Patent GB-608186-A (GB)
Title: Method of preparing guanamine-aldehyde condensation products
IPC: C08G12/30
Filed: 1946-02-18
Abstract: Condensation products are prepared by heating formaldehyde or a polymer thereof and one or more guanamines of the general formula <FORM:0608186/IV(a)/1> where R is a substituted or unsubstituted divalent straight-chain aliphatic or phenylene radical (see Group IV (a)).  The reaction medium may be water or an organic solvent.  An alcohol may be present during the reaction or the product may be reacted with an alcohol.  A list of suitable alcohols is included in the Specification.  Melamine, urea, phenol, aniline, dicyandiamide or thiourea may be mixed with the guanamine.  Impure mixtures of guanamine with guanides or aminodiazines obtained by reacting two mols. of biguanide with one mol. of a dicarboxylic acid in a solvent such as methanol and, if desired, in presence of a catalyst such as a metal alkoxide may be used.  The products may be used, if desired, with other resinous material in drying oil varnishes, for treating fibrous materials such as paper, textiles or leather, as a binder for abrasives or cork, for moulding compositions, as casting resins, in coating compositions, if desired together with cellulose derivatives, natural or synthetic resins, and plasticisers, for affixing dyes to fabrics, particularly of cellulose or its derivatives, or for insolubilising dyes, lakes or pigments.  Aqueous syrups or emulsions are particularly useful for treating textiles or paper (see Group VIII).  They may also contain wetting agents and compatible emulsifiers, of which a list is to be found in the Specification.  By keeping the time and temperature of the reaction low, it is possible to obtain ethers of the methylol guanamine in substantially monomeric condition.  The condensation products may be cured to the insoluble condition by heating under acid, basic or neutral conditions.  In example (1), sebacoguanamine is condensed with formaldehyde.  The solid product is soluble in ethanol, butanol and hot water.  It may be reacted with or dissolved in alcohol to yield a lacquer, or is suitable for modifying resins formed from formaldehyde and urea and/or melamine; (2) a lacquer is prepared by heating formalin, sebacoguanamine and butanol for some time, adding phosphoric acid and dehydrating; (3) succinoguanamine is condensed with formaldehyde in presence of triethanolamine.  The product is heated with butanol, yielding a film-forming solution; (4) adipoguanamine is condensed with formalin and the product reacted with butanol; (5) terephthaloguanamine is reacted with formalin and then with butanol. The product may be mixed with phosphoric acid to yield a film-forming composition which hardens on baking.  Sebacoguanamine is prepared by reacting biguanide and butyl sebacate in methanol and purified by dissolving in ethanol and acetic acid, suspending the acetate in water and hydrolysing it with alkali.  The other guanamines used in the example are prepared in a similar manner with appropriate esters in place of butyl sebacate.ALSO:Ethers of methylol guanamines may be prepared in substantially monomeric condition by keeping the time and temperature of the reaction low.  The methylol compounds are formed from formaldehyde or a polymer thereof and a guanamine of the general formula <FORM:0608186/IV(b)/1> where R is a straight chain aliphatic or phenylene radical.  The alcohol may be present during the reaction or the preformed methylol compound may be reacted with the alcohol. Sebacoguanamine is prepared by reacting biguanide and butyl sebacate in methanol and purified by dissolving in ethanol and acetic acid suspending the acetate in water and hydrolysing it with alkali. Other guanamines may be prepared in a similar manner with appropriate esters in place of butyl sebacate.ALSO:Condensation products prepared by heating formaldehyde or a polymer thereof and one or more guanamines of the general formula <FORM:0608186/IV (c)/1> where R is a substituted or unsubstituted divalent straight chain aliphatic or phenylene radical (see Group IV (a)) may be used for affixing dyes to fabrics particularly of cellulose or its derivatives or for insolubilising dyes, lakes or pigments.