Ink jet ink and recording material

Abstract

The present invention relates to an ink jet ink, an ink jet recording material or an ink jet system comprising at least one sterically hindered N-hydroxylamine strong acid salt, for example 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium chloride or bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate dihydrochloride; or comprising at least one dialkyl N-hydroxylamine salt, for example chloride, bisulfate, sulfate, phosphate, nitrate, ascorbate, formate, acetate, benzoate, oxalate, citrate, a carboxylate of ethylenediaminetetraacetic acid or of diethylenetriaminepentaacetic acid or polyacrylate salts of N,N-diethylhydroxylamine, N,N-bis(2-hydroxypropyl)hydroxylamine, N,N-bis(3-hydroxypropyl)hydroxylamine, N,N-dibenzylhydroxylamine or the N,N-di(alkyl)hydroxylamine produced by the direct oxidation of N,N-di(hydrogenated tallow)amine.

1 . An ink jet ink or ink jet recording material comprising at least one sterically hindered N-hydroxylamine strong acid salt of the formula  
     
       
         
         
             
             
         
       
     
     wherein 
 G 1  and G 2  are independently alkyl of 1 to 4 carbon atoms or are together pentamethylene;  
 Z 1  and Z 2  are each methyl, or Z 1  and Z 2  together form an unsubstituted linking moiety or a linking moiety substituted by one or more groups selected from an ester, ether, hydroxy, oxo, cyanohydrin, amide, amino, carboxy or an urethane group,  
 X is an anion of a strong acid,  
 wherein the total charge of cations h is equal to the total charge of anions j, and  
 wherein the strong acid has a pKa <about 4.  
 
   
   
       2 . An ink jet ink or ink jet recording material according to  claim 1  comprising at least one sterically hindered N-hydroxylamine strong acid salt.  
   
   
       3 . An ink jet ink or ink jet recording material according to  claim 2  where the strong acid is a mineral acid, sulfuric acid, methanesulfonic acid or phosphoric acid.  
   
   
       4 . An ink jet ink or ink jet recording material according to  claim 2  where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     wherein 
 R is hydrogen or methyl; and  
 in formula A*,  
 n is 1 or 2, and  
 when n is 1,  
 R 1  is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R 1  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO − ) n M n+  where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group N n+ (R 2 ) 4  where R 2  is alkyl of 1 to 8 carbon atoms or benzyl,  
 when n is 2,  
 R 1  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups;  
 in formula B*,  
 m is 1 to 4, and  
 when m is 1,  
 R 2  is alkyl of 1 to 18 carbon atoms, alkyl of 3 to 18 carbon atoms interrupted by —COO—, alkyl of 3 to 18 carbon atoms substituted by COOH or COO—, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 3  where n is 1 to 12, or R 2  is cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl groups of 1 to 4 carbon atoms, or R 2  is —NHR 3  where R 3  is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aryl of 6 to 12 carbon atoms, or said aryl substituted by one to four alkyl of 1 to 4 carbon atoms, or R 2  is —N(R 3 ) 2  where R 3  is as defined above,  
 when m is 2,  
 R 2  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene, alkylene of 2 to 12 carbon atoms interrupted by —COO—, alkylene of 3 to 18 carbon atoms substituted by COOH or COO—, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 2 — where n is 1 to 12, or R 2  is cycloalkylene of 5 to 12 carbon atoms, aralkylene of 7 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or R 2  is —NHR 4 NH— where R 4  is alkylene of 2 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or R 2  is —N(R 3 )R 4 N(R 3 )— where R 3  and R 4  are as defined above, or R 2  is —CO— or —NH—CO—NH—,  
 when m is 3,  
 R 2  is alkanetriyl of 3 to 8 carbon atoms or benzenetriyl, or  
 when m is 4,  
 R 2  is alkanetetrayl of 5 to 8 carbon atoms or benzenetetrayl,  
 in formula C*,  
 R 10  is hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, alkanoyl of 2 to 18 carbon atoms, alkenoyl of 3 to 5 carbon atoms or benzoyl,  
 x is 1 or 2, and  
 when x is 1,  
 R 11  is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, propargyl, glycidyl, alkyl of 2 to 50 carbon atoms interrupted by one to twenty oxygen atoms, said alkyl substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R 11  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl, or where Z is said alkyl substituted by —(COO − ) n M n+  where n is 1-3 and M is a metal ion from the 1st, 2nd or 3rd group of the periodic table or is Zn, Cu, Ni or Co, or M is a group N n+ (R 2 ) 4  where R 2  is hydrogen, alkyl of 1 to 8 carbon atoms or benzyl, or  
 when x is 2,  
 R 11  is alkylene of 1 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, xylylene or alkylene of 1 to 50 carbon atoms interrupted by one to twenty oxygen atoms, substituted by one to ten hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,  
 in formula D*,  
 y is 1 to 4,  
 R 10  is as defined above, and  
 R 12  is defined as R 2  above,  
 in formula H*,  
 p is 1 or 2,  
 T 4  is as defined for R 11  when x is 1 or 2,  
 M and Y′ are independently methylene or carbonyl,  
 in formula I*,  
 this formula denotes a recurring structural unit of a polymer where T 1  is ethylene or 1,2-propylene or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate, and where  
 q is 2 to 100,  
 Q 1  is —N(R 3 )— or —O— where R 3  is as defined above,  
 in formula J*,  
 r is 1 or 2,  
 T 7  is as defined for R 1  when n is 1 or 2 in formula A*,  
 wherein in formulae X* to CC*,  
 h is 2 or 3,  
 G 1  is hydrogen, methyl, ethyl, butyl or benzyl,  
 m is 1 to 4,  
 x is 1 to 4,  
 when x is 1,  
 R 1  and R 2  are independently alkyl of 1 to 18 carbon atoms, said alkyl interrupted by one to five oxygen atoms, said alkyl substituted by 1 to 5 hydroxyl groups or said alkyl both interrupted by said oxygen atoms and substituted by said hydroxyl groups; cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 8 carbon atoms, or R 1  is also hydrogen, or R 1  and R 2  are together tetramethylene, pentamethylene, hexamethylene or 3-oxapentamethylene,  
 when x is 2,  
 R 1  is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or said alkyl both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,  
 R 2  is alkylene of 2 to 18 carbon atoms, said alkylene interrupted by one to five oxygen atoms, said alkylene substituted by 1 to 5 hydroxyl groups or said alkylene both interrupted by said oxygen atoms and substituted by said hydroxyl groups; o-, m- or p-phenylene or said phenylene substituted by one or two alkyl of 1 to 4 carbon atoms, or R 2  is —(CH 2 ) k O[(CH 2 ) k O] h (CH 2 ) k — where k is 2 to 4 and h is 1 to 40, or R 1  and R 2  together with the two N atoms to which they are attached are piperazin-1,4-diyl,  
 when x is 3,  
 R 1  is hydrogen,  
 R 2  is alkylene of 4 to 8 carbon atoms interrupted by one nitrogen atom,  
 when x is 4,  
 R 1  is hydrogen,  
 R 2  is alkylene of 6 to 12 carbon atoms interrupted by two nitrogen atoms,  
 R 3  is hydrogen, alkyl of 1 to 8 carbon atoms, said alkyl interrupted by one or two oxygen atoms, said alkyl substituted by a hydroxyl group, or both interrupted by one or two oxygen atoms and substituted by a hydroxyl group,  
 p is 2 or 3, and  
 Q is an alkali metal salt, ammonium or N + (G 1 ) 4 , and  
 in formula DD*,  
 m is 2 or 3,  
 when m is 2,  
 G is —(CH 2 CHR—O) r CH 2 CHR—, where r is 0 to 3, and R is hydrogen or methyl, and  
 when m is 3,  
 G is glyceryl.  
 
   
   
       5 . An ink jet ink or ink jet recording material according to  claim 4  where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formulae A*, B*, C*, D*, S*, X*, Y* and Z*, 
 wherein    R is hydrogen,    in formula A*,    n is 1 or 2,    when n is 1,    R 1  is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2-6 carbon atoms, propargyl, glycidyl, alkyl of 2 to 20 carbon atoms interrupted by one to ten oxygen atoms, said alkyl substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R 1  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by —COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,    when n is 2,    R 1  is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, alkylene of 1 to 20 carbon atoms interrupted by one to ten oxygen atoms, substituted by one to five hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups,    in formula B*,    m is 1 or 2,    when m is 1,    R 2  is alkyl of 1 to 4 carbon atoms or R 2  is CH 2 (OCH 2 CH 2 ) n OCH 3  where n is 1 to 12, or R 2  is phenyl, or said phenyl substituted by one to three methyl groups, or R 2  is —NHR 3  where R 3  is alkyl of 1 to 4 carbon atoms or phenyl, or said phenyl substituted by one or two methyl groups,    when m is 2,    R 2  is alkylene of 1 to 8 carbon atoms, alkenylene of 4 to 8 carbon atoms, or R 2  is —CH 2 (OCH 2 CH 2 ) n OCH 2 — where n is 1 to 12, or R 2  is NHR 4 NH where R 4  is of 2 to 6 carbon atoms, aralkylene of 8 to 15 carbon atoms or arylene of 6 to 12 carbon atoms, or R 2  is —CO— or —NHCONH,    in formula C*,    R 10  is hydrogen or, alkanoyl of 1 to 3 carbon atoms,    x is 1 or 2,    when x is 1,    R 11  is hydrogen, alkyl of 1 to 6 carbon atoms or glycidyl, or R 11  is alkyl of 1 to 4 carbon atoms substituted by a carboxy group or by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,    when x is 2,    R 1 , is alkylene of 1 to 6 carbon atoms,    in formula D*,    R 10  is hydrogen,    y is 1 or 2,    R 12  is defined as R 2  above,    in formula Y* and Z*,    x is 1 or 2,    when x is 1,    R 1  and R 2  are independently alkyl of 1 to 4 carbon atoms or R 1  and R 2  are together tetramethylene, or pentamethylene, R 2  is hydrogen or alkyl of 1 to 4 carbon atoms, said alkyl group substituted by a hydroxyl group,    when x is 2,    R 1  is hydrogen, alkyl of 1 to 4 carbon atoms, said alkyl substituted by a hydroxyl group,    R 2  is alkylene of 2 to 6 carbon atoms, and    R 3  is as defined above.    
   
   
       6 . An ink jet ink or ink jet recording material according to  claim 4  where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formulae A*, B*, C* and D*,  
     wherein 
 R is hydrogen,  
 in formula A*,  
 n is 1,  
 R 1  is hydrogen, alkyl of 1 to 4 carbon atoms, glycidyl, alkyl of 2 to 4 carbon atoms interrupted by one or two oxygen atoms, said alkyl substituted by one or two hydroxyl groups or both interrupted by said oxygen atoms and substituted by said hydroxyl groups, or R 1  is alkyl of 1 to 4 carbon atoms substituted by —COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,  
 in formula B*,  
 m is 1 or 2,  
 R 2  is alkyl of 1 to 4 carbon atoms or R 2  is CH 2 (OCH 2 CH 2 ) n OCH 3  where n is 1 to 4,  
 when m is 2,  
 R 2  is alkylene of 1 to 8 carbon atoms,  
 in formula C*,  
 R 10  is hydrogen or alkanoyl of 1 or 2 carbon atoms,  
 x is 1 or 2,  
 when x is 1,  
 R 11  is hydrogen, alkyl of 1 to 4 carbon atoms or glycidyl,  
 R 11  is alkyl of 1 to 4 carbon atoms substituted by COOZ where Z is hydrogen or alkyl of 1 to 4 carbon atoms,  
 when x is 2,  
 R 11  is alkylene of 1 to 6 carbon atoms,  
 in formula D*,  
 R 10  is hydrogen,  
 y is 1 or 2,  
 R 12  is defined as R 2  above.  
 
   
   
       7 . An ink jet ink or ink jet recording material according to  claim 4  where the sterically hindered N-hydroxylamine strong acid salts are selected from the group consisting of formula B* where X is chloride or bromide.  
   
   
       8 . An ink jet ink or ink jet recording material according to  claim 4  where the sterically hindered N-hydroxylamine strong acid salts are 1-hydroxy-2,2,6,6-tetramethyl-4-hydroxypiperidinium chloride or bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate dihydrochloride.  
   
   
       9 - 14 . (canceled)  
   
   
       15 . An ink jet ink according to  claim 1  which comprises about 0.01 to about 30% by weight of at least one sterically hindered N-hydroxylamine strong acid salt, based on the weight of the ink jet ink.  
   
   
       16 . An ink jet recording material according to  claim 1  which comprises about 1 to about 10000 mg/m 2  of at least one sterically hindered N-hydroxylamine strong acid salt.  
   
   
       17 . An ink jet ink or ink jet recording material according to  claim 1  further comprising a UV absorber selected from the group consisting of the hydroxyphenylbenzotriazoles, the tris-aryl-s-triazines, the benzophenones, α-cyanoacrylates, the oxanilides, the benzoxazinones, the benzoates and the α-alkyl cinnamates.  
   
   
       18 . An ink jet ink or ink jet recording material according to  claim 1  further comprising a UV absorber selected from the group consisting of the hydroxyphenylbenzotriazoles, the tris-aryl-s-triazines and the benzophenones.  
   
   
       19 . An ink jet ink or ink jet recording material according to  claim 1  further comprising a UV absorber selected from the group consisting of 
 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;    2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;    2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;    2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole;    2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole;    2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;    2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole;    2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole-5-sulfonic acid, sodium salt;    3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamic acid;    12-hydroxy-3,6,9-trioxadodecyl 3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamate;    octyl 3-tert-butyl-4-hydroxy-5-(2H-benzotriazol-2-yl)-hydrocinnamate;    2-(3-t-butyl-2-hydroxy-5-(2-(ω-hydroxy-octa-(ethyleneoxy)carbonyl-ethyl)-phenyl)-2H-benzotriazole;    4,6-bis(2,4-dimethylphenyl)-2-(4-octyloxy-2-hydroxyphenyl)-s-triazine;    2,4-bis(2-hydroxy-4-butyloxyphenyl)-6-(2,4-bis-butyloxyphenyl)-1,3,5-triazine;    2-[4-(dodecyloxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)1,3,5-triazine;    the reaction product of tris(2,4-dihydroxyphenyl)-1,3,5-triazine with the mixture of α-chloropropionic esters (made from isomer mixture of C 7 -C 9 alcohols);    2,4-dihydroxybenzophenone;    2,2′,4,4′-tetrahydroxy-5,5′-disulfobenzophenone, disodium salt;    2-hydroxy-4-octyloxybenzophenone;    2-hydroxy-4-dodecyloxybenzophenone;    2,4-dihydroxybenzophenone-5-sulfonic acid and salts thereof;    2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof;    2,2′-dihydroxy-4,4′dimethoxybenzophenone-5,5′-disodium sulfonate;    3-(2H-benzotriazol-2-yl)-4-hydroxy-5-sec-butylbenzenesulfonic acid, sodium salt; and    2-(2′-hydroxy-3′-tert-butyl-5′-polyglycolpropionate-phenyl)benzotriazole.    
   
   
       20 . An ink jet system, comprising a recording material and at least one colored ink to be applied to the recording material by means of an ink jet nozzle, wherein at least either the recording material or at least one colored ink comprises at least one sterically hindered N-hydroxylamine strong acid salt according to  claim 1 .  
   
   
       21 . A process for stabilizing ink jet prints, 
 which process comprises applying to a recording material for ink jet printing an ink composition comprising    an aqueous or an organic solvent dye solution and    at least one sterically hindered N-hydroxylamine strong acid salt according to  claim 1  and    drying said recording material.    
   
   
       22 . A process for stabilizing ink jet prints, 
 which process comprises applying to a recording material for ink jet printing    a casting or coating dispersion or an aqueous or organic solution comprising    at least one sterically hindered N-hydroxylamine strong acid salt according to  claim 1  and    further applying either an ink composition comprising    an aqueous or an organic solvent dye solution, or an ink composition comprising an aqueous or an organic solvent dye solution and at least one sterically hindered N-hydroxylamine strong acid salt according to  claim 1  and    drying said recording material.