US 4,551,508 A · Polyglycidyl ethers, process for production thereof, and cured products thereof

Abstract

Polyglycidyl ethers of the formula ##STR1## wherein: G represents hydrogen, ##STR2## R.sup.1 represents a hydrogen atom, an aliphatic, alicyclic, or aromatic hydrocarbon group, or a 5- or 6-membered oxygen or sulfur atom containing heterocyclic group which groups, other than hydrogen, may be substituted by halogen or the group --OG, R.sup.2 is hydrogen or ##STR3## n is a positive number up to 10, and at least two G groups in the molecule are other than hydrogen. The polyglycidyl ether is produced by condensing alpha-naphthol with an aldehyde, such as acetaldehyde, in the presence of an acid catalyst such as nitric acid, and optionally in the presence of an inert medium such as toluene, to form a novolak-type phenol which is thereafter condensed with an epihalohydrin. The polyglycidyl ethers may be cured with conventional curing agents. Composite materials containing a matrix formed from the cured polyglycidyl ether and a filler dispersed in the matrix have excellent heat resistance and low water absorption.

Claims20

Dependent claims

A polyglycidyl ether represented by the following formula (I) ##STR44## wherein G represents a hydrogen atom, ##STR45## R.sup.1 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 5 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a 5- or 6-membered heterocyclic group containing an oxygen or sulfur atom as a hetero atom, provided that the foregoing groups other than the hydrogen atom may be substituted by a halogen atom or the group --OG in which G is as defined,

R.sup.2 represents a hydrogen atom or the group ##STR46## in which G and R.sup.1 are as defined, and n is a positive number up to 10,
provided that all groups G, all groups R.sup.1 and all groups R.sup.2 in the molecule may respectively be identical or different but at least two G groups in the molecule are ##STR47##

A process for producing a polyglycidyl ether represented by the following formula (I) ##STR49## which comprises condensing alpha-naphthol with at least one aldehyde represented by the following formula (II)

R.sup.3 --CHO (II)
wherein R.sup.3 represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 5 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a 5- or 6-membered heterocyclic group containing an oxygen or sulfur atom as a hetero atom, provided that the foregoing groups other than the hydrogen atom may be substituted by
a halogen atom or a hydroxyl group, in the presence of an acid catalyst and optionally in the further presence of an inert reaction medium to form a polyol represented by the following formula (III) ##STR50## wherein R.sup.3 is as defined,
R.sup.4 represents a hydrogen atom or ##STR51## in which R.sup.3 is as defined, and m is a positive up to 10 number, provided that all R.sup.3 groups and all R.sup.4 groups may respectively be identical or different,
and thereafter condensing the resulting polyol with an epihalohydrin represented by the following formula (IV) ##STR52## wherein R.sup.5 represents a hydrogen atom or a methyl group, and X represents a halogen atom.

2 more elements

Dependencies are inferred from the claim text.

Polyglycidyl ethers, process for production thereof, and cured products thereof

Life of this patent

Polyglycidyl ethers, process for production thereof, and cured products thereof

Life of this patent

Abstract

Claims20