Patent GB-773152-A (GB)
Title: Improvements relating to bis-triazinylamino stilbene compounds and their use as optical brightening agents
IPC: D21H21/30
Filed: 1954-11-24
Abstract: The invention comprises bis-triazinyl-amino-stilbene compounds corresponding to the general formula <FORM:0773152/IV(b)/1> wherein R represents a methyl or ethyl group and A represents a phenyl radical which can be substituted by chlorine, acylamino, alkyl or alkoxy groups, and alkali metal salts thereof. Fluorescent symmetrical bis-triazinylamino-stilbene compounds and their alkali metal salts are produced by a process characterized by reacting 1 mol. of 4.41-bis-[4.6-dihalogen-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acids or their salts, obtained from 4.41-diamino - stilbene - 2.21 - disulphonic acid and cyanuric halides, with 2 mols. of a primary aromatic amine of the benzene series which can contain chlorine, acylamino alkyl or alkoxy substituents in the ring and with 2 mol. of a secondary alkylethanolamine in which the alkyl group is methyl or ethyl, the reaction being performed in steps in any order desired in aqueous solution in the presence of an agent neutralizing the mineral acid formed in the reaction so that symmetrical compounds of the above general formula in which R and A have the meaning given above, result: primary aromatic amines of the benzene series mentioned include aminobenzene, 2- and 3-methyl-1 - aminobenzene, 3 - chloro - 1 - aminobenzene, 2-, 3- or 4-methoxy-1-aminobenzenes, 2-ethoxy-1 - aminobenzene, 4 - phenoxy - 1 - amino - benzene, 2.5 - dimethyl - 1 - aminobenzene, 3-methoxy-4-methyl-1-aminobenzene. Sodium carbonate, bicarbonate and acetate may be employed as acid binding agent in the first step and an excess of amine in the second. In examples: the sodium salt of 4.41-bis-[phenylamino - 6 - (b  - hydroxyethylmethylamino) - 1.3.5-triazinyl - (2) - amino - stilbene - 2.21 - disul - phonic acid is obtained by reacting with aniline sodium salt of 4.4-bis-[4.6-dichloro-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid, obtained by reacting the sodium salt of 4.41 - diamino - stilbene - 2.21 - disulphonic acid with cyanuric chloride, and heating the product with N-methylethanolamine; similar products are obtained when the aniline in the above process is replaced by o- or m-toluidine, m-chloraniline, m- or o-anisidine or p-xylidine (1); in a similar process the disodium salt of 4.41-bis-[4-(p - methoxyphenylamino) - 6 - (N - ethyl - b  - hydroxyethylamino - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid is obtained from 4.41-bis-[4.6-dichloro-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid, N-ethyl-monoethanolamine and p-methoxy aniline; similar products are obtained using aniline, m-anisidine or m-phenetidine instead of p-methoxy aniline (2); the disodium salt of 4.41 - bis - [3 - methoxy - 4 - methyl - phenyl - amino) - 6 - (N - methyl - b  - hydroxyethyl - amino) - 1.3.5 - triazinyl - (2) - amino] - stilbene-2.21-disulphonic acid is similarly obtained using the disodium salt of 4.41-bis-[4.6 - dichloro - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21-disulphonic acid, 3 - methoxy - 4 - methyl - aniline and N - methyl - monoethanolamine; similar products are obtained when the 3-methoxy-4-methyl aniline is replaced by 3-chloro-4-methyl- or -2-methyl-aniline (3); the sodium salt of 4.41-bis-[4-(p-methoxy-phenylamino) - 6 - (N - methyl - b  - hydroxyethyl - amino) - 1.3.5 - triazinyl - (2) - amino] - stilbene-2.21-disulphonic acid is similarly obtained using p - anisidine chlorhydrate, 4.41 - bis - [4.6 - di - chloro - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid disodium salt and N-methyl-monoethanol; similar compounds are obtained when p-anisidine chlorohydrate is replaced by p-aminodiphenyl ether and o-phenetidine chlorohydrates (4); the sodium salt of 4.41 - bis - [2 - p - acetylaminophenylamino) - 4 - (b - hydroxyethylmethylamino) - triazinyl - (6) - amino] - stilbene - 2.21 - disulphonic acid is obtained in a process similar to (1) when aniline is replaced by p-aminoacetanilide (5).  The products of the invention are employed as optical brightening agents, e.g. for cellulose, e.g. in form of fibres and textiles and in washing and cleaning agents (see Group IV (c)).ALSO:Bis-triazinylamino - stilbene compounds corresponding to the general formula <FORM:0773152/IV(b)/1> wherein R represents methyl or ethyl, A represents a phenyl radical which can be substituted by chlorine, acylamino, alkyl or alkoxy groups and alkali metal salts thereof (see Group IVb) are employed as optical brightening agents for cellulose in the form of fibres and textiles and in washing and cleaning compositions. In examples: white cotton poplin is treated in a bath containing the sodium salt of 4 - 41 - bis - [4 - phenylamino - 6 (b  - hydroxyethyl - methylamino) - 1 : 3 : 5 - triazinyl - (2) - amino] - stilbene - 2, 21 - disulphonic acid and Glauber's salt (6); and pillow-cases &c. are boiled in a washing liquor containing a soap and perborate washing agent and the sodium salt of 4 : 41 - bis [4 - (p - methoxyphenylamino) - 6 - (b  - hydroxyethyl - methylamino) - 1 : 3 : 5 - triazinyl - (2) - amino] - stilbene - 2 : 21 - disulphonic acid.