JP6511068B2 - Refrigeration oil - Google Patents
Refrigeration oil Download PDFInfo
- Publication number
- JP6511068B2 JP6511068B2 JP2016555211A JP2016555211A JP6511068B2 JP 6511068 B2 JP6511068 B2 JP 6511068B2 JP 2016555211 A JP2016555211 A JP 2016555211A JP 2016555211 A JP2016555211 A JP 2016555211A JP 6511068 B2 JP6511068 B2 JP 6511068B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- mass
- compound
- epoxy
- epoxy compound
- 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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- 238000005057 refrigeration Methods 0.000 title description 18
- 150000001875 compounds Chemical class 0.000 claims description 75
- 239000003921 oil Substances 0.000 claims description 66
- 235000019198 oils Nutrition 0.000 claims description 66
- 239000004593 Epoxy Substances 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 26
- 229930195729 fatty acid Natural products 0.000 claims description 26
- 239000000194 fatty acid Substances 0.000 claims description 26
- 239000003507 refrigerant Substances 0.000 claims description 25
- -1 glycidyl ester Chemical class 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 17
- 239000002199 base oil Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- 239000008158 vegetable oil Substances 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 239000010726 refrigerant oil Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 description 26
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000010687 lubricating oil Substances 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 2
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 2
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 2
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-SYDPRGILSA-N (1s,5r)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC[C@H]2O[C@H]21 GJEZBVHHZQAEDB-SYDPRGILSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- CUXYLFPMQMFGPL-BGDVVUGTSA-N (9Z,11E,13Z)-octadecatrienoic acid Chemical compound CCCC\C=C/C=C/C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-BGDVVUGTSA-N 0.000 description 1
- FFTOUVYEKNGDCM-OWOJBTEDSA-N (e)-1,3,3-trifluoroprop-1-ene Chemical compound F\C=C\C(F)F FFTOUVYEKNGDCM-OWOJBTEDSA-N 0.000 description 1
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 description 1
- ZUAQTIHDWIHCSV-UPHRSURJSA-N (z)-1,2,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)F ZUAQTIHDWIHCSV-UPHRSURJSA-N 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 description 1
- ZCZCZLVSKGCRTD-UHFFFAOYSA-N 2-(tridecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCOCC1CO1 ZCZCZLVSKGCRTD-UHFFFAOYSA-N 0.000 description 1
- HNJSJLKMMRCGKX-UHFFFAOYSA-N 2-(undecoxymethyl)oxirane Chemical compound CCCCCCCCCCCOCC1CO1 HNJSJLKMMRCGKX-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- WAPRZVXVTPSWEB-UHFFFAOYSA-N 2-[(2-butan-2-ylphenoxy)methyl]oxirane Chemical compound CCC(C)C1=CC=CC=C1OCC1OC1 WAPRZVXVTPSWEB-UHFFFAOYSA-N 0.000 description 1
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical compound CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- RRXIBRLPSOBLIQ-UHFFFAOYSA-N 2-[(2-decylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCC1=CC=CC=C1OCC1OC1 RRXIBRLPSOBLIQ-UHFFFAOYSA-N 0.000 description 1
- ABTAANTUIVCOTF-UHFFFAOYSA-N 2-[(2-heptylphenoxy)methyl]oxirane Chemical compound CCCCCCCC1=CC=CC=C1OCC1OC1 ABTAANTUIVCOTF-UHFFFAOYSA-N 0.000 description 1
- LEYWCVIABUVRSU-UHFFFAOYSA-N 2-[(2-hexylphenoxy)methyl]oxirane Chemical compound CCCCCCC1=CC=CC=C1OCC1OC1 LEYWCVIABUVRSU-UHFFFAOYSA-N 0.000 description 1
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 description 1
- MVGLGWVANWQXLJ-UHFFFAOYSA-N 2-[(2-octylphenoxy)methyl]oxirane Chemical compound CCCCCCCCC1=CC=CC=C1OCC1OC1 MVGLGWVANWQXLJ-UHFFFAOYSA-N 0.000 description 1
- UYBCNHLHWUHLOF-UHFFFAOYSA-N 2-[(2-pentylphenoxy)methyl]oxirane Chemical compound CCCCCC1=CC=CC=C1OCC1OC1 UYBCNHLHWUHLOF-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- YXLHBXPGRDAQSH-UHFFFAOYSA-N 2-ethylhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(CC)C(O)=O YXLHBXPGRDAQSH-UHFFFAOYSA-N 0.000 description 1
- CEUXMUYHMURJFZ-UHFFFAOYSA-N 2-heptadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1CO1 CEUXMUYHMURJFZ-UHFFFAOYSA-N 0.000 description 1
- GXOYTMXAKFMIRK-UHFFFAOYSA-N 2-heptyloxirane Chemical compound CCCCCCCC1CO1 GXOYTMXAKFMIRK-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- LXVAZSIZYQIZCR-UHFFFAOYSA-N 2-nonyloxirane Chemical compound CCCCCCCCCC1CO1 LXVAZSIZYQIZCR-UHFFFAOYSA-N 0.000 description 1
- BHZBVWCLMYQFQX-UHFFFAOYSA-N 2-octadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCCC1CO1 BHZBVWCLMYQFQX-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
- ZKAPVLMBPUYKKP-UHFFFAOYSA-N 2-undecyloxirane Chemical compound CCCCCCCCCCCC1CO1 ZKAPVLMBPUYKKP-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- WRQOPPZJPSGEDO-UHFFFAOYSA-N 5-oxabicyclo[4.1.0]heptane Chemical compound C1CCOC2CC21 WRQOPPZJPSGEDO-UHFFFAOYSA-N 0.000 description 1
- QLUXGAQOXHOFIO-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C=C)C1O2 QLUXGAQOXHOFIO-UHFFFAOYSA-N 0.000 description 1
- XOIZUVFIXICDDB-UHFFFAOYSA-N 6-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2(C)CC1C1(C)CO1 XOIZUVFIXICDDB-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- VDDYWOTYVYUCQA-UHFFFAOYSA-N C.F.F.F.I Chemical compound C.F.F.F.I VDDYWOTYVYUCQA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
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- 239000005977 Ethylene Substances 0.000 description 1
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- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- OHNNZOOGWXZCPZ-UHFFFAOYSA-N exo-norbornene oxide Chemical compound C1CC2C3OC3C1C2 OHNNZOOGWXZCPZ-UHFFFAOYSA-N 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-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
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- CUXYLFPMQMFGPL-UYWAGRGNSA-N trichosanic acid Natural products CCCCC=C/C=C/C=CCCCCCCCC(=O)O CUXYLFPMQMFGPL-UYWAGRGNSA-N 0.000 description 1
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/18—Epoxides
-
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
本発明は、冷凍機油に関する。 The present invention relates to refrigeration oil.
一般的に、摺動部等の機械要素における潤滑性を確保するために潤滑油が用いられる。そして、潤滑油は、鉱油、合成油などの基油と、所望の特性に応じて基油に添加される添加剤とを含有している。かかる添加剤としては、例えば、摺動部の摩耗防止を目的とする摩耗防止剤が用いられる。 In general, lubricating oil is used to ensure lubricity in mechanical elements such as sliding parts. The lubricating oil then contains a base oil, such as a mineral oil, a synthetic oil, etc., and an additive that is added to the base oil according to the desired properties. As such an additive, for example, an antiwear agent for preventing wear of the sliding portion is used.
ところで、潤滑油にはその用途に応じて特有の性能が要求されることがあるため、潤滑油の用途によって使用可能な添加剤の種類が異なる。例えば特許文献1に記載されているように、冷凍機用の潤滑油(冷凍機油)においては、冷凍機油への摩耗防止剤等の添加は、条件によってはキャピラリー閉塞などの問題を引き起こす原因となる。したがって、冷凍機油の分野においては、他の用途の潤滑油と比べて摩耗防止剤の選択の自由度が極めて小さく、潤滑性(耐摩耗性)と安定性とを両立するために、トリクレジルホスフェート等のリン酸エステルなどを摩耗防止剤として用いるのが一般的である(特許文献1参照)。 By the way, since the lubricating oil may be required to have specific performance depending on its application, the types of usable additives differ depending on the application of the lubricating oil. For example, as described in Patent Document 1, in lubricating oil for refrigerator (refrigerant oil), addition of anti-wear agent to refrigerator oil may cause problems such as capillary block depending on conditions. . Therefore, in the field of refrigeration oil, the degree of freedom in selecting the anti-wear agent is extremely small as compared with lubricating oils for other applications, and Tricresyl is used in order to achieve both lubricity (abrasion resistance) and stability. It is common to use phosphate esters such as phosphate as an antiwear agent (see Patent Document 1).
本発明は、耐摩耗性と安定性とを高水準で両立することが可能な冷凍機油を提供することを目的とする。 An object of the present invention is to provide a refrigerator oil capable of achieving both wear resistance and stability at a high level.
本発明は、基油と、下記一般式(1)で表される化合物と、エポキシ化合物と、を含有する冷凍機油を提供する。
本発明者らは、当技術分野において一般的に用いられるトリクレジルホスフェート等のリン酸エステルよりも活性が高い(すなわち冷凍機油の安定性を阻害しやすい)摩耗防止剤を敢えて用いた冷凍機油の検討を行ったところ、上記一般式(1)で表される化合物とエポキシ化合物とを組み合わせて冷凍機油に用いた場合に、耐摩耗性と安定性とを高水準で両立することが可能になることを見出し、本発明を完成するに至った。 The present inventors have used a refrigerator oil intentionally using an antiwear agent that is more active than phosphate esters such as tricresyl phosphate generally used in the art (that is, tends to inhibit the stability of the refrigerator oil). In the case where a compound represented by the above general formula (1) and an epoxy compound were combined and used as a refrigerator oil, it was possible to achieve both abrasion resistance and stability at a high level. The present invention has been completed.
一般式(1)で表される化合物及びエポキシ化合物は、下記式(2)で表される条件を満たすことが好ましい。
本発明によれば、耐摩耗性と安定性とを高水準で両立することが可能な冷凍機油を提供することができる。 According to the present invention, it is possible to provide a refrigerator oil capable of achieving both wear resistance and stability at a high level.
本実施形態に係る冷凍機油は、基油と、下記一般式(1)で表される化合物と、エポキシ化合物と、を含有する。
基油としては、炭化水素油、含酸素油などを用いることができる。炭化水素油としては、鉱油系炭化水素油、合成系炭化水素油が例示される。含酸素油としては、エステル、ポリビニルエーテル、ポリアルキレングリコール、カーボネート、ケトン、ポリフェニルエーテル、シリコーン、ポリシロキサン、パーフルオロエーテルが例示される。基油は、含酸素油を含有することが好ましく、エステルを含有することがより好ましい。 As the base oil, hydrocarbon oil, oxygen-containing oil and the like can be used. As a hydrocarbon oil, mineral oil type hydrocarbon oil and synthetic type hydrocarbon oil are illustrated. Examples of oxygen-containing oils include esters, polyvinyl ethers, polyalkylene glycols, carbonates, ketones, polyphenyl ethers, silicones, polysiloxanes, and perfluoroethers. The base oil preferably contains an oxygen-containing oil, and more preferably contains an ester.
鉱油系炭化水素油は、パラフィン系、ナフテン系などの原油を常圧蒸留及び減圧蒸留して得られた潤滑油留分を、溶剤脱れき、溶剤精製、水素化精製、水素化分解、溶剤脱ろう、水素化脱ろう、白土処理、硫酸洗浄などの方法で精製することによって得ることができる。これらの精製方法は、1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。 Mineral oil-based hydrocarbon oils are solvent-depleted, solvent-refined, hydrorefined, hydrocracked, solvent-degraded, and lubricating oil fractions obtained by atmospheric distillation and vacuum distillation of crude oils such as paraffinic and naphthenic crude oils. It can be obtained by purification by methods such as wax, hydrodewaxing, clay treatment, sulfuric acid washing and the like. These purification methods may be used alone or in combination of two or more.
合成系炭化水素油としては、アルキルベンゼン、アルキルナフタレン、ポリα−オレフィン(PAO)、ポリブテン、エチレン−α−オレフィン共重合体などが挙げられる。 Examples of synthetic hydrocarbon oils include alkylbenzenes, alkylnaphthalenes, poly α-olefins (PAO), polybutenes, ethylene-α-olefin copolymers, and the like.
エステルとしては、芳香族エステル、二塩基酸エステル、ポリオールエステル、コンプレックスエステル、炭酸エステル及びこれらの混合物などが例示される。エステルとしては、ポリオールエステルが好ましい。 Examples of the ester include aromatic esters, dibasic acid esters, polyol esters, complex esters, carbonic esters and mixtures thereof. As ester, polyol ester is preferable.
ポリオールエステルは、多価アルコールと脂肪酸とのエステルである。脂肪酸としては、飽和脂肪酸が好ましく用いられる。脂肪酸の炭素数は、4〜20であることが好ましく、4〜18であることがより好ましく、4〜9であることが更に好ましく、5〜9であることが特に好ましい。ポリオールエステルは、多価アルコールの水酸基の一部がエステル化されずに水酸基のまま残っている部分エステルであってもよく、全ての水酸基がエステル化された完全エステルであってもよく、また部分エステルと完全エステルとの混合物であってもよい。ポリオールエステルの水酸基価は、好ましくは10mgKOH/g以下、より好ましくは5mgKOH/g以下、更に好ましくは3mgKOH/g以下である。 The polyol ester is an ester of a polyhydric alcohol and a fatty acid. As fatty acid, saturated fatty acid is preferably used. The carbon number of the fatty acid is preferably 4 to 20, more preferably 4 to 18, still more preferably 4 to 9, and particularly preferably 5 to 9. The polyol ester may be a partial ester in which a part of hydroxyl groups of polyhydric alcohol is not esterified and remains as a hydroxyl group, or may be a complete ester in which all the hydroxyl groups are esterified, or a partial ester It may be a mixture of an ester and a complete ester. The hydroxyl value of the polyol ester is preferably 10 mg KOH / g or less, more preferably 5 mg KOH / g or less, and still more preferably 3 mg KOH / g or less.
ポリオールエステルを構成する脂肪酸のうち、炭素数4〜20の脂肪酸の割合が20〜100モル%であることが好ましく、50〜100モル%であることがより好ましく、70〜100モル%であることが更に好ましく、90〜100モル%であることが特に好ましい。 It is preferable that the ratio of a C4-C20 fatty acid is 20-100 mol% among fatty acids which comprise polyol ester, it is more preferable that it is 50-100 mol%, and it is 70-100 mol%. Is more preferable, and 90 to 100 mol% is particularly preferable.
炭素数4〜20の脂肪酸としては、具体的には、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、ウンデカン酸、ドデカン酸、トリデカン酸、テトラデカン酸、ペンタデカン酸、ヘキサデカン酸、ヘプタデカン酸、オクタデカン酸、ノナデカン酸、イコサン酸が挙げられる。これらの脂肪酸は、直鎖状であっても分岐状であってもよい。さらに具体的には、α位及び/又はβ位に分岐を有する脂肪酸が好ましく、2−メチルプロパン酸、2−メチルブタン酸、2−メチルペンタン酸、2−メチルヘキサン酸、2−エチルペンタン酸、2−メチルヘプタン酸、2−エチルヘキサン酸、3,5,5−トリメチルヘキサン酸、2−エチルヘキサデカン酸などがより好ましく、中でも2−エチルヘキサン酸、3,5,5−トリメチルヘキサン酸が更に好ましい。 Specifically as a C4-C20 fatty acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid And hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid and icosanic acid. These fatty acids may be linear or branched. More specifically, fatty acids having a branch at the α position and / or the β position are preferred, and 2-methylpropanoic acid, 2-methylbutanoic acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-Methylheptanoic acid, 2-ethylhexanoic acid, 3,5,5-trimethylhexanoic acid, 2-ethylhexadecanoic acid and the like are more preferable, and among them, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid are more preferable. preferable.
脂肪酸は、炭素数4〜20の脂肪酸以外の脂肪酸を含んでいてもよい。炭素数4〜20の脂肪酸以外の脂肪酸としては、例えば炭素数21〜24の脂肪酸であってよい。具体的には、ヘンイコ酸、ドコサン酸、トリコサン酸、テトラコサン酸等が挙げられる。これらの脂肪酸は、直鎖状であっても分岐状であってもよい。 The fatty acid may contain fatty acids other than fatty acids having 4 to 20 carbon atoms. As fatty acids other than a C4-C20 fatty acid, a C21-C24 fatty acid may be sufficient, for example. Specific examples thereof include henicoic acid, docosanoic acid, trichosanic acid and tetracosanoic acid. These fatty acids may be linear or branched.
ポリオールエステルを構成する多価アルコールとしては、2〜6個の水酸基を有する多価アルコールが好ましく用いられる。多価アルコールの炭素数としては、4〜12が好ましく、5〜10がより好ましい。具体的には、ネオペンチルグリコール、トリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、ジ−(トリメチロールプロパン)、トリ−(トリメチロールプロパン)、ペンタエリスリトール、ジペンタエリスリトールなどのヒンダードアルコールが好ましい。冷媒との相溶性及び加水分解安定性に特に優れることから、ペンタエリスリトール、又はペンタエリスリトールとジペンタエリスリトール)との混合エステルがより好ましい。 As a polyhydric alcohol which comprises polyol ester, the polyhydric alcohol which has a 2-6 hydroxyl group is used preferably. As a carbon number of polyhydric alcohol, 4-12 are preferable and 5-10 are more preferable. Specifically, hindered alcohols such as neopentyl glycol, trimethylol ethane, trimethylol propane, trimethylol butane, di- (trimethylol propane), tri- (trimethylol propane), pentaerythritol, and dipentaerythritol are preferable. . Pentaerythritol or a mixed ester of pentaerythritol and dipentaerythritol) is more preferable because it is particularly excellent in compatibility with a refrigerant and in hydrolysis stability.
基油の含有量は、冷凍機油全量基準で、好ましくは80質量%以上、より好ましくは90質量%以上、更に好ましくは95質量%以上である。 The content of the base oil is preferably 80% by mass or more, more preferably 90% by mass or more, still more preferably 95% by mass or more, based on the total amount of the refrigerator oil.
本実施形態に係る冷凍機油は、下記一般式(1)で表される化合物を含有する。
式(1)中、R1、R2、R3、R4、R5、R6、R7及びR8は、それぞれ独立に水素原子又は1価の炭化水素基を表す。当該炭化水素基としては、アルキル基が例示される。R1、R2、R3、R4、R5、R6、R7、R8で表される基における炭素数の合計は、例えば1以上、4以上、又は8以上とすることができ、例えば20以下、16以下、又は12以下とすることができる。R1、R2、R3、R4、R5、R6、R7、R8がそれぞれ1価の炭化水素基を表す場合、各炭化水素基の炭素数は、例えば1〜5とすることができる。In formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or a monovalent hydrocarbon group. An alkyl group is illustrated as the said hydrocarbon group. The total carbon number in the group represented by R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 can be, for example, 1 or more, 4 or more, or 8 or more. For example, it can be 20 or less, 16 or less, or 12 or less. When R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each represent a monovalent hydrocarbon group, the carbon number of each hydrocarbon group is, for example, 1 to 5 be able to.
式(1)中、Aは、1又は2以上の芳香環を有する2価の炭化水素基を表す。Aで表される2価の炭化水素基の炭素数は、例えば1以上、2以上、又は3以上とすることができ、例えば20以下、10以下、又は5以下とすることができる。Aで表される2価の炭化水素基としては、下記式(3)で表される基、下記式(4)で表される基、下記式(5)で表される基が例示される。式中、*印は結合手を表す。 In formula (1), A represents a bivalent hydrocarbon group having one or more aromatic rings. The carbon number of the divalent hydrocarbon group represented by A can be, for example, 1 or more, 2 or more, or 3 or more, and can be, for example, 20 or less, 10 or less, or 5 or less. Examples of the divalent hydrocarbon group represented by A include a group represented by the following formula (3), a group represented by the following formula (4), and a group represented by the following formula (5) . In the formula, the symbol * represents a bond.
式(1)で表される化合物の含有量は、潤滑性の向上の観点から、冷凍機油全量基準で、好ましくは0.05質量%以上、より好ましくは0.1質量%以上、更に好ましくは0.2質量%以上である。式(1)で表される化合物の含有量は、安定性の向上の観点から、冷凍機油全量基準で、好ましくは10質量%以下、より好ましくは8質量%以下、更に好ましくは5質量%以下である。式(1)で表される化合物の含有量は、潤滑性と安定性との両立の観点から、冷凍機油全量基準で、好ましくは、0.05〜10質量%、0.05〜8質量%、0.05〜5質量%、0.1〜10質量%、0.1〜8質量%、0.1〜5質量%、0.2〜10質量%、0.2〜8質量%、又は0.2〜5質量%である。 The content of the compound represented by the formula (1) is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, still more preferably from the viewpoint of improving the lubricity, based on the total amount of the refrigerator oil. It is 0.2 mass% or more. The content of the compound represented by the formula (1) is preferably 10% by mass or less, more preferably 8% by mass or less, still more preferably 5% by mass or less based on the total amount of the refrigerator oil from the viewpoint of improving stability. It is. The content of the compound represented by the formula (1) is preferably 0.05 to 10% by mass, 0.05 to 8% by mass, based on the total amount of refrigeration oil, from the viewpoint of achieving both lubricity and stability. , 0.05 to 5% by mass, 0.1 to 10% by mass, 0.1 to 8% by mass, 0.1 to 5% by mass, 0.2 to 10% by mass, 0.2 to 8% by mass, or It is 0.2-5 mass%.
本実施形態に係る冷凍機油は、エポキシ化合物を含有する。エポキシ化合物としては、グリシジルエーテル型エポキシ化合物、グリシジルエステル型エポキシ化合物、オキシラン化合物、アルキルオキシラン化合物、脂環式エポキシ化合物、エポキシ化脂肪酸モノエステル、エポキシ化植物油などが挙げられる。これらのエポキシ化合物は、1種を単独で、又は2種以上を組み合わせて用いることができる。 The refrigeration oil according to the present embodiment contains an epoxy compound. As an epoxy compound, a glycidyl ether type epoxy compound, a glycidyl ester type epoxy compound, an oxirane compound, an alkyl oxirane compound, an alicyclic epoxy compound, an epoxidized fatty acid monoester, an epoxidized vegetable oil etc. are mentioned. These epoxy compounds can be used individually by 1 type or in combination of 2 or more types.
グリシジルエーテル型エポキシ化合物としては、例えば下記一般式(6)で表されるアリールグリシジルエーテル型エポキシ化合物又はアルキルグリシジルエーテル型エポキシ化合物を用いることができる。
式(6)で表されるグリシジルエーテル型エポキシ化合物としては、n−ブチルフェニルグリシジルエーテル、i−ブチルフェニルグリシジルエーテル、sec−ブチルフェニルグリシジルエーテル、tert−ブチルフェニルグリシジルエーテル、ペンチルフェニルグリシジルエーテル、ヘキシルフェニルグリシジルエーテル、ヘプチルフェニルグリシジルエーテル、オクチルフェニルグリシジルエーテル、ノニルフェニルグリシジルエーテル、デシルフェニルグリシジルエーテル、デシルグリシジルエーテル、ウンデシルグリシジルエーテル、ドデシルグリシジルエーテル、トリデシルグリシジルエーテル、テトラデシルグリシジルエーテル、2−エチルヘキシルグリシジルエーテルが好ましい。 As a glycidyl ether type epoxy compound represented by Formula (6), n-butylphenyl glycidyl ether, i-butylphenyl glycidyl ether, sec-butylphenyl glycidyl ether, tert-butylphenyl glycidyl ether, pentylphenyl glycidyl ether, hexyl Phenyl glycidyl ether, heptyl phenyl glycidyl ether, octyl phenyl glycidyl ether, nonyl phenyl glycidyl ether, decyl phenyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, 2-ethylhexyl Glycidyl ether is preferred.
R11で表されるアルキル基の炭素数が5以上であると、エポキシ化合物の安定性が確保され、水分、脂肪酸、酸化劣化物と反応する前に分解したり、エポキシ化合物同士が重合する自己重合を起こしたりするのを抑制でき、目的の機能が得られやすくなる。一方、R11で表されるアルキル基の炭素数が18以下であると、冷媒との溶解性が良好に保たれ、冷凍装置内で析出して冷却不良などの不具合を生じにくくすることができる。When the carbon number of the alkyl group represented by R 11 is 5 or more, the stability of the epoxy compound is secured, and it is decomposed before reacting with moisture, fatty acid, and oxidatively degraded products, or self-polymerization where the epoxy compounds are polymerized. It is possible to suppress the occurrence of polymerization and to easily obtain the desired function. On the other hand, if the number of carbon atoms in the alkyl group represented by R 11 is a 18 or less, it is possible solubility with the refrigerant is maintained satisfactorily, and deposited in the refrigeration apparatus hardly occurs problems such as insufficient cooling .
グリシジルエーテル型エポキシ化合物として、式(6)で表されるエポキシ化合物以外に、ネオペンチルグリコールジグリシジルエーテル、トリメチロルプロパントリグリシジルエーテル、ペンタエリスリトールテトラグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、ソルビトールポリグリシジルエーテル、ポリアルキレングリコールモノグリシジルエーテル、ポリアルキレングリコールジグリシジルエーテルなどを用いることもできる。 As a glycidyl ether type epoxy compound, neopentyl glycol diglycidyl ether, trimetylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether in addition to the epoxy compound represented by the formula (6) Sorbitol polyglycidyl ether, polyalkylene glycol monoglycidyl ether, polyalkylene glycol diglycidyl ether and the like can also be used.
グリシジルエステル型エポキシ化合物としては、例えば下記一般式(7)で表されるものを用いることができる。
式(7)で表されるグリシジルエステル型エポキシ化合物としては、グリシジルベンゾエート、グリシジルネオデカノエート、グリシジル−2,2−ジメチルオクタノエート、グリシジルアクリレート、グリシジルメタクリレートが好ましい。 As a glycidyl ester type epoxy compound represented by Formula (7), glycidyl benzoate, glycidyl neodecanoate, glycidyl-2, 2- dimethyl octanoate, glycidyl acrylate, and glycidyl methacrylate are preferable.
R12で表されるアルキル基の炭素数が5以上であると、エポキシ化合物の安定性が確保され、水分、脂肪酸、酸化劣化物と反応する前に分解したり、エポキシ化合物同士が重合する自己重合を起こしたりするのを抑制でき、目的の機能が得られやすくなる。一方、R12で表されるアルキル基又はアルケニル基の炭素数が18以下であると、冷媒との溶解性が良好に保たれ、冷凍機内で析出して冷却不良などの不具合を生じにくくすることができる。When the carbon number of the alkyl group represented by R 12 is 5 or more, the stability of the epoxy compound is secured, and it is decomposed before reacting with water, fatty acid, and oxidatively degraded products, or the epoxy compounds are polymerized themselves It is possible to suppress the occurrence of polymerization and to easily obtain the desired function. On the other hand, if the carbon number of the alkyl group or alkenyl group represented by R 12 is 18 or less, the solubility with the refrigerant is well maintained, and precipitation in the refrigerator makes it difficult to cause problems such as cooling failure. Can.
脂環式エポキシ化合物は、下記一般式(8)で表される、エポキシ基を構成する炭素原子が直接脂環式環を構成している部分構造を有する化合物である。
脂環式エポキシ化合物としては、例えば、1,2−エポキシシクロヘキサン、1,2−エポキシシクロペンタン、3’,4’−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、エキソ−2,3−エポキシノルボルナン、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート、2−(7−オキサビシクロ[4.1.0]ヘプト−3−イル)−スピロ(1,3−ジオキサン−5,3’−[7]オキサビシクロ[4.1.0]ヘプタン、4−(1’−メチルエポキシエチル)−1,2−エポキシ−2−メチルシクロヘキサン、4−エポキシエチル−1,2−エポキシシクロヘキサンが好ましい。 Examples of alicyclic epoxy compounds include 1,2-epoxycyclohexane, 1,2-epoxycyclopentane, 3 ', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, bis (3,4-) Epoxycyclohexylmethyl) adipate, exo-2,3-epoxy norbornane, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 2- (7-oxabicyclo [4.1.0] hept-3-yl ) -Spiro (1,3-dioxane-5,3 '-[7] oxabicyclo [4.1.0] heptane, 4- (1'-methylepoxyethyl) -1,2-epoxy-2-methylcyclohexane 4-epoxyethyl-1,2-epoxycyclohexane is preferred.
アリルオキシラン化合物としては、1,2−エポキシスチレン、アルキル−1,2−エポキシスチレンなどが例示できる。 Examples of the allyl oxirane compound include 1,2-epoxystyrene, alkyl-1,2-epoxystyrene and the like.
アルキルオキシラン化合物としては、1,2−エポキシブタン、1,2−エポキシペンタン、1,2−エポキシヘキサン、1,2−エポキシヘプタン、1,2−エポキシオクタン、1,2−エポキシノナン、1,2−エポキシデカン、1,2−エポキシウンデカン、1,2−エポキシドデカン、1,2−エポキシトリデカン、1,2−エポキシテトラデカン、1,2−エポキシペンタデカン、1,2−エポキシヘキサデカン、1,2−エポキシヘプタデカン、1,2−エポキシオクタデカン、1,2−エポキシノナデカン、1,2−エポキシイコサンなどが例示できる。 As the alkyl oxirane compound, 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1, 2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1, Examples thereof include 2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxy nonadecane, and 1,2-epoxyicosane.
エポキシ化脂肪酸モノエステルとしては、エポキシ化された炭素数12〜20の脂肪酸と、炭素数1〜8のアルコール又はフェノールもしくはアルキルフェノールとのエステルなどが例示できる。エポキシ化脂肪酸モノエステルとしては、エポキシステアリン酸のブチル、ヘキシル、ベンジル、シクロヘキシル、メトキシエチル、オクチル、フェニルおよびブチルフェニルエステルが好ましく用いられる。 Examples of the epoxidized fatty acid monoester include esters of an epoxidized fatty acid having 12 to 20 carbon atoms and an alcohol having 1 to 8 carbon atoms or phenol or an alkylphenol. As epoxidized fatty acid monoesters, butyl, hexyl, benzyl, cyclohexyl, methoxyethyl, octyl, phenyl and butylphenyl esters of epoxystearic acid are preferably used.
エポキシ化植物油としては、大豆油、アマニ油、綿実油等の植物油のエポキシ化合物などが例示できる。 Examples of epoxidized vegetable oils include epoxy compounds of vegetable oils such as soybean oil, linseed oil and cottonseed oil.
エポキシ化合物の含有量は、安定性の向上の観点から、冷凍機油全量基準で、好ましくは0.1質量%以上、より好ましくは0.15質量%以上、更に好ましくは0.2質量%以上である。エポキシ化合物の含有量は、潤滑性の向上の観点から、冷凍機油全量基準で、好ましくは5.0質量%以下、より好ましくは3.0質量%以下、更に好ましくは2.0質量%以下である。エポキシ化合物の含有量は、潤滑性と安定性との両立の観点から、冷凍機油全量基準で、好ましくは、0.1〜5.0質量%、0.1〜3.0質量%、0.1〜2.0質量%、0.15〜5.0質量%、0.15〜3.0質量%、0.15〜2.0質量%、0.2〜5.0質量%、0.2〜3.0質量%、又は0.2〜2.0質量%である。 The content of the epoxy compound is preferably 0.1% by mass or more, more preferably 0.15% by mass or more, still more preferably 0.2% by mass or more, based on the total amount of the refrigerator oil, from the viewpoint of improving the stability. is there. The content of the epoxy compound is preferably 5.0% by mass or less, more preferably 3.0% by mass or less, still more preferably 2.0% by mass or less, based on the total amount of refrigeration oil, from the viewpoint of improving lubricity. is there. The content of the epoxy compound is preferably 0.1 to 5.0% by mass, 0.1 to 3.0% by mass, or 0.1% to 3.0% by mass, based on the total amount of the refrigerator oil, from the viewpoint of achieving both lubricity and stability. 1 to 2.0% by mass, 0.15 to 5.0% by mass, 0.15 to 3.0% by mass, 0.15 to 2.0% by mass, 0.2 to 5.0% by mass, 0. It is 2-3.0 mass%, or 0.2-2.0 mass%.
式(1)で表される化合物及びエポキシ化合物は、下記式(2)で表される条件を満たすことが好ましい。
式(2)中、NEはエポキシ化合物1分子当たりのエポキシ基の数を示し、MEはエポキシ化合物の分子量を示し、WEは冷凍機油全量基準でのエポキシ化合物の含有量(単位:質量%)を示し、NPは一般式(1)で表される化合物1分子当たりのリン原子の数を示し、MPは一般式(1)で表される化合物の分子量を示し、WPは冷凍機油全量基準での一般式(1)で表される化合物の含有量(単位:質量%)を示す。In Formula (2), N E indicates the number of epoxy groups per molecule of epoxy compound, M E indicates the molecular weight of the epoxy compound, and W E indicates the content of epoxy compound based on the total amount of refrigerator oil (unit: mass N P represents the number of phosphorus atoms per molecule of the compound represented by the general formula (1), M P represents the molecular weight of the compound represented by the general formula (1), and W P represents The content (unit: mass%) of the compound represented by General formula (1) on a refrigerator oil whole quantity basis is shown.
以下では、便宜的に式(2)の第二辺の項をE/Pとして(すなわち、E=(NE/ME)・WE、P=(NP/MP)・WPとして)説明する。E/Pは、好ましくは0.08以上、より好ましくは0.09以上、更に好ましくは0.10以上である。E/Pが0.08以上であることによって、冷凍機油の安定性を向上させることができる。E/Pは、好ましくは13以下、より好ましくは12以下、更に好ましくは11以下である。E/Pが13以下であることによって、冷凍機油の耐摩耗性を向上させることができる。E/Pは、安定性と耐摩耗性との両立の観点から、好ましくは、0.08〜13、0.08〜12、0.08〜11、0.09〜13、0.09〜12、0.09〜11、0.10〜13、0.10〜12、又は0.10〜11である。In the following, for convenience, the term of the second side of Formula (2) is E / P (that is, E = (N E / M E ) · W E , P = (N P / M P ) · W P )explain. E / P is preferably 0.08 or more, more preferably 0.09 or more, and still more preferably 0.10 or more. When E / P is 0.08 or more, the stability of the refrigerator oil can be improved. E / P is preferably 13 or less, more preferably 12 or less, and further preferably 11 or less. When the E / P is 13 or less, the abrasion resistance of the refrigerator oil can be improved. E / P is preferably 0.08 to 13, 0.08 to 12, 0.08 to 11, 0.09 to 13, 0.09 to 12 from the viewpoint of achieving both stability and wear resistance. , 0.09-11, 0.10-13, 0.10-12, or 0.10-11.
冷凍機油が複数種のエポキシ化合物を含有する場合には、各エポキシ化合物についてEi=(NE/ME)・WEを算出し、算出したEiすべての和をEとして式(2)に用いる。同様に、冷凍機油が複数種の式(1)で表される化合物を含有する場合には、各化合物についてPi=(NP/MP)・WPを算出し、算出したPiすべての和をPとして式(2)に用いる。When refrigeration oil contains multiple types of epoxy compounds, E i = (N E / M E ) · W E is calculated for each epoxy compound, and the sum of all the calculated E i is represented by E (2) Use for Similarly, in the case where the refrigeration oil contains a plurality of compounds represented by the formula (1), P i = (N P / M P ) · W P is calculated for each compound, and all calculated P i The sum of is used as P in equation (2).
冷凍機油は、式(1)で表される化合物及びエポキシ化合物に加えて、他の添加剤を更に含有していてもよい。他の添加剤としては、酸化防止剤、摩擦調整剤、式(1)で表される化合物以外の摩耗防止剤、極圧剤、防錆剤、金属不活性化剤などが例示される。 The refrigerator oil may further contain other additives in addition to the compound represented by the formula (1) and the epoxy compound. Examples of other additives include antioxidants, friction modifiers, antiwear agents other than compounds represented by the formula (1), extreme pressure agents, rust inhibitors, metal deactivators and the like.
冷凍機油の40℃における動粘度は、好ましくは3mm2/s以上、より好ましくは4mm2/s以上、更に好ましくは5mm2/s以上とすることができる。冷凍機油の40℃における動粘度は、好ましくは1000mm2/s以下、より好ましくは500mm2/s以下、更に好ましくは400mm2/s以下とすることができる。冷凍機油の100℃における動粘度は、好ましくは1mm2/s以上、より好ましくは2mm2/s以上とすることができる。冷凍機油の100℃における動粘度は、好ましくは100mm2/s以下、より好ましくは50mm2/s以下とすることができる。本発明における動粘度は、JIS K2283:2000に準拠して測定された動粘度を意味する。The kinematic viscosity at 40 ° C. of the refrigerator oil can be preferably 3 mm 2 / s or more, more preferably 4 mm 2 / s or more, and still more preferably 5 mm 2 / s or more. The kinematic viscosity at 40 ° C. of the refrigerator oil can be preferably 1000 mm 2 / s or less, more preferably 500 mm 2 / s or less, and still more preferably 400 mm 2 / s or less. The kinematic viscosity at 100 ° C. of the refrigerator oil can be preferably 1 mm 2 / s or more, more preferably 2 mm 2 / s or more. The kinematic viscosity at 100 ° C. of the refrigerator oil can be preferably 100 mm 2 / s or less, more preferably 50 mm 2 / s or less. The kinematic viscosity in the present invention means a kinematic viscosity measured in accordance with JIS K 2283: 2000.
冷凍機油の流動点は、好ましくは−10℃以下、より好ましくは−20℃以下とすることができる。本発明における流動点は、JIS K2269−1987に準拠して測定された流動点を意味する。 The pour point of the refrigerator oil can be preferably −10 ° C. or less, more preferably −20 ° C. or less. The pour point in the present invention means a pour point measured in accordance with JIS K 2269-1987.
冷凍機油の体積抵抗率は、好ましくは1.0×109Ω・m以上、より好ましくは1.0×1010Ω・m以上、更に好ましくは1.0×1011Ω・m以上とすることができる。特に、密閉型の冷凍機用に用いる場合には高い電気絶縁性であると好ましい。本発明における体積抵抗率は、JIS C2101:1999「電気絶縁油試験方法」に準拠して測定した25℃での体積抵抗率を意味する。The volume resistivity of the refrigeration oil is preferably 1.0 × 10 9 Ω · m or more, more preferably 1.0 × 10 10 Ω · m or more, still more preferably 1.0 × 10 11 Ω · m or more be able to. In particular, when it is used for a closed type refrigerator, it is preferable that it has high electrical insulation. The volume resistivity in the present invention means the volume resistivity at 25 ° C. measured in accordance with JIS C2101: 1999 “Electric Insulating Oil Testing Method”.
冷凍機油の水分含有量は、冷凍機油全量基準で、好ましくは200ppm以下、より好ましくは100ppm以下、更に好ましくは50ppm以下とすることができる。特に密閉型の冷凍機用に用いる場合には、冷凍機油の熱・化学的安定性や電気絶縁性への影響の観点から、水分含有量が少ないことが好ましい。 The water content of the refrigerator oil can be preferably 200 ppm or less, more preferably 100 ppm or less, still more preferably 50 ppm or less, based on the total amount of the refrigerator oil. In particular, when used for a closed type refrigerator, it is preferable that the water content be small from the viewpoint of the influence on the heat and chemical stability of the refrigerator oil and the electrical insulation.
冷凍機油の酸価は、冷凍機又は配管に用いられている金属への腐食を防止する観点から、好ましくは1.0mgKOH/g以下、より好ましくは0.1mgKOH/g以下とすることができる。本発明における酸価は、JIS K2501:2003「石油製品及び潤滑油−中和価試験方法」に準拠して測定された酸価を意味する。 The acid value of the refrigerator oil can be preferably 1.0 mg KOH / g or less, more preferably 0.1 mg KOH / g or less, from the viewpoint of preventing corrosion to metals used in the refrigerator or piping. The acid value in the present invention means an acid value measured in accordance with JIS K 2501: 2003 "Petroleum products and lubricants-Test method for neutralization number".
冷凍機油の灰分は、冷凍機油の熱・化学的安定性を高めスラッジ等の発生を抑制する観点から、好ましくは100ppm以下、より好ましくは50ppm以下とすることができる。本発明における灰分は、JIS K2272:1998「原油及び石油製品−灰分及び硫酸灰分試験方法」に準拠して測定された灰分を意味する。 The ash content of refrigeration oil is preferably 100 ppm or less, more preferably 50 ppm or less, from the viewpoint of enhancing the thermal and chemical stability of refrigeration oil and suppressing the generation of sludge and the like. The ash content in the present invention means ash content measured in accordance with JIS K 2272: 1998 "Crude oil and petroleum products-ash and sulfated ash content test method".
本実施形態に係る冷凍機油は、冷媒と共に用いられる。本実施形態に係る冷凍機用作動流体組成物は、本実施形態に係る冷凍機油と、冷媒とを含有する。かかる冷媒としては、飽和フッ化炭化水素冷媒、不飽和フッ化炭化水素冷媒、炭化水素冷媒、パーフルオロエーテル類等の含フッ素エーテル系冷媒、ビス(トリフルオロメチル)サルファイド冷媒、3フッ化ヨウ化メタン冷媒、及び、アンモニア、二酸化炭素等の自然系冷媒が例示される。 The refrigeration oil according to the present embodiment is used together with a refrigerant. The working fluid composition for a refrigerator according to the present embodiment contains the refrigerator oil according to the present embodiment and a refrigerant. As such refrigerants, saturated fluorinated hydrocarbon refrigerants, unsaturated fluorinated hydrocarbon refrigerants, hydrocarbon refrigerants, fluorine-containing ether refrigerants such as perfluoroethers, bis (trifluoromethyl) sulfide refrigerants, trifluoride iodide Methane refrigerants and natural refrigerants such as ammonia and carbon dioxide are exemplified.
飽和フッ化炭化水素冷媒としては、好ましくは炭素数1〜3、より好ましくは1〜2の飽和フッ化炭化水素が挙げられる。具体的には、ジフルオロメタン(R32)、トリフルオロメタン(R23)、ペンタフルオロエタン(R125)、1,1,2,2−テトラフルオロエタン(R134)、1,1,1,2−テトラフルオロエタン(R134a)、1,1,1−トリフルオロエタン(R143a)、1,1−ジフルオロエタン(R152a)、フルオロエタン(R161)、1,1,1,2,3,3,3−ヘプタフルオロプロパン(R227ea)、1,1,1,2,3,3−ヘキサフルオロプロパン(R236ea)、1,1,1,3,3,3−ヘキサフルオロプロパン(R236fa)、1,1,1,3,3−ペンタフルオロプロパン(R245fa)、および1,1,1,3,3−ペンタフルオロブタン(R365mfc)、又はこれらの2種以上の混合物が挙げられる。 The saturated fluorinated hydrocarbon refrigerant preferably includes saturated fluorinated hydrocarbons having preferably 1 to 3 carbon atoms, and more preferably 1 to 2 carbon atoms. Specifically, difluoromethane (R32), trifluoromethane (R23), pentafluoroethane (R125), 1,1,2,2-tetrafluoroethane (R134), 1,1,1,2-tetrafluoroethane (R134a), 1,1,1-trifluoroethane (R143a), 1,1-difluoroethane (R152a), fluoroethane (R161), 1,1,1,2,3,3,3-heptafluoropropane (R134a) R227ea), 1,1,1,2,3,3-hexafluoropropane (R236ea), 1,1,1,3,3,3-hexafluoropropane (R236fa), 1,1,1,3,3 Pentafluoropropane (R245fa), and 1,1,1,3,3-pentafluorobutane (R365mfc), or a mixture of two or more thereof Thing, and the like.
飽和フッ化炭化水素冷媒としては、上記の中から用途や要求性能に応じて適宜選択されるが、例えばR32単独;R23単独;R134a単独;R125単独;R134a/R32=60〜80質量%/40〜20質量%の混合物;R32/R125=40〜70質量%/60〜30質量%の混合物;R125/R143a=40〜60質量%/60〜40質量%の混合物;R134a/R32/R125=60質量%/30質量%/10質量%の混合物;R134a/R32/R125=40〜70質量%/15〜35質量%/5〜40質量%の混合物;R125/R134a/R143a=35〜55質量%/1〜15質量%/40〜60質量%の混合物などが好ましい例として挙げられる。さらに具体的には、R134a/R32=70/30質量%の混合物;R32/R125=60/40質量%の混合物;R32/R125=50/50質量%の混合物(R410A);R32/R125=45/55質量%の混合物(R410B);R125/R143a=50/50質量%の混合物(R507C);R32/R125/R134a=30/10/60質量%の混合物;R32/R125/R134a=23/25/52質量%の混合物(R407C);R32/R125/R134a=25/15/60質量%の混合物(R407E);R125/R134a/R143a=44/4/52質量%の混合物(R404A)などを用いることができる。 The saturated fluorinated hydrocarbon refrigerant is appropriately selected from the above depending on the application and required performance, but, for example, R32 alone; R23 alone; R134a alone; R125 alone; R134a / R32 = 60 to 80% by mass / 40 R32 / R125 = 40-70% by mass / 60-30% by mass mixture; R125 / R143a = 40-60% by mass / 60-40% by mass mixture; R134a / R32 / R125 = 60 A mixture of mass% / 30 mass% / 10 mass%; R134a / R32 / R125 = 40-70 mass% / 15-35 mass% / 5-40 mass% mixture; R125 / R134a / R143a = 35-55 mass% A mixture of 1 to 15% by mass and 40 to 60% by mass is a preferable example. More specifically, a mixture of R134a / R32 = 70/30% by mass; a mixture of R32 / R125 = 60/40% by mass; a mixture of R32 / R125 = 50/50% by mass (R410A); R32 / R125 = 45 Mixture of 55% by mass (R410B); mixture of R125 / R143a = 50/50% by mass (R507C); mixture of R32 / R125 / R134a = 30/10/60% by mass; R32 / R125 / R134a = 23/25 A mixture of 52% by mass (R407C); a mixture of R32 / R125 / R134a = 25/15/60% by mass (R407E); a mixture of R125 / R134a / R143a = 44/4/52% by mass (R404A) and the like be able to.
不飽和フッ化炭化水素(HFO)冷媒としては、フッ素数が3〜5のフルオロプロペンが好ましく、1,2,3,3,3−ペンタフルオロプロペン(HFO−1225ye)、1,3,3,3−テトラフルオロプロペン(HFO−1234ze)、2,3,3,3−テトラフルオロプロペン(HFO−1234yf)、1,2,3,3−テトラフルオロプロペン(HFO−1234ye)、及び3,3,3−トリフルオロプロペン(HFO−1243zf)のいずれかの1種又は2種以上の混合物であることが好ましい。冷媒物性の観点からは、HFO−1225ye、HFO−1234ze及びHFO−1234yfから選ばれる1種又は2種以上であることが好ましい。 As the unsaturated fluorinated hydrocarbon (HFO) refrigerant, fluoropropene having a fluorine number of 3 to 5 is preferable, and 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 1,3,3,3 3-tetrafluoropropene (HFO-1234ze), 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,2,3,3-tetrafluoropropene (HFO-1234ye), and 3,3,3, It is preferable that it is a 1 type, or 2 or more types of mixture of 3-trifluoro propene (HFO-1243zf) in any one. From the viewpoint of refrigerant physical properties, one or more selected from HFO-1225ye, HFO-1234ze and HFO-1234yf are preferable.
炭化水素冷媒としては、炭素数1〜5の炭化水素が好ましく、具体的には例えば、メタン、エチレン、エタン、プロピレン、プロパン(R290)、シクロプロパン、ノルマルブタン、イソブタン、シクロブタン、メチルシクロプロパン、2−メチルブタン、ノルマルペンタンまたはこれらの2種以上の混合物が挙げられる。これらの中でも、25℃、1気圧で気体のものが好ましく用いられ、プロパン、ノルマルブタン、イソブタン、2−メチルブタン又はこれらの混合物が好ましい。 The hydrocarbon refrigerant is preferably a hydrocarbon having 1 to 5 carbon atoms. Specifically, for example, methane, ethylene, ethane, propylene, propane (R290), cyclopropane, normal butane, isobutane, cyclobutane, methylcyclopropane, 2-methyl butane, normal pentane, or a mixture of two or more thereof. Among these, those which are gaseous at 25 ° C. and 1 atm are preferably used, and propane, normal butane, isobutane, 2-methyl butane or a mixture thereof is preferable.
本実施形態に係る冷凍機油は、通常、冷凍機において、冷媒と混合された冷凍機用作動流体組成物の形で存在している。本実施形態に係る冷凍機用作動流体組成物における冷凍機油の含有量は、特に制限されないが、冷媒100質量部に対して、好ましくは1〜500質量部、より好ましくは2〜400質量部である。 The refrigeration oil according to this embodiment is usually present in the form of a working fluid composition for a refrigeration mixed with a refrigerant in the refrigeration. The content of the refrigerator oil in the working fluid composition for a refrigerator according to the present embodiment is not particularly limited, but preferably 1 to 500 parts by mass, more preferably 2 to 400 parts by mass with respect to 100 parts by mass of the refrigerant. is there.
本実施形態に係る冷凍機油及び冷凍機用作動流体組成物は、往復動式や回転式の密閉型圧縮機を有するエアコン、冷蔵庫、開放型又は密閉型のカーエアコン、除湿機、給湯器、冷凍庫、冷凍冷蔵倉庫、自動販売機、ショーケース、化学プラント等の冷却装置、遠心式の圧縮機を有するもの等に好適に用いられる。 The refrigerator oil and the working fluid composition for a refrigerator according to the present embodiment are an air conditioner having a reciprocating or rotary closed type compressor, a refrigerator, an open or closed type car air conditioner, a dehumidifier, a water heater, a freezer It is suitably used for refrigeration freezers, vending machines, showcases, coolers such as chemical plants, and those having centrifugal compressors.
以下、実施例に基づき本発明を更に具体的に説明するが、本発明は以下の実施例に何ら限定されるものではない。 EXAMPLES Hereinafter, the present invention will be more specifically described based on examples, but the present invention is not limited to the following examples.
実施例及び比較例においては、表1に示す基油(多価アルコールと、脂肪酸A及び脂肪酸Bの混合脂肪酸とのエステル)と、以下に示す添加剤とを用いて、表2〜5に示す組成を有する冷凍機油を調製した。また、実施例及び比較例の各冷凍機油について、以下に示す耐摩耗性試験及び安定性試験を実施した。 In Examples and Comparative Examples, the base oil shown in Table 1 (ester of polyhydric alcohol and mixed fatty acid of fatty acid A and fatty acid B) and additives shown below are used and shown in Tables 2 to 5 A refrigerator oil having the composition was prepared. Moreover, the abrasion resistance test and stability test shown below were implemented about each refrigerator oil of an Example and a comparative example.
<添加剤>
B1:グリシジルネオデカノエート
B2:2−エチルヘキシルグリシジルエーテル
B3:1,2−エポキシテトラデカン
C1:下記式(9)で表される化合物
C2:下記式(10)で表される化合物
C3:下記式(11)で表される化合物
C4:下記式(12)で表される化合物及び下記式(13)で表される化合物の混合物
D1:トリクレジルホスフェート<Additives>
B1: glycidyl neodecanoate B2: 2-ethylhexyl glycidyl ether B3: 1,2-epoxytetradecane C1: compound C2 represented by the following formula (9): compound C3 represented by the following formula (10): Compound C4 represented by (11): Mixture of a compound represented by the following formula (12) and a compound represented by the following formula (13) D1: Tricresyl phosphate
(耐摩耗性試験)
耐摩耗性試験には、実コンプレッサと類似の冷媒雰囲気にできる、神鋼造機(株)製の高圧雰囲気摩擦試験機(回転ベーン材と固定ディスク材との回転摺動方式)を用いた。試験条件は、油量:600ml、試験温度:110℃、試験容器内圧力:1.1MPa、回転数:400rpm、負荷荷重:70kgf、試験時間:1時間で、冷媒としてはR32、R410A又はHFO−1234yf、ベーン材としてはSKH−51、ディスク材としてはFC250をそれぞれ用いた。耐摩耗性の評価は、ディスク材の摩耗量が極めて少ないことから、ベーン材の摩耗深さによって行った。得られた結果を表2〜5に示す。(Abrasion resistance test)
In the abrasion resistance test, a high-pressure atmosphere friction tester (rotational sliding method between a rotating vane material and a fixed disk material) manufactured by Shinko Engineering Co., Ltd., which can make a refrigerant atmosphere similar to an actual compressor, was used. The test conditions are: oil amount: 600 ml, test temperature: 110 ° C., pressure in test container: 1.1 MPa, rotation speed: 400 rpm, load: 70 kgf, test time: 1 hour, R32, R410A or HFO- as a refrigerant 1234yf, SKH-51 was used as the vane material, and FC250 was used as the disc material. The wear resistance was evaluated by the wear depth of the vane material because the amount of wear of the disk material was extremely small. The obtained results are shown in Tables 2 to 5.
(安定性試験)
安定性試験は、JIS K2211−09(オートクレーブテスト)に準拠し、含有水分量を300ppmに調整した試料油80gをオートクレーブに秤取し、触媒(鉄、銅、アルミの線、いずれも外径1.6mm×長さ50mm)と、冷媒(R32、R410A又はHFO−1234yf)20gとを封入した後、150℃に加熱し、150時間後の試料油の外観と酸価(JIS C2101)を測定した。得られた結果を表2〜5に示す。(Stability test)
In the stability test, 80 g of a sample oil whose water content was adjusted to 300 ppm was weighed in an autoclave according to JIS K 2211-09 (autoclave test), and the catalyst (iron, copper, aluminum wire, all had an outer diameter of 1) .6 mm × length 50 mm) and 20 g of a refrigerant (R32, R410A or HFO-1234yf), and then heated to 150 ° C., and after 150 hours, the appearance and acid value (JIS C2101) of the sample oil were measured. . The obtained results are shown in Tables 2 to 5.
Claims (4)
前記一般式(1)で表される化合物及び前記エポキシ化合物が、下記式(2)で表される条件を満たす、冷凍機油。
[式(1)中、R1、R2、R3、R4、R5、R6、R7及びR8は、それぞれ独立に水素原子又は1価の炭化水素基を表し、Aは、1又は2以上の芳香環を有する2価の炭化水素基を表す。]
[式(2)中、N E は前記エポキシ化合物1分子当たりのエポキシ基の数を示し、M E は前記エポキシ化合物の分子量を示し、W E は前記冷凍機油全量基準での前記エポキシ化合物の含有量を示し、N P は前記一般式(1)で表される化合物1分子当たりのリン原子の数を示し、M P は前記一般式(1)で表される化合物の分子量を示し、W P は前記冷凍機油全量基準での前記一般式(1)で表される化合物の含有量を示す。] A base oil, a compound represented by the following general formula (1), and an epoxy compound ,
Refrigerant oil in which the compound represented by the said General formula (1) and the said epoxy compound satisfy | fill the conditions represented by following formula (2) .
[In formula (1), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or a monovalent hydrocarbon group, and A is It represents a divalent hydrocarbon group having one or more aromatic rings. ]
[In Formula (2), N E represents the number of epoxy groups per molecule of the epoxy compound, M E represents the molecular weight of the epoxy compound, and W E represents the content of the epoxy compound based on the total amount of the refrigerator oil indicates the amount, N P represents the number of phosphorus atoms of the compound 1 per molecule represented by the general formula (1), M P represents the molecular weight of the compound represented by the general formula (1), W P These show content of the compound represented by the said General formula (1) on the basis of the said refrigerator oil whole quantity basis. ]
前記エポキシ化合物が、グリシジルエーテル型エポキシ化合物、グリシジルエステル型エポキシ化合物、オキシラン化合物、アルキルオキシラン化合物、脂環式エポキシ化合物、エポキシ化脂肪酸モノエステル、及びエポキシ化植物油からなる群より選ばれる少なくとも一種を含有する、請求項1に記載の冷凍機油。The epoxy compound contains at least one selected from the group consisting of glycidyl ether type epoxy compounds, glycidyl ester type epoxy compounds, oxirane compounds, alkyl oxirane compounds, alicyclic epoxy compounds, epoxidized fatty acid monoesters, and epoxidized vegetable oils The refrigerator oil according to claim 1.
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