Ciba-Geigy Corporation

Ciba-Geigy Corproation

Charles E Monnier

Martin Roth

Sameer H Eldin

Friedrich Lohse

Roland Darms

Sheik A Zahir

Vratislav Kvita

Friedrich Stockinger

Peter Flury

The invention relates to compounds of the formula I or II ##STR1## in which A is a radical ##STR2## R.sup.1 is hydrogen or methyl, R.sup.2 is the radical of an aliphatic, cycloaliphatic, aromatic or araliphatic diol after both of the hydroxyl groups have been removed, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, chlorine or bromine, R.sup.7 is a radical of the formula III, IV, V or VI ##STR3## R.sup.8, R.sup.10, R.sup.12 and R.sup.14 are hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl, R.sup.9, R.sup.11, R.sup.13 and R.sup.15 are hydrogen or C.sub.1 -C.sub.6 alkyl and the average value of n (number average) is a number from 1 to 20, it being possible for the radicals R.sup.1 to R.sup.15, within a given molecule, to assume different meanings within the scope of the definitions given. These compounds or also the epoxidized intermediates of the formula X ##STR4## in which R.sup.1 to R.sup.3 are as defined above and R.sup.7 is a radical of the formula IV or VI can be processed to give cured products having a high glass transition temperature and a low tendency to discoloration.

Advanced epoxide resins based on cyclohex-1-ylmethylenediphenol

The invention relates to compounds of the formula I or II ##STR1## in which A is a radical ##STR2## R.sup.1 is hydrogen or methyl, R.sup.2 is the radical of an aliphatic, cycloaliphatic, aromatic or araliphatic diol after both of the hydroxyl groups have been removed, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another are hydrogen, C.sub.1 -C.sub.6 alkyl, chlorine or bromine, R.sup.7 is a radical of the formula III, IV, V or VI ##STR3## R.sup.8, R.sup.10, R.sup.12 and R.sup.14 are hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl, R.sup.9, R.sup.11, R.sup.13 and R.sup.15 are hydrogen or C.sub.1 -C.sub.6 alkyl and the average value of n (number average) is a number from 1 to 20, it being possible for the radicals R.sup.1 to R.sup.15, within a given molecule, to assume different meanings within the scope of the definitions given. These compounds or also the epoxidized intermediates of the formula X ##STR4## in which R.sup.1 to R.sup.3 are defined above and R.sup.7 is a radical of the formula IV or VI can be processed to give cured products having a high glass transition temperature and a low tendency to discoloration.

So-called advanced epoxide resins based on

The invention relates to compounds of the formula I ##STR1## in which A is a group ##STR2## R.sup.1 is hydrogen or methyl R.sup.2 is C.sub.1 -C.sub.6 -alkyl, halogen or phenyl,

Multifunctional epoxide resins

Novel epoxidised phenol ethers of formula I ##STR1## are described wherein R.sup.1 denotes C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.9 cycloalkyl or C.sub.7 -C.sub.14 aralkyl, R.sup.2 has one of the meanings of R.sup.1 or is, in addition hydrogen or a radical or formula II ##STR2## R.sup.3 denotes C.sub.1 -C.sub.6 alkyl or halogen, R.sup.4 and R.sup.5 denotes hydrogen or C.sub.1 -C.sub.6 alkyl, R.sup.6 denotes hydrogen or methyl, m is 0, 1 or 2 and n is an integer from 0 to 30, with the proviso that at least two radicals, R.sup.2, must be epoxide groups of formula II. The compounds are especially suitable for encasing electronic components.

Phenol ethers containing epoxide groups

2,6-Disubstituted 4-epoxypropyl glycidyl ethers of the formula ##STR1## wherein X is a group R' or X is a group of the formula ##STR2## and each of R and R' independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, a halogen atom or C.sub.6 -C.sub.10 aryl, can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for application in the electronics industry, or as adhesives. Compounds of the formula are also valuable reactive diluents for curable epoxy resin mixtures.

2,6-disubstituted 4-epoxypropylphenyl glycidyl ethers and the use thereof

A process for the preparation of glycidyl compounds by reacting a compound containing at least one phenolic group with at least the equivalent amount, based on the phenolic group, of a halohydrin in a substantially anhydrous, aprotonic solvent in the presence of a solid, substantially anhydrous catalyst, is described, which process comprises carrying out the reaction at a temperature in the range from 40.degree. to 80.degree. C. in the presence of an alkali metal carbonate, an aprotonic dipolar solvent with a static relative dielectric constant of more than 25 (at 25.degree. C.) and a permanent electric dipole moment of more than 2.5 D being used, an additional feature of said solvent being that the transition energy of the solvatochromic absorption band of the dissolved N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate is in the range from 168 to 197.4 kJ/mole (at 25.degree. C.), or which process comprises carrying out the reaction at a temperature in the range from 60.degree. to 80.degree. C. in the presence of an alkali metal hydroxide and a phase transfer catalyst chosen from the group consisting of ammonium and/or phosphonium compounds, the water of reaction formed being removed continuously and an inert, aprotonic, apolar solvent with a static relative dielectric constant of less than 8.0 (at 25.degree. C.) and a permanent electric dipole moment of less than 2.0 D being used, an additional feature of said solvent being that the transition energy of the solvatochromic absorption band of the dissolved N-(3,5-diphenyl-4-hydroxyphenyl)-2,4,6-triphenylpyridinium perchlorate is in the range from 140 to 165 kJ/mole (at 25.degree. C.). The resins obtained in this manner have a high degree of epoxidation and a low content of hydrolysable or ionic halogen. They are particularly suitable as potting resins for electronic components.

Process for the preparation of glycidyl compounds

The invention relates to polyepoxides which are obtainable by reacting compounds of formula I ##STR1## wherein n is 1 or 2, and X, if n is 1, is a group R.sub.3, or, if n is 2, X is a group of the formula ##STR2## each of R.sub.1 and R.sub.3 independently of the other is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, allyl, a halogen atom or C.sub.6 -C.sub.10 aryl and R.sub.2 is allyl, 1-propenyl or 2-propenyl, with compounds containing phenolic OH groups, and subsequently epoxidizing the resultant adducts in the presence of a peracid. Said polyepoxides can be used, together with customary epoxy resin hardeners, for the preparation of cured products, in particular for coating electronic components, or as adhesives.

Polyepoxides and the use thereof

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 process for the preparation of allyl ethers of the formula

Process for the preparation of di- and poly-allyl ethers

1,5-Dimethyl-1,2;5,6-diepoxycyclooctane is prepared by epoxidizing 1,5-dimethylcycloocta-1,5-diene with aqueous peracetic or perpropionic acid at a temperature not exceeding 50.degree. C. and within a pH range from 1.5 to 5.5. The diepoxide according to the invention can be cured by means of curing agents for epoxide resins to give moulded materials having valuable mechanical properties. It is also suitable for use as a reactive, latent diluent.

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Villars-sur-Glane, Switzerland

Charles E Monnier