US2597838A - Lubricant containing selenium compounds - Google Patents
Lubricant containing selenium compounds Download PDFInfo
- Publication number
- US2597838A US2597838A US103937A US10393749A US2597838A US 2597838 A US2597838 A US 2597838A US 103937 A US103937 A US 103937A US 10393749 A US10393749 A US 10393749A US 2597838 A US2597838 A US 2597838A
- Authority
- US
- United States
- Prior art keywords
- selenium
- silver
- thiazine
- compounds
- mercapto
- 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
- 239000000314 lubricant Substances 0.000 title claims description 18
- 229940065287 selenium compound Drugs 0.000 title description 24
- 150000003343 selenium compounds Chemical class 0.000 title description 24
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 40
- 229910052711 selenium Inorganic materials 0.000 claims description 39
- 239000011669 selenium Substances 0.000 claims description 39
- 229910052709 silver Inorganic materials 0.000 claims description 39
- 239000004332 silver Substances 0.000 claims description 39
- 239000010687 lubricating oil Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 12
- KDSXXMBJKHQCAA-UHFFFAOYSA-N disilver;selenium(2-) Chemical compound [Se-2].[Ag+].[Ag+] KDSXXMBJKHQCAA-UHFFFAOYSA-N 0.000 claims description 8
- YZZWZWGTNAEJIN-UHFFFAOYSA-N 2-sulfanylthiazine Chemical compound SN1SC=CC=C1 YZZWZWGTNAEJIN-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 37
- -1 dialkyl selenides Chemical class 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 19
- 150000002739 metals Chemical class 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 239000003223 protective agent Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 229910052791 calcium Inorganic materials 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000003346 selenoethers Chemical class 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- DLBJODXBDQMKRQ-UHFFFAOYSA-N 4,6,6-trimethyl-3h-1,3-thiazine-2-thione Chemical compound CC1=CC(C)(C)SC(=S)N1 DLBJODXBDQMKRQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 210000000707 wrist Anatomy 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- WYBNBJUTWWUYEF-UHFFFAOYSA-N 1-(dodecyldiselanyl)dodecane Chemical compound CCCCCCCCCCCC[Se][Se]CCCCCCCCCCCC WYBNBJUTWWUYEF-UHFFFAOYSA-N 0.000 description 1
- OLAMEXHKEKPEOY-UHFFFAOYSA-N 1-(octadecyldiselanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCC[Se][Se]CCCCCCCCCCCCCCCCCC OLAMEXHKEKPEOY-UHFFFAOYSA-N 0.000 description 1
- UUWLZGKDIBYHGH-UHFFFAOYSA-N 1-(octyldiselanyl)octane Chemical compound CCCCCCCC[Se][Se]CCCCCCCC UUWLZGKDIBYHGH-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
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- JMPVDLQJWPKEOX-UHFFFAOYSA-N 1-sulfanylselanyldodecane Chemical compound C(CCCCCCCCCCC)[Se]S JMPVDLQJWPKEOX-UHFFFAOYSA-N 0.000 description 1
- PYVGPIWTSZUWGZ-UHFFFAOYSA-N 1-sulfanylselanyloctadecane Chemical compound C(CCCCCCCCCCCCCCCCC)[Se]S PYVGPIWTSZUWGZ-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- RLHFVQZGAHOKPT-UHFFFAOYSA-N 2h-thiazine-3-thiol Chemical compound SC1=CC=CSN1 RLHFVQZGAHOKPT-UHFFFAOYSA-N 0.000 description 1
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical class SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 1
- DVSVFZYHLJZODI-UHFFFAOYSA-N 5-ethyl-3h-1,3-thiazole-2-thione Chemical compound CCC1=CN=C(S)S1 DVSVFZYHLJZODI-UHFFFAOYSA-N 0.000 description 1
- 229910000897 Babbitt (metal) Inorganic materials 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000035217 Ring chromosome 1 syndrome Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- DHJGVCITGOCTCA-UHFFFAOYSA-L calcium;hexadecyl phosphate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O DHJGVCITGOCTCA-UHFFFAOYSA-L 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000010730 cutting oil Substances 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
- 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
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- ZLELDFZZMFTDAO-UHFFFAOYSA-N potassium cyanide hydrochloride Chemical compound Cl.[C-]#N.[K+] ZLELDFZZMFTDAO-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003342 selenium Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- BMCYFOQLZQQNNH-UHFFFAOYSA-N sulfanylselanylmethane Chemical compound C[Se]S BMCYFOQLZQQNNH-UHFFFAOYSA-N 0.000 description 1
- CAMAJDKQHOHBFU-UHFFFAOYSA-N sulfanylselanylmethylbenzene Chemical compound C(C1=CC=CC=C1)[Se]S CAMAJDKQHOHBFU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003475 thallium Chemical class 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/72—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing sulfur, selenium or tellurium
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
-
- 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
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Definitions
- the present invention relates to lubricatin oils compoundedwith selenium-containing compounds, such as dialkyl selenides, which attack silver and like metals, thereby decreasing the effectiveness of the selenium compound in lubricating oils.
- selenium-containing compounds such as dialkyl selenides
- certain protective agents such as 2mercapto-4,6,6-trimethylthiazine are added to the lubricating oils.
- lubricating oils have been compounded with various improving or stabilizing agents.
- various lubricating oil compounding agents a group of highly effective additives is the selenium-containing organic compounds.
- aliphatic mono-, di-, and higher poly-selenides, seleno-mercaptans, metal selenomercaptides, etc. are highly effective oxidation inhibitors.
- oils compounded with such selenium-containing compounds are adversely affected by silver and like metals.
- the deleterious action involves a direct attack of the metal by selenium, resulting in a rapid discoloration of the metal surface and formation of metal selenides and the subsequent sloughing ofi' of these metal selenides during engine operation.
- the selenium of the selenium-containing compounds attacks the metals during engine operation, the effectiveness of the selenium compounds as addition agents in lubricating oils is considerably decreased.
- the selenium-containing compound attacks the metals in an engine, there is a substantial loss of bearing metal and a pitting of bearing surfaces.
- the present invention concerns the combination of a lubricant compounded with selenium compounds, and a silver-protective agent which greatly minimizes attack on silver by the selenium compounds, whereby the essential functions of the selenium compounds are maintained at maximum activity.
- lubricating oils compounded with selenium-containing additives can be used in Diesel oils, aviation oils, and any other oils Where selenium attack on sensitive metals is a problem, to provide a stable lubricant having selenium compounds of increased effectiveness. While the outstanding advantages of the action of the silver protective agents in lubricants containing selenium compounds is particularly apparent in heavy-duty motor oils, the inventive combination finds application in turbine oils, gear oils, such as for use in hypoid gears, cutting oils, soluble oils,
- the silver protective agents include 2-thiothiazine compounds of which Z-mercapto-thiazine is the simplest member. Also included are the derivatives of said simplest member, wherein the mercapto-hydrogen may be replaced by a hydrolyzable group, and where there may be shortchain saturated and unsaturated aliphatic groups substituted on the ring carbon atoms.
- phatic groups is meant aliphatic groups contain-- ing not more than 8 carbon atoms
- the hydrolyzable group is one which -may;react on hydrolysis to yield hydrogen in the-mercapto group, and includes cationic salt-forming atoms and radicals including metals (e. g., sodium,,.-po -1 tassium, barium, calcium, zinc, aluminum, etc); I
- amines e. g., trimethylamine, n-butylamine, dodecylamine, ammonia, etc.
- amide radicals e. g., cy-
- -2-thio-thiazine compounds are: .2-
- mercapto-4,6,6-trimethyl thiazine zinc. salt of. 2-" mercapto-4,6,6-trimethyl thiazine; Z-mercaptoe l,3-dihydrothiazine; 3-mercapto 2,4,1-thiazine; 2 mercapto4-methyl thiazine; 2 mercapto 4- ethyl thiazine; 2mercapto-4,6-dimethyl thiazine;
- Examples of .1 2-thio-thiazine compounds also include the reaction products obtained by reactinga 2-mercapto-thiazine with the follow! ing: carboxylic acids,-alpha-beta unsaturated ketones, esters, olefins, nitriles, organometallic compounds, sulfonyl halides, ethylene oxide, anhydrides and acyl halides.
- the 2-thio-thiazines embraced in this invention vary in effectiveness-in minimizing the lossof the effectiveness of the selenium compounds; some of the 2-thio-thiazines,-for example, are: effective when used in amounts as low as 0.001 (by weight of total composition) Certain of the 2-thio-thiazines have only limited solubility in the lubricating oil and are effective at that solubility. All
- on-silver and like metals may be obtainedby us-- ing 2-thio-thiazole compounds in conjunction with the Z-thiazine compounds.
- Suitable baseoils include a wide variety of lubricating oils such as naphthenic base, paraflin base, and mixed base mineraloils, other hydro' carbon" lubricants, e. g., lubricating -oil derived from'coalproducts, and-synthetic oils, e. g., alkylg ene polymers '(such as polymers. of propylene,
- alkylene oxide type polymers; dicarboxylic acid GStBI'SIaIId liquid esters; of acids of phosphorus.
- Synthetic oils of. the alkyleneoxide-type polymer vwhich may be used include those exemplified by the al-'
- the major kylene oxide polymers e. g., propylene oxide polymers
- derivatives including alkylene oxide polymers prepared by polymerizing alkylene oxides, e. g., propylene oxide, in the presence of wa- .;;ter:-or.alcohols, e.
- esters of 'alkylene oxide-type polymers e. g., acetylated propyleneoxidepolymers prepared by acetylat- 'ing prop-yleheoxide polymers containing hydrox- Synthe'ticoils of. the dicarboxylic acid ester type include.
- dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, 2-ethyl-hexyl alcohol; -,dode.cyl alcohol; etc.
- dicarbOXYliCifiCid ester synthetic oils include di-butyl adipate, di,hexyl adipate, di-Z-ethyl-hexylseb-.:
- Syntheticioils. of thetypeof liquid esters-of. acidsi of phosphorus. include the esters, of l PhOS-r phoric: acid, 'e. g.,;tricresyl' phosphate ;r* the esters:
- droxyl-containing' compounds such as phenols andaliphatic alcohols, and with olefin oxides such i as-propylene .oxide, as described in Jenseniet -al., U. S. patent application No. 86,856, new abanw doned.
- the improved lubricant of the present .inven-.-. tion is used where the effectiveness of selenium: compounds as lubricant additives. is decreased by the attack on metals by the selenium of the"- .selenium compounds; In order to evaluate. the;
- silver-protective agents of this invention for their effectiveness in inhibiting reduction of activity of. selenium compounds, lubricants containing the selenium compounds and the. protective agents were subjected to a silver strip test which was:
- the protective agents of this invention are eifective ,in protecting other selenium-sensitive metals from selenium attack.
- Such other selenium sensitive metals includecopper, aluminum, and alloys of copper and aluminum.
- alkyl selenides e. g., didodecyl monoselenide, octadecyl methyl monoselenide, octadecyl ethyl moncselenidaoctyl dodecyl monoselenide, di eic'osyl' monoselenide, dioctyl diselenide, di-eicosyl diselenide, dilauryl diselenide, dioctadecyl diselenide, and the various monoand polyselenides prepared by reacting sodiumor other alkali metal monoor polyselenides with halogenated, e.
- alkyl selenides e. g., didodecyl monoselenide, octadecyl methyl monoselenide, octadecyl ethyl moncselenidaoctyl dodecyl mono
- chlorinated hydrocarbons such as decyl'chloride, dodecyl chloride, tetradecyl chloride, octadecyl chloride, heptadecyl chloride, chlorinated lubricating oil and chlorinated wax
- selenomercaptans e.g., chlorinated hydrocarbons, such as decyl'chloride, dodecyl chloride, tetradecyl chloride, octadecyl chloride, heptadecyl chloride, chlorinated lubricating oil and chlorinated wax
- the agents of this invention may be used in lubricating oils containing, in addition to the selenium compounds, other additives such as polyvalent metal phenates (e. g., calcium cetyl phenate), metal organo-sulfonates (e. g., calcium petroleum sulfonate), polyvalent metal salts of acids of phosphorus, such as phosphates (e. g., calcium cetyl phosphate), phosphonates (e. g., calcium white oil phosphonate), thiophosphates (e. g., calcium cetyl thiophosphates), phenols (e. g., 2,6-di-tertiary-butyl-4-methylphenol), etc.
- polyvalent metal phenates e. g., calcium cetyl phenate
- metal organo-sulfonates e. g., calcium petroleum sulfonate
- polyvalent metal salts of acids of phosphorus such as phosphates (e.
- the lubricant compositions of this invention may also contain other agents which are advantageously present, such as oiliness agents, blooming agents, viscosity index improvers, pour point depressants, peptizing agents, etc.
- the silver protective agents of this invention were incorporated in a California solvent.
- Table II below presents the results obtained when freshly polished silver strips were immersed for 30 minutes at a temperature of 300 F. in a California solvent refined S.
- A. E. 30 paraffinic base oil containing calcium petroleum sulfonate, sulfurized calcium cetyl phenate and 0.2% by weight of various selenium compounds 6 with and. without 2 mercapto 4,6,6 trimethyl thiazine as'a silver protective agent. The darker the appearance of the silver strip, the more pronounced the attack on the silver by the selenium compound.
- a lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition corrosive to silver, and a small amount, sufficient substantially to inhibit the formation of silver selenide resulting from the selenium attack on silver, of a Z-mercapto-thiazine wherein not more than four of the ring carbons contain aliphatic groups each of which has not more than 4 carbon atoms.
- a lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which is corrosive to silver, and a 7 small amount, sufficient substantially to inhibit the reaction between the selenium of said lubrieating oil composition and silver, a Z-mercaptothiazine wherein not more than four of the ring carbons contain short chain aliphatic groups, said aliphatic groups containing a total of no more than 16 carbon atoms.
- a lubricating oil composition at least of which is composed of an admixture of an oil of lubricating viscosity and lubricating oil additives having present selenium which reacts with silver-wearing surfaces, and a small amount, sufiicient substantially to inhibit the reaction between the selenium and silver, of a 2 -mercapto-thiazine wherein not more than four of the ring carbons of the said mercapto-thiazine contain short chain aliphatic carbons.
- a lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which attacks silver directly to form silver selenide, and a small amount, sumcient substantially to reduce the selenium attack on silver, of a Z-mercapto-thiazine wherein not more than 4 of the ring carbons contain shortchain aliphatic groups.
- a lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which attacks silver-wearing surfaces to form silver selenide, and a small amount, sufiicient substantially to reduce the selenium attack on silver, of a 2-mercapto-4,6,6-trimethyl thiazine.
Description
Patented May 20, 1952 UNITED STATES LUBRICANT CONTAINING SELENIUM COMIPOUNDS Warren Lowe, William T. Stewart, and James 0. Clayton, Berkeley, Calif., assignors to California Research Corporation, San Francisco, Calif., a
corporation of Delaware No Drawing. Application July 9, 1949, Serial No. 103,937
9 Claims.
The present invention relates to lubricatin oils compoundedwith selenium-containing compounds, such as dialkyl selenides, which attack silver and like metals, thereby decreasing the effectiveness of the selenium compound in lubricating oils. In order to prevent the loss of effectiveness of the selenium compounds by attack on silver and like metals, certain protective agents such as 2mercapto-4,6,6-trimethylthiazine are added to the lubricating oils.
As is well known, the present-day problems involved in the lubrication of internal combustion engines are extremely complex and difficult to overcome due mainly to the great load imposed on the bearings, the high engine speeds, and. the elevated operating temperatures. To avoid rapid deterioration resulting from such severe operating conditions, lubricating oils have been compounded with various improving or stabilizing agents. Of the various lubricating oil compounding agents, a group of highly effective additives is the selenium-containing organic compounds. For example, aliphatic mono-, di-, and higher poly-selenides, seleno-mercaptans, metal selenomercaptides, etc. are highly effective oxidation inhibitors. Unfortunately, oils compounded with such selenium-containing compounds are adversely affected by silver and like metals. The deleterious action involves a direct attack of the metal by selenium, resulting in a rapid discoloration of the metal surface and formation of metal selenides and the subsequent sloughing ofi' of these metal selenides during engine operation. As the selenium of the selenium-containing compounds attacks the metals during engine operation, the effectiveness of the selenium compounds as addition agents in lubricating oils is considerably decreased. For example, when a selenium compound is added to a lubricating oil to inhibit oxidation, the effectiveness of the selenium com- 3 pound is considerably decreased as the seleniumcontaining compound attacks the metal. Also, when the selenium-containing compound attacks the metals in an engine, there is a substantial loss of bearing metal and a pitting of bearing surfaces.
Thus, it may readily be seen that when the selenium of a selenium-containing oxidation inhibitor attacks metals of bearing surfaces, etc., there is a two-fold loss to the system, namely, a reduction in the efiectivenss of the seleniumcontaining compound as an oxidation inhibitor and a loss of sensitive metal from the bearing surfaces during engine operation. It is apparent that in spite of the long desire to lubricate silver bearings with lubricants compounded with selenium compounds, it has been impractical to do so in view of the aforementioned diificulties.
Because of these difficulties with lubricants containing selenium compounds, there is a tendency to eliminate the highly eifective seleniumcontaining additives from the Diesel lubricating oils, thereby losing the remarkable benefits of theseadditives. For example, heretofore, it has been undesirable to use these effective selenium anti-oxidants in lubricants employed for engines containing silver bearings, such as in certain railroad Diesel engines containing silver wrist pin bushings. Alternative practices have been to eliminate the selenium-containing additives from the oil, allowing the oil to deteriorate more rapidly through oxidation; or include the selenium-containing additives, allowing the oil to,
deteoriate less rapidly through oxidation with a consequent selenium attack on the silver wrist pin bushings. Because of the presence of the silver in many aircraft engines, it has not been feasible to use the highly effective selenium-containing aviation oil additives.
Therefore, it is an object of this invention to provide a selenium compound-containing lubricant which is stable to sensitive metals such as silver, whereby the effectiveness of the selenium compounds as oxidation inhibitors is not reduced by the reaction of the selenium compounds with the sensitive metal surfaces.
In the attainment of these objects, the present invention concerns the combination of a lubricant compounded with selenium compounds, and a silver-protective agent which greatly minimizes attack on silver by the selenium compounds, whereby the essential functions of the selenium compounds are maintained at maximum activity.
Now, through the use of the silver-protective agents in accordance with the present invention, lubricating oils compounded with selenium-containing additives can be used in Diesel oils, aviation oils, and any other oils Where selenium attack on sensitive metals is a problem, to provide a stable lubricant having selenium compounds of increased effectiveness. While the outstanding advantages of the action of the silver protective agents in lubricants containing selenium compounds is particularly apparent in heavy-duty motor oils, the inventive combination finds application in turbine oils, gear oils, such as for use in hypoid gears, cutting oils, soluble oils,
greases, etc.
The silver protective agents include 2-thiothiazine compounds of which Z-mercapto-thiazine is the simplest member. Also included are the derivatives of said simplest member, wherein the mercapto-hydrogen may be replaced by a hydrolyzable group, and where there may be shortchain saturated and unsaturated aliphatic groups substituted on the ring carbon atoms. The shortferred that the thiazine ring contain not more than 4 substituents having a total of not more than 16 carbon atoms. It is preferred that each...
substituent group on the thiazineringcontainnot.
more than 4 carbon atoms. By short-chain 'ali-.:
phatic groups is meant aliphatic groups contain-- ing not more than 8 carbon atoms;
The hydrolyzable group is one which -may;react on hydrolysis to yield hydrogen in the-mercapto group, and includes cationic salt-forming atoms and radicals including metals (e. g., sodium,,.-po -1 tassium, barium, calcium, zinc, aluminum, etc); I
groups obtained by salt formation with amines (e. g., trimethylamine, n-butylamine, dodecylamine, ammonia, etc.) amide radicals (e. g., cy-
clohexylamide radical and organic carboxyl and. thionyl radicals such as 'benzoic anddiethyldie thiocarbonyl radicals) Examples of -2-thio-thiazine compounds are: .2-
mercapto-4,6,6-trimethyl thiazine; zinc. salt of. 2-" mercapto-4,6,6-trimethyl thiazine; Z-mercaptoe l,3-dihydrothiazine; 3-mercapto 2,4,1-thiazine; 2 mercapto4-methyl thiazine; 2 mercapto 4- ethyl thiazine; 2mercapto-4,6-dimethyl thiazine;
2 mercapto-i-isobutenyl-6,6-dimethyl thiazine;..
4,6,6 trimethyl thiazine 2 cyclohexyl sulfenamidej and the butyrate ester of 2-mercapto-thiazine. Examples of .1 2-thio-thiazine compounds also include the reaction products obtained by reactinga 2-mercapto-thiazine with the follow! ing: carboxylic acids,-alpha-beta unsaturated ketones, esters, olefins, nitriles, organometallic compounds, sulfonyl halides, ethylene oxide, anhydrides and acyl halides.
Because of the greater effectiveness obtained, it is preferred to use-2-mercapto-4,6,6-trimethyl thiazine to prevent selenium attack on silver.
The 2-thio-thiazines embraced in this invention vary in effectiveness-in minimizing the lossof the effectiveness of the selenium compounds; some of the 2-thio-thiazines,-for example, are: effective when used in amounts as low as 0.001 (by weight of total composition) Certain of the 2-thio-thiazines have only limited solubility in the lubricating oil and are effective at that solubility. All
on-silver and like metals may be obtainedby us-- ing 2-thio-thiazole compounds in conjunction with the Z-thiazine compounds.
Examples of 2-thio-thiazoles-are: Z-mercaptobenzothiazole, N-cyclohexyl '2-benzothiazyl sulfenamide; dodecyl aminesalt of mercaptobenzo thiazole; zinc salt of mercapto-benzothiazole; 2-
mercapto-S-methyl, thiazole; 2-mercapto-5-ethyl thiazole; Z-mercaptoi-methyl thiazole; etc:
Suitable baseoils include a wide variety of lubricating oils such as naphthenic base, paraflin base, and mixed base mineraloils, other hydro' carbon" lubricants, e. g., lubricating -oil derived from'coalproducts, and-synthetic oils, e. g., alkylg ene polymers '(such as polymers. of propylene,
butylene', etc;,' and mixtures thereof), alkylene oxide=type polymers; dicarboxylic acid GStBI'SIaIId liquid esters; of acids of phosphorus. Synthetic oils of. the alkyleneoxide-type polymer vwhich may be used include those exemplified by the al-' For example, it is preferred to The major kylene oxide polymers (e. g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing alkylene oxides, e. g., propylene oxide, in the presence of wa- .;;ter:-or.alcohols, e. g., ethyl alcohol, and esters of 'alkylene oxide-type polymers, e. g., acetylated propyleneoxidepolymers prepared by acetylat- 'ing prop-yleheoxide polymers containing hydrox- Synthe'ticoils of. the dicarboxylic acid ester type include. those-which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, 2-ethyl-hexyl alcohol; -,dode.cyl alcohol; etc. Examples of dicarbOXYliCifiCid ester synthetic oils include di-butyl adipate, di,hexyl adipate, di-Z-ethyl-hexylseb-.:
acate, ;di-:n -hexyl 'fumarate polymer, etc.
Syntheticioils. of thetypeof liquid esters-of. acidsi of phosphorus. include the esters, of l PhOS-r phoric: acid, 'e. g.,;tricresyl' phosphate ;r* the esters:
of ,phosphonic acid, :e.-g.,"di,-ethy1 ester, of decane phosphonic'sacid or'other suchestersas obtained by reacting alkyl phosphonyl chlorides withv hy-.
droxyl-containing' compounds such as phenols andaliphatic alcohols, and with olefin oxides such i as-propylene .oxide, as described in Jenseniet -al., U. S. patent application No. 86,856, new abanw doned.
The improved lubricant of the present .inven-.-. tionis used where the effectiveness of selenium: compounds as lubricant additives. is decreased by the attack on metals by the selenium of the"- .selenium compounds; In order to evaluate. the;
silver-protective agents of this invention for their effectiveness in inhibiting reduction of activity of. selenium compounds, lubricants containing the selenium compounds and the. protective agents were subjected to a silver strip test which was:
performed as follows:
A silvermetal strip having the dimensions .of
2 x x gg". was first cleaned with a wire brush until the strip was highly polished. The strip was weighed and the weight recorded. This highly polished silver strip was then placed in a 600 ml. beaker in such a manner that the strip was completely immersed when 300 g. of the oil being tested was poured into the beaker. The .oil
was stirred at a temperature of 300 F.'for twenty hours, at which time the silver strip'was removed and" cleaned, first with chloroform, then with The appearance of the strip was noted. 7 Those strips which had been severely attacked were quite black. The tested silver strip petroleum ether.
was washed in-a concentrated solution of cadmium chloride containing 10% of potassium cyanide to remove the selenide film adhering tothestrip; After the strip had been-washed with thiscadmium chloride-potassium cyanide solution and dried, it was weighed. The diiference in weight of the original strip and the strip after the cadmium chloride wash was noted and recorded asthe weight lost due to reaction with the selenium compound.
In addition to being especially eifectiveas pro-- tectiv'e agents for silver, the protective agents of this invention are eifective ,in protecting other selenium-sensitive metals from selenium attack.
Such other selenium sensitive metals includecopper, aluminum, and alloys of copper and aluminum.
The following are illustrative of various selenium-containing oxidation inhibitors reactive with silver: alkyl selenides (e. g., didodecyl monoselenide, octadecyl methyl monoselenide, octadecyl ethyl moncselenidaoctyl dodecyl monoselenide, di eic'osyl' monoselenide, dioctyl diselenide, di-eicosyl diselenide, dilauryl diselenide, dioctadecyl diselenide, and the various monoand polyselenides prepared by reacting sodiumor other alkali metal monoor polyselenides with halogenated, e. g., chlorinated hydrocarbons, such as decyl'chloride, dodecyl chloride, tetradecyl chloride, octadecyl chloride, heptadecyl chloride, chlorinated lubricating oil and chlorinated wax) selenomercaptans (e. g., methyl selenomercaptan, octyl selenomercaptan, dodecyl selenomercaptan, tetradecyl selenomercaptan, hexadecyl selenomercaptan, octadecyl selenomercaptan, eicosyl selenomercaptan, parafiin wax selenomercaptan, phenyl methyl selenomercaptan, phenyl octyl selenomercaptan, phenyl dodecyl selenomercaptan, phenyl octadecyl selenomercaptan, cyclohexyl selenomercaptan, octyl cyclohexyl selenomercaptan, octadecyl cyclohexyl selenomercaptan, etc); metal selenomercaptan (e. g., the barium, calcium, sodium, zinc, strontium, aluminum, cadmium, nickel, lead and thallium salts of the above selenomercaptans).
Some of the above-indicated additives are more vigorous in their attack on silver than others, and, consequently, such attack is more difiicult to minimize. However, the silver-protective agents are advantageously used, even with the more active selenium additives.
The agents of this invention may be used in lubricating oils containing, in addition to the selenium compounds, other additives such as polyvalent metal phenates (e. g., calcium cetyl phenate), metal organo-sulfonates (e. g., calcium petroleum sulfonate), polyvalent metal salts of acids of phosphorus, such as phosphates (e. g., calcium cetyl phosphate), phosphonates (e. g., calcium white oil phosphonate), thiophosphates (e. g., calcium cetyl thiophosphates), phenols (e. g., 2,6-di-tertiary-butyl-4-methylphenol), etc.
The lubricant compositions of this invention may also contain other agents which are advantageously present, such as oiliness agents, blooming agents, viscosity index improvers, pour point depressants, peptizing agents, etc.
For the purpose of the tests described hereinbelow, the silver protective agents of this invention were incorporated in a California solvent.
refined S. A. E. 30 parafiinic base oil containing calcium petroleum sulfonate, sulfurized calcium cetyl phenate and a didodecyl monoselenide.
Table I below presents data obtained in the "silver strip test.
Table II below presents the results obtained when freshly polished silver strips were immersed for 30 minutes at a temperature of 300 F. in a California solvent refined S. A. E. 30 paraffinic base oil containing calcium petroleum sulfonate, sulfurized calcium cetyl phenate and 0.2% by weight of various selenium compounds 6 with and. without 2 mercapto 4,6,6 trimethyl thiazine as'a silver protective agent. The darker the appearance of the silver strip, the more pronounced the attack on the silver by the selenium compound.
1 0.4% by weight of selenium compound present.
We claim:
1. A lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition corrosive to silver, and a small amount, sufficient substantially to inhibit the formation of silver selenide resulting from the selenium attack on silver, of a Z-mercapto-thiazine wherein not more than four of the ring carbons contain aliphatic groups each of which has not more than 4 carbon atoms.
2. A lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which is corrosive to silver, and a 7 small amount, sufficient substantially to inhibit the reaction between the selenium of said lubrieating oil composition and silver, a Z-mercaptothiazine wherein not more than four of the ring carbons contain short chain aliphatic groups, said aliphatic groups containing a total of no more than 16 carbon atoms.
3. A lubricating oil composition at least of which is composed of an admixture of an oil of lubricating viscosity and lubricating oil additives having present selenium which reacts with silver-wearing surfaces, and a small amount, sufiicient substantially to inhibit the reaction between the selenium and silver, of a 2 -mercapto-thiazine wherein not more than four of the ring carbons of the said mercapto-thiazine contain short chain aliphatic carbons.
4. A lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which attacks silver directly to form silver selenide, and a small amount, sumcient substantially to reduce the selenium attack on silver, of a Z-mercapto-thiazine wherein not more than 4 of the ring carbons contain shortchain aliphatic groups.
5. A lubricant consisting essentially of a major portion of a selenium-containing lubricating oil composition which attacks silver-wearing surfaces to form silver selenide, and a small amount, sufiicient substantially to reduce the selenium attack on silver, of a 2-mercapto-4,6,6-trimethyl thiazine.
6. A selenium-containing lubricating oil composition which forms silver selenide on silverwearing surfaces, and a small amount, sufiicient substantially to reduce this silver selenide formation, of a 2-mercapto-thiazine wherein not more than four of the ring carbons contain short chain.::;aliphatic groups.:= said. i aliphatic "groups .1 containingra total-. of: not more-than 16 carbon:
atoms.
'7. -A selenium-containing lubricating joil' com-- position which forms silver selenide on silver- 85' mation, .of ':2-mercapto- 4,6,firtrimethyl thiazine. 9. 'Alubricantcompositioncomprising a 'major' proportion of an oil of. lubricating wiscosity-,;-' a selenium -.compound which attacks silver -wear' ing surfacesto form: silver selenide, and a small-w amount; sufiicien-tsubstantially .1 to reduce the Y selenium attack on silver," 1 of" a r Z-mercaptothiazinawherein not moi-Ethan four ofthe ring -1- ca'rbons contain-short chain aliphatic groups.
WARREN LOW'E. W-I-LLIAM-- T; STEWARE: J AMES- 0. CLAYTON-.-
No references cited.-
Claims (1)
1. A LUBRICANT CONSISTING ESSENTIALLY OF A MAJOR PORTION OF A SELENIUM-CONTAINING LUBRICATING OIL COMPOSITION CORROSIVE TO SILVER, AND A SMALL AMOUNT, SUFFICIENT SUBSTANTIALLY TO INHIBIT THE FORMATION OF SILVER SELENIDE RESULTING FROM THE SELENIUM ATTACK ON SILVER, OF A 2-MERCAPTO-THIAZINE WHEREIN NOT MORE THAN FOUR OF THE RING CARBONS CONTAIN ALIPHATIC GROUPS EACH OF WHICH HAS NOT MORE THAN 4 CARBON ATOMS.
Priority Applications (1)
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US103937A US2597838A (en) | 1949-07-09 | 1949-07-09 | Lubricant containing selenium compounds |
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US103937A US2597838A (en) | 1949-07-09 | 1949-07-09 | Lubricant containing selenium compounds |
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US2597838A true US2597838A (en) | 1952-05-20 |
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ID=22297797
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US103937A Expired - Lifetime US2597838A (en) | 1949-07-09 | 1949-07-09 | Lubricant containing selenium compounds |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2703785A (en) * | 1953-02-27 | 1955-03-08 | Standard Oil Co | Soluble compositions containing a 2, 5-dimercapto-1, 3, 4-thiadiazole derivative |
US2719125A (en) * | 1952-12-30 | 1955-09-27 | Standard Oil Co | Oleaginous compositions non-corrosive to silver |
DE1234348B (en) * | 1954-02-09 | 1967-02-16 | Douglas Aircraft Co Inc | lubricant |
RU2746245C1 (en) * | 2019-12-06 | 2021-04-09 | Федеральное государственное бюджетное учреждение науки Институт машиноведения им. А.А. Благонравова Российской академии наук (ИМАШ РАН) | Method for producing self-lubricating anti-frictional composition in friction pair |
-
1949
- 1949-07-09 US US103937A patent/US2597838A/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2719125A (en) * | 1952-12-30 | 1955-09-27 | Standard Oil Co | Oleaginous compositions non-corrosive to silver |
US2703785A (en) * | 1953-02-27 | 1955-03-08 | Standard Oil Co | Soluble compositions containing a 2, 5-dimercapto-1, 3, 4-thiadiazole derivative |
DE1234348B (en) * | 1954-02-09 | 1967-02-16 | Douglas Aircraft Co Inc | lubricant |
RU2746245C1 (en) * | 2019-12-06 | 2021-04-09 | Федеральное государственное бюджетное учреждение науки Институт машиноведения им. А.А. Благонравова Российской академии наук (ИМАШ РАН) | Method for producing self-lubricating anti-frictional composition in friction pair |
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