hexanedihydrazide

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the dropping tank of a reaction vessel (tank) equipped with a stirrer, a thermometer, a nitrogen-sealing tube, a condenser and a dropping tank were placed 30.0 parts of PA-1, 22.0 parts of methyl methacrylate (referred to hereinafter as MMA), 10.0 parts of n-butyl acrylate (referred to hereinafter as BA), 0.5 part of acrylic acid (referred to hereinafter as AA), 2.5 parts of diacetoneacrylamide (referred to hereinafter as DAAA), 1.0 part of 2,2′-azobis-2-isobutyronitrile (referred to hereinafter as AIBN), 25 parts of MEK and 25 parts of IPA, and then well mixed. Separately, in the reaction tank were placed 30.0 parts of PA-1, 22.0 parts of MMA, 10.0 parts of BA, 0.5 part of AA, 2.5 parts of DAAA, 10 parts of MEK and 10 parts of IPA, and then uniformly mixed. Subsequently, the reaction tank was heated to 75° C. and the liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours. Thereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours. Thereafter, 2.0 parts of triethylamine (referred to hereinafter as TEA) was added to the reaction mixture to sufficiently neutralize the same, after which aqueous hydrazide consisting of 149 parts of distilled water and 2.6 parts of adipic acid dihydrazide (referred to hereinafter as ADH) was added and the reaction mixture was emulsified. Thereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr to obtain an aqueous emulsion of a self-emulsifiable acryl-urethane copolymer having a solid content of 40.1% (the emulsion is referred to hereinafter as EA-1). In the dropping tank of a reaction vessel (tank) equipped with a stirrer well mixed uniformly mixed the liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours Thereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours was added Thereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 200 g of phosgene in 1.6 kg of phenol was introduced at 20° C. into a 4-liter phosgenation apparatus, and 174 g of adipic acid dihydrazide were added thereto. The mixture was heated to 85° C. within one hour, with stirring; gas evolved above a reaction temperature of 45° C. Phosgene was then introduced into the reaction mixture at 85° C. over 5 hours (approx. 30 g per hour), with stirring. The solution was then purged with nitrogen at 85 to 90° C. for 30 minutes, and the major part of the phenol was finally removed by vacuum distillation at from 50 to 60° C. The remaining product was dissolved in 1 liter of toluene at 60° C. and precipitated by cooling to 20° C. The precipitate was suction filtered, washed with toluene and dried under vacuum. were added evolved above a reaction temperature of 45° C with stirring The solution was then purged with nitrogen at 85 to 90° C. for 30 minutes the major part of the phenol was finally removed by vacuum distillation at from 50 to 60° C The remaining product was dissolved in 1 liter of toluene at 60° C. precipitated by cooling to 20° C filtered washed with toluene dried under vacuum

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 200 g of phosgene in 1.6 kg of phenol was introduced at 20° C. into a 4-liter phosgenation apparatus, and 174 g of adipic acid dihydrazide were added thereto. The mixture was heated to 85° C. within one hour, with stirring; gas evolved above a reaction temperature of 45° C. Phosgene was then introduced into the reaction mixture at 85° C. over 5 hours (approx. 30 g per hour), with stirring. The solution was then purged with nitrogen at 85 to 90° C. for 30 minutes, and the major part of the phenol was finally removed by vacuum distillation at from 50 to 60° C. The remaining product was dissolved in 1 liter of toluene at 60° C. and precipitated by cooling to 20° C. The precipitate was suction filtered, washed with toluene and dried under vacuum. were added evolved above a reaction temperature of 45° C with stirring The solution was then purged with nitrogen at 85 to 90° C. for 30 minutes the major part of the phenol was finally removed by vacuum distillation at from 50 to 60° C The remaining product was dissolved in 1 liter of toluene at 60° C. precipitated by cooling to 20° C filtered washed with toluene dried under vacuum

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

Procedure: In a stainless steel flask equipped with an agitator, 45.6 grams of water were added, the agitator was turned on, then 25 grams of adipic acid dihydrazide were added. The mixture was agitated for at least 10 minutes until a stable dispersion was formed. 16.4 grams of 2-propanone were then added under mixing. A clear solution formed after a few minutes. Mixing was continued for at least another hour until reaction product precipitated and formed a stable dispersion. The temperature of the dispersion was allowed to drop to 105° F. or below, and 10 grams of an acrylic latex containing 51% of methacrylate and butyl acrylic polymer were added, followed by 3.0 grams of AQUAFLOW NLS-200. The Stormer viscosity of the dispersion was 105 Kreb units at 77° F. were added were added was formed under mixing A clear solution formed after a few minutes Mixing until reaction product precipitated formed a stable dispersion to drop to 105° F. or below were added at 77° F.

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

Procedure: In a stainless steel flask equipped with an agitator, 45.6 grams of water were added, the agitator was turned on, then 25 grams of adipic acid dihydrazide were added. The mixture was agitated for at least 10 minutes until a stable dispersion was formed. 16.4 grams of 2-propanone were then added under mixing. A clear solution formed after a few minutes. Mixing was continued for at least another hour until reaction product precipitated and formed a stable dispersion. The temperature of the dispersion was allowed to drop to 105° F. or below, and 10 grams of an acrylic latex containing 51% of methacrylate and butyl acrylic polymer were added, followed by 3.0 grams of AQUAFLOW NLS-200. The Stormer viscosity of the dispersion was 105 Kreb units at 77° F. were added were added was formed under mixing A clear solution formed after a few minutes Mixing until reaction product precipitated formed a stable dispersion to drop to 105° F. or below were added at 77° F.

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

Procedure: In a stainless steel flask equipped with an agitator, 54.6 grams of water were added, the agitator was turned on, then 25 grams of adipic acid dihydrazide were added. The mixture was agitated for at least 10 minutes until a stable dispersion was formed. 16.4 grams of 2-propanone were then added under mixing. A clear solution formed after a few minutes. Mixing was continued for at least another hour until reaction product precipitated and formed a stable dispersion. 4 grams of AQUAFLOW NLS-200 (rheology additive) were added to the dispersion under agitation. were added were added was formed under mixing A clear solution formed after a few minutes Mixing until reaction product precipitated formed a stable dispersion 4 grams of AQUAFLOW NLS-200 (rheology additive) were added to the dispersion under agitation

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

Procedure: In a stainless steel flask equipped with an agitator, 58.6 grams of water were added, the agitator was turned on, then 25 grams of adipic acid dihydrazide were added. The mixture was agitated for at least 10 minutes until a stable dispersion was formed. 16.4 grams of 2-propanone were then added under mixing. A clear solution formed after a few minutes. Mixing was continued for at least another hour until reaction product precipitated and formed a stable dispersion. were added were added was formed under mixing A clear solution formed after a few minutes Mixing until reaction product precipitated formed a stable dispersion

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

Procedure: In a stainless steel flask equipped with an agitator, 58.6 grams of water were added, the agitator was turned on, then 25 grams of adipic acid dihydrazide were added. The mixture was agitated for at least 10 minutes until a stable dispersion was formed. 16.4 grams of 2-propanone were then added under mixing. A clear solution formed after a few minutes. Mixing was continued for at least another hour until reaction product precipitated and formed a stable dispersion. were added were added was formed under mixing A clear solution formed after a few minutes Mixing until reaction product precipitated formed a stable dispersion

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

Procedure: In addition, as a further difference, feed stream 1 was metered in at a uniform rate over 5 minutes rather than 40 minutes, and feed stream 2 was metered in at a uniform rate over 125 minutes rather than 90 minutes. The additions of the 12.0 g of deionized water each took place following the ends of feed streams 1 and 2, and the additions of the aqueous ammonia solution took place at the same distance from the beginning of the reaction as in example 3, and, furthermore, instead of 40.9 g of a 13.2% strength by weight aqueous solution of adipic dihydrazide, 36.4 g of a 2.5% strength by weight aqueous solution of adipic dihydrazide were used. feed stream 2 was metered in at a uniform rate over 125 minutes rather than 90 minutes from the beginning of the reaction as in example 3

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the dropping tank of a reaction vessel (tank) equipped with a stirrer, a thermometer, a nitrogen-sealing tube, a condenser and a dropping tank were placed 30.0 parts of PA-1, 22.0 parts of methyl methacrylate (referred to hereinafter as MMA), 10.0 parts of n-butyl acrylate (referred to hereinafter as BA), 0.5 part of acrylic acid (referred to hereinafter as AA), 2.5 parts of diacetoneacrylamide (referred to hereinafter as DAAA), 1.0 part of 2,2′-azobis-2-isobutyronitrile (referred to hereinafter as AIBN), 25 parts of MEK and 25 parts of IPA, and then well mixed. Separately, in the reaction tank were placed 30.0 parts of PA-1, 22.0 parts of MMA, 10.0 parts of BA, 0.5 part of AA, 2.5 parts of DAAA, 10 parts of MEK and 10 parts of IPA, and then uniformly mixed. Subsequently, the reaction tank was heated to 75° C. and the liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours. Thereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours. Thereafter, 2.0 parts of triethylamine (referred to hereinafter as TEA) was added to the reaction mixture to sufficiently neutralize the same, after which aqueous hydrazide consisting of 149 parts of distilled water and 2.6 parts of adipic acid dihydrazide (referred to hereinafter as ADH) was added and the reaction mixture was emulsified. Thereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr to obtain an aqueous emulsion of a self-emulsifiable acryl-urethane copolymer having a solid content of 40.1% (the emulsion is referred to hereinafter as EA-1). In the dropping tank of a reaction vessel (tank) equipped with a stirrer well mixed uniformly mixed the liquid mixture in the dropping tank was dropped into the reaction tank over 5 hours Thereafter, the resulting mixture was further subjected to reaction at the same temperature for 4 hours was added Thereafter, the MEK and the IPA present in the system were removed at 60° C. at 100 Torr

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

Procedure: Doxycycline-HCl (100 mg) was finely ground with 90 mg DSS (Mw, 500,000) and 8 mg adipic dihydrazide. The mixture was loaded into a 3-ml syringe fitted with a Luer plug. Oxidized dextran solution (1 ml, Mw of 500,000; 66 mg/ml) was loaded into a second syringe. An injectable formulation was formed after connecting the syringes and performing 30 reciprocations of the syringe plungers. The mixture was loaded into a 3-ml syringe fitted with a Luer plug was loaded into a second syringe An injectable formulation was formed

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

Procedure: Amikacin Sulfate (100 mg), DBM (200 mg), and 8 mg of adipic acid dihydrazide were placed into a beaker and mixed thoroughly. Oxidized dextran solution (Mw, 500,000; 66 mg/ml; 1 ml) was added to the mixture. Tobramycin-sulfate or tobramycin-sulfate/clindamycin-HCl (1/1) can be used in place of amikacin-sulfate. mixed thoroughly