EP0510633A1 - Schmierölzusammensetzung und ihre Verwendung - Google Patents
Schmierölzusammensetzung und ihre Verwendung Download PDFInfo
- Publication number
- EP0510633A1 EP0510633A1 EP92106937A EP92106937A EP0510633A1 EP 0510633 A1 EP0510633 A1 EP 0510633A1 EP 92106937 A EP92106937 A EP 92106937A EP 92106937 A EP92106937 A EP 92106937A EP 0510633 A1 EP0510633 A1 EP 0510633A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- group
- formula
- expressed
- phosphate
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 74
- 239000002199 base oil Substances 0.000 claims abstract description 88
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 142
- 229910019142 PO4 Inorganic materials 0.000 claims description 118
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 118
- 239000010452 phosphate Substances 0.000 claims description 118
- -1 oxypropylene group Chemical group 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000003342 alkenyl group Chemical group 0.000 claims description 55
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 30
- 239000003921 oil Substances 0.000 claims description 19
- 239000012530 fluid Substances 0.000 claims description 18
- 125000005011 alkyl ether group Chemical group 0.000 claims description 9
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000006353 oxyethylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 abstract description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract description 11
- 235000019404 dichlorodifluoromethane Nutrition 0.000 abstract description 10
- 239000000654 additive Substances 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 230000000996 additive effect Effects 0.000 abstract description 5
- 230000002708 enhancing effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 54
- 239000007983 Tris buffer Substances 0.000 description 34
- 238000002156 mixing Methods 0.000 description 23
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 17
- CFRNDJFRRKMHTL-UHFFFAOYSA-N [3-octanoyloxy-2,2-bis(octanoyloxymethyl)propyl] octanoate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC CFRNDJFRRKMHTL-UHFFFAOYSA-N 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000003507 refrigerant Substances 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 6
- JJJOZVFVARQUJV-UHFFFAOYSA-N 2-ethylhexylphosphonic acid Chemical compound CCCCC(CC)CP(O)(O)=O JJJOZVFVARQUJV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000002411 adverse Effects 0.000 description 4
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 4
- SVMUEEINWGBIPD-UHFFFAOYSA-N dodecylphosphonic acid Chemical compound CCCCCCCCCCCCP(O)(O)=O SVMUEEINWGBIPD-UHFFFAOYSA-N 0.000 description 4
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical compound CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 4
- NJGCRMAPOWGWMW-UHFFFAOYSA-N octylphosphonic acid Chemical compound CCCCCCCCP(O)(O)=O NJGCRMAPOWGWMW-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- YLXGYLLBXARBDE-UHFFFAOYSA-N 6-methylheptylphosphonic acid Chemical compound CC(C)CCCCCP(O)(O)=O YLXGYLLBXARBDE-UHFFFAOYSA-N 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 2
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical compound CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- FTMKAMVLFVRZQX-UHFFFAOYSA-N octadecylphosphonic acid Chemical compound CCCCCCCCCCCCCCCCCCP(O)(O)=O FTMKAMVLFVRZQX-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- VWAORQHKDOEGEF-UHFFFAOYSA-N (1-decoxy-2-ethylhexoxy)-(2-ethylhexyl)phosphinic acid Chemical compound CCCCCCCCCCOC(C(CC)CCCC)OP(=O)(CC(CC)CCCC)O VWAORQHKDOEGEF-UHFFFAOYSA-N 0.000 description 1
- HLYJMQXEZUUONQ-UHFFFAOYSA-N (4-methylbenzoyl)phosphonic acid Chemical compound CC1=CC=C(C(=O)P(O)(O)=O)C=C1 HLYJMQXEZUUONQ-UHFFFAOYSA-N 0.000 description 1
- GSWJYCKKASJYIQ-UHFFFAOYSA-N (5-butyl-6-ethyldecan-5-yl) dihydrogen phosphate Chemical compound CCCCC(CC)C(CCCC)(CCCC)OP(O)(O)=O GSWJYCKKASJYIQ-UHFFFAOYSA-N 0.000 description 1
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical group CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GIDPGCUQMJPVDI-UHFFFAOYSA-N 11-heptan-3-ylhenicosan-11-yl dihydrogen phosphate Chemical compound CCCCCCCCCCC(C(CC)CCCC)(OP(O)(O)=O)CCCCCCCCCC GIDPGCUQMJPVDI-UHFFFAOYSA-N 0.000 description 1
- BQPLPLNUWVOHIH-UHFFFAOYSA-N 11-heptylhenicosan-11-yl dihydrogen phosphate Chemical compound CCCCCCCCCCC(CCCCCCC)(OP(O)(O)=O)CCCCCCCCCC BQPLPLNUWVOHIH-UHFFFAOYSA-N 0.000 description 1
- VBKJMKYMBLMMSV-UHFFFAOYSA-N 11-propylhenicosan-11-yl dihydrogen phosphate Chemical compound CCCCCCCCCCC(CCC)(OP(O)(O)=O)CCCCCCCCCC VBKJMKYMBLMMSV-UHFFFAOYSA-N 0.000 description 1
- ITCYJWRELFDETD-UHFFFAOYSA-N 13-heptan-3-ylpentacosan-13-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCCC(C(CC)CCCC)(OP(O)(O)=O)CCCCCCCCCCCC ITCYJWRELFDETD-UHFFFAOYSA-N 0.000 description 1
- OZORYNWOKGGCOO-UHFFFAOYSA-N 13-pentylpentacosan-13-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCCC(CCCCC)(OP(O)(O)=O)CCCCCCCCCCCC OZORYNWOKGGCOO-UHFFFAOYSA-N 0.000 description 1
- LUSCVEUWBBBBLZ-UHFFFAOYSA-N 13-propylpentacosan-13-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCCC(CCC)(OP(O)(O)=O)CCCCCCCCCCCC LUSCVEUWBBBBLZ-UHFFFAOYSA-N 0.000 description 1
- HBXSEBXLYKFFJS-UHFFFAOYSA-N 2-butoxyethylphosphonic acid Chemical compound CCCCOCCP(O)(O)=O HBXSEBXLYKFFJS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NZWIYPLSXWYKLH-UHFFFAOYSA-N 3-(bromomethyl)heptane Chemical compound CCCCC(CC)CBr NZWIYPLSXWYKLH-UHFFFAOYSA-N 0.000 description 1
- XDUHTEGWLSIFBY-UHFFFAOYSA-N 5-butylheptadecan-5-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCCC(CCCC)(CCCC)OP(O)(O)=O XDUHTEGWLSIFBY-UHFFFAOYSA-N 0.000 description 1
- CMHWYQHPKFZQCC-UHFFFAOYSA-N 5-butylhexadecan-5-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCC(CCCC)(CCCC)OP(O)(O)=O CMHWYQHPKFZQCC-UHFFFAOYSA-N 0.000 description 1
- QJJHQIDBFYJADS-UHFFFAOYSA-N 8-methylnonylphosphonic acid Chemical compound CC(C)CCCCCCCP(O)(O)=O QJJHQIDBFYJADS-UHFFFAOYSA-N 0.000 description 1
- KLCDNHOIOPWJLZ-UHFFFAOYSA-N 9-(5-methylhexyl)heptadecan-9-yl dihydrogen phosphate Chemical compound CCCCCCCCC(OP(O)(O)=O)(CCCCC(C)C)CCCCCCCC KLCDNHOIOPWJLZ-UHFFFAOYSA-N 0.000 description 1
- XBUWCSHNUCTORI-UHFFFAOYSA-N 9-heptan-3-ylheptadecan-9-yl dihydrogen phosphate Chemical compound CCCCCCCCC(C(CC)CCCC)(OP(O)(O)=O)CCCCCCCC XBUWCSHNUCTORI-UHFFFAOYSA-N 0.000 description 1
- MUSWNVXQDVMLPG-UHFFFAOYSA-N 9-octylicosan-9-yl dihydrogen phosphate Chemical compound CCCCCCCCCCCC(CCCCCCCC)(CCCCCCCC)OP(O)(O)=O MUSWNVXQDVMLPG-UHFFFAOYSA-N 0.000 description 1
- BQSHJGBYWVBBDL-UHFFFAOYSA-N 9-octyloctadecan-9-yl dihydrogen phosphate Chemical compound CCCCCCCCCC(CCCCCCCC)(CCCCCCCC)OP(O)(O)=O BQSHJGBYWVBBDL-UHFFFAOYSA-N 0.000 description 1
- UTJYCLWPKFCHKD-UHFFFAOYSA-N 9-pentylheptadecan-9-yl dihydrogen phosphate Chemical compound CCCCCCCCC(CCCCC)(OP(O)(O)=O)CCCCCCCC UTJYCLWPKFCHKD-UHFFFAOYSA-N 0.000 description 1
- ZIBISRIUMHVUEV-ARJAWSKDSA-N CC(C)CCCCCCC/C=C\CCCCCCCCOP(O)(O)=O Chemical compound CC(C)CCCCCCC/C=C\CCCCCCCCOP(O)(O)=O ZIBISRIUMHVUEV-ARJAWSKDSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- XEDLVIBRXVIWLS-UHFFFAOYSA-N benzoylphosphonic acid Chemical compound OP(O)(=O)C(=O)C1=CC=CC=C1 XEDLVIBRXVIWLS-UHFFFAOYSA-N 0.000 description 1
- QPKOILOWXGLVJS-UHFFFAOYSA-N bis(2-methylpropoxy)-oxophosphanium Chemical compound CC(C)CO[P+](=O)OCC(C)C QPKOILOWXGLVJS-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- KDIHALZSEJFHBB-UHFFFAOYSA-N didecyl dodecyl phosphate Chemical compound P(=O)(OCCCCCCCCCC)(OCCCCCCCCCC)OCCCCCCCCCCCC KDIHALZSEJFHBB-UHFFFAOYSA-N 0.000 description 1
- LOLGINHRZSNUDZ-UHFFFAOYSA-N didodecyl methyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OC)OCCCCCCCCCCCC LOLGINHRZSNUDZ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DIRDIASJKSKUIQ-UHFFFAOYSA-N dimethyl tridecyl phosphate Chemical compound P(=O)(OC)(OC)OCCCCCCCCCCCCC DIRDIASJKSKUIQ-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QTDSLDJPJJBBLE-PFONDFGASA-N octyl (z)-octadec-9-enoate Chemical compound CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC QTDSLDJPJJBBLE-PFONDFGASA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000010726 refrigerant oil Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- WVPGXJOLGGFBCR-UHFFFAOYSA-N trioctyl phosphate Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)OCCCCCCCC WVPGXJOLGGFBCR-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- FSLSJTZWDATVTK-UHFFFAOYSA-N tris(6-methylheptyl) phosphate Chemical compound CC(C)CCCCCOP(=O)(OCCCCCC(C)C)OCCCCCC(C)C FSLSJTZWDATVTK-UHFFFAOYSA-N 0.000 description 1
- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 1
- KUHPLTBUBAGTDV-UHFFFAOYSA-N tris-decyl phosphate Chemical compound CCCCCCCCCCOP(=O)(OCCCCCCCCCC)OCCCCCCCCCC KUHPLTBUBAGTDV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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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- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M107/34—Polyoxyalkylenes
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Definitions
- This invention relates to a lubricating oil composition for refrigerating machine using 1,1,1.2-tetrafluoroethane (HFC-134a) as refrigerant.
- HFC-134a 1,1,1.2-tetrafluoroethane
- chlorofluorocarbons containing fluorine and chlorine have been used, such.as trichloromonofluoromethane (CFC-11), dichlorodifluoromethane (CFC-12), and monochlorodifluoromethane (HCFC-22).
- CFC-11 and CFC-12 are designated as fully halogenated fluorocarbons because they destroy the ozone layer in the stratosphere, and their use is being limited at the present, and it is nearly decided that their use will be completely banned-in the future.
- HCFC-22 is also likely to be designated as the subject of restriction in the future.
- CFC-12 is widely used in the refrigerating machines such as household refrigerators and automotive air-conditioners, and as the substitute after the use is banned, a chlorine-free 1,1,1,2-tetrafluoroethane (HFC-134a) is expected to be used.
- the HFC-134a not containing chlorine in its molecule, does not act as extreme-pressure agent, unlike CFC-12, which poses the problem of wear of metallic parts exposed inside the compressor.
- the HFC-134a is also inferior in solubility with existing mineral oils, synthetic oils, and other lubricating oils for refrigerating machines (base oils), and ordinary additives blended in such lubricating oils.
- solubility may be nearly solved by using, as the substitutes for hitherto used base oils, for examples, polyalkylene glycol (see Japanese Patent Unexamined Publications No. 102296/1990, 276880/1990), ester base fluid (see Japanese Patent Unexamined Publications No. 24197/1991, 33192/1991, 33193/1991), or fluorinated oil (see Japanese Patent Unexamined Publications No. 93896/1991).
- polyalkylene glycol see Japanese Patent Unexamined Publications No. 102296/1990, 276880/1990
- ester base fluid see Japanese Patent Unexamined Publications No. 24197/1991, 33192/1991, 33193/1991
- fluorinated oil see Japanese Patent Unexamined Publications No. 93896/1991.
- anti-wear property the property of the composition itself to prevent wear of metallic parts
- the invention presents a lubricating oil composition for refrigerating machine comprising at least one organic phosphorus compound selected from a group comprising organic phosphonate expressed in Formula (I), organic phosphate expressed in Formula (V), and organic phosphate expressed in Formula (VI), out of polyalkylene glycol, ester base fluid , fluorinated oil and organic phosphorus compound as specified above, wherein, if composed of polyalkylene glycol and the organic phosphate expressed in Formula (V), the content of the organic phosphate in the base oil exceeds 10 wt.%. where R1, R2 are either identical or different, expressing any one of the groups (1) to (4) below.
- the organic phosphonate expressed in Formula (I), the organic phosphate expressed in Formula (V), and the organic phosphate expressed in Formula (VI) may be all used as the base oil for the lubricating oil composition for refrigerating machine, and are all stable and compounds with excellent anti-wear property, and the lubricating oil composition for refrigerating machine using such compounds as the base oil is superior in antiwear property to the existing materials.
- these compounds are excellent in solubility with existing known base oils such as polyalkylene glycol, ester base fluid and fluorinated oil, and may be also used as antiwear agents for enhancing the anti-wear property of the base oils without adversely affecting the stability.
- the lubricating oil composition for refrigerating machine of the invention containing any one of the above compounds as the base oil or the additive (antiwear agent) for the known base oil exhibits, by itself, an excellent anti-wear property superior to that of the existing lubricating oil composition using CFC-12, and therefore it improves the anti-wear property of the system using HFC-134a not acting as extreme-pressure agent as refrigerant, and hence extremely reduces the wear of metallic parts exposed inside the compressor. Moreover, its anti-wear property is extremely excellent as compared with the anti-wear property of the lubricating oil composition for refrigerating machine using CFC-12 as refrigerant.
- organic phosphonates presented above may be prepared by known methods.
- O,O-diisooctyl isooctylphosphonate may be prepared by reaction of triisooctyl phosphite and isooctyl bromide.
- the content of the organic phosphonate in the base oil is not particularly defined in the invention.
- the organic phosphonate can be used not only as the base oil but also as the additive (anti-wear agent) for other base oil, and its content may be arbitrary including 100 wt.% (that is, the whole base oil may be an organic phosphonate).
- the content should be 0.01 wt.% or more. If the content of the organic phosphonate is less than 0.01 wt.%, its additive effect is insufficient, and sufficient anti-wear property may not be achieved.
- known base oils such as polyalkylene glycol, ester base fluid and fluorinated oil, and organic phosphate expressed in Formula (V) or (VI) may be used.
- organic phosphate may be prepared by known methods.
- tris(2-ethylhexyl)phosphate may be prepared by the reaction of 2-ethylhexanol and phosphorus oxychloride in the presence of dehydrohalogenating agent.
- base oils to be used together with the organic phosphate include known base oils such as polyalkylene glycol, ester base fluid and fluorinated oil, organic phosphonate expressed in Formula (I), and organic phosphate expressed in Formula (VI).
- the rate of the organic phosphate in the base oil must exceed 10 wt.%.
- the polyalkylene glycol is high in moisture absorption rate, and it may absorb more than 1.0% of moisture, which may adversely affect the stability of the lubricating oil composition for refrigerating machine. It is accordingly necessary to increase the content of the organic phosphate which does not absorb moisture so as to lower the moisture content of the entire composition, and hence the content of the organic phosphate is limited in a range exceeding 10 wt.%.
- the organic phosphate expressed in Formula (V) is blended by more than 10 wt.%, it is also effective to suppress the temperature of the sliding surface, which further contributes to decrease of decomposition of refrigerant (enhancement of stability).
- the content of the organic phosphate expressed in Formula (V) in the base oil is desired to be 0.01 wt.% or more, owing to the same reason as in the case of organic phosphonate.
- the upper limit of content of the organic phosphate is, in any case above, is 100 wt.% same as in the case of organic phosphonate mentioned above.
- organic phosphate may be prepared by known methods.
- tris[di(oxyethylene)-2-ethylhexyl]phosphate is prepared by the reaction of phosphorus oxychloride and dioxyethylene-2-ethylhexylether in the presence of dehydrohalogenating agent.
- the content of the organic phosphate in the base oil is, same as specified above, desired to be in a range of 0.01 to 100 wt.%.
- Other base oils to be used together with the organic phosphate may include known base oils such as polyalkylene glycol, ester base fluid and fluorinated oil, organic phosphonate expressed in Formula (I), and organic phosphate expressed in Formula (V).
- polyalkylene glycol to be used together with any one of the organic phosphonate expressed in Formula (I), the organic phosphate expressed in Formula (V), and the organic phosphate expressed in Formula (VI), various known polyalkylene glycols may be used, and in particular, the compound expressed in Formula (XI) is desired.
- EO denotes an oxyethylene group
- PO is an oxypropylene group
- m and n are 0 or integers of 1 or more, but m and n are not 0 at the same time; if m and n are both integers of 1 or more, the oxyethylene group and oxypropylene group may be bonded either at random or in block; the ratio of m and m, m/n, is desired to be 1 or less; and p is an integer of 1 to 4.
- A1 is any one of the following:
- A1 represents a residue by removing hydroxy group from dihydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic dihydroxy compound, unsaturated aliphatic dihydroxy compound, or aromatic dihydroxy compound is preferably used, such as ethylene glycol and propylene glycol.
- A1 represents a residue by removing hydroxy group from trihydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic trihydroxy compound, unsaturated aliphatic trihydroxy compound, or aromatic trihydroxy compound is preferably used, such as gylcerin and trimethylolpropane.
- A1 represents a residue by removing hydroxy group from tetrahydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic tetrahydroxy compound, or unsaturated aliphatic tetrahydroxy compound is preferably used, such as pentaerythritol.
- A2 represents one of the following:
- the kinematic viscosity at 40 deg. C of polyalkylene glycol expressed in Formula (XI) is desired to be in a range of 5 to 300 cSt. If the kinematic viscosity is less than 5 cSt, the lubricating performance as the base oil including anti-wear property is not sufficient, and if exceeding 300 cSt, the solubility may be inferior. More preferably, the kinematic viscosity of polyalkylene glycol at 40 deg. C should be in a range of 15 to 150 cSt.
- polyalkylene glycol expressed in Formula (XI) may include compounds expressed in Formula (XIII), of which kinematic viscosity at 40 deg. C is 32 cSt. where m and n are integers of which ratio m/n is 0.6
- ester base fluid used together with the base oil
- various hitherto known ester base fluids may be used, and in particular the oils expressed in Formula (XIV) are used preferably.
- A4 represents any one of the following:
- A4 represents a residue by removing hydroxy group from dihydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic dihydroxy compound, unsaturated aliphatic dihydroxy compound, or aromatic dihydroxy compound is preferably used, such as ethylene glycol and propylene glycol.
- A4 represents a residue by removing hydroxy group from trihydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic trihydroxy compound, unsaturated aliphatic trihydroxy compound, or aromatic trihydroxy compound is preferably used, such as gylcerin and trimethylolpropane.
- A4 represents a residue by removing hydroxy group from tetrahydroxy compound.
- a residue by removing hydroxy group from saturated aliphatic tetrahydroxy compound, or unsaturated aliphatic tetrahydroxy compound is preferably used, such as pentaerythritol.
- alkyl group or alkenyl group not possessing hydrogen in ⁇ -carbon is desired.
- A5 represents one of the following:
- ester base fluid expressed in Formula (XIV) include, among others, octyl oleate, trimethylol propane triheptanoate, and pentaerythritol tetraoctanoate.
- diester dicorboxylate expressed in Formula (XV) may be used.
- the dicarboxylic acid as the material for the diester dicarboxylate may include, for example, succinic acid, adipic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, tetradecanoic diacid, and hexadecanoic diacid, and practical examples of ester base fluid expressed in Formula (XV) include, among others, 1,9-azelaic dioctyl ester, 1,14-tetradecanoic dioctyl ester, and 1,16-hexadecanoic dioctyl ester.
- the carbonate ester expressed in Formula (XVI) may be known, for example.
- R18, R20 are identical or different, representing alkyl group with 1 to 18 carbon atoms, alkenyl group with 3 to 18 carbon atoms, or aryl group with 6 to 18 carbon atoms (which may possess either alkyl group with 1 to 12 carbon atoms or alkenyl group with 2 to 12 carbon atoms as a substituent)
- R19 represents an alkylene group with 2 to 4 carbon atoms
- r is 0 or an integer of 1 or more.
- carbonate ester includes a compound of which kinematic viscosity at 40 deg. C is 32 cSt as expressed-in Formula (XVIa): where C4H9 is an n-buty group.
- the ester base fluid explained herein is desired to have the kinematic viscosity at 40 deg. C in a range of 5 to 300 cSt, especially in a range of 15 to 60 cSt, considering its use in refrigerating machine.
- the fluorinated oil used together with the base oil includes various known fluorinated oils, and in particular the compound in Formula (XVII) is desired.
- A8 - [O - (C s F 2s ) t - C u F 2u -OA9] v (XVII) where A8 denotes a perfluoroalkyl group with 1 to 12 carbon atoms, A9 represents a perfluoroalkyl group with 1 to 4 carbon atoms or an acyl group expressed in Formula (XVIII), s is an integer of 1 to 4, t is an integer of 1 or more, and u and v are either identical or different, representing integers of 1 to 3.
- a practical example of such fluorinated oil includes a compound expressed in Formula (XIX).
- fluorinated oil consisting of a constituent unit expressed in Formula (XX).
- XX the fluorinated oil consisting of a constituent unit expressed in Formula (XX).
- the acid value of the lubricating oil composition for refrigerating machine is too high, the stability is lowered, which may induce corrosion of metal and adverse effects on anti-wear property Therefore, the acid value should be as low as possible, and in particular it is desired to be 0.01 [mg KOH/g] or less.
- aromatic phosphate or the like is used as extreme-pressure agent, but when its content increases, it may adversely affect the stability.
- the content of the organic phosphorus compound expressed in Formula (I), (V) or (VI) is increased, the anti-wear property is enhanced without impairing the stability.
- the ordinary additive added conventionally to the lubricating oil composition may be added by the conventional blending rate.
- Such additives may include, for example, an epoxy compounds for stabilizing the lubricating oil composition.
- an epoxy compounds for stabilizing the lubricating oil composition are, among others, condensate of polyalkylene glycol and epichlorohydrine, condensate of phenol and glycidyl alcohol, and epoxy fatty ester.
- the epoxy compounds are usually blended to the base oil in a range of 0.1 to 10 wt.%. If the content of the epoxy compounds are less than the specified range, the effect of adding the epoxy compounds are insufficient, or, to the contrary, if the blending of the epoxy compounds are more than the range, it may be harmful for the antiwear property of the lubricating oil composition.
- additives than the stabilizer may include antioxidant of phenol and amine compounds, oilness of sulfur compounds, metal deactivator of benzotriazole compounds.
- the lubricating oil composition for refrigerating machine of the invention is prepared by adding, as required, polyalkylene glycol, ester base fluid, fluorinated oil, or other base oils, and various additives to the organic phosphonate expressed in Formula (I), organic phosphate expressed in Formula (V), or organic phosphate expressed in Formula (VI), and agitating and dissolving at room temperature to 80 deg. C, or preferably, room temperature to 40 deg. C.
- the lubricating oil composition for refrigerating machine of the invention is preferably used in the refrigerating machine such as refrigerator, car cooler, freezer, and refrigerated display case incorporating a compressor of rotary type, reciprocating type, centrifugal type or the like.
- P Polyalkylene glycol expressed in Formula (XIII), of which kinematic viscosity at 40 deg. C is 32 cSt. where m and n are integers of which ratio m/n is 0.6.
- V Organic phosphate of which R8, R9, R10 are commonly 2-ethylhexyl groups.
- the aromatic phosphate expressed below was blended with polyalkylene glycol as base oil expressed in Formula (XIII), and dissolved uniformly to prepare the lubricating oil composition for refrigerating machine of Comparative Example 4.
- the blending rate of aromatic phosphate in the base oil was 1.0 wt.%.
- the compound expressed below was blended with pentaerythritol tetraoctanoate as base oil, and dissolved uniformly to prepare the lubricating oil composition for refrigerating machine of Comparative Example 6.
- the blending rate of the compound in the base oil was 1.0 wt.%. (C18H350)2P(O)H
- the phosphate expressed below was blended with pentaerythritol tetraoctanoate as base oil, and dissolved uniformly to prepare the lubricating oil composition for refrigerating machine of Comparative Example 7.
- the compound expressed below was blended with pentaerythritol tetraoctanoate as base oil, and dissolved uniformly to prepare the lubricating oil composition for refrigerating machine of Comparative Example 8.
- the blending rate of-the compound in the base oil was 1.0 wt.%. (C18H350)3-P
- the lubricating oil compositions for refrigerating machines of the Examples and Comparative Examples were dissolved in HFC-134a as refrigerant at the blending rates of 3 wt.%, 10 wt.%, 50 wt.% as calculated in the formula below.
- the solution was poured in a glass tube which was sealed tightly, and cooled to -50 deg. C, and presence or absence of separation of solution was observed. It was evaluated as O if not separated at -50 deg. C, and X if separated before reaching -50 deg. C.
- Blend (wt.%) X (g) X (g) + Y (g) X100 where
- the lubricating oil compositions for refrigerating machine of Examples 1 to 40 were all found to be excellent in anti-wear property, solubility, and stability.
- organic phosphonate of which R1 to R3 in Formula (I) are commonly 2-ethylhexyl groups, and polyalkylene glycol expressed in Formula (XIII) as base oil were blended so that the blending rate of the organic phosphonate in the base oil might be as shown in Table 6, and dissolved uniformly to prepare lubricating oil compositions for refrigerating machine of Examples 41 to 49.
- the organic phosphonate of which R1 to R3 in Formula (I) are commonly 2-ethylhexyl groups was blended with the base oil shown in Table 9, and dissolved uniformly to prepare lubricating oil compositions for refrigerating machine of Examples 66 to 76.
- the blending rate of organic phosphonate in the base oil was 1.0 wt.%.
- the symbols represent the following compounds respectively.
- P1/E1 (99/1) Mixed base oil of 99 parts by weight of polyalkylene glycol of P1 and 1 part by weight of pentaerythritol tetraoctanoate of E1
- P1/E1 (1/99) Mixed base oil of 1 part by weight of polyalkylene glycol of P1 and 99 parts by weight of pentaerythritol tetraoctanoate of E1
- compositions of Examples 77 to 99 were excellent in all of anti-wear property, solubility, and stability.
- the polyalkylene glycol expressed in Formula (XIII) was used as the base oil at the moisture content of 1.0% without dehumidifying to 0.3% of moisture content as used in the foregoing Examples and Comparative Examples, and this base oil was blended with the organic phosphate of which R1 to R3 in Formula (V) are commonly 2-ethylhexyl groups at the blending rate of the organic phosphate in the base oil as shown in Table 12, and dissolved uniformly to prepare the lubricating oil compositions for refrigerating machine of Examples 100 to 102, and Comparative Example 11. Without adding organic phosphate, Comparative Example 10 was prepared.
- the organic phosphate of which R1 to R3 in Formula (V) are commonly 2-ethylhexyl groups was blended with the base oil shown in Table 15, and dissolved uniformly to prepare the lubricating oil compositions for refrigerating machine of Examples 121 to 128.
- the blending rate of the organic phosphate in the base oil was 1.0 wt.%.
- the symbols in the base oil column in the table represent the same compounds as specified above.
- compositions of Examples 141 to 183 were excellent in anti-wear property, solubility and stability.
- organic phosphate of which the first to the third substituents in Formula (VI) are commonly the group of symbol (8) above, and the polyalkylene glycol expressed in Formula (XIII) as base oil were blended so that the blending rate of the organic phosphate in the base oil might be as shown in Table 22, and dissolved uniformly, and the lubricating oil compositions for refrigerating machine of Examples 184 to 193 were prepared.
- the organic phosphate of which the first to the third substituents in Formula (VI) are commonly the group of symbol (8) above was blended with the base oil in Table 25, and dissolved uniformly to prepare the lubricating oil compositions for refrigerating machine of Examples 212 to 222.
- the blending rate of organic phosphate in the base oil was 1.0 wt.%.
- the symbols in the base oil column in the table denote the same compounds as specified above.
- the organic phosphorus compounds and base oil shown in Table 26 were blended so that the blending rate of the organic phosphorus compound in the base oil might be 10 wt.%, and dissolved uniformly, and the sample compositions of which total acid value is 0.00[mg KOH/g] were prepared.
- the lubricating oil compositions for refrigerating machine of Examples 223 to 230 and Comparative Examples 12 to 14 adjusted the total acid value as shown in the table were prepared.
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Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9386691 | 1991-04-24 | ||
| JP93866/91 | 1991-04-24 | ||
| JP174181/91 | 1991-07-15 | ||
| JP17418191 | 1991-07-15 | ||
| JP253855/91 | 1991-10-01 | ||
| JP25385591 | 1991-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0510633A1 true EP0510633A1 (de) | 1992-10-28 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92106937A Withdrawn EP0510633A1 (de) | 1991-04-24 | 1992-04-23 | Schmierölzusammensetzung und ihre Verwendung |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0571091A1 (de) * | 1992-04-29 | 1993-11-24 | The Lubrizol Corporation | Carbonsaüreester enthaltende flüssige Zusammensetzungen |
| EP0640681A1 (de) * | 1992-04-28 | 1995-03-01 | Tonen Corporation | Schmierölzusammensetzung |
| WO1996036682A1 (en) * | 1995-05-18 | 1996-11-21 | Castrol Limited | Lubricating compositions |
| EP1312663A4 (de) * | 2000-07-26 | 2006-07-12 | Idemitsu Kosan Co | Schmieröl für kältemaschine und dieses enthaltende hydraulikflüssigkeit |
| WO2016071231A1 (en) * | 2014-11-04 | 2016-05-12 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
| CN105829511A (zh) * | 2013-11-01 | 2016-08-03 | 捷客斯能源株式会社 | 润滑油组合物 |
| CN109072114A (zh) * | 2016-07-28 | 2018-12-21 | Jxtg能源株式会社 | 冷冻机油 |
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| US4857215A (en) * | 1986-03-25 | 1989-08-15 | Wong John L | Semi-fluid lubricant for extreme climates |
| WO1990009387A1 (en) * | 1989-02-09 | 1990-08-23 | The Lubrizol Corporation | Carboxylic esters, liquid compositions containing said carboxylic esters and methods of lubricating metal parts |
| EP0384724A1 (de) * | 1989-02-22 | 1990-08-29 | Nippon Oil Co. Ltd. | Schmierverfahren für Kühlvorrichtungen |
| EP0435253A1 (de) * | 1989-12-28 | 1991-07-03 | Nippon Oil Company, Limited | Kühlschranköle zum Gebrauch mit Hydrogen enthaltenden Halogenocarbonkühlmitteln |
| WO1991018073A1 (en) * | 1990-05-17 | 1991-11-28 | The Lubrizol Corporation | Phosphorus-containing compositions for refrigeration systems |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0640681A1 (de) * | 1992-04-28 | 1995-03-01 | Tonen Corporation | Schmierölzusammensetzung |
| US5514292A (en) * | 1992-04-28 | 1996-05-07 | Tonen Corporation | Lubricating oil composition |
| EP0571091A1 (de) * | 1992-04-29 | 1993-11-24 | The Lubrizol Corporation | Carbonsaüreester enthaltende flüssige Zusammensetzungen |
| WO1996036682A1 (en) * | 1995-05-18 | 1996-11-21 | Castrol Limited | Lubricating compositions |
| US5824628A (en) * | 1995-05-18 | 1998-10-20 | Castrol Limited | Lubricating compositions |
| EP1312663A4 (de) * | 2000-07-26 | 2006-07-12 | Idemitsu Kosan Co | Schmieröl für kältemaschine und dieses enthaltende hydraulikflüssigkeit |
| EP2284249A3 (de) * | 2000-07-26 | 2011-05-18 | Idemitsu Kosan Co., Ltd. | Schmieröl für eine Kühlanlage und Kühlmittelzusammensetzung dafür dieses enthaltend |
| US8648022B2 (en) | 2000-07-26 | 2014-02-11 | Idemitsu Kosan Co., Ltd. | Lubricating oil for refrigerator and hydraulic fluid composition for refrigerator using the same |
| CN105829511B (zh) * | 2013-11-01 | 2019-05-07 | 捷客斯能源株式会社 | 润滑油组合物 |
| CN105829511A (zh) * | 2013-11-01 | 2016-08-03 | 捷客斯能源株式会社 | 润滑油组合物 |
| CN107148463A (zh) * | 2014-11-04 | 2017-09-08 | 国际壳牌研究有限公司 | 润滑组合物 |
| WO2016071231A1 (en) * | 2014-11-04 | 2016-05-12 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
| RU2704028C2 (ru) * | 2014-11-04 | 2019-10-23 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Смазывающая композиция |
| US10913916B2 (en) | 2014-11-04 | 2021-02-09 | Shell Oil Company | Lubricating composition |
| CN109072114A (zh) * | 2016-07-28 | 2018-12-21 | Jxtg能源株式会社 | 冷冻机油 |
| EP3492563A4 (de) * | 2016-07-28 | 2019-07-31 | JXTG Nippon Oil & Energy Corporation | Kühlmaschinenöl |
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