US3585137A - Synthetic ester lubricating oil composition - Google Patents
Synthetic ester lubricating oil composition Download PDFInfo
- Publication number
- US3585137A US3585137A US836613A US3585137DA US3585137A US 3585137 A US3585137 A US 3585137A US 836613 A US836613 A US 836613A US 3585137D A US3585137D A US 3585137DA US 3585137 A US3585137 A US 3585137A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- oil
- esters
- ester
- acid
- 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.)
- Expired - Lifetime
Links
- 150000002148 esters Chemical class 0.000 title abstract description 28
- 239000010687 lubricating oil Substances 0.000 title abstract description 20
- 239000000203 mixture Substances 0.000 title description 45
- 239000003921 oil Substances 0.000 abstract description 50
- -1 C1-C12 ALKYL Chemical class 0.000 abstract description 30
- 239000000654 additive Substances 0.000 abstract description 26
- 239000002253 acid Substances 0.000 abstract description 23
- 229910052751 metal Inorganic materials 0.000 abstract description 21
- 239000002184 metal Substances 0.000 abstract description 21
- 239000001257 hydrogen Substances 0.000 abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 15
- 150000007513 acids Chemical class 0.000 abstract description 13
- 239000003963 antioxidant agent Substances 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 150000004982 aromatic amines Chemical class 0.000 abstract description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract description 8
- 150000008301 phosphite esters Chemical class 0.000 abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 abstract description 8
- 230000007935 neutral effect Effects 0.000 abstract description 7
- 230000003078 antioxidant effect Effects 0.000 abstract description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract description 6
- 239000000539 dimer Substances 0.000 abstract description 3
- 150000001408 amides Chemical group 0.000 abstract description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract description 2
- VJZWIFWPGRIJSN-XRHABHTOSA-N dilinoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/CCCCCCCC(O)=O VJZWIFWPGRIJSN-XRHABHTOSA-N 0.000 abstract description 2
- 239000010695 polyglycol Substances 0.000 abstract description 2
- 229920000151 polyglycol Polymers 0.000 abstract description 2
- 150000007519 polyprotic acids Chemical class 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 abstract 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 46
- 239000010696 ester oil Substances 0.000 description 23
- 238000005260 corrosion Methods 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 230000007797 corrosion Effects 0.000 description 19
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 16
- 229950000688 phenothiazine Drugs 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- 239000002199 base oil Substances 0.000 description 13
- 150000002431 hydrogen Chemical class 0.000 description 12
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 11
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 6
- 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 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- 150000005691 triesters Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000010913 used oil Substances 0.000 description 4
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 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
- 238000013329 compounding Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical class COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- DWFUTNJGNBYHNN-UHFFFAOYSA-N 2,2,4-trimethylhexanedioic acid Chemical compound OC(=O)CC(C)CC(C)(C)C(O)=O DWFUTNJGNBYHNN-UHFFFAOYSA-N 0.000 description 1
- CWPPDTVYIJETDF-UHFFFAOYSA-N 2,2,4-trimethylpentan-1-ol Chemical compound CC(C)CC(C)(C)CO CWPPDTVYIJETDF-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-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
- AAIUWVOMXTVLRG-UHFFFAOYSA-N 8,8-dimethylnonan-1-amine Chemical compound CC(C)(C)CCCCCCCN AAIUWVOMXTVLRG-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 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
- 238000007664 blowing Methods 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
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical class OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
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Definitions
- R and R ar each hydrogen, C C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C C alkyl, (l -C acyl or phenyl, and R is hydrogen, C C alkyl or halo C -C alkyl.
- the nuclear amino radical is ortho to the amide group.
- An arylamine may be also employed, as an antioxidant, in conjunction with the anthranilamide-type compound.
- An arylthiazine may be used in conjunction with the antioxidant.
- additives such as phosphate esters or phosphite esters, dimer acids (dilinoleic acid) and the like are also incorporated into the ester lubricating oil for the purpose of improving its extreme pressure, antiwear and/ or load carrying properties. If desired, still further additives may be incorporated for the purpose of reducing acidity or minimizing acidity increases during usage of the oil.
- Turbine engines are customarily employed in aircraft today. They are, however, subjected to extreme temperatures, and excessive corrosion difliculties are encountered because of the bearings and seals employed in such engines. Alloyed bearings are customarily used in such engines and the seals which are employed to retain the oil in the engine are also subjected to extremes of temperatures, which conditions necessitate the employment of highly specialized synthetic ester oils. Heretofore these oils have been improved by the use of minor amounts, i.e. of the order of 0.01 up to as high as 5.0 wt. percent of various special purpose additives, in an effort to overcome some of the deficiencies of the synthetic ester oils. The severity of operating conditions far exceeds those encountered in internal combustion automotive engines.
- the synthetic neutral saturated carboxylic acid ester lubricants have employed phenothiazine or the nuclearly substituted C C alkyl derivatives thereof as an antioxidant. See, U.S. Pat. 3,218,256, column 2, as well as British Pat. 824,114, which latter mentioned patent also shows the use of benzotriazole in such capacity with or without the use of phenothiazine. Additionally, amine antioxidants as shown in column 3 of U.S. Pat. 3,247,111 have been employed in conjunction with the phenothiazine and benzotriazoles for the purpose of inhibiting the undue rapid oxidation of such synthetic ester oils. Phenolic antixodiants have been employed as well.
- the load carrying additives which have been employed are generally the phosphate esters and phosphite esters; see, for example, U.S. Pats. 2,971,912, column 6; 3,215,720, column 1; and 3,247,111, column 4.
- dibutyl posphite and tricresyl phosphate have been widely used for the purpose of imparting antiwear or load carrying characteristics to the synthetic ester oils although any of the specific materials mentioned in the last three stated U.S. patents are also applicable conventionally for imparting load carrying properties to such oils.
- 3,247,111 most often are N-phenyl alpha naphthylamine, N-phenyl beta naphthylamine or p,p-di-isooctyl diphenylamine, although any of the aromatic amines mentioned therein (lines 36-48) may be used in the instant novel oil compositions.
- the synthetic neutralized saturated carboxylic acid ester lubricating oils which serve as the base oil and to which one or more of the aforementioned additives are added may be of several kinds. Numerous patents disclose these types of ester oils as being conventionally produced and used as shown by the following patents: 1,993,736; 2,249,768; 2,766,273; 2,015,088; 2,723,286; 2,743,234; 2,575,196; 3,218,256 and 3,360,465.
- ester base oils As examples of the specific types of oils to which the present invention relates, the following ester base oils are described; the triester and tetraester lubricating oils, the complex ester oils and the diester oils all of which are conventional articles of commerce.
- Such oils have heretofore all been used at one time or another and are still used in turbine engines that power aircraft. These engines are of the turbo jet, turbo prop, turbo fan and supersonic jet transport types. Because these engines and drive mechanisms for powering aircraft are all operated under extremely wide temperature ranges, the use of synthetic ester oils is presently almost an absolute necessity.
- esters as referred to in the above patents, can be described as being formed in the following manner.
- the triester and tetraester types are formed by reacting tri and tetra polyols such as trimethylol propane, pentaerythritol, trimethylol ethane, and higher trimethylol alkanes, and so forth, with C C e.g. C C normal or branched chain monocarboxylic acid or mixtures of two or more of such types of acids.
- n-butanoic acid valeric acid, caproic acid, heptanoic acid, caprylic acid, pivalic acid, 2-ethyl hexanoic acid, pelargonic acid, lauric acid and the like.
- the hexaesters of dipentaerythritol are also useful alone or admixed with the aforementioned tetraesters of monopentaerythritol.
- Complex or polyester oils are also conventionally used. These are formed by esterifying polyols such as the glycols, the neopolyols previously mentioned, and the straight chain alkane diols with such dicarboxylic acids as succinic, glutaric, adipic, 2,2,4-trimethyl adipic acid, pimelic, suberic, azelaic, sebacic, brassylic acids, and dibasic dimer acids of oleic and/or linoleic acids.
- the diols or polyethoxylated diols of C C alkylene groups or mixtures thereof are also employed in preparing polyesters from the dibasic acids.
- the complex esters and their methods of preparation are conventional and are disclosed in representative US. patents such as 2,575,195 and 2,743,234, columns 36, inclusive.
- diesters are conventionally formed from monohydric alcohols and dibasic acids. There are numerous references in the literature to their formation. These diesters are formed from the same dibasic acids used in connection with the formation of the complex esters hereinbefore described.
- the alcohols are such alcohols as the 0x0 alcohols or 0x0 alcohol mixtures such as C C oxo alcohols, or from 2-ethyl hexyl alcohols, n-octyl alcohol, nonyl alcohol,
- the synthetic ester oils or blends thereof generally have physical properties and specifications as follows: a viscosity index of at least 100, a pour or freezing point not exceeding 40 F., a boiling or decomposition temperature of at least 600 F., a Cleveland Open Cup Flash 'Point of at least 400 F., and a kinematic viscosity of less than 10 centistokes at 210 F.
- the supersonic turbine engine oils have a more exacting specification and requirement.
- a viscosity index of at least 100 a pour or freezing point not exceeding 65 F., a boiling or decomposition temperature of at least 600 F., a Cleveland Open Cup Flash Point of at least 450 F., and a kinematic viscosity of less than 5.5 to 6.0 centistokes at 210 F.
- the novel additive incorporated into the synthetic ester oils in accordance with the presently discovered advance in the art is applicable to the more generally used synthetic aviation ester oils of less exacting specification as well as to the more exacting requirements of the supersonic aviation turbine ester oils.
- the acidity of the ester oil is increased with continued use even though conventional nitrogen-containing additives (aromatic amino compounds) have been used as antioxidants therein.
- aromatic amino compounds aromatic amino compounds
- the use of the aminobenzamide-type compounds not only reduces the acidity and viscosity increase during oil usage but additionally dramatically reduces corrosion of copper and magnesium as well as that of other metals present in the turbine engines.
- R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C -C acyl, or phenyl, and R is hydrogen, C -C alkyl or halo C -C alkyl.
- typical alkyl radicals are methyl, ethyl, isopropyl, n-proply, butyl, hexyl, octyl, decyl, or dodecyl, of either straight chain or branched chain configuration;
- typical phenalkyl radicals are benzyl, phenethyl, phenpropyl, etc.;
- typical cycloalkyl radicals are cyclohexyl and cyclopentyl;
- typical acyl radicals are acetyl, propionyl, butyryl, lauroyl, caproyl, capryl, caprylyl, etc.; and halo alkyl may be fiuoro or chloro mono or di-substituted methyl, ethyl, etc., i.e.
- Orthoaminobenzamide anthranilamide
- metaaminobenzamide may be employed.
- Other useful compounds are:
- the synthetic ester oils will contain between about 0.01 and 5.0 wt. percent, preferably between about 0.05 and about 0.2 wt. percent. Such small amounts do not necessitate a high degree of oil solubility of the anthranilamide-type component.
- the solubility of anthranilamide, per se, is sufficiently high in ester oils that it is unnecessary to substitute onto either the amino or amido nitrogen, an alkyl or cycloalkyl radical for the purpose of improving the oil solubility of the anthranilamide.
- Anthranilamide, or its simple hydrocarbon substituted or chlorhydrocarbon substituted derivatives find great utility when these are used in association with the usual aromatic amino hydrocarbon antioxidants heretofore employed.
- these compounds are also of quite high effectiveness in passivating or inhibiting metals such as copper and/or magnesium when used in association with mono or di, or mixed mono and dialkyl phosphate or phosphite esters or the primary amine salts of dibasic or monobasic chloralkyl-phosphoric acid as described in U.S. Pat. 2,858,332.
- One useful antiwear load bearing phosphate ester is a mixture of mono and dimethyl phosphate esters neutralized with a branched chain mixed primary C -C alkyl amine.
- Other similar types of acidic phosphate or phosphite esters neutralized with primary or secondary long chain alkyl amines are also equally eificacious.
- a mixture of C -C mono and di'alkyl hydrogen phosphates partially or completely neutralized with Primene 81-R (a commercial mixture of C -C alkyl primary amine) is also suitable.
- the conventional materials previously employed such as phenothiazine, the benzotriazoles, quinizarin and its analogues, and the primary and secondary aromatic amino antioxidants may also be used in association with the anthranilamides or their nitrogen substituted hydrocarbon derivatives.
- the amount employed of the conventional additives are those which have here tofore been employed. These amounts range between about 0.01 and about 5.0 wt. percent. -It has, however, been discovered that it is unnecessary to employ benzotriazole, heretofore used as a specific copper corrosion inhibitor, when one employs the aminobenzamide or its derivatives as a metal passivator. Benzotriazole, while effectively minimizing metal corrosion, markedly increases magnesium corrosion and increases total acidity buildup.
- Anthranilamide may be prepared by a number of processes but the one which is generally employed involves the reaction of anthranilic acid with chloro carbonic esters of the lower aliphatic alcohols to form isatoic anhydride which is then reacted with ammonia or with a suitable primary or secondary amine to produce anthranilamide or the amino nitrogen substituted alkyl derivatives thereof.
- the amino nitrogen is substituted as heretofore set forth instead of using anthranilic acid
- the corresponding N-alkyl 0r N-cycloalkyl derivatives of anthranilic acid are used.
- test data have been obtained using standard tests for determining the suitability of the aviation ester lubricants for their intended use.
- One of the tests which have been employed is the so-called Oxidation/ Corrosion Stability Test. This is a standardized test procedure described in Specification FTMSTD 791 Method 5308. Briefly, this test involves blowing air through the oil to be tested at a specified temperature for a specified length of time (usually 347 F. for 72 hours or 400 F. for 72 hours) in the presence of metal specimens consisting of aluminum, magnesium, steel and copper tied together to form a square with a silver specimen inserted as a diagonal between the copper and steel and the aluminum and magnesium junctions.
- the number of hours of test and the temperatures can be varied from those above specified but if and when such is the case in connection with the following tests, expressed mention of this deviation or variation will be made.
- the test is a severe test, the results being affected by the specific chemical nature of the ester base oil and by the nature of the additive or additives present in the oil during test.
- the test is designed to measure the attack on the various metal specimens, the percentage of change in viscosity measured in centistokes at F. (usually this is an increase in viscosity), the total increase in acidity meas ured as total acid number (TAN) measured in milligrams of KOH per gram of oil.
- TAN total acid number
- the attack on the various metals is measured in milligrams per square centimeter (although in some cases a protection film or deposit forms resulting in a plus value instead of a minus value) and finally, although not always, the amount of sludge or insolubles formed in grams per 100 mls. of oil is also determined.
- EXAMPLE 1 The following compounded synthetic aviation oil was prepared: 100 parts constituted the tetraester and the hexaester of a mixture of 90% monopentaerythritol and 10% dipentaerythritol poly esterified with mixed C -C normal alkanoic acids. Based on the 100 parts of the ester base oil, (this and all subsequent oil compositions are also based on 100 parts by weight of ester base oil) the following additives (also in parts by weight per 100 parts of base oil) were added:
- EXAMPLE 5 Same base composition as in Example 4 but contains, in addition, 0.1 quinizarin.
- EXAMPLE 6 35 parts monopentaerythritol ester of a mixture of C -C normal alkanoic acids
- EXAMPLE 8 50 parts of base oil of Example 1 (without additives);
- TAB LE Used oil Percent Corrosion, change in Total acid .8 ase oil, Add. mg./em. viscosity, number, Example amount, increase increase- Example N0. N0. Additives pts. Cu Mg cs. at 100 F. Mg-KOH/gm.
- a lubricating oil composition comprising a major portion of a synthetic neutral saturated carboxylic acid ester lubricating oil, and an amount, sufficient to inhibit metal corrosion, of an amino-benzamide having the formula:
- R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C -C acyl, or phenyl and R is hydrogen, C -C alkyl, or halo C -C alkyl.
- a lubricating oil composition comprising a major portion of a synthetic neutral saturated carboxylic acid ester lubricating oil, an amount, sufiicient to inhibit oxidation, of an aromatic amine antioxidant, and an amount, sufficient to inhibit metal corrosion, of an aminobenzamide having the formula:
- R and R are each hydrogen, C -C alkyl, phenyl, phenalkyl or cycloalkyl, R and R are each hydrogen, C -C alkyl, C C acyl, or phenyl and R is hydrogen, C -C alkyl, or halo C -C alkyl.
- An oil composition as in claim 7 which also contains phenothiazine and the aromatic amine is p,p-dioctyl diphenylamine.
- ester oil is the tetraester of pentaerythritol with a mixture of C -C normal alkanoic acids.
- An oil composition as in claim 15 wherein the aryl- W. J. SHINE, Assistant Examiner thiazine is phenothiazine, the aromatic amine is p,p'-dioctyl 10 diphenylamine and the composition also contains an amine addition salt of a phosphorus ester.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83661369A | 1969-06-25 | 1969-06-25 | |
| US3643670A | 1970-05-11 | 1970-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3585137A true US3585137A (en) | 1971-06-15 |
Family
ID=26713171
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US836613A Expired - Lifetime US3585137A (en) | 1969-06-25 | 1969-06-25 | Synthetic ester lubricating oil composition |
| US00036436A Expired - Lifetime US3720612A (en) | 1969-06-25 | 1970-05-11 | Synthetic ester lubricating oil compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00036436A Expired - Lifetime US3720612A (en) | 1969-06-25 | 1970-05-11 | Synthetic ester lubricating oil compositions |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US3585137A (enrdf_load_stackoverflow) |
| BE (1) | BE759166A (enrdf_load_stackoverflow) |
| DE (1) | DE2029906C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2047933B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1256999A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857791A (en) * | 1972-05-25 | 1974-12-31 | Cities Service Oil Co | Lubricating oil additive and lubricating oil compositions containing same |
| US3984337A (en) * | 1973-07-02 | 1976-10-05 | Mobil Oil Corporation | Lubricant compositions containing naphthylamino benzamide antioxidants |
| US4107054A (en) * | 1977-06-27 | 1978-08-15 | Continental Oil Company | Lubricating oil compositions |
| US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
| EP0320281A3 (en) * | 1987-12-11 | 1989-10-25 | Exxon Research And Engineering Company | Corrosion inhibitor |
| US5560848A (en) * | 1995-05-26 | 1996-10-01 | Exxon Research And Engineering Company | Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236) |
| US5780400A (en) * | 1996-10-07 | 1998-07-14 | Dover Chemical Corp. | Chlorine-free extreme pressure fluid additive |
| US5798321A (en) * | 1995-05-23 | 1998-08-25 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US6043199A (en) * | 1997-08-26 | 2000-03-28 | Exxon Research And Engineering Co. | Corrosion inhibiting additive combination for turbine oils |
| CN103703114A (zh) * | 2011-05-31 | 2014-04-02 | 卢布里佐尔公司 | 具有改进tbn保持性的润滑组合物 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1392600A (en) * | 1971-11-24 | 1975-04-30 | Exxon Research Engineering Co | Lubricating oil compositions |
| BE795113A (fr) * | 1972-02-07 | 1973-05-29 | Tenneco Chem | Esters synthetiques lubrifiants pour compresseurs d'air a mouvement alternatif |
| US3979308A (en) * | 1974-03-27 | 1976-09-07 | Texaco Inc. | Lubricant compositions with improved viscosity index |
| US3931023A (en) * | 1974-07-22 | 1976-01-06 | Fmc Corporation | Triaryl phosphate ester functional fluids |
| US4178260A (en) * | 1974-10-31 | 1979-12-11 | Exxon Research & Engineering Co. | Ester based metal working lubricants |
| US3986965A (en) * | 1975-10-31 | 1976-10-19 | Monsanto Company | Ester base lubricating compositions having improved oxidative resistance |
| GB1583873A (en) * | 1976-05-05 | 1981-02-04 | Exxon Research Engineering Co | Synthetic lubricating oil composition |
| FR2414547A1 (fr) * | 1978-01-11 | 1979-08-10 | Exxon Research Engineering Co | Composition d'huile lubrifiante synthetique de type ester |
| US4514312A (en) * | 1982-07-22 | 1985-04-30 | Witco Chemical Corporation | Lubricant compositions comprising a phosphate additive system |
| US4514311A (en) * | 1983-05-09 | 1985-04-30 | Texaco Inc. | Wear-resistant aircraft engine lubricating oil |
| US4661271A (en) * | 1984-08-09 | 1987-04-28 | Mobil Oil Corporation | Friction reducing, antiwear additives |
| US4780229A (en) * | 1984-10-01 | 1988-10-25 | Akzo America Inc. | High temperature polyol ester/phosphate ester crankcase lubricant composition |
| US4879052A (en) * | 1987-11-05 | 1989-11-07 | Akzo America Inc. | High temperature polyol ester/phosphate ester crankcase lubricant composition |
| US5750478A (en) * | 1995-12-22 | 1998-05-12 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid |
| US5789358A (en) * | 1995-12-22 | 1998-08-04 | Exxon Research And Engineering Company | High load-carrying turbo oils containing amine phosphate and thiosemicarbazide derivatives |
| CA2311385A1 (en) * | 1998-01-09 | 1999-07-15 | Paul Joseph Berlowitz | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US9969950B2 (en) * | 2012-07-17 | 2018-05-15 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless TBN sourcces |
| US10077922B2 (en) * | 2014-05-12 | 2018-09-18 | Panasonic Intellectual Property Management Co., Ltd. | Compressor and refrigeration cycle device using same |
| CN106460840B (zh) * | 2014-05-12 | 2019-11-05 | 松下知识产权经营株式会社 | 压缩机和使用其的制冷循环装置 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2723286A (en) * | 1951-10-06 | 1955-11-08 | Exxon Research Engineering Co | Reduction of acidity in synthetic ester lubes with ethylene carbonate |
| US2839468A (en) * | 1956-05-10 | 1958-06-17 | California Research Corp | Jet turbine lubricant composition |
| BE557513A (enrdf_load_stackoverflow) * | 1956-05-14 | |||
| NL247300A (enrdf_load_stackoverflow) * | 1959-01-14 | |||
| US3247111A (en) * | 1963-04-08 | 1966-04-19 | Socony Mobil Oil Co | High temperature jet lubricant |
-
0
- BE BE759166D patent/BE759166A/xx not_active IP Right Cessation
-
1969
- 1969-06-25 US US836613A patent/US3585137A/en not_active Expired - Lifetime
-
1970
- 1970-05-11 US US00036436A patent/US3720612A/en not_active Expired - Lifetime
- 1970-06-12 GB GB1256999D patent/GB1256999A/en not_active Expired
- 1970-06-18 DE DE2029906A patent/DE2029906C3/de not_active Expired
- 1970-06-24 FR FR7023451A patent/FR2047933B1/fr not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857791A (en) * | 1972-05-25 | 1974-12-31 | Cities Service Oil Co | Lubricating oil additive and lubricating oil compositions containing same |
| US3984337A (en) * | 1973-07-02 | 1976-10-05 | Mobil Oil Corporation | Lubricant compositions containing naphthylamino benzamide antioxidants |
| US4107054A (en) * | 1977-06-27 | 1978-08-15 | Continental Oil Company | Lubricating oil compositions |
| US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
| EP0320281A3 (en) * | 1987-12-11 | 1989-10-25 | Exxon Research And Engineering Company | Corrosion inhibitor |
| US4877541A (en) * | 1987-12-11 | 1989-10-31 | Exxon Research And Engineering Company | Corrosion inhibitor |
| US5798321A (en) * | 1995-05-23 | 1998-08-25 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US5560848A (en) * | 1995-05-26 | 1996-10-01 | Exxon Research And Engineering Company | Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236) |
| WO1999035216A1 (en) * | 1996-02-09 | 1999-07-15 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US5780400A (en) * | 1996-10-07 | 1998-07-14 | Dover Chemical Corp. | Chlorine-free extreme pressure fluid additive |
| US5939366A (en) * | 1996-10-07 | 1999-08-17 | Dover Chemical Corp. | Lubrication process using chlorine-free lubricant |
| US6043199A (en) * | 1997-08-26 | 2000-03-28 | Exxon Research And Engineering Co. | Corrosion inhibiting additive combination for turbine oils |
| CN103703114A (zh) * | 2011-05-31 | 2014-04-02 | 卢布里佐尔公司 | 具有改进tbn保持性的润滑组合物 |
| US9222051B2 (en) | 2011-05-31 | 2015-12-29 | The Lubrizol Corporation | Lubricating composition with improved TBN retention |
| CN103703114B (zh) * | 2011-05-31 | 2016-02-10 | 路博润公司 | 具有改进tbn保持性的润滑组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2047933B1 (enrdf_load_stackoverflow) | 1974-05-03 |
| US3720612A (en) | 1973-03-13 |
| DE2029906A1 (de) | 1971-01-07 |
| BE759166A (fr) | 1971-05-19 |
| DE2029906B2 (de) | 1980-09-04 |
| GB1256999A (enrdf_load_stackoverflow) | 1971-12-15 |
| FR2047933A1 (enrdf_load_stackoverflow) | 1971-03-19 |
| DE2029906C3 (de) | 1981-06-04 |
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