Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-06-02
1995-03-21
Lee, Mary C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548520, C07D20724
Patent
active
053997158
DESCRIPTION:
BRIEF SUMMARY
FIELD OF ART
This invention relates to novel polyamino oligomers, a process for preparing the same, polymaleimide compounds derived from said polyamino oligomers, resin compositions containing said compounds, and copper-clad laminates using said compositions.
The polyamino oligomers of this invention find a wide scope of use, such as preparation of curing agents for laminate resins which are low in melting point (or softening point) and desirably used without a solvent, and intermediates for various types of resins such as polymaleimide resins, polyamide resins, etc.
The polymaleimide compounds of this invention can be also used for laminate resins which are low in melting point, capable of use without a solvent and also low in dielectric constant and water absorptivity, and molding resins with excellent single workability.
BACKGROUND ART
As the art regarding the polyamino oligomers of this invention, there is known a process for preparing bis(p-aminocumyl)benzenes through acid catalytic reaction of aniline derivatives and diisopropenylbenzenes.
For instance, in German Patent No. 2,111,194, U.S. Pat. No. 3,365,347 and Japanese Patent Application Kokai No. 44/1986, it is proposed to react aniline derivatives and diisopropenylbenzenes under the appropriate conditions by using an acid catalyst and further carry out a purification operation such as crystallization for obtaining pure bis(p-aminocumyl)benzenes.
Bis(p-aminocumyl)benzenes obtained according to these methods are a crystalline solid with a melting point of 100.degree. C. or higher, so that when they are blended in a resin, it is necessary to apply a pertinent treatment such as heating them to a temperature higher than their melting point or dissolving them in a suitable solvent. These treatments, however, would give rise to such problems as increase of viscosity of the resin due to the advancement of reaction and formation of voids in the course of curing reaction, so that a compound which unnecessitates these treatments has been desired.
The polymaleimide compounds are being made practical use of by utilizing their excellent heat resistance, but they have the defects that they singly are hard to dissolve in general-purpose organic solvents and are also low in water absorptivity and poor in electrical properties due to their high polarity.
For overcoming these defects, bis(p-aminocumyl)benzenes obtained from an acid catalytic reaction of aniline derivatives and diisopropenylbenzenes, such as mentioned above, are further reacted with maleic anhydride in the presence of a dehydrating agent, a catalyst and a base to obtain bis(p-N-maleimidecumyl)benzenes, as described in International Application Laid-Open No. W087/00835. However, these compounds, being a crystalline solid with a high melting point, need to be subjected to a pertinent treatment such as melting by heating to a temperature above their melting point or dissolving in a suitable solvent, before molding. In the former case, since the difference between the compound melting point and the maleimide group reaction temperature is reduced, the time available for molding might be limited, and in the latter case, there is a risk of causing formation of voids in the course of molding. Also, these compounds are not necessarily satisfactory in water resistance and electrical properties.
Thermosetting resins have been popularly used as matrix resin for printed wiring boards. With operational speedup of semiconductor elements in multi-layer printed wiring boards for high-speed computers in recent years, necessity is increasing for corresponding speedup of response of circuitries on the printed board. Signal propagation speed in circuitries on the printed board depends on dielectric constant of the insulating material holding the circuitries, and generally the lower the dielectric constant of a material, the higher signal propagation speed it offers. Hitherto, polyimide resins and heat resistant epoxy resins have been used for such purpose.
The conventional polyimide resins and heat resistant epoxy r
REFERENCES:
patent: 3365347 (1968-01-01), Lund et al.
patent: 4205160 (1980-05-01), Gloth et al.
CA 107:23734; A new bismaleimide-chemistry and application. Lee et al., p. 2, 1987.
Chemitech, Aug. 1986, pp. 500-504, Howard A. Colvin et al., "Polymers from diisopropenyibenzene".
Endo Yasuhiro
Kamio Kunimasa
Naitoh Shigeki
Ueda Youichi
Lee Mary C.
McKane Joseph K.
Sumitomo Chemical Company Limited
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