# US 5,707,543 A · Reversible display medium

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- Number: US 5,707,543 A
- Document ID: US5707543A
- Status: Granted
- Kind: A
- Application number: 08/411,201
- Filed: 1995-03-27
- Granted: 1998-01-13
- Earliest claimed: 1994-05-11
- Assignees: Fuji Xerox Co., Ltd.
- Inventors: Ryojiro Akashi; Takashi Morikawa; Masanobu Ninomiya; Takashi Uematsu
- Web page: https://patentgrep.com/patent/US5707543A

## CPC

- C09K 19/3852: {Poly(meth)acrylate derivatives}
- C09K 2323/025: Polyamide
- C09K 2323/03: Viewing layer characterised by chemical composition
- G02F 1/133365: {Cells in which the active layer comprises a liquid crystalline polymer}
- 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

A reversible display medium capable of repeatedly exhibiting a transparent state and a light-scattering state by an action of at least one of heat, electric field, and magnetic field, the medium comprising a substrate having thereon a recording layer comprising a side-chain high molecular weight liquid crystal, which is a copolymer comprising at least a liquid-crystal monomer component and a non-liquid-crystal monomer component having a substituent capable of making a hydrogen bond.

## Claims

### Claim 1

A reversible display medium capable of repeatedly exhibiting a transparent state and a light-scattering state by an action of at least one of heat, electric field, and magnetic field, said medium comprising a substrate having thereon a recording layer comprising a side-chain high molecular weight liquid crystal, which is a copolymer comprising at least a liquid-crystal monomer component and a non-liquid-crystal monomer component having a substituent capable of making a hydrogen bond, wherein said non-liquid-crystal monomer component is in a range of 0.1 to 50% by weight based on a total amount of said liquid-crystal monomer component and said non-liquid-crystal monomer component and the copolymer has a weight-average molecular weight between 1,000 and 1,000,000.

### Claim 2 (depends on 1)

A reversible display medium as claimed in claim 1, wherein said copolymer further comprises a non-liquid-crystal monomer component having no substituent capable of making a hydrogen bond.

### Claim 3 (depends on 1)

A reversible display medium as claimed in claim 1, wherein said substituent capable of making a hydrogen bond is selected from the group consisting of a carboxyl group, a sulfonic group, a phosphoric group, and a hydroxyl group.

### Claim 4 (depends on 1)

A reversible display medium as claimed in claim 1, wherein said side-chain high molecular weight liquid crystal constituting said recording layer has a multi-domain structure in which the diameter of domains at the maximum distributed number of domains is not more than 3 .mu.m.

### Claim 5 (depends on 1)

A reversible display medium as claimed in claim 1, wherein a protective layer is provided on said recording layer.

### Claim 6 (depends on 4)

A reversible display medium as claimed in claim 4, wherein said multi-domain structure is prepared by heating said recording layer to a temperature higher than the temperature at which said high molecular weight liquid crystal transfer from a liquid crystal state to an isotropic state, and cooling to room temperature at a cooling rate of -1.times.10.sup.2.degree. C./sec or less.

### Claim 7 (depends on 1)

A reversible display medium according to claim 1, wherein the liquid-crystal monomer is selected from the group consisting of acrylic ester molecules, methacrylic ester molecules and vinyl groups bonded by a non-hydrogen bond chemical bond to a rigid liquid-crystal functional group.

### Claim 8 (depends on 7)

A reversible display medium according to claim 7, wherein the rigid liquid-crystal functional group is selected from the group consisting of biphenyl, phenyl, benzoate, cyclohexylbenzene, azoxybenzene, azobenzene, azomethine, phenylpyrimidine, diphenylacetylene, biphenyl benzoate, cyclohexyl biphenyl and terphenyl.

### Claim 9 (depends on 7)

A reversible display medium according to claim 7, wherein said non-hydrogen bond chemical bond comprises a bond to an alkyl spacer.

### Claim 10 (depends on 1)

A reversible display medium according to claim 1, wherein the liquid-crystal monomer component is represented by at least one formula selected from the group consisting of Formula a and Formula b:
CH.sub.2 =C(R)--COO--(CH.sub.2).sub.m --O--A (a) CH.sub.2 =CH(CH.sub.2).sub.m --O--A (b)
wherein R represents a hydrogen atom or a methyl group; m represents an integer of 1 to 30; and A represents a liquid-crystal molecule (mesogen) residue represented by a formula selected from the group consisting of: ##STR10## wherein x and y may be the same or different and represent a single bond, --N=N--, --N(.fwdarw.O)=N--, --CH=N--, --N=CH--, --COO--, --O(C=O)-- and --CH=CH--; R' represents at least one moiety selected from the group consisting of halogen atom, alkyl group, alkoxy group, carboxyl group and cyano group, and n represents an integer of 1 to 5.

### Claim 11 (depends on 1)

A reversible display medium according to claim 1, wherein the substituent capable of making a hydrogen bond comprises at least one substituent selected from the group consisting of hydroxyl group, carboxyl group, sulfonic group, phosphoric group, primary amino group, secondary amino group, acid amide group and thiol group.

### Claim 12 (depends on 1)

A reversible display medium according to claim 1, wherein the non-liquid-crystal monomer component comprises at least one component selected from the group consisting of acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl acrylate, glyceryl methacrylate, acrylamide, methacrylamide, 2-acryloyloxyethyl succinate, 2-methacryloyloxyethyl succinate, 2-acryloyloxyethyl phthalate, 2-methacryloyloxyethyl phthalate, 2-acryloyloxyethyl-2-hydroxyethyl phthalate, 2-methacryloyloxyethyl-2-hydroxyethyl phthalate, 2-acryloyloxyethyl hexahydrophthalate, 2-methacryloyloxyethyl hexahydrophthalate, 4-(acryloyloxyalkyloxy)benzoic acid, 4-(methacryloyloxyalkyloxy)benzoic acid, mono-2-acryloyloxyethyl phosphate, mono-2-methacryloyloxyethyl phosphate, di-2-acryloyloxyethyl phosphate, di-2-methacryloyloxyethyl phosphate, hydroxy-substituted styrene, vinylsulfonic acid, 2-propene-1-ol and 5-hexene-1-ol.

### Claim 13 (depends on 1)

A reversible display medium according to claim 1, wherein the non-liquid-crystal monomer component comprises at least one compound selected from the group consisting of acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate and 2-hydroxy-3-phenoxypropyl methacrylate.

### Claim 14 (depends on 1)

A reversible display medium according to claim 1, wherein the copolymer has a weight-average molecular weight between 10,000 and 500,000.

### Claim 15 (depends on 1)

A reversible display medium according to claim 1, wherein said non-liquid-crystal monomer component is contained in said medium in a range of 1 to 40% by weight based on the total amount of said liquid-crystal monomer component and said non-liquid-crystal monomer component.

### Claim 16 (depends on 15)

A reversible display medium according to claim 15, wherein the range is 1 to 20% by weight.

### Claim 17 (depends on 2)

A reversible display medium as claimed in claim 2, wherein said non-liquid-crystal monomer having no substituent capable of making a hydrogen bond is selected from the group consisting of alkoacylate, alkomethacyrolate, styrene, vinyl acetate, vinyl chloride, vinylidene chloride, vinyl pyrrolidone, isoprene, 1-hexene and 1-octene.
