Phthalocyanines and Their Use In Ink-Jet Printers

Abstract

A mixture of phthalocyanine dyes of Formula (1) and salts thereof: wherein M is Cu or Ni; Pc represents a phthalocyanine nucleus; L is, for example, C 1-20 alkylene; R 1 , R 2 , R 3 and R 4 independently are H or optionally substituted C 1-4 alkyl; R 5 is H or an optionally substituted hydrocarbyl; or R 4 and R 5 together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system; x, y and z are each 0.1 to 3.8 where the sum of (x+y+z) is 4; and the substituents, represented by x, y and z, are attached only to a β-position on the phthalocyanine ring. This mixture can be used to make inks suitable for use in an ink jet printer.

1 .- 14 . (canceled) 
   
   
       15 . A process for forming an image on a substrate comprising applying a composition which is an ink suitable for use in an ink jet printer by means of an ink-jet printer,
 wherein the composition comprises a mixture of phthalocyanine dyes and a liquid medium,   wherein the phthalocyanine dyes are of a Formula (1) and salts thereof:   
     
       
         
         
             
             
         
       
       wherein:
 M is Cu or Ni; 
 Pc represents a phthalocyanine nucleus of formula; 
 
     
     
       
         
         
             
             
         
       
       
         L is optionally substituted C 1-20  alkylene, alkyenylene or alkynylene, optionally interrupted by —O—, —NH— or —S—: 
         R 1 , R 2 , R 3 , and R 4  independently are H or optionally substituted C 1-4 alkyl: 
         R 5  is H or an optionally substituted hydrocarbyl; or R 4  and R 5  together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system; 
         x is 0.1 to 3.8; 
         y is 0.1 to 3.8; 
         z is 0.1 to 3.8; 
         the sum of (x+y+z) is 4; 
         the substituents, represented by x, y and z, are attached only to a 13-position on the phthalocyanine ring; and 
         the mixture of dyes of Formula (1) are obtainable by a process which comprises cyclisation of β-sulfo substituted phthalic acid, phthalonitrile, iminoisoindoline, phthalic anhydride, phthalimide or phthalamide. 
       
     
   
   
       16 . A material printed with a composition comprising a mixture of phthalocyanine dyes and a liquid medium,
 wherein the phthalocyanine dyes are of a Formula (1) and salts thereof:   
     
       
         
         
             
             
         
       
       wherein:
 M is Cu or Ni; 
 Pc represents a phthalocyanine nucleus of formula: 
 
     
     
       
         
         
             
             
         
       
       
         L is optionally substituted C 1-20  alkylene, alkyenylene or alkynylene, optionally interrupted by —O—, —NH— or —S—: 
         R 1 , R 2 , R 3  and R 4  independently are H or optionally substituted C 1-4 alkyl; 
         R 5  is H or an optionally substituted hydrocarbyl: or R 4  and R 5  together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system; 
         x is 0.1 to 3.8; 
         y is 0.1 to 3.8: 
         z is 0.1 to 3.8; 
         the sum of (x+y+z) is 4; 
         the substituents, represented by x, y and z, are attached only to a β-position on the phthalocyanine ring; and 
         the mixture of dyes of Formula (1) are obtainable by a process which comprises cyclisation of β-sulfo substituted phthalic acid, phthalonitrile, iminoisoindoline, phthalic anhydride, phthalimide or phthalamide. 
       
     
   
   
       17 . An ink-jet printer cartridge comprising a chamber and a composition which is an ink wherein the composition is in the chamber and comprises a mixture of phthalocyanine dyes and a liquid medium, wherein the phthalocyanine dyes are of a Formula (1) and salts thereof: 
     
       
         
         
             
             
         
       
       wherein:
 M is Cu or Ni: 
 Pc represents a phthalocyanine nucleus of formula: 
 
     
     
       
         
         
             
             
         
       
       
         L is optionally substituted C 1-20 alkylene, alkyenylene or alkynylene, optionally interrupted by —O—, —NH— or —S—: 
         R 1 , R 2 , R 3  and R 4  independently are H or optionally substituted C 1-4 alkyl; 
         R 5  is H or an optionally substituted hydrocarbyl; or R 4  and R 5  together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system; 
         x is 0.1 to 3.8; 
         y is 0.1 to 3.8; 
         z is 0.1 to 3.8; 
         the sum of (x+y+z) is 4; 
         the substituents, represented by x, y and z, are attached only to a β-position on the phthalocyanine ring; and 
         the mixture of dyes of Formula (1) are obtainable by a process which comprises cyclisation of β-sulfo substituted phthalic acid, phthalonitrile, iminoisoindoline, phthalic anhydride, phthalimide or phthalamide. 
       
     
   
   
       18 . A material printed with a mixture of phthalocyanine dyes, wherein the phthalocyanine dyes are of a Formula (1) and salts thereof: 
     
       
         
         
             
             
         
       
       wherein:
 M is Cu or Ni; 
 Pc represents a phthalocyanine nucleus of formula; 
 
     
     
       
         
         
             
             
         
       
       
         L is optionally substituted C 1-20  alkylene, alkyenylene or alkynylene, optionally interrupted by —O—, —NH— or —S—; 
         R 1 , R 2 , R 3  and R 4  independently are H or optionally substituted C 1-4 alkyl; 
       
       R 5  is H or an optionally substituted hydrocarbyl; or R 4  and R 5  together with the nitrogen atom to which they are attached represent an optionally substituted aliphatic or aromatic ring system;
 x is 0.1 to 3.8; 
 y is 0.1 to 3.8; 
 z is 0.1 to 3.8; 
 the sum of (x+y+z) is  4 ; 
 the substituents, represented by x, y and z, are attached only to a β-position on the phthalocyanine ring; and 
 the mixture of dyes of Formula (1) are obtainable by a process which comprises cyclisation of β-sulfo substituted phthalic acid, phthalonitrile, iminoisoindoline, phthalic anhydride, phthalimide or phthalamide.