Non-symmetric, partially fluorinated lubricant additives

A process for preparing a non-symmetric, partially fluorinated composition having a molecular structure:

• R1f—F′—R2—F″—R3h
• wherein R1f represents a wholly or partially fluorinated C1 to C40 organic residue end group;
• F′ and F″ represent functional linkages which are either alike or different and are selected from the group consisting of carboxylic esters, thioesters, sulfonic esters, ureas, thioureas, amides, phosphates, thiophosphates, imines, amines, ethers, thioethers, urethanes, thiourethanes, sulfoxides, sulfones, and mixtures thereof;
• R2 represents the hydrocarbon backbone selected from the group consisting of a C1 to C30 alkyl, C3 to C30 cycloalkyl, an aromatic group and mixtures thereof;
• and
• R3h represents a non-fluorinated C1 to C40 organic residue end group, said process comprising:
• (i) combining A and B, wherein A itself is a mixture of two or more compounds wherein at least one A compound is a partially fluorinated compound and at least one other A compound is a non-fluorinated compound, and wherein B is a compound having at least two functional groups that are the same or different, and wherein A and B independently are selected from the group consisting of
• (a) alcohol, mercaptan and amine, or
• (b) carboxylic acid, carboxylic acid anhydride, carboxylic acid halide, carboxylic ester, nitrile, sulfonyl halide, isocyanate, isothiocyanate, aldehyde, ketone, alkyl halide, phosphoryl halide, thiophosphoryl halide, phosphoric anhydride, and thiophosphoryl anhydride, with the provisio:
• (i) that when the functional groups of either A or B are alcohols, then the functional groups of B or A, respectively, are selected from the group consisting of carboxylic acid, acid anhydride, acid chloride, carboxylic ester, acid anhydride, nitrile, sulfonyl halide, isocyanate, isothiocyanate, phosphoryl halide, thiophosphoryl halide and alkyl halide;
• (ii) that when the functional groups of either A or B are mercaptans, then the functional groups of B or A, respectively, are selected from the group consisting of acid halide, isocyanate and alkyl halide;
• and (iii) that when the functional groups of either A or B are amines, then the functional groups of B or A, respectively, are selected from the group consisting of carboxylic acid, acid anhydride, acid chloride, carboxylic ester, isocyanate, aldehyde and ketone;
• to form said F′ and F″ functional linkages
• (ii) recovering non-symmetric, partially fluorinated composition.