DE1271880B - Schmieroel - Google Patents
SchmieroelInfo
- Publication number
- DE1271880B DE1271880B DEP1271A DE1271880A DE1271880B DE 1271880 B DE1271880 B DE 1271880B DE P1271 A DEP1271 A DE P1271A DE 1271880 A DE1271880 A DE 1271880A DE 1271880 B DE1271880 B DE 1271880B
- Authority
- DE
- Germany
- Prior art keywords
- zinc
- mol
- dithiophosphate
- reaction product
- oxide
- 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.)
- Pending
Links
- 239000010687 lubricating oil Substances 0.000 title claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 40
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 15
- 150000002924 oxiranes Chemical class 0.000 claims description 10
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 19
- -1 methylcyclohexyl Chemical group 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 150000003751 zinc Chemical class 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 229910052725 zinc Inorganic materials 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 6
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- GULWIZIWMXAAKV-UHFFFAOYSA-M [Zn+].CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC Chemical compound [Zn+].CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC GULWIZIWMXAAKV-UHFFFAOYSA-M 0.000 description 4
- HKTYKKGNRKGXSL-UHFFFAOYSA-M [Zn+].CCCCCCCCOP([O-])(=S)SCCCCCCCC Chemical compound [Zn+].CCCCCCCCOP([O-])(=S)SCCCCCCCC HKTYKKGNRKGXSL-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- FEXXLIKDYGCVGJ-UHFFFAOYSA-N butyl 8-(3-octyloxiran-2-yl)octanoate Chemical compound CCCCCCCCC1OC1CCCCCCCC(=O)OCCCC FEXXLIKDYGCVGJ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012084 conversion product Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 2
- FIWYWGLEPWBBQU-UHFFFAOYSA-N 2-heptylphenol Chemical compound CCCCCCCC1=CC=CC=C1O FIWYWGLEPWBBQU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 150000001661 cadmium Chemical class 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 1
- FWVNVNLDZOTFAT-UHFFFAOYSA-M C1(CCCCC1)SP(=S)(OC1CCCCC1)[O-].[Zn+] Chemical compound C1(CCCCC1)SP(=S)(OC1CCCCC1)[O-].[Zn+] FWVNVNLDZOTFAT-UHFFFAOYSA-M 0.000 description 1
- ULMCFLNZDVBZOZ-UHFFFAOYSA-N CCCCCCCC1=CC=CC([S+]=P([O-])([O-])[S-])=C1CCCCCCC.CCCCCCCC1=CC=CC([S+]=P([O-])([O-])[S-])=C1CCCCCCC.[Ba+2].[Ba+2].[Ba+2] Chemical compound CCCCCCCC1=CC=CC([S+]=P([O-])([O-])[S-])=C1CCCCCCC.CCCCCCCC1=CC=CC([S+]=P([O-])([O-])[S-])=C1CCCCCCC.[Ba+2].[Ba+2].[Ba+2] ULMCFLNZDVBZOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- DHHCPMGCLXWUQS-UHFFFAOYSA-H P(=S)([S-])([O-])[O-].[Ba+2].P(=S)([S-])([O-])[O-].[Ba+2].[Ba+2] Chemical class P(=S)([S-])([O-])[O-].[Ba+2].P(=S)([S-])([O-])[O-].[Ba+2].[Ba+2] DHHCPMGCLXWUQS-UHFFFAOYSA-H 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 244000186561 Swietenia macrophylla Species 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- MEGCHDFJJUAPQS-UHFFFAOYSA-M [Zn+].CCCCCCCCCOP([O-])(=S)SCCCCCCCCC Chemical compound [Zn+].CCCCCCCCCOP([O-])(=S)SCCCCCCCCC MEGCHDFJJUAPQS-UHFFFAOYSA-M 0.000 description 1
- IDSGDIQXDSUTHX-UHFFFAOYSA-M [Zn+].CCCCCCCOP([O-])(=S)SCCCCCCC Chemical compound [Zn+].CCCCCCCOP([O-])(=S)SCCCCCCC IDSGDIQXDSUTHX-UHFFFAOYSA-M 0.000 description 1
- BGTLSDQMKYQERJ-UHFFFAOYSA-M [Zn+].CCCCCOP([O-])(=S)SCCCCC Chemical compound [Zn+].CCCCCOP([O-])(=S)SCCCCC BGTLSDQMKYQERJ-UHFFFAOYSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000010000 carbonizing Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XFAYHOVTJNPDJW-UHFFFAOYSA-N di(nonoxy)-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCCCCCOP(S)(=S)OCCCCCCCCC XFAYHOVTJNPDJW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 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
- 125000001424 substituent group Chemical group 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- UXHYTRGVMSDNEI-UHFFFAOYSA-L zinc;4-methylpentan-2-yloxy-(4-methylpentan-2-ylsulfanyl)-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)CC(C)OP([O-])(=S)SC(C)CC(C)C.CC(C)CC(C)OP([O-])(=S)SC(C)CC(C)C UXHYTRGVMSDNEI-UHFFFAOYSA-L 0.000 description 1
- ZBDJNBFTEIUHPK-UHFFFAOYSA-L zinc;dihexoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCOP([S-])(=S)OCCCCCC.CCCCCCOP([S-])(=S)OCCCCCC ZBDJNBFTEIUHPK-UHFFFAOYSA-L 0.000 description 1
- VYEHCXHIPZIYIJ-UHFFFAOYSA-L zinc;dodecoxy-dodecylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC.CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC VYEHCXHIPZIYIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- C10M137/105—Thio derivatives not containing metal
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2205/026—Butene
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10M2225/00—Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
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- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
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Description
Int. Cl.:
ClOm
DEUTSCHES
PATENTAMT
AUSLEGESCHRIFT
Deutsche Kl.: 23 c-1/01
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:
Aktenzeichen:
Anmeldetag:
Auslegetag:
P 12 71 880.8-43 (L 41610)
30. März 1962
4. Juli 1968
Es ist bekannt, Umsetzungsprodukte organischer Epoxide mit Metallsalzen der Dithiophosphorsäuren
als Zusätze in Schmierölen zu verwenden. So ist in der deutschen Auslegeschrift 1 012 416 ein Schmieröl
mit einem Gehalt an einem Umsetzungsprodukt eines Metallsalzes einer Thiophosphorsäure mit
mindestens etwa der äquivalenten Menge eines organischen Epoxids beschrieben. Bei Verwendung
der Metallsalze von Dithiophosphorsäuren muß man dem Schmieröl ein Umsetzungsprodukt aus
1 Mol Dithiophosphat mit mindestens etwa 2 Mol Epoxid zusetzen. Es sind ferner Schmiermittelzusätze
bekannt, die durch Umsetzen von 1 bis 3 Mol eines Alkylenoxide mit 1 Mol eines Metallsalzes
der I. und II. Gruppe des Periodensystems einer Dithiophosphorsäure erhalten wurden. Diese
bekannten Umsetzungsprodukte dienen als Oxydationsinhibitoren in Schmierölen. Sie haben jedoch
den Nachteil, daß sie nur unter normalen Arbeitsbedingungen eine gute Wirksamkeit besitzen, unter
extremen Arbeitsbedingungen jedoch eine ungenügende Wirksamkeit aufweisen.
Gegenstand der Erfindung ist ein Schmieröl mit einem Gehalt an Umsetzungsprodukten von Alkylen-
oder Arylalkylenoxiden, vorzugsweise Propylenoxid, mit Metallsalzen der Dithiophosphorsäure der allgemeinen
Formel I
Schmieröl
R1Ox
R, O'
(D
in der Ri und R2 Alkyl-, Cycloalkyl-, Alkaryl- oder
Arylalkylreste bedeuten, wobei die Summe der aliphatischen Kohlenstoffzahlen von Ri und R2
je Phosphoratom größer als etwa 7,6 ist und die Metalle der II. Gruppe des Periodensystems angehören,
und das dadurch gekennzeichnet ist, daß es ein Umsetzungsprodukt enthält, das durch
Kondensation von bis zu 0,75 Mol, vorzugsweise 0,25 bis 0,5 Mol Epoxid pro Mol Dithiophosphat
hergestellt worden ist.
Das Schmieröl der Erfindung besitzt überraschenderweise auch unter strengen Betriebsbedingungen
eine gute Oxydationsbeständigkeit.
Die Metalldithiophosphate, aus denen die verbesserten Oxydationsinhibitoren hergestellt werden,
sind vorzugsweise die Calcium-, Barium-, Strontium-, Zink- und Cadmiumsalze der Dithiophosphorsäuren
der allgemeinen Formel I. Die Zink- und Bariumdithiophosphate ergeben besondere wirksame Zusätze
und werden daher bevorzugt verwendet.
Anmelder:
The Lubrizol Corporation,
Cleveland, Ohio (V. St. A.)
Vertreter:
Dr. E. Jung und Dr. V. Vossius, Patentanwälte,
8000 München 23, Siegesstr. 26
Als Erfinder benannt:
Alan Rhodes, Cleveland, Ohio (V. St. A.)
Beanspruchte Priorität:
V. St. v. Amerika vom 14. April 1961 (102 933)
Die oben angegebene Grenze für die niedrigste Zahl der aliphatischen Kohlenstoffatome in den
Resten Ri und R2 beruht auf der Löslichkeit der
Metalldithiophosphate. Salze von Dithiophosphorsäuren, in denen Ri und R2 zusammen weniger als
etwa 7,6 aliphatische Kohlenstoffatome aufweisen, sind in Schmierölen nicht hinreichend löslich und
daher, als Zusätze nicht geeignet.
Die Reste Ri und R2 sind vorzugsweise Alkyl-
oder Alkylphenylreste mit bis zu etwa 30 Kohlenstoffatomen im Alkylrest. Beispiele für Alkylreste
sind die Methyl-, Äthyl-, n-Heptyl- und Decylgruppe. Beispiele für Cycloalkyl- und Alkylphenylreste sind
die Cyclopentyl-, Methylcyclohexyl-, Butylphenyl- und Diamylphenylgruppe sowie die durch einen
Polyisobutenylrest vom Molekulargewicht 1000 substituierte Phenylgruppe. Die Reste Ri und R2
können auch substituierte Alkylreste sein wie die 3-Brombutyl- und Chloräthylgruppe.
Die Dithiophosphorsäuren werden nach an sich bekannten Verfahren durch Umsetzung von 1 Mol
Phosphorpentasulfid mit 4 Mol eines Alkohols oder Phenols erhalten. Die Herstellung des Metallsalzes
dieser Säure erfolgt durch Umsetzung der Säure mit einem Neutralisationsmittel, wie Zink, Zinkoxid
oder Bariumoxid.
Zur Herstellung der Epoxid-Dithiophosphat-Umsetzungsprodukte werden als Epoxide Alkylen- oder
809 568/505
Arylalkylenoxide eingesetzt. Als Alkylenoxide werden in der Regel Verbindungen mit bis zu 6 Kohlenstoffatomen
in der Alkylengruppe verwendet. Diese Epoxide können einen polaren Substituenten, z. B.
ein Halogenatom, einer Äther- oder Estergruppe enthalten. Spezielle Beispiele sind Epichlorhydrin,
9,10-Epoxystearinsäurebutylester, epoxydiertes Sojabohnenöl
und epoxydiertes Tungöl.
Die Epoxid-Dithiophosphat-Umsetzungsprodukte werden durch Vermischen des Metalldithiophosphats
mit dem Epoxid hergestellt. Die Reaktion verläuft exotherm und wird zwischen 0 und 3000C durchgeführt.
Die Reaktion kann auch in einem Lösungsmittel, wie Benzol, Mineralöl, Naphtha odern-Hexan,
durchgeführt werden.
Die obere Grenze des Molverhältnisses von Epoxid zu Metalldithiophosphat ist kritisch. Diese
Grenze liegt bei 0,75 Mol Epoxid pro Mol Metalldithiophosphat und ist unter Berücksichtigung der
Eigenschaften der Reaktionsprodukte festgelegt. Die Verwendung einer Epoxidmenge unter dieser Grenze
hat eine verbesserte oxydationshemmende Wirkung des Metalldithiophosphats zur Folge. Andererseits
führt der Einsatz größerer Epoxidmengen oberhalb der genannten Grenze zu Produkten, die offenbar
die Korrosion der Metallteile und starkes Schäumen des Schmieröls begünstigen; auch haben derartige
Produkte nur eine begrenzte öllöslichkeit. Obwohl die Verwendung jeder Epoxidmenge unterhalb der
genannten oberen Grenze zu Produkten mit besserer Oxydationshemmung führt, wurde eine besonders
deutliche Verbesserung gewöhnlich dann beobachtet, wenn wenigstens 0,1 Mol Epoxid pro Mol Metalldithiophosphat
verwendet wurde. Produkte aus 1 Mol Metalldithiophosphat und etwa 0,25 bis etwa 0,5 Mol eines niederen Alkylenoxide sind besonders
wirksam.
Das Epoxid-Dithiophosphat-Umsetzungsprodukt wird Schmierölen gewöhnlich in einer Menge von
0,01 bis 3,5 Gewichtsprozent, bezogen auf das fertige Schmieröl, zugemischt. Die günstigste Menge
kann durch Versuche leicht ermittelt werden.
Das Schmieröl kann synthetischen, tierischen, pflanzlichen oder mineralischen Ursprungs sein.
Die Schmieröle sollen möglichst einen Viskositätsbereich von etwa 40 SUS (Saybolt Universal Sekunden)
bei 38°C bis etwa 200 SUS bei 93°C haben.
Dem Schmieröl der Erfindung können außerdem noch andere bekannte Zusätze einverleibt werden,
z. B. Reinigungsmittel, Viskositätsindexverbesserer, Fließpunktverminderer, Antischaummittel, Hochdruckzusätze,
Rostschutzmittel und zusätzliche oxydations- und korrosionsverhindernde Mittel.
Nachstehend werden Vorschriften zur Herstellung von Epoxid-Dithiophosphat-Umsetzungsprodukten
gegeben, die in den Mineralölen der Erfindung enthalten sein können.
A. 394 Gewichtsteile Zink-di-n-octyldithiophosphat mit einem Phosphorgehalt von 7% werden bei 75
bis 85°C mit 13 Teilen Propylenoxid (0,5 Mol pro Mol Dithiophosphat) innerhalb von 20 Minuten
versetzt. Das Gemisch wird 1 Stunde auf 82 bis 85°C erhitzt und dann filtriert.
B. 885 g einer Mineralöllösung, die 1 Mol Zinkdi-n-octyldithiophosphat
enthält, werden bei 75 bis 850C mit 0,25 Mol Propylenoxid versetzt. Das
Gemisch wird so lange bei dieser Temperatur gehalten, bis die Reaktion beendet ist.
C. Das Verfahren gemäß B wird wiederholt, es werden jedoch nur 0,125 Mol Propylenoxid eingesetzt.
D. 15 g (0,26 Mol) Propylenoxid werden bei 90 bis· 1000C innerhalb einer Stunde zu 307 g (0,4 Mol)
Zink-di-(4-methyl-2-pentyl)-dithiophosphat gegeben. Das Gemisch wird 6 Stunden auf diese Temperatur,
dann auf 90°C/20 Torr erhitzt und anschließend filtriert.
E. 15 g (0,26 Mol) Propylenoxid werden innerhalb einer Stunde bei 90 bis 1000C zu dem Zinksalz einer
Dithiophosphorsäure gegeben, die durch Umsetzung von Phosphorpentasulfid mit einer Mischung von
47% Isopropanol und 53% 4-Methyl-2-pentanol erhalten wurde. Das Gemisch wird 6 Stunden auf
bis 100°C und dann auf 90°C/20Torr erhitzt und schließlich filtriert.
F. Das Verfahren gemäß E wird wiederholt, jedoch werden 323 g (0,5 Mol) des Zinksalzes
einer Dithiophosphorsäure eingesetzt, die durch Umsetzung von Phosphorpentasulfid mit einer Mischung
von 65% Isobutanol und 35% n-Pentanol erhalten wurde.
G. Das Verfahren gemäß B wird mit Zink-di-(p-heptylphenol)-dithiophosphat
wiederholt.
Weitere Beispiele für Epoxid-Dithiophosphat-Umsetzungsprodukte sind:
Das Umsetzungsprodukt von 0,5 Mol Propylenoxid mit dem Zinksalz einer Dithiophosphorsäure,
die durch Umsetzung von Phosphorpentasulfid mit einer äquimolaren Mischung von Methanol und n-Octanol erhalten wurde;
das Umsetzungsprodukt des Bariumsalzes der Di-n-nonyldithiophosphorsäure mit 0,75 Mol
1,2-Butylenoxid;
das Umsetzungsprodukt von Zink-di-n-octyldithiophosphat mit 0,6 Mol Epichlorhydrin;
das Umsetzungsprodukt des Zinksalzes einer äquimolaren Mischung von Dicyclohexyl- und
piisobutyldithiophosphorsäure mit 0,5 Mol Äthylenoxid;
das Umsetzungsprodukt einer äquimolaren Mischung von Zink-di-cyclohexyl- und Zink-didodecyldithiophosphat
mit 0,75 Mol 1,2-Pentenoxid;
das Umsetzungsprodukt von Barium-di-heptylphenyldithiophosphat
mit 0,1 Mol Styroloxid; das Umsetzungsprodukt des Cadmiumsalzes einer Dithiophosphorsäure, die durch Umsetzung
von Phosphorpentasulfid mit einer Mischung von 60 Molprozent p-Butylphenol
und 40 Molprozent n-Pentanol erhalten wurde, mit 0,5 Mol Cyclohexenoxid;
das Umsetzungsprodukt von Strontium-di-hexyldithiophosphat mit 0,5 Mol Propylenoxid;
das Umsetzungsprodukt von Calcium-di-n-octyldithiophosphat
mit 0,5 Mol Äthylenoxid; das Umsetzungsprodukt des Zinksalzes einer
äquimolaren Mischung von Diisopropyl- und Di - η - decyldithiophosphorsäure mit 0,5 Mol
1,2-Hexenoxid;
das Umsetzungsprodukt von Zink-di-cyclohexyldithiophosphat
mit 0,3 Mol Äthylenoxid; das Umsetzungsprodukt von Zink-di-nonyldithiophosphat
mit 0,25 Mol 1,2-Hexenoxid; das Umsetzungsprodukt von Zink-di-heptyldithiophosphat
mit 0,5 Mol 1,2-Butylenoxid;
das Umsetzungsprodukt von Zink-di-n-octyldithiophosphat
mit 0,25 Mol Propylenoxid;
das Umsetzungsprodukt von Zink-di-n-hexyldithiophosphat mit 0,5 Mol Epichlorhydrin;
das Umsetzungsprodukt von 0,5 Mol Propylenoxid mit dem Zinksalz einer Dithiophosphorsäure, die durch Umsetzung von Phosphorpentasulfid mit einer äquimolaren Mischung von n-Butanol und Dodecylalkohol hergestellt worden ist;
das Umsetzungsprodukt von Zink-di-n-hexyldithiophosphat mit 0,5 Mol Epichlorhydrin;
das Umsetzungsprodukt von 0,5 Mol Propylenoxid mit dem Zinksalz einer Dithiophosphorsäure, die durch Umsetzung von Phosphorpentasulfid mit einer äquimolaren Mischung von n-Butanol und Dodecylalkohol hergestellt worden ist;
das Umsetzungsprodukt von Zink-di-(isobutylphenyl)-dithiophosphat mit 0,4 Mol Epichlorhydrin
;
das Umsetzungsprodukt von Zink-di-n-pentyldithiophosphat
mit 0,3 Mol Styroloxid und
das Umsetzungsprodukt von Zink-di-dodecyldithiophosphat mit 0,25 Mol 3,4-Hexenoxid.
das Umsetzungsprodukt von Zink-di-dodecyldithiophosphat mit 0,25 Mol 3,4-Hexenoxid.
Schmieröle der Erfindung wurden hinsichtlich ihrer Oxydationsbeständigkeit folgendem Test unterworfen.
Luft in einer Menge von 341 pro Stunde wird bei 1500C in 350 g eines Getriebeschmieröls,
in das 125 g Eisen, 128 g Kupfer und 31 g Blei in Form von Blechstreifen getaucht wird, so lange
eingeblasen, bis sich Schlamm bildet, was am Auftreten einer Trübung oder eines Niederschlages
erkennbar ist. Das bei dem Test verwendete Basisöl ist ein Mineralschmieröl mit einer Viskosität von
112 SUS bei 380C und einem Viskositätsindex von 85. Es enthält 2,3 Volumprozent eines überbasischen
Bariumsalzes mit einem Bariumsulfataschegehalt von 35% (hergestellt durch Erhitzen einer Mischung
aus 1000 Gewichtsteilen Spermöl, 294 Teilen Heptylphenol, 2870 Teilen Mineralöl, 285 Teilen Wasser
und 1540 Teilen Bariumoxid auf 149 0C, Carbonisieren der Mischung bei 135°C bis zum Erreichen des
Neutralpunktes und Filtrieren des Produktes), 0,92 Volumprozent eines überbasischen Bariumsulfonats
mit einem Bariumsulfataschegehalt von 38,5% (hergestellt durch Erhitzen einer Mischung
aus 805 Gewichtsteilen Mineralöl, 625 Teilen Bariummahoganisulfonat, 210 Teilen Wasser, 146 Teilen
Heptylphenol und 740 Teilen Bariumoxid auf 146°C, Carbonisieren der Mischung bei dieser
Temperatur bis zur Erreichung des Neutralpunktes, Verdünnen der Mischung mit 520 Teilen Mineralöl
und Filtrieren des Produktes), 20 ppm eines PoIyalkylsiloxans als Antischaummittel und 3,64% eines
Polyalkylmethacrylats als Viskositätsindexverbesserer.
Die Überlegenheit der Schmieröle der Erfindung
hinsichtlich ihrer Oxydationsbeständigkeit gegenüber Schmierölen nach dem Stand der Technik
zeigen die folgenden Beispiele in Tabelle I.
Beispiel | Schmieröl + Zusatz (0,1 Gewichtsprozent als P) |
0I0 Viskositätse 42 Stunden |
rhöhung nach 48 Stunden |
Stunden bis zur Schlammbildung |
la) | Umsetzungsprodukt von Zink-di-(polypropenyl)- dithiophosphat und 0,75 Mol Styroloxid |
12,6 | 19,2 | 48 bis 66 |
Ib) | Umsetzungsprodukt von Zink-di-(polypropenyl)- dithiophosphat und 2,0 Mol Styroloxid |
46,5 | 68,5 | 24 bis 42 |
2 a) | Umsetzungsprodukt von Cadmium - di - (methyl- cyclohexyl)-dithiophosphat und 0,75 Mol Pro pylenoxid |
10,3 . | 9,8 | 66 bis 72 |
2 b) | Umsetzungsprodukt von Cadmium - di - (methyl- cyclohexyl)-dithiophosphat und 2,0 Mol Pro pylenoxid |
10,4 | 10,9 | 48 bis 66 |
3 a) | Umsetzungsprodukt von Calcium-di-tridecyldithio- phosphat und 0,75 Mol Propylenoxid |
63,3 | 98,4 | 24 bis 42 |
3 b) | Umsetzungsprodukt von Calcium-di-tridecyldithio- phosphat und 2,0 Mol Propylenoxid |
506,9 | 4316,9 | 24 bis 42 |
4 a) | Umsetzungsprodukt von Zink-di-dodecyldithio- phosphat und 0,75 Mol Propylenchlorhydrin |
6,5 | 10,6 | 48 bis 66 |
4 b) | Umsetzungsprodukt von Zink-di-dodecyldithio- phosphat und 2,0 Mol Propylenchlorhydrin |
83,8 | 105,1 | 24 bis 42 |
Eine Anzahl von Umsetzungsprodukten von 65 wurde ein Metalldithiophosphat verwendet, das
Metalldithiophosphaten mit Epoxiden, die in einem entweder mit 0,75 Mol oder mit 2,0 Mol des Epoxides
Schmieröl aufgelöst waren, wurde dem Schaumtest umgesetzt worden war.
nach ASTM-D 892 unterworfen. In allen Fällen
Tabelle II Schaumtest nach ASTM-D 892
Schaumvolumen nach Lagerung bei 65,5'C während
0 Wochen
1 Woche
Getriebeschmieröl mit 4 Gewichtsprozent Umsetzungsprodukt
von Zink-di-(polypropenyl)-dithiophosphat und 0,75 Mol Styroloxid
von Zink-di-(polyprophenyl)-dithiophosphat und 2,0 Mol Styroloxid
von Zink-di-(polypropenyl)-dithiophosphat
von Zink-di-dodecyldithiophosphat und 2,0 Mol Octenoxid
des Zinksalzes eines Gemisches einer Dialkyldithiophosphorsäure, in der 60%
der Alkylreste 2-Methylamyl-4- und 40% Isopropylreste sind, und 0,75 Mol
9,10-Epoxystearinsäurebutylester
des Zinksalzes eines Gemisches einer Dialkyldithiophosphorsäure, in der 60%
der Alkylreste 2-Methylamyl-4- und 40% Isopropylreste sind, und 2,0 Mol
9,10-Epoxystearinsäurebutylester
0 240
0 490
50
Claims (1)
- Patentanspruch:Schmieröl mit einem Gehalt an Umsetzungsprodukten von Alkylen- oder Arylalkylenoxiden, vorzugsweise Propylenoxid, mit Metallsalzen der Dithiophosphorsäure der allgemeinen FormelR1On3°in der Ri und R2 Alkyl-, Cycloalkyl-, Alkaryl- oder Arylalkylreste bedeuten, wobei die Summeder aliphatischen Kohlenstoffzahlen von Ri und R-2 je Phosphoratom größer als etwa 7,6 ist und die Metalle der II. Gruppe des Periodensystems angehören, dadurch gekennzeichnet, daß es ein Umsetzungsprodukt enthält, das durch Kondensation von bis zu 0,75 Mol, vorzugsweise 0,25 bis 0,5 Mol Epoxid pro Mol Dithiophosphat hergestellt worden ist.In Betracht gezogene Druckschriften:
Deutsche Auslegeschrift Nr. 1012 416;
britische Patentschrift Nr. 796 181.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US102933A US3190833A (en) | 1961-04-14 | 1961-04-14 | Oxidation-resistant lubricating composition |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1271880B true DE1271880B (de) | 1968-07-04 |
Family
ID=22292471
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP1271A Pending DE1271880B (de) | 1961-04-14 | 1962-03-30 | Schmieroel |
Country Status (3)
Country | Link |
---|---|
US (1) | US3190833A (de) |
DE (1) | DE1271880B (de) |
GB (1) | GB991647A (de) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
US3259575A (en) * | 1963-11-26 | 1966-07-05 | Lubrizol Corp | Lubricating compositions containing isatoic anhydride |
US4466895A (en) * | 1983-06-27 | 1984-08-21 | The Lubrizol Corporation | Metal salts of lower dialkylphosphorodithioic acids |
US4634541A (en) * | 1985-01-28 | 1987-01-06 | Standard Oil Company | Color stabilizers for zinc dithiophosphates |
US5178782A (en) * | 1985-03-12 | 1993-01-12 | The Lubrizol Corporation | Metal salts of mixed aromatic/aliphatic phosphorodithioic acids |
DE3868949D1 (de) * | 1987-01-21 | 1992-04-16 | Amoco Corp | Veschleissschutz-schmiermittelzusammensetzungen mit geringem phosphorgehalt. |
JPH01503392A (ja) * | 1987-05-07 | 1989-11-16 | ザ ルブリゾル コーポレーション | 成分の相乗的な結合物を含有する,ギア潤滑剤パッケージ |
CN109679728B (zh) * | 2017-10-18 | 2022-06-24 | 中国石油化工股份有限公司 | 汽油发动机润滑油组合物及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1012416B (de) * | 1955-01-27 | 1957-07-18 | Lubrizol Corp | Schmieroel |
GB796181A (en) * | 1954-11-29 | 1958-06-04 | Exxon Research Engineering Co | Dithiophosphate esters and salts thereof and lubricating compositions containing them |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496508A (en) * | 1946-06-26 | 1950-02-07 | Standard Oil Co | Stabilized organic sulfur-containing compounds |
US2914478A (en) * | 1953-09-28 | 1959-11-24 | Union Oil Co | Antirust composition |
US3341633A (en) * | 1955-01-27 | 1967-09-12 | Lubrizol Corp | Reaction of o, o-dihydrocarbyl phosphorodithioic acids with epoxides |
US3004996A (en) * | 1956-04-09 | 1961-10-17 | Lubrizol Corp | Phosphorus and sulfur containing compositions and method for preparing same |
-
1961
- 1961-04-14 US US102933A patent/US3190833A/en not_active Expired - Lifetime
-
1962
- 1962-03-30 DE DEP1271A patent/DE1271880B/de active Pending
- 1962-04-09 GB GB13611/62A patent/GB991647A/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB796181A (en) * | 1954-11-29 | 1958-06-04 | Exxon Research Engineering Co | Dithiophosphate esters and salts thereof and lubricating compositions containing them |
DE1012416B (de) * | 1955-01-27 | 1957-07-18 | Lubrizol Corp | Schmieroel |
Also Published As
Publication number | Publication date |
---|---|
GB991647A (en) | 1965-05-12 |
US3190833A (en) | 1965-06-22 |
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