Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
1999-02-16
2001-12-25
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031780, C106S410000, C106S413000, C540S133000, C540S134000
Reexamination Certificate
active
06332918
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 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 H, metal, halometal, oxymetal and/or hydroxymetal;
k is the inverse of half of the valency of M;
Pc comprises a phthalocyanine nucleus of Formula (2):
L comprises a linking group comprising an optionally substituted C
1-30
carbyl;
A comprises —O—, —S— or —NR
3
—, where R
3
independently comprises H or optionally substituted C
1-30
carbyl;
R
1
comprises at least one group independently selected from: an optional substituent and optionally substituted C
1-15
carbyl;
R
2
comprises an optionally substituted C
1-30
carbyl that comprises at least one alkyl group substituted by at least one group selected from: hydroxy, carboxy and sulpho;
z comprises an integer from 0 to 4; w comprises an integer from 1 to 5; and the sum of w+z comprises from 1 to 5; and
x and y each independently comprises a non-zero number; and the mean of the sum of x+y comprises from about 1 to about 6;
where the optional substituents comprise at least one of: carboxy, sulpho, hydroxy, amino, mercapto, cyano, nitro and halo.
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, methoxy and/or combinations thereof. These optional groups include all chemically possible combinations in the same moiety of a plurality (preferably two) of the aforementioned groups (e.g. amino and sulphonyl combined represent a sulphamoyl radical). 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: alkyl, alkoxy, alkanoyl, carboxy, carbonyl, formyl and/or combinations thereof; optionally in combination with one or more of the following heteroatom containing moieties: oxy, thio, sulphinyl, sulphonyl, amino, imino, nitrilo and/or combinations thereof. Carbyl moieties include all chemically possible combinations in the same moiety of a plurality (preferably two) of the aforementioned carbon containing and/or heteroatom moieties (e.g. alkoxy and carbonyl combined represent an alkoxycarbonyl radical):
Any radical group or moiety mentioned herein (e.g. as a substituent) refers to a monovalent radical unless otherwise stated or the context clearly indicates otherwise (e.g. an alkylene moiety is bivalent and links two other moieties). 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
carbyl, signifies an carbyl 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 effective for use in ink jet printing (IJP-effective) comprising a medium and a colorant comprising a IJP-effective compound of Formula (1) as defined herein. Preferably in the ink of the present invention the compounds of Formula (1) comprise dyes, more preferably dyes comprising a predominately cyan colour.
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 inkjet 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.
In Formula (1) when M is a metal it may be selected from any IJP-effective metal or mixture thereof in the same complex. The metal may exist in any suitable oxidation state and may be neutral or charged (i.e. an ion). M may also comprise a metal bonded to one or more oxygen atoms, halo atoms or hydroxy groups, for example at least one of: AlCl, AlOH, RhCl, RhOH, InBr, InCl, InOH, GaCl, GaOH, ScCl and ScOH. Preferably M comprises a metal selected from Li, Na, K, Mg, Ca, Ba, Al, In, Ga, Zn, Si, Sn, Pb, Rh, Sc, Ti, V, Cr, Mn, Fe, Co, Ni and Cu; more preferably from Zn, Sc, Ti, V, Cr, Mn, Fe, Co, Ni and Cu; and most preferably from Ni and Cu. Especially preferred compounds of Formula (1) are those in which M comprises Cu.
Preferred compounds of Formula (1) are those in which:
z is 0, 1 or 2; and when z is other than 0, R
1
represents an optionally substituted 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 (e.g. benzamido), C
1-7
alkanoylamino; C
1-6
alkylcarbamoyl and C
1-6
alkylsulphamoyl;
L represents a C
1-15
carbyl group, which may be attached to the benzene ring at the position para to the sulphonylamino group attached to the Pc nucleus;
A represents —S— or a protonable amino group comprising —NR
3
— where R
3
represents H or an optionally substituted C
1-22
carbyl that comprises at least one alkyl group substituted by hydroxy, carboxy and/or sulpho;
R
2
independently represents an optionally substituted C
1-22
carbyl that comprises at least one alkyl group substituted by hydroxy, carboxy and/or sulpho;
w is 1 and;
x and y each represent from 1 to 3 and the sum of x+y is from 1 to 4.
More preferred compounds of Formula (1) are those preferred compounds in which:
M is Cu;
L represents sulphonylC
1-15
alkylene;
A represe
Avecia Limited
Klemanski Helene
Rothwell Figg Ernst & Manbeck
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