Substituted phthalocyanine

Details Substituted phthalocyanine Substituted phthalocyanine

2001-03-12

2002-09-03

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C540S122000, C540S132000, C540S133000, C540S134000, C540S136000, C540S137000, C540S140000

Reexamination Certificate

active

06444807

ABSTRACT:

The invention relates to novel phthalocyanine compounds and to their use as colourants.
Phthalocyanines have long been known as colourants, especially as blue pigments, for example C.I Pigment Blue 15 and Pigment Blue 16. By means of substituents, the colour of the parent substance can be influenced within certain limits, substituted products generally being poorly defined mixtures of a large number of components, the composition and colour of which are greatly dependent on the preparation conditions.
Modern technologies, however, demand colourants that are ever better characterised and the shade of which can be produced under a very wide variety of conditions in as reproducible a manner as possible. Such a property is important especially in the case of colourants that are used in a readily soluble latent form and are only thereafter to be converted to the final pigment form.
The known substituted phthalocyanines do not, however, adequately meet that demand.
WO98/14520 discloses the selective preparation of formylated and acylated phthalocyanines, as well as products obtainable therefrom.
There are known from EP 648 817 phthalocyanines having alkoxycarbonylamino groups that are bonded to the phthalocyanine nucleus directly or via a C
1
-C
4
-1,1-alkylene group or a sulfone group. WO98/32802 discloses various possible applications thereof.
WO98/32802 describes the readily soluble compound of formula
and the thermal decomposition thereof.
Surprisingly, it has been found, however, that such latent phthalocyanines can lead to unexpected difficulties in practical use. In contrast to other latent pigments, thermal decomposition produces undesirable colour shades, and the fastness properties thereof are not sufficiently satisfactory, which poses a problem particularly in the case of high-quality applications, polychromatic systems and, especially, light-sensitive compositions (resists), where high demands and very precise shades must be achieved, for example in colour filters.
U.S. Pat. No. 3,972,904 describes water-soluble textile colourants which cannot, however, be used in conventional high-quality, polychromatic and light-sensitive compositions.
Example 8 of U.S. Pat. No. 4,381,261 describes the preparation of the compound of formula
which, however, owing to its high viscosity, cannot be used in conventional high-quality, polychromatic and light-sensitive compositions.
U.S. Pat. No. 4,000,158 describes alcohol- and ketone-soluble phthalocyanine compounds which, since their final solubility in the developer is too high, cannot be used in conventional light-sensitive compositions.
Surprisingly, it has been possible to solve such problems with the compounds according to the invention.
Accordingly, the invention relates to a compound of formula
wherein
M is a divalent metal, oxo metal, halogenometal or hydroxymetal, or 2 hydrogen atoms,
A is a radical
 which may be unsubstituted or substituted by phenoxy, naphthyloxy, phenylthio or by naphthylthio,
X is a hetero atom selected from the group consisting of N, O and S, m being the number 0 when X is O or S and the number 1 when X is N,
Y is any desired substituent that is inert towards alkylating reagents,
Z is hydrogen, Z′ or COOB,
Z′ is C
2
-C
12
alkylene-N(COOB)
2
, C
2
-C
12
alkylene-NHCOOB, C
2
-C
12
alkylene-OCOOB or C
2
-C
12
alkylene-SCOOB,
x is a number from 1 to 4, and y is a number from 0 to 15,
wherein the sum of x and y is a maximum of 16 and, optionally, a plurality of radicals X, Y, Z and/or Z′ may be identical or different, and
B is a group of the formula
wherein
R
1
is hydrogen or C
1
-C
6
alkyl,
R
2
and R
3
are each independently of the other C
1
-C
6
alkyl,
R
4
and R
8
are each independently of the other C
1
-C
6
alkyl, C
1
-C
6
alkyl interrupted by O, S or by NR
12
, phenyl or biphenyl unsubstituted or substituted by C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halogen, cyano or by nitro,
R
5
, R
6
and R
7
are each independently of the others hydrogen or C
1
-C
6
alkyl,
R
9
is hydrogen, C
1
-C
6
alkyl or a group of the formula
R
10
and R
11
are each independently of the other hydrogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, halogen, cyano, nitro, N(R
12
)
2
, or phenyl unsubstituted or substituted by halogen, cyano, nitro, C
1
-C
6
alkyl or by C
1
-C
6
alkoxy,
R
12
and R
13
are each C
1
-C
6
alkyl, R
14
is hydrogen or C
1
-C
6
alkyl and R
15
is C
1
-C
6
alkyl, or phenyl unsubstituted or substituted by C
1
-C
6
alkyl,
E is p,q-C
2
-C
6
alkylene unsubstituted or mono- or poly-substituted by C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or by C
2
-C
12
dialkylamino, wherein p and q are different position numbers,
X′ is a hetero atom selected from the group consisting of N, O and S, m′ being the number 0 when X′ is O or S and the number 1 when X′ is N,
and
L
1
and L
2
are each independently of the other C
1
-C
6
alkyl or [—(p′,q′-C
2
-C
6
alkylene)—Z″—]
n
-C
1
-C
6
alkyl unsubstituted or mono- or poly-substituted by C
1
-C
6
alkoxy, C
1
-C
6
alkylthio, C
2
-C
12
dialkylamino, C
6
-C
12
aryloxy, C
6
-C
12
arylthio, C
7
-C
18
arylalkylamino or by C
12
-C
24
diarylamino, wherein n is a number from 1 to 1000 and p′ and q′ are different position numbers, each Z″ independently of the other(s) is a hetero atom O, S or C
1
-C
12
alkyl-substituted N, and the C
2
-C
6
alkylene radicals in the repeating units [—C
2
-C
6
alkylene—Z″—] may be identical or different,
and L
1
and L
2
may be saturated or unsaturated from one to ten times, may be uninterrupted or interrupted at any positions by from 1 to 10 groups selected from the group consisting of —(C═O)— and —C
6
H
4
—, and may carry no further substituents or from 1 to 10 further substituents selected from the group consisting of halogen, cyano and nitro.
C
2
-C
12
Alkylene is, for example, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, 1,4-butylene, 2-methyl-1,2-propylene or an isomer of pentylene, hexylene, octylene, decylene or dodecylene.
C
6
-C
12
Aryloxy is O—C
6
-C
12
aryl, for example phenoxy or naphthyloxy, preferably phenoxy.
C
1
-C
6
Alkylthio is S—C
1
-C
6
alkyl, preferably S—C
1
-C
4
alkyl.
C
6
-C
12
Arylthio is S—C
6
-C
12
aryl, for example phenylthio or naphthylthio, preferably phenylthio.
C
2
-C
12
Dialkylamino is N(alkyl
1
)(alkyl
2
) wherein the sum of the carbon atoms in the two groups alkyl
1
and alkyl
2
is from 2 to 12, preferably N(C
1
-C
4
alkyl)-C
1
-C
4
alkyl.
C
7
-C
18
Alkylarylamino is N(alkyl
1
)(aryl
2
) wherein the sum of the carbon atoms in the two groups alkyl
1
and aryl
2
is from 7 to 18, preferably methylphenylamino or ethylphenylamino.
C
12
-C
24
Diarylamino is N(aryl
1
)(aryl
2
) wherein the sum of the carbon atoms in the two groups aryl
1
and aryl
2
is from 12 to 24, for example diphenylamino or phenylnaphthylamino, preferably diphenylamino.
Substituents that are inert towards alkylating reagents are, for example, those which do not react with pyrocarbonates under the conditions indicated hereinbelow, for example those which do not contain hydroxy, amino or thiol groups.
The substituents SO
2
(Z)
m
Z′ and Y may be located at any aromatic carbon of the radicals A, for example at the peripheral positions of a phthalocyanine or naphthalocyanine and/or optionally at any desired position of the phenoxy, naphthyloxy, phenylthio or naphthylthio substituents.
The compound of formula (I) may especially be a compound of formula
In a compound of formula (II), the substituents SO
2
(Z)
m
Z′ and Y are advantageously attached at the peripheral positions of the phenyl rings, preferably at the outer positions (2, 3, 9, 10, 16, 17, 23 and/or 24 according to“Nomenklatur von Porphyrinen und Gallenpigmente”[Nomenclature of porphyrins and bile pigments]/May 1989):
M is preferably Cu, Pd, Pb, Co, Ni, Zn, Mn or V(═O).
A is preferably a radical
X is preferably N or O, especially N.
Y is preferably Cl or Br.
Z is preferably H or COOB, especially COOB.
Z′ is preferably C
2
-C
12
al

Affiliated with

Also associated with

Rating

Substituted phthalocyanine does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2863987