Patent GB-1119306-A (GB)
Title: Organic substituted sulphonyl diamides and their use in hardening gelatine
IPC: C07D303/16
Filed: 1967-03-29
Abstract: Compounds of the formula <FORM:1119306/C3/1> wherein R1 and R2 represent residues bound to the -CO- group by hetero atoms, the residues being capable of reacting with a compound containing one or more reactive H atoms with the formation of one or more homopolar bonds, e.g. R1 and R2 may be X-R1 where X is -OCH2-NH-CH2-, -OCO-, -NHCO-, -NH-SO2- and R1 is a residue capable of reacting with a compound containing one or more reactive hydrogens to form one or more homopolar bonds, e.g. residues of aldehydes, epoxy compounds, ethylene-imine compounds, N-heterocyclic halogen compounds with a reactive halogen in the a -position to the nitrogen, aliphatic halogen compounds, a ,b -ethylenically unsaturated carboxylic acids, a ,b - or b ,g -ethylenically unsaturated sulphonic acids, a -and b -halogeno-carboxylic acids, b -hydroxy sulphonates or -sulphates of aliphatic carboxylic acids, halides or anhydrides of carboxylic acids and halides of sulphonic acids;  Compounds of the invention where R1 contains ethylenic unsaturation may be self-polymerized or copolymerized, for example, with acrylonitrile.  An example describes the self-polymerization of CH2=CH.CO.NH.CONH. SO2.NH.CO.NH.CO.CH=CH2 and its copolymerization with acrylonitrile; polymerization is effected by heating in dimethylformamide. The products are suitable as thickening agents.ALSO:Novel compounds of formula <FORM:1119306/C2/1> wherein R1 and R2 each represent a residue bound to the -CO- group by a hetero atom, the residue being capable of reacting with a compound containing one or more mobile H atoms with the formation of one or more homopolar bonds, e.g. R1 and R2 may be X-R1 where X is -OCH2-, -NHCH2-, -OCO-, -NHCO-, -NHSO2-, and R1 is a residue capable of reacting with a compound containing one or more mobile H atoms to form one or more homopoler bonds e.g. residues of aldehydes, epoxy compounds, ethylene-imine compounds, N-heterocyclic halogen compounds with a reactive halogen in the a -position to the nitrogen, aliphatic halogen compounds, a ,b -ethylenically unsaturated carboxylic acids, a ,b - or b ,y-ethylenically unsaturated sulphonic acids, a -and b -halogenocarboxylic acids, b -hydroxy sulphonates or -sulphates of aliphatic carboxylic acids, halides or anhydrides of carboxylic acids and halides of sulphonic acids; are produced by reacting sulphonyl di-isocyanate: O = C = N-SO2-N = C = O, in a molecular ratio of 1:2 with a compound containing a mobile hydrogen atom bound to a hetero atom and a residue capable of reacting with a compound containing one or more mobile hydrogen atoms with the formation of one or more homopoler bonds.  An alternative method of preparation consists of reacting sulphamide (H2N-SO2-NH2) with acylisocyanates, chlorocarbonic acid esters, or carbamic acid chlorides in a molecular ratio of 1:2 in one or two reaction stages.  Another method consists of reacting sulphonyl-bis-carbamic acid esters, with compounds containing amino groups.  2-Carbamoylmethylamino-4,6-dichloro-triazine is prepared from cyanuric chloride and aminoacetamide.