Isoxindigos useful as colorants and preparation thereof

Details Isoxindigos useful as colorants and preparation thereof Isoxindigos useful as colorants and preparation thereof

1998-09-03

2001-11-27

Michl, Paul R. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C549S302000

Reexamination Certificate

active

06323267

ABSTRACT:

This invention relates to the use of (E)-[3,3′]-bibenzofuranylidene-2,2′-diones (“isoxindigos”) as colorants for the mass coloration of high molecular weight organic materials, to novel compositions of matter comprising isoxindigos, to novel isoxindigos and also to a novel process for preparing isoxindigos.
Isoxindigos are closely related to Pechmann dyes and are sometimes even referred to as such. Pechmann dyes, as disclosed in Chem. Reviews 54, 59 (1954), are known for dyeing wool and silk, but the results are unsatisfactory, since the light stability in particular proves to be inadequate. Like Pechmann dyes, isoxindigos are chemically relatively unstable and are converted, for example, by base catalysis or even thermally into the differently coloured, thermodynamically more stable naphthyrone isomers:
Isoxindigos have a wide range of colours which varies with the substitution pattern and extends from yellow via red and blue through to black [J. Org. Chem. 47/6, 1095 (1982); J. Chem. Soc. Perkin I, 2479 (1992)]. The colour results mainly from a charge transfer absorption which is enhanced by methoxy substituents, although twisting and length of the central double bond due to steric hindrances is additionally said to play a part [Aust. J. Chem. 38, 85 (1985)].
It has now been found that, surprisingly, isoxindigos are excellent colorants for mass coloration of polymers, producing nonmigrating colours which are very light- and heat-fast. Unlike conventional colorants having comparable colour properties, the colorants of this invention advantageously contain no heavy metals. The solubility of the isoxindigos of this invention in organic solvents is highly structure-dependent, making them readily conformable to the desired specifications, which is an advantage. The isoxindigos of this invention are highly useful as colorants for the mass coloration of a high molecular weight organic material, and they can be present in the substrate to be coloured in a dissolved state (like dyes) and/or in a finely dispersed state (like pigments).
The present invention accordingly provides a process for coloration of a high molecular weight material, in particular in the mass, which comprises admixing said high molecular weight organic or inorganic material, preferably high molecular weight organic material, preferably prior to processing, with at least one compound of the formula
where A
1
and A
2
are independently unsubstituted, monosubstituted, disubstituted, trisubstituted or tetrasubstituted o-C
6
-C
18
arylene.
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. In the case of substituted o-C
6
-C
18
arylene the substituents may be independently of each or one another any desired atoms, groups of atoms or radicals which, depending on their valency, may be singly or multiply attached to A
1
or to A
2
. Bivalent radicals for example, such as 1,3-butadien-1,4-ylene or —CH═CH—NH—, may form an additional 5- or 6-membered ring fused onto A
1
and A
2
.
The compounds of the formula (I) are, for example, symmetrical or asymmetrical isoxindigos. In the case of substituted o-C
6
-C
18
arylene the substituent can be, for example, a bridge leading to a further isoxindigo. In this bisisoxindigo structure, two isoxindigos may be joined together, for example, via an alkylene, cycloalkylene, polycycle, aryl or heteroaryl bridge.
Preference is given to using an isoxindigo of the formula
a bisisoxindigo of the formula:
where A
3
is a single bond or unsubstituted or halogen-, hydroxyl-, oxo-, cyano-, R
6
OOC—, X
+
O
−
C—, R
6
O
3
S—, X
+
O
3
+
S-monosubstituted or -polysubstituted C
1
-C
24
alkylene or C
5
-C
12
cycloalkylene, or a polycycle which may be interrupted by heteroatoms such as O, N, S or P, or C
6
-C
24
aryl and C
5
-C
18
heteroaryl which may be uninterrupted or singly or multiply interrupted by O, S or NR
6
,
R
100
, R
101
, R
102
, R
100′
, R
102′
and also R
103
, R
104
, R
105
and R
106
each independently have the same meaning as R
1
,
R
1
, R
2
, R
3
, R
4
and also R
28
, R
29
, R
30
or R
31
, are independently H, halogen, 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
, (C
1
-C
12
alkyl)-COOR, COO
−
X
+
, SR
5
, SOR
5
, SO
2
R
5
, SO
2
NR
7
R
8
, SO
3
R
5
or SO
3
−
X
+
,
and optionally 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
may each be additionally joined together by a direct bond (with abstraction of a hydrogen on each of the two atoms connected by the bond) to form a 5- or 6-membered ring,
R
5
is hydrogen, unsubstituted or halogen- or hydroxyl-, oxo-, cyano-, R
6
OOC— or X
+
O
−
OC-monosubstituted or -polysubstituted C
1
-C
25
alkyl, C
5
-C
12
cycloalkyl or C
2
-C
24
alkenyl, which may be uninterrupted or singly or multiply interrupted by O, S or NR
6
, or is unsubstituted or halogen-, nitro-, cyano-, R
6
O—, R
6
S—, R
8
R
7
N—, R
8
R
7
NOC—, R
6
OOC—, X
+
O
−
OC—, R
6
O
2
S—, R
8
R
7
NO
2
S—, R
6
O
3
S—, X
+
O
3
−
S—R
6
OCR
7
or R
6
OOCR
7
N-monosubstituted or -polysubstituted C
6
-C
18
aryl, C
7
-C
18
aralkyl or A
5
-A
18
heteroaryl,
R
6
is hydrogen, unsubstituted or halogen- or hydroxyl-, oxo- or cyano-monosubstituted or -polysubstituted C
1
-C
25
alkyl or C
2
-C
24
alkenyl, which may be uninterrupted or singly or multiply interrupted by O, S or NR
7
, or is unsubstituted or halogen-, nitro-, cyano-, hydroxyl-, R
7
O—, R
7
S—, R
8
R
7
N—,R
8
R
7
NOC—, R
7
OOC—, HOOC—, or X
+
O
−
OC-monosubstituted or -polysubstituted C
6
-C
18
aryl, C
7
-C
18
aralkyl or A
5
-A
18
heteroaryl,
R
7
and R
8
are singly H, C
6
-C
18
aryl, C
7
-C
18
aralkyl, unsubstituted or halogen-, hydroxyl- or C
1
-C
12
alkoxy-monosubstituted or -polysubstituted C
1
-C
25
alkyl or C
2
-C
24
alkenyl, or
R
7
and R
8
combine with the common N to form unsubstituted or C
1
-C
4
alkyl-monosubstituted, -disubstituted, -trisubstituted or -tetrasubstituted pyrrolidine, piperidine, piperazine or morpholine or to form carbazole, phenoxazine or phenothiazine,
X
+
is a cation Li
+
, Na
+
, K
+
, Mg
++
½
, Ca
++
½
, Sr
++
½
, Ba
++
½
, Cu
+
, Cu
++
½
, Zn
++
½
, Al
+++
⅓
, or [NR
7
R
8
R
10
R
11]
+
, and
R
10
and R
11
are singly H, C
1
-C
25
alkyl, C
6
-C
18
aryl or C
7
-C
18
aralkyl.
In the case of a polysubstituted group, various substituents may be combined.
In a further embodiment of the process of this invention, the high molecular weight organic or inorganic material may optionally also be admixed with a plurality of compounds, preferably 2 to 10, particularly preferably 2 or 3, compounds, of the formula (I).
Alkyl, alkenyl or alkylene can be straight-chain, branched, monocyclic or polycyclic. Preference is given to C
1
-C
12
alkyl, C
2
-C
12
alkenyl or C
2
-C
24
alkylene. C
1
-C
12
Alkyl is therefore, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, trimethylcyclohexyl, decyl, menthyl, thujyl, bornyl, 1-adamantyl, 2-adamantyl or dodecyl.
C
1
-C
24
Alkylene is therefore, for example, methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, cyclobutylene, n-pentylene, 2-pentylene, 3-pentylene, 2,2-dimethylpropylene, cyclopentylene, cyclohexylene, n-hexylene, n-octylene, 1,1,3,3-tetramethylbutylene, 2-ethylhexylene, nonylene, trimethylcydohexylene, decylene, menthylene, thujylene, bornylene, 1-adamantylene, 2-adamantylene, dodecylene, tetradecylene, hexadecylene, heptadecylene, octadecylene, eicosylene, heneicosylene, d

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