Novel cationic ester compounds, novel polymers and copolymers thereof, their preparation and use

摘要

1,140,520. Cationic ester compounds containing a quaternary nitrogen atom. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 19 July, 1966, No. 32402/66. Heading C2C. [Also in Divisions B2, C3, C6 and D2] The invention comprises cationic ester compounds of the general formula wherein R is C 1 -C 20 alkyl, R1 is an aliphatic hydrocarbon group having from 2 to 7 carbon atoms and 1 or 2 ethylenic linkages, X is Cl or Br and n is 1 or 2 with the proviso that if n is 2 R1 has not more than 4 carbon atoms. They may be obtained by reacting the corresponding glycidyl trialkyl ammonium halide with the corresponding unsaturated mono- or di-carboxylic acid in the liquid phase. The liquid phase may be water which may contain other solvents, e.g. C 1 -C 4 alcohols. The reaction is preferably effected at between 45‹ C. and 140‹ C. The R groups are preferably C 1 -C 4 alkyl groups. In an alternative procedure the compounds are obtained by directly reacting the corresponding trialkylamine and the corresponding 2,3-epoxy-1-halo-propane with the corresponding unsaturated mono- or di-carboxylic acid in an inert polar solvent, e.g. a sulphone, N,N-disubstituted alkyl amide, a sulphoxide or a secondary or tertiary alcohol. The reaction, in either type of process, should preferably be carried out in the presence of a polymerization inhibitor and suitable reaction temperatures are from 30‹ to 110‹ C. The products may be polymerized, or co-polymerized with an ethylenically unsaturated monomer, to form polymeric esters which are useful as agents for treating fibrous materials and for the separation of clays and ores from aqueous suspensions. They may also be esterified or etherified on the hydroxyl group, or the ethylenio linkage in the group R1 may be epoxidized to form epoxy resin precursors.