Process for producing urethane (meth)acrylate

• US 8,148,567 B2
• Filed: 03/12/2009
• Issued: 04/03/2012
• Est. Priority Date: 03/14/2008
• Status: Expired due to Fees

• Current Assignee: DIC Corporation
• Original Assignee: DIC Corporation
• Inventors: Ishiyama, Fumihiko, Hizawa, Takeshi, Watanabe, Hideki
• Primary Examiner(s): Katakam, Sudhakar
• Application Number:
  US12/922,207
• Publication Number:
  US 20110087041A1
• Time in Patent Office: 1,118 Days
• Field of Search: None
• US Class Current: 560/26
• CPC Class Codes: C07C 269/02 from isocyanates with formation of carbamate groups
• CPC Class Codes: C07C 271/28 to a carbon atom of a non-condensed six-membered aromatic ring

Abstract

An object of the present invention is to provide a process for producing a urethane (meth)acrylate safely with good productivity, and for achieving the object, the invention provides a process for continuously producing a urethane (meth)acrylate, containing causing a mixed liquid of a compound (A) having a hydroxyl group and a (meth)acryloyl group and a compound (B) having an isocyanate group to pass continuously and densely through a tubular microchannel formed in a heat-conducting reaction device, and reacting the hydroxyl group of the compound (A) with the isocyanate group of the compound (B), in which the tubular microchannel in the reaction device has a space size making a fluid cross-sectional area, through which the mixed liquid passes densely, of from 0.1 to 4.0 mm², and the process contains heating the heat-conducting reaction device to a temperature of from 100 to 250° C., reacting the mixed liquid to provide a Reynolds number of a reaction liquid passing through the tubular microchannel in a range of from 0.2 to 300, and after completing reaction, cooling continuously a reaction product discharged from the heat-conducting reaction device.

Claims

1. A process for continuously producing a urethane (meth)acrylate, comprising causing a mixed liquid of a compound (A) having a hydroxyl group and a (meth)acryloyl group and a compound (B) having an isocyanate group to pass continuously and densely through a tubular microchannel formed in a heat-conducting reaction device, and reacting the hydroxyl group of the compound (A) with the isocyanate group of the compound (B),

the tubular microchannel in the reaction device having a space size making a fluid cross-sectional area, through which the mixed liquid passes densely, of from 0.1 to 4.0 mm², and the process comprising heating the heat-conducting reaction device to a temperature of from 100 to 250°

C., reacting the mixed liquid to provide a Reynolds number of a reaction liquid passing through the tubular microchannel in a range of from 0.2 to 300, and after completing reaction, cooling continuously a reaction product discharged from the heat-conducting reaction device.

2. The production process according to claim 1, wherein the reaction product after completing reaction is cooled under a temperature condition of from 50 to 90°

C.

3. The process for producing a urethane (meth)acrylate according to claim 1, wherein the compound (A) having a hydroxyl group and a (meth)acryloyl group and the compound (B) having an isocyanate group are mixed in advance to form a mixed liquid, and the mixed liquid is fed continuously to the heat-conducting reaction device.

4. The process for producing a urethane (meth)acrylate according to claim 3, wherein reaction is performed by using a reaction apparatus containing a plurality of the heat-conducting reaction devices connected in series each having the tubular microchannel formed therein.

5. The process for producing a urethane (meth)acrylate according to claim 3, wherein the heat-conducting reaction device having the tubular microchannel formed therein has a structure containing a plurality of heat-conducting plate structures each having plural trenches on a surface thereof, which are laminated on each other.

6. The process for producing a urethane (meth)acrylate according to claim 1, wherein the mixed liquid is caused to pass through the tubular microchannel at a flow velocity of from 0.9×

10<sup>−

4</sup> to 4.2 m/sec.

7. The process for producing a urethane (meth)acrylate according to claim 1, wherein the compound (A) is a compound having a hydroxyl value of from 50 to 500, and the compound (B) is a compound having an isocyanate percentage of from 15 to 60.

8. The process for producing a urethane (meth)acrylate according to claim 1, wherein the continuous cooling is performed by causing the reaction product to pass continuously through a cooling heat exchange device having a tubular microchannel formed therein connected to an exit of a reaction liquid of the heat-conducting reaction device.

9. The process for producing a urethane (meth)acrylate according to claim 2, wherein the compound (A) having a hydroxyl group and a (meth)acryloyl group and the compound (B) having an isocyanate group are mixed in advance to form a mixed liquid, and the mixed liquid is fed continuously to the heat-conducting reaction device.

10. The process for producing a urethane (meth)acrylate according to claim 9, wherein reaction is performed by using a reaction apparatus containing a plurality of the heat-conducting reaction devices connected in series each having the tubular microchannel formed therein.

11. The process for producing a urethane (meth)acrylate according to claim 9, wherein the heat-conducting reaction device having the tubular microchannel formed therein has a structure containing a plurality of heat-conducting plate structures each having plural trenches on a surface thereof, which are laminated on each other.

12. The process for producing a urethane (meth)acrylate according to claim 2, wherein the continuous cooling is performed by causing the reaction product to pass continuously through a cooling heat exchange device having a tubular microchannel formed therein connected to an exit of a reaction liquid of the heat-conducting reaction device.