Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2000-09-29
2002-10-08
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C534S795000, C427S466000, C428S195100
Reexamination Certificate
active
06461416
ABSTRACT:
This invention relates to compositions, dyes, cartridges, ink jet printers and to their use in ink jet printing.
Ink jet printing methods involve a non-impact printing technique for printing an image onto a substrate using ink droplets 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 ink jet printer. For example they should desirably exhibit some or all of the following properties. They should provide sharp, non-feathered images having good water-fastness, light fastness and/or 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. The most popular ink jet printers are the thermal and piezoelectric ink jet printers.
We have now found that very good ink jet printing inks may be prepared having the compositions defined below using a specific class of dyes that give stable dye resin inks with some or all of these advantageous properties.
According to the present invention there is provided a composition comprising water, a water-dissipatable polymer and one or more dyes of Formula (1):
wherein:
R
1
and D are each independently H or a substituent;
R
2
and R
3
are each independently optionally substituted alkyl, aryl or aralkyl, or R
2
and R
3
together with the carbon atom to which they are attached form an optionally substituted ring;
R
4
and R
5
are each independently H or optionally substituted alkyl, aryl or aralkyl; and
R
6
is optionally substituted alkyl, aryl or aralkyl.
When R
1
or D is a substituent it is preferably halo; optionally substituted alkyl, aryl or aralkyl; or a group of formula —X—R
7
wherein X is O, S, SO, SO
2
or NR
8
wherein R
7
and R
8
are each independently H or optionally substituted alkyl, aryl or aralkyl.
When R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
or R
8
is optionally substituted alkyl it is preferably optionally substituted C
1-6
-alkyl.
When R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
or R
8
is optionally substituted aryl it is preferably optionally substituted C
6-12
-aryl, more preferably optionally substituted phenyl or naphthyl.
When R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
or R
8
is optionally substituted aralkyl it is preferably optionally substituted benzyl or xylyl.
R
1
and D are preferably each independently H, optionally substituted C
1-6
-alkyl, or a group of formula —X—R
7
wherein X is O, S, SO, SO
2
or NR
8
wherein R
7
and R
8
are each independently H or optionally substituted C
1-6
-alkyl.
X is preferably O, S or NR
8
wherein R
8
is H or C
1-6
-alkyl.
R
2
and R
3
are preferably each independently optionally substituted C
1-6
-alkyl, or R
2
and R
3
together with the carbon atom to which they are attached form an optionally substituted 5- or 6-membered ring, especially an optionally substituted cyclopentane or cyclohexane ring.
R
4
and R
5
are preferably each independently H or optionally substituted C
1-6
-alkyl, more preferably H or C
1-6
-alkyl.
R
6
is preferably optionally substituted C
1-6
-alkyl, more preferably C
1-6
-alkyl.
R
7
is preferably optionally substituted C
1-6
-alkyl, more preferably optionally substituted C
1-4
-alkyl.
R
8
is preferably H or C
1-6
-alkyl.
The optional substituents which may be present on R
1
to R
8
or on D are preferably each independently selected from carboxy, sulpho, nitro, halo (especially bromo, chloro and fluoro), alkyl (especially C
1-4
-alkyl), alkoxy (especially C
1-4
-alkoxy), hydroxy, amine (especially —NHR
9
), mercapto, thioalkyl (especially C
1-4
-thioalkyl), cyano, ester (especially —OCOR
9
or —COOR
9
) and amide (especially —CONHR
9
), wherein R
9
is H or optionally substituted C
1-4
-alkyl (preferably H or C
1-4
-alkyl).
In one embodiment of the present invention R
2
and R
3
are free from the following substituents: —NO
2
, —CN, —Cl, —Br, —F, —OH, —OC
1-4
-alkyl, —CONH(C
1-4
-alkyl), —CONH
2
, —COOC
1-4
—(CH
2
)
1-4
—CN, —OCO(C
1-4
-alkyl) and —COO(C
1-4
-alkyl).
In a second embodiment of the present invention at least one of R
2
and R
3
carries a substituent selected from —NO
2
, —CN, —Cl, —Br, —F, —OH, —OC
1-4
-alkyl, —COOC
1-4
—(CH
2
)
1-4
—CN, —CONH
2
, —CONH(C
1-4
-alkyl), —OCO(C
1-4
-alkyl) and —COO(C
1-4
-alkyl).
The preferred optional substituents for R
8
are said optional substituents are each independently selected from carboxy, sulpho, nitro, halo, alkyl, alkoxy, hydroxy, amine, mercapto, thioalkyl, cyano, ester and amide, more preferably from —NO
2
, —CN, —Cl, —Br, —F, —OH, —OC
1-4
-alkyl, —OC
1-4
-alkylene—CN, —CONH
2
, —COOC
1-4
—(CH
2
)
1-4
—CN, —OCO(C
1-4
-alkyl) and —COO(C
1-4
-alkyl), especially from —CN and —COO(C
1-4
-alkyl), especially —CN. Preferably R
8
carries one or two substituents, more preferably one substituent.
Any alkyl groups in dyes of Formula (1) may be branched or straight chain. Preferred branched chain alkyl groups are &agr;-branched alkyl groups.
The dyes may be in any form, for example in the form of a salt. Formula (1) includes all tautomers, stereoisomers, zwitterions, polymorphs, and isotopes of dyes falling within the formula.
Salts of Formula (1) may be formed from one or more organic and/or inorganic bases or acids. Preferred salts of Formula (1) are insoluble in water.
The compositions preferably contain from 1 to 10, more preferably from 1 to 6, especially from 1 to 3, more especially 1 dye of Formula (1).
The dye of Formula (1) is preferably insoluble in water and soluble in the water-dissipatable polymer. Therefore the dye is preferably free from carboxy and sulpho groups, for example it is preferably a disperse or solvent-soluble dye. Disperse and solvent soluble dyes are distinct from pigments in that pigments are insoluble in organic solvents and polyesters whereas disperse and solvent soluble dyes are soluble in organic solvents and polymers.
According to a second feature of the present invention there is provided a dye of Formula (1) as hereinbefore defined. The preferences for the dye of Formula (1) are as hereinbefore described in relation to the preferred dyes used in the inks of the invention.
The dyes of Formula (1) may be prepared by diazotising a suitable amine, using a diazotising agent, preferably below 5° C., and coupling to a suitable coupling component. A preferred diazotising agent is sodium nitrite. A suitable amine is of Formula (2) and a suitable coupling component is of Formula (3):
wherein R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and D are as hereinbefore defined.
Generally from 3 to 5 molar equivalents of the amine are used relative to the amount of the coupling component. If desired the resultant dye may be further reacted, for example by condensation with an acyl halide or an anhydride to convert some or all of any hydroxy groups to ester groups.
The composition may contain further dyes other than those of Formula (1), although this is not normally necessary.
The water-dissipatable polymer preferably bears ionised carboxy and/or sulphonate groups, especially ionised sulphonate groups, because these assist water dissipatability of the polymer. Such groups can be chain pendant and/or terminal.
The water-dissipatable polymer is preferably a water-dissipatable polyester. The water-dissipatable polyester can be prepared using conventional polymerisation procedures known to be effective for polyester synthesis. Thus, it is well known that polyesters contain carbonyloxy (i.e. —C(═O)—O—) linking groups and may be prepared by a condensation polymerisation process in which an acid component (including ester-forming derivatives thereof) is reacted with a hydroxyl component. The acid component may be selected from one or more polybasic carboxylic acids, e.g. di- and tri-carboxylic acids or ester-forming derivatives thereof, for example acid halides, an
Bradbury Roy
Holbrook Mark
Meyrick Barry Huston
Shawcross Andrew Paul
Avecia Limited
Klemanski Helene
Pillsbury & Winthrop LLP
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