Fluorescent yellow azo pigments

• US 5,863,459 A
• Filed: 05/09/1997
• Issued: 01/26/1999
• Est. Priority Date: 05/09/1997
• Status: Expired due to Term

• Current Assignee: Sun Chemical Corporation
• Original Assignee: Sun Chemical Corporation
• Inventors: Zwirgzdas, Anthony C., Gregorio, Manuel Z., Merchak, Paul A., Schwartz, Russell J.
• Primary Examiner(s): KOSLOW, CAROL M
• Application Number:
  US08/855,725
• Time in Patent Office: 627 Days
• Field of Search: 106/496, 106/31.64, 106/31.79, 106/31.8, 106/31.81, 252/301.16, 252/301.35, 118/668, 118/712, 283/62, 428/187, 428/195, 428/690
• US Class Current: 252/301.16
• CPC Class Codes: C09B 67/0015 of azoic pigments
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: Y10T 428/24736 Ornamental design or indicia
• CPC Class Codes: Y10T 428/24802 Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Abstract

Yellow azo fluorescent pigments and a process for a preparing same. Yellow azo fluorescent pigments as a component of printing ink, coating, plastic compositions and articles of manufacture and used for controlling manufacturing operations.

Claims

1. A fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

2. The pigment of claim 1 selected from disazo yellow and monoazo yellow pigments.

3. The pigment of claim 2 wherein the pigment is a diarylide yellow pigment.

4. The pigment of claim 3 being Pigment Yellow 63.

5. The pigment of claim 4 having an average crystallite size greater than 350 Angstroms.

6. The pigment of claim 3 being Pigment Yellow 12.

7. The pigment of claim 3 being Pigment Yellow 14.

8. A printing ink composition having incorporated therein at least one flourescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

9. The composition of claim 8 wherein the pigment is selected from disazo yellow and monoazo yellow pigments.

10. The composition of claim 9 wherein the pigment is a diarylide yellow pigment.

11. The composition of claim 10 wherein the pigment is Pigment Yellow 63.

12. The composition of claim 11 wherein the pigment has an average crystallite size greater than 350 Angstroms.

13. The composition of claim 10 wherein the pigment is Pigment Yellow 12.

14. The composition of claim 10 wherein the pigment is Pigment Yellow 14.

15. A coating composition having as a constituent thereof at least one fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

16. The composition of claim 15 wherein the pigment is selected from disazo yellow and monoazo yellow pigments.

17. The composition of claim 16 wherein the pigment is a diarylide yellow pigment.

18. The composition of claim 17 wherein the pigment is Pigment Yellow 63.

19. The composition of claim 18 wherein the pigment has an average crystallite size greater than 350 Angstroms.

20. The composition of claim 17 wherein the pigment is Pigment Yellow 12.

21. The composition of claim 17 wherein the pigment is Pigment Yellow 14.

22. A plastic composition containing at least one fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

23. The composition of claim 22 wherein the pigment is selected from disazo yellow and monoazo yellow pigments.

24. The composition of claim 23 wherein the pigment is a diarylide yellow pigment.

25. The composition of claim 24 wherein the pigment is Pigment Yellow 63.

26. The composition of claim 25 wherein the pigment has an average crystallite size greater than 350 Angstroms.

27. The composition of claim 24 wherein the pigment is Pigment Yellow 12.

28. The composition of claim 24 wherein the pigment is Pigment Yellow 14.

29. A process for preparing a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum response between wavelengths of 520 to 560 nanometers exceeds the response at 600 nanometers comprising:

(a) preparing a solution of tetrazotized 3,3'"'"'dichlorobenzidine by adding 3,3'"'"'dichlorobenzidine to hydrochloric acid and sodium nitrite;

(b) preparing a coupling suspension by dissolving a coupler in a sodium hydroxide solution, and forming a suspended precipitate of the coupling suspension with acetic acid;

(c) reacting the solution of tetraotized 3,3'"'"'dichlorobenzidine with the suspended precipitate to form a pigment intermediate;

(d) filtering said intermediate;

(e) water washing said intermediate;

(f) drying said intermediate at a temperature ranging from about 80°

C. to about 85°

C.;

(g) forming a slurry of said intermediate in a solvent; and

(h) heating said slurried intermediate optionally under pressure ranging up to about 100 pounds per square inch.

30. The process of claim 29 wherein the solvent is selected from aromatic hydrocarbons, chlorinated aromatic hydrocarbons, aliphatic hydrocarbons, chlorinated aliphatic hydrocarbons, C₁ -C₆ alcohols, C₁ -C₆ ketones, ethers, C₁ -C₆ acetates and water.

31. The process of claim 30 wherein the solvent is ethanol.

32. The process of claim 30 wherein the solvent is water.

33. The process of claim 29 wherein the pigment prepared is a monoazo yellow pigment.

34. The process of claim 29 wherein the pigment prepared is a disazo yellow pigment.

35. The process of claim 34 wherein the pigment prepared is a diarylide yellow pigment.

36. The process of claim 35 wherein the pigment prepared is a fluorescent Pigment Yellow 63.

37. The process of claim 36 wherein the fluorescent Pigment Yellow 63 is prepared by using as a coupler acetoacet-o-chloroanilide.

38. The process of claim 35 wherein the pigment prepared is a fluorescent Pigment Yellow 12.

39. The process of claim 38 wherein the fluorescent Pigment Yellow 12 is prepared by using as a coupler acetoacetanilide.

40. The process of claim 35 wherein the pigment prepared is a fluorescent Pigment Yellow 14.

41. The process of claim 40 wherein the fluorescent Pigment Yellow 14 is prepared by using as a coupler acetoacet-o-toluidide.

42. An improved method for controlling operations to an article of manufacture involving (a) affixing a non-migrating mark of organic polar or ionic material to a heat-sealable polyolefin web;

(b) detecting the presence of said mark on said web by sensing the presence of emitted radiation; and

(c) performing operations to said web;

wherein said improvement comprises;

substituting or combining said organic polar or ionic material with a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum spectral response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

43. An improved web of thermoplastic polyolefin material, which fuses under application of heat and pressure, suitable for fabrication into a series of connected but separable articles, and carrying a series of marks of organic polar or ionic material that essentially do not migrate in the web and emits wavelength-shifted radiation when exposed to incident radiation;

wherein said improvement comprises;

substituting or combining said organic polar or ionic material with a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum spectral response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

44. An improved web capable of being moved along a path relative to an operating mechanism, said web comprising a thermoplastic polyolefin material, which fuses under application of heat and pressure, suitable for operations including at least heat sealing into a series of articles useful as at least a part of a container, and indicia at location on said web correlated with said articles for controlling operations of the mechanism upon the web, said indicia being comprised of a polar or ionic organic material which emits wavelength-shifted radiation in the non-visible spectrum, that essentially does not migrate in the web, is essentially invisible to the human eye and detectable to control the operating mechanism;

wherein said improvement comprises;

substituting or combining said organic polar or ionic material with a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum spectral response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

45. An improved article of manufacture comprising a thermoplastic polyolefin foil, which fuses under application of heat and pressure, and a mark on the foil, said mark being comprised of an organic ionic or polar material which responds to incident electromagnetic radiation by emitting radiation of a different wavelength to allow detection of the presence of said mark;

said improvement comprises;

substituting or combining said organic polar or ionic material with a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum spectral response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.

46. An improved article useful in the packaging or container art and capable of being moved along a path relative to a fabricating mechanism, said article comprising a sheet or web of thermoplastic polyolefin material to be fabricated, which fuses under application of heat and pressure and indicia carried by the article for controlling the fabrication, said indicia being comprised of an organic polar or ionic material that emits wavelength-shifted radiation under incident electromagnetic radiation and that is essentially non-migrating in said material and that is essentially invisible to the human eye under electromagnetic radiation in the visible spectrum;

said improvement comprises;

substituting or combining said organic polar or ionic material with a fluorescent yellow azo pigment exhibiting a spectral response to incident radiation wherein the maximum spectral response between wavelengths of 520 and 560 nanometers exceeds the response at 600 nanometers.