AZO dyes and compositions comprising such dyes

Details AZO dyes and compositions comprising such dyes AZO dyes and compositions comprising such dyes

1999-03-18

2001-09-18

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031770, C534S797000, C534S803000, C427S466000, C428S195100

Reexamination Certificate

active

06290763

ABSTRACT:

This invention relates to dyes, to inks and to their use 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 dyes 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.
According to the present invention there is provided at least one compound of Formula (1):
which comprises any suitable form of the compound: such as salt; stereoisomer, zwifterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: n represents from 1 to 5 inclusive; R
1
, R
1B
, R
4
and R
4B
each independently comprises at least one of the following substituents, optionally substituted:
H, C
1-8
alkyl; C
1-8
alkoxy; —NHCOH, C
1-8
alkylcarbonylamino; and —NHCONR
5
R
6
where R
5
and R
6
each independently comprises at least one of the
following substituents: H, C
1-8
alkyl and aryl; and
R
2
and R
3
each independently comprises at least one of the following substituents, optionally substituted:
H; C
1-8
alkoxy; —NHC
1-8
alkyleneOH, —SC
1-8
-alkyleneSO×hd
3
H;
—NHC
1-8
alkyleneN(C
1-8
alkyl)
2
;
where X comprises one of the following: —NHC
1-8
alkylene;
—NHphenyISO
2
NHC
1-8
alkylene; and a direct link,
where X comprises one of the following: —NHC
1-8
alkylene;
—NHphenyISO
2
NHC
1-8
alkylene; and a direct link;
a moiety of Formula(2)
where m and p is each independently from 0 to 5 inclusive, provided that
(m+p) is from 1 to 5 inclusive; and
R
1A
, R
2A
, R
4A
and R
4C
each independently comprises at least one of those
optionally substituted subsfituents as defined herein for R
1
, R
2
, R
4
and R
4B
respectively; and
any other suitable labile or non-labile substituent not mentioned above; where the optional substituents herein comprise: C
1-4
alkyl (optionally substituted with at least one halo)., C
1-4
alkoxy (optionally substituted with at least one halo), carboxy, sulpho. hydroxy, amino, mercapto, cyano, nitro and halo with the proviso that one of R
2
and R
3
is a moiety of the Formula (2), then the other R
2
or R
3
is:
a moiety of Formula (2), SC
1-8
alkyleneSO
3
H or —NHC
1-8
alkyleneN (C
1-8
alkyl)
2
; wherein X
1
is NHC
1-8
alkylene or -NHphenylSO
1-8
alkylene.
When R
2
and/or R
3
represent a labile atom or group, it is preferably an atom or group which is bound by a chemical bond to the triazine nucleus which is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the triazine nucleus and cellulose. Labile atoms and groups that may be represented by R
2
and/or R
3
independently comprise: halo (preferably F and Cl); sulphonic acid groups; thiocyano groups; optionally substituted quatemary ammonium groups (preferably trialkylammonium groups) and/or optionally substituted pyridinium groups (preferably 3−and 4−carboxy pyridinium groups).
Preferred non-labile groups represented by R
2
and/or R
3
independently comprise groups of the formulae —OR
7
, —SR
8
and/or —NR
9
R
10
, more preferably —OH,—NH
2
, —NH (C
1-4
alkyl) and/or -NH(hydroxyC
2-4
alkyl). In the preceding formulae R
7
, R
8
, R
9
and/or R
10
are each independently selected from the following optionally substituted substituents: H; alkyl (preferably C
1-10
alkyl, especially C
1-4
alkyl); cycloalkyl; aryl (preferably phenyl); aralkyl [preferably -(CH
2
)
1-4
phenyl, especially benzyl]; and R
9
and R
10
together with the nitrogen atom to which they are attached form an optionally substituted 5−or 6−membered ring, preferably an optionally substituted morpholine, piperidine or piperazine ring, more preferably piperazine in which the free ring N-atom is optionally substituted by a C
1-4
alkyl or hydroxy-C
2-4
-alkyl group. When R
7
, R
8
, R
9
and/or R
10
is substituted, the substituent is preferably selected from the optional substituents listed above, more preferably is selected from: hydroxy, methyl, methoxy, sulpho and carboxy.
Advantageous dyes of Formula (1) are those in which: n is 2; R
1B
and R
4B
represent H; R
1
represents H, C
1-8
alkyl; C
1-8
alkoxy; -NHCOH, C
1-8
alkylcarbonylamino; or -NHCONR
5
R
6
; R
4
represents H, C
1-8
alkyl or C
1-8
alkoxy; and R
2
and R
3
each independently represents: H; C
1-8
alkoxy; —NHC
1-8
alkyleneOH, —SC
1-8
-alkyleneSO
3
H; —NHC
1-8
alkyleneN(C
1-8
alkyl)
2
,
where X is —NHC
1-8
alkylene; or a direct link,
where X is —NHC
1-8
alkylene; or a direct link; and/or a moiety of Formula(2) where m is 2, p is 0 and R
4C
represents H; with the proviso that when one of R
2
and R
3
is a moiety of the Formula (2) where m is 2, p is 0 and R
4c
represents H, then the other of R
2
and R
3
is
—SC
1-8
alkyleneSO
3
H, —NHC
1-8
alkyleneN(C
1-8
alkyl)
2
or a moiety of Formula (2) where m is 2, p is 0 and R
4c
is H, wherein X
1
is NHC
1-8
alkylene.
Any radical group mentioned above 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 (induding spiro and/or fused rings). The total number of certain atoms is specified for certain substituents for example C
1-n
alkyl, signifies an alkyl group 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 —CO
2
H groups 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. Hydrocarbon substituents or parts of substituents may comprise one or more double and/or triple carbon to carbon bonds and the term ‘alkyl’ as used herein encompasses alkenyl and alkynyl. The term ‘aryl’ as used herein comprises any suitable hydrocarbon comprising an aromatic moiety. The term ‘halo’ as used herein signifies fluoro, chloro, bromo and iodo.
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 Formula (1) may be Ames negative.
According to a first preferred aspect of the present invention there is provided at least one mono azo dye of Formula (1), including any suitable salts and tautomers thereof, in which: n is 2; R
1B
, R
4
and R
4B
are all H; R
1
is H, C
1-4
alkyl, C
1-4
alkoxy, NHCOH, C
1-4
alkylcarbonylamino, or -NHCONR
5
R
6;
where R
5
and R
6
is each independently: H, C
1-4
alkyl or aryl; and R
2
and R
3
is each independently: —NHC
1-4
alkyleneOH, —SC
1-4
alkyleneSO
3
H, —NHC
1-4
alkyleneN(C
1-4
-alkyl)
2
; or
where X is —NHC
1-4
alkylene or a direct link.
More preferred monoazo dyes of Formula (1) in this first preferred aspect of the invention are those in which: the carboxy groups on the phenyl ring in Formula (1) are meta to the azo group; and R
1
is methyl or NHCOCH
3
.
According to a second preferred aspect of the present invention there is provided at least one bisazo dye of Formula (1), including any suitable salts and tautomers thereof, in which: n is 2; R
1B
and R
4B
a

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