US3751367A - Compositions comprising boron compounds and polyphenyl thioethers - Google Patents
Compositions comprising boron compounds and polyphenyl thioethers Download PDFInfo
- Publication number
- US3751367A US3751367A US00167463A US3751367DA US3751367A US 3751367 A US3751367 A US 3751367A US 00167463 A US00167463 A US 00167463A US 3751367D A US3751367D A US 3751367DA US 3751367 A US3751367 A US 3751367A
- Authority
- US
- United States
- Prior art keywords
- bis
- sulfide
- compositions
- polyphenyl
- boroxin
- 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
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- 239000000203 mixture Substances 0.000 title abstract description 60
- 229920006389 polyphenyl polymer Polymers 0.000 title abstract description 24
- 150000003568 thioethers Chemical class 0.000 title abstract description 14
- 150000001639 boron compounds Chemical class 0.000 title description 2
- 239000012530 fluid Substances 0.000 abstract description 15
- VOXXGUAZBWSUSS-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5,2,4,6-trioxatriborinane Chemical compound O1B(C=2C=CC=CC=2)OB(C=2C=CC=CC=2)OB1C1=CC=CC=C1 VOXXGUAZBWSUSS-UHFFFAOYSA-N 0.000 abstract description 9
- 230000001590 oxidative effect Effects 0.000 abstract description 7
- 229910052709 silver Inorganic materials 0.000 abstract description 5
- 239000004332 silver Substances 0.000 abstract description 5
- -1 phenoxy, phenylmercapto Chemical class 0.000 description 80
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 67
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 26
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- BRTALTYTFFNPAC-UHFFFAOYSA-N boroxin Chemical compound B1OBOBO1 BRTALTYTFFNPAC-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 239000000314 lubricant Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229910052717 sulfur Chemical group 0.000 description 6
- 239000011593 sulfur Chemical group 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- GXYUTKVRTNINRK-UHFFFAOYSA-N 1,2-bis(phenylsulfanyl)benzene Chemical class C=1C=CC=C(SC=2C=CC=CC=2)C=1SC1=CC=CC=C1 GXYUTKVRTNINRK-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- YUDPDPSBLSRFNW-UHFFFAOYSA-N 1-phenoxy-2-phenylsulfanylbenzene Chemical compound C=1C=CC=C(SC=2C=CC=CC=2)C=1OC1=CC=CC=C1 YUDPDPSBLSRFNW-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- FOXSXNJTWXVMEA-UHFFFAOYSA-N 1,3-bis(phenylsulfanyl)benzene Chemical compound C=1C=CC(SC=2C=CC=CC=2)=CC=1SC1=CC=CC=C1 FOXSXNJTWXVMEA-UHFFFAOYSA-N 0.000 description 1
- WGBYOWIYAKVOLO-UHFFFAOYSA-N 1,4-bis(phenylsulfanyl)benzene Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 WGBYOWIYAKVOLO-UHFFFAOYSA-N 0.000 description 1
- BJPQXKZKPJTGPR-UHFFFAOYSA-N 1-chloro-3-[3-[3-(3-chlorophenoxy)phenyl]sulfanylphenoxy]benzene Chemical compound ClC=1C=C(OC=2C=C(C=CC2)SC2=CC(=CC=C2)OC2=CC(=CC=C2)Cl)C=CC1 BJPQXKZKPJTGPR-UHFFFAOYSA-N 0.000 description 1
- WUMVPPBLKRXNOS-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenyl)sulfanylbenzene Chemical compound C=1C=CC(SC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 WUMVPPBLKRXNOS-UHFFFAOYSA-N 0.000 description 1
- DWNVROMUKKAWBF-UHFFFAOYSA-N 1-phenylsulfanyl-2-(2-phenylsulfanylphenyl)sulfanylbenzene Chemical compound C=1C=CC=C(SC=2C(=CC=CC=2)SC=2C=CC=CC=2)C=1SC1=CC=CC=C1 DWNVROMUKKAWBF-UHFFFAOYSA-N 0.000 description 1
- NLFCHUPXKBJHEL-UHFFFAOYSA-N 1-phenylsulfanyl-2-(3-phenylsulfanylphenyl)sulfanylbenzene Chemical compound C=1C=CC(SC=2C(=CC=CC=2)SC=2C=CC=CC=2)=CC=1SC1=CC=CC=C1 NLFCHUPXKBJHEL-UHFFFAOYSA-N 0.000 description 1
- ZHMUOEOLSNHBRN-UHFFFAOYSA-N 2,4,6-tris(3-methylphenyl)-1,3,5,2,4,6-trioxatriborinane Chemical compound CC1=CC=CC(B2OB(OB(O2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 ZHMUOEOLSNHBRN-UHFFFAOYSA-N 0.000 description 1
- SQKUBUQVFDXGDI-UHFFFAOYSA-N 2,4,6-tris(4-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane Chemical compound C1=CC(OC)=CC=C1B1OB(C=2C=CC(OC)=CC=2)OB(C=2C=CC(OC)=CC=2)O1 SQKUBUQVFDXGDI-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920004511 Dow Corning® 200 Fluid Polymers 0.000 description 1
- 239000005069 Extreme pressure additive Substances 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000006003 dichloroethyl group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GBHRVZIGDIUCJB-UHFFFAOYSA-N hydrogenphosphite Chemical compound OP([O-])[O-] GBHRVZIGDIUCJB-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- 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
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
-
- 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
- C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2219/089—Overbased salts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
- C10M2227/062—Cyclic esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/041—Siloxanes with specific structure containing aliphatic substituents
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- compositions comprising polyphenyl thioethers, polyphenyl ethers-thioethers or mixtures thereof and a triphenylboroxin exhibit improved corrosiveness toward copper and silver Without loss of oxidative stability. Such compositions are useful as functional fluids.
- compositions comprising polyphenyl thioethers, polyphenyl ethers-thioethers or mixtures thereof, containing from 3 to 8 aromatic groups and a corrosion inhibiting amount of a triphenylboroxin.
- the compositions of this invention are useful as functional fluids.
- Polyphenyl thioethers and polyphenyl ether-thioether combinations have found wide application as functional fluids due to their excellent thermal stability and lubricity. For example they have been found to be valuable as hydraulic fluids and as lubricants in motor operation, par ticularly in jet engines, and as heat transfer agents. Two of the most rigorous demands on fluids are made by jet aircraft hydraulic systems and jet engine lubrication systerns. For example, as the speed and altitude of operation of jet powered aircraft increases, lubrication problems also increase because of higher operating temperatures and higher bearing pressures resulting from the increased thrust needed to obtain higher speeds and altitudes. Thus, the service conditions encountered by functional fluids become increasingly severe, and therefore, the useful life of such fluids is shortened.
- any lubricant or hydraulic fluid can be adjudged on the basis of many criteria such as the extent of viscosity increase, the extent of corrosion to metal surfaces in contact with the lubricant and the extent of engine deposits.
- Those skilled in the art have found various ways to improve lubricants and to thus retard or prevent the elfects which shorten the useful life of a lubricant.
- small amounts of other materials, or additives can be added to lubricants in order to affect one or more of the properties of the base lubricant.
- an object of this invention is to extend the useful life of polyphenyl thioethers, polyphenyl etherthioethers or mixtures thereof by reducing their corrosivity toward certain metals without adversely affecting oxidative stability of the ethers.
- the above and other object of this invention are carried out by admixing polyphenyl thioethers, polyphenyl ether-thioethers or mixtures thereof with a corrosion inhibiting amount of a triphenylboroxin.
- the ether-boron compositions of this invention exhibit reduced corrosiveness toward metals without an adverse effect on oxidative stability of the base ether and thus have an extended service life even under the severe conditions encountered in jet engines and other devices operating at temperatures of the order of 600 F.
- the compositions exhibit markedly reduced corrosion toward copper and silver.
- compositions of this invention comprise a major amount of ether base fluid of the formula wherein R is phenyl, alkyl-substituted phenyl wherein the alkyl is of not more than 4 carbon atoms, alkoxy-substituted phenyl wherein the alkoxy is of not more than 4 carbon atoms or halogenated phenyl wherein the halogen is bromine, fluorine of chlorine, R is phenylene, alkyl or alkoxy-substituted phenylene wherein the alkyl contains no more than 4 carbon atoms or halogenated phenylene wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and a is an integer having a valuel of 1 to 6 and a corrosion inhibiting amount of at least one triphenylboroxin of the formula R, 0 R, R1... a
- R is alkyl of not more than 4 carbon atoms, alkoxy of not more than 4 carbon atoms, halogen (Cl, Br and F) haloallryl of not more than 4 carbon atoms and 3 halogen atoms (Cl, Br and F) haloalkoxy of not more than 4 carbon atoms and 3 halogen atoms (Cl, Br and F), phenoxy, phenylmercapto or N0
- R is halogen (Cl, Br and F) or alkyl of not more than 4 carbon atoms, 71 is an integer of 0 to 3 and m' is an integer of 0 to 2.
- R in the above formula include halogen (Cl, Br and F), N0 phenoxy, thiophenoxy, alkyl such as methyl, ethyl, propyl, .isopropyl, n-butyl, secbutyl and t-butyl, alkoxy such as methoxy, ethoxy, butoxy, haloalkyl such as chloromethyl, bromomethyl, chloroethyl, bromoethyl, trichloromethyl, tribrornomethyl, trifiuoroethyl, dichloroethyl, chloro-n-propyl, bromo-n-propyl, bromo-n-butyl, brorno-tert-butyl, 1,3,3-trichlorobutyl and 1,3,3 tribromobutyl and haloalkoxy such as chloromethoxy, l,2-dichlorobutoxy and fiuoropropoxy.
- boron compounds of the above formula include triphenylb oroxin tri B-methylphenyl) boroxin tri (4-n-butylpheny1) boroxin tri (2,4-dimethylphenyl boroxin tri (4-methoxyphenyl boroxin tri (4-chloromethylphenyl boroxin tri (3-fiuoromethylphenyl) boroxin tri (4-trifluoromethylphenyl) boroxin tri 4-chlorophenyl boroxin tri (2,4-dichlorophenyl) boroxin tri S-fluorophenyl boroxin tri 4-phenoxyphenyl boroxin tri (4-nitrophenyl boroxin tri 4-ph enylmercaptophenyl) boroxin tri(2-fluoro-4-methylpheny1)boroxin tri 2-methyl-4-chlorophenyl boroxin tri (2-chloro-4-phenoxyphenyl) boroxin The amount of trip
- the polyphenyl thioethers employed in the composition of this invention have from 3 to 8 benzene rings and from 1 to 7 sulfur atoms with the sulfur atoms joining the benzene rings in chains as ether linkages.
- polyphenyl thioether as used herein means a compound or physical mixture of compounds wherein all of the Ys in the above formula are sulfur.
- polyphenylether-thioether as used herein means compounds or physical mixtures of compounds wherein at least one but not all of the Ys in the above formula is sulfur.
- compositions of this invention contain a major amount of the polyphenyl thioether or polyphenyl etherthioether base stock, i.e., at least 50% by Weight of the total composition comprises an ether. It is preferred that at least 60% by weight of the composition be an ether base stock and even more preferred that at least 85% by weight of the total composition comprise an ether.
- Illustrations of the alkyl-substituents present in the phenyl and phenylene groups of the ethers are for example, methyl, ethyl, propyl, butyl and the like. Illustrations of the alkoxy-substituents are, for example, methoxy, ethoxy, propoxy, butoxy and their isomers.
- compositions of this invention can also contain from 0.01 to 10% by weight of the total composition of a dialkyl hydrogen phosphite extreme pressure additive.
- the dialkyl hydrogen phosphites useful are those wherein the alkyl groups contain from 1 to 12 carbon atoms.
- the alkyl groups are for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, hexyl, decyl, isodecyl, dodecyl and the like.
- polyphenyl thioethers which can be employed as base stocks for the compositions of this invention are the bis(phenylmercapto)benzenes.
- bis(phenylmercapto)benzenes for example rn-bis (phenylmercapto) benzene o-bis (phenylmercapto benzene p-bis (phenylmercapto) benzene bis m-phenylmercaptophenyl) sulfide bis (o-phenylmercaptophenyl) sulfide bis (p-phenylmerc aptophenyl) sulfide (m-phenylmercaptophenyl) (o-phenylmercaptophenyl) sulfide p-phenylmercapto-m'-phenylmercapto diphenyl sulfide o-bis (o-phenylmercaptophenylmercapto benzene p-bis (p-pheny
- triphenylboroxins useful in the compositions of this invention are well known to the art and can be prepared by dehydration of phenylboric acids as set forth in The Organic Chemistry of Boron, Academic Press, New York, 68 (1961). Phenylboric acids can be prepared by the procedures set forth in articles by R. M. Washburn et al., Advances in Chemistry Series, 32, 20-8 (1961) and W. Gerrard, The Organic Chemistry of Boron, Academic Press, New York, 59 (1961) or US. Pat. No. 3,092,652.
- Polyphenyl thioether-polyphenyl ether-thioether lubricant compositions are prepared by combining 0.10 gm. of various triphenylboroxins with 100 grams of a thioether of the following composition:
- the useful life of a functional fluid can be determined on the basis of many criteria such as the extent of viscosity increase (oxidative stability) and corrosiveness toward metals under the conditions of use.
- the major bench scale method used for evaluating the oxidative stability of a functional fluid is the procedure given in Federal Test Specification 791, Method 5308 according to which the lubricant composition is heated at a specified temperature in the presence of certain metals and oxygen and the viscosity increase of the lubricant is determined.
- compositions of this example were tested according to the procedure of Federal Test Specification 791, Method 5308, i.e., 500 F. for 48 hours with five liters/ hour of air in the presence of steel, copper, silver, titanium, magnesium alloy and aluminum alloy. Information with respect to corrosiveness of the compositions to metals was also obtained. However, only the results upon copper and silver are reported since all the compositions tested has essentially no effect on the other metals employed. Viscosity measurements were made according to ASTM Method D-445-5 3T using a Cannon-Fenske modified Ostwald viscosimeter. The control base fluid ether and the compositions of this invention exhibited substantially the same viscosity increase.
- compositions of this invention exhibit markedly reduced corrosivity toward metals with no loss of oxidative stability and therefore have an extended useful life.
- compositions of the invention may also contain other additives, such as oxidation inhibitors, rust and corrosion inhibitors, antifoaming agents, detergents, viscosity index improvers such as polymeric materials for example, polyacrylate alkyl esters, polymethacrylate alkyl esters, polyoxyalkylene compounds, polyurethanes and the like.
- additives are usually employed in amounts as low as 10 parts per million for antifoaming agent to as much as 15 parts by Weight of the total compositions for viscosity index improvers.
- Composition consisting essentially of a major amount of a base fluid selected from the group consisting of polyphenyl thioethers, polyphenyl ether-thioethers, and mixtures thereof having the formula wherein R is phenyl, alkyl-substituted phenyl wherein the alkyl is of not more than 4 carbon atoms, alkoxy-substituted phenyl wherein the alkoxy is of not more than 4 carbon atoms or halogenated phenyl wherein the halogen is bromine, fluorine or chlorine, R is phenylene, alkyl or alkoxy-substituted phenylene wherein the alkyl contains no more than 4 carbon atoms or halogenated phenylene wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and a is an integer having a value of 1 to 6 and a corrosion inhibiting amount of at least one
- R is alkyl of not more than 4 carbon atoms, alkoxy of not more than 4 carbon atoms, halogen selected from Cl, Br and F, haloalkyl of not more than 4 carbon atoms and 3 halogen atoms selected from Cl, Br and F, haloalkoxy of not more than 4 carbon atoms and 3 halogen atoms selected from Cl, Br and F, phenoxy, phenylmercapto or N0
- R is halogen selected from Cl, Br and F or alkyl of not more than 4 carbon atoms, n is an integer of 0 to 3 and m is an integer of 0 to 2.
- composition of claim 1 wherein the boroxin is triphenylboroxin.
- Composition of claim 1 wherein the boroxin is tri- (B-trifluoromethylphenyl)boroxin.
- composition of claim 1 wherein the bOrOXin is tri- (3-fluoropheny1)boroxin.
- composition of claim 1 wherein the boroxin is tri- (3-methylphenyl)boroxin.
- composition of claim 1 wherein the boroxin is tri- (4-methoxyphenyl)boroxin.
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Abstract
COMPOSITIONS COMPRISING POLYPHENYL THIOETHERS, POLYPHENYL ETHERS-THIOETHERS OR MIXTURES THEREOF AND A TRIPHENYLBOROXIN EXHIBIT IMPROVED CORROSIVENESS TOWARD COPPER AND SILVER WITHOUT LOSS OF OXIDATIVE STABILITY. SUCH COMPOSITIONS ARE USEFUL AS FUNCTIONAL FLUIDS.
Description
United States Patent Olhce 3,751,367 Patented Aug. 7, 1973 ABSTRACT BF THE ENCLOSURE Compositions comprising polyphenyl thioethers, polyphenyl ethers-thioethers or mixtures thereof and a triphenylboroxin exhibit improved corrosiveness toward copper and silver Without loss of oxidative stability. Such compositions are useful as functional fluids.
This invention relates to compositions comprising polyphenyl thioethers, polyphenyl ethers-thioethers or mixtures thereof, containing from 3 to 8 aromatic groups and a corrosion inhibiting amount of a triphenylboroxin. The compositions of this invention are useful as functional fluids.
Polyphenyl thioethers and polyphenyl ether-thioether combinations have found wide application as functional fluids due to their excellent thermal stability and lubricity. For example they have been found to be valuable as hydraulic fluids and as lubricants in motor operation, par ticularly in jet engines, and as heat transfer agents. Two of the most rigorous demands on fluids are made by jet aircraft hydraulic systems and jet engine lubrication systerns. For example, as the speed and altitude of operation of jet powered aircraft increases, lubrication problems also increase because of higher operating temperatures and higher bearing pressures resulting from the increased thrust needed to obtain higher speeds and altitudes. Thus, the service conditions encountered by functional fluids become increasingly severe, and therefore, the useful life of such fluids is shortened.
The useful life of any lubricant or hydraulic fluid can be adjudged on the basis of many criteria such as the extent of viscosity increase, the extent of corrosion to metal surfaces in contact with the lubricant and the extent of engine deposits. Those skilled in the art have found various ways to improve lubricants and to thus retard or prevent the elfects which shorten the useful life of a lubricant. Thus, for example, small amounts of other materials, or additives, can be added to lubricants in order to affect one or more of the properties of the base lubricant. However, it is difiicult, especially as operating temperatures are increased, to find additives which will still perform the function for which they are added and yet not inject other problems.
Therefore, an object of this invention is to extend the useful life of polyphenyl thioethers, polyphenyl etherthioethers or mixtures thereof by reducing their corrosivity toward certain metals without adversely affecting oxidative stability of the ethers.
These and other objects will become evident upon consideration of the following specification and examples.
The above and other object of this invention are carried out by admixing polyphenyl thioethers, polyphenyl ether-thioethers or mixtures thereof with a corrosion inhibiting amount of a triphenylboroxin. The ether-boron compositions of this invention exhibit reduced corrosiveness toward metals without an adverse effect on oxidative stability of the base ether and thus have an extended service life even under the severe conditions encountered in jet engines and other devices operating at temperatures of the order of 600 F. The compositions exhibit markedly reduced corrosion toward copper and silver.
The improved compositions of this invention comprise a major amount of ether base fluid of the formula wherein R is phenyl, alkyl-substituted phenyl wherein the alkyl is of not more than 4 carbon atoms, alkoxy-substituted phenyl wherein the alkoxy is of not more than 4 carbon atoms or halogenated phenyl wherein the halogen is bromine, fluorine of chlorine, R is phenylene, alkyl or alkoxy-substituted phenylene wherein the alkyl contains no more than 4 carbon atoms or halogenated phenylene wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and a is an integer having a valuel of 1 to 6 and a corrosion inhibiting amount of at least one triphenylboroxin of the formula R, 0 R, R1... a
wherein R is alkyl of not more than 4 carbon atoms, alkoxy of not more than 4 carbon atoms, halogen (Cl, Br and F) haloallryl of not more than 4 carbon atoms and 3 halogen atoms (Cl, Br and F) haloalkoxy of not more than 4 carbon atoms and 3 halogen atoms (Cl, Br and F), phenoxy, phenylmercapto or N0 R is halogen (Cl, Br and F) or alkyl of not more than 4 carbon atoms, 71 is an integer of 0 to 3 and m' is an integer of 0 to 2.
Representative groups for R in the above formula include halogen (Cl, Br and F), N0 phenoxy, thiophenoxy, alkyl such as methyl, ethyl, propyl, .isopropyl, n-butyl, secbutyl and t-butyl, alkoxy such as methoxy, ethoxy, butoxy, haloalkyl such as chloromethyl, bromomethyl, chloroethyl, bromoethyl, trichloromethyl, tribrornomethyl, trifiuoroethyl, dichloroethyl, chloro-n-propyl, bromo-n-propyl, bromo-n-butyl, brorno-tert-butyl, 1,3,3-trichlorobutyl and 1,3,3 tribromobutyl and haloalkoxy such as chloromethoxy, l,2-dichlorobutoxy and fiuoropropoxy. Representative groups for R include the halogen and alkyl listed above for R.
Representative boron compounds of the above formula include triphenylb oroxin tri B-methylphenyl) boroxin tri (4-n-butylpheny1) boroxin tri (2,4-dimethylphenyl boroxin tri (4-methoxyphenyl boroxin tri (4-chloromethylphenyl boroxin tri (3-fiuoromethylphenyl) boroxin tri (4-trifluoromethylphenyl) boroxin tri 4-chlorophenyl boroxin tri (2,4-dichlorophenyl) boroxin tri S-fluorophenyl boroxin tri 4-phenoxyphenyl boroxin tri (4-nitrophenyl boroxin tri 4-ph enylmercaptophenyl) boroxin tri(2-fluoro-4-methylpheny1)boroxin tri 2-methyl-4-chlorophenyl boroxin tri (2-chloro-4-phenoxyphenyl) boroxin The amount of triphenylboroxin employed in the compositions of this invention can range from about 0.01 to about 1.5% by weight. It is preferred to employ the acids in the compositions of this invention in amounts of from 3 about 0.05 to about 01.5% by weight based upon the total composition.
The polyphenyl thioethers employed in the composition of this invention have from 3 to 8 benzene rings and from 1 to 7 sulfur atoms with the sulfur atoms joining the benzene rings in chains as ether linkages.
The term polyphenyl thioether as used herein means a compound or physical mixture of compounds wherein all of the Ys in the above formula are sulfur. The term "polyphenylether-thioether as used herein means compounds or physical mixtures of compounds wherein at least one but not all of the Ys in the above formula is sulfur.
The compositions of this invention contain a major amount of the polyphenyl thioether or polyphenyl etherthioether base stock, i.e., at least 50% by Weight of the total composition comprises an ether. It is preferred that at least 60% by weight of the composition be an ether base stock and even more preferred that at least 85% by weight of the total composition comprise an ether.
Illustrations of the alkyl-substituents present in the phenyl and phenylene groups of the ethers are for example, methyl, ethyl, propyl, butyl and the like. Illustrations of the alkoxy-substituents are, for example, methoxy, ethoxy, propoxy, butoxy and their isomers.
The compositions of this invention can also contain from 0.01 to 10% by weight of the total composition of a dialkyl hydrogen phosphite extreme pressure additive. The dialkyl hydrogen phosphites useful are those wherein the alkyl groups contain from 1 to 12 carbon atoms. The alkyl groups are for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, hexyl, decyl, isodecyl, dodecyl and the like.
Illustrative of the polyphenyl thioethers which can be employed as base stocks for the compositions of this invention are the bis(phenylmercapto)benzenes. For example rn-bis (phenylmercapto) benzene o-bis (phenylmercapto benzene p-bis (phenylmercapto) benzene bis m-phenylmercaptophenyl) sulfide bis (o-phenylmercaptophenyl) sulfide bis (p-phenylmerc aptophenyl) sulfide (m-phenylmercaptophenyl) (o-phenylmercaptophenyl) sulfide p-phenylmercapto-m'-phenylmercapto diphenyl sulfide o-bis (o-phenylmercaptophenylmercapto benzene p-bis (p-phenylmercaptophenylmercapto benzene p-bis o-phenylmercaptophenylmercapto benzene p-bis (m-phenylmercaptophenylmercapto benzene m-bis (p-phenylmercaptophenylmercapto benzene o-bis (p-phenylmercaptophenylmercapto) benzene and the like and mixtures thereof.
Illustrative of the mixed polyphenyl ether-thioether compounds which can be employed as base stocks in the compositions of this invention are for example,
o-phenylmercapto-m-phenoxy benzene p-phenylmercapto-o-pheuoxy benzene m-phenoxy-p-phenylmercapto benzene o-phenylmercapto-p phenoxydiphenyl sulfide o-phenylmercapto-m-phenoxydiphenyl sulfide o-phenoxy-m'-phenylmercaptodiphenyl sulfide m-phenoxy-p'-phenylmercaptodiphenyl sulfide o-phenoxy-p'-phenylmercaptodiphenyl sulfide p-phenoxy-p-phenylmercaptodiphenyl sulfide o-phenoxy-o'-phenylmercaptodiphenyl sulfide o,o'-bis(phenylmercapto)diphenyl ether o-phenylmercapto-m-phenylmercaptodiphenyl ether ophenylmercapto-p-phenylmercaptodiphenyl ether m-(m-phenylmercaptophenylmercapto) (m-phenoxyphenylmercapto)benzene [m- (m-phenylmerc aptophenylmercapto phenyl] [mm-phenoxyphenylmerc apto phenyl] sulfide 3- (m-phenylmercaptophenylmercapto -3- (mmercaptophenoxy) diphenyl sulfide 3,3 -bis (m-phenylmercaptophenylmercapto diphenyl ether 3 (m-phenylmercaptophenylmercapto) -3 (m-phenoxyphenoxy diphenyl sulfide 4- (m-phenylmercaptophenylmercapto-4- (m-phenylmercaptophenoxy) diphenyl ether 3- (m-phenylmercaptophenylmercapto -3- (m-phenoxyphenylmercapto diphenyl ether 4,4'-bis (m-phenylmercaptophenoxy diphenyl sulfide 4,4'-bis (m-phenoxyphenylmercapto) diphenyl sulfide 3- (m-phenoxyphenylmercapto -3'- (m-phenylmercaptophenoxy diphenyl sulfide 3 3 '-bis (m-phenylmercaptophenoxy diphenyl ether 4- m-phenylmercaptophenylmercapto) -4'- (m-phenoxyphenoxy) diphenyl ether 3 (p phenylmercaptophenoxy) -3'- (p-phenoxyphenoxy) diphenyl sulfide 3- (m-phenylmercaptophenoxy -3 (m-phenoxyphenylmercapto diphenyl ether 3 ,3 -bis (m-phenoxyphenylmercapto diphenyl ether and 3- m-phenoxyphenylmercapto -3'- (m-phenoxyphenoxy) diphenyl sulfide In addition to the foregoing compounds, the phenyl and phenylene of such compounds can contain substituents, such as alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halogen such as chlorine, bromine and fluorine. Examples of such compounds are as follows:
4,4'-bis(m-tolylmercapto diphenyl ether 3 ,3 -bis (m-tolylmercapto diphenyl ether 2,4-bis (m-tolylmercapto diphenyl ether 3,4-bis (m-tolylmercapto diphenyl ether 3,3 -bis (p-tolylmercapto diphenyl ether 3, 3 '-bis xylylmerc apto diphenyl ether 4,4'-bis (xylylmercapto) diphenyl ether 3,4'-bis(xylylmercapto diphenyl ether 3 ,4'-bis m-isopropylphenylmercapto diphenyl ether 3,3 '-bis(m-isopropylphenylmercapto diphenyl ether 2,4'-bis (m-isopropylphenylmercapto diphenyl ether 3 ,4'-bis (p-tert-butylphenylmercapto) diphenyl ether 4,4'-bis (p-tert-butylphenylmercapto) diphenyl ether 3 ,3 '-bis (p-tert-butylphenylmercapto diphenyl ether 3,3 '-bis (2,4-di-tert-butylphenylmercapto) diphenyl ether 3,3 '-bis 3-chlorophenylmercapto) diphenyl ether 4,4-bis 3-chlorophenylmercapto diphenyl ether 3,3 '-bis (m-trifluoromethylphenylmercapto diphenyl ether 4,4'-bis (m-trifluoromethylphenylmercapto diphenyl ether 3,4'-bis (m-trifluoromethylphenylmercapto diphenyl ether 2,3 '-bis (m-trifiuoromethylphenylmercapto) diphenyl ether 3,3 '-bis (p-trifluoromethylphenylmercapto diphenyl ether 3,3 '-bis (o-trifiuoromethylphenylmercapto diphenyl ether 3 ,3 -bis (m-methoxyphenylmercapto diphenyl ether 3,4'-bis (m-isopropoxyphenylmercapto diphenyl ether 3,4-bis(m-perfiuorobutylphenylmercapto) diphenyl ether 2- (m-tolyloxy) -2'-phenylmercaptodiphenyl sulfide 2- (p-tolyloxy 3-phenylmercaptodiphenyl sulfide 2- (o-tolyloxy) -4'-phenylmercaptodiphenyl sulfide 3- (m-tolyloxy) -3'-phenylmercaptodiphenyl sulfide 3- (m-tolyloxy) -4-'-phenylmercaptodiphenyl sulfide 4- (m-tolyloxy) -4'-phenylmercaptodiphenyl sulfide 3-xylyloxy-4'-phenylmercaptodiphenyl sulfide 3-xyly1oxy-3'-phenylmercaptodiphenyl sulfide 3-phenoxy-3'- (m-tolylmercapto) diphenyl sulfide 3-phenoxy-4'- (m-tolylmercapto) diphenyl sulfide 2-phenoxy-3 (p-tolylmercapto diphenyl sulfide 3-phenoxy-4'- (m-isopropylphenylmercapto diphenyl sulfide 3 -phenoXy-3 (m-isopropylphenylmercapto) diphenyl sulfide 3-m-toloxy-3'- (m-isopropylphenylmercapto diphenyl sulfide 4- (rn-trifluoromethylphenoxy) -4'-phenylmercaptodiphenyl sulfide 3- (m-trifiuoromethylphenoxy -4-phenylmercaptodiphenyl sulfide 2- (m-trifiuoromethylphen oxy) -3 '-phenylmercaptodiphenyl sulfide 3 (m-trifluoromethylphenoxy) -3 -phe nylmerc aptodiphenyl sulfide 3-(p-chlorophenoxy)-3'-plienylmercaptodiphenyl sulfide 3- (m-bromophenoxy) -3 '-phenylmercaptodiphenyl sulfide bis [m- (m-chlorophenoxy) phenyl] sulfide m-bis [3- (p-rnethylphenylmercapto phenoxy] benzene m-bis [3 (m-trifiuoromethylphenoxy phenylmercapto] benzene m-bis [3- (m-bromophenoxy) phenylmercapto] benzene 3,3'-bis [m- (p-methylphenylmercapto phenoxy] diphenyl sulfide 3,4-bis [m- (p-methylphenylmercapto phenoxy] diphenyl sulfide 3- (p-xenyloxy) -3'-phenylmercapto diphenyl sulfide,
and the like and mixtures thereof. It is also contemplated within the scope of this invention to employ mixtures of polyphenyl ether-thioethers as base stocks.
The triphenylboroxins useful in the compositions of this invention are well known to the art and can be prepared by dehydration of phenylboric acids as set forth in The Organic Chemistry of Boron, Academic Press, New York, 68 (1961). Phenylboric acids can be prepared by the procedures set forth in articles by R. M. Washburn et al., Advances in Chemistry Series, 32, 20-8 (1961) and W. Gerrard, The Organic Chemistry of Boron, Academic Press, New York, 59 (1961) or US. Pat. No. 3,092,652.
The following examples serve to further illustrate the invention. All parts are parts by Weight unless otherwise expressly set forth.
EXAMPLES Polyphenyl thioether-polyphenyl ether-thioether lubricant compositions are prepared by combining 0.10 gm. of various triphenylboroxins with 100 grams of a thioether of the following composition:
Percent by wt.
M eta-bis (phenylmercapto) benzene S Bis (m-phenoxyphenyl) sulfide 12.5 (m-Phenoxyphenyl) (m phenylmercaptophenyl) sulfide 23.5 Bis(rn-phenylmercaptophenyl)sulfide 12.65 3 ring and 5 ring thioethers 1.35
and containing parts per million of a dimethyl silicone antifoam agent (Dow-Corning-200, 350 cs. fluid). After stirring at 40 C. to dissolve the anhydride, the mixture is cooled to room temperature and filtered. Lubricant compositions without boron additives were used as control.
The useful life of a functional fluid can be determined on the basis of many criteria such as the extent of viscosity increase (oxidative stability) and corrosiveness toward metals under the conditions of use. The major bench scale method used for evaluating the oxidative stability of a functional fluid is the procedure given in Federal Test Specification 791, Method 5308 according to which the lubricant composition is heated at a specified temperature in the presence of certain metals and oxygen and the viscosity increase of the lubricant is determined.
The compositions of this example were tested according to the procedure of Federal Test Specification 791, Method 5308, i.e., 500 F. for 48 hours with five liters/ hour of air in the presence of steel, copper, silver, titanium, magnesium alloy and aluminum alloy. Information with respect to corrosiveness of the compositions to metals was also obtained. However, only the results upon copper and silver are reported since all the compositions tested has essentially no effect on the other metals employed. Viscosity measurements were made according to ASTM Method D-445-5 3T using a Cannon-Fenske modified Ostwald viscosimeter. The control base fluid ether and the compositions of this invention exhibited substantially the same viscosity increase. The corrosiveness to metals was determined by weighing metal specimens of known size before and after the test. Results and further details are given in the table below From the above it is clearly evident that the compositions of this invention exhibit markedly reduced corrosivity toward metals with no loss of oxidative stability and therefore have an extended useful life.
It will be appreciated that the compositions of the invention may also contain other additives, such as oxidation inhibitors, rust and corrosion inhibitors, antifoaming agents, detergents, viscosity index improvers such as polymeric materials for example, polyacrylate alkyl esters, polymethacrylate alkyl esters, polyoxyalkylene compounds, polyurethanes and the like. Such additives are usually employed in amounts as low as 10 parts per million for antifoaming agent to as much as 15 parts by Weight of the total compositions for viscosity index improvers.
While the invention has been described with respect to specific examples and embodiments, it is to be understood that the invention is not limited thereto and that it can be variously practiced within the scope of the following claims.
The embodiments of this invention in which a particular property or privilege is claimed are defined as follows:
1. Composition consisting essentially of a major amount of a base fluid selected from the group consisting of polyphenyl thioethers, polyphenyl ether-thioethers, and mixtures thereof having the formula wherein R is phenyl, alkyl-substituted phenyl wherein the alkyl is of not more than 4 carbon atoms, alkoxy-substituted phenyl wherein the alkoxy is of not more than 4 carbon atoms or halogenated phenyl wherein the halogen is bromine, fluorine or chlorine, R is phenylene, alkyl or alkoxy-substituted phenylene wherein the alkyl contains no more than 4 carbon atoms or halogenated phenylene wherein the halogen is fluorine, bromine or chlorine, and Y is selected from oxygen and sulfur but at least one of the Ys is sulfur and a is an integer having a value of 1 to 6 and a corrosion inhibiting amount of at least one triphenylboroxin of the formula Rh 0 R R (5 l) R m \B/ Irwin,
wherein R is alkyl of not more than 4 carbon atoms, alkoxy of not more than 4 carbon atoms, halogen selected from Cl, Br and F, haloalkyl of not more than 4 carbon atoms and 3 halogen atoms selected from Cl, Br and F, haloalkoxy of not more than 4 carbon atoms and 3 halogen atoms selected from Cl, Br and F, phenoxy, phenylmercapto or N0 R is halogen selected from Cl, Br and F or alkyl of not more than 4 carbon atoms, n is an integer of 0 to 3 and m is an integer of 0 to 2.
2. Composition of claim 1 wherein the boroxin is present in an amount from about 0.01% to about 1.5% by weight based on the total weight of the composition.
3. Composition of claim 1 wherein the boroxin is triphenylboroxin.
4. Composition of claim 1 wherein the boroxin is tri- (B-trifluoromethylphenyl)boroxin.
5. Composition of claim 1 wherein the bOrOXin is tri- (3-fluoropheny1)boroxin.
6. Composition of claim 1 wherein the boroxin is tri- (3-methylphenyl)boroxin.
7. Composition of claim 1 wherein the boroxin is tri- (4-methoxyphenyl)boroxin.
8. Composition of claim 1 wherein n is zero.
9. Composition of claim 1 wehrein m is zero.
10. Composition of claim 1 wherein R is alkyl and m is zero.
11. Composition of claim 1 wherein R is halogen and n is zero.fl
12. Composition of claim 1 wherein R is haloalkyl and m is zero.
13. Composition of claim 1 wherein R is phenyl and R is phenylene.
14. Composition of claim 1 wherein R is phenyl.
8 15. Composition of claim 1 wherein R is haloalkyl and R is alkyl.
References Cited UNITED STATES PATENTS 2,312,208 2/1943 Clayton et al. 252-75 3,108,966 10/1963 Dadura et al. 25246.3 3,518,287 6/1970 Rinse 252389 X 3,518,314 6/1970 Gieseking 252-78 X 3,538,166 11/1970 Campbell et al. 252-78 X 3,078,305 2/ 196-3 Dobratz 260-545 3,125,528 3/1964 Kay et al 252-49.6 3,321,529 5/1967 Campbell 252--78 X 3,450,770 6/ 1969 Campbell et a1. 252--78 X 3,455,846 7/1969 Bannister 252-78 X OTHER REFERENCES Chemical Abstracts, vol. 59, 1679 (f) (1963).
LEON D. ROSDOL, Primary Examiner H. A. PITLICK, Assistant Examiner US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16746371A | 1971-07-29 | 1971-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3751367A true US3751367A (en) | 1973-08-07 |
Family
ID=22607464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00167463A Expired - Lifetime US3751367A (en) | 1971-07-29 | 1971-07-29 | Compositions comprising boron compounds and polyphenyl thioethers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3751367A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853776A (en) * | 1972-09-29 | 1974-12-10 | Monsanto Co | Low pour point fluids and blends containing same |
| US5885943A (en) * | 1997-12-18 | 1999-03-23 | Exxon Chemical Patents Inc. | Sulfur boron antiwear agents for lubricating compositions |
| US6191080B1 (en) * | 1995-06-16 | 2001-02-20 | Tonen Corporation | Heat resistant lubricating oil composition |
-
1971
- 1971-07-29 US US00167463A patent/US3751367A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853776A (en) * | 1972-09-29 | 1974-12-10 | Monsanto Co | Low pour point fluids and blends containing same |
| US6191080B1 (en) * | 1995-06-16 | 2001-02-20 | Tonen Corporation | Heat resistant lubricating oil composition |
| US6586376B1 (en) | 1995-06-16 | 2003-07-01 | Exxonmobil Research And Engineering Company | Heat resistant lubricating oil composition |
| US5885943A (en) * | 1997-12-18 | 1999-03-23 | Exxon Chemical Patents Inc. | Sulfur boron antiwear agents for lubricating compositions |
| US6028210A (en) * | 1997-12-18 | 2000-02-22 | Exxon Chemical Patents, Inc. | Process for making sulfur boron antiwear agents for lubricating compositions |
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