Bleaching and dyeing; fluid treatment and chemical modification – Dye or potential dye composition – additive – treatment,... – Phthalocyanine dye
Reexamination Certificate
1999-09-17
2001-04-24
Einsmann, Margaret (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dye or potential dye composition, additive, treatment,...
Phthalocyanine dye
C008S680000, C008S681000, C008S685000, C008S687000, C008S919000, C546S049000, C552S210000, C540S133000, C540S139000
Reexamination Certificate
active
06221114
ABSTRACT:
BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
The present invention relates to novel dye salts which are free from fiber-reactive radicals and have the formula I
where
Chr is an (m+n)-valent radical of a chromophore from the series of the metal-free or metal-containing phthalocyanines, of the quinacridones, of the mono-, dis- or polyazo dyes, of the anthraquinones or copper formazans,
Ar is phenyl or naphthyl each of which is unsubstituted or substituted,
x
⊕
is a metal cation or ammonium ion,
y
⊕
is a proton, metal cation or ammonium ion,
m is 1 to 6, and
n is 1 to 6, the sum of m and n being not more than 7,
to a method of dyeing or printing paper and to dye preparations comprising dye salts.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide novel dye salts which are suitable advantageously for dyeing or printing polymeric materials, especially paper, both in the pulp and by means of the inkjet process. These novel dye salts should feature advantageous performance properties, in particular a good fastness to water and to light.
We have found that this object is achieved by the dye salts of the formula I defined at the outset.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The dye salts of the formula I are free from fiber-reactive radicals. In other words, they do not carry any of the radicals which are customary in reactive dyes and which react, for example, additively or substitutively with the hydroxyls of cellulose.
All alkyls appearing in the formulae specified herein can be either straight-chain or branched.
Any substituted phenyls or naphthyls in the formulae specified herein generally have 1 to 3, preferably 1 or 2, substituents which are, for example, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, halogen, cyano, nitro, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylsulfonyl or C
1
-C
6
-alkoxysulfonyl.
Examples of alkyls occurring in this application are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl (the terms isooctyl, isononyl, isodecyl and isotridecyl are trivial names and derived from the alcohols obtained by oxo synthesis; cf. in this respect Ullmann's Encyclopedia of Industrial Chemistry, 5
th
Edition, Vol. A 1, pages 290 to 293, and also Vol. A 10, pages 284 and 285), 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl or 2- or 4-hydroxybutyl.
Examples of alkoxys are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy or 2-methylpentyloxy.
Halogen is fluorine, chlorine or bromine, for example.
Examples of alkoxycarbonyls are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl or hexyloxycarbonyl.
Examples of alkyl- and alkoxysulfonyls are methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, pentyl-, hexyl-, methoxy-, ethoxy-, propoxy-, isopropoxy-, butoxy-, isobutoxy-, pentyloxy- or hexyloxysulfonyl.
Particular examples of Ar are phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-isopropylphenyl, 2-, 3- or 4-butylphenyl, 2,3-, 2,4- or 2,6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4- or 2,6-dimethoxyphenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl, 2-, 3- or 4-nitrophenyl or 2-, 3- or 4-cyanophenyl.
X
⊕
and Y
⊕
can each be a metal cation or an ammonium ion.
Particularly suitable metal cations are the lithium, sodium and potassium ions.
For the purposes of the invention ammonium ions are substituted or unsubstituted. Examples of substituted ammonium ions are monoalkyl-, dialkyl-, trialkyl-, tetraalkyl- or benzyltrialkylammonium ions or those cations which are derived from nitrogen-containing 5- or 6-membered saturated heterocycles, such as pyrrolidinium, piperidinium, morpholinium or piperazinium cations or their N-monoalkyl- or N,N-dialkyl-substituted products. Alkyl here is generally straight-chain or branched C
1
-C
20
-alkyl which can in general be substituted by 1 or 2 hydroxyls and/or interrupted by 1 to 4, preferably 1 or 2, oxygens in ether function. Where the ammonium ions have two or more alkyls, the latter can be identical or different.
Ions deserving of particular mention are mono-C
1
-C
6
-alkylammonium, di-(C
1
-C
6
-alkyl)ammonium, tri-(C
1
-C
6
-alkyl)ammonium, tetra-(C
1
-C
6
-alkyl)ammonium, benzyltri-(C
1
-C
6
-alkyl)ammonium, pyrrolidinium, piperidinium, morpholinium, piperazinium or N-(C
l
-C
4
-alkyl)piperazinium ions.
Examples of suitable amines from which the ammonium ions are derived are:
monoalkylamines, such as methylamine, ethylamine, propylamine, isopropylamine, butylamine, sec-butylamine, isobutylamin, 1,2-dimethylpropylamine or 2-ethylhexylamine,
dialkylamines, such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, di-sec-butylamine, bis(2-ethylhexyl)amine, N-methyl-n-butylamine or N-ethyl-n-butylamine,
alkoxyalkylamines, such as 2-methoxyethylamine, bis(2-methoxyethyl)amine, 3-methoxypropylamine, 3-ethoxypropylamine or 3-(2-ethylhexoxy)propylamine,
trialkylamines, such as trimethylamine, triethylamine, tripropylamine, tributylamine, N,N-dimethylethylamine, N,N-dimethylisopropylamine, N,N-dimethylbenzylamine and
hydroxy amines, such as mono- or diethanolamine, mono- or dipropanolamine, mono- or diisopropanolamine, N-mono- or N,N-di-(C
1
-C
4
-alkyl)ethanolamines, -propanolamines or -isopropanolamines, such as N-mono- or N,N-dimethylethanolamine, -propanolamine or -isopropanolamine, N-mono- or N,N-diethylethanolamine, -propanolamine or -isopropanolamine, N-mono- or N,N-dipropylethanolamine, -propanolamine or -isopropanolamine, N-mono- or N,N-diisopropylethanolamine, -propanolamine or -isopropanolamine or N-mono- or N,N-dibutylethanolamine, -propanolamine or -isopropanolamine, N-(C
1
-C
4
-alkyl)diethanolamines, -dipropanolamines or -diisopropanolamines, such as N-methyldiethanolamine, -dipropanolamine or -diisopropanolamine, N-ethyldiethanolamine, -dipropanolamine or -diisopropanolamine, N-propyldiethanolamine, -dipropanolamine or -diisopropanolamine, N-isopropyldiethanolamine, -dipropanolamine or -diisopropanolamine or N-butyldiethanolamine, -dipropanolamine or -diisopropanolamine, triethanolamine, tripropanolamine, triisopropanolamine, N-(2-hydroxyethyl)pyrrolidine, N-(2- or 3-hydroxypropyl)pyrrolidine, N-(2-hydroxyethyl)piperidine, N-(2- or 3-hydroxypropyl)piperidine, N-(2-hydroxyethyl)morpholine, N-(2- or 3-hydroxypropyl)morpholine, N-(2-hydroxyethyl)piperazine, N-(2- or 3-hydroxypropyl)piperazine or N,N-dimethyl- or N,N-diethyl-N-(5-hydroxy-3-oxapentyl)amine.
Appropriate chromophore radicals are derived in particular from the series of the metal-free phthalocyanines or of the phthalocyanines whose central unit is copper, zinc, nickel, AlCl or vCl, particular emphasis being placed on copper phthalocyanine.
The phthalocyanines preferably carry no substituents in their structure.
If Chr is the radical of a chromophore from the series of the metal-free or metal-containing phthalocyanines, m is preferably 1 to 2 and n is preferably 2 to 3, the sum of m and n being not more than 4.
Preference is given to dye salts of the formula I in which Ar is phenyl which is
Etzbach Karl-Heinz
Sens Rudiger
Seybold Gunther
Wurthner Frank
BASF - Aktiengesellschaft
Einsmann Margaret
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
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