Patent GB-361910-A (GB)
Title: Manufacture of condensation products of high molecular weight
IPC: C08F8/00
Filed: 1930-08-14
Abstract: Condensation products suitable for use as emulsifying agents are manufactured by condensing polyvinyl alcohol in aqueous solution with formaldehyde and urea at 45-50 DEG  C., or with aldol and resorcinol at 70-75 DEG  C.ALSO:Condensation products; moulding compositions; sizes; emulsions, making; printing; textiles, treating.--Condensation products of high molecular weight are manufactured by condensing a polyvinyl alcohol with an aldehyde and a body capable of condensing with aldehydes.  The three components may be condensed simultaneously or the polyvinyl alcohol may be first condensed with the aldehyde and the product then condensed with the body capable of condensing with aldehydes.  Under mild conditions products soluble in water are formed, whilst stronger heating causes the separation of an insoluble mass.  As compounds capable of condensing with aldehydes are specified : phenols and derivatives thereof, aromatic amines such as aniline, acid amides such as urea, thiourea and p-toluenesulphamide, also substances of high molecular weight such as gelatin, casein, starch and mucilage.  The reaction may be accelerated by substances which promote saponification or esterification.  The procedure may be such that the formation of the polyvinyl alcohol and the condensation with the other components constitutes one operation.  When the compound capable of condensing with aldehydes is a phenol, the products have a phenolic character and may be acylated or alkylated at the phenolic hydroxyl, or can be sulphonated.  In examples : (1) polyvinyl alcohol (prepared by saponification of a fatty acid ester of polyvinyl alcohol, such as polyvinyl acetate, chloracetate or butyrate, in the presence of an acid or an alkaline catalyst) is condensed simultaneously with formaldehyde and urea in aqueous solution at 90-100 DEG  C.; the product is a white, horn-like mass which can be used as a moulding composition; (2) a similar condensation is carried out at 45-50 DEG  C. yielding a viscous homogeneous product which can be used for making emulsions, as a material for sizing and dressing, or for preparing dyestuff pastes for printing; (3) polyvinyl alcohol and glyoxal are condensed in aqueous solution at 50-60 DEG  C. and the product condensed at the same temperature with thiourea; (4) an aqueous solution of polyvinyl alcohol, formaldehyde and phenol with a small amount of ammonia is boiled; the whitish plastic mass obtained is useful as a moulding composition; (5) chips of polyvinyl alcohol are suspended in ethanol and condensed at 50-60 DEG  C. with benzaldehyde in the presence of hydrogen chloride; the product is condensed with commercial cresol by gently boiling, yielding a solution suitable for a lacquer; the resin may be isolated by distilling off the alcohol and is likewise useful for preparing lacquers; (6) polyvinyl alcohol, aldol and resorcinol are condensed in aqueous solution at 70-75 DEG  C., yielding a viscous solution useful for making emulsions, as a material for sizing and dressing, or for preparing dyestuff pastes for printing; (7) polyvinyl alcohol (obtained by saponification of polyvinyl acetate and still containing about one-third of the acetyl groups originally present) is condensed by boiling in aqueous solution with formaldehyde and p-toluenesulphamide in the presence of sulphuric acid; the product is soluble in alcohol to produce lacquers; (8) polyvinyl alcohol (obtained by saponifying polyvinyl chloracetate) is condensed in methanol solution at 50-60 DEG  C. with acetaldehyde in the presence of lactic acid, and the product is boiled on a water bath with aniline; the product is useful for preparing lacquers; (9) polyvinyl alcohol is condensed with formaldehyde in aqueous solution at 50 DEG  C. and the product is gently boiled with an aqueous solution of casein; the product is useful as a moulding composition. Azo dyes may be produced by coupling a diazo-component with a condensation product prepared as above in which the compound capable of reacting with aldehydes is a phenol.  The Specification as open to inspection under Sect. 91 (3) (a) comprises also an alternative process in which the aldehyde is first condensed with the third component and the product is caused to react with the polyvinyl alcohol.  This subject-matter does not appear in the Specification as accepted.ALSO:Condensation products of high molecular weight are manufactured by condensing a polyvinyl alcohol with an aldehyde and a body capable of condensing with aldehydes.  The three components may be condensed simultaneously, or the polyvinyl alcohol may be first condensed with the aldehyde and the product then condensed with the third component.  Under mild conditions products soluble in water are formed, whilst stronger heating causes the separation of an insoluble mass.  As compounds capable of condensing with aldehydes are specified: phenols and derivatives thereof, aromatic amines such as aniline, acid amides such as urea, thiourea, and p-toluenesulphamide, also substances of high molecular weight such as gelatin, casein, starch, and mucilage.  The reaction may be accelerated by substances which promote saponification or esterification.  The procedure may be such that the formation of the polyvinyl alcohol and the condensation with the other components constitutes one operation.  In examples: (1) polyvinyl alcohol is condensed simultaneously with formaldehyde and urea in aqueous solution at 90-100 DEG  C., yielding a white horn-like mass useful as a moulding composition; (2) the same substances are condensed at 45-50 DEG  C., yielding a viscous homogeneous product suitable for sizing; (3) polyvinyl alcohol and glyoxal are condensed in aqueous solution at 50-60 DEG  C. and the product condensed at the same temperature with thiourea; (4) an aqueous solution of polyvinyl alcohol, formaldehyde, and phenol with a small amount of ammonia is boiled; the whitish plastic mass obtained is useful as a moulding composition; (5) chips of polyvinyl alcohol suspended in ethanol are condensed at 50-60 DEG  C. with benzaldehyde in the presence of hydrogen chloride and the product is condensed with commercial cresol by gently boiling; (6) polyvinyl alcohol, aldol, and resorcinol are condensed in aqueous solution at 70-75 DEG  C. yielding a viscous solution useful for sizing; (7) polyvinyl alcohol (obtained by saponifying polyvinyl acetate and still containing about one-third of the acetyl groups originally present) is condensed by boiling in aqueous solution with formaldehyde and p-toluenesulphamide in the presence of sulphuric acid; (8) polyvinyl alcohol is condensed in methanol solution at 50-60 DEG  C. with acetaldehyde in the presence of lactic acid, and the product is boiled on a water bath with aniline; (9) polyvinyl alcohol is condensed with formaldehyde in aqueous solution at 50 DEG C. and the product is gently boiled with an aqueous solution of casein; the product is useful as a moulding composition.  The Specification as open to inspection under Sect. 91 (3) (a) comprises also an alternative process in which the aldehyde is first condensed with the third component and the product is caused to react with the polyvinyl alcohol.  This subject-matter does not appear in the Specification as accepted.