DE1151085B - Schmiermittelgemisch - Google Patents
SchmiermittelgemischInfo
- Publication number
- DE1151085B DE1151085B DES68011A DES0068011A DE1151085B DE 1151085 B DE1151085 B DE 1151085B DE S68011 A DES68011 A DE S68011A DE S0068011 A DES0068011 A DE S0068011A DE 1151085 B DE1151085 B DE 1151085B
- Authority
- DE
- Germany
- Prior art keywords
- lubricant mixture
- mixture according
- acid
- carbon atoms
- lubricant
- 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
- 239000000203 mixture Substances 0.000 title claims description 31
- 239000000314 lubricant Substances 0.000 title claims description 14
- 239000000654 additive Substances 0.000 claims description 19
- -1 n-decyl Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000010687 lubricating oil Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000006698 induction Effects 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003879 lubricant additive Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- MJZCELCYTRONIX-UHFFFAOYSA-N sulfanylmethylphosphonic acid Chemical compound OP(O)(=O)CS MJZCELCYTRONIX-UHFFFAOYSA-N 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 description 14
- 235000010446 mineral oil Nutrition 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 230000001476 alcoholic effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
- ARRDXFYXBCFIAI-UHFFFAOYSA-N decylsulfanylmethylphosphonic acid Chemical compound C(CCCCCCCCC)SCP(O)(O)=O ARRDXFYXBCFIAI-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 239000003963 antioxidant agent Substances 0.000 description 2
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- JPIROWHTPUZLPV-UHFFFAOYSA-N phenylsulfanylmethylphosphonic acid Chemical compound OP(O)(=O)CSC1=CC=CC=C1 JPIROWHTPUZLPV-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- SCBZVYUGGVFJIZ-UHFFFAOYSA-N 2-dodecyl-2-sulfanylbutanedioic acid Chemical compound CCCCCCCCCCCCC(S)(C(O)=O)CC(O)=O SCBZVYUGGVFJIZ-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- VJGHSPGETLFPHX-UHFFFAOYSA-N 3-hexadecylhexanedioic acid Chemical compound CCCCCCCCCCCCCCCCC(CC(O)=O)CCC(O)=O VJGHSPGETLFPHX-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- JAWZFTORYMQYDT-UHFFFAOYSA-N 6-hexoxy-6-oxohexanoic acid Chemical compound CCCCCCOC(=O)CCCCC(O)=O JAWZFTORYMQYDT-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- MURLRNMJALMOKA-UHFFFAOYSA-L C(CCCCCCCCC)SCP([O-])([O-])=O.[K+].[K+] Chemical compound C(CCCCCCCCC)SCP([O-])([O-])=O.[K+].[K+] MURLRNMJALMOKA-UHFFFAOYSA-L 0.000 description 1
- MVWGPENDPGDDOO-UHFFFAOYSA-N C(CCCCCCCCCCC)SCP(O)(O)=O Chemical compound C(CCCCCCCCCCC)SCP(O)(O)=O MVWGPENDPGDDOO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- WIGPRRHBXLHOMH-UHFFFAOYSA-N OP1(OCC1S)=O Chemical class OP1(OCC1S)=O WIGPRRHBXLHOMH-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000015241 bacon Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- LAYURVHZIIBYAP-UHFFFAOYSA-N benzylsulfanylmethylphosphonic acid Chemical compound OP(O)(=O)CSCC1=CC=CC=C1 LAYURVHZIIBYAP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 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
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010688 mineral lubricating oil Substances 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000001993 wax Substances 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
- C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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Description
Im allgemeinen werden Schmiermittel mit verschiedenen öllöslichen Verbindungen vermischt, nämlich
mit Stabilisatoren und Antioxydationsmitteln, wie phenolische Verbindungen, z. B. Alkylphenole und
Bisphenole, mit Reinigungsmitteln und Korrosions-Verhinderern, wie organische Salze, z. B. Carbonsäuresalze,
Phenolate, Phosphate, Sulfonate und Thiocarbamate; mit verschleißhindernden Mittel- und Hochdruckzusätzen,
wie Ester von Carbonsäuren oder Phosphorsäuren, z. B. Teilester von Fettsäuren und
mehrwertigen Alkoholen oder Alkyl- oder Arylphosphite
oder -phosphate oder freie .Fettsäuren sowie Schwefelderivate derselben, wie C10.18-Fettsäuren
und sulfurierte ungesättigte Fettsäuren, z.B. sulfurierte ölsäure. Wenn -jedoch derartige Verbindüngen
in Mischungen mit solchen Schmierölen benutzt werden, welche hohen Temperaturen und
Drücken ausgesetzt sind, zersetzen sie sich und sind nicht mehr in der Lage, unter solchen extremen Bedingungen
die erwarteten Wirkungen zu erfüllen.
Es ist nun gefunden worden, daß solche Schmiermittel hinsichtlich ihrer Stabilität, der Verhinderung
von Abnutzung und in bezug auf Hochdruckeigenschaften
verbessert werden können, wenn man ihnen eine untergeordnete Menge einer öHöslichenPhosphon-Verbindung
mit der nachstehenden Formel einverleibt:
• Schmiermittelgemisch
R-S-CH2-P
(D
XR1
In dieser Formel bedeutet R einen Kohlenwasserstoffrest mit mindestens 6 Kohlenstoffatomen, wobei
es sich vorzugsweise um einen geradkettigen Alkylrest
mit 10 bis 18 Kohlenstoffatomen handelt. Die
R1, welche gleich oder verschieden sein können, bedeuten
Wasserstoff, einen aliphatischen oder cycloaliphatischen Rest oder einen kationischen Rest, gebildet
aus einem mehrwertigen Metall oder einem aliphatischen Amin, während X Sauerstoff oder Schwefel
ist und die X ebenfalls gleich oder verschieden sein können. Bevorzugte Verbindungen von der allgemeinen
Formel (I) haben folgende Struktur:
C10-18—Alkyl — S — CH2 — P ;
,OH
OH
(Π) Anmelder:
. SheU Internationale Research , Maatschappij N.V., Den Haag
Vertreter: Dr. K. Schwarzhans
und DipL-Chem. Dr. phil. E. Jung, Patentanwälte,
München 19, Romanplatz 10
Beanspruchte Priorität: " V. St v. Amerika vom 13. April 1959 (Nr. 805 686)
George Milton Calhoun, Berkeley, Calif; '(V. St. Α.),
ist als Erfinder genannt worden
bzw. die Struktur der Aminsalze wie:
OH
/OH-(A)
0-I8-Alkyl- S-CH2- K
(IV)
OH · (A)
Bei den vorstehend angegebenen Formeln wird bevorzugt, daß A ein primäres oder sekundäres Amin,
z. B. ein C8_30-primäres geradkettiges Amin bedeutet,
z.B. Octylamin, Laurylamin, Stearylamin, oder ein verzweigtkettiges primäres aliphatisches Amin, z. B.
ein tert. C8_24-Alkylamin oder ein C5 _ .^-sekundäres
aliphatisches Amin, wie Diamylamin, Di-2-äthylhexylamin,
Didecylamin. Unter den metallischen kationischen Resten werden solche von Erdalkalimetallen,
z. B. Ca oder Ba, bevorzugt.
Es sind bereits halogenhaltige Phosphonsäuremonoester als Zusatzstoffe für Schmiermittel bekanntgeworden,
die gegebenenfalls auch Schwefel enthalten können und bei denen dann der Schwefel koordinativ
309 619/231
an das Phosphoratom gebunden ist. Abgesehen davon, daß ein Halogengehalt nicht immer bei Hochdruckzusatzstoffen
erwünscht ist, unterscheiden sich die Phosphonsäureester gemäß der Erfindung auch dadurch
von den bekannten Zusatzstoffen, daß sich bei ersteren der Schwefel in der an das Phosphoratom
gebundenen Kette mit dem Kohlenwasserstoffrest R befindet.
Weiterhin ist die Herstellung ganz spezieller, in durch Behandlung von Decylmercaptomethylphosphonsäure
mit Butylalkohol in einer alkoholischen Lösung bei etwa 60° C und nachfolgendes Extrahieren
des Esters mit Äther.
Das Di-2-äthylhexylaminsalz von Decylmercaptomethylphosphonsäure
wird hergestellt durch Umsetzen
ihrer Zusammensetzung von den erfindungsgemäß io des Reaktionsproduktes von Beispiel 1 mit Di-2-äthyleingesetzten
Phosphonverbindungen verschiedenen hexylamin in ausreichender Menge zwecks vollstän-Mercaptoäthanophosphonsäurederivate
beschrieben diger Neutralisierung beider Säuregruppen bei etwa worden, die unter anderem als Weichmacher, Insekti- 50° C in einer alkoholischen Lösung, worauf das
zide, Schmierstoffe und hydraulische Flüssigkeiten Aminsalz aus der alkoholischen Lösung gewonnen
Verwendung finden sollen. Das besondere Problem 15 wird.
der Wirkung als Hochdruckzusätze und verschleiß- Beispiel5
verhindernde Mittel wird dabei außerdem nicht ange- μ
geben. Nach der Arbeitsweise des Beispiels 4 wird das
Die erfindungsgemäß verwendeten Phosphonver- tert.-Octadecylaminsalz von Decylmercaptomethylbindungen
werden hergestellt durch Umsetzen eines ao phosphonsäure hergestellt unter Anwendung von
Mercaptans oder Mercaptids mit mindestens 6 Kohlen- tert-Octadecylamin an Stelle von Di-2-äthylhexylstoffatomen
mit einer Halogenmethylphosphonver- amin.
bindung, wie z. B. Halogenmethylphosphonsäure oder Es wurden ferner die folgenden Verbindungen her-
Halogenmethylphosphonat, oder mit ihren Thioderi- gestellt: vaten in geeigneten Lösungsmitteln, z. B. in einer
wäßrigen alkoholischen Lösung bei Siedetemperatur unter Rückfluß, bis die Reaktion beendet ist, was
normalerweise 1 bis etwa 5 Tage erfordert.
Eine bevorzugte Arbeitsweise zur Herstellung der Zusatzstoffe besteht in der Umsetzung eines Natrium-
oder KaIiUm-C10 _18-alkylmercaptids mit einem Natrium-
oderKaliumsalz einer Halogenmethylphosphonsäure, vorzugsweise der Chlormethylphosphonsäure,
in einer alkoholischen Lösung unter Rückfluß und unter einer inerten Atmosphäre. Das sich bildende
Salz wird dann mit einer starken Säure, wie Salzsäure, behandelt, um die freie Alkylmercaptomethylphosphonsäure
in Freiheit zu setzen, welche in die entsprechenden Metallsalze oder Aminsalze von
Teilestern oder vollständigen Estern übergeführt werden kann.
Die folgenden Beispiele erläutern die Herstellung der Phosphonverbindungen. Für das Herstellungsverfahren
an sich wird jedoch im Rahmen dieser Erfindung kein Schutz beansprucht.
Octyhnercaptomethylphosphonsäure, Dodecylmercaptomethylphosphonsäure,
Cyclohexylmercaptomethylphosphonsäure, Benzylmercaptomethylphosphonsäure,
Phenylmercaptomethylphosphonsäure, Dibutyldecylmercaptomethylphosphonsäure,
Dithiobutyldodecyhnercaptomethylphosphonat, Dibutylphenylmercaptomethylphosphonat,
Dithiooctylcyclohexyhnercaptomethylthiophosphonat,
Dioctylaminodecylmercaptomethylphosphonat, Dioctadecylaminphenyhnercaptomethylphosphonat,
tert.-Octadecylamindodecyhnercaptomethylphosphonat.
Die gemäß vorliegender Erfindung eingesetzten Phosphorverbindungen stellen öllösliche Stoffe dar
und sie können in Mengen von etwa 0,1 bis etwa %, vorzugsweise zu etwa 0,5 Vo bis etwa 5,0 Gewichtsprozent,
berechnet auf die gesamte Mischung als Schmierzusätze, verwendet werden.
Geeignete Schmieröle sind mineralische oder synthetische Öle mit einem Viskositätsbereich von
SUS bei 37,8° C bis 250 SUS bei 98,9° C. Die mineralischen Schmieröle können aus paraffinischen,
naphthenischen oder asphaltischen Roherdölmischun-
Stöchiometrische Mengen des Kaliumsalzes von
Decylmercaptan und Monochlormethylphosphonsäure werden in einer wäßrigen Lösung von Äthylalkohol
dispergjert und das Gemisch am Rückfluß bei 78° C in einer Stickstoffatmosphäre während etwa eines
Tages erhitzt. Das gebildete Kaliumdecylmercaptomethylphosphonat wird dann mit starker Salzsäure
behandelt zwecks Freisetzung der freien Phosphon- 55 gen oder Mischungen derselben gewonnen werden.
säure, die durch Extrahieren mit Äther gewonnen Synthetische Öle umfassen die Kohlenwasserstofföle,
wird. wie polymerisierte Olefine, alkylierte Aromaten, isoBeispiel
2 merisierte Wachse sowie sauerstoffhaltige Öle, wie
Polymerisate von Alkylenglykolen und Alkylenoxyden, Gemäß der Arbeitsweise von Beispiel 1 wird die 60 z. B. Mischpolymerisate aus Äthylen- und 1,2-Pro-
Verbindung Phenylmercaptomethylphosphonsäure pylenoxyd, den Mono- und Diolen sowie ihren Esterderivaten.
Andere geeignete synthetisch sauerstoffhaltige Öle sind die Ester aliphatischer zweibasischer
Säuren, wie Di-2-äthylhexylsebazat oder Di-2-äthyl-65
hexyladipat. Die Kohlenwasserstofföle können vermischt werden mit trocknenden ölen, wie Rizinusöl,
Specköl u. dgl., und/oder mit synthetischen Ölen, wie oben erwähnt bzw. mit Silikonpolymeren. Zwei
unter Verwendung des Kaliumsalzes von Phenylmercaptan als Ausgangsmaterial hergestellt.
Der Dibutylester von Decyhnercaptomethylphosphonsäure gemäß Beispiel 1 wird hergestellt
typische Öle A und B von paraffinischem bzw«
naphthenischem Charakter haben folgende Eigenschaften:
. -.-. ■■,:.=:.. .
Mischung H
Fließpunkt, 0C...
Flammpunkt, ° C .
Flammpunkt, ° C .
Viskosität,
SUS bei 98,9° C
Viskositätsindex ..
A (SAElOW)
-23,3 198,9
44 90
(SAE 30) Zusatzstoff nach Beispiel 1 .,....:..:... ,5%
Polyäthylenpropylenglycol mit einer SUS-Viskosität bei 37,8° C von 660 Rest
Mischung I
-20,6 212,8
58 60
Zusatzstoff nach Beispiel 1 2%
Di-2-äthylhexylsebazat ...:.... Rest
Andere geeignete Öle sind die Gasturbinen-Schmieröle mit folgenden Eigenschaften:
Sorte | 1010 | 1065 | |
148,9 | 240,6 | ||
Flammpunkt, 0C | -23,3 | -17,8 | |
Fließpunkt, 0C | |||
Viskosität, | 59,4 | 530 | |
SUS bei 37,8° C | 0,02 | 0,01 | |
Neutralisationszahl | keine | kerne | |
Asche | |||
Die folgenden Zusammensetzungen dienen als Beispiele für die Erfindung, wobei sich die Prozentsätze
auf Gewicht beziehen.
Mischung A
Zusatzstoff nach Beispiel 1 ............. 2e/o
1010-Mineralöl Rest
Mischung B
Zusatzstoff nach Beispiel 2 2%
1010-Mineralöl Rest
Mischung C ν '.""'...
Zusatzstoff nach Beispiel 5 2%
1010-Mineralöl , Rest
Mischung D -
Zusatzstoff nach Beispiel 4 .........: 2%
1010-Mineralöl ._. Rest
Mischung E
Zusatzstoff nach Beispiel 2 1%
SAE-30-Mineralöl Rest
Mischung F
Zusatzstoff nach Beispiel 1 2%
SAE-90-Mineralöl .................... Rest
Mischung G
Zusatzstoff nach Beispiel 1 2%
Laurinsäure .;.................. 2%
SAE-90-Mineralöl . . . - ...... Rest
Gemische gemäß vorliegender Erfindung wurden hinsichtlich ihrer Hochdruckeigenschaften besonders
geprüft auf einer Vorrichtung mit Stirnradgetriebe. Die Vorrichtung besteht im wesentlichen aus zwei
geometrisch ähnlichen Zahnradpaaren, die durch zwei parallele Wellen verbunden sind. Die Zahnradpaare
sind in getrennten Getriebsgehäusen angeordnet, welche auch die tragenden Kugellager enthalten. Eine
der Wellen besteht aus zwei Teilen^ die durch eine Kupplung verbunden sind! Die Belastung wird herbeigeführt
durch Bremsen einer Seite der Kupplung und Einwirkung eines Drehmoments auf die andere Seite.
Die Prüfungsbedingungen waren folgende:
Geschwindigkeit, U/min 3200
Öltemperatur, 0C 100
Ölumlaufgeschwindigkeit, cm3/sec .. 10
Belastungserhöhung
jeweils nach 5 Minuten
Die Ergebnisse der Prüfung skid in Tabelle I zusammengestellt,
und zu Vergleichszwecken sind auch die Resultate angegeben, die bei Anwendung des
Basisöls allein oder mit anderen bekannten Hochdruckgemischen erzielt werden. . ;
Mischung
' ■ ■"■ ■
Mischung A bis I
1010-Mineralöl
+ 21Vo C16-Alkenylbernsteinsäure
1010-Mineralöl
+ 2fl/o Malonsäure
1010-Mineralöl ........
+ 2% 3-Hexadecyladipinsäure ...
1010-Mineralöl
4- 2% Dodecylmercaptobernstein—
säure ..;........
1010-Mineralöl "-"--■-
+ lOfl/oGlycerinmonooleat ........
1010-Mineralöl
+ 2«/o C13H27OH (»OXQ«-Prozeß>
1010-Mineralöl
Belastung bis zum Pressen kg/cm2
392 98
196 98
98 .126
42 ■42
Die folgenden Zusammensetzungen wurden ebenfalls hinsichtlich ihrer Beständigkeit geprüft nach dem
Dornte-Oxydationstest. (beschrieben in »Natural Pe-
troleum News« vom 17. Dezember 1941, S. 294 bis 296). Es wurden folgende Bedingungen eingehalten:
150° C, Eisenkatalysator; mineralische Weißölbasis. Die. Zusatzmenge in jedem Beispiel betrug . etwa
Gewichtsprozent. Die Ergebnisse sind in Tabelle JI zusammengestellt.
Tabelle Π
Zusatzstoff
1. n-Decylmercaptomethylphosphonsäure
Xi-C10H21-S-CH2-P-(OH)2
2. 2-Äthylhexyünercaptomethylphosphonsäure
CH | ,CH2CH-S- | -CH. | O | |
CH3CH5 | I C2H5 |
-P-(OH)2 | ||
3. n-Decyhnercaptoäthylphosphonsäure
I!
n-C10H21 — S — CH2CH2 — P — (OH)2
Induktionsperiode
Stunden
Stunden
140
Die Mercaptomethylphosphonverbindungen der vorliegenden Erfindung sind auch brauchbar bei der
Herstellung von schwerbelasteten Schmierölen, die noch untergeordnete Mengen anderer üblicher Zusatzstoffe
enthalten können, wie Silikon-Antischäumungsmittel, ein Alkylphenol als Antioxydationsmittel,
Polyacrylester als Verbesserungsmittel für den Viskositätsindex, langkettige Fettsäuren, wie
Laurin- und Ölsäure, Mittel zur Verbesserung der Öligkeit.
Es ist gefunden worden, daß die kombinierte Zugäbe der Phosphonoverbindungen gemäß vorliegender
Erfindung und eines phenolischen Antioxydationsmittels, vorzugsweise eines ρ,ρ'-Methylenbisphenols
zu einem Schmieröl zu einem synergetischen oxydationshindernden Effekt führt. Dies kann erläutert
werden durch die folgenden Ergebnisse, die bei dem umstehend erwähnten Dornte-Oxydationstest erhalten
wurden, wobei die Zusatzkonzentration 0,6 Gewichtsprozent betrug.
beständigkeit und können demnach innerhalb weiter Grenzen (z. B. von 3 :1 bis 1: 3) schwanken.
Claims (8)
1. Schmiermittelgemisch auf Schmierölbasis, gekennzeichnet durch einen untergeordneten Gehalt
einer öllöslichen Phosphonverbindung der allgemeinen Formel
j!
XR1
Tabelle III
50
55
60
Die Mengenverhältnisse der jeweils bei den letztbeschriebenen Versuchen verwendeten. Zusatzstoffe
haben nur einen geringen Einfluß auf die Oxydationsin welcher R einen Kohlenwasserstoffrest mit
mindestens 6 Kohlenstoffatomen darstellt, R1 gleich oder verschieden ist und Wasserstoff, einen
aliphatischen oder cycloaliphatischen Rest oder einen kationischen Rest, gebildet aus einem mehrwertigen
Metall oder einem aliphatischen Amin, darstellt, X Sauerstoff oder Schwefel darstellt und
ebenfalls gleich oder verschieden sein kann.
2. Schmiermittelgemisch nach Anspruch 1, dadurch gekennzeichnet, daß R einen Alkylrest mit
10 bis 18 Kohlenstoffatomen darstellt.
3. Schmiermittelgemisch nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß X Sauerstoff
ist.
4. Schmiermittelgemisch nach Anspruch 1 bis 3, dadurch gekennzeichnet, daß das mehrwertige
Metall ein Erdalkalimetall ist.
5. Schmiermittelgemisch nach Anspruch 1 bis 3, dadurch gekennzeichnet, daß das aliphatische
Amin ein primäres Amin mit 8 bis 30 Kohlenstoffatomen, vorzugsweise ein tert. C8_24-Alkylamin
ist.
6. Schmiermittelgemisch nach Anspruch 1 bis 5, gekennzeichnet durch einen Gehalt an der Phos-
phonverbindung in einer Menge von 0,1 bis 25, vorzugsweise 0,5 bis 5 Gewichtsprozent, berechnet
auf das Gesamtgemisch.
7. Schmiermittelgemisch nach Anspruch 1 bis 6, dadurch gekennzeichnet, daß es zusätzlich eine
untergeordnete Menge eines als Schmiermittelzusatz bekannten Alkylphenols, vorzugsweise p,p'-Methylenbisphenol,
enthält.
8. Schmiermittelgemisch nach Anspruch 1 bis 7, dadurch gekennzeichnet, daß es eine Phosphonverbindung
enthält, die durch Umsetzung eines Mercaptans oder Mercaptides mit mindestens 6 Kohlenstoffatomen mit einer Halogenmethyl-
phosphonverbindung der allgemeinen Formel
Halogen — CH2
XR1
in einem inerten Lösungsmittel unter Rückfluß erhalten worden ist, wobei R1 und X die umstehend
erwähnte Bedeutung haben.
In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 935 547, 912251;
USA.-Patentschrift Nr. 2535 174.
© 309 619/231 6.63
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US805686A US3112271A (en) | 1959-04-13 | 1959-04-13 | Liquid hydrocarbon composition |
US77817A US3238131A (en) | 1960-12-23 | 1960-12-23 | Lubricating compositions containing bis(phosphono-methyl) disulfides |
US77830A US3112269A (en) | 1960-12-23 | 1960-12-23 | Lubricating compositions containing sulfoxy alkyl phosphono compounds |
US162924A US3226322A (en) | 1961-12-28 | 1961-12-28 | Liquid hydrocarbon composition and additives therefor |
US183036A US3232882A (en) | 1962-03-28 | 1962-03-28 | Lubricating oil compositions |
US305809A US3198826A (en) | 1959-04-13 | 1963-08-30 | Alkyl mercaptomethylphosphonic acids |
US312329A US3316332A (en) | 1959-04-13 | 1963-09-30 | Sulfoxy alkyl phosphono compounds |
US472663A US3309428A (en) | 1959-04-13 | 1965-07-16 | Oil-soluble bis(methylphosphonodisulfides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1151085B true DE1151085B (de) | 1963-07-04 |
Family
ID=27574562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES68011A Pending DE1151085B (de) | 1959-04-13 | 1960-04-11 | Schmiermittelgemisch |
Country Status (5)
Country | Link |
---|---|
US (3) | US3198826A (de) |
BE (2) | BE611851A (de) |
DE (1) | DE1151085B (de) |
GB (4) | GB904968A (de) |
NL (5) | NL250415A (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2221646A1 (de) * | 1971-05-05 | 1972-11-09 | Esso Res And Engineering Co | Schmieroelzubereitungen |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3957858A (en) * | 1970-04-13 | 1976-05-18 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
US4082793A (en) * | 1977-02-09 | 1978-04-04 | The United States Of America As Represented By The Secretary Of The Navy | Aromatic phosphinic acids containing sulfone linkage |
US4317795A (en) * | 1979-04-05 | 1982-03-02 | Phillips Petroleum Company | Catalytic alkylation of hydrocarbons |
FR2631039A1 (de) * | 1988-05-06 | 1989-11-10 | Elf France | |
US5443744A (en) * | 1993-12-17 | 1995-08-22 | Exxon Chemical Patent Inc. | Non silicone aggresive alkyl phosphates as lubrication oil additives |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2535174A (en) * | 1949-04-07 | 1950-12-26 | Us Rubber Co | Mercaptoethanephosphonates |
DE912251C (de) * | 1950-08-11 | 1954-05-28 | Bataafsche Petroleum | Schmiermittel mit einem Gehalt an halogen- und phosphorhaltigen Verbindungen |
DE935547C (de) * | 1952-12-09 | 1955-11-24 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Kondensationsprodukten mit organisch gebundenem Phosphor |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE542600A (de) * | 1954-11-06 | |||
US2857304A (en) * | 1954-11-23 | 1958-10-21 | Monsanto Chemicals | Dithiodimethylene diphosphonates |
US2793225A (en) * | 1955-08-19 | 1957-05-21 | Union Oil Co | Process for preparing phosphonic acid esters |
-
0
- NL NL272804D patent/NL272804A/xx unknown
- BE BE626579D patent/BE626579A/xx unknown
- BE BE611851D patent/BE611851A/xx unknown
- NL NL287245D patent/NL287245A/xx unknown
- NL NL109943D patent/NL109943C/xx active
- NL NL272803D patent/NL272803A/xx unknown
- NL NL250415D patent/NL250415A/xx unknown
-
1960
- 1960-04-11 DE DES68011A patent/DE1151085B/de active Pending
- 1960-04-11 GB GB12814/60A patent/GB904968A/en not_active Expired
-
1961
- 1961-12-21 GB GB45905/61A patent/GB955357A/en not_active Expired
- 1961-12-21 GB GB45909/61A patent/GB1010536A/en not_active Expired
-
1962
- 1962-12-27 GB GB48702/62A patent/GB957772A/en not_active Expired
-
1963
- 1963-08-30 US US305809A patent/US3198826A/en not_active Expired - Lifetime
- 1963-09-30 US US312329A patent/US3316332A/en not_active Expired - Lifetime
-
1965
- 1965-07-16 US US472663A patent/US3309428A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2535174A (en) * | 1949-04-07 | 1950-12-26 | Us Rubber Co | Mercaptoethanephosphonates |
DE912251C (de) * | 1950-08-11 | 1954-05-28 | Bataafsche Petroleum | Schmiermittel mit einem Gehalt an halogen- und phosphorhaltigen Verbindungen |
DE935547C (de) * | 1952-12-09 | 1955-11-24 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Kondensationsprodukten mit organisch gebundenem Phosphor |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2221646A1 (de) * | 1971-05-05 | 1972-11-09 | Esso Res And Engineering Co | Schmieroelzubereitungen |
Also Published As
Publication number | Publication date |
---|---|
US3309428A (en) | 1967-03-14 |
NL109943C (de) | |
GB955357A (en) | 1964-04-15 |
GB1010536A (en) | 1965-11-17 |
NL250415A (de) | |
GB904968A (en) | 1962-09-05 |
BE611851A (de) | |
US3316332A (en) | 1967-04-25 |
BE626579A (de) | |
NL287245A (de) | |
US3198826A (en) | 1965-08-03 |
NL272803A (de) | |
NL272804A (de) | |
GB957772A (en) | 1964-05-13 |
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