Patent GB-1019575-A (GB)
Title: ª‡,ª‰-bis-(benzoxazolyl-(2))-ethylene derivatives and method of preparing the same
IPC: D06L4/614
Filed: 1962-07-23
Abstract: Optical brightening agents of the formula <FORM:1019575/C3/1> or acid salts thereof, wherein R1 and R2 are hydrogen or C1- 4 alkyl, Y1 is hydrogen or -CH2NR3R4 and Y2 is -CH2NR3R4, where R3 and R4 are hydrogen or aliphatic, aromatic, cycloaliphatic or heterocyclic groups or together with the nitrogen make up a heterocyclic ring (see Division C2), are introduced into plastic materials during the manufacture thereof.  In examples, a brightening agent as above is added to a solution of acrylonitrile-vinyl chloride copolymer in acetone/acetic acid, and the solution spread on a glass plate and dried to produce a copolymer film; to a solution of polyacrylonitrile in dimethyl formamide; and a mixture of acrylonitrile, methyl acrylate, and potassium persulphate and a brightening agent as above, in solution in dimethyl sulphoxide, is heated to produce a copolymer liquor.  Other plastic materials are listed, viz. copolymers of acrylonitrile with vinyl pyridine or vinyl acetate, polyethylene, polypropylene and polyvinylacetal.ALSO:The invention comprises a compound of formula <FORM:1019575/C2/1> or an acid salt thereof, wherein R1 and R are2 hydrogen or C1- 4 alkyl, Y1 is hydrogen or ..CH2NR3R4 and Y2 is -CH2NR3R4, where R3 and R4 are hydrogen or aliphatic, aromatic, cycloaliphatic or heterocyclic groups or together with the nitrogen make up a heterocyclic ring: and their production by reacting a corresponding halogenomethyl compound with HNR3R4, or by reacting a corresponding halogenomethyl derivative of a 1,2-di-(benzoxazolyl)-ethane with HNR3R4, and treating the product with a mild oxidant in an aqueous acidic or organic solution at 50-180 DEG  C., e.g. with H2O2, nitrobenzene, mercuric acetate or HgO, or with SOCl2 or SO2Cl2 in the presence of iodine. Specified groups R3 or R4 are methyl, ethyl, butyl, octyl, hydroxyethyl, dimethylaminoethyl, cyclohexyl, phenyl, tolyl, guanidino or thiazolyl; or they may make up a piperidino, alkylpiperidino or morpholino radical.  The halogenomethyl compounds may be prepared from the di-benzoxazolyl ethylene or ethane and (i) CH2O, H2SO4 and a halogenosulphuric acid at 20-80 DEG  C., or (ii) a dihalogenomethyl ether and H2SO4 or ZnCl2.  The ethane derivative may be oxidized as described above to produce the ethylene compound.  The compounds of the invention are optical brightening agents (see Divisions B5, C3 and D1).ALSO:Optical brightening agents for brightening textile fabrics and fibres have the formula <FORM:1019575/D1-D2/1> or an acid salt thereof, wherein R1 and R2 are hydrogen or C1-4 alkyl, Y1 is hydrogen or -CH2NR3R4 and Y2 is -CH2NR3R4, where R3 and R4 are hydrogen or aliphatic, aromatic, cycloaliphatic or heterocyclic groups or make up with the nitrogen a heterocyclic ring (see Division C2).  The agents may be employed in organic solution or aqueous dispersion.  Conventional bleaching, washing and finishing agents may be present.  Polyacrylanitrile, polyamide, polypropylene, polyethylene, polyvinylacetate, viscose rayon, cellulose acetate, wool and cotton fibres may be brightened.