Patent GB-1086068-A (GB)
Title: Process for the whitening of polymeric materials and nitrogen-containing polycyclic compounds for use therein
Inventor: KEATS GEORGE HAROLD
IPC: D06L4/614
Filed: 1964-09-02
Abstract: Compounds which contain in the molecule at least one group of the formula <FORM:1086068/C2/1> are prepared by reacting a compound of the formula R-NH-NH2 with a compound of the formula <FORM:1086068/C2/2> in solution in the presence of an acid catalyst, or with a compound of the formula <FORM:1086068/C2/3> in solution in the presence of an alkaline catalyst, A being an aromatic nucleus which may form part of a larger aromatic system, R being an aromatic radical, R1 being hydrogen or an alkyl, aryl or aralkyl radical, X being any divalent radical such that the CH2 group in a compound of the formula <FORM:1086068/C2/4> is capable of reacting with an aldehyde to give an ylidene derivative, A, R, R1 and X being free from chromophoric groups, Z being a group such that the molecule HZ is readily split off from the compound of Formula IV under the reaction conditions. The invention also comprises those compounds of Formula I above wherein R represents an unsubstituted or substituted phenyl radical or a heterocyclic radical. In Examples 24 and 25 a b -hydroxyethylsulphonyl side chain is converted to the potassium salt of a b -sulphatoethylsulphonyl side-chain and thence to a vinylsulphonyl side chain.  In Example 26 a substituent carbonyl group is methylated.  4-Methoxynaphthylidene-1-tetralone is prepared by reacting 1-tetralone with 1-methoxy-4-naphthaldehyde in the presence of caustic potash solution.  A monochloro-1-tetralone is prepared by reacting chlorobenzene with g -butyrolactone in the presence of AlCl3 and is subsequently reacted with benzaldehyde in alcoholic KOH to give 2-benzal-monochloro-1-tetralone.  2 - (Piperidinomethyl) - 1 - tetralone hydrochloride is prepared from 1-tetralone, piperidine hydrochloride and paraformaldehyde.  3 - (Benzylaminomethyl) - 6 - methyl - thiachroman-4-one hydrochloride is prepared from benzylamine hydrochloride, 6-methyl-thiachroman-4-one and paraformaldehyde.ALSO:Fibrous polymeric materials are whitened by the incorporation therein of a compound of the general formula <FORM:1086068/D1-D2/1> wherein A represents an aromatic nucleus which may form part of a larger aromatic system, R represents an aromatic radical, R1 represents hydrogen or an alkyl, aryl or aralkyl radical, and X represents any divalent radical such that the CH2 group of a compound of the general formula <FORM:1086068/D1-D2/2> is capable of reacting with an aldehyde to give an ylidene derivative, and in which A, R, R1 and X are free from chromophoric groups.  The incorporation may be achieved by treating the polymeric material with an aqueous dispersion or solution of the whitening compound.  Surface-active agents and/or other whitening agents may also be present.  Specified polymeric materials are polyamides such as polyhexa-methylene adipomide, polyesters such as polyethylene terephthalate, polyurethanes, polyacrylonitrile, hydrolysed polyacrylonitriles, polymethyl methacrylate, polystyrene, polyethylene, polypropylene, secondary cellulose acetate, cellulose triacetate, regenerated cellulose such as viscose, cotton, paper, silk and wool.