초록

Fluorinated dialkyl dithiophosphoric acids according to formula (I) and metallic salts thereof:the compounds are useful, for example, as additives for lubricant compositions.

대표청구항 ▼

1. A compound according to formula (I) or metallic salts thereof:wherein R 1 and R 2 are each independently selected from the group consisting of C 1 to C 40 organic residues; andwherein R 1 and R 2 are different, or R 1 and R 2 may form a ring, and at least one of R 1 and R 2 is fluorinat

1. A compound according to formula (I) or metallic salts thereof:wherein R 1 and R 2 are each independently selected from the group consisting of C 1 to C 40 organic residues; andwherein R 1 and R 2 are different, or R 1 and R 2 may form a ring, and at least one of R 1 and R 2 is fluorinated; wherein fluorine is present at in an amount greater than 1 weight percent, but not more than 50 weight percent. 2. A compound according to claim 1, wherein either R 1 or R 2 is formed from an alcohol independently selected from the group consisting of primary, secondary, tertiary or aromatic fluorinated alcohols and primary, secondary, tertiary or aromatic non-fluorinated alcohols, such that at least one of R 1 and R 2 is derived from a fluorinated alcohol. 3. A compound according to claim 2, wherein the fluorinated alcohol is selected from the group consisting of alcohols having the molecular formulae:F(CF 2 ) x CH 2 OH wherein x is from 1 to about 20.H (CF 2 ) x CH 2 OH, wherein x is from 1 to about 20,F(CF 2 CF 2 ) x CH 2 CH 2 OH, wherein x is from 1 to about 10.F(CF 2 CF 2 ) x (CH 2 CH 2 O) y OH, wherein x is from 1 to about 10 and y is from 1 to about 20, andF(CFCF 3 CF 2 O) x CF (CF 3 )CH 2 OH, wherein x is from 1 to about 20. 4. A compound according to claim 3, wherein the fluorinated alcohol is selected from the group consisting of 1H, 1H-heptafluoro-1-butanol and 1H, 1H-perfluoro-1-octanol, 1H, 1H, 5H-octafluoro-1-pentanol and 1H, 1H, 2H, 2H-perfluoro-1-octanol. 5. A compound according to claim 4, wherein the fluorinated alcohol is 1H, 1H, 2H, 2H-perfluoro-1-octanol. 6. A compound according to claim 2, wherein either R 1 or R 2 is formed from a non-fluorinated alcohol selected from the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, 4-methyl-2-pentanol, 2-ethylhexanol, isotridecanol, cyclohexanol, cyclododecanol, phenol, cresol, higher alcohols and fatty alcohols. 7. A compound according to claim 1, which is a metallic salt comprising a metal atom selected from the group consisting of zinc, molybdenum, barium, aluminum, sodium, calcium, lithium, lead, tin, copper, cadmium, cobalt, strontium, nickel and combinations thereof. 8. A compound according to claim 1, wherein the metallic salt comprises a metal atom selected from the group consisting of zinc, molybdenum and combinations thereof. 9. A compound according to claim 1, wherein the metallic salt is zinc. 10. A compound of the formula (I) or metallic salts thereof:wherein R 1 and R 2 are each independently selected from the group consisting of C 1 to C 40 organic residues; and wherein R 1 and R 2 are the same or different, or R 1 and R 2 may form a ring, and at least one of R 1 and R 2 is a fluorinated C 1 to C 40 organic residue, provided that when R 1 and R 2 are the same, neither R 1 nor R 2 can be —(CH 2 (CF 2 ) x CF 2 H), where x is 1, 3 or 5; and wherein fluorine is present in an amount greater than 1 weight percent, but not more than 50 weight percent. 11. A lubricant composition comprising a lubricant base fluid and one or more compounds according to claim 1. 12. An anti-wear additive comprising one or more compounds of claim 1. 13. An anti-wear additive comprising a compound of formula (I) or metallic salts thereof:wherein R 1 and R 2 are each independently selected from the group consisting of C 1 to C 40 organic residues;and wherein at least one of R 1 and R 2 is a fluorinated C 1 to C 40 organic residue, and wherein fluorine is present in an amount greater than 1 weight percent, but not more than 50 weight percent. 14. An anti-wear additive according to claim 13, wherein the metallic salt is a compound of the formula (II): x4 ][S 2 P(OR) 2 ] x   (II)wherein M is a metal atom and x is the valency of the metal atom; wherein the R groups are selected from R 1 and R 2 , as defined above, provided that at least one or R 1 or R 2 is fluorinated. 15. A lubricant composition comprising a mineral oil base fluid and at least one fluorinated compound according to formula (I):wherein at least one of R 1 and R 2 is a fluorinated C 1 to C 40 organic residue; andwherein R 1 and R 2 are the same or different, or R 1 and R 2 may form a ring, and wherein fluorine is present in an amount greater than 1 weight percent, but not more than 50 weight percent. 16. A lubricant composition according to claim 15, further comprising at least one fluorinated dialkyl dithiophosphate salt. 17. A lubricant composition according to claim 16, wherein the fluorinated dialkyl dithiophosphate salt is a compound according to formula (II): x+ ][S 2 P(OR) 2 ] x   (II)wherein M is a metal atom and x is the valency of the metal atom;wherein the R groups are selected from R 1 and R 2 , as defined above, provided that at least one of R 1 or R 2 is fluorinated. 18. A formulated lubricant for use in internal combustion engines comprising a lubricant base fluid and at least one fluorinated compound according to claim 1, and optionally comprising one or more other additives selected from the group consisting of viscosity modifiers, oxidation inhibitors, pour point depressants, detergents, dispersants, friction modifiers, anti-wear agents, foam inhibitors, corrosion inhibitors and metal deactivators.