Azopyridone compounds, compositions and use

Details Azopyridone compounds, compositions and use Azopyridone compounds, compositions and use

2002-03-20

2004-04-20

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C008S466000, C008S495000, C008S639000, C008S641000, C008S673000, C106S031280, C106S031450, C106S031480, C347S086000, C349S106000, C534S649000

Reexamination Certificate

active

06723835

ABSTRACT:

This invention relates to compounds, compositions, patterned substrates (such as displays and colour filters) comprising these colorants and to methods of making thesame.
The ability to produce brightly coloured patterns or images on substrates, where the colour has high resistance (fastness) to light, water, heat and/or solvents is important in many areas of for instance the electronics and printing industries. Examples of this are in the production of colour filters, in ink-jet printing and in electrophotographic imaging. Thus it is important to discover colorants which can be readily used (and/or formulated into inks for use) in such applications.
Colour filters, alternatively known as optical filters, are a component of coloured liquid crystal displays (LCDs) used as flat screen displays, for example, in small television receivers or portable computers.
Dyes of the following formulae are known:
Dyes of structures II & III are water soluble monoazo pyridones used as cellulose reactive dyes as described in EP 169,457 B1 (Hoechst). The dye of structure IV is described in GB 1,359,171 (Ciba-Geigy), as a dye for wool or cellulosics. The dye of structure I in which a pyridone moiety is bound to a zinc phthalocyanine is described in JP-A 01-303407 (Nippon Kayaku) as a one component green dye for colour filters. This is different from the present invention in which a yellow dye is used as a separate component of a green ink for colour filters. This offers much greater flexibility in adjusting the precise shade of the ink and also is advantageous over zinc phthalocyanines which are less favoured due to poor light fastness.
Known mixtures of copper phthalocyanines and azopyridone yellow dyes (such as the dyes exemplified in JP2701387B2 [Mitsubishi Kasei Corp]) are unsatisfactory for use in colour filter applications because of poor light fastness. However, green colour filters containing azopyridone yellow dyes are significantly brighter than those produced using alternative yellow chromophores such as azobenzenes, azopyrazolones, metallised azo dyes and yellow pigments, which are prevalent in the art.
It is desirable therefore to find improved colorants for use in colour filters, in particular colorants which can be used either alone for example as a yellow or as a yellow component in a mixture (e.g. with cyan colorants such as phthalocyanines). It is a preferred object of a preferred aspect of the invention to discover a green colorant comprising a mixture of one or more yellow colorants with one or more cyan colorants which is of particular use in a colour filter, optionally with improved properties such as light fastness and/or brightness.
The present invention provides azopyridone compounds of use in preparing patterned colored substrates such as colour filters. The compounds give stable inks with advantageous properties. As a preferred aspect of the present invention the applicant has surprisingly discovered certain simple pyridone dyes containing carboxy groups ortho to the azo linkage have a significant advantage in terms of light fastness versus related ortho-sulpho analogues, with no loss in brightness.
According to the present invention there is provided a composition comprising a solvent and at least one compound of Formula (1)
in which:
R
1
represents H, an optionally substituted C
1-8
carbyl derived group, or a group of Formula A:
where:
c is from 2 to 6;
R
3
represents H or optionally substituted C
1-8
carbyl derived group;
R
4
and R
5
independently represent an optional substituent;
R
2
represents an optionally substituted C
1-8
carbyl derived group;
X, Y and Z independently represent H or an optional substituent group;
M represents H or a cation; and
m and n independently represent 0, 1 or 2.
The azopyridones of Formula (1) are particularly suitable for use in colour filters, giving very bright yellow films with good light fastness, and as components of ink-jet inks. Conveniently compounds of Formula (1) are not pyridinium pyridones (i.e. Z is not pyridinium).
Preferred compounds of Formula (1) are those in which:
R
1
represents H, optionally substituted alkyl, a group of Formula [R
9
O]
a
R
6
, or a group of Formula A
R
2
represents alkyl, especially C
1-4
alkyl more especially methyl, or CH
2
SO
3
M,
X and Y independently represent SO
3
M, CO
2
M, PO
3
M
2
, SO2NR
6
R
7
, CONR
6
R
7
, CO
2
R
6
, COR
6
, alkyl, alkoxy, NR
6
COR
7
, halogen, NO
2
, NR
7
R
8
;
where R
6
and R
7
independently represent H, optionally substituted C
1-6
alkyl, optionally substituted aryl; and R
8
represents R
6
or a substituted triazinyl group;
Z represents CN, CONH
2
, H or CH
2
SO
3
M;
R
3
represents H or optionally substituted C
1-8
carbyl derived group;
R
4
and R
5
independently represent halo, SO
3
M, NR
6
R
7
, OR
6
or SR
7
;
M represents H, alkali metal ion, ammonium, or a quatemary ammonium cation (hereinafter QAC); more preferably M is Li
+
, Na
+
, K
+
or NH
4
+
;
m, n is 0, 1 or 2;
a is an integer from 1 to 10, more preferably from 1 to 5, especially 2 to 3;and each R
9
is independently ethylene or propylene:
with the proviso that at least one of R
1
to R
8
, X, Y or Z comprises a group of Formula SO
3
M or PO
3
M
2
; and the compound of Formula (1) is other than a compound of Formula II, III or IV as described herein.
Preferred QAC's are those containing C
1-30
, alkyl chains. More preferred QAC cations may be selected from one or more of the following: N,N-diethyl-N-dodecyl-N-benzylammonium; N,N-dimethyl-N-octadecyl-N-(dimethylbenzyl) ammonium; N,N-dimethyl-N,N-didecyl ammonium; N,N-dimethyl-N,N-didodecyl ammonium; N,N,N-trimethyl-N-tetradecylammonium; N-benzyl-N,N-dimethyl-N-(C
12-18
alkyl)ammonium; N-(dichlorobenzyl)-N,N-dimethyl-N-dodecylammonium; N-hexadecyl pyridinium; N-hexa decyl-N,N,N-trimethylammonium, dodecylpyridinium; N-benzyl-N-dodecyl-N,N-bis(hydroxyethyl)ammonium; N-dodecyl-N-benzyl-N,N-dimethylammonium; N-benzyl-N,N-dimethyl-N-(C
12-18
alkyl)ammonium; N-dodecyl-N,N-dimethyl-N-(1-naphthylmethyl) ammonium and N-hexadecyl-N,N-dimethyl-N-benzylammonium cations.
Suitable QAC cations may also be formed from suitable amines for example from one or more amines selected from: isononylamine, dodecylamine, octadecylamine, didecylamine, didodecylamine, tetradecylamine, hexadecylamine, mixed C
12-18
alkylamines and N-benzyl amines. Preferred amines which may be used to from suitable QAC comprise N-C
1-6
alkyl primary amines, N,N-di-C
1-8
alkyl secondary amines and N-benzyl amines. Particularly preferred amines comprise methyl and ethyl amine derivatives.
Preferably at least one of R
1
, R
2
, X, Y or Z comprises a group of Formula SO
3
M or PO
3
M
2
where M is independently as represented herein; when n is 0; m is 1; X is a sulpho group para to the azo group; Z is H and R
2
is methyl then R
1
is other than ethyl and the compound of Formula (1) is other than a compound of Formula II, III or IV as described herein.
More preferred compounds of Formula (1) are of Formula (2):
in which
Z is CONH
2
, CN or H;
R
1
is optionally substituted C
2-8
alkyl (preferably hydroxy substituted) or a glycol group (for example CH
2
CH
2
OCH
2
CH
3
or CH
2
CH
2
OCH
2
CH
2
OH);
with the proviso that if the SO
3
M group is in the 4-position of the benzene ring then either R
1
is other than ethyl or Z is other than H.
In general, preferred compounds of the invention are those which give particularly bright yellow films and prints, and are easily synthesised from readily available intermediates. Solubility in an aqueous ink is also desirable, hence compounds of Formula (1) comprise at least one SO
3
M or PO
3
M
2
group, comprise substituent (e.g. R
1
) of C
8
(or less) carbyl-derived groups. To improve solubility optionally R
1
comprises at least one PEG and/or OH group.
Compounds of the present invention can be prepared by analogy to any of the methods known in the art, for example as in GB 1,271,226.
According to a further aspect of the present invention there is provided a compound of Formula (1) as hereinbefore defi

Affiliated with

Also associated with

Rating

Azopyridone compounds, compositions and use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Azopyridone compounds, compositions and use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Azopyridone compounds, compositions and use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3190152