Patent GB-942875-A (GB)
Title: Condensation products
Inventor: BAIRD WILLIAM
IPC: D06M15/423
Filed: 1961-01-11
Abstract: Water-soluble polyamines are prepared from alkylene oxide condensates having at least two terminal hydroxy groups by reaction with thionylchloride to replace the hydroxyl groups by chlorine atoms followed by reaction with ammonia or a primary amine or a polyamine containing at least one primary amino group, or by reaction with acrylonitrile followed by catalytic hydrogenation of the products. All or part of the primary and secondary amino groups of the polyamines may be converted to aldehyde precondensate groups of the formulae: <FORM:0942875/C2/1> <FORM:0942875/C2/2> <FORM:0942875/C2/3> <FORM:0942875/C2/4> <FORM:0942875/C2/5> <FORM:0942875/C2/6>  The primary amino-groups may be converted to a group of formula I by reaction with nitrourea followed by reaction with formaldehyde, or by reaction with sodium cyanate and hydrochloric acid followed by reaction with formaldehyde; into a group of formula II by reaction of the compounds containing a group of formula I with glyoxal; into a group of formula III by reaction with dimethylolurea followed by reaction with formaldehyde or into a group of formula IV by reaction with cyanuric chloride followed by replacement of the remaining chlorine atoms by amino and finally by reaction with formaldehyde. Similarly the secondary amino groups of the polyamine may be converted into a group of formula V by reaction with nitrourea followed by reaction with formaldehyde or into a group of formula VI by reaction with cyanuric chloride followed by amination and methylolation. Examples of the alkylene oxide condensates specified are polyoxyethylene glycols; ethylene oxide condensates of polyhydroxy compounds such as glycerol, sorbitol, or pentaerythritol; ethylene oxide condensates of amines such as methylamine, ethylamine or cetylamine and ethylene oxide condensates of amides.ALSO:Heat hardenable aldehyde condensation products are prepared from water-soluble polyamines which are derived from alkylene oxide condensates containing hydroxyl groups by converting the hydroxyl groups to amino groups or to g -aminopropoxy groups and which contain at least two primary or secondary amino-groups, by (a) reacting the polyamine with an aldehyde resin precondensate or by (b) converting part or all of the primary and secondary amino groups of the polyamine into aldehyde resin precondensate groups of the formula:-NM.CO.NH.CH2OM, <FORM:0942875/C3/1> <FORM:0942875/C3/2> <FORM:0942875/C3/3> <FORM:0942875/C3/4> and <FORM:0942875/C3/5> and optionally thereafter reacting further with the polyamine or with an aldehyde resin precondensate. Aldehyde resin precondensates specified are, for example, dimethylolurea, trimethylolmelamine, hexamethylolmelamine, dimethylolethyleneurea, 1,3-dimethylol-5-b -hydroxyethyl - hexahydrotriazin - 2 - one and their alkyl ethers. Alkylene oxide condensates specified include polyoxyethylene glycols; ethylene oxide condensates of polyhydroxy compounds such as glycerol, sorbitol or pentaerythritol; ethylene oxide condensates of amines such as methylamine, ethylamine or cetylamine and ethylene oxide condensates of amides.  The hydroxy groups may be converted to amino-groups by reaction with thionyl chloride followed by ammonia, a primary amine or a polyamine or by reaction with acrylonitrile followed by catalytic reduction.  The amino-groups may be converted to aldehyde resin precondensate groups by reacting primary amino groups with nitrourea followed by formaldehyde or with sodium cyanate and hydrochloric acid followed by formaldehyde to give I, then I with glyoxal to give II, with dimethylolurea followed by formaldehyde to give III, or with cyanuric chloride followed by amination and methylolation to give IV; or by reacting secondary amino groups with nitrourea followed by formaldehyde to give V, or with cyanuric chloride followed by amination and methylolation to give VI. Reaction with aldehyde resin precondensates may take place simultaneously with hardening in the presence of acid catalysts such as ammonium thiocyanate, zinc nitrate and acetic acid.  The products may be used for treating textiles and producing protective coatings.ALSO:Coatings are prepared from aqueous solutions of heat hardenable aldehyde condensation products (see Divisions C2, C3) which are prepared from water soluble polyamines (derived from alkylene oxide condensates containing hydroxlys groups by converting the hydroxyl groups to amine or g -aminopropoxyl groups) which contain at least two primary or secondary amine-groups, by (a) reacting the polyamine with an aldehyde resin precondensate or by (b) converting part or all of the primary or secondary amine groups of the polyamine into aldehyde resin precondensate groups.  In examples watch glasses are coated by evaporating aqueous solutions of a polyoxyethylene diamine and (1) dimethylolurea, (2) trimethylol melamine and (3) dimethylolethyleneurea.  The resultant films were cured by heating for 30 minutes at 150  DEG C. to give hard, adherent and water-sensitive coatings.ALSO:Nylon, polyethylene terephthalate and polyacrylonitrile textiles are treated to give permanent anti-static finishes by impregnation with heat-hardenable aldehyde condensation products (see Divisions C2 and C3) which are prepared from water soluble polyamines (derived from alkylene oxide condensates containing hydroxyl groups by conversion of such groups to amine or g -aminopropoxyl groups) which contain at least two primary or recording amine groups, by (a) reacting the polyamine with an aldehyde resin precondensate or by (b) converting part or all of the primary or secondary amine groups of the polyamine into aldehyde resin precondensate groups and optionally thereafter with further polyamine or with an aldehyde resin precondensate. Impregnation may be from aqueous solution and the hardenable condensation product may be prepared in situ simultaneously with the curing of the product formed.  The hardenable condensation product is cured by heat treatment preferably in the presence of an acid catalyst, e.g. ammonium thiocyanate, zinc nitrate and acetic acid.