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WO1993013185A1 - Huile lubrifiante pour refrigerateur - Google Patents

Huile lubrifiante pour refrigerateur Download PDF

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Publication number
WO1993013185A1
WO1993013185A1 PCT/JP1992/001707 JP9201707W WO9313185A1 WO 1993013185 A1 WO1993013185 A1 WO 1993013185A1 JP 9201707 W JP9201707 W JP 9201707W WO 9313185 A1 WO9313185 A1 WO 9313185A1
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WO
WIPO (PCT)
Prior art keywords
group
polymer
lubricating oil
acid
repeating unit
Prior art date
Application number
PCT/JP1992/001707
Other languages
English (en)
Japanese (ja)
Inventor
Takehisa Sato
Hironari Ueda
Toshiaki Kuribayashi
Satoshi Asano
Tadashi Niwa
Hiroshi Ueno
Takeaki Fujii
Sadakatsu Suzuki
Original Assignee
Tonen Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP34448491A external-priority patent/JPH06122888A/ja
Priority claimed from JP2901392A external-priority patent/JPH05194654A/ja
Priority claimed from JP4284896A external-priority patent/JPH06192671A/ja
Priority claimed from JP29096092A external-priority patent/JPH06199966A/ja
Priority claimed from JP29191792A external-priority patent/JPH06116579A/ja
Priority claimed from JP29191692A external-priority patent/JPH06116578A/ja
Priority claimed from JP29191892A external-priority patent/JPH06145246A/ja
Application filed by Tonen Corporation filed Critical Tonen Corporation
Priority to DE69229859T priority Critical patent/DE69229859T2/de
Priority to EP93900440A priority patent/EP0586705B1/fr
Publication of WO1993013185A1 publication Critical patent/WO1993013185A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/28—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • 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
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/16—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate polycarboxylic
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24—Only one single fluoro component present
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
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Definitions

  • the present invention relates to a lubricating oil for a refrigerator using an alternative Freon refrigerant, and more particularly, to a lubricating oil for a refrigerator using a hydrogenated halogenated hydrocarbon refrigerant.
  • the present invention also relates to a fumarate copolymer suitable as the lubricating oil.
  • R22 CHC 1 F 2) , R 123 (CF 3 CHC 12), R141b N ⁇ CC 1 2 FCH 3), R134a (CF 3 ⁇ 4 CH 2 Hydrogenated halogenated hydrocarbon refrigerants such as F) and R152a (CHF 9 CH 3) have been developed.
  • non-chlorinated halogenated carbonitride hydrogen for example R 134a ⁇ CF 3 CH 2 F ), R152a (CH F 2 CH3), R125 (CHF 2 CF 3), R32 (CH 2 F 2) , etc. and their Promising mixed refrigerants.
  • Lubricating oils for refrigerators generally have a wide range of compatibility temperature with the refrigerant (compatibility), that is, they do not show up at high temperatures (the solvation of the refrigerant with the lubricating oil is large), and the molecular polarity of the lubricating oil Is large, and there is no precipitation of lubricating oil at low temperatures (the solubility of the lubricating oil in the refrigerant is high).
  • various chillers have different kinematic viscosity ranges.
  • a composition for a high viscosity refrigerator based on polyoxypropylene glycol monobutyl ether is also known (Japanese Patent Publication No. 57-42119).
  • Polyoxyalkylene glycols having at least two hydroxyl groups in the molecule have been proposed (U.S.P. 4,755,316).
  • a glycidyl methyl ether-propylene oxide copolymer or a glycidyl methyl ether polymer having terminal groups of methoxy group and hydroxyl group is known as a lubricating oil for refrigerators (JP-A-3-205492).
  • the present invention provides a lubricating oil for a refrigerator comprising a bumaric acid ester polymer mainly comprising a repeating unit represented by the following general formula (I) and, if desired, a line repeating unit represented by the following general formula ( ⁇ ). It is a lubricating oil for refrigerators characterized by containing.
  • C OOR 1 a lubricating oil for refrigerators characterized by containing.
  • each R 2 may mutually identical or different, from the group consisting of alkylene and substituted alkylene group At least two repeating units (I) and at least the same number as the repeating units (II) in the polymer; and the units (II) need not be present.
  • the units (I) and (II) can form a random copolymer or a block copolymer.
  • FIG. 1 is a chart showing the results of 1H-NMR analysis of the fumarate ester copolymer of the present invention produced in Example 18.
  • FIG. 2 shows the fumarate ester copolymer of the present invention produced in Example 18.
  • FIG. 3 shows the results of the production of the fumaric acid ester copolymer of the present invention produced in Example 19.
  • FIG. 4 shows the fumaric acid ester copolymer of the present invention produced in Example 19.
  • 13 is a chart showing the results of 13 C analysis.
  • Figure 5 is a chart showing the results of analysis according to 1 H-NMR of fumarate Jechiru polymer prepared in Comparative Example 1 0 3 ⁇ 4
  • FIG. 6 is a chart showing the results of 13 C-HMR analysis of the getyl fumarate polymer produced in Comparative Example 10.
  • FIG. 7 shows the 1 H-NMR of the getyl fumarate polymer produced in Comparative Example 11. 6 is a chart showing the results of the analysis.
  • FIG. 8 is a chart showing the results of 13 C-NMR analysis of the getyl fumarate polymer produced in Comparative Example 11.
  • the above fumaric acid ester polymer is a fumaric acid ester or a polymerization product of a fumaric acid ester and a copolymerizable alkylene, and both ends thereof are residues of a polymerization initiator used in the polymerization.
  • 1 ⁇ is linear or branched.
  • c 9 alkyl Le group including Aruaruki group
  • a C _j to c 6 alkyl group preferably a C _j to c 6 alkyl group
  • Ariru group including alkaryl
  • terminal substituted or unsubstituted A polyalkylene oxide residue, preferably a compound of the formula-(AO) ,,-X wherein A is an ethylene, propylene or butylene group, X is a hydrogen atom or a Cj- 4 alkyl group, and X is Which is an integer of 1 to 4], especially those having 4 to 6 carbon atoms excluding the number of carbon atoms of the terminal group X (the more carbon atoms, the lower the compatibility with cold).
  • a diethylene glycol monoethyl ether residue and an ethylene glycol monoethyl ether residue are preferable.
  • R-! Is a butyl group, or a butyl group and an ethyl group (ratio of 8: 2 or more), and a polymer containing 8 or more repeating units (I) is particularly preferable in terms of viscosity, viscosity index and phase with the refrigerant. Excellent balance of solubility
  • H 2 is a substituted or unsubstituted alkylene group (including an alkyl group), preferably a c 2 to c 12 linear, branched or cycloalkylene group or oxoalkylene group. These are particularly substituted with ethylene, propylene, butene and styrene. ⁇ Return unit
  • the viscosity index can be further improved.
  • the repeating unit (II) is more present in the polymer than the repeating unit (I). Must not be. That is, the proportion of the repeating unit (II) in the copolymer is at most 50 mol%, preferably at most 30 mol%. If this exceeds 50 mol%, the compatibility of the copolymer with the refrigerant will be poor.
  • the degree of polymerization of the fumaric acid ester polymer is determined so as to have an appropriate kinematic viscosity as a lubricating oil for a refrigerator described below.
  • Kinematic viscosity is preferably in the range of 2 ⁇ 100c S t (100 e C) .
  • the molecular weight (number average) is preferably from 400 to 3000, more preferably from 400 to 1600. As the molecular weight increases, the viscosity index increases, but tends to be solid at room temperature, and the compatibility with the refrigerant tends to decrease.
  • One type of fumaric acid ester copolymer may be used, and two or more types of copolymers having different structures, molecular weights and the like may be used.
  • a fumaric acid ester copolymer having a molecular weight of 400 to 3,000 and a molecular weight of 3000 to 10,000 to improve kinematic viscosity and viscosity index.
  • the fumaric acid ester polymer is obtained by polymerizing the monomer corresponding to the repeating unit (I) and, if desired, the repeating unit (() by heating under reflux in the presence of a polymerization initiator.
  • an isomerization catalyst is additionally used.
  • an isomerization catalyst is added, it is thought that the maleate ester is firstly isomerized to a fumarate ester, and this polymerizes (Acta Polymerica 39 (1988) No. 1, 5-8.
  • the polymerization can be carried out in the same manner as in the case of the above-mentioned polymerization of fumaric acid ester, except that it is added to the polymerization reaction system in a molar ratio of 1 to 27 to 1700 with respect to the starting ester.
  • Morpholine, piperidine, dipyramine, propylamine, and preferably morpholine can be used.
  • Suitable polymerization initiators can be used for the polymerization reaction.
  • Azonitrile compounds such as 2,2'-azobisisobutyronitrile, 1- 1'-azobiscyclohexanecarbonitrile, 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis (2,4-dimethylvaleronitrile), etc .
  • azoamidine compounds For example, 2,2'-azobis (2-methylphenylpropionamidine, 2,2'-azobis (2-methylpropionamidine) dihydrochloride, 2,2'-azobis [2- (2-imidazoline- 2-yl) propane] dihydrochloride, etc .
  • azoamide compounds such as 2,2'-azobis (isobutylamide) dihydrochloride, 2,2'-azobis ⁇ 2-methyl [1,1-bis (hydroxymethyl) ) -2-hydroxyethyl] propionamide ⁇
  • alkylazo compounds such as azodi
  • ketone peroxides such as methylethyl ketone peroxide, cyclohexanone peroxide, methylcyclohexanone peroxide, and the like
  • peroxyketals such as 1,1-bis (t-butylperoxy) 3 1,3,5-trimethylcyclohexane, 1,1-bis (t-butyloxy) cyclohexane, 2,2-bis (t-butylperoxy) butane, etc .
  • hydroperoxide for example t-butyl high Dropperoxide, di-isopropylpropyl benzene high dropperoxide, etc .
  • dialkyl peroxide for example, di-t-butylperoxide, di-cumylperoxide, t-butylcumylperoxide, etc .
  • a silver oxide for example, acetyl peroxide, isoptyryl peroxide Peroxydicarbonates
  • Preferred initiators are 2,2'-azobisisobutyronitrile, 1,1'-azobis (cyclohexane-1-carbonitrile), t-butyl peroxide and di-t-butyl peroxyside. t-Butyl peroxide! Preferred for!
  • the polymerization initiator is preferably used in a molar ratio of at least 1Z100, particularly at least 3Z100, based on the raw materials. Even if the total amount is too large, there is no particularly advantageous effect, and generally the molar ratio is 2 to 10 or less.
  • the polymerization temperature is preferably from 50 to 180, especially from 80 to 160. It is preferred that after all of the initiator is added, reflux stirring is continued while maintaining this temperature. It takes 6 to 72 hours, preferably 10 to 30 hours, from the start of the addition of the initiator to the termination of the polymerization reaction.
  • the polymerization reaction system may further include a solvent.
  • the amount of the solvent is preferably such that the starting ester concentration is 10% by weight or more.
  • the solvent those commonly used in radical Polymerization, for example, cyclohexanone methyl E chill ketone, methyl isobutyl Ke Bokun, cyclohexane, p - xylene, 0 - xylene, benzene, toluene, tetrahydrofuran and the like ⁇
  • Particularly preferred lubricating oils for refrigerators according to the invention have the formula (III)
  • each R is independently a linear or branched alkyl group having 3 to 8 carbon atoms. Contains coalescence.
  • copolymer components for example, repeating units (II) can be contained.
  • Such other copolymer components include, for example, ethylene, butene, styrene and the like.
  • the repeating unit (I) is
  • R 1 is made of repeating units from 50 to 99 mol% is ⁇ to units 1-50 mol% and a linear or branched 1-8 alkyl group is Echiru group, ⁇ and units (II) is copolycondensation It constitutes 0 to 20 mol% of the whole combined components.
  • R in the formula (IV) examples include a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group and the like, and structural isomers thereof.
  • R is an n-butyl group.
  • R may be the same or different. If the structural unit represented by the formula () is more than 50 mol%, that is, if the number of units derived from getyl fumarate is larger than the number of units derived from dialkyl fumarate, the viscosity index is extremely lowered.
  • the copolymer can be any copolymer such as a random copolymer or a block copolymer.
  • Such an alkyl fumarate copolymer can be produced, for example, as follows. First, getyl fumarate and an alkyl fumarate are used as raw materials, and getyl fumarate is 50 mol% or less. Mix in such proportions.
  • the polymerization of fumarate ester occurs after the isomerization of maleate ester (Acta Polymer ica). 39 (1988) No. 1, 5-8), the corresponding getyl maleate and alkyl maleate can also be used as raw materials.
  • polymerization can be carried out in the same manner as described above.
  • fumaric acid esters having other structural units for example, other fumaric acid esters represented by the above general formulas (I) and (II) can also be used.
  • the lubricating oil for a refrigerator comprises 5-45 mol% of a structural unit represented by the following formula (V) and 95-55 mol% of a structural unit represented by the following formula (VI). And a fumaric acid ester copolymer having a molecular weight of 800 to 3,000.
  • the repeating unit (I) is a repeating unit of 5 to 45 mol% in which II is an ethyl group and a repeating unit 95 to 55 in which II is a linear or branched butyl group. It consists of mol% and does not contain the repeating unit (II).
  • C 4 Ho in the formula (VI) includes all structural isomers such as n-butyl, sec-butyl, tert-butyl and isobutyl.
  • the ratio of the structural unit formula (V) is 5 to 45 mol%, preferably 6 to 39 mol%, and the ratio of the structural unit formula (VI) is 95 to 55 mol%, preferably 94 to 61 mol%. It is.
  • the copolymer may be any copolymer such as a random copolymer or a block copolymer. Can be coalesced.
  • Such a fumarate ester copolymer can be produced, for example, as follows. First, raw materials such as getyl fumarate and dibutyl fumarate are adjusted so that the respective proportions become the proportions of the respective structural units described above. Merge with. Getyl maleate and dibutyl maleate can also be used as raw materials. Hereinafter, the raw material is polymerized in the presence of a polymerization initiator in the same manner as described above.
  • the viscosity index of the fumaric acid ester copolymer is preferably from 100 to 200.
  • a fumaric acid ester having another structural unit for example, another fumaric acid ester represented by the above general formulas (I) and (H) or (III) and (IV) Acid esters can also be used.
  • the lubricating oil for refrigerators of the present invention for various refrigerators, in addition to the above-mentioned fumaric acid ester polymer, for example, an organic carboxylic acid ester, Conventionally used lubricating oil components for refrigerators, such as polyalkylene glycol, alkylbenzene, and mineral oil, which can be used in desired proportions, can be used in a desired ratio.
  • the fumaric acid ester copolymer it further contains an organic carboxylic acid ester having a kinematic viscosity at 100 C of 2 to 3 OcSt and Z or polyalkylene glycol.
  • the organic carboxylic acid ester and Z or the polyalkylene glycol are preferably used in an amount of not more than 80 parts by weight based on 20 parts by weight of the fumaric acid ester polymer. If too much, the compatibility of high temperature Or tend to lower the viscosity.
  • organic carboxylic acid esters include the following having high molecular polarity.
  • polyol esters of an aliphatic polyhydric alcohol and a linear or branched fatty acid can be used.
  • Examples of the aliphatic polyhydric alcohol forming such polyol esters include trimethylolpropane, ditrimethylolpropane, trimethylolethane, ditrimethylolethane, pentaerythritol, dipentaerythritol, and tripentaerythritol.
  • the fatty acid those having 3 to 12 carbon atoms are preferable, and preferable examples are propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, and decanoic acid.
  • Perdecanoic acid dodecanoic acid, isovaleric acid, neopentanoic acid, 2-methylbutyric acid, 2-ethylbutyric acid, 2-methylhexanoic acid, 2-ethylhexanoic acid, isooctanoic acid, isononanoic acid, isodecanoic acid, 2, 2 '-Dimethyloctanoic acid, 2-butyloctanoic acid and the like.
  • Preferred polyesters of the above-mentioned aliphatic polyhydric alcohols and fatty acids are, in particular, pentaerythritol, dipentaerythritol, pentaerythritol and the like or a mixture thereof, with 5 to 12 carbon atoms, more preferably 5 to 5 carbon atoms.
  • fatty acids such as valeric acid, hexanoic acid, heptanoic acid, 2-methylhexanoic acid, 2-ethylhexanoic acid, isooctanoic acid, isononanoic acid, isodecanoic acid, 1,1, dimethyloctanoic acid, 2-butyl Ester oils with octanoic acid or the like or a mixture thereof, which can improve the compatibility with the refrigerant particularly at low temperatures.
  • partial esters of an aliphatic polyhydric alcohol and a linear or branched fatty acid can also be used.
  • the above-mentioned polyhydric alcohol can be used as the polyhydric alcohol.
  • Fatty acids include those with 3 to 9 carbon atoms.
  • Preferred and preferred examples include propionic acid, butyric acid, valeric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, 2-methylhexanoic acid, 2-ethylhexane, isooctanoic acid, isononanoic acid and the like. Is mentioned.
  • These partial esters can be obtained by appropriately adjusting the number of moles of the reaction between the aliphatic polyhydric alcohol and the fatty acid for the reaction.
  • Neopentyl glycol is used as an aliphatic polyalcohol, and is used in combination with linear or branched fatty acids having 6 to 9 carbon atoms, such as hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, 2- Diesters with ethyl butyric acid, 2-methylhexanoic acid, 2-ethylhexane acid, isooctanoic acid, isononanoic acid and the like can also be used.
  • linear or branched fatty acids having 6 to 9 carbon atoms such as hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, 2- Diesters with ethyl butyric acid, 2-methylhexanoic acid, 2-ethylhexane acid, isooctanoic acid, isononanoic acid and the like can also be used.
  • Complex esters with group polybasic acids can also be used.
  • aliphatic polyalcohols examples include trimethylolpropane, trimethylolethane, pentaerythritol, and dipentaerythritol.
  • straight-chain or branched fatty acids having 3 to 12 carbon atoms include propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, Dodecanoic acid, 2-methylbutyric acid, 2-ethylbutyric acid, 2-methylhexanoic acid, 2-ethylhexanoic acid, isooctanoic acid, isononanoic acid, isodecanoic acid, 2,2'-dimethyloctanoic acid, 2-butyric acid Cutanoic acid and the like can be used.
  • the obtained ester oil can improve the compatibility with the refrigerant particularly at low temperatures.
  • fatty acids Isovaleric acid, valeric acid, hexanoic acid, 2-methylbutyric acid, 2-ethylbutyric acid or a mixture thereof is used, and those having 5 carbon atoms and 6 carbon atoms are in a weight ratio of 10: 90 to 9 Fatty acids mixed at a ratio of 0:10 can be suitably used.
  • Aliphatic dibasic acids that can be used for esterification with polyhydric alcohols together with this fatty acid include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, pendecanedioic acid, Examples include decandioic acid, tridecandioic acid, carboxiooctadecanoic acid, carboxymethylthioctadecanoic acid, docosantioic acid and the like.
  • Examples of the aromatic dibasic acid include phthalic acid and isophthalic acid, and examples of the aromatic tribasic acid include trimellitic acid, and examples of the aromatic tetrabasic acid include pyromellitic acid. No.
  • the ratio of the fatty acid to the aliphatic dibasic acid and / or the aromatic or polybasic acid is preferably 6: 1 (molar ratio). In the esterification reaction, these acids (fatty acids, aliphatic or aromatic) are used. The ratio of the total amount of polybasic acid) to the amount of polyhydric alcohol used should be 7: 1.
  • esterification reaction first, a polyhydric alcohol is reacted with an aliphatic dibasic acid and / or an aromatic polybasic acid at a predetermined ratio to perform partial esterification, and then, the partially esterified product is reacted with a fatty acid.
  • the reaction sequence of the acid may be reversed, or the acid may be mixed and subjected to esterification.
  • Dialkyl esters of linear or branched aliphatic dibasic acids (C 1-22 may be used).
  • Examples of the aliphatic dibasic acids preferably aliphatic dibasic acids 3 ⁇ 4 which can be used an aliphatic dibasic acid shown above (3) include succinic acid, adipic acid, sebacic acid, Undekan acid, dodecanedioic Acid, Carboxyoctadecane Acid, carboxymethyl octadecanoic acid and the like.
  • As the alkyl alcohol component alcohols having 5 to 8 carbon atoms can be used, and examples thereof include amyl alcohol, hexyl alcohol, heptyl alcohol and octyl alcohol, and isomers thereof. Isoamyl alcohol and isohexyl alcohol are preferred.
  • octyl alcohol Specific examples include dioctyl adipate, diisoheptyl adipate, dihexyl sebacate, diheptyl succinate and the like.
  • Dialkyl esters of aromatic dibasic acids (having 18 to 26 carbon atoms) can also be used.
  • aromatic dibasic acid examples include phthalic acid, isophthalic acid, and derivatives thereof.
  • alkyl alcohol component the above
  • Preferred alcohols in which the alcohol having 5 to 8 carbon atoms shown in (4) can be used are isoamyl alcohol, isoheptyl alcohol and octyl alcohol.
  • diesters include dimethyl phthalate, diisoheptyl phthalate, diisoamyl phthalate and the like.
  • monohydric alcohols selected from methanol, ethanol, propanol, butanol, etc. and their isomers, polyhydric alcohols such as glycerin, trimethylolpropane, etc .; and, for example, ethylenoxide, propylene oxide, butylene oxide
  • Organic carboxylic acid esters using an adduct of 1 to 10 moles, preferably 1 to 6 moles of an alkylene oxide selected from amides, amylenoxides and the like and their isomers can also be used.
  • the acid for the alkylene oxide adduct of a monohydric alcohol the aliphatic dibasic acids and aromatic polybasic acids shown in the above (3) can be used.
  • the acid for the alkylene oxide adduct of polyalcohol The linear or branched fatty acids having 3 to 12 carbon atoms shown in (1) can be used.
  • fatty acid constituting the above-mentioned organic carboxylic acid ester a linear or branched fatty acid can be used.
  • a branched fatty acid when used, the hydrolysis stability is more excellent, and the hermetic is more preferable. Compatibility with coils and the like can be achieved.
  • organic carboxylic acid esters can be obtained by esterifying alcohols and fatty acids in the presence of an acid catalyst such as phosphoric acid.
  • an acid catalyst such as phosphoric acid.
  • the total acid value is 0.1 to 0.5 mg KOH / g
  • the peroxide value is 0.1 to 5 meq Z kg
  • the aldehyde value is 0.1 to 5 mg KOH / g
  • the bromine number index is 1 to 100 mg / g. 100 g
  • an ash content of 5 to 50 ppm and a water content of 300 to 100 ⁇ are obtained.
  • lubricating oil for refrigerators has a total acid value of 0. 0 5 mgKOH / g or less is preferred
  • the peroxide value, aldehyde value, and bromine value index are kept low to further increase the stability of the refrigerant, and the ash content is suppressed to suppress sludge, etc. It is preferable to suppress the water content. Therefore, by refining the above esters obtained by ordinary esterification reaction and adjusting the index indicating the above properties of the ester oil to a range suitable for refrigerating machine oil, a more excellent refrigerating machine oil can be obtained. Can be.
  • polyalkylene glycols usable in the present invention include homopolymers of alkylene glycols such as polyethylene glycol and polypropylene glycol, and copolymers such as alkylene oxides such as ethylene oxide and propylene oxide.
  • the terminal group may be substituted with a methyl group, an ethyl group, a propyl group, a butyl group or the like.
  • the average molecular weight is usually from 500 to 180; preferably from 800 to 160. If it is less than 500, the compatibility with the refrigerant at high temperatures is high, but the kinematic viscosity is And the thermal stability tends to decrease. If it exceeds 180, the kinematic viscosity is high, but the compatibility with the refrigerant tends to decrease.
  • the lubricating oil for refrigerators of the present invention may be added with a viscosity index improver for the purpose of obtaining desired kinematic viscosity and viscosity index required for various refrigerators.
  • a viscosity index improver for the purpose of obtaining desired kinematic viscosity and viscosity index required for various refrigerators.
  • Conventional materials can be used, for example, polyolefins (eg, polybutene, poly ⁇ -olefin, ethylene-olefin copolymer, etc., including hydrogenated products), polymethacrylates (eg, homopolymers of methacrylate, acrylate, and acrylic acid).
  • a copolymer containing methacrylic acid as a component polyisobutylene, polyalkylstyrene, ethylene-propylene copolymer, styrene-gen copolymer, styrene-maleic anhydride copolymer and the like.
  • the compounding amount of these viscosity index improvers is usually 0.1 to 20% by weight, preferably 1 to 10% by weight based on the base oil.
  • the lubricating oil for refrigerators of the present invention generally has a kinematic viscosity range (at 100) of 2 to 10 O cSt, preferably 2 to 80 cSt. If the temperature is less than 2 cSt, the compatibility with the refrigerant at high temperature is high, but the kinematic viscosity is low and lubrication occurs. The properties and sealing properties are reduced, and the thermal stability also tends to be reduced. If it exceeds 10 O cSt, the compatibility with the refrigerant tends to decrease. However, even within this range, the kinematic viscosity range varies depending on the model used. For example, for refrigerators, it is 2 to 9 cSt, preferably 3 to 7 CSt.
  • the reciprocating type compressor has a pressure of 7 to 15 cS ⁇ , preferably 8 to 1 lcSt
  • the rotary type compressor has a pressure of 15 to 4 OcSt, preferably 20 to 3 cSt. 5 cSt.
  • a refrigerator if it exceeds 9 cSt, there is a problem that the friction loss in the sliding part becomes large.
  • the lubricity decreases. If it exceeds, there is a problem that the friction loss in the sliding portion becomes large, and in the case of a rotary-type car air conditioner, if it is less than 15 CSt, there is a problem that the sealing property is deteriorated.
  • R is an alkyl group, aryl group, phenyl group
  • Sulfides such as phenyl sulfide, diphenyl disulfide, di-n-butyl sulfide, di-n-butyl disulfide, di-ter
  • Sulfurized oils and fats such as dosperm oil and sulfalide dodipentene, and thiocarbonates such as xanthic disulphide, first-class Zinc alkyl thiophosphate, zinc secondary alkyl thiophosphate, zinc alkyl-aryl thiophosphate, zinc aryl thiophosphate, etc.
  • Phosphorus-based antiwear agents include benzyl diphenyl phosphate, aryl diphenyl phosphate, triphenyl renophosphate, tricresino rephosphate, ethinoresphenyl phosphate, tributyl phosphate, dibutyl phosphate, dibutyl phosphate, resin / resin.
  • wear inhibitors may be used alone or in combination of two or more.
  • the use ratio of the antiwear agent is usually from 0.01 to 5% by weight, preferably from 0.1 to 3% by weight, based on the base oil.
  • Antioxidants can also be used, for example, amine antioxidants such as dioctyldiphenylamine, phenyl- ⁇ -naphthylamine, alkyldiphenylamine, ⁇ -ditrosodiphenylamine, 6-di-butyl valacresol, 4,4′-methylenebis (2,6-di-t-butylphenol), 2,6-di-butyl- ⁇ -dimethylamamine paracresol, 2,6- Phenolic antioxidants such as dibutyl phenol, tris (2,4-diphenylphenyl) phosphite, trisnonylphenylphosphite, And phosphorus-based antioxidants such as triphenylphosphite. These may be used alone or in combination of two or more. The proportion of the antioxidant to be used is usually 0.01 to 10% by weight, preferably 0.01 to 1.0% by weight, based on the base oil.
  • Corrosion inhibitors can also be used, for example, isostearate, n-octadecylammonium stearate, duomin T-diolate, lead naphthenate, sorbitan oleate, pendus eryslit, oleate, oreile sarcosine And alkyl succinic acid, alkenyl succinic acid, and derivatives thereof. These may be used alone or in combination of two or more.
  • the use ratio of the corrosion inhibitor is usually 0.001 to: 1.0% by weight, preferably 0.01 to 0.5% by weight, based on the base oil.
  • An antifoaming agent such as silicone can also be used.
  • the proportion used is usually from 0.0001 to 0.003% by weight, preferably from 0.0001 to 0.001% by weight, based on the base oil.
  • Metal deactivators can also be used, for example, benzotriazole, benzotriazole-induced rest, thiadiazole, thiadiazole derivative, triazole, triazole-induced rest, dithiolbamate, etc. These can be used alone. However, two or more kinds can be used in combination.
  • the usage ratio of the metal deactivator is usually from 0.01 to: 0% by weight of the base oil, preferably from 0.01 to: 0% by weight of the base oil.
  • an antibacterial agent may be used, and examples thereof include succinic acid, succinic acid ester, oleic acid tallow amide, barium sulfonate, and calcium sulfonate. These may be used alone or in combination of two or more.
  • the proportion of the protective agent used is usually from 0.01 to: 0% by weight of the base oil, preferably from 0.01 to: 1.0% by weight.
  • As the stabilizer 0.1 to 20% by weight of the following can be added.
  • Epoxy compounds such as styrene oxide, binenoxide, limonene oxide, 3,4-epoxycyclohexyl / remethy / re, and 3,4-epoxycyclohexylca / repoxylate.
  • Preferred polymerization initiator
  • tert-butyl baroxide is preferred as a polymerization initiator for obtaining an alkyl fumarate polymer or copolymer.
  • the fumaric acid alkyl ester polymer or copolymer is defined by the above formula (I)
  • the copolymer which is a homopolymer or a copolymer having the structural unit represented by, can be any copolymer such as a random copolymer and a block copolymer.
  • R include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. R may be the same or different.
  • a polymerization initiator tert - butyl bar oxides, and preferably the amount of against the raw 0 4 initiator used 1-5 mol% is too small tends yield is lowered, too much.
  • the kinematic viscosity tends to increase.
  • the polymerization temperature is preferably from 130 to 17 CTC. If the polymerization temperature is lower than this, the yield tends to decrease. If the polymerization temperature is higher than this, the coloration tends to occur. If the reaction time is too short, the yield tends to decrease.
  • the yield of the polymer obtained by these polymerizations has a special alkyl group. Low except for monomers, especially straight-chain alkyl group, for example ⁇ - propyl group, (hereinafter 3 0%) yield is low in the case of having a n- butyl group as an ester group 4 such polymerization reactions, It is carried out in a solvent such as isopropyl alcohol in the presence of a polymerization initiator such as 2,2'-azobisisobutyronitrile.
  • the present inventors have found that when a diester monomer of fumaric acid or maleic acid is polymerized in the presence of a polymerization initiation bar to obtain an alkyl fumarate polymer or copolymer, the polymerization is carried out in a tetrahydrofuran solvent. It was found that a polymer was obtained in high yield, and that the polymer was particularly suitable as a lubricating oil for refrigerators.
  • the alkyl ester fumarate polymer or copolymer is defined by the above formula (I)
  • a homopolymer or copolymer having a structural unit represented by The copolymer can be any copolymer such as a random copolymer and a block copolymer.
  • R include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. R may be the same or different.
  • the polymerization initiator As the polymerization initiator, the above-mentioned known ones can be used.
  • the polymerization initiator is preferably used in a molar ratio of at least 1Z100 to the raw material. In order to improve the yield, the initiator should not be added to the polymerization reaction system at once. It is preferable to add palindrically or continuously. *
  • the polymerization temperature is preferably 60 to 145, and the reaction time is preferably 24 to 72 hours. If the time is too short, the yield will decrease.
  • TH F tetrahydrofuran
  • the amount of ⁇ solvents the volume ratio> is too small relative to the raw material Since the kinematic viscosity of the polymer becomes too high, the compatibility with the refrigerant decreases, and when it is too high, the yield tends to decrease.
  • the present inventors have found that it is preferable to use P-xylene as a solvent in the same manner as described above.
  • the obtained polymer has a high viscosity index and has a wide temperature range in which it is compatible with the alternative CFC-based refrigerant.
  • the present inventors have found that the yield of the polymerization reaction can be improved by adding the radical polymerization initiator in a specific manner. That is, in a method for producing a polymer by polymerizing a dialkyl fumarate or a dialkyl maleate in the presence of a radical polymerization initiator, at least the radical polymerization initiator is added at least over a 2-hour addition time. It is preferable to add the amount more than 23 times the total amount of the radical polymerization initiator at the specific time interval of 1 to 5 of the above-mentioned addition time.
  • the total amount of the added radical polymerization initiator (hereinafter sometimes simply referred to as the initiator) is preferably at least 100: 1, more preferably at least 3100 moles to the raw material ester. Ratio. If the total amount is too large, there is no particularly advantageous effect, and it is generally less than 2 to 10 molar ratio.
  • the present invention is characterized in that the initiator is added to the polymerization reaction system batchwise or continuously, rather than all at once, whereby the yield is favorable. Or 70% or more, especially 80 to 100%.
  • the addition of the initiator takes at least 2 hours, preferably 3 to 12 hours. During this addition time, the total amount of initiator is added batchwise or continuously in at least 4 portions, preferably at least 10 portions. Increasing the number of batches will result in a continuous addition. Increasing the number of batches tends to reduce the total amount of initiator.
  • the effect of this embodiment may be lost due to adding a large amount of initiator at once.
  • a specific time interval corresponding to 1 Z 5 of the initiator addition time no more than 2 to 3 of the total starting thorn should be added.
  • no more than 1 to 5 of the total initiator is added during a specific time interval corresponding to 1 Z 10 of the addition time.
  • the total amount of the initiator is divided into approximately equal amounts of 10 to 20 times and added at approximately equal time intervals. In industrial mass production, it is operationally easy to add the initiator continuously at a constant flow rate.
  • the alkyl group in the starting material dialkyl fumarate and maleic acid dialkyl ester in this embodiment is preferably an alkyl group having 8 or less carbon atoms, particularly 4 or less carbon atoms.
  • the alkyl group is direct, the effect of this embodiment is more remarkable since the yield was particularly poor in the conventional method.
  • Known radical polymerization initiators can be used. Polymerization ⁇ preferably 5 0: is at L 6 0: L 8 0 e C, especially 8 0. After adding all the initiator, it is preferable to continue the reflux stirring while maintaining this temperature. From the start of the addition of the initiator to the termination of the polymerization reaction, preferably for 6 to 40 hours, particularly 10 to 3 hours Take 0 hours
  • the lubricating oil for refrigerators of the present invention includes, for example, air conditioners for buildings and homes, refrigerators, It can be used as lubricating oil in refrigerators used in refrigeration systems in a wide range of fields such as freezers and car air conditioners.
  • the lubricating oil of the present invention can also be added as an additive to lubricating oils for refrigerators based on other substances, for example, organic carboxylic acid esters, polyalkylene glycols, alkylbenzenes, mineral oils and the like.
  • the lubricating oil for refrigerators of the present invention uses the above-mentioned alkyl fumarate copolymer having a specific structure, it is compatible with alternative Freon-based refrigerants such as hydrogen-containing halogenated hydrocarbons, especially with R134a. Temperature range is wide and viscosity index is high. It is also thermally and chemically stable and has excellent lubricity.
  • the yield was determined as the ratio of the weight of the residue to the total weight of the starting ester monomer by removing light components from the polymerization reaction system by distillation under reduced pressure.
  • Sample oil and refrigerant (1,1,1,2-tetrafluoroethane, R134a) are collected in a glass tube and mixed at a rate of 15% by volume of the sample oil to a total of 2 nH and mixed. Then, the glass tube was placed in a thermostat having a cooling device, and the separation temperature of the sample oil and the refrigerant at a low temperature was measured. Next, the sample oil and the refrigerant were collected and mixed in another glass tube so that the sample oil became 10% by volume of the total so that the total volume became 2 nH, and the glass tube was placed in a thermostat having a heating device. Then, the separation temperature of the sample oil and the refrigerant at high temperature was measured. In addition, in Example 12 and thereafter, since the measurement is not possible at a temperature below 1 and at a temperature of 80 ° C. or more due to the equipment, the temperature is shown in the table where applicable.
  • a reaction product was prepared in the same manner as in Example 1 except that getyl fumarate was 305 rmol, o-xylene was 250 l, AIBN 50 ranol, the reaction temperature was 135 C, and the reaction time was 4 hours. I got Table 1 below shows the viscosity and compatibility of the reaction products.
  • Example 1 The same equipment as in Example 1 except that getyl fumarate was set to 310 ⁇ A, no solvent was used, AIBmOraiBO was used, the reaction temperature was 80, and the reaction time was 8 hours. I got something. Table 1 below shows the viscosity and compatibility of the reaction products.
  • Example 1 The same apparatus as in Example 1 was used, except that getyl fumarate was set at 310 ° C., no solvent was used, ⁇ 2 ⁇ , the reaction temperature was 80, and the reaction time was 8 hours.
  • the reaction product was obtained in the same manner. Table 1 below shows the viscosity and compatibility of the reaction products.
  • Example 1 The same apparatus as in Example 1 was used, except that getyl fumarate was 305HI1IO I, and no solvent was used. C. A reaction product was obtained in the same manner as in Example 1 except that the reaction time was changed to 12 hours. Table 1 below shows the reaction products Shows viscosity and compatibility.
  • Example 7 In the same apparatus as in Example 1, dibutyl fumarate was set to 217 raraol, the reaction temperature was set to 118 ° C., and a solution of AIBN27.5-methyl isobutyl ketone (MIBK) was added dropwise over 12 hours. A reaction product was obtained in the same manner as in Example 1 except that the time was changed to 24 hours. Table 1 below shows the viscosity and compatibility of the reaction products.
  • MIBK AIBN27.5-methyl isobutyl ketone
  • Example 4 the reaction product of 49% prepared in, and to prepare a Jipentaerisuri Torr and mixed oil consisting of an ester reaction product of 51% of C 6 acid as a refrigeration lubricant.
  • Table 1 shows the viscosity and compatibility of the mixed oil.
  • Table 1 below shows the viscosity and compatibility of the mixed oil
  • Example 2 In the refrigerator oil prepared in Example 2, the refrigerator oil prepared in Example 4 was distilled under reduced pressure, and the solid content obtained by cutting the component having a low polymerization degree was 5%. A lubricating oil for a refrigerator was prepared. Table 1 below shows the viscosity and compatibility of the mixed oil
  • the lubricating oil for refrigerators prepared in Example 2 was mixed with 5% of polymethyl methacrylate having a weight average molecular weight of 12000 to prepare lubricating oil for refrigerators.
  • Table 1 below shows the viscosity and compatibility of the mixed oil.
  • Polypropylene glycol dimethyl ether was evaluated as a lubricating oil for refrigerators. Table 1 below shows the viscosity and compatibility.
  • the lubricating oil for refrigerators of the present invention has high compatibility with the hydrogen-containing refrigerant, is mature and chemically stable, and has excellent lubricity.
  • the kinematic viscosity of the obtained polymer was measured, and the viscosity index was determined. A compatibility test was also performed. Table 2 shows the results.
  • Example 15 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 12, and the viscosity index was determined. The result of a compatibility test was also shown in Table 2.
  • Example 15 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 12, and the viscosity index was determined. The result of a compatibility test was also shown in Table 2.
  • St is the dimethyl ether of polypropylene glycol, 80:20 (Weight ratio) to obtain a lubricating oil.
  • the kinematic viscosity of the obtained lubricating oil was measured in the same manner as in Example 12, and the viscosity index was determined. A compatibility test was also performed. The results are shown in Table 2.
  • the kinematic viscosity of the obtained lubricating oil was measured in the same manner as in Example 12, and the viscosity index was determined.
  • Table 2 shows the results of the compatibility test.
  • the kinematic viscosity of the obtained polymer was measured in the same manner as in Example 12, and the viscosity index was determined. A compatibility test was also performed. Table 2 shows the results.
  • the yield was determined as a ratio of the weight of the residue to the total weight of the starting ester monomer after removing light components from the polymerization reaction system by vacuum distillation.
  • the obtained polymer was analyzed by Jfi-NMR and 13 C-NMR. The results are shown in Figures 1 and 2.
  • the amounts of di-n-butyl fumarate and getyl fumarate were 402 mmol (91.8 g, 92.7 ml) and 45 mmol (7.7 g, 73 ml), respectively, except for a molar ratio of 9: 1.
  • a polymerization reaction was carried out in the same manner as in Example 18. Thus, 89.6 g of a polymer was obtained. 90% yield.
  • the obtained polymer was analyzed by 1 H-NMR and 13 C-NMR under the same conditions as in Example 18. The results are shown in FIGS.
  • the obtained polymer was analyzed by 1 H-NMR and 13 C-NHR under the same conditions as in Example 18. The results are shown in FIGS. From these results, it was confirmed that this polymer was a homopolymer of di-n-butyl fumarate.
  • the number average molecular weight (Mn) was determined to be 840 in the same manner as in Example 18. Further, the kinematic viscosity was measured, the viscosity index was determined, and a compatibility test was also performed.
  • the kinematic viscosity of the obtained polymer was measured, and the viscosity index was determined. A compatibility test was also performed. Table 4 shows the results.
  • a 200 mi one-necked flask was charged with 402 mmol of di-n-butyl fumarate (91.8 e 92.7 mU and 45 mmol of getyl fumarate (7.7 e, 7.3 ml)) (molar ratio 9: 1).
  • the cooling pipe After installing the cooling pipe, it was set in an oil bath, and the temperature was stirred while stirring with a magnetic stirrer. The temperature was kept at 150 ° C., and 2 mmol (0.4 ml) of t-butyl vaginate oxide (TBPO) was added, and the mixture was heated and stirred at this temperature for 72 hours. Thereafter, light components were distilled off under reduced pressure to obtain a polymer 93.3 e. The polymer was not colored. 94% yield.
  • TBPO t-butyl vaginate oxide
  • Example 22 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 20, and the viscosity index was determined. Table 4 shows the results of the compatibility test.
  • Example 22 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 20, and the viscosity index was determined. Table 4 shows the results of the compatibility test.
  • the kinematic viscosity of the obtained polymer was measured, and the viscosity index was determined. A compatibility test was also performed. Table 5 shows the results.
  • the polymerization reaction was carried out in the same manner as in Example 23 except that the amount of tetrahydrofuran was changed to 1 Oml using a 100 ml one-necked flask. Thus, 45.1 g of a polymer was obtained. Yield 91%.
  • Example 25 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 23, and the viscosity index was determined. ⁇ A compatibility test was also conducted. Table 5 shows the results.
  • Example 25 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 23, and the viscosity index was determined. ⁇ A compatibility test was also conducted. Table 5 shows the results.
  • Example 25 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 23, and the viscosity index was determined. ⁇ A compatibility test was also conducted. Table 5 shows the results. Example 25
  • a polymerization reaction was carried out in the same manner as in Example 24 except that 10 ml of tetrahydrofuran was not added. Thus, 10.9 g of a polymer was obtained. Yield 22%.
  • Example 15 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 23, the viscosity index was determined, and a compatibility test was performed. The results are shown in Table 5. Comparative Example 15 A polymerization reaction was carried out in the same manner as in Example 23, except that 10 O ml of isopropyl alcohol was used instead of tetrahydrofuran as a solvent. Thus, a polymer 33.2 e was obtained in a yield of 67%.
  • a polymerization reaction was carried out in the same manner as in Example 23 except that 100 ml of heptane was used instead of tetrahydrofuran as a solvent. Thus, a polymer 33.2 was obtained. Yield 6%.
  • a polymerization reaction was carried out in the same manner as in Example 23 except that 100 ml of r-butyrolactone was used instead of tetrahydrofuran as a solvent. Thus, 28.7 g of a polymer was obtained. Yield 57%.
  • the polymerization reaction was carried out in the same manner as in Example 23 except that 100 ml of o-xylene was used instead of tetrahydrofuran as a solvent. 6.2 e was obtained. Yield 5 3%,
  • a polymerization reaction was carried out in the same manner as in Example 23 except that 100 ml of methylethyl ketone was used instead of tetrahydrofuran as a solvent. Thus, a polymer 31.2 ⁇ was obtained. Yield 63%.
  • the polymerization reaction was carried out in the same manner as in Example 23, except that ethanol was used as the solvent instead of tetrahydrofuran, and 100 O ml was used. Thus, polymers 34 and 2e were obtained. Yield 69%.
  • a polymerization reaction was carried out in the same manner as in Example 23 except that 100 ml of n-butanol was used instead of tetrahydrofuran as a solvent. Thus, a polymer 23.8 e was obtained. Yield 48%.
  • the kinematic viscosity of the obtained polymer was measured in the same manner as in Example 23.
  • the viscosity index was determined.
  • a compatibility test was also performed.
  • Table 5 shows the results. Table 5 shows that high yield was achieved by using tetrahydrofuran.
  • THF tetrahydrofuran
  • tributylamine isopropyl alcohol
  • ⁇ - ⁇ ⁇ -xylene
  • GBL r-petit mouth ratatatone
  • o-XY o-xylene
  • HEK methylethyl ketone
  • Et0H ethanol
  • Bu0H n-butanol
  • the kinematic viscosity of the obtained polymer was measured, and the viscosity index was determined. A compatibility test was also performed. Table 6 shows the results.
  • a polymerization reaction was carried out in the same manner as in Example 26, except that the amount of P-xylene was changed to 10 ml using a 100 ml one-necked flask, thereby obtaining 35.1 g of a polymer. Yield 71%.
  • Example 28 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 26, and the viscosity index was determined. A compatibility test was also performed. The results are shown in Table 6.
  • Example 28 The kinematic viscosity of the obtained polymer was measured in the same manner as in Example 26, and the viscosity index was determined. A compatibility test was also performed. The results are shown in Table 6.
  • the polymerization reaction was carried out in the same manner as in Example 26 except that 100 ml of isopropyl alcohol was used instead of P-xylene as the solvent.
  • the product 33, 2e was obtained. Yield 6%.
  • the polymerization reaction was carried out in the same manner as in Example 26 except that o-xylene 10 Oml was used instead of ⁇ -xylene as a solvent. Thus, a polymer 26.2 was obtained. Yield 53%.
  • the polymerization reaction was carried out in the same manner as in Example 26 except that 100 ml of ethanol was used instead of P-xylene as the solvent. Thus, a polymer 34.2 e was obtained. Yield 69%.
  • the polymerization reaction was carried out in the same manner as J26, except that n-butanol 10 O ml was used instead of P-xylene as a solvent.
  • the polymer 23.8 ⁇ was thus obtained in a yield of 48%.
  • the kinematic viscosity of the obtained polymer was measured in the same manner as in Example 26, the viscosity index was determined, and a compatibility test was also performed. Table 6 shows the results. Table 6 shows that a high viscosity index can be achieved by using ⁇ -xylene. 6
  • Example 31 was repeated except that the amount of P-xylene was set to 40 Oml and heating and refluxing were continued for 19 hours after completion of the addition of AIBN, to obtain a polymer 49.1 e (yield 94%).
  • Mn 440
  • Example 31 was repeated except that 0-xylene 5 Oml was used instead of P-xylene and the reaction temperature was 145 ° C. Polymer 54e was obtained (yield 100%).
  • Example 31 was repeated except that 50 ml of 4-methyl-2-pentanone (MIBK) was used instead of P-xylene, and the reaction temperature was set at 118. Polymer 54e was obtained (yield 100%).
  • MIBK 4-methyl-2-pentanone
  • Example 31 was repeated except that cyclohexanone 5 Oml was used in place of P-xylene and the reaction temperature was set to 150. 52.5 e of a polymer was obtained (yield: 100%).
  • Example 35 was repeated except that di-n-butyl fumarate 21.7 inmol (49.5 e ) was used as the starting ester and the amount of AIBN was 27.5 ml (4.5 e). e was obtained (100% yield).
  • Example 31 was repeated except that 310 mmol (53.5 e , 50 ml) of getyl maleate was used as the starting ester, and 1.14 mmol (0.1 mi) of morpholine was further added to the reaction system first. Polymer 53e was obtained (100% yield). Comparative Example 30
  • Comparative Example 30 was repeated except that 25-ml of 2-butanone (MEK) was used instead of P-xylene and the reaction temperature was set to 80. ⁇ Polymer 23.5 e was obtained (yield: 45%) .
  • MEK 2-butanone
  • a polymer 21.6 e was obtained by repeating Comparative Example 30 except that cyclohexanone 25 Oml was used instead of P-xylene and the reaction temperature was set to 155 (yield 43%).
  • the lubricating oil for refrigerators of the present invention can be used as lubricating oil in refrigerators used in refrigeration systems in a wide range of fields, such as air conditioners for buildings and homes, refrigerators, freezers, car air conditioners, and the like.
  • the lubricating oil of the present invention can also be added as an additive to lubricating oils for refrigerators based on other substances, for example, organic carboxylic acid esters, polyalkylene glycols, alkylbenzenes, mineral oils and the like.
  • the lubricating oil for refrigerators of the present invention uses the above-mentioned alkyl fumarate copolymer having a specific structure, it is compatible with alternative Freon-based refrigerants such as hydrogen-containing halogenated hydrocarbons, especially with R134a. Temperature range is wide and viscosity index is high. It is also thermally and chemically stable and has excellent lubricity.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)

Abstract

L'invention se rapporte à une huile lubrifiante pour réfrigérateurs, qui utilise un substitut au chlorofluorocarbone comme réfrigérant et qui contient un polymère d'un ester fumarique ou un copolymère d'un ester fumarique avec un alkylène copolymérisable et, si désiré, un ester carboxylique organique ou un polyalkylèneglycol avec une viscosité cinématique de 2 à 30 cSt. Cette huile est compatible avec un réfrigérant comprenant un substitut au chlorofluorocarbone tel qu'un hydrochlorofluorocarbone, en particulier R134a, dans une gamme de températures étendue, elle possède un indice de viscosité élevé, elle est thermiquement et chimiquement stable et elle se caractérise par un excellent pouvoir lubrifiant.
PCT/JP1992/001707 1991-12-26 1992-12-25 Huile lubrifiante pour refrigerateur WO1993013185A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE69229859T DE69229859T2 (de) 1991-12-26 1992-12-25 Schmieröl für kühlschrank
EP93900440A EP0586705B1 (fr) 1991-12-26 1992-12-25 Huile lubrifiante pour refrigerateur

Applications Claiming Priority (14)

Application Number Priority Date Filing Date Title
JP3/344484 1991-12-26
JP34448491A JPH06122888A (ja) 1991-12-26 1991-12-26 冷凍機用潤滑油
JP4/29013 1992-01-21
JP2901392A JPH05194654A (ja) 1992-01-21 1992-01-21 フマル酸又はマレイン酸ジアルキルエステルの重合体の製造法
JP4/284896 1992-10-01
JP4284896A JPH06192671A (ja) 1992-10-01 1992-10-01 冷凍機用潤滑油
JP4/290960 1992-10-06
JP29096092A JPH06199966A (ja) 1992-10-06 1992-10-06 フマル酸エステル共重合体
JP29191792A JPH06116579A (ja) 1992-10-07 1992-10-07 冷凍機用潤滑油
JP4/291917 1992-10-07
JP4/291916 1992-10-07
JP29191692A JPH06116578A (ja) 1992-10-07 1992-10-07 冷凍機用潤滑油
JP4/291918 1992-10-07
JP29191892A JPH06145246A (ja) 1992-10-07 1992-10-07 フマル酸もしくはマレイン酸ジアルキルエステルの重合体の製造法

Publications (1)

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WO1993013185A1 true WO1993013185A1 (fr) 1993-07-08

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021100634A1 (fr) * 2019-11-19 2021-05-27 Ｅｎｅｏｓ株式会社 Huile pour machine frigorifique, composition de fluide de travail pour machine frigorifique, procédé de lubrification et procédé de production d'huile pour machine frigorifique
WO2021221063A1 (fr) * 2020-04-30 2021-11-04 Ｅｎｅｏｓ株式会社 Huile pour machine frigorifique
KR102808799B1 (ko) 2019-11-19 2025-05-16 에네오스 가부시키가이샤 냉동기유, 냉동기용 작동 유체 조성물, 윤활 방법 및 냉동기유의 제조 방법

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02502385A (ja) * 1987-10-23 1990-08-02 アライド‐シグナル・インコーポレーテッド 冷却用潤滑剤
JPH03172391A (ja) * 1989-11-17 1991-07-25 Akzo Nv α，β―不飽和ジカルボン酸エステルとオレフィン性不飽和化合物より作られる組成物並びに該組成物の製造方法
JPH03205492A (ja) * 1989-05-08 1991-09-06 Idemitsu Kosan Co Ltd 圧縮型冷凍機用潤滑油

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH02502385A (ja) * 1987-10-23 1990-08-02 アライド‐シグナル・インコーポレーテッド 冷却用潤滑剤
JPH03205492A (ja) * 1989-05-08 1991-09-06 Idemitsu Kosan Co Ltd 圧縮型冷凍機用潤滑油
JPH03172391A (ja) * 1989-11-17 1991-07-25 Akzo Nv α，β―不飽和ジカルボン酸エステルとオレフィン性不飽和化合物より作られる組成物並びに該組成物の製造方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ACTA POLYMERICA, vol. 39, no. 1, 1988, pages 5 - 8
See also references of EP0586705A4 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021100634A1 (fr) * 2019-11-19 2021-05-27 Ｅｎｅｏｓ株式会社 Huile pour machine frigorifique, composition de fluide de travail pour machine frigorifique, procédé de lubrification et procédé de production d'huile pour machine frigorifique
US12227712B2 (en) 2019-11-19 2025-02-18 Eneos Corporation Refrigerating machine oil, working fluid composition for refrigerating machine, lubricating method, and method for producing refrigerating machine oil
KR102808799B1 (ko) 2019-11-19 2025-05-16 에네오스 가부시키가이샤 냉동기유, 냉동기용 작동 유체 조성물, 윤활 방법 및 냉동기유의 제조 방법
WO2021221063A1 (fr) * 2020-04-30 2021-11-04 Ｅｎｅｏｓ株式会社 Huile pour machine frigorifique
US12122976B2 (en) 2020-04-30 2024-10-22 Eneos Corporation Refrigerating machine oil
JP7659545B2 (ja) 2020-04-30 2025-04-09 Ｅｎｅｏｓ株式会社 冷凍機油

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