Process for incorporation of uv-luminescent compounds in polymeric materials

Abstract

The invention relates to a process for the preparation of luminescent textile fibres characterized in that the fibres are ated with a composition comprising (a) one or more luminescent lanthanide chelates containing three organic anionic ligands having at least one UV absorbing group and (b) one or more solvents.

1 . A process for the preparation of luminescent polymeric fibres, wherein the fibres are treated with a composition comprising 
 (a) one or more luminescent lanthanide chelates containing three or four organic anionic ligands having at least one UV absorbing group and    (b) one or more solvents.    
   
   
       2 . A process according to  claim 1 , wherein component (a) is a compound of formula I  
       L m -Ln 3+ (Ch − ) n   (I),  
     wherein Ln represents a lanthanide, 
 Ch −  is a negatively charged ligand containing at least one UV absorbing double bond,  
 n denotes 3 or 4, m denotes a number from 0 to 4, wherein  
 when n is 3, m denotes a number from 0 to 4 and L is a neutral monodentate or polydentate nitrogen-, oxygen- or sulfur-containing ligand or, when n is 4, m denotes 1 and L is a single-charged cation.  
 
   
   
       3 . A process according to  claim 1 , wherein component (a) is a compound of formula I, II, III or IV  
       
     
       
         
         
             
             
         
       
     
       
     wherein Ln represents a lanthanide, 
 n denotes 3 or 4, m denotes a number from 0 to 4, in which when n is 3, m denotes a number from 0 to 4 and L is a neutral monodentate or polydentate nitrogen-, oxygen- or sulfur-containing ligand or, when n is 4, m denotes 1 and L is a single-charged cation,  
 Ch −  is a negatively charged ligand containing at least one UV absorbing double bond,  
 R 2 , is hydrogen or C 1 -C 6 alkyl, and  
 R 1  and R 3  are each independently of the other hydrogen, C 1 -C 6 alkyl, CF 3 , C 5 -C 24 aryl or C 4 -C 24 heteroaryl.  
 
   
   
       4 . A process according to  claim 3 , wherein component (a) is a compound of formula I, II, III or IV wherein n denotes 3 and L is a nitrogen-containing ligand.  
   
   
       5 . A process according to  claim 3 , wherein component (a) is a compound of formula I, II, III or IV wherein L is a compound of formulae V to XII  
     
       
         
         
             
             
         
       
        or a cation of the formula H—N + (R 7 ) 3 ,  
       wherein R 4 , R 5  and R 6  are each independently of the other hydrogen, halogen, C 1 -C 6 alkyl, C 5 -C 24 aryl, C 6 -C 24 aralkyl, C 1 -C 6 alkoxy, amino, dialkylamino or a cyclic amino group and R 7  is hydrogen, C 1 -C 6 alkyl, C 5 -C 24 aryl, C 6 -C 24 aralkyl or vinyl.  
     
   
   
       6 . A process according to  claim 5 , wherein component (a) is a compound of formula II wherein L is a compound of formula V, VI, VII, VIII, IX, X, XI or XII wherein R 4 , R 5  and R 6  are hydrogen, methyl, amino, pyrrolidino or dimethylamino or L is a cation of the formula H—N + (R 7 ) 3  wherein R 7  is C 1 -C 6 alkyl.  
   
   
       7 . A process according to  claim 3 , wherein component (a) is a compound of formula I, II, III or IV wherein Ln is Eu, Tb, Dy, Sm or Nd.  
   
   
       8 . A process according to  claim 3 , wherein component (a) is a compound of formula II or III wherein R 1  and R 3  are methyl, t-butyl, n-pentyl or phenyl.  
   
   
       9 . A process according to  claim 3 , wherein component (a) is a compound of formula II wherein R 2  is hydrogen.  
   
   
       10 . A process according to  claim 3 , component (a) is a compound of formula XIII to LII  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       11 . A process according to  claim 1 , wherein component (b) is water, one or more water-miscible organic solvents or a mixture of water and one or more water-miscible organic solvents.  
   
   
       12 . A process according to  claim 11 , wherein the water-miscible organic solvent is an aliphatic alcohol, etheralcohol, glycol, aliphatic ketone, carboxylic acid ester, carboxylic acid amide, aliphatic nitrile, aliphatic polyether or aliphatic sulfoxide.  
   
   
       13 . A process according to  claim 11 , wherein the water-miscible organic solvent is selected from the group consisting of ethanol, 2-butoxyethanol, ethylene glycol, propylene glycol, acetone, 2-butanone, ethyl acetate, tetrahydrofurane (THF), dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), acetonitrile, polyethyleneglycol dimethylether and dimethylsulfoxide (DMSO).  
   
   
       14 . A process according to  claim 1 , wherein the composition contains 0.01 to 20.0% by weight of component (a) and 80.0 to 99.99% by weight of component (b), based on the total amount of components (a)+(b).  
   
   
       15 . A process according to  claim 1 , wherein the composition contains additionally (c) one or more colorants.  
   
   
       16 . A process for the preparation of luminescent plastics, wherein the plastics material is extruded in the presence of 0.01-10.0% by weight, based on the amount of polymeric material, of a compound of formula II or III according to  claim 3 .  
   
   
       17 . A luminescent textile fibre prepared by the process according to  claim 1 .  
   
   
       18 . A luminescent plastic prepared by the process according to  claim 16 .  
   
   
       19 . A process according to  claim 1  wherein the polymeric fibres are paper fibres or synthetic fibres.  
   
   
       20 . A method for the preparation of anti-counterfeit documents, cards, cheques or banknotes which comprises incorporating therein a luminescent polymeric fibre prepared by the process according to  claim 1.