Durable fluorescent organic pigments and methods of making

Abstract

Daylight fluorescent articles are disclosed that utilize durable fluorescent pigment particles resulting from a fluorescent dye incorporated within a matrix polymer selected from polycarbonate, polyester and mixtures thereof and where the particles are of various desired shapes and sizes. Embodiments of such fluorescent pigment particles may also be retroreflective and are especially useful for pavement marking surfaces and retroreflective products for highway transportation safety.

What is claimed is:  
     
         1 . A fluorescent pigment comprising in particle form: 
 a fluorescent dye selected from the group of thioxanthone, perylene, perylene imide, xanthene compounds and mixtures thereof;    a polymeric matrix selected from the group of polycarbonate, polyester, and mixtures thereof; wherein the fluorescent dye is incorporated into the polymeric matrix.    
     
     
         2 . The pigment of  claim 1 , further comprising: 
 microstructured surfaces on the pigment, forming a retroreflective fluorescence pigment.    
     
     
         3 . The pigment of  claim 2 , wherein: 
 the microstructured surfaces have a reflective coating thereon.    
     
     
         4 . The pigment of  claim 2 , wherein: 
 the microstructured surfaces have a sealing member thereon.    
     
     
         5 . The pigment of  claim 1 , wherein the fluorescent pigment has an equivalent diameter between about 10 microns to about 5000 microns.  
     
     
         6 . The pigment of  claim 1 , wherein the dye comprises about 0.01 to about 2 weight percent of the fluorescent pigment.  
     
     
         7 . The pigment of  claim 1 , further comprising a hindered amine light stabilizer; wherein the hindered amine light stabilizer comprises about 0.1 to about 0.8 weight percent of the fluorescent pigment.  
     
     
         8 . The pigment of  claim 7 , wherein the hindered amine light stabilizer is a 2,2,6,6-tetramethyl piperidine compound.  
     
     
         9 . The pigment of  claim 1 , further comprising retroreflective elements.  
     
     
         10 . The pigment of  claim 9 , wherein the retroreflective elements are selected from the group of microspheres and microstructured elements.  
     
     
         11 . The pigment of  claim 1  having a fluorescence luminance factor greater than 2.  
     
     
         12 . A fluorescent article, comprising: 
 a binder having a first major viewing surface; and    fluorescent pigment comprising, in particle form, a fluorescent dye selected from the group of thioxanthone, perylene, perylene imide, xanthene compounds and mixtures thereof; and    a polymeric matrix selected from the group of polycarbonate, polyester and mixtures thereof; wherein the fluorescent dye is incorporated in the polymeric matrix; and wherein at least some of the fluorescent pigment particles are disposed on or in the binder so as to be visible on the first major viewing surface of the binder.    
     
     
         13 . The article of  claim 12 , wherein the binder is a thermoplastic or thermoset polymer, or mixtures thereof.  
     
     
         14 . The article of  claim 12 , wherein the binder is a polymer selected from the group of polyurethane, polyacrylates, plasticized polyvinyl chloride, polyolefins, and mixtures thereof.  
     
     
         15 . The article of  claim 12 , wherein the binder is a multilayer film.  
     
     
         16 . The article of  claim 12 , wherein the binder further comprises fillers selected from the group of glass beads, ceramic microspheres, anti-skid particles, and inorganic powders.  
     
     
         17 . The article of  claim 12 , further comprising: 
 a colored backing layer; and    a fluorescent layer comprising the fluorescent pigment and the binder, wherein the backing layer is disposed adjacent the fluorescent layer.    
     
     
         18 . The article of  claim 12 , wherein the fluorescent pigment is disposed throughout the binder.  
     
     
         19 . A method of making a fluorescent article, comprising the steps of: 
 providing at least one fluorescent dye selected from the group of thioxanthone, perylene, perylene imide, xanthene compounds, and mixtures thereof;    providing a polymer matrix selected from the group of polycarbonate, polyester, and mixtures thereof;    extruding a mixture of said fluorescent dye and the polymer matrix;    fracturing the extrudate to form a fluorescent pigment in a particle form; and    disposing the fluorescent pigment on or in a binder to form the fluorescent article.    
     
     
         20 . The method of  claim 19 , comprising the additional steps of: 
 fracturing the binder to yield a binder particulate;    providing microstructured surfaces on the fluorescent pigment to form retroreflective fluorescent pigment;    mixing the fluorescent retroreflective pigment with the binder particulate to form a powder blend; and    flame spraying the powder blend onto a suitable substrate.    
     
     
         21 . The method of  claim 19 , comprising the additional steps of: 
 providing the binder as a liquid dispersion;    providing microstructured surfaces on the fluorescent pigment to form retroreflective fluorescent pigment;    mixing the retroreflective fluorescent pigment with the liquid binder to form a liquid blend;    coating the liquid blend onto a suitable substrate; and    curing the liquid blend onto the substrate to form a retroreflective fluorescent article.    
     
     
         22 . The method of  claim 20 , wherein the suitable substrate is a pavement marking surface.