Title of Invention

"A PYRIMIDOPTERIDINE OF FORMULAE I AND/OR II"

Abstract A pyrimidopteridine of formulae I and/or II wherein one or two of the radicals A and D, and B and C, are identical and either A and D or B and C are -OH or -NH2 and the radicals of the other pair are hydrogen, methyl; phenyl which is unsubstituted or substituted by -NH2, or -NHCOR2, and R2 is methyl, ethyl or phenyl."
Full Text Process for colouring high molecular weight organic material and novel polvcvclic pigments
The present invention relates to a process for mass colouring high molecular weight organic
material with pyrimidopteridines as well as to novel pyrimidopteridines.
Pyrimidopteridines are known compounds. In Ann., 545. 209 (1940), H. Wieland et al.
mention hydroxy-substituted pyrimidopteridines as reaction products of wing pigments of
butterflies. JACS, 77, 2243-2248 (1955), an article devoted to the synthesis of amino- and
hydroxy-substituted pyrimidopteridines, describes these products as sparingly soluble yellow
substances. Pyrimidopteridines which are substituted at at least two nitrogen atoms of the
ring system are disclosed as fluorescent pigments in JP-A 93-202046, JP-A 93-202053,
JP-A 94-41135 and JP-A 95-278456. DE-A 4415656 discloses pyrimidopteridine salts as
pigments. The known mixtures of pyrimidopteridine compounds with high molecular organic
materials normally already have good lightfastness properties which, however, are still not
sufficiently good for a number of applications, especially when used as automotive lacquers.
High requirements are placed on pigments which are suitable for a wide range of applications
in high molecular weight organic material, such as high chroma, high colour strength,
excellent fastness properties, such as fastness to light, weathering, migration and heat, good
dispersibility and easy accessibility.
Accordingly, it is the object of this invention to provide a high molecular weight organic
material coloured with pyrimidopteridine compounds and having improved fastness to light.
In particular, a cumulation of the above-mentioned advantages was to be attained with the
pyrimidopteridines which are unsubstituted at the nitrogen atoms of the ring system and
which are not saline.
An improved process has accordingly been found for mass colouring high molecular weight
organic material with pyrimidopteridines in a manner known per se by using a pyrimidopteridine
of formula I and/or II
wherein A, B, C and D are each independently of one another -NH2, -OH, hydrogen, d-C4-
alkyl; phenyi, biphenyl or naphthyl which are unsubstituted or substituted by halogen, -OH,
-NH2, d-C4alkyl or d-C4alkoxy; -NHR1f -N(Ri)2 or
Ou
RI is d-dalkyl; phenyl which is unsubstituted or substituted by halogen, d-dalkyl or d-dalkoxy,
or -COXR2,
X is a direct bond, -O- or -NH-, and
R2 is d-dalkyl; phenyl which is unsubstituted or substituted by halogen, d-dalkyl or d-dalkoxy,
with the proviso that at least two of the radicals A, B, C and D are -NH2 or -OH.
The compounds of formulae I and II can also be obtained in another tautomeric form, i.e.
those tautomeric forms are also included under formulae I and II.
Should some substituents be halogen, then they are typically fluoro, bromo or chloro, in
particular bromo or chloro and, preferably, chloro.
d-dAlkyl is typically methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl or tert-butyl,
and d-dalkoxy is typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-, i- or
tert-butoxy.
A special embodiment of this invention relates to a process for colouring high molecular
weight organic materials by using pyrimidopteridines of formulae I or II or a mixture thereof,
wherein
A, B, C and D are each independently of one another -NH2, -OH, hydrogen, methyl, ethyl;
phenyl which is unsubstituted or substituted by -OH or -NH2, typically p-hydroxyphenyl and paminophenyl,
or NHCOXR2, wherein
X is a direct bond, -O- or -NH-, and
R2 is C1-C4alkyl; phenyl which is unsubstituted or substituted by chloro, methyl, ethyl,
methoxy or ethoxy,
with the proviso that at least two of the radicals A, B, C and D are -NH2 or -OH.
A particularly preferred embodiment of this invention relates to a process for colouring high
molecular weight organic material by using pyrimidopteridines of formula I or II or a mixture
thereof, wherein A, B, C and D are each independently of one another -NH2, -OH, hydrogen,
methyl; phenyl which is unsubstituted or substituted by -NH2, or -NHCOR2, and R2 is methyl,
ethyl or phenyl, and wherein A and D, and B and C, are identical and at least one of the pairs
A and D or B and C is -NH2 or -OH.
Particularly preferred pyrimidopteridines of formula I and/or II are those, wherein at least one
group of A, B, C or D is the radical -NH2. In a particularly preferred embodiment of this
invention, at least one of the following pyrimidopteridines is used:
NH
The preparation of the pyrimidopteridines of formulae I and II is usually carried out by
methods known per se, such as those described in JACS, 77, 2243-2248 (1955) or in
DE-A 4 415 656, for example
(I) by oxidative dimerisation of corresponding aminopyrimidines according to the schemes
or also by condensation, e.g. according to the schemes
Compounds of formulae I and II, wherein one or two of the radicals A, B, C or D are
hydrogen, alkyl, substituted aryl, -NHRi or-NCR^, and the others are -OH or -NH2, are
novel. Accordingly, this invention also relates to pyrimidopteridines of formula I and/or II,
wherein one or two of the radicals A, B, C or D are hydrogen, C1-C4alkyl; phenyl, biphenyl or
naphthyl which are unsubstituted or substituted by halogen, -OH, -NH2, CrC4alkyl or C-|-
alkoxy; -NHR,, -N2, or
, wherein
RI is CiC4-alkyl; phenyl which is unsubstituted or substituted by halogen, d-C4alkyl or d-dalkoxy,
or -COXR2,
X is a direct bond, -O- or -NH-, and
R2 is d-C4aIkyl; phenyl which is unsubstituted or substituted by halogen, d-dalkyl or d-dalkoxy,
and the other radicals A, B, C or D are -OH or -NH2.
Particularly interesting pyrimidopteridines are those of the above structure, wherein one or
two of the radicals A, B, C or D are hydrogen, methyl, ethyl; phenyl which is unsubstituted or
substituted by -OH or -NH2, or NHCOXR2, wherein
X is a direct bond, -O- or -NH-, and
R2 is d-dalkyl, or phenyl which is unsubstituted or substituted by chloro, methyl, ethyl,
methoxy or ethoxy, and in particular those, wherein the radicals A and D, and B and C, are
identical and either A and D or B and C are -OH or -NH2, the radicals of the other pair being
hydrogen, methyl, phenyl which is unsubstituted or substituted by -NH2, or -NHCOR2, and R2
is methyl, ethyl or phenyl.
Illustrative examples of the novel pyrimidopteridines are the following:
,NH,
These novel pyrimidopteridines can be prepared in general analogy to the above-mentioned
processes. The starting products are usually known substances. Should some of them still
be novel they can usually be obtained in general analogy to commonly known methods.
Depending on their substituents and on the polymer to be coloured, the pyrimidopteridines of
formulae I and II may be used in the form of polymer-soluble chromophores or, preferably, in
the form of pigments. In the latter case it is advantageous to convert the products obtained
from the synthesis to a finely dispersed form. This may be effected in different manner, for
example:
a) by grinding or kneading, conveniently in the presence of grinding assistants, such as
inorganic or organic salts with or without the addition of organic solvents. After grinding, the
assistants are removed in customary manner; soluble inorganic salts e.g. with water, and
water-insoluble organic solvents e.g. by steam distillation,
b) by precipitation from sulfuric acid, methanesulfonic acid, trichloroacetic acid or polyphosphoric
acid,
c) by converting the crude pigment into an alkali metal salt or amine salt and by hydrolysing
the latter. This is effected, for example, by mixing the crude pigment with a base, typically
with an alkali metal hydroxide or alkali metal alcoholate, ammonia or amine, in a polar
organic solvent, such as dimethylformamide, whereupon the pigment dissolves completely or
partially. The pigment is precipitated by hydrolysis, preferably by acidifying the solution which
may have been filtered.
It may be found to be convenient to aftertreat the crude pigments or the pigments treated
according to a), b) or c) with organic solvents, preferably with solvents that boil at above
100°C.
Particularly suitable for use are benzenes substituted by halogen atoms, alkyl groups or
nitro groups, such as xylenes, chlorobenzene, o-dichlorobenzene or nitrobenzene, and
pyridine bases, such as pyridine, picoline or quinoline, and also ketones, such as cyclohexanone,
ethers, such as ethylene glycol monomethyl ether or ethylene glycol monoethyl ether,
amides, such as dimethylformamide or N-methylpyrrolidone as well as dimethylsulfoxide,
sulfolane or water by itself, if required under pressure. It is also possible to carry out the
aftertreatment in water in the presence of organic solvents and/or with addition of surfaceactive
substances or liquid ammonia or aliphatic amines.
The pigments preferably have a BET surface of 5-150 m2/g. Pigments having a BET surface
of 5-30 m2/g usually tend to have an opaque character whereas those having BET surfaces
of 30-150 m2/g usually tend to be transparent. The BET surface and the particle-size
distribution can normally be controlled by the above aftertreatments.
Depending on the envisaged end use it is advantageous to use the pigments as toners or in
the form of formulations.
The high molecular weight organic material to be coloured can be of natural or synthetic
origin. It may be, for example, natural resins or drying oils, rubber or casein or modified
natural substances, such as chlorinated rubber, oil-modified alkyd resins, viscose, cellulose
ethers or esters, such as cellulose acetate, cellulose propionate, cellulose acetobutyrate or
nitrocellulose and, preferably, synthetic organic polymers (thermosets as well as thermoplastics)
such as are obtained by polymerisation, polycondensation or polyaddition. Compounds
to be mentioned from the class of the polymerisation resins are, in particular, polyolefins,
such as polyethylene, polypropylene or polyisobutylene, and substituted polyolefins,
such as polymers from vinyl chloride, vinyl acetate, styrene, acrylonitrile of the acrylate
and/or methacrylate or butadiene and also copolymers of the mentioned monomers, in
partiuclar ABS or EVA.
Compounds to be mentioned from the series of the polyaddition resins and polycondensation
resins are the condensation products of formaldehyde with phenols, the so-called phenolic
plastics, and the condensation products of formaldehyde with urea, thiourea and melamine,
the so-called amino plastics, the polyesters used as surface coating resins, including the
saturated ones, such as alkyd resins, as well as the unsaturated ones, such as maleinate
resins, and also the linear polyesters and polyamides orsilicones.
The mentioned high molecular weight compounds can be obtained singly or in admixture, as
plastic masses or melts which, if desired, may be spun to fibres.
These compounds can also be obtained in the form of their monomers or in polymerised
state in dissolved form as film formers or binders for varnishes or printing inks, such as
boiled linseed oil, nitrocellulose, alkyd resins, melamine resins, urea/formaldehyde resins or
acrylic resins.
The pigmenting of the high molecular weight organic materials with the pigments of formulae
and II is typically effected by incorporating such a pigment by itself or in the form of masterbatches
in these substrates using roll mills, mixing or milling apparatus. The pigmented
material is then brought into the desired final form by methods which are known per se,
conveniently by calendering, moulding, extruding, coating, casting or by injection moulding. It
is often desirable to incorporate plasticisers into the high molecular weight compounds
before processing in order to produce non-brittle mouldings or to diminish their brittleness.
Suitable plasticisers are typically esters of phosphoric acid, phthalic acid or sebacic acid. In
the novel process, the plasticisers may be incorporated before or after working the pigments
into the polymers. To obtain different shades, it is also possible to add to the high molecular
weight organic materials fillers or other chromophoric components such as white, coloured
or black pigments in any amount, in addition to the pyrimidopteridines of formulae I and II.
For pigmenting paints and printing inks, the high molecular weight organic materials and the
pyrimidopteridines of formulae I and II, together with optional additives such as fillers, other
pigments, siccatives or plasticisers, are finely dispersed or dissolved in a common organic
solvent or solvent mixture. The procedure may be such that the individual components by
themselves, or also several jointly, are dispersed or dissolved in the solvent and thereafter
all the components are mixed.
The colorations so obtained, e.g. in plastic materials, fibres, paint systems or prints, are
distinguished by a yellow to red shade, superior colour strength, high chroma, good
dispersibility, good fastness to re-coating, migration, heat, light and weathering as well as
by good gloss and good IR remission behaviour.
Accordingly, another embodiment of this invention also relates to a mass coloured high
molecular weight organic material, which comprises a pyrimidopteridine of formula I and/or II
and, preferably, to a mass coloured high molecular weight organic material, which comprises
a pyrimidopteridine of formula I and/or II, which material comprises
(a) 0.05 to 20 % by weight of pyrimidopteridines I and/or II, based on the sum of (a) and (b),
and
(b) 99.95 to 80 % by weight of a high molecular weight organic material, based on the sum
of (a) and (b) and,
(c) if desired, additives.
Accordingly, another embodiment of this invention relates to the use of the pyrimidopteridines
of formulae I and/or II for mass colouring high molecular weight organic material in
a manner known per se.
If the pyrimidopteridines of formulae I and II are obtained dissolved in the polymers used,
then they are also distinguished by having a pure shade, high colour strength, high fastness
to light and also high fluorescence. They are suitable for use in solar energy collectors and
for the production of laser radiation.
The following Examples illustrate the invention in more detail.
Example 1: 198.8 g of commercial 90 % 2,4,5,6-tetraaminopyrimidine sulfate are made into
a slurry in 1 I of deionised water and this suspension is adjusted to pH 7.9 by addition of
30 % aqueous sodium hydroxide solution (measured with a pH glass electrode). At the start
of the oxidation process the pH is kept at 7.9, 30 % sodium hydroxide solution being added if
necessary. The reaction mixture is first stirred for 15 minutes at room temperature and is
then heated to 55°C over 30 minutes. A moderate stream of air is then blown through a tube
below surface into the by then almost clear orange solution and the temperature is raised to
85°C over another 30 minutes. The increasingly thickening orange suspension is then stirred
for another 20 hours at 85°C while blowing in air. After 3 hours, 150 ml of water are added,
the pH control is terminated (total consumption of 30 % sodium hydroxide solution: 197 ml).
The fine orange precipitate is isolated by filtration over a hard filter paper while still hot and
the filter cake is washed with 2 I of water. The still moist filter cake is made into a slurry in
10 I of glacial acetic acid and the reaction mixture is stirred for 90 min at 115°C and filtered
over a hard filter paper while still hot. The yellow residue obtained, which still contains some
acetic acid, is stirred in 5 I of water and the suspension is adjusted to pH 7 with sodium
hydroxide solution and stirred for 15 hours at 95°C. The suspension is filtered over a hard
filter paper while still hot and the filter cake is washed with 1.5 I of water. The still moist filter
cake is recrystallised in 700 ml of boiling dimethylacetamide for 18 hours (first distilling off
some solvent/water mixture until the boiling temperature is 140°C). The reaction product is
filtered hot over a hard filter paper, washed with 250 ml of dimethylacetamide, 300 ml of
methanol and 500 ml of water and is then dried, giving 36.07 g (47 % of theory) of a yellow
powder of formula III
Elemental composition: 38.79 % C, 3.49 % H, 56.15 %N
(calculated for C8H8N10 • 0.25 H2O: 38.63 % C 3.44 % H 56.31 % N)
Example 2: The filtrate mentioned in Example 1, which consists of 10 I of still warm glacial
acetic acid, is stood overnight at room temperature. The resultant fine precipitate is isolated
by filtration over a hard filter paper and the orange-red residue is stirred in 600 ml of water.
The suspension, which has a pH of 4.37, is adjusted to pH 7 with 30 % sodium hydroxide
solution and is then heated to 90°C and adjusted once more to pH 7 by further addition of
sodium hydroxide solution. The suspension is stirred for one hour at 90°C and is then filtered
hot over a hard filter paper and the filter cake washed with 1200 ml of water. While still
moist, the orange-red filter cake is made into a slurry in 600 ml of dimethylacetamide and is
heated to boiling temperature, at first distilling off solvent/water mixture until the temperature
of the suspension reaches 140°C. The suspension is recrystallised for 17 hours at 140°C
and the reaction product is cooled to 90°C, filtered over a hard filter paper and washed first
with 600 ml of methanol and then with 1 I of water and is then dried, giving 1.96 g (2.5 % of
theory) of an orange-red powder of formula (IV)
Elemental composition: 38.84 % C 3.52 % H 55.33 % N
(calculated for C8H8N10 x 0.25 H2O: 38.63 % C 3.44 % H 56.31 % N)
Example 3: 24.66 g of commercial 97 % 6-hydroxy-2.4.5-triaminopyrimidinesulfate are made
into a slurry in 450 ml of deionised water and the suspension is adjusted to pH 7.5 by adding
30 % aqueous sodium hydroxide solution (measured with a pH glass electrode). The
tion mixture is heated to 80°C over 30 minutes, the pH being continually adjusted to 7.5 by
addition of sodium hydroxide solution. A moderate stream of air is then blown into the
brownish yellow suspension through a tube below surface, the temperature always being
kept at 80°C. After 22 hours, the stream of air is stopped, the orange suspension is cooled to
60°C and filtered over a hard filter paper. After washing with 150 ml water, the still moist filter
cake is mixed with 300 ml of glacial acetic acid (laboratory mixer) and this suspension is
placed in a Soxhlet tube and extracted with a further 1200 ml of boiling glacial acetic acid
over 2 hours. The orange residue is collected by suction from the Soxhlet tube on a hard
filter paper and then washed with 300 ml of water. The still moist filter cake is recrystallised
in 350 ml of boiling dimethylformamide for 17 hours (at first distilling off solvent/water mixture
until the boiling temperature is 135°C). The reaction product is filtered over a hard filter
paper, washed with 130 ml of dimethylformamide, then with 150 mi of methanol and finally
with 200 ml of water and is then dried, giving 5.7 g (46 %) of an orange powder of formula
(V), the isomeric compound of formula (VI)
also being assumed to be present.
Elemental composition: 37.45 % C 3.29 % H 43.44 % N
(calculated for C8H6N8O2 x 0.6 H2O: 37.38 %C 2.82 % H 43.60 % N)
Example 4: 25.31 g of commercial 97 % 4.5.6-triaminopyrimidinesulfate are made into a
slurry in 300 ml of deionised water and 16.5 ml of 30 % sodium hydroxide solution are
added. This mixture is heated to 55°C over 10 min and a moderate stream of air is introduced
below surface. The temperature is raised to 80°C over another 10 min. The mixture is
stirred for a total of 22 hours at 80°C with a constant stream of air, another 5.5 ml of
30 % sodium hydroxide solution being added after one hour (on reaching the temperature of
80°C). The yellowish orange supension is then filtered hot over a hard filter paper and the
filter cake is washed with 200 ml of water. The still moist filter cake is made into a slurry in
140 ml of 1 N sodium hydroxide solution and stirred for one hour at 90°C. The reaction
mixture is filtered over a hard filter paper and the filter cake is washed with 100 ml of water
until neutral. The moist filter cake is stirred in 140 ml of glacial acetic acid and recrystallised
for one hour at 105°C. The reaction product is filtered over a hard filter paper, washed with
100 ml of water and then dried, giving 2.00 g (17 %) of a yellow powder of formula (VII), the
isomeric compound of formula (VIII)
also being assumed to be present.
Elemental composition: 43.58 % C 3.98 % H 48.67 % N
(calculated for C8H6N8 x 0.4 H2O: 43.40 % C 3.10 % H 50.61 % N)
Example 5: 13.23 g of commercial 90 % 2.4.5.6-tetraaminopyrimidinesulfate are stirred at
room temperature in 180 ml of water. 12.14 g of commercial 97 % alloxanetetrahydrate are
added to this suspension, the colour of the reaction mixture changing from pale yellow to
yellowish orange. The pH is then momentarily raised from about 0.5 to 6.5 by addition of
30 % sodium hydroxide solution and the orange suspension is heated to 85°C and stirred for
18 hours at this temperature. The suspension is allowed to cool to room temperature and is
then filtered over a hard filter paper and the filter cake is washed with 500 ml of water. The
still moist filter cake is made into a slurry in 500 ml of water and stirred for 4 hours at 90°C.
The reaction mixture is filtered hot over a hard filter paper and and the residue is washed
with 500 ml of water. The still moist residue is then recrystallised in 350 ml of dimethylformamide
for 18 hours at 130°C (at first distilling off solvent/water mixture). The reaction product
is filtered over a hard filter paper, washed with 150 ml of dimethylformamide and 200 ml of
methanol and dn'ed, giving 9.1 g (74 % of theory) of a yellowish orange powder of
Elemental composition: 35.75 % C 3.38 % H 41.64%N
(calculated for C8H6N802x1.25 H2O: 35.76 % C 3.19 %H 41.70%N)
Example 6: 12.33 g of commercial 97 % 6-hydroxy-2.4.5-triaminopyrimidinesulfate and
16.55 g of commercial 97 % alloxanetetrahydrate are stirred in 300 ml of water at room
-13-
temperature. The violet suspension is heated to 90°C and stirred for 17 hours at this temperature.
The reaction mixture, now yellow, is filtered over a hard filter paper and'and the filter
cake is washed with 450 ml of water. The still moist filter cake is stirred in 300 ml of dimethylformamide
and recrystallised for 6 hours at 130°C (at first distilling off solvent/water
mixture). The reaction product is filtered over a hard filter paper and washed with 200 ml of
methanol, then with 200 ml of water and is then dried, giving 8.37 g (63 % of theory) of a
yellow powder of formula (X)
34.71 % C 2.91 % H 35.72 % N
34.81 % C 2.99 % H 35.52 % N)
Elemental composition:
(calculated for C8H5N7O3 x 1.6 H2O:
Examples 7-12: Colorations in HOPE (high density polyethylene).
The general procedure is as follows:
A mixture consisting of 1.0 g of pigment, 1.0 g of antioxidant (IRGANOX®1010, Ciba) and
1000 g of polyethylene HD granulate (VESTOLENO60-16, Hiils) is premixed for 15 minutes
in a glass flask on a roller gear table. Subsequently, the mixture is extruded in two passes on
a single screw extruder and the resulting granulate is moulded to plates on an injection
moulding machine (Allround Aarburg 200) at 220°C and then post-moulded for 5 minutes at
180°C.
Example.
No.
7
8
9
10
11
12
Compound
of formula of Example
(III)
(IV)
(V)
(VII)
(IX)
(X)
1
2
3
4
5
6
Colour obtained
yellow
orange-red
yellowish orange
yellow
yellow
yellow
Fastnesses
obtained
very good
very good
good
very good
very good
good
Examples 13-18: Colorations in PVC
The general procedure is as follows:
0.6 g of pigment is mixed with 67 g of polyvinyl chloride, 33 g of dioctyl phthalate, 2 g of
dibutyltin dilaurate and 2 g of titanium dioxide and processed to a thin film on a roll mill for
15 minutes at 160°C.
Example
No.
13
14
15
16
17
18
Compound
of formula of Example
(III)
(IV)
(V)
(VII)
(IX)
(X)
1
2
3
4
5
6
Colour obtained
yellow
orange-red
yellowish orange
yellow
yellow
yellow
Fastnesses
obtained
very good
very good
very good
very good
very good
good
Examples 19-24: Colorations in AM varnish
The general procedure is as follows:
2 g of pigment and 48 g of stoving lacquer consisting of
56 g of alkyd resin ALKYDAL®F310 (Bayer AG; 60 % in xylene)
13 g of melamine resin CYMEL®327 (Cyanamid; 90 % in butanol)
25 g of xylene
25 g of butanol
2.5 g of 1-methoxy-2-propanol and
1 g of silicone oil (1 % in xylene)
are mixed by conventional methods. The resultant colour lake is drawn to a film on a glass
plate. Before stoving in a circulating air oven (30 minutes at 120°C) the coating is allowed to
dry in the air for 30 minutes at an inclination of 25°.
-15-
xample
No.
19
20
21
22
23
24
Compound
of formula of Example
(III)
(IV)
(V)
(VII)
(IX)
(X)
1
2
3
4
5
6
Colour obtained
yellow
orange-red
yellowish orange
yellow
yellow
yellow
Fastnesses
.obtained
very good



We Claim:
1. A pyrimidopteridine of formulae I and/or II

(Formula Removed)

wherein one or two of the radicals A and D, and B and C, are identical and either A and D or B and C are -OH or -NH2 and the radicals of the other pair are hydrogen, methyl; phenyl which is unsubstituted or substituted by -NH2, or -NHCOR2, and R2 is methyl, ethyl or phenyl."
A pyrimidopteridine of formulae I and/or II

(Formula Removed)

wherein one or two of the radicals A and D., and B and C, are identical and either A and D or B and C are -NH2 and the radicals of the other pair are hydrogen, methyl; phenyl which is unsubstituted or substituted by -NH2, or -NHCOR2, and R2, is methyl, ethyl or phenyl.


Documents:

1420-DEL-2005-Abstract-(14-01-2009).pdf

1420-del-2005-abstract.pdf

1420-DEL-2005-Claims-(14-01-2009).pdf

1420-del-2005-claims.pdf

1420-DEL-2005-Correspondence-Others-(04-05-2009).pdf

1420-DEL-2005-Correspondence-Others-(14-01-2009).pdf

1420-del-2005-correspondence-others.pdf

1420-del-2005-description (complete).pdf

1420-DEL-2005-Form-1-(09-08-2011).pdf

1420-DEL-2005-Form-1-(14-01-2009).pdf

1420-del-2005-form-1.pdf

1420-del-2005-form-13-(04-05-2009).pdf

1420-del-2005-form-18.pdf

1420-DEL-2005-Form-2-(14-01-2009).pdf

1420-del-2005-form-2.pdf

1420-DEL-2005-Form-3-(14-01-2009).pdf

1420-del-2005-form-3.pdf

1420-del-2005-form-5.pdf

1420-DEL-2005-GPA-(04-05-2009).pdf

1420-DEL-2005-GPA-(14-01-2009).pdf

1420-del-2005-gpa.pdf

1420-DEL-2005-Others-Document-(04-05-2009).pdf

1420-DEL-2005-Petition-137-(14-01-2009).pdf

1420-DEL-2005-Petition-138-(14-01-2009).pdf

237-DELNP-2004-Correspondence Others-(09-08-2011).pdf

abstract.jpg


Patent Number 234039
Indian Patent Application Number 1420/DEL/2005
PG Journal Number 21/2005
Publication Date 22-May-2009
Grant Date 30-Apr-2009
Date of Filing 02-Jun-2005
Name of Patentee CIBA SPECIALTY CHEMICALS HOLDING INC,
Applicant Address KLYBECKSTRASSE 141, 4057 BASEL, SWITZERLAND.
Inventors:
# Inventor's Name Inventor's Address
1 NA NA
2 THOMAS EICHENBERGER JUNGSTRASSE 17, 4056 BASEL, SWITZERLAND.
3 MAX HUGIN U FEM BARG 18, 1734 TENTLINGEN, SWITZERLAND
PCT International Classification Number C09B 17/00
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2634/96 1996-10-25 Switzerland