Production method for polymerizable liquid crystal composition

Patent metadata

Field	Value
Publication number	US-2016237351-A1
Application number	US-201415030011-A
Country	US
Kind code	A1
Filing date	Oct 7, 2014
Priority date	Oct 17, 2013
Publication date	Aug 18, 2016
Grant date	—

Abstract

The present invention provides a method for producing a polymerizable liquid crystal composition which produces films being uncolored and having no cissinq 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

1 . 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 hea ting and stirring the resultant mixture; and a step (II) of mixing the polymerizable solution with a polymerization initiator.

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

3 . The method for producing a polymerizable liquid crystal composition 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 according to claim 1 , wherein in the step of preparing the polymerizable solution by heating and stilling, the heating temperature during heating and stirring is 15° C. to 100° C.

5 . The method for producing a polymerizable liquid crystal composition according to claim 1 , wherein the temperature of the solution in mixing with the polymerization initiator is 0° C. to 80° C.

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

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

8 . The method for producing a polymerizable liquid crystal composition according to claim 1 , wherein the polymerizable compound is a compound represented by general formula (1).
P-(Sp) m -MG-R 1   (1)
(in the formula, P represents a polymerizable functional group, Sp represents an alkylene group having 0 to 18 carbon atoms (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)

(in the formula, 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).

9 . The method for producing a polymerizable liquid crystal composition according to claim 8 , wherein in the general formula (1), MG is represented by general formula (1-b),
-Z0-(A1-Z1) n -A2-Z2-A3-Z3-  (1-b)
(in the formula, A1, A2, and A3 each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a 1,4-cydohexenyl 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 decahydronaphthaiene-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′]dithophene-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]selenopb.ene-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, m alkanoyl group, an alkanoyloxy group, an alkenyl group having 2 to 8 carbon atoms, an alkenvloxv group, an aikenoyl group, an alkenoyloxy group, and or general formula (1-a)
-(Sp) m -P  (1-a)

(in the formula, 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 presents, they may be the same or different), 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).

10 . The method for producing a polymerizable liquid crystal composition according to claim 8 , wherein a compound represented by the general formula (1) in which R 1 is general formula (1-a) is contained.

11 . The method for producing a polymerizable liquid crystal composition according to claim 8 , wherein a compound represented by the general formula (1) and having a melting point of 100° C. or more is contained.

12 . A polymerizable liquid crystal composition produced by the method according to claim 1 .

13 . An optically anisotropic body using the polymerizable liquid crystal composition according to claim 12 .

Assignees

• Dainippon Ink & Chemicals

Inventors

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

Classifications

• C08F222/1025

  of aromatic dialcohols · CPC title

• C08F222/1035

  of aromatic trialcohols · CPC title

• C08F220/303

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

• C09K19/2014

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n- · CPC title

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title