Compound is an efficient initiator capable of producing a polymer with a phenol group at the initiating end of the chain. Derivative may be used as a polymerization initiator to produce large quantities of phenol-terminated polymers

Hirshfield, S. M.

English

NASA Technical Reports Server

1972	 B72-10223 
NASA TECH BRIEF 
Ames Research Center	 -4r 
NASA Tech Briefs announce new technology derived from the U.S. space program. They are issued to encourage 
commercial application. Tech Briefs are available on a subscription basis from the National Technical Information 
Service, Springfield, Virginia 22151. Requests for individual copies or questions relating to the Tech Brief program may 
be directed to the Technology Utilization Office, NASA, Code KT, Washington, D.C. 20546. 
Initiation of Polymerization
by Tetrabutylammoniuhi p-Litbiophenoxide 
The new compound, tetrabutylammonium p-lithio-
phenoxide, has been found to be an efficient poly-
merization initiator that is also capable of producing 
a polymer-with a phenol group at the initiating end of 
the chain. Analogous initiators, such as lithium p-
lithiophenoxide, can produce the same phenol-termi-
nated polymer; however, such compounds are insol-
uble in solvents like tetrahydrofuran (<0.4 g/liter) 
because of the presence of the inorganic atom in their 
structures. The limited solubility precludes use of the 
inorganic metal salts for large-scale polymerizations. 
The rationale behind the preparation of the new 
compound was predicated on the assumption that 
replacement of the inorganic atom with the organic 
tetrabutylammonium group would provide a much 
more soluble initiator, and this was indeed shown to 
be true. The tetrabutylammonium derivative has been 
found to be much more soluble than the lithium 
derivative (>8.0 g/liter). Consequently, the tetra-
butylammonium derivative may be freely used as a 
polymerization initiator to produce large quantities 
of phenol-terminated polymers. 
The new compound is prepared by forming tetra-
butylammonium p-bromophenoxide from p-bromo-
phenol and tetrabutylammonium hydroxide and then 
treating the tetraalkyl-substituted phenoxide with n-
butyl lithium in tertahydrofuran. 
Reference: 
Hirshfield, S. M.: Polymer Containing Functional 
End Groups is Base for New Polymers. NASA Tech 
Brief 71-10184, June 1971. 
Note: 
No additional documentation is available. Specific 
questions, however, may be directed to: 
Technology Utilization Officer 
Ames Research Center 
Moffett Field, California 94035 
Reference: B72-10223 
Patent status: 
No patent action is contemplated by NASA. 
Source: Stanley M. Hirshfield of 
Rocketdyne/North American Rockwell Corp.

under contract to

Ames Research Center 
(ARC-10553) 
Category 04 
Thisdocumentwas prepared under the sponsorship of the National	 Government assumes any liability resulting from the use of the 
Aeronautics and Space Administration. Neither the United States 	 information contained in this document, or warrants that such use 
Government nor any person acting on behalf of the United States	 will be free from privately owned rights.
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Initiation of polymerization by tetrabutylammonium p-lithophenoxide p-lithiophenoxide

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