Patent GB-1114516-A (GB)
Title: Quaternary ammonium compounds and textiles treated therewith and production thereof
IPC: D06M15/568
Filed: 1966-02-01
Abstract: Compounds of the formula <FORM:1114516/C2/1> wherein R1 is an alkyl radical containing from 1 to 3 carbon atoms, a hydroxyalkyl radical containing from 1 to 3 carbon atoms or a hydroxy terminated polyoxyalkylene ether group containing from 1 to 5 moles of alkylene oxide (e.g. a group of the formula <FORM:1114516/C2/2> wherein y is an integer from 1 to 5, n is an integer from 1 to 3 and m is an integer from 2 to 4); R2 and R3 are each an alkyl radical containing from 16 to 22 carbon atoms; at least one of M1 and M2 is a methylol radical and the other is a hydrogen atom or a methylol radical; x is 0 or an integer from 1 to 3; and X - is a halide ion and preparation thereof by reacting a tertiary amine having two long-chain alkyl groups containing from 16 to 22 carbon atoms derived from one or more fatty acids attached to the nitrogen atom thereof with a halogenoalkanoic acid amide quaternizing agent and then reacting the amido group in the product thus formed with formaldehyde or a suitable source thereof such as paraformaldehyde.  The reaction is preferably carried out by refluxing the reactants in a suitable solvent, e.g. iso-propanol, and the desired quaternary salt is obtained as a paste containing 25% of the solvent.  The preferred tertiary amine starting material is a methyl dihydrogenated tallow amine.  The products of the invention are cationic surface-active compounds with application in treating textile materials to impart softness or tear strength.  Reference has been directed by the Comptroller to Specification 1,046,417.ALSO:Textile articles with durable softness have deposited on the surface thereof from 0.1% to 15%, based on the dry weight of the said textile, of a cationic surface active quaternary ammonium compound of the formula: <FORM:1114516/D1-D2/1> wherein R1 is an alkyl radical containing from 1 to 3 carbon atoms, a hydroxy alkyl radical containing from 1 to 2 carbon atoms or a hydroxy terminated polyoxyalkylene ether group containing from 1 to 5 moles of alkylene oxide (e.g. a group of the formula CnH2nO(Cm  H2mO)yH wherein y is an integer from 1 to 5, n is an integer from 1 to 3 and m is an integer from 2 to 4); R2 and R3 are each an alkyl radical containing from 16 to 22 carbon atoms; at least one of M1 and M2 is a methylol radical and the other is a hydrogen atom or a methylol radical; x is 0 or an integer from 1 to 3; and X- is a halide ion and preparation thereof by applying an aqueous dispersion of a compound of the above formula, optionally in association with a catalyst such as ammonium chloride, zinc nitrate or magnesium chloride, to the textile which is then dried and subsequently cured at an elevated temperature. The preferred softening agent is derived from a methyl dihydrogenated tallow amine by quaternisation with chloracetamide followed by methylation of the amido group in the product with formaldehyde.  Cellulosic textiles, e.g. scoured cotton crash towelling or cotton poplin are particularly suitable for treatment since the methylol groups (CH2OH) in the softening agent may condense at the curing stage with hydroxyl groups in the cellulose.  Other textiles, e.g. wool, nylon and polyesters, which contain suitable reactive groups are also specified.  The softening agent, optionally in association with a urea resin finish, may be applied by conventional immersion or spraying methods and the treated textile is preferably dried at 140 DEG F. before being cured at 320 DEG F.  The above compounds, which retain their softening action after repeated laundering, also act as waterproofing agents and impart improved tear strength.  Reference has been directed by the Comptroller to Specifications 1,046,417