Patent GB-666732-A (GB)
Title: Improvements in or relating to thermosetting resins containing a diphenol and a diglycidyl ether
IPC: C08G59/62
Filed: 1949-04-20
Abstract: The invention relates to the production of diglycidyl ethers of diphenols and to thermosetting compositions prepared therefrom by admixing the diglycidyl ether and a diphenol in proportions of 0.2-1 mol. diphenol per mol. diglycidylether.  The diphenols employed are compounds of the dihydroxy diphenyl methane series including their isomers, homologues and substituent compounds and the diglycidylethers of diphenols are compounds of the general formula <FORM:0666732/IV (a)/1> having a content of epoxy groups corresponding to at least 80 per cent pure diglycidyl ether.  These ethers are prepared by reacting diphenol and epichlorhydrin (or the corresponding amount of glycerol dichlorhydrin) in the molar ratio of at least two mols. of epichlorhydrin per mol. diphenol and maintaining such excess by adding the diphenol gradually to the epichlorhydrin, e.g. 228 parts 4,41-dihydroxydiphenyl dimethylmethane are dissolved in 800 parts water, 80 parts NaOH and 400 parts ethanol, the resulting solution is added stepwise to 400 parts epichlorhydrin in 400 parts ethanol at 50 DEG  C., and the reaction mixture is heated to 80 DEG  C. for one hour; the mixture is distilled to remove excess salt and epichlorhydrin and the residue washed and purified by redistillation.  Numerous examples illustrate mixing in various proportions the diglycidylethers thus prepared with various diphenolol methanes in presence of about 1 per cent of alkali metal hydroxides as catalyst and at temperatures of 90-175 DEG  C. Ammonia, amines, e.g. di-acid trimethylamine, triethylamine, 1,3-propane diamine, trimethylamino methyl phenol, quaternary ammonium compounds, sodium acetate, boron trifluoride, phosphoric acid copper and other metal surfaces may be used as catalysts. The compositions may be moulded, cast, made into paper composites, mixed with other resin, e.g. polyvinyl alcohol, polyamides, phenol formaldehyde resins or with wood flour &c. fillers, oils, tars, sand (for mould cores) abrasives, asbestos, rubber.  Tables show that where the molar ratio of diphenol to glycidyl ether is 1.1-1 the mixture does not gel at 160 DEG  C., with a ratio of 1.05-1 the mixture is a stiff liquid which does not gel within 20 minutes, while with a ratio of 0.95-1 hardening takes place in 4 minutes.ALSO:Diglycidyl ethers of diphenols having a content of epoxy groups corresponding to at least 80 per cent pure diglycidyl ether and having the general formula <FORM:0666732/IV (b)/1> in which R1 and R2 are hydrogen, alkyl (C1 to C6), phenyl, tolyl or with the linking carbon, cyclohexylidene, the sum of R1 and R2 not exceeding 12, are prepared by reacting at least two mols of epichlorhydrin (or the corresponding amount of glycerol dichlorhydrin) with one mol. diphenol and maintaining such excess by adding the diphenol gradually to the epichlorhydrin.  A solution of 4,41-dihydroxydiphenyldimethylmethane in aqueous alcoholic soda is heated with epichlorhydrin and the mixture first distilled to remove excess solvent and epichlorhydrin and then washed and redistilled.