# US 2018/0022922 A1 · Method for preparing a colorant for use in a hot melt ink

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2018/0022922 A1
- Document ID: US20180022922A1
- Status: Published application
- Kind: A1
- Application number: 15/655,502
- Filed: 2017-07-20
- Published: 2018-01-25
- Earliest claimed: 2016-07-21
- Assignees: Océ Holding B.V.
- Applicants: Océ Holding B.V.
- Inventors: Peter M.A. WETJES; Gerardus C.P. VERCOULEN; Ronald M.J. HOFSTRA; Nick H.M. ROUBROEKS
- Web page: https://patentgrep.com/patent/US20180022922A1

## CPC

- C09B 5/14: Benz-azabenzanthrones (anthrapyridones)
- C09B 67/0096: {Purification; Precipitation; Filtration}
- C09B 69/04: of anionic dyes with nitrogen containing compounds
- C09D 11/328: characterised by dyes
- C09D 11/34: Hot-melt inks
- C09D 11/36: based on non-aqueous solvents
- 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)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A method for preparing a colorant for use in an ink composition including a substantially non-aqueous carrier composition includes providing a chromophore precursor including one or multiple functional groups which may be subjected to a chemical reaction to form a salt with a preselected counter ion; providing a salt including the preselected counter ion; and providing an organic solvent that is not miscible with water and wherein the reaction product of the chromophore precursor and the salt including the preselected counter ion is soluble; preparing a chromophore precursor solution in water by dissolving a quantity of the chromophore precursor in water adding a quantity of the organic solvent while stirring; adding the salt including the preselected counter ion while stirring to form a resalted chromophore; separating the resalted chromophore from the reaction mixture. The addition of the salt including the preselected counter ion is performed until a molar excess of counter ion has been added with respect to the molar amount of functional groups comprised in the chromophore precursor; A colorant is obtainable and an ink composition includes such a colorant.

## Claims

### Claim 1

A method for preparing a colorant for use in an ink composition comprising a substantially non-aqueous carrier composition, the method comprising the steps of:
a. providing a chromophore precursor comprising one or multiple functional groups which may be subjected to a chemical reaction to form a salt with a preselected counter ion; a salt comprising the preselected counter ion; and an organic solvent that is not miscible with water and wherein the reaction product of the chromophore precursor and the salt comprising the preselected counter ion is soluble;
b. preparing a chromophore precursor solution in water by dissolving a quantity of the chromophore precursor in water;
c. adding a quantity of the organic solvent while stirring;
d. adding the salt comprising the preselected counter ion while stirring to form a resalted chromophore;
e. optionally filtering the mixture obtained in step d;
f. separating the resalted chromophore from the mixture obtained in step d or optionally in step e;
wherein step d is performed until a molar excess of counter ion has been added with respect to the molar amount of functional groups comprised in the chromophore precursor;

### Claim 2 (depends on 1)

The method according to claim 1, wherein the molar excess of counter ion is expressed as the ratio of the molar amount of counter ion and the molar amount of functional groups comprised in the chromophore precursor which ratio ranges from 1.01:1 to 2.5:1.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the separating step f comprises the sub-steps:
f1. allowing the mixture obtained in step d or optionally in step e to separate into an aqueous phase and an organic phase by allowing the mixture to rest;
f2. removing the aqueous phase;
f3. optionally rinsing the organic phase multiple times, each time with more or less a similar amount of water;
f4. optionally filtering the organic phase; and
f5. concentrating the organic phase by evaporation of the organic solvent.

### Claim 4 (depends on 3)

The method according to claim 3, wherein step f3 comprises multiple rinsing steps which are performed with decreasing amounts (mass) of water in each subsequent step.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the initial rinsing step is performed with an amount (mass) of water that is larger than the amount (mass) of the organic phase, preferably in a mass ratio water:organic phase of between 1.1:1 and 2.5:1.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the chromophore precursor comprises a colorant from the anthrapyridone series.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the chromophore precursor comprises at least one sulphonic acid group and/or a derivate thereof as functional group(s).

### Claim 8 (depends on 1)

The method according to claim 1, wherein the salt comprises a counter ion selected from the group consisting of phosphonium groups and ammonium groups.

### Claim 9 (depends on 1)

The method according to claim 1, wherein the salt is a chloride salt.

### Claim 10 (depends on 1)

A colorant obtained by the method according to claim 1.

### Claim 11 (depends on 10)

The colorant according to claim 10, wherein the counter ion is tetra butyl phosphonium or tetra butyl ammonium.

### Claim 12 (depends on 10)

An ink composition comprising a colorant according to claim 10.

### Claim 13 (depends on 12)

The ink composition according to claim 12, wherein the ink composition is a hot melt ink composition, which is solid at room temperature and liquid at a higher temperature and comprising a substantially non aqueous carrier composition.

### Claim 14 (depends on 13)

The ink composition according to claim 13, wherein the non aqueous carrier composition comprises an amorphous binder and a crystalline component.

### Claim 15 (depends on 2)

The colorant obtained by the method according to claim 2.

### Claim 16 (depends on 3)

The colorant obtained by the method according to claim 3.

### Claim 17 (depends on 4)

The colorant obtained by the method according to claim 4.

### Claim 18 (depends on 5)

The colorant obtained by the method according to claim 5.

### Claim 19 (depends on 6)

The colorant obtained by the method according to claim 6.

### Claim 20 (depends on 7)

The colorant obtained by the method according to claim 7.
