JP5746886B2 - 冷凍機油組成物 - Google Patents
冷凍機油組成物 Download PDFInfo
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- JP5746886B2 JP5746886B2 JP2011059626A JP2011059626A JP5746886B2 JP 5746886 B2 JP5746886 B2 JP 5746886B2 JP 2011059626 A JP2011059626 A JP 2011059626A JP 2011059626 A JP2011059626 A JP 2011059626A JP 5746886 B2 JP5746886 B2 JP 5746886B2
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- 239000000203 mixture Substances 0.000 title claims description 106
- 125000004432 carbon atom Chemical group C* 0.000 claims description 217
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 239000010721 machine oil Substances 0.000 claims description 52
- 239000002199 base oil Substances 0.000 claims description 25
- 239000000654 additive Substances 0.000 claims description 23
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 19
- 230000000996 additive effect Effects 0.000 claims description 18
- 229920001289 polyvinyl ether Polymers 0.000 claims description 12
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 5
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 claims description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims 1
- -1 polyol ester Chemical class 0.000 description 240
- 239000002253 acid Substances 0.000 description 99
- 150000002430 hydrocarbons Chemical class 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 68
- 150000002148 esters Chemical class 0.000 description 67
- 239000003507 refrigerant Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 40
- 239000003921 oil Substances 0.000 description 37
- 235000019198 oils Nutrition 0.000 description 37
- 229910019142 PO4 Inorganic materials 0.000 description 32
- 239000010452 phosphate Substances 0.000 description 32
- 235000014113 dietary fatty acids Nutrition 0.000 description 29
- 229930195729 fatty acid Natural products 0.000 description 29
- 239000000194 fatty acid Substances 0.000 description 29
- 150000004665 fatty acids Chemical class 0.000 description 29
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 28
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 28
- 229920005862 polyol Polymers 0.000 description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 27
- 125000003118 aryl group Chemical group 0.000 description 26
- 125000000753 cycloalkyl group Chemical group 0.000 description 25
- 239000004593 Epoxy Substances 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 239000002480 mineral oil Substances 0.000 description 15
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 15
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- 150000003077 polyols Chemical class 0.000 description 14
- 150000005846 sugar alcohols Polymers 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000002947 alkylene group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 125000002877 alkyl aryl group Chemical group 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 150000007519 polyprotic acids Polymers 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 229930195733 hydrocarbon Natural products 0.000 description 11
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 11
- 229940117969 neopentyl glycol Drugs 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 10
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 10
- 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 10
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 10
- 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 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 235000010446 mineral oil Nutrition 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000600 sorbitol Substances 0.000 description 9
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
- 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 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 125000001400 nonyl 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])[H] 0.000 description 8
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 8
- 235000013772 propylene glycol Nutrition 0.000 description 8
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000005057 refrigeration Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 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 6
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 125000000913 palmityl 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])[H] 0.000 description 6
- 229920001451 polypropylene glycol Polymers 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 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 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 239000010779 crude oil Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- ILUAAIDVFMVTAU-UHFFFAOYSA-N cyclohex-4-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC=CCC1C(O)=O ILUAAIDVFMVTAU-UHFFFAOYSA-N 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 125000002960 margaryl 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])[H] 0.000 description 5
- 125000001421 myristyl 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])[H] 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000002958 pentadecyl 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])[H] 0.000 description 5
- 229920005604 random copolymer Polymers 0.000 description 5
- 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 5
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 5
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- 125000002948 undecyl 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])[H] 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
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- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- YVFHKLYMBACKFA-UHFFFAOYSA-N trioctoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound CCCCCCCCOP(=S)(OCCCCCCCC)OCCCCCCCC YVFHKLYMBACKFA-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- OEOJDBBVRPAIDK-UHFFFAOYSA-N tripentadecyl phosphate Chemical compound CCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCC OEOJDBBVRPAIDK-UHFFFAOYSA-N 0.000 description 1
- KRGWQWQLDWWLIB-UHFFFAOYSA-N tripentoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound CCCCCOP(=S)(OCCCCC)OCCCCC KRGWQWQLDWWLIB-UHFFFAOYSA-N 0.000 description 1
- QJAVUVZBMMXBRO-UHFFFAOYSA-N tripentyl phosphate Chemical compound CCCCCOP(=O)(OCCCCC)OCCCCC QJAVUVZBMMXBRO-UHFFFAOYSA-N 0.000 description 1
- CVWUIWZKLYGDNJ-UHFFFAOYSA-N tripentyl phosphite Chemical compound CCCCCOP(OCCCCC)OCCCCC CVWUIWZKLYGDNJ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- HEZNXCFAEKFTNB-UHFFFAOYSA-N tris(2-propan-2-ylphenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound CC(C)C1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C HEZNXCFAEKFTNB-UHFFFAOYSA-N 0.000 description 1
- XHTMGDWCCPGGET-UHFFFAOYSA-N tris(3,3-dichloropropyl) phosphate Chemical compound ClC(Cl)CCOP(=O)(OCCC(Cl)Cl)OCCC(Cl)Cl XHTMGDWCCPGGET-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- SVETUDAIEHYIKZ-IUPFWZBJSA-N tris[(z)-octadec-9-enyl] phosphate Chemical compound CCCCCCCC\C=C/CCCCCCCCOP(=O)(OCCCCCCCC\C=C/CCCCCCCC)OCCCCCCCC\C=C/CCCCCCCC SVETUDAIEHYIKZ-IUPFWZBJSA-N 0.000 description 1
- WYFGCJADJYRNAK-UHFFFAOYSA-N tritetradecyl phosphate Chemical compound CCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCC)OCCCCCCCCCCCCCC WYFGCJADJYRNAK-UHFFFAOYSA-N 0.000 description 1
- XEQUZHYCHCGTJX-UHFFFAOYSA-N tritridecyl phosphate Chemical compound CCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC XEQUZHYCHCGTJX-UHFFFAOYSA-N 0.000 description 1
- SUZOHRHSQCIJDK-UHFFFAOYSA-N triundecyl phosphate Chemical compound CCCCCCCCCCCOP(=O)(OCCCCCCCCCCC)OCCCCCCCCCCC SUZOHRHSQCIJDK-UHFFFAOYSA-N 0.000 description 1
- UKPASDNOVTUNJT-UHFFFAOYSA-N triundecyl phosphite Chemical compound CCCCCCCCCCCOP(OCCCCCCCCCCC)OCCCCCCCCCCC UKPASDNOVTUNJT-UHFFFAOYSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Description
[上記式(II)中、R2は炭素数1〜24のアルキル基を示す。]
−O−CO−O− (III−1)
で表される炭酸エステル結合を有する化合物である。なお、上記式(III−1)で表される炭酸エステル結合の個数は一分子当たり1個でもよく2個以上でもよい。
(X11O)b−B−[O−(A11O)c−CO−O−(A12O)d−Y11]a (III−2)
[式(III−2)中、X11は水素原子、アルキル基、シクロアルキル基又は下記一般式(III−3):
Y12−(OA13)e− (III−3)
(式(III−3)中、Y12は水素原子、アルキル基又はシクロアルキル基を表し、A13は炭素数2〜4のアルキレン基を示し、eは1〜50の整数を示す)
で表される基を表し、A11及びA12は同一でも異なっていてもよく、それぞれ炭素数2〜4のアルキレン基を表し、Y11は水素原子、アルキル基又はシクロアルキル基を表し、Bは水酸基3〜20個を有する化合物の残基を表し、aは1〜20、bは0〜19で且つa+bが3〜20となる整数を表し、cは0〜50の整数を表し、dは1〜50の整数を表す]
で表される構造を有するものが好ましい。
R11−〔(OR12)f−OR13〕g (III−4)
[式(III−4)中、R11は水素原子、炭素数1〜10のアルキル基、炭素数2〜10のアシル基又は水酸基を2〜8個有する化合物の残基を表し、R12は炭素数2〜4のアルキレン基を表し、R13は水素原子、炭素数1〜10のアルキル基又は炭素数2〜10のアシル基を表し、fは1〜80の整数を表し、gは1〜8の整数を表す]
で表される化合物が挙げられる。
CH3O−(C3H6O)h−CH3 (III−5)
(式中、hは6〜80の数を表す)
で表されるポリオキシプロピレングリコールジメチルエーテル、並びに下記一般式(III−6):
CH3O−(C2H4O)i−(C3H6O)j−CH3 (III−6)
(式中、i及びjはそれぞれ1以上であり且つiとjとの合計が6〜80となる数を表す)
で表されるポリオキシエチレンポリオキシプロピレングリコールジメチルエーテルが経済性及び前述の効果の点で好適であり、また、下記一般式(III−7):
C4H9O−(C3H6O)k−H (III−7)
(式中、kは6〜80の数を示す)
で表されるポリオキシプロピレングリコールモノブチルエーテル、さらには下記一般式(III−8):
CH3O−(C3H6O)l−H (III−8)
(式中、lは6〜80の数を表す)
で表されるポリオキシプロピレングリコールモノメチルエーテル、下記一般式(III−9):
CH3O−(C2H4O)m−(C3H6O)n−H (III−9)
(式中、m及びnはそれぞれ1以上であり且つmとnとの合計が6〜80となる数を表す)
で表されるポリオキシエチレンポリオキシプロピレングリコールモノメチルエーテル、下記一般式(III−10):
C4H9O−(C2H4O)m−(C3H6O)n−H (III−10)
(式中、m及びnはそれぞれ1以上であり且つmとnとの合計が6〜80となる数を表す)
ポリオキシエチレンポリオキシプロピレングリコールモノブチルエーテル、下記一般式(III−11):
CH3COO−(C3H6O)l−COCH3 (III−11)
(式中、lは6〜80の数を表す)
で表されるポリオキシプロピレングリコールジアセテートが、経済性等の点で好適である。
で表される基を表し、R18〜R21の少なくとも1つが一般式(III−13)で表される基である]
で表される構成単位を少なくとも1個有するポリオキシアルキレングリコール誘導体を使用することができる。
で表される構成単位からなる共重合体の三種類に大別することができる。上記単独重合体の好適例は、一般式(III−12)で表される構成単位Aを1〜200個有するとともに、末端基がそれぞれ水酸基、炭素数1〜10のアシルオキシ基、炭素数1〜10のアルコキシ基あるいはアリーロキシ基からなるものを挙げることができる。一方、共重合体の好適例は、一般式(III−12)で表される二種類の構成単位A、Bをそれぞれ1〜200個有するか、あるいは一般式(III−12)で表される構成単位Aを1〜200個と一般式(III−12)で表される構成単位Cを1〜200個有するとともに、末端基がそれぞれ水酸基、炭素数1〜10のアシルオキシ基、炭素数1〜10のアルコキシ基あるいはアリーロキシ基からなるものを挙げることができる。これらの共重合体は、構成単位Aと構成単位B(あるいは構成単位C)との交互共重合、ランダム共重合、ブロック共重合体あるいは構成単位Aの主鎖に構成単位Bがグラフト結合したグラフト共重合体のいずれの重合形式であってもよい。
で表される構成単位を有するポリビニルエーテル系化合物が挙げられる。
で表される構成単位とを有するブロック共重合体又はランダム共重合体からなるポリビニルエーテル系化合物も使用することができる。
で表されるものであり、且つ他方が下記一般式(III−19)又は(III−20):
で表される構造を有するもの;及び
その末端の一方が、上記一般式(III−17)又は(III−18)で表され、且つ他方が下記一般式(III−21):
で表される構造を有するものが好ましい。このようなポリビニルエーテルの中でも、次に挙げるものが特に好適である。
(1)末端の一方が一般式(III−17)又は(III−18)で表され、他方が一般式(III−19)又は(III−20)で表される構造を有しており、一般式(III−15)におけるR31〜R33がいずれも水素原子であり、sが0〜4の数であり、R34が炭素数2〜4の2価の炭化水素基であり、且つR35が炭素数1〜20の炭化水素基であるもの;
(2)一般式(III−15)で表される構成単位のみを有するものであって、その末端の一方が一般式(III−17)で表され、他方が一般式(III−18)で表される構造を有しており、一般式(III−15)におけるR31〜R33がいずれも水素原子であり、sが0〜4の数であり、R34が炭素数2〜4の2価の炭化水素基であり、且つR35が炭素数1〜20の炭化水素基であるもの;
(3)末端の一方が一般式(III−17)又は(III−18)で表され、他方が一般式(III−19)で表される構造を有しており、一般式(III−15)におけるR31〜R33がいずれも水素原子であり、sが0〜4の数であり、R34が炭素数2〜4の2価の炭化水素基であり、且つR35が炭素数1〜20の炭化水素基であるもの;
(4)一般式(III−15)で表される構成単位のみを有するものであって、その末端の一方が一般式(III−17)で表され、他方が一般式(III−20)で表される構造を有しており、一般式(III−15)におけるR31〜R33がいずれも水素原子であり、sが0〜4の数であり、R34が炭素数2〜4の2価の炭化水素基であり、且つR35が炭素数1〜20の炭化水素基であるもの。
で表される構造を有するポリビニルエーテル系化合物も使用することができる。
で表される構成単位からなり、かつ質量平均分子量が300〜5,000であって、末端の一方が下記一般式(III−25)又は(III−26):
で表される構造を有するアルキルビニルエーテルの単独重合物又は共重合物からなるポリビニルエーテル系化合物も使用することができる。
酸性リン酸エステルとしては、モノブチルアシッドホスフェート、モノペンチルアシッドホスフェート、モノヘキシルアシッドホスフェート、モノヘプチルアシッドホスフェート、モノオクチルアシッドホスフェート、モノノニルアシッドホスフェート、モノデシルアシッドホスフェート、モノウンデシルアシッドホスフェート、モノドデシルアシッドホスフェート、モノトリデシルアシッドホスフェート、モノテトラデシルアシッドホスフェート、モノペンタデシルアシッドホスフェート、モノヘキサデシルアシッドホスフェート、モノヘプタデシルアシッドホスフェート、モノオクタデシルアシッドホスフェート、モノオレイルアシッドホスフェート、ジブチルアシッドホスフェート、ジペンチルアシッドホスフェート、ジヘキシルアシッドホスフェート、ジヘプチルアシッドホスフェート、ジオクチルアシッドホスフェート、ジノニルアシッドホスフェート、ジデシルアシッドホスフェート、ジウンデシルアシッドホスフェート、ジドデシルアシッドホスフェート、ジトリデシルアシッドホスフェート、ジテトラデシルアシッドホスフェート、ジペンタデシルアシッドホスフェート、ジヘキサデシルアシッドホスフェート、ジヘプタデシルアシッドホスフェート、ジオクタデシルアシッドホスフェート、ジオレイルアシッドホスフェート等;
酸性リン酸エステルのアミン塩としては、前記酸性リン酸エステルのメチルアミン、エチルアミン、プロピルアミン、ブチルアミン、ペンチルアミン、ヘキシルアミン、ヘプチルアミン、オクチルアミン、ジメチルアミン、ジエチルアミン、ジプロピルアミン、ジブチルアミン、ジペンチルアミン、ジヘキシルアミン、ジヘプチルアミン、ジオクチルアミン、トリメチルアミン、トリエチルアミン、トリプロピルアミン、トリブチルアミン、トリペンチルアミン、トリヘキシルアミン、トリヘプチルアミン、トリオクチルアミン等のアミンとの塩等;
塩素化リン酸エステルとしては、トリス・ジクロロプロピルホスフェート、トリス・クロロエチルホスフェート、トリス・クロロフェニルホスフェート、ポリオキシアルキレン・ビス[ジ(クロロアルキル)]ホスフェート等;
亜リン酸エステルとしては、ジブチルホスファイト、ジペンチルホスファイト、ジヘキシルホスファイト、ジヘプチルホスファイト、ジオクチルホスファイト、ジノニルホスファイト、ジデシルホスファイト、ジウンデシルホスファイト、ジドデシルホスファイト、ジオレイルホスファイト、ジフェニルホスファイト、ジクレジルホスファイト、トリブチルホスファイト、トリペンチルホスファイト、トリヘキシルホスファイト、トリヘプチルホスファイト、トリオクチルホスファイト、トリノニルホスファイト、トリデシルホスファイト、トリウンデシルホスファイト、トリドデシルホスファイト、トリオレイルホスファイト、トリフェニルホスファイト、トリクレジルホスファイト等、が挙げられる。また、これらの混合物も使用できる。
(E1)フェニルグリシジルエーテル型エポキシ化合物
(E2)アルキルグリシジルエーテル型エポキシ化合物
(E3)グリシジルエステル型エポキシ化合物
(E4)アリルオキシラン化合物
(E5)アルキルオキシラン化合物
(E6)脂環式エポキシ化合物
(E7)エポキシ化脂肪酸モノエステル
(E8)エポキシ化植物油。
で表される化合物が挙げられる。
(ii)多価アルコールと一塩基酸とのエステル、
(iii)一価アルコールと多塩基酸とのエステル、
(iv)多価アルコールと多塩基酸とのエステル、
(v)一価アルコール、多価アルコールとの混合物と多塩基酸との混合エステル、
(vi)多価アルコールと一塩基酸、多塩基酸との混合物との混合エステル、
(vii)一価アルコール、多価アルコールとの混合物と一塩基酸、多塩基酸との混合エステル。
実施例1〜14及び比較例1〜7においては、それぞれ以下に示す基油及び添加剤を用いて表1〜3に示す組成を有する冷凍機油組成物を調製した。
基油1:ペンタエリスリトールと2−エチルヘキサン酸及び3,5,5−トリメチルヘキサン酸の等モル混合物とのテトラエステル(40℃における動粘度:68.5mm2/s、流動点:−25℃)、
基油2:ポリプロピレングリコール(40℃における動粘度:46mm2/s,重量平均分子量:1000)、
基油3:ビニルエチルエーテルとビニルイソブチルエーテルとのランダム共重合体(ビニルエチルエーテルとビニルイソブチルエーテルとのモル比:7/1、数平均分子量:900、40℃における動粘度:68.5mm2/s、100℃における動粘度:8mm2/s、流動点:−40℃)、
基油4:1,2−シクロヘキサンジカルボン酸と2−エチルヘキサノールとのジエステル(40℃における動粘度:15mm2/s、流動点:−40℃)、
基油5:ナフテン系鉱油(40℃における動粘度:56mm2/s)、
基油6:パラフィン系鉱油(40℃における動粘度:68mm2/s)。
添加剤A1:没食子酸メチル、
添加剤A2:没食子酸プロピル、
添加剤A3:没食子酸2−エチルヘキシル、
添加剤A4:没食子酸ラウリル、
添加剤A5:没食子酸ステアリル、
添加剤B:トリフェニルホスフォロチオネート、
添加剤C:トリクレジルホスフェート、
添加剤E3:グリシジル−2,2’−ジメチルオクタノエート、
添加剤F3:ステアリン酸ブチル。
先ず、冷凍機油組成物の含有水分を、基油1〜4を用いた場合には500ppmに、基油5〜6を用いた場合には200ppmに調整した。次に、その冷凍機油組成物100gを200mlのオートクレーブに入れ、触媒として2gの鉛片を浸漬させ、さらに冷媒15gを封入し、175℃で2週間保持した。冷媒は、R410A、R134a及びR22を表1〜3に示すように組み合わせて使用した。そして、2週間後の冷凍機油組成物の酸価(mgKOH/g)及びPb含有量(ppm)を測定した。得られた結果を表1〜3に示す。なお、Pb含有量は、ICPを用いて測定した。
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US4877541A (en) * | 1987-12-11 | 1989-10-31 | Exxon Research And Engineering Company | Corrosion inhibitor |
US5021179A (en) * | 1990-07-12 | 1991-06-04 | Henkel Corporation | Lubrication for refrigerant heat transfer fluids |
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