Patent GB-1065033-A (GB)
Title: Derivatives of tris-aziridinyl phosphine oxides and sulphides, and their use for treating surfaces
IPC: D06M13/493
Filed: 1964-06-16
Abstract: The invention comprises reaction products of 0.5 to 7.2 mols of a tris-aziridinyl phosphine oxide or sulphide or homologue thereof and one mol. of a fluoroalkanoic acid of the formula QCOOH, wherein Q is a C3 to C21 fluoroalkyl group in which 75 to 100% of the H atoms are replaced by F atoms and which terminates as -CF3.  They may be prepared by reacting the appropriate tris-aziridinyl phosphine oxide or sulphide with the appropriate fluoroalkanoic acid in solution in a solvent at temperatures in the range of 15 DEG  to 100 DEG  C.  An example is given for the production of one of the products. Other similar reaction products are also specified. They are useful for treating and coating surfaces of materials such as textiles, wood, metal and ceramics (see Division B2), for flame-proofing and giving crease-resistant properties, shrinkage-resistant properties, and oil and water repellency to textiles (see Division D1).ALSO:Reaction products of 0.5 to 7.2 moles of a tris-azirininyl phosphine oxide or sulphide or homologue thereof and one mole of a fluoroalkanoic acid of the formula:-a COOH wherein a  is a C3-C21 fluoro alkyl group with 75 to 100% of its H atoms replaced by F atoms and terminating as -CF3 (see Division C2) are used as flame-proofing agents, for crease and shrink proofing, and for imparting water and oil repellency properties to textiles such as cotton.  Also the compounds may be prepared in situ at from 15 to 100 DEG C by immersing the textile in an aqueous solution of the aziridinyl phosphine oxide or sulphide and adding the appropriate fluoroalkanoic acid in molar proportions such that the reaction product has at least one but not more than two aziridinyl groups.  Or the compounds may be applied in an organic solvent to the surface of the material to be treated at room temperature, or the substrate may be heated to below its softening or charring temperature for at least 1 minute and up to 5 minutes.ALSO:Surfaces of materials such as textiles, wood, metal and ceramics are treated with reaction products of 0.5 to 7.2 moles of a tris-aziridinyl phosphine oxide or sulphide or homologue thereof and one mole of a fluoroalkanoic acid of the formula a COOH wherein a  is a C3 to C21 fluoroalkyl group with 75 to 100% of the H atoms replaced by F atoms and which terminates as -CF3 (see Division C2).  The derivatives wherein one or two aziridine radicals have been replaced by fluoroalkanoic-acid radicals are reactive with substrates having reactive hydrogen, for example, natural or regenerated cellulose, wool, and natural or synthetic proteinaceous materials.  The corresponding trisubstituted derivatives are not reactive with substrates having reactive hydrogen but can be used to film or coat surfaces not having reactive hydrogen, for example, metals, ceramics including glass, elastomers and resins.  The compounds may be prepared in situ on the material to be treated at temperatures from 15 to 100 DEG C. by immersing the material to be treated in an aqueous solution of the aziridinyl phosphine oxide or sulphide and the fluoroalkanoic acid is then added to the solution in molar proportions such that the reaction product has at least one but not more than two aziridinyl groups.  The fluoroalkanoic acid derivative of the phosphine oxide or sulphide may be applied, in an organic solvent, to the surface to be treated at room temperature or the coated substrate may be heated to a temperature below its softening or charring point, preferably in the range 121 to 177 DEG C. for at least 1 minute and up to 5 minutes.