1-[2-[bis(2-hydroxypropyl)amino]ethylamino]propan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine[bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet); 3350(broad OH); NMR(CDCl3): δ 3.8(broad m,3H); 2.5(broad m,10H); 1.1(d,9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: (VI-a): Glycidyl methacrylate (5.0 g, 35.5 mmol) was added, dropwise, to a solution of N,N,N'-tris(2-hydroxypropyl)ethylenediamine (V-a) (8.3 g, 35.5 mmol) in 10 mL of CH2Cl2 at room temperature. 4-Methoxyphenol (0.03 g) was added to prevent polymerization. The reaction was maintained for 72 hours at room temperature, then warmed to 30° C. for an additional 24 hours. The reaction was followed by TLC (4 percent MeOH in CCl4 ; glycidyl methacrylate Rf 0.69). Quadrol methacrylate (VI-a) was obtained in quantitative yield after removal of the solvent. The product was further purified by dissolving 5 g of (VI-a) in 200 mL distilled water followed by addition of sodium chloride to saturation. The product, which separated out as an oil, was collected, dissolved in CH2Cl2, and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed to give Quadrol-methacrylate [yield, 53 percent; IR(neet):3350(broad OH); 1720(C=O); 1640(C=C); NMR(CDCl3 ): δ6.2(s, 1H); 5.6(s, 1H); 4.0(broad m, 6); 2.5(broad m, 12H); 2.0 (s, 3H); 1.1(d, 9H)]. at room temperature polymerization warmed to 30° C. for an additional 24 hours

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

Procedure: (VI-a): Glycidyl methacrylate (5.0 g, 35.5 mmol) was added, dropwise, to a solution of N,N,N'-tris(2-hydroxypropyl)ethylenediamine (V-a) (8.3 g, 35.5 mmol) in 10 mL of CH2Cl2 at room temperature. 4-Methoxyphenol (0.03 g) was added to prevent polymerization. The reaction was maintained for 72 hours at room temperature, then warmed to 30° C. for an additional 24 hours. The reaction was followed by TLC (4 percent MeOH in CCl4 ; glycidyl methacrylate Rf 0.69). Quadrol methacrylate (VI-a) was obtained in quantitative yield after removal of the solvent. The product was further purified by dissolving 5 g of (VI-a) in 200 mL distilled water followed by addition of sodium chloride to saturation. The product, which separated out as an oil, was collected, dissolved in CH2Cl2, and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed to give Quadrol-methacrylate [yield, 53 percent; IR(neet):3350(broad OH); 1720(C=O); 1640(C=C); NMR(CDCl3 ): δ6.2(s, 1H); 5.6(s, 1H); 4.0(broad m, 6); 2.5(broad m, 12H); 2.0 (s, 3H); 1.1(d, 9H)]. at room temperature polymerization warmed to 30° C. for an additional 24 hours

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine [bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet): 3350(broad OH); NMR(CDCl3): δ 3.8(broad m, 3H); 2.5(broad m, 10H); 1.1(d, 9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil

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

Procedure: (VI-a): Glycidyl methacrylate (5.0 g, 35.5 mmol) was added, dropwise, to a solution of N,N,N'-tris(2-hydroxypropyl)ethylenediamine (V-a) (8.3 g, 35.5 mmol) in 10 mL of CH2Cl2 at room temperature. 4-Methoxyphenol (0.03 g) was added to prevent polymerization. The reaction was maintained for 72 hours at room temperature, then warmed to 30° C. for an additional 24 hours. The reaction was followed by TLC (4 percent MeOH in CCl4 ; glycidyl methacrylate Rf 0.69). Quadrol methacrylate (VI-a) was obtained in quantitative yield after removal of the solvent. The product was further purified by dissolving 5 g of (VI-a) in 200 mL distilled water followed by addition of sodium chloride to saturation. The product, which separated out as an oil, was collected, dissolved in CH2Cl2, and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed to give Quadrol-methacrylate [yield, 53 percent; IR(neet):3350(broad OH); 1720(C=O); 1640(C=C); NMR(CDCl3 ): δ6.2(s, 1H); 5.6(s, 1H); 4.0(broad m, 6); 2.5(broad m, 12H); 2.0 (s, 3H); 1.1(d, 9H)]. at room temperature polymerization warmed to 30° C. for an additional 24 hours

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

Procedure: Examples of suitable hydroxyalkylated ethylenediamines include, but are not limited to N,N,N′,N′-tetrakis-(2-hydroxypropyl)ethylenediamine and N,N,N′,N′-tetrakis-(hydroxyethyl)ethylenediamine. N-hydroxyethyl, N,N′,N′-tris(2-hydroxypropyl)ethylenediamine, and combinations of two or more thereof will not give solid. Preferably the hydroxyalkylated ethylenediamine is N,N,N′,N′-tetrakis-(2-hydroxypropyl)ethylenediamine or N,N,N′,N′-tetrakis-(hydroxyethyl)ethylenediamine. The hydroxyalkylated ethylene diamine, N,N,N′,N′-tetrakis-(2-hydroxypropyl)ethylenediamine, is available commercially, for example, from BASF Corporation, Mount Olive, N.J., under the name QUADROL polyol.

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

Procedure: (V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine[bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet); 3350(broad OH); NMR(CDCl3): δ 3.8(broad m,3H); 2.5(broad m,10H); 1.1(d,9H)]. distilled water at 80° C The reaction mixture was cooled concentrated to give a milky white viscous suspension dried over anhydrous sodium sulfate Unreacted (IV-a) precipitated was removed by filtration Ether was removed from the clear filtrate to produce a viscous liquid Fractional distillation of the oil