Patent GB-842112-A (GB)
Title: Anti-halation layers and filter layers for photographic materials
IPC: C07D277/64
Filed: 1957-01-11
Abstract: p - (N - methyl - N - p1 - ethoxy - phenyl-amino)-benzaldehyde is prepared by introducing p-ethoxy-N-methyl-diphenylamine into a mixture of formyl-monomethyl-aniline and phosphorus oxychloride, and pouring the product into ice and and water.  Sulphonation of the product with sulphuric acid monohydrate and oleum gives p - (N - methyl - N - p1 - ethoxy - m1 - sulphophenylamino) - benzaldehyde.  p ; p1 - Diformyl-N - ethyl diphenylamine is prepared by adding N-ethyl diphenylamine to a mixture of dimethyl formamide and phosphorus oxychloride.  The corresponding N-methyl derivative is similarly prepared.  2 - Cyanacetamido - naphthalene - 6 - carboxylic acid is obtained by reacting b -naphthylamine-6-carboxylic acid with cyanacetic ester in pyridine.  3 ; 4 - Dimethyl - cyanacetobenzene is prepared by treating o-dimethyl benzene with chloracetic acid and aluminium chloride to give the chloracetyl compound and treating this with potassium cyanide.  p-Methoxy cyanacetobenzene is prepared by adding aqueous potassium cyanide to p-methoxy chloroacetobenzene in aqueous ethanol.  4 ; 5 ; 7 - Trihydroxy coumarin - 8 - carboxylic acid ethyl ester is prepared by refluxing acetone dicarboxylic acid diethyl ester with sodium in benzene.  Specifications 742,112, 760,739, and 818,639 are referred to.ALSO:Methine dyes having one of the general formulae:  <FORM:0842112/IV (c)/1> and <FORM:0842112/IV (c)/2> wherein A and B are -CN, -COX1 or -CONHR1 (where X1 is an alkyl, alkoxy, aryl or substituted aryl group and R1 is H, aryl or substituted aryl), or A and B together complete a heterocyclic ketomethylene ring, or A is H and B is a quaternary heterocyclic nitrogen base, X and X11 are aryl residues which may carry substituents and R is H or a substituted or unsubstituted alkyl group, are prepared by condensing an aldehyde OCH-X-NR-X11 or OCH-X-NR-X-CHO with an appropriate compound containing a reactive methyl or methylene group. Suitable monoaldehydes are those wherein X is phenyl, R is H, methyl or ethyl, and X11 is phenyl, p-methoxyphenyl, p-methoxy-m-sulphophenyl, p-ethoxyphenyl, p-ethoxy-m-sulphophenyl, or p-tolyl.  Symmetrical di-aldehydes are p; p1-diformyl-N-methyl (or ethyl)-diphenylamine and p; p1-diformyl-diphenylamine-N-acetic acid.  Compounds having an active methyl or methylene group are 5-pyrazolones such as 3-methyl- or 3-carboxypyrazolones having in the 1-position a 6-sulpho-2-naphthyl group or a phenyl group which may be substituted with one or more of the groups methyl, sulpho, carboxy, hydroxy or chlore, or amides or esters of such 3-carboxy-pyrazolones, isoxazolones, 3-hydroxythiophenes, 4-hydroxy coumarins such as 4; 5; 7-trihydroxy-coumarin-8-carboxylic acid ethyl ester, oxindoles, cyanacetoaryl compounds such as p-methoxy-cyanacetobenzene and 3; 4-dimethyl-cyanaceto-benzene, cyanacetamide and substituted cyanacetanilide compounds, 6-carboxy-cyanaceto-naphthylamine-2, malodinitrile, malonic acid esters and amides, acetoacetanilide, benzoyl-acetanilide, and quaternary salts of thiazole, benzthiazole, naphthathiazole, oxazole, benzoxazole, naphthoxazole, benzselenazole, pyridine, quinoline, benzimidazole and indolenine, which have an active a - or #j-methyl group, especially internal sulphonates of such bases such as are described in Specification 742,112, e.g. 2-methyl benzthiazole-N-butane sulphonic acid betaine. Specifications 760,739 and 818,639 also are referred to.