Patent GB-939025-A (GB)
Title: Heterocyclic glycidyl ethers and the treatment of cellulosic fabrics therewith
IPC: C07D407/12
Filed: 1960-02-01
Abstract: The invention comprises compounds of the formula <FORM:0939025/IV(a)/1> wherein one of the R groups is H, another of the R groups is a <FORM:0939025/IV(a)/2> group or a <FORM:0939025/IV(a)/3> group, with the proviso that there are at least two carbon atoms between each pair of oxygen atoms in the compound of the above formula, and each of the other two R groups is either H or CH3.  The novel compounds may be made by dehydrochlorinating an appropriate condensation product of epichlorohydrin and b -tetrahydrofuryl alcohol, or a tetrahydrofurfuryl alcohol or a methyl substituted derivative thereof, the dehydrochlorination being carried out in the presence of a hydrogen chloride acceptor. The reaction of the alcohol with epichlorohydrin takes place at 40 DEG  to 100 DEG C. in 3 to 6 hours to form the 3-chloro-2-hydroxypropyl ether.  An inert solvent and an acidic catalyst may be used.  The dehydrochlorination is effected in the presence of a base such as an alkali metal hydroxide or carbonate or an organic tertiary amine at a temperature in the region from 0 DEG  to 80 DEG C. for 3 to 6 hours.  An inert solvent such as ether, dioxane, alcohols or water may be employed if desired.  Detailed examples are given.ALSO:Textile fabrics formed of cellulosic fibres such as cotton and regenerated cellulose fibres are treated for crease-proofing and stabilization against shrinkage on washing by impregnating the fabrics with an aqueous solution of a compound of the formula <FORM:0939025/IV(a)/1> wherein one of the R groups is H, another of the R groups is a <FORM:0939025/IV(a)/2> group or a <FORM:0939025/IV(a)/3> group, with the proviso that there are at least two carbon atoms between each pair of oxygen atoms in the compound of the above formula, and each of the other two R groups is either H or CH3, and curing the impregnated fabric to react the glycidyl ether with the cellulosic fibres.  The concentration of the ether in the aqueous solution may vary from 1 to 30% by weight, preferably from 5 to 12%.  The treatment is preferably effected in the presence of a catalyst comprising a metal salt of an acid having the composition Ha(XYb), where H is hydrogen, a has a value of 1, 2 or 3 depending on the valence of the complex ion, X is boron, silicon, sulphur, or chlorine, Y is fluorine or oxygen, and b is an integer of 4 or 6, the metals being those of Group Ib, II, IIIb, IV or VIII of the Periodic Table, which have an atomic weight of at least 12.  Other acidic compounds, e.g. oxalic acid, may also be used as catalysts.  The catalysed solution of the ether is compatible with other textile finishing agents such as synthetic polymer lattices and aminoplast resins or precondensates.  The aqueous solution may be applied by spraying or impregnation, conveniently with machines such as pads or jigs or on a tumble wheel, laundry machine, or other suitable equipment.  The excess solution is removed by squeezing the fabric between rollers, or by shaking or centrifuging it.  The treated fabric may be air-dried at normal temperature or heated at 140 DEG F. or more.  The drying and curing are preferably done with the fabric open and flat.  Preferably, the fabric immediately after impregnation is carried in open width by a tenter frame through a curing oven at 250 DEG  to 400 DEG F.  Examples describe the treatment of rayon challis and cotton printcloth.