Self-dispersed pigments and methods for making and using the same

• US 8,118,924 B2
• Filed: 05/17/2011
• Issued: 02/21/2012
• Est. Priority Date: 08/23/2007
• 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, Shing, Vincent, Bogomolny, Michael
• Primary Examiner(s): GREEN, ANTHONY J
• Application Number:
  US13/109,865
• Publication Number:
  US 20110308430A1
• Time in Patent Office: 280 Days
• Field of Search: 106/410, 106/412, 106/413, 106/472, 106/473, 106/476, 106/493, 106/494, 106/495, 106/496, 106/497, 106/498, 106/499, 427/506, 427/212, 427/215
• US Class Current: 106/506
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C01P 2002/52 containing elements as dopants
• CPC Class Codes: C01P 2002/85 by XPS, EDX or EDAX data
• CPC Class Codes: C01P 2004/64 Nanometer sized, i.e. from 1-100 nanometer
• CPC Class Codes: C01P 2006/12 Surface area
• CPC Class Codes: C01P 2006/22 Rheological behaviour as dispersion, e.g. viscosity, sedimentation stability
• CPC Class Codes: C01P 2006/40 Electric properties
• CPC Class Codes: C01P 2006/60 Optical properties, e.g. expressed in CIELAB-values
• CPC Class Codes: C09B 68/24 Azo-coupling
• CPC Class Codes: C09B 68/41 Polymers attached to the pigment surface C09B68/444, C09B68/446 take precedence
• CPC Class Codes: C09B 68/443 Carboxylic acid derivatives, e.g. carboxylic acid amides, carboxylic acid esters or CN groups
• CPC Class Codes: C09B 68/446 Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
• CPC Class Codes: C09B 68/46775 Triazine C09B68/427 takes precedence
• CPC Class Codes: C09C 1/56 Treatment of carbon black ; Purification
• CPC Class Codes: C09C 3/08 Treatment with low-molecular-weight non-polymer organic compounds C09C3/006, C09C3/048 take precedence
• CPC Class Codes: C09C 3/10 Treatment with macromolecular organic compounds C09C3/006 takes precedence
• CPC Class Codes: C09D 11/322 Pigment inks
• CPC Class Codes: C09D 17/003 containing an organic pigment process features in the making of dye stuff preparations C09B67/00

Abstract

A method of modifying a pigment 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. A pigment is reacted with the substituted reactive intermediate [Y]_a—X—(N—S—ZM)_b to attach the substituted reactive intermediate to the surface of the pigment to form a surface modified pigment. X may be a sulfonyl, phosphoryl, or 1,3,5-triazinyl group, Y may be a halogen leaving group, N may be a basic nucleophilic group, S may be an organic group, and 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 if b is 2 or 3, each. N—S—ZM can be the same or different.

Claims

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

reacting cyanuric chloride with about three equivalents of a secondary compound or a mixture of secondary compounds to displace all reactive chlorines to form a substituted triazine; and

reacting the substituted triazine with a surface of a pigment to form a surface modified pigment.

2. The method of claim 1, further comprising reacting the substituted triazine with the surface of the pigment using a radical initiator to form a surface modified pigment.

3. The method of claim 2, wherein the radical initiator comprises a persulfate.

4. The method of claim 1, wherein the mixture of secondary compounds may include one, two, or three different secondary compounds.

5. The method of claim 1, wherein the method is carried out at a temperature of about 25°

C. to about 90°

C.

6. The method of claim 1, wherein the secondary compound or mixture of secondary compounds 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, tetramethylammonium 4-aminobenxoate, sodium 4-aminophenolate, taurine, oleic acid (amino), sodium aminooleate, organic polymeric substrates, linear polyethoxy polymeric amines, linear propoxy polymeric amines, a diamino aromatic, a polyethyleneimine, a polyguanidine, a quarternary ammonium compound, or a combination thereof.

7. The method of claim 1, wherein the pigment comprises at least one of carbon black, pigment red 122, pigment violet 19, pigment violet 23, pigment red 202, pigment red 188, pigment yellow 155, pigment yellow 97, pigment green 7, pigment blue 15:

3, pigment blue 15;

4, and pigment yellow 74, and combinations thereof.

8. The method of claim 1, further comprising milling the pigment to less than about 100 nm before, during, or after reacting the pigment with the substituted triazine.

9. The method of claim 1, wherein the surface modified pigment comprises about 0.01 to about 1.0 mMoles of S and about 0.01 to about 2.0 mMoles of active hydrogen per gram of pigment.