Bridged perinones/quinophthalones

Details Bridged perinones/quinophthalones Bridged perinones/quinophthalones

2002-11-22

2004-12-21

McKenzie, Thomas (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S110000, C546S154000, C546S173000, C546S174000, C544S245000, C548S301700, C008S689000, C106S031270, C106S287210

Reexamination Certificate

active

06833455

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to bridged perinones, quinophthalones and perinone-quinophthalones, processes for their preparation and their use for mass coloration of plastics.
2. Brief Description of the Prior Art
It is known to use perinone dyes as described for example in FR-A-1 075 110 or U.S. Pat. No. 5,466,805 for mass coloration of plastics. It is also known to use quinophthalone dyes as described for example in DE-A-44 35 714 or DE-A-21 32 681 for mass coloration of plastics. Compounds of this type are notable for good thermal stability and high light fastness, but their sublimation fastness is still in need of improvement. Illustratively, temperatures of above 240° C. which occur in the coloration process in the injection moulding machines, lead all too commonly to an undesirable sublimation of the dye, contaminating the working equipment and necessitating costly and inconvenient cleaning measures. EP-A-827 986 already discloses doubled quinophthalone and perinone dyes possessing good sublimation fastness.
It is an object of the present invention to provide further sublimation-fast dyes for the mass coloration of plastic, which are preferably readily soluble in the monomeric starting materials of the plastic too in order that greater flexibility in the coloration of plastics may be ensured.
SUMMARY OF THE INVENTION
There have now been found compounds of the general formula (I) or tautomeric forms thereof
where
Ar
1
and Ar
2
are independently radicals needed to complete optionally substituted carbocyclic aromatics,
B is a radical of the formula -T
1
-W-T
2
-, where
T
1
and T
2
are independently O or S and
W is alkylene, especially C
1
-C
6
-alkylene, C
6
-C
10
-arylene, especially phenylene or cycloalkylene, which are each optionally substituted or is the radical of the formula (a)
 where the phenyl rings are optionally substituted and
A is a radical of the formula O, S, SO, SO
2
or CO, optionally substituted alkylene, or optionally substituted cycloalkylene, said alkylene or cycloalkylene being attached to the adjacent phenyl rings itself or else via its substituents, or
W is a radical of the formulae
 where
s and t are independently from 1 to 6,
the ends of the radical B each being attached to an aromatic carbon atom of the two radicals Ar
1
and Ar
2
,
and
X
1
and X
2
are independently a radical of the formulae selected from the group consisting of
each being located in the ring in such a way that the
is adjacent to the C—C double bond,
where
Y is a radical of an optionally substituted benzene or naphthalene ring,
Z is optionally substituted ortho-phenylene, ortho-naphthylene, peri-(1,8)-naphthylene or arylene composed of more than two fused-together benzene rings, aryl radicals which have more than two fused-together benzene rings being bridged ortho or in a manner corresponding to a peri position in naphthalene,
R
a
is H or OH, and
R
b
is H or halogen, especially F, Br or Cl.
The peri position actually denotes the 1,8-position in naphthalene. Both in the literature and in the context of the present application, however, this meaning is extended to include arylenes composed of more than two fused-together benzene rings.
Possible substituents for Z and for the two phenyl rings of the radical of the formula (a) include for example: C
1
-C
6
-alkyl, halogen, nitro, aryl, aryloxysulphonyl, hydroxyl, C
1
-C
6
-alkoxy, aryloxy, optionally alkyl- or acyl-substituted amino, optionally alkyl- or aryl-substituted aminosulphonyl, optionally alkyl-substituted carboxamide or a fused-on aromatic, cycloaliphatic or heterocyclic ring.
Preferred substituents are: chlorine, bromine, nitro, methoxy, NH
2
, benzyloxy, hydroxyl, —SO
2
O(C
6
H
5
), —SO
2
N(CH
3
)
2
, —SO
2
NHCH
3
, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, NHCOCH
3
, —N(C
2
H
5
)
2
or optionally substituted phenyl.
Possible substituents for the benzene or naphthalene radical completed by Y include for example: halogen, especially Cl and Br, —COOH, —COOR, where R is C
1
-C
10
alkyl, preferably C
1
-C
4
-alkyl, especially methyl or ethyl, C
6
-C
10
-aryl or C
5
-C
8
-cycloalkyl, and C
1
-C
6
-alkyl, especially methyl.
Possible substituents for the carbocyclic aromatic completed by Ar
1
and Ar2 include for example: C
1
-C
6
-alkyl, especially methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl and tert-butyl, halogen, especially Cl or Br, alkylcarbonyl, arylcarbonyl, alkylsulphonyl, arylsulphonyl, nitro, aryl, especially optionally substituted phenyl, aryloxysulphonyl, especially —SO
2
OC
6
H
5
, hydroxyl, C
1
-C
6
-alkoxy, such as methoxy or benzyloxy, aryloxy, such as phenoxy, optionally alkyl- or acyl-substituted amino such as NH
2
, NHCOCH
3
or —N(C
2
H
5
)
2
, optionally alkyl- or aryl-substituted aminosulphonyl such as SO
2
N(CH
3
)
2
or SO
2
NHCH
3
or a fused-on aromatic, cycloaliphatic or heterocyclic ring.
Particularly preferably Ar
1
and Ar2 are independently a radical needed to complete an optionally substituted benzene or naphthalene ring, especially an optionally substituted benzene ring.
Possible substituents for the alkylene group in W and A, which can be not only straight-chain but also branched, include for example halogen such as F or Cl, CF
3
, O, S, optionally substituted phenyl and C
1
-C
6
-alkyl.
Possible substituents for the cycloalkyl group, especially the C
5
-C
6
-cycloalkylene group, particularly preferably the cyclohexylidene group, include for example one or more C
1
-C
4
-alkyl radicals.
Particular preference is given to compounds of the formula (I) which conform to the formula (II) or tautomeric forms thereof
where
Y
1
and Y
2
are independently the radical of an optionally substituted benzene or naphthalene ring,
R
a1
and R
a2
are independently H or OH, and
R
b1
and R
b2
are independently H or halogen, especially Br or Cl and
Ar
1
, Ar
2
and B are each as defined above.
Possible substituents for the radicals Y
1
and Y
2
are for example the substituents indicated for the radical Y.
Particularly preferably R
b1
and R
b2
are each hydrogen.
Particular preference is given to compounds of the formula (II) which conform to the formula (IIa) or tautomeric forms thereof
where
n and m are independently from 0 to 4,
R
1
and R
2
each independently have the same or different meanings as indicated for the substituents for the radicals completed by Y
1
and Y
2
,
o and p are independently from 0 to 2, especially 0 or 1,
R
3
and R
4
each independently have the same or different meanings as indicated for the substituents for the carbocyclic aromatics completed by Ar
1
and Ar
2
,
R
b1
and R
b2
are each as defined above and are preferably H,
R
a1
and R
a2
are each as defined above and are preferably OH, and
B is as defined above. The preferred B include
 and also the corresponding dithio compounds (T
1
and T
2
=S).
Also, the preferred B are those wherein W or A have the following meanings:
—CH
2
—, —CH
2
—CH
2
—, —CH
2
CH
2
CH
2
—, —CH
2
CH
2
CH
2
CH
2
—,
Very particular preference is given to compounds of the formula (II) where
Y
1
=Y
2
R
a1
=R
a2
R
b1
=R
b2
and
Ar
1
=Ar
2
.
Preference is also given to compounds of the formula (IIa) where
n=m,
R
1
=R
2
,
R
a1
=R
a2
,
R
b1
=R
b2
,
o=p and
R
3
=R
4
,
where in particular
n, m, o and p are each 0.
Particular preference is given to compounds of the formula (II) which conform to the formula (IIb) or tautomeric forms thereof
where
n, m, R
1
, R
2
, R
b1
, R
b2
and B are each as defined above.
The compounds of the formula (I) according to the invention are notable for excellent sublimation fastness in the mass coloration of plastics. They also possess very good light fastness, good thermal stability and particularly high colour strength. A colour strength comparison of for example the compounds of formula (II) with the non-doubled quinophthalones shows a disproportionately large increase (based on molecular weight increase).
When the quinophthalones o

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