US3226323A - Lubricant composition containing a haloalkanoic compound - Google Patents
Lubricant composition containing a haloalkanoic compound Download PDFInfo
- Publication number
- US3226323A US3226323A US277024A US27702463A US3226323A US 3226323 A US3226323 A US 3226323A US 277024 A US277024 A US 277024A US 27702463 A US27702463 A US 27702463A US 3226323 A US3226323 A US 3226323A
- Authority
- US
- United States
- Prior art keywords
- bis
- ether
- polyphenyl
- haloalkanoic
- acid
- 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 43
- 239000000314 lubricant Substances 0.000 title claims description 24
- 150000001875 compounds Chemical class 0.000 title claims description 19
- 229920013636 polyphenyl ether polymer Polymers 0.000 claims description 50
- 239000012530 fluid Substances 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 17
- 229910001385 heavy metal Inorganic materials 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000002585 base Substances 0.000 description 31
- 239000000654 additive Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- -1 t-butylphenyl Chemical group 0.000 description 18
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229960004319 trichloroacetic acid Drugs 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000005461 lubrication Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZFQAUDJGELQDAN-UHFFFAOYSA-L zinc;2,2,2-trichloroacetate Chemical compound [Zn+2].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl ZFQAUDJGELQDAN-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 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
- 231100000241 scar Toxicity 0.000 description 3
- 229940066528 trichloroacetate Drugs 0.000 description 3
- SDUQWTDEBSFSIV-UHFFFAOYSA-N 1,2-bis(2-phenoxyphenoxy)benzene Chemical class C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 SDUQWTDEBSFSIV-UHFFFAOYSA-N 0.000 description 2
- KOKDSALTQSQPDH-UHFFFAOYSA-N 1,3-bis(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=C(OC=4C=CC=CC=4)C=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 KOKDSALTQSQPDH-UHFFFAOYSA-N 0.000 description 2
- KYSKNYFGWVBAOD-UHFFFAOYSA-N 1,3-bis(4-phenoxyphenoxy)benzene Chemical compound C=1C=C(OC=2C=C(OC=3C=CC(OC=4C=CC=CC=4)=CC=3)C=CC=2)C=CC=1OC1=CC=CC=C1 KYSKNYFGWVBAOD-UHFFFAOYSA-N 0.000 description 2
- UDANIBGCYQAQDP-UHFFFAOYSA-N 2,2-dichloro-2-fluoroacetic acid Chemical compound OC(=O)C(F)(Cl)Cl UDANIBGCYQAQDP-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WVOCXQKXUBYPNN-UHFFFAOYSA-N 1,4-diphenoxy-2-(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C(=CC=C(OC=3C=CC=CC=3)C=2)OC=2C=CC=CC=2)=CC=1OC1=CC=CC=C1 WVOCXQKXUBYPNN-UHFFFAOYSA-N 0.000 description 1
- CEUKNEYMDJIDAA-UHFFFAOYSA-N 1-(2,3-diphenoxyphenoxy)-2,3-diphenoxybenzene Chemical class C=1C=CC(OC=2C(=C(OC=3C=CC=CC=3)C=CC=2)OC=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 CEUKNEYMDJIDAA-UHFFFAOYSA-N 0.000 description 1
- XSUIICSNIGDRBH-UHFFFAOYSA-N 1-(2-phenoxyphenoxy)-2-(2-phenylphenoxy)benzene Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1 XSUIICSNIGDRBH-UHFFFAOYSA-N 0.000 description 1
- NDDDKTFZNYMIQO-UHFFFAOYSA-N 1-[2-(2,3-diphenoxyphenoxy)phenoxy]-2,3-diphenoxybenzene Chemical class C=1C=CC(OC=2C(=CC=CC=2)OC=2C(=C(OC=3C=CC=CC=3)C=CC=2)OC=2C=CC=CC=2)=C(OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 NDDDKTFZNYMIQO-UHFFFAOYSA-N 0.000 description 1
- CHSBGBACAWVJTL-UHFFFAOYSA-N 1-methyl-2,4-diphenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(C)=CC=C1OC1=CC=CC=C1 CHSBGBACAWVJTL-UHFFFAOYSA-N 0.000 description 1
- AQBWMQFSISCNGJ-UHFFFAOYSA-N 1-methyl-4-[4-[4-(4-methylphenoxy)phenoxy]phenoxy]benzene Chemical compound C1=CC(C)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(C)C=C1 AQBWMQFSISCNGJ-UHFFFAOYSA-N 0.000 description 1
- QKHCUKLDPPXGFA-UHFFFAOYSA-N 1-phenoxy-2-(2-phenoxyphenoxy)benzene Chemical compound C=1C=CC=C(OC=2C(=CC=CC=2)OC=2C=CC=CC=2)C=1OC1=CC=CC=C1 QKHCUKLDPPXGFA-UHFFFAOYSA-N 0.000 description 1
- MVCITNPWSJQCBC-UHFFFAOYSA-N 1-phenoxy-3-(3-phenoxyphenoxy)benzene Chemical compound C=1C=CC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=CC=1OC1=CC=CC=C1 MVCITNPWSJQCBC-UHFFFAOYSA-N 0.000 description 1
- BPFHJDPZBIEKSI-UHFFFAOYSA-N 1-phenoxy-4-[4-[4-(4-phenoxyphenoxy)phenoxy]phenoxy]benzene Chemical compound C=1C=C(OC=2C=CC(OC=3C=CC(OC=4C=CC(OC=5C=CC=CC=5)=CC=4)=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 BPFHJDPZBIEKSI-UHFFFAOYSA-N 0.000 description 1
- GUIIFQCDPWDDOU-UHFFFAOYSA-N 1-phenyl-2-[2-[2-(2-phenylphenoxy)phenoxy]phenoxy]benzene Chemical compound C1(=C(C=CC=C1)OC1=C(C=CC=C1)OC1=C(C=CC=C1)OC1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 GUIIFQCDPWDDOU-UHFFFAOYSA-N 0.000 description 1
- NTCQTDXDCNIKCB-UHFFFAOYSA-N 1-tert-butyl-4-[4-[4-(4-tert-butylphenoxy)phenoxy]phenoxy]benzene Chemical compound C1=CC(C(C)(C)C)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(C(C)(C)C)C=C1 NTCQTDXDCNIKCB-UHFFFAOYSA-N 0.000 description 1
- MTVIFDMVZHUZOV-UHFFFAOYSA-N 2,2,3,3,3-pentachloropropanoic acid Chemical compound OC(=O)C(Cl)(Cl)C(Cl)(Cl)Cl MTVIFDMVZHUZOV-UHFFFAOYSA-N 0.000 description 1
- MUAAJWUMDCFMTO-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptachlorobutanoic acid Chemical compound OC(=O)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)Cl MUAAJWUMDCFMTO-UHFFFAOYSA-N 0.000 description 1
- RYISNIJQCCRLKV-UHFFFAOYSA-N 2,3,3-trichloro-2,3-difluoropropanoic acid Chemical compound OC(=O)C(F)(Cl)C(F)(Cl)Cl RYISNIJQCCRLKV-UHFFFAOYSA-N 0.000 description 1
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- RHMYEOYYPYBQCN-UHFFFAOYSA-N 3,3,3-trichloropropanoic acid Chemical class OC(=O)CC(Cl)(Cl)Cl RHMYEOYYPYBQCN-UHFFFAOYSA-N 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical class [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010752 Ullmann ether synthesis reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 150000001621 bismuth Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- VYIIWGOEOXLBMO-UHFFFAOYSA-L cadmium(2+);2,2,2-trichloroacetate Chemical compound [Cd+2].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl VYIIWGOEOXLBMO-UHFFFAOYSA-L 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 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
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- ASAXSMNIHNHUDF-UHFFFAOYSA-L mercury(2+);2,2,2-trichloroacetate Chemical compound [Hg+2].[O-]C(=O)C(Cl)(Cl)Cl.[O-]C(=O)C(Cl)(Cl)Cl ASAXSMNIHNHUDF-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical class [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- MBEOPKCJKKUUND-UHFFFAOYSA-J tris[(2,2,2-trichloroacetyl)oxy]stannyl 2,2,2-trichloroacetate Chemical compound ClC(C(=O)[O-])(Cl)Cl.ClC(C(=O)[O-])(Cl)Cl.ClC(C(=O)[O-])(Cl)Cl.ClC(C(=O)[O-])(Cl)Cl.[Sn+4] MBEOPKCJKKUUND-UHFFFAOYSA-J 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
-
- 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
-
- 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
-
- 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
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/044—Acids; Salts or esters thereof
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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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- C—CHEMISTRY; METALLURGY
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- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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- C10N2010/04—Groups 2 or 12
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
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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
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- C10N2010/10—Groups 5 or 15
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/12—Groups 6 or 16
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- C—CHEMISTRY; METALLURGY
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- C10N2010/14—Group 7
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10N2010/16—Groups 8, 9, or 10
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- 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
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- 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
- C10N2030/32—Light or X-ray resistance
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- C—CHEMISTRY; METALLURGY
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- 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
- This invention relates to liquid fluids of high thermal stability, and more particularly, provides functional fluids comprising polyphenyl ethers and certain haloalkanoic compounds as additives therefor.
- Polyphenyl ethers have found wide application as functional fluids owing to their very good thermal stability, lubricity, and resistance to foam. For example, they have been found to be valuable as hydraulic fluids, as heatexchange media, as atomic reactor coolants, as diffusion pump fluids, as lubricants in motor operation generally, and particularly as jet engine lubricants.
- petroleum lubricants in addition to the petroleum base stock, generally include additives which impart specific desired properties to the base stock, such as rust inhibitors, anti-oxidants, extreme pressure resisting agents, lubricity improvers, detersives and the like.
- the additives proposed heretofore have been designed to provide petroleum base compositions for lubrication in conventional equipment such as internal combustion engines of the automotive type, diesel engines and the like, in which the temperature of use is not excessive, not exceeding about 400 F.
- Advanced designs such as jet aircraft design have called for effective lubrication at higher temperatures, such as 500 F. and above, and for these designs, it was found that neither the petroleum base stock nor the conventional additives used therewith were practical.
- the temperatures of operation exceeded the boiling point of some lubricant composition compo-- nents, and generally were in a range at which both lubricant and additives were thermally unstable and decomposed.
- the lubricity characteristics of a lubricant include its load-carrying abilities and its wear properties. Compared to other synthetic high temperature lubricant fluids, the polyphenyl ethers rank high in lubricity characteristics. However, severe design requirements for applications such as aircraft engines include effective lubrication under high pressure as Well as at high temperatures which the uncompounded polyphenyl ethers do not meet. Thus there is a demand for polyphenyl ether base composition having improved lubricity properties.
- An object of the present invention is the provision of improved lubricant compositions employing polyphenyl ether fluids as base stocks.
- a particular object of the present invention is to provide polyphenyl ether base compositions having improved lubricity properties.
- compositions consisting essentially of a polyphenyl ether base fluid and an additive amount of a haloalkanoic compound of the formula where HalR- is a perhalogenated saturated aliphatic carbon chain of from 1 to 6 carbon atoms in which each of the carbon atom substituents is halogen having an atomic weight of below 40, X is a cation selected from the class consisting of hydrogen and heavy metals, and y is an integer equal to the valence of X, have unusual ability to lubricate under ultra high loads at high temperatures.
- the improvement in lubricity characteristics achieved by addition of a compound of the stated kind to the polyphenyl ether base fluids is unusual and surprising. Wear is decreased at each of the test temperatures of 167 F., 400 F. and 600 F., whereas the effect of Wear-diminishing additives on polyphenyl ether base fluids is frequently temperature-dependent, apparent at only one or two points in this temperature range, and activity at one temperature is often accompanied by an actual increase in wear at another of the temperature points.
- the load-carrying ability of the base fluid has been raised to a different order of magnitude in accordance with this invention, which is a unique performance.
- the polyphenyl ethers employed in the compositions of this invention have from 3 to 7 benzene rings and from 1 to 6 oxygen atoms, with the stated oxygen atoms joining the stated benzene rings in chains as ether linkages.
- One or more of the stated benzene rings in these polyphenyl ethers may be hydrocarbyl substituted.
- the hydrocarbyl substituents for thermal stability, must be free of CH and aliphatic CH, so that preferred aliphatic substituents are lower saturated hydrocarbon radicals (1 to 6 carbon atoms) like methyl and tert-butyl, and preferred aromatic substituents are aryl radicals like phenyl, tolyl, t-butylphenyl and u-cumyl.
- the benzene ring supplied in the hydrocarbyl substituent contributes to the total number of benzene rings in the molecule.
- Polyphenyl ethers consisting exclusively of chains of from 3 to 7 benzene rings with at least one oxygen atom joining the stated benzene rings in the chains as an ether linkage have particularly desirable thermal stability.
- alkyl polyphenyl ethers suitable for base fluids are 3-ring polyphenyl ethers like l-(p-methylphenoxy)-4-phenoxybenzene and 2,4-diphenoxy-1-methylbenzene, 4-ring polyphenyl ethers like bis[p-(p-methylphenoxy)phenyl]ether and bis[p-(p-tert-butylphenoxy) phenyl]ether, and so forth.
- Polyphenyl ethers consisting exclusively of benzene rings and ether oxygen atoms linking said rings are exemplified by the triphenoxy benzenes and aryl-substituted polyphenyl ethers such as biphenyl phenoxyphenyl ether, biphenylyloxyphenyl phenoxyphenyl ether, biphenylyl 3 ether, dibiphenylyloxy-benzene, bis(biphenylyloxyphenyl) ether, and the like.
- a preferred class of the polyphenyl ethers comprises those consisting of benzene rings joined in a chain by oxygen atoms as ether linkages between each ring.
- polyphenyl ethers contemplated in this class are the bis(phenoxyphenyDethers (4 benzene rings joined in a chain by 3 oxygen atoms), illustrative of which is bis(m-phenoxyphenyl)ether.
- the bis(phenoxyphenoxy)benzenes are particularly valuable in the present connection. Illustrative of these are mbis(m-phenoxyphenoxy)benzene, m bis(p phenoxyphenoxy)benzene, o-bis(o-phenoxyphenoxy)benzene, and so forth.
- polyphenyl ethers contemplated herein include the bis(phenoxyphenoxyphenyl) ethers such as bis[m-(mphenoxyphenoxy)phenyl] ether, bis[p-(p-phenoxyphenoxy)phenyl] ether, m-(m-phenoxyphenoxy)phenyl m- (o-phenoxyphenoxy)phenyl ether and the bis(phenoxyphenoxyphenoxy)benzenes such as rn-bis[m-(m-phenoxyphenoxy phenoxy] benzene, p-bis [pm-phenoxyphenoxy) phenoxy] benzene and m-bis [m- (p-phenoxyphenoxy phenoxy] benzene.
- bis(phenoxyphenoxyphenyl) ethers such as bis[m-(mphenoxyphenoxy)phenyl] ether, bis[p-(p-phenoxyphenoxy)phenyl] ether, m-(m-phenoxyphenoxy)phenyl m- (o
- the preferred polyphenyl ethers are those having all their ether linkages in the meta-positions since the allmeta-linked ethers are particularly advantageous because of their wide liquid range and high thermal stability.
- mixtures of the polyphenyl ethers either isomeric mixtures or mixtures of homologous ethers, can also advantageously be used in some applications, especially where particular properties such as lower solidification points are required.
- Mixtures of polyphenyl ethers in which the non-terminal phenylene rings are linked through oxygen atoms in the meta and para positions have been found to be particularly suitable to provide compositions with wide liquid ranges.
- a preferred polyphenyl ether mixture of this invention is the mixture of 5 ring polyphenyl ethers wherein the non-terminal phenylene rings are linked through oxygen atoms in the meta and para position, and composed by weight of about 65% m-bis (m-phenoxyphenoxy) benzene, 30% m-[(m-phenoxyphenoxy) (p-phenoxyphenoxy)]benzene and 5% m-bis (p-phenoxyphenoxy)benzene.
- Such a mixture is liquid at room temperature (about 70 F.) whereas the three components solidify individually at temperatures above normal room temperatures.
- polyphenyl ethers can be obtained by known procedures such as, for example, by the Ullmann ether synthesis, by a procedure involving reaction of alkali metal phenoxides such as sodium and potassium phenoxides with aromatic halides such as bromobenzene in the presence of a catalyst such as metallic copper, copper hydroxides, or copper salts.
- alkali metal phenoxides such as sodium and potassium phenoxides
- aromatic halides such as bromobenzene
- a catalyst such as metallic copper, copper hydroxides, or copper salts.
- chloroalkanoic acid compounds wherein the organic radical attached to the carboxyl function is a saturated lower aliphatic hydrocarbon radical, of from 1 to 6 carbon atoms, wherein all of the hydrogen atoms of such hydrocarbon radical have been replaced by halogen atoms having an atomic weight of below about 40, that is, chlorine or fluorine, and preferably chlorine.
- acids contemplated are perchloralkanoic acids such as trichloroacetic acid, pentachloropropionic acid, heptachlorobutyric acid, pentachloroisopropionic acid, nonachlorovaleric acid, nonachloroisovaleric acid and the like.
- halogen atoms substituting the hydrocarbon nucleus of the alkanoic compound may be replaced by fluorine, and the remainder by chlorine, whereby there are provided additives such as dichlorofluoroacetic acid, chlorodifluoroacetic acid, 2,3,3-trichlorodifluoropropionic acid, tetrachloro-3-fluoropropionic acid, pentachlorodifluorobutyric acid, tetrachlorotrifiuorobutyric acid, 2,2-difluoroheptachlorovaleric acid and so forth.
- additives such as dichlorofluoroacetic acid, chlorodifluoroacetic acid, 2,3,3-trichlorodifluoropropionic acid, tetrachloro-3-fluoropropionic acid, pentachlorodifluorobutyric acid, tetrachlorotrifiuorobutyric acid, 2,2-difluoro
- the substituent of the carboxyl group may and preferably will be hydrogen, providing acids such as the above-stated acids.
- acids such as the above-stated acids.
- heavy metals of group II of the periodic table including mercury, cadmium, and asthe salt-forming metal of choice, zinc, and of group IV, especially tin and lead.
- salts of other heavy metals such as those of group I, like copper, silver and so forth; of group III, like indium and thallium; of group IV, like thorium; of group V, like antimony and bismuth; of group VI, like tungsten and tellurium; and of the transition elements, like iron, cobalt, nickel and so forth.
- illustrative of the salts employed in accordance with this invention are zinc bis(trichloroacetate), cadmium bis(trichloroacetate), mercury bis(trichloroacetate), tin bis(trichloroacetate), tin tetrakis(trichloroacetate), lead tetrakis(trichloroacetate), cupric bis(trichloroacetate), cuprous trichloroacetate, bismuth tris(pent-achloropropionate), zinc bis(pentachloropropionate), zinc bis(heptachlorobutyrate), nickel bis(dichlorofluoroacetate), zinc bis(dichlorofluoroacetate), copper bis(trichlorodifluoropropionate) and the like.
- the haloalkanoic acid compound is combined with the fluid polyphenylether base fluid to the extent of, generally, between about 0.01% and 10% by weight of the fluid.
- Particular effective amounts depend on the nature of the individual additive and of the ether fluid. In most cases the ability of the agent with respect to extreme pressure lubrication improvement increases as the concentration is increased.
- Remarkably low concentrations of the additives in the compositions presently provided are eflective to give extremely high lubricity properties. Indeed, it has been shown that treatment of frictionally contacting metal surfaces with an additive of the invention prior to lubrication thereof with a polyphenyl ether fluid provides a suflicient residue on the metal surfaces to produce better than double the weld point values obtained without such prior treatment. Concentration limits may also affect the selection of a. suitable proportion of additive and base fluid in the lubricant compositions.
- compositions of this invention in addition to the polyphenyl ether base fluid and the haloalkanoic compound additive, may additionally include any of a wide variety of further additives.
- the polyphenyl ethers are inclined to increase in viscosity on prolonged exposure to elevated temperatures on the order of 550 F., particularly in the presence of air.
- the polyphenyl ether base fluids are frequently combined with an antioxidant, such as a high molecular weight amine, an organo-metallic compound, and so forth.
- viscosity index improvers such as polymeric materials like polymethacrylate alkyl esters, dispersants and additives improving other aspects of the lubricant composition may be employed in these compositions if desired.
- the antiwear and extreme pressure lubrication char- ;acteristics of the lubricant compositions are evaluated by means of the well known Shell 4-Ball Extreme Pressure Tester and the Shell 4-Ba1l Wear Machine, as described, for example, in the Lubrication Engineers Manual (US. Steel Corp., 1960).
- These testers include 4 balls of stainless steel arranged in the form of an equilateral tetrahedron. The three lower balls are held immovably clamped in a holder to form a cradle in which the fourth upper ball is caused to rotate at 1200-4800 r.p.m. about a vertical axis in contact with the three lower stationary balls.
- the contacting surfaces of the balls are immersed in the test fluid which is held in a cup surrounding the assembly.
- a modified cup and heater assembly is used to evaluate lubricants at elevated temperature and provisions are made to permit high temperature testing under an inert atmosphere: see The Study of Lubrication in Using the 4-Ball Type Machine by R. G. Larsen, Lubrication Engineering, vol. 1, 35-43, 59 (March 1945).
- the upper ball is rotated while the load is gradually increased by increments of kg. until the balls are welded together Within a 1-minute test period.
- the upper ball is rotated under a load of 40 kg. for one hour at each of the temperatures for which wear scar diameters worn in the surface of the three lower stationary balls are reported.
- Example 1 A lubricant composition is prepared by combining trichloroacetic acid with a polyphenyl ether of the following composition, by weight: 65% m-bis(m-phenoxyphenoxy) benzene, 30% m-[m-phenoxyphenoxy)(p-phenoxyphenoxy) benzene, 5 m-bis (p-phenoxyphenoxy)benzene, in a proportion of 1 gram (g.) of the acid to 100 g. of the base fluid.
- a portion of the base fluid used to provide the abovedescribed composition is reserved, free of additive, and run through the same sequence of tests, to provide a basis for comparison.
- the balls weld at a pressure of 150 kg.
- the extreme pressure tester is taken to its load limit, 1000 kg. without achieving a weld of the balls.
- the wear scar diameters determined for the lubricant composition of this example including trichloroacetic acid and for the base fluid without additive are as follows:
- Example 2 Four of the stainless steel balls used in the Shell 4- ball test are soaked in molten trichloroacetic acid for two hours, and then wiped clean and used to determine the weld point of untreated polyphenyl ether of the composition described in Example 1.
- the weld point obtained is constant at 350 kg., whereas the same polyphenyl ether fluid when employed with untreated balls welds at 150 kg.
- Weld points of 350-400 kg. are also obtained when the treatment time for soaking in molten trichloroacetic acid is diminished to one-half hour.
- Example 3 A lubricant composition is prepared by combining zinc bis(trichloroacetate) with a polyphenyl ether base fluid of the composition stated in Example 1, to the limit of the solubility of the salt at room temperature.
- Zinc bis(trichloroacetate) is prepared by heating 2 parts (by weight) of trichloroacetic acid to form a melt, adding 1 part of zinc acetate and stirring, washing the cooled mixture with petroleum ether to remove acetic acid, and drying.
- the filtered solution of the additive in the polyphenyl ether is subjected to test of its extreme pressure properties as compared to the untreated base fluid. The weld point is increased.
- a lubricant composition comprising a major amount of a polyphenyl ether base fluid and a haloalkanoic acid compound of the formula (HalRCOO) X where Hal-R is a perhalogenated saturated aliphatic carbon chain of from one to six carbon atoms in which each of the carbon atom substituents is a halogen atom having an atomic weight below 40, X is a cation selected from the class consisting of hydrogen and heavy metal cations, and y is equal to the valence of X, said haloalkanoic acid compound being present in said composition in an amount sufficient to improve a lubricity property of said polyphenyl ether fluid selected from the group consisting of wear resistance and load-carrying ability 2.
- said haloalkanoic compound is a perchloroalkanoic acid.
- composition of claim 1 wherein said haloalkanoic compound is trichloroacetic acid.
- composition of claim 1 wherein said haloalkanoic compound is an oil-soluble heavy metal salt of trichloroacetic acid.
- composition of claim 1 wherein said haloalkanoic compound is a salt of trichloroacetic acid with a heavy metal of Group II of the Periodic Table.
- compositions of claim 1 wherein said haloalkanoic compound is zinc trichloroacetate.
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Description
United States Patent Office 3,226,323 Patented Dec. 28, 1965 3,226,323 LUBRICANT COMPOSITION CONTAINING A HALOALKANOIC COMPOUND John R. Stemniski, Swampscott, Mass., assignor to Monsanto Research Corporation, 't. Louis, Mo., a corporation of Delaware No Drawing. Filed Apr. 30, 1963, Ser. No. 277,024 6 Claims. (Cl. 25233.6)
This invention relates to liquid fluids of high thermal stability, and more particularly, provides functional fluids comprising polyphenyl ethers and certain haloalkanoic compounds as additives therefor.
Polyphenyl ethers have found wide application as functional fluids owing to their very good thermal stability, lubricity, and resistance to foam. For example, they have been found to be valuable as hydraulic fluids, as heatexchange media, as atomic reactor coolants, as diffusion pump fluids, as lubricants in motor operation generally, and particularly as jet engine lubricants.
As is known in the art, petroleum lubricants, in addition to the petroleum base stock, generally include additives which impart specific desired properties to the base stock, such as rust inhibitors, anti-oxidants, extreme pressure resisting agents, lubricity improvers, detersives and the like. The additives proposed heretofore have been designed to provide petroleum base compositions for lubrication in conventional equipment such as internal combustion engines of the automotive type, diesel engines and the like, in which the temperature of use is not excessive, not exceeding about 400 F. Advanced designs such as jet aircraft design have called for effective lubrication at higher temperatures, such as 500 F. and above, and for these designs, it was found that neither the petroleum base stock nor the conventional additives used therewith were practical. The temperatures of operation exceeded the boiling point of some lubricant composition compo-- nents, and generally were in a range at which both lubricant and additives were thermally unstable and decomposed.
Development of synthetic base stocks like the polyphenyl ethers has provided lubricant fluids stable at temperatures above the useful range of the mineral oils. There is now a demand for compositions in which such functional fluids, with thermal stability superior to that of the mineral oils, are compounded with additives enhancing desirable properties thereof. Many materials known as useful mineral oil additives are, as stated, excluded from utility in this connection by volatility and lack of thermal stability at the temperatures of use of the polyphenyl ethers. Furthermore, it has been found that additives conventional in mineral oil lubricants do not perform predictably upon combination with synthetic base stocks. There are significant differences in chemical structure of the stocks which can affect the response to additives: for example, whereas the mineral oils consist of aliphatic hydrocarbons, the polyphenyl ethers are, by contrast, aromatic ethers. Indeed, base stocks chemically different from the mineral oils may actually suffer chemical attack by certain additives, with deleterious effects on their superior high temperature properties. Temperature of operation can also affect the performance of additives, and so forth. Thus, an empirical approach has been required for the provision of improved lubricants including the polyphenyl ethers as base stocks.
One of the aspects in which the properties of the polyphenyl ether base stocks are considered deficient consists in their lubricity characteristics. The lubricity characteristics of a lubricant include its load-carrying abilities and its wear properties. Compared to other synthetic high temperature lubricant fluids, the polyphenyl ethers rank high in lubricity characteristics. However, severe design requirements for applications such as aircraft engines include effective lubrication under high pressure as Well as at high temperatures which the uncompounded polyphenyl ethers do not meet. Thus there is a demand for polyphenyl ether base composition having improved lubricity properties.
An object of the present invention is the provision of improved lubricant compositions employing polyphenyl ether fluids as base stocks.
A particular object of the present invention is to provide polyphenyl ether base compositions having improved lubricity properties.
These and other objects will become evident upon consideration of the following specification and claims.
It has now been found that compositions consisting essentially of a polyphenyl ether base fluid and an additive amount of a haloalkanoic compound of the formula where HalR- is a perhalogenated saturated aliphatic carbon chain of from 1 to 6 carbon atoms in which each of the carbon atom substituents is halogen having an atomic weight of below 40, X is a cation selected from the class consisting of hydrogen and heavy metals, and y is an integer equal to the valence of X, have unusual ability to lubricate under ultra high loads at high temperatures.
The improvement in lubricity characteristics achieved by addition of a compound of the stated kind to the polyphenyl ether base fluids is unusual and surprising. Wear is decreased at each of the test temperatures of 167 F., 400 F. and 600 F., whereas the effect of Wear-diminishing additives on polyphenyl ether base fluids is frequently temperature-dependent, apparent at only one or two points in this temperature range, and activity at one temperature is often accompanied by an actual increase in wear at another of the temperature points. The load-carrying ability of the base fluid has been raised to a different order of magnitude in accordance with this invention, which is a unique performance.
The polyphenyl ethers employed in the compositions of this invention have from 3 to 7 benzene rings and from 1 to 6 oxygen atoms, with the stated oxygen atoms joining the stated benzene rings in chains as ether linkages. One or more of the stated benzene rings in these polyphenyl ethers may be hydrocarbyl substituted. The hydrocarbyl substituents, for thermal stability, must be free of CH and aliphatic CH, so that preferred aliphatic substituents are lower saturated hydrocarbon radicals (1 to 6 carbon atoms) like methyl and tert-butyl, and preferred aromatic substituents are aryl radicals like phenyl, tolyl, t-butylphenyl and u-cumyl. In the latter case, the benzene ring supplied in the hydrocarbyl substituent contributes to the total number of benzene rings in the molecule. Polyphenyl ethers consisting exclusively of chains of from 3 to 7 benzene rings with at least one oxygen atom joining the stated benzene rings in the chains as an ether linkage have particularly desirable thermal stability.
Exemplary of the alkyl polyphenyl ethers suitable for base fluids are 3-ring polyphenyl ethers like l-(p-methylphenoxy)-4-phenoxybenzene and 2,4-diphenoxy-1-methylbenzene, 4-ring polyphenyl ethers like bis[p-(p-methylphenoxy)phenyl]ether and bis[p-(p-tert-butylphenoxy) phenyl]ether, and so forth.
Polyphenyl ethers consisting exclusively of benzene rings and ether oxygen atoms linking said rings are exemplified by the triphenoxy benzenes and aryl-substituted polyphenyl ethers such as biphenyl phenoxyphenyl ether, biphenylyloxyphenyl phenoxyphenyl ether, biphenylyl 3 ether, dibiphenylyloxy-benzene, bis(biphenylyloxyphenyl) ether, and the like.
A preferred class of the polyphenyl ethers comprises those consisting of benzene rings joined in a chain by oxygen atoms as ether linkages between each ring.
Examples of the polyphenyl ethers contemplated in this class are the bis(phenoxyphenyDethers (4 benzene rings joined in a chain by 3 oxygen atoms), illustrative of which is bis(m-phenoxyphenyl)ether. The bis(phenoxyphenoxy)benzenes are particularly valuable in the present connection. Illustrative of these are mbis(m-phenoxyphenoxy)benzene, m bis(p phenoxyphenoxy)benzene, o-bis(o-phenoxyphenoxy)benzene, and so forth. Further, the polyphenyl ethers contemplated herein include the bis(phenoxyphenoxyphenyl) ethers such as bis[m-(mphenoxyphenoxy)phenyl] ether, bis[p-(p-phenoxyphenoxy)phenyl] ether, m-(m-phenoxyphenoxy)phenyl m- (o-phenoxyphenoxy)phenyl ether and the bis(phenoxyphenoxyphenoxy)benzenes such as rn-bis[m-(m-phenoxyphenoxy phenoxy] benzene, p-bis [pm-phenoxyphenoxy) phenoxy] benzene and m-bis [m- (p-phenoxyphenoxy phenoxy] benzene.
The preferred polyphenyl ethers are those having all their ether linkages in the meta-positions since the allmeta-linked ethers are particularly advantageous because of their wide liquid range and high thermal stability. However, mixtures of the polyphenyl ethers, either isomeric mixtures or mixtures of homologous ethers, can also advantageously be used in some applications, especially where particular properties such as lower solidification points are required. Mixtures of polyphenyl ethers in which the non-terminal phenylene rings are linked through oxygen atoms in the meta and para positions have been found to be particularly suitable to provide compositions with wide liquid ranges. Of the mixtures having only meta and para linkages a preferred polyphenyl ether mixture of this invention is the mixture of 5 ring polyphenyl ethers wherein the non-terminal phenylene rings are linked through oxygen atoms in the meta and para position, and composed by weight of about 65% m-bis (m-phenoxyphenoxy) benzene, 30% m-[(m-phenoxyphenoxy) (p-phenoxyphenoxy)]benzene and 5% m-bis (p-phenoxyphenoxy)benzene. Such a mixture is liquid at room temperature (about 70 F.) whereas the three components solidify individually at temperatures above normal room temperatures.
The aforesaid polyphenyl ethers can be obtained by known procedures such as, for example, by the Ullmann ether synthesis, by a procedure involving reaction of alkali metal phenoxides such as sodium and potassium phenoxides with aromatic halides such as bromobenzene in the presence of a catalyst such as metallic copper, copper hydroxides, or copper salts.
Referring to the additives combined with the abovedescribed polyphenyl ether base fluids in accordance with this invention, these are chloroalkanoic acid compounds wherein the organic radical attached to the carboxyl function is a saturated lower aliphatic hydrocarbon radical, of from 1 to 6 carbon atoms, wherein all of the hydrogen atoms of such hydrocarbon radical have been replaced by halogen atoms having an atomic weight of below about 40, that is, chlorine or fluorine, and preferably chlorine. Thus, illustrative of the acids contemplated are perchloralkanoic acids such as trichloroacetic acid, pentachloropropionic acid, heptachlorobutyric acid, pentachloroisopropionic acid, nonachlorovaleric acid, nonachloroisovaleric acid and the like. Part of the halogen atoms substituting the hydrocarbon nucleus of the alkanoic compound may be replaced by fluorine, and the remainder by chlorine, whereby there are provided additives such as dichlorofluoroacetic acid, chlorodifluoroacetic acid, 2,3,3-trichlorodifluoropropionic acid, tetrachloro-3-fluoropropionic acid, pentachlorodifluorobutyric acid, tetrachlorotrifiuorobutyric acid, 2,2-difluoroheptachlorovaleric acid and so forth. The substituent of the carboxyl group (represented by X in the formula above) may and preferably will be hydrogen, providing acids such as the above-stated acids. Alternatively, it is within the scope of the invention to employ the oil-soluble salts of said acids with heavy metals, by which are meant metals having a density of 4 or more. Particularly preferred in this connection are heavy metals of group II of the periodic table, including mercury, cadmium, and asthe salt-forming metal of choice, zinc, and of group IV, especially tin and lead. Alternatively, the selection depending on such considerations as the reactivity and availability of the metals, there may be employed salts of other heavy metals, such as those of group I, like copper, silver and so forth; of group III, like indium and thallium; of group IV, like thorium; of group V, like antimony and bismuth; of group VI, like tungsten and tellurium; and of the transition elements, like iron, cobalt, nickel and so forth.
Thus, illustrative of the salts employed in accordance with this invention are zinc bis(trichloroacetate), cadmium bis(trichloroacetate), mercury bis(trichloroacetate), tin bis(trichloroacetate), tin tetrakis(trichloroacetate), lead tetrakis(trichloroacetate), cupric bis(trichloroacetate), cuprous trichloroacetate, bismuth tris(pent-achloropropionate), zinc bis(pentachloropropionate), zinc bis(heptachlorobutyrate), nickel bis(dichlorofluoroacetate), zinc bis(dichlorofluoroacetate), copper bis(trichlorodifluoropropionate) and the like.
The haloalkanoic acid compound is combined with the fluid polyphenylether base fluid to the extent of, generally, between about 0.01% and 10% by weight of the fluid. Particular effective amounts depend on the nature of the individual additive and of the ether fluid. In most cases the ability of the agent with respect to extreme pressure lubrication improvement increases as the concentration is increased. Remarkably low concentrations of the additives in the compositions presently provided are eflective to give extremely high lubricity properties. Indeed, it has been shown that treatment of frictionally contacting metal surfaces with an additive of the invention prior to lubrication thereof with a polyphenyl ether fluid provides a suflicient residue on the metal surfaces to produce better than double the weld point values obtained without such prior treatment. Concentration limits may also affect the selection of a. suitable proportion of additive and base fluid in the lubricant compositions.
It will be appreciated that the compositions of this invention, in addition to the polyphenyl ether base fluid and the haloalkanoic compound additive, may additionally include any of a wide variety of further additives. For example, the polyphenyl ethers are inclined to increase in viscosity on prolonged exposure to elevated temperatures on the order of 550 F., particularly in the presence of air. To diminish this undesirable tendency, the polyphenyl ether base fluids are frequently combined with an antioxidant, such as a high molecular weight amine, an organo-metallic compound, and so forth. Furthermore, viscosity index improvers such as polymeric materials like polymethacrylate alkyl esters, dispersants and additives improving other aspects of the lubricant composition may be employed in these compositions if desired.
The invention is illustrated but not limited by the following examples, in which the tests employed to determine the reported adjuvant effects of the haloalkanoic compounds when employed with the polyphenyl ether lubricant base fluid are conducted as follows:
The antiwear and extreme pressure lubrication char- ;acteristics of the lubricant compositions are evaluated by means of the well known Shell 4-Ball Extreme Pressure Tester and the Shell 4-Ba1l Wear Machine, as described, for example, in the Lubrication Engineers Manual (US. Steel Corp., 1960). These testers include 4 balls of stainless steel arranged in the form of an equilateral tetrahedron. The three lower balls are held immovably clamped in a holder to form a cradle in which the fourth upper ball is caused to rotate at 1200-4800 r.p.m. about a vertical axis in contact with the three lower stationary balls. The contacting surfaces of the balls are immersed in the test fluid which is held in a cup surrounding the assembly. A modified cup and heater assembly is used to evaluate lubricants at elevated temperature and provisions are made to permit high temperature testing under an inert atmosphere: see The Study of Lubrication in Using the 4-Ball Type Machine by R. G. Larsen, Lubrication Engineering, vol. 1, 35-43, 59 (August 1945).
For determination of the extreme pressure properties in the 4-ball EP tester, the upper ball is rotated while the load is gradually increased by increments of kg. until the balls are welded together Within a 1-minute test period.
For measurement of wear in the wear machine, the upper ball is rotated under a load of 40 kg. for one hour at each of the temperatures for which wear scar diameters worn in the surface of the three lower stationary balls are reported.
Example 1 A lubricant composition is prepared by combining trichloroacetic acid with a polyphenyl ether of the following composition, by weight: 65% m-bis(m-phenoxyphenoxy) benzene, 30% m-[m-phenoxyphenoxy)(p-phenoxyphenoxy) benzene, 5 m-bis (p-phenoxyphenoxy)benzene, in a proportion of 1 gram (g.) of the acid to 100 g. of the base fluid.
A portion of the base fluid used to provide the abovedescribed composition is reserved, free of additive, and run through the same sequence of tests, to provide a basis for comparison.
Using the base fluid alone, in the extreme pressure test, the balls weld at a pressure of 150 kg.
Employing the lubricant composition described above, consisting of 1% of trichloroacetic acid combined with the same polyphenyl ether, the extreme pressure tester is taken to its load limit, 1000 kg. without achieving a weld of the balls.
Using the Shell 4-ball wear tester, the wear scar diameters determined for the lubricant composition of this example including trichloroacetic acid and for the base fluid without additive are as follows:
Wear Scar Diameter, mm. 167 F. 400 F. 600 F.
With Additive 1.36 2.48 2.10 Without Additive 1.79 3.30 2.93
Example 2 Four of the stainless steel balls used in the Shell 4- ball test are soaked in molten trichloroacetic acid for two hours, and then wiped clean and used to determine the weld point of untreated polyphenyl ether of the composition described in Example 1. The weld point obtained is constant at 350 kg., whereas the same polyphenyl ether fluid when employed with untreated balls welds at 150 kg. Weld points of 350-400 kg. are also obtained when the treatment time for soaking in molten trichloroacetic acid is diminished to one-half hour.
6 Example 3 A lubricant composition is prepared by combining zinc bis(trichloroacetate) with a polyphenyl ether base fluid of the composition stated in Example 1, to the limit of the solubility of the salt at room temperature. Zinc bis(trichloroacetate) is prepared by heating 2 parts (by weight) of trichloroacetic acid to form a melt, adding 1 part of zinc acetate and stirring, washing the cooled mixture with petroleum ether to remove acetic acid, and drying. The filtered solution of the additive in the polyphenyl ether is subjected to test of its extreme pressure properties as compared to the untreated base fluid. The weld point is increased.
Using the tin, antimony, lead and bismuth salts of trichloracetic acid, trichloropropionic acid and dichlorofluoroacetic acid, similar results demonstrating an enhancement in the lubricant characteristics of the polyphenyl ether base fluid are obtained.
While the invention has been described with reference to specific preferred embodiments thereof, it is to be appreciated that modifications and variations can be made without departing from the scope of the invention, which is limited only as defined in the appended claims.
What is claimed is:
1. A lubricant composition comprising a major amount of a polyphenyl ether base fluid and a haloalkanoic acid compound of the formula (HalRCOO) X where Hal-R is a perhalogenated saturated aliphatic carbon chain of from one to six carbon atoms in which each of the carbon atom substituents is a halogen atom having an atomic weight below 40, X is a cation selected from the class consisting of hydrogen and heavy metal cations, and y is equal to the valence of X, said haloalkanoic acid compound being present in said composition in an amount sufficient to improve a lubricity property of said polyphenyl ether fluid selected from the group consisting of wear resistance and load-carrying ability 2. The composition of claim 1 wherein said haloalkanoic compound is a perchloroalkanoic acid.
3. The composition of claim 1 wherein said haloalkanoic compound is trichloroacetic acid.
4. The composition of claim 1 wherein said haloalkanoic compound is an oil-soluble heavy metal salt of trichloroacetic acid.
I 5. The composition of claim 1 wherein said haloalkanoic compound is a salt of trichloroacetic acid with a heavy metal of Group II of the Periodic Table.
6. The compositions of claim 1 wherein said haloalkanoic compound is zinc trichloroacetate.
References Cited by the Examiner UNITED STATES PATENTS 2,559,629 7/1951 Berry 25258 X 2,802,028 8/1957 England 25235 X 2,940,929 6/1960 Diamond 252-33.6 3,080,321 3/1963 Blake et al. 252-52 X FOREIGN PATENTS 752,383 7/1956 Great Britain.
842,647 7/ 1960 Great Britain.
851,651 10/1960 Great Britain.
DANIEL E. WYMAN, Primary Examiner.
Claims (1)
1. A LUBRICANT COMPOSITION COMPRISING MAJOR AMOUNT OF A POLYPHENYL ETHER BASE FLUID AND A HALOALKANOIC ACID COMPOUND OF THE FORMULA (HAL-R-COO)Y-X WHERE HAL-R IS A PERHALOGENATED SATURATED ALIPHATIC CARBON CHAIN OF FROM ONE TO SIX CARBON ATOMS IN WHICH EACH OF THE CARBON ATOM SUBSTITUENTS IS A HALOGEN ATOM HAVING AN ATOMIC WEIGHT BELOW 40, X IS A CATION SELECTED FROM THE CLASS CONSISTING OF HYDROGEN AND HEAVY METAL CATIONS, AND Y IS EQUAL TO THE VALENCE OF X, SAID HALOALKANOIC ACID COMPOUND BEING PRESENT IN SAID COMPOSITION IN AN AMOUNT SUFFICIENT TO IMPROVE A LUBRICITY PROPERTY OF SAID POLYPHENYL ETHER FLUID SELECTED FROM THE GROUP CONSISTING OF WEAR RESISTANCE AND LOAD-CARRYING ABILITY.
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US277024A US3226323A (en) | 1963-04-30 | 1963-04-30 | Lubricant composition containing a haloalkanoic compound |
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US277024A US3226323A (en) | 1963-04-30 | 1963-04-30 | Lubricant composition containing a haloalkanoic compound |
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US3284355A (en) * | 1963-09-12 | 1966-11-08 | Mobil Oil Corp | Lubricating compositions |
US3476684A (en) * | 1967-08-18 | 1969-11-04 | Chevron Res | High dropping point aluminum grease |
US3720614A (en) * | 1970-09-25 | 1973-03-13 | Monsanto Co | Polyphenyl thioether lubricating compositions |
US4803005A (en) * | 1986-08-06 | 1989-02-07 | Exfluor Research Corporation | Perfluoropolyether solid fillers for lubricants |
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US2559629A (en) * | 1948-12-13 | 1951-07-10 | Du Pont | Polyfluoroalkanoic compounds and their preparation |
GB752383A (en) * | 1953-04-14 | 1956-07-11 | Bataafsche Petroleum | Lubricating oil compositions |
US2802028A (en) * | 1956-03-28 | 1957-08-06 | Du Pont | Preparation of polyfluorocarboxylic acids and amides from 1, 1-difluoro-1-alkenes, alkali metal cyanides and water |
US2940929A (en) * | 1958-06-26 | 1960-06-14 | Shell Oil Co | High-temperature lubricants |
GB842647A (en) * | 1956-02-20 | 1960-07-27 | Renault | Improvements in and relating to lubricants |
GB851651A (en) * | 1957-12-09 | 1960-10-19 | Bataafsche Petroleum | Polyphenyl ether compositions and their use as lubricants |
US3080321A (en) * | 1957-08-09 | 1963-03-05 | Monsanto Chemicals | Isomeric mixtures of diphenoxy-, ditoloxy-, and phenoxytoloxybenzenes as functional fluids |
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US2559629A (en) * | 1948-12-13 | 1951-07-10 | Du Pont | Polyfluoroalkanoic compounds and their preparation |
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GB842647A (en) * | 1956-02-20 | 1960-07-27 | Renault | Improvements in and relating to lubricants |
US2802028A (en) * | 1956-03-28 | 1957-08-06 | Du Pont | Preparation of polyfluorocarboxylic acids and amides from 1, 1-difluoro-1-alkenes, alkali metal cyanides and water |
US3080321A (en) * | 1957-08-09 | 1963-03-05 | Monsanto Chemicals | Isomeric mixtures of diphenoxy-, ditoloxy-, and phenoxytoloxybenzenes as functional fluids |
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US3284355A (en) * | 1963-09-12 | 1966-11-08 | Mobil Oil Corp | Lubricating compositions |
US3476684A (en) * | 1967-08-18 | 1969-11-04 | Chevron Res | High dropping point aluminum grease |
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