Phthalocyanine ink-jet dyes

Details Phthalocyanine ink-jet dyes Phthalocyanine ink-jet dyes

2001-02-27

2003-05-27

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Process of printing permanently on substrate, other than...

C008S661000, C008S919000, C540S133000, C540S134000, C540S139000, C106S031490

Reexamination Certificate

active

06569212

ABSTRACT:

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.
The applicant has discovered that certain phthalocyanine compounds have particular utility as colorants for use in IJP as they may produce prints with unexpectedly good optical density, light fastness and/or water fastness.
According to the present invention there is provided a compound of Formula (1):
which includes all IJP-effective forms of such compounds; and in which
M represents a metal or H;
Pc represents a phthalocyanine nucleus of Formula (2)
x+y+z represents an average from 3 to 4; and z may be zero.
A represents C
1-4
-alkylene;
R
1
, R
3
each independently represent H or C
1-4
alkyl;
R
4
represents H; or C
1-4
-alkyl optionally substituted with hydroxy;
R
5
represents a carboxylic acid substituted aryl group; and
R
2
represents H, C
1-4
-alkyl or a group of formula BD
where
B represents C
1-4
-alkylene; and
D represents NR
6
R
7
;or SC
1-4
alkyleneSO
3
H;
where
R
6
represents H; or C
1-4
alkyl, optionally subsititued by hydroxy;
R
7
represents H; C
1-4
alkyl, optionally subsititued by hydroxy or morpholino;
or R
6
and R
7
together with the N atom to which they are attached form a morpholino or piperazino ring.
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 and especially from Ni and Cu.
Preferred dyes of Formula (1) are either those dyes in which: R
1
, R
2
, R
3
and R
4
are H; A is —CH
2
CH
2
—; and R
5
is carboxylic acid substituted phenyl, more preferably 3-carboxyphenyl; or
those dyes in which:
M is Cu, z is 0, R
1
is H, R
2
is BD where B is —CH
2
CH
2
—and D is NR
6
R
7
, more preferably NHCH
2
CH
2
OH.
It is preferred that (x+y)>z and/or x>y. More preferably either: x is an average of about 3.0 and y is an average of about 1.0 and z is zero; or x is an average of about 1.3, y is an average of about 1.2 and z is an average of about 1.5.
Any radical group mentioned herein as a substituent refers to a monovalent radical unless otherwise stated. A group which comprises a chain of three or more atoms signifies a group in which the chain may be straight or branched or the chain or part of the chain may form a ring. For example, an alkyl group may comprise: propyl which includes n-propyl and isopropyl; butyl which includes n-butyl, sec-butyl, isobutyl and tert-butyl; and an alkyl group of three or more carbon atoms may comprise a cycloalkyl group. The total number of certain atoms is specified herein for certain substituents, for example C
1-n
alkyl, signifies an alkyl group having from 1 to ‘n’ carbon atoms. The term ‘halo’ as used herein signifies fluoro, chloro, bromo and iodo radicals.
The term ‘IJP effective’ (for example with reference to the inks, compositions, ingredients, substituents and/or compounds described herein) will be understood to mean effective for use in ink-jet printing by for example: providing desirable properties to the ink, being compatible with any inert carriers and/or diluents suitable for formulating such inks, being compatible with ink jet printers and/or capable of being ink-jet printed. In relation to the processes described herein effective compounds are those which will undergo the specified reactions to form the compounds of the present invention. To be particularly acceptable for use in IJP compounds of Formula (1) may be Ames negative.
IJP-effective forms of compounds of Formula (1) may be selected from one or more of the following (including mixtures thereof and combinations thereof in the same molecular moiety): salts, stereoisomers, zwitterions, polymorphic forms, complexes and isotopically substituted forms. Specific compounds of Formula (1) comprise those compounds exemplified herein; all IJP-effective salts thereof, preferably their potassium, sodium or ammonium salts; and IJP-effective mixtures thereof.
Compounds of Formula (1) may be in the form as shown in the structures herein (i.e. free acid form) but are preferably in the form of salts. Salts of Formula (1) may be formed from one or more organic and/or inorganic bases and/or acids and compounds of Formula (1) which are acidic and/or basic (for example acid and/or base addition salts). Salts of Formula (1) comprise all IJP-effective salts that may be formed from monovalent and/or multivalent acids and/or bases. Salts of Formula (1) also comprise all enantiomeric salts formed with IJP-effective chiral acids and/or bases and/or any mixtures of enantiomers of such salts (for example racemic mixtures). The dyes may be converted into a salt using known techniques. The present invention comprises all IJP-effective salts of Formula (1) and IJP-effective mixtures thereof.
Preferred salts of Formulae (1) are alkali metal salts (especially lithium, sodium and potassium salts), and optionally substituted ammonium salts (especially salts with ammonia and volatile amines). More preferred salts are those with a cation of formula
+
NT
4
where each T is independently H or optionally substituted alkyl, or two groups represented by T are H or optionally substituted alkyl and the remaining two groups represented by T, together with the N atom to which they are attached, form a 5 or 6 membered ring (preferably a morpholine, pyridine or piperidine ring). Most preferably each T is independently H or C
1-4
alkyl, especially H, CH
3
or CH
3
CH
2
, more especially H. Examples of cations which are IJP-effective comprise:
+
NH
4
, morpholinium, piperidinium, pyridinium, (CH
3
)
3
N
+
H, (CH
3
)
2
N
+
H
2
, H
2
N
+
(CH
3
)(CH
2
CH
3
), CH
3
N
+
H
3
, CH
3
CH
2
N
+
H
3
, H
2
N
+
(CH
2
CH
3
)
2
, CH
3
CH
2
CH
2
N
+
H3, CH
3
CH
2
CH
2
N
+
H
3
, (CH
3
)
2
CHN
+
H
3
, N
+
(CH
3
)
4
, N
+
(CH
2
CH
3
)
4
, N-methyl pyridinium, N,N-dimethyl piperidinium and N,N-dimethyl morpholinium.
Certain compounds of Formula (1) may exist as one or more stereoisomers, for example, enantiomers, diastereoisomers, geometric isomers, tautomers, conformers and/or combinations thereof within the same moiety. The present invention comprises all IJP-effective stereoisomers of compounds of Formula (1) and IJP-effective mixtures thereof.
Certain compounds of Formula (1) may exist as one or more zwitterions, for example, moieties which comprise two or more centres of ionic charge. The present invention comprises all IJP-effective zwitterions of Formula (1) and IJP-effective mixtures thereof.
Certain compounds of Formula (1) may exist as one or more polymorphs, for example, phases, crystalline forms, amorphous forms, solid solutions, interstitial compounds and/or any mixtures thereof. The present invention comprises all IJP-effective polymorphs of Formula (1) and IJP-effective mixtures thereof.
Certain compounds of Formula (1) may exist in the form of one or more other complexes in addition to the metal complexes shown herein, for example, chelates, solvates, other organometallic complexes, and/or complexes with other IJP-effective ligands. Such complexes may be formed between an suitable substrate in which the compound of Formula (1) and/or the substrate may act as a ligand. The substrate may comprise one or more solvents to form solvate

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