2-[2-(2-butoxyethoxy)ethoxy]ethanol

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)150 -OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)50 -OH (surfactant) and 2 parts of toluene. Both flasks were heated to azeotropically distill off the water with stirring +N2 sparge. After the water concentration in each flask was less than 50 ppm the mixture was cooled to 55° C. Sodium methoxide was added to each flask in an amount that OH:NaOMe=1:1 based on the calculated hydroxyl value of surfactant. Heat was applied to distill off formed methanol by distilling off half of the initial weight of toluene from the flask. In the first flask, the reaction mixture was then refluxed for 1 hour. The flask was cooled to 60° C. afterwhich 1.1 moles of epichlorohydrin were added per mole sodium alkoxide. The reaction mixture was then maintained at 70° C. for about 2 hours. When alkalinity by titration approached zero, the excess epichlorohydrin was vacuum stripped. A 4.0 gram aliquot of the reaction mixture +4 grams of tetraethylammonium bromide were dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The difference in the total alkalinity minus the HClO4 titration equals the amount of epoxide. The contents of the first and second flasks were mixed in a third flask such that the epoxy/alkoxide molar ratio was equal to 1:1 and the contents heated to 75°-85° C. for 2 hours. When the epoxy titration value equaled zero, 1-chlorooctane was added such that the mole ratio of Cl:ONa was 1:1. The reaction mixture was then refluxed until the alkalinity titration value was zero. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight. To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube Both flasks were heated to azeotropically distill off the water sparge After the water concentration in each flask Sodium methoxide was added to each flask in an amount that OH Heat to distill off formed methanol by distilling off half of the initial weight of toluene from the flask In the first flask, the reaction mixture was then refluxed for 1 hour The reaction mixture was then maintained at 70° C. for about 2 hours the contents heated to 75°-85° C. for 2 hours was added such that the mole ratio of Cl The reaction mixture was then refluxed until the alkalinity titration value

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ink 27 was prepared with reference to Example 1 of Patent Literature 4 (Japanese Patent Application Laid-Open No. 2010-018741). A mixture of 20.0 parts of carbon black (trade name: Monarch (M) 1000, product of Cabot), 12.0 parts of a polymer dispersant (trade name: BYK190, product of BYK Japan) and 68.0 parts of ion-exchanged water was treated by a Nano mill in which the packing rate of zirconia beads having a diameter of 0.5 mm was set to 80%, thereby preparing a pigment dispersion having a pigment content of 20 mass %. Fifteen parts of the resultant pigment dispersion, 10.0 part of a water-soluble polyurethane polymer (trade name: SF126, product of DAI-ICHI KOGYO SEIYAKU), 30.0 parts of diethylene glycol methyl ethyl ether, 0.2 parts of a silicone compound (trade name: FZ-2105, product of Dow Corning Toray), 0.4 parts of a stabilizer (trade name: ADEKA PLURONIC F-108, product of ADEKA) and 44.4 parts of ion-exchanged water were mixed, sufficiently stirred and dispersed, and the resultant dispersion was then filtered under pressure through a microfilter (product of Fuji Photo Film Co., Ltd.) having a pore size of 3.0 μm to prepare Ink 27. Ink 27 was prepared with reference to Example 1 of Patent Literature 4 (Japanese Patent Application Laid-Open No preparing a pigment dispersion dispersed the resultant dispersion was then filtered under pressure through a microfilter (product of Fuji Photo Film Co., Ltd.) to prepare Ink 27

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedure followed that of Reference Example 4, except for use of n-octyl bromide and triethylene glycol n-butyl ether instead of butyl bromide and diethylene glycol butyl ether, respectively. Triethylene glycol n-butyl n-octyl ether (abbreviated as “TEG-BO” hereafter) was obtained by distillation (b.p.: 140-145° C. at 70 Pa). TEG-BO has a corresponding boiling point of about 350° C. under normal pressure. The solubility of glycolide in this compound at 25° C. was 2.0%.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedure followed that of Reference Example 4, except for use of n-octyl bromide and triethylene glycol n-butyl ether instead of butyl bromide and diethylene glycol butyl ether, respectively. Triethylene glycol n-butyl n-octyl ether (abbreviated as “TEG-BO” hereafter) was obtained by distillation (b.p.: 140-145° C. at 70 Pa). TEG-BO has a corresponding boiling point of about 350° C. under normal pressure. The solubility of glycolide in this compound at 25° C. was 2.0%.

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP--(EO)150 --OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP--(EO)50 --OH (surfactant) and 2 parts of toluene. Both flasks were heated to azeotropically distill off the water with stirring +N2 sparge. After the water concentration in each flask was less than 50 ppm the mixture was cooled to 55° C. Sodium methoxide was added to each flask in an amount that OH:NaOMe =1:1 based on the calculated hydroxyl value of surfactant. Heat was applied to distill off formed methanol by distilling off half of the initial weight of toluene from the flask. In the first flask, the reaction mixture was then refluxed for 1 hour. The flask was cooled to 60° C. after which 1.1 moles of epichlorohydrin were added per mole sodium alkoxide. The reaction mixture was then maintained at 70° C. for about 2 hours. When alkalinity by titration approached zero, the excess epichlorohydrin was vacuum stripped. A 4.0 gram aliquot of the reaction mixture +4 grams of tetraethylammonium bromide were dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The difference in the total alkalinity minus the HClO4 titration equals the amount of epoxide. The contents of the first and second flasks were mixed in a third flask such that the epoxy/alkoxide molar ratio was equal to 1:1 and the contents heated to 75-85° C. for 2 hours. When the epoxy titration value equaled zero, 1-chlorooctane was added such that the mole ratio of Cl:ONa was 1:1. The reaction mixture was then refluxed until the alkalinity titration value was zero. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight. To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube a distillation head were added 1 part of NP To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube a distillation head were added 1 part of NP Both flasks were heated to azeotropically distill off the water sparge After the water concentration in each flask Sodium methoxide was added to each flask in an amount that OH Heat to distill off formed methanol by distilling off half of the initial weight of toluene from the flask In the first flask, the reaction mixture was then refluxed for 1 hour The reaction mixture was then maintained at 70° C. for about 2 hours the contents heated to 75-85° C. for 2 hours was added such that the mole ratio of Cl The reaction mixture was then refluxed until the alkalinity titration value

反応条件: temp:42.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three neck flask were added 102.1 grams of the dithiophosphoric acid obtained from Example 9 and 10.6 grams of calcium hydroxide. The reaction was heated to 42° C. The temperature then increased rapidly to 115° C. The reaction was placed in a water bath and the temperature decreased back to 30° C. This gave a viscous product, to which 20.3 grams of triethylene glycol monobutyl ether were added. The reaction was then heated back to 98° C., and was then stopped heating. After cooling back to 37° C., 4.4 grams of 35% hydrogen peroxide were added over a period of one and one half hours. The reaction was then heated back to 119° C. under vacuum and water was removed by distillation. The product was then filtered with diatomaceous earth. The temperature then increased rapidly to 115° C The reaction was placed in a water bath decreased back to 30° C This gave a viscous product The reaction was then heated back to 98° C. was then stopped heating After cooling back to 37° C. was removed by distillation The product was then filtered with diatomaceous earth

反応条件: temp:42.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a three neck flask were added 102.1 grams of the dithiophosphoric acid obtained from Example 9 and 10.6 grams of calcium hydroxide. The reaction was heated to 42° C. The temperature then increased rapidly to 115° C. The reaction was placed in a water bath and the temperature decreased back to 30° C. This gave a viscous product, to which 20.3 grams of triethylene glycol monobutyl ether were added. The reaction was then heated back to 98° C., and was then stopped heating. After cooling back to 37° C., 4.4 grams of 35% hydrogen peroxide were added over a period of one and one half hours. The reaction was then heated back to 119° C. under vacuum and water was removed by distillation. The product was then filtered with diatomaceous earth. The temperature then increased rapidly to 115° C The reaction was placed in a water bath decreased back to 30° C This gave a viscous product The reaction was then heated back to 98° C. was then stopped heating After cooling back to 37° C. was removed by distillation The product was then filtered with diatomaceous earth

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: This example illustrates the production of a compound of formula I wherein B3 and B4 are ether linkages. To a round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head, were added 70 millimoles of tridecyl alcohol ethoxylate (nominal 100 ethyleneoxy units per mole of ethoxylate), 30 millimoles of polyethylene glycol having a molecular weight of about 8,000 grams/mole and 400 grams of toluene. To this mixture was added 140 millimoles of sodium hydroxide (as an aqueous solution at 50% by weight sodium hydroxide). The flask was then heated to azeotropically distill off most of the water with stirring and nitrogen gas sparging. The conditions of distillation were such that about 1,000 ppm of water remained in the toluene solution. The solution was then cooled to 80° C. after which 90 millimoles of epichlorohydrin were added. The reaction mixture was then maintained at 80° C. until the epoxide titration reached approximately zero. (A 4.0 gram aliquot of the reaction mixture and 4 grams of tetraethylammonium bromide can be dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The reaction mixture was then neutralized to a substantially neutral pH (about pH 7) with aqueous hydrochloric acid. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight. To a round bottom flask equipped with a stirrer, nitrogen inlet tube The flask was then heated to azeotropically distill off most of the water nitrogen gas sparging The conditions of distillation were added

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Polymerization of styrene with the system NaNH2 and triethylene glycol monobutyl ether. Polymerization is allowed to proceed from 8.32 g (8·10-22 mole) of styrene in in 30 cc THF in the presence of 0.98 g (25·10-3 mole) of sodium amide and 1.71 g (8.3·10-3 mole) of triethylene glycol monobutyl ether. The reaction mixture which is obtained prior to the addition of the monomer has a yellow color which is more pronounced than that obtained with diethylene glycol monoethyl ether, contrary to the results which have been obtained with glycol monomethyl ether. At the end of four hours, a polymer is obtained in 50% yield, with Mn=8500. Polymerization The reaction mixture which is obtained to the addition of the monomer

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)150 -OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)50 -OH (surfactant) and 2 parts of toluene. Both flasks were heated to azeotropically distill off the water with stirring +N2 sparge. After the water concentration in each flask was less than 50 ppm the mixture was cooled to 55° C. Sodium methoxide was added to each flask in an amount that OH:NaOMe=1:1 based on the calculated hydroxyl value of surfactant. Heat was applied to distill off formed methanol by distilling off half of the initial weight of toluene from the flask. In the first flask, the reaction mixture was then refluxed for 1 hour. The flask was cooled to 60° C. afterwhich 1.1 moles of epichlorohydrin were added per mole sodium alkoxide. The reaction mixture was then maintained at 70° C. for about 2 hours. When alkalinity by titration approached zero, the excess epichlorohydrin was vacuum stripped. A 4.0 gram aliquot of the reaction mixture +4 grams of tetraethylammonium bromide were dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The difference in the total alkalinity minus the HClO4 titration equals the amount of epoxide. The contents of the first and second flasks were mixed in a third flask such that the epoxy/alkoxide molar ratio was equal to 1:1 and the contents heated to 75°-85° C. for 2 hours. When the epoxy titration value equaled zero, 1-chlorooctane was added such that the mole ratio of Cl:ONa was 1:1. The reaction mixture was then refluxed until the alkalinity titration value was zero. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight. To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube Both flasks were heated to azeotropically distill off the water sparge After the water concentration in each flask Sodium methoxide was added to each flask in an amount that OH Heat to distill off formed methanol by distilling off half of the initial weight of toluene from the flask In the first flask, the reaction mixture was then refluxed for 1 hour The reaction mixture was then maintained at 70° C. for about 2 hours the contents heated to 75°-85° C. for 2 hours was added such that the mole ratio of Cl The reaction mixture was then refluxed until the alkalinity titration value

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Polymerization of styrene with the system NaNH2 and triethylene glycol monobutyl ether. Polymerization is allowed to proceed from 8.32 g (8·10-22 mole) of styrene in in 30 cc THF in the presence of 0.98 g (25·10-3 mole) of sodium amide and 1.71 g (8.3·10-3 mole) of triethylene glycol monobutyl ether. The reaction mixture which is obtained prior to the addition of the monomer has a yellow color which is more pronounced than that obtained with diethylene glycol monoethyl ether, contrary to the results which have been obtained with glycol monomethyl ether. At the end of four hours, a polymer is obtained in 50% yield, with Mn=8500. Polymerization The reaction mixture which is obtained to the addition of the monomer

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)150 -OH (surfactant) and 2 parts of toluene. To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube, and a distillation head were added 1 part of NP-(EO)50 -OH (surfactant) and 2 parts of toluene. Both flasks were heated to azeotropically distill off the water with stirring +N2 sparge. After the water concentration in each flask was less than 50 ppm the mixture was cooled to 55° C. Sodium methoxide was added to each flask in an amount that OH:NaOMe=1:1 based on the calculated hydroxyl value of surfactant. Heat was applied to distill off formed methanol by distilling off half of the initial weight of toluene from the flask. In the first flask, the reaction mixture was then refluxed for 1 hour. The flask was cooled to 60° C. afterwhich 1.1 moles of epichlorohydrin were added per mole sodium alkoxide. The reaction mixture was then maintained at 70° C. for about 2 hours. When alkalinity by titration approached zero, the excess epichlorohydrin was vacuum stripped. A 4.0 gram aliquot of the reaction mixture +4 grams of tetraethylammonium bromide were dissolved in 50 ml of glacial acetic acid and the resulting solution titrated with a 0.1036 N HClO4 in glacial acetic acid solution to a methyl violet end point for the amount of epoxide (epoxy titration). The difference in the total alkalinity minus the HClO4 titration equals the amount of epoxide. The contents of the first and second flasks were mixed in a third flask such that the epoxy/alkoxide molar ratio was equal to 1:1 and the contents heated to 75°-85° C. for 2 hours. When the epoxy titration value equaled zero, 1-chlorooctane was added such that the mole ratio of Cl:ONa was 1:1. The reaction mixture was then refluxed until the alkalinity titration value was zero. Butoxytriglycol (BTG) and water were added to give a clear yellow BTG/H2O/product ratio of 1:2:2 by weight. To a first 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube To a second 250 ml round bottom flask equipped with a stirrer, nitrogen inlet tube Both flasks were heated to azeotropically distill off the water sparge After the water concentration in each flask Sodium methoxide was added to each flask in an amount that OH Heat to distill off formed methanol by distilling off half of the initial weight of toluene from the flask In the first flask, the reaction mixture was then refluxed for 1 hour The reaction mixture was then maintained at 70° C. for about 2 hours the contents heated to 75°-85° C. for 2 hours was added such that the mole ratio of Cl The reaction mixture was then refluxed until the alkalinity titration value