Patent GB-859456-A (GB)
Title: Improvements in or relating to the production of polyglycidyl ethers of tetrakis (alkyl-substituted hydroxyphenyl) alkanes
IPC: C07C37/20
Filed: 1959-03-05
Abstract: The invention comprises a polyglycidyl ether of alpha, alpha, omega, omega-tetrakis (alkylsubstituted hydroxyphenyl) alkane in which at least three of the hydroxyl groups on the phenyl radicals are para to the alkane chain, each alkyl substituent on at least three of the phenyl radicals is ortho to the hydroxyl groups, and the alkane chain has at least two carbon atoms.  The ether is prepared by reacting the corresponding hydroxy compound with epichlorohydrin or dichlorohydrin in the presence of an alkali metal hydroxide.  Preferably 2 to 10 molecules of chlorhydrin per phenolic hydroxyl group are used, the reaction being effected by gradual addition of aqueous alkali metal hydroxide to a refluxing mixture of the reactants, with azeotropic distillation of the water with the epichlorhydrin.  The products are solid epoxy resins, generally containing 3 to 4 glycidyl radicals. They may also contain as etherifying groups some dihydroxy glyceryl chlorohydroxy radicals.  In Examples (2) and (3) 1, 1, 2, 2-tetrakis (m-methyl-p-hydroxyphenyl) ethane and epichlorohydrin are reacted to give the polyglycidyl ether which is mixed in acetone solution with boron trifluoride-monethylamine catalyst and used for laminating glass cloth enclosed in regenerated cellulose film.  The polyglycidyl ethers may also be prepared from 1, 1, 3, 3-tetrakis (m-ethyl-p-hydroxyphenyl) propane 1, 1, 4, 4-tetrakis (m-methyl-p-hydroxy phenyl) butane; 1, 1, 5, 5-tetrakis (m-butyl-p-hydroxyphenyl)-3-methyl pentane; 1, 1, 2-tri (3-m-methyl-4-hydroxyphenyl)-2-(2-hydroxy-3-methylphenyl) ethane; 1, 1, 3-tri(3-ethyl-4-hydroxyphenyl) propane; 1, 1, 4-tri(3-propyl-4-hydroxyphenyl)-4-(2-hydroxy-3-propylphenyl) butane, 1, 1, 5-tri(3-methyl-4-hydroxyphenyl)-5-(2-hydroxy-3-methylphenyl) pentane and compounds with substituents on the alkane chain such as 1, 1, 3, 3-tetrakis (m-methyl-p-hydroxy-phenyl)-2-chloropropane and 1, 1, 4, 4-tetrakis (m-ethyl-p-hydroxyphenyl)-2, 3-dibromobutane. The preparation of the hydroxy compounds is described (see Group IV (b)).ALSO:The invention comprises alpha, alpha, omega, omega-tetrakis (alkyl-substituted hydroxyphenyl) alkanes in which at least three of the hydroxyl groups on the phenyl radicals are para to the alkane chain, each alkyl substituent on at least three of the phenyl radicals is ortho to the hydroxyl groups, and the alkane chain has at least two carbon atoms.  They are obtained by reacting the appropriate dialdehyde with at least 4 moles of an o-alkylphenol. o-Methyl, ethyl, propyl and butylphenols, ortho-xylenol and di-ortho-ethyl phenol are specified phenols.  In an example (1) 1, 1, 2, 2-tetrakis-(m-methyl-p-hydroxyphenyl) ethane is prepared by reacting glyoxal and o-cresol.  Other products referred to are 1, 1, 3, 3-tetrakis-(m ethyl-p-hydroxyphenyl) propane ; 1, 1, 4, 4-tetrakis (m methyl-p-hydroxyphenyl) butane ; 1, 1, 5, 5-tetrakis (m-butyl-p-hydroxyphenyl)-3-methylpentane ; 1, 1, 2-tri (3-methyl-4-hydroxyphenyl)-2-(2-hydroxy-3-methylphanyl) ethane ; 1, 1, 3-tri (3-ethyl-4-hydroxyphenyl).-3-(2-hydroxy-3-ethylphenyl) propane ; 1, 1, 4-tri (3-propyl-4-hydroxy-phenyl)-4-(2-hydroxy-3- propyl phenyl butane; 1, 1, 5-tri (3-methyl-4-hydroxy-phenyl)-5-(2-hydroxy-3-methylphenyl) pentane ; and compounds with substituents on the alkane chain such as 1, 1, 3, 3-tetrakis-(m-methyl-p-hydroxyphenyl)-2-chloropropane and 1, 1, 4, 4-tetrakis (m-ethyl-p-hydroxyphenyl)-2, 3-dibromobutane. The products are used for the preparation of epoxy resins, (see Group IV(a)).