Novel toner compounds and compositions for black offset inks

• US 20030110977A1
• Filed: 10/26/2001
• Published: 06/19/2003
• Est. Priority Date: 10/26/2001
• Status: Active Grant

• Current Assignee: Milliken & Company
• Original Assignee: Milliken & Company
• Inventors: Batlaw, Rajnish
• Granted Patent: US 6,664,311 B2
• Time in Patent Office: Days
• US Class Current: 106/31.13
• CPC Class Codes: C08G 18/2825 having at least 6 carbon atoms
• CPC Class Codes: C08G 18/38 having heteroatoms other than oxygen C08G18/32 takes precedence
• CPC Class Codes: C08G 18/71 Monoisocyanates or monoisothiocyanates
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C09D 11/037 characterised by the pigment
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Abstract

A novel colorant compound is provided which is the addition product of an organic chromophore having at least one reactive hydroxyl or amine substituent, a mono or polyisocyanate, and/or an alcohol. Such a compound provides solubility in oil-based ink compositions, complete water resistance and excellent oil based ink compositions. Furthermore, such colorants provide an easy and efficient way to tone shades of oil based inks. In addition, such colorants provide a way to tone carbon black based lithographic inks that gives the images a appearance of jet black on various types of printing substrates. A method for producing such a colorant is also provided, as well as offset ink compositions comprising such a colorant (including other colorants that provide the same toner performance within black pigment formulations).

Claims

1. A compound comprising the addition product of (a) an organic chromophore having at least one reactive hydroxyl or amine substituent group;

(b) a mono or polyisocyanate; and

(c) a long chain alcohol wherein said monoisocyanate reacts with said reactive hydroxyl or amine substituent groups to form a urethane colorant;

wherein said polyisocyanate reacts with each of said reactive hydroxyl or amine substituent groups to form isocyanate terminal groups on said organic chromophore and, subsequently, said long chain alcohols reacts with said isocyanate terminal groups to form urethane or urea moieties on the resulting compound.

2. The compound of claim 1 wherein said organic chromophore is selected from the group consisting of azo, diphenylmethane, triarylmethane, xanthene, methine, acridine, quinoline, thiazole, indamine, indophenol, azine, oxazine, thiazine, anthraquinone, indigoid, and phthalocyanine chromophores.

3. The compound of claim 2 wherein said organic chromophore is selected from the group consisting of azo, triarylmethane, xanthene, methine, and phthalocyanine chromophores.

4. The compound of claim 2 wherein said organic chromophore comprises at least one poly(oxyalkylene) substituent, having a straight or branched chain of from 3 to 200 residues of C_2-18 alkylene oxides.

5. The compound of claim 4 wherein said alkylene oxide residues are selected from the group consisting of ethylene oxide, propylene oxide, and mixtures thereof.

6. The compound of claim 1 wherein said monoisocyanate is selected from the group consisting of octadecenylisocyanate, butylisocyanate, and any mixtures thereof,

7. The compound of claim 1 wherein said polyisocyanate is selected from the group consisting essentially of 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4′

-biphenylene diisocyanate, 2,2′

-diphenylmethane diisocyanate, 4,4′

-diphenylmethane diisocyanate, 2,4′

-diphenylmethane diisocyanate, tetramethyl-m-xylene diisocyanate, p-xylene diisocyanate, methylenedi-p-phenyl diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, 4,4′

-diisocyanatodiphenyl ether, bis(4-isocyanatophenyl)sulfone, isopropylidene bis(4-phenyl isocyanate), naphthalene-1,5-diisocyanate, 1-chloro-2,4-phenylene diisocyanate, 3,3′

-bitolylene-4,4′

-diisocyanate, 3,3′

-dimethoxy-4,4′

-biphenylene diisocyanate, 3,3′

-dichloro-4,4′

-biphenylene diisocyanate, 2,2′

,5,5′

-tetramethyl-4,4′

-biphenylene diisocyanate, diphenylethane-4,4′

-diisocyanate, dicyclohexylmethane-4,4′

-diisocyanate, and any mixtures thereof.

8. The compound of claim 6 wherein said polyisocyanate is selected from the group consisting of tetra methyl xylene diisocyanate, isophorone diisocyanate, and mixtures thereof.

9. The compound of claim 1 wherein said long chain alcohol is selected from the group consisting of octanol, tetradecanol, undecanol, stearyl alcohol, 2-decanol, 1,12-dodecanol, 1,2-decanol, 1,10-decanol, 4-decanol, 2-octanol, 3-octanol, 3-octanol, nonanol, 2-undecanol, 2-tetradecanol, 1,2-tetradecanol, 1,14-tetradecanediol, heptadecanol, and mixtures thereof.

10. The compound of claim 1 wherein said compound conforms to the structure of Formula (I)

11. The compound of claim 10 wherein A is a group exhibiting one of the following chromophoric backbones selected from the group consisting of such backbones as nitro so, nitro, azo, diarylmethane, triarylmethane, xanthene, acridine, quinoline, methine, thiazole, indamine, indophenol, lactone, aminoketone, hydroxyketone, stilbene, azine, oxazine, thiazine, anthraquinone, phthalocyanine or indigoid.

13. The compound of claim 10 wherein B is N and a is 2.

14. The compound of claim 10 wherein B is O and a is 1.

15. The compound of claim 10 wherein Q is a combination of ethyleneoxy and propyleneoxy groups with from about 3 to about 50 moles thereof.

16. The compound of claim 10 wherein y is 0.

17. The compound of claim 13 wherein y is 0.

18. The compound of claim 14 wherein y is 0.

19. The compound of claim 15 wherein y is 0.

20. The compound of claim 10 wherein y is 1.

21. The compound of claim 13 wherein y is 1.

22. The compound of claim 14 wherein y is 1.

23. The compound of claim 15 wherein y is 1.

24. A substantially water-insoluble compound as defined by claim 1.

25. A substantially water-insoluble colorant as defined in claim 10.

26. An offset ink solution comprising from about 0.01 to about 90% of the compound of claim 1 and from about 10 to about 99% of a diluent.

27. The offset ink solution of claim 26 wherein said diluent is selected from the group consisting of mineral oils, hydrocarbon solvents, vegetable oils and mixtures thereof.

28. An offset ink solution comprising from about 0.01 to about 90% of the compound of claim 10 and from about 10 to about 99% of a diluent.

29. The offset ink solution of claim 28 wherein said diluent is selected from the group consisting of mineral oils, hydrocarbon solvents, vegetable oils and mixtures thereof.

30. A printed substrate selected from the group consisting of a textile, a polymeric film, and a paper, a portion of which is contacted with the ink solution of claim 26.

31. A printed substrate selected from the group consisting of a textile, a polymeric film, and a paper, a portion of which is contacted with the ink solution of claim 27.

32. A printed substrate selected from the group consisting of a textile, a polymeric film, and a paper, a portion of which is contacted with the ink solution of claim 28.

33. A printed substrate selected from the group consisting of a textile, a polymeric film, and a paper, a portion of which is contacted with the ink solution of claim 29.

34. A method of coloring a paper, polymeric film, or textile substrate comprising the steps of

(a) providing a substrate selected from the group consisting of a paper article, a polymeric film, and a textile article;

(b) contacting at least a portion of said substrate with the ink solution of claim 26;

and

(c) heating said contacted substrate to a temperature and for a period of time sufficient to effectively fix said compound to the surface of said substrate.

35. A method of coloring a paper, polymeric film, or textile substrate comprising the steps of

(a) providing a substrate selected fiom the group consisting of a paper article, a polymeric film, and a textile article;

(b) contacting at least a portion of said substrate with the ink solution of claim 27;

and

(c) heating said contacted substrate to a temperature and for a period of time sufficient to effectively fix said compound to the surface of said substrate.

36. A method of coloring a paper, polymeric film, or textile substrate comprising the steps of

(a) providing a substrate selected from the group consisting of a paper article, a polymeric film, and a textile article;

(b) contacting at least a portion of said substrate with the ink solution of claim 28;

and

(c) heating said contacted substrate to a temperature and for a period of time sufficient to effectively fix said compound to the surface of said substrate.

37. A method of coloring a paper, polymeric film, or textile substrate comprising the steps of

(a) providing a substrate selected from the group consisting of a paper article, a polymeric film, and a textile article;

(b) contacting at least a portion of said substrate with the ink solution of claim 29;

and

(c) heating said contacted substrate to a temperature and for a period of time sufficient to effectively fix said compound to the surface of said substrate.

12. The compound of claim 12 wherein said chromophore is a triphenylmethane, azo, methine, or anthraquinone.