Phthalocyanine compounds

Details Phthalocyanine compounds Phthalocyanine compounds

1998-04-07

2000-02-15

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540125, 540133, 106410, C09B 6750, C09B 4704, C07D48722

Patent

active

060254866

DESCRIPTION:

BRIEF SUMMARY
This invention relates to phthalocyanine compounds, a process for making such compounds, inks containing the compounds and processes for printing the inks especially by ink jet printing and substrates when printed with the inks.
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 Formula (1) and salts thereof: ##STR2## wherein: M is a metal or hydrogen; aralkyl; 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, AlCl, PbCl.sub.2.
Each R.sup.1 independently 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.
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 T are preferably selected from optionally substituted alkyl, aryl, aralkyl, aryl ester 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.
R.sup.4 is preferably H, optionally substituted C.sub.1-4 -alkyl or optionally substituted phenyl, especially an optionally substituted C.sub.1-4 -alkyl group. 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 L.sup.1 in R.sup.4 is optionally substituted C.sub.2-6 -alkylene, more preferably a group of Formula --C.sub.n H.sub.2n --, especially --(CH.sub.2).sub.n --, wherein n is as hereinbefore defined.
When R.sup.1, R.sup.2, R.sup.3, R.sup.4, W or the divalent linking group L.sup.1 is optionally substituted it is preferred that the substituents are selected from C.sub.1-4 alkyl, especially methyl; C.sub.1-4 -alkoxy, especially methoxy; carboxy; sulpho; amin

REFERENCES:
patent: 2459771 (1949-01-01), Fox
patent: 3784599 (1974-01-01), Jefferies et al.
patent: 3989692 (1976-11-01), Jager et al.
patent: 5503666 (1996-04-01), Mennicke et al.

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