Indian Patents. 254625:METHOD FOR THE PRODUCTION OF 2, 4, 6-TRIMERCAPTO-1, 3, 5-TRIAZINE

Title of Invention	METHOD FOR THE PRODUCTION OF 2, 4, 6-TRIMERCAPTO-1, 3, 5-TRIAZINE
Abstract	The present invention is directed towards a method for the production of 2,4,6-trimercapto-1,3,5-triazine (TMT-H3) . In particular, the method of the subject matter relates to the operation of acidifying the salts of 2,4,6-trimercapto- 1,3,5-triazine in aqueous solution and in a defined pH range.

Full Text	1 Method for the production of 2,4,6-trimercapto-l,3,5- triazine The present invention is directed towards a method for the production of 2,4,6-trimercapto-l,3,5-triazine (TMT-H3) . In particular, the method of the subject matter relates to the operation of acidifying the salts of 2,4,6-trimercapto- 1,3,5-triazine (TMT) in aqueous solution and in a defined pH range. 2,4,6-Trimercapto-l,3,5-triazine [CAS-No. 638-16-4], whose readily water-soluble trisodium salt [CAS-No. 17766-26-6] has already been in industrial use for a relatively long time for purifying heavy metal-containing wastewater and exhaust gas streams, can be used in the form of the free acid in various ways in the rubber industry sector. Especially epichlorohydrin rubbers and their copolymers with, e.g. ethylene oxide (what are termed ECO rubbers), which are crosslinked by ethylene thiourea to improve the physical and chemical properties, can mature to form an important field of use. This is because this crosslinking has to date additionally required lead compounds such as red lead or lead phosphate which bind the hydrochloric acid formed in vulcanization. The environmental pollution due to lead and also fundamental considerations on the toxicity of ethylene thiourea (ETU) have lead to the fact that lead is no longer being used at least in the car manufacturing sector. An effective substitute for the ETU/Pb system has proved to be TMT-H3, with which, if appropriate, in addition to activators, nontoxic calcium or magnesium compounds can be used. Methods for the production of TMT-H3 are described in a plurality of publications. In addition to methods which use ammonium thiocyanate or other salts of thiocyanic acid as starting material and 2 obtain the TMT-H3 by cyclotrimerization in the strongly acidic system, most processes start from cyanuric chloride which is reacted with salts of hydrosulphuric acid, if appropriate in the presence of a lye. For instance, according to CS 230344, cyanuric chloride is hydrolysed in aqueous acetone with concentrated Na2S solution at 80°C for 4 h and subsequently acidified. The yield is said to be 80%. CS 2 65150 describes the reaction of a cyanuric chloride suspension with an NaSH/Na2S/Na2C03 mixture and acidification with sulphuric acid (yield 90%, purity 95%). In US 5563267, trialkali metal and triammonium salts of TMT-H3 are produced, the free acid being precipitated out by addition of NaSH to a solution of cyanuric chloride in acetone. In addition, the product is acidified with hydrochloric acid. Diagram 1: leads to products which do not satisfy the requirements of the rubber industry for a TMT-H3 crosslinker. The purity is Our work has found that the trimercaptotriazine synthesis which actually can be carried out according to the diagram 2: 3 strong and untypical. Apparently, in this direct synthesis, side reactions occur such as hydroxyl derivatives and bridged systems. The nature of the impurities is not yet known in detail. A successful synthesis of a pure TMT-H3 proceeds via the formation of water-soluble salts of TMT, from which the pure TMT-H3 is then precipitated by acidification: Diagram 3: Preferably, disodium or trisodium salt is used. A method for the production of the trisalt is described in DE 3729029. Customarily, a TMT-Na3 solution (pH approximately 12) is admixed, with stirring, with a strong acid until a pH is present and as a result acid precipitation occurs. In this method, that is also occasionally reported in the abovementioned patents, a fundamental difficulty occurs which makes carrying it out industrially virtually impossible in practice. Formation of the free acid on acidification proceeds with intermediate formation of the following intermediates: 4 Diagram 4: Therefore, from pH 6 the monosodium salt precipitates out which, at pH reaction to give the free acid. In this customary procedure, it emerges that the reaction batch, with increasing solids precipitation, becomes increasingly more difficult to mix, since the precipitates cannot be drawn into the stirring zone and thus homogeneous mixing cannot be achieved. As a result of the poor mixing, the Na salt can thus not be completely converted to the free acid. A consequence is that a TMT-H3 obtained by filtration according to this method still has a high ash content. In addition, the precipitated product proves to be extremely finely divided, so that very long filtration times and especially also wash times are required in order to remove the dissolved sodium salts (e.g. NaCl or Na2SO4) • This results in very low space-time yields and thus high production costs. It was therefore an object of the present invention to specify a further method which is superior in economic and ecological aspects to the method of the prior art and helps to overcome the above-described disadvantages of the known methods. 5 This object is achieved according to the claims. As a result of the fact that a pH range from 1.5 to 2.5 is maintained in a method for the production of 2,4,6- trimercapto-1,3,5-triazine by acidification of a solution of the corresponding salts of 2,4,6-trimercapto-l,3,5- triazine in aqueous solution during the operation of acidification, extremely surprisingly, but no less advantageously, the solution of the object of interest is achieved. The quality of the 2,4,6-trimercapto-l, 3 , 5- triazine precipitate obtained by this method is sufficient to establish substantially shorter filtration times and wash and drying times in the method and thus to arrive at an economically more expedient method. In a preferred embodiment, in the inventive method a procedure is followed such that an aqueous solution adjusted to a pH of approximately 2 is charged and to this is added, with pH control (e.g. by adding acid), a solution of the corresponding salts of 2,4,6-trimercapto-l,3,5- triazine in aqueous solution. In this case, those skilled in the art are free to choose how the pH can be controlled. Advantageously, this can be achieved by the fact that, simultaneously with the addition of the solution of the corresponding salts of 2,4,6-trimercapto-l,3,5-triazine, an acidic aqueous solution, which is preferably produced from an inorganic acid and water (see below), is added in such a manner that the above-specified pH range can be maintained. The control can proceed using means known to those skilled in the art, for example using a pH electrode. Particularly advantageous is the fact that the acidification of the corresponding salts of 2,4,6- trimercapto-1,3,5-triazine proceeds in a pH range from 1.75 to 2.25, preferably 1.75 to 2.1. Further advantageous is an inventive method in which, during the acidification of the salts of 2,4,6-trimercapto- 6 1,3,5-triazine, small amounts of an organic high-molecular- weight polyacrylamide are present. Such high-molecular- weight substances are sufficiently known to those skilled in the art and are commercially available (Praestol and Praestol 2500). The inventive method is preferably carried out at a temperature of 40-70°C, more preferably at 50-65°C, and very particularly preferably at 55-62°C. The concentration of the salts used of 2,4,6-trimercapto-l,3,5-triazine is to be such that, in the feed solution, a concentration of 0.80-1.45 mol/1, preferably 0.90-1.25 mol/1, and very particularly preferably 0.95-1.20 mol/1, is present. The present invention describes an industrial method for producing, from the readily water-soluble trisodium salt of TMT (~ 300 g/1) or disodium salt (~ 750 g/1), the practically water-insoluble acid (~ 0.8 g/1). Surprisingly, the TMT-H3 suspension which has been precipitated out according to the invention remains of low viscosity. Since over the entire method duration no pH change occurs, no significant increase in viscosity is measured towards the end of addition either. The free acid is produced in pure form and, because of the constant pH condition, without contamination by the monosodium salt. In addition, it has been found that the filterability is significantly improved. In addition, this can be improved if an organic high-molecular-weight polyacrylamide is added (as 0.1-0.5% strength aqueous solution) in amounts of 0.01 to 1 g/1, preferably 0.1 to 0.4 g/1, of reaction solution. The inventive method produces, in a particularly simple manner, pure 2,4,6-trimercapto-l,3,5-triazine having contents of > 99% and ash contents of been unexpected from the outset. Acidification or production of acidic aqueous solutions preferably proceeds using strong organic or inorganic 7 acids. It is advantageous to use strong inorganic acids selected from the group consisting of hydrochloric acid, sulphuric acid, phosphoric acid, but strong organic acids can also be used, e.g. trifluoroacetic acid, p-toluenesulphonic acid and the like. The examples hereinafter are intended to explain the inventive method in more detail; the comparative example represents the delimitation from the prior art. 8 Comparative example: To a precharged solution consisting of 137.5 g of trimercaptotriazine trisodium salt molecular weight 243.2 = 0.565 mol in 412.5 g of distilled water (equivalent to ~ 25% strength solution) are added, in the course of 30 min, with stirring at room temperature 207.6 g of sulphuric acid 40% molecular weight 98.07 = 0.847 mol, the reaction temperature increasing to 40-45°C. The TMT-H3 formed precipitates out in very finely divided form, the batch becomes extremely thick in the last third of addition, aluminous [cream-cheese-like] and can scarcely be stirred any longer. 1 1/2 h postreaction. Final pH of the suspension =1.9 The product is filtered off by suction through a 0 16 cm vacuum filter, filtration time: 3 h a pasty, runny filtercake being obtained. Subsequent washing salt-free with distilled water required 6-8 h. The moist product is dried at 105°C in a vacuum cabinet. Yield: 92.6 g TMT-H3 molecular weight 177.2 equivalent to 92.50% of theory. Ash content: 1.7% 9 Example No. 1: To 130 g of precharged distilled water, adjusted to pH 2.0 by addition of a little hydrochloric acid, in the course of 60 min, 550 g of a 25% strength solution of trimercaptotriazine trisodium salt in water at a temperature of 40-50°C, to which 21 g of a 0.43% strength aqueous Praestol 2500 solution have been added, and also 170 g of 37% strength hydrochloric acid are added simultaneously, so that in the system a pH of 1.8-2.0 is always present. The reaction temperature increases in the course of this to approximately 50-60°C and the TMT-H3 forming immediately precipitates out in flocculent, constantly very readily stirrable form. 1 h postreaction at 60°C and pH 1.9-2.0. Filtration using suction through a 0 16 cm porcelain vacuum filter, filtration time: 20 sec. Wash salt-free using distilled water, time: 30 min and dry in vacuum at 105°C. Yield: 98.5 g of TMT-H3 equivalent to 98.4% of theory molecular weight 177.2 Ash content: « 0.1% TMT-H3 content: 99.4% Example No. 2 A 25% strength solution is produced from 250 kg of TMT-55 (trimercaptotriazine trisodium salt) and 300 kg of deionized water at T = 60°C, to this solution are added 25 kg of Praestol 2500 solution [~ 0.4% strength] and the mixture is homogenized. In a suitable reaction vessel, 150 kg of deionized water (adjusted to pH 2.0 using H2SO4) are then charged and, with stirring, and pH measurement, 10 210 kg of sulphuric acid 40% strength and the TMT solution are pumped in simultaneously in the course of 60-90 min, so that a pH of approximately 2 is always present. 2 h postreaction at approximately 60°C, pH 1.7-1.9. Filter and wash salt-free with deionized water, dry. Yield: 100 kg of TMT-H3 equivalent to 99.8% of theory molecular weight 177.2 TMT-H3 content: 99.6% Ash content: « 0.1% 11 Claims: 1. Method for the production of 2,4,6-trimercapto-l,3,5- triazine by acidification of a solution of the corresponding salts of 2,4,6-trimercapto-l,3,5- triazine in aqueous solution, characterized in that during the operation of acidification a pH range of 1.5 to 2.5 is maintained. 2. Method according to Claim 1, characterized in that an aqueous solution adjusted to a pH of approximately 2 is charged and to this is added, with pH control, a solution of the corresponding salts of 2,4,6-trimer- capto-l, 3 , 5-triazine in aqueous solution. 3. Method according to Claim 1 and/or 2, characterized in that acidification is performed in a pH range of 1.75 to 2.25, preferably 1.75 to 2.1. 4. Method according to one or more of the preceding claims, characterized in that the salts of 2,4,6-trimercapto-l,3,5-triazine are acidified in the presence of small amounts of an organic high-molecular-weight polyacrylamide. The present invention is directed towards a method for the production of 2,4,6-trimercapto-1,3,5-triazine (TMT-H3) . In particular, the method of the subject matter relates to the operation of acidifying the salts of 2,4,6-trimercapto- 1,3,5-triazine in aqueous solution and in a defined pH range.

Full Text

1
Method for the production of 2,4,6-trimercapto-l,3,5-
triazine
The present invention is directed towards a method for the
production of 2,4,6-trimercapto-l,3,5-triazine (TMT-H3) . In
particular, the method of the subject matter relates to the
operation of acidifying the salts of 2,4,6-trimercapto-
1,3,5-triazine (TMT) in aqueous solution and in a defined
pH range.
2,4,6-Trimercapto-l,3,5-triazine [CAS-No. 638-16-4], whose
readily water-soluble trisodium salt [CAS-No. 17766-26-6]
has already been in industrial use for a relatively long
time for purifying heavy metal-containing wastewater and
exhaust gas streams, can be used in the form of the free
acid in various ways in the rubber industry sector.
Especially epichlorohydrin rubbers and their copolymers
with, e.g. ethylene oxide (what are termed ECO rubbers),
which are crosslinked by ethylene thiourea to improve the
physical and chemical properties, can mature to form an
important field of use. This is because this crosslinking
has to date additionally required lead compounds such as
red lead or lead phosphate which bind the hydrochloric acid
formed in vulcanization.
The environmental pollution due to lead and also
fundamental considerations on the toxicity of ethylene
thiourea (ETU) have lead to the fact that lead is no longer
being used at least in the car manufacturing sector. An
effective substitute for the ETU/Pb system has proved to be
TMT-H3, with which, if appropriate, in addition to
activators, nontoxic calcium or magnesium compounds can be
used.
Methods for the production of TMT-H3 are described in a
plurality of publications.
In addition to methods which use ammonium thiocyanate or
other salts of thiocyanic acid as starting material and

2
obtain the TMT-H3 by cyclotrimerization in the strongly
acidic system, most processes start from cyanuric chloride
which is reacted with salts of hydrosulphuric acid, if
appropriate in the presence of a lye.
For instance, according to CS 230344, cyanuric chloride is
hydrolysed in aqueous acetone with concentrated Na2S
solution at 80°C for 4 h and subsequently acidified. The
yield is said to be 80%.
CS 2 65150 describes the reaction of a cyanuric chloride
suspension with an NaSH/Na2S/Na2C03 mixture and
acidification with sulphuric acid (yield 90%, purity 95%).
In US 5563267, trialkali metal and triammonium salts of
TMT-H3 are produced, the free acid being precipitated out
by addition of NaSH to a solution of cyanuric chloride in
acetone. In addition, the product is acidified with
hydrochloric acid.
Diagram 1:

leads to products which do not satisfy the requirements of
the rubber industry for a TMT-H3 crosslinker. The purity is
Our work has found that the trimercaptotriazine synthesis
which actually can be carried out according to the
diagram 2:

3
strong and untypical. Apparently, in this direct synthesis,
side reactions occur such as hydroxyl derivatives and
bridged systems. The nature of the impurities is not yet
known in detail. A successful synthesis of a pure TMT-H3
proceeds via the formation of water-soluble salts of TMT,
from which the pure TMT-H3 is then precipitated by
acidification:
Diagram 3:

Preferably, disodium or trisodium salt is used. A method
for the production of the trisalt is described in DE
3729029.
Customarily, a TMT-Na3 solution (pH approximately 12) is
admixed, with stirring, with a strong acid until a pH is present and as a result acid precipitation occurs. In
this method, that is also occasionally reported in the
abovementioned patents, a fundamental difficulty occurs
which makes carrying it out industrially virtually
impossible in practice.
Formation of the free acid on acidification proceeds with
intermediate formation of the following intermediates:

4
Diagram 4:

Therefore, from pH 6 the monosodium salt precipitates out
which, at pH reaction to give the free acid.
In this customary procedure, it emerges that the reaction
batch, with increasing solids precipitation, becomes
increasingly more difficult to mix, since the precipitates
cannot be drawn into the stirring zone and thus homogeneous
mixing cannot be achieved. As a result of the poor mixing,
the Na salt can thus not be completely converted to the
free acid. A consequence is that a TMT-H3 obtained by
filtration according to this method still has a high ash
content. In addition, the precipitated product proves to be
extremely finely divided, so that very long filtration
times and especially also wash times are required in order
to remove the dissolved sodium salts (e.g. NaCl or Na2SO4) •
This results in very low space-time yields and thus high
production costs.
It was therefore an object of the present invention to
specify a further method which is superior in economic and
ecological aspects to the method of the prior art and helps
to overcome the above-described disadvantages of the known
methods.

5
This object is achieved according to the claims.
As a result of the fact that a pH range from 1.5 to 2.5 is
maintained in a method for the production of 2,4,6-
trimercapto-1,3,5-triazine by acidification of a solution
of the corresponding salts of 2,4,6-trimercapto-l,3,5-
triazine in aqueous solution during the operation of
acidification, extremely surprisingly, but no less
advantageously, the solution of the object of interest is
achieved. The quality of the 2,4,6-trimercapto-l, 3 , 5-
triazine precipitate obtained by this method is sufficient
to establish substantially shorter filtration times and
wash and drying times in the method and thus to arrive at
an economically more expedient method.
In a preferred embodiment, in the inventive method a
procedure is followed such that an aqueous solution
adjusted to a pH of approximately 2 is charged and to this
is added, with pH control (e.g. by adding acid), a solution
of the corresponding salts of 2,4,6-trimercapto-l,3,5-
triazine in aqueous solution. In this case, those skilled
in the art are free to choose how the pH can be controlled.
Advantageously, this can be achieved by the fact that,
simultaneously with the addition of the solution of the
corresponding salts of 2,4,6-trimercapto-l,3,5-triazine, an
acidic aqueous solution, which is preferably produced from
an inorganic acid and water (see below), is added in such a
manner that the above-specified pH range can be maintained.
The control can proceed using means known to those skilled
in the art, for example using a pH electrode.
Particularly advantageous is the fact that the
acidification of the corresponding salts of 2,4,6-
trimercapto-1,3,5-triazine proceeds in a pH range from 1.75
to 2.25, preferably 1.75 to 2.1.
Further advantageous is an inventive method in which,
during the acidification of the salts of 2,4,6-trimercapto-

6
1,3,5-triazine, small amounts of an organic high-molecular-
weight polyacrylamide are present. Such high-molecular-
weight substances are sufficiently known to those skilled
in the art and are commercially available (Praestol and
Praestol 2500).
The inventive method is preferably carried out at a
temperature of 40-70°C, more preferably at 50-65°C, and
very particularly preferably at 55-62°C. The concentration
of the salts used of 2,4,6-trimercapto-l,3,5-triazine is to
be such that, in the feed solution, a concentration of
0.80-1.45 mol/1, preferably 0.90-1.25 mol/1, and very
particularly preferably 0.95-1.20 mol/1, is present.
The present invention describes an industrial method for
producing, from the readily water-soluble trisodium salt of
TMT (~ 300 g/1) or disodium salt (~ 750 g/1), the
practically water-insoluble acid (~ 0.8 g/1). Surprisingly,
the TMT-H3 suspension which has been precipitated out
according to the invention remains of low viscosity. Since
over the entire method duration no pH change occurs, no
significant increase in viscosity is measured towards the
end of addition either. The free acid is produced in pure
form and, because of the constant pH condition, without
contamination by the monosodium salt. In addition, it has
been found that the filterability is significantly
improved. In addition, this can be improved if an organic
high-molecular-weight polyacrylamide is added (as 0.1-0.5%
strength aqueous solution) in amounts of 0.01 to 1 g/1,
preferably 0.1 to 0.4 g/1, of reaction solution.
The inventive method produces, in a particularly simple
manner, pure 2,4,6-trimercapto-l,3,5-triazine having
contents of > 99% and ash contents of been unexpected from the outset.
Acidification or production of acidic aqueous solutions
preferably proceeds using strong organic or inorganic

7
acids. It is advantageous to use strong inorganic acids
selected from the group consisting of hydrochloric acid,
sulphuric acid, phosphoric acid, but strong organic acids
can also be used, e.g. trifluoroacetic acid,
p-toluenesulphonic acid and the like.
The examples hereinafter are intended to explain the
inventive method in more detail; the comparative example
represents the delimitation from the prior art.

8
Comparative example:
To a precharged solution consisting of
137.5 g of trimercaptotriazine trisodium salt
molecular weight 243.2 = 0.565 mol
in
412.5 g of distilled water (equivalent to ~ 25% strength
solution)
are added, in the course of 30 min, with stirring
at room temperature
207.6 g of sulphuric acid 40% molecular weight 98.07 =
0.847 mol,
the reaction temperature increasing to 40-45°C.
The TMT-H3 formed precipitates out in very finely divided
form, the batch becomes extremely thick in the last third
of addition, aluminous [cream-cheese-like] and can scarcely
be stirred any longer. 1 1/2 h postreaction. Final pH of
the suspension =1.9
The product is filtered off by suction through a 0 16 cm
vacuum filter, filtration time: 3 h
a pasty, runny filtercake being obtained.
Subsequent washing salt-free with distilled water required
6-8 h.
The moist product is dried at 105°C in a vacuum cabinet.
Yield: 92.6 g TMT-H3 molecular weight 177.2
equivalent to 92.50% of theory.
Ash content: 1.7%

9
Example No. 1:
To 130 g of precharged distilled water, adjusted to pH 2.0
by addition of a little hydrochloric acid, in the course of
60 min, 550 g of a 25% strength solution of
trimercaptotriazine trisodium salt in water at a
temperature of 40-50°C, to which 21 g of a 0.43% strength
aqueous Praestol 2500 solution have been added, and also
170 g of 37% strength hydrochloric acid are added
simultaneously, so that in the system a pH of 1.8-2.0 is
always present. The reaction temperature increases in the
course of this to approximately 50-60°C and the TMT-H3
forming immediately precipitates out in flocculent,
constantly very readily stirrable form. 1 h postreaction at
60°C and pH 1.9-2.0. Filtration using suction through a
0 16 cm porcelain vacuum filter, filtration time: 20 sec.
Wash salt-free using distilled water, time: 30 min and dry
in vacuum at 105°C.
Yield: 98.5 g of TMT-H3
equivalent to 98.4% of theory molecular
weight 177.2
Ash content: « 0.1%
TMT-H3 content: 99.4%
Example No. 2
A 25% strength solution is produced from 250 kg of TMT-55
(trimercaptotriazine trisodium salt) and 300 kg of
deionized water at T = 60°C, to this solution are added
25 kg of Praestol 2500 solution [~ 0.4% strength] and the
mixture is homogenized. In a suitable reaction vessel,
150 kg of deionized water (adjusted to pH 2.0 using H2SO4)
are then charged and, with stirring, and pH measurement,

10
210 kg of sulphuric acid 40% strength and the TMT solution
are pumped in simultaneously in the course of 60-90 min, so
that a pH of approximately 2 is always present. 2 h
postreaction at approximately 60°C, pH 1.7-1.9. Filter and
wash salt-free with deionized water, dry.
Yield: 100 kg of TMT-H3
equivalent to 99.8% of theory molecular
weight 177.2
TMT-H3 content: 99.6%
Ash content: « 0.1%

11
Claims:
1. Method for the production of 2,4,6-trimercapto-l,3,5-
triazine by acidification of a solution of the
corresponding salts of 2,4,6-trimercapto-l,3,5-
triazine in aqueous solution,
characterized in that
during the operation of acidification a pH range of
1.5 to 2.5 is maintained.
2. Method according to Claim 1,
characterized in that
an aqueous solution adjusted to a pH of approximately
2 is charged and to this is added, with pH control, a
solution of the corresponding salts of 2,4,6-trimer-
capto-l, 3 , 5-triazine in aqueous solution.
3. Method according to Claim 1 and/or 2,
characterized in that
acidification is performed in a pH range of 1.75 to
2.25, preferably 1.75 to 2.1.
4. Method according to one or more of the preceding
claims,
characterized in that
the salts of 2,4,6-trimercapto-l,3,5-triazine are
acidified in the presence of small amounts of an
organic high-molecular-weight polyacrylamide.

The present invention is directed towards a method for the
production of 2,4,6-trimercapto-1,3,5-triazine (TMT-H3) . In
particular, the method of the subject matter relates to the
operation of acidifying the salts of 2,4,6-trimercapto-
1,3,5-triazine in aqueous solution and in a defined pH
range.

Documents:

00489-kolnp-2008-abstract.pdf

00489-kolnp-2008-claims.pdf

00489-kolnp-2008-correspondence others.pdf

00489-kolnp-2008-description complete.pdf

00489-kolnp-2008-form 1.pdf

00489-kolnp-2008-form 2.pdf

00489-kolnp-2008-form 3.pdf

00489-kolnp-2008-form 5.pdf

00489-kolnp-2008-gpa.pdf

00489-kolnp-2008-international publication.pdf

00489-kolnp-2008-international search report.pdf

00489-kolnp-2008-pct priority document notification.pdf

00489-kolnp-2008-pct request form.pdf

00489-kolnp-2008-translated copy of priority document.pdf

489-KOLNP-2008-(13-10-2011)-ABSTRACT.pdf

489-KOLNP-2008-(13-10-2011)-DESCRIPTION (COMPLETE).pdf

489-KOLNP-2008-(13-10-2011)-EXAMINATION REPORT REPLY RECEIVED.pdf

489-KOLNP-2008-(13-10-2011)-FORM 1.pdf

489-KOLNP-2008-(13-10-2011)-FORM 2.pdf

489-KOLNP-2008-(13-10-2011)-FORM 3.pdf

489-KOLNP-2008-(13-10-2011)-OTHERS.pdf

489-KOLNP-2008-(17-10-2011)-PETITION UNDER SECTION 8(1).pdf

489-KOLNP-2008-(27-01-2012)-CORRESPONDENCE.pdf

489-KOLNP-2008-CORRESPONDENCE OTHERS 1.1.pdf

489-KOLNP-2008-CORRESPONDENCE OTHERS 1.2.pdf

489-KOLNP-2008-CORRESPONDENCE.pdf

489-KOLNP-2008-EXAMINATION REPORT.pdf

489-KOLNP-2008-FORM 18 1.1.pdf

489-kolnp-2008-form 18.pdf

489-KOLNP-2008-FORM 3.pdf

489-KOLNP-2008-FORM 5.pdf

489-KOLNP-2008-GPA.pdf

489-KOLNP-2008-GRANTED-ABSTRACT.pdf

489-KOLNP-2008-GRANTED-CLAIMS.pdf

489-KOLNP-2008-GRANTED-DESCRIPTION (COMPLETE).pdf

489-KOLNP-2008-GRANTED-FORM 1.pdf

489-KOLNP-2008-GRANTED-FORM 2.pdf

489-KOLNP-2008-GRANTED-SPECIFICATION.pdf

489-KOLNP-2008-INTERNATIONAL PRELIMINARY REPORT.pdf

489-KOLNP-2008-INTERNATIONAL SEARCH AUTHORITY REPORT 1.1.pdf

489-KOLNP-2008-OTHERS-1.1.pdf

489-KOLNP-2008-OTHERS.pdf

489-KOLNP-2008-PETITION UNDER RULE 134.pdf

489-KOLNP-2008-REPLY TO EXAMINATION REPORT 1.1.pdf

489-KOLNP-2008-REPLY TO EXAMINATION REPORT.pdf

489-KOLNP-2008-TRANSLATED COPY OF PRIORITY DOCUMENT.pdf

« Previous Patent

Next Patent »

Patent Number

254625

Indian Patent Application Number

489/KOLNP/2008

PG Journal Number

48/2012

Publication Date

30-Nov-2012

Grant Date

27-Nov-2012

Date of Filing

04-Feb-2008

Name of Patentee

EVONIK DEGUSSA GMBH.

Applicant Address

RELLINGHAUSER STRASSE 1-11, 45128 ESSEN

Inventors:

#	Inventor's Name	Inventor's Address
1	PETER WERLE	IM BORNER 43, 63571 GELNHAUSEN
2	MICHAEL BECK	GEORG-WOLFF-STR. 7A, 63454 HANAU
3	MARTIN TRAGESER	SCHULSTR. 1A, 63571 GELNHAUSEN

PCT International Classification Number

C07D 251/38

PCT International Application Number

PCT/EP2006/063795

PCT International Filing date

2006-07-03

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	10 2005 036 693.7	2005-08-04	Germany