Patent GB-799629-A (GB)
Title: Improvements in or relating to epoxyalkyl aryl ethers and epoxy resins
Inventor: CLAIR WILLIAM EDWARD ST
IPC: C08G59/08
Filed: 1957-02-04
Abstract: Epoxy alkyl aryl ethers are made by dissolving a monomeric hydroxy aromatic compound in an amount of a haloepoxyalkane in excess of that required for etherification, heating the solution to at least 60 DEG C. and below the decomposition temperature of said haloepoxyalkane and adding gradually thereto an alkali hydroxide dissolved in an aliphatic alcohol having less than five carbon atoms.  Many haloepoxyalkanes are specified, examples being epichlorohydrin, 1-chloro-2,3-epoxybutane, 1-bromo-2,3-epoxypentane, 4 - chloro - 2 - methyl - 2,3 - epoxy pentane and 1 - chloro - 2 - methyl - 2,3 - epoxydecane. Aromatic hydroxy compounds specified are resorcinol, catechol, hydroquinone, phenol, cresol, xylonol, mesitol, durenol, thymol, quinol, pentamethyl phenol, orcinol, dihydroxyxylol, resorcinol, thymoquinol, pyrogallol, tetrahydroxy benzene, pentahydroxy benzene, naphthol, hexahydroxy benzene, anthrol and bis phenol. Alkali hydroxides specified are lithium, sodium, potassium, rubidium and caesium hydroxides.  In examples: (XI) to (XIII) resorcinol is dissolved in and reacted with epichlorohydrin in the presence of: (XI) a solution of potassium hydroxide in ethanol; (XII) a solution of sodium hydroxide in ethanol; and (XIII) a solution of sodium hydroxide in methanol.  In examples (XIV) and (XV) phenol is dissolved in and reacted with epichlorohydrin in the presence of an ethanolic solution of (XIV) potassium hydroxide and (XV) sodium hydroxides whilst in examples (XVI) and (XVII) hydroquinone is dissolved in and reacted with epichlorohydrin in the presence of an ethanolic solution of (XVI) potassium hydroxide and (XVII) sodium hydroxide.ALSO:Epoxy resins and epoxy alkyl aryl ethers are made by dissolving a monomeric hydroxy aromatic compound, a phenol-aldehyde resin or a mixture thereof in an amount of a haloepoxyalkane in excess of that required for etherification, heating the solution to at least 60 DEG  C. and below the decomposition temperature of said haloepoxyalkane, and adding gradually thereto an alkali hydroxide dissolved in an aliphatic alcohol having less than five carbon atoms. Many haloepoxyalkanes are specified, examples being epichlorohydrin, 1-chloro-2,3-epoxybutane, 1-bromo-2,3-epoxypentane, 4 - chloro - 2 - methyl - 2,3 - epoxypentane and 1 - chloro - 2 - methyl - 2,3 - epoxydacane. Preferred aromatic hydroxy compounds are resorcinol, hydroquinone and catechol.  Alkali hydroxides specified are lithium, sodium, potassium, rubidium and caesium hydroxides.  In the examples, epichlorohydrin is used as a solvent for and is reacted with: (iii) a cresolformaldehyde resin in the presence of an ethanolic solution of potassium hydroxide; (iv) as in (iii), but using an ethanolic solution of sodium hydroxide; (v) a phenol-formaldehyde resin in the presence of an ethanolic solution of potassium hydroxide; (vi) as in (v) but using an ethanolic solution of sodium hydroxide; (vii) an acid-catalysed resorcinol-formaldehyde resin in the presence of an ethanolic solution of potassium hydroxide; (viii) a base-catalysed resorcinol-formaldehyde resin in the presence of an ethanolic solution of potassium hydroxide; (ix) as in (viii) but using an ethanolic solution of sodium hydroxide; (x) resorcinol and an acid-catalysed resorcinol-formaldehyde resin in the presence of an ethanolic solution of potassium hydroxide; (xi) resorcinol in the presence of an ethanolic solution of potassium hydroxide; (xii) as in (xi), but using an ethanolic solution of sodium hydroxide; (xiii) as in (xi), but using a methanolic solution of sodium hydroxide; (xvi) hydroquinone in the presence of an ethanolic solution of potassium hydroxide; (xvii) as in (xvi), but using an ethanolic solution of sodium hydroxide.  The resinous products of the invention may be used as adhesives, binders, potting compounds, laminating agents and surface coatings.