Soluble chromophores having improved solubilizing groups

Details Soluble chromophores having improved solubilizing groups Soluble chromophores having improved solubilizing groups

1999-12-16

2001-08-14

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S453000, C548S460000, C548S306400, C552S212000, C560S026000, C430S342000, C430S343000, C347S212000, C106S493000, C106S494000, C106S495000, C106S496000, C106S497000, C106S498000, C534S732000, C534S733000, C540S122000, C544S074000, C544S075000, C544S076000, C544S077000, C544S125000, C544S144000, C544S296000, C544S300000, C544S333000, C546S037000, C546S038000, C546S049000, C546S057000, C546S154000, C546S167000, C546S174000

Reexamination Certificate

active

06274728

ABSTRACT:

The present Application relates to novel soluble chromophores having removable solubilising oxy-, thio- or amino-alkylene-oxycarbonyl groups. Those compounds have improved properties, especially a surprisingly higher solubility. In dissolved form those chromophores can be incorporated very readily into substrates in high concentrations and can then be converted back into the corresponding insoluble pigments with an especially high degree of conversion. Those groups can also be introduced into chromophores that cannot be reacted, or react only unsatisfactorily, with known groups.
EP 648 770 and EP 648 817 disclose soluble, carbamate-group-containing chromophores that can be converted into the corresponding pigments by heating to relatively high temperatures, which results in the removal of the carbamate radicals. Among other numerous combinations, C
1
-C
4
alkylthio-C
1
-C
14
alkylenecarbamate radicals are also possible.
Quinophthalone carbonates having limited solubility are known from U.S. Pat. No. 5 243 052 and can be used in heat-sensitive registration systems.
It has now been found that soluble chromophores having markedly improved properties are obtained when oxy-, thio- or amino-alkylene-oxycarbonyl groups are used as solubilising groups.
The present invention accordingly relates to compounds of formula
A(B)
x
  (I),
wherein x is an integer from 1 to 8,
A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, indanthrone, isoindolinone, isoindoline, dioxazine, azo, phthalocyanine or diketopyrrolopyrrole series that is bonded to x groups B via one or more hetero atoms, those hetero atoms being selected from the group consisting of N, O and S and forming part of the radical A,
each group B independently of any other(s) is hydrogen or a group of the formula
 at least one group B being a group of the formula
wherein
Q is p,q—C
2
-C
12
alkylene that is unsubstituted or mono- or poly-substituted by C
1
-C
12
alkoxy, C
1
-C
12
alkylthio or by C
2
-C
24
dialkylamino, p and q being different position numbers,
X is a hetero atom selected from the group consisting of N, O and S, m being the number 0 when X is O or S and m being the number 1 when X is N, and
L
1
and L
2
are each independently of the other [—(p′,q′—C
2
-C
12
alkylene)-Z—]
n
—C
1
-C
12
alkyl or C
1
-C
12
alkyl that is unsubstituted or mono- or poly-substituted by C
1
-C
12
alkoxy, C
1
-C
12
alkylthio, C
2
-C
24
dialkylamino, C
6
-C
12
aryloxy, C
6
-C
12
arylthio, C
7
-C
24
arylalkylamino or by C
12
-C
24
diarylamino, wherein n is a number from 1 to 1000, p′ and q′ are different position numbers, each Z independently of any other(s) is a hetero atom O, S or C
1
-C
12
alkyl-substituted N, and C
2
-C
12
alkylene in the repeating units [—C
2
-C
12
alkylene-Z—] may be identical or different,
and L
1
and L
2
may be saturated or one- to ten-fold unsaturated, uninterrupted or interrupted at any desired points by from 1 to 10 groups selected from the group consisting of —(C═O)— and —CH
4
—, and may carry no substituents or may carry from 1 to 10 further substituents selected from the group consisting of halogen, cyano and nitro,
with the proviso that when —Q— is —(CH
2
)
r
—, wherein r is a number from 2 to 12, and X is S, L
2
may not be unsubstituted, saturated and uninterrupted C
1
-C
4
alkyl.
Except for in the case of phthalocyanines, A preferably has at each hetero atom bonded to x groups B at least one immediately adjacent or conjugated carbonyl group.
A is the radical of a known chromophore having the basic structure:
A(H)
x
,
such as, for example,
and in each case all known derivatives thereof.
Alkyl or alkylene may be straight-chain, branched, monocyclic or polycyclic.
C
1
-C
12
Alkyl is therefore, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl, n-octyl, 1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, trimethylcyclohexyl, decyl, menthyl, thujyl, bornyl, 1-adamantyl, 2-adamantyl or dodecyl.
If C
2
-C
12
alkyl is mono- or poly-unsaturated, it is C
2
-C
12
alkenyl, C
2
-C
12
alkynyl, C
2
-C
12
alkapolyenyl or C
2
-C
12
alkapolyynyl, it being possible for two or more double bonds optionally to be isolated or conjugated, for example vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1-yl, 1,3-butadien-2-yl, 2-cyclobuten-1-yl, 2-penten-1-yl, 3-penten-2-yl, 2-methyl-1-buten-3-yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-1-yl, 1,4-pentadien-3-yl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, 2,4-cyclohexadien-1-yl, 1-p-menthen-8-yl, 4(10)-thuien-10-yl, 2-norbornen-1-yl, 2,5-norbornadien-1-yl, 7,7-dimethyl-2,4-norcaradien-3-yl or the various isomers of hexenyl, octenyl, nonenyl, decenyl or dodecenyl.
C
2
-C
4
Akylene is, for example, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-butylene, 1,3-butylene, 2,3-butylene, 1,4-butylene or 2-methyl-1,2-propylene. C
5
-C
12
Akylene is, for example, an isomer of pentylene, hexylene, octylene, decylene or dodecylene.
C
1
-C
12
Alkoxy is O—C
1
-C
12
alkyl, preferably O—C
1
-C
4
alkyl.
C
6
-C
12
Aryloxy is O—C
1
-C
12
aryl, for example phenoxy or naphthoxy, preferably phenoxy.
C
1
-C
12
Alkylthio is S—C
1
-C
12
alkyl, preferably S—C
1
-C
4
alkyl.
C
6
-C
12
Arylthio is S—C
6
-C
12
aryl, for example phenylthio or naphthylthio, preferably phenylthio.
C
2
-C
24
Dialkylamino is N(alkyl
1
)(alkyl
2
), the sum of the carbon atoms in the two groups alkyl
1
and alkyl
2
being from 2 to 24, preferably N(C
1
-C
4
alkyl)-C
1
-C
4
alkyl.
C
7
-C
24
Alkylarylamino is N(alkyl
1
)(aryl
2
), the sum of the carbon atoms in the two groups alkyl
1
and aryl
2
being from 7 to 24, for example methylphenylamino, ethylnaphthyiamino or butylphenanthrylamino, preferably methylphenylamino or ethylphenylamino.
C
12
-C
24
Diarylamino is N(aryl
1
)(aryl
2
), the sum of the carbon atoms in the two groups aryl
1
and aryl
2
being from 12 to 24, for example diphenylamino or phenylnaphthylamino, preferably diphenylamino.
Halogen is chlorine, bromine, fluorine or iodine, preferably fluorine or chlorine.
n is preferably a number from 1 to 100, especially a number from 2 to 12.
Q is preferably C
4
-C
12
alkylene in which the carbon atom bonded to the chromophore radical via oxycarbonyl is tertiary.
Special interest is accorded to compounds of formula (I) wherein Q is C
2
-C
4
alkylene, and to those compounds wherein L
1
and L
2
are [—C
2
-C
12
alkylene-Z—]
n
—C
1
-C
12
alkyl or are C
1
-C
12
alkyl that is mono- or poly-substituted by C
1
-C
12
alkoxy, C
1
-C
12
alkylthio or by C
2
-C
24
dialkylamino.
Very special interest is accorded to compounds of formula (I) wherein Q is C
2
-C
4
alkylene, X is O, and L
2
is [—C
2
-C
12
alkylene-O—]
n
—C
1
-C
12
alkyl or is C
1
-C
12
alkyl that is mono- or poly-substituted by C
1
-C
12
alkoxy, especially to those compounds wherein —Q—X— is a group of the formula —C(CH
3
)
2
—CH
2
—O—.
Preferred compounds of formula I are:
a) perylenecarboxylic acid imides of formula
 wherein D is hydrogen, C
1
-C
6
alkyl, unsubstftuted or halo- or C
1
-C
6
alkyl-substituted phenyl, benzyl or phenethyl, or is B,
b) quinacridones of formula
 wherein R
1
and R
2
are each independently of the other hydrogen, halogen, C
1
-C
24
alkyl, C
1
-C
6
alkoxy or phenyl,
c) dioxazines of formula
 wherein R
3
is hydrogen, halogen or C
1
-C
24
alkyl,
or of formula
wherein R
4
and R
5
are each independently of the other C
1
-C
4
alkyl,
d) isoindolines of formula
 wherein R
6
is a group
 R
7
is hydrogen, C
1
-C
24
alkyl, benzyl or a group
R
8
is hydrogen, E or R
6
,
R
9
, R
10
, R
11
and R
12
are each independently of the others hydrogen, C
1
-C
24
alkyl, C
1
-C
6
alkoxy, halogen or trifluoromethyl,
e) indigo derivatives of formula
 wherein R
13
is hydrogen, CN, C
1
-C
6
alkyl, C
1
-C
6
alkoxy or halogen,
f) isoindolinones of formula
 wherein R
14
and R
15
are each independently

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