2-hydroxyethyl prop-2-enoate

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

Procedure: To a mixed solution containing 1 M of 2,4,6,8-tetramethylcyclotetrasiloxane and 0.01 g of Zn(CH3CO2)2 was slowly added 1 M of 2-hydroxyethyl acrylate. The resulting mixture was stirred for 12 hours at a room temperature. Thereafter, 200 mL of benzene and 200 mL of cold water were added. The organic layer was separated, washed with 200 mL of cold water, dried over MgSO4, filtered, and concentrated by distillation to provide the title compound of Formula 1A (yield: 97%). The organic layer was separated washed with 200 mL of cold water dried over MgSO4 filtered concentrated by distillation

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

Procedure: A benzylidenecyanoacetate-capped PLURACOL HP1250D was made as described in Example 1. An adhesive composition was made by mixing 39.25 weight percent of the benzylidenecyanoacetate-capped PLURACOL HP1250D, 39.25 weight percent vinyl toluene, 4.00 weight percent of the reaction product of caprolactone, phosphorus pentoxide and 2-hydroxyethylacrylate (commercially available from Nippon Kayaku Co. under the trade designation KAYAMER PM 21), 3.00 weight percent divinyl benzene, 1.40 weight percent diisopropanol-p-toluidine, 0.60 weight percent dimethyl aniline and 5.00 weight percent silica to form side A. 7.50 weight percent benzoyl peroxide initiator then was mixed with side A and immediately thereafter the resulting adhesive was applied to five steel coupons that were bonded together to form lap shear joints as per ASTM D-1002-94. The lap shear joints were allowed to fully cure overnight and then tested according to ASTM D-1002-94. The joints exhibited an average strength of 1241 psi and an adhesive failure mode (in other words, the adhesive failed before any destruction of the steel). Weight percents are based on the total amount of sides A and B.

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

Procedure: Cyclopentadiene of Formula VI and 2-hydroxyethylacrylate of the following Formula VII are dissolved at the same rate in ether or tetrahydrofuran and reacted at a temperature of about −30 to 60° C. for 24 hours. Thereafter, the solvent is removed by use of a rotary evaporator and the residue is distilled in vacuo to give 2-hydroxyethyl 5-norbornene-2-carboxylate of the following Formula VIII, which occurs in an endo- and exo-mixture. Thereafter, the solvent is removed by use of a rotary evaporator the residue is distilled in vacuo

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

Procedure: Into a reaction vessel equipped with a stirrer were charged 5.5 parts of tolylene diisocyanate, 42.0 parts of a ring-opening copolymer from tetrahydrofuran and 3-methyltetrahydrofuran, having a number average molecular weight of 2,000, and 0.01 part of 2,6-di-t-butyl-p-cresol, as a polymerization inhibitor. The mixture was cooled with ice to a temperature of below 10° C., while stirring. When the temperature was lower than 10° C., 0.04 part of dibutyltindilaurate was added and the mixture was stirred for 2 hours while controlling the temperature at 20-30° C. Then, after the addition of 2.2 parts of hydroxyethyl acrylate, the mixture was stirred for 4 hours at 50-60° C., until the amount of remaining isocyanate is 0.1% by weight or less. The Liquid urethane acrylate obtained in this manner is hereinafter referred to as UA-2. Into a reaction vessel equipped with a stirrer The mixture was cooled with ice to a temperature of below 10° C. was lower than 10° C. 0.04 part of dibutyltindilaurate was added the mixture was stirred for 2 hours at 20-30° C

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

Procedure: Into a reaction vessel equipped with a stirrer were charged 3.0 parts of tolylene diisocyanate, 50.5 parts of a ring-opening copolymer from ethylene oxide and butene oxide, having a number average molecular weight of 4,000, and 0.01 part of 2,6-di-t-butyl-p-cresol, as a polymerization inhibitor. The mixture was cooled with ice to a temperature of below 10° C., while stirring. When the temperature was lower than 10° C., 0.04 part of dibutyltindilaurate was added and the mixture was stirred for 2 hours while controlling the temperature at 20-30° C. Then, after the addition of 0.3 part of γ-mercaptopropyltrimethoxy silane, the mixture was stirred for a further one hour at 30-40° C., whereupon 1.2 parts of hydroxyethyl acrylate was added. The mixture was stirred for 4 hours at 50-60° C., until the amount of remaining isocyanate is 0.1% by weight or less. The liquid urethane acrylate obtained in this manner is hereinafter referred to as UA-1. Into a reaction vessel equipped with a stirrer The mixture was cooled with ice to a temperature of below 10° C. was lower than 10° C. 0.04 part of dibutyltindilaurate was added the mixture was stirred for 2 hours at 20-30° C was added

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

Procedure: A mixture of 140 g of N-carbamylmaleimide (1 mole), 121.8 g of 2-hydroxyethyl acrylate (1.05 moles) and 1.36 g of zinc chloride (0.01 moles) in 200 mL of acetonitrile was heated to reflux. After 5 hours, the mixture was poured into 500 mL of water. The solid was filtered, washed with water and dried to afford 240.7 g (94% yield) of 2-hydroxyethyl acrylate maleurate. M.P.: 88°-90° C. (dec.); 1H NMR (CDCl3): δ10.4 (br s, 1H), 8.2 (br s, 1H), 6.4 (m, 3H), 6.2 (d of d, 1H), 5.9 (m, 2H), 4.4 (A2B2, 4H); 13C NMR (CDCl3): δ165.9, 165.3, 165.2, 155.1, 133.1, 131.6, 129.5, 127.8, 63.2, 61.9; HPLC (10% CH3CN/H2O, C18): Rt=5.7 minutes. was heated to reflux The solid was filtered washed with water dried

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2-liter 3-necked flask provided with a stirrer and thermometer were metered in 365.4 parts of 2-hydroxyethyl acrylate, 0.45 parts of di-n-butyltin dilaurate, and 0.4 parts of hydroquinone monomethylether, followed by stirring at 55° C. and adding dropwise in 3 hours, 543.1 parts of a triisocyanate (tradename: Duranate TPA-100, manufactured by Asahi Kasei Kogyo Co., Ltd.), a trimer of hexamethylene diisocyanate and having an isocyanurate skeleton. After the end of the dropwise addition, the reaction was further continued for 8 hours at 70° C. when the viscosity increased so that n-butyl acetate was used to dilute to give a urethane triacrylate (UPA-3) having a final solids concentration of 90% by weight. A 2-liter 3-necked flask provided with a stirrer adding dropwise in 3 hours After the end of the dropwise addition to dilute

Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a 1-liter 3-necked flask provided with a stirrer and thermometer were metered in 425 parts of dodecabutyleneglycol (tradename: PTG-850, manufactured by Hodogaya Chemical Industries Co., Ltd, molecular weight 850), 0.43 parts of di-n-butyltin dilaurate, 0.4 parts of hydroquinone monomethylether, followed by stirring at 55° C. and adding dropwise, 222 parts of isophorone diisocyanate in 3 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours at 70° C. and then temperature was reduced to 60° C., then 122 parts of 2-hydroxyethyl acrylate was added dropwise in 2 hours. Since the viscosity increased, 193 parts of n-butyl acetate was added and the reaction was continued for 5 hours at 70° C. to give an urethane diacrylate (UPA-2) with a solids concentration of 80% by weight. Into a 1-liter 3-necked flask provided with a stirrer adding dropwise After completion of the dropwise addition was reduced to 60° C. Since the viscosity increased the reaction was continued for 5 hours at 70° C.

Conditions: temp:57.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A flask equipped with an agitator, condenser, nitrogen inlet tube and an addition funnel was charged with isooctyl acrylate (155.75 g), N-vinyl-2-pyrrolidone (15.75 g) and hydroxyethyl acrylate (3.50 g) premixed in a mixture of ethyl acetate (249.38 g) and methanol (13.13 g). 2,2'-Azobis-(2-methyl-butyronitrile) (0.26 g, Wako™ V-59) was added to initiate reaction. The mixture was purged with nitrogen to remove oxygen. The mixture was agitated and heated to 57° C. and the reaction was run for about 24 hours at this temperature. After termination of the reaction additional ethyl acetate (178.13 g) and methanol (9.38 g) were added. The inherent viscosity was 1.27 dl/g. A flask equipped with an agitator, condenser, nitrogen inlet tube and an addition funnel reaction The mixture was purged with nitrogen to remove oxygen After termination of the reaction additional ethyl acetate (178.13 g) and methanol (9.38 g) were added

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

Procedure: Cyclopentadiene of Formula VI and 2-hydroxyethylacrylate of the following formula VII were dissolved at a same rate in ether or tetrahydrofuran. Thereafter, this was reacted at a temperature of about -30 to 60° C. for 24 hours. Thereafter, the solvent was removed by use of a rotary evaporator and the residues were distilled in vacuo to give 2-hydroxyethyl 5-norbornene-2-carboxylate of the following formula VIII which was in an endo- and exo-mixture. ##STR5## Thereafter, this was reacted at a temperature of about -30 to 60° C. for 24 hours Thereafter, the solvent was removed by use of a rotary evaporator the residues were distilled in vacuo

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

Procedure: 2 moles of isophorone diisocyanate, 1 mole of triethylene glycol, and 2 moles of 2-hydroxyethyl acrylate were reacted by a predetermined method so as to yield urethane acrylate as a monomer of a ultraviolet-curing resin. Subsequently, a monomeric composition was prepared by mixing 50 grams of the urethane acrylate, 25 grams of the acrylic ester compound obtained in Example 1, 25 grams of 1,6-hexanediol diacrylate as a monomer of the ultraviolet-curing resin, and 3 grams of benzylmethyl ketal as a photopolymerization initiator (produced by Ciba-Geigy and marketed under the trade name "Irgacure 651").

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

Procedure: A master batch was prepared by combining isooctyl acrylate (714.00 g), 2-hydroxyethyl acrylate (523.00 g), polymethylmethacrylate macromonomer (52.00 g) of ELVACITE™ 1010 available from ICI Acrylics), 2,2′-azobis(2-methylbutyronitrile) (2.60 g), ethyl acetate (1245.50 g) and isopropanol (45.50 g). The resulting solution was divided in equal portions and placed into six 1 quart (0.95 L) amber glass bottles. The bottles were purged for 2 minutes with nitrogen at a flow rate of 1 L per minute. The bottles were sealed and placed in a rotating water bath at 57° C. for 24 hours. At 24 hours the bottles were removed from the rotating water bath, unsealed, diluted with 76 g methanol per bottle, mixed until homogenous, and recombined into a 1 gallon (3.8 L) glass jar. The percent solids of the resultant copolymer was 40.5%. The inherent viscosity, I.V., (of a 0.15 g/dL solution of polymer in ethyl acetate measured at 27° C.) was 0.77 dL/g. A master batch was prepared The bottles were purged for 2 minutes with nitrogen at a flow rate of 1 L per minute The bottles were sealed At 24 hours the bottles were removed from the rotating water bath unsealed, diluted with 76 g methanol per bottle mixed until homogenous, and measured at 27° C.