Patent GB-993596-A (GB)
Title: Improvements in or relating to the modification of polymers
IPC: D06M13/13
Filed: 1963-04-23
Abstract: b -Hydroxyglutaronitrile is prepared by reacting an aqueous solution of potassium cyanide with 1,3-dichloro-propanol-2 and converted to: b -Methoxyglutaronitrile by reacting with dimethyl sulphate in the presence of sodium hydroxide.  b -Methyoxyadiponitrile is prepared by reacting 1,4-dicyanobutene-2 with a solution of sodium in methanol. N,N - Methylene - bis - (methoxypropionamide) is prepared by reacting N,N-methylene-bis-(acrylamide) with a solution of sodium in methanol. Methoxypropionamidomethylacrylamide is prepared by reacting N-methylolacrylamide and methoxypropionamide in the presence of hydrochloric acid.  1,4 - Dinitro-2,3-butandiol is prepared by reacting a methanol solution of nitromethane with aqueous glyoxal in the presence of sodium hydroxide.  1,4 - Bis - (b  - methoxypropionyl)piperazine is prepared by reacting b  - methoxypropionyl chloride or methyl b -methoxypropionate with piperazine.  N,N1 - Bis - (b  - methoxypropionyl) - N,N1-dimethyl -1,2-ethylenediamine is prepared by b -methoxypropionyl chloride with N,N1-dimethyl-1,2-ethylenediamine.  N,N1 - Bis - (b  - methoxypropionyl)hexamethylenediamine is prepared by reacting N,N-hexamethylene bis-(acrylamide) with a solution of sodium in methanol.  1,3,5 - Tris - (b  - methoxypropionyl, b  - ethoxypropionyl or b  - butoxypropionyl)hexahydro-s-triazine is prepared by reacting b -methoxy-, b -ethoxy or b -butoxypropionitrile with trioxane.  1,3,5 - Tris - (b  - hydroxypropinyl)hexahydro-s-triazine is prepared by reacting tris - (acryloyl)-hexahydro-5-triazine with aqueous sodium hydroxide.  Bis - (b  - methoxypropionyl) - octadecylthio-propionyl-hexahydro -s-triazine is prepared by reacting tris - (acryloyl)hexahydro-s-triazine and octadecyl mercaptan with a solution of sodium in methanol.ALSO:A process for the modification of polymers containing active hydrogen atoms comprises reacting the polymers with a compound containing at least one group of formula <FORM:0993596/C3/1> or <FORM:0993596/C3/2> wherein X is an electron attracting, activating group and Y is hydrogen or an alkyl group containing 1 to 6 carbon atoms, in the presence of an alkaline catalyst at an elevated temperature. The polymer may be cellulose or a cellulose derivative, e.g. hydroxyethyl cellulose, starch or polyvinyl alcohol, and may be in the form of a textile material or fabric.  Specified catalysts are alkali metal hydroxides, carbonates, bicarbonates, phosphates and silicates, and quaternary ammonium hydroxides.  The polymer may be treated with the compound in solution in water or organic solvents such as alcohols, ketones, ethers and hydrocarbons. Preferred activating groups are -CO-, -CN, -NO2, -CF3 and -CF2-.  Many suitable compounds are listed, and examples describe the treatment of cotton fabrics with (1 and 20) 1,3,5-tris(b -methoxypropionyl)hexahydro - s - triazine, (2) b  - hydroxyglutaronitrile, (3) 1,4 - dinitro - 2,3 - butane diol, (4) 4-chloro-3-hydroxybutyronitrile, (5) N,N1-methylene bis b -methoxypropionamide, (16) N,N1-bis b -methoxypropionyl piperazine, (17) 1,3,5-tris (b -hydroxypropionyl)-hexahydro - s - triazine, (18) 1,3,5 - tris(b - ethoxypropionyl)hexahydro - s - triazine, and (19) bis b  - methoxypropionyl - octadecylthiopropionyl hexahydro - s - triazine; of rayon fabric with (6) N,N-methylene-bis-b -methoxypropionamide and (7) 1,3,5-tris(b -methoxypropionyl)-hexahydro - s - triazine; of polyvinyl alcohol with (8) N,N-methylene bis-methoxypropionamide and (9) 1,3,5-tris(b -methoxypropionyl)-hexahydro - s - triazine; of soluble starch with (10) N,N-methylene bis-methoxypropionamide and (11) 1,3,5-tris(b -methoxypropionyl)-hexahydro - s - triazine; of hydroxyethyl cellulose with (12) 1,3,5 - tris(b  - methoxypropionyl)hexahydro - s - triazine and (13) N,N-methylene bis-methoxypropionamide:  of polyvinyl alcohol fibres with (14) N,N-methylene bis methoxypropionamide; and cotton yarn with (15) 1,3,5-tris(b -methoxypropionyl) hexahydro-s-triazine.ALSO:The crease recovery, heat and dimensional stability, tensile and tear strengths and abrasion resistance of textile materials made of polymers containing active hydrogen atoms are improved by treating the materials at elevated temperature in the presence of an alkaline catalyst with compounds containing at least one group <FORM:0993596/D1-D2/1> where X is an electron attracting, activating group and Y is hydrogen or an alkyl group containing 1 to 6 carbon atoms.  The material may be in the form of fibres, yarns or fabrics, and may be of cotton, linen, rayon, wool, silk, polyamide or polyvinyl alcohol.  The catalyst may be an alkali metal hydroxide, carbonate, bicarbonate, phosphate or silicate, or a quaternary ammonium hydroxide, and the treatment may be effected with the compound in solution, e.g. in water or an alcohol, ketone, ether or hydrocarbon.  Many suitable compounds are listed and examples describe the treatment of cotton fabrics with (1 and 20) 1, 3, 5-tris (b -methoxypropinyl) hexahydro-s-triazine, (2) b -hydroxyglutaronitrile, (3) 1, 4-dinitro-2, 3-butanediol, (4) 4-chloro-3-hydroxybutyronitrile, (5)N, N-methylane-bis methoxypropionamide (16) N, N1-bis b -methoxy-propionyl piperazine, (17) 1, 3, 5-tris(b -hydroxypropionyl) hexahydro-s-triazine, (18) 1, 3, 5-tris(b -ethoxypropionyl) hexahydro-s-triazine and (19) bis b -methoxypropionyl-octadecylthio propionyl hexahydro-s-triazine; rayon fabrics with (6) N, N-methylene bis b -methoxypropionamide and (7) 1, 3, 5-tris(b -methoxypropionyl) hexahydro-s-triazine; polyvinyl alcohol yarn with (14) N, N-methylene bis b -methoxypropionamide; and (15) cotton yarn with 1, 3, 5-tris(b -methoxypropionyl) hexahydro-s-triazine.