Patent GB-900372-A (GB)
Title: Water-soluble compounds containing epoxide groups
IPC: D06M15/423
Filed: 1960-09-14
Abstract: Water-soluble resins of formula <FORM:0900372/IV(a)/1> where Z is an organic residue containing an epoxide group and Y is -CH=CH2 or -CH2-CH2-O-Z, may be cured by heating with catalysts, e.g. ammonium chloride, sulphate or silicofluoride, magnesium chloride, zinc nitrate, aluminium chloride, boron fluoride or zinc fluoborate.  Z may be a residue of the formula <FORM:0900372/IV(a)/2> or of the formula <FORM:0900372/IV(a)/3> where R is a hydrogen atom or a methyl group.  Textiles are impregnated with an aqueous solution of the resin and the catalyst, dried, and hardened at 120 DEG  to 160 DEG C. The resin may be mixed with a plasticizer, polyvinyl alcohol, or an aminoplast, e.g. a formaldehyde condensation product with melamine, urea or ethyleneurea.ALSO:The invention comprises compounds of formula <FORM:0900372/IV (b)/1> wherein Z is an organic residue containing at least one epoxide group and Y is a residue of formula -CH=CH2 or -CH2-CH2-O-Z.  The compounds are prepared either (A) by reacting with an epoxidizing agent a derivative of triacrylyl perhydro triazine of formula <FORM:0900372/IV (b)/2> where Z1 is an organic residue containing at least one epoxidizable group and Y1 is a residue of formula -CH=CH2 or -CH2-CH2-O-Z1, or (B) by adding at least 2 molecular proportions of an alcohol of formula Z-OH on to 1 molecular proportion of triacrylyl perhydro triazine.  The starting material of method (A) may be obtained by adding at least 2 mols of an alcohol of formula Z1OH on to 1 mol of triacrylyl perhydro triazine.  The residue Z1 may contain a halohydrin grouping which may be converted into an epoxide group by reaction with a dehydrohalogenating agent, e.g. sodium hydroxide; the residue Z1 may be a glycerol monochlorhydrin residue and the alcohol Z1-OH may be a glycerol monochlorhydrin.  The alcohol Z1-OH also may be a D 3-tetrahydrobenzyl alcohol which may be substituted. Examples of the alcohol Z-OH used in method (B) are glycidol and 3:4-epoxy-hexahydrobenzyl alcohol.  The addition of the alcohol Z1-OH or Z-OH to the triacrylyl perhydro triazine may be performed in the presence of a catalyst, e.g. sodium hydroxide, sulphuric acid or boron trifluoride.  The epoxidation of carbon-to-carbon double bonds is performed with the aid of a per-acid, e.g. peracetic acid, or with hypochlorous acid.  In examples, (1) a mixture of triacrylyl perhydro triazine and glycerol monochlorohydrin in benzene is reacted with sodium hydroxide to acetic acid to obtain a diepoxide of formula <FORM:0900372/IV (b)/3> and (2) triacrylyl perhydro triazine is reacted with tetrahydrobenzyl alcohol and sodium hydroxide solution, and the product is reacted with sodium acetate, peracetic acid and glacial acid to obtain a diepoxide of formula <FORM:0900372/IV (b)/4>ALSO:Textiles are rendered crease-resistant by impregnating with water-soluble resins of formula <FORM:0900372/IV (b)/1> where Z is an organic residue containing an epoxide group and Y is -CH=CH2 or -CH2-CH2-O-Z, and then curing by heating with catalysts, e.g. ammonium chloride, sulphate or silicofluoride, magnesium chloride, zinc nitrate, aluminium chloride, boron fluoride or zinc fluoborate. Z may be a residue of the formula <FORM:0900372/IV (b)/2> or of the formula <FORM:0900372/IV (b)/3> where R is a hydrogen atom or a methyl group.  Textiles are impregnated with an aqueous solution of the resin and the catalyst, dried, and hardened at 120 DEG  to 160 DEG C.  The resin may be mixed with a plasticizer, polyvinyl alcohol, or an aminoplast, e.g. a formaldehyde condensation product with melamine, urea or ethyleneurea.  The textile fibres may be of native or regenerated cellulose or of polyvinyl alcohol.