Ethane, 1-(2,3-epoxypropoxy)-2-(vinyloxy)-

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

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

Procedure: To a mixture of hydoxyethyl vinyl ether (500 g) and tetra-n-butyl ammonium hydrogen sulfate (50 g), an aqueous solution of sodium hydroxide (340 g) dissolved in water ax (380 ml) was added over 30 minutes and then further stirred at room temperature for 1 hour. Further, chloromethyloxysilane (78.8 g) was added thereto and stirred at 60° C. for 2 hour. Then, ethyl acetate was added to the reaction mixture, followed by washing with water. The organic layer was extracted and dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents. The resulting liquid was purified by vacuum distillation, to obtain 530 g of the 2-glycidyloxyethyl vinyl ether (A-37) (boiling point 65° C., 532 Pa). was added over 30 minutes stirred at 60° C. for 2 hour by washing with water The organic layer was extracted dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents The resulting liquid was purified by vacuum distillation

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

Procedure: To a mixture of hydoxyethyl vinyl ether (500 g) and tetra-n-butyl ammonium hydrogen sulfate (50 g), an aqueous solution of sodium hydroxide (340 g) dissolved in water ax (380 ml) was added over 30 minutes and then further stirred at room temperature for 1 hour. Further, chloromethyloxysilane (78.8 g) was added thereto and stirred at 60° C. for 2 hour. Then, ethyl acetate was added to the reaction mixture, followed by washing with water. The organic layer was extracted and dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents. The resulting liquid was purified by vacuum distillation, to obtain 530 g of the 2-glycidyloxyethyl vinyl ether (A-37) (boiling point 65° C., 532 Pa). was added over 30 minutes stirred at 60° C. for 2 hour by washing with water The organic layer was extracted dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents The resulting liquid was purified by vacuum distillation

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

Procedure: Glutaric acid (1.32 g; 0.01 moles) was added slowly over about 20 minutes to a stirred reaction flask containing 2-vinyloxyethyl glycidyl ether (prepared as described by Sawamoto et. Al in J. Polym. Sci., Part A 1987, V. 25, 2717) at 80° C. After all the acid was added, heating and stirring was continued for a further 2 hours. On cooling, the product, bis-[α-(2-glycidoxyethoxy)ethyl]glutarate, was obtained in quantitative yield. The structure of the product was confirmed by 1H NMR and IR analysis. Previous synthesis of polyepoxides by addition of 2-vinyloxyethyl glycidyl ether to polycarboxylic acids has previously been reported to occur in the presence of acid catalysts by Tofimov et. al (Review Heteroatom Chem. 1993, V.9, 205). Such catalysts are undesirable as they tend to reduce the storage stability of the epoxide monomer and reduce the degradation temperature of the cured adhesive polymer. After all the acid was added heating On cooling

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1000 ml three-necked round bottom flask, equipped with a thermocouple, magnetic stirrer and heating mantle, was added ethylene glycol vinyl ether (35.2 g; 0.400 moles), epibromohydrin (62.4 g; 0.456 mole), toluene (200 ml), and tetrabutylammonium bromide (1.5 g). Sodium hydroxide pellets (32 g 0.8 moles) were then added portionwise, with the reaction temperature maintained at 80° C. The reaction mixture was vigorously stirred for a period of time of about 1 hour at a temperature of 80° C. The mixture was then filtered and rinsed with a small amount of toluene. The toluene was removed using a rotary evaporator under reduced pressure and the crude product distilled under vacuum to yield 2-vinyloxyethylglycidyl ether (“VEGE”) (34.6 g; 60% yield), b.p. 55-57° C. at 0.75 torr. The structure of VEGE was confirmed by 1H NMR analysis (300 MHz; CDCl3): δ 6.5 (q, 1H, CH2═CH—), δ 4.0 and 4.2 (two d, 2H, CH2═CH—), δ 3.85 (m, 4H, O—CH2—CH2—O), δ 3.8 and 3.45 (m, 2H, O—CH2—CH—), δ 3.2 (m, 1H, epoxide ring —CH(CH2)—O), δ 2.6 and 2.8 (m, 2H, epoxide ring —CH(CH2)—O). To a 1000 ml three-necked round bottom flask, equipped with a thermocouple, magnetic stirrer heating mantle were then added portionwise, with the reaction temperature The mixture was then filtered rinsed with a small amount of toluene The toluene was removed a rotary evaporator under reduced pressure the crude product distilled under vacuum

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

Procedure: To a mixture of hydoxyethyl vinyl ether (500 g) and tetra-n-butyl ammonium hydrogen sulfate (50 g), an aqueous solution of sodium hydroxide (340 g) dissolved in water ax (380 ml) was added over 30 minutes and then further stirred at room temperature for 1 hour. Further, chloromethyloxysilane (78.8 g) was added thereto and stirred at 60° C. for 2 hour. Then, ethyl acetate was added to the reaction mixture, followed by washing with water. The organic layer was extracted and dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents. The resulting liquid was purified by vacuum distillation, to obtain 530 g of the 2-glycidyloxyethyl vinyl ether (A-37) (boiling point 65° C., 532 Pa). was added over 30 minutes stirred at 60° C. for 2 hour by washing with water The organic layer was extracted dried with magnesium sulfate, and condensed at reduced pressure to distill off the solvents The resulting liquid was purified by vacuum distillation

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

Procedure: Glutaric acid (1.32 g; 0.01 moles) was added slowly over about 20 minutes to a stirred reaction flask containing 2-vinyloxyethyl glycidyl ether (prepared as described by Sawamoto et. Al in J. Polym. Sci., Part A 1987, V. 25, 2717) at 80° C. After all the acid was added, heating and stirring was continued for a further 2 hours. On cooling, the product, bis-[α-(2-glycidoxyethoxy)ethyl]glutarate, was obtained in quantitative yield. The structure of the product was confirmed by 1H NMR and IR analysis. Previous synthesis of polyepoxides by addition of 2-vinyloxyethyl glycidyl ether to polycarboxylic acids has previously been reported to occur in the presence of acid catalysts by Tofimov et. al (Review Heteroatom Chem. 1993, V.9, 205). Such catalysts are undesirable as they tend to reduce the storage stability of the epoxide monomer and reduce the degradation temperature of the cured adhesive polymer. After all the acid was added heating On cooling