Self-dispersing pigments

Patent metadata

Field	Value
Publication number	US-10316209-B2
Application number	US-201314441235-A
Country	US
Kind code	B2
Filing date	Oct 24, 2013
Priority date	Nov 13, 2012
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

The disclosure provides self-dispersing pigment having an isoelectric point of at least about 8 comprising an inorganic particle, and in particular a titanium dioxide (TiO 2 ) pigment, treated sequentially by: hydrolyzing an aluminum compound or basic aluminate to deposit a hydrous alumina surface; and adding a dual-functional compound comprising an anchoring group that attaches the dual-functional compound to the pigment surface, and a basic amine group comprising a primary, secondary or tertiary amine. These self-dispersing pigments are useful in making décor paper that may be used in paper laminates.

First claim

What is claimed is:

1. A self-dispersing pigment having an isoelectric point of at least about 8, comprising an inorganic particle treated sequentially by
(a) hydrolyzing an aluminum compound or basic aluminate to deposit a hydrous alumina surface; and
(b) adding a dual-functional compound comprising
i. an anchoring group that attaches the dual-functional compound to the pigment surface selected from a carboxylic acid functional group, a di-carboxylic acid group, an oxoanion functional group, a 1,3-diketone, 3-ketoamide, derivative of 1,3-diketone, or derivative of 3-ketoamide, and
i. ii a basic amine group comprising a primary, secondary or tertiary amine, and
ii. a tethering group that chemically connects the anchoring group to the basic amine group wherein the tethering group comprises an alkyl chain of 1-8 carbon atoms; a carbon atom, an oxygen atom, a nitrogen atom, a phosphorus atom, a sulfur atom; or a polyetheramine comprising poly(oxyethylene) or poly(oxypropylene), or mixtures thereof; whereby the weight average molecular weight of the polyetheramine tether is about 220 to about 2000.

2. The self-dispersing pigment of claim 1 wherein inorganic particle is ZnO, TiO 2 , SrTiO 3 , BaSO 4 , PbCO 3 , BaTiO3, Ce 2 O 3 , Al 2 O 3 , CaCO 3 or ZrO 2 .

3. The self-dispersing pigment of claim 2 wherein the inorganic particle is a titanium dioxide pigment having a surface area of at least about 10 m 2 /g.

4. The self-dispersing pigment of claim 1 wherein the anchoring group is a carboxylic acid functional group that comprises acetate or salts thereof or a di-carboxylic acid group that comprises malonate, succinate, glutarate, adipate or salts thereof.

5. The self-dispersing pigment of claim 1 wherein the anchoring group is a 1,3-diketone or derivative of 1,3-diketone selected from 2,4-pentanedione, 3-(2-aminoethyl)-2,4-pentanedione, or a derivative of 2,4-pentanedione substituted at C-3 with ammine, an amine-containing functional group or salts thereof.

6. The self-dispersing pigment of claim 1 wherein the anchoring group is an oxoanion functional group selected from a substituted phosphate, phosphonate, sulfate, or sulfonate.

7. The self-dispersing pigment of claim 3 wherein the basic amine comprises ammine; an N-alkyl amine of 1 to 8 carbon atoms; an N-cycloalkyl amine of 3 to 6 carbon atoms; an N,N-dialkyl amine of 2 to 16 carbon atoms; N,N-dicycloalkyl amine of 6 to 12 carbon atoms; or mixtures of both alkyl and cycloalkyl substituents.

8. The self-dispersing pigment of claim 3 wherein the dual functional compound comprises alpha-amino acids selected from the group consisting of lysine, argenine, aspartic acid and salts thereof or alpha-omega aminoacids selected from the group consisting of beta-alanine, gamma-aminobutyric acid, epsilon-aminocaproic acid and salts thereof.

9. The self-dispersing pigment of claim 3 wherein the dual-functional compound comprises
(i) an aminomalonate derivative having the structure:

wherein X is a tethering group that chemically connects the anchoring group to the basic amine group;
R′ and R″ are each individually selected from hydrogen, alkyl, cycloalkyl, alkyl-aryl, alkenyl, cycloalkenyl, alkene, alkylene, arylene, alkylarylene, arylalkylene or cycloalkylene;
R 1 and R 2 are each individually selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkene, alkylene, or cycloalkylene; and n=0-50;
(ii) an aminosuccinate derivative having the structure:

wherein X is a tethering group that chemically connects the anchoring group to the basic amine group;
R′ and R″ are each individually selected from hydrogen, alkyl, cycloalkyl, alkyl-aryl, alkenyl, cycloalkenyl, alkene, alkylene, arylene, alkylarylene, arylalkylene or cycloalkylene;
R 1 and R 2 are each individually selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkene, alkylene, or cycloalkylene; and n=0-50;
(iii) a 2,4-pentanedione derivative having the structure:

wherein X is a tethering group that chemically connects the anchoring group to the basic amine group;

R 1 and R 2 are each individually selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkene, alkylene, and cycloalkylene; and
n=0-50; or
(iv) a 3-ketobutanamide derivative having the structure:

wherein X is a tethering group that chemically connects the anchoring group to the basic amine group;
R 1 and R 2 are each individually selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkene, alkylene, and cycloalkylene.

10. The self-dispersing pigment of claim 9 wherein the tethering group “X” comprises:
(a) an alkyl chain of 1-8 carbon atoms;
(b) a polyether chain comprising poly(oxyethylene) or poly(oxypropylene), or mixtures thereof whereby the weight average molecular weight of the tethering group is about 220 to about 2000; or
(c) polyetheramine co-polymers comprising both oxoethylene and oxopropylene monomers.

11. The self-dispersing pigment of claim 9 wherein R′ and R″ are hydrogen, methyl or ethyl and R 1 and R 2 are hydrogen, methyl, ethyl or propyl.

12. The self-dispersing pigment of claim 9 wherein the dual-functional compound is an aminomalonate derivative selected from methyl ester of 2-(2-aminoethyl)malonic acid or an ethyl ester of 2-(2-aminoethyl)malonic acid or 2-(2-aminoethyl)dimethylmalonate.

13. The self-dispersing pigment of claim 9 wherein the dual-functional compound is an aminosuccinate derivative selected from methyl ester of N-substituted aspartic acid, an ethyl ester of N-substituted aspartic acid or N-(2-aminoethyl)aspartic acid.

14. The self-dispersing pigment of claim 9 wherein the dual-functional compound is a 3-ketobutanamide (amidoacetate) derivative selected from an ethylenediamine amide, a diethylenetriamine amide or N-(2-aminoethyl)-3-oxo-butanamide.

15. The self-dispersing pigment of claim 3 wherein the aluminum compound is made from the salts comprising aluminium chloride, aluminum sulfate, or aluminum nitrate or mixtures thereof or a basic aluminate from sources comprising sodium or potassium aluminate.

16. The self-dispersing pigment of claim 1 further comprising at least one oxide treatment comprising aluminum oxide, silicon dioxide, zirconium oxide, cerium oxide, aluminosilicate or aluminophosphate.

17. The self-dispersing pigment of claim 3 wherein the titanium dioxide pigment comprises first an oxide layer comprising at least about 4% Al 2 O 3 and at least about 1.5% P 2 O 5 , and a second layer comprising at least about 3% Al 2 O 3 and about 2 mmole % to about 10 mmole % of the dual functional compound, based on the total weight of the treated pigment.

Assignees

• Chemours Company Tt Llc
• Chemours Co Fc Llc

Inventors

• Vanhecke Franck Andre
• Chinn Mitchell Scott

Classifications

• D21H27/26

  characterised by the overlay sheet or the top layers of the structures (decorative panels B44C5/04; wood grain effects B44F9/02) · CPC title

• C09C3/006

  Combinations of treatments provided for in groups C09C3/04 - C09C3/12 · CPC title

• C09C1/16

  White lead · CPC title

• C01P2006/12

  Surface area · CPC title

• C09D17/008 Primary

  Titanium dioxide · CPC title