Phthalocyanine compounds

Compositions: coating or plastic – Coating or plastic compositions – Marking

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106 3149, 540124, 540125, 427466, 428195, C09D 1102, C09B 4704

Patent

active

059221160

DESCRIPTION:

BRIEF SUMMARY
This application is the national phase of international application PCT/GB96/02298 filed Sep. 20, 1996 which designated the U.S.
This invention relates to phthalocyanine compounds, inks their preparation and use.
Ink jet printing is a non-impact printing technique which involves ejecting, thermally or by action of an oscillating piezo crystal, droplets of ink continuously or on demand from a fine nozzle directly onto a substrate such as paper, plastics, textile, metal or glass. The ink may be aqueous, solvent or hot melt based and must provide sharp, non-feathered images which have good water fastness, light fastness and optical density, have fast fixation to the substrate and cause no clogging of the nozzle.
According to the present invention there is provided a compound of the Formula (1) and salts thereof: ##STR2## wherein: M is a metal or hydrogen; substituted alkyl, aryl or aralkyl;
M is preferably copper, nickel, scandium, titanium, vanadium, chromium, manganese, iron, cobalt, zinc, lithium, sodium, potassium, magnesium, calcium, barium, aluminium, silicon, tin, lead or rhodium, more preferably copper, nickel, scandium, titanium, vanadium, chromium, manganese, iron, cobalt or zinc, especially copper or nickel and more especially copper. When M is tri- or tetra-valent the valencies above 2 may be taken by coordination with halogen atoms or oxygen e.g. VO, AICI, PbCI.sub.2.
Each R.sup.1 , W.sup.1 and W.sup.2 is preferably H; optionally substituted C.sub.1-4 -alkyl, especially C.sub.1-4 -alkyl; optionally substituted phenyl; C.sub.7-11 -aralkyl, especially benzyl. It is particularly preferred that R.sup.1 is H and W.sup.1 and W.sup.2 are H or C.sub.1-4 -alkyl.
The divalent organic linking group represented by L.sup.1 is preferably alkylene, especially C.sub.1-6 -alkylene, more especially C.sub.2-4 -alkylene; aralkylene, preferably C.sub.7-11 -aralkylene, especially phenyl-C.sub.1-4 -alkylene; or arylene, preferably arylene having up to ten carbon atoms, especially, phenylene; which may be substituted or unsubstituted.
As examples of alkylene and aralkylene groups represented by L.sup.1, there may be mentioned: ##STR3##
As examples of arylene radicals represented by L.sup.1 there may be mentioned 1,2-1,3- and 1,4-phenylene and 1,4-naphthylene which are optionally sulphonated.
It is preferred that the divalent linking group L.sup.1 is an optionally substituted C.sub.2 -C.sub.6 alkylene linking group, especially a group of the Formula --C.sub.n H.sub.2n -- wherein n is 2 to 6, preferably 2 to 4, more preferably 2.
The optional substituents which may be present on the piperazinyl group Z are preferably selected from optionally substituted alkyl, aryl, aralkyl, acyl and H.
When substituted, the piperazinyl group Z may contain up to 5 substituents, preferably up to 3. The substituents may be at the 2-, 3-, 4-, 5- or 6- positions of the piperazinyl group Z, especially at one or more of the 3-, 4- and 5- positions.
Accordingly, Z is preferably of Formula (2): ##STR4## wherein: R.sup.2 and R.sup.3 each independently is H or optionally substituted alkyl; and group. -alkyl, more preferably H or CH.sub.3, especially H.
When R.sup.1, R.sup.2, R.sup.3, R.sup.4, W.sup.1, W.sup.2 or the divalent linking group L.sup.1 is substituted it is preferred that the substituents are selected from C.sub.1-4 alkyl, especially methyl; --OH; C.sub.1-4 -alkoxy, especially methoxy; carboxy; sulpho; amino, especially NH.sub.2 ; halo; --CN; and NO.sub.2.
R.sup.4 is preferably H, optionally substituted C.sub.1-4 -alkyl or optionally substituted phenyl, more preferably optionally substituted C.sub.1-4 -alkyl. Preferred ester and acyl groups are of the Formula --CO.sub.2 W and --COW respectively wherein W is optionally substituted aryl or optionally substituted alkyl, especially C.sub.1-4 alkyl, phenyl or benzyl.
When R.sup.4 is an optionally substituted alkyl group, it is preferably of Formula (3): ##STR5## wherein: L.sup.1 and each R.sup.1 independently are as hereinbefore defined.
It is preferred that the divalent organic linking group

REFERENCES:
patent: 3053849 (1962-09-01), Clark et al.
patent: 4069064 (1978-01-01), Mett et al.
patent: 4448722 (1984-05-01), Crounse
patent: 4647409 (1987-03-01), Groll et al.
patent: 5123960 (1992-06-01), Shirota et al.
patent: 5503666 (1996-04-01), Mennicke et al.

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