Bleed reduction agents for ink printing inks

Details Bleed reduction agents for ink printing inks Bleed reduction agents for ink printing inks

1999-08-05

2001-07-03

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031770, C544S197000, C544S198000, C544S208000, C544S209000, C544S211000, C544S212000, C544S218000, C544S217000, C544S219000, C544S180000, C544S298000, C544S299000, C544S300000, C544S301000, C544S302000, C544S303000, C544S304000, C544S310000, C544S311000, C544S313000, C544S314000, C544S316000, C544S317000, C544S318000, C544S321000, C544S324000, C544S325000, C544S328000, C544S329000, C544S331000

Reexamination Certificate

active

06254669

ABSTRACT:

The present invention relates to compounds which reduce colour bleed in ink jet printing inks and to inks incorporating such compounds.
A problem associated with certain ink jet printing processes is that colour can bleed between different coloured regions of the printed substrate. When colour bleed occurs, the boundary between adjacent coloured regions becomes indistinct or blurred, resulting in a low resolution printed image. To produce high resolution colour images using ink jet printing there is a need for inks which exhibit low colour bleed.
Prior solutions to the problem of colour bleed have involved the addition of large quantities of surfactant to the inks to enhance the penetration of the ink into the substrate used for printing. However, the presence of large quantities of surfactant in the ink may reduce the optical density of the printed image and can result in the ink being visible on the opposite side of the paper. Both of these effects reduce the print quality of the image.
EP 0,534,635 discloses a method for reducing colour bleed by using colorants which become insoluble under defined pH conditions. U.S. Pat. No. 5,198,023 discloses the use of a multivalent salt in yellow inks containing a cationic dye, the salt acting as a precipitating agent for anionic dyes contained in differently coloured inks. Both of these methods control colour bleed by causing the colorant present in an ink to precipitate when the ink contacts another ink of a different colour on the printed substrate. The degree of colour bleed reduction obtained using these methods is controlled primarily by the speed of the precipitation reaction at the interface between the differently coloured regions on the printed substrate.
According to a first aspect of the present invention there is provided a compound of the Formula (1) and salts thereof:
wherein:
Ar and Ar
1
each independently is an optionally substituted aromatic group and at least one of Ar and Ar
1
carries at least one group selected from —COOH and —PO
3
H
2
;
J and J
1
each independently is —O—, —S—, —NR
1
— or a group of the Formula (2) or (3):
V and V
1
each independently is —O—, —S— or —NR
1
—;
X and X
1
each independently is a group of the Formula (4), (5) or (6):
T is —OR
2
, —SR
2
, —NR
3
R
4
or a labile atom or group;
Y is H, CN or T;
E is Cl or CN;
each R
1
independently is H or optionally substituted alkyl;
R
2
, R
3
and R
4
each independently is H, alkenyl, substituted alkenyl, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl or substituted cycloalkyl, or R
3
and R
4
together with the nitrogen atom to which they are attached form a 5 or 6 membered ring;
W and W
1
each independently is —O—, —S—, or —NR
5
—;
R
5
is H or optionally substituted alkyl; or the group —NR
5
— is an optionally substituted piperazinylene group;
L is a divalent organic linking group; or
the group —WLW
1
— forms an optionally substituted piperazinylene group; and
m is 0, 1 or 2.
Ar and Ar
1
are preferably optionally substituted monocyclic or polycyclic aromatic groups containing up to 10 carbon atoms and optionally contain one or more heteroatoms.
Preferred monocyclic aromatic groups are optionally substituted phenyl, pyridyl, thiophenyl and furanyl groups. Preferred polycyclic aromatic groups are optionally substituted naphthyl, quinolinyl, indolinyl, benzthiophenyl, benzofuranyl and bi-phenyl groups.
The optional substituents on Ar and Ar
1
are preferably selected from carboxy; halogen; —NO
2
; —CF
3
; —CN; —PO
3
H
2
; a C
1-6
-alkyl, C
2-6
-alkenyl, C
5-8
-cycloalkyl or C
1-6
-alkoxy group optionally substituted by —OH, —NH
2
, —NO
2
, —SO
3
H or halogen; and groups of the formula —OR
6
, —COR
6
; —SR
6
, —NR
6
R
7
, —SO
2
NR
6
R
7
, —NR
6
COR
7
, —CONR
6
R
7
, or —OCOR
6
, wherein R
6
and R
7
each independently represent H, C
1-4
-alkyl, C
5-8
-cycloalkyl, phenyl or R
6
and R
7
together with the nitrogen to which they are attached form a 5 or 6 membered ring, preferably morpholine or piperazine.
More preferably the optional substituents on Ar and Ar
1
are selected from —COOH, —SO
3
H, —PO
3
H
2
, —OH, —NH
2
, C
1-4
-hydroxyalkyl, —Cl, C
1-4
-alkyl, C
1-4
-alkoxy and hydroxy —C
1-4
-alkoxy, provided always that at least one of Ar and Ar
1
carries at least one group selected from —COOH and —PO
3
H
2
.
It is preferred that at least one of Ar and Ar
1
carry at least one carboxy group.
Ar and Ar
1
are preferably independently selected from substituted naphthyl and substituted phenyl, especially substituted phenyl (in either case at least one of Ar and Ar
1
carries at least one group selected from —COOH and PO
3
H
2
). It is preferred that both Ar and Ar
1
carry at least one, more preferably two carboxy substituents. Accordingly, in a preferred embodiment of the present invention, Ar and Ar
1
each independently represent a group of the Formula (7):
wherein:
n is 1 or 2; and
A is H, alkyl, substituted alkyl, alkoxy, substituted alkoxy, halogen, —SO
3
H, —PO
3
H
2
, —OR
6
or —NR
6
R
7
, wherein R
6
and R
7
are as hereinbefore defined.
A is preferably selected from H, C
1-4
-alkyl, substituted C
1-4
-alkyl, C
1-4
-alkoxy, substituted C
1-4
-alkoxy, halogen (especially Cl), —OH, —PO
3
H
2
, —NR
6
R
7
and —SO
3
H. More preferably A is selected from H, C
1-4
-alkyl, C
1-4
-hydroxyalkyl, —SO
3
H, —PO
3
H
2
, —OH, —Cl, —C
1-4
-alkoxy and hydroxy —C
1-4
-alkoxy. It is especially preferred that A is H.
Preferably n is 2. When n is 2, preferably the two —COOH groups are meta with respect to the groups represented by J and J
1
in Formula (1).
Each R
1
is preferably independently selected from H, C
1-4
-alkyl or C
1-4
-alkyl substituted by —OH, —SO
3
H or COOH, more preferably H or C
1-4
-alkyl and especially H, methyl and ethyl.
Preferably the groups represented by V and V
1
are each independently —O— or a group of the formula —NR
1
—, wherein R
1
is as hereinbefore defined, more preferably —NH—.
When X or X
1
is of the Formula (5) it is preferred that T is attached to the carbon atom between the two ring nitrogen atoms and that Y is para with respect to T. It is, however, preferred that X and X
1
each independently is of the Formula (4).
R
2
, R
3
and R
4
are preferably independently selected from H, optionally substituted C
2-10
-alkenyl, optionally substituted C
1-20
-alkyl, optionally substituted phenyl, optionally substituted phenyl-(C
1-4
-alkylene) and optionally substituted C
5-8
-cycloalkyl; more preferably H, optionally substituted C
1-18
-alkyl, allyl, phenyl, benzyl, phenylethyl and cyclohexyl; and especially H, optionally substituted C
1-12
-alkyl, allyl, phenyl, benzyl, and cyclohexyl.
Substituents which may be present on R
2
, R
3
and R
4
are preferably independently selected from C
1-6
-alkyl (preferably C
1-4
-alkyl); C
1-6
-alkoxy (preferably methoxy and ethoxy); halogen, (preferably Cl and Br); hydroxy; nitro; —CN; —CF
3
; —NH
2
, —SO
3
H and —COOR wherein R is H, C
1-4
-alkyl or phenyl. It is especially preferred that the substituents are independently selected from —OH and COOH.
R
2
is preferably selected from H, C
1-12
-alkyl or C
1-12
-alkyl substituted by —OH, carboxy or sulpho. More preferably R
2
is H or C
1-10
-alkyl substituted by —OH, carboxy or sulpho and especially H, methyl, ethyl, n-propyl, carboxyethyl and sulphopropyl.
When T
4
is a labile atom or group, it is preferably an atom or group which is bound by a chemical bond to the compound of Formula (1) which is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the compound of Formula (11) and cellulose.
Preferred labile atoms and groups represented by T include halogen atoms (preferably F and Cl); thiocyano groups; quaternary ammonium groups, for example trialkylammonium groups and optionally substituted pyridinium groups.
Preferably T is —OR
2
, —SR
2
, —NR
2
R
3
or Cl, more preferably —OR
2
, —SR
2
or —NR
2
R
3
wherein R
2
and R
3
are as hereinbefore defined.
When T is —NR
3
R
4
, it is preferred that R
3
and R
4
are ea

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