US3344068A - Ester base lubricants - Google Patents
Ester base lubricants Download PDFInfo
- Publication number
- US3344068A US3344068A US457222A US45722265A US3344068A US 3344068 A US3344068 A US 3344068A US 457222 A US457222 A US 457222A US 45722265 A US45722265 A US 45722265A US 3344068 A US3344068 A US 3344068A
- Authority
- US
- United States
- Prior art keywords
- composition
- percent
- phenothiazine
- ester base
- ester
- 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 description 41
- 239000000314 lubricant Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 55
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 150000003336 secondary aromatic amines Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 6
- BIJMTMUECQSXDH-UHFFFAOYSA-N 10-benzyl-3,7-dioctylphenothiazine Chemical compound C12=CC=C(CCCCCCCC)C=C2SC2=CC(CCCCCCCC)=CC=C2N1CC1=CC=CC=C1 BIJMTMUECQSXDH-UHFFFAOYSA-N 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 239000010687 lubricating oil Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- -1 N-substituted phenothiazine Chemical class 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000009472 formulation Methods 0.000 description 12
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 229950000688 phenothiazine Drugs 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- NUCFNMOPTGEHQA-UHFFFAOYSA-N 3-bromo-2h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C(Br)=NNC2=C1 NUCFNMOPTGEHQA-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229940067597 azelate Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920006389 polyphenyl polymer Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical class OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000002990 phenothiazines Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZUMHPFURPMPMSM-UHFFFAOYSA-N 1-phenyl-10h-phenothiazine Chemical compound C=12NC3=CC=CC=C3SC2=CC=CC=1C1=CC=CC=C1 ZUMHPFURPMPMSM-UHFFFAOYSA-N 0.000 description 1
- GCQKBIIYEXTNCP-UHFFFAOYSA-N 10-(2-methylphenyl)-3,7-dioctylphenothiazine Chemical compound C1(=C(C=CC=C1)N1C2=CC=C(C=C2SC=2C=C(C=CC12)CCCCCCCC)CCCCCCCC)C GCQKBIIYEXTNCP-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- FIFXMZHMRFLFLK-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methylaminomethyl)phenol Chemical compound CNCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FIFXMZHMRFLFLK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical class OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- YZCUTUISEQOGKX-UHFFFAOYSA-N 3,7,10-trioctylphenothiazine Chemical compound C(CCCCCCC)N1C2=CC=C(C=C2SC=2C=C(C=CC12)CCCCCCCC)CCCCCCCC YZCUTUISEQOGKX-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- VSYHLAOXGCCECX-UHFFFAOYSA-N 5-(3,7-dioctylphenothiazin-10-yl)pentanenitrile Chemical compound C1=C(CCCCCCCC)C=C2SC3=CC(CCCCCCCC)=CC=C3N(CCCCC#N)C2=C1 VSYHLAOXGCCECX-UHFFFAOYSA-N 0.000 description 1
- GHUDJFJZFUVPIQ-UHFFFAOYSA-N 5-phenyl-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2C=CC=CC=2)=N1 GHUDJFJZFUVPIQ-UHFFFAOYSA-N 0.000 description 1
- VPTQEOQBSABCKV-UHFFFAOYSA-N 5-pyridin-2-yl-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2N=CC=CC=2)=N1 VPTQEOQBSABCKV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008583 Chloroma Diseases 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- ZWYAVGUHWPLBGT-UHFFFAOYSA-N bis(6-methylheptyl) decanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCCCCCC(=O)OCCCCCC(C)C ZWYAVGUHWPLBGT-UHFFFAOYSA-N 0.000 description 1
- WLLCYXDFVBWGBU-UHFFFAOYSA-N bis(8-methylnonyl) nonanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC(C)C WLLCYXDFVBWGBU-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 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
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- HMMPCBAWTWYFLR-UHFFFAOYSA-N n-pyridin-2-ylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=N1 HMMPCBAWTWYFLR-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- WNPWLKMMKYONQE-UHFFFAOYSA-N nonanoic acid propane Chemical compound C(CCCCCCCC)(=O)O.C(CCCCCCCC)(=O)O.C(CCCCCCCC)(=O)O.CCC WNPWLKMMKYONQE-UHFFFAOYSA-N 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
-
- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
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- 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
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- 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
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/30—Heterocyclic compounds
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- 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
- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- 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
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- 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
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- 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
- C10M2223/042—Metal salts thereof
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- 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
- C10M2223/047—Thioderivatives not containing metallic elements
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- 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
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/063—Ammonium or amine salts
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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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/02—Unspecified siloxanes; Silicones
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- 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
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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- C—CHEMISTRY; METALLURGY
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- 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
- C10N2040/12—Gas-turbines
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- 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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to an ester base lubricant having good oxidation stability which is particularly useful for lubricating gas turbine engines.
- Oils of the invention comprise major amounts of an ester base oil and minor amounts suflicient to enhance the oxidation stability of (1)
- the hydrocarbyl group can be alkyl, aryl, alkaryl, or aralkyl.
- N-substituted phenothiazines of the present invention preferably have one alkyl or alkoxy'radical as substituent in each aromatic ring comprising the phenothiazine molecule and 3,7-substitution is most preferred.
- Preparation of N-substituted phenothiazines is described, for example, in British Patent No. 873,066, issued July 19, 1961, to Shimmin and Mofiatt.
- N-substituted phenothiazines which are particularly useful for the purposes of the present invention are -methyl-3,7-dioctyl phenothiazine, lO-n-butyl-3,7-dioctyl phenothiazine, 10-n-octyl- 3,7-dioctyl phenothiazine, l0-phenyl-3,7-dioctyl phenothiazine, 10-tolyl-3,7-dioctyl phenothiazine, lO-cyanoethyl 3,7 dioctyl phenothiazine, lO-cyanopropy1-3,7- dioctyl phenothiazine, 10-cyanobutyl-3,7-dioctyl phenothiazine, l0-benzyl-3,7-dioctyl phenothiazine,
- Any secondary aromatic amine may be used in conjunction with the N-substituted phenothiazines for the purposes of the present invention; certain diphenylamines and N-aryl naphthylamines are, however, preferred.
- Suitable diphenylamines are unsubstituted diphenylamineand 'those having an alkyl or alkoxy radical containing from to 20 carbon atoms, include phenyl-ot-naphthylamine, phenyl-B-naphthylamine and 13,,3-dinaphthylamine; phenyl phenothiazine, lO-benzyl-Bfl-dibutoxy phenothiazine and 3,344,068 Patented Sept.
- ester comprising the major proportion of the present ester base composition is a simple ester it is preferable to use diphenylamines, e.g., p,p'-dioctyldiphenylamine, especially in admixture with N-aryl naphthylamines, as the secondary aromatic amine, Whereas N-aryl naphthylamines, e.g. phenyl-a-naphthylamine, appear to be preferable for use with ployesters.
- diphenylamines e.g., p,p'-dioctyldiphenylamine
- N-aryl naphthylamines e.g. phenyl-a-naphthylamine, appear to be preferable for use with ployesters.
- the additives of the invention are employed in minor amounts sufiicient to enhance the oxidation stability of the oil; in general, they will be present in an amount of 0.05 to 10% by weight, preferably 0.1 to 5% by weight of the final composition.
- Esters suitable as the ester base in the composition of the present invention are simple esters, complex esters, polyesters, or mixtures thereof to which may be added other additives, depending upon the properties desired for the composition and the temperature conditions under which it is to be used.
- simple ester is meant an ester formed between an aliphatic dicarboxylic acid and an aliphatic monohydric alcohol, preferred simple esters being formed from an aliphatic dicarboxylic acid containing from 6 to .10 carbon atoms in the molecule and a branched chain monohydric alcohol containing from 6 to 12 carbon atoms in the molecule, especially those alcohols having no hydrogen on the beta carbon atom.
- Examples of simple esters useful for the purposes of the present invention are diisooctyl sebacate, di(2-ethyl hexyl) sebacate, diisooctyl azelate, di(3,5,5-t-rimethyl hexyl) adipate, Z-ethyl hexyl-3,5,5-trimethyl hexyl sebacate and 2,2,4-trimethyl pentyl azelate.
- complex ester an ester formed from various combinations of an aliphatic dicarboxylic acid, a glycol or polyglycol and either or both of an aliphaticmonohydric alcohol 'and an aliphatic monocarboxylic acid.
- AD GD
- A(DG)nM A(DG)nM
- MG(DG)nM a complex ester structure
- A, D, G and M represent the esterification residues from an aliphatic monohydric alcohol, an aliphatic dicarboxylic acid, a glycol or polyglycol and an aliphatic monocarboxylic acid respectively and n is a number from 1 to ethyl hexyl alcohol, caproic acids, pelargonic acid, capric acid, neopentyl glycol, ethylene glycol, propylene glycol, polyglycols such as polyethylene glycols, sebacic acid, adipic acid, azelaic acid and pimelic acid.
- polyesters in meant esters made from aliphatic alcohols having therein at least 3 hydroxyl groups, for example esters made from trimethylol propane. Tetraesters such as pentaerythritol tetraesters of dimers or trimers of the same and dipentaerythritol esters of C -C acids, especially C C acids, are particularly preferred. These esters are commerically available from Hercules Chemical Company.
- Thickeners may also be added to oils of the invention to improve viscosity properties.
- Suitable thickeners are polymers of esters of acrylic or an alkyl substituted acrylic acid, for example lauryl methacrylate, or an ether of a polyoxyalkylene glycol of the general formula R O(R O),,R wherein R is an alkyl group, R is hydrogen or an alkyl group, R is an alkylene group of 2 to 4 carbon atoms and n is a number greater than unity.
- Suitable compounds are marketed under the trade name Uncon, specific examples being b13385, b13525, LB625.
- Alsosuitable are copolymers of propylene oxide and ethylene oxide marketed under the trade name Gxilube, e.g. Oxilube /140.
- the thickeners may be used in proportions of up to 40% by weight calculated on the final lubricant composition depending upon the viscomet-ric properties'required for said lubricant.
- ester base compositions of the present invention may additionally contain extreme pressure additives, additional antioxidants, metal deactivators, anti-corrosion agents, anti-foaming agents, dyestuffs, and other additives chloromethylphosphonic acid salts of C1842 tertiary alkyl primary amines.
- a wide variety of materials may be used as metal deactivators and anti-corrosion agents, depending on the known to be suitable for use with ester base lubricant 5 metal or metals with which the ester base composition formulations. of the present invention will come into contact.
- Materials Suitable E.P. agents are esters of acids of phosphorus, which are particularly useful as affording protection of, such as triphenyl phosphorothionate, tritolyl phosphoro for example, copper, copper alloys and silver against corthionate, and trixylyl phosphorothionate; phosphate esrosive attack are the triazoles, for example, 1,2,3-benzters e.g.
- triphenyl phosphate and tritolyl phosphate may triazole, methyl-1,2,3-benztriazole, 3-amino-5-methyl-1, also be used but are preferably used in conjunction with 2,4-triazole, especially 3-amino-5-phenyl-1,2,4-triazole, a minor proportion e.g.
- diaryl haloalkyl phosphates are minor amounts, e.g. up to 1% by weight, preferably e.g. diphenyl-2,2-bis(chloromethyl)3-chloromethyl phosup to 0.5% by weight of pyridylamines, particularly diphorothionate.
- pyridylamines particularly diphorothionate.
- BF. additives which pyridylarnines, e.g. 2,2'-dipyridylamine.
- chlorinated dior polyphenyls i.e. dior adipic acid are useful as inhibitors of lead corrosion phenyls, terphenyls, higher polyphenyls or mixtures therewhile metal petroleum sulfonates, e.g. calcium petroleum of containing at least one chlorine atom attached directsulfonate, are useful as rust inhibitors.
- metal petroleum sulfonates e.g. calcium petroleum of containing at least one chlorine atom attached directsulfonate
- chlorinated di Suitable antirfoaming agents are the polydimethyl siloxor polyphenyls sold under the trade name Arochlor.
- ester base compositions of the present invention are sub- To illustrate the ester base compositions of the present stituted oxetane polymers, i.e. polymers prepared from invention, compositions as shown in Table I (Examples oxetanes having the formula I-III and VII-VIII) were formulated and thereafter compared with corresponding compositions (Examples IV- XaC 0H, VI and IX-X) not in accordance with the present invention by means of one or more of three test procedures, viz. the oxidation/corrosion test at 175 C.
- compositions in accordance with are chosen from hydrogen, chlorine or bromine, e.g. 3,3- the Pmsent invention and Comparative eXamPIBS not in bis(chloromethyl)oxetane. accordance with the present invention were stored in con- A class of BF.
- additives which are particularly useful miners having loosely fitting lids, maintained at p for imparting extra resistance to extreme pressure contures 01 'afld and examined PeFiOdiCaHY ditions are the monochloromethylphosphonic acid salts after periods up to three months for the presence of susof tertiary alkyl primary amines, for example the monopended matter.
- Aroclor 3 1254 percent wt "Irlphenyl phosphorothionate, percent Wt. s-methyl benzotriazole, p.p.m 3-an1ino-5-anilido-l,2,4-trlazole p p Azelaic acid, percent wt. Silicone MS 200 12500, p.p. Polymer of 3,3 -bis(chlorom l) (m 450, Cl content 45%), percent wt l C C"; acid esters of pentaerythritol. 1 Copolymers of ethylene oxide and propylene oxide. Chlorinated diphenyl.
- Example XII gave less benzene insolubles, a small viscosity increase and a smaller acidity increase than did the composition of Example XIII, which comprised a simple ester and phenyl-a-naphthylamine in conjunction with an N- substituted phenothiazine.
- N-cyanoalkyl substituted phenothiazines suitable for the purposes of the present invention are those having up to 20, preferably from 2 to 8, carbon atoms in the alkyl chain of the cyano alkyl radical and preferably have one Condition of Sample after- Example No. 15 C. 80 C.
- Example XI which comprised a simple ester and a mixture of secondary aromatic amines in conjunction with an N-substituted phenothiazine, gave less benzene insolubles, a smaller viscosity increase and a smaller acidity increase than did the composition of Example XII, which comprised a simple ester and a diphenylamine in conjunc- TABLE VII Example/ Composition, percent wt.
- Arochlor 1254 a chlorinated diphenyl) Azelaic acid 3-amino-5-phenyl-1,2,4-triazole (p.p.m.) Silicone MS 200/12500 (p.p.m.)
- Example XV which comprises an N-cyanoalkyl substituted phenothiazine and a secondary aromatic amine gives a performance in the Rolls Royce Blown Oxidation Test which is at least as good as that given by the composition of Example XVI (a composition of the present invention) comprising 10-benzyl-3,7-dioctyl phenothiazine.
- Example XXII A further example still (Example XXII) of a composition in accordance with the present invention is given at Table X.
- Example XXII When subjected to the Rolls Royce Blown Oxidation Test carried out at a test temperature of 225 C., the formulation of Example XXII (Table X) gave only 0.01% weight benzene insolubles and an increase in acidity of 4.9 mg. KOH/ g. Furthermore the composition gave no deposition after storage for twelve weeks at a tem- Z8 perature of C. and has highly desirable load-carrying properties, giving an I.A.E.. gear rig scufiing load of 66 lbs. lever load under condition C of LP. Method No. 166 and a Ryder gear rig scufling load in excess of 3,300 lbs.
- a lubricating composition comprising a major amount of an ester base lubricating oil and minor amounts sufiicient to increase the oxidation stability of the oil of (1) 10-benzyl-3,7-dioctylphenothiazine, and
- composition of claim 1 wherein the secondary aromatic amine is a diphenylamine.
- composition of claim 1 wherein the secondary aromatic amine is a p,p-disubstituted diphenylamine.
- composition of claim 1 wherein the secondary aromatic amine is a N-aryl naphthylamine.
- composition of claim 1 wherein the secondary aromatic amine is phenyl-a-naphthylamine.
- a lubricating composition comprising a major amount of an ester base lubricating oil and about 0.1 to about 5% by weight of each of 10-benzyl-3,7-dioctylphenothiazine and phenyl-u-naphthylamine.
- a lubricating composition comprising a major amount of an ester base lubricating oil and about 0.1 to about 5% by weight of each of l0-benzyl-3,7-dioctylphenothiazine and p,p'-dioctyl diphenylamine.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Fixed Capacitors And Capacitor Manufacturing Machines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10263/64A GB1036695A (en) | 1964-03-11 | 1964-03-11 | Improvements in or relating to ester base compositions |
| GB2546664 | 1964-06-19 | ||
| GB3493064 | 1964-08-26 | ||
| GB4374764 | 1964-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3344068A true US3344068A (en) | 1967-09-26 |
Family
ID=27448040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US457222A Expired - Lifetime US3344068A (en) | 1964-03-11 | 1965-05-19 | Ester base lubricants |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3344068A (no) |
| BE (1) | BE660935A (no) |
| CH (1) | CH459427A (no) |
| DE (1) | DE1279270B (no) |
| DK (1) | DK105819C (no) |
| FR (1) | FR1432875A (no) |
| GB (1) | GB1036695A (no) |
| MY (1) | MY6700034A (no) |
| NL (1) | NL6503025A (no) |
| NO (1) | NO120647B (no) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539515A (en) * | 1968-04-03 | 1970-11-10 | Mobil Oil Corp | Lubricating oil compositions containing peroxide-treated phenothiazine as an antioxidant |
| US3869394A (en) * | 1971-06-11 | 1975-03-04 | Grace W R & Co | Lubricant composition and method |
| US3912727A (en) * | 1972-11-22 | 1975-10-14 | Grace W R & Co | Preparation of phenothiazines |
| US3925215A (en) * | 1973-05-11 | 1975-12-09 | Exxon Research Engineering Co | Antioxidant mixture comprising a mixture of phenothiazine oralkyl substituted phenothiazine and an oxidized diarylamine and lubricating oils containing said antioxidant mixture |
| US4203854A (en) * | 1974-02-20 | 1980-05-20 | The Ore-Lube Corporation | Stable lubricant composition containing molybdenum disulfide and method of preparing same |
| EP0286595A2 (de) * | 1987-04-08 | 1988-10-12 | Ciba-Geigy Ag | Schwefelhaltige Verbindungen als Antioxidantien für Schmiermittel und Elastomere |
| US4785095A (en) * | 1986-09-16 | 1988-11-15 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| WO1988009787A1 (en) * | 1987-06-09 | 1988-12-15 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US4915858A (en) * | 1987-06-09 | 1990-04-10 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US5024774A (en) * | 1987-06-09 | 1991-06-18 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US5034019A (en) * | 1988-06-23 | 1991-07-23 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5157118A (en) * | 1986-09-16 | 1992-10-20 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5178784A (en) * | 1986-09-16 | 1993-01-12 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5211862A (en) * | 1986-12-31 | 1993-05-18 | Ciba-Geigy Corporation | Substituted N-thiomethylphenothiazines as lubricant stabilizers |
| US5269954A (en) * | 1988-12-05 | 1993-12-14 | Elf France | Nitrogenous additives with an antioxidant action and lubricating compositions containing the said additives |
| WO1994010270A1 (en) * | 1992-10-30 | 1994-05-11 | Castrol Limited | Corrosion inhibiting lubricant composition |
| US5798321A (en) * | 1995-05-23 | 1998-08-25 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US6797677B2 (en) | 2002-05-30 | 2004-09-28 | Afton Chemical Corporation | Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587661A (en) * | 1952-03-04 | Chzchjcn | ||
| GB824521A (en) * | 1957-12-20 | 1959-12-02 | Shell Res Ltd | Improvements in or relating to hydrocarbon compositions |
| US2930758A (en) * | 1956-09-28 | 1960-03-29 | Texaco Inc | Ester-base lubricant containing anti-oxidant mixtures |
| US2971912A (en) * | 1956-05-14 | 1961-02-14 | Castrol Ltd | Lubricating oil compositions |
| US3014888A (en) * | 1957-12-20 | 1961-12-26 | Shell Oil Co | Stabilized hydrocarbon compositions |
| FR1296477A (fr) * | 1960-08-09 | 1962-06-15 | British Petroleum Co | Mélange lubrifiant |
| GB933505A (en) * | 1960-08-09 | 1963-08-08 | British Petroleum Co | Synthetic lubricants |
| US3218256A (en) * | 1959-01-14 | 1965-11-16 | Castrol Ltd | Lubricating compositions |
-
1964
- 1964-03-11 GB GB10263/64A patent/GB1036695A/en not_active Expired
-
1965
- 1965-03-10 NL NL6503025A patent/NL6503025A/xx unknown
- 1965-03-11 CH CH343465A patent/CH459427A/de unknown
- 1965-03-11 DE DES95904A patent/DE1279270B/de active Pending
- 1965-03-11 FR FR8802A patent/FR1432875A/fr not_active Expired
- 1965-03-11 DK DK124765AA patent/DK105819C/da active
- 1965-03-11 BE BE660935D patent/BE660935A/xx unknown
- 1965-03-11 NO NO65157170A patent/NO120647B/no unknown
- 1965-05-19 US US457222A patent/US3344068A/en not_active Expired - Lifetime
-
1967
- 1967-12-31 MY MY196734A patent/MY6700034A/xx unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2587661A (en) * | 1952-03-04 | Chzchjcn | ||
| US2971912A (en) * | 1956-05-14 | 1961-02-14 | Castrol Ltd | Lubricating oil compositions |
| US2930758A (en) * | 1956-09-28 | 1960-03-29 | Texaco Inc | Ester-base lubricant containing anti-oxidant mixtures |
| GB824521A (en) * | 1957-12-20 | 1959-12-02 | Shell Res Ltd | Improvements in or relating to hydrocarbon compositions |
| US3014888A (en) * | 1957-12-20 | 1961-12-26 | Shell Oil Co | Stabilized hydrocarbon compositions |
| US3218256A (en) * | 1959-01-14 | 1965-11-16 | Castrol Ltd | Lubricating compositions |
| FR1296477A (fr) * | 1960-08-09 | 1962-06-15 | British Petroleum Co | Mélange lubrifiant |
| GB933505A (en) * | 1960-08-09 | 1963-08-08 | British Petroleum Co | Synthetic lubricants |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3539515A (en) * | 1968-04-03 | 1970-11-10 | Mobil Oil Corp | Lubricating oil compositions containing peroxide-treated phenothiazine as an antioxidant |
| US3869394A (en) * | 1971-06-11 | 1975-03-04 | Grace W R & Co | Lubricant composition and method |
| US3912727A (en) * | 1972-11-22 | 1975-10-14 | Grace W R & Co | Preparation of phenothiazines |
| US3925215A (en) * | 1973-05-11 | 1975-12-09 | Exxon Research Engineering Co | Antioxidant mixture comprising a mixture of phenothiazine oralkyl substituted phenothiazine and an oxidized diarylamine and lubricating oils containing said antioxidant mixture |
| US4203854A (en) * | 1974-02-20 | 1980-05-20 | The Ore-Lube Corporation | Stable lubricant composition containing molybdenum disulfide and method of preparing same |
| US5157118A (en) * | 1986-09-16 | 1992-10-20 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| EP0326567B1 (en) * | 1986-09-16 | 1996-05-15 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US4785095A (en) * | 1986-09-16 | 1988-11-15 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5178784A (en) * | 1986-09-16 | 1993-01-12 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5319081A (en) * | 1986-12-31 | 1994-06-07 | Ciba-Geigy Corporation | Substituted N-thiomethyl phenothiazines as lubricant stabilizers |
| US5211862A (en) * | 1986-12-31 | 1993-05-18 | Ciba-Geigy Corporation | Substituted N-thiomethylphenothiazines as lubricant stabilizers |
| EP0286595A3 (en) * | 1987-04-08 | 1990-12-19 | Ciba-Geigy Ag | Sulfur containing compounds as antioxidants for lubricants and elastomers |
| EP0286595A2 (de) * | 1987-04-08 | 1988-10-12 | Ciba-Geigy Ag | Schwefelhaltige Verbindungen als Antioxidantien für Schmiermittel und Elastomere |
| US4915858A (en) * | 1987-06-09 | 1990-04-10 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US4798684A (en) * | 1987-06-09 | 1989-01-17 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| WO1988009787A1 (en) * | 1987-06-09 | 1988-12-15 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US5024774A (en) * | 1987-06-09 | 1991-06-18 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| US5034019A (en) * | 1988-06-23 | 1991-07-23 | The Lubrizol Corporation | N-substituted thio alkyl phenothiazines |
| US5269954A (en) * | 1988-12-05 | 1993-12-14 | Elf France | Nitrogenous additives with an antioxidant action and lubricating compositions containing the said additives |
| WO1994010270A1 (en) * | 1992-10-30 | 1994-05-11 | Castrol Limited | Corrosion inhibiting lubricant composition |
| US5681506A (en) * | 1992-10-30 | 1997-10-28 | Castrol Limited | Corrosion inhibiting lubricant composition |
| US5798321A (en) * | 1995-05-23 | 1998-08-25 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| WO1999035216A1 (en) * | 1996-02-09 | 1999-07-15 | Exxon Research And Engineering Company | Rust resistant turbo oils containing monobasic amino phosphates and dicarboxylic acids |
| US6797677B2 (en) | 2002-05-30 | 2004-09-28 | Afton Chemical Corporation | Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine |
Also Published As
| Publication number | Publication date |
|---|---|
| CH459427A (de) | 1968-07-15 |
| BE660935A (no) | 1965-09-13 |
| DK105819C (da) | 1966-11-14 |
| NO120647B (no) | 1970-11-16 |
| NL6503025A (no) | 1965-09-13 |
| DE1279270B (de) | 1968-10-03 |
| GB1036695A (en) | 1966-07-20 |
| MY6700034A (en) | 1967-12-31 |
| FR1432875A (fr) | 1966-03-25 |
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