Chemical compositions for authenticatable polymers and articles, and authentication methods thereof

A method for authenticating that an article is an authenticatable article having a standard signal, said authenticatable article comprising a taggant, the method comprising

• irradiating a test portion of the article with ultraviolet radiation by using an optical tester comprising an ultraviolet radiation source and a fluorescence detector,
• measuring a test signal emitted by said article, and
• authenticating that the article is an authenticatable article if the test signal matches the standard signal;
• wherein said taggant composition comprises at least one [benzo[4,5]imidazo(heterocycle)] compound, said at least one [benzo[4,5]imidazo(heterocycle)] compound being present in said taggant composition at a concentration sufficient to cause said taggant composition to exhibit upon exposure to an excitation radiation having a wavelength of from about 330 nanometers to about 390 nanometers, a maximum fluorescence emission wavelength of greater than or equal to about 470 nanometers;
• and a Stokes shift of greater than or equal to about 80 nanometers

A method for preparing a [2,2′]bis{[benzo[4,5]imidazo[2,1-α]isoindolyl]-11-one} compound, said method comprising:

• contacting an aromatic dianhydride having a structure III:
• wherein L is a linking group, and “r” is 0 or 1;
• with an aromatic diamine having a structure IV:
• wherein R1 is selected from the group consisting of a hydrogen atom, electron withdrawing group, organic group, divalent 1,2-cycloalkylidene group, or combinations thereof;
• and “q” is an integer from 0-4;
• and
• forming said [2,2′]bis {[benzo[4,5]imidazo[2,1-α]isoindolyl]-11-one}compound having a structure I:

A method for preparing a [7,7′]bis{[benzo[4,5]imidazo[2,1-α]isoindolyl]-11-one} compound, the method comprising:

• contacting an aromatic tetraamine having a structure V:
• wherein “L” is a linking group, and ‘r’ is 0 or 1;
• with an aromatic monoanhydride having a structure VI:
• wherein R2 is selected from the group consisting of a hydrogen atom, electron withdrawing group, organic group, divalent 1,2-cycloalkylidene group, or combinations thereof;
• and “q” is an integer from 0-4;
• forming a first intermediate product;
• treating said first intermediate product with a first solvent,
• isolating a second intermediate product,
• treating said intermediate product with a second solvent, and
• isolating said [7,7′]bi[benzo[4,5]imidazo[2,1-α]isoindolyl]-11,11′-dione compound having a structure II:
• wherein said compound upon exposure to an excitation radiation having a wavelength of from about 330 nanometers to about 390 nanometers exhibits a fluorescence emission having a wavelength of from about 470 nanometers to less than 530 nanometers, and wherein the wavelengths are measured in bisphenol A polycarbonate matrix;
• said compound being present in a concentration sufficient to produce a composition capable of exhibiting said fluorescence emission.