US2813828A - Stabilized grease composition containing a thiodiarylamine and a dialkyl telluride or selanide - Google Patents
Stabilized grease composition containing a thiodiarylamine and a dialkyl telluride or selanide Download PDFInfo
- Publication number
- US2813828A US2813828A US503809A US50380955A US2813828A US 2813828 A US2813828 A US 2813828A US 503809 A US503809 A US 503809A US 50380955 A US50380955 A US 50380955A US 2813828 A US2813828 A US 2813828A
- Authority
- US
- United States
- Prior art keywords
- grease
- oil
- dialkyl
- weight
- selenide
- 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
- 239000004519 grease Substances 0.000 title claims description 56
- 239000000203 mixture Substances 0.000 title description 25
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 title description 5
- 239000003921 oil Substances 0.000 claims description 25
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 17
- 230000001050 lubricating effect Effects 0.000 claims description 12
- 239000010687 lubricating oil Substances 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- 229950000688 phenothiazine Drugs 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- KUUNNVBBPBDFJZ-UHFFFAOYSA-N 1-dodecylselanyldodecane Chemical compound CCCCCCCCCCCC[Se]CCCCCCCCCCCC KUUNNVBBPBDFJZ-UHFFFAOYSA-N 0.000 claims description 7
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 claims description 7
- 239000002480 mineral oil Substances 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- -1 aliphatic radical Chemical group 0.000 description 45
- 150000003346 selenoethers Chemical class 0.000 description 27
- 239000000344 soap Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 20
- 239000011669 selenium Substances 0.000 description 18
- 239000000654 additive Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 150000003871 sulfonates Chemical class 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 229910052711 selenium Inorganic materials 0.000 description 14
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 11
- 150000004772 tellurides Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000010688 mineral lubricating oil Substances 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
- 229910052714 tellurium Inorganic materials 0.000 description 8
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 150000003498 tellurium compounds Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 description 3
- JPIIVHIVGGOMMV-UHFFFAOYSA-N ditellurium Chemical compound [Te]=[Te] JPIIVHIVGGOMMV-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940065287 selenium compound Drugs 0.000 description 3
- 150000003343 selenium compounds Chemical class 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- ZNNRMNHQIYLRMV-UHFFFAOYSA-N 1,1,2,2-tetraethoxy-2-phenoxyethanol Chemical class CCOC(O)(OCC)C(OCC)(OCC)OC1=CC=CC=C1 ZNNRMNHQIYLRMV-UHFFFAOYSA-N 0.000 description 2
- XEFAJZOBODPHBG-UHFFFAOYSA-N 1-phenoxyethanol Chemical class CC(O)OC1=CC=CC=C1 XEFAJZOBODPHBG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000003959 diselenides Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229940072106 hydroxystearate Drugs 0.000 description 2
- IWLIGYVIVUNEFA-UHFFFAOYSA-N lithium;octadecaneperoxoic acid Chemical compound [Li].CCCCCCCCCCCCCCCCCC(=O)OO IWLIGYVIVUNEFA-UHFFFAOYSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- OFYZVDBRERSYHS-UHFFFAOYSA-N (1,1,2,2-tetraethoxy-2-octoxyethoxy)benzene Chemical compound CCCCCCCCOC(OCC)(OCC)C(OCC)(OCC)OC1=CC=CC=C1 OFYZVDBRERSYHS-UHFFFAOYSA-N 0.000 description 1
- BCEJGOSVOXYAIR-UHFFFAOYSA-N 1-(decyldiselanyl)decane Chemical compound CCCCCCCCCC[Se][Se]CCCCCCCCCC BCEJGOSVOXYAIR-UHFFFAOYSA-N 0.000 description 1
- WYBNBJUTWWUYEF-UHFFFAOYSA-N 1-(dodecyldiselanyl)dodecane Chemical compound CCCCCCCCCCCC[Se][Se]CCCCCCCCCCCC WYBNBJUTWWUYEF-UHFFFAOYSA-N 0.000 description 1
- PAYATZOFFVMGOG-UHFFFAOYSA-N 1-(hexadecyldiselanyl)hexadecane Chemical compound CCCCCCCCCCCCCCCC[Se][Se]CCCCCCCCCCCCCCCC PAYATZOFFVMGOG-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- FGIOHOBVUCNHBY-UHFFFAOYSA-N 1-chloroheptadecane Chemical compound CCCCCCCCCCCCCCCCCCl FGIOHOBVUCNHBY-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- AFGNVSCTEXUEJE-UHFFFAOYSA-N 1-chloroicosane Chemical compound CCCCCCCCCCCCCCCCCCCCCl AFGNVSCTEXUEJE-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- CHONGHNRPGYYSL-UHFFFAOYSA-N 1-tetradecylselanyltetradecane Chemical compound C(CCCCCCCCCCCCC)[Se]CCCCCCCCCCCCCC CHONGHNRPGYYSL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UVHNEJFREAIXLX-UHFFFAOYSA-N S-(N-phenylanilino)thiohydroxylamine Chemical class NSN(C1=CC=CC=C1)C1=CC=CC=C1 UVHNEJFREAIXLX-UHFFFAOYSA-N 0.000 description 1
- IQTMWNQRJYAGDL-UHFFFAOYSA-N [SeH2]=[Se] Chemical class [SeH2]=[Se] IQTMWNQRJYAGDL-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 150000003962 selenoxides Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003497 tellurium Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 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
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/046—Hydroxy ethers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
-
- 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
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- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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- C10N2040/02—Bearings
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- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
Definitions
- This invention is concerned with improved grease compositions. More particularly, it is directed to soap-base greases containing a combination of additive materials for improving the durability of the grease.
- Greases are primarily subject to the degenerating influences of air and heat.
- the degradation of the ingredients present in grease compositions results in the formation of materials such as acids and the like which are corrosive to bearings and furthermore generate additional decomposition of certain of the grease ingredients.
- Numerous additives have been investigated for improving various properties of greases including their corrosion resistance, thermal stability, oxidation resistance and extreme pressure properties. It has been the experience of most investigators to find that the addition of many materials, while improving the grease composition with respect to a certain function thereof, simultaneously causes or increases a disadvantageous property of the grease. More specifically, certain corrosion inhibitors have been found to improve the corrosion resistance of the grease compositions but at the same time to cause the latter to have poorer oxidation (or bearing performance) properties.
- alkali metal soap greases which have been previously stabilized against corrosion by the addition of oil-soluble sulfonates and/ or the presence of alkylphenoxypolyethoxy ethanols
- alkali metal soap greases containing the combination of oil-soluble petroleum sulfonates together with the alkylphenoxypolyethoxy ethanols have been found to be improved in resistance 'to corrosiorr but their oxidation (or bearing performance) properties have been impaired by the presence of these combined additives.
- the present invention comprises the discovery that this disadvantageous property is unexpectedly overcome to a surprisingly great degree by the combined presence of the thiodiarylamines and the dialkyl selenides or tellurides (or the corresponding mercaptans). This is especially unexpected in view of the fact that the use of the individual additives is of a relatively minor order but that when employing both of the materials together far more than an additive efiect results.
- the soaps which are utilized as the gelling agent for the subject grease compositions comprise the alkali metal soaps of fatty or hydroxy fatty acids wherein single acids or mixtures thereof may be employed, the acids predominating in members having carbon atom chain lengths of between about 12 and about 24 carbon atoms and preferably between about 16 and 22 carbon atoms.
- the alkali metal radical may be either sodium, lithium or potassium, or mixtures thereof, while the greatest response is found when modifying greases gelled with either soaps predominating in lithium l2-hydroxy stearate or soaps predominating in lithium stearate, or mixtures of said soaps.
- the proportion of soap utilized in the subject composition may vary depending upon the consistency desired, but should be suflicient to gel the lubricating oil to a grease consistency. Normally, the soap content will'be within the range from about 5% to about 25% by weight of the composition.
- R is an aliphatic radical
- R1 is a substituent of the group consisting of hydrogen atoms and aliphatic radicals
- X is an element of the group consisting of selenium and tellurium
- n is a whole number less than 3, i. e., 1 or 2, said compound containing at least 8 carbon atoms per molecule.
- the constituents R and R1 are aliphatic hydrocarbon radicals and the element X is selenium.
- the three principal groups of compounds falling within the general formula, as defined above, include dialkyl selenides, dialkyl diselenides and alkyl selenomercaptans as well as the analagoustellurium compounds and substituted or unsaturated analogs of the same.
- dialkyl selenides dialkyl diselenides and alkyl selenomercaptans as well as the analagoustellurium compounds and substituted or unsaturated analogs of the same.
- 1S0 Ditetradecyl selenide is C14H29 Se C14H29iso Dihep-tadecyl selenide, iso C17H35 Se C17 Has-iso Polar substituted monoselenides Bis (beta-chlorocetyl) selenide 0 Hair 0 H' C HgSe-CH:' C H- 014E ('11 $1 Bis beta-hydroxy cetyl) selenide 0 H19- 0 H- C Hg-Se-CHg- C H- C Hg: 1a: H
- Dilauryl selenoxide
- dialkyl selenides anddialkyl tellurides preferably containing at least'8. carbon atoms in an alkyl group
- the alkyl groups R and R1 may be not only straight and branched chain saturated alkyl groups C11H21L+l, but also straight and-branched chain unsaturated aliphatic groups CnHZn-l, C71H21L3, etc., and also cycloalkyl or cy'cloaliphatic groups. 'That is,--the1 groups attached to selenium and tellurium in the compounding agents of the present invention, may be saturated, unsaturated or cyclic aliphatic groups.
- the groups R and R1 may be substituted by aromatic groups, such as thephenyl, hydroxy phenyl' and amino phenyl groups, provided such groups are spaced at least one carbon atom from the group (X11).
- Polar groups such as chlorine, bromine, hydroxyl, ether, keto, amino, free carboxyl, metallo carboxyl, carboxy ester, mercapto, mercaptide," inono-, diand poly-sulfide, etc., may be substituted in the groups R and R1 of the selenides and tellurides of the present invention. Two or more selenide or telluride groups (X)'n may be present in the molecule.
- selenium and tellurium compounds of the present invention decyl methyl menoselenide, cetyl ethyl monoselenide, octyl decyl monoselenide; dieicosyl monoselenidejdioctyl diselenide, didecyl diselenide, diheptadecyl dise'lenide, dieicosyl diselenide; decyl methyl monotelluride, cetyl ethyl monotelluride, octyl decyl monotelluride didecyl monotelluride, diundecyl monotelluride, dilauryl monotelluride, ditetradecyl monotelluride, dicetyl monotelluride, diheptadecyl monotelluride, dieicosyl monotelluride; dioctyl ditelluride
- chlorinated hydrocarbons such as decyl chloride, dodecyl chloride, tetradecyl chloride, cetyl chloride, heptadecyl chloride, eicosyl chloride, chlorinated lubricating oil and chlorinated wax.
- the selenides are preferred to the tellurides, because they are more stable and more easily prepared. However, the tellurides are highly effective as oil stabilizers and may be preferred in certain cases. Mixtures of selenides or tellurides are suitable, such as those prepared by condensing a metal selenide, polyselenide, telluride or polytelluride with a chlorinated or brominated mixture of hydrocarbons, for example, chlorinated or brominated lubricating oil or parafiin wax. It is not essential that all of the halogen be removed in the condensation reaction; thus a chlorinecontaining dialkyl selenide ortelluride or mixture of dialkyl selenides or tellurides may be used. Also, a mixture of selenides and tellurides may be used.
- seleno-"-or' telluro-mercaptans are also effective. These selenium compounds arethe aliphatic selenomercaptans. Tellurium may be substituted for selenium,
- R1, R2 and R3 are hydrogen or organic radicals (any two of which may be joined to form a single, bivalent radical), C is an aliphatic carbon atom (i. e., a carbon atom other than a carbon atom forming part of a benzenoid ring), and X is selenium or tellurium.
- the preferred compounds of the invention are those containing 8 to 30 carbon atoms, most advantageously, 10 to 30 carbon atoms in the molecule.
- the selenium compounds are preferred to the tellurium compounds.
- selenium and tellurium compounds of the invention are Z-ethylhexyl, decyl, lauryl, cetyl, octadecyl, and paraflin selenomercaptans and 2-ethylhexyl, lauryl and octadecyl telluromercaptans.
- Other-radicals i.
- alkyl radicals such as undecyl and tetradecyl
- aralkyl radicals such as 'cetylbenzyl and cycloaliphatic radicals such as ethylcyclohexyl and butyl cyclohexyl
- the organic radical attached to selenium may contain an .unsaturated group or may be substituted by a non-hydrocarbon substituent such as chlorine, hydroxyl, alkoxyl,
- parafiin as used herein to designate an organic radical is meant a radical derived from paraffin wax; e. g., parafiin selenomercaptan is a selenomercaptau (actually, a mixing of selenomercaptan), such as can'be prepared by using chlorinated paraffin wax as an organic chloride, R.Cl, to be reacted, with NazSez to form a dialkyl diselenide, RSeSeR.
- aliphatic as used herein without qualification to designate an organic radical attached to selenium or tellurium, is meant an organic radical whose attachment to selenium or tellurium is through a non-benzenoid carbon atom; e. g., octadecyl, benzyl and cyclohexyl selenomercaptans are all aliphatic selenomercaptans as aliphatic is herein defined.
- the second class of additives to be incorporated together with the above-described selenides, tellurides and the corresponding mercaptans comprise the thiodiarylamines.
- R is an aromatic radical.
- Three principal .classes of inhibitors fall within the above general 'formula. These comprise species based upon thiodiphenylamine, those based on thiophenyl naphthylamine and finally, those based upon thiodinaphthylamine.
- the preferred class of inhibitors of this type comprise the thiodiphenylamines as typified by phenothiazine.
- the aryl radicals contained in these materials may be modified by such substituents as alkyl radicals having less than 6 carbon atoms each, hydroxy groups or amino radicals and any amino radicals in the compound may be likewise modified by replacement of hydrogen atoms with alkyl, aryl, hydroxy or amino substituents.
- the general formulae and species thereunder of these three classes of materials are given herewith:
- a particularly effective type of additive comprises the amino thiodiphenylamines which have the general R and R in the above formula may be substituents such as hydrogen, alkyl, aryl, heterocyclic or cycloparaflin groups. Species falling within this class are given below.
- the combination of these two materials produced an entirely unexpected magnitude of efiect in extending the bearing life of greases and in overcoming the disadvantages which are created by the incorporation of other additives utilized for special purposes.
- the results are especially outstanding and surprising when the additives comprise oil-soluble sulfonates or alkylphenoxypolyethoxy ethanols or combinations of these materials.
- the incorporation of the latter two materials decreases the bearing life of the grease even though they may at the same time provide increased protection against corrosion.
- the sulfonates may be oil-soluble sulfonic compounds derived from the treatment of heavy hydrocarbon oils with strong sulfuric acid, followed by neutralization.
- Suitable sulfonic acids from which the salts are formed are well known in the art as possessing rust-proofing properties, and as set forth in expired U. S. Patent No. 1,630,101 granted to the Standard Oil Company of Indiana, May 24, 1927, and in other U. S. patents including Nos. 1,795,993, 2,923,367, 2,119,553, 2,182,992, 2,348,715 and 2,349,785.
- sulfonates contain a polar type of molecule which is oil-soluble, and further, they possess the property of adhering to the metal to which they are applied, thereby preventing scufiing or pushing away of the oil films. Therefore, sulfonates keep the metal surfaces constantly covered with a film of the lubricant and also act as a rust-proofing agent.
- Various soaps of the sulfonates may be used including metal soaps such as sodium, lithium and calcium sulfonates.
- Lithium petroleum sulfonate is found to be a very satisfactory rust-proofing agent.
- Many of the other metal sulfonates are well known in the art to act as rustproofing agents when incorporated in a lubricating grease.
- lithium petroleum sulfonate that is, the lithium soap of the product produced by reacting a lithium salt with the sulfonate resulting from the treatment of heavy hydrocarbon oils with strong sulfuric acid, is thought to be novel with the applicants.
- organic amino oil-soluble sulfonates function satisfactorily as a rust-proofing agent when incorporated in lithium soap and sodium soap when the molecular weight of said sulfonates approach the molecular weight of the oil.
- Short chain molecules are not as soluble in oil as the larger chain molecules.
- alkali petroleum sulfonates and the synthetic hydrocarbon sulfonates which give the best results are those which have an average molecular Weight of 300 to 500, thereby tending to make the sulfonate quite soluble in both naphthenic and paraffinic base oils.
- the phenoxy ethanols have the general formula where R is an aromatic nucleus of the benzene, anthracene, phenanthrene, naphthalene or other condensed ring series, Y is an aliphatic, cycloaliphatic, arylaliphatic or aryl group having at least four carbon atoms, and n is a whole number between 3 and 10 (preferably 4).
- rust-preventive additives in greases of this invention are substituted phenoxy tetraethoxy ethanols, substituted naphthoxy tetraethoxy ethanols, sub stituted anthroxy tetraethoxy ethanols, substituted phenanthroxy tetraethoxy ethanols, and the like, wherein at least one of the substituents in the aromatic nucleus is a group such as butyl, amyl, hexyl, octyl, dodecyl, tetradecyl, hexadecyl, oleyl or other alkyl group containing up to 30 carbon atoms; a cycloaliphatic group, such as cyclohexyl, octyl-cyclohexyl, lauryl-cyclohexyl, cetyl-cyclohexyl, butyl-cyclohexyl,
- the substituents above mentioned may have straight or branched chains and the aromatic nucleus of the -above-defined compounds may have more than one substituent which .may' eitherbe the sameor a different group.
- the aromatic nucleus of the above compounds may contain four orrnore carbon atoms; the remaining substituent'or substituents may then optionally contain less than four carbon.
- the. diand poly-substituted compounds of thetype described above are more eifective in inhibiting rustformation when. incorporated in greases than the mono-substituted compounds.
- the use of the former type compounds accordinglyrepresents a preferred embodiment of this invention.
- thesubstituted phenoxy tetraethoxy ethanols. are suitably employed as rust-preventive additives in the greases of the present invention.
- n is an integer between about 3 and 1:0, preferably 5, X is a halogen atom, said condensation taking place in the presence of an alkali to split out an alkali metal halide and thus yield the desired inhibitor.
- Example I A grease prepared by gellinga 4:1 weight ratio of bis(2-ethylhexyl) sebacate and light mineral lubricating oil with lithium stearate was used as the primary grease tobe modified by additives and is labeled grease A.
- Grease B was formed by incorporating in this. grease 1.5% by Weight of sodium petroleum sulfonates having an average molecular weight of about 470 and 1% by Weight of octyl phenoxy tetraethoxy ethanol.
- Grease C was prepared by modifying grease B With the addition of 1% by weight of phenothiazine and 1% by'weight of dilauryl selenide.
- the table given below lists the data obtained by utilizing these three greases in a high temperature bearing test at temperatures of 250 and 300 F. at 10,000 R. P. M.
- Example II A grease was prepared by gelling a medium viscosity mineral lubricating oil with lithium l2-hydroxy stearate.
- a lubricating grease comprising a major amount of a mixed lubricating oil, said oil comprising a major amount of bis(2-ethylhexyl) sebacate and a minor amount of a mineral oil, a minor amount of lithium stearate sufficient to thicken saidoil to a grease consistency, and 0.252% by weight each of sodium petroleum sulfonates, octylphenoxytetraethoxyethanol, dilauryl selenide and phenothiazine.
- a lubricating grease composition comprising a major amount of a mineral lubricating oil, a minor amount sufficient to gel said oil to a grease consistency, of lithium hydroxy stearate, and 0.25-2% by; weight each of sodium petroleum sulfonates, octylphenoxytetraethoxyethanol, dilauryl selenide and phenothiazine.
- a lubricating grease comprising a major amount of a mineral lubricating oil, a minor amount of lithium stearate sufficient to gel said oil to a grease consistency, and from about 0.1% to about 3% -by weight each of an alkali metal hydrocarbon sulfonate, an alkyl-substituted phenoxy polyethoxy ethanol,.-a dialkyl selenide and a thiodiphenylamine.
- a lubricatinggrease comprising a major amount of a mixed lubricating oil, saidoil comprising a major amount of bis(2-e thylhexyl) sebacateandaminor amount of a mineral oil, a minor amount of lithium stearate sufficient to thicken said oil to a grease consistency, and from about 0.1% to about;3% by Weight each of an alkali metal hydrocarbon'sulfonate, an alkyl-substituted phenoxy polyethoxy ethanol, a dialkyl selenide and a thiodiphenylamine.
- a lubricating grease comprising a major amount of a mixed lubricating oil, said oil comprising a major amount of bis(2-ethylhe,xyl) sebacate and a minor amount of a mineral oil, a minor amount of lithium stearate sufiicient to thicken said oil to a grease consistency, and from about 0.1% to about 3% by weight of phenothiazine and dilauryl selenide.
- a lubricating grease comprising a major amount of mineral lubricating oil, a minor amount of lithium hydroxy stearate sufiicient to thicken said-oil to a grease consistency, and from about 0.1% to about 3% by weight each of phenothiazine and dilauryl selenide.
- a lubricatinggrease comprising a major amount of a mixed lubricating oil, said oil comprising a major amount of .an aliphatic ester of a dicarboxylic acid and a minor amountof a mineral lubricating oil, a minor amount of lithium. soaps of fatty acids sufficient to thicken said oil to a grease consistency, and from about 0.1% ,to about 3% by Weight each of a dialkyl selenide and a gthiodiphenylamine.
- a lubricating grease comprising a major amount of amineral lubricating oil, a minor amount oflithium soap of hydroxy fatty acids suflicient to thicken the oil to a grease consistency, and from about 0.1% to about 3% by weight each of a dialkyl selenide and a thiodiphenylamine.
- a lubricating grease comprising a major amount of a mixed lubricating oil, said oil comprising a major amount of an aliphatic ester of a dicarboxylic acid and a minor amount of a mineral lubricating oil, and a minor amount of a lithium soap sufficient to thicken the oil to a grease consistency, and from about 0.1% to about 3% by weight each of a dialkyl selenide and a thiodiphenylamine.
- a lubricating grease comprising a major amount of a lubricating oil, a minor amount of a lithium soap suflicient to thicken the oil to a grease consistency, and from about 0.1% to about 3% by weight each of a dialkyl selenide and a thiodiphenylamine.
- a lubricating grease comprising a major amount of a mineral lubricating oil, a minor amount of a lithium soap sufiicient to thicken the oil to a grease consistency, and from about 0.1% to about 3% by weight each of a dialkyl selenide and a thiodiphenylamine.
- a lubricating grease comprising a major amount of a lubricating oil, a minor amount of an alkali metal soap sufficient to thicken the oil to a grease consistency, and from about 0.1% to about 3% by weight each of a dialkyl selenide and a thiodiphenylamine.
- R is an aliphatic radical
- R1 is a substituent of the group consisting of hydrogen atoms and aliphatic radicals
- X is an element of the group consisting of selenium and tellurium
- n is a full integer less than 3, said compound containing at least 8 carbon atoms per molecule.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL94870D NL94870C (forum.php) | 1955-04-25 | ||
| BE547241D BE547241A (forum.php) | 1955-04-25 | ||
| US503809A US2813828A (en) | 1955-04-25 | 1955-04-25 | Stabilized grease composition containing a thiodiarylamine and a dialkyl telluride or selanide |
| FR1162143D FR1162143A (fr) | 1955-04-25 | 1956-04-23 | Composition de graisse lubrifiante |
| GB12377/56A GB789947A (en) | 1955-04-25 | 1956-04-23 | Lubricating grease compositions |
| DEN12154A DE1003901B (de) | 1955-04-25 | 1956-04-23 | Schmierfett |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US503809A US2813828A (en) | 1955-04-25 | 1955-04-25 | Stabilized grease composition containing a thiodiarylamine and a dialkyl telluride or selanide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2813828A true US2813828A (en) | 1957-11-19 |
Family
ID=24003600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US503809A Expired - Lifetime US2813828A (en) | 1955-04-25 | 1955-04-25 | Stabilized grease composition containing a thiodiarylamine and a dialkyl telluride or selanide |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2813828A (forum.php) |
| BE (1) | BE547241A (forum.php) |
| DE (1) | DE1003901B (forum.php) |
| FR (1) | FR1162143A (forum.php) |
| GB (1) | GB789947A (forum.php) |
| NL (1) | NL94870C (forum.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2998386A (en) * | 1959-01-26 | 1961-08-29 | Sinclair Refining Co | Lubricant containing a fatty acid amide of phenothiazine |
| US3389124A (en) * | 1965-01-28 | 1968-06-18 | Universal Oil Prod Co | Organic substance stabilized with amino-substituted polycyclic heterocyclic inhibitor |
| WO2018165760A1 (en) * | 2017-03-17 | 2018-09-20 | University Of Ottawa | Azaphenothiazines and azaphenoxazines as antioxidants |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2227908A (en) * | 1937-03-19 | 1941-01-07 | Tide Water Associated Oil Comp | Lubricating oil and lubrication therewith |
| US2450321A (en) * | 1947-04-09 | 1948-09-28 | Socony Vacuum Oil Co Inc | Rust-inhibiting greases |
| US2609343A (en) * | 1948-07-12 | 1952-09-02 | Charles E Saunders | Oxidation inhibitor for lubricating oils |
| US2652365A (en) * | 1949-06-24 | 1953-09-15 | Shell Dev | Manufacture of grease compositions |
| US2693449A (en) * | 1948-08-13 | 1954-11-02 | George M Hain | Silicone greases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE874823C (de) * | 1942-08-22 | 1953-04-27 | Ruhrchemie Ag | Verfahren zur Herstellung bestaendiger synthetischer Schmieroele |
| GB700804A (en) * | 1949-06-18 | 1953-12-09 | California Research Corp | Lubricating oil compositions |
-
0
- NL NL94870D patent/NL94870C/xx active
- BE BE547241D patent/BE547241A/xx unknown
-
1955
- 1955-04-25 US US503809A patent/US2813828A/en not_active Expired - Lifetime
-
1956
- 1956-04-23 DE DEN12154A patent/DE1003901B/de active Pending
- 1956-04-23 GB GB12377/56A patent/GB789947A/en not_active Expired
- 1956-04-23 FR FR1162143D patent/FR1162143A/fr not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2227908A (en) * | 1937-03-19 | 1941-01-07 | Tide Water Associated Oil Comp | Lubricating oil and lubrication therewith |
| US2450321A (en) * | 1947-04-09 | 1948-09-28 | Socony Vacuum Oil Co Inc | Rust-inhibiting greases |
| US2609343A (en) * | 1948-07-12 | 1952-09-02 | Charles E Saunders | Oxidation inhibitor for lubricating oils |
| US2693449A (en) * | 1948-08-13 | 1954-11-02 | George M Hain | Silicone greases |
| US2652365A (en) * | 1949-06-24 | 1953-09-15 | Shell Dev | Manufacture of grease compositions |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2998386A (en) * | 1959-01-26 | 1961-08-29 | Sinclair Refining Co | Lubricant containing a fatty acid amide of phenothiazine |
| US3389124A (en) * | 1965-01-28 | 1968-06-18 | Universal Oil Prod Co | Organic substance stabilized with amino-substituted polycyclic heterocyclic inhibitor |
| WO2018165760A1 (en) * | 2017-03-17 | 2018-09-20 | University Of Ottawa | Azaphenothiazines and azaphenoxazines as antioxidants |
| US11512262B2 (en) | 2017-03-17 | 2022-11-29 | University Of Ottawa | Azaphenothiazines and azaphenoxazines as antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| NL94870C (forum.php) | |
| BE547241A (forum.php) | |
| FR1162143A (fr) | 1958-09-09 |
| GB789947A (en) | 1958-01-29 |
| DE1003901B (de) | 1957-03-07 |
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