Preparation of Polyimides Utilizing the Diels−Alder Reaction. 1,4-[N,N‘-Bis(butadienyl-2-methyl)diamido]-2,3,5,6- tetramethylbenzenes with Bismaleimides

Bis(amide-1,3-diene) monomers were prepared from 1,4-[N,N‘- bis(butadienyl-2-methyl)diamino]-2,3,5,6-tetramethylbenzene and several alkyl and aryl acid chlorides. The corresponding poly(amide imide)s were prepared by the Diels−Alder reaction involving these bis(amide-1,3-diene)s with bismaleimides....

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Bibliographic Details
Published in:Macromolecules 1996-02, Vol.29 (4), p.1123-1130
Main Authors: Smith, Joseph G, Sun, Fred, Ottenbrite, Raphael M
Format: Article
Language:English
Subjects:
Applied sciences
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polycondensation
Preparation, kinetics, thermodynamics, mechanism and catalysts
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Summary:Bis(amide-1,3-diene) monomers were prepared from 1,4-[N,N‘- bis(butadienyl-2-methyl)diamino]-2,3,5,6-tetramethylbenzene and several alkyl and aryl acid chlorides. The corresponding poly(amide imide)s were prepared by the Diels−Alder reaction involving these bis(amide-1,3-diene)s with bismaleimides. The polymers exhibited inherent viscosities of 0.21−0.81 dL/g and glass transition temperatures ranging from 202 to 269 °C. Moderate thermal stability was observed by dynamic thermogravimetric analysis, with 10% weight loss occurring between 318 and 350 °C in helium. The polymers were soluble in N,N-dimethylacetamide and chlorinated solvents. Creasable films were obtained by solution casting from chloroform. The chemistry and physical properties of the monomers and polymers are discussed.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma9464332