Mitsui Toatsu Chemicals, Incorporated

Amdahl Corporation

Saburo Kawashima

Akihiro Yamaguchi

Shoji Tamai

Hideaki Oikawa

Masahiro Ohta

Katsuaki Iiyama

Yoshiho Sonobe

Kouji Ohkoshi

Kenichi Sugimoto

Keizaburo Yamaguchi

Makoto Asano

Tadashi Asanuma

Tadashi Kobayashi

Yoshimitsu Tanabe

Toshiyuki Nakakura

Satoru Kishi

Hideo Sakai

Yuko Ishihara

Tomohito Koba

Chiaki Maruko

Misao Masuda

Toshiyuki Kataoka

Masao Yoshikawa

Hideaki Okikawa

Nobuhito Koga

Hisamichi Murakami

Yoshimitu Tanabe

Yoshiho Snobe

Katsuaki Liyama

In one aspect, the present invention relates to polyimides having excellent thermal resistance and process for preparing the same comprising carrying out condensation of 4,4'-bis(3-aminophenoxy)biphenyl with pyromellitic dianhydride in the presence of a different diamine compound and optionally with a different tetracarboxylic acid dianhydride. In a second aspect, the present invention relates to a heat resistant resin composition consisting essentially of an aromatic polyetherimide and a defined polyimide. In a third aspect, the present invention relates to a polyimide resin composition comprised on a defined polyimide and a separate high-temperature engineering polymer. In a fourth aspect, the present invention relates to a resin composition comprised of a defined polyimide and an aromatic polyamideimide.

Polyimides, process for the preparation thereof and polyimide resin

Disclosed are a novel aromatic diamine; a polymide comprising 1,3-bis(3-aminobenzoyl)benzene or 4,4'-bis(3-aminobenzoyl)biphenyl as a diamine component and having recurring structural units represented by the formula (III): ##STR1## wherein R is a tetravalent radical selected from the group consisting of an aliphatic radical having from 2 to 27 carbon atoms, alicyclic radical, monoaromatic radical, condensed polyaromatic radical, and noncondensed aromatic radical connected each other with a direct bond or a bridge member, and X is a divalent radical of ##STR2## and a polyimide having a terminal aromatic group which is essentially unsubstituted or substituted with a radical having no reactivity with amines or dicarboxylic acid anhydrides or a composition comprising said polyimide.

Aromatic diamine intermediates useful in the preparation of polyimide

The heat resistant adhesive of the invention comprises polyamic acid and/or polyimide which are prepared by using 1,3-bis(3-aminophenoxy)benzene as an aromatic diamine component and 3,3',4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride and/or 3,3',4,4'-diphenylethertetracarboxylic dianhydride as tetracarboxylic acid dianhydrides, and further by blocking the polymer chain end with dicarboxylic anhydride or a monoamine compound; or comprises a polyimide solution containing the polyimide in a good solvent. The adhesive of the invention is a heat-resistant adhesive capable of adhering under mild temperature/mild pressure conditions. The adhesive of polyimide solution can provide desired adhesion by simple procedures such as applying to the adherend and heating under pressure and exhibits excellent adhesive strength. Consequently, the heat-resistant adhesive of the invention is very useful for the adhesion of structural and electronic materials and other industrial materials.

Heat-resistant adhesive and method of adhesion by using adhesive

Polyimide having repeating units of the following formula (I) and its polyamic acid precursor having repeating units of the following formula (II) are disclosed; ##STR1## (where Y is a radical selected from the group consisting of a bond, divalent hydrocarbon having 1 to 10 carbons, hexafluorinated isopropylidene, carbonyl, thio, sulfinyl, sulfonyl and oxide, and R is a tetra-valent radical selected from the group consisting of aliphatic radical having 2 and more carbons, cyclo-aliphatic radical, monoaromatic radical, condensed polyaromatic radical, and non-condensed polyaromatic radical wherein aromatic radicals are mutually connected with a bond or a crosslinking function). Typical examples of polyimide and polyamic acid include where Y is thio radical and R is ##STR2## Y is a bond and R is III or IV, and Y is isopropylidene radical and R is IV. The polymers can be prepared from corresponding diamine and tetracarboxylic acid dianhydride. Polyimide or polyamic acid of this invention is excellent for high-temperature adhesive.

Polyimide and high-temperature adhesive of polyimide

The heat resistant adhesive of the invention comprises polyamic acid and/or polyimide which are prepared by using 1,3-bis(3-aminophenoxy)benzene as an aromatic diamine component and 3,3', 4,4'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-benzophenonetetracarboxylic dianhydride and/or 3,3',4,4'-diphenylethertetracarboxylic dianhydride as tetracarboxylic acid dianhydrides, and further by blocking the polymer chain end with dicarboxylic anhydride or a monoamine compound; or comprises a polyimide solution containing the polyimide in a good solvent. The adhesive of the invention is a heat-resistant adhesive capable of adhering under mild temperature/mild pressure conditions. The adhesive of polyimide solution can provide desired adhesion by simple procedures such as applying to the adherend and heating under pressure and exhibits excellent adhesive strength. Consequently, the heat-resistant adhesive of the invention is very useful for the adhesion of structural and electronic materials and other industrial materials.

A novel aromatic diamine; a polyimide comprising 1,3-bis(3-aminobenzoyl)benzene or 4,4'-bis(3-aminobenzoyl)biphenyl as a diamine component and having recurring structural units represented by the formula (III): ##STR1## wherein R is a tetravalent radical selected from the group consisting of an aliphatic radical having from 2 to 27 carbon atoms, alicyclic radical, monoaromatic radical, condensed polyaromatic radical, and noncondensed aromatic radical connected each other with a direct bond or a bridge member, and X is a divalent radical of ##STR2## and a polyimide having a terminal aromatic group which is essentially unsubstituted or substituted with a radical having no reactivity with amines or dicarboxylic acid anhydrides or a composition comprising said polyimide.

Aromatic diamine compound, preparation process of same and polyimide

This invention relates to molding resin compositions, and more particularly relates to polyimide resin compositions having markedly improved molding ability in addition to excellent high temperature stability, chemical resistance and mechanical strength. The polyimide resin compositions of this invention comprises 99.9 to 50.0% by weight of the polyimide and 0.1 to 50.0% by weight of polyphenylene sulfide and/or aromatic polysulfone and/or aromatic polyetherimide high-temperature engineering polymer. The polyimide consists essentially of recurring units of the following formula: ##STR1##

Polyimide resin composition

Polyimide having repeating units of the following formula (I) and its polyamic acid precursor having repeating units of the following formula (II) are disclosed; ##STR1## (where Y is a radical selected from the group consisting of a bond, divalent hydrocarbon having 1 to 10 carbons, hexafluorinated isopropylidene, carbonyl, thio, sulfinyl, sulfonyl and oxide, and R is a tetra-valent radical selected from the group consisting of aliphatic radical having 2 and more carbons, cyclo-aliphatic radical, monoaromatic radical, condensed polyaromatic radical, and noncondensed polyaromatic radical wherein aromatic radicals are mutually connected with a bond or a crosslinking function). Typical examples of polyimide and polyamic acid include where Y is thio radical and R is ##STR2## Y is a bond and R is III or IV, and Y is isopropylidene radical and R is IV. The polymers can be prepared from corresponding diamine and tetracarboxylic acid dianhydride. Polyimide or polyamic acid of this invention is excellent for high-temperature adhesive.

Polyimide and high-temperature adhesive of polyimide based on

This invention relates to molding resin compositions, and more particularly relates to polyimide resin compositions having markedly improved molding ability in addition to excellent high temperature stability, chemical resistance and mechanical strength. The polyimide resin composition of this invention comprises 99.9 to 50% by weight of the polyimide and 0.1 to 50% by weight of high temperature engineering polymer. The polyimide has recurring units of the following formula: ##STR1## wherein X is a sulfonyl radical or a carbonyl radical and R is a tetravalent radical selected from an aliphatic radical, alicyclic radical, monoaromatic radical, condensed aromatic radical and non-condensed aromatic radical. R is, for example, ##STR2## The high temperature engineering polymer is, for example, polyphenylene sulfide consisting of recurring units of the formula: ##STR3## aromatic polysulfone consisting of recurring units of the formula: ##STR4## or aromatic polyetherimide consisting of recurring units of the formula: ##STR5##

This invention relates to a method for preparing a polyimide having good heat-stability and excellent flowability in a molten state. The polymide is prepared by reacting aromatic diamines such as 4,4'-bis(3-aminophenoxy)biphenyl, bis[4-(3-aminophenoxy)phenyl] ketone and bis [4-(3-aminophenoxy)phenyl] sulfone; tetracarboxylic dianhydrides such as pyromellitic dianhydride, 3,3', 4,4'-benzophenonetetracarboxylic dianhydride and bis(3,4-dicarboxyphenyl) ether dianhydride; and dicarboxylic anhydrides such as glutaric anhydride, 1,2-hexanedicarboxylic anhydride, phthalic anhydride and 3,4-benzophenonedicarboxylic anhydride. The molar ratio of aromatic diamine: tetracarboxylic dianhydride: dicarboxylic anhydride is 1:(0.9 to 1.0):(0.001 to 1.0). The invention also relates to polyimide composite materials which are excellent in mechanical strengths and processability. The materials contain the polyimide and fibrous reinforcing materials such as yarn, roving, tow, fabrics, mats and felts of glass fiber, carbon fibers or aromatic polyamide fibers.

Process for preparing a polyimide and a composite material containing

Disclosed is a process for preparing a polyimide by reacting certain reactants. The reactants include an aromatic diamine which is 3,3'-diaminobenzophenone and/or bis(3-aminophenyl)sulfone, a tetrocarboxylic dianhydride and a dicarboxylic anhydride. A thermally stable polyimide can be obtained which displays excellent processability.

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Yokosuka, Japan

Saburo Kawashima