Patent GB-1101688-A (GB)
Title: Poly aziridinyl phosphinic acid esters
Inventor: INGRAM ARTHUR PRESTON
IPC: C08G73/02
Filed: 1965-03-26
Abstract: Polyaziridinyl phosphinic acid esters are prepared by reacting a halophosphinic acid ester with ethylene imine or a substituted ethylene imine containing at least one C1- 10 hydrocarbon group bonded to a carbon atom thereof, in substantially stoichiometric proportions of the imine and the halogen of the halophosphinic acid ester, wherein the halophosphinic ester employed in the ester of a dihalophosphinic acid and a polyoxyalkyene polyol containing at least 6 carbon atoms and at least two ether groups and one phosphinic acid residue for each hydroxyl group on the polyol.  The invention also includes aziridinyl phosphinic acid esters containing two aziridinyl groups for each phosphinic acid group and one phosphinic acid group for each hydroxyl group of a polyoxyalkylene polyol containing at least 6 carbon atoms and containing from 2 to 8 hydroxyl groups and at least 2 ether groups.  The reaction is suitably effected by adding the ethyleneimine to the halophosphinic ester which is maintained at a temperature between 2 DEG  and 50 DEG  C., preferably at atmospheric pressure in the presence of an acid acceptor and an organic solvent.  The polyoxyalkylene polyol starting material advantageously has a molecular weight in the range 700 to 33,000 and is preferably a polyoxyethylene, polyoxypropylene or polyoxybutylene diol or a polyoxyalkylene adduct of a polyol containing three or more hydroxy groups per molecule, e.g. a glycerolpropylene oxide adduct having a molecular weight in the range 400 to 29,000.  The halophosphinic ester starting material is prepared by reacting the polyol with 1 mole proportion of phosphorus oxyhalide for each hydroxyl group in the polyol and is suitably subsequently employed in situ.ALSO:Polyaziridinyl phosphinic acid esters are prepared by reacting a halophosphinic acid ester with ethyleneimine or a substituted ethyleneimine containing at least one C1- 10 hydrocarbon group bonded to a carbon atom thereof, in substantially stoichiometric proportions of the imine and the halogen of the halophosphinic acid ester, wherein the halophosphinic ester employed is the ester of a dihalophosphinic acid and a polyoxyalkylene polyol containing at least 6 carbon atoms and at least two ether groups and one phosphinic acid residue for each hydroxyl group on the polyol. The invention also includes aziridinyl phosphinic acid esters containing two aziridinyl groups for each phosphinic acid group and one phosphinic acid group for each hydroxyl group of a polyoxyalkylene polyol containing at least 6 carbon atoms and containing from 2 to 8 hydroxyl groups and at least 2 ether groups. The reaction is suitably effected by adding the ethyleneimine to the halophosphinic ester which is maintained at a temperature of 2-50 DEG C., preferably at atmospheric pressure in the presence of an acid acceptor and an organic solvent.  The halophosphinic ester starting material is prepared by reacting the polyol with 1 mole proportion of phosphorus oxyhalide for each hydroxyl group in the polyol and is suitably subsequently employed in situ.