Patent GB-1113638-A (GB)
Title: Process for modification of cellulose
Inventor: GAZZARD EDWARD GEORGE
IPC: D06M15/423
Filed: 1964-11-20
Abstract: N - Methylol - 3,4 - dihydro - 2H - pyran - 2 - carbonamide carbonamide is prepared by heating a mixture of 3,4 - dihydro - 2H - pyran - 2 - carbonamide, paraformaldehyde and solid sodium hydroxide to 100-115 DEG  C. until molten and then stirring and heating the mixture at 85-90 DEG  C. for 4 hours and then cooling it, the resulting product being crystallized from methanol, recrystallized from acetone and further recrystallized from methylated spirits.  2 - N - Stearoylaminomethyl - 3,4 - dihydro-2H-pyran is prepared by heating together a mixture of a solution of stearoyl chloride in benzene and a mixture of 2-aminomethyl-3,4-dihydro-2H-pyran and sodium bicarbonate in benzene under reflux, cooling, filtering, distilling the benzene off the filtrate under vacuum and crystallizing the resulting residue from acetone.ALSO:Cellulosic textile materials and paper may be creaseproofed, waterproofed and given a modified handle, and an affinity for acid dyestuffs by reacting them in the presence as catalyst of a acid or substance capable of generating an acid under the reaction conditions used, with a compound containing at least one 3,4-dihydro - 2H - pyranyl radical.  The compound may be 3,4 - dihydro - 2H - pyran itself having the formula <FORM:1113638/D1-D2/1> 2 - aminomethyl - 3,4 - dihydro - 2H - pyran, 2 - NN - dimethylaminomethyl - 3,4 - dihydro - 2H - pyran, 2 - N - stearoyl aminomethyl - 3,4 - dihydro - 2H - pyran, the neopentyl bisester of 3,4 - dihydro - 2H - pyran - 2 - carboxylic acid, benzyl tris - (3,4 dihydro - 2H - pyran - 2 - carboxyethyl) ammonium chloride, quaternary salts of the triethanolamine tris-ester of 3,4 - dihydro - 2H - pyran - 2 - carboxylic acid, an amide derived from a 2 - amino methyl - 3, 4 - dihydro - 2H - pyran and a 3,4 - dihydro - 2H - pyran - 2 - carboxylic acid, or N - methylol - 3,4 - dihydro - 2H - pyran - 2 - carbonamide obtained by the reaction of formaldehyde on 3,4 - dihydro - 2H - pyran - 2 - carbonamide.  The material may be impregnated with a solution or dispersion of the 3,4 - dihydro - 2H - pyranyl compound and catalyst in for example water, dried at a temperature not exceeding 120 DEG C and baked at a temperature of 120 DEG -200 DEG C for from 10 seconds to 30 minutes suitable catalysts being ammonium dihydrogen phosphate or ammonium thiocyanate, butanolamine hydrochloride, tartaric, oxalic or maleic acid, zinc chloride or nitrate or magnesium chloride.  Alternatively the material may be immersed in a solution or dispersion of the 3,4 - dihydro - 2H - pyranyl compound and a strong acid, e.g. nitric, hydrochloric, phosphoric, sulphuric or trichloro acetic acid, at the ordinary temperature until reaction has taken place or the material may be padded with the solution or dispersion, batched and allowed to stand until reaction has taken place care being taken to ensure that the material does not dry out during this period.  The treatment may be combined with the application of a nitrogen resin precondensate, e.g. methylol derivatives of urea, ethylene urea, thiourea, dicyandiamide, amines, amides, carbamates, aminotriazines, urons, ureins, ureides, imidazolidones, pyrimidones and triazones and lower alkyl ethers thereof, or with the application of an aldehyde, e.g. formaldehyde, glyoxal, succindialdehyde or hydroxyadiphaldehyde, Textile materials made from cotton, linen, viscose rayon including polynosic rayons in the form of fibres, rovings, yarns or woven, non-woven or knitted fabrics may be treated.  (D1B of Examples 1 and 2).