Patent GB-973259-A (GB)
Title: Dyestuffs derived from n-substituted perinaphtholactams
IPC: C08K5/00
Filed: 1962-09-20
Abstract: Naphtholactam derivatives for use in the preparation of dyestuffs (see Division C4) are prepared by reacting naphtholactam-(1, 8) with 4-ethoxy-N-methyldiphenylamine in the presence of chlorobenzene and phosphorus oxychloride (a); 4-chloronaphtholactam with N, N-diethyl-aniline (b); 4-chloronaphtholactam with 4-ethoxy-N-methyl-diphenylamine (c); 2, 4-dichloronaphtholactam-(1, 8) with diethyl aniline (d); monobromo-N-ethyl-peri-naphtho-lactam with bromine (e); N-ethyl-(N1, N1-bis-acetyl)-amino-peri-naphtholactam is prepared by nitrating N-ethyl-peri-naphtholactam, reducing the mononitroderivative to the corresponding amino derivative and heating with excess acetic anhydride (g); N-ethyl-(dimethylamino)-naphtholactam is prepared by reacting ethylaminonaphtholactam with dimethyl sulphate (h) and in a further process naphtholactam-(1, 8) is reacted with 1-dimethylamino-naphtholene. Specification 973,260 is referred to.ALSO:The invention comprises dyestuffs of the general formula <FORM:0973259/C4-C5/1> wherein R1 denotes an alkyl, cycloalkyl, aryl or aralkyl radical, Ar represents an aromatic radical, and R2 and R3 which may be the same or different, denote hydrogen atoms or alkyl, cycloalkyl, aryl or aralkyl radicals, or may be joined to form a saturated heterocyclic ring system and wherein the aromatic rings, as well as the alkyl and cycloalkyl radicals may be substituted by non-ionic substituents and wherein X denotes an anionic residue.  The dyes are prepared (a) by heating a naphtholactam of the general formula <FORM:0973259/C4-C5/2> where R1 has the meaning given above and the aromatic rings, as well as the alkyl or cycloalkyl radical may be substituted as indicated above, in the presence of a condensation agent having water-eliminating activity with an amine of the general formula <FORM:0973259/C4-C5/3> wherein Ar, R2 and R3 have the meaning given above or (b) by treating with an alkylating agent a compound of the formula <FORM:0973259/C4-C5/4> in which R5 stands for a hydrogen atom or an alkyl or cycloalkyl radical and R6 is a hydrogen atom or an alkyl or aryl radical and wherein the aromatic and aliphatic radicals are free of sulphonic and carboxylic acid groups but may contain non-ionic substituents.  Non-ionic substituents which may be present in both alkyl radicals and aromatic rings include chlorine, bromine and fluorine atoms, hydroxy, alkoxy, carboxylic acid ester and amide, arylazo and cyano radicals and the aromatic rings may also contain alkyl and sulphonamide radicals. Condensing agents specified include phosphorus oxychloride, oxybromide, pentachloride and trichloride, sulphuryl and thionyl chlorides, phosgene, stannic chloride, titanium tetrachloride, zinc and aluminium chlorides, boron trifluoride, silicon tetrachloride and mixtures thereof.  Solvents specified include various chlorinated hydrocarbons, nitrobenzene, phosphorus oxychloride and thionyl chloride.  An excess of amine may also be employed as solvent. X may represent the anion from hydrochloric, sulphuric or acetic acid. Alkylating agents specified include dimethyl and diethyl sulphates, benzene sulphonic ethyl ester, p-toluene sulphonic methyl ester, methyl and ethyl chlorides, bromides and iodides, n-propyl bromide, i-butyl iodide and n-butyl bromide.  Naphthalactams for use as starting materials in process (a) may be obtained by the process of Specification 973,260 acid dyestuffs for use as starting materials in process (b) may be obtained by condensing unsubstituted or substituted naphtholactams with appropriate aromatic amines in an inert solvent by means of phosphorus oxychloride or thionyl chloride and liberating the bases by means of alkali.  The dyes are suitable for dyeing and printing materials consisting wholly or largely of polymerized acrylonitrile or vinylidene cyanide, tanned cotton, cellulose esters, e.g. cellulose acetate and paper pulp. Specification 289,692 also is referred to.