Water-soluble or dispersible polyester resins made from terephthalate plastic materials useful as dispersant resins for inks

Patent metadata

Field	Value
Publication number	US-11236213-B2
Application number	US-202017265078-A
Country	US
Kind code	B2
Filing date	Jan 6, 2020
Priority date	Jan 7, 2019
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

The present invention provides water-soluble or water-dispersible polyester resins prepared by depolymerizing a terephthalate plastic material in an alcoholysis/glycolysis reaction, and re-polymerizing the product by reacting with a polybasic acid and/or anhydride. The polyester resins of the invention contain 70% to 95% by weight of the terephthalate material, based on the total weight of the composition. The polyester resins of the present invention are useful as dispersants, for example in pigment preparations, and as binders in let-down varnishes, inks, coatings, etc, and as adhesion promoters in aqueous-based inks.

First claim

What is claimed:

1. A method of preparing a water-soluble or water-dispersible polyester resin composition comprising subjecting a terephthalate polymer to a glycolysis/alcoholysis reaction, and re-polymerization reaction;
wherein said glycolysis/alcoholysis reaction comprises reacting:
(A) 73% to 95% by weight of at least one terephthalate polymer, based on the total weight of the composition; and
(B) 0.5% to 30% by weight of at least one mono-, bi-, or higher-valent alcohol or oxyalkylated alcohol, based on the total weight of the composition;

in order to get a reaction mixture; wherein the OH equivalents from the alcohol are less than the OH equivalents from the terephthalate polymer; and
wherein said re-polymerization comprises adding to the reaction mixture:
(C) 0.5% to 30% by weight of at least one polybasic carboxylic acid and/or anhydride, based on total weight of the composition;

wherein the addition of the polybasic acid and/or anhydride is done either:
i) sequentially, wherein all of the polybasic acid or anhydride is added to the reaction mixture after the glycolysis reaction has run for about 30 to 200 minutes, and/or the mixture exhibits a 15-minute clear peel, and/or the glycolysis reaction is run until there is essentially no reflux; or
ii) essentially sequentially, wherein a portion of the polybasic acid and/or anhydride is added to the reaction mixture in the beginning at the same time as the terephthalate polymer and alcohol, with the remainder of the polybasic acid and/or anhydride being added:
a) after the glycolysis reaction has run for about 30 to 200 minutes; and/or
b) after the reaction mixture exhibits a 15-minute clear peel; and/or
c) after the glycolysis reaction is run until there is essentially no reflux;

wherein the ratio of the polybasic acid and/or anhydride added at the beginning of the reaction to the polybasic acid added after the glycolysis reaction has run for about 30 to 200 minutes, and/or the mixture exhibits a 15-minute clear peel, and/or the glycolysis reaction is run until there is essentially no reflux is 1:99 to 99:1;
wherein the polyester resin has an acid value greater than 50 mg KOH/g; and
wherein the polyester resin has a glass transition temperature (Tg) equal to or greater than 40° C.

2. The method of claim 1 , wherein the terephthalate polymer comprises a waste material.

3. The method of claim 1 , wherein (C) further comprises 0.5% to 30% by weight of at least one fatty acid, based on the total weight of the composition.

4. The method of claim 3 , wherein the fatty acid is a dimer acid.

5. The method of claim 1 , wherein (C) comprises isophthalic acid.

6. The method of claim 3 , comprising isophthalic acid or a dimer acid, or a combination thereof.

7. The method of claim 1 , wherein the reaction mixture comprises 73% to 93% by weight of polyethylene terephthalate, 0.1% to 10% by weight of diethylene glycol, 0.1% to 15% by weight of glycerol, 1% to 20% by weight of a fatty acid, 1% to 30% by weight of isophthalic acid, all based on the total weight of the composition.

8. The method of claim 7 , wherein the reaction mixture further comprises 3% to 15% by weight of trimellitic acid or trimellitic anhydride, based on the total weight of the composition.

9. The method of claim 1 , wherein the reaction mixture further comprises a catalyst in an amount of 0.001% to 3% by weight, based on the total weight of the composition.

10. The method of claim 1 , wherein the polyester resin has a number average molecular weight of 1,000 to 7,000 Da, and a weight average molecular weight of 4,000 to 30,000 Da.

11. The method of claim 1 , comprising heating waste terephthalate polymer and glycol(s) above 150° C. to produce an intermediate product characterized by a 15 minute clear peel, and heating the thus obtained intermediate product with a polybasic acid at a temperature of at least 150° C.

12. A water-soluble or water-dispersible polyester resin prepared by the method of claim 1 .

13. A composition comprising the resin of claim 12 , dissolved or dispersed in water, wherein the water optionally contains an alkali metal, or ammonium hydroxide, or ammonium carbonate.

14. The composition of claim 13 , diluted with water to a resin solids content of 0.5% to 30%.

15. A solid pigment preparation comprising:
a) 5% to 99% by weight of at least one pigment, based on the total weight of the pigment preparation;
b) 0.1% to 90% by weight of the resin of claim 12 , based on the total weight of the pigment preparation;
c) 0% to 2% by weight of one or more auxiliary materials selected from the group consisting of fillers, flame retardants, preservatives, photoprotectants, pigmentary dispersants, nonpigmentary dispersants, surfactants, antioxidants, defoamers, resins, and antistatic agents, each based on the total weight of the pigment preparation.

16. The pigment preparation of claim 15 , wherein the pigment is selected from the group consisting of monoazo, diazo, lacked azo, β-naphthol, Naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments, phthalocyanine, quinacridone, perylene, perinone, thioindigo, anthanthrone, anthraquinone, flavanthrone, indanthrone, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, isoindoline and diketopyrrolopyrrole pigments or the acidic to alkaline carbon blacks selected from the group consisting of furnace blacks and gas blacks, and blends thereof.

17. The pigment preparation of claim 15 , wherein the preparation is in the form of powder, granulate, or presscake.

18. A composition comprising the pigment preparation of claim 17 , and water, or an organic solvent, or a mixture of water and organic solvent.

19. A pigmented material comprising the pigment preparation of claim 15 .

20. A printed article or food packaging article comprising the pigmented material of 19.

21. The method of claim 1 , wherein the acid value of the polyester resin is greater than 55 mg KOH/g.

22. The method of claim 1 , wherein the reaction mixture comprises 80% to 95% by weight of at least one terephthalate polymer, based on the total weight of the composition.

Assignees

• Sun Chemical Corp

Inventors

• Dieker Jürgen
• Deighton Robert
• Gaudl Kai-Uwe W
• Nurcaj-Dreshaj Leonora

Classifications

• C08J2367/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence) · CPC title

• Y02W30/62

  Plastics recycling; Rubber recycling · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08J11/24 Primary

  containing hydroxyl groups · CPC title

• C08G63/85

  Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)} · CPC title