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

2000-03-02

2001-05-22

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031780, C106S410000, C106S413000, C540S133000, C540S134000

Reexamination Certificate

active

06235097

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 compounds listed below are known from the prior art:
EP 0684292 discloses the following compounds (where Pc is a phthalocyanine nucleus as defined below):
Chemical Abstracts (CAS) 105038-63-9 discloses a compound of Formula I:
CAS 104994-17-4 discloses a compound of Formula II:
CAS 104994-15-4 discloses a compound of Formula III:
The preceding compounds are known per se but are not known for use as colorants in IJP.
Surprisingly, 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 at least one compound of Formula (1):
which comprises any form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where:
M represents a metal or H;
Pc represents a phthalocyanine nucleus of Formula (2):
L represents a linking group comprising an optionally substituted C
1-30
hydrocarbyl;
A represents a group comprising at least one of: amino and optionally substituted
C
1-30
hydrocarbyl comprising at least one protonable nitrogen atom; but where A comprises other than an alkyl group substituted by at least one of: hydroxy, carboxy and sulpho;
R
1
represents a group independently comprising at least one of: an optional substituent and optionally substituted C
1-15
hydrocarbyl;
z represents an integer from 0 to 4; w represents an integer from 1 to 5; and the sum of w+z is from 1 to 5; and
x and y each independently represent a non-zero number; and the mean of the sum of x+y is from about 1 to about 6;
where the optional substituents comprise at least one of: carboxy, sulpho, hydroxy, amino, mercapto, cyano, nitro and halo;
with the provisos that:
when M is Cu; x and y are both 1.5; z is 0, w is 1 and L is p-SO
2
C
2
H
4
then A is other than —NHCN; and
Formula (1) is other than a compound selected from: Formulae I, II and III as defined herein and proton salts thereof.
The term “hydrocarbyl” as used herein denotes any radical moiety which comprises one or more hydrogen atoms with one or more carbon atoms and optionally one or more other suitable heteroatoms, preferably nitrogen, oxygen and/or sulphur. More preferably the term ‘hydrocarbyl’ comprises any of the following moieties and combinations thereof in the same moiety: alkyl, alkoxy, alkanoyl, carboxy, alkanoyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, sulphamoyl, alkylamino, and/or alkanoylamino. Hydrocarbyl moieties may also comprise one or more double and/or triple carbon to carbon bonds and/or aromatic moieties. It will be understood that the terms ‘alkyl’ or its equivalents (e.g. ‘alk’) as used above may be readily replaced where appropriate by terms encompassing moieties comprising double bonds, triple bonds and/or aromatic moieties (e.g. alkenyl, alkynyl and/or aryl). The term ‘halo’ as used herein signifies fluoro, chloro, bromo and iodo, preferably fluro and chloro.
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 wholly or in part may be linear, branched and/or form a ring (including spiro and/or fused rings). The total number of certain atoms is specified for certain substituents for example C
1-n
hydrocarbyl, signifies an hydrocarbyl moiety comprising from 1 to n carbon atoms. In any of the formulae drawn herein if one or more ring substituents are not indicated as attached to any particular atom on the ring [for example the substituent R
1
in Formula (1)] the substituent may replace any H attached to an atom in the ring and may be located at any available position on the ring which is chemically suitable.
According to a further feature of the present invention there is provided an ink suitable for use in IJP comprising a suitable medium and a colorant comprising a suitable compound of Formula (3):
which comprises any suitable form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where:
M represents a suitable metal or H;
Pc represents a phthalocyanine nucleus of Formula (2) as defined herein;
L represents a suitable linking group comprising an optionally substituted C
1-30
hydrocarbyl;
A represents a group comprising at least one of: amino and optionally substituted C
1-30
hydrocarbyl comprising at least one protonable nitrogen atom; but where A comprises other than an alkyl group substituted by at least one of: hydroxy, carboxy and sulpho;
R
1
represents a suitable group independently comprising at least one of: an optional substituent and optionally substituted C
1-15
hydrocarbyl;
z represents an integer from 0 to 4; w represents an integer from 1 to 5; and the sum of w+z is from 1 to 5; and
x and y each independently represent a non-zero number; and the mean of the sum of x+y is from about 1 to about 6;
where the optional substituents comprise at least one of: carboxy, sulpho, hydroxy, amino, mercapto, cyano, nitro and halo.
Preferably in the ink of the present invention the compounds of Formula (3) comprise dyes, more preferably dyes comprising a predominately cyan colour.
The terms ‘acceptable’ or ‘suitable’ (for example with reference to composition ingredients, substituents and/or compounds described herein) will be understood to mean suitable for use in IJP for example by providing desirable properties to the ink or being compatible with any inert carriers and/or diluents suitable for formulating such inks. In relation to the processes described herein suitable compounds are those which will, in addition, undergo the specified reactions. To be particularly acceptable for use in IJP compounds of Formulae (1) and (3) may be Ames negative.
In Formulae (1) and (3) when M is a metal it may be selected from any suitable metal or mixtures thereof in the same complex. The metal may exist in any suitable oxidation state and may be neutral or charged (i.e. an ion). The metal may also be bonded to one or more oxygen atoms. Preferred metals for M comprise Li, Na, K, Mg, Ca, Ba, Al, Si, Sn, Pb, Rh, Sc, Ti, V, Cr, Mn, Fe, Co, Ni and/or Cu, more preferably Sc, Ti, Va, Cr, Mn, Fe, Co, Zn, Ni and/or Cu and most preferably Ni and/or Cu. Especially preferred compounds of Formulae (1) and (3) are those in which M is Cu.
Preferred compounds of Formulae (1) and (3) are those in which: z is 0 or 1; when z is 1, R
1
represents a group independently selected from: carboxy, carboxyC
1-6
alkyl, sulpho, C
1-6
alkyl, C
1-6
alkoxy, halo, cyano, nitro, amino, C
1-6
alkylamino di(C
1-6
alkyl)amino, C
6-12
arylamido (for example benzamido) and C
1-6
alkylsulphamoyl;
L represents a C
1-15
hydrocarbyl group;
A represents an optionally substituted group selected from:
piperazinyl (optionally N-substituted by R
2
); —OR
3
; —SR
3
; and amino optionally substituted by one or more R
3
; where:
R
2
comprises C
1-6
alkyl optionally substituted by one or more amino (the amino being optional

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