Pigment particle growth and/or crystal phase directors

Abstract

Pigment particle growth and/or crystal phase directors of the following formula: (MO 3 S) m —Q—(CH 2 —(X)—(Y) n ) o wherein: Q represents a pigment moiety; M represents a metal cation, quaternary N cation or H; X is an aromatic group, a cyclo-hetero aliphatic group with at least one 5 atom or 6 atom ring or a hetero aromatic group with at least one 6 atom ring and which is not a phthalimido group; Y is a sulfonic or carboxylic acid or salt thereof; m and n independently from each other represent an integer from 0 to 2.5; and o is an integer from 0.05 to 4.

What is claimed:  
     
         1 . A compound of formula I  
       (MO 3 S) m —Q—[CH 2 —(X)—(Y) n ] o   (I)  
       wherein: 
 Q represents a pigment moiety;  
 M represents a metal cation, quaternary N cation or H;  
 X is an aromatic group, a cyclo-hetero aliphatic group with at least one 5 atom or 6 atom ring or a hetero aromatic group with at least one 6 atom ring and which is not a phthalimido group;  
 Y is a sulfonic or carboxylic acid or salt thereof;  
 m and n independently from each other are numbers from 0 to 2.5; and  
 o is a number from 0.05 to 4.  
 
     
     
         2 . A compound of    claim 1   , wherein said pigment moiety is a pigment selected from the group of anthraquinone, phthalocyanine, perinone, perylene, diketopyrrolopyrrole, thioindigo, iminoisoindoline, iminoisoindolinone, quinacridone, flavanthrone, dioxazine, indanthrone, anthrapyrimidine and quinophthalone pigments.  
     
     
         3 . A compound of    claim 1   , wherein the pigment moiety is a pigment selected from the group of quinacridone or diketopyrrolopyrrole pigments.  
     
     
         4 . A compound of    claim 1   , wherein the pigment is a quinacridone of the formula II:  
                   
       wherein A and D are independently substituents selected from H, F, Cl, C 1 -C 3 alkyl and C 1 -C 3 alkoxy.  
     
     
         5 . A compound of    claim 1   , wherein the pigment is an unsubstituted quinacridone.  
     
     
         6 . A compound of    claim 1   , wherein the metal cation M is sodium, potassium, calcium, magnesium or aluminum.  
     
     
         7 . A compound of    claim 1   , wherein X is an aromatic group selected from a 5 carbon or 6 carbon ring and a polycyclic groups comprising two to six fused 5 carbon and/or 6 carbon rings.  
     
     
         8 . A compound of    claim 7   , wherein said aromatic group is phenylene, naphthalene, anthracene, phenanthrene, pyrene or perylene.  
     
     
         9 . A compound of    claim 8   , wherein the aromatic group is a phenylene or naphthalene.  
     
     
         10 . A compound of    claim 1   , wherein X is a cyclo-hetero aliphatic group comprising at least one 5 or 6 atom ring.  
     
     
         11 . A compound of    claim 10   , wherein said cyclo-hetero aliphatic group is barbituric acid.  
     
     
         12 . A compound of    claim 1   , wherein said hetero-aromatic group which is not a phthalimido group comprises a 6 atom ring or fused 5 and/or 6 atom rings, and wherein said hetero-aromatic group contains 1 to 4 hetero atoms selected from N, S and/or O.  
     
     
         13 . A compound of    claim 12   , wherein said hetero-aromatic group is a pyridine, quinoline or carbazole group.  
     
     
         14 . A compound of    claim 1   , wherein said aromatic, cyclo-hetero aliphatic or hetero-aromatic group is optionally substituted with one or more halogen, oxy, hydroxy, imino, amino, C 1 -C 18 alkyl or C 1 -C 18  alkoxy groups.  
     
     
         15 . A compound of    claim 14   , wherein said aromatic, cyclo-hetero aliphatic or hetero-aromatic group is optionally substituted with one or more C 1 -C 3 alkyl or C 1 -C 3  alkoxy groups.  
     
     
         16 . A compound of    claim 1   , wherein said aromatic group is toluene, ortho- meta- or para-xylene, chlorobenzene, ortho- meta- or para-dichlorobenzene, 1- or 2-methyinaphthalene or anthraquinone.  
     
     
         17 . A compound of    claim 1   , wherein said hetero-aromatic group is derived from melamine, 1,3,7-trimethylxanthin, hydantoin, 2-methylbenzimidazole, 2,6,8-trihydroxypurine, 1,8-naphtosultam, o-benzoic acid sulfimide or 2,4-dihydroxyprimidine.  
     
     
         18 . A compound of    claim 1   , wherein Y is a free carboxylic acid or sulfonic acid group or a sodium, potassium, magnesium, calcium or aluminum salt thereof.  
     
     
         19 . A compound of    claim 18   , wherein Y is a free sulfonic acid group or a sodium, potassium or aluminum salt thereof.  
     
     
         20 . A composition containing a mixture of compounds of    claim 1   , wherein m represent is on average a number from 0-0.1, n is on average from 0-1.2, and o is on average a number from 0.2 to 1.5.  
     
     
         21 . A process for the preparation of a compound of    claim 1   , wherein: 
 A) dissolving a pigment of the pigment moiety Q in concentrated sulfuric acid;    B) adding and dissolving at temperature less than 50° C. the intermediate X to the solution;    C) adding para-formaldehyde at a temperature less than 50° C.;    D) heating the mixture of step C) to about 50 to about 100° C.;    E) isolating a precipitate from the reaction in step D.    
     
     
         22 . A process according to    claim 21    wherein the mixture is heated in step D for about 30 minutes to about 6 hours and wherein the process further comprises the step of drowning the reaction mixture from step D in water to provide a precipitate.  
     
     
         23 . A process according to    claim 21   , wherein the molar ratio of the pigment moiety Q:intermediate X:formaldehyde is 1:1 to 1.2:1 to 2.  
     
     
         24 . A process for the direct synthesis of a pigmentary grade anthraquinone, phthalocyanine, perinone, perylene, diketopyrrolopyrrole, thioindigo, iminoisoindoline, iminoisoindolinone, quinacridone, flavanthrone, dioxazine, indanthrone, anthrapyrimidine or quinophthalone pigment wherein said pigment is synthesized in the presence of 0.1 to 25 weight percent of a pigment particle growth and/or crystal phase director compound of    claim 1   , based on the weight pigment being synthesized.  
     
     
         25 . A process for the preparation of a direct pigmentary diketopyrrolopyrrole or quinacridone pigment or a solid solution thereof comprising the step of adding to the reaction mixture from which said pigment or solid solution is synthesized, 0.1 to 25 percent by weight of at least one compound of    claim 1   , based on the pigment being synthesized.  
     
     
         26 . A process according to    claim 25   , wherein said pigment or solid solution is quinacridone, 2,9-dichloroquinacridone, 4,11-dichloroquinacridone, 2,9-dimethylquinacridone pigment or solid solutions thereof.  
     
     
         27 . A method of improving the heat stability, rheological and flocculant properties of pigment particles, said method comprising adding to said pigment particles at least one compound of    claim 1    in an amount sufficient to reduce flocculation or improve the heat stability.