Day-Glo Color Corp.

Thomas C DiPietro

Wayne R Likavec

John F Waters

Christopher Newbacher

Liming Tang

Provided herein are hybrid pigments and methods of making the same. The hybrid pigments include a natural polyamide substrate and an acid dye disposed on the natural polyamide substrate. The hybrid pigments are biodegradable, compostable, or both, and provide an environmentally friendly alternative to synthetic polymer particle-based pigments.

Hybrid pigments and methods of making same

A fluorescent naphthalimide diester dye that is miscible or soluble in a variety of organic compounds such as, for example, mineral oil, polyalkylene glycols, polyolesters, motor oil, gear oil, synthetic oils, and polyalphaolefins, is provided. The fluorescent naphthalimide diester is useful as a tracer to detect leaks within a fluid systems such as, for example, refrigerant systems, transmission systems, and hydraulic systems. The fluorescent naphthalimide diester dye is comprised of a chromophore having the following structure:

Naphthalimide diester fluorescent tracers having improved solubility and fluorescence

Thermoplastic, non-water soluble, fluorescent pigments having improved lightfastness are provided which are suitable for coloring a variety of materials including plastics, particularly polyolefins, as well as paints, inks and textiles. The pigments of the present invention referred to herein as the 'light fast pigments' demonstrate good color, migration resistance, heat stability, water insolubility, friability and resistance to plateout. The light fast pigments of the present invention have several embodiments, the polyamide embodiment, polyamide ester embodiment and the polyester embodiment. The pigments of the present invention comprises a polymer which comprises polymerized units of fluorescent dye and polymerized monomers such as for example dicarboxylicacids, polycarboxylicacids, diamines, polyamines, alkanolamines, carboxyalcohols, carboxyamines and difunctional alcohols, and/or polyhydric alcohols. The polyamide pigment embodiment and polyamide-ester pigment embodiment are polymers which comprise polyamide linkages. The polyester pigment embodiment are polymers that comprise polyester linkages, but substantially lacks polyamide linkages. The light fast pigments of the present invention contain a fluorescent dye reacted into, and covalently bound to the polymer backbone; this distinguishes the light fast pigment from conventional pigments which typically exist as a solid state solution of fluorescent dye and polymer carrier. In the polyester pigment embodiment, the fluorescent dye, which is physically incorporated into the backbone of polymer chain, is the BXDA fluorescent dye or an analog thereof. In the polyamide pigment and polyamide-ester pigment embodiments, the fluorescent dye is the BXDA fluorescent dye or its analogs thereof, or certain conventional dyes. While the light fast pigment of the present invention demonstrate improved lightfastness, the addition of an optional light stabilizer enhances the lightfastness of the pigment. The invention also relates to a method of making such light fast pigment.

Fluorescent polymeric pigments

The present invention provides a novel, non-formaldehyde thermoset fluorescent pigment which is useful to color plastics, particularly flexible vinyl, which is solvent resistant, particularly to acetone. Moreover, the pigment does not bleed in plastics. The pigment comprises a polymer matrix and a fluorescent dye. The polymer matrix has a molecular weight of greater than about 330, preferably greater than about 1000. Embodiments which lack the water insoluble resin, have a molecular weight greater than about 330, preferably greater than about 500. The polymer matrix contains: from about 15 to 50 mole percent, preferably 30 to 40 mole percent, of a carboxylate functional oligomer; 30 to 80 mole percent, preferably 50 to 60 mole percent, of a metal ion; and 0 to 40 mole percent, preferably about 1 to 40 mole percent, more preferably from 1 to 30 mole percent, most preferably from about 3 to 10 mole percent of a water insoluble resin. In embodiments where no water insoluble resin is used, the metal is present from at least 51 mole percent. The oligomer comprises from about 10 to about 60 mole percent, preferably 20 to 35 mole percent of a first monomer, 40 to 90 mole percent, preferably 65 to 80 mole percent of second monomer. The weight average molecular weight of the oligomer is 330 to 2000, preferably about 560 to 600. The invention also relates to a novel method for producing the fluorescent pigments.

Solvent resistant non-formaldehyde thermoset fluorescent pigment

A thermoplastic, organic, fluorescent pigment affording good viscosity control in solvent. A one-pot production of the pigment. Pigment having a fluorescent dye and a polymer matrix containing a dicarboxylic acid, an organic diamine and, optionally, alkanolamine, aliphatic alkanolamine, aliphatic diol, cycloaliphatic diol, modifiers, and cross-linkers.

Fluorescent pigments

A fluorescent pigment includes a fluorescent dye and a resin carrier which is the polyamide reaction product of a diamine and a diacid. The fluorescent pigments are especially useful to color plastics and have improved resistance to plateout during molding. The pigments may be melt-blended with plastic to provide a color concentrate. The polyamide resins have a molecular weight in the range of 3,000 to 50,000 and may be readily ground to micron sized particles.

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Medina, OH, United States of America

Thomas C DiPietro