# US 10,441,936 B2 · Liquid crystal capsule and method for producing the same

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- Number: US 10,441,936 B2
- Document ID: US10441936B2
- Status: Granted
- Kind: B2
- Application number: 15/506,251
- Filed: 2015-07-10
- Published: 2017-08-31
- Granted: 2019-10-15
- Earliest claimed: 2014-09-02
- Assignees: Jnc Corporation; Jnc Petrochemical Corporation; National University Corporation Chiba University
- Applicants: Jnc Corporation; Jnc Petrochemical Corporation; National University Corporation Chiba University
- Inventors: Tatsuo Taniguchi; Sho Hidaka; Eiji Okabe; Fumitaka Kondo
- Web page: https://patentgrep.com/patent/US10441936B2

## CPC

- B01J 13/18: In situ polymerisation with all reactants being present in the same phase
- B01J 13/08: Simple coacervation, i.e. addition of highly hydrophilic material {(combined with spraying B01J13/043; combined with mechanical division B01J13/04)}
- B01J 13/14: Polymerisation; cross-linking
- C09B 67/0097: {Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes}
- C09K 19/3001: {Cyclohexane rings}
- C09K 19/3028: {in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds}
- C09K 19/3059: {in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds}
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/544: {as dispersing or encapsulating medium around the liquid crystal}
- G02F 1/133528: {Polarisers}
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/181: {Ph-C≡C-Ph}
- C09K 2019/2035: {Ph-COO-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3019: {Cy-Cy-Ph-Ph}
- C09K 2019/3063: {Cy-Ph-C≡C-Ph}
- C09K 2219/00: Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS

## Abstract

Shown is a method for producing a liquid crystal capsule having a particle diameter of 30 to 150 nanometers, and a method for producing a liquid crystal capsule without using a homogenizer. The disclosure concerns a method for producing a liquid crystal capsule, including a step of preparing an emulsion by performing phase inversion emulsification of a mixed material obtained by mixing a liquid crystal composition, a monomer, a surfactant, and a polymerization initiator; and a step of producing a liquid crystal capsule by applying a coacervation method to the emulsion. The disclosure also concerns a liquid crystal capsule having a liquid crystal composition, a surfactant and a capsule wall, wherein the capsule wall has a closed curved shape, the liquid crystal composition and a hydrophobic moiety of the surfactant are arranged inside the capsule wall, and a hydrophilic moiety of the surfactant is arranged outside the capsule wall.

## Claims

### Claim 1

A method of forming a liquid crystal capsule comprising a liquid crystal composition inside a capsule wall, said method comprising the steps of:
mixing the liquid crystal composition, a monomer having a polymerization group, a surfactant that is a block copolymer having a hydrophilic moiety and a hydrophobic group, and a polymerization initiator, wherein a water-in-oil emulsion is formed by the hydrophobic group of the block copolymer orienting outward and the hydrophilic moiety orienting inward, to form a mixed material;
adding water to the mixed material to form an oil-in-water emulsion;
adding water to the oil-in-water emulsion; and
polymerizing the monomer to form a polymer which is the capsule wall wrapping the liquid crystal composition.

### Claim 2 (depends on 1)

The method according to claim 1, wherein in the step of polymerizing the monomer, interfacial tension γ in the liquid crystal composition, the polymer, and water satisfies the following three expressions (a) to (c):
γ23−(γ12+γ13)<0 (a);
γ13−(γ12+γ23)>0 (b); and
γ12−(γ13+γ23)<0 (c),
where, in expressions (a) to (c), a subscript 1 represents the liquid crystal composition, a subscript 2 represents the polymer, a subscript 3 represents water, and γ12, γ13 and γ23 are represented by the following equations:
γ12=γ1+γ2−2(γ1dγ2d)1/2−2(γ1hγ2h)1/2;
γ13=γ1+γ3−2(γ1dγ3d)1/2−2(γ1hγ3h)1/2; and
γ23=γ2+γ3−2(γ2dγ3d)1/2−2(γ2hγ3h)1/2,
where, each γi (i is 1, 2 or 3) satisfies an equation: γi=γid+γih, wherein γid represents a non-polar dispersion force component of γi, and γih represents a polar hydrogen bonding component of γi.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the liquid crystal composition comprises liquid crystal component 1 composed of a compound represented by formula (1), and liquid crystal component 2 composed of a compound represented by formula (2), in which a proportion of a compound having cyano is less than 3% by weight based on the total of the liquid crystal composition:
wherein, in formula (1) and formula (2), R1, R2 and R3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons or alkenyl having 2 to 12 carbons; rings A1, A2, A3, A4 and A5 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, 2,6-difluoro-1,4-phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl or tetrahydropyran-2,5-diyl; Z1, Z2, Z3, Z4 and Z5 are independently a single bond, ethylene, vinylene, methyleneoxy, carbonyloxy, difluoromethyleneoxy, tolan or tetrafluoroethylene, in which at least one of Z1 and Z2 is tolan; X1, X2, X3, X4, X5 and X6 are independently hydrogen or fluorine, in which a case where X1 and X2 are simultaneously fluorine is excluded, and a case where X4 and X5 are simultaneously fluorine is excluded; Y1 is fluorine, chlorine, alkyl having 1 to 12 carbons in which at least one piece of hydrogen may be replaced by halogen, alkoxy having 1 to 12 carbons in which at least one piece of hydrogen may be replaced by halogen, or alkenyl having 2 to 12 carbons in which at least one piece of hydrogen may be replaced by halogen; 1 and m are 0, 1 or 2, and when 1 and m are 2, a plurality of ring A2, ring A4, Z2 and Z4 existing therein may be identical to or different from each other.

### Claim 4 (depends on 1)

A liquid crystal capsule, produced by the method according to claim 1.

### Claim 5 (depends on 4)

The liquid crystal capsule according to claim 4, wherein a diameter of the liquid crystal capsule is 30 to 150 nanometers.

### Claim 6 (depends on 4)

A liquid crystal device, comprising a set of substrates arranged facing each other, an electrode formed on one or the set of the substrates, the liquid crystal capsule according to claim 4, and an electric field application means for applying an electric field to the liquid crystal capsule through the electrode.

### Claim 7 (depends on 6)

The liquid crystal device according to claim 6, wherein at least one of the substrates is transparent, and the liquid crystal device further comprises a polarizing plate arranged outside the at least one of the substrates.