Patent GB-1056057-A (GB)
Title: Production of n-substituted 2-amino-1,3,5-triazines
IPC: D06P1/642
Filed: 1965-06-01
Abstract: The invention relates to compounds of the formula <FORM:1056057/C2/1> in which R1, R4 and R7 each denote hydrogen, an alkyl group of up to 6 carbon atoms or an aralkyl group, or each of the pairs R1 and R4 or R4 and R7 denotes a -CH2CH2- group or a substituted -CH2CH2- group, R2, R3, R5 and R6 each denote hydrogen or an alkyl group of up to 6 carbon atoms, or each of the pairs R2 and R3 or R5 and R6 denotes a -CH2CH2CH2CH2- group or a substituted - CH2CH2CH2CH2- group, R8 denotes an aryl, aralkyl or cycloalkyl radical, n is 1 or 2 and X1 and X2, which may be identical or different, denote chlorine or bromine or any of the radicals R9, -OR9 or -SR9 or a radical -N(R10)(R11), in which R9 denotes an alkyl, cycloalkyl, aralkyl or aryl radical and R10 and R11 denote hydrogen or a radical R9, or R11 may denote a carbacyl group.  The compounds are obtainable by reacting 1 mol. of cyanuric chloride or bromide with 1 mol. of an amine of the formula <FORM:1056057/C2/2> and, optionally, with 1 or 2 mols. of (a) a Grignard reagent of the formula Hal-Mg-R9, in which Hal denotes chlorine, bromine or iodine, or (b) a compound of the formula HO-R9 or an alkali-metal salt thereof, or (c) a compound of the formula HS-R9 or a water-soluble salt thereof, or (d) a compound of the formula HN(R10)R11.  The reactions may be effected in any order.  Typical examples describe the reaction of cyanuric chloride (a) with ammonia and N-phenyl-N,N1-dimethylethylene diamine to yield a product of the formula <FORM:1056057/C2/3> (b) with ammonia and N-phenyl-N1-(b -methyl-aminoethyl piperazine to yield a product of the formula <FORM:1056057/C2/4> (c) with N-phenyl-N,N1-dimethylethylene diamine to yield a product of the formula <FORM:1056057/C2/5> and (d) with N-phenylpiperazine to yield a product of the formula <FORM:1056057/C2/6> Other examples are given also in which (e) the product of Example (c) above is heated with ammonia to yield a product of the formula <FORM:1056057/C2/7> (f) the product of Example (e) is treated with n-propanol to yield a product of the formula <FORM:1056057/C2/8> (g) the product of Example (e) is treated with ethyl mercaptan to yield a product of the formula <FORM:1056057/C2/9> (h) the product of Example (c) is treated with phenol to yield a product of the formula (i) the product of Example (d) is treated with ammonia to yield a product of the formula <FORM:1056057/C2/101> (j) the product of Example (i) is treated with ethanol to yield a product of the formula <FORM:1056057/C2/112> (k) the product of Example (d) is treated with ethyl mercaptan to yield a product of the formula <FORM:1056057/C2/123> and (l) the product of Example (i) is treated with acetamide to yield a product of the formula <FORM:1056057/C2/134> Many other products of the invention are specified also.  The products are useful for preventing gas fading in dyed cellulose esters and ethers and polyurethanes.  Also, they may be used to prevent the yellowing of polyurethane plastics.ALSO:For improving the fastness to gas fading (due to combustion gases or nitric oxide) of uncoloured elastomeric polyurethanes, use is made of compounds of the formula <FORM:1056057/C3/1> in which R1, R4 and R7 each denote hydrogen, an alkyl group of up to 6 carbon atoms or an aralkyl group, or each of the pairs, R1 and R4 or R4 and R7, denotes a -CH2CH2- group o a substituted -CH2CH2- group, R2, R3, R5 and R6 each denote hydrogen or an alkyl group of up to 6 carbon atoms, or each of the pairs R2 and R3 or R5 and R6 denotes a -CH2CH2CH2CH2- group or a substituted -CH2CH2CH2CH2- group, R8 denotes an aryl, aralkyl or cycloalkyl radical, n is 1 or 2 and X1 and X2, which may be identical or different, denote chlorine or bromine or any of the radicals R9, -OR9 or -SR9 or a radical -N(R10)(R11), in which R9 denotes an alkyl, cycloalkyl, aralkyl or aryl radical and R10 and R11 denote hydrogen or a radical R9, or R11 may denote a carbacyl group (see Division C2). Typical compounds described have the formulae <FORM:1056057/C3/2> <FORM:1056057/C3/3> <FORM:1056057/C3/4> <FORM:1056057/C3/5> <FORM:1056057/C3/6> <FORM:1056057/C3/7> <FORM:1056057/C3/8> <FORM:1056057/C3/9> <FORM:1056057/C3/100> <FORM:1056057/C3/111> <FORM:1056057/C3/122> <FORM:1056057/C3/133>ALSO:For improving the fastness to gas fading of cellulose ester or ether or polyurethane dyeings, use is made of compounds of the formula:-  <FORM:1056057/D1-D2/1> in which R1, R4 and R7 each denote hydrogen, an alkyl group of up to 6 carbon atoms or an aralkyl group, or each of the pairs, R1 and R4 or R4 and R7 denotes a -CH2CH2- group or a substituted -CH2CH2- group, R2, R3, R5 and R6 each denote hydrogen or an alkyl group of up to 6 carbon atoms, or each of the pairs R2 and R3 or R5 and R6 denotes a -CH2CH2CH2 CH2- group or a substituted -CH2CH2CH2CH2-group, R8 denotes an aryl, aralkyl or cycloalkyl radical, n is 1 or 2 and X1 and X2, which may be identical or different, denote chlorine or bromine or any of the radicals R9, -OR9 or -SR9 or a radical -N(R10)(R11), in which R9 denotes on alkyl, cycloalkyl, aralkyl or aryl radical and R10 and R11 denote hydrogen or a radical R9, or R11 may denote a carbacyl group (see Division C2).  Typical compounds described have the formulae:-  <FORM:1056057/D1-D2/2> <FORM:1056057/D1-D2/3> <FORM:1056057/D1-D2/4> <FORM:1056057/D1-D2/5> <FORM:1056057/D1-D2/6> <FORM:1056057/D1-D2/7> <FORM:1056057/D1-D2/8> <FORM:1056057/D1-D2/9> <FORM:1056057/D1-D2/100> <FORM:1056057/D1-D2/111> <FORM:1056057/D1-D2/122> <FORM:1056057/D1-D2/133> The products prevent fading due to combustion gases or nitric oxide, and may be used before, during or after dyeing.  Examples 44-46 describe (1) the pretreatment of a cellulose acetate fabric with a product of the invention and its subsequent dyeing with a specified mixture of disperse dyes, (2) the simultaneous dyeing and drawing into sheets of a cellulose acetate solution and (3) the pretreatment of yarn for Spandex fibres.