* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Stage #1: With 10H-phenothiazine; 4-methoxy-phenol In xylene at 70℃; Heating / reflux Stage #2: at 70 - 103℃; Heating / reflux Stage #3: at 103 - 150℃; for 4 h; Heating / reflux
In the process of Example 1, to a 500 ml flask, equipped with a thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged xylene 20 g, methyl methacrylate (MMA, Aldrich) 62.7 g and phenothiazine (PTZ) 0.31 g. The mixture was heated toward to reflux with a very slow dry air purge. When the batch temperature reached 70° C., dibutyltin oxide (Bu2SnO, Eurecat 9555 from Crompton) 2.81 g was added. Heating was continued. When the batch began to boil at 103° C., dimethylaminopropylamine (DMAPA from BASF) 8.0 g was added quickly. Distillate started to come out after 20 minutes and within 30 minutes the batch became free from insoluble catalyst and clear. Then, 33.0 g DMAPA was added over 3 hours and the batch temperature was allowed to rise to 140° C. Distillate was collected. After the addition, the batch was held at 140-150° C. for two hours. A total 20 grams of methanol/methacrylate azeotrope was collected. Note that little distillate was collected 30 minutes after DMAPA addition, indicating the reaction was almost done. The remaining methyl methacrylate and xylene was distillated in vacuum until the batch temperature decreased to 135° C. at -17.5 inch Hg. A total 29 g of the distillate was collected, which could be recycled, and 74.2 gram residual was left in the reactor. HPLC analysis showed 89.7percent DMAPMA and 2.0percent methacrylic acid. This accounted for 97.4percent yield from DMAPA (Ex No.1, Table 1).; The process of Example 5 was run according to that described above for the process of Example 1, except more xylene as solvent and less dibutyl tin oxide catalyst were used. Addition of DMAPA was done over 1.5 hours. Similar yield to Example 1 was obtained.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
96.9 - 97.4 %Chromat.
Stage #1: With 10H-phenothiazine In xyleneHeating / reflux Stage #2: at 70 - 103℃; Heating / reflux Stage #3: at 103 - 150℃; for 5.5 h; Heating / reflux
In the process of Example 1, to a 500 ml flask, equipped with a thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged xylene 20 g, methyl methacrylate (MMA, Aldrich) 62.7 g and phenothiazine (PTZ) 0.31 g. The mixture was heated toward to reflux with a very slow dry air purge. When the batch temperature reached 70° C., dibutyltin oxide (Bu2SnO, Eurecat 9555 from Crompton) 2.81 g was added. Heating was continued. When the batch began to boil at 103° C., dimethylaminopropylamine (DMAPA from BASF) 8.0 g was added quickly. Distillate started to come out after 20 minutes and within 30 minutes the batch became free from insoluble catalyst and clear. Then, 33.0 g DMAPA was added over 3 hours and the batch temperature was allowed to rise to 140° C. Distillate was collected. After the addition, the batch was held at 140-150° C. for two hours. A total 20 grams of methanol/methacrylate azeotrope was collected. Note that little distillate was collected 30 minutes after DMAPA addition, indicating the reaction was almost done. The remaining methyl methacrylate and xylene was distillated in vacuum until the batch temperature decreased to 135° C. at -17.5 inch Hg. A total 29 g of the distillate was collected, which could be recycled, and 74.2 gram residual was left in the reactor. HPLC analysis showed 89.7percent DMAPMA and 2.0percent methacrylic acid. This accounted for 97.4percent yield from DMAPA (Ex No.1, Table 1).; The process of Example 2 was run according to that described above for the process of Example 1, except that DMAPA was fed less evenly, and rate fluctuation was allowed. Similar yield to Example 1 was obtained.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
95.2 %Chromat.
Stage #1: Heating / reflux; Neat (no solvent) Stage #2: at 70 - 103℃; Heating / reflux; Neat (no solvent) Stage #3: at 103 - 150℃; for 5.5 h; Heating / reflux; Neat (no solvent)
In the process of Example 1, to a 500 ml flask, equipped with a thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged xylene 20 g, methyl methacrylate (MMA, Aldrich) 62.7 g and phenothiazine (PTZ) 0.31 g. The mixture was heated toward to reflux with a very slow dry air purge. When the batch temperature reached 70° C., dibutyltin oxide (Bu2SnO, Eurecat 9555 from Crompton) 2.81 g was added. Heating was continued. When the batch began to boil at 103° C., dimethylaminopropylamine (DMAPA from BASF) 8.0 g was added quickly. Distillate started to come out after 20 minutes and within 30 minutes the batch became free from insoluble catalyst and clear. Then, 33.0 g DMAPA was added over 3 hours and the batch temperature was allowed to rise to 140° C. Distillate was collected. After the addition, the batch was held at 140-150° C. for two hours. A total 20 grams of methanol/methacrylate azeotrope was collected. Note that little distillate was collected 30 minutes after DMAPA addition, indicating the reaction was almost done. The remaining methyl methacrylate and xylene was distillated in vacuum until the batch temperature decreased to 135° C. at -17.5 inch Hg. A total 29 g of the distillate was collected, which could be recycled, and 74.2 gram residual was left in the reactor. HPLC analysis showed 89.7percent DMAPMA and 2.0percent methacrylic acid. This accounted for 97.4percent yield from DMAPA (Ex No.1, Table 1). ; The process of Example 3 was run according to that described above for the process of Example 1, except no solvent was used. A slightly lower yield was obtained.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
96.9 %Chromat. - 97.4 %
Stage #1: With 10H-phenothiazine In hexane; xyleneHeating / reflux Stage #2: at 70 - 103℃; Heating / reflux Stage #3: at 103 - 150℃; for 4.5 h; Heating / reflux
In the process of Example 1, to a 500 ml flask, equipped with a thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged xylene 20 g, methyl methacrylate (MMA, Aldrich) 62.7 g and phenothiazine (PTZ) 0.31 g. The mixture was heated toward to reflux with a very slow dry air purge. When the batch temperature reached 70° C., dibutyltin oxide (Bu2SnO, Eurecat 9555 from Crompton) 2.81 g was added. Heating was continued. When the batch began to boil at 103° C., dimethylaminopropylamine (DMAPA from BASF) 8.0 g was added quickly. Distillate started to come out after 20 minutes and within 30 minutes the batch became free from insoluble catalyst and clear. Then, 33.0 g DMAPA was added over 3 hours and the batch temperature was allowed to rise to 140° C. Distillate was collected. After the addition, the batch was held at 140-150° C. for two hours. A total 20 grams of methanol/methacrylate azeotrope was collected. Note that little distillate was collected 30 minutes after DMAPA addition, indicating the reaction was almost done. The remaining methyl methacrylate and xylene was distillated in vacuum until the batch temperature decreased to 135° C. at -17.5 inch Hg. A total 29 g of the distillate was collected, which could be recycled, and 74.2 gram residual was left in the reactor. HPLC analysis showed 89.7percent DMAPMA and 2.0percent methacrylic acid. This accounted for 97.4percent yield from DMAPA (Ex No.1, Table 1).; The process of Example 4 was run according to that described above for the process of Example 1, except a mixture of hexane and xylene was used as solvent. Addition of DMAPA was done over 2 hours and hexane was distilled out during the early stage of reaction. Similar yield to Example 1 was obtained.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
Stage #1: Heating / reflux; Neat (no solvent) Stage #2: at 70 - 101℃; Heating / reflux; Neat (no solvent)
In the process of Example 6, to a 500 ml flask, equipped with thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged methyl methacrylate (Aldrich) 206.7 g and phenothiazine 0.3 g. The mixture was heated toward to reflux with a very slow dry air purge. When batch temperature reached 70° C., dibutyltin oxide (Eurecat 9555 from Crompton) 5.01 g was added. Heating continued. When the batch began to boil at 101° C., dimethylethanolamine (DMEA from BASF) 11.8 g was added quickly. Distillate started to come out after 15 minutes and the batch became free from insoluble catalyst and clear. Then, 35.3 g DMEA was added over 45 minutes and the batch temperature was allowed to rise. Distillate was collected. After finishing DMEA, Tyzor TPT 0.35 g was added, the batch was held at reflux at 103-107° C. for one hour then DMAPA 53.34 g was added over 90 minutes. Continue to collect distillate at 60-65° C. and to allow the reaction temperature to rise. After the addition, the batch was held at 120-150° C. for three hours. The batch temperature rose gradually. A total 57 grams of methanol/methacrylate azeotrope was collected. The remaining methyl methacrylate was distilled under vacuum until the batch temperature decreased to 130° C. at -17.5 inch Hg. A total 63.5 g of the distillate was collected, which would be recycled. HPLC analysis showed 185 gram residual contained 45.4percent DMAPMA, 41.9percent dimethylaminoethyl methacrylate (DMAEMA) and 1.6percent methacrylic acid. This accounted for 95percent yield for DMAPMA from DMAPA and 94percent for DMAEMA from DMEA (Ex No.6).; The process of Example 11 was run according to that described above for the process of Example 6.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
99.6%
Stage #1: With 10H-phenothiazine; 4-methoxy-phenol In hexaneHeating / reflux Stage #2: at 70 - 101℃; Heating / reflux
In the process of Example 6, to a 500 ml flask, equipped with thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged methyl methacrylate (Aldrich) 206.7 g and phenothiazine 0.3 g. The mixture was heated toward to reflux with a very slow dry air purge. When batch temperature reached 70° C., dibutyltin oxide (Eurecat 9555 from Crompton) 5.01 g was added. Heating continued. When the batch began to boil at 101° C., dimethylethanolamine (DMEA from BASF) 11.8 g was added quickly. Distillate started to come out after 15 minutes and the batch became free from insoluble catalyst and clear. Then, 35.3 g DMEA was added over 45 minutes and the batch temperature was allowed to rise. Distillate was collected. After finishing DMEA, Tyzor TPT 0.35 g was added, the batch was held at reflux at 103-107° C. for one hour then DMAPA 53.34 g was added over 90 minutes. Continue to collect distillate at 60-65° C. and to allow the reaction temperature to rise. After the addition, the batch was held at 120-150° C. for three hours. The batch temperature rose gradually. A total 57 grams of methanol/methacrylate azeotrope was collected. The remaining methyl methacrylate was distilled under vacuum until the batch temperature decreased to 130° C. at -17.5 inch Hg. A total 63.5 g of the distillate was collected, which would be recycled. HPLC analysis showed 185 gram residual contained 45.4percent DMAPMA, 41.9percent dimethylaminoethyl methacrylate (DMAEMA) and 1.6percent methacrylic acid. This accounted for 95percent yield for DMAPMA from DMAPA and 94percent for DMAEMA from DMEA (Ex No.6).; The process of Example 10 was run according to that described above for the process of Example 7, except that small amount of hexane was used to remove any residual amount of water from the system. A lightly better yield was observed.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
84.4%
Stage #1: Heating / reflux; Neat (no solvent) Stage #2: at 70 - 101℃; Heating / reflux; Neat (no solvent)
In the process of Example 6, to a 500 ml flask, equipped with thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged methyl methacrylate (Aldrich) 206.7 g and phenothiazine 0.3 g. The mixture was heated toward to reflux with a very slow dry air purge. When batch temperature reached 70° C., dibutyltin oxide (Eurecat 9555 from Crompton) 5.01 g was added. Heating continued. When the batch began to boil at 101° C., dimethylethanolamine (DMEA from BASF) 11.8 g was added quickly. Distillate started to come out after 15 minutes and the batch became free from insoluble catalyst and clear. Then, 35.3 g DMEA was added over 45 minutes and the batch temperature was allowed to rise. Distillate was collected. After finishing DMEA, Tyzor TPT 0.35 g was added, the batch was held at reflux at 103-107° C. for one hour then DMAPA 53.34 g was added over 90 minutes. Continue to collect distillate at 60-65° C. and to allow the reaction temperature to rise. After the addition, the batch was held at 120-150° C. for three hours. The batch temperature rose gradually. A total 57 grams of methanol/methacrylate azeotrope was collected. The remaining methyl methacrylate was distilled under vacuum until the batch temperature decreased to 130° C. at -17.5 inch Hg. A total 63.5 g of the distillate was collected, which would be recycled. HPLC analysis showed 185 gram residual contained 45.4percent DMAPMA, 41.9percent dimethylaminoethyl methacrylate (DMAEMA) and 1.6percent methacrylic acid. This accounted for 95percent yield for DMAPMA from DMAPA and 94percent for DMAEMA from DMEA (Ex No.6).; The process of Example 8 was run according to that described above for the process of Example 6, except that dioctyltin oxide (Eurecat DOTO, Crompton) was used as the transesterification catalyst.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
90 %Chromat. - 100 %
Stage #1: Heating / reflux; Neat (no solvent) Stage #2: at 70 - 101℃; Heating / reflux; Neat (no solvent)
In the process of Example 6, to a 500 ml flask, equipped with thermometer, gas inlet, addition port, magnetic stirrer and distillation column of 5-plates topped with a distillation head connecting to a condenser, were charged methyl methacrylate (Aldrich) 206.7 g and phenothiazine 0.3 g. The mixture was heated toward to reflux with a very slow dry air purge. When batch temperature reached 70° C., dibutyltin oxide (Eurecat 9555 from Crompton) 5.01 g was added. Heating continued. When the batch began to boil at 101° C., dimethylethanolamine (DMEA from BASF) 11.8 g was added quickly. Distillate started to come out after 15 minutes and the batch became free from insoluble catalyst and clear. Then, 35.3 g DMEA was added over 45 minutes and the batch temperature was allowed to rise. Distillate was collected. After finishing DMEA, Tyzor TPT 0.35 g was added, the batch was held at reflux at 103-107° C. for one hour then DMAPA 53.34 g was added over 90 minutes. Continue to collect distillate at 60-65° C. and to allow the reaction temperature to rise. After the addition, the batch was held at 120-150° C. for three hours. The batch temperature rose gradually. A total 57 grams of methanol/methacrylate azeotrope was collected. The remaining methyl methacrylate was distilled under vacuum until the batch temperature decreased to 130° C. at -17.5 inch Hg. A total 63.5 g of the distillate was collected, which would be recycled. HPLC analysis showed 185 gram residual contained 45.4percent DMAPMA, 41.9percent dimethylaminoethyl methacrylate (DMAEMA) and 1.6percent methacrylic acid. This accounted for 95percent yield for DMAPMA from DMAPA and 94percent for DMAEMA from DMEA (Ex No.6).; The process of Example 7 was run according to that described above for the process of Example 6, except that dibutyltin oxide from Aldrich was used as the transesterification catalyst.; The process of Example 9 was run according to that described above for the process of Example 7, except that part of the MMA was recycled from previous reactions.; EXAMPLE 12DMAPMA distillate from the above reactions, containing water-insoluble organotin catalysts and 1300 ppm methacrylic acid (MMA) 170.0 g was mixed with 25percent NaOH 2 g and phenothiazine 0.05 g. The mixture was subjected to vacuum distillation. The distillate was collected at 91-93° C. and -30.3 inch Hg to yield 105 g pure DMAPMA (91percent yield) containing no water-insoluble and non-detectable MAA (<10 ppm) by HPLC analysis.
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, product of RAFT polymerization; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 44500, PDI 1.62 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 33300, PDI 1.32 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 47100, PDI 1.08 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 37700, PDI 1.07 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 32400, PDI 1.06 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(N-[3-(dimethylamino)propyl]methacrylamide), terminated with 4-carboxy-2-cyanobutyl-2-yl and thiobenzoylsulfanyl units, Mn 28100, PDI 1.07 by ASEC; monomer(s): N-[3-(dimethylamino)propyl]methacrylamide; 4-carboxy-2-cyanobutyl-2-yl dithiobenzoate[ No CAS ]
poly(acrylic acid-co-pentaerythritol triallyl ether-co-N-[3-(dimethylamino)propyl]methacrylamide-co-stearyl methacrylate)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With dilauryl peroxide; Belsil DMC 6031; tert-butyl peroctoate; In ethyl acetate; at 75 - 100℃; for 10h;Product distribution / selectivity;
The initial charge was heated to 75 C. under a nitrogen atmosphere and with stirring in an apparatus fitted with stirrer, reflux counter, internal thermometer and four feed devices. Feeds 1, 2 and 3 were added over the course of 3 h and the mixture was stirred for a further 2 h at 75 C. Feed 4 was added in 1 h at 80 C. and the mixture was then stirred for a further 1 h. The temperature was increased to 100 C. and, at this temperature, the mixture was stirred for a further 3 h. The resulting white suspension was then quaternized with 40 g of methyl chloride. The product was filtered, washed with acetone and dried under reduced pressure at 70 C.
With Belsil DMC 6031; tert-butyl peroctoate; potassium carbonate; di-(2-ethylhexyl)-peroxydicarbonate; In cyclohexane; ethyl acetate; at 50 - 100℃; for 11.5h;Product distribution / selectivity;
The initial charge was heated to 50 C. under a nitrogen atmosphere and with stirring in an apparatus fitted with stirrer, reflux counter, internal thermometer and three feed devices. Feed 1 was added over the course of 1.5 h and feed 2 was added over the course of 2 h and the mixture was stirred for a further 2 h at 60 C. Feed 3 was added in 1 h at 60 C. and the mixture was then stirred for a further 2 h at 70 C. The temperature was increased to 100 C. and, at this temperature, the mixture was stirred for a further 3 h. The resulting white suspension was filtered, washed with acetone and dried under reduced pressure at 70 C.
poly(3-dimethylaminopropyl methacrylate-co-vinylpyrrolidone)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With tert-butyl peroxypivalate; tert-amylperoxy pivalate; In water; at 60 - 85℃; for 5.5h;
The optimized reaction cycling time is very short (1.5 hours at 60 C. and 4 hours at 85 C.). The process includes the steps of: [00029] (1) Clean, dry, and tare a 1-liter glass resin reaction flask. [00030] (2) Install the reactor with agitator, heating mantle, condenser, thermocouple, septum for initiator addition, and nitrogen purging. [00031] (3) Add part of water solvent, all VP monomer, all DMAPMA monomer, all the BIS crosslinker, and all the Lupersol 11 initiator, into the reactor. [00032] The VP/DMAPMA ratio will vary depending on the kind of hydrogel to be made. A preferred initial concentration of VP and DMAPMA in the system is 20% by weight. The preferred weight ratio of crosslinker to VP and DMAPMA is 0.20%. The preferred weight ratio of Lupersol 11 to VP and DMAPMA is 1.10%. [00033] (4) At room temperature, start a purge with nitrogen until the reaction is complete. [00034] (5) Raise the temperature to 60 C. and maintain for 1.5 hours. [00035] (6) During the 60 C. period, when gelation occurs and the system is too viscous to agitate, add water to dilute the system from 20% to 10% solids. [00036] (7) Raise the temperature to 85 C. and maintain for 4 hours to reduce the residual monomer level. [00037] (8) When reaching 85 C., directly inject Lupersol 554 hourly through the syringe and rubber septum on the top of reactor into the reaction mixture. Four (4) additions of Lupersol 554 as booster are sufficient to reduce the residual monomer to acceptable levels. [00038] (9) During the 85 C. heating period, when the system is too viscous to agitate, all water to further dilute the system from 10% to 7.5% solids. [00039] (10) When the reaction is complete, cool the system to room temperature, and transfer the product into a large beaker. [00040] (11) A Ross Homogenizer is used to break up the gel. Addition of water to further dilute the system to 5% solids is used to enable the product to flow in and out of the homogenizer.
With 2,2'-azobis(isobutyronitrile) In ethyl acetate at 80℃; for 24h; Inert atmosphere;
9 Example 9
Under an argon atmosphere, 328 mg (2 mmol) of azobisisobutyronitrile (available from NACALAI TESQUE, INC.) was dissolved in a mixture of 17.0 g (100 mmol) of N-[3-(dimethylamino)propyl]methacrylamide (available from Tokyo Chemical Industry Co., Ltd.), 19.6 g (100 mmol) of 3-mercaptopropyltrimethoxysilane (available from Shin-Etsu Chemical Co., Ltd.), and 100 ml of dehydrated ethyl acetate, the inside of the reaction system was replaced with argon gas bubbled through the solution, and then, the solution was heated and stirred for 24 hours at 80° C. under an argon atmosphere, after which ethyl acetate was removed to obtain 35.6 g of a compound (H) in which a methacrylic group of N-[3-(dimethylamino)propyl]meth- acrylamide was bonded to a 3-(trimethoxysilyl)propyl group through a thioether bond.In 1H-NMR measurement, disappearance of signals (5.30 and 5.74 ppm) attributed to protons of the methacrylic group of N-[3-(dimethylamino)propyl]methacrylamide being a raw material was confirmed.
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