Tertiaryaminoalkyllithium initiators and the preparation thereof
AssigneeBridgestone Corporation
InventorsWilliam L. Hergenrother, Michael L. Kerns, David F. Lawson
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Abstract
Relatively pure tertiaryaminoalkyllithium initiators suitable for anionic polymerization reactions are prepared at low temperatures in an organic ether by reacting an equivalent excess of lithium metal with a tertiaryaminoalkylhalide. The lithium initiators are very stable at moderate temperatures when the ether is replaced by an aliphatic, a cycloaliphatic, or an aromatic solvent. Yields of the initiator in excess of 98% are readily achieved.
Claims15
An initiator solution, comprising;
- a moderate temperature stable anionic initiator composition contained in a hydrocarbon solution, said moderate temperature being from about -20.degree. C. to about 60.degree. C.,
- said anionic initiator being an aminoalkyllithium initiator of the formula ##STR3## wherein R.sup.1 and R.sup.2.sup.2, independently, are an alkyl having from 1 to 12 carbon atoms, wherein R is an alkylene or cycloalkylene having 1 to 10 carbon atoms, and optionally including from 1 to 4 alkyl substituents on each ring wherein said alkyl contains from 1 to 4 carbon atoms, wherein the amount of said anionic initiator in said composition is at least a 60 percent yield based upon a starting material which is a halide of said Formulas I, II, III, IV, or V, or combinations thereof.
A process for producing an anionic initiator solution, comprising the steps of:
- reacting an aminoalkylhalide compound of the formula ##STR4## wherein R.sup.1 and R.sup.2, independently, are an alkyl having from 1 to 12 carbon atoms, wherein R is an alkylene or cycloalkylene having from 1 to 10 carbon atoms, wherein X is a halide, and optionally including from 1 to 4 alkyl substituents on each ring wherein said alkyl substituent contains from 1 to 4 carbon atoms,
- with an excess of lithium in the presence of an organic ether at or below the temperature of the boiling point of said organic ether to form an anionic initiator, said organic ether having the formula R.sup.3 -O-R.sup.4 where R.sup.3 and R.sup.4, independently, are an alkyl having from 1 to 4 carbon atoms, and
- removing said organic ether and adding a hydrocarbon solvent to form an ambient temperature stable initiator.
An anionic initiator solution made by reacting a tertiaryaminoalkylhalide with an excess of lithium in the presence of an organic ether at or below the boiling point of said ether and replacing said ether with a hydrocarbon solvent, said organic ether having the formula R.sup.3 -O-R.sup.4 where R.sup.3 and R.sup.4, independently, are an alkyl having from 1 to 4 carbon atoms,
- wherein said initiator is stable in said hydrocarbon solvent at a moderate temperature, wherein the stability of said anionic initiator is less than 1 percent mole decay per week at 20.degree. C., and wherein the purity of said anionic initiator solution is at least 80 percent by weight.
Dependencies are inferred from the claim text.