Ciba-geigy Corporation

Roland Darms

Gerd Greber

Vratislav Kvita

Siegfried Wyler

Josef Pfeifer

Dieter Lohmann

Theobald Haug

Hubert Meindl

Harry Beyeler

Andreas Kramer

Martin Roth

Charles E Monnier

Peter Furrer

The present invention relates to amides of formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each independently hydrogen or methyl, m is 1 to 5 and n is 1 to 5 and R.sup.4 is --NH.sub.2 or is derived from a mono- to pentavalent amine. Intermediates of formula VIII ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and m are as defined above and X is a carboxylic acid or acid ester group, --COCl, --COBr, --CHO or --CN, are also described. The compounds of formula I can be polymerized thermally. They are suitable for the preparation of adhesives, matrix resins or electrical insulating materials.

Polymers obtained by heating allybicyclo[2.2.1]hept-5-ene-2-carboxylic

The present invention relates to amides of formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen or methyl, m is 1 to 5 and n is 1 to 5 and R.sup.4 is --NH.sub.2 or is derived from a mono- to pentavalent amine. Intermediates of formula VIII ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and m are as defined above and X is a carboxylic acid or acid ester group, --COCl, --COBr, --CHO or --CN, are also described. The compounds of formula I can be polymerized thermally. They are suitable for the preparation of adhesives, matrix resins or electrical insulating materials.

Allylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid amides

Novel glycidyloxy diketones of the formula I ##STR1## (in which, for example, X is glycidyloxy, Y is H and R is 1,3-phenylene) are described. The compounds of the formula can be used together with customary curing agents and/or curing catalysts for the preparation of crosslinked (cured) products which have good thermal and mechanical properties.

Glycidyloxy diketones

Novel phthalic acid derivatives are described which are substituted by 2-propynyloxy groups, of the formula I ##STR1## in which Q.sub.1, and Q.sub.2 independently of one another are --OH or --O.sup.- M.sup.+, or Q.sub.1 and Q.sub.2 together form the grouping --O--, [O.sup.- ].sub.2 M.sub.1.sup.++ or --N(R.sub.2)--, M.sup.+ is an alkali metal ion, a trialkyl ammonium ion having 3-24 carbon atoms or a quaternary ammonium ion and M.sub.1.sup.++ is an alkaline earth metal ion, R.sub.2 is an alkyl group or an unsubstituted or substituted aryl group, n is 1 or 2 and R.sub.1 is hydrogen, if n is 1, or a direct bond, if n is 2, are described. The phthalic anhydrides which are substituted by 2-propynyloxy, of the formula I, can be used for curing epoxy resins, cured products with outstanding physical properties being obtained.

Phthalic acid derivatives which are substituted by 2-propynyloxy groups,

A flexible, printed circuit with excellent adhesion of the printed tracks, which is obtained by coating one side of a metal foil without an intermediate layer with a polymer consisting of a polyamide, polyimide or polyamide-imide containing siloxane groups, which is obtainable by crosslinking a silicon-modified polyamide prepolymer, polyamide-acid prepolymer or polyamide-amido-acid prepolymer of the formula I, heating the coated metal foil in the temperature range from 50.degree. to 300.degree. C. till a tack-free coating is obtained, exposing the opposite side of the coated metal foil, which side is provided with a photolacquer, through a photo mask, and developing the exposed metal foil.

Flexible, printed circuit

Flexible base materials consisting of a metal foil and a film, firmly adhering thereto without an interlayer, of a polyamide/polyimide block copolymer of the formula I, or of a polyamide/polyimide copolymer prepared from a polyamide acid block of the formula IVa or Va and a dicarboxylic acid dichloride of the formula XI and a diamine of the formula XII. The individual symbols are defined in claim 1. The base materials according to the invention are suitable for the preparation of flexible printed circuits.

Flexible base materials, their preparation and their use for printed

Flexible base materials consisting of a metal foil and a film of a polyamide, polyamide-imide and/or polyimide, firmly adhering thereto without an intermediate layer, the film being obtained by heating a polyamide, polyamide-amidoacid and/or polyamide-acid containing the structural units of the formulae I and II. The individual symbols are as defined in claim 1. The base materials according to the invention are useful for the production of flexible printed circuits.

New crosslinkable bis-imidyl derivatives are described which can be produced by reaction of imidylphthalic acid derivatives, such as maleimidyl-phthalic acid anhydrides, with monomeric, oligomeric or polymeric diamines. The new crosslinkable bis-imidyl derivatives can be used for producing crosslinked polymers which are distinguished, in particular, by their stability to oxidation and to heat.

Crosslinkable bis-imidyl derivatives

The Si-modified bis-phthalic acid derivatives according to the invention are monomeric, oligomeric or polymeric compounds. An example of a monomeric compound of the invention is the amidoacid of the formula ##STR1## which is formed by reacting 4,4'-diaminodiphenylmethane and 4-N,N'-bis-[3-tri-n-propoxy)-silyl-propyl]-aminophthalic anhydride in solution, in a molar ratio of 1:2. To produce oligomeric or polymeric compounds, the reaction has to be carried out with a 3rd component, for example pyromellitic dianhydride. The products are used as adhesion promoters, for example between inorganic solids and organic resins.

Silicon-modified bis-phthalic acid derivatives

The invention relates to Si-modified phthalic acid derivatives (acids, esters and anhydrides) of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are --OH, alkoxy with 1-12 C atoms or phenoxy or R.sub.1 and R.sub.2 together are the --O--group, X is a ##STR2## R.sub.3 is alkyl with 2-7 C atoms, cycloalkyl with 5-7 C atoms, benzyl or ##STR3## Q is methyl, phenyl or --OQ.sub.3 and Q.sub.1, Q.sub.2 and Q.sub.3 independently of one another are alkyl with 1-6 C atoms or phenyl. The products of the invention are prepared by reacting the corresponding allylamino-phthalic anhydrides or allylamino-phthalic acid esters with compounds of the formula III ##STR4## They are used as adhesion promoters, for example between inorganic solids and organic resins. They may also be used for the preparation of other Si-modified adhesion promoters, and as curing agents for epoxide resins.

Silicon-modified phthalic acid derivatives

New polynuclear aromatic diamines, such as 2,2'-di-(p-aminophenoxy)-biphenyl, a process for their manufacture and their use as polycondensation components for the manufacture of polyamide, polyamide-imide and polyimide polymers are described. The polymers obtained with the aromatic diamines according to the invention are readily soluble and can also be processed from the melt and are distinguished by good thermal, electrical and/or mechanical properties.

Aromatic diamines and their use as polycondensation components for the

New imidyl-benzene-dicarboxylic and -tricarboxylic acid derivatives, in particular 5-maleimidyl-trimellitic acid derivatives and 3,5-bis-(maleimidyl)-phthalic acid derivatives, and a process for their manufacture are described. These imidylbenzene-dicarboxylic and -tricarboxylic acid derivatives are suitable for the manufacture of crosslinkable polymers, above all polycondensation and polymerization products, which are distinguished by good processability and good solubility in customary organic solvents. Imidyl compounds, according to the definition, which have anhydride groups can also be used as curing agents for optionally modified epoxide resins.

Imidyl-benzene-dicarboxylic and -tricarboxylic acid derivatives

New crosslinkable bis-imidyl derivatives are described which can be produced by reaction of imidylphthalic acid derivatives, such as maleimidyl-phthalic acid anhydrides, with monomeric, oligomeric or polymeric diamines. The new crosslinkable bis-imidyl derivatives can be used for producing crosslinked polymers wich are distnguished, in particular, by their stability to oxidation and to heat.

The compounds according to the invention are Si-modified imidyl-phthalic acid derivatives of the formula ##STR1## and the corresponding cyclized imide derivatives; in the formula, A is a radical which completes to a substituted or unsubstituted imidyl group, R is a divalent organic radical, R.sub.1 and R.sub.2 are each hydrogen or a monovalent organic radical and Q, Q.sub.1 and Q.sub.2 are each a monovalent organic radical. A typical example is 3-dimethylmaleimidyl-phthalic acid N-(di-n-propoxymethylsilyl)propylimide, which is obtained by reacting 3-dimethylmaleimidyl-phthalic acid N-allylimide and di-n-propoxymethylsilane in solution, followed by cyclization. The products are used as adhesion promoters, for example between inorganic solids and organic resins.

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Therwil, Switzerland

Roland Darms