of glycol ether carbonate as refrigeration lubricant

Abstract: The lubricant oil composition according to the present invention comprises a glycol ether carbonate represented by the general formula [I] R₁-O(R₃-O)CO(OR₄)OR₂ [I) wherein R₁ and R₂ are each independently a member selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group and an aromatic-­ substituted aliphatic group each having not greater than 20 carbon atoms, R₃ and R₄ are each independently an ethylene group or an isopropylene group, and m and n are each independently an integer of 2 to 100. The lubricant oil composition according to this invention can be widely used for industrial gear oil, automotive engine oil, automotive gear oil, lubricant oil for refrigerators, lubricant oil for fibers and rolling lubricant oil. Furthermore, the lubricant oil composition of the invention can be used for refrigerators using, as a refrigerant, ozone layer-nondestructive Freon such as Freon R-134a. Still furthermore, of the lubricant oil compositions of the invention, there can be used, as refrigerator lubricant oil, a lubricant oil composition containing ozone layer-­ nondestructive Freon such as Freon R-134a in addition to a glycol ether carbonate represented by the above-described general formula [I].

Description: FIELD OF THE INVENTION The present invention relates to the use of a glycol ether carbonate as a lubricant oil used for refrigerators having excellent lubricating properties and detergency. The present invention relates still more particularly to the use of a glycol ether carbonate as a lubricant oil for refrigerators where hydrogenated fluorocarbon (HFC) such as Freon R-134a (CH₂FCF₃) which is non-destructive to the ozone layer is used as a refrigerant. BACKGROUND OF THE INVENTION DE-A-1 962 491 discloses specific glycol ether carbonate compounds which may be used in the preparation of brake fluids and as synthetic lubricants. It is necessary for brake fluids to be corrosion resistant, for example in the case of steel or copper. GB-A-2 216 541 discloses a lubricant composition comprising a hydrofluorocarbon, a hydrochlorofluorocarbon or a chlorofluorocarbon and a lubricant. Said lubricant composition comprises an ester having a molecular weight in excess of 250. Such a composition is used in a heat transfer device. With the alteration of a refrigerant gas for refrigerators to Freon R-134a (CH₂F-CF₃) which is an ozone layer-nondestructive HFC, mineral oil and alkylbenzenes, which heretofore have been used for lubricant oil for refrigerators, have come not to be used therefor because they have no mutual solubility with the refrigerant gas. Glycol ether type lubricant oil has currently been developed for the lubricant oil for refrigerators where the above-mentioned refrigerant is used. For example, U.S. Patent No. 4,755,316 discloses a compression refrigerator composition composed of tetrafluoroethane and a polyoxyalkylene glycol having a molecular weight of 300 to 2,000 and a kinematic viscosity at 37°C of about 25 to 150 mm²/s (cSt). Such glycol ether lubricant oil, however, generally has insufficient thermal stability and high hygroscopicity, and in addition it has been pointed out that the glycol ether lubricant oil has such a drawback that it shrinks rubber sealing materials such as nitrile rubber (NBR) and increases their hardness. U.S. Patent No. 3,627,810 discloses a process for preparing carbonates of higher alcohols represented by the formula R'OCOOR'', and the carbonates are described to be useful as hydraulic oil, lubricant oil and plasticizers. The specification, however, does not clearly describe their concrete use, for example, for lubricant oil for refrigerators, especially refrigerator lubricant oil excellent in mutual solubility with ozone layer-nondestructive Freon. In the above formula, R' and R'' are each a higher alcohol residue. U. S. Patent No. 3,657, 310 discloses a process for preparing carbonates represented by the formula ROCOO(AO) n R'. Though these carbonates are described to be useful as lubricant oil, hydraulic oil and plasticizers, their concrete use, for example, for lubricant oil for refrigerators, especially refrigerator lubricant oil excellent in mutual solubility with ozon layer-nondestructive Freon has not been disclosed. In the above-mentioned formula, R and R' each denote a monovalent aliphatic group, and A indicates an alkylene group having 2 to 4 carbon atoms, with n denoting an integer of not less than 1. European Patent No. 089,709 discloses a process for preparing a carbonate of a higher alcohol by ester interchange reaction between a higher alcohol having a molecular weight of 100 to 270 and an alcohol carbonate having a low boiling point, and a lubricant oil composition containing such a carbonate of a higher alcohol. Japanese Patent L-O-P No. 37,568/1973 discloses a motor transmitting liquid containing at least one of carbonates represented by the general formula wherein R¹ and R² are each independently hydrogen, an aliphatic group, an aromatic-substituted aliphatic group, an aromatic group, an acyl group, an alkoxycarbonyl group or an aryloxy group, n is a number of 1 to 10, and X is an alkylene group having at least two carbon atoms in the main molecular carbon chain, the molecular chain optionally containing a cycloalkylene group, an aralkylene group, an arylene group or at least one hetero atom. The use of the carbonate esters disclosed in the publication, however, are for transmitting liquid and not for lubricant oil. Furthermore, Japanese Patent Publication No. 4727/1971 discloses a process for preparing polyethylene glycol monomethyl ether carbonates represented by the general formula wherein x and y are each 2 or 3. The publication teaches that the polyetylene glycol monomethyl ether carbonates described above are useful for the preparation of a brake liquid, and they are also useful as synthetic lubricants. However, it does not clearly describe concrete use as a lubricant oil for refrigerators, especially refrigerator lubricant oil excellent in mutual solubility with ozone layer-nondestructive Freon. The present invention is intended to solve the above-described problems involved in the prior art method, and an object of this invention is to provide a lubricant oil composition for refrigerators having excellent lubricating properties and detergency, and also having excellent mutual solubility with ozone layer-nondestructive Freon such as Freon R-134a (CH₂FCF₃). SUMMARY OF THE INVENTION The present invention resides in the use of a glycol ether carbonate represented by the general formula [I] wherein R₁ and R₂ are each independently a member selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group and an aromatic-substituted aliphatic group each having not greater than 20 carbon atoms, R₃ and R₄ are each independently an ethylene group or an isopropylene group, and m and n are each independently an integer of 2 to 100, as a lubricant oil for refrigerators. The lubricant oil composition according to this invention has excellent lubricating properties and detergency, and its viscosity at low temperature can be easily decreased compared with mineral oil or ester lubricant oil. The lubricant oil composition according to this invention is excellent not only in the above-described properties but also in mutual solubility with ozone layer-non-destructive hydrofluorocarbons (Freon R ) such as Freon R-134a R , and can therefore be used as a lubricant oil for refrigerators where ozone layer-non-destructive hydrofluorocarbons (Freon R ) such as Freon R-134a (CH₂FCF₃) is employed as a refrigerant. In the lubricant oil for refrigerators of this invention, there can also be used the one containing ozone layer-non-destructive hydrofluorocarbons (Freon R ) such as R-134a in addition to a glycol ether carbonate represented by the general formula [I] described above. The term "lubricant oil composition" in this specification includes lubricant oil comprising a glycol ether carbonate of this invention and other ingredients, and lubricant oil composed only of said glycol ether carbonate. DETAILED DESCRIPTION OF THE INVENTION The lubricant oil composition of the present invention is concretely illustrated hereinafter. The lubricant oil composition according to the present invention comprises a glycol ether carbonate represented by the general formula [I] wherein R₁ and R₂ are each independently a member selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group and an aromatic-substituted aliphatic group each having not greater than 20 carbon atoms . Here, concrete examples of an aliphatic hydrocarbon group represented by R₁ and R₂ include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, n-undecyl, isoundecyl, n-dodecyl, isododecyl, n-tridecyl, isotridecyl, n-tetradecyl, isotetradecyl, n-pentadecyl, isopentadecyl, n-hexadecyl, isohexadecyl, n-heptadecyl, isoheptadecyl, n-octadecyl, isooctadecyl, n-nonyldecyl, isononyldecyl, n-eicosanyl and isoeicosanyl. Concrete examples of an alicyclic hydrocarbon group represented by R₁ and R₂ include cyclohexyl, 1-cyclohexenyl, methylcyclohexyl, dimethylcyclohexyl, decahydronaphtyl and tricyclodecanyl. Furthermore, concrete examples of an aromatic hydrocarbon group represented by R₁ and R₂ include phenyl, o-tolyl, p-tolyl, m-tolyl, 2,4-xylyl, mesityl and 1-naphtyl. Still furthermore, concrete examples of an aromatic-substituted aliphatic hydrocarbon group represented by R₁ and R₂ include benzyl, methylbenzyl, β-phenylethyl (phenethyl), 1-phenylethyl, 1-methyl-1-phenylethyl, p-methylbenzyl, styryl and cinnamyl. In the above-described general formula [I], R₃ and R₄ are each independently an ethylene group or an isopropylene group. Moreover, in the general formula [I] described above, m and n are each independently an integer of 2 to 100. In the present invention, R₁, R₂, R₃, R₄, m and n in the above general formula [I] are selected in accordance with the use. For example, when R₁, R₂, R₃, R₄, m and n for the glycol ether carbonate represented by the general formula [I] are selected in such a manner that the resultant glycol ether carbonate has a kinematic viscosity (JIS K-2283) of about 8 mm²/s (cSt) at 100°C, a lubricant oil composition containing the resultant glycol ether carbonate described above is preferably used for lubricant oil for refrigerators where ozone layer-nondestructive hydrofluorocarbons Freon R such as Freon R R-134a (CH₂FCF₃) is employed as a refrigerant. The preferable use of the above-mentioned glycol ether carbonate is due to its especially excellent mutual solubility with ozone layer-nondestructive hydrofluorocarbons (Freon R ) at temperatures as low as -20°C and as high as 90°C. Glycol ether carbonates represented by the general formula [I] described above can be prepared, for example, by ester interchange reaction of a polyalkylene glycol monoalkyl ether in the presence of an excessive amount of a carbonate of an alcohol having a relatively low boiling point. Such a process does not require the use of a highly toxic gas, as is the case with the phosgene process, and is therefore preferable from the standpoint of safety. Concrete examples of polyalkylene glycol monoalkyl ethers described above include ethylene glycol monoalkyl ethers, diethylene glycol monoalkyl ethers, triethylene glycol monoalkyl ethers, tetraethylene glycol monoalkyl ethers, propylene glycol monoalkyl ethers, dipropylene glycol monoalkyl ethers, tripropylene glycol monoalkyl ethers and tetrapropylene glycol monoalkyl ethers. Moreover, in the present invention, polyalkylene glycol monoalkyl ethers formed as by-products during the manufacture of the polyalkylene glycol monoalkyl ethers concretely mentioned above and having relatively high boiling points may also be singly used in place thereof, and they may also be used in a mixture with the polyalkylene glycol monoalkyl ethers concretely mentioned above. Furthermore, a glycol ether carbonate represented by the general formula [I] having a viscosity appropriate for desired use may be prepared by suitably selecting the length of the hydrocarbon group and the polymerization degree of the polyalkylene glycol. Moreover, characteristics such as the low temperature characteristics, heat resistance and rubber swelling properties of the polyalkylene glycol can be freely adjusted by selecting the structure of the hydrocarbon group and polyalkylene glycol group thereof. The thus obtained glycol ether carbonates have excellent lubricating properties, low hygroscopicity and good detergency compared with glycol ethers, and therefore they can be used for industrial gear oil, automotive engine oil, automotive gear oil, lubricant oil for fibers, lubricant oil for rolling and lubricant oil for refrigerators. The lubricant oil composition according to the present invention comprises a glycol ether carbonate in an amount of 1 to 100 parts by weight based on 100 parts by weight of the total lubricant oil composition. As a result, the glycol ether carbonate can be used solely as lubricant oil, and it can also be used in combination with other components to form lubricant oil. The lubricant oil composition of this invention is used as lubricant oil for refrigerators, and the lubricant oil composition may be incorporated with other usable components including glycol ethers and mineral oil such as neutral oil and bright stock in addition to the glycol ether carbonate. It may also be incorporated with an α-olefin oligomer such as liquid polybutene and liquid decene oligomer, a carboxylic acid ester such as di-isooctyl adipate, di-isooctyl sebacate and dilauryl sebacate, and vegetable oil. In the case of using the lubricant oil composition of the invention as lubricant oil for refrigerators where HFC such as Freon R-134a (tetrafluoroethane) is specifically employed as a refrigerant gas nondestructive to the ozone layer, usable other additives are limited to glycol ethers and carboxylic acid esters from the standpoint of the mutual solubility. The addition amount of these additives, however, is required to be less than 60% by weight of the entire lubricant oil composition from the standpoint of not deteriorating heat resistance, mutual solubility with Freon R-134a (CH₂FCF₃) and hygroscopicity resistance. Moreover, the lubricant oil composition may contain known lubricant oil additives as described above. Furthermore, the lubricant oil for refrigerators may also contain ozone layer-nondestructive hydrofluorocarbons (Freon R ) such as Freon R-134a (CH₂FCF₃). EFFECT OF THE INVENTION The lubricant oil according to this invention comprises a specific glycol ether carbonate, and therefore it has excellent lubricating properties and detergency. In addition, its viscosity at low temperature can be easily decreased compared with mineral oil or ester lubricant oil. The lubricant oil according to this invention is excellent not only in the above-described properties but also in mutual solubility with ozone layer-nondestructive Freon including Freon R-134a (CH₂FCF₃), and therefore it can be used as lubricant oil or refrigerators where ozone layer-nondestructive hydrofluorocarbons (Freon R ) such as Freon R-134a (CH₂FCF₃) is employed as a refrigerant. Concrete effects obtained when a lubricant oil composition according to this invention is used as the lubricant oil for refrigerators are described below. Since the lubricant oil composition of this invention comprises a specific glycol ether carbonate, it is soluble in Freon R-134a (CH₂F-CF₃) which is a HFC nondestructive to the ozone layer and used as a refrigerant gas, has moreover excellent thermal stability and hygroscopicity resistance, and it prevents shrinkage of rubber sealing materials such as NBR to maintain sealing effects. In addition, the lubricant oil of the invention can also maintain similar sealing effects for EPDM and SBR, and accordingly EPDM and SBR can be employed as rubber sealing materials. The present invention is illustrated below with reference to examples, but it should be construed that the invention is in no way limited to those examples. Test procedures described below were applied to perform evaluation of properties of lubricant oil in Examples and Comparative Examples. (1) Evaluation methods a. Kinematic viscosity by JIS K-2283 b. Viscosity at low temperature by ASTM D 2983 c. Friction characteristics Friction coefficients of sample materials were measured under the following conditions by using a friction tester (trade name of SRV, manufactured by Optimol K.K.): load: 200 N; temperature: 50°C; period of time: 10 min; amplitude: 1 mm; number of vibration: 50 Hz; and test pieces: a disc in combination with a sphere, both made SUJ-2 (JIS G 4805). The depth of the resultant wear defect was determined by measuring the defect depth of the disc after test using a surface roughness meter (trade name of Surfcom 200B, manufactured by Tokyo Seimitsu K.K.). d. Thermal stability A 20-g sample is placed in a 100 ml beaker, and the beaker is heated at 100°C for 6.5 hours in an oven. The thermal stability thereof is evaluated from an (amount of sample weight decrease)/(initial sample weight) ratio. The sample has better thermal stability when it shows a smaller change (decrease) ratio. e. Detergency A 1-g sample is placed in a lid 5 cm in diameter of a container for ointment, and heated at 230°C for 48 hours or 300°C for 6 hours. In the case where the sample remains, it is black and solidified (in a carbonized state). The weight of the sample before and after the test is measured, and a remaining ratio of the sample is defined as a sludge formation ratio, from which detergency of the sample is evaluated. f. Hygroscopicity A 100 ml beaker is charged with a 30-g sample, and allowed to stand still for 48 hours in an air-conditioning bath kept at a temperature of 25°C and relative humidity of 75%. The water concentration of the sample before and after the test is measured by Karl Fischer's method. g. Rubber swelling properties A flask containing a 20-ml sample is charged with 2 kinds of O-rings (P-22), that is, a nitrile rubber O-ring (JIS B 2401 1B) and a fluororubber O-ring (JIS B 2401 4D), equipped with a condenser, and immersed in an oil bath at 120°C for 70 hours. The two O-rings are taken out from the flask after the test, freed from the sample by wiping sufficiently, and the weight change of the O-rings is measured. h. Mutual solubility with Freon R-134a (CH₂FCF₃) A test tube having an inner diameter of 10 mm and height of 20 cm is charged with a 1 ml-sample, and Freon R-134a (CH₂FCF₃) is slowly introduced into the test tube in an amount slightly larger than that of the sample from a bomb container while the test tube is being cooled in a dry ice-acetone bath. Then, the content is stirred by a spatula, and the test tube is transferred to a cooling bath at -20°C. The solubility of the sample is observed when the volume ratio of sample/(Freon R-134a (CH₂FCF₃)) becomes 1/1. The mutual solubility is designated as O (mark) when the mixture becomes completely uniform, and it is designated as X (mark) when complete dissolution of the mixture is not observed. Example 1 A 5 liter 3 neck round bottom flask with a 10-plate Oldershow type distillation column and a thermometer was charged with 821 g (5 mols) of triethylene glycol monomethyl ether, 1351 g (15 mols) of dimethyl carbonate and 9 g of a methanol solution containing 30% by weight of NaOCH₃ (0.05 mol as NaOCH₃). The mixture was refluxed by heating in an oil bath with stirring under a nitrogen ambient atmosphere to react. Resultant methanol was distilled off 5 hours after the initiation of the reaction, and the reaction was continued until the internal temperature of the round bottom flask reached 130°C. The reaction was continued while resultant methanol and dimethyl carbonate were being distilled off by connecting the round bottom flask to an evacuating apparatus and stepwise increasing evacuation degree of the ambient pressure. The reaction was terminated at the stage when the ambient pressure and the internal temperature of the round bottom flask reached 1999,5 Pa (15 mmHg) and 135°C, respectively. The reaction solution was neutralized by introducing 2.9 g of an aqueous solution containing 85% by weight of phosphoric acid into the round bottom flask. Resultant precipitated salt was filtered out. The filtrate was distilled at wall temperature of 205 to 220°C of the round bottom flask and under a reduced pressure of 226,61 Pa (1.7 mmHg) by using a thin film distillation apparatus, and a low boiling point component was distilled off. The removed low boiling point component was in an amount of 25% by weight based on the entire reaction solution. A high boiling point component of the reaction solution remaining in the round bottom flask was distilled off at a wall temperature of 260°C under a reduced pressure of 20 Pa (0.15 mmHg). The removed high boiling point component was in an amount of 15% by weight based on the entire remaining reaction solution. Bis{2-[2-(2-methoxyethoxy)ethoxy]ethyl} carbonate in an amount of 567 g was obtained by removing a low boiling point component and a high boiling point component from the reaction solution as described above. Bis{2-[2-(2-methoxyethoxy)ethoxy]ethyl} carbonate was thus obtained in purity of 98.5% and in a yield of 64%. The fundamental properties as a lubricant oil of the thus obtained carbonate are evaluated, and the results are shown shown in Table 1. Example 2 The reaction conducted in Example 1 was repeated except that 1,031 g of triethylene glycol monobutyl ether was used in place of triethylene glycol monomethyl ether. The procedure of Example 1 was repeated at a wall temperature of 220°C and under a reduced pressure of 199,95 Pa (1.5 mmHg) to remove a low boiling point component from the reaction solution. A high boiling component was also removed by repeating the procedure of Example 1 at a wall temperature of 260°C and under a reduced pressure of 26,66 Pa (0.2 mmHg). Bis{2-[2-(2-butoxyethoxy)ethoxy]ethyl} carbonate was thus obtained in an amount of 614 g. Bis{2-[2-(2-butoxyethoxy)ethoxy]ethyl} carbonate was thus obtained in purity of 98.0% and in a yield of 56%. The fundamental properties as a lubricant oil of the thus obtained carbonate are evaluated, and the results are shown in Table 1. Comparative Example 1 A propylene oxide type glycol ether ( M n of 1520, M w/ M n of 1.1) was similarly evaluated as lubricant oil. Evaluation results of the fundamental properties thereof as lubricant oil are shown in Table 1. Comparative Example 2 Similar evaluation was conducted on mineral oil of lubricant oil (trade name of Suniso 331, prepared by Nihon Sun Sekiyu K.K.) for refrigerators where currently used Freon R-12 (CCl₂F₂) was employed. Evaluation results of the fundamental properties thereof as lubricant oil are shown in Table 1. The lubricant oil is not mutually soluble with Freon R-134a which is nondestructive to the ozone layer. Ex. 1 Ex. 2 Comp. Ex. 1 Comp. Ex. 2 Viscosity characteristics 100°C Kinematic viscosity mm²/s [cSt] 2.77 3.21 10.6 6.0 40°C Kinematic viscosity mm²/s [cSt] 10.21 11.86 55.8 54.9 -20°C Viscosity 0,1 Pa·s [poise] 9.9 3.6 40 160 Friction characteristics Friction coefficient 0.11 0.11 0.13 0.22 Wear depth [µm] 0.6 0.4 2.8 1.2 Thermal stability (wt. change) [%] -6.3 -3.5 -6.5 -10.5 Detergency 230°C, 48 h 0.2 0.4 4.9 15.1 300°C, 6 h <0.1 <0.1 2.2 5.0 Hygroscopicity (Water content %) Initial 0.09 0.05 0.08 0.006 After test 0.16 0.10 2.45 0.007 Rubber swelling properties (Wt. change) [%] Nitrile rubber +17.0 +24.2 -1.5 +2.6 Fluororubber +9.6 +2.2 +0.4 +0.3 Mutual solubility with Freon R-134a (CH₂FCF₃) ○ ○ ○ X

Claims: Claims for the following Contracting States : AT, BE, CH, DE, DK, FR, GB, GR, IT, LI, LU, NL, SE Use of a glycol ether carbonate represented by the general formula [I] R₁-0 ( R₃-0 ) m CO ( 0-R₄ ) n 0-R₂ [I] wherein R₁ and R₂ are each independently a member selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group and an aromatic-substituted aliphatic group each having not greater than 20 carbon atoms, R₃ and R₄ are each independently an ethylene group or isopropylene group, and m and n are each independently an integer of 2 to 100 as a lubricant oil for refrigerators. Use according to claim 1, wherein R₁ and R₂ are each independently an alkyl group, and R₃ and R₄ are each an ethylene group. Use according to claim 1 wherein the glycol ether carbonate is bis ( 2-[2-(2-butoxyethoxy)ethoxy]ethyl ) carbonate or bis ( 2-[2-(2-methoxyethoxy)ethoxy]ethyl ) carbonate. Use according to any one of the claims 1 to 3, wherein an ozone layer non-destructive hydrofluorocarbon is further comprised in the lubricant oil. Use according to claim 4, wherein the ozone layer non-destructive hydrofluorocarbon is CH₂FCF₃. Use according to claim 4 or 5, wherein the lubricant oil comprises glycol ethers and carboxylic acid esters as other additives in an amount of less than 60% by weight of the entire lubricant oil composition. Claims for the following Contracting State : ES Process for lubricating refrigerators wherein a glycol ether carbonate is used as a lubricant oil, represented by the general formula [I] R₁-0 ( R₃-0 ) m CO ( 0-R₄ ) n 0-R₂ [I] wherein R₁ and R₂ are each independently a member selected from the group consisting of an aliphatic group, an alicyclic group, an aromatic group and an aromatic-substituted aliphatic group each having not greater than 20 carbon atoms, R₃ and R₄ are each independently an ethylene group or isopropylene group, and m and n are each independently an integer of 2 to 100. Process according to claim 1, wherein R₁ and R₂ are each independently an alkyl group, and R₃ and R₄ are each an ethylene group. Process according to claim 1, wherein the glycol ether carbonate is bis ( 2-[2-(2-butoxyethoxy)-ethoxy]ethyl ) carbonate or bis ( 2-[2-(2-methoxyethoxy)ethoxy]ethyl ) carbonate. Process according to claim 1, wherein the lubricant oil is used together with an ozone layer non-destructive hydrofluorocarbon. Process according to claim 4, wherein the ozone layer non-destructive hydrofluorocarbon is CH₂FCF₃. Process according to claim 4 or 5, wherein the lubricant oil is used together with glycol ethers and carboxylic acid esters as other additives in an amount of less than 60 % by weight of the entire lubricant oil composition.

Inventors: FURUYA YOSHIAKI C O MITSUI PET, MIZUI KINYA C O MITSUI PETROCH, FURUYA, YOSHIAKI C/O MITSUI PETROCHEMICAL IND. LTD, MIZUI, KINYA, C/O MITSUI PETROCHEMICAL IND. LTD.
Applicants: MITSUI PETROCHEMICAL IND, MITSUI PETROCHEMICAL INDUSTRIES, LTD.
Application year: 1990
Main classification: C10M107
IPC codes: C10M105, F02B75, C10N30, C10M129, C10M107, C10M171, C10N40, C07C69, C09K5