Synthesis and Characterization of a New Class of Thermosetting Resins: Allyl and Propargyl Substituted Cyclopentadiene Derivatives
Abstract
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 allyl/propargyl substituted resin (7:1 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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Jul 15, 1994
- Accession Number
- ADA281976
Entities
People
- J. Muthiah
- L. J. Mathias
Organizations
- University of Southern Mississippi