Triphendioxazine compounds

Details Triphendioxazine compounds Triphendioxazine compounds

2000-05-19

2001-10-16

Shah, Mukund J. (Department: 1624)

Bleaching and dyeing; fluid treatment and chemical modification

Process of printing permanently on substrate, other than...

C008S918000, C008S919000, C008S924000, C106S031470, C544S075000, C544S076000, C544S077000

Reexamination Certificate

active

06302923

ABSTRACT:

The invention relates to new triphendioxazine compounds, to a process for producing the new triphendioxazine compounds and to their use as direct dyestuffs.
SUMMARY OF THE INVENTION
According to the invention compounds of formula (I)
wherein
DESCRIPTION OF PREFERRED EMBODIMENTS
R
1
and R
1
′ independently from each other are hydrogen or halogen,
R
2
and R
2
′ independently from each other are hydrogen or C
1-4
-alkyl,
X and X′ independently from each other are optionally substituted aliphatic, aromatic, cycloaliphatic or heterocyclic amino or O-alkyl optionally substituted by a group selected from —OH, —COOH, —NH
2
, —NHalkyl, —N(alkyl)
2
, —SO
3
H, —O-alkyl,
Y and Y′ independently from each other and from X and X′ have the same meaning as X and X′,
m and n independently from each other have the value 1 or 2;
with the provisos that
(i) if Y═Y′ is a &bgr;-sulfoethylamino radical then X═X′ is neither &bgr;-sulfoethylamino nor amino nor morpholino nor 3-(&bgr;-sulfatoethyl-sulfonyl)-phenylamino nor 3-sulfo-phenylamino
(ii) if Y═Y′ is morpholino then X═X′ is neither morpholino nor 4-sulfo-phenylamino,
and salts thereof as well as mixtures of such compounds are provided.
In preferred compounds, mixtures and salts thereof R
1
and R
1
′ are halogen radicals, X, X′, Y and Y′ are optionally substituted aliphatic, aromatic, cycloaliphatic or heterocyclic amines and m and n have the value 1.
In most preferred compounds R
1
and R
1
′ are chlorine and R
2
and R
2
′ are hydrogen.
Examples for HX, HX′, HY and HY′ are monoethanolamine, diethanotamine, tetrahydro-1,4-oxazine, diethylaminopropylamine, 2-amino-propylamine, I-amino-diethylaminoethane, 1-amino-dimethylaminopropane, N-(2-amino-ethyl)-tetrahydro-1,4-oxazine, N-(2-aminopropyl)-tetrahydro- 1,4-oxazine, N,N-dibutylamino-propylamine, 3-methylamino-propylamine, 2-(3-aminopropyl)-aminoethanol, isopropylamino-ethylamine, N-(3-aminopropyl )-cyclohexyl-amine, N-(2-aminoethyl)-N-methylaniline, N,N-bis-(2-hydroxyethyl)-,2-diaminopropane, N-(2-aminoethyl)-pyrrolidine, N-(3-aminopropyl)-pyrrolidine, 2-piperidino-ethylamine, N-(2-aminoethyl)-piperazine, N-phenyl-piperazine, N-methyl-ethanolamine 3-methoxypropylamine, 1-methylamino-ethyl-2-sulphonic acid, 1-aminobenzene-2-sulfonic acid, 1-aminobenzene-3-sulfonic acid, 1-amino-benzene-4-sulfonic acid, 2-amino-benzoic acid, 3-amino-benzoic acid, 4-amino-benzoic acid, 3-amino-6-methoxy-benzoic acid, 5-amino-isophthalic acid, 2-amino-naphthaline-6-sulfonic acid and 2-aminonaphthaline-1-sulfonic acid.
According to another aspect of the invention a process for producing compounds of formula (I) is provided which is characterized in that a compound of formula (II)
with the above-defined meanings of the symbols is reduced to the corresponding leuco form of formula (IIa)
with the same meanings for the substituents as defined above, which is then reacted with one mole of the compound of formula (III)
The remaining chlorine atoms of the triazine ring are replaced by X′ and Y′ by condensation and after oxidation a compound of formula (I) is obtained that can be isolated by known methods.
Depending on the meaning of X, X′, Y and Y′ the dioxazine compound can be symmetrically or asymmetrically substituted.
It is possible to prepare dioxazine compounds according to formula (I) with up to four different substituents attached to the triazine rings. In this way it is possible to design the compounds according to the desired needs. For example substituents with opposite ionogenicity may be introduced.
Alternatively, by replacement of all chlorine atoms with the same amino group, compounds with X═X′═Y═Y′ may be obtained.
An alternative way to produce compounds according to formula (I) is to use triazine compounds according to formulae (IIIa) respectively (IIIb)
wherein P and Q signify X, X′, Y or Y′as defined above.
Another procedure for producing the new dioxazine compounds is characterized in that first a compound of formula (IV)
with the above defined meaning for R
1
, R
1
′, R
2
, R
2
′, m and n is reduced to the corresponding leuco form (V)
with the same definitions for substituents as defined above.
In the next step two moles of a compound of formula (III)
react with the compound of formula (V). The product of this reaction is a compound of formula (VI)
with the above-defined meanings of the symbols.
In the next steps first of all two moles of a compound HX or HX′ and two moles of a compound HY or HY′ are reacted with the compound of formula (VI). A compound according to formula (I) is then obtained after oxidation.
Depending upon the methods of synthesis and purification, the new dyestuff can be obtained in free- or salt form. When the new dyestuff is obtained in salt form, the cation associated therewith is not critical and may be any one of those non-chromophoric cations conventional in the field of dyes provided that the corresponding salts are water-soluble. Examples of such cations are alkali metal cations and unsubstituted and substituted ammonium cations, e.g. lithium, sodium, potassium, ammonium, mono-, di-, tri- and tetra-methylammonium, tri- ethylammonium and mono-, di- and tri- ethanolammonium. The preferred cations are the alkali metal cations and ammonium, with sodium or lithium being the most preferred.
In the procedure of producing the new triphendioxazine compounds the starting compound of formula (II) can be synthesized by known processes. Preferably in a first step the cyanuric chloride is condensed to triphendioxazine backbone at a temperature of 0-10° C. at a pH of 8-8.5. In a second step HX is condensed to the triazine ring at a temperature of 40-60° C. at a pH of 5.5-6.5 and in a third step HY is condensed to the triazine ring at a temperature between 90-95° C. at a pH of 8-8.5. As an alternative method mono- or bi-substituted cyanuric chlorides may be condensed to triphendioxazine backbone.
The reduction to the corresponding leuco form according to formula (IIa) respectively according to formula (V) can be done by known reducing agents under an inert gas atmosphere. Preferably powdery tin at room temperature is used at an acid pH value.
The condensation of the unsubstituted cyanuric chloride according to formula (III) with the corresponding leuco form according to formula (IIa) respectively according to formula (V) can be done under known conditions. Preferably at a pH between 5.5-6.5 and a temperature of 0-10° C. under an inert gas atmosphere.
The condensation of the mono-substituted cyanuric chloride according to formula (IIIa) with the corresponding leuco form according to formula (IIa) respectively according to formula (V) can be done under known conditions. Preferably at a pH between 5.5-6.5 and a temperature of 40-60° C. under an inert gas atmosphere.
The condensation of the bi-substituted cyanuric chloride according to formula (IIIb) with the corresponding leuco form according to formula (IIa) respectively according to formula (V) can be done under known conditions. Preferably at a pH between 5.5-8.5 and a temperature of 75-95° C. under an inert gas atmosphere.
The oxidation of the triphendioxazine compound is done by known oxidizing agent under known conditions. Preferred oxidizing agent is oxygen.
The isolation is done under known conditions. Preferably it is done by precipitation with NaCl or ethanol.
In a new dyestuff according to the invention, the cations can be the same or different, e.g., they can also be a mixture of the above mentioned cations meaning that the dyestuff can be in a mixed salt form.
The compounds according to the invention, mixtures thereof or their salts may be used for dyeing cationic dyeable materials such as: homo- or mixed-polymers of acrylonitrile, acid modified polyester or polyamide; wool; leather including low affinity vegetable-tanned leather; cotton; bast fibers such as hemp, flax, sisal, jute, coir and straw; regenerated cel

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