US2902450A - Lubricating oil composition - Google Patents
Lubricating oil composition Download PDFInfo
- Publication number
- US2902450A US2902450A US477955A US47795554A US2902450A US 2902450 A US2902450 A US 2902450A US 477955 A US477955 A US 477955A US 47795554 A US47795554 A US 47795554A US 2902450 A US2902450 A US 2902450A
- Authority
- US
- United States
- Prior art keywords
- lubricating oil
- glycol
- corrosion
- boric acid
- xylylenediamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 48
- 239000010687 lubricating oil Substances 0.000 title description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 26
- 238000005260 corrosion Methods 0.000 claims description 26
- 230000007797 corrosion Effects 0.000 claims description 26
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 19
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 14
- 239000004327 boric acid Substances 0.000 claims description 14
- 238000002485 combustion reaction Methods 0.000 claims description 9
- 239000000314 lubricant Substances 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 239000010688 mineral lubricating oil Substances 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 26
- 235000010338 boric acid Nutrition 0.000 description 16
- 239000000654 additive Substances 0.000 description 13
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 13
- 229910052791 calcium Inorganic materials 0.000 description 12
- 239000011575 calcium Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- -1 glycol boric acids Chemical class 0.000 description 11
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- TTZGACSBMSVUOJ-UHFFFAOYSA-N benzene-1,2-diol;boric acid Chemical group OB(O)O.OC1=CC=CC=C1O TTZGACSBMSVUOJ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WIKSRXFQIZQFEH-UHFFFAOYSA-N [Cu].[Pb] Chemical compound [Cu].[Pb] WIKSRXFQIZQFEH-UHFFFAOYSA-N 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910002065 alloy metal Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 125000003827 glycol group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- SCWWDULYYDFWQV-UHFFFAOYSA-N (2-hydroxyphenoxy)boronic acid Chemical class OB(O)OC1=CC=CC=C1O SCWWDULYYDFWQV-UHFFFAOYSA-N 0.000 description 1
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical class CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- NACLMQVDUHEFQS-UHFFFAOYSA-N 2-ethylhexane-1,2-diol Chemical compound CCCCC(O)(CC)CO NACLMQVDUHEFQS-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- DOZTVCNDWFRDHD-UHFFFAOYSA-N B(O)(O)O.C(C)C(CO)C(CCC)O.C(C)C(CO)C(CCC)O Chemical compound B(O)(O)O.C(C)C(CO)C(CCC)O.C(C)C(CO)C(CCC)O DOZTVCNDWFRDHD-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229940067597 azelate Drugs 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 210000000078 claw Anatomy 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral 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
- 125000005609 naphthenate group Chemical group 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 239000010723 turbine oil Substances 0.000 description 1
- 230000004580 weight loss Effects 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric 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
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/06—Well-defined aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/088—Neutral salts
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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Definitions
- This invention relates to a new lubricating oil composition. More particularly, the invention is concerned with a novel lubricant composition having superior corrosion inhibiting properties.
- lubricating oil compositions tend to become corrosive to metals. This is particularly so when they are employed in modern internal combustion engines which are operated under conditions involving increased temperature changes, higher speeds and reduced clearances, all of which conditions aggravate the formation of corrosive decomposition products in the oil. Alloy metal bearings commonly employed in such engines make the problem all the more serious, since they are especially subject to corrosive attack and furthermore, may have a catalytic effect on the decomposition of lubricating oils with which they come into contact, thereby causing additional corrosivity in the oil.
- inhibitors to lubricating oil compositions, generally, for the purpose of improving their resistance to the formation and effect of corrosive products has not been entirely satisfactory.
- a great many of these additives are only moderately effective and permit the bearings and other metal surfaces coming into contact with the lubricating oil composition to be slowly but eventually corroded to a degree where interruption of engine operation for overhaul and replacement of parts becomes necessary.
- many of the more effective additives are active only for a limited period and require replenishing or a complete change of the lubricating oil composition.
- Still other additives, although effective as corrosion inhibitors, are so insoluble in oils of lubricating viscosity that special solubilizing or dispersing agents are necessary to retain them in the composition.
- Corrosion inhibitors for lubricating oil compositions are further handicapped by the fact that oils of this type are commonly compounded with other additives such as detergents, sludge inhibitors and the like which are designed to loosen, suspend and otherwise minimize the effect of decomposition products formed in the oils during their normal service. Many of these compounding agents, besides adding to the corrosivity of the oil themselves, have an adverse effect on the activity of the corrosion inhibitors employed heretofore, and it is necessary to find inhibitors which will function in combination with them.
- additives for the inhibition of oxidation or corrosion in lubricating oil compositions prior to this invention have generally contained some form of active sulfur. This has made such compositions undesirable for the lubrication of silver and similar metal-containing bearings which are especially susceptible to attack by active sulfur. Since silver and similar metal-containing bearings are being increasingly employed today, particularly in certain important classes of internal combustion enginessuch as marine and railroad diesel engines, it has become necessary to find a lubricant composition which is inhibited against corrosion without the use of sulfur-containing additives.
- a new and unusually effective lubricating oil composition having improved cor- 2,902,450 Patented Sept. 1, 1959 rosion inhibiting properties has been found comprising a major portion of an oil of lubricating viscosity and a minor portion, suflicient to inhibit corrosion, of a p-xylylenediamine salt of an acid compound selected from the group consisting of glycol boric acids and vicinal dihydroxy benzene boric acids.
- the new lubricating oil composition in accordance with the present invention is characterized by remarkable corrosion inhibiting properties for metal surfaces and alloy bearings over extended periods of operation.
- the composition is unusually stable under normal operating conditions without the use of stabilizers and dispersing agents. There is no reduction of corrosion inhibition due to deposition of the additive.
- a further outstanding characteristic of the composition lies in the fact that these beneficial properties are obtained without adverse eifect from other conventional additives commonly employed in lubricant compositions.
- the lubricating oil compositions of the invention possess still another advantage in that they are unusually effective lubricants for particular alloy metal bearings such as the silver metal-containing bearings of marine and railroad diesel engines.
- the p-xylylenediamine salts of glycol boric acids or vicinal dihydroxy benzene boric acids which provide the new and unusually effective corrosion inhibited lubricat-- ing oil compositions according to the invention are novel compounds. They are prepared by the addition of p-xylylenediamine to the glycol boric acid or vicinal dihydroxy benzene boric acid. The reaction is straightforward, and the salt is obtained merely by heating a mixture of p-xylylenediamine and the glycol boric acid or vicinal dihydroxy benzene boric acid at a temperature at which reaction occurs until the reaction is complete.
- Stoichiometric amounts of p-xylylenediamine are reacted with the glycol boric acid or vicinal dihydroxy benzene boric acid.
- Temperatures of from about 50 C. to about C. are preferred, although some reaction will occur at temperatures below and above this range, as, for example, from 25 C. up to C. and higher.
- Inert solvents may be used, if desired, in the reaction to facilitate the handling of materials.
- glycol boric acids and vicinal dihydroxy benzene boric acids referred to above are complexes prepared by the reaction of a mixture of boric acid and glycol or polyhydroxy benzene.
- the mixtures are ordinarily heated to accelerate the reaction.
- two of the hydroxyl groups of a single glycol or polyhydroxy benzene react with the boric acid to form what is commonly termed a metal chelate compound.
- These compounds are characterized by a claw type of structure in which one or more rings of a similar or unlike structure due to the use of mixed glycols or polyhydroxy benzenes are formed to include the boron.
- Di-beta glycol borates 2,902,450 3 4 R R R invention include hydrocarbon or mineral lubri- ⁇ l cating oils of naphthenic, paraffinic, and mixed naphthenic R G O ⁇ and paraflinic types. They may be refined by any of B B the conventional methods such as solvent refining and 5 acid refining. Synthetic hydrocarbon oils of the alkylene I I polymer type or those derivedfrom coal and shale may R also be employed.
- Alkylene-oxide polymers-and their MWWWMTQYOOWOM Monmbotw'glywlmmes derivatives such as the propylene oxide polymers and their ethyl esters and acetyl derivatives in which the terminal hydroxyl groups have been modified are'also Mono-pyrocatechol borates I o o Dl-(pyrocatechol) borates wherein R'ishydrogenor a group ofhydrocarbon structure ashereinafter defined.
- glycols which are reacted with the boric acid are preferably 04- and ,B-alkanediols containing from 2 to 18 carbon atoms.
- Such glycols include, for example, ethylene glycol, 1,2- and 1,3-propanediol, 1,3-pentanediol, 2,3- butanediol, 1,2-hexanediol, 2.-methyl--1,3-pentanediol,1,2- and 1,3-octylene glycols including 2-ethyl-1,3-hexanediol, 1,2-dodecanediol, 2,4-diethyl-l,3-octanediol, and 2,4,6- triethyl-l,3-decanediol.
- Glycols containing from 6 to 10 carbon .atoms are more preferred, since they impart an optimum degree of oil solubility to the final product.
- ocand B-Octylene glycols such as 2-ethyl-1,2 -hexanediol and 2-ethyl-1,3-hexanediol are most satisfactory for present purposes.
- the polyhydroxy benzenes are preferably vicinal dihydric phenols such as catechol, 3,4-dihydroxy toluene, tert.-butylcatechol, cetylcatechol, and the like. They may contain additional hydroxyl groups, as for example, 1,2,4-trihydroxy benzene.
- Alkyl catechols containing from 2 to 18 carbon atoms in the alkyl group are at present most preferred since the compounds prepared from them possess the most satisfactory oil solubility characteristics.
- the acid compounds of boric acid and glycols or polyhydroxy benzenes referred to above are more fully described in the co-pending patent application of John R. Thomas and Oliver L. Harle, Serial No. 440,264, filed June 29, 1954, now Patent No. 2,795,548.
- the p-xylylenediamine is a known compound and may be conveniently obtained by'the conversion of terephthalic acid to terephathalodinitrile, which may then be hydrogenated to give the p-xylylenediamine.
- the p-xylylenediamine salt of the acid compound of boric acid and a member selected from the group consisting of glycols and vicinal polyhydroxy benzenes, as already mentioned, is present in the lubricating oil composition in a minor portion, sufficient to inhibit corrosion. Generally, amounts from 0.01 to about 10.0% by weight of the lubricating oil composition are very satisfactory.
- Lubricating oil concentrates containing larger amounts of the corrosion inhibitor, up to 30% by weight or more, constitute a specific embodiment of the invention.
- the unusual stability of these lubricating oil compositions is particularly adapted to the preparation of such concentrates which would not be possible with conventional additives.
- the preferred lubricating oil compositions contain from about 0.1 to 5.0% by weight. Such compositions are unusually stable and provide remarkably efiective corrosion inhibition for extended periods in the operation of internal combustion engines.
- oils of lubricating viscosity are suitable base oils for the compositions of the suitable.
- Synthetic oils of the dicarboxylic acid ester type including dibutyl adipate, di-2-ethylhexyl "sebacate, di-n-hexyl fumaric polymer, di-lauryl azelate, and the like may be used.
- Alkyl benzene types of synthetic oils such as tetradecyl benzene, etc., are also included.
- Liquid esters of acids of phosphorus including tricresyl phosphate, diethyl esters of decane phosphonic acid, and the like may also be employed.
- polysiloxane oils of the type of polyalkyl-, polyaryl-, polyalkoxyand polyaryloxy siloxanes such as polymethyl siloxane, polymethylphenyl siloxane and polymethoxyphenoxy siloxane and silicate ester oils such as tetraalkyland tetraaryl silicates of the tetra-Z-ethylhexyl silicate and tetra-p-tert.-butylphenyl silicate types.
- the corrosion inhibiting'corripositions of this invention are outstanding in that they are unusually effective in the form of compoundedlubricating oils containing conventional additives such as oxidation inhibitors, detergents or dispersants, sludge inhibitors, pour depressants, VI improvers, antifoaming agents, rust inhibitors, oiliness or film strengthening agents, wear inhibitors, dyes and the like.
- conventional additives such as oxidation inhibitors, detergents or dispersants, sludge inhibitors, pour depressants, VI improvers, antifoaming agents, rust inhibitors, oiliness or film strengthening agents, wear inhibitors, dyes and the like.
- a great many of these compounded oils are generally corrosive to metal surfacesand alloy metal bearings in particuIar,-a'nd it is an exceptional attribute of the present compositions whereby corrosion inhibited compounded lubricating oils are provided.
- compositions according to the invention are very desirable features of the compositions according to the invention.
- the corrosion inhibition is obtained Without any noticeable adverse etfect on the other additives, thus permitting more (efficient allaround lubrication of internal combustion engines and other types of machines where unusually severe conditions of service are more and more commonly encountered.
- EXAMPLE I the p-xylylenediamine salt of di( -2-ethyl- 1,2-hexanediol)boric. acid was prepared. 1.36 parts of p-xylylenediamine and 3.06 parts of di(2-ethyl-l,2-hex-anediol)boric acid were charged to a reaction vesselequipped with stirring and heating means. The mixture was stirred at 200 F. for about 10 minutes. The product was a viscous brown liquid which was soluble in mineral oil.
- EXAMPLE II In this example a lubricating oil composition containing 1% by Weight of the p-xylylenediamine salt of di(2-ethyl- 1,2-h'ex'anediol)boric acid was prepared. 346.5 parts of a solvent refined SAE 30 mineral lubricating oil containing 10 mM/kg. basic calcium petroleum sulfonate analyzing 1.67% calcium and 36 mM/kg. sulfurized basic calcium alkyl phenate analyzing 3.10% calcium was charged to a reaction vessel equipped with stirring and heating means. 3.5 parts of the p-xylylenediamine salt of di(2-ethyl-l,2-hexanediol)boiic acid prepared in Example I was then added. The mixture was stirred at about F. for 20 minutes. The product was astable lubricating oil composition completely clear in appearance indicating uniform miscibility of lubricating oil base and corrosion inhibitor.
- the test is continued for 20 hours.
- the copper-lead strip is then removed, rubbed vigorously with a soft cloth and weighed to determine the net weight loss.
- the reference oil of the compositions tested is a conventional compounded oil, namely, solvent refined SAE 30 mineral lubricating oil containing mM/ kg. of basic calcium petroleum sulfonate analyzing 1.67% calcium and 36 mM/ kg. of sulfurized basic calcium alkyl phenate analyzing 3.10% calcium.
- concentrations of pxylylenediamine salt of the glycol borate complex are given in percent by Weight of the composition.
- lubricating oil compositions in accordance with the invention employing only 1% of the p-xylylenediamine salt of the glycol boric acid give a very low corrosion loss of only 7.4 mg.
- Such outstanding effectiveness of the present compositions is all the more remarkable, since it is not shared by similar compositions containing other amine salts of glycol and catechol boric acids, including the isomeric m-xylylenediamine salt.
- lubricating oil compositions of the invention have been described primarily for their effectiveness as internal combustion engine lubricants, a great many other applications are also possible. Such applications include their use as turbine oils, hydraulic fluids, instrument oils, constituent oils in grease manufacture, ice machine oils and the like.
- a lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic alkaline earth metal petroleum sulfonate and basic sulfurized alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and a minor portion, sufficient to inhibit corrosion of a p-xylylenediamine salt of a diglycol boric acid in which the glycol groups are identical aand ,B-glycol groups containing from 6 to 10 carbon atoms in each glycol group.
- a lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic calcium petroleum sulfonate and basic sulfurized calcium alkyl phenate which is normally corrosive to alloy bearings and a minor portion, sufiicient to inhibit corrosion, of a p-xylylenediamine salt of di(2-ethyl-l,3-hexanediol)boric acid.
- a lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic calcium petroleum sulfonate and basic sulfurized calcium alkyl phenate which is normally corrosive to alloy bearings and a minor portion sufificient to inhibit corrosion of a p-xylylenediamine salt of di(1,2-hexanediol) boric acid.
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Description
United States Patent Cfiice LUBRICATING OIL COMPOSITION Warren Lowe, Berkeley, Calif., assign'or to California Research Corporation, San Francisco, Calif., a corporation of Delaware I No Drawing. Application December 27, 1954 Serial No. 477,955
3 Claims. (Cl. 252-3345) This invention relates to a new lubricating oil composition. More particularly, the invention is concerned with a novel lubricant composition having superior corrosion inhibiting properties.
During their normal service, lubricating oil compositions tend to become corrosive to metals. This is particularly so when they are employed in modern internal combustion engines which are operated under conditions involving increased temperature changes, higher speeds and reduced clearances, all of which conditions aggravate the formation of corrosive decomposition products in the oil. Alloy metal bearings commonly employed in such engines make the problem all the more serious, since they are especially subject to corrosive attack and furthermore, may have a catalytic effect on the decomposition of lubricating oils with which they come into contact, thereby causing additional corrosivity in the oil.
The addition of inhibitors to lubricating oil compositions, generally, for the purpose of improving their resistance to the formation and effect of corrosive products has not been entirely satisfactory. A great many of these additives are only moderately effective and permit the bearings and other metal surfaces coming into contact with the lubricating oil composition to be slowly but eventually corroded to a degree where interruption of engine operation for overhaul and replacement of parts becomes necessary. Furthermore, many of the more effective additives are active only for a limited period and require replenishing or a complete change of the lubricating oil composition. Still other additives, although effective as corrosion inhibitors, are so insoluble in oils of lubricating viscosity that special solubilizing or dispersing agents are necessary to retain them in the composition.
Corrosion inhibitors for lubricating oil compositions are further handicapped by the fact that oils of this type are commonly compounded with other additives such as detergents, sludge inhibitors and the like which are designed to loosen, suspend and otherwise minimize the effect of decomposition products formed in the oils during their normal service. Many of these compounding agents, besides adding to the corrosivity of the oil themselves, have an adverse effect on the activity of the corrosion inhibitors employed heretofore, and it is necessary to find inhibitors which will function in combination with them.
Furthermore, additives for the inhibition of oxidation or corrosion in lubricating oil compositions prior to this invention have generally contained some form of active sulfur. This has made such compositions undesirable for the lubrication of silver and similar metal-containing bearings which are especially susceptible to attack by active sulfur. Since silver and similar metal-containing bearings are being increasingly employed today, particularly in certain important classes of internal combustion enginessuch as marine and railroad diesel engines, it has become necessary to find a lubricant composition which is inhibited against corrosion without the use of sulfur-containing additives.
According to the present invention, a new and unusually effective lubricating oil composition having improved cor- 2,902,450 Patented Sept. 1, 1959 rosion inhibiting properties has been found comprising a major portion of an oil of lubricating viscosity and a minor portion, suflicient to inhibit corrosion, of a p-xylylenediamine salt of an acid compound selected from the group consisting of glycol boric acids and vicinal dihydroxy benzene boric acids.
The new lubricating oil composition in accordance with the present invention is characterized by remarkable corrosion inhibiting properties for metal surfaces and alloy bearings over extended periods of operation. The composition is unusually stable under normal operating conditions without the use of stabilizers and dispersing agents. There is no reduction of corrosion inhibition due to deposition of the additive. A further outstanding characteristic of the composition, however, lies in the fact that these beneficial properties are obtained without adverse eifect from other conventional additives commonly employed in lubricant compositions. The lubricating oil compositions of the invention possess still another advantage in that they are unusually effective lubricants for particular alloy metal bearings such as the silver metal-containing bearings of marine and railroad diesel engines.
The p-xylylenediamine salts of glycol boric acids or vicinal dihydroxy benzene boric acids which provide the new and unusually effective corrosion inhibited lubricat-- ing oil compositions according to the invention are novel compounds. They are prepared by the addition of p-xylylenediamine to the glycol boric acid or vicinal dihydroxy benzene boric acid. The reaction is straightforward, and the salt is obtained merely by heating a mixture of p-xylylenediamine and the glycol boric acid or vicinal dihydroxy benzene boric acid at a temperature at which reaction occurs until the reaction is complete. Stoichiometric amounts of p-xylylenediamine are reacted with the glycol boric acid or vicinal dihydroxy benzene boric acid. Preferably molar excesses of p-xylylenediamine up to 30% or more are used to insure complete reaction. Temperatures of from about 50 C. to about C. are preferred, although some reaction will occur at temperatures below and above this range, as, for example, from 25 C. up to C. and higher. Inert solvents may be used, if desired, in the reaction to facilitate the handling of materials.
The glycol boric acids and vicinal dihydroxy benzene boric acids referred to above are complexes prepared by the reaction of a mixture of boric acid and glycol or polyhydroxy benzene. The mixtures are ordinarily heated to accelerate the reaction. Although the nature of the reaction is not definitely known, it is believed that two of the hydroxyl groups of a single glycol or polyhydroxy benzene react with the boric acid to form what is commonly termed a metal chelate compound. These compounds are characterized by a claw type of structure in which one or more rings of a similar or unlike structure due to the use of mixed glycols or polyhydroxy benzenes are formed to include the boron. For contrated by the following formulae:
Di-beta glycol borates 2,902,450 3 4 R R R invention. They include hydrocarbon or mineral lubri- \l cating oils of naphthenic, paraffinic, and mixed naphthenic R G O\ and paraflinic types. They may be refined by any of B B the conventional methods such as solvent refining and 5 acid refining. Synthetic hydrocarbon oils of the alkylene I I polymer type or those derivedfrom coal and shale may R also be employed. Alkylene-oxide polymers-and their MWWWMTQYOOWOM Monmbotw'glywlmmes derivatives such as the propylene oxide polymers and their ethyl esters and acetyl derivatives in which the terminal hydroxyl groups have been modified are'also Mono-pyrocatechol borates I o o Dl-(pyrocatechol) borates wherein R'ishydrogenor a group ofhydrocarbon structure ashereinafter defined.
The glycols which are reacted with the boric acid are preferably 04- and ,B-alkanediols containing from 2 to 18 carbon atoms. Such glycols include, for example, ethylene glycol, 1,2- and 1,3-propanediol, 1,3-pentanediol, 2,3- butanediol, 1,2-hexanediol, 2.-methyl--1,3-pentanediol,1,2- and 1,3-octylene glycols including 2-ethyl-1,3-hexanediol, 1,2-dodecanediol, 2,4-diethyl-l,3-octanediol, and 2,4,6- triethyl-l,3-decanediol. Glycols containing from 6 to 10 carbon .atoms are more preferred, since they impart an optimum degree of oil solubility to the final product. ocand B-Octylene glycols such as 2-ethyl-1,2 -hexanediol and 2-ethyl-1,3-hexanediol are most satisfactory for present purposes. g
The polyhydroxy benzenes are preferably vicinal dihydric phenols such as catechol, 3,4-dihydroxy toluene, tert.-butylcatechol, cetylcatechol, and the like. They may contain additional hydroxyl groups, as for example, 1,2,4-trihydroxy benzene. Alkyl catechols containing from 2 to 18 carbon atoms in the alkyl group are at present most preferred since the compounds prepared from them possess the most satisfactory oil solubility characteristics.
The acid compounds of boric acid and glycols or polyhydroxy benzenes referred to above are more fully described in the co-pending patent application of John R. Thomas and Oliver L. Harle, Serial No. 440,264, filed June 29, 1954, now Patent No. 2,795,548. The p-xylylenediamine is a known compound and may be conveniently obtained by'the conversion of terephthalic acid to terephathalodinitrile, which may then be hydrogenated to give the p-xylylenediamine.
The p-xylylenediamine salt of the acid compound of boric acid and a member selected from the group consisting of glycols and vicinal polyhydroxy benzenes, as already mentioned, is present in the lubricating oil composition in a minor portion, sufficient to inhibit corrosion. Generally, amounts from 0.01 to about 10.0% by weight of the lubricating oil composition are very satisfactory. Lubricating oil concentrates containing larger amounts of the corrosion inhibitor, up to 30% by weight or more, constitute a specific embodiment of the invention. The unusual stability of these lubricating oil compositions is particularly adapted to the preparation of such concentrates which would not be possible with conventional additives. For present purposes, the preferred lubricating oil compositions contain from about 0.1 to 5.0% by weight. Such compositions are unusually stable and provide remarkably efiective corrosion inhibition for extended periods in the operation of internal combustion engines.
Any of the well-known types of oils of lubricating viscosity are suitable base oils for the compositions of the suitable. Synthetic oils of the dicarboxylic acid ester type including dibutyl adipate, di-2-ethylhexyl "sebacate, di-n-hexyl fumaric polymer, di-lauryl azelate, and the like may be used. Alkyl benzene types of synthetic oils such as tetradecyl benzene, etc., are also included. Liquid esters of acids of phosphorus including tricresyl phosphate, diethyl esters of decane phosphonic acid, and the like may also be employed. Also suitable are the polysiloxane oils of the type of polyalkyl-, polyaryl-, polyalkoxyand polyaryloxy siloxanes such as polymethyl siloxane, polymethylphenyl siloxane and polymethoxyphenoxy siloxane and silicate ester oils such as tetraalkyland tetraaryl silicates of the tetra-Z-ethylhexyl silicate and tetra-p-tert.-butylphenyl silicate types.
As already mentioned, the corrosion inhibiting'corripositions of this invention are outstanding in that they are unusually effective in the form of compoundedlubricating oils containing conventional additives such as oxidation inhibitors, detergents or dispersants, sludge inhibitors, pour depressants, VI improvers, antifoaming agents, rust inhibitors, oiliness or film strengthening agents, wear inhibitors, dyes and the like. A great many of these compounded oils are generally corrosive to metal surfacesand alloy metal bearings in particuIar,-a'nd it is an exceptional attribute of the present compositions whereby corrosion inhibited compounded lubricating oils are provided. 'A further very desirable feature of the compositions according to the invention is the fact that the corrosion inhibition is obtained Without any noticeable adverse etfect on the other additives, thus permitting more (efficient allaround lubrication of internal combustion engines and other types of machines where unusually severe conditions of service are more and more commonly encountered.
The following examples are submitted as additional illustrations of the invention. These examples show the preparation of the various lubricant compositions and the evaluation of their effectiveness as corrosion inhibitors. The proportions given in these examples, unless otherwise specified, are on a weight basis and include both percent and millimoles per kilogram (mM/kg.) of the various additives.
EXAMPLE I In this example the p-xylylenediamine salt of di( -2-ethyl- 1,2-hexanediol)boric. acid was prepared. 1.36 parts of p-xylylenediamine and 3.06 parts of di(2-ethyl-l,2-hex-anediol)boric acid were charged to a reaction vesselequipped with stirring and heating means. The mixture was stirred at 200 F. for about 10 minutes. The product was a viscous brown liquid which was soluble in mineral oil.
EXAMPLE II In this example a lubricating oil composition containing 1% by Weight of the p-xylylenediamine salt of di(2-ethyl- 1,2-h'ex'anediol)boric acid was prepared. 346.5 parts of a solvent refined SAE 30 mineral lubricating oil containing 10 mM/kg. basic calcium petroleum sulfonate analyzing 1.67% calcium and 36 mM/kg. sulfurized basic calcium alkyl phenate analyzing 3.10% calcium was charged to a reaction vessel equipped with stirring and heating means. 3.5 parts of the p-xylylenediamine salt of di(2-ethyl-l,2-hexanediol)boiic acid prepared in Example I was then added. The mixture was stirred at about F. for 20 minutes. The product was astable lubricating oil composition completely clear in appearance indicating uniform miscibility of lubricating oil base and corrosion inhibitor.
Other p-xylylenediamine salts of glycol boric acid compounds and lubricating oil compositions containing them were prepared in accordance with the above-described procedures. The properties of these compositions and their eifectiveness are illustrated by the following typical results of standard lubricating oil tests for determining corrosion inhibition. In the Copper-Lead Strip Corrosion Test, a polished copper-lead strip is weighed and immersed in 300 ml. of test oil contained in a 400 ml., lipless Berzelius beaker. The test oil is maintained at 340 F. under a pressure of 1 atmosphere of air and stirred with the mechanical stirrer at 1000 r.p.m. After 2 hours, a synthetic naphthenate catalyst is added to provide the following catalytic metals:
Percent by weight Iron 0.008 Lead 0.004 Copper 0.002 Manganese 0.0005 Chromium 0.004
The test is continued for 20 hours. The copper-lead strip is then removed, rubbed vigorously with a soft cloth and weighed to determine the net weight loss.
The reference oil of the compositions tested is a conventional compounded oil, namely, solvent refined SAE 30 mineral lubricating oil containing mM/ kg. of basic calcium petroleum sulfonate analyzing 1.67% calcium and 36 mM/ kg. of sulfurized basic calcium alkyl phenate analyzing 3.10% calcium. The concentrations of pxylylenediamine salt of the glycol borate complex are given in percent by Weight of the composition.
Table COPPER-LEAD STRIP CORROSION TEST The above tests show that the reference oil, a conventional compounded lubricating oil containing a representative heavy duty oil detergent additive of the alkaline earth metal petroleum sulfonate type and stabilizer of the alkaline earth metal phenate type, when used alone, gives a copper-lead strip loss of over 250 mg. The addition of 2% by weight of di(2-ethyl-1,3-hexanediol) boric acid to the reference oil in the test causes an even greater copper-lead strip loss of about 354 mg. By way of distinction, lubricating oil compositions in accordance with the invention employing only 1% of the p-xylylenediamine salt of the glycol boric acid give a very low corrosion loss of only 7.4 mg. Such outstanding effectiveness of the present compositions is all the more remarkable, since it is not shared by similar compositions containing other amine salts of glycol and catechol boric acids, including the isomeric m-xylylenediamine salt.
Although the lubricating oil compositions of the invention have been described primarily for their effectiveness as internal combustion engine lubricants, a great many other applications are also possible. Such applications include their use as turbine oils, hydraulic fluids, instrument oils, constituent oils in grease manufacture, ice machine oils and the like.
I claim:
1. A lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic alkaline earth metal petroleum sulfonate and basic sulfurized alkaline earth metal alkyl phenate which is normally corrosive to alloy bearings and a minor portion, sufficient to inhibit corrosion of a p-xylylenediamine salt of a diglycol boric acid in which the glycol groups are identical aand ,B-glycol groups containing from 6 to 10 carbon atoms in each glycol group.
2. A lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic calcium petroleum sulfonate and basic sulfurized calcium alkyl phenate which is normally corrosive to alloy bearings and a minor portion, sufiicient to inhibit corrosion, of a p-xylylenediamine salt of di(2-ethyl-l,3-hexanediol)boric acid.
3. A lubricant composition consisting essentially of a major portion of a mineral lubricating oil for internal combustion engines containing minor amounts of basic calcium petroleum sulfonate and basic sulfurized calcium alkyl phenate which is normally corrosive to alloy bearings and a minor portion sufificient to inhibit corrosion of a p-xylylenediamine salt of di(1,2-hexanediol) boric acid.
References Cited in the file of this patent UNITED STATES PATENTS 1,975,890 Williams Oct. 9, 1934 2,497,521 Trautman Feb. 14, 1950 2,582,191 Curtis Jan 8, 1952 2,795,548 Thomas et a1. June 11, 1957
Claims (1)
1. A LUBRICANT COMPOSITION CONSISTING ESSENTIALLY OF A MAJOR PORTION OF A MINERAL LUBRICATING OIL FOR INTERNAL COMBUSTION ENGINES CONTAINING MINOR AMOUNTS OF BASIC ALKALINE EARTH METAL PETROLEUM SULFONATE AND BASIC SULFURIZED ALKALINE EARTH METAL ALKYL PHENATE WHICH IS NORMALLY CORROSIVE TO ALLOY BEARINGS AND A MINOR PORTION, SUFFICIENT TO INHIBIT CORROSION F A P-XYLYLENEDIAMINE SALT OF A DIGLYCOL BORIC ACID IN WHICH THE GLYCOL GROUPS ARE IDENTICAL A-AND B-GLYCOL GROUPS CONTAINING FROM 6 TO 10 CARBON ATOMS IN EACH GLYCOL GROUP.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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US477955A US2902450A (en) | 1954-12-27 | 1954-12-27 | Lubricating oil composition |
US550483A US2883412A (en) | 1954-12-27 | 1955-12-01 | P-xylylenediamine salts of glycol boric acids |
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US477955A US2902450A (en) | 1954-12-27 | 1954-12-27 | Lubricating oil composition |
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US477955A Expired - Lifetime US2902450A (en) | 1954-12-27 | 1954-12-27 | Lubricating oil composition |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US3028411A (en) * | 1959-12-09 | 1962-04-03 | United States Borax Chem | Preparation of organic monoborate salts |
US3111383A (en) * | 1961-06-21 | 1963-11-19 | American Potash & Chem Corp | Boron extractants |
US3267126A (en) * | 1962-11-08 | 1966-08-16 | Fmc Corp | Complex spirocyclic esters of boric acid |
US5581010A (en) * | 1994-07-22 | 1996-12-03 | Rockwell International Corporation | Semi-organic crystals for nonlinear optical devices |
WO2016138248A1 (en) * | 2015-02-26 | 2016-09-01 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
WO2018017911A1 (en) * | 2016-07-22 | 2018-01-25 | The Lubrizol Corporation | Aliphatic tetrahedral borate compounds for lubricating compositions |
US11680217B2 (en) | 2015-03-23 | 2023-06-20 | Lanxess Corporation | Low ash lubricant and fuel additive comprising alkoxylated amine |
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US1975890A (en) * | 1932-06-17 | 1934-10-09 | Du Pont | Salts of pyrocatechol borate and methods for preparing the same |
US2497521A (en) * | 1947-12-03 | 1950-02-14 | Gulf Research Development Co | Oil compositions containing amine salts of boro-diol complexes |
US2582191A (en) * | 1946-09-30 | 1952-01-08 | Curtis David | Amino salts of boric acid-aliphatic polyhydroxy carboxylic acid condensation product |
US2795548A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricant compositions |
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- 1954-12-27 US US477955A patent/US2902450A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1975890A (en) * | 1932-06-17 | 1934-10-09 | Du Pont | Salts of pyrocatechol borate and methods for preparing the same |
US2582191A (en) * | 1946-09-30 | 1952-01-08 | Curtis David | Amino salts of boric acid-aliphatic polyhydroxy carboxylic acid condensation product |
US2497521A (en) * | 1947-12-03 | 1950-02-14 | Gulf Research Development Co | Oil compositions containing amine salts of boro-diol complexes |
US2795548A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricant compositions |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3028411A (en) * | 1959-12-09 | 1962-04-03 | United States Borax Chem | Preparation of organic monoborate salts |
US3111383A (en) * | 1961-06-21 | 1963-11-19 | American Potash & Chem Corp | Boron extractants |
US3267126A (en) * | 1962-11-08 | 1966-08-16 | Fmc Corp | Complex spirocyclic esters of boric acid |
US5581010A (en) * | 1994-07-22 | 1996-12-03 | Rockwell International Corporation | Semi-organic crystals for nonlinear optical devices |
US10336963B2 (en) | 2015-02-26 | 2019-07-02 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
CN107406786A (en) * | 2015-02-26 | 2017-11-28 | 路博润公司 | Aromatics tetrahedron borate compound for lubricating composition |
WO2016138248A1 (en) * | 2015-02-26 | 2016-09-01 | The Lubrizol Corporation | Aromatic tetrahedral borate compounds for lubricating compositions |
CN107406786B (en) * | 2015-02-26 | 2023-06-06 | 路博润公司 | Aromatic tetrahedral borate compounds for lubricating compositions |
US11680217B2 (en) | 2015-03-23 | 2023-06-20 | Lanxess Corporation | Low ash lubricant and fuel additive comprising alkoxylated amine |
WO2018017911A1 (en) * | 2016-07-22 | 2018-01-25 | The Lubrizol Corporation | Aliphatic tetrahedral borate compounds for lubricating compositions |
WO2018017913A1 (en) * | 2016-07-22 | 2018-01-25 | The Lubrizol Corporation | Aliphatic tetrahedral borate compounds for fully formulated lubricating compositions |
CN109715767A (en) * | 2016-07-22 | 2019-05-03 | 路博润公司 | The aliphatic tetrahedron borate compound of lubricating composition for preparing completely |
US10774283B2 (en) | 2016-07-22 | 2020-09-15 | The Lubrizol Corporation | Aliphatic tetrahedral borate compounds for fully formulated lubricating compositions |
CN109715767B (en) * | 2016-07-22 | 2022-01-21 | 路博润公司 | Aliphatic tetrahedral borate compounds for fully formulated lubricating compositions |
US11459520B2 (en) | 2016-07-22 | 2022-10-04 | The Lubrizol Corporation | Aliphatic tetrahedral borate compounds for lubricating compositions |
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