Dibenzonaphthyrones

Details Dibenzonaphthyrones Dibenzonaphthyrones

1999-03-29

2001-08-28

Owens, Amelia (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S264000

Reexamination Certificate

active

06281361

ABSTRACT:

The present invention relates to novel dibenzonaphthyrones, to processes for the preparation thereof, to a process for colouring/pigmenting organic or inorganic, high-molecular-weight or low-molecular-weight material with dibenzonaphthyrones and to substance compositions comprising dibenzonaphthyrones.
Dibenzonaphthyrones of the formula
H. D. Becker et al., Aust. J. Chem., 38(1), 97-110, 1985 describe the compounds of formulae (II) to (V).
Dibenzonaphthyrones of formulae (VI) to (XIII) are known from J. Indian. Chem. Soc., 45, 35 (1968), J. N. Chatterjea et al.
The dibenzonaphthyrone of formula (XIV) is known from Chem. Ber., 117(2), 666-671, 1984, Saalfrank, R. W. et al.
The dibenzonaphthyrone of formula (XV) is known from Bull. Soc. Chim. Fr., 5
e
sér.,T.9, 826 (1942), Ch. Marschalk et al.
The industrial use of dibenzonaphthyrones has been negligible hitherto since their difficult preparation from complicated starting materials is uneconomic and/or the use of oxidising agents containing heavy metals is ecologically unsound.
Aust. J. Chem., 38(1), 97-110, 1985, H. D. Becker et al. disclose, for example, the preparation of dibenzonaphthyrone from isoxindigo, which is difficult to obtain synthetically, by base-catalysed isomerisation, or, Chem. Ber. 117(2), 666-671, Saalfrank, R. W. et al., the isomerisation of coumarin, which has to be prepared in several stages, and, Chem. Lett., 1301-1304, 1979, Shibata K. et al., photo-oxidative multiple-stage preparation from flava-nonol compounds, or J. Indian Chem. Soc. 45, 35-44, 1968, Chatterjea, J. N. et al., condensation from coumarin or trans-2,2dimethoxydicyanostilbene.
Tet. Left., 39, 4671-4674, 1966, Kubota, T. et al. discloses the preparation of dibenzonaphthyrone by oxidation with potassium permanganate and, Bull.Soc.Chim. Fr., 5
e
sér.,T.9, 826 (1942), Ch. Marschalk et al., oxidation with iron chloride or chromic acids.
Fluorescing properties of dibenzonaphthyrones, both in solution and in the crystalline state, are mentioned in Aust. J. Chem., 38(1), 97-110, 1985, H. D. Becker et al.
The use of dibenzonaphthyrones as colourants is not known.
Their difficult preparation makes them too expensive for most purposes.
The problem underlying the invention was therefore to find novel dibenzonaphthyrones that are suitable as colourants or fluorescent agents, especially for colouring/pigmenting organic or inorganic, high-molecular-weight or low-molecular-weight material, but especially high-molecular-weight organic material. In addition, the problem consisted of finding a simpler and cheaper process for the preparation of dibenzonaphthyrones.
The present invention relates to novel dibenzonaphthyrones of the general formula (I)
wherein A
1
, and A
2
are each independently of the other unsubstituted or mono- to tetra-substituted o-C
6
-C
18
arylene, with the proviso that formula (I) does not represent a dibenzonaphthyrone of the formula
o-C
6
-C
18
Arylene is, for example, 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene, 1,2-phenanthrylene, 2,3-phenanthrylene, 3,4-phenanthrylene or 9,10-phenanthrylene. If o-C
6
-C
18
arylene is substituted, the substituents may, independently of one another, be any desired atoms, groups of atoms or radicals, which, depending on their valency, may be bonded to A
1
or to A
2
by one or more bonds. For example, divalent radicals, such as 1,3-butadien-1,4-ylene or —CH═CH—NH—, may then produce an additional 5- or 6-membered ring fused to A
1
and A
2
, with the proviso that formula (I) does not represent a dibenzonaphtyrone of formulae (II) to (XV).
The compounds of formula (I) are, for example, symmetric or asymmetric dibenzonaphthyrones. If o-C
6
-C
18
arylene is substituted, the substituent may, for example, be a bridge to a further dibenzonaphthyrone. In that bis-dibenzonaphthyrone structure, two dibenzonaphthyrones may be linked to each other, for example, by an alkylene or cycloalkylene bridge.
Preference is given to the use of dibenzonaphthyrone of the formula
wherein A
3
is a single bond, or C
1
-C
24
alkylene unsubstituted or mono- or poly-substituted by halogen, hydroxy, oxo, cyano, OCOR
6
, COOR
6
, COO
−
X
30
, SO
3
−
X
+
or by SO
3
R
6
, a polycyclic radical or C
5
-C
12
cycloalkylene, each of which may be uninterrupted or interrupted one or more times by O, N, P, S or by NR
6
, and C
6
-C
24
arylen and A
1
-A
24
heteroarylen,
and R
100
, R
101
, R
102
and R
100′
, R
101′
, R
102′
and R
103
, R
104
, R
105
, R
106
have independently of one another the same meanings as R
1
, and
R
1
, R
2
, R
3
, R
4
and R
28
, R
29
, R
30
or R
31
are each independently of the others cyano, NO
2
, R
5
, NR
5
R
6
, NR
7
COR
5
, NR
7
COOR
5
, N═CR
5
R
6
, CONR
7
R
8
, OR
5
, COOR
5
, COO
−
X
+
, SR
5
, SOR
5
, SO
2
R
5
, SO
2
NR
7
R
8
, SO
3
R
5
or SO
3
−
X
+
, it being possible, where applicable, for the pairs of radicals R
1
and R
2
, R
2
and R
3
, R
3
and R
4
or R
5
and R
6
, and also R
28
and R
29
, R
29
and R
30
or R
30
and R
31
to be, in addition, joined together by a direct bond (with the removal of a hydrogen atom at each of the two atoms joined by the bond), so that a 5- or 6-membered ring is produced;
R
5
is hydrogen, or C
1
-C
25
alkyl, C
5
-C
12
cycloalkyl or C
2
-C
24
alkenyl each of which is unsubstituted or mono- or poly-substituted by halogen, hydroxy, oxo, cyano, OCOR
6
, COOR
6
or by COO
−
X
+
and each of which may be uninterrupted or interrupted one or more times by O, S or by NR
6
, or is C
6
-C
18
aryl, C
7
-C
18
aralkyl or A
5
-A
18
heteroaryl each of which is unsubstituted or mono- or poly-substituted by halogen, nitro, cyano, OR
6
, SR
6
, NR
7
R
8
, CONR
7
R
8
, OCOR
6
, COOR
6
, COO
−
X
+
, SO
2
R
6
, SO
2
NR
7
R
8
, SO
3
R
6
, SO
3
−
X
+
, NR
7
COR
6
or by NR
7
COOR
6
,
R
6
is hydrogen, or C
1
-C
25
alkyl unsubstituted or mono- or poly-substituted by halogen, hydroxy, oxo or by cyano, or OCO—R
10
, COO—R
10
or COO
−
X
+
, or C
2
-C
24
alkenyl, each of which may be uninterrupted or interrupted one or more times by O, S or NR
7
, or is C
6
-C
18
aryl, C
7
-C
18
aralkyl or A
5
-A
18
heteroaryl each of which is unsubstituted or mono- or poly-substituted by halogen, nitro, cyano, hydroxy, OR
7
, SR
7
, NR
7
R
8
, CONR
7
R
8
, COOR
7
, OCOR
7
, COOH or by COO
−
X
+
,
R
7
and R
8
independently of each other are hydrogen, C
6
-C
18
aryl, C
7
-C
18
aralkyl, or are C
1
-C
25
alkyl or C
2
-C
24
alkenyl each unsubstituted or mono- or poly-substituted by halogen, hydroxy, C
1
-C
12
alkoxy, OCO—R
10
, COO—R
10
or by COO
−
X
+
, or
R
7
and R
8
together with the common N are pyrrolidine, piperidine, piperazine or morpholine each unsubstituted or mono- to tetra-substituted by C
1
-C
4
alkyl, or are carbazole, phenoxazine or phenothiazine,
X
+
is a cation Li
+
, Na
+
, K
+
, Mg
++
1/2
, Ca
++
1/2
, Sr
++
1/2
, Ba
++
1/2
, Cu
+
, Cu
++
1/2
, Zn
++
1/2
, Al
+++
1/3
or [NR
7
R
8
R
10
R
11
]
+
, and
R
10
and R
11
independently of each other are hydrogen, C
1
-C
25
alkyl, C
6
-C
18
aryl or C
7
-C
18
-aralkyl, with the proviso that, in formula (XVIa), dibenzonaphthyrones of formulae (II) to (XV) are excluded.
If a group is poly-substituted, different substituents may be combined.
The present invention further relates to a process for the preparation of dibenzonaphthyrones, which is described in detail hereinafter.
The invention also relates to substance compositions comprising at least one dibenzonaphthyrone selected from the group of compounds of formulae (I) to (XV) and organic or inorganic, high-molecular-weight or low-molecular-weight material, especially high-molecular-weight organic material.
The present invention furthermore relates to a process for colouring/pigmenting organic or inorganic, high-molecular-weight or low-molecular-weight material, especially high-molecular-weight organic material, with at least one dibenzo

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