1-[(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)methyl]-5,5-dimethylimidazolidine-2,4-dione

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 268.3 g of 1,1'-methylene-bis-(5,5-dimethylhydantoin) [1 mol], 600 ml of dimethylformamide and 2.11 g of lithium chloride is stirred at 60° C. 134.0 g of propene oxide (2.3 mols) are slowly added dropwise to this mixture over the course of 1 hour and 45 minutes. Thereafter the mixture is heated to 100° C. over the course of 1.5 hours and stirred at 100° C. for a further 2 hours. The hot reaction mixture is now filtered and cooled to room temperature, neutralized with 20% strength sulphuric acid and concentrated to dryness on a rotary evaporator. The crude product is recrystallised from ethanol. 327.0 g of pure 1,1'-methylene-bis-(3-β-hydroxy-n-propyl-5,5-dimethylhydantoin) [85.3% of theory] of melting point 131°-133° C. are obtained. Microanalysis shows 14.50% N (calculated, 14.58% N); analysis by gel permeation chromatography shows that the substance is of uniform molecular weight. The N--NMR (nuclear magnetic resonance) spectrum and the IR (infrared) spectrum can be reconciled with the following structure: ##STR9## Thereafter the mixture is heated to 100° C. over the course of 1.5 hours stirred at 100° C. for a further 2 hours The hot reaction mixture is now filtered cooled to room temperature concentrated to dryness on a rotary evaporator The crude product is recrystallised from ethanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 268.3 g of 1,1'-methylene-bis-(5,5-dimethylhydantoin) [1 mol], 600 ml of dimethylformamide and 2.11 g of lithium chloride is stirred at 60° C. 134.0 g of propene oxide (2.3 mols) are slowly added dropwise to this mixture over the course of 1 hour and 45 minutes. Thereafter the mixture is heated to 100° C. over the course of 1.5 hours and stirred at 100° C. for a further 2 hours. The hot reaction mixture is now filtered and cooled to room temperature, neutralized with 20% strength sulphuric acid and concentrated to dryness on a rotary evaporator. The crude product is recrystallised from ethanol. 327.0 g of pure 1,1'-methylene-bis-(3-β-hydroxy-n-propyl-5,5-dimethylhydantoin) [85.3% of theory] of melting point 131°-133° C. are obtained. Microanalysis shows 14.50% N (calculated, 14.58% N); analysis by gel permeation chromatography shows that the substance is of uniform molecular weight. The N--NMR (nuclear magnetic resonance) spectrum and the IR (infrared) spectrum can be reconciled with the following structure: ##STR9## Thereafter the mixture is heated to 100° C. over the course of 1.5 hours stirred at 100° C. for a further 2 hours The hot reaction mixture is now filtered cooled to room temperature concentrated to dryness on a rotary evaporator The crude product is recrystallised from ethanol

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 268.3 g of 1,1'-methylene-bis-(5,5-dimethylhydantoin) [1 mol], 600 ml of dimethylformamide and 2.11 g of lithium chloride is stirred at 60° C. 134.0 g of propene oxide (2.3 mols) are slowly added dropwise to this mixture over the course of 1 hour and 45 minutes. Thereafter the mixture is heated to 100° C. over the course of 1.5 hours and stirred at 100° C. for a further 2 hours. The hot reaction mixture is now filtered and cooled to room temperature, neutralized with 20% strength sulphuric acid and concentrated to dryness on a rotary evaporator. The crude product is recrystallised from ethanol. 327.0 g of pure 1,1'-methylene-bis-(3-β-hydroxy-n-propyl-5,5-dimethylhydantoin) [85.3% of theory] of melting point 131°-133° C. are obtained. Microanalysis shows 14.50% N (calculated, 14.58% N); analysis by gel permeation chromatography shows that the substance is of uniform molecular weight. The N--NMR (nuclear magnetic resonance) spectrum and the IR (infrared) spectrum can be reconciled with the following structure: ##STR9## Thereafter the mixture is heated to 100° C. over the course of 1.5 hours stirred at 100° C. for a further 2 hours The hot reaction mixture is now filtered cooled to room temperature concentrated to dryness on a rotary evaporator The crude product is recrystallised from ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1'-Methylene-bis[3-glycidyl-5,5-dimethylhydantoin] is prepared by the reaction of epichlorohydrin and 1,1'-methylene-bis[5,5-dimethylhydantoin] according to Example 1 of U.S. Pat. No. 3,592,923. 1,1'-Methylene-bis[5,5-dimethylhydantoin] is prepared by the general procedure of Example I of U.S. Pat. No. 3,793,248 using paraformaldehyde and 5,5-dimethylhydantoin.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 268.3 g of 1,1'-methylene-bis-(5,5-dimethylhydantoin) [1 mol], 600 ml of dimethylformamide and 2.11 g of lithium chloride is stirred at 60° C. 134.0 g of propene oxide (2.3 mols) are slowly added dropwise to this mixture over the course of 1 hour and 45 minutes. Thereafter the mixture is heated to 100° C. over the course of 1.5 hours and stirred at 100° C. for a further 2 hours. The hot reaction mixture is now filtered and cooled to room temperature, neutralized with 20% strength sulphuric acid and concentrated to dryness on a rotary evaporator. The crude product is recrystallised from ethanol. 327.0 g of pure 1,1'-methylene-bis-(3-β-hydroxy-n-propyl-5,5-dimethylhydantoin) [85.3% of theory] of melting point 131°-133° C. are obtained. Microanalysis shows 14.50% N (calculated, 14.58% N); analysis by gel permeation chromatography shows that the substance is of uniform molecular weight. The N--NMR (nuclear magnetic resonance) spectrum and the IR (infrared) spectrum can be reconciled with the following structure: ##STR9## Thereafter the mixture is heated to 100° C. over the course of 1.5 hours stirred at 100° C. for a further 2 hours The hot reaction mixture is now filtered cooled to room temperature concentrated to dryness on a rotary evaporator The crude product is recrystallised from ethanol