Alizarin-Based Polymer Colorants

• US 20140342280A1
• Filed: 05/20/2013
• Published: 11/20/2014
• Est. Priority Date: 05/20/2013
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Farrugia, Valerie M., Birau, Mihaela Maria, Iftime, Gabriel, Abraham, Biby Esther
• Granted Patent: US 9,181,389 B2
• Time in Patent Office: Days
• US Class Current: 430/108.4
• CPC Class Codes: C08G 2261/344 containing heteroatoms
• CPC Class Codes: C08G 63/133 Hydroxy compounds containing aromatic rings
• CPC Class Codes: C08G 63/183 Terephthalic acids
• CPC Class Codes: C08G 63/193 containing two or more aromatic rings
• CPC Class Codes: C08G 63/199 Acids or hydroxy compounds containing cycloaliphatic rings
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: G03G 9/08755 Polyesters
• CPC Class Codes: G03G 9/08795 characterised by their chemical properties, e.g. acidity, molecular weight, sensitivity to reactants
• CPC Class Codes: G03G 9/08797 characterised by their physical properties, e.g. viscosity, solubility, melting temperature, softening temperature, glass transition temperature
• CPC Class Codes: G03G 9/0908 Anthracene dyes
• CPC Class Codes: G03G 9/0912 Indigoid; Diaryl and Triaryl methane; Oxyketone dyes

Abstract

A polymer colorant including polymer monomer units, and at least one alizarin unit which is incorporated into the polymer and which provides color to the polymer colorant and a process for preparing the polymer colorant. An article or composition containing the polymer colorant. A toner including the polymer colorant, and optionally, one or more ingredients selected from the group consisting of crystalline polyester resins, amorphous polyester resins, colorants, waxes, coagulants, mordants, and mixtures and combinations thereof. A polymer latex including an aqueous dispersion of polymer colorant, wherein the polymer colorant comprises polymer monomer units and at least one alizarin unit which is incorporated into the polymer and which provides color to the polymer colorant; and optionally, a mordant.

Claims

1. A polymer colorant comprising:

polymer monomer units; and

at least one alizarin unit which is incorporated into the polymer and which provides color to the polymer colorant.

2. The polymer colorant of claim 1, wherein the polymer monomer units are selected from the group consisting of polyester monomer units, polyamide monomer units, polyurethane monomer units, and combinations thereof.

3. The polymer colorant of claim 1, wherein the polymer monomer units are bio-based, wherein the alizarin is bio-renewable, or wherein both the polymer monomer units are bio-based and the alizarin is bio-renewable.

4. The polymer colorant of claim 1, wherein the polymer monomer units provide an amorphous polyester, a crystalline polyester, or a combination thereof.

5. The polymer colorant of claim 1, wherein polymer is a bio-based, branched polyester resin comprising (i) the condensation product of (a) a hydroxyl donor;

(b) a cyclic polyhydroxyl acceptor; and

(c) an optional catalyst, and (ii) a polyacid, wherein said bio-based, branched polyester resin is greater than about 90% bio-based.

6. The polymer colorant of claim 1, wherein the polymer is a bio-based, branched polyester resin comprising (i) the polycondensation product of (a) glycerine carbonate and/or glycerol;

and (b) a rosin acid selected from the group consisting of abietic acid, neoabietic acid, palustric acid, levopimaric acid, dihydroabietic acid, pimaric acid, isopimaric acid and combinations thereof; and

(ii) a polyacid selected from the group consisting of succinic acid, fumaric acid, maleic acid, itaconic acid, dodecylsuccinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and azelaic acid.

7. The polymer colorant of claim 1, wherein the polymer is 1-decyl-12-methyl dodecanedioate of the formula

8. The polymer colorant of claim 1, wherein the polymer is a branched polyester comprising a compound of the formula:

9. The polymer colorant of claim 1, wherein the alizarin is a compound of the formula

10. The polymer colorant of claim 1, wherein the alizarin is selected from the group consisting of 1,3-dihydroxyanthraquinone, 1,4-dihydroxyanthraquinone, 1,5-dihydroxyanthraquinone, 1,6-dihydroxyanthraquinone, 1,7-dihydroxyanthraquinone, 1,8-dihydroxyanthraquinone, 2,3-dihydroxyanthraquinon, 2,6-dihydroxyanthraquinone, 2,7-dihydroxyanthraquinone, and mixtures and combinations thereof.

11. The polymer colorant of claim 1, wherein the color of the polymer colorant is tuned by selecting a mole percent of alizarin based on the total mole percent of polymer units including polymer monomer units and alizarin units.

12. The polymer colorant of claim 1, wherein the polymer monomer units are selected from the group consisting of 1,6-heaxnediol, succinic acid, dimethyl terephthalate, 1,12-dodecanedioic acid, propanediol, isophthalic acid, azelaic acid, isosorbide, and combinations thereof.

13. The polymer colorant of claim 1, wherein the color of the polymer colorant is pink, brown, grey, or black.

14. The polymer colorant of claim 1, wherein the polymer colorant has a final color that is determined by one or more of the following:

amount of alizarin units, type of monomer units, amount of monomer units;

treatment of alizarin with a mordant, interaction of the alizarin monomeric unit with the other monomers comprising the polymer colorant.

15. The polymer colorant of claim 1, provided in an article selected from the group consisting of toners, inks, toys, paints, fibers, machine parts, molded products, extruded products, and combinations thereof.

16. The polymer colorant of claim 1, provided in a composition comprising the polymer colorant and optionally, a mordant.

17. A polymer latex comprising:

an aqueous dispersion of polymer colorant, wherein the polymer colorant comprises polymer monomer units and at least one alizarin unit which is incorporated into the polymer and which provides color to the polymer colorant; and

optionally, a mordant.

18. A toner comprising:

a polymer colorant comprising polymer monomer units and at least one alizarin unit which is incorporated into the polymer and which provides color to the polymer; and

optionally, one or more ingredients selected from the group consisting of crystalline polyester resins, amorphous polyester resins, colorants, waxes, coagulants, mordants, and mixtures and combinations thereof.

19. The toner of claim 18, wherein the polymer monomer units are selected from the group consisting of polyester monomer units, polyamide monomer units, polyurethane monomer units, and combinations thereof;

and

wherein the alizarin is selected from the group consisting of 1,3-dihydroxyanthraquinone, 1,4-dihydroxyanthraquinone, 1,5-dihydroxyanthraquinone, 1,6-dihydroxyanthraquinone, 1,7-dihydroxyanthraquinone, 1,8-dihydroxyanthraquinone, 2,3-dihydroxyanthraquinon, 2,6-dihydroxyanthraquinone, 2,7-dihydroxyanthraquinone, and mixtures and combinations thereof.

20. A process for preparing a polymer colorant comprising:

contacting at least one polymer monomer with at least one alizarin unit and polymerizing to form a polymer colorant wherein the alizarin is incorporated into the polymer and wherein the alizarin provides color to the polymer colorant; and

determining the final color of the polymer colorant by one or more of the following;

(a) selecting a ratio of alizarin units relative to polymer monomer units, (b) selecting type of monomer units, (c) treating alizarin with a mordant prior to polymerizing, (d) treating alizarin with a mordant during polymerizing, e) treating the polymer colorant with a mordant after polymerizing, (f) selecting a ratio of alizarin units relative to polymer monomer units and selecting type of monomer units to control interaction of the alizarin monomeric unit with the other monomers comprising the polymer colorant.