Cyclohexyl-group-containing glycidyl ethers
AssigneeCiba-Geigy Corporation
InventorsHeinz Wolleb, Andreas Kramer
Life of this patent
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Abstract
Novel cyclohexyl-group-containing glycidyl ethers of formulae I to IV according to claim 1, which are distinguished especially by a low chlorine content and a low viscosity and which can be used, for example, in epoxy resin formulations as reactive diluents, flexibilisers or adhesion enhancers, or can also be polymerised per se and used as coatings or casting resins, the products having only slight water absorption and having good external weather resistance.
Claims11
A cyclohexyl-group-containing glycidyl ether of formula I, II, III or IV having a chlorine content of less than 0.4% by weight and which is prepared from polyhydroxy compounds and epihalohydrin by adding an aqueous alkali hydroxide solution in the presence of a transfer catalyst selected from the group consisting of tetramethylammonium chloride, tetrabutylammonium bromide, N,N-dimethyl-pyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium iodide, N-butyl-N-methylpyrrolidinium bromide, N-benzyl-N-methylpyrrolidinium chloride, N-ethyl-N-methylpyrrolidinium bromide, N-butyl-N-methyl-morpholinium bromide, N-butyl-N-methylmorpholinium iodide, N-ethyl-N-hydroxyethylmorpholinium iodide, N-allyl-N-methylmorpholinium bromide, N-methyl-N-benzylpiperidinium chloride, N-methyl-N-benzyl-piperidinium bromide, N,N-dimethylpiperidinium iodide, N-methyl-N-ethylpiperidinium acetate and N-methyl-N-ethylpiperidinium iodide:
- ##STR17## wherein the individual symbols are defined as follows:
- R.sub.1, R.sub.2 and R.sub.3 are each independently of the others hydrogen, a C.sub.1 -C.sub.10 alkyl radical or a hydrogenated aryl radical;
- R.sub.4 and R.sub.5 are each independently of the other hydrogen or a C.sub.1 -C.sub.20 alkyl radical;
- R.sub.6 is hydrogen, a C.sub.1 -C.sub.10 alkyl radical or a hydrogenated aryl radical;
- X is a bridge member of the formula --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, --CO--, --O--, --S--, --SO.sub.2 --, ##STR18## Y=O (when n=1) or N (when n=2);
- m is the number 1, 2 or 3;
- n=l (when Y=O) or2 (when Y=N);
- o is a number from 1 to 30;
- and
- Z is a direct bond or a bridge member of the formula --CH.sub.2 -- or ##STR19##
Dependencies are inferred from the claim text.