Synthesis and Characterization of a New Class of Thermosetting Resins: Allyl and Propargyl Substituted Cyclopentadiene Derivatives
Technical rept. 1 Jun 1993-31 May 1994
UNIVERSITY OF SOUTHERN MISSISSIPPI HATTIESBURG DEPT OF POLYMER SCIENCE
Pagination or Media Count:
A series of all-hydrocarbon resins were synthesized by reacting cyclopentadiene with allyl chloride, propargyl chloride, or a mixture of allyl chloride and propargyl chloride, under phase transfer conditions. Phase transfer reactions with and without added solvents, and with either quaternary ammonium or crown ether type catalysts, yielded similar products consisting of a mixture oa 1,1-disubstituted cyclopentadiene minor amount and 2-3 isomers each of tri- , penta-, and hexa-substituted derivatives. No further reaction of each of these components was possible. The overall substitution pattern varied little with changes in reaction conditions although limiting the allyl chloride content led to still reactive, partially substituted products. Incorporation of all- propargyl and high propargyl-to-allyl mixed functionalities on cyclopentadiene yielded products whose stability was very low, hindering their thorough characterization. Preliminary evaluation was therefore carried out for mixed resins with lower propargyl functionality. The allyl substituted resin allylated cyclopentadiene, ACP underwent thermal cure without initiator at around 200 deg C while allylpropargyl substituted resin 71 ratio, APCP showed a faster, lower temperature cure at around 120 deg C. Cationic cure of ACP was also initiated by a novel sulfonium salt at around 100 deg C.
- Inorganic Chemistry
- Organic Chemistry
- Physical Chemistry