US3869394A - Lubricant composition and method - Google Patents
Lubricant composition and method Download PDFInfo
- Publication number
- US3869394A US3869394A US379821A US37982173A US3869394A US 3869394 A US3869394 A US 3869394A US 379821 A US379821 A US 379821A US 37982173 A US37982173 A US 37982173A US 3869394 A US3869394 A US 3869394A
- Authority
- US
- United States
- Prior art keywords
- bis
- octylphenyl
- lubricant
- weight
- phenothiazine
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 195
- 239000000314 lubricant Substances 0.000 title claims abstract description 170
- 238000000034 method Methods 0.000 title abstract description 27
- -1 N-substituted phenothiazine Chemical class 0.000 claims abstract description 200
- 229950000688 phenothiazine Drugs 0.000 claims abstract description 54
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 18
- 230000001050 lubricating effect Effects 0.000 claims abstract description 15
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 41
- 150000003512 tertiary amines Chemical class 0.000 claims description 26
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 24
- 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 claims description 23
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 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 claims description 12
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 10
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 8
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 7
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 claims description 6
- CIEWGZJDEDBECJ-UHFFFAOYSA-N 1-chloro-4-methylbenzene Chemical compound [CH2]C1=CC=C(Cl)C=C1 CIEWGZJDEDBECJ-UHFFFAOYSA-N 0.000 claims description 6
- IHXYISPZQCLSIX-UHFFFAOYSA-N 6-o-(6-methylheptyl) 1-o-(8-methylnonyl) hexanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCC(=O)OCCCCCC(C)C IHXYISPZQCLSIX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 abstract description 35
- 125000003545 alkoxy group Chemical group 0.000 abstract description 22
- 230000003749 cleanliness Effects 0.000 abstract description 18
- 230000001590 oxidative effect Effects 0.000 abstract description 18
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 15
- 238000003860 storage Methods 0.000 abstract description 15
- 230000001965 increasing effect Effects 0.000 abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 9
- 125000001424 substituent group Chemical group 0.000 abstract description 9
- 150000003513 tertiary aromatic amines Chemical class 0.000 abstract description 8
- 125000002947 alkylene group Chemical group 0.000 abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 46
- 239000010802 sludge Substances 0.000 description 38
- 125000000217 alkyl group Chemical group 0.000 description 35
- 230000003647 oxidation Effects 0.000 description 26
- 238000007254 oxidation reaction Methods 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- 230000008859 change Effects 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 17
- 239000002253 acid Substances 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 150000003336 secondary aromatic amines Chemical class 0.000 description 12
- STGFANHLXUILNY-UHFFFAOYSA-N 3,7-dioctyl-10h-phenothiazine Chemical compound C1=C(CCCCCCCC)C=C2SC3=CC(CCCCCCCC)=CC=C3NC2=C1 STGFANHLXUILNY-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000005260 corrosion Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 230000007797 corrosion Effects 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical group C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 8
- 230000002079 cooperative effect Effects 0.000 description 8
- 150000003852 triazoles Chemical class 0.000 description 8
- 239000012964 benzotriazole Substances 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 150000002990 phenothiazines Chemical class 0.000 description 7
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 239000010687 lubricating oil Substances 0.000 description 6
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 4
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FSLSJTZWDATVTK-UHFFFAOYSA-N tris(6-methylheptyl) phosphate Chemical compound CC(C)CCCCCOP(=O)(OCCCCCC(C)C)OCCCCCC(C)C FSLSJTZWDATVTK-UHFFFAOYSA-N 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- IWASLBFJTMJYHF-UHFFFAOYSA-N 5-(2h-benzotriazol-5-ylmethyl)-2h-benzotriazole Chemical compound C1=CC2=NNN=C2C=C1CC1=CC2=NNN=C2C=C1 IWASLBFJTMJYHF-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005461 lubrication Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 2
- OAXZVLMNNOOMGN-UHFFFAOYSA-N bis(8-methylnonyl) decanedioate Chemical compound CC(C)CCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC(C)C OAXZVLMNNOOMGN-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
- WPHVRMGBXBGKTC-UHFFFAOYSA-N 1,2-dioctyl-10h-phenothiazine Chemical compound C1=CC=C2NC3=C(CCCCCCCC)C(CCCCCCCC)=CC=C3SC2=C1 WPHVRMGBXBGKTC-UHFFFAOYSA-N 0.000 description 1
- BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical compound S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-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 compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 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
- 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 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- OZRGLPAXIYOWIG-HZPUXBNGSA-N 4-nitrobenzylamine Chemical compound CC(C)C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CCCC[C@]4(C)[C@H]3CC[C@]12C)=O OZRGLPAXIYOWIG-HZPUXBNGSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010049940 Lipogranuloma Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- ZDWGXBPVPXVXMQ-UHFFFAOYSA-N bis(2-ethylhexyl) nonanedioate Chemical compound CCCCC(CC)COC(=O)CCCCCCCC(=O)OCC(CC)CCCC ZDWGXBPVPXVXMQ-UHFFFAOYSA-N 0.000 description 1
- LYHRWRRIMHVFFZ-UHFFFAOYSA-N bis(4-methylpentan-2-yl) hexanedioate Chemical compound CC(C)CC(C)OC(=O)CCCCC(=O)OC(C)CC(C)C LYHRWRRIMHVFFZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical group CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003562 lightweight material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 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
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated 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
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/304—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monohydroxy compounds, dihydroxy compounds and dicarboxylic acids only and having no free hydroxy or carboxyl 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/11—Complex polyesters
- C10M2209/112—Complex polyesters having dihydric acid centres
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
Definitions
- the invention disclosed is directed to an improved ester base lubricant composition which includes minor stabilizing amounts of N-substituted phenothiazine and secondary or monoaralkyl tertiary aromatic amine.
- the substituent on the phenothiazine nitrogen atom is an aralkyl group which, in a preferred aspect, is (a) chloro substituted on its alkylene link, (b) ring substituted by at least one of the following: halo, nitro, alkoxy, hydroxy, and like groups, or (c) substituted both as in (a) and (b).
- aralkyl group which, in a preferred aspect, is (a) chloro substituted on its alkylene link, (b) ring substituted by at least one of the following: halo, nitro, alkoxy, hydroxy, and like groups, or (c) substituted both as in (a) and (b).
- the composition exhibits good storage stability, better cleanliness and enhanced oxidative stability in use. Also disclosed is an improved method for lubricating surfaces which provides increased effectiveness and longer service life of lubricated parts. Advantages provided by the present composition and method are observed even at elevated lubricant temperature.
- the present invention relates to an improved ester base lubricant composition including small amounts of N-substituted phenothiazine and secondary or monoaralkyl tertiary aromatic amine, and to a method for lubricating surfaces using this composition.
- the substituents on the phenothiazine nitrogen is an aralkyl group which is substituted by at least one member of the group consisting of halo, nitro, alkoxy, and hydroxy groups.
- the present composition exhibits better cleanliness and improved oxidative stability even at elevated use temperature.
- Ester base lubricants have been available to the art and have beenused with some success for high temperature lubrication.
- synthetic lubricants based on organic esters of the diester type such as diesters derived from adipic, azelaic and sebacic acids by esterification of C to C alcohols.
- An example of such a widely used synthetic lubricant is di(2-ethylhexyl) sebacate which has been employed in jet engine oils and in related lubricants.
- recent heavy demands and price competition have led to use of a variety of diesters from more readily available dicarboxylic acids.
- ester base or synthetic lubricating compositions have often included minor amounts (e.g., about 0.5 to 1 weight percent) of phenothiazine for stabilization against oxidation. While oxidation stability of these lubricants has been somewhat improved using phenothiazine, overall improvement has been minimized by associated formation of insolubles and deposition of often substantial amounts of sludge. Failure of the prior art to effectively solve oxidation stability and especially cleanliness problems associated with synthetic lubricants containing phenothiazines, especially at higher temperatures, has given rise to the term phenothiazine dirtiness.”
- lubricant compositions including various phenothiazine derivatives have been proposed.
- Edwards, et al., U.S. Pat. No. 3,218,256 describes a lubricating composition which consists essentially of 1 a synthetic lubricating oil consisting essentially of a carboxylic acid ester base, the oil having dissolved therein (2) a non-N-substituted, phenylene ring alkylated or alkoxylated phenothiazine (preferably 3,7- dioctyl phenothiazine), (3) a secondary aromatic amine selected from diphenylamines and N- phenylnaphthylamines, and (4) benzotriazole.
- U.S. Pat. No. 3,344,068 to Waight, et al. describes a lubricating composition which includes a major amount of an ester base lubricating oil and minor amounts of an N-substituted phenothiazine and a secondary aromatic amine having two aromatic groups attached to the amine nitrogen atom.
- the substituent on the phenothiazine nitrogen is selected from a hydrocarbyl group having I to 12 carbons and a cyanoalkyl group having 1 to carbons.
- the hydrocarbyl group can be alkyl, aryl, alkaryl, or aralkyl.
- At least one of the aromatic rings of the phenothiazine is substituted by an alkyl or alkoxy group having from 1 to 12 carbons.
- the composition is illustrated in the patent by a variety of specific formulations, the majority of which include 10- benzyl-3,7-dioctylphenothiazine as the N-substituted phenothiazine component. Data representing results of oxidation/corrosion tests at 175C.
- U.S. Pat. No. 2,308,282 to l-Iowland, et al. teaches corrosion inhibitors or retarders for protecting metal surfaces.
- the corrosion inhibitors are disclosed to be ammonia compounds of the formula aralkyl-N(X,)X wherein X and X are hydrogen, alkyl, or aralkyl.
- N-(C -C alkyl)-p,p'-dioctyldiphenylamines as antioxidants for lubricating oils is taught in U.S. Pat. No. 3,368,975 to Davis, et a1.
- British Pat. No. 1,124,904, Carswell teaches a lubrieating grease comprising a lubricating oil, a thickener. and a minor proportion of a 1,2,4-triazole which may be 3-amino-l,2,4-triazole.
- This British patent corresponds to Dutch Patent Publication No. 68/095507.
- the present lubricant composition typically exhibits good storage stability, better cleanliness and improved oxidative stability at high temperatures, e.g., about 250F to about 400F and higher. Surfaces lubricated by the the present composition often show increased service life, decreased wear and less corrosion.
- the present lubricant composition includes a major amount of a carboxylic acid ester component; a minor stabilizing amount of an aromatic amine component which may be a secondary aromatic amine having two aromatic groups, a tertiary aromatic amine having two aromatic groups and an aralkyl group, or a mixture thereof, where the aromatic nuclei of the aromatic groups and the substituted alkyl moiety of the aralkyl group are attached directly to amine nitrogen atom; an N-substituted phenothiazine component having the following general formula:
- R is a C to about C aralkyl group which, as more fully described below, is characterized by (a) being ring substituted by at least one member selected from the group consisting of halo, nitro, alkoxy, hydroxy, and alkyl groups, (b) having a particularly defined alkylene linkage, or (c) both characteristics (a) and (b); and R R R and R are members selected from the group consisting of a hydrogen atom, and alkyl, alkoxy, and aralkyl groups having from I to about l2 carbon atoms; and optionally, a triazole component and/or a phosphorus-containing acid ester component.
- a suitable amount of the present improved composition may be applied to a surface to be lubricated, or the lubricant may be circulated about parts to be lubricated, as desired.
- the carboxylic acid ester component of the present lubricant composition may be almost any carboxylic acid ester which is suitable for lubricating.
- Suitable esters include aliphatic diesters having the general formula R QOC(CH ),,COOR wherein n is an integer from aboutZ to about 34, and R and R are members selected from the group consisting of straight and branched chain alkyl, phenoxyalkyl, and alkyloxyalkyl groups having from about 6 to about carbon atoms.
- n is from about 4 to about 8 and R and R are selected from straight and branched chain alkyl groups having from about 8 to about 16 carbon atoms.
- esters of this type include di(Z-ethylhexyl) sebacate, di( 2-ethylhexyl) azelate, diisodecyl sebacate, diisooctyl azelate, isooctylisodecyl adipate, di(l,3- dimethylbutyl) adipate, and the like.
- the carboxylic acid ester component may also include esters derived from aliphatic monocarboxylic acids by esterifying these acids with polyols, i.e., aliphatic alcohols having 2 or more hydroxy groups. Acids suitable for deriving these esters include aliphatic acids having from about 3 to about 18, and preferably from about 4 to about 12 carbon atoms. Suitable polyols include, for example, trimethylolpropane, neopentyl glycol, pentaerythritol, dipentaerythritol, tripentaerythritol and mixtures thereof.
- esters of this class include pentaerythrityl tetrabutyrate, pentaerythrityl tetracaproate, pentacrythrityl dibutyratedicaproate, mixed C to C saturated fatty acid esters of pentaerythritol, dipentaerythrityl mixed hexaesters of C to C fatty acids, trimethylolpropane tricaprylate, and the like.
- the carboxylic acid ester component may further include aliphatic polyesters having the following general formula:
- R is an alkyl group having from I to about 12 carbon atoms, and preferably from about 5 to about 12 carbon atoms in branched chain configuration with a tertiary carbon atom adjacent the carbon atom which is linked to the oxygen atom.
- R is an alkylene group having from about 6 to about 20 carbon atoms in straight or branched chain configuration
- R is an alkylene or oxyalkylene group having from about 2 to about 20 carbon atoms.
- These polyesters may be prepared, for example, by esterifying two moles of aliphatic dicarboxylic acid per mole of glycol, followed by esterifying the resulting diester product having two COOI-I groups with two moles of monohydric alcohol per mole of the product.
- the ester component of the present lubricant com position may include mixtures of the above-described carboxylic acid esters.
- the composition includes the ester component in a major amount.
- the aromatic amine component of the present lubricant may be selected from secondary amines having two aromatic groups attached to a nitrogen atom of the amine.
- the aromatic groups may be heterocyclic or homocyclic, desired.
- the aromatic groups are homocyclic aromatic groups of the benzene series and alkyl substituted derivatives thereof. Phenothiazine and phenothiazine derivatives having one or more substituents on their phenylene rings may prove useful as the secondary aromatic amine component.
- the two aromatic groups included in the amine component are free of interconnecting atoms other than nitrogen.
- the aromatic groups of the amine component may have the same or different formulas, as desired.
- the secondary aromatic amine component may be selected from the group consisting of N-phenylnaphthylamines and diphenylamines.
- Exemplary aromatic amines suitable herein are N-phenyl-l-naphthylamine, diphenylamine, N-phenyl- 2-naphthylamine, alkyl or alkoxy substituted derivatives of these compounds, and mixtures thereof.
- At least one of the aromatic groups on each of the various amines is alkyl or alkoxy substituted, e.g., N-(4- octyl)phenyI-Z-naphthylamine, N-(4-octyl)phenyl-lnaphthylamine, and the like.
- the alkyl and alkoxy groups may have from about 4 to about 12 carbon atoms and preferably about 8 carbon atoms.
- a preferred amine component is p,p'-dioctyldiphenylamine, which may be, for example, 4,4-(2,2,3,3-tetramethylbutyl)-diphenylamine.
- aromatic amines includes N-4-octylphenyll-octyl-2- naphthylamine.
- Especially preferred amines include N-4-( 1,1,3,3-tetramethylbutyl)-phenyl-lnaphthylamine, N-4-(1,1,3,3-tetramethylbutyl)- phenyl-2-naphthylamine, N-4-( l l ,3 ,3-
- Mixtures of suitable secondary aromatic amines may be included in the present lubricant composition.
- the secondary amine may be included in a minor stabilizing amount, for example, from slightly above 0 (e.g., about 0.1) to about 8 parts by weight or more, typically from about 0.5 to about 8 parts by weight, and preferably from about 1 to about 4 parts by weight, per 100 parts by weight of the carboxylic acid ester component.
- N-substituted phenothiazine component of the present lubricant may be represented by the following general formula:
- R is a particularly defined aralkyl group having from 7 to about 22 carbon atoms.
- R is ring substituted by at least one member selected from the group consisting of halo, nitro, alkyl, alkoxy, and hydroxy groups.
- R may be selected from the groups having the following general formulas:
- n is an integer in the range from 0 to about 4;
- R10 and R are selected from chlorine atom, hydrogen atom and methyl group; and
- A, B, D, E, F, G, and J are members selected from the group consisting of hydrogen atom and halo, nitro, hydroxy, alkyl, and alkoxy groups such that at least one of the members A, B, D, E, F, G, and .l is other than hydrogen atom when both R and R are hydrogen atoms.
- Preferred alkyl and alkoxy groups having 1 to about 12 carbon atoms.
- Pre ferred halo substituents are fluoro, bromo and chloro
- the present lubricant composition exhibits even better stability where A, B, D, E, F, G, and J are selected from the subgenus consisting of hydrogen atom, fluoro, chloro, bromo, nitro, hydroxy, and C to about C alkoxy groups such that at least one of A, B, D, E, F, G and .l is other than hydrogen atom when both R and R are other than chlorine atoms.
- suitable R groups are 2,4-dichlorobenzyl; 3,4-
- R R R and R are members selected from the group consisting of hydrogen atom and alkyl, alkoxy, and aralkyl groups having from 1 to about 12 carbon atoms.
- at least one of R R R and R is C to about C alkyl or alkoxy.
- 2 of these substituents are selected from straight and branched chain octyl groups.
- the 2 groups may be on the same or different phenylene rings of the phenothiazine structure, as desired.
- the N-substituted phenothiazine component may be an N-(R)-3,7-dioctylphenothiazine wherein R is a member selected from the group consisting of 2- chlorobenzyl; 4-chlorobenzyl; 2,4-dichlorobenzyl; 3,4- dichlorobenzyl; a,a-dichlorophenylmethyl; 2- fluorobenzyl; 4-fluorobenzyl; 2-nitrobenzyl; 4- nitrobenzyl; 2-methylbenzyl; 4-methylbenzyl; and 2,2-dimethyl-2-phenylethyl.
- R is a member selected from the group consisting of 2- chlorobenzyl; 4-chlorobenzyl; 2,4-dichlorobenzyl; 3,4- dichlorobenzyl; a,a-dichlorophenylmethyl; 2- fluorobenzyl; 4-fluorobenzyl; 2-nitrobenzyl; 4- nitrobenzyl;
- R is selected from the group consisting of 2-chlorobenzyl; 4- chlorobenzyl; 2,4-dichlorobenzyll; 3,4-dichlorobenzyl; a,a-dichlorophenylmethyl; Z-fluorobenzyl; 2- nitrobenzyl; and 4-,nitrobenzyl.
- the octyl groups in the N-(R)-3,7-dioctylphenothiazines may be, for example, 2,2,3,3-tetramethylbutyl groups, and preferably l,l ,3,3-tetramethylbutyl groups.
- N-substituted phenothiazine component is N-(2,4-dichlorobenzyl)-3,7-dioctylphenothiazine.
- R and R are octyl groups, e.g., l,l,3,3-tetramethylbutyl groups, while R are R, are hydrogen atoms.
- Lubricants of the present invention which typi cally have excellent lubricant qualities include those which contain N-substituted phenothiazines having l,l,3,3-tetramethylbutyl substituents attached as shown by R and R e.g., N-(2,4-dichlorobenzyl)-3,7- (l,l,3,3-tetramethylbutyl)-phenothiazine.
- the N-substituted phenothiazine component together with the aromatic amine component aids in improving cleanliness and oxidative stability of the present lubricant composition.
- the N-substituted phenothiazine component may be included in the composition in a minor stabilizing amount, for example, from slightly above 0 (e.g., about 0.1) to about 10 parts by weight or more, typically from about 0.5 to about 10 parts by weight, and preferably from about 0.5 to about 3 parts by weight, per I00 parts by weight of the carboxylic acid ester component.
- N-(3,4-dichlorobenzyl)-3,7-(2,2,3,3-tetramethylbutyl)phenothiazine may be prepared substantially as next described.
- 1.5 moles of dimethylsulfoxide is added to a 3 liter reaction flask equipped with a condenser, stirrer, nitrogen inlet, thermometer and dropping funnel.
- 1.1 moles of 60 perce nt by weight 5 sodium hydride dispersed in mineral oil is added with stirring.
- the reaction mixture turns slightly orange with evolution of hydrogen. Stirring is continued for about /2-hour after hydrogen evolution has substantially ceased.
- the viscous oil is extracted with, 400 milliliters of toluene and washed with 200 milliliters of aqueous 10 percent by weight sodium bicarbonate solution. Washing is repeated, as necessary, using water until the washings have a pH of from about 6 to about 8. Remaining solvents and volatiles are removed by heating to about 150C. under moderate vacuum to yield an N-(3,4- dichlorobenzyl)-3,7-(2,2,3,3-tetramethylbutyl) phenothiazine product, which may be cooled and recovered as desired.
- included triazole component of the present lubricant may be exemplified by metal passivators such as 3-amino-1,2,4- triazole; 4-amino-l,2,4-triazole; 1,2,3-benzotriazole and alkyl substituted derivatives thereof wherein the alkyl substituents or substituents have, for example, from 1 to about 12 carbon atoms, e.g., 5-methyl-l,2,3- benzotriazole; and 5,5 '-methylene bis-(1,2,3- benzotriazole).
- the triazole component may be included in any effective amount in the range of solubility of the triazole in the composition. Generally, the triazole component may be included in an amount from to about 1 part by weight, and preferably from about 0.01 to about 0.2 parts by weight per 100 parts by weight of the carboxylic acid ester component.
- included phosphorus-containing acid ester component may be selected from triesters of phosphoric acid with alcohols such as straight and branched chain aliphatic alcohols having from 1 to about 8 carbon atoms.
- esters such as straight and branched chain aliphatic alcohols having from 1 to about 8 carbon atoms.
- exemplary of these esters are triethyl phosphate, tributyl phosphate and triisooctyl phosphate.
- Other suitable phosphoric acid esters include esters of phenol and naphthol. These esters may have from 1 to about 3 C to C alkyl substitutents on one or more of the aryl moieties.
- Exemplary of these esters are tricresyl phosphate, triphenyl phosphate and the like.
- the phosphoruscontaining acid ester component may be included in an amount from 0 to about 10 parts by weight, and preferably from about 0.5 to about parts by weight per 100 parts by weight of the carboxylic acid este
- the aromatic amine component of the present composition may be a tertiary aromatic amine having attached to its amine nitrogen atom (a) a first aromatic group, (b) a second aromatic group, and (c) an aralkyl group which may be selected from those groups herein denominated R and having the general formulas (1), (11), and (Ill):
- R and R may be selected from chlorine atom, hydrogen atom and methyl group; n is an integer in the range offrom O to about 4; and R R R R R R R and R may be selected from hydrogen atom, alkyl, or. alkoxy groups having from 1 to about 12 carbon atoms, halo (preferably, fluoro or chloro), nitro, hydroxy and like groups.
- these tertiary amines unexpectedly cooperate with the N-substituted phenothiazine component in providing improved oxidative stability and increased cleanliness relative to that obtained when either of these two components is included in the absence of the other.
- the first aromatic group may be alkyl or alkoxy substituted phenyl
- the second aromatic group may be selected from phenyl, alkyl, or alkoxy substituted phenyl, l-naphthyl, 2- naphthyl, and alkyl or alkoxy substituted 2-naphthyl.
- the alkyl and alkoxy groups which may be substituted on the first and second aromatic groups may have from about 1 to about 12 carbon atoms, and preferably about 8 carbon atoms.
- a preferred alkyl group which may be substituted on the aromatic groups is octyl, which may be, for example, 2,2,3,3-tetramethylbuty1.
- Lubricants of the present invention typically have excellent lubricant qualities in embodiments including 1,1 ,3,3-tetramethylbutyl substituents on one or more of the first and second aromatic groups of the tertiary aromatic amines.
- Suitable tertiary amines include those compounds having a general formula selected from the group consistingof:
- R is an aralkyl group selected from those groups having the general formulas I, II, and III which are set forth and defined in the preceding paragraph;
- R R R R and R are selected from the group consisting of hydrogen atom, C to about C alkyl groups, and C to about C alkoxy groups such that at least one of R R R and R is other than hydrogen; and
- R and R are selected from the group consisting of C to about C alkyl groups and C, to C alkoxy wherein R is octyl, forexample,
- R is an aralkyl group which is defined above. It is to be understood that mixtures of suitable tertiary amines may be included in the present composition.
- Tertiary amines which may be included herein may be exemplified by N,N-bis-4-octylphenyl-benzylamine, for example, N,N-bis-4-(2,2,3,3-tetramethylbutyl)- phenylbenzylamine, and preferably N,N-bis-4-( l,l,3,3- tetramethylbutyl)-phenyl-benzylamine; N,N-bis-4- octylphenyl-2-phenylethylamine, for example N,N-bis- 4-(2,2,3,3-tetramethylbutyl)-phenyl-2- phenylethylamine, and preferably N,N-bis-4-(l,l,3,3- tetramethylbutyl)-phenyl-2-phenylethylamine; N-4- octylphenyl-N-l-naphthylbenzylamine, preferably N-4- (
- tertiary amines which may be included herein may i be exemplified by N,N-bis-4-octylphenyl-2- methylbenzylamine; N,N-bis-4-octylphenyl-4- methylbenzylamine; N,l ⁇ l-bis-4-octylphenyl2- chlorobenzylamine; N,N-bis-4-octylphenyl-4- chlorobenzylamine; N,N-bis-4-octylphenyl-2,4- dichlorobenzylamine; N,N-bis-4-octylphenyl-3,4- diehlorobenzylaminc; N,N-bis-4-octylphenyl-a,adichlorohenzylamine; N.N-bis-4-oetylphenyl-2- 10 fluorobenzylamine, N,N-bis-4-octylphenyl-4- fluorobenzyl
- the octyl groups in the preceding amines are l,l,3,3-tetramethylbutyl groups.
- N-(2,4-dichlorobenzyl)-3,7-dioctylphenothiazine e.g., N-(2,4-dichlorobenzyl)-3,7-(2.2,3.3- tetramethylbutyl)-phenothiazine, and preferably N- (2,4-dichlorobenzyl)-3,7-( l, l ,3,3-tetramethylbutyl phenothiazine; N-( 3 ,4-dichlorobenzyl )-3,7-dioctylphenothiazine, e.g., N-(3,4-dichlorobenzyl)-3,7- (2,2,3,3-tetramethylbutyl)-phenothiazine, and preferably N-( 3,4-
- Tertiary amines which may be included in the present composition may be prepared, for example, using the method caught in the Daniels application U.S. Ser. No. 152,372, which is referenced supra in connection with preparation of the N-substituted phenothiazine component hereof, and the method taught in application U.S. Ser. No. 379,835 filed July 16, 1973 under attorney docket number 4230 a eontinuation-in-part'of said application Ser. No. 152,372 and assigned to the assignee hereof).
- the tertiary amine may be included in a minor stabilizing amount, for example, from slightly above 0 (e.g., about 0.1) to about 8 parts by weight or more, typically from about 0.5 part by weight to about 8 parts by weight, and preferably from about 1 to about 4 parts by weight, per parts by weight of carboxylic acid ester component.
- a minor stabilizing amount for example, from slightly above 0 (e.g., about 0.1) to about 8 parts by weight or more, typically from about 0.5 part by weight to about 8 parts by weight, and preferably from about 1 to about 4 parts by weight, per parts by weight of carboxylic acid ester component.
- the present lubricant composition may further include metal deactivating agents, anti-corrosion agents, anti-rusting agents, anti-foaming agents, dyes, thickening agents, additional anti-oxidants and other suitable agents known in the art for use in ester-containing lubricants.
- the present method for lubricating includes contacting a surface to be lubricated with the improved composition of this invention.
- surfaces of two parts which may be moved relatively to each other in a zone of near-contact are lubricated by this method.
- the lubricant may be placed in the zone in a manner such that the parts may be moved relatively with substantially no surface-to-surface contact.
- the lubricant may be circulated through the zone, if desired. in many instances it is preferred to circulate the lubricant along a flow path such that lubricant which may be frictionally heated flows from a near-contact zone to a heat sink from which cooled lubricant may be returned to the near-contact zone.
- any suitable circulation means may be used.
- highly desirable lubrication may be effected by merely applying a suitable amount of the lubricant to a surface to be lubricated.
- Liquid lubricant compositions were prepared by uniformly mixing the various components in the amounts indicated in Table 1 below.
- the compositions of l'lxampics 1 to 6 inclusive were formulated including either phenothiazine or 3,7-dioctylphenothiazine, as indicated, These compounds have been used in prior art attempts to enhance oxidative stability of ester base lu- 12 with potassium hydroxide to an end point of pH ll using the procedure of ASTM Standard D 664.
- the compositions were observed and rated for sludge content at the end of the 72 hour oxidation corrosion tests.
- the lubricant compositions of Examples 7 to A sludge rating of nil means essentially no sludge was inclusive are embodiments of the present invention. observed, while ratings of light, moderate, heavy, etc., The composition of Example 10A was prepared for were assigned for increasing amounts of observed comparative purposes more fully described below. sludge.
- compositions were tested for corrosiveness and oxidative stability.
- the test included placing 0.032 inch X 1 inch X 1 inch metal test specimens in glass test tubes and adding 100 milliliter samples of the various compositions to cover the test metals. The samples were heated to a substantially constant temperature of about 347F, and thereafter 5 liters per hour of clean dry air was flowed upwardly through the liquid compositions.
- the metals used included magnesium, alumi-
- the observed absence of sludge in those compositions of the invention which are illustrated by Examples 7 to l0 illustrates improved cleanliness and increased resistance to oxidation of these compositions relative to the compositions of Examples 1 to 4 and 6 containing phenothiazine and no N-substituted phenothiazine.
- Example 1 1 exhibited no change from Parts by its original appearance and exhibited decreased corro- H 12 l3 l4 5 siveness and improved resistance to oxidation.
- lsooctylisodecyl adipate 100 V 100 100 100 100 Tricresyl phosphate 1 1 1 N-(3,4 dichlorobenzyl)- 1.5
- Example 1 1 sample containing N-( 3,4- substantially no sludge is observed for the compositions dichlorobenzyl)-3,7-dioctylphenothiazine showed that f Examples 15 to 26.
- Example 31 which contain either an N-substituted phenothiazine compound in the absence of atertiary amine or contain a tertiary amine in the absence of an N-substituted phenothiazine compound.
- the data for the composition of Example 31 ature the compositions of Examples 31 to 33 exhibit excellent suppression of sludge formation, increased resistance to oxidation, and substantial freedom from corrosiveness, rendering them eminently suitable for containing N-(2,4-dichlorobenzyl)3,7-( l,l,3,3- 5 lubricating.
- the tests results are shown below in Table tetramethylbutyl)-phenothiazine and N,N-bis-4- VI.
- Example 32 A cooperative effect, similar to that exhibited by the Example 31 composition, was observed for the Example 32 composition wherein the 2,4-dichlorobenzyl group of the N- substituted phenothiazine was substituted by its 3,4- dichlorobenzyl isomer, relative to the compositions of Examples 28 and 29.
- the cooperative effect exhibited by the Example 32 composition is evidenced, in part, by comparison of the negligible amount of sludge observed therefor with the higher amounts of sludge observed for the Example 28 and Example 29 compositions which do not include the N-substituted phenothiazine in conjunction with the tertiary amine.
- An unexpected cooperative effect was also observed for the Excomposition.
- Liquid lubricant compositions are prepared by uniformly mixing the various components in the amounts indicated in Table VII below.
- the compositions of Examples 34 to 39 inclusive are formulated including either phenothiazine or 3,7-dioctylphenothiazine, as indicated. These compounds have been used in prior art attempts to enhance oxidative stability of ester base lubricants.
- the lubricant compositions of Examples 40 to 43 inclusive are embodiments of the present invention.
- the composition of Example 44 was prepared for comample 33 composition including N-(3,4 parative purposes more fully described below.
- the data shows that at high temper- These compositions are tested for corrosiveness and oxidative stability using the procedure of Examples 1 to 10 A.
- the compositions are observed and rated for sludge content at the end of the 72 hour oxidation corrosion tests.
- Tests of the lubricant compositions of Examples 40 to 43 show minor variations in viscosity change, acid value change, and weight change for the various metal specimens, relative to the corresponding data for the compositions of Examples 7 to 10 (sec Tables 1 and 11). Substantially no sludge is observed for the compositions of Examples 40 to 43.
- Example 51 TABLE Vlll N-substituted phenothiazine in conjunction with the tertiary amine.
- An unexpected cooperative effect is also observed for the Example 51 composition including N-(3,4-dichlorobenzyl)3,7-(2,2,3,3-tetramethylbutyl)-phenothiazine and N,N-bis-4-(2.2,3.3- tetramethylbutyl)-phenyl-2-phenylethylaminc in that substantially no sludge is observed therefor.
- Example 47 In contrast a moderate amount of sludge is observed for the Example 47 composition and an amount of sludge rated heavy is observed for the Example 48 composition, which includes this N-substituted phenothiazine in the absence of this tertiary amine, and includes this tertiary amine without this N-substituted phenothiazine, respectively.
- the data shows that at high temperature the compositions of Example 49 to 51 exhibit excellent suppression of sludge formation, increased resistance to oxidation, and substantial freedom from corrosiveness, rendering them eminently suitable for lubricating. Substantially the same results are obtained for the compositions of Examples 45, 46, 47, 48, 49, 50 and 51 as were obtained for the compositions of Examples 27,
- Example No. and Approximate Parts by Weight Component 45 4t 47 These compositions are tested for corrosiveness and oxidative stability using the procedure of Examples 1 to 10A.
- the observed absence of sludge in those compositions of the invention which are illustrated by Examples 49 to 51 inclusive illustrates cooperative improvements in cleanliness and increased resistance to oxidation of these compositions relative to the compositions of Examples 45 to 48, inclusive, which contain either an N- substituted phenothiazine compound in the absence of a tertiary amine or contain a tertiary amine in the absence of an N-substituted phenothiazine compound.
- Example 49 containing N-(2,4-dichlorobenzyl)3,7-(2,2,3,3-tetramethylbutylphenothiazine and N,N-bis-4-(2,2,3,3- tetramethylbutyl)-phenylbenzylamine shows substantially less sludge formation, relative to that observed for the composition of Example 45 including this N- substituted phenothiazine compound in the absence of this tertiary amine compound, and shows a similar improvement relative to the composition of Example 47 including the tertiary amine in the absence of the N- substituted phenothiazine.
- Example 50 A cooperative effect, similar to that exhibited by the Example 49 composition, is observed for the Example 50 composition wherein the 2,4-dichlorobenzyl group of the N-substituted phenothiazine is substituted by its 3,4-dichlorobenzyl isomer, relative to the compositions of Examples 46 and 47.
- the cooperative effect exhibited by the Example 50 composition is evidenced, in part, by comparison of the negligible amount of sludge observed therefor with the higher amounts of sludge observed for the Example 46 and Example 47 compositions which do not include the 28, 29, 30, 31, 32 and 33, respectively. (See Tables V and VI.)
- compositions of Examples 49 to 51 are tested, substantially as described in the procedure of Examples ll to 14, for their performance in the presence of peroxide. All of these compositions exhibit excellent storage stability in this test and show substantially no evidence of formation of insoluble matter in the presence of peroxides at an elevated storage temperature of lF for 2 weeks.
- compositions of the present invention exhibit cooperative activity respecting improvements in cleanliness and oxidative stability not only where the amine component is a tertiary amine, but also where a secondary amine is included.
- the data of Tables II and VI show that the composition of Example 7 exhibits in' use, inter alia, substantially less sludge formation (Table II) than one skilled in the art would expect in view of that observed for the composition of Example 10A (Table II) and that observed for the composition of Example 27 (Table VI).
- Desirable cooperative effect is further illustrated, for example, by the improved sludge rating for the composition of Example 8 (Table II), relative to the sludge rating for the composition of Example 10A (Table II) and to that for the composition of Example .28 (Table VI).
- EXAMPLE 52 A lubricant composition illustrating an aspect of the present invention wherein the amine component is a secondary aromatic amine was prepared by uniformly 19 mixing the various essential and optional components in the amounts indicated below:
- Lubricant A 5,5 '-methylene-bis-( 1,2,3-benzotriazole) This lubricant composition will be referred to hereinafter as Lubricant A.
- EXAMPLE 53 A lubricant composition illustrating an aspect of the present invention wherein the amine component is a tertiary aromatic amine was prepared by uniformly mixing the various essential and optional components in the amounts indicated below:
- Lubricant B This lubricant composition will be referred to hereinafter as Lubricant B.
- EXAMPLE 54 A composition not within the present invention was prepared by uniformly mixing the various components in the amounts indicated below:
- the octyl groups in this compound are 1.1,3.3tctrumethylhutyl groups.
- Lubricant C This composition will be referred to hereinafter as Lubricant C.
- N-substituted phenothiazine compounds of Examples 52 to 54 were prepared using the procedure of the previously noted U.S. patent application, Ser. No. 152,372. Tests showed that the melting point for the N-substituted phenothiazine compound included in Lubricant A and Lubricant B was 1 15 to 1 17C. and that for the N-substituted phenothiazine compound included in Lubricant C was 123 to 125C, indicating substantial purity for both N-substituted phenothiazine products.
- Lubricants A and B which illustrate lubricants of the present invention, are characterized with a balance of resistance to oxidation and freedom from corrosiveness which is in a range from generally as good as to better than the balance observed for Lubricant C.
- the substantially better performance shown by Lubricants A and B respecting aluminum is especially important in lubricant applications in the field of lightweight engine assemblies.
- the amount of filter retained sludge for Lubricant A and Lubricant B was in a range from about 15 to percent less than that for Lubricant C, illustrating substantially better cleanliness, and
- a plus sign signifies gain; a minus sign (-1 signifies loss; N.C. signifies substantially no change in weight.
- EXAMPLE 55 Portions of Lubricant A, Lubricant B, and Lubricant C were tested for oxidation stability and cleanliness using the Alcor High Temperature Deposition Test with a test temperature of 525F.
- a lubricant composition being tested is circulated for a 48- hour period through an Alcor Deposition Tester, Model HTDT 1003, manufactured by Alcor, Inc., San Antonio, Texas.
- the Alcor Tester includes a Type 446 stainless steel tube having a heated section inches in length, a lower end of which is electrically heated to and maintained at 525F. for the first 2 hours of the test. Thereafter, the electrical power input to the metal tube is maintained at a substantially constant value of about 1,000 watts.
- the lubricant is circulated from a sump-cooler at a substantially constant rate of 300 milliliters per minute using a suitablepump driven by constant speed drive means and rated for high temperature service. Air saturated with water is injected, at a rate ,of about 1,000 milliliters (200F., 14.7 pounds per square inch, absolute) per minute, into the lubricant at a location in the lubricant flow path in advance of the heated tube. The lubricant-air mixture enters the tube zone near the lower end of the tube and flows upwardly adjacent the heated tube. After discharging from the tube zone. air is vented and the lubricant returns to the sump-cooler, associated with which is a I00 mesh (U.S. 'Standard) filter screen disposed in a conduit connecting the sump outlet with the pump inlet.
- I00 mesh U.S. 'Standard
- the power input simulates the frictional heat imparted to lubricants in high-temperature lubrication of bearings in heavy duty applications such as high speed gas turbine engines in jet aircraft where lightweight materials, e.g., aluminum, are often required.
- This power input is manifested typically by an increase in lubricant temperature, for example, from about 3009F. at the metal tube section inlet to about 450F. at the outlet.
- the temperature near the upper end of the metal tube typically is in the range from 650 to 700F., depending in part on the specific heat of the lubricant being tested.
- Deviations from perfection are measured by a quantity designated Overall Rating which is calculated by summing the tube deposit weight in milligrams plus the filter screen deposit weight in milligrams plus the visual tube evaluation and dividing the resulting sum by two. In this regard, perfection is indicated by an Overall Rating of zero.
- the terms tube deposit weight: and filter screen deposit weight” mean the weight of deposits which form during the test on the tube and screen, respectively.
- the term visualtube evaluation means a numerical rating assigned to the lubricant taking into account type of tube deposit and the thickness of the deposit. In general, the type of tube deposits which can be detected in this test are carbon deposits, sludge and varnish. Carbon deposits are classified in this test as flaked, blistered, crinkled, and smooth.
- the test description generic to all these carbon deposits is a carbonaceous coating which cannot be removed by wiping with a rag.
- the carbon deposits are further classified in the four following classes corresponding to the descriptions given parenthetically: (I) flaked carbon (broken blisters, peeling), (ll) blistered carbon (non-broken blisters, bubbled), (Ill) crinkled carbon (ridges, not smooth), and (IV) smooth carbon (smooth coating).
- Sludge type deposits (V) are described as shiny oily emulsions of carbon and oil which can be wiped off with a rag.
- Varnish type deposits (Vl) are described as shiny varnjshor lacquerlike coatings.
- each one-inch segment of the 10-inch metal tube is observed for the presence and type of deposit. Thereafter, the thickness of deposit for each of the 10 segments is measured, followed by stripping and weighing the deposits for each segment.
- a base numerical demerit value is assigned for each segment according to the following scheme, the Roman numerals used herein referring to the various classes of deposits-described previously: I-18, Il-l5, III-12, IV-9, V6, V1 5, and zero if no deposit is observed.
- a numerical demerit value for each segment is calculated by adding to the base value a number from 0 to 2, as may be required, according to the description next given.
- the number 2 is added for carbon deposits (Classes I to IV) where the deposit thickness is more than 3/64 inch and for Class V deposits of more than I/l6 inch.
- the number I is added for Class I to IV deposits where the deposit thickness is from more than l/64 inch to 3/64 inch inclusive and for Class V deposits in the range from more than I132 to l/l 6 inch inclusive.
- the numerical demerit value is taken to be the base value, with the proviso that where a segment includes portions of two or more different classes or two or more different thicknesses of deposits of the same class, the demerit value for such segment is calculated using a pro tanto modification of the above procedure based on extent of lateral coverage for each such portion, as will be apparent to those skilled in the art.
- a numerical demerit rating is calculated for each segment by multiplying-the numerical demerit value therefor by the deposit weight therefor.
- the visual tube evaluation rating used in the previously described calculation of the Overall Rating is calculated by adding the numerical demerit ratings for the 10 segments and dividing by 10.
- Samples of the test lubricant are taken at the start and conclusion of the test for measuring changes in kinematic viscosity and total acid value.
- the metal tube is removed from the test section and after cooling to room temperature, is immersed without agitation in hexane and then allowed to dry at room temperature.
- the filter is removed, allowed to drain and thereafter dried in air at 200F. for 1 hour.
- the dried filter is weighed and the weight of filter deposits is calculated by weight difference.
- Example 55A for Lubricant A (the lubricant of Example 52).
- Example 52 The procedure of Example 52 was repeated except tetramethylbutyl)phenothiazine 0.45 that all the N-(2,4-dichlorobenzyl)-3,7-( 1 ,1,3,3-tetggx g tggf f igg1 5 i; 0 46 ramethylbutyl) phenothiazine was replaced by the fol- 7 N-(4 nitmbemy
- Example 55A The lubricants of Examples 66 to 72 were tested Approximate using the Alcor High Temperature Deposition Test de- Phfinmhlazme scribed in Example 55A. The results were substantially Ex. Component by Weight I the same as the results shown in Example 55A for Lu- 56 N-(2-chl0robenzyl)-3.7-(l.l 3.3- bricant B (the lubricant of Example 53).
- Example 53 The procedure of Example 53 was again repeated extetramet y uty p enot iazine 59 N (awdichlomphenylmethyl) 37 cept that all the N,N bis 4 (1,133 tetramethylbutyl) (Ll.3,3-tetramethylbutyl)phenothiazine 0.50 phenylbenzylamme was replaced by the following ter- 60 N-(2-fluorobenzyl)-3,7-(l,l,3,3- etrumethylbutyl)phenothiazine 0A5 tiary amine components in the amounts indicated. 6
- bricant A (the lubricant of Example 52). 7 4 chlorobenzylamine 2m 7 N,N-bis-4-octylphenyl- EXAMPLES 63 to 65 2,4-dichlorobenzylamine 2.85 78 N N-bis-4-oct l hen l- The procedure of Example 52 was again repeated ex- 34 dichtombgnfiylmflne 185 cept that all the 4,4'-(1,1,3,3-tetramethylbutyl)- 79 'H Y P Y f a,a-dichlorobenzylamine 2.85 dlphenylamine was replaced by the following secon- 8O NN bis 4 octylphenyl dary amine components in the amounts indicated: 2-fluorobenzylamine 2.59
- EXAMPLE 84 A lubricant composition illustrating as aspect of the present invention wherein the amine component is a secondary aromatic amine was prepared by uniformly mixing the various components in the amounts indicated below:
- Lubricant A This lubricant composition will be referred to hereinafter as Lubricant A.
- EXAMPLE 85 A lubricant composition containing a secondary aromatic amine and an N-substituted phenothiazine and not within the present invention was prepared by uniformly mixing the various components in the amounts indicated below:
- Lubricant D The octyl groups in these compounds were 1,1.3,3-tctramcthylbutyl groups.
- EXAMPLE 86 A composition not within the present invention was prepared by uniformly mixing the various components in the amounts indicated below:
- Lubricant A ZOO-milliliter amounts of Lubricant A, Lubricant D and Lubricant E were tested for storage stability using an accelerated storage test.
- the lubricants were placed in 400 ml. glass beakers and stored for one week in contact with air at 160F. in a static air oven. Observations of Lubricant D at the end of each day during the week showed that this composition remained free from insolubles while retaining its pre-storage clearness and brightness. Daily observation of Lubricant A showed at least as good results in these respects relative to Lubricant D.
- Lubricant E had an increase of 4.01 milligrams of potassium hydroxide per gram of lubricant (mg. KOH/g.); Lubricant D, 0.05 mg. KOH/g.; and Lubricant A, 0.03 mg KOH/g.
- the data shows that Lubricant A is characterized with storage stability which is as good as to better than that of Lubricant D containing an N-benzyl-3,7-dioctylphenothiazine and substantially better than that of Lubricant E containing a 3,7-dioctylphenothiazine.
- halo means a substituent selected from the group consisting of fluoro, chloro and bromo.
- minor stablizing amount means an effective amount of the respective component sufficient to enhance the lubricant composition with respect to at least one of the following: storage stability, cleanliness, oxidative stability, relative freedom from corrosiveness, relative resistance: to degradation, relative resistance to oxidation, relative resistance to deposit formation, and equivalents thereof.
- storage stability cleanliness
- oxidative stability relative freedom from corrosiveness
- relative resistance to degradation
- relative resistance to oxidation relative resistance to deposit formation
- minor stabilizing amount means an amount effective for enhancing cleanliness and oxidation stability.
- Peroxide content is expressed herein in milliequivalrnts of as determined by iodometric titration.
- a lubricant composition comprising:
- a secondary amine selected from a first group consisting of diphenylamine, N-phenyl-lnaphthylamine, N-phenyl-2-naphthylamine, p,pdicotyldiphenylamine, N-4-octylphenyl-lnaphthylamine, N-4-octylphenyl-2-naphthylamine, and N-4-octylphenyl-1-octyl-2-naphthylamine; or ii.
- a tertiary amine selected from a second group consisting of N,N-bis-4-octylphenylbenzylamine, N,N-bis-4-octylphenyl-2-phenylethylamine, N-4-octylphenyl-N-l-naphtylbenzylamine, N-4-octylphenyl-N-1-naphthyl-Z-phenylethylamine, N-4-octylphenyl-N-Z-naphthylbenzylamine, N-4-octylphenyl-N-2-naphthyl-Z-phenylethylamine, N,N-bis-4-octylphenyl-2-methylbenzylamine, N,N-bis-4-octylphenyl-4-methylbenzylaminc, N,N-bis-4-octylphenyl-2-chlorobenzy
- a triazole selected from a fourth group consisting of 3 -amino- 1,2,4-triazole, 4-amino- 1 ,2,4-triazole, 1,2 ,3- benzotriazole, S-methyl-1,2,3-benzotriazole, and 5 ,5 -methylene-bis-(l ,2,3-benz otriazole); and
- a phosphorus containing ester selected from a fifth group consisting of triethyl phosphate, tributyl phosphate, triisooctyl phosphate, tricresyl phosphate, and triphenyl phosphate.
- R is; a 2-chlorobenzyl radical, a 4-chlorobenzyl radical, a 2,4-dichlorobenzyl radical, or a 3,4- dichlorobenzyl radical, and
- R and R are octyl groups.
- N,N-bis-4-octylphenylbenzylamine is N,Nbis-4- (1 ,1 ,3 3 -tetramethylbutyll p henylbenzylamine.
- a lubricant composition comprising:
- a minor stabilizing amount of a secondary amine selected from a first group consisting of diphenylamine, N-phenyl-l-naphthylamine, N-phenyl-Z- naphthylamine, p,p-dioctyldiphenylamine, N-4- octylphenyl-l-naphthylamine, N-4-octylphenyl-2- naphthylamine, and N-4-octylphenyl-l-octyl-Z- naphthylamine;
- phenothiazine having the formula s R2 -Ra /OY m III] 7 1 in which R, and R are hydrogen, R is an alkyl group having 1-12 carbon atoms, R, is an alkyl group having 1-12 carbon atoms, and R is a radical selected from a second group consisting of 2-chlorobenzyl, 4- chlorobenzyl, 2,4-dichlorobenzyl, 3,4-dichlorobenzyl, and a,a-dichlorphenylmethyl;
- a phosphorus containing ester selected from a fourth group consisting of triethyl phosphate, tributyl phosphate, triisooctyl phosphate, tricresyl phosphate, and triphenyl phosphate.
- R is; a 2-chlorobenzyl radical, a 4-chlorobenzyl radical, a 2,4-dichlorobenzyl radical, or a 3,4- dichlorobenzyl radical, and
- R and R are octyl groups.
- a lubricant composition comprising:
- a minor stabilizing amount of a phenothiazine having the formula in which R and R are hydrogen, R is an alkyl group having 1-l2 carbon atoms, R- is an alkyl group having l-l 2 carbon atoms, and R is a radical selected from a second group consisting of 2-chlorobenzyl, 4- chlorobenzyl, 2,4-dichlorobenzyl, 3,4-dichlorobenzyl, and a,adichlorophenylmethyl;
- a triazole selected from a third group consisting of 3-amino- 1,2,4-triazole, 4-amino- 1 ,2,4-triazole, l,2,3- benzotriazole, S-methyl-l,2,3-benzotriazole, and 5 ,5 -meth ylene-bis-( l ,2,3-benzotriazole); and
- a phosphorus containing ester selected from a fourth group consisting of triethyl phosphate, tributyl phosphate, triisooctyl phosphate, tricrcsyl phosphate, and triphenyl phosphate.
- R is; a 2-chlorobcnzyl radical, a 4-chlorobenzyl radical, a 2,4-dichlorobenzyl radical. or a 3,4 dichlorobenzyl radical, and
- R and R are octyl groups.
- octyl groups of thc phenothiazine are l,l,3,3-tctramethylbutyl groups.
- a lubricant composition comprising:
- a lubricant composition comprising:
- amine selected from the group consisting of N,N-bis-4- octylphenylbenzylamine and N,N-bis-4- octylphenyl-2-phenylethylamine;
- N substituted phenothiazine selected from the group consisting of N'(2,4-dichlorobenzyl)3,7-dioctylphenothiazine and N-(3,4--dichlorobenzyl)-3,4- dioctylphenothiazine; and
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Abstract
Description
Claims (19)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US379821A US3869394A (en) | 1971-06-11 | 1973-07-16 | Lubricant composition and method |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15243571A | 1971-06-11 | 1971-06-11 | |
US379821A US3869394A (en) | 1971-06-11 | 1973-07-16 | Lubricant composition and method |
Publications (1)
Publication Number | Publication Date |
---|---|
US3869394A true US3869394A (en) | 1975-03-04 |
Family
ID=26849559
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US379821A Expired - Lifetime US3869394A (en) | 1971-06-11 | 1973-07-16 | Lubricant composition and method |
Country Status (1)
Country | Link |
---|---|
US (1) | US3869394A (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US4908145A (en) * | 1987-09-30 | 1990-03-13 | Amoco Corporation | Engine seal compatible dispersants for lubricating oils |
US5288432A (en) * | 1985-12-20 | 1994-02-22 | Akzo America Inc. | High temperature synthetic lubricants and related engine lubricating systems |
US5302304A (en) * | 1990-12-21 | 1994-04-12 | Ethyl Corporation | Silver protective lubricant composition |
US5942471A (en) * | 1992-07-01 | 1999-08-24 | Ethyl Corporation | Dispersant and antioxidant VI improvers based on olefin copolymers containing phenothiazine and aromatic amine groups |
US6159966A (en) * | 1997-05-30 | 2000-12-12 | Reddy-Cheminor Inc. | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them |
US6194360B1 (en) | 1998-12-22 | 2001-02-27 | International Business Machines Corporation | Magnetic recording device |
US6652962B1 (en) * | 1998-05-29 | 2003-11-25 | Mitsui Mining & Smelting Co. Ltd. | Resin-coated composite foil, production and use thereof |
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 |
US20040192563A1 (en) * | 2003-03-28 | 2004-09-30 | Exxonmobil Research And Engineering Company | Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant |
US20040267373A1 (en) * | 2003-06-25 | 2004-12-30 | Dwyer Kimberly Ann | Assembly tool for modular implants and associated method |
US20050033444A1 (en) * | 2003-06-25 | 2005-02-10 | Jones Michael C. | Assembly tool for modular implants and associated method |
US20080139422A1 (en) * | 2006-12-06 | 2008-06-12 | Loper John T | Lubricating Composition |
GB2449363A (en) * | 2007-05-16 | 2008-11-19 | Afton Chemical Corp | Lubricating composition |
US20100035779A1 (en) * | 2006-10-06 | 2010-02-11 | Idemitsu Kosan Co., Ltd | Grease |
JP2011500729A (en) * | 2007-11-16 | 2011-01-06 | ケムチュア コーポレイション | Bicyclic aromatic amine derivatives as antioxidants |
US8518050B2 (en) | 2007-10-31 | 2013-08-27 | DePuy Synthes Products, LLC | Modular taper assembly device |
US8998919B2 (en) | 2003-06-25 | 2015-04-07 | DePuy Synthes Products, LLC | Assembly tool for modular implants, kit and associated method |
US9095452B2 (en) | 2010-09-01 | 2015-08-04 | DePuy Synthes Products, Inc. | Disassembly tool |
US9101495B2 (en) | 2010-06-15 | 2015-08-11 | DePuy Synthes Products, Inc. | Spiral assembly tool |
US9504578B2 (en) | 2011-04-06 | 2016-11-29 | Depuy Synthes Products, Inc | Revision hip prosthesis having an implantable distal stem component |
US9717545B2 (en) | 2007-10-30 | 2017-08-01 | DePuy Synthes Products, Inc. | Taper disengagement tool |
WO2020095957A1 (en) * | 2018-11-07 | 2020-05-14 | 株式会社Adeka | Thermal stabilizer, thermal stabilizer composition containing same, polyamide resin composition containing said thermal stabilizer or said thermal stabilizer composition, and molded article of said polyamide resin composition |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2308282A (en) * | 1937-12-28 | 1943-01-12 | Us Rubber Co | Corrosion inhibitor |
US2957022A (en) * | 1957-04-30 | 1960-10-18 | Exxon Research Engineering Co | Esters of cyclopentane-1, 3-dicarboxylic acid |
US3218256A (en) * | 1959-01-14 | 1965-11-16 | Castrol Ltd | Lubricating compositions |
US3344068A (en) * | 1964-03-11 | 1967-09-26 | Shell Oil Co | Ester base lubricants |
US3475412A (en) * | 1960-12-09 | 1969-10-28 | Geigy Chem Corp | Dibenzazepine compounds useful as stabilizers for oxidizable organic compositions |
-
1973
- 1973-07-16 US US379821A patent/US3869394A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2308282A (en) * | 1937-12-28 | 1943-01-12 | Us Rubber Co | Corrosion inhibitor |
US2957022A (en) * | 1957-04-30 | 1960-10-18 | Exxon Research Engineering Co | Esters of cyclopentane-1, 3-dicarboxylic acid |
US3218256A (en) * | 1959-01-14 | 1965-11-16 | Castrol Ltd | Lubricating compositions |
US3475412A (en) * | 1960-12-09 | 1969-10-28 | Geigy Chem Corp | Dibenzazepine compounds useful as stabilizers for oxidizable organic compositions |
US3344068A (en) * | 1964-03-11 | 1967-09-26 | Shell Oil Co | Ester base lubricants |
Cited By (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US5288432A (en) * | 1985-12-20 | 1994-02-22 | Akzo America Inc. | High temperature synthetic lubricants and related engine lubricating systems |
US4908145A (en) * | 1987-09-30 | 1990-03-13 | Amoco Corporation | Engine seal compatible dispersants for lubricating oils |
US5302304A (en) * | 1990-12-21 | 1994-04-12 | Ethyl Corporation | Silver protective lubricant composition |
US5942471A (en) * | 1992-07-01 | 1999-08-24 | Ethyl Corporation | Dispersant and antioxidant VI improvers based on olefin copolymers containing phenothiazine and aromatic amine groups |
US6159966A (en) * | 1997-05-30 | 2000-12-12 | Reddy-Cheminor Inc. | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them |
US6652962B1 (en) * | 1998-05-29 | 2003-11-25 | Mitsui Mining & Smelting Co. Ltd. | Resin-coated composite foil, production and use thereof |
US6194360B1 (en) | 1998-12-22 | 2001-02-27 | International Business Machines Corporation | Magnetic recording device |
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 |
US7176168B2 (en) | 2003-03-28 | 2007-02-13 | Exxonmobil Research And Engineering Company | Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant |
US20040192563A1 (en) * | 2003-03-28 | 2004-09-30 | Exxonmobil Research And Engineering Company | Lubricant containing a synergistic combination of rust inhibitors, antiwear agents, and a phenothiazine antioxidant |
US8419799B2 (en) | 2003-06-25 | 2013-04-16 | Depuy Products, Inc. | Assembly tool for modular implants and associated method |
US9381097B2 (en) | 2003-06-25 | 2016-07-05 | DePuy Synthes Products, Inc. | Assembly tool for modular implants, kit and associated method |
US7297166B2 (en) | 2003-06-25 | 2007-11-20 | Depuy Products, Inc. | Assembly tool for modular implants and associated method |
US20080091212A1 (en) * | 2003-06-25 | 2008-04-17 | Depuy Products, Inc. | Assembly tool for modular implants and associated method |
US20050033444A1 (en) * | 2003-06-25 | 2005-02-10 | Jones Michael C. | Assembly tool for modular implants and associated method |
US8998919B2 (en) | 2003-06-25 | 2015-04-07 | DePuy Synthes Products, LLC | Assembly tool for modular implants, kit and associated method |
US8685036B2 (en) | 2003-06-25 | 2014-04-01 | Michael C. Jones | Assembly tool for modular implants and associated method |
US7582092B2 (en) | 2003-06-25 | 2009-09-01 | Depuy Products, Inc. | Assembly tool for modular implants and associated method |
US20040267373A1 (en) * | 2003-06-25 | 2004-12-30 | Dwyer Kimberly Ann | Assembly tool for modular implants and associated method |
US20100035779A1 (en) * | 2006-10-06 | 2010-02-11 | Idemitsu Kosan Co., Ltd | Grease |
US8703678B2 (en) * | 2006-10-06 | 2014-04-22 | Idemitsu Kosan Co., Ltd. | Grease |
US20080139422A1 (en) * | 2006-12-06 | 2008-06-12 | Loper John T | Lubricating Composition |
GB2449363B (en) * | 2007-05-16 | 2009-12-09 | Afton Chemical Corp | Lubricating composition |
US20080287328A1 (en) * | 2007-05-16 | 2008-11-20 | Loper John T | Lubricating composition |
GB2449363A (en) * | 2007-05-16 | 2008-11-19 | Afton Chemical Corp | Lubricating composition |
US9717545B2 (en) | 2007-10-30 | 2017-08-01 | DePuy Synthes Products, Inc. | Taper disengagement tool |
US8518050B2 (en) | 2007-10-31 | 2013-08-27 | DePuy Synthes Products, LLC | Modular taper assembly device |
US9119601B2 (en) | 2007-10-31 | 2015-09-01 | DePuy Synthes Products, Inc. | Modular taper assembly device |
JP2011500729A (en) * | 2007-11-16 | 2011-01-06 | ケムチュア コーポレイション | Bicyclic aromatic amine derivatives as antioxidants |
US9101495B2 (en) | 2010-06-15 | 2015-08-11 | DePuy Synthes Products, Inc. | Spiral assembly tool |
US10166118B2 (en) | 2010-06-15 | 2019-01-01 | DePuy Synthes Products, Inc. | Spiral assembly tool |
US9867720B2 (en) | 2010-09-01 | 2018-01-16 | DePuy Synthes Products, Inc. | Disassembly tool |
US10292837B2 (en) | 2010-09-01 | 2019-05-21 | Depuy Synthes Products Inc. | Disassembly tool |
US9095452B2 (en) | 2010-09-01 | 2015-08-04 | DePuy Synthes Products, Inc. | Disassembly tool |
US9737405B2 (en) | 2011-04-06 | 2017-08-22 | DePuy Synthes Products, Inc. | Orthopaedic surgical procedure for implanting a revision hip prosthesis |
US9949833B2 (en) | 2011-04-06 | 2018-04-24 | DePuy Synthes Products, Inc. | Finishing RASP and orthopaedic surgical procedure for using the same to implant a revision hip prosthesis |
US10064725B2 (en) | 2011-04-06 | 2018-09-04 | DePuy Synthes Products, Inc. | Distal reamer for use during an orthopaedic surgical procedure to implant a revision hip prosthesis |
US9504578B2 (en) | 2011-04-06 | 2016-11-29 | Depuy Synthes Products, Inc | Revision hip prosthesis having an implantable distal stem component |
US10226345B2 (en) | 2011-04-06 | 2019-03-12 | DePuy Synthes Products, Inc. | Version-replicating instrument and orthopaedic surgical procedure for using the same to implant a revision hip prosthesis |
US9597188B2 (en) | 2011-04-06 | 2017-03-21 | DePuy Synthes Products, Inc. | Version-replicating instrument and orthopaedic surgical procedure for using the same to implant a revision hip prosthesis |
US10603173B2 (en) | 2011-04-06 | 2020-03-31 | DePuy Synthes Products, Inc. | Orthopaedic surgical procedure for implanting a revision hip prosthesis |
US10772730B2 (en) | 2011-04-06 | 2020-09-15 | DePuy Synthes Products, Inc. | Finishing rasp and orthopaedic surgical procedure for using the same to implant a revision hip prosthesis |
US10888427B2 (en) | 2011-04-06 | 2021-01-12 | DePuy Synthes Products, Inc. | Distal reamer for use during an orthopaedic surgical procedure to implant a revision hip prosthesis |
US10925739B2 (en) | 2011-04-06 | 2021-02-23 | DePuy Synthes Products, Inc. | Version-replicating instrument and orthopaedic surgical procedure for using the same to implant a revision hip prosthesis |
WO2020095957A1 (en) * | 2018-11-07 | 2020-05-14 | 株式会社Adeka | Thermal stabilizer, thermal stabilizer composition containing same, polyamide resin composition containing said thermal stabilizer or said thermal stabilizer composition, and molded article of said polyamide resin composition |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3869394A (en) | Lubricant composition and method | |
US3224971A (en) | Borate esters and lubricant compositions containing said esters | |
US2795552A (en) | Lubricant compositions | |
US3897351A (en) | Lubricant compositions | |
US3048608A (en) | Neopentyl glycol esters | |
US4104179A (en) | Lubricating and petroleum fuel oil compositions containing azole polysulfide wear inhibitors | |
US3914241A (en) | Oil soluble derivatives of 2,5-di-mercapto-1,3,4-thiadiazole and process for preparation thereof | |
US3536706A (en) | Phenothiazine compounds | |
US3849322A (en) | Alkylated tertiary amines as high-temperature antioxidants for ester base lubricants | |
US2737492A (en) | Lubricating oil compositions | |
US2795549A (en) | Lubricating oil compositions | |
US4283296A (en) | Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same | |
US2341565A (en) | Compounded oil | |
US2786812A (en) | Mineral oil compositions containing tincontaining dithiophosphate compounds | |
US4064059A (en) | Synthetic aircraft turbine oil | |
US2344988A (en) | Compounded mineral oil | |
US2796404A (en) | Extreme pressure lubricant compositions | |
US4210541A (en) | Stabilized hydraulic fluid composition | |
US2274302A (en) | Compounded oil | |
US2971912A (en) | Lubricating oil compositions | |
US4122021A (en) | Antioxidant stabilized lubricating oils | |
US2836565A (en) | Lubricating compositions | |
US3642632A (en) | Anthranilic acid esters as lubricant additives | |
US2346153A (en) | Compounded oil | |
CA1240336A (en) | Multifunctional additives for functional fluids and lubricants |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: HATCO CHEMICAL CORPORATION, KING GEORGE POST RD., Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:WALTER E. HELLE FACTORS, INC.;REEL/FRAME:003850/0858 Effective date: 19810417 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED FILE - (OLD CASE ADDED FOR FILE TRACKING PURPOSES) |
|
AS | Assignment |
Owner name: MASSMUTUAL PARTICIPATION INVESTORS, MASSACHUSETTS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HATCO CORPORATION, A NEW JERSEY CORP.;REEL/FRAME:008442/0836 Effective date: 19970127 Owner name: PNC BANK, N.A. AS PER AGENT FOR OTHER SECURED PART Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HATCO CORPORATION, A NEW JERSEY CORP.;REEL/FRAME:008442/0836 Effective date: 19970127 Owner name: MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY, MASSA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HATCO CORPORATION, A NEW JERSEY CORP.;REEL/FRAME:008442/0836 Effective date: 19970127 Owner name: MASSMUTUAL CORPORATE VALUE PARTNERS LIMITED, CAYMA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HATCO CORPORATION, A NEW JERSEY CORP.;REEL/FRAME:008442/0836 Effective date: 19970127 Owner name: CM LIFE INSURANCE COMPANY, C/O MASSACHUSETTS MUTUA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HATCO CORPORATION, A NEW JERSEY CORP.;REEL/FRAME:008442/0836 Effective date: 19970127 |
|
AS | Assignment |
Owner name: PNC BANK, NATIONAL ASSOCIATION AND FIRST UNION NAT Free format text: MORTGAGE AND SECURITY AGREEMENT;ASSIGNOR:ROYAL LUBRICANTS, INC.;REEL/FRAME:009833/0445 Effective date: 19990122 |
|
AS | Assignment |
Owner name: PNC BANK, NATIONAL ASSOCIATION AND FIRST UNION NAT Free format text: DISCHARGE OF SECURITY INTEREST IN PATENTS;ASSIGNOR:HATCO CORPORATION;REEL/FRAME:010133/0603 Effective date: 19990616 |