Patent GB-929257-A (GB)
Title: 2-imino-1, 3-di-n-heterocyclic compounds, their production and use
IPC: C07D233/44
Filed: 1961-07-31
Abstract: 2-Imino-1,3-di-N-heterocyclic compounds of formula <FORM:0929257/IV(a)/1> where A is an aliphatic radical bound at , - or , Y-carbon atoms, or a cycloaliphatic radical bound at , - carbon atoms, to the N atoms; R1 and R2 are H or a possibly substituted, saturated or unsaturated, normal, branched or ring-formed hydrocarbon radical; X is O or S, Y is a possibly substituted hydrocarbon radical, or NH2, or an amino group mono-substituted by a hydrocarbon radical, are used to make dyeings and synthetic substances, e.g. polyurethane, cellulose ester and ether fibres and films, fast to fading from gases, e.g. nitrogen oxides.  Preferably A is an alkylene radical, especially a 1,2-ethylene or 1,3-propylene radical, R1 and R2 are phenylalkyl radicals, Y is a secondary amino group, where the hydrocarbon residue is aromatic or araliphatic, e.g. a phenyl or benzyl group, and C(X)Y is a carbamyl or thiocarbamyl residue. For the preparation of the compounds (see Group IV(b).  The compounds may be incorporated in spinning masses.  In examples (34) a sheet of cellulose acetate containing 1-benzyl-2-benzylcarbamylimino-hexahydropyrimidine and 1-phenylamino-4-aminoanthraquinone is formed from acetone solution, and in (36) filaments are formed from a mass containing segmented polyurethane in N,N-dimethylformamide, titanium dioxide, ultramarine blue pigment, poly(N,N-diethyl-b -aminoethyl-methacrylate) and 1-benzyl - 2 - benzylthiocarbamyliminohexahydropyrimidine. Specification 881,635 is referred to.ALSO:The invention comprises 2-imino-1,3-di-Nheterocyclic compounds of formula: <FORM:0929257/IV(a)/1> where A represents an aliphatic radical bound at a ,b  or a ,g  carbon atoms, or a cycloaliphatic radical bound at a ,b -carbon atoms, to the nitrogen atoms; R1 and R2 independently each represent a hydrogen atom or a possibly substituted, saturated or unsaturated, normal, branched or ring-formed hydrocarbon radical; X represents sulphur or oxygen; Y represents a possibly substituted hydrocarbon radical, or NH2, or an amino group monosubstituted by a hydrocarbon radical, which may be made by the reaction of the corresponding 2 imino compound with an agent for introducing the -C(=X)-Y group.  A is preferably an alkylene radical e.g. 1,2-ethylene or 1,3-propylene, R1 and R2 are preferably phenylalkyl These agents are isocyanates, urethanes, mustard oils, thiourethanes, alkali metal cyanates, alkali metal rhodanides, carbamic acid halides or in some cases carboxfiylic acid esters or halides or ketones. Isocyanates and mustard oils are preferred, especially when of the aromatic or araliphatic series.  The reaction is preferably carried out in an inert organic solvent, e.g. an aromatic hydrocarbon, if necessary with heating, but may also take place in aqueous dispersion, or by melting the reactants together.  Amongst the examples given are preparations for 1-benzyl- 2-phenylcarbamyliminoimidazolidine, 1 benzyl- 2-benzoylimino-hexahydropyrimidine, 1 benzyl-2-thiocarbamyl-iminohexahydropyrimidine, 1-dodecyl-2-phenylthiocarbamylimino-imidazolidine, 1,3-diphenyl- 2-benzylcarbamyliminoimidazolidine, 1-benzyl- 2-benzylthiocarbamylimino- 4, 5-tetramethylene-imidazolidine, 1-cyclohexyl- 2-butylthiocarbamyl -iminohexahydropyrimidine, 1-benzyl- 2-dodecylthiocarbamyliminohexahydropyrimidine, pchlorobenzyl- 2-benzylcarbamylimino-hexahydropyrimidine, 1 benzyl- 2-m, p-dichlorobenzyl-thiocarbamylimino- -hexahydropyrimidine, 1-benzyl- 2-pmethoxybenzylthiocarbamyl imino-hexahydropyrimidine and 2phenyl-acetylimino-imidazolidine. The compounds may be used to prevent the fading of dyes (see Group IV(c)).  Specification 881,635 is referred to.ALSO:2-Imino-1,3-di-N-heterocyclic compounds of formula <FORM:0929257/IV(a)/1> where A is an aliphatic radical bound at a ,b - or a ,g - carbon atoms, or a cycloaliphatic radical bound at a ,b -carbon atoms, to the N atoms; R1 and R2 are H or a possibly substituted, saturated or unsaturated, normal, branched or ring-formed hydrocarbon radical; X is O or S, Y is a possibly substituted hydrocarbon radical, or NH2, or an amino group monosubstituted by a hydrocarbon radical, are used to make dyeings and synthetic substances, e.g. polyurethane, cellulose ester and ether fibres and films, fast to fading from gases, e.g. nitrogen oxides.  Preferably A is an alkylene radical, especially a 1,2-ethylene or 1,3-propylene radical, R1 and R2 are phenylalkyl radicals, Y is a secondary amino group, where the hydrocarbon residue is aromatic or araliphatic, e.g. a phenyl or benzyl group, and C(X)Y is a carbamyl or thiocarbamyl residue. For the preparation of the compounds (see Group IV(b)).  The compounds may be applied before, during or after dyeing.  The yellowing of polyurethane fibres is lessened by treatment with a solution or dispersion of the compounds. In examples (33) a cellulose acetate fabric is treated with a solution of 1-benzyl-2-phenylcarbamylimino-imidazoline and then dyed, and in (35) polyurethane fibres are impregnated with a solution of 1-benzyl-2-benzylthiocarbamyliminohexahydropyrimidine. Specification 881,635 is referred to.