Patent GB-834226-A (GB)
Title: Improvements in organic polymers and the preparation thereof
Filed: 1956-01-20
Abstract: The invention comprises water-soluble poly-1,2-alkylene glycols containing quaternary ammonium groups in the side chains and having on the average at least 6 identical or different units of the formula <FORM:0834226/IV (b)/1> in which m is an integer of from 1 to 5, at least one of the substituents R, R1, R2 represent an alkyl or substituted alkyl group of 1-5 carbon atoms, the remainder being monovalent organic radicals which in part or together may form a saturated heterocyclic ring, and which may contain hydroxyl, carboxyl ester, carboxyl, carboxylate, amide, sulphonic acid and/or sulphonate groups, and wherein R3 represents hydrogen or an alkyl group of 1 to 5 carbon atoms.  These compounds are made by reacting, preferably in solution, a poly-1,2-alkylene glycol containing side chains of 1 to 5 carbon atoms substituted by a halogen or sulphonate radical with one or more tertiary amines of the formula R, R1, R2N, in which the substituents have the above meanings.  The polyglycol may be reacted successively with different amines.  The halogen derivative of the poly-1,2-alkylene glycol may be polyepibromohydrin of a degree of polymerization of 8.  Ester groups present in the quaternized polymer may be saponified.  The amine may be gluconic acid dimethylaminoethyl amide, dimethylaminopropanediol-2,3, trimethylamine, dimethylaminoethanol, N-methyl diethanolamine, gamma-(dimethylamino)-butyric acid methyl ester, N,N-dimethyl-butylamine, N-methyl-morpholine, N,N-dimethylglycine - amide, N,N - dimethyl - (beta - ethoxyethyl) - amine, N,N - dimethylglycine - N1,N1-dimethyl - amide, acetic acid - 3 - dimethylaminopropylamide, or an amino-derivative of a monosaccharide or disaccharide.  In Example 1 polyepibromohydrin of an average degree of polymerization of 8, is heated with dimethylaminopropanediol-2,3, and the quaternized polymer isolated; in Example 2 the same polymer is heated with dimethyl formamide and dimethylaminoacetic acid methyl ester, cooled, and after the addition of methanolic trimethyl amine solution heated in an autoclave at 50 DEG  C., and then the ester groups in the quaternized polymer saponified with an excess 2N sodium hydroxide; in Example 3 the same polymer as in Example 1 is heated with gluconic acid dimethylaminoethylamide in the presence of dimethyl formamide.  The polyepibromohydrin having an average degree of polymerization of 8 is made by polymerizing epibromohydrin dissolved in chloroform in the presence of boron trifluoride etherate dissolved in chloroform at a temperature between 5 DEG  and 10 DEG  C. for a period of about seven hours.ALSO:Water-soluble poly-1,2-alkylene glycols containing quaternary ammonium groups in the side chains and having on the average at least 6 identical or different units of the formula <FORM:0834226/IV (a)/1> in which at least one of the substituents R, R1, R2 represent an alkyl or substituted alkyl group of 1-5 carbon atoms, the remaining two, monovalent organic radicals which in part or together may form a saturated heterocyclic ring, and which substituents may contain hydroxyl, carboxylester, carboxyl, carboxylate, sulphonic acid and/or sulphonate groups, and wherein R3 represents hydrogen or an alkyl group of 1 to 5 carbon atoms are made by reacting, preferably in solution, a poly-1,2-alkylene glycol containing side chains of 1 to 5 carbon atoms substituted by a halogen or sulphonate radical with one or more tertiary amines of the formula R, R1, R2, N, wherein the substituents have the meanings set out above.  The polyglycol may be reacted successively with different amines. The halogen derivative of the poly-1,2-alkylene glycol may be polyepibromohydrin having an average degree of polymerization of 8. Ester groups present in the quaternized polymer may be saponified. The amine may be dimethylaminopropanediol-2,3 trimethylamine, gluconic acid dimethylaminoethyl amide, dimethylaminoethanol, N - methyl diethanolamine, gamma-(dimethylamino)-butyric acid methyl ester, N,N - dimethyl - butylamine, N - methyl - morpholine, N,N - dimethylglycine - amide, N,N-dimethyl (beta - ethoxy - ethyl) - amine, N,N-dimethylglycine - N1,N1 - dimethyl - amide, acetic acid - 3 - dimethylaminopropylamide, or an amino-derivative of a monosaccharide or disaccharide.  The quaternized polymer may be used in the pharmaceutical field, e.g. for dissolving or greatly reducing the viscosity of slimes such as saliva, synovial fluid, or vitreous body solutions, or in the form of ointments.