Anionic polymerization initiators and reduced hysteresis products therefom

A method of preparing a hydrocarbon soluble anionic polymerization initiator comprising the steps of:

• forming a reaction product by reacting an organolithium compound with a functionalizing agent;
• said functionalizing agent being selected from the group consisting of cyclic amines having the general formula ##STR14## where R.sub.2 is selected from the group consisting of a divalent alkylene, oxy- or amino-alkylene group having from about 3 to about 12 methylene groups;
• and mixing said reaction product with an organic alkali metal compound selected from the group consisting of compounds having the general formula R.sub.3 M, R.sub.4 OM, [R.sub.5 C(O)OF] R.sub.5 C(O)OM, R.sub.6 R.sub.7 NM, and R.sub.8 SO.sub.3 M, where R.sub.3, R.sub.4, R.sub.5, R.sub.6 R.sub.7, and R.sub.8 are each selected from the group consisting of alkyls, cycloalkyls, alkenyls, aryls, or phenyls, having from about 1 to about 12 carbon atoms, and where M is selected from the group consisting of Na, K, Rb or Cs;
• and optionally, a chelating reagent;
• said organolithium compound having the general formula RLi where R is selected from the group consisting of alkyls, cycloalkyls, alkenyls, aryls and aralkyls having from 1 to about 20 carbon atoms and short chain length low molecular weight polymers from diolefin and vinyl aryl monomers having up to about 25 units.

A hydrocarbon soluble, anionic polymerization initiator comprising a mixture of:

• (i) a lithio amine having the general formula
• (A)Li(SOL)y
• where y is from about 0.5 to about 3;
• SOL is a solubilizing component selected from the group consisting of dienyl and vinyl aromatic oligomers having a degree of polymerization of from about 3 to about 300 polymerization units;
• and, A is selected from the group consisting of dialkyl, alkyl, cycloalkyl or dicycloalkyl amine radicals having the general formula ##STR15## and cyclic amine radicals having the general formula ##STR16## where each R.sub.1 is independently selected from the group consisting of alkyls, cycloalkyls and aralkyls having from 1 to about 12 carbon atoms, and R.sub.2 is selected from the group consisting of a divalent alkylene, oxy- or amino-alkylene group having from about 3 to about 12 methylene groups;
• (ii) an organic alkali metal compound;
• and, optionally,
• (iii) a chelating reagent.

A method of preparing a hydrocarbon soluble anionic polymerization initiator comprising the steps of:

• forming a reaction product by reacting an organolithium compound with a functionalizing agent and a solubilizing agent;
• said functionalizing agent being selected from the group consisting of alkyl, dialkyl, cycloalkyl or dicycloalkyl amines having the general formula ##STR17## and cyclic amines having the general formula ##STR18## where each R.sub.1 is independently selected from the group consisting of alkyls, cycloalkyls and aralkyls having from 1 to about 12 carbon atoms, and R.sub.2 is selected from the group consisting of a divalent alkylene, oxy- or aminoalkylene group having from about 3 to about 12 methylene groups;
• and, said solubilizing agent being selected from the group consisting of dienyl and vinyl aromatic oligomers having a degree of polymerization of from about 3 to about 300 polymerization units;
• and mixing said reaction product with an organic alkali metal compound;
• and optionally, a chelating reagent;
• said organolithium compound having the general formula RLi where R is selected from the group consisting of alkyls, cycloalkyls, alkenyls, aryls and aralkyls having from 1 to about 20 carbon atoms and short chain length low molecular weight polymers from diolefin and vinyl aryl monomers having up to about 25 units.