Method for manufacturing (meth)acryloyl group-containing polyol compound, (meth)acryloyl group-containing polyol compound, and urethane (meth)acrylate
A polyol compound and acrylate technology, applied in the field of urethane acrylate, can solve the problems of low acrylate yield and difficult hydrolysis reaction, and achieve the effect of an effective preparation method
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[0020] The production method of the (meth)acryloyl group-containing polyol compound (x3) according to the present invention includes the following three steps.
[0021] Step 1: The polyol compound (A) having at least 3 hydroxyl groups in the molecular structure and the cyclic ketone compound (B) are combined with the above-mentioned cyclic ketone compound ( B) The molar ratio [(OH) / (CO)] of the carbonyl group (CO) contained in the ratio in the range of 3 to 12, the reaction is carried out in the organic solvent (S) and in the presence of an acid catalyst , and the step of making the ketal compound (x1) containing hydroxyl;
[0022] Step 2: a step of (meth)acrylating the hydroxyl group contained in the obtained hydroxyl group-containing ketal compound (x1) to obtain a (meth)acrylate compound (x2);
[0023] Step 3: A step of hydrolyzing the obtained (meth)acrylate compound (x2).
[0024] According to the method of the present invention, the polyol compound (x3) containing a (m...
Embodiment 1
[0094] Embodiment 1: Production example 1 of pentaerythritol diacrylate
[0095] (1) Ketalization step (1)
[0096] Into the flask equipped with thermometer, stirrer, condenser and Dean-Stark (Dean Stark) apparatus, add 136g (1.0mol) pentaerythritol, 600ml N,N-dimethylformamide and 60ml cyclohexane, and 3.7 g of p-toluenesulfonic acid were added as catalyst. The temperature was raised to 110° C. while stirring, and pentaerythritol was dissolved in N,N-dimethylformamide. Afterwards, 78 g (0.8 mol) of cyclohexanone were added. The reaction was continued while the reaction temperature was kept at 120° C., while removing generated water by distillation. When no water production was observed, it was refluxed for another 1 hour. Cool to room temperature while continuing to stir, and remove unreacted pentaerythritol by filtration under reduced pressure. N,N-dimethylformamide in the filtrate was removed under reduced pressure, ethyl acetate was added, and precipitated pentaerythr...
Embodiment 2
[0105] Embodiment 2: Production example 2 of pentaerythritol diacrylate
[0106] (1) Ketalization step (2)
[0107] 55 g of brown solids were obtained in the same manner as in Example 1, except that cyclohexanone was changed to 67 g (0.8 mol) of cyclopentanone. by GC-MS and 13 As a result of C-NMR analysis of the obtained solid, it was confirmed that the solid was a ketal compound of pentaerythritol represented by the following structural formula (III) (hereinafter referred to as "hydroxyl-containing ketal compound (x1-2)"). The yield of this reaction was 34% based on the number of moles of cyclopentanone charged.
[0108]
[0109]
[0110] (2) Acrylation step (2)
[0111] 29 g of yellow solids were obtained in the same manner as in Example 1 except that the hydroxyl group-containing ketal compound (x1-1) was changed to 20.2 g (0.1 mol) of the hydroxyl group-containing ketal compound (x1-2). by GC-MS and 13 As a result of C-NMR analysis of the obtained solid, it was ...
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