CA2129380A1 - Lubricant oil composition comprising a fluorine-containing aromatic compound and an alkyl- or alkyl derivative-substituted aromatic compound, and a refrigerant composition containing the same - Google Patents
Lubricant oil composition comprising a fluorine-containing aromatic compound and an alkyl- or alkyl derivative-substituted aromatic compound, and a refrigerant composition containing the sameInfo
- Publication number
- CA2129380A1 CA2129380A1 CA002129380A CA2129380A CA2129380A1 CA 2129380 A1 CA2129380 A1 CA 2129380A1 CA 002129380 A CA002129380 A CA 002129380A CA 2129380 A CA2129380 A CA 2129380A CA 2129380 A1 CA2129380 A1 CA 2129380A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- substituted
- fluorine
- alkyl
- carbon atoms
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 236
- 239000000314 lubricant Substances 0.000 title claims abstract description 233
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 211
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 204
- 239000003507 refrigerant Chemical class 0.000 title claims abstract description 199
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 140
- 239000011737 fluorine Substances 0.000 title claims abstract description 140
- 125000000217 alkyl group Chemical class 0.000 title claims abstract description 130
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 145
- 125000003118 aryl group Chemical group 0.000 claims abstract description 101
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims abstract description 54
- 125000001424 substituent group Chemical group 0.000 claims abstract description 46
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- 239000003921 oil Substances 0.000 claims description 343
- 229940060037 fluorine Drugs 0.000 claims description 138
- 235000019000 fluorine Nutrition 0.000 claims description 138
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 95
- 125000001153 fluoro group Chemical group F* 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 53
- 150000002148 esters Chemical class 0.000 claims description 39
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 30
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- 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 claims description 26
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 150000001721 carbon Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 16
- 229910052727 yttrium Inorganic materials 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 150000001555 benzenes Chemical class 0.000 claims description 13
- 125000004991 fluoroalkenyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000002790 naphthalenes Chemical class 0.000 claims description 10
- 125000002560 nitrile group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 229940075566 naphthalene Drugs 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 366
- 238000010521 absorption reaction Methods 0.000 abstract description 31
- 238000005057 refrigeration Methods 0.000 abstract description 28
- 230000001050 lubricating effect Effects 0.000 abstract description 21
- 238000010292 electrical insulation Methods 0.000 abstract description 8
- 230000002035 prolonged effect Effects 0.000 abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 73
- -1 polyol ester compounds Chemical class 0.000 description 62
- 238000000034 method Methods 0.000 description 38
- 150000002430 hydrocarbons Chemical class 0.000 description 37
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 36
- 238000012360 testing method Methods 0.000 description 35
- 150000004996 alkyl benzenes Chemical class 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000460 chlorine Substances 0.000 description 31
- 230000009102 absorption Effects 0.000 description 30
- 239000000654 additive Substances 0.000 description 28
- 229910019142 PO4 Inorganic materials 0.000 description 27
- 239000010452 phosphate Substances 0.000 description 27
- 235000021317 phosphate Nutrition 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 238000002156 mixing Methods 0.000 description 19
- 239000010702 perfluoropolyether Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 239000007983 Tris buffer Substances 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 239000002480 mineral oil Substances 0.000 description 17
- 229940042472 mineral oil Drugs 0.000 description 16
- 235000010446 mineral oil Nutrition 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 238000004566 IR spectroscopy Methods 0.000 description 14
- 231100000704 bioconcentration Toxicity 0.000 description 14
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000010696 ester oil Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 11
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 231100000693 bioaccumulation Toxicity 0.000 description 10
- 150000002989 phenols Chemical class 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 8
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 229920001515 polyalkylene glycol Polymers 0.000 description 8
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 238000005299 abrasion Methods 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 150000007942 carboxylates Chemical group 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000004185 ester group Chemical group 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000001747 exhibiting effect Effects 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940057995 liquid paraffin Drugs 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 4
- 230000004224 protection Effects 0.000 description 4
- 150000005691 triesters Chemical class 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 3
- ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000012964 benzotriazole Substances 0.000 description 3
- 150000001565 benzotriazoles Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 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 3
- 150000005828 hydrofluoroalkanes Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229940056211 paraffin Drugs 0.000 description 3
- 239000012188 paraffin wax Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 235000014786 phosphorus Nutrition 0.000 description 3
- 229920000515 polycarbonate Chemical class 0.000 description 3
- 239000004417 polycarbonate Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 2
- BZPCMSSQHRAJCC-UHFFFAOYSA-N 1,2,3,3,4,4,5,5,5-nonafluoro-1-(1,2,3,3,4,4,5,5,5-nonafluoropent-1-enoxy)pent-1-ene Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)=C(F)OC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)F BZPCMSSQHRAJCC-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- OIVQVBDAMYDDEM-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-[1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy]propanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F OIVQVBDAMYDDEM-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 2
- KNDDEFBFJLKPFE-UHFFFAOYSA-N 4-n-Heptylphenol Chemical compound CCCCCCCC1=CC=C(O)C=C1 KNDDEFBFJLKPFE-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 102100038916 Caspase-5 Human genes 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
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- NSGFVWUIFGKMMY-UHFFFAOYSA-N trifluoromethyl nonanoate Chemical compound CCCCCCCCC(=O)OC(F)(F)F NSGFVWUIFGKMMY-UHFFFAOYSA-N 0.000 description 1
- JJPJJLMBJWRLAT-UHFFFAOYSA-N trifluoromethyl octanoate Chemical compound CCCCCCCC(=O)OC(F)(F)F JJPJJLMBJWRLAT-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- PPBMHSGZZYZYBO-UHFFFAOYSA-N triheptyl phosphite Chemical compound CCCCCCCOP(OCCCCCCC)OCCCCCCC PPBMHSGZZYZYBO-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- VRRIVXLVXXAHJA-UHFFFAOYSA-N tris(2,3,4-tribromophenyl) phosphate Chemical compound BrC1=C(Br)C(Br)=CC=C1OP(=O)(OC=1C(=C(Br)C(Br)=CC=1)Br)OC1=CC=C(Br)C(Br)=C1Br VRRIVXLVXXAHJA-UHFFFAOYSA-N 0.000 description 1
- LRSNDFOWYYKLHB-UHFFFAOYSA-N tris(2,3-dibromophenyl) phosphate Chemical compound BrC1=CC=CC(OP(=O)(OC=2C(=C(Br)C=CC=2)Br)OC=2C(=C(Br)C=CC=2)Br)=C1Br LRSNDFOWYYKLHB-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-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
- LFRFOEVCFVCHEV-UHFFFAOYSA-N tris(2-chlorophenyl) phosphate Chemical compound ClC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)Cl)OC1=CC=CC=C1Cl LFRFOEVCFVCHEV-UHFFFAOYSA-N 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-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
- UKPASDNOVTUNJT-UHFFFAOYSA-N triundecyl phosphite Chemical compound CCCCCCCCCCCOP(OCCCCCCCCCCC)OCCCCCCCCCCC UKPASDNOVTUNJT-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- MBBWTVUFIXOUBE-UHFFFAOYSA-L zinc;dicarbamodithioate Chemical compound [Zn+2].NC([S-])=S.NC([S-])=S MBBWTVUFIXOUBE-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
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- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/18—Ethers, e.g. epoxides
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- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
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- 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
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
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- C10M137/04—Phosphate esters
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- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
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- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
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- C10M2205/022—Ethene
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- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/30—Heterocyclic compounds
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/32—Wires, ropes or cables lubricants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/34—Lubricating-sealants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/36—Release agents or mold release agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/38—Conveyors or chain belts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/40—Generators or electric motors in oil or gas winning field
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/44—Super vacuum or supercritical use
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/50—Medical uses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5-199527 | 1993-08-11 | ||
| JP19952793 | 1993-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2129380A1 true CA2129380A1 (en) | 1995-02-12 |
Family
ID=16409319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002129380A Abandoned CA2129380A1 (en) | 1993-08-11 | 1994-08-03 | Lubricant oil composition comprising a fluorine-containing aromatic compound and an alkyl- or alkyl derivative-substituted aromatic compound, and a refrigerant composition containing the same |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5547593A (https=) |
| EP (2) | EP0638629B1 (https=) |
| KR (1) | KR970010176B1 (https=) |
| CN (2) | CN1106453A (https=) |
| CA (1) | CA2129380A1 (https=) |
| DE (2) | DE69422347T2 (https=) |
| MY (1) | MY130041A (https=) |
| TW (2) | TW294718B (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5711895A (en) * | 1994-12-12 | 1998-01-27 | Nippon Oil Co., Ltd. | Fluid composition for use in a refrigerating machine in which the refrigerating machine oil is at least one hydrocarbon compound of a formula consisting of two phenyl groups joined through an alkylene or alkenylene group |
| EP0882780A4 (en) * | 1995-12-28 | 2000-08-16 | Daikin Ind Ltd | REFRIGERATOR OIL AND REFRIGERATOR FOR USE THEREOF |
| DE19628477C1 (de) * | 1996-07-15 | 1998-01-22 | Gruenzweig & Hartmann | Nadelhilfsmittel und dessen Verwendung zur Herstellung von Nadelfilzen und damit hergestellter Nadelfilz |
| US5839311A (en) * | 1996-09-17 | 1998-11-24 | Minnesota Mining And Manufacturing Company | Composition to aid in the forming of metal |
| US6043201A (en) * | 1996-09-17 | 2000-03-28 | Minnesota Mining And Manufacturing Company | Composition for cutting and abrasive working of metal |
| US6294508B1 (en) | 1996-09-17 | 2001-09-25 | 3M Innovative Properties Company | Composition comprising lubricious additive for cutting or abrasive working and a method therefor |
| US6150306A (en) * | 1999-03-04 | 2000-11-21 | Morton Internatioanl Inc. | Fluorescent tracer dyes |
| WO2000058956A1 (en) * | 1999-03-26 | 2000-10-05 | Pennzoil-Quaker State Company | Lubricant for magnetic recording medium and use thereof |
| US6374907B1 (en) * | 1999-10-08 | 2002-04-23 | 3M Innovative Properties Company | Hydrofluoroether as a heat-transfer fluid |
| US6899820B2 (en) * | 2002-06-10 | 2005-05-31 | E. I. Du Pont De Nemours And Company | Fluorocarbon, oxygenated and non-oxygenated lubricant, and compatibilizer composition, and method for replacing refrigeration composition in a refrigeration system |
| US6841088B2 (en) * | 2002-06-10 | 2005-01-11 | E. I. Du Pont De Nemours And Company | Fluorocarbon, oxygenated and non-oxygenated lubricant, and compatibilizer composition, and method for replacing refrigeration composition in a refrigeration system |
| US20040099838A1 (en) * | 2002-08-08 | 2004-05-27 | Leck Thomas J | Refrigerant compositions comprising performance enhancing additives |
| WO2005012467A1 (ja) * | 2003-08-01 | 2005-02-10 | Nippon Oil Corporation | 冷凍機油組成物 |
| US7531700B2 (en) * | 2003-09-24 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Fluorinated arylethers and methods for use thereof |
| CN1886628B (zh) * | 2003-09-29 | 2011-09-07 | 自推进研发专家公司 | 热泵式干衣机 |
| US7560044B2 (en) * | 2003-11-13 | 2009-07-14 | E. I. Du Pont De Nemours And Company | Compositions and methods for reducing fire hazard of flammable refrigerants |
| EP1792970B1 (en) * | 2004-09-14 | 2013-01-23 | Idemitsu Kosan Co., Ltd. | Refrigerator oil composition containing an aromatic sulfur compound |
| JP5122740B2 (ja) * | 2005-11-15 | 2013-01-16 | 出光興産株式会社 | 冷凍機油組成物 |
| JP4885534B2 (ja) * | 2005-12-20 | 2012-02-29 | 出光興産株式会社 | 冷凍機油組成物、これを用いた冷凍機用圧縮機及び冷凍装置 |
| US8716201B2 (en) | 2009-10-02 | 2014-05-06 | Exxonmobil Research And Engineering Company | Alkylated naphtylene base stock lubricant formulations |
| US9062236B2 (en) * | 2009-11-02 | 2015-06-23 | Arkema Inc. | Random copolymer oil return agents |
| JP5972639B2 (ja) | 2012-03-30 | 2016-08-17 | 出光興産株式会社 | 冷凍機用潤滑油組成物 |
| US20150133353A1 (en) * | 2012-06-05 | 2015-05-14 | Jx Nippon Oil & Energy Corporation | Grease composition |
| US8962879B2 (en) | 2012-11-14 | 2015-02-24 | E I Du Pont De Nemours And Company | Perfluoropolyvinyl modified aryl intermediates/monomers |
| US9365476B2 (en) | 2012-11-14 | 2016-06-14 | E I Du Pont De Nemours And Company | Aryl compounds modified with perfluorovinyl ethers |
| US9145356B2 (en) | 2012-11-14 | 2015-09-29 | E I Du Pont De Nemours And Company | Perfluoropolyvinyl modified aryl intermediates and monomers |
| US9193702B2 (en) | 2013-10-31 | 2015-11-24 | E I Du Pont De Nemours And Company | Fluorinated aryl epoxide compounds |
| US20150170688A1 (en) * | 2013-12-18 | 2015-06-18 | Western Digital Technologies, Inc. | Grease composition additive for pivot bearing assemblies |
| CN103756767B (zh) * | 2014-01-15 | 2015-08-12 | 北京科技大学 | 一种高速宽幅铝板带轧制油及其制备方法 |
| EP3164473A4 (en) | 2014-07-02 | 2018-01-03 | Basf Se | Sulfonate esters to improve fluoropolymer seal compatibility of lubricant compositions |
| JP6466879B2 (ja) * | 2016-04-04 | 2019-02-06 | トヨタ自動車株式会社 | 冷却液組成物及びこれを用いた内燃機関の運転方法 |
| JP7142405B2 (ja) * | 2018-01-24 | 2022-09-27 | 出光興産株式会社 | 潤滑油組成物及び冷凍機用組成物 |
| CN110832051B (zh) * | 2018-06-13 | 2020-12-18 | 日立江森自控空调有限公司 | 制冷剂组合物以及使用其的冷冻循环装置 |
| CN111088091B (zh) * | 2018-10-23 | 2022-03-11 | 中国石油化工股份有限公司 | 一种汽油机油组合物及其制备方法 |
| EP3900102B1 (en) * | 2018-12-20 | 2023-04-05 | Solvay Specialty Polymers Italy S.p.A. | Method for exchanging heat with a battery using fluorinated compounds having a low gwp |
| CN112920027B (zh) * | 2021-02-02 | 2024-04-09 | 山东盛华电子新材料有限公司 | 一种含氟液晶材料及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE246788C (https=) * | ||||
| US4359394A (en) * | 1978-10-30 | 1982-11-16 | Thermo King Corporation | Thermally stable lubricants for refrigerator systems |
| JPS58171487A (ja) * | 1982-04-02 | 1983-10-08 | Hitachi Ltd | 冷凍機油組成物 |
| US4405529A (en) * | 1982-09-20 | 1983-09-20 | American Cyanamid Company | Method for the preparation of difluoromethoxyaromatic compounds |
| JPS6096684A (ja) * | 1983-11-01 | 1985-05-30 | Asahi Glass Co Ltd | 耐熱性が向上した作動媒体組成物 |
| US4753745A (en) * | 1985-12-30 | 1988-06-28 | The Lubrizol Corporation | Methylene linked aromatic pour point depressant |
| US4880553A (en) * | 1985-12-30 | 1989-11-14 | The Lubrizol Corporation | Methylene linked aromatic pour point depressant |
| JPS63258992A (ja) * | 1987-04-16 | 1988-10-26 | Hitachi Metals Ltd | 薄膜潤滑用合成潤滑剤及び磁気記録媒体 |
| US4755316A (en) * | 1987-10-23 | 1988-07-05 | Allied-Signal Inc. | Refrigeration lubricants |
| JP2771539B2 (ja) * | 1987-11-02 | 1998-07-02 | 出光興産株式会社 | フロン冷媒用潤滑油 |
| JPH01307761A (ja) * | 1988-06-07 | 1989-12-12 | Hitachi Ltd | 電子写真用感光体及びその製造方法 |
| US5254274A (en) * | 1989-01-06 | 1993-10-19 | Mobil Oil Corporation | Alkylaromatic lubricant fluids |
| EP0432273B1 (en) * | 1989-06-05 | 1993-12-22 | Asahi Kasei Kogyo Kabushiki Kaisha | Refrigerant composition |
| KR950005694B1 (ko) * | 1989-07-05 | 1995-05-29 | 가부시끼가이샤 교오세끼 세이힝기주쓰 겡뀨쇼 | 냉각윤활제 |
| JP2801703B2 (ja) * | 1989-09-01 | 1998-09-21 | 花王株式会社 | 冷凍機油 |
| GB9010517D0 (en) * | 1990-05-10 | 1990-07-04 | Ici Plc | Lubricants |
| KR950008087B1 (ko) * | 1990-09-17 | 1995-07-25 | 미쓰이세끼유 가가꾸고오교오 가부시끼가이샤 | 폴리카보네이트, 그 용도, 그 제조방법 및 정제방법 |
| JPH0586382A (ja) * | 1991-02-06 | 1993-04-06 | Asahi Chem Ind Co Ltd | 潤滑剤 |
| TW203098B (https=) * | 1991-09-27 | 1993-04-01 | Mitsui Petroleum Chemicals Ind | |
| AU655345B2 (en) * | 1992-02-18 | 1994-12-15 | Idemitsu Kosan Co. Ltd | Lubricant for refrigerating machine employing refrigerant comprising tetrafluoroethane |
| AU661756B2 (en) * | 1992-02-18 | 1995-08-03 | Idemitsu Kosan Co. Ltd | Lubricant for refrigerating machine employing refrigerant comprising tetrafluoroethane |
-
1994
- 1994-08-03 CA CA002129380A patent/CA2129380A1/en not_active Abandoned
- 1994-08-09 MY MYPI94002070A patent/MY130041A/en unknown
- 1994-08-11 DE DE69422347T patent/DE69422347T2/de not_active Expired - Lifetime
- 1994-08-11 EP EP94305933A patent/EP0638629B1/en not_active Expired - Lifetime
- 1994-08-11 KR KR94019844A patent/KR970010176B1/ko not_active Expired - Fee Related
- 1994-08-11 DE DE69431635T patent/DE69431635D1/de not_active Expired - Lifetime
- 1994-08-11 CN CN94109505A patent/CN1106453A/zh active Pending
- 1994-08-11 EP EP99101201A patent/EP0913454B1/en not_active Expired - Lifetime
- 1994-08-11 US US08/289,220 patent/US5547593A/en not_active Expired - Lifetime
- 1994-10-03 TW TW083107171A patent/TW294718B/zh active
- 1994-10-03 TW TW085112235A patent/TW304939B/zh active
-
1997
- 1997-10-15 CN CN97120470A patent/CN1072640C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0638629B1 (en) | 1999-12-29 |
| EP0638629A2 (en) | 1995-02-15 |
| EP0913454A1 (en) | 1999-05-06 |
| KR950005965A (ko) | 1995-03-20 |
| US5547593A (en) | 1996-08-20 |
| KR970010176B1 (en) | 1997-06-21 |
| TW294718B (https=) | 1997-01-01 |
| DE69431635D1 (de) | 2002-12-05 |
| CN1193008A (zh) | 1998-09-16 |
| EP0913454B1 (en) | 2002-10-30 |
| CN1072640C (zh) | 2001-10-10 |
| CN1106453A (zh) | 1995-08-09 |
| TW304939B (https=) | 1997-05-11 |
| EP0638629A3 (en) | 1995-08-23 |
| DE69422347T2 (de) | 2000-08-24 |
| DE69422347D1 (de) | 2000-02-03 |
| MY130041A (en) | 2007-05-31 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |