Method of making amorphous resin for use in robust solid ink applications

Patent metadata

Field	Value
Publication number	US-9296680-B2
Application number	US-201113306549-A
Country	US
Kind code	B2
Filing date	Nov 29, 2011
Priority date	Nov 29, 2011
Publication date	Mar 29, 2016
Grant date	Mar 29, 2016

Abstract

Methods for making amorphous resins for use in robust solid ink applications are disclosed in which an organic acid is reacted with an alcohol in the presence of a solvent in the amount of from about 0.5 to about 1.5 grams of solvent per gram of reaction product. The reaction product is an ester of tartaric acid or an ester of citric acid.

First claim

What is claimed is:

1. A method of making an amorphous resin, comprising the steps of:
reacting a tartaric acid with at least one alcohol of the formula R—OH, for a period of time, and at a temperature, in the presence of an optional catalyst, and a solvent in an amount of from 0.65 to less than 1 grams of solvent per gram of an ester of tartaric acid of the formula:

wherein the at least one alcohol of the formula R—OH is selected from the group consisting of

and mixtures thereof
wherein R 1 and R 2 are each independently selected from the definitions for R in ROH;
wherein the tartaric acid is selected from the group consisting of L-(+)-tartaric acid, D-(−)-tartaric acid, DL-tartaric acid, mesotartaric acid, and mixtures thereof.

2. The method of claim 1 , wherein the alcohol is

3. The method of claim 1 , wherein the solvent is one or more solvents selected from the group consisting of pentane, hexane, cyclohexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, toluene, xylene, benzene, mesitylene, and mixtures thereof.

4. The method of claim 3 , wherein the solvent is mesitylene.

5. The method of claim 1 , wherein the amount of solvent used is from about 0.75 to about 0.85 grams of solvent per gram of product.

6. The method of claim 1 , wherein the reaction is carried out in the presence of a catalyst selected from the group consisting of sulfuric acid, phosphoric acid, hydrochloric acid, p-toluenesulfonic acid (PTSA), zinc chloride, magnesium chloride, zinc acetate, magnesium acetate, dibutyl tin laurate, and butylstannoic acid, and mixtures and combinations thereof.

7. The method of claim 6 , wherein the catalyst is PTSA.

8. The method of claim 1 , wherein the reacting step is performed at a temperature from about 40 to about 250° C.

9. The method of claim 8 , wherein the temperature is from about 155 to about 160° C.

10. The method of claim 1 , wherein the reacting step is carried out for a period of time from about 1 to about 10 hours.

11. The method of claim 10 , wherein the reacting step is carried out for a period of time from about 3 to about 6 hours.

12. The method of claim 8 , further comprising cooling the reaction to a temperature from about 65° C. to about 95° C.

13. The method of claim 1 , further comprising subjecting the ester of tartaric acid to aqueous extraction and phase separation.

14. The method of claim 1 , wherein the ester of tartaric acid is a compound of the formula:

15. The method of claim 1 , wherein the reacting step produces the ester of tartaric acid in a yield of from about 70% to about 80% in less than 10 hours.

16. The method of claim 1 , wherein the method affords a reaction throughput to be about 420 grams of product per liter of reactor space.

Assignees

• Gaynor Roger E
• Tahmoures-Zadeh Tila
• Xerox Corp

Inventors

• Gaynor Roger E
• Tahmoures-Zadeh Tila

Classifications

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C69/70

  Tartaric acid esters · CPC title

• C07C2101/14

  Chemistry & Metallurgy · mapped topic

• C07C2601/14

  The ring being saturated · CPC title