Patent GB-506999-A (GB)
Title: Improvements in or relating to the manufacture and use of new chemical substances
IPC: C08G65/40
Filed: 1937-12-04
Abstract: 506,999. Synthetic resins ; cellulosic compositions ; crease - proofing textiles. MOSS, W.H. Dec. 4, 1937, No. 33621. [Classes 2 (ii), 2 (iii), and 15 (ii)] Synthetic resins are prepared by reacting a phenol, an aromatic sulphonamide, and a compound containing at least two halogen atoms attached to different carbon atoms of an aliphatic grouping. Preferably the phenol is a di-p-phenylol compound in which each phenylol group is unsubstituted or is alkyl- or halogensubstituted in the nucleus only, and both phenylol groups are attached to the same carbon atom of a hydrocarbon residue containing not more than about 7 carbon atoms and free from aliphatic unsaturated linkages. The reaction may be carried out in aqueous alkali under reflux, or on the fibre of textile materials, such as cotton, linen, regenerated cellulose, or cellulose derivatives; for example di-(4-hydroxyphenyl) - dimethyl - methane and p - toluene sulphonamide in mildly alkaline solution are applied to cellulose acetate followed by glycerol dichlorhydrin. The reactants may be used in equimolecular or other proportions, e.g. the phenol, sulphonamide, and halogen compound may be in the ratio 1 : 1 : 2, when thermosetting resins are obtained. There are specified : phenols-monohydric phenols, e.g. phenol, o-, m-, and p-cresols, and alpha-naphthols, o- and ptertiary-amylphenols, 1,3,5-xylenol ; polyhydric phenols, e.g. resorcinol, 4,4<1>-dihydroxydiphenyl; phenols containing two phenylol groups attached to an aliphatic grouping, e.g. di-(4-hydroxyphenyl)-methylmethane, -ethylmethane, -propylmethane, -dimethylmethane, -methylethylmethane, -dipropylmethane, -phenylmethane, 'and 1,1 - di - (4 - hydroxyphenyl) - cyclohexane; alkyl or halogen nuclear-substitution products of the above, e.g. di-(4-hydroxy-3-methyl phenyl) - dimethylmethane, di - (4 - hydroxy - 3,5 - dimethylphenyl) - dimethylmethane, di - (4 - hydroxy - 3 - methyl - 5 - chlorphenyl) - dimethylmethane, di - (4 - hydroxy - 3,5 - dichlorphenyl)-methylmethane, -ethylmethane, -pro pylmethane, -dimethyl-methane, or -methylethylmethane, or the corresponding bromine derivatives ; sulphonamides-mono- or polynuclear sulphonamides which may be nuclearsubstituted, e.g. by alkyl (e.g. methyl or ethyl), acidylamino, halogen or hydroxyl groups, or N-substituted by an alkyl or aralkyl group, e.g. benzene, o- and p-toluene, xylene, and naphthalene sulphonamides, ethyl-toluene sulphonamide ; halogen compounds-alkylene halides, e.g. amylene dichloride, substituted oxy-compounds, e.g. #,#<1>-dichlordiethylether, dichloracetone, dichlor-derivatives of sec.-butyl alcohol, or halogenhydrins, e.g. syn.- or assym.- glycerol dichlorhydrins. The products may be moulded, used in coating compositions, or for creaseproofing textiles. In examples (1), (2) resins soluble in acetone, alcohol and benzene are prepared by condensing diphenylol propane, p-toluenesulphonamide and sym.-glycerol dichlorhydrin, in molar proportions of (1) 1 : 1 : 2 and (2) 1 : 1 : 1 ; (8) cellulose acetate artificial silk is creaseproofed by immersion in an alcohol solution of the product of example (1), drying, and heating. Compositions may comprise the resins together with film-forming substances, e.g. nitrocellulose, organic esters of cellulose such as the formate, acetate, .propionate, and butyrate, cellulose ethers such as methyl, ethyl, and benzyl cellulose, and vinyl resins, e.g. polyvinyl acetate. The resin may be precipitated from solution on to a finely divided cellulose derivative, or may be absorbed thereby from solution or dispersion. Solutions of these compositions in volatile solvents, e.g. acetone, with or without plasticizers, medium or high boiling solvents, natural or synthetic resins, fire retardants, pigments, dyes, or effect, materials may be used as adhesives or coating or impregnating compositions, e.g. for protecting rubber or other insulation or as insulating materials. Solutions containing, the resins and cellulose ester or ethers may be formed into threads or films or used as aeroplane fabric dopes (e.g. with addition of aluminium powder). Those con-, taining colouring materials also may be used as printing inks for plastic material, e.g. cellulose acetate films. The compositions may be moulded, e.g. to form interlayers for safety glass, rods, tubes, or blocks. In examples : (3) a lacquer consists of the resin of example (2), cellulose acetate, alkyl toluene sulphonamide or diethyl phthalate, acetone, ethyl alcohol, benzene, and ethyl lactate, with or without titanium oxide ; (4) a moulding powder consists of the resin of example (2), cellulose acetate, and dimethyl phthalate ; (5) a solution for spinning or for making thin films consists of the resin of example (2), cellulose acetate, and acetone ; (6) an ink for cellulose acetate and like films or for paper consists of the resin of example (2), cellulose acetate, triacetin, methyl ethyl ketone, diacetone alcohol, and crimson lake ; (7) an adhesive for cellulose acetate or leather consists of the resin of example (2), cellulose acetate, triacetin, methyl ethyl ketone, and acetone. The Provisional Specifcation refers to the use of " aliphatic halides " in general and to the use as phenols of the side-chain-halogenation products of those listed above.