Patent GB-681108-A (GB)
Title: Improvements in and relating to epoxide compositions suitable for use as adhesives
IPC: C08G59/24
Filed: 1950-04-28
Abstract: A fluid composition having a viscosity of 3-100 poises at 25 DEG  C. and curable with a hardening agent to a hard resin comprises (1) a glycidyl ether of a polyhydric phenol having a 1,2-epoxy equivalency greater than one, and (2) a liquid mono-epoxy compound having a boiling-point above 100 DEG  C.  The composition may also contain a glycidyl ether of a polyhydric alcohol having a 1,2-epoxy equivalency greater than one.  Specified mono-epoxy compounds are 2,3-hexylene oxide; 3,4-hexylene oxide; 3-ethyl-2,3-pentylene oxide; 2,5-dimethyl-1,2-hexylene oxide; styrene oxide; glycide; decylene oxide; beta-methyl glycidol; and methyl-, ethyl-, isopropyl-, allyl-, isoamyl-, phenyl-, o-tolyl-, p-tolyl-, thymyl-, and naphthyl - glycidyl ethers.  Specified polyhydric phenols are resorcinol; catechol; hydroquinone; bis - (4 - hydroxyphenyl) - 2,2 - propane (i.e. bis-phenol); 4,41-dihydroxybenzophenone; bis - (4 - hydroxyphenyl) - 1,1 - ethane; bis - (4 - hydroxyphenyl) - 1,1 - isobutane; bis - (4 - hydroxyphenyl) - 2,2 - butane; bis - (4 - hydroxy - 2 - methylphenyl) - 2,2 - propane; bis - (4 - hydroxy - 2 - tertiary - butylphenyl) - 2,2 - propane; bis - (2 - hydroxynaphthyl) - methane; and 1,5-dihydroxy naphthalene. Specified polyhydric alcohols are ethylene-, propylene-, trimethylene-, butylene-, diethylene-, triethylene-, and tripropylene-glycol; glycerol; diglycerol; erythritol; pentaglycerol; pentaerythritol; mannitol; sorbitol; polyallyl alcohol; and polyvinyl alcohol.  Specified hardening agents are sodium or potassium hydroxides; sodium phenoxide; formic acid, oxalic acid and phthalic anhydride; aluminium chloride, zinc chloride, ferric chloride and boron trifluoride and complexes thereof with ethers, acid anhydrides, ketones and diazonium salts; phosphoric acid, n-butyl orthophosphate, diethyl orthophosphate and hexaethyl tetraphosphate; triethylamine, diethylamine, ethylene diamine, diethylene triamine, triethylene tetramine, dicyandiamide and melamine.  The composition may be used for uniting wood to wood, wood to metal, wood to resin, metal to metal, metal to glass, glass to glass or resin to resin.  In examples: (1) epoxy resin I having an epoxy equivalency of 1.94 is prepared by heating a mixture of sodium hydroxide and bis-phenol, cooling and adding epichlorhydrin, then adding sodium hydroxide and washing and drying; (2) epoxy resin I having an epoxy equivalency of 1,57 is prepared by adding epichlorhydrin to a solution of bis-phenol in caustic soda, adding successively two further quantities of caustic soda, washing and drying; (3) epoxy resin III having an epoxy equivalency of 2.18 is prepared by adding boron trifluoride in diethyl ether to a mixture of glycerol and epichlorhydrin, dissolving the resulting condensate in dioxane containing sodium aluminate, filtering off insoluble material and then distilling to remove low boiling substances.  Tables 1 and 2 disclose compositions of epoxy resin II and glycidyl phenyl ether, glycidyl isopropyl ether, glycidyl allyl ether, styrene monoxide and beta-methyl glycidol, together with diethylenetriamine or diethylamine as curing catalysts. Table 3 discloses compositions of epoxy resin III, allyl glycidyl ether, triethylamine, and (a) epoxy resin I and (b) epoxy resin II. Table 4 discloses compositions of epoxy resin II, epoxy resin III and (a) phenyl glycidyl ether, (b) allyl glycidyl ether, (c) isopropyl glycidyl ether; (d) styrene monoxide, together with diethylene triamine or triethylamine as curing catalysts.  Specification 681,099 is referred to.