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With Kohlensaeure-bis-<2,2,6,6-tetramethyl-piperidinyl-(4)-ester-N-oxyl>; In Hexadecane; at 20 - 150℃; for 12h;Product distribution / selectivity; |
Example 2-1 and Comparative Examples 2-1 to 2-3; Comparative Compound 2 (bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate) was synthesized as described below.; The following compounds were mixed together: 4 ml of 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine, 1 ml of methyl sebacate, 0.06 g of sodium methoxide, and 30 ml of heptane. Methanol was removed from the mixture under reflux. After the absence of methyl sebacate in the reaction liquid was confirmed by gas chromatography, the reaction liquid was washed with water such that sodium methoxide and 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine were removed from the reaction liquid. The solvent was removed from the reaction liquid washed with water, whereby a solid was obtained. The solid was recrystallized from hexane, whereby 1.5 g of bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate was obtained. In 25 ml of n-hexadecane, 10 mg of each polymerization inhibitor shown in Table 2 was dissolved, whereby a solution was prepared. A mixture of 1 mul of the solution and 5 mul of stearyl methacrylate was heated from room temperature to 150C at 15C/minute in a differential scanning calorimeter. The time from the moment of reaching 150C to an exothermic peak due to polymerization was thereby measured and defined as polymerization inhibitory activity (hours). The measurement results are summarized in Table 2. As is clear from Table 2, the compound according to the present invention is suitable for the long-term stabilization of a monomer and exhibits a stabilizing effect higher than that of Comparative Compound 1, which has a low molecular weight, and that of Comparative Compound 2, which has a high molecular weight. As a polymerization inhibitor, the compound according to the present invention is clearly superior to a known hindered amine compound having a nitroxyl structure. |
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With TEMPOL; In Hexadecane; at 20 - 150℃; for 6h;Product distribution / selectivity; |
Example 2-1 and Comparative Examples 2-1 to 2-3; Comparative Compound 2 (bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate) was synthesized as described below.; The following compounds were mixed together: 4 ml of 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine, 1 ml of methyl sebacate, 0.06 g of sodium methoxide, and 30 ml of heptane. Methanol was removed from the mixture under reflux. After the absence of methyl sebacate in the reaction liquid was confirmed by gas chromatography, the reaction liquid was washed with water such that sodium methoxide and 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine were removed from the reaction liquid. The solvent was removed from the reaction liquid washed with water, whereby a solid was obtained. The solid was recrystallized from hexane, whereby 1.5 g of bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate was obtained. In 25 ml of n-hexadecane, 10 mg of each polymerization inhibitor shown in Table 2 was dissolved, whereby a solution was prepared. A mixture of 1 mul of the solution and 5 mul of stearyl methacrylate was heated from room temperature to 150C at 15C/minute in a differential scanning calorimeter. The time from the moment of reaching 150C to an exothermic peak due to polymerization was thereby measured and defined as polymerization inhibitory activity (hours). The measurement results are summarized in Table 2. As is clear from Table 2, the compound according to the present invention is suitable for the long-term stabilization of a monomer and exhibits a stabilizing effect higher than that of Comparative Compound 1, which has a low molecular weight, and that of Comparative Compound 2, which has a high molecular weight. As a polymerization inhibitor, the compound according to the present invention is clearly superior to a known hindered amine compound having a nitroxyl structure. |
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With bis(1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl)sebacate; In Hexadecane; at 20 - 150℃; for 9h;Product distribution / selectivity; |
Example 2-1 and Comparative Examples 2-1 to 2-3; Comparative Compound 2 (bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate) was synthesized as described below.; The following compounds were mixed together: 4 ml of 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine, 1 ml of methyl sebacate, 0.06 g of sodium methoxide, and 30 ml of heptane. Methanol was removed from the mixture under reflux. After the absence of methyl sebacate in the reaction liquid was confirmed by gas chromatography, the reaction liquid was washed with water such that sodium methoxide and 1-oxy-2,2,6,6-tetramethyl-4-hydroxypiperidine were removed from the reaction liquid. The solvent was removed from the reaction liquid washed with water, whereby a solid was obtained. The solid was recrystallized from hexane, whereby 1.5 g of bis(1-oxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate was obtained. In 25 ml of n-hexadecane, 10 mg of each polymerization inhibitor shown in Table 2 was dissolved, whereby a solution was prepared. A mixture of 1 mul of the solution and 5 mul of stearyl methacrylate was heated from room temperature to 150C at 15C/minute in a differential scanning calorimeter. The time from the moment of reaching 150C to an exothermic peak due to polymerization was thereby measured and defined as polymerization inhibitory activity (hours). The measurement results are summarized in Table 2. As is clear from Table 2, the compound according to the present invention is suitable for the long-term stabilization of a monomer and exhibits a stabilizing effect higher than that of Comparative Compound 1, which has a low molecular weight, and that of Comparative Compound 2, which has a high molecular weight. As a polymerization inhibitor, the compound according to the present invention is clearly superior to a known hindered amine compound having a nitroxyl structure. |
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