1,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dione

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

Procedure: The purpose of the present example was to determine the pH conditions required to dissolve approximately 1% 1,3,4,6-tetrachloroglycoluril in water in the presence of detergent.

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 590 g (5 mols) of 4,5-dihydroxy-2-imidazolidinone and 300 g (5 mols) of urea were dissolved in 1 liter of water. 30 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred at 90° C. for 1 hour. After cooling, the crystals thus precipitated were collected by filtration, washed with water and dried to obtain 526 g (yield: 74%) of glycoluril. The melting point of glycoluril was above 300° C. After cooling the crystals thus precipitated were collected by filtration washed with water dried

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 590 g (5 mols) of 4,5-dihydroxy-2-imidazolidinone and 300 g (5 mols) of urea were dissolved in 1 liter of water. 30 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred at 90° C. for 1 hour. After cooling, the crystals thus precipitated were collected by filtration, washed with water and dried to obtain 526 g (yield: 74%) of glycoluril. The melting point of glycoluril was above 300° C. After cooling the crystals thus precipitated were collected by filtration washed with water dried

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

Procedure: Into a suitable reaction vessel equipped with a stirrer, thermometer, and reflux condenser there was introduced 950 parts (30 moles) of methanol and 40 parts of concentrated hydrochloric acid. To this mixture, 262 parts (1 mole of tetramethylol glycoluril) were added and the reaction mixture was stirred at 25°-30° C. In about 15-20 minutes, all the tetramethylol glycoluril went into solution. After half an hour, the reaction mixture was neutralized with 140 parts of sodium bicarbonate and 20 parts of sodium carbonate at 22°-23° C. The pH after neutralization was about 8. The salt was filtered. The filtrate was concentrated at 60° C. under reduced pressure. The yield of the syrupy product after filtration of the salt was 290 parts, which was diluted to 90% solids with cellosolve. The product characteristics were as follows: Foil Solids: 91.4%; Pan Solids: 82.2%; and Gardner-Holdt Viscosity (25° C.): Z1. I.R. of the product indicated that the methylated product has a significant amount of unreacted methylol groups. Into a suitable reaction vessel equipped with a stirrer thermometer, and reflux condenser After half an hour The salt was filtered The filtrate was concentrated at 60° C. under reduced pressure The yield of the syrupy product after filtration of the salt was diluted to 90% solids with cellosolve Gardner-Holdt Viscosity (25° C.)

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

Procedure: The purpose of the present example was to determine the pH conditions required to dissolve approximately 1% 1,3,4,6-tetrachloroglycoluril in water in the presence of detergent.

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

Procedure: The purpose of the present example was to determine the pH conditions required to dissolve approximately 1% 1,3,4,6-tetrachloroglycoluril in water in the presence of detergent.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reaction vessel equipped as in Example A was charged 1064 grams tetramethoxymethyl glycoluril (TMMGU) and 532 grams hydrogenated bisphenol-A which was melted and heated to 120° C. 14 grams of Polycat 200 catayst was added slowly over a 30-minute period at 110°-120° C. to control foaming. The batch temperature was then raised slowly to 160° C. and foaming controlled with 2 grams additions of Quadrol. Total Quadrol added is 10.4 grams. Upon reaching a tack temperature of 80°-85° C., the batch was discharged into a tray. The product, a methoxy-methyl-functional copolymer of TMMGU and HBPA, has a tack temperature of 84° C., a viscosity at 50% non-volatile content in meta-pyrol of K and a methoxy equivalent weight of 212. A small amount of self-condensation had also occurred in this reaction in addition to the primary methoxyhydroxyl reaction. Into a reaction vessel equipped as in Example A The batch temperature was then raised slowly to 160° C. a tack temperature of 80°-85° C. a tack temperature of 84° C. A small amount of self-condensation

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a reaction vessel equipped as in Example A was charged 1064 grams tetramethoxymethyl glycoluril (TMMGU) and 532 grams hydrogenated bisphenol-A which was melted and heated to 120° C. 14 grams of Polycat 200 catayst was added slowly over a 30-minute period at 110°-120° C. to control foaming. The batch temperature was then raised slowly to 160° C. and foaming controlled with 2 grams additions of Quadrol. Total Quadrol added is 10.4 grams. Upon reaching a tack temperature of 80°-85° C., the batch was discharged into a tray. The product, a methoxy-methyl-functional copolymer of TMMGU and HBPA, has a tack temperature of 84° C., a viscosity at 50% non-volatile content in meta-pyrol of K and a methoxy equivalent weight of 212. A small amount of self-condensation had also occurred in this reaction in addition to the primary methoxyhydroxyl reaction. Into a reaction vessel equipped as in Example A The batch temperature was then raised slowly to 160° C. a tack temperature of 80°-85° C. a tack temperature of 84° C. A small amount of self-condensation

Conditions: temp:300.02; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The following experimental procedure was utilized to test physical properties of nonwoven substrates impregnated with the tetramethylol glycoluril-containing VAE copolymer emulsions. The copolymer binder was applied to the substrate using the Atlas padding technique. The emulsions were initially diluted with deionized water to 9.0% solids and the pH was adjusted to 4.0 with ammonium chloride. Whatman #4 chromatography paper was saturated with the binder, the samples were dried, heated at 300° F. for five minutes and then subjected to tensile testing. The strips were immersed in solvent for three minutes and then placed in an Instron (2" jaw span, 1"/min. crosshead speed) for testing. containing VAE copolymer emulsions the samples were dried

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 590 g (5 mols) of 4,5-dihydroxy-2-imidazolidinone and 300 g (5 mols) of urea were dissolved in 1 liter of water. 30 ml of concentrated hydrochloric acid was added to the solution and the mixture was stirred at 90° C. for 1 hour. After cooling, the crystals thus precipitated were collected by filtration, washed with water and dried to obtain 526 g (yield: 74%) of glycoluril. The melting point of glycoluril was above 300° C. After cooling the crystals thus precipitated were collected by filtration washed with water dried

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

Procedure: Into a suitable reaction vessel equipped with a stirrer, thermometer, and reflux condenser there was introduced 950 parts (30 moles) of methanol and 40 parts of concentrated hydrochloric acid. To this mixture, 262 parts (1 mole of tetramethylol glycoluril) were added and the reaction mixture was stirred at 25°-30° C. In about 15-20 minutes, all the tetramethylol glycoluril went into solution. After half an hour, the reaction mixture was neutralized with 140 parts of sodium bicarbonate and 20 parts of sodium carbonate at 22°-23° C. The pH after neutralization was about 8. The salt was filtered. The filtrate was concentrated at 60° C. under reduced pressure. The yield of the syrupy product after filtration of the salt was 290 parts, which was diluted to 90% solids with cellosolve. The product characteristics were as follows: Foil Solids: 91.4%; Pan Solids: 82.2%; and Gardner-Holdt Viscosity (25° C.): Z1. I.R. of the product indicated that the methylated product has a significant amount of unreacted methylol groups. Into a suitable reaction vessel equipped with a stirrer thermometer, and reflux condenser After half an hour The salt was filtered The filtrate was concentrated at 60° C. under reduced pressure The yield of the syrupy product after filtration of the salt was diluted to 90% solids with cellosolve Gardner-Holdt Viscosity (25° C.)

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

Procedure: The purpose of the present example was to determine the pH conditions required to dissolve approximately 1% 1,3,4,6-tetrachloroglycoluril in water in the presence of detergent.