Patent GB-988511-A (GB)
Title: Treatment of polymeric materials with sulphonium compounds
Inventor: VALENTINE LESLIE MACKENZIE
IPC: C07C381/12
Filed: 1960-02-23
Abstract: least one reactive -OH, >NH or -SH group in each molecule of the material is reacted in the presence of an alkaline catalyst with a sulphonium salt which, in the presence of the catalyst, forms the following cation:- <FORM:0988511/C3/1> where R1 and R2 may each be hydrogen or an alkyl radical containing from 1 to 3 carbon atoms and may be the same or different, and R3 and R4 may each be the group <FORM:0988511/C3/2> or an alkyl, substituted alkyl (where the substituent is not an -SH or >NH group and is substantially stable to alkali) or aralkyl radical and may be the same or different, the polymeric material being impregnated with an aqueous solution or emulsion of the sulphonium salt and the catalyst being present in an amount sufficient to neutralize any acid liberated and to provide a slight excess sufficient to catalyse the reaction with the polymeric material, and the impregnated material being heated, if necessary, to bring about the desired reaction.  The polymeric material may be, for example, polyvinyl alcohol, a cellulosic material or derivative, such as cellulosic film and cellulose acetate, or a proteinaceous material, such as gelatin.  The cellulosic and proteinaceous materials may be additionally treated with an amido-formaldehyde resin.  Examples illustrate the treatment of regenerated cellulose film and a gelatin coated cellulose acetate film with an aqueous solution of potassium bicarbonate and the disodium salt of tris-(b -sulphatoethyl) sulphonium inner salt.  Specification 988,512 is referred to.ALSO:A polymeric organic material, for example leather, containing at least one reactive -NH, >NH or -SH group in each molecule of the material is reacted in the presence of an alkaline catalyst with a sulphonium salt which, in the presence of the catalyst, forms the following cation:- <FORM:0988511/C6-C7/1> where R1 and R2 may each be hydrogen or an alkyl radical containing from 1-3 carbon atoms and may be the same or different, and R3 and R4 may each be the group <FORM:0988511/C6-C7/2> or an alkyl, substituted alkyl (where the substituent is not an -SH or >NH group and is substantially stable to alkali) or aralkyl radical and may be the same or different, the polymeric material being impregnated with an aqueous solution or emulsion of the sulphonium salt and the catalyst being present in an amount sufficient to neutralize any acid liberated and to provide a slight excess sufficient to catalyse the reaction with the polymeric material, and the impregnated material being heated, if necessary, to bring about the desired reaction. Leather treated according to the invention has increased resistance to attack by mildew. Specification 988,512 is referred to.ALSO:In an example, a gelatin coated cellulose acetate film is soaked in an aqueous solution of potassium bicarbonate and the disodium salt of tris-(b -sulphatoethyl) sulphonium inner salt and dried at 80  DEG C. The gelatin coating has improved resistance to swelling, as compared with an untreated coating, when boiled in water.  Specification 988,512 is referred to.ALSO:A polymeric organic material containing at least one reactive -OH, >NH or -SH group in each molecule of the material is reacted in the presence of an alkaline catalyst with a sulphonium salt which, in the presence of the catalyst, forms the following cation:-  <FORM:0988511/D1-D2/1> where R1 and R2 may each be hydrogen or an alkyl radical containing from 1 to 3 carbon atoms and may be the same or different, and R3 and R4 may each be the group (CR1 = CHR2) or an alkyl, substituted alkyl (where the substituent is not an -SH or >NH group and is substantially stable to alkali) or aralkyl radical and may be the same or different, the polymeric material being impregnated with an aqueous solution or emulsion of the sulphonium salt and the catalyst being present in an amount sufficient to neutralise any acid liberated and to provide a slight excess sufficient to catalyse the reaction with the polymeric material, and the impregnated material being heated, if necessary, to bring about the desired reaction.  The polymeric material may be cellulosic, such as paper, wood or cellulosic film, a cellulose derivative such as cellulose acetate, proteinaceous material, such as wool or leather, or textile material derived from such cellulosic or proteinaceous materials, for example, in the form of fibres, yarns or fabrics including woven or knitted fabrics or non-woven fabrics.  The textile materials may be treated additionally with amido-formaldehyde resins or other known crease-resisting agents. The treated textiles have the following improved properties: dry crease resistance, resistance to swelling, smooth drying, resistance to shrinkage, resistance to abrasion, fixation of stiffening agents such as starch, less tendency to retain chlorine from chlorine-containing bleach and less tendency to attack by mildew; treated paper has improved breaking strength; and textiles, paper and films have increased affinity for anionic dyes.  Furthermore, if in the sulphonium compounds, the group R3 and/or R4 is an alkyl group containing from 10 to 18 carbon atoms, the compounds can act as softeners, lubricants or water-repellents when reacted with the polymeric material; and if R3 and/or R4 contain chromophonic groups or are the residues of a dyestuff, then the sulphonium compounds are capable of providing wash-fast dyeings with certain materials, e.g. cellulosic materials. Examples illustrate the treatment and dyeing of cotton fabric, and the treatment of paper, cellulose acetate fabric, non-woven viscose rayon/nylon fabric and spun viscose rayon fabric using, as sulphonium compounds, the disodium salt of tris-(b -sulphatoethyl) sulphonium inner salt, tris-(b -chloroethyl) sulphonium chloride, a mixture of bis-(b -hydroxyethyl) ethyl sulphonium bromide and the phosphorus pentoxide reaction product thereof, and methyl 2-sulphatoethyl lauryl sulphonium inner salt.  Specification 988,512 is referred to.