Patent EP-0053775-B1 (EP)
IPC: C07D251/52
Filed: 1981-11-28
Granted: 1986-05-07
Abstract: 1. Claims for the Contracting States : BE CH DE FR GB IT LI NL SE A poly-bis-triazinylamine of the general formula (I)  see diagramm : EP0053775,P24,F1  in which n is an integer from 1 to 200, R**1 and R**2 are identical or different and denote hydrogen, C1 to C37 -alkyl, cycloalkyl which is unsubstituted or substituted by up to four C1 to C4 alkyl groups, C7 to C14 aralkyl or a group of the formula (II)  see diagramm : EP0053775,P24,F2  in which R**6 represents hydrogen or C1 to C6 alkyl, R**3 and R**4 are identical or different and have the meanings indicated under R**1 and R**2 , R**5 is halogen, phenyl, -OR**7 or -NR**8 R**9 , R**7 representing hydrogen, C1 to C18 alkyl, C3 to C12 alkenyl, C5 to C12 cycloalkyl, C7 to C18 aralkyl, C6 to C10 aryl or a radical of the formula (II), and R**8 and R**9 being identical or different and denoting hydrogen, C1 to C37 alkyl which is unsubstituted or substituted by a hydroxyl group, a C1 to C18 alkoxy group or a C1 to C4 dialkylamino group, C3 to C12 alkenyl, C5 to C12 cycloalkyl, C7 to C18 aralkyl, phenyl, naphthyl or a radical of the formula (II), or R**8 and R**9 , together with the common nitrogen atom, forming a pyrrolidine ring or a piperidine, morpholine or hexamethyleneimine ring which is unsubstituted or substituted by up to four C1 to C4 alkyl groups, X and Y are identical or different and represent C2 to C18 alkylene or C2 to C12 bis-(propoxy)-alkylene or C6 to C18 monocycloalkylene, dicycloalkylene or tricycloalkylene which are unsubstituted or substituted by up to four methyl groups and in which in the case of the group first mentioned, two C atoms can be replaced by N atoms which can be substituted by propylene groups, or X and Y represent C6 to C18 arylene or C7 to C18 aralkylene, or piperazinylene radicals are present instead of the groupings  see diagramm : EP0053775,P24,F3 or  see diagramm : EP0053775,P24,F4  E**1 is a halogen atom or a group  see diagramm : EP0053775,P24,F5   see diagramm : EP0053775,P24,F6  -O-R**7 or -NR**8 R**9 and E**2 is hydrogen or an acyl group, R**3 , R**4 , R**7 , R**8 and R**9 having the meanings indicated above and at least one of the radicals R**1 , R**2 , R**3 , R**4 , R**7 , R**8 and R**9 being of necessity a group of the formula (II), with the proviso that R**1 , R**2 , R**3 and R**4 are identical, if X and Y are different, and X and Y are identical, if at least one of the radicals R**1 or R**2 are different from R**3 and R**4 . 1. Claims for the Contracting State : AT A process for the preparation of poly-bis-triazinylamines of the general formula (I) see diagramm : EP0053775,P26,F1  in which n is an integer from 1 to 200, R**1 and R**2 are identical or different and denote hydrogen, C1 to C37 alkyl, cycloalkyl which is unsubstituted or substituted by up to four C1 to C4 alkyl groups, C7 to C14 aralkyl or a group of the formula (II)  see diagramm : EP0053775,P26,F2  in which R**6 represents hydrogen or C1 to C6 alkyl, R**3 and R**4 are identical or different and have the meanings indicated under R**1 and R**2 , R**5 is halogen, phenyl, -OR**7 or -NR**8 R**9 , R**7 representing hydrogen, C1 to C18 alkyl, C3 to C12 alkenyl, C5 to C12 cycloalkyl, C7 to C18 aralkyl, C6 to C10 aryl or a radical of the formula (II), and R**8 and R**9 being identical or different and denoting hydrogen, C1 to C37 alkyl which is unsubstituted or substituted by a hydroxyl group, a C1 to C18 alkoxy group or a C1 to C4 dialkylamino group, C3 to C12 alkenyl, C5 to C12 cycloalkyl, C7 to C18 aralkyl, phenyl, naphthyl or a radical of the formula (II), or R**8 and R**9 , together with the common nitrogen atom, forming a pyrrolidine ring or a piperidine, morpholine or hexamethyleneimine ring which is unsubstituted or substituted by up to four C1 to C4 alkyl groups, X and Y are identical or different and represent C2 to C18 alkylene or C2 to C12 bis-(propoxy)-alkylene or C6 to C18 monocycloalkylene, dicycloalkylene or tricycloalkylene which are unsubstituted or substituted by up to four methyl groups and in which in the case of the group first mentioned, two C atoms can be replaced by N atoms which can be substituted by propylene groups, or X and Y represent C6 to C18 arylene or C7 to C18 aralkylene, or piperazinylene radicals are present instead of the groupings  see diagramm : EP0053775,P26,F3 or  see diagramm : EP0053775,P26,F4  E**1 is a halogen atom or a group  see diagramm : EP0053775,P27,F1   see diagramm : EP0053775,P27,F2  -O-R**7 or -NR**8 R**9 and E**2 is hydrogen or an acyl group, R**3 , R**4 , R**7 , R**8 and R**9 having the meanings indicated above and at least one of the radicals R**1 , R**2 , R**3 , R**4 , R**7 , R**8 and R**9 being of necessity a group of the formula (II), with the proviso that R**1 , R**2 , R**3 and R**4 are identical, if X and Y are different, and X and Y are identical, if at least one of the radicals R**1 or R**2 are different from R**3 and R**4 , which comprises reacting, in an inert organic solvent, either A. a dihalogeno-bis-triazinyldiamine of the formula (III)  see diagramm : EP0053775,P27,F3  at 50 to 200 degrees C with a 0.8 to 1.4 molar amount of a diamine of the formula (IV)  see diagramm : EP0053775,P27,F4  Hal, R**1 , R**2 , R**3 , R**4 , R**5 , X and Y in these formulae having the meanings indicated above, in the presence of an equivalent amount - relative to the compound (IV) - of an inorganic base which acts as a hydrogen halide acceptor, or B. a poly-bis-triazinylamine of the general formula (V)  see diagramm : EP0053775,P27,F5  at 50 to 200 degrees C with a 0.8 to 1.4 equivalent amount of a compound of the formula (VI) H-R**5 Hal, R**1 , R**2 , R**3 , R**4 , R**5 , X and Y in these formulae having the meanings indicated in claim 1, but R**5 not being Hal or phenyl, in the presence of an equivalent amount - relative of the compound (VI) - of an inorganic base, or C. a cyanuric halide and a 0.8 to 1.3 molar amount of a compound of the formula (VI) in which, however, R**5 is not Hal or phenyl, initially at -5 to 40 degrees C and in the presence of an equivalent amount of a hydrogen halide acceptor, to give a dihalogenotriazine of the formula (VII)  see diagramm : EP0053775,P27,F6  then, without intermediate isolation of the latter, deriving from it, at 10 to 70 degrees C and in the presence of an equivalent amount of a hydrogen halide acceptor, by reaction with a 0.4 to 0.7 molar amount of a diamine of the formula (VIII)  see diagramm : EP0053775,P28,F1  a dihalogeno-bis-triazinyldiamine of the formula (III) and reacting the compounds (III) thus obtained, in situ in accordance with process A, to give the desired end products, Hal, R**1 , R**2 , R**3 , R**4 , R**5 , X and Y in the formulae having the meanings indicated above.