Triphendioxazine pigments

Details Triphendioxazine pigments Triphendioxazine pigments

1999-03-24

2001-04-10

Shah, Mukund J. (Department: 1611)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C054S014000, C054S076000, C054S050000

Reexamination Certificate

active

06214989

ABSTRACT:

The present invention relates to novel triphendioxazine compounds containing carbamate groups, their preparation and their use as pigments and also as pigment precursors which are readily convertible into the corresponding pigments.
The present invention provides novel carbamate group-containing triphendioxazine compounds which not only can be used as pigments, but are also readily convertible into the corresponding triphendioxazine pigments without carbamate groups and accordingly clear the way to unexpected applications. Including compounds having N-alkoxycarbonyl groups whose alkyl radicals are branched at the carbon which is attached to the oxygen.
The present invention accordingly provides compounds of the formula (I)
in which the nuclei designated A and B independently of each other comprise annelated rings which are fused on linearly, in 2,3- and 9,10-position, or angularly, in 1,2- and 8,9 or in 3,4- and 10,11-position, to feature the complementary members selected from the group consisting of the moieties (1) to (11)
wherein
R
1
is hydrogen, C
1-8
alkyl, unsubstituted phenyl or phenyl which is mono- or poly- substituted by radicals selected from the group consisting of halogen, nitro groups, C
1-8
alkyl and C
1-2
alkoxy, preferably chlorine or C
1-4
alkyl,
R
2
is hydrogen, C
1-8
alkyl, unsubstituted phenyl, an amino group or phenyl which is mono- or poly-substituted by radicals selected from the group consisting of halogen, nitro groups, C
1-8
alkyl and C
1-2
alkoxy, preferably chlorine or C
1-4
alkyl;
and the bond designated with an * leads to the nitrogen atom and the angular molecules in 3- and 10-position or in 2- and 9-position may each bear a C
1-2
alkoxy group,
the radicals R
3
are selected from the group consisting of the formulae (II), (III) and (IV)
wherein
m, n and p are independently of each other zero or 1;
X is C
1-4
alkylene or C
2-8
alkenylene;
Y is a group —V—(CH
2
)
q
—;
Z is a group —V—(CH
2
)
r
—;
V is C
3-6
cycloalkylene;
q is an integer from 1 to 6; and
r is an integer from 0 to 6,
R
4
and R
5
are independently hydrogen, C
1-6
alkyl, C
1-4
alkoxyl, halogen, —CN, —NO
2
, unsubstituted phenyl or phenoxy or phenyl or phenoxy substituted by C
1-4
alkyl, C
1-4
alkoxyl or halogen;
Q is hydrogen, —CN, Si(R
4
)
3
, a group C(R
8
)(R
9
)(R
10
), wherein R
8
, R
9
and R
10
are halogen, a group
 in which
R
4
and R
5
are as defined above,
a group SO
2
—R
11
or SR
11
, wherein R
11
is C
1-4
alkyl,
a group CH(R
12
)
2
, wherein R
12
is unsubstituted phenyl or phenyl substituted by C
1-4
alkyl, C
1-4
alkoxyl or halogen, or
a group of the formula
R
6
and R
7
are independently of each other hydrogen, C
1-18
alkyl, a group of the formula
 in which
X, Y, R
4
, R
5
, m and n are as defined above, or
R
6
and R
7
together with the nitrogen atom to which they are bonded form a pyrrolidinyl, piperidinyl or morpholinyl radical,
with the proviso that, when R
3
is a group of the formula (III), Q is hydrogen and n is zero, then m shall be 1 and X shall be a C
2-14
alkylene or C
2-8
alkenylene group which is branched at the carbon which is attached to the oxygen.
If X denotes C
1-4
alkylene X is a straight-chain or branched alkylene, for example methylene, dimethylene, trimethylene, 1-methyl-methylene, 1,1-dimethyl-methylene, 1,1-dimethyl-dimethylene, 1,1-dimethyl-trimethylene, 1-ethyl-dimethylene, 1-ethyl-1-methyl-dimethylene, tetramethylene, 1,1-dimethyl-tetramethylene, 2,2-dimethyl-trimethylene, hexamethylene, decamethylene, 1,1-dimethyl-decamethylene, 1,1-diethyl-decamethylene or tetradecamethylene.
If X stands for C
2-8
-alkenylene X is a straight-chain or branched alkenylene, for example vinylene, allylene, methallylene, 1-methyl-2-butenylene, 1,1-dimethyl-3-butenylene, 2-butenylene, 2-hexenylene, 3-hexenylene or 2-octenylene.
Is any substitutent halogen then it is for example iodine, fluorine, especially bromine and preferably chlorine;
C
1-6
Alkyl is for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-amyl, tert-amyl, hexyl and C
1-8
alkyl is additionally for example heptyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl;
C
1-4
Alkoxy signifies for example methoxy, ethoxy, n-propoxy, isopropoxy, butyloxy, and C
1-8
alkoxy is additionally for example hexyloxy, decyloxy, dodecyloxy, hexadecyloxy or octadecyloxy;
C
1-18
Alkylmercapto is for example methylmercapto, ethylmercapto, propylmercapto, butylmercapto, octylmercapto, decylmercapto, hexadecylmercapto or octadecylmercapto;
C
1-18
Alkylamino is for example methylaminio, ethylamino, propylamino, hexylamino, decylamino, hexadecylamino or octadecylamino.
C
5-6
Cycloalkyl is for example cyclopentyl and especially cyclohexyl.
C
3-6
Cycloalkylene is for example cyclopropylene, cyclopentylene and especially cyclohexylenes.
In preferred compounds of the formula (I), the moieties
preferably correspond to the formulae (a) to (p)
Preferred are compounds of the formula (I) in which R
3
represents a group of the formula (V), (VI) or (IV)
wherein
m is zero or 1,
X is C
1-4
alkylene or C
2-5
alkenylene,
R
4
and R
5
are independently of each other hydrogen, C
1-4
alkyl, methoxy, chlorine or —NO
2
, and
Q is hydrogen, CN, CCl
3
, a group
 —SO
2
CH
3
or SCH
3
,
R
6
and R
7
are independently of each other hydrogen, C
1-4
alkyl or a group
or R
6
and R
7
form together a piperidinyl radical,
with the proviso that, when R
3
is a group of the formula (VI) and Q is hydrogen, then X shall be a group
especially if the radical R
3
signifies a group selected from the group containing of the following formulae
The invention further provides a process for preparing triphendioxazine compounds of the formula (I), characterized in that a compound of the formula (VII)
wherein
the nuclei designated A and B have the same meaning as in formula (I) but R
3
is hydrogen,
is reacted in the desired molar ratio with a dicarbonate of the formula (VIII)
R
3
—O—R
3
  (VIII)
or with a trihaloacetic ester of the formula (IX)
(R
13
)
3
C—R
3
  (IX)
or with a 1:1 mixture of a dicarbonate of the formula (VIII) and a dicarbonate of the formula (X)
R′
3
—O—R′
3
  (X)
or with a 1:1 mixture of a trihaloacetic ester of the formula (IX) and a trihaloacetic ester of the formula (XI)
(R
13
)
3
C—R′
3
  (XI)
or with an azide of the formula (XII)
R
3
N
3
  (XII)
which may also be used in a 1:1 mixture with
 R′
3
N
3
  (XIII)
or with a carbonate of the formula (XIV)
R
3
—OR
14
  (XIV)
which may also be used in a 1:1 mixture with
R′
3
—OR
14
  (XV)
or with an alkylideneiminooxyformic ester of the formula (XVI)
which may also be used in a 1:1 mixture with
wherein
R
3
is as defined above and R′
3
has a meaning of R
3
which is different from R
3
,
R
13
is chlorine, fluorine or bromine,
R
14
is C
1-4
alkyl or unsubstituted phenyl or phenyl substituted by halogen, C
1-4
alkyl, C
1-4
alkoxyl or —CN,
R
15
is —CN or —COOR
14
, and R′
15
has a meaning of R
15
which is different from R
15
, and
R
16
is unsubstituted phenyl or phenyl substituted by halogen, C
1-4
alkyl, C
1-4
alkoxyl or —CN, and R′
16
has a meaning of R
16
which is different from R
16
,
in an aprotic organic solvent in the presence of a base as catalyst, advantageously at temperatures between 0 and 200° C., preferably between 10 and 100° C., for 2 to 48 hours.
Preferably, the compound of the formula (VII) is reacted with a dicarbonate of the formula (VIII) or with a 1:1 mixture of a dicarbonate of the formula (VIII) and a dicarbonate of the formula (X).
Compounds of the formula (VII), dicarbonates of the formulae (VIII) and (X), trihaloacetic esters of the formulae (IX) and (XI), azides of the formulae (XII) and (XIII), carbonates of the formulae (XIV) and (XV) and alkylideneiminooxyformic esters of the formulae (XVI) and (XVII) are known substances. Should any be novel nonetheless, they can be prepared in analogy to commonly known methods.
The necessary molar r

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