Self-dispersing particles and methods for making and using the same

• US 9,221,986 B2
• Filed: 04/07/2010
• Issued: 12/29/2015
• Est. Priority Date: 04/07/2009
• Status: Active Grant

• Current Assignee: Sensient Colors, LLC (Sensient Technologies Corporation)
• Original Assignee: Sensient Colors, LLC (Sensient Technologies Corporation)
• Inventors: Sujeeth, Puthalath K., Kane, John P., Ouellette, Daniel A., Ulrich, Mark
• Primary Examiner(s): Faison, Veronica F
• Application Number:
  US12/756,175
• Publication Number:
  US 20100251932A1
• Time in Patent Office: 2,092 Days
• Field of Search: 106/31.6, 106/400, 106/401, 106/412, 106/413, 106/425, 106/436, 106/456
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/412 Microsized, i.e. having sizes between 0.1 and 100 microns
• CPC Class Codes: A61K 2800/622 by organic compounds
• CPC Class Codes: A61K 8/445 aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: C01P 2002/85 by XPS, EDX or EDAX data
• CPC Class Codes: C01P 2004/62 Submicrometer sized, i.e. from 0.1-1 micrometer
• CPC Class Codes: C01P 2006/22 Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
• CPC Class Codes: C01P 2006/62 L* (lightness axis)
• CPC Class Codes: C01P 2006/63 a* (red-green axis)
• CPC Class Codes: C01P 2006/64 b* (yellow-blue axis)
• CPC Class Codes: C07D 251/54 Three nitrogen atoms
• CPC Class Codes: C09B 67/0002 Grinding; Milling with solid grinding or milling assistants
• CPC Class Codes: C09B 67/0009 containing organic acid derivatives
• CPC Class Codes: C09B 67/0086 anionic dispersing agents
• CPC Class Codes: C09C 1/24 Oxides of iron
• CPC Class Codes: C09C 1/3684 Treatment with organo-silicon compounds
• CPC Class Codes: C09C 3/12 Treatment with organosilicon compounds C09C3/006 takes precedence
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: C09D 11/326 characterised by the pigment dispersant
• CPC Class Codes: C09D 11/328 characterised by dyes
• CPC Class Codes: C09D 15/00 : Woodstains
• CPC Class Codes: C09D 7/41 : Organic pigments; Organic dyes
• CPC Class Codes: G02B 5/223 : containing organic substances, e.g. dyes, inks or pigments

Abstract

A method of modifying a particle that includes reacting a reactive compound having an X—[Y]_n reactive group with a secondary compound N—S-ZM to form a substituted reactive intermediate [Y]_a—X—(N—S-ZM)_b, and reacting the particle with the substituted reactive intermediate [Y]_a—X—(N—S-ZM)_b to attach the substituted reactive intermediate to the surface of the particle to form a surface modified particle. The particle may comprise at least one of a dye particle, an inorganic pigment particle, an additive, or a combination thereof. X may be a sulfonyl, phosphoryl, or 1,3,5-triazinyl group. Y may be a halogen leaving group. N may be a nucleophilic group. S may be an organic group. ZM may be an ionizable end group. Also, n is an integer between 1 and 3, b is an integer between 1 and 3, and a=n−b. When n is equal to or greater than b, and wherein if b is 2 or 3, each N—S-ZM can be the same or different.

Claims

1. A method of modifying a particle, the method comprising:

reacting a reactive compound having an X—

[Y]_n reactive group with a secondary compound N—

S-ZM to form a substituted reactive intermediate [Y]_a—

X—

(N—

S-ZM)_b; and

reacting the particle with the substituted reactive intermediate [Y]_a—

X—

(N—

S-ZM)_b to attach the substituted reactive intermediate to the surface of the particle to form a surface modified particle, the particle comprising at least one of a dye particle, an inorganic pigment particle, an additive, or a combination thereof;

wherein X is a sulfonyl, phosphoryl, or 1,3,5-triazinyl group;

Y is a halogen leaving group;

N is a nucleophilic group;

S is an organic group;

ZM is an ionizable end group;

n is an integer between 1 and 3;

b is an integer between 1 and 3; and

a=n−

b;

wherein n is equal to or greater than b; and

wherein if b is 2 or 3, each N—

S-ZM can be the same or different.

2. The method of claim 1, wherein X is a 1,3,5-triazinyl group.

3. The method of claim 1, wherein b is 2 or 3, and each N—

S-ZM is different.

4. The method of claim 3, wherein the X—

[Y]_n reactive group comprises cyanuric chloride, and the secondary compounds comprise 4-aminobenzoic acid and a polymeric amine.

5. The method of claim 1, wherein Y comprises at least one of fluorine, chlorine, bromine, or iodine.

6. The method of claim 1, wherein N comprises at least one of an amine, an imine, a pyridine, or a thiol group.

7. The method of claim 1, wherein S comprises at least one of substituted or unsubstituted alkyls, aryls and polymer chains having a molecular weight range from about 300 to about 8000.

8. The method of claim 1, wherein Z comprises at least one of a carboxyl, sulfonyl, phenolic, or phosphoryl group and M comprises at least one of a proton or cation in salt form.

9. The method of claim 1, wherein the secondary compound N—

S-ZM comprises at least one of a polymer, an amine, an amino acid, an alcohol, a thiol, and a combination thereof.

10. The method of claim 9, wherein the secondary compound N—

S-ZM comprises at least one of amino benzoic acids, amino benzene sulfonic acids, amino phenols, amino sulfonic acids, polyethoxylated amino acids, sodium sulfanilate, sulfanilic acid, sodium p-aminobenzoate, p-aminophenol, ethyl 4-aminobenzoate, taurine, oleic acid (amino), tetramethylammonium 4-aminobenzoate, sodium 4-aminophenolate, sodium aminooleate, organic polymeric substrates, and combinations thereof.

11. The method of claim 10, wherein the organic polymeric substrates comprises at least one of linear alkyl and branched ethoxy and propoxy chain polymers with a molecular weight of about 300 to about 3000, linear polyethoxy polymeric amines, linear propoxy polymeric amines, styrene acrylic copolymers, polyethyleneimines, and combinations thereof.

12. The method of claim 1, wherein Z comprises at least one of ammonium, trimethylammonium, or tributylammonium and M comprises at least one of a halide or a negatively charged ion.

13. The method of claim 1, wherein the secondary compound N—

S-ZM comprises at least one of a diamino aromatic, a polyethyleneimine, a polyguanidine, a quaternary ammonium compound, or a combination thereof.

14. The method of claim 1, wherein the particle comprises at least one of Disperse Blue 14, Disperse Blue 19, Disperse Blue 72, Disperse Blue 334, Disperse Blue 359, Disperse Blue 360, Disperse Orange 25, Disperse Yellow 54, Disperse Yellow 64, Disperse Red 55, Disperse Red 60, Macrolex Red H, Disperse Brown 27, Solvent Blue 67, Solvent Blue 70, Solvent Red 49, Solvent Red 146, Solvent Red 160, Solvent Yellow 162, Solvent Violet 10, Solvent Black 29, Acid Yellow 204, Acid Yellow 151, Acid Orange 60, Acid Red 182, Acid Red 357, Acid Red 359, Acid Blue 193, Acid Brown 355, Acid Violet 90, Acid Black 172, Acid Black 194, Acid Black 52, Acid Black 60, titanium (IV) oxide, iron (III) oxide, zinc oxide, and combinations thereof.

15. The method of claim 1, further comprising milling the particle to less than about 200 nm before, during, or after reacting the pigment with the substituted reactive intermediate.

16. The method of claim 1, wherein the substituted reactive intermediate [Y]_a—

X—

(N—

S-ZM)_b is associated with charge-balancing counterions, further comprising at least partially substituting the counterions with at least one of alkali metals, alkaline earth metals, NR₁R₂R₃H⁺, and combinations thereof, wherein R₁, R₂, and R₃ are independently H or substituted or unsubstituted C₁-C₅ alkyl groups.

17. The method of claim 16, wherein the counterions are at least partially substituted with at least one of K⁺, Li⁺, NH₄⁺, monoethanolammonium, tetraethylammonium, triethanolammonium, tetramethylammonium, tetrabutylammonium, and combinations thereof.

18. The method of claim 1, further comprising incorporating the surface modified particle into an aqueous particle dispersion.

19. A wood stain, coating, inkjet ink, color filter, or textile printing ink, comprising the surface modified particle produced by the method of claim 1.

20. The method of claim 1, wherein the X—

[Y]_n reactive group is cyanuric chloride and the secondary compound N—

S-ZM is at least one of 4-aminobenzoic acid, sulfanilic acid, 4-aminophenolate, taurine, oleic acid (amino), linear polyethoxy polymeric amines, linear propoxy polymeric amines, or combinations thereof.

21. The method of claim 1, wherein the surface modified particle is a self-dispersing particle.

22. The method of claim 1, wherein the surface modified particle comprises about 0.1 to about 0.8 mMoles of active hydrogen per gram of particle.

23. The method of claim 1, wherein the surface modified particle comprises a total amount of alkali metal equivalent to about 0.1 to about 0.8 mMoles of active hydrogen per gram of particle.

24. The method of claim 23, wherein the surface modified particle comprises the dye particle.

25. The method of claim 23, wherein the surface modified particle comprises the inorganic pigment particle, about 2 to about 7 percent of carbon, about 0.1 to about 2 percent of hydrogen, and about 0.1 to about 0.5 mMoles of active hydrogen per gram of the inorganic pigment particle.

26. The method of claim 23, wherein the particle comprises a least one of titanium oxide, iron oxide, or zinc oxide.