Dye compositions

Details Dye compositions Dye compositions

1998-12-15

2001-05-15

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031580

Reexamination Certificate

active

06231653

ABSTRACT:

COMPOSITIONS
This invention relates to compositions, to inks and to their use in ink jet printing (“IJP”). IJP is a non-impact printing technique in which droplets of ink are ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
There are many demanding performance requirements for dyes and inks used in IJP. For example they desirably provide sharp, non-feathered images having good water-fastness and optical density. The inks are often required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jet nozzle because this will stop the printer from working. The inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle and they should not fade too quickly when printed onto substrates.
Meeting all of these requirements has proved difficult in practice and an improvement to one feature can often lead to a loss in performance of another.
We have now derived a composition which improves the light-fastness of prints prepared by IJP. This can enable inks to be prepared from dyes having hitherto unacceptable light fastness properties. In this way one has much greater flexibility in choosing dyes for ink jet printers. Furthermore, the composition can be used to improve the light fastness of dyes which are already acceptable in the home or office environment so they may be used outdoors where exposure to light is much greater, e.g. on billboards and posters.
According to the present invention there is provided an ink composition comprising:
(a) from 0.1 to 50 parts of a dye;
(b) from 0.1 to 50 parts of a sugar;
(c) from 0.1 to 50 parts of a compound selected from phosphoric acid and a carboxylic acid or a salt thereof;
(d) from 0 to 10 parts of a pH buffer; and
(e) from 10 to 99 parts of a liquid medium;
wherein all parts are by weight and the total number of parts (a) + (b) + (c) + (d) + (e) = 100.
The number of parts of component (a) is preferably from 0.5 to 40, more preferably 1 to 30, especially 2 to 20, more especially 2 to 15.
The number of parts of component (b) is preferably from 0.5 to 40, more preferably 1 to 30, especially 1.5 to 25, more especially 2 to 20.
The number of parts of component (c) is preferably from 0.5 to 40, more preferably 0.2 to 10, especially 0.2 to 5, more especially 0.5 to 5.
The number of parts of component (d) is preferably from 0 to 5, more preferably 0 to 3, especially 0 to 2, more especially 0 to 1.
The number of parts of component (e) is preferably from 50 to 99, more preferably 0 to 99, especially 80 to 95, more especially 85 to 95.
Preferably component (c) is a carboxylic acid, more preferably an aliphatic or aromatic carboxylic acid. The acid may contain a single carboxy group or two or more carboxy groups, more preferably it contains from I to 5 and especially 1 to 4 carboxy groups. Optionally the acid is further substituted by one or more atom or group(s) other than carboxy.
Preferred aliphatic carboxylic acids contain up to 20, more preferably 2 to 15 and especially 2 to 10 carbon atoms. The aliphatic carboxylic acid may be saturated or unsaturated.
Preferred saturated aliphatic acids are alkane derivatives and preferred unsaturated aliphatic acids are alkene and alkyne derivatives. The alkane, alkene and alkyne groups from which the aliphatic acids are derived may be straight chain, branched chain or cyclic and are optionally interrupted by one or more groups or heteroatoms. Preferred interrupting atoms and groups are selected from —O—, —S—, —NR
1
-, phenyl, piperazine, —C(O)O and —C(O)—; wherein R
1
is H, alkyl or phenyl.
When the aliphatic carboxylic acid is further substituted by one or more atom or group other than carboxy, the substituent(s) are preferably selected from —OH, —NH
2
, —NO
2
—SH, —SO
3
H, —PO
3
H
2
, halo (preferably —F or —Cl), Cl—calkyl, C
1-4
-hydroxyalkyl, C,
4
-alkoxy and C
1-4
-hydroxyalkoxy. It is especially preferred that the aliphatic acid is further substituted by one or more group(s) selected from —OH, —SO
3
H and —PO
3
H
2
. More especially the acid is further substituted by one or more —OH group(s).
Preferred saturated aliphatic acids which carry a single carboxy group include for example, acetic acid, phosphonoacetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, dodecanoic acid and cyclohexanecarboxylic acid.
Preferred saturated aliphatic acids which carry two or more carboxy groups include for example, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid azelaic acid, 1,2,3,4-butanetetracarboxylic acid, ethylenediamine tetraacetic acid, diglycolic acid, iminodiacetic acid 1,1-cyclohexane diacetic acid and nitriliotriacetic acid.
Preferred unsaturated aliphatic acids include for example, maleic acid, fumaric acid and citraconic acid.
Preferred aliphatic acids which carry one or more —OH groups include for example, glycolic acid, lactic acid, tartronic acid, malic add, citric acid, tartaric acid, ascorbic acid and mucic acid.
When the acid is an aromatic carboxylic acid it is preferably a monocyclic or polycyclic aromatic or heteroaromatic group which is substituted by one or more carboxy group or a group which carries a carboxy group.
Preferred monocyclic aromatic groups include optionally substituted benzene, pyridine, pyridone, thiophene and furan groups.
Preferred polycyclic aromatic groups include a polycyclic aromatic group wherein the cyclic rings are fused together or linked by a single covalent bond or a linker group. Preferred linker groups include —O—, —S—, —NR
a
-, —C(O)—, alkylene and alkenylene groups, wherein R
a
is H or C
1-4
-alkyl.
Preferred polycyclic aromatic groups wherein the cyclic rings are fused together include optionally substituted naphthalene, quinoline, indoline and benzofuran.
Preferred polycyclic aromatic groups wherein the cyclic rings are linked by a single covalent bond or a linker group include biphenyl, stillbene and diphenylmethane.
When the aromatic acid is substituted by a group which carries a carboxy group, the substituent is preferably carboxy substituted alkyl, more preferably C
1
,
6
-carboxyalkyl.
When the aromatic group is further substituted by an atom or group other than carboxy or a group which carries a carboxy group, the preferred substituents are selected from halogen (especially F or Cl); —NO
2
; —CF
3
; —CN; —SO
3
H, —PO
3
H
2
; or a C
1-6
-alkyl, C
2-6
-alkenyl, C
5-8
-cycloalkyl or C
1-6
-calkoxy group optionally substituted by —OH, —NH
2
, —NO
2
-SO
3
H, —PO
3
H
2
or halogen; a group of the formula —SR
2
, or —COOR
2
wherein R
2
is H, C
1-4
-alkyl, C
5-8
-cycloalkyl or phenyl; and groups of the formula —OR
3
, —COR
3
; —NR
3
R
4
, -SO
2
NR
3
R
4
, —SOR
3
1
—SO
2
R
3
, —NR
3
COR
4
, —CONR
3
R
4
, or —OCOR
3
, wherein R
3
and R
4
each independently is H, C
1-4
-alkyl, C
5-8
-cycloalkyl, phenyl or R
3
and R
4
together with the nitrogen to which they are attached form a 5 or 6 membered ring, for example piperazine or morpholine.
Especially preferred aromatic carboxylic acids are naphthalene or benzene derivatives which carry one or more carboxy group and optionally one or more group(s) selected from —OH, —SO
3
H and —PO
3
H
2
(especially one or more —OH group(s)).
Examples of preferred aromatic acids which carry one or more carboxy group include for example, pyromellitic acid, trimesic acid, trimellitic acid, 4-sulphophthalic acid, 3,5-disulphobenzoic acid, phthalic acid, isophthalic acid, terephthalic acid and p- mercaptobenzoic acid.
Examples of preferred aromatic acids which carry one or more carboxy group and one or more -OH group include for example thiosalicylic acid and sulphosalicylic acid.
Especially preferred carboxylic acids are aliphatic carboxylic acids with from 2 to carbon atoms and which are optionally substituted by one or more —OH group. More especially the acid is selected from acsorbic acid, succinic acid and citric acid.
When component (c) is in the form of a sa

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