Patent GB-511143-A (GB)
Abstract: 511,143. Reaction products of cyanuric halides. GROVES, W. W. (Geigy Akt.-Ges., J. R.). Feb. 10, 1938, No. 4188. [Class 2 (iii)] [Also in Group VIII] One molecule of a cyanuric halide is condensed with two or three molecules (not more than two being identical) of a compound or compounds of the aliphatic, araliphatic or benzene series containing hydrogen linked to nitrogen, oxygen or sulphur, but not containing any group or substituent which imparts colour to the condensation product or renders the latter suitable for use as a coupling component or diazo component in the manufacture of azo dyes ; the compounds may be taken as such or as their alkali-metal derivatives. The reagents must be so selected that the products contain at least one halogen atom external to the cyanuric nucleus and at least one sulphonic acid group, or alternatively the products are halogenated and (or) sulphonated so that the final products contain at least one halogen atom and at east one sulphonic acid group; products alreadv containing a halogen atom and (or) a sulphonic acid group may also be further halogenated and (or) sulphonated. When only two halogen atoms of the cyanuric halide are replaced as described above, the remaining halogen atom may be retained or replaced by an amino or hydroxy group. The products are colourless compounds, useful for protecting wool and like materials against insect pests. In the examples (1) one mol. of cyanuric chloride is condensed with one mol. each of 2-amino-2<1>-sulpho-4-4<1>-dichlorodiphenyl ether, 3 : 4-dichloraniline, and 1-amino- 3 : 4-dichlorobenzene-6-sulphonic acid ; (2) a suspension of cyanuric chloride in aqueous acetone is treated in succession with the reagents used in example 1, the liberated hydrochloric acid being neutralized after each treatment by means of sodium carbonate ; (3) one mol. of cyanuric chloride is condensed with two mols. of 4 : 4<1>-dichloro-2-aminodiphenyl ether and one mol. of caustic soda, and the product is sulphonated with sulphuric acid ; (4) one mol. of cyanuric chloride is condensed with two mols. of 4-amino-3<1>-methyl-2-sulphodiphenyl ether and one mol. of caustic soda, and the product is chlorinated with gaseous chlorine or with sodium chlorate and hydrochloric acid ; (5) one mol. of cyanuric chloride is condensed with one mol. each of sodium methylate, 4- amino-2-sulphodiphenyl ether, and 4-amino-3<1>- methyl-2-sulphodiphenyl ether, and the product is treated with gaseous chlorine and then, if desired, brominated in acetic acid or chloroform solution. A table is given also in which reference is made to the condensation of one mol. of cyanuric chloride with (1) one mol. each of 4-chlorophenylmercaptan, 1-amino-2 : 4-dichloro-5-sulphobenzene, and 1-amino-3 : 4- dichloro-6-sulphobenzene; (2) one mol. each of 2 : 4-dichloro-6-sulphophenol, caustic soda, and 4-amino-4<1>-chloro-3<1> : 5<1>-dimethyl-2-sulphodiphenyl ether ; (3) one mol. each of 4-amino- . 41-chloro (or bromo-)-2-sulphodiphenyl ether, 2 : 4-dichloro-6-sulphophenol, and 1-amino-2 : 4- dichloro-5-sulphobenzene; (4) one mol. each of 4-amino-4<1>-chloro-2-sulphodipbenyl ether, 3 : 4-dichloraniline, and 1-amino-3 : 4-dichloro- 6-sulpbobenzene ; (5) one mol. each of 3 : 4- dichloro-6-sulphophenol, ammonia, and 4-amino-4<1>-chloro-5<1>-methyl-2-sulphodiphenyl ether ; (6) one mol. each of 2-amino-31-methyl- 4<1>-chloro-4-sulphodiphenyl ether; 3 : 4-dichloraniline (or 4-bromaniline), and 4-amino-4<1>- chloro-5<1>-methyl-2-sulphodiphenyl ether; (7) one mol. each of 2-amino-4-sulpho-4<1>-chlorodiphenyl sulphide, 3 : 4-dichloraniline (or 4-bromaniline), and 4-amino-<1>4-chloro-5<1>- methyl-2-sulphodiphenyl ether; (8) and (9) one mol. each of 4-amino-31-methyl-41-chloro- 2-sulphodiphenyl ether, 4-amino-4<1>-chloro-2- sulphodiphenyl ether, and 4-chlorobenzenesulphonamide or 3 : 4-dichlorobenzenesulphonamide ; (10) one mol. each of 4-amino-31- methyl-4<1>-chloro-2-sulphodiphenyl ether and 4-amino-4<1>-chloro-2-sulphodiphenyl ether ; the third chloroine atom of the cyanuric chloride may be left unchanged or replaced by a hydroxy or alkoxy group ; (11) one mol. each of 4-amino- 2-sulphophenol bromo- 'or chloro-xylyl ether (prepared from halogenated crude xylenol), 4-amino-4<1>-chloro-2-sulphodiphenyl ether, and 1-amino-3 : 4-dichloro-6-sulphobenzene; (12) one mol. each of 3 : 4-dichloro-6-sulphophenol, caustic soda, and 4-amino-41-chloro-51-methyl- 2-sulphodiphenyl ether; (13) one mol. each of 3 : 4 : 6-trichloro-2-sulphophenol, aniline, and 4-amino-4<1>-chloro-5<1>-methyl-2-sulphodiphenyl ether ; (14) one mol. each of 3 : 4 : 6-trichloro- 2-sulphophenol, 3-chloraniline, and 2-amino- 4 : 4<1>-dichloro-2<1>-sulphodiphenyl ether; (15) one mol. each of 2: 4-dichloro-6-sulphcphenol, 3 : 4-dichloraniline, and 2-amino-4 : 4'-dichloro- 2<1>-sulphodiphenyl ether (16) and (17) one mol. each of 1-amino-3 : 4-dichloro-6-sulphobenzene, 3 : 4-dichloraniline, and 4-amino- 2<1> : 4<1> : 5<1>-trichloro-2-sulphodiphenyl ether or 2-amino-2<1> : 4<1> : 5<1>-trichloro-4-sulphodiphenyl ether; (18) and (19) one mol. each of 3 : 4- dichloraniline, sodium ethylate or dimethylamine, and 4-amino-4<1>-chloro-2-sulphodiphenyl ether ; (20)-(22) one mol. each of (a) 3 : 4 : 5- trichloraniline, (b) sodium methylate, ammonia or caustic soda, and (c) 2-amino-4 : 41-dichloro- 2<1>-sulphodiphenyl ether ; (23) one mol. each of 3 : 4 : 5-trichloraniline and 2-amino-4 : 4<1>- dichloro-2<1>-sulpho-diphenyl ether; (24) one mol. of 4-chlorophenyl-mercaptan and two mols. of 1-amino-3 : 4-dichloro-6-sulphobenzene; (25) and (26) one mol. each of 3 : 4-dichloraniline, ammonia or caustic soda; and 2-amino- 4 : 4<1>-dichloro-2<1>-sulphodiphenyl ether; (27) and (28) one mol. each of 3 : 4 : 5-trichloraniline or aniline, 3 : 4 : 6-trichloro-2-sulphophenol, and 2-amino-4 : 4<1>-dichloro-2<1>-sulphodiphenyl ether ; (29) and (30) one mol. each of 3 : 4 : 5- trichloraniline or 4-chloraniline, 3 : 5-dimethyl- 4-chloro-2-sulphophenol, and 2-amino-4 : 4<1>- dichloro-2-sulphodiphenyl ether ; (31) one mol. each of 3 : 4 : 5-trichloraniline, 3-methyl-4- chloro-6-sulphophenol, and 2-amino-4 : 4'- dichloro-2<1>-sulphodiphenyl ether; (32) two mols. of 4-amino-2 : 4<1>-dichloro-5<1>-methyl-2<1>- sulphodiphenyl ether and one mol. of ammonia ; (33) one mol. each of 3-methyl-4-chloro-6- sulphophenol, caustic soda, and 4-amino-3<1> : 5<1> dimethyl-4<1>-chloro-2-sulphodiphenyl ether; (34) and (35) one mol. of sodium methylate or caustic soda and two mols of 4-chloro-4<1>-amino- 2<1>-sulphodiphenyl ether; (36) one mol. of sodium methylate and two mols of 2<1>: 4- dichloro-5-methyl - 4<1> - amino-2 - sulphodiphenyl ether; (37) one mol. of 3:4-dichloraniline and' two mols. of 4<1>-chloro-2-amino-4-sulphodiphenyl ether; (38) one mol. of sulphanilic acid and two mols of 2-chloro-4-amylphenol; (39) one mcl. of caustic soda and two mols. of 4<1>-chloro-3<1>-methyl-4-amino-2-sulphodiphenyl ether; (40) one mol. of sodium methylate and two mols. of 4<1>-chloro-4-amino-2-sulphodiphenyl ether ; (41) two mols. of 3:4-dichloraniline and one mol. of 4<1>-chloro-2-amino-4-sulphodiphenyl sulphide; (42) one mol. of caustic soda and two mols. of 4<1>-chloro-4-amino-3<1>: 5<1>- dimethyl-2-sulphodiphenyl ether ; (43) one mol. each of 3:4:5-trichloraniline, sodium methylate, and 4<1>-chloro-4-amino-2-sulphodiphenyl ether,; (44) and (45) two mols. of 3:4-dichloraniline or 3:4:5-trichloraniline and one mol. of 41-chloro- 4-amino-3<1>methyl-2-sulphodiphenyl ether; (46) one mol. each of caustic soda, 4:4'-dichloro-2- amino-2<1>-sulphodiphenyl ether, and 4<1>-chloro- 4-amino-3<1>-methyl-2-sulphodiphenyl ether ; (47) one mol. each of 3-4-dichloraniline, sodium methylate, and 2:4<1>-dichloro-3<1>: 5<1>- dimethyl- 4-amino-2<1>-sulphodiphenyl ether ; (48)-(52) one mol. of sodium n- or isopropylate, n- or isobutylate or isoamylate and two mols of 2-amino- 4:4<1>-dichloro-2<1>-sulphodiphenyl ether ; (53) one mol. of caustic soda and two mols. of 2:4<1>: 5<1>- trichloro-4-amino-2<1>-sulphodiphenyl ether,; (54) one mol each of caustic soda, 2:4-dichloro-6-. sulphophenol, and 4<1>-chloro-5<1>-methyl-4-amino- 2-sulphodiphenyl ether ; (55) one mol. each of caustic soda, 4<1>-chloro-4-amino-2-sulphodiphenyl ether, and 4-4<1>-dichloro-2-amino-2<1>-sulphodiphenyl ether ; (56); (58) one mol. each of (a) sodium methylate, ammonia or dimethylamine, (b) 3:4-dichloro-6-sulphophenol, and (c) 4'- chloro-4-amino-2-sulphodiphenyl ether; (59) and (60) one mol. each of 4-chloraniline or 3:4- dichloraniline, 3:4-dichloro-6-sulphophenol, and 4:4<1>-dichloro-2-amino-2<1>-sulphodiphenyl ether ; (61) and (62) one mol. each of 3:4:5- or 2:4:5- trichloraniline, 3:4-dichloro-6-sulphophenol, and 4-4<1>-dichloro-2-amino-2<1>-sulpho diphenyl ether ; (63) one mol. each of sodium methylate, 4<1>- methyl-4-amino-2-sulphodiphenyl ether, and 4<1>-chloro-4-amino-2-sulphodiphenyl ether ; (64) one mol. each of caustic soda, 3:4-dichloraniline, and 4:4<1>:5-trichloro-5<1>-methyl-2-amino-2<1>-sulphodiphenyl ether ; (65) one mol. each of caustic soda, 4<1>-chloro-4-amino-2-sulphodiphenyl ether, and 4<1>-chloro-4-amino-2-sulphodiphenyl sulphone; (66) one mol. each of 4-chlorobenzylamine and two mols. of 1-amino-3:4-dichloro-6- sulpho-benzene. Specification 221,843, [Class 2 (iii)], is referred to. The Provisional Specification. refers to the condensation of cyanuric halides with heterocyclic compounds containing an exchangeable hydrogen atom, and indicates that a halogen atom of the cyanuric halide may be replaced by a mercapto or thiosulphate group. It refers also to products obtained by condensing one mol. of cyanuric chloride with (1) one mol. each of 4-chlorobenzyl mercaptan, 1-amino-2:4- dichloro-5-sulphobenzene, and 1-amino-3:4-dichloro-6-sulphobenzene; (2) one mol. each of 4-amino-4<1>-chloro-2-sulphodiphenyl ether, 3:4- dichlorobenzylanliline, and 1-amino-3:4-dicchloro-6-siilphobenzene ; (3),