Phthalocyanine compounds used in inks for ink-jet printing

Details Phthalocyanine compounds used in inks for ink-jet printing Phthalocyanine compounds used in inks for ink-jet printing

2001-01-31

2002-09-24

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031780, C540S133000, C540S134000

Reexamination Certificate

active

06454845

ABSTRACT:

This application is the national phase of international application PCT/GB99/02453 filed Jul. 28, 1999 which designated the U.S.
This invention relates to compounds, to ink compositions comprising them and to the use of such inks in ink jet printing (“IJP”). 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 colorants 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.
It is essential that colorants used in IJP have good solubility (preferably in aqueous systems) so they can be dissolved in an ink and fired from the ink-jet head without coming out of solution and blocking the nozzle. Yet colorants that have good operability (i.e. high water solubility) are likely to produce prints of poor water fastness due to the same high water solubility. A significant challenge in designing new colorants for IJP is to provide in the same molecule the apparently mutually exclusive properties of good operability for the ink and yet high water fastness for the print. This often requires the synthesis of a colorant molecule of complex structure comprising many different functional groups and such complex molecules can be expensive and difficult to prepare in high yield.
It would be advantageous to provide colorants which overcome some or all of the preceding disadvantages.
Therefore according to the present invention there are provided one or more compounds of Formula (1) and salts thereof:
M
v
Pc(SO
2
NHAr)
x
  Formula (1)
in which:
M represents a metal or H;
Pc represents a phthalocyanine nucleus;
Ar represents an aromatic moiety optionally substituted by one or more groups selected from an optional substituent or optionally substituted C
1-30
carbyl;
v is the valence of Pc divided by the valence of M; and
x is from 2.5 to 4.5.
The applicant has discovered that the above phthalocyanine compounds have particular utility as colorants for use in IJP. For example they can produce IJ prints which exhibit good optical density, water fastness, light fastness and/or a particularly attractive cyan shade. They are particularly useful for formulating IJP inks comprising a resin component.
The compounds of the present invention described herein include all chemical and physical forms thereof (such as those described herein). Preferred compounds are those which are IJP-effective.
The terms ‘optional substituent’ and/or ‘optionally substituted’ as used herein (unless followed by a list of other substituents) signifies the one or more of following groups (or substitution by these groups): carboxy, sulpho, formyl, hydroxy, amino, imino, nitrilo, mercapto, cyano, nitro, halo, methyl and/or methoxy; and includes all direct combinations of a plurality (preferably two) of these groups (e.g. amino and sulphonyl combined are sulphamoyl). Preferred optional substituents comprise: carboxy, sulpho, hydroxy, amino, mercapto, cyano, halo, methyl (optionally substituted by one or more halo) and/or methoxy (optionally substituted by one or more halo).
The term ‘carbyl’ as used herein denotes any organic radical moiety which comprises one or more carbon atoms and optionally one or more other heteroatoms preferably selected from: hydrogen, phosphorus, halo, nitrogen, oxygen and/or sulphur, more preferably from hydrogen, nitrogen, oxygen and/or sulphur. The term ‘hydrocarbyl’ as used herein denotes any radical moiety which comprises one or more hydrogen atoms and one or more carbon atoms. Most preferably ‘carbyl’ moieties comprise one or more of the following carbon containing moieties (including combinations thereof in the same moiety): alkyl, alkoxy, alkanoyl, carboxy, and/or formyl in optional combination with one or more of the following hetero-atom containing moieties (including direct combinations of a plurality (preferably two) of the hetero-atom moieties, (e.g. amino and sulphinyl combined are sulphinamoyl): oxy, thio, sulphinyl, sulphonyl, amino, imino and/or nitrilo. Carbyl moieties may also comprise one or more double and/or triple carbon to carbon bonds and/or aromatic moieties. The optional hetero-atom and/or unsaturated groups may be located in any position in a carbyl moiety, optionally interrupting a chain.
The term ‘alkyl’ or its equivalent (e.g. ‘alk’) as used herein may be readily replaced, where appropriate, by terms encompassing other similar moieties (e.g. other hydrocarbyl moieties) such as those comprising double bonds, triple bonds, and/or aromatic moieties (e.g. alkenyl, alkynyl and/or aryl) as well as multivalent species attached to two or more substituents (such as alkylene). The term ‘halo’ as used herein signifies fluoro, chloro, bromo and iodo, preferably fluro and chloro.
When M is a metal it is preferably selected from Li, Na, K, Mg, Ca, Ba, Al, Si, Sn, Pb, Rh, Sc, Ti, V, Cr, Mn, Fe, Co, Ni and Cu, more preferably from Sc, Ti, Va, Cr, Mn, Fe, Co, Zn, Ni and Cu; especially from Ni and Cu, particularly Cu.
It will be appreciated that v (which denotes the stoichiometric ratio of M to Pc) is the molar ratio which produces a stable complex. It can readily be determined from the relative valences of Pc and M (e.g. v=Pc/M). Preferably, where Pc can be represented as a radical moiety of formula (2):
(where the valence of Pc is 2) then v is inverse half the valence of M.
It will also be appreciated that because of the nature of the preparation of compounds of the present invention, in general they may exist as a mixture of different compounds. Thus in Formula (1) the values for v and x may represent averages for the mixture. Insofar as purification techniques will allow, it is preferred that the mixture comprises one compound as the major component, more preferably the mixture is substantially free of other compounds of Formula (1).
Preferably x is from 2.8 to 4.2, more preferably from 3.0 to 4.0, most preferably 3 or 4.
In the plurality of —SO
2
NHAr groups attached to the Pc nucleus, the Ar group when substituted may be independently substituted by different substituents on each Ar group.
Preferably Ar represents an aromatic moiety, more preferably aryl, most preferably phenyl, where the aromatic moiety is optionally substituted by one or more C
1-30
hydrocarbyl groups optionally interrupted by one or more bivalent radical moieties selected from —O—; —CO—; —OCO—; —COO—; —S—; —SO— and —SO
2
.
Preferred compounds of Formula (1) are those in which:
M is Cu or Ni,
Ar is a aryl group optionally substituted by one or more groups selected from: halo; cyano, nitro, optionally substituted C
1-18
hydrocarbyl; COOR
1
; OCOR
1
; COR
1
; COCOR
1
; SO
2
R
1
; SO
2
OR
1
; OSO
2
R
1
; NHCOR
1
and CONHR
1
; where R
1
independently represents H or optionally substituted C
1-18
hydrocarbyl; and any of the above hydrocarbyl groups may independently be optionally interrupted by one or more of —O—; —CO—; —OCO—; —COO—; —S—; —SO— and —SO
2
.
More preferred compounds of Formula (1) are those in which:
M is Cu,
Ar is phenyl optionally substituted by one or more groups selected from: halo; cyano, nitro, optionally substituted C
1-12
alkyl; optionally substituted C
1-12
alkenyl; optionally substituted C
1-12
alkynyl; optionally substituted aryl; (optionally fused to the aryl ring to/form polycyclic aromatic system); COOR
1
; OCOR
1
; COR
1
; COCOR
1
; SO
2
R
1
; SO
2
R
1
; OSO
2
OR
1
; NHCOR
1
and CONHR
1
; where R
1
independently represents H or optionally substituted C
1-12
alkyl; optionally substituted C
1-12
alkenyl; optionally substituted C
1-12
alkynyl; and any of the above alkyl, alkenyl and

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