Gulf Oil Corporation

Patricia A Antonoplos

William J Heilman

Clarence D Bertino

The applicants have provided laminates prepared by (a) impregnating a glass fabric with an N-methyl-2-pyrrolidone solution of a compound having the structure of Formula A shown in FIG. 1 of the drawings, (b) heating the impregnated glass fabric to remove solvent therefrom and to covert the amic acid groups to imide groups, and (c) assembling a plurality of the impregnated glass fabrics from (b) and heating the assembly under pressure to a temperature in the range of 177.degree.-260.degree. C.

Laminates prepared from solutions of resins containing amic acid groups

The products of the invention are partial acetylene end-capped oligomers which have the structure as shown in FIG. 3 in which terminal R' group is derived from a mixture consisting of about 14-40 mol % of an aromatic monoamine and the balance an acetylene substituted aromatic monoamine. The products are prepared from either of two (2) precursors. The first precursor has the structure shown in FIG. 2. The second precursor is a complex amine salt having the structure shown in FIG. 5.

Novel partially acetylene end-capped polyimide oligomers

The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4',4'-benzophenonetetracarboxylic acid, an aromatic diamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.

Novel end-capped polyimide oligomers

The products of the invention are end-capped polyimide oligomers prepared from a dianhydride of an aromatic tetracarboxylic acid such as 3,3'4,4'-benzophenonetetracarboxylic acid, an aromatic triamine, and a 1-(aminoaryl)-3-hydroxy-3-methyl-1-butyne. The structure of the polyimide oligomers is shown in FIG. 3.

End-capped polyimide oligomers

Acetylene end-capped polyimide oligomers are prepared by a process including the following sequential steps:

Process for preparation of acetylene end-capped polyimide oligomers

The applicants have provided novel heat curable resin compositions consisting predominately of a chemical compound having the structure of Formula A shown in FIG. 1 of the drawings. A desirable characteristic of the novel resin compositions of the invention is that they have a high solubility in selected solvents such as N-methyl-2-pyrrolidone (NMP) so that resin solutions containing at least 30 weight % resin solids at ambient temperature can be prepared. Glass fabric laminates having a high loading of resin are easily prepared from such solutions. Typically, high solids solutions of the compounds of Formula A are prepared by a three-step process. A solution containing at least 17 weight % of 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride (BTDA) in N-methyl-2-pyrrolidone (NMP) is prepared by heating the BTDA and NMP to a temperature of at least 150.degree. C with stirring. The solution then is cooled to a temperature of about 60.degree. C and substantially 0.5 molar portion (based on 1 molar portion of BTDA) of a bis(aminophenoxy) benzene (APB) is added thereto to prepare a high solids solution of a compound having the structure of Formula B shown in FIG. 1. Subsequently, while maintaining this solution at a temperature of about 60.degree. C, substantially 1.0 molar portion of a 3-aminophenylacetylene (APA) is added thereto to prepare a high solids solution of a compound having the structure of Formula A.

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Houston, TX, United States of America

Patricia A Antonoplos