Simplified process for sustainable toner resin

Patent metadata

Field	Value
Publication number	US-9329510-B2
Application number	US-201313973662-A
Country	US
Kind code	B2
Filing date	Aug 22, 2013
Priority date	Aug 22, 2013
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

The disclosure describes a one reaction process for making a bio-based polyester resin. The resultant polyester resin retains thermal properties as compared to a similar resin but made using previous multi-step processes conducted in separate vessels.

First claim

We claim:

1. A process for the preparation of a bio-based polyester polymer consisting of (i) preparing a rosin derivative comprising plural alcohol groups in a single reactor and wherein said rosin derivative is generated by the reaction, in the presence of a catalyst, of a rosin acid with bis-(epoxy-propyl)-neopentylene glycol; (ii) reacting said rosin derivative containing hydroxyl groups with (a) dimethyl terephthalate or terephthalic acid, (b) succinic acid and (c) 1,2-propanediol in said single reactor to form said polyester polymer; and (iii) optionally recovering said polyester polymer.

2. The process of claim 1 , wherein said rosin acid is selected from the group consisting of a disproportionated rosin and a hydrogenated rosin to obtain said rosin derivative.

3. The process of claim 1 , wherein said polyester polymer is recovered.

4. The process of claim 1 , wherein said rosin derivative is reacted with said dimethyl terephthalate.

5. The process of claim 1 , wherein said said catalyst is selected from the group consisting of tetraethyl ammonium bromide and tetraethyl ammonium iodide.

6. The process of claim 5 , wherein said catalyst is tetraethyl ammonium bromide.

7. The process of claim 1 , wherein (i) is accomplished under elevated temperatures.

8. The process of claim 1 , wherein said rosin acid is a dehydroabietic acid.

9. The process of claim 5 , wherein said catalyst is tetraethyl ammonium iodide.

10. A process for the preparation of a bio-based polyester polymer consisting of (i) preparing a rosin derivative containing plural alcohol groups in a single reactor and wherein said rosin derivative is generated, in the presence of a catalyst, by the reaction of a rosin acid with bis-(epoxy-propyl)-neopentylene glycol; (ii) reacting said rosin derivative containing hydroxyl groups with (a) dimethyl terephthalate or terephthalic acid, (b) succinic acid and (c) 1,2-propanediol in said single reactor to form said polyester polymer; and (iii) recovering said polyester polymer and wherein said catalyst is selected from the group consisting of-tetraethyl ammonium bromide and tetraethyl ammonium iodide.

11. A process in accordance with claim 10 , wherein said catalyst is tetraethyl ammonium bromide and said rosin derivative is reacted with said dimethyl terephthalate.

12. A process in accordance with claim 10 , wherein said catalyst is tetraethyl ammonium bromide and said rosin derivative is reacted with said terephthalic acid.

13. A process in accordance with claim 10 wherein said rosin acid is selected from the group consisting of a disproportionated rosin and a hydrogenated rosin.

14. A process in accordance with claim 10 wherein the reaction is conducted at elevated temperatures of from about 100 degrees Centigrade to about 220 degrees Centigrade.

15. A toner process which comprises the mixing of a colorant and a polyester resin and wherein said resin is generated by (i) preparing a rosin derivative comprising plural alcohol groups and wherein said rosin derivative is generated by the reaction of a rosin with bis-(epoxy-propyl)-neopentylene glycol; (ii) reacting said rosin derivative containing hydroxyl groups with (a) dimethyl terephthalate or terephthalic acid, (b) succinic acid and (c) 1,2-propanediol in said single reactor; and (iii) recovering said polyester polymer.

16. The process of claim 15 , wherein subsequent to said mixing said toner is subjected to emulsion/aggregation methods, and wherein said rosin derivative is generated in the presence of a catalyst.

17. The process of claim 16 , wherein said catalyst is selected from the group consisting of tetraethyl ammonium bromide and tetraethyl ammonium iodide and said colorant is a pigment.

18. A process of claim 1 , where in (ii) said rosin derivative is heated in the same reactor with said terephthalic acid, and 1,2-propanediol at a pressure of about 200 kPa; then (iii) reducing the pressure until a resin softening point for said polyester is about 122 degrees Centigrade; (iv) adding thereto said succinic acid until an acid value of from about 10 to about meg of KOH/gram results.

19. A developer comprising the toner of claim 16 .

20. The developer of claim 19 , further including carrier particles.

Assignees

• Xerox Corp

Inventors

• Sacripante Guerino G
• Zhou Ke
• Zwartz Edward G
• Hawkins Michael S
• Laberge Veronique
• Toth Alan Ej
• Mahmood Rashid
• Elliott Mark R
• Abate John

Classifications

• G03G9/0806

  whereby chemical synthesis of at least one of the toner components takes place · CPC title

• G03G9/08755 Primary

  Polyesters · CPC title