Patent GB-1088672-A (GB)
Title: Reactions of polymeric materials with vinyl phosphonium compounds
Inventor: VALENTINE LESLIE MACKENZIE
IPC: D06M15/356
Filed: 1963-10-03
Abstract: Cellulosic or proteinaceous material such as wool, glue, gelatin or leather is reacted in the presence of an alkaline catalyst with a vinyl phosphonium compound or with a substance which forms or liberates a vinyl phosphonium compound under the reaction conditions. The cellulosic or proteinaceous material contains at least one reactive -OH, -NH- or -SH group in the molecule and may be paper, wood, cellulosic film, cellulose ethers and esters, wool, glue, gelatin or leather.  The vinyl phosphonium compound suitably has the formula <FORM:1088672/C3/1> wherein R1 is a vinyl or substituted vinyl group, R2, R3 and R4 each represents R1 or a grou R which is alkyl, substituted alkyl, alicyclic, aralkyl, aryl or heterocyclic or alkenyl other than R1 and X- represents the anion of an acid or a hydroxyl anion.  Substances which form or liberate vinyl phosphonium compounds are especially the esters of b -hydroxyalkyl phosphonium compounds of the formula <FORM:1088672/C3/2> wherein R5, R6 and R7 independently represent hydrogen or an alkyl group of 1 to 3 carbon atoms and R8, R9 and R10 each represent a group of the formula -CHR5CR6R7OH or the group R.  The cellulosic or proteinaceous materials are preferably in the form of a textile material (see Division D1)ALSO:Triethyl acetoxyethyl phosphonium chloride or iodide may be prepared by first preparing triethyl phosphine by reaction of phosphorus trichloride with a reaction product of ethyl bromide and magnesium turnings in diethyl ether and then reacting the triethyl phosphine with b -chloro-(or iodo-)ethyl acetate.  Similarly tris-(b -cyanoethyl) b -acetoxyethyl phosphonium iodide may be prepared by reacting tris-(b -cyanoethyl) phosphine with b -iodoethyl acetate. On heating the phosphonium compounds with an alkaline catalyst they form the corresponding vinyl phosphonium compounds.ALSO:Cellulosic or proteinaceous textile materials may have various properties improved, e.g. crease-resistance, swelling resistance and shrink resistance, by treatment with a vinyl phosphonium compound or with a substance which forms or liberates a vinyl phosphonium compound.  Alternatively a textile material may be treated with a cellulosic or proteinaceous polymer and a vinyl phosphonium compound.  The vinyl phosphonium compound suitably has the formula:  <FORM:1088672/D1-D2/1> wherein R1 represents a vinyl or substituted vinyl group, R2, R3 and R4 represent the group R1 or a group R which represents an alkyl, substituted alkyl, alicyclic, aralkyl, aryl or heterocyclic group or an alkenyl group other than R1 and X- represents the anion of an acid or a hydroxyl anion.  Substances which form or liberate the vinyl phosphonium compounds may be the esters of b -hydroxyalkyl phosphonium compounds.  A combined treatment wherein, the vinyl phosphonium compound is used in conjunction with or independently of a synthetic thermosetting resin, resin precursor or formaldehyde may also be used.  The vinyl phosphonium compound is suitably applied in the form of an aqueous solution.  Examples describe the treatment of mercerised cotton poplin fabric with (1) methyltrivinylphosphonium iodide, (2) a mixture of methyltrivinylphosphonium iodide and dimethylol ethylene urea (5) triethyl acetoxyethyl phosphonium chloride (8) methyltrivinyl phosphonium iodide and 1,3-dimethylol hexahydropyrimidone-2, viscose rayon staple fibre fabric with (3) methyltrivinyl phosphonium iodide, cotton cloth with (6) triethyl acetoxyethyl phosphonium iodide and (7) tris-(b -cyanoethyl) b -acetoxyethyl phosphonium iodide and a polyethylene terephthalate fibre fabric with (4) hydroxyethylated cellulose and methyltrivinylphosphonium iodide.