Patent GB-962019-A (GB)
Title: Naphthalimide optical whitening agents
IPC: D06L3/12
Filed: 1962-04-04
Abstract: The invention comprises optical whitening agents of formula: <FORM:0962019/C1/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2. The compounds may be made by treating a compound of the above formula, where X replaces R1O, X being a sulpho group, or a salt thereof, a nitro group or a halogen atom, in the presence of a condensing agent, with a compound of formula R, OH, or a salt thereof; or by etherifying a compound where X is OH, or a salt thereof; or by condensing an appropriate dicarboxylic acid, or anhydride thereof, with an amine of formula R2NH2. Representative of specified values for R1 are methyl, iso-pentyl, n-tridecyl, hydroxyethyl, propoxypropyl, aminopropyl, N,N-dimethylaminoethyl, N-trimethyl ammonium propyl, naphthyl, benzyl and cyclohexyl. Indicated substituents for R1 when aryl are alkyl, alkoxy, hydroxy, alkoxyalkyl, hydroxy-alkyl, amino, sec. and tert.-aminoalkyl, great-ammonium alkyl, nitro and halogen. Representative of indicated amines of formula R2NH2 are ethyl, iso-decyl and propanolamines, ethylene diamine, N,N-dimethylpropylene diamine, ethoxyethylamine, naphthylamine, benzylamine and cyclohexylamine. R2, when aryl may contain such groups as alkyl, alkoxy, hydroxy, alkoxyalkyl, hydroxy-alkyl, nitro, amino and halogen. R2 may also be <FORM:0962019/C1/2> The first method is preferably effected with caustic soda, or potash, as condensation agent and the second with conventional etherifying agents in the presence of alkaline substances. In all methods solvents or diluents may be present and temperatures of up to 200 DEG C. used. Numerous examples are provided of the preparation of the compounds and their uses for whitening textiles (see Division D1) and synthetic resins (see Division C3).ALSO:Moulded materials from synthetic resins e.g. polyvinyl chloride, polyacrylate, polyester, polycarbonate, polyurethane, polyamide, polyolefine and polystyrene resins, are white-enhanced by the addition, during, or after their manufacture, of an optional whitening agent of formula: <FORM:0962019/C3/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2. In Example 68 0.2%, by weight, of one of the agents, e.g. N-phenyl-4-methoxy-naphthalimid and, optionally, 2 to 5% by weight of titanium dioxide, is incorporated in a polystyrene, polyvinylchloride, polyacrylate, polyamide, polyester or polycarbonate resin which, after kneading, is formed into plates.ALSO:Textile materials are treated with an optical whitening agent of formula <FORM:0962019/D1-D2/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2.  Materials treated are especially synthetic organic high molecular weight substances such as polyesters e.g. polyethylene terephthalate, polyvinyls e.g. polyacrylonitrile and polyvinylchloride, polyamides, polyolefines e.g. polypropylene and cellulose esters e.g. cellulose acetate. In examples (63) polyester material is treated with an aqueous dispersion of N-methyl-4-methoxy-naphthalimide in the presence of chlorobenzenes and a condensate of naphthalene-2-sulphonic acid and formaldehyde (65) and (66) the same naphthalimide, dispersed in water with a condensate of 2-mephthol-6-sulphonic acid, creol and formaldehyde, is used to treat cellulose acetate and polypropylene materials respectively, (64) polyester material is treated with N-butyl-4-methoxy-naphthalimide under the conditions of (65) and in (67) polyacrylonitrile material is treated with an acetic acid, sodium acetate aqueous solution of compounds where either R1 is Me and R2 is (CH2)3-N+(CH3)3 or R1 is (CH3)3N+-(CH2)2 and R2 is Me, all the treated textiles being soaped, rinsed and dried.