# US 8,465,579 B2 · Solid ink compositions comprising crystalline esters of tartaric acid

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

- Number: US 8,465,579 B2
- Document ID: US8465579B2
- Status: Granted
- Kind: B2
- Application number: 13/095,715
- Filed: 2011-04-27
- Published: 2012-11-01
- Granted: 2013-06-18
- Earliest claimed: 2011-04-27
- Assignees: Xerox Corporation
- Applicants: Kentaro Morimitsu; Jennifer L. Belelie; Naveen Chopra; Stephan V. Drappel; Corey Tracy; Peter G. Odell
- Inventors: Kentaro Morimitsu; Jennifer L. Belelie; Naveen Chopra; Stephan V. Drappel; Corey Tracy; Peter G. Odell
- Web page: https://patentgrep.com/patent/US8465579B2

## CPC

- C09D 11/34: Hot-melt inks
- C09D 11/38: characterised by non-macromolecular additives other than solvents, pigments or dyes
- 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 solid ink composition comprising an amorphous component, a crystalline component, and optionally, a colorant, which are suitable for ink jet printing, including printing on coated paper substrates. In embodiments, the crystalline component is synthesized from an esterification reaction of tartaric acid.

## Claims

### Claim 1

A phase change ink comprising:
at least an amorphous component, wherein the amorphous component is selected from the group consisting of di-L-menthyl L-tartrate, di-DL-menthyl L-tartrate, di-L-menthyl DL-tartrate, di-DL-menthyl DL-tartrate, and any stereoisomers and mixtures thereof; and
at least a crystalline component, wherein the crystalline component is an ester of tartaric acid having a formula of
wherein R1 and R2 each, independently of the other, is selected from the group consisting of alkyl group, wherein the alkyl portion can be straight, branched or cyclic, saturated or unsaturated, substituted or unsubstituted, having from 1 to 40 carbon atoms, or an substituted or unsubstituted aromatic or heteroaromatic group, and mixtures thereof, and further wherein the tartaric acid backbone is selected from L-(+)-tartaric acid, D-(−)-tartaric acid, DL-tartaric acid, or mesotartaric acid, and mixtures thereof.

### Claim 2 (depends on 1)

The phase change ink of claim 1, wherein the amorphous component is present in an amount of from 5 percent to 40 percent by weight of the total weight of the phase change ink.

### Claim 3 (depends on 2)

The phase change ink of claim 2, wherein the amorphous component is present in an amount of from 5 percent to 35 percent by weight of the total weight of the phase change ink.

### Claim 4 (depends on 1)

The phase change ink of claim 1, wherein the crystalline component is present in an amount of from 60 percent to 95 percent by weight of the total weight of the phase change ink.

### Claim 5 (depends on 4)

The phase change ink of claim 4, wherein the crystalline component is present in an amount of from 65 percent to 95 percent by weight of the total weight of the phase change ink.

### Claim 6 (depends on 1)

The phase change ink of claim 1, wherein the crystalline and amorphous components are blended in a range of weight ratios of from 1.5 to 20.

### Claim 7 (depends on 6)

The phase change ink of claim 6, wherein the crystalline and amorphous components are blended in a range of weight ratios of from 2 to 10.

### Claim 8 (depends on 1)

The phase change ink of claim 1, wherein the crystalline component is selected from the group consisting of dibenzyl L-tartrate, diphenethyl L-tartrate, bis(3-phenyl-1-propyl) L-tartrate, bis(2-phenoxyethyl) L-tartrate, diphenyl L-tartrate, bis(4-methylphenyl) L-tartrate, bis(4-methoxylphenyl) L-tartrate, bis(4-methylbenzyl) L-tartrate, bis(4-methoxylbenzyl) L-tartrate, dicyclohexyl L-tartrate, bis(4-tert-butylcyclohexyl) L-tartrate, and any stereoisomers and mixtures thereof.

### Claim 9 (depends on 1)

The phase change ink of claim 1 further comprising a colorant selected from the group consisting of a pigment, dye or mixtures thereof.

### Claim 10 (depends on 1)

The phase change ink of claim 1, wherein the crystalline component has a viscosity of from 1 to 10 cps at a temperature of 140° C.

### Claim 11 (depends on 1)

The phase change ink of claim 1, wherein the crystalline component is in crystallized form at room temperature.

### Claim 12 (depends on 1)

The phase change ink of claim 1 having a viscosity of less than 15 cps at a temperature of 140° C.

### Claim 13 (depends on 12)

The phase change ink of claim 12 having a viscosity of from 2 to 15 cps at a temperature of 140° C.

### Claim 14 (depends on 1)

The phase change ink of claim 1 having a viscosity of greater than 106 cps at room temperature.

### Claim 15

A phase change ink comprising:
an amorphous component, wherein the amorphous component is selected from the group consisting of di-L-menthyl L-tartrate, di-DL-menthyl L-tartrate, di-L-menthyl DL-tartrate, di-DL-menthyl DL-tartrate, and any stereoisomers and mixtures thereof;
a crystalline component; and
optionally a colorant, wherein the crystalline component is an ester of tartaric acid having a formula of
wherein R1 and R2 each, independently of the other, is selected from the group consisting of
and mixtures thereof, and wherein the tartaric acid backbone is selected from L-(+)-tartaric acid, D-(−)-tartaric acid, DL-tartaric acid, or mesotartaric acid, and mixtures thereof, and further wherein the crystalline and amorphous components are blended in a range of weight ratios of from 1.5 to 20.

### Claim 16 (depends on 15)

The phase change ink of claim 15, wherein the amorphous component is synthesized by an esterification reaction with at least one alcohol.

### Claim 17 (depends on 15)

The phase change ink of claim 15, wherein the crystalline and amorphous components are blended in a range of weight ratios of from 1.5 to 20.

### Claim 18

A phase change ink comprising:
an amorphous component, wherein the amorphous component is selected from the group consisting of di-L-menthyl L-tartrate, di-DL-menthyl L-tartrate, di-L-menthyl DL-tartrate, di-DL-menthyl DL-tartrate, and any stereoisomers and mixtures thereof; and
a crystalline component, wherein the crystalline component is an ester of tartaric acid synthesized by an esterification reaction with at least one alcohol.

### Claim 19 (depends on 18)

The phase change ink of claim 18, wherein the alcohol is R—OH being selected from the group consisting of
and mixtures thereof.