Patent GB-681991-A (GB)
Title: Compositions of matter suitable for the production of resinous products, a process for using the same and the resinous products formed therefrom
IPC: C08G59/14
Filed: 1949-05-02
Abstract: Glycidyl ethers, formed by reacting a polyhydric compound with a compound containing a glycidyl radical or a radical yielding a glycidyl radical under the conditions of the reaction, and having a 1,2-epoxy equivalency greater than 1 are hardened by the addition thereto of a phosphorus-containing compound of the formula RO-P(OH)2=O (where R is H or an alkyl radical) and heating the mixture from 20-250 DEG  C.  The invention includes compositions of the above components which, in solution in solvents, e.g. dioxane, xylene, benzene, toluene, ketones, e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl cyclohexanone; esters such as ethyl acetate, isopropyl acetate, butyl acetate, isoamyl acetate; monoalkyl ethers, monomeric alkyl ethers of ethylene glycol, and in admixture with the usual pigments and fillers, e.g. titanium oxide, iron oxides, carbon black, wood flour, talc, a -cellulose, and silica, may be applied as coatings to glass and metal surfaces and hardened in situ by baking.  In coating metals the phosphorus compound acts as a phosphatizing agent.  Phosphorus compounds specified are orthophosphoric acid or mono alkyl derivatives thereof, e.g. methyl, ethyl, butyl, amyl, 2-ethyl hexyl, lauryl or stearyl orthophosphates.  Glycidyl ethers having a 1,2-epoxy equivalency greater than 1 are defined as (a) having two or more glycidyl groups, e.g. diglycidyl ether, dimethyl or polyglycidyl ethers, e.g. the diglycidyl ethers of glycols, glycerols, erythritol, mannitol, sorbitol, polyallyl or butyvinyl alcohol; (b) complex epoxy compounds comprising a mixture of compounds of similar chemical constitution but different molecular weights and which have an epoxy equivalency which is not integral but is greater than one e.g. glycidyl ethers of polyhydric alcohols or phenols.  The preferred compounds of this class are the epoxy ethers made by reacting polyhydric phenols, particularly bis phenol with excess epichlorhydrin and alkali, e.g. the resinous product obtained by reacting 4 mols. bis-phenol with 5 mols. epichlorhydrin in presence of 6.43 mols. NaOH as 10 per cent aqueous solution, the reaction mixture being heated under reflux to 100 DEG  C. and maintained at 100-104 DEG  C. for 60 minutes.  A 50 per cent solution of this resin in equal parts of xylene and butyl ether of ethylene glycol was mixed with (a) 3.9 per cent orthophosphoric acid; (b) 8.8 per cent monomethyl orthophosphate; (c) 7.8 per cent monoethyl orthophosphate; (d) 10 per cent mono n-butyl orthophosphate; (e) 12 per cent monoamyl orthophosphate; (f) 10 per cent mixture of mono- and dilauryl orthophosphate; (g) 10 per cent octadecyl diacid orthophosphate, the solutions were applied as films to glass plates, allowed to dry and baked at 150 DEG  C. for 30 minutes.  In the case of compositions (a)-(f) the films remained tough under the scratch test and showed no softening when the film was treated with a drop of toluene for 15 minutes.  In the case of compositions (f) and (g) the film was softened or dissolved.  The products are also suitable for moulding purposes, or as adhesives. Specification 629,111 is referred to.  A sample has been furnished under Sect. 2 (5) of a film of polyglycidyl ether of glycerol with epoxy equivalency 2-18, mixed with butyl dihydrogen phosphate.  The film was cured by baking at 105-110 DEG  C. for 2 hours.ALSO:Ferruginous metal is rust-proofed by applying thereto a coating containing a glycidyl ether of polyhydric compound (see Group IV(a)) and phosphorus compound of the formula Ro-P(OH)2=O (where R is hydrogen or an alkyl radical).  The preferred compound is orthophosphoric acid employed in the proportion 1/2 -1\ba1/2 mols per epoxy group in the glycidyl ether. The composition is baked at 150 DEG  to 250 DEG C and the phosphorus compound cures the resin and phosphatizes the metal.  If desired the glycidyl ethers may be partially esterified with drying oil fatty acids.