# US 4,391,886 A · Methine colorant materials and the use thereof in electrophoretic migration imaging layers and processes

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- Number: US 4,391,886 A
- Document ID: US4391886A
- Status: Granted
- Kind: A
- Application number: 06/289,574
- Filed: 1981-08-03
- Granted: 1983-07-05
- Earliest claimed: 1980-06-23
- Assignees: Eastman Kodak Company
- Inventors: Mark D. Frishberg; James J. Krutak, Sr.
- Web page: https://patentgrep.com/patent/US4391886A

## CPC

- C07D 513/04: Ortho-condensed systems
- C07D 235/28: Sulfur atoms
- C07D 265/36: condensed with one six-membered ring
- C09B 23/04: one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
- G03G 17/04: using photoelectrophoresis
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

Disclosed are novel methine colorant materials having the structure ##STR1## Also disclosed is the use of such materials in electrophoretic migration imaging layers and processes.

## Claims

### Claim 1

An electrophoretic migration imaging recording method comprising the steps of:
(a) providing an electrically photosensitive imaging layer comprising an electrically photosensitive particulate material having the following general structure: ##STR32## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, cyano, phenyl, lower alkylsulfonamido or lower alkoxycarbonyl and A.sup.1 is a monovalent and A.sup.2 is a divalent residue of an aniline, 1,2,3,4-tetrahydroquinoline, benzomorpholine or indoline compound attached to the .dbd.CH-- group by an aromatic ring carbon atom in the position para to the aromatic amine nitrogen atom,
(b) applying an electrical field across said layer; and
(c) exposing said layer to an image pattern of electromagnetic radiation to which said electrically photosensitive material is photosensitive; and
(d) if necessary, at least partially liquifying said layer before, during or after exposure and application of the electric field to permit some migration of said electrically photosensitive material in said layer,
thereby forming a record of the image pattern of electromagnetic radiation in said layer.

### Claim 2 (depends on 1)

A method as in claim 1, further comprising the steps of:
(a) positioning said layer between two electrodes during the exposure and application of the electric field; and then
(b) separating the electrodes thereby forming a visual record of the image pattern of electromagnetic radiation on at least one of the electrodes.

### Claim 3 (depends on 1)

A method as in claim 1, further comprising the steps of:
(a) placing said layer between two support sheets to form an imaging element;
(b) positioning the element between two electrodes during the exposure and application of the electric field; and
(c) separating the two support sheets thereby forming a visual record of the image pattern of electromagnetic record on the support sheets.

### Claim 4 (depends on 2, 3)

A method as in claims 2 or 3, wherein said layer is liquified in the presence of an electric field some time subsequent to exposure.

### Claim 5 (depends on 1)

A method as in claim 1, further comprising the step of developing a visual record of the image pattern of electromagnetic radiation by removing the exposed or unexposed portion of said layer.

### Claim 6 (depends on 1, 2, 3)

A method as in claims 1, 2 or 3 wherein said electrically photosensitive particulate material has the structure ##STR33## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, cyano, phenyl, lower alkylsulfonamido or lower alkoxycarbonyl and A.sup.1 has the formula ##STR34## in which R.sup.2 is hydrogen, lower alkyl, lower alkoxy or halogen; n is 0, 1 or 2; R.sup.3 and R.sup.4 are unsubstituted or substituted alkyl containing up to about 12 carbon atoms; cyclohexyl; unsubstituted or substituted aryl; or when R.sup.4 is phenyl R.sup.3 can be hydrogen; R.sup.5, R.sup.6 and R.sup.7 are hydrogen or lower alkyl; R.sup.8 and R.sup.9 are lower alkyl or aryl; R.sup.17 is hydrogen or, when R.sup.5, R.sup.6 and R.sup.7 each is hydrogen, R.sup.17 is halogen derived from halogen or hydroxy.

### Claim 7 (depends on 6)

A method as in claim 6 wherein said material has the structure ##STR35## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.14 is hydrogen, methyl, methoxy or ethoxy;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR36## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene; and
R.sup.4 is lower alkyl; cyclohexyl; lower alkylcyclohexyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine or bromine; aryl; or a group having the formula --R.sup.11 --R.sup.17 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.17 is lower alkanoyloxy, lower alkoxycarbonyloxy, aroyloxy or lower alkoxy,
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 8 (depends on 6)

A method as in claim 6 wherein said material has the structure ##STR37## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR38## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.8, R.sup.9 and R.sup.10 each is hydrogen or methyl; and
R.sup.17 is hydrogen or, when R.sup.8, R.sup.9 and R.sup.10 each is hydrogen, R.sup.17 is one of the substituents which R.sup.15 can represent;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 9 (depends on 6)

A method as in claim 6 wherein said material has the structure ##STR39## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR40## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.9 is hydrogen or methyl;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 10 (depends on 6)

A method as in claim 6 wherein said material has the structure ##STR41## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR42## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.4 is lower alkyl; cyclohexyl; lower alkylcyclohexyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine or bromine; aryl; or a group having the formula --R.sup.11 --R.sup.17 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.17 is lower alkanoyloxy, lower alkoxycarbonyloxy, aroyloxy or lower alkoxy;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 11 (depends on 6)

A method as in claim 6 wherein said material is selected from the group consisting of ##STR43##

### Claim 12

An electrophoretic migration imaging layer comprising an electrically photosensitive particulate material having the structure ##STR44## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, cyano, phenyl, lower alkylsulfonamido or lower alkoxycarbonyl and A.sup.1 is a monovalent and A.sup.2 is a divalent residue of an aniline, 1,2,3,4-tetrahydroquinoline, benzomorpholine or indoline compound attached to the .dbd.CH-- group by an aromatic ring carbon atom in the position para to the aromatic amine nitrogen atom.

### Claim 13 (depends on 12)

A layer as in claim 12 wherein said material has the structure ##STR45## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, cyano, phenyl, lower alkylsulfonamido or lower alkoxycarbonyl and A.sup.1 has the formula ##STR46## in which R.sup.2 is hydrogen, lower alkyl, lower alkoxy or halogen; n is 0, 1 or 2; R.sup.3 and R.sup.4 are unsubstituted or substituted alkyl containing up to about 12 carbon atoms; cyclohexyl; unsubstituted or substituted aryl; or when R.sup.4 is phenyl R.sup.3 can be hydrogen; R.sup.5, R.sup.6 and R.sup.7 are hydrogen or lower alkyl; R.sup.8 and R.sup.9 are lower alkyl or aryl; R.sup.17 is hydrogen or, when R.sup.5, R.sup.6 and R.sup.7 each is hydrogen, R.sup.17 is halogen derived from halogen or hydroxy.

### Claim 14 (depends on 13)

A layer as in claim 13 wherein said material has the structure ##STR47## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy, or chlorine;
R.sup.14 is hydrogen, methyl, methoxy or ethoxy;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR48## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene; and
R.sup.4 is lower alkyl; cyclohexyl; lower alkylcyclohexyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine or bromine; aryl; or a group having the formula --R.sup.11 --R.sup.17 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.17 is lower alkanoyloxy, lower alkoxycarbonyloxy, aroyloxy or lower alkoxy,
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 15 (depends on 13)

A layer as in claim 13 wherein said material has the structure ##STR49## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR50## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.8, R.sup.9 and R.sup.10 each is hydrogen or methyl; and
R.sup.17 hydrogen or, when R.sup.8, R.sup.9 and R.sup.10 each is hydrogen, R.sup.17 is one of the substituents which R.sup.15 can represent;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 16 (depends on 13)

A layer as in claim 13 wherein said material has the structure ##STR51## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR52## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.9 is hydrogen or methyl;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 17 (depends on 13)

A layer as in claim 13 wherein said material has the structure ##STR53## wherein R.sup.13 is hydrogen, methyl, methoxy, ethoxy or chlorine;
R.sup.3 is lower alkyl, phenethyl; cyclohexylmethyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine, bromine or lower alkoxycarbonyl; aryl; or a group having the formula --R.sup.11 --R.sup.15 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.15 is lower alkanoyloxy, cyano, lower alkoxycarbonyloxy, arylcarbamoyloxy, lower alkylcarbamoyloxy, aroyloxy, lower alkoxycarbonylbenzoyloxy, lower alkoxy, chlorine, aryloxy, 2-benzothiazolylthio, or a group having the formula ##STR54## in which Y is --CO--, --SO.sub.2 --, or --CH.sub.2 -- and R.sup.16 is ethylene, propylene, trimethylene or o-arylene;
R.sup.4 is lower alkyl; cyclohexyl; lower alkylcyclohexyl; benzyl; benzyl substituted with lower alkyl, lower alkoxy, chlorine or bromine; aryl; or a group having the formula --R.sup.11 --R.sup.17 in which R.sup.11 is ethylene, propylene, trimethylene or tetramethylene and R.sup.17 is lower alkanoyloxy, lower alkoxycarbonyloxy, aroyloxy or lower alkoxy;
in which each aryl moiety is phenyl, tolyl, lower alkoxyphenyl, or chlorophenyl.

### Claim 18 (depends on 13)

A layer as in claim 13 wherein said material is selected from the group consisting of ##STR55##

### Claim 19

An electrophoretic migration image comprising an electrically photosensitive particulate material having the structure ##STR56## wherein R.sup.1 is hydrogen, lower alkyl, lower alkoxy, nitro, halogen, cyano, phenyl, lower alkylsulfonamido or lower alkoxycarbonyl and A.sup.1 is a monovalent and A.sup.2 is a divalent residue of an aniline, 1,2,3,4-tetrahydroquinoline, benzomorpholine or indoline compound attached to the .dbd.CH-- group by an aromatic ring carbon atom in the position para to the aromatic amine nitrogen atom.