Aromatic bismaleimide derivatives and process for preparing same

Details Aromatic bismaleimide derivatives and process for preparing same Aromatic bismaleimide derivatives and process for preparing same

1987-07-22

1991-05-07

Wax, Robert A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548521, 548461, 548549, C07D207452

Patent

active

050138480

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to aromatic bismaleimide derivatives useful as the monomer of high temperature resistant polymers and the method for preparing the same.


BACKGROUND ART

Heretofore, thermosetting resins having imide structure have been widely used in industry due to their excellent properties such as electrical insulation, high-temperature stability and dimensional stability of molded articles.
Particularly, the thermosetting resin derived from aromatic bismaleimide is an insoluble and infusible material having excellent high-temperature stability. However, it has drawbacks of inferior impact resistance and poor flexibility.
Therefore, as a method for improving the impact strength and flexibility of the resin derived from aromatic bismaleimide, aromatic bismaleimide was tried to use in combination with aromatic diamines. For example, polyamino-bismaleimide resin (trade mark KERIMIDE, a product from Rhone-Poulenc Ind.) has impact strength and flexibility superior to the resin from aromatic bismaleimide alone. Thus the former resin is widely used for impregnation varnish, laminated boards, molded articles etc.
The above thermosetting resins, however, have been still unsatisfactory in the impact strength and flexibility viewpoint.
Therefore, monomers have not yet been provided for the thermosetting resins being satisfied with these properties.


DISCLOSURE OF THE INVENTION

An object of this invention is to provide novel and useful aromatic bismaleimide derivatives being useful as the raw material for the aromatic bismaleimide type thermosetting resin which is widely employed in industry in recent years.
Another object of this inventions is to provide novel and useful aromatic bismaleimide derivatives being useful as the raw material for the aromatic bismaleimide type thermosetting resin which is excellent in impact strength, flexibility and toughness.
This invention provides the following aromatic bismaleimide derivative:
An aromatic bismaleimide derivative represented by the formula (I): ##STR4## wherein X is ##STR5## where R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are a hydrogen atom or a methyl group.
This invention also provides the following process for preparing the above aromatic bismaleimide derivative:
A process for preparing the aromatic bismaleimide derivative having the formula (I) which comprises reacting an aromatic diamine having the formula (II): ##STR6## wherein X is the same as in the formula (I), with maleic anhydride and then ring-closing resultant aromatic bismaleamic acid.
The aromatic bismaleimides represented by the aforementioned formula are novel compounds. The aromatic bismaleimide resins derived from these novel aromatic bismaleimides as the monomer, have excellent impact strength, flexibility and toughness in addition to the characteristics of conventional thermosetting resins.


THE BEST MODE FOR CARRYING OUT THE INVENTION

The ether-linkage containing diamines of the formula (II) are employed as the materials for preparing the novel aromatic bismaleimide derivatives of this invention.
The diamines include, for example, 4,4'-bis(3-aminophenoxy)biphenyl, 4,4'-bis(3-aminophenoxy)-diphenyl sulfide, 4,4'-bis(3-aminophenoxy)benzophenone, 2,2-bis[4-(3-aminophenoxy)phenyl]propane, 2,2-bis[3-methyl-4-(3-aminophenoxy)phenyl]propane, 2,2-bis[3,5-dimethyl-4-(3-aminophenoxy)phenyl]propane, 2-[3,5-dimethyl-4-(3-aminophenoxy)phenyl]-2-[4-(3-aminophenoxy)phenyl]prop ane, and 2-[3-methyl-4-(3-aminophenoxy)phenyl]-2-[4-(3-aminophenoxy)phenyl]propane, and the like.
These ether linkage containing diamines are those having amino groups located at m-positions to the ether linkages. These diamines can be favorably prepared by the following method which was found by the inventors of the present invention.
These diamines are prepared by condensing m-dinitrobenzene with dihydroxy compounds and then reducing the resultant intermediates.
In particular, a dihydroxy compound having the formula (III): m-dinitrobenzene in an aprotic polar solvent in the presence of a base to obtain

REFERENCES:
patent: 4376206 (1983-03-01), Oba et al.
patent: 4460783 (1984-07-01), Nishikawa et al.
patent: 4691025 (1987-09-01), Domeier
Morrison and Boyd, Organic Chemistry, 3rd ed. 1973, pp. 734-738.

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