Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
2001-05-30
2003-08-12
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031350, C106S031600, C106S031670, C427S466000, C428S032100
Reexamination Certificate
active
06605142
ABSTRACT:
This invention relates to aqueous compositions which are particularly suitable for use in ink jet printing (IJP), to substrates carrying such compositions, to cartridges containing the compositions and to ink jet printing methods.
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, light-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.
We have found that the incorporation of certain forms of soluble transition metal ions into inks for IJP provides prints which exhibit enhanced light-fastness. We have also found that this effect may be achieved when a composition containing these soluble transition metal ions is added to the substrate separately or is carried by the substrate prior to or after ink jet printing.
According to the present invention there is provided an ink comprising:
a) an aqueous medium;
b) colorant; and
c) a compound of Formula (1);
M[X]
n
(1)
wherein:
M is a copper, nickel, cobalt and manganese cation;
X is a carboxylic acid anion comprising at least four carbon atoms; and
n is from 1 to 2 inclusive.
The cation represented by M may be any one of copper, nickel, cobalt and manganese cations or a mixture of two or more of such cations. Preferably M is copper or nickel. It is especially preferred that M is copper (I) or, more preferably, copper (II).
X is preferably a carboxylic acid anion comprising from 4 to 20, more preferably from 4 to 8 carbon atoms (including the carbon atom in the acid group). The carbon atoms are preferably arranged in a cyclic group or in a straight chain or branched chain.
Preferred cyclic groups are 5- and 6-membered rings, especially homocyclic and heterocyclic rings. Examples of homocyclic rings include phenyl, naphthyl, cyclopentyl and cyclohexyl rings. Examples of heterocyclic rings include thiophene and especially furanyl, dihydrofuranyl, tetrahydrofuranyl, pyranyl, dihydropyranyl and tetrahydropyranyl rings.
The compound of Formula (1) is preferably in the form of a complex between the group(s) represented by X and the cation represented by M. In a preferred embodiement X is a bidentate or higher-dentate ligand for M, especially a bidentate, tridentate, quadridentate, pentadentate or hexadentate ligand for M. Accordingly X preferably carries one or more electron donor groups. These electron donor groups may work in combination with the carboxylic anion (i.e. —COO
−
) to tightly bind X to M, thereby lowering the likelihood of M leaking into the environment or having any undesirable properties associated with free metal ions.
The compound of Formula (1) may also have other small molecules co-ordinated to the metal cation represented by M, for example H
2
O molecules commonly co-ordinate with transition metals by means of the lone pair of electrons on their oxygen atom. In this way copper salicylate normally has the formula Cu(salicylate)
2
.2H
2
O in which the carboxylate anions bind ionically to the copper cation, the phenolic hydroxy groups act as an electron donor contributing their oxygen electrons to the copper and two water molecules donate their electrons to the copper to give what can be described as a ‘bi-pyramidal shell’ around a central copper cation. It will be understood that such compounds having small molecules coordinated to the metal cation fall within the scope of the present invention.
The electron donor groups may be any of those commonly used in transition metal complexes, particularly groups containing an oxygen (e.g. hydroxy or ether), sulphur (e.g. thiol or thioether), amino (e.g. primary, secondary, tertiary or —N═N—) or tertiary phosphine atom.
The electron donor groups and the carboxylic anion in X will usually be arranged relative to each other such that the complex formed by X with M is thermally stable, for example they form a 3-, 4-, 5-, 6-, or 7-membered ring or bridge with M, especially a 5- or 6-membered ring or bridge. Preferably X is free from —N═N— groups.
Preferred anions represented by X are heterocyclic carboxylic acid anions comprising at least four carbon atoms, more especially anionic carboxylic acid derivatives of mono-, di- and tri-saccharides, for example, aldonic acids (e.g. 6-phosphogluconic acid) and particularly, glucuronic acid, muramic acid and sialic acid.
The anion represented by X is preferably of the formula RCOO
−
wherein R is an optionally substituted organic group comprising at least 3 carbon atoms. Preferably R is an optionally substituted organic group comprising from 3 to 12, more preferably 4 to 8 carbon atoms. The optional substituents are preferably selected from hydroxy, sulpho, carboxy, phosphate, phosphonate, amino (including —N═N—, but more preferably primary, secondary or tertiary amino), amido (especially C
1-4
-alkanoylamino) cyano, alkoxy (especially C
1-4
-alkoxy) and ester (especially —CO
2
—C
1-4
-alkyl). Equally the optional substituents for R may be thiol, thioalkoxy (especially C
1-4
-alkoxy, optionally carrying a carboxy group) or tertiary phosphine. Preferably the compounds of Formula (1), and the groups represented by R, are free from —N═N— groups.
In one embodiement preferred anions represented by X are carboxylic acid anions comprising 4 to 8 carbon atoms (including the carbon atom in the acid group), optionally substituted by one or more hydroxy groups and/or optionally interrupted by one or more amino, ether, thioether or carbonyl groups, for example; tartaric acid, oxaloacetic acid, malic acid, citric acid. It is especially preferred that X is gluconic acid.
Examples of carboxylic acid anions comprising at least four carbon atoms which may form a complex with M include the following categories:
(i) compounds comprising an aromatic ring carrying a carboxylic acid anion on a first carbon atom of the ring and an electron donor group on a second carbon atom of the ring, wherein the first and second carbon atoms are separated from each other by one covalent bond. Specific examples of such compounds include the anions of 4- or 5-sulpho salicylic acid, 1-hydroxy-2-carboxy-5-sulphonaphthalene, 4- or 5-sulfoanthranilic acid, 4-sulfo-N-phenylanthranailic acid, 4- or 5-hydroxythiosalicylic acid, 4- or 5-sulfothiosalylic acid, 2,4-dicarboxythiophenol, 4-sulfophthalic acid, 1-hydroxy-2,4-dicarboxynaphthalene, 2-amino-3-hydroxybenzoic acid, 2,4,5-trihydroxybenzoic acid, 2,2′-dithiosalicylic acid, 1-thio-2-carboxy-4-sulfonaphthalene and 1-amino-2-carboxy-4-sulfonaphthalene; and
(ii) compounds comprising an aliphatic chain of carbon atoms carrying a carboxylic acid anion on a first carbon atom of the chain and an electron donor group on a second carbon atom of the chain, wherein the first and second carbon atoms are the same carbon atom or they are separated from each other by one, two or three covalent bonds. In this embodiment the electron donor group(s) may form part of the chain or be pendant on the chain. Specific examples of such compounds include the anions of ethylenediamine tetraacetic acid (“EDTA”) citric acid, tartric acid, L-tyrosine, malic acid, gluconic acid, mucic acid, quinic acid, chelidonic acid, 3,3′-thiodipropionic acid, meso-2,3-dimercaptosuccinic acid, mercaptosuccinic acid, 2-isoporpylmalic acid, nitrilotriacetic acid, 1,6-diaminohexane-N,N,N′,N′-tetracacetic acid, diethylenetriaminepentaacetic acid, diethylenetriaminehexaacetic acid, tricine, bicine and lanthionine;
(iii) mixtures comprising two or more of the foregoing.
As will be understood, the p
Kenworthy Mark
Macfaul Philip
Tallant Neil Anthony
Avecia Limited
Klemanski Helene
Pillsbury & Winthrop LLP
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