Patent GB-743647-A (GB)
Title: Improvements in and relating to methylol phenol compounds
IPC: C07D303/26
Filed: 1952-03-18
Abstract: Compounds of the general formula <FORM:0743647/IV(a)/1> (wherein R1, R2 and R3 represent hydrogen or alkyl, aryl or aralkyl radicals, Z represents an alkylene radical and n is 1, 2 or 3) may be used in the production of synthetic resins as follows: (a) on heating, preferably with an acidic catalyst, they are converted to an insoluble and infusible product; (b) by reaction with polycarboxylic acids or anhydrides (e.g. phthalic acid or anhydride, oxalic, succinic, malonic, isophthalic or terephthalic acid, or chlorinated phthalic acids or anhydrides) they yield alkydtype resins, which may be modified by the addition of other polyhydric alcohols (e.g. glycerol, pentaerythritol or ethylene glycol), monohydric alcohols, monobasic acids (e.g. acetic or propionic acid, or linseed or coconut oil acids), or oils (e.g. castor oil, dehydrated castor oil, oiticica oil or tung oil).  In the case of process (a), the starting materials may be mixed with fillers (e.g. iron oxide, lithopone, silica, zinc oxide, glass fibres, asbestos floats or mica flakes) for making moulded articles, or may be used in the form of solutions as coating compositions or for the impregnation of sheet material (e.g. glass fibre cloth, asbestos cloth, or asbestos paper) for making laminated products.  In examples (1) the reaction product of epichlorhydrin with 2 : 6 - dimethylol - p - cresol is dissolved in alcohol and heated with toluenesulphonic acid to form a film; (2) the reaction product of epichlorhydrin with saligenin is heated with p-toluenesulphonic acid, alone or dissolved in alcohol; (3) the reaction product of epichlorhydrin with the condensation product of potassium phenolate and approximately two molecular proportions of formaldehyde is heated alone; (7) the reaction product of epichlorhydrin with the condensation product of sodium phenate with slightly over two molecular proportions of formaldehyde is twice washed with warm dilute hydrochloric acid and then dehydrated to a fusible soluble resin, which may be rendered infusible and insoluble with larger amounts of acid.  Specifications 557,513 and 712,525 [Group IV (b)], are referred to.ALSO:Compounds of the general formula <FORM:0743647/IV(a)/1> (wherein R1, R2 and R3 represent hydrogen or alkyl, aryl or aralkyl radicals, Z represents an alkylene radical and n is 1, 2 or 3) are manufactured by reacting an alkylene oxide of the general formula <FORM:0743647/IV(a)/2> (wherein R represents a halogenated saturated aliphatic radical) with one or more compounds of the general formula <FORM:0743647/IV(a)/3> (wherein M represents sodium, potassium or barium).  As side reactions, some of the epoxide groups may be hydrolysed to give the corresponding hydroxy derivative or may intercondense to give polymers, whilst if excess over an equimolecular amount of the alkylene oxide is used some etherification of the methylol group or groups may occur.  In examples, epichlorhydrin is reacted in aqueous alcoholic caustic alkali with (1) and (4) 2:6-dimethylol-p-cresol; (2) saligenin; (3) the condensation product of potassium phenate with approximately two molecular proportions of formaldehyde; (5) the condensation product of sodium phenate with 1.9 molecular proportions of formaldehyde; (6) the condensation product of sodium p-phenylethylphenate with 2.23 molecular proportions of formaldehyde; (7) the condensation product of sodium phenate with slightly over two molecular proportions of formaldehyde.  Specifications 557,513 and 712,525 are referred to.