Isoindolenineamide dyestuffs

Details Isoindolenineamide dyestuffs Isoindolenineamide dyestuffs

1997-06-02

2001-03-13

Richter, Johann (Department: 1613)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S161000, C548S173000, C548S217000, C548S222000, C548S305100, C548S306100, C548S953000, C548S954000, C546S201000, C546S270100, C546S270700, C546S271700, C546S273400, C544S135000, C544S143000, C544S153000, C540S602000, C540S603000, C540S607000, C008S571000, C008S572000, C008S573000, C008S574000

Reexamination Certificate

active

06201126

ABSTRACT:

The invention relates to isoindolenineamide dyestuffs, processes for their preparation and their use for dyeing hydrophobic synthetic materials.
DE-A 1,670,748 already discloses isoindolenineamide dyestuffs similar to those of the formula (I), but those dyestuffs still have disadvantages in practical application. Disadvantages in practical application are understood to mean, for example, poor exhaustion or build-up properties in polyester dyeing, or poor light fastness, in particular hot light fastness, i.e. properties which are required when textiles dyed with these dyestuffs are used in the automobile sector.
Isoindolenineamides have been found which have the formula I or correspond to tautomeric forms thereof
in which
A represents N or a cyanomethylene radical,
B represents S, O or NH,
R
1
represents a saturated or unsaturated aliphatic or cycloaliphatic radical having 1 to 12 C atoms, in particular 1 to 10 C atoms, which is uninterrupted or interrupted by one or more oxygen atoms and/or is unsubstituted or substituted by one or more identical or different substituents selected from the group consisting of alkoxy, acyloxy, halogen, CN, aryl, in particular phenyl,
R
2
denotes hydrogen or aryl or adopts one of the meanings given for R
1
, R
1
and R
2
being identical or different, or R
1
and R
2
, together with the N atom to which they are bonded, form a heterocyclic ring,
R
3
denotes halogen, in particular Cl, F and Br, C
1
-C
4
-alkyl, a saturated or unsaturated aliphatic alkoxy radical having 1 to 4 C atoms, in particular C
1
-C
4
-alkoxy, which is unsubstituted or substituted by C
1
-C
4
-alkoxy, CN or NO
2
, and
x denotes a number from 0 to 4.
Examples of suitable radicals R
1
and R
2
are methyl, ethyl, n-propyl, allyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodedyl, 2-acetoxy-ethyl, 2-propionyloxy-ethyl, 2-acetoxy-propyl, 2-methoxy-ethyl, 2-ethoxy-ethyl, 2-butoxy-ethyl,
3
-methoxy-propyl,
3
-ethoxy-propyl, 3-butoxy-propyl,
3
-allyloxy-propyl, 2-ethyl-hexyl,
3
-(2-ethyl-hexyloxy)-propyl, phenyl, benzyl and cyclohexyl. Suitable branched radicals R
1
are preferably those having a methyl side chain, such as, for example, iso-butyl or iso-pentyl. Examples of preferred heterocyclic rings are aliphatic 5-, 6- or 7-membered rings.
Preferred compounds of the formula I are those in which radicals R
1
and R
2
, together with the N atom to which they are bonded, form the secondary amines listed below: diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, methyl-butyl-amine, methyl-(2-acetoxyethyl)-amine, ethyl-(2-acetoxyethyl)-amine, methyl-(2-acetoxypropyl)-amine, bis-(2-acetoxyethyl)-amine, bis-(
2
-acetoxypropyl)-amine, pyrrolidine, piperidine,
2
-methylpiperidine, 4-methylpiperidine, hexamethyleneimine, morpholine, benzyl-methylamine and cyclohexyl-methylamine.
Preferred radicals R
3
are chlorine, methyl, methoxy and ethoxy.
Particularly preferred dyestuffs of the formula (I) are those in which
x represents 0 or 1.
Very particularly preferred dyestuffs are those having the formula (II) or those corresponding to tautomeric forms thereof
in which
A and R
1
-R
3
have the above meaning, x preferably representing 0.
Preferred isoindolenineamides of the formula (I) are those in which A represents N.
Although all the formulae described in this application only represent one tautomeric form of the compound(s) in question, if several forms are possible, they are representative of all the possible tautomeric forms.
Furthermore, an E or a Z isomer described by a formula includes also the other isomer in each case, especially with respect to exocyclic double bond(s). This applies unless expressly stated otherwise.
Furthermore, the invention also provides a process for preparing compounds of the formula (I), which is characterized in that a compound of the formula (III)
is condensed with a compound of the formula (IV)
which is present in the form of the compounds of the formulae IVa or IVb or tautomeric forms thereof
or an amainoisoindolenine of the formula (V)
is condensed with a cyanoacetamide of the formula (VI)
where
R
1
, R
2
, R
3
, A, B and x have the abovementioned meaning.
Individual examples of the compounds of the formula (III) can be represented by the formulae (Va) and (Vb) or tautomeric formulae thereof.
Compounds of the formula (III) can be prepared by methods similar to those of the analogous compounds described in DE-A-1,670,748 or in DE-A-2,041,999.
Particularly preferred compounds of the formula (III) are those in which R
2
is different from hydrogen. Compounds of this type are novel.
In a process for their preparation, amino-imino-isoindoline is reacted with a cyanoacetamide of the formula (VI), the reaction being preferably carried out in a polar, in particular a hydrophilic, organic solvent. Water and mixtures of water with solvents are also suitable. Examples of polar solvents include amides, such as dimethylformamide, formamide, dimethylacetamide, N-methylpyrrolidone, furthermore dimethyl sulphoxide, acetonitrile, acetic acid or, preferably, alcohols, such as, for example, methanol, ethanol, propanol, isopropanol, butanol, methyl glycol or ethyl glycol. In addition, mixtures of these solvents can also be used.
The required reaction temperatures are between about 0 and 100° C., preferably between 20 and 80° C.
In another process for preparing compounds of the formula (III), first an alcohol is subjected to an addition reaction with a phthalodinitrile in the presence of an alkoxide as catalyst to give an intermediate (see I. Chembrier and M. J. Cook, J. Chem. Research, 322 (1990) and F. Baumann et al., Angew. Chem., 68, 133 (1956) and EP 510,436). This intermediate can then be reacted further, without prior isolation, with a cyanoacetamide of the formula (VI), it being possible to add organic acids in order to accelerate the reaction. Suitable alcohols are in particular lower alcohols, such as, for example, methanol, ethanol, propanol and isopropanol. The required reaction temperatures are preferably between 20 and 80° C.
The compounds of the formula (III) can be isolated as intermediates. However, they can also be subjected to condensation directly from the reaction batch, if desired after addition of further solvent and/or water.
Compounds of the formulae (Va) and (Vb) are also described in DE-A-1,670,748.
In a preferred embodiment of the process according to the invention for preparing compounds of the formula (I), condensation is carried out in water, in a polar, in particular a hydrophilic, organic solvent or in mixtures thereof.
Examples of polar solvents include amides, such as dimethylformamide, formamide, dimethylacetamide, N-methylpyrrolidone, ftuthermore dimethyl sulphoxide, acetonitrile, acetic acid or, preferably, alcohols, such as, for example, methanol, ethanol, butanol, methyl glycol or ethyl glycol. In addition, mixtures of these solvents can also be used.
Particularly preferably, the process according to the invention is carried out in the presence of an organic acid. This leads to acceleration of the reaction, often also resulting in higher yields and higher purity. Examples of suitable organic acids are lower aliphatic, saturated or unsaturated mono- or dicarboxylic acids, such as, for example, formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, fumaric acid, maleic acid, succinic acid, glutaric acid, adipic acid, but also aromatic acids, such as, for example, benzoic acid, phthalic acid, phenylacetic acid, isophthalic acid and terephthalic acid. The acids are added in amounts of 0.2-3 mole equivalents, preferably 1-2 mole equivalents. However, higher amounts of acid can also be used, preferably in those cases where the acid is also used as solvent, for example acetic acid.
The components can be used in equivalent amounts or in excess.
The reaction temperatures for the process according to the invention are preferably 10 to 140° C., in particular 20 to 120° C., and can be varied depending on the reactivity of the starting materials.
The reaction of compounds of th

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