Patent GB-921994-A (GB)
Title: Substituted aziridines
IPC: D06P5/22
Filed: 1959-07-03
Abstract: C-aminomethyl ethylene imine and its reaction products with ethylene oxide are polymerized in the presence of strong acids such as concentrated hydrochloric acid by adding said acid to the aziridine at room or lower temperatures, followed by heating the acid mixture at a temperature not exceeding 180 DEG C. under atmospheric pressure. Specifications 600,851 and 602,332 are referred to.ALSO:The invention comprises 3-aminomethyl aziridines of the formula: <FORM:0921994/IV(a)/1> wherein R1, R2 and R3 represent hydrogen, C1-6 alkyl groups, C1-6 hydroxyalkyl groups, polyoxyethylene groups, C8-18 alkanoyl groups and/or benzoyl or benzenesulphonyl groups which may be optionally further substituted (e.g. with alkyl, nitro, chlorine or substituents), and R4 represents hydrogen or a C1-6 alkyl group. The above compounds are prepared (1) by reacting compounds of the formulae:-  <FORM:0921994/IV(a)/2> <FORM:0921994/IV(a)/3> where R11, R12 and R13 represent hydrogen, C1-6 alkyl groups or C1-6 hydroxyalkyl groups with concentrated sulphuric acid or oleum to form the corresponding sulphuric ester inner salt sulphates, reacting the latter with an excess of alkali hydroxide at a raised temperature and, if desired, reacting compounds in which R11, R12 and/or R13 represent hydrogen with ethylene oxide or with alkylating, alkanoylating, benzoylating or benzenesulphonylating agents; or (2) by reacting compounds of the formulae:  <FORM:0921994/IV(a)/4> <FORM:0921994/IV(a)/5> with an inorganic acid chloride or bromide to form the corresponding 1:3-diamino-2-halogen or 2:3-diamino-1-halogen propane, reacting the latter with an organic or inorganic base and, if desired, further treating the products as in (1).  3-Aminomethyl aziridine or its reaction products with ethylene oxide may be polymerized in the presence of strong acids or reacted with salicylaldehyde to give compounds which are effective as copper deactivators in benzene.  1:3-Dichloro-2-ethylpropanol-2 is prepared by reacting 2-chloromethylbutene-1 with hypochlorous acid.  1 - Diethylamino-3-ethylaminopropanol-2 is prepared by reacting 1-diethylamino-2:3-epoxypropane with ethylamine. 1:3-Diamino-2-methyl- or ethylpropanol-2 is prepared by reacting 1:3-dichloro-2-hydroxy-2-methyl-or ethyl-propane with ammonia. Specifications 600,851 and 602,332 are referred to.ALSO:In a process for the animalization and subsequent dyeing of cotton, bleached unfinished cotton sheeting is impregnated and heated with 3-aminomethyl aziridines of the formula <FORM:0921994/IV(a)/1> wherein R1, R2 and R3 represent hydrogen, C1-6 alkyl groups, C1-6 hydroxyalkyl groups, polyoxyethylene groups, C8-18 alkanoyl groups and/or benzoyl or benzenesulphonyl groups which may be optionally further substituted (e.g. with alkyl, nitro, chlorine or bromine substituents), and R4 represents hydrogen or a C1-6 alkyl group, thoroughly rinsed with distilled water and the resulting animalized cotton (which is also more resilient and elastic than the corresponding untreated cotton) dyed at the boil with a 1% aqueous solution of the acid dyestuffs Polar Brilliant Blue RAW, Polar Brilliant Blue GAW or Erio Fast Cyanine S.  Specifications 600,851 and 602,332 are referred to.