Phthalocyanine compounds

Details Phthalocyanine compounds Phthalocyanine compounds

1998-04-07

2000-01-18

Shah, Mukund J.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540122, 540123, 540124, 540125, 540131, 540133, 540139, 106 22, C09D 1102, C09D48722, C09B 4704

Patent

active

060158964

DESCRIPTION:

BRIEF SUMMARY
This invention relates to coloured phthalocyanine compounds, inks, their preparation and use. The compounds are particularly useful as the coloured component of ink jet printing 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 a first aspect of the present invention there is provided a colorant 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, AlCl, PbCl.sub.2.
R.sup.1, R.sup.2, W.sup.1 and W.sup.2 are 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, R.sup.2 is H or C.sub.1-4 -alkyl and W.sup.1 and W.sup.2 are each independently H or C.sub.1-4 -alkyl.
The divalent organic linking group represented by L in Formula (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, there may be mentioned: ##STR3##
As examples of arylene radicals represented by L there may be mentioned 1,2-, 1,3- and 1,4-phenylene and 1,4-naphthylene which are optionally sulphonated.
It is particularly preferred that L is an optionally substituted C.sub.2 -C.sub.6 -alkylene group, more preferably a group of the Formula --C.sub.n H.sub.2n -- wherein n is 2 to 6. It is preferred that n is 2 to 4, more preferably n is 2.
R.sup.3 can be a primary, secondary or tertiary aminoalkyl group, preferably a group of the Formula --C.sub.n H.sub.2n -NR.sup.4 R.sup.5 wherein n is as hereinbefore defined and R.sup.4 and R.sup.5 each independently is H; optionally substituted alkyl, aryl or aralkyl; or R.sup.4 and R.sup.5 together with the nitrogen atom to which they are attached form a 5 or 6 membered ring other than a piperazino ring.
Preferably R.sup.4 and R.sup.5 each independently is H, optionally substituted C.sub.1-4 -alkyl, phenyl or benzyl, more preferably H or C.sub.1-4 -alkyl, especially methyl.
When R.sup.4 and R.sup.5 together with the nitrogen to which they are attached form a 5 or 6 membered ring they preferably form a pyridine, piperidine or morpholine ring, more preferably a morpholine ring.
As examples of group s represented by R.sup.3 there may be mentioned: ##STR4##
When R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, W.sup.1, W.sup.2 or L is optionally substituted, the substituent(s) is or are preferably selected from H; alkyl, preferably C.sub.1-4 -alkyl and especially methyl; alkoxy, preferably C.sub.1-4 -alkoxy and especially methoxy; carboxy; sulpho; --OH; amino; --CN; --NO.sub.2 ; and halo.
It is preferred that x is from 0.8 to 2. Preferred values of y are from 1 to 2. Preferred values of t are from 0.8 to 2.
The sum of (x+y+t) is preferably 4.
It is to be understood that colorants of the present invention include not only compounds of Formula (1) but also mixtur

REFERENCES:
patent: 3989692 (1976-11-01), Jager et al.

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