Production method for polymerizable liquid crystal composition

Patent metadata

Field	Value
Publication number	US-10196568-B2
Application number	US-201415030011-A
Country	US
Kind code	B2
Filing date	Oct 7, 2014
Priority date	Oct 17, 2013
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

The present invention provides a method for producing a polymerizable liquid crystal composition which produces films being uncolored and having no cissing and good alignment when applied to a substrate, and also provides a polymerizable liquid crystal composition produced by the method and an optically anisotropic body using the polymerizable liquid crystal composition. Specifically, the present invention provides a method for producing a polymerizable liquid crystal composition, the method comprising a step (I) of preparing a polymerizable solution by mixing at least one polymerizable compound having at least one polymerizable functional group and one or two or more organic solvents and heating and stirring the resultant mixture; and a step (II) of mixing the polymerizable solution with a polymerization initiator, and also provides a polymerizable liquid crystal composition produced by the method and an optically anisotropic body using the polymerizable liquid crystal composition.

First claim

The invention claimed is:

1. A method for producing a polymerizable liquid crystal composition solution, the method comprising:
a step (I) of preparing a uniform polymerizable solution comprising:
mixing at least one polymerizable compound having at least one polymerizable functional group and showing liquid crystallinity, and one or two or more organic solvents to provide a mixture; and
heating and stirring the mixture at a temperature to provide the uniform polymerization solution; and

a step (II) of mixing the uniform polymerizable solution with a polymerization initiator at a temperature of 15° C. to 50° C., the temperature of the Step (II) being lower than the temperature of the Step (I).

2. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , further comprising performing filtration after the step (II).

3. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein the concentration of the polymerizable compound in the polymerizable solution is 5% by mass to 50% by mass.

4. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein the temperature of the Step (II) is 20° C. or more, lower than the temperature of the Step (I).

5. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein in the step of preparing the polymerizable solution by heating and stirring, the stirring rotational speed is 10 rpm to 1000 rpm.

6. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein in the step of preparing the polymerizable solution, a polymerization initiator and/or an antioxidant is mixed.

7. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein the at least one polymerizable compound is a compound represented by general formula (1),
P-(Sp) m -MG-R 1   (1)

wherein in the formula (1), P represents a polymerizable functional group,
Sp represents an alkylene group having 0 to 18 carbon atoms in which a hydrogen atom in the alkylene group may be substituted by one or more halogen atoms or CN, and one CH 2 group or two or more unadjacent CH 2 groups present in the alkylene group may be each independently substituted by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C— in a form in which oxygen atoms are not directly bonded to each other,
m represents 0 or 1,
MG represents a mesogenic group,
R 1 represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, the alkyl group may be substituted by one or more halogen atoms or CN, and one CH 2 group or two or more unadjacent CH 2 groups present in the alkyl group may be each independently substituted by —O—, —S—, —NH—, —N(CH 3 )—, —CO—, —COO—, —OCO—, —OCOO—, —SCO—, —COS—, or —C≡C— in a form in which oxygen atoms are not directly bonded to each other, or R 1 represents a structure represented by general formula (1-a),
-(Sp) m -P  (1-a)

wherein in the formula (1-a), P represents a reactive functional group, Sp represents a spacer group having 0 to 18 carbon atoms, and m represents 0 or 1, and when a plurality of each of P and Sp are present, they may be the same or different.

8. The method for producing a polymerizable liquid crystal composition solution according to claim 7 , wherein in the general formula (1), MG is represented by general formula (1-b),
-Z0-(A1-Z1) n -A2-Z2-A3-Z3-  (1-b)

wherein in the formula (1-b), A1, A2, and A3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cyclohexenyl group, a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, a tetrahydrothiopyran-2,5-diyl group, a 1,4-bicyclo(2,2,2)octylene group, a decahydronaphthalene-2,6-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a pyrazine-2,5-diyl group, a thiophene-2,5-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a 2,6-naphthylene group, a phenanthrene-2,7-diyl group, a 9,10-dihydrophenanthrene-2,7-diyl group, a 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, a 1,4-naphthylene group, a benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl group, a benzo[1,2-b:4,5-b′]diselenophene-2,6-diyl group, a [1]benzothieno[3,2-b]thiophene-2,7-diyl group, a [1]benzoselenopheno[3,2-b]selenophene-2,7-diyl group, or a fluorene-2,7-diyl group, which may have as a substituent one or more of F, Cl, CF 3 , OCF 3 , a CN group, an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenyloxy group, an alkenoyl group, an alkenoyloxy group, and/or the general formula (1-a),
Z0, Z1, Z2, and Z3 each independently represent —COO—, —OCO—, —CH 2 CH 2 —, —OCH 2 —, —CH 2 O—, —CH═CH—, —C≡C—, —CH═CHCOO—, —OCOCH═CH—, —CH 2 CH 2 COO—, —CH 2 CH 2 OCO—, —COOCH 2 CH 2 —, —OCOCH 2 CH 2 —, —CONH—, —NHCO—, an alkyl group having 2 to 10 carbon atoms which may have a halogen atom, or a single bond,
n represents 0, 1, or 2, and when a plurality of each of A1 and Z1 are present, they may be the same or different.

9. The method for producing a polymerizable liquid crystal composition solution according to claim 7 , wherein a compound represented by the general formula (1) in which R 1 is general formula (1-a) is contained.

10. The method for producing a polymerizable liquid crystal composition solution according to claim 7 , wherein a compound represented by the general formula (1) and having a melting point of 100° C. or more is contained.

11. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , further comprising filtering the polymerizable liquid crystal composition solution after the step (II), wherein when a degree of coloring of the polymerizable liquid crystal composition solution is measured by using an ultraviolet/visible spectrophotometer, the degree of coloring is less than 3.

12. The method for producing a polymerizable liquid crystal composition solution according to claim 1 , wherein when the polymerizable liquid crystal composition solution is stored at 40° C. for 1 month followed by observing a state of the polymerizable liquid crystal composition solution, no precipitate is found and the polymerizable liquid crystal composition solution remains uniform.

Assignees

• Dainippon Ink & Chemicals

Inventors

• ENDOU Koichi
• Kuwana Yasuhiro
• Nakata Hidetoshi
• Yamamoto Mika
• Kotani Kunihiko
• Hasebe Hiroshi
• Ono Yoshiyuki

Classifications

• C08F220/303

  and one or more carboxylic moieties in the chain · CPC title

• C08F222/1025

  of aromatic dialcohols · CPC title

• C08F222/1035

  of aromatic trialcohols · CPC title

• C09K2019/3083

  Cy-Ph-COO-Ph · CPC title

• C09K19/54 Primary

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title