Ex Parte Broell et al

Patent Trial and Appeal Board

Aug 30, 2017

14351981 (P.T.A.B. Aug. 30, 2017)

United States Patent and Trademark Office
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O.Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
14/351,981 04/15/2014 Dirk Broell 432103US99PCT 3438
22850 7590 09/01/2017
OBLON, MCCLELLAND, MAIER & NEUSTADT, L.L.P.
1940 DUKE STREET
ALEXANDRIA, VA 22314
EXAMINER
KUMAR, SHAILENDRA
ART UNIT PAPER NUMBER
1672
NOTIFICATION DATE DELIVERY MODE
09/01/2017 ELECTRONIC
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
following e-mail address(es):
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PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte DIRK BROELL, BENEDIKT LAUX,
CHRISTIAN MAUL, PATRICK PETER, and CLAUS ZIMMER
Appeal 2016-004329
Application 14/351,9811
Technology Center 1600
Before FRANCISCO C. PRATS, JEFFREY N. FREDMAN, and
JOHN E. SCHNEIDER, Administrative Patent Judges.
PRATS, Administrative Patent Judge.
DECISION ON APPEAL
This appeal under 35 U.S.C. § 134(a) involves claims to a method for
preparing an N-alkyl(meth)acrylamide. The Examiner rejected the claims
for obviousness.
We have jurisdiction under 35 U.S.C. § 6(b). We affirm.
STATEMENT OF THE CASE
The sole rejection before us for review is the Examiner’s rejection of
claims 1, 3—5, and 7—12, under 35 U.S.C. § 103(a), for obviousness over
1 Appellants state that the “real party in interest is Evonik Roehm GMBH of
Darmstadt, Germany.” Appeal Br. 1.
Appeal 2016-004329
Application 14/351,981
Knebel2 and Morris3 (Ans. 3—4).
Claim 1, the sole independent claim on appeal, is representative and
reads as follows (Appeal Br. 9):
1. A process for preparing an N-alkyl(meth)acrylamide
of formula (1), the process comprising:
charging (meth)acrylic anhydride in a reaction vessel;
reacting (meth)acrylic anhydride with an aqueous
solution of an alkylamine of formula (2) at a temperature of
from -5°C to 40°C and a pressure of from 0.5 to 6 bar, thereby
obtaining the N-alkyl(meth)acrylamide in a reaction solution,
wherein the initial reaction temperature does not exceed
25°C;
cooling the reaction vessel to a temperature above a
crystallization temperature of the N-alkyl(meth)acrylamide in
the reaction solution; and
separating the N-alkyl(meth)acrylamide:
R,
■A
R;:
•R-i
O
(1), R2R3NH (2),
where
Ri is H or a CH3 group, and
R2 and R3 are hydrogen or a linear, branched or cyclic
alkyl radical or aryl radical comprising from 1 to 12 carbon
atoms,
wherein uncontrolled precipitates in the form of lumps or
deposits do not form on the walls of the reaction vessel.
2 US 2011/0218312 A1 (published Sept. 8,2011).
3 WO 2010/021956 A2 (published Feb. 25, 2010).
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Application 14/351,981
OBVIOUSNESS
The Examiner’s Prima Facie Case
In rejecting the pending claims, the Examiner found that Knebel
teaches a “process of making an N-alkyl(meth)acrylamide starting from
(meth)acrylic anhydride and an alkyl amine, similar to claimed in herein.
See claims, examples 1-3. The difference between the reference and herein
claimed process, if any, will be temperature, pressure and the ratio of the
reactants.” Ans. 3.
Like Knebel, the Examiner found that Morris teaches a “process of
making an N-alkyl(meth)acrylamide starting from (meth)acrylic anhydride
and an alkyl amine, similar to claimed in herein, see the summary, page 4,
example 1 and claims. Again the difference between the reference and
herein claimed process is molar ratio, temperature, pressure etc.” Id.
The Examiner reasoned that an ordinary artisan would have
considered the claimed process obvious in view of the combined teachings
of Knebel and Morris “because the references are expressly teaching similar
process under similar conditions and the difference if any between the
temperature, pressure and molar ratio can be worked out under routine
optimization, with the reasonable expectation of achieving of high yield of
N-(meth)acrylamide, absent evidence to the contrary.” Id. at 4.
Analysis
As stated in In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992):
[T]he examiner bears the initial burden ... of presenting a
prima facie case of unpatentability. . . .
After evidence or argument is submitted by the applicant
in response, patentability is determined on the totality of the
record, by a preponderance of evidence with due consideration
to persuasiveness of argument.
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Application 14/351,981
In the present case, Appellants do not persuade us that the
preponderance of the evidence fails to support the Examiner’s conclusion
that the process recited in representative claim 1 would have been prima
facie obvious to an ordinary artisan.
Appellants contend initially that the reaction between (meth)acrylic
anhydride and an alkylamine, which produces N-alkyl(meth)acrylamides, is
exothermic, and thus requires cooling. Appeal Br. 3. Appellants contend
however, that “cooling the reaction mixture also creates a problem in that the
desired N-alkyl(meth)acrylamides precipitate from solution if the reaction
temperature is too low. This generally requires that the reaction be stopped
so that the precipitate can be removed from the reactor, reducing reaction
efficiency.” Id. at 4.
Appellants contend that the combination of reaction parameters
recited in claim 1 is specifically directed to avoiding the precipitation of
N-alkyl(meth)acrylamides that occurs when cooling the reaction vessel. Id.
at 4—5. In addition to the specific process parameters recited in claim 1,
Appellants note that claim 1 recites that “uncontrolled precipitates in the
form of lumps or deposits do not form on the walls of the reaction vessel.”
Id. at 5. In contrast to this requirement in claim 1, Appellants contend, both
Knebel and Morris disclose that precipitates form in their processes. Id. at
5—6; see also Reply Br. 6—7.
We are not persuaded. We first note that claim 1 does not exclude all
precipitates. Rather, claim 1 excludes only “uncontrolled precipitates”
which are “in the form of lumps or deposits . . . [which] form on the walls of
the reaction vessel.” Appeal Br. 9 (emphasis added).
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Application 14/351,981
Although we acknowledge Knebel’s disclosure of precipitate
formation, rather than disclosing “uncontrolled” precipitation, Knebel
purposely uses precipitation as its purification method:
After the end of the addition [of the alkylamine to the
meth(acrylic) anhydride], a portion of the product formed has
generally already crystallized out and can, optionally after
cooling the product solution to complete the precipitation, be
filtered off. To increase the yield, the (meth)acrylic acid
present in the mother liquor can be neutralized, which leads to
further precipitation of product. The product is formed
virtually quantitatively. The substituted (meth)acrylamide
obtained possesses a high purity, which is usually above 95%.
Knebel 1 5.
Moreover, although two of the three examples of Knebel, cited by the
Examiner, describe the final product as precipitating out, neither example
describes the formation of lumps or deposits forming on the reaction vessel
wall. See id. 27 (in stirred reaction of methacrylic anhydride and
isopropylamine at 20-C “crystals precipitate out” and are then filtered and
washed (Example 1)); id. 31 (stirred reaction of methacrylic anhydride and
isopropylamine at 30-C cooled to room temperature; “precipitated crystals”
then filtered and washed (Example 3)).
Appellants do not persuade us, therefore, that the precipitation
described in Knebel is exclude by the current language in claim 1.
We acknowledge Morris’s disclosure, cited by Appellants, that, as
required by Appellants’ claim 1, and as described in Knebel, “an aqueous
solution of base and (alkyl)acrylic anhydride can be prepared and then the
N-alkyl amine added. The produced N-alkyl (alkyl)acrylamide monomer,
formed by reaction between the amine and the anhydride, can precipitate
from the reaction mixture as a relatively pure product.” Morris 123
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Application 14/351,981
(emphasis added). We acknowledge also the disclosure in the sole example
of Morris that, when methacrylic anhydride was added to a solution of
isopropylamine over a one hour period at 30-C, “a precipitate formed in the
reaction mixture,” which was then stirred and the contents filtered. Id. 133
(Example 1).
Similar to Knebel discussed above, Morris thus appears to purposely
use precipitation as a purification method, rather than suffering from the
uncontrolled precipitation excluded by Appellants’ claim 1. In any event,
the precipitated final product is not described as lumps or deposits that form
on the walls of the reaction vessel, and the precipitation is not described an
inevitable result, but simply “can occur.” Id. 123. We are not persuaded,
therefore, that the precipitation described in Morris is excluded by
Appellants’ claim 1.
Appellants contend:
[TJhere is no teaching or suggestion in the reference of
(a) reacting (meth)acrylic anhydride with an aqueous solution
of an alkylamine of formula (2) at a temperature of from -5°C
to 40°C, (c) the initial reaction temperature does not exceed
25°C, and (d) cooling the reaction vessel to a temperature
above a crystallization temperature of the N-
alkyl(meth)acrylamide in the reaction solution.
Appeal Br. 7 (emphasis in original).
We are not persuaded. Appellants, thus, aver that the cited references
do not suggest a process that includes, in particular, claim l’s step of cooling
the reaction vessel to a temperature above the crystallization temperature
after reacting (meth)acrylic anhydride with an alkylamine.
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Application 14/351,981
We note, however, that Knebel’s Example 2 describes cooling the
reaction vessel with no mention of crystallization or precipitation of the final
product:
After the end of the addition [of the N-dodecylamine],
the liquid, slightly viscous mixture is stirred at 40 ... 45° C. for
a further 3 h and cooled to room temperature. To distil off the
methacrylic acid, the reaction vessel is provided with a
distillation apparatus and heated to bottom temperature 97° C.
in an oil-pump vacuum (1 mbar) within 3h, which gives 154 g
of methacrylic acid (92% of theory). The distillation residue
consists of 490 g of N-dodecylmethacrylamide (99% of theory)
with a purity determined by gas chromatography of 98%.
Knebel 130 (Example 2).
We note, moreover, that although Knebel’s Example 2 uses an initial
reaction temperature of 30-35-C, Knebel discloses that N-dodecylamine has
a melting point of 25—28°C (see id.), thus suggesting the suitability of an
initial reaction temperature as low as the maximum of 25°C recited in
Appellants’ claim 1. To that end, we note also that Knebel’s Example 1
discloses the suitability of initial reaction temperatures below 20-C. Id. 127.
Thus, when viewing the teachings of the cited references as a whole,
we discern no error in the Examiner’s finding (Ans. 4—5) that an ordinary
artisan would have reasoned from those teachings that each of the steps and
associated parameters recited in the process recited in claim 1 would have
been suitable for preparing an N-alkyl(meth)acrylamide from (meth)acrylic
anhydride and an alkylamine. As the Supreme Court has explained, “when a
patent ‘simply arranges old elements with each performing the same
function it had been known to perform’ and yields no more than one would
expect from such an arrangement, the combination is obvious.” KSR Int’l
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Application 14/351,981
Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (quoting Sakraida v. Ag Pro,
Inc., 425 U.S. 273 (1976)).
It might be true that Appellants selected the specific series of steps
and parameters from the various teachings in the cited references for a
different reason—elimination of uncontrolled precipitates in the form of
lumps or deposits that form on the reaction vessel wall—than taught in the
references. That fact, however, does not demonstrate that the process recited
in claim 1 would have been unobvious. See id. at 419 (“In determining
whether the subject matter of a patent claim is obvious, neither the particular
motivation nor the avowed purpose of the patentee controls. What matters is
the objective reach of the claim. If the claim extends to what is obvious, it is
invalid under § 103.”).
In sum, for the reasons discussed, Appellants do not persuade us that a
preponderance of the evidence fails to support the Examiner’s prima facie
case that the process recited in claim 1 would have been obvious to an
ordinary artisan. Because Appellants do not advance secondary evidence of
nonobviousness that might outweigh the evidence of prima facie
obviousness, we affirm the Examiner’s rejection of claim 1. Because they
were not argued separately, claims 3—5 and 7—12 fall with claim 1. 37
C.F.R. § 41.37(c)(l)(iv).
SUMMARY
For the reasons discussed, we affirm the Examiner’s rejection of
claims 1, 3—5, and 7—12 over Knebel and Morris.
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Application 14/351,981
TIME PERIOD
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a).
AFFIRMED
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