Mixture of polymerizable compound and method of producing the same

Patent metadata

Field	Value
Publication number	US-10934246-B2
Application number	US-202016744489-A
Country	US
Kind code	B2
Filing date	Jan 16, 2020
Priority date	Mar 31, 2015
Publication date	Mar 2, 2021
Grant date	Mar 2, 2021

Abstract

Disclosed is a mixture containing compound (I) and polymerizable compound (II) wherein compound (I) accounts for 50 mol % or more of the entire mixture and 1,4-cyclohexanedicarboxylic acid accounts for less than 5 mol % of the entire mixture; a method of producing the mixture which includes reacting in a water-immiscible organic solvent 1,4-cyclohexanedicarboxylic acid dichloride with compound (IV) in the presence of a base, and washing the obtained reaction solution with a weakly acidic buffer solution; etc. The disclosure provides mixtures useful for low-cost production of polymerizable compounds which have low melting points suitable for practical use, show superior solubility to general-purpose solvents, can be produced at low costs, and allow for provision of optical films capable of uniform polarized light conversion over a wide wavelength range, and methods of producing the mixtures.

where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20.

First claim

The invention claimed is:

1. A mixture comprising:
compound (I) having the following Formula (I):

where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20; and
polymerizable compound (II) having the following Formula (II):

where A and n are as defined above
wherein compound (I) accounts for 50 mol % or more of the entire mixture, and 1,4-cyclohexanedicarboxylic acid as an impurity accounts for less than 5 mol % of the entire mixture.

2. A method of producing a mixture of claim 1 , comprising:
reacting in a water-immiscible organic solvent 1,4-cyclohexanedicarboxylic acid dichloride with compound (IV) having the following formula (IV):

where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20 in the presence of a base to afford a reaction solution; and
washing the reaction solution with a buffer solution having a pH of 5.0 to 6.0.

3. A method of producing a mixture of claim 1 , comprising:
reacting in a water-immiscible organic solvent 1,4-cyclohexanedicarboxylic acid dichloride with compound (IV) having the following formula (IV):

where A represents hydrogen, methyl group or chlorine, and n represents an integer of 1 to 20 in the presence of a base to afford a reaction solution;
washing the reaction solution with water; and
washing the reaction solution after washing with water with a buffer solution having a pH of 5.0 to 6.0.

4. The method of claim 2 , wherein the buffer solution is a mixed buffer solution of acetic acid and sodium acetate, or a mixed buffer solution of potassium hydrogen phthalate and sodium hydroxide.

5. The method of claim 2 , wherein the water-immiscible organic solvent is an organic solvent having a Hildebrand solubility parameter of 14.0 to 22.0 (MPa 1/2 ).

6. The method of claim 2 , further comprising, after washing with the buffer solution, cooling an obtained organic layer to 5° C. or lower to precipitate polymerizable compound (II), and removing the precipitate.

Assignees

• Zeon Corp

Inventors

• Sakamoto Kei
• Okuyama Kumi
• SANUKI Kanako

Classifications

• C07C67/58 Primary

  by liquid-liquid treatment · CPC title

• G02B5/30

  Polarising elements (light-modulating devices with active elements G02F1/00) · CPC title

• C07C69/757

  having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety · CPC title

• C07C67/14 Primary

  from carboxylic acid halides · CPC title

• C07D277/82

  Nitrogen atoms · CPC title