2-(oxiran-2-ylmethoxymethyl)oxirane

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

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 mL, round bottom 3-neck flask equipped with a condenser, a nitrogen in/out let, a mechanical stirrer, a thermo-watch, and a heating mantle, a mixture of 30 g of 10,000 Mw PEG and toluene (80 mL) was heated to 60° C. At this temperature, KOH (2.19 g, 0.04 mol, in 2 g of water) was added and the reaction mixture was stirred for 1 hour. Dodecyl glycidyl ether (8.71 g, 0.04 mole) was added and the reaction temperature was kept at 110° C. for 5 hours. After the reaction mass was cooled to 60° C., toluene (80 mL) was further added. The solution was precipitated into 300 mL of hexane. After filtration and washing with ethyl acetate (100 mL×3×) and drying in vaccuo, a white polymer (33 g) was obtained. 1H NMR showed 11% hydrophobe incorporation. The Brookfield viscosity of a 5% aqueous solution of this oligomer was >200,000 cps (BF LV, S-63, 0.3 rpm at 25° C.). Paint performance: SG10 M (standard formulation). The material was not soluble in this paint. For UCAR 379 G, TE %=0.52, VLT=−6 KU. In a 250 mL, round bottom 3-neck flask equipped with a condenser the reaction temperature was kept at 110° C. for 5 hours After the reaction mass was cooled to 60° C. The solution was precipitated into 300 mL of hexane After filtration washing with ethyl acetate (100 mL×3×) drying in vaccuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 mL, round bottom 3-neck flask equipped with a condenser, a nitrogen in/out let, a mechanical stirrer, a thermo-watch, and a heating mantle, a mixture of 30 g of 10,000 Mw PEG and toluene (80 mL) was heated to 60° C. At this temperature, KOH (1.52 g, 0.04 mol, in 1.5 g of water) was added and the reaction mixture was stirred for 1 hour. Dodecyl glycidyl ether (5.81 g, 0.024 mole) was added and the reaction temperature was kept at 110° C. for 5 hours. After the reaction mass was cooled to 60° C., toluene (80 mL) was further added. The solution was precipitated into 300 mL of hexane. After filtration and washing with ethyl acetate (100 mL×3×) and drying in vacuum, a white polymer (31.8 g) was obtained. 1H NMR showed 11% hydrophobe incorporation. The Brookfield viscosity of a 5% aqueous solution of this oligomer was >400000 cps (BF LV, S-63, 0.3 rpm at 25° C.). Paint performance: SG10 M (standard formulation). The material was not soluble in this paint. For UCAR 379 G, TE %=0.52, VLT=−17 KU. In a 250 mL, round bottom 3-neck flask equipped with a condenser the reaction temperature was kept at 110° C. for 5 hours After the reaction mass was cooled to 60° C. The solution was precipitated into 300 mL of hexane After filtration washing with ethyl acetate (100 mL×3×) drying in vacuum

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

Procedure: To a five neck, two liter round bottom flask equipped with an addition funnel, thermometer, nitrogen dispersant tube, mechanical stirrer, and a decanting head with a water-cooled condenser were added 220 grams (1.00 mole) of nonylphenol and 250 milliliters of cyclohexane. The solution was then heated to reflux and 2.8 grams (1.3 wt. % based on nonylphenol) of potassium hydroxide in 10 milliliters of water was slowly added to the flask. After essentially all the water was recovered in the decanting head (10 milliliters+1 milliliter formed), 250.7 grams (0.91 mole) of nonylphenyl glycidyl ether as added dropwise. During the addition of the glycidyl ether, the reaction temperature was maintained between 60° and 80° C. After the addition was complete, the solution was refluxed for four hours. The contents of the flask were then washed with a five percent aqueous solution of phosphoric acid, and the organic layer was separated from the water layer and washed twice with deionized water. The reaction mixture was then placed in a one liter round bottom flask, and the remaining cyclohexane and unreacted nonylphenol were recovered by distillation, first at atmospheric pressure, then under vacuum at 0.2 mm Hg. The kettle temperature was not allowed to exceed 180° C. during the distillation to prevent discoloration of the product. The concentrated solution was then refiltered to give 425 grams of a pale-yellow liquid. End-group MW analysis gave a molecular weight of 506.8 (theoretical MW=496.8). Ir and nmr spectra were identical to previously recorded spectra for the compound. To a five neck, two liter round bottom flask equipped with an addition funnel The solution was then heated to reflux as added dropwise the reaction temperature was maintained between 60° and 80° C After the addition the solution was refluxed for four hours The contents of the flask were then washed with a five percent aqueous solution of phosphoric acid the organic layer was separated from the water layer washed twice with deionized water The reaction mixture was then placed in a one liter round bottom flask the remaining cyclohexane and unreacted nonylphenol were recovered by distillation, first at atmospheric pressure to exceed 180° C. during the distillation

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

Procedure: To a five neck, two liter round bottom flask equipped with an addition funnel, thermometer, nitrogen dispersant tube, mechanical stirrer, and a decanting head with a water-cooled condenser were added 220 grams (1.00 mole) of nonylphenol and 250 milliliters of cyclohexane. The solution was then heated to reflux and 2.8 grams (1.3 wt. % based on nonylphenol) of potassium hydroxide in 10 milliliters of water was slowly added to the flask. After essentially all the water was recovered in the decanting head (10 milliliters+1 milliliter formed), 250.7 grams (0.91 mole) of nonylphenyl glycidyl ether as added dropwise. During the addition of the glycidyl ether, the reaction temperature was maintained between 60° and 80° C. After the addition was complete, the solution was refluxed for four hours. The contents of the flask were then washed with a five percent aqueous solution of phosphoric acid, and the organic layer was separated from the water layer and washed twice with deionized water. The reaction mixture was then placed in a one liter round bottom flask, and the remaining cyclohexane and unreacted nonylphenol were recovered by distillation, first at atmospheric pressure, then under vacuum at 0.2 mm Hg. The kettle temperature was not allowed to exceed 180° C. during the distillation to prevent discoloration of the product. The concentrated solution was then refiltered to give 425 grams of a pale-yellow liquid. End-group MW analysis gave a molecular weight of 506.8 (theoretical MW=496.8). Ir and nmr spectra were identical to previously recorded spectra for the compound. To a five neck, two liter round bottom flask equipped with an addition funnel The solution was then heated to reflux as added dropwise the reaction temperature was maintained between 60° and 80° C After the addition the solution was refluxed for four hours The contents of the flask were then washed with a five percent aqueous solution of phosphoric acid the organic layer was separated from the water layer washed twice with deionized water The reaction mixture was then placed in a one liter round bottom flask the remaining cyclohexane and unreacted nonylphenol were recovered by distillation, first at atmospheric pressure to exceed 180° C. during the distillation

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

Procedure: 100 parts of hydrogenated polyisoprene glycol (PIP-H, average molecular weight of 2500, made by Idemitsu Petrochemicals Corp. Japan), 9 parts of epichlorohydrin, 0.15 part of trifluoroborondiethylether complex and 50 parts of toluene were fed and carried out addition reaction under vigorous stirring at 55 degrees C. for 5 hours in the nitrogen atmosphere. Then, 9.5 parts of 48% aqueous solution of sodium hydroxide were added and a ring-closing reaction was carried out at 65 degrees C. for 5 hours. After the reaction 100 parts of water were added and the following procedures were carried out same as described in Reference Example No. 1 and 95 parts of glycidyl ether of hydrogenated polyisoprene glycol (b) were obtained. The glycidyl ether (b) had an epoxy equivalent weight of 1,430 g/eq. carried out addition reaction a ring-closing reaction was carried out at 65 degrees C for 5 hours were added

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 parts of hydrogenated polyisoprene glycol (PIP-H, average molecular weight of 2,500, made by Idemitsu Petrochemicals Corp. Japan), 35 parts of epichlorohydrin, 16 parts of pelletized sodium hydroxide, 1 part of benzyl trimethyl ammonium chloride and 50 parts of toluene were fed and reacted under a vigorous stirring at 50 degrees C. for 5 hours in the nitrogen atmosphere. After the reaction, 100 parts of water were added and the product was washed while stirring for 10 minutes. After laying it quietly, the upper layer was separated and filtered, and then the remaining epichlorohydrin and toluene were removed under vacuum. Thus 90 parts of glycidyl ether of hydrogenated polyisoprene glycol (a) was obtained as a residue. This glycidyl ether (a) had an epoxy equivalent weight of 1,650 g/eq. reacted under were added the product was washed while stirring for 10 minutes the upper layer was separated filtered the remaining epichlorohydrin and toluene were removed under vacuum

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

Procedure: Glycidyl ether of novolak type substituted phenolic resin was produced from the novolak type phenolic resin synthesized in Example 1, using a 1-liter flask equipped with a thermometer, dropping funnel, stirrer, and separating tube with cooler. In the flask were placed 1.0 mol (as phenolic hydroxyl group) of novolak type phenolic resin, 7.0 mols of epichlorohydrin, and 0.4 times (by weight) as much dioxane as epichlorohydrin. Then, 48% NaOH (1.0 mol as NaOH) was added dropwise over 4 hours. During this time, epichlorohydrin, dioxane, and water were azeotropically boiled at 58° to 60° C. under reduced pressure (150 mmHg) and cooled in the separating tube, whereby the organic layer containing major amounts of epichlorohydrin and dioxane were returned to the reaction system whereas the water layer was discharged from the reaction system. After the reaction was completed, epichlorohydrin and dioxane were distilled away, and the reaction product was dissolved in methyl isobutyl ketone. Then the salt formed as a by-product was filtered out, and then methyl isobutyl ketone was distilled away. Thus, there was obtained a glycidyl ether of the novolak type substituted phenolic resin. This product was found to contain 0.029% (290 ppm) of hydrolyzable chlorine and to have an epoxy equivalent of 203, a softening point of 62° C., and a density of 1.19 g/cm3. equipped with a thermometer separating tube with cooler cooled in the separating tube, whereby the organic layer epichlorohydrin and dioxane were distilled away the reaction product was dissolved in methyl isobutyl ketone Then the salt formed as a by-product was filtered out methyl isobutyl ketone was distilled away

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

Procedure: 1.0 mol (in terms of phenolic hydroxyl group) of the novolak type substituted phenolic resin obtained in the above step (1) was dissolved in 6.0 mols of epichlorohydrin in a 1-liter flask equipped with a thermometer, separating tube, dropping funnel, and stirrer. 48% NaOH (1.05 mols as NaOH) was added dropwise over 6 hours. During this time epichlorohydrin and water were azeotropically boiled at 66° C. under reduced pressure (150 mmHg) and cooled by the separating tube, whereby the epichlorohydrin layer was returned to the reaction system whereas the water layer was discharged from the reaction system. After the reaction was completed, the epichlorohydrin was distilled away and the reaction product was dissolved in toluene. The salt formed as a by-product was filtered out, and then toluene was distilled away. Thus there was obtained a glycidyl ether of the novolak type substituted phenolic resin. This glycidyl ether was found to contain 500 ppm of hydrolyzable chlorine and to have an epoxy equivalent of 200, a softening point of 61° C., and a density of 1.19 g/cm3. The 13C-NMR of this glycidyl ether was also measured in the same way as in step (1). The results are shown in FIG. 2. obtained in the above step (1) equipped with a thermometer separating tube the epichlorohydrin was distilled away the reaction product was dissolved in toluene The salt formed as a by-product was filtered out toluene was distilled away

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

Procedure: Into a round bottom flask having a capacity of 500 ml and equipped with a reflux condenser, a thermometer, a dropping funnel, a nitrogen gas supply tube, and a stirring means, 81.2 g (1.4 moles) of acetone, and 2.0 g (0.014 mole) of boron trifluoride etharate were charged and stirred while supplying a nitrogen gas. Then, 64.9 g (0.2 mole) of oleyl glycidyl ether was gradually added dropwise while supplying a nitrogen gas. The reaction mixture generates heat as the glycidyl ether is added. Therefore, the reaction mixture was cooled to maintain a temperature of from 20° to 30° C., and it took about one hour for the addition of the glycidyl ether. The stirring was continued for further one hour. After confirming by the gas chromatograph of the reaction mixture that the glycidyl ether completely disappeared, the reaction mixture was poured into a dilute aqueous solution of sodium bicarbonate whereby the acid was neutralized. Ether was added thereto and the mixture was stirred, and thereafter the ether layer was collected by separation. Anhydrous sodium sulfate was added for dehydration, and the solvent was removed by distillation under a reduced pressure thereby to obtain 68.8 g (yield: 90%) of colourless, transparent 2,2-dimethyl-4-oleyloxymethyl- 1,3-dioxolan. Into a round bottom flask having a capacity of 500 ml and equipped with a reflux condenser is added Therefore, the reaction mixture was cooled to maintain a temperature of from 20° to 30° C., and it the mixture was stirred the ether layer was collected by separation Anhydrous sodium sulfate was added for dehydration the solvent was removed by distillation under a reduced pressure