Ex Parte Kowarsch et al

Patent Trial and Appeal Board

Oct 12, 2018

12527706 (P.T.A.B. Oct. 12, 2018)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR
12/527,706 08/19/2009 Heinrich Kowarsch
22850 7590 10/16/2018
OBLON, MCCLELLAND, MAIER & NEUSTADT, L.L.P.
1940 DUKE STREET
ALEXANDRIA, VA 22314
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
ATTORNEY DOCKET NO. CONFIRMATION NO.
346556USOPCT 7556
EXAMINER
0 DELL, DAVID K
ART UNIT PAPER NUMBER
1625
NOTIFICATION DATE DELIVERY MODE
10/16/2018 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):
patentdocket@oblon.com
OBLONPAT@OBLON.COM
iahmadi@oblon.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte HEINRICH KOW ARSCH, JOSEF HETZENEGGER,
ANDREAS STOHR, and HANS-JOACHIM USCHMANN
Appeal2017-004602 1
Application 12/527,706
Technology Center 1600
Before FRANCISCO C. PRATS, JEFFREY N. FRED MAN, and
DEBORAH KATZ, Administrative Patent Judges.
PRATS, Administrative Patent Judge.
DECISION ON APPEAL
This appeal under 35 U.S.C. § 134 involves claims to processes of
preparing a perylenebis( dicarboximide ), such as Pigment Red 149. The
Examiner rejected the claims for obviousness.
We have jurisdiction under 35 U.S.C. § 6(b). We reverse.
STATEMENT OF THE CASE
The sole rejection before us for review is the Examiner's rejection of
claims 1-5, 7-9, 11, 13, 15, 17, 20, and 21 under 35 U.S.C. § 103(a), for
1 Appellants state that the real party in interest in this appeal is BASF SE.
Appeal Br. 2.
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Application 12/527,706
obviousness over Spietschka, 2 Paul, 3 Dalziel, 4 Urban, 5 Herbst, 6 Wiirthner, 7
Schulz, 8 Wolska, 9 Wescott, 10 and Nagao. 11 Ans. 2-9.
Claims 1, 8, and 15 are the independent claims on appeal. Claim 1 is
illustrative and reads as follows:
Claim 1: A process for preparing N,N'-di(3 ',5 '-dimethyl
phenyl)perylenebis( dicarboximide ), the process comprising
reacting perylene-3,4,9, IO-tetra carboxylic dianhydride with
3,5-dimethylaniline in the presence of a secondary amine as
catalyst, wherein:
a molar ratio between the 3,5-dimethylaniline and the
perylene-3,4,9, 10-tetracarboxylic dianhydride ranges from 2: 1
to 3:1;
the reaction occurs in an aqueous reaction medium and in
2 US 4,831,140 (issued May 16, 1989).
3 Edward L. Paul et al., Organic crystallization processes, 150 POWDER
TECHNOLOGY 133--43 (2005) ("Paul").
4 US 2003/0152500 Al (published Aug. 14, 2003).
5 US 5,626,662 (issued May 6, 1997).
6 WILLY HERBST & KLAUS HUNGER, INDUSTRIAL ORGANIC PIGMENTS, 4 7 4--
77 (3rd ed. 1998) ("Herbst").
7 Frank Wiirthner et al., Preparation and Characterization of
Regioisomerically Pure 1, 7-Disubstituted Perylene Bisimide Dyes, 69 J.
0RG. CHEM. 7933-39 (2004) ("Wiirthner").
8 US 6,391,104 Bl (issued May 21, 2002).
9 Anna Wolska et al., Soluble Polycyclic Dyes, 46 DYES, AUXILARY
PRODUCTS 15-26 (2002) (as translated) ("Wolska").
10 Lyle D. Wescott & Daniell Lewis Mattern, Donor-(J-Acceptor Molecules
Incorporating a Nonadecyl-Swallowtailed Perylenediimide Acceptor, 68 J.
0RG. CHEM. 10058---66 (2003) ("Wescott").
11 Yukinori Nagao & Takahisa Misono, Synthesis and Reactions of
Perylenecarboxylic Add Derivatives. VIII. Synthesis of N-Alkyl-3, 4: 9, 10-
Perylenetetracarboxylic Monoanhydride Monoimide, 54 BULL. CHEM. Soc.
JPN. 1191-94 (1981) ("Nagao").
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the presence of added seed crystals ofN,N'-di(3',5'-
dimethylphenyl) perylene bis ( dicarboximide ), wherein the seed
crystals are present prior to the beginning of the reaction;
the aqueous reaction medium is present at the
beginning of the reaction;
the reaction occurs at a temperature in the range from
130°C to 170°C and at a pressure in the range from 2 bar to 13
bar; and
the process provides Pigment Red 149 in the alpha form,
such that the Pigment Red 149 comprises less than 5% by
weight of a monoimide by-product.
Appeal Br. 22 (Claims App'x) (emphasis added to show limitation at issue);
see also id. at 23 (independent claim 8 reciting similar process in which "the
aqueous reaction medium is present at the beginning of the reaction"); id. at
24 (independent claim 15 reciting same).
OBVIOUSNESS
The Examiner's Prima Facie Case
The Examiner cited Spietschka as disclosing processes in which the
reactants recited in Appellants' claims-perylene-3,4,9,10-tetra carboxylic
dianhydride, 3,5-dimethylaniline, and a secondary amine as catalyst-were
reacted together to yield Pigment Red 149, a perylene bis(dicarboximide).
Ans. 3--4.
The Examiner found that Appellants' claims differ from the processes
described in Spietschka in that Appellants' claims "require that the reaction
is in the presence of added seed crystals ofN,N'-di(3',5'-dimethylphenyl)
perylenebis( dicarboximide) and that water is present 'prior to the beginning
of the reaction'." Id. at 4.
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The Examiner found that the level of ordinary skill in the relevant art
"is high. An organic process chemist would be apprised of the effect of
solvent on the course of the reaction and would appreciate known methods
of obtaining pure materials such as crystallization. It is routine for a process
chemist to perform a solvent optimization for reactive crystallization." Id.
The Examiner cited Paul as evidence that an ordinary artisan would
have considered it obvious, at the beginning of Spietschka's synthesis, to
include seed crystals of the final product to be obtained, and cited Dalziel as
evidence that adding water to Spietschka's synthesis "would promote
crystallization since it is an antisolvent that the product hydrocarbons are
poorly soluble in. This is sometimes referred to as drowning out." Id. at 5.
The Examiner cited Urban as evidence of the obviousness of grinding the
recovered crystals, as recited in dependent claim 9. See id. at 6.
The Examiner found that, "[i]n addition to these considerations, there
is a large amount of evidence showing that water is a standard reaction
medium for the reaction ofperylene-3,4,9,10-tetracarboxylic dianhydride
with amines" (id. at 6), and cited Herbst, Wiirthner, Schulz, and Wolska in
support of that finding (id. at 6-7).
As to the requirement in Appellants' claims for the molar ratio
between the 3,5-dimethylaniline and the perylene-3,4,9, 10-tetracarboxylic
dianhydride to be from 2: 1 to 3: 1, the Examiner found that Spietschka' s
Example 5 "use[d] only a 3.2 fold excess of 3,5-dimethylaniline which is
near the [ claimed] range." Id. at 7. The Examiner additionally found that
"[ d]etermining the optimal equivalents of aniline is mere optimization of a
prior art process, within the scope of what one skilled in the art would be
capable of and is insufficient to establish patentable unobviousness,
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especially since it is clear the Spietschka is altering the equivalents of
aniline." Id. at 7-8.
As to the requirement in Appellants' claims that the processes be
conducted at a pressure in the range from 2 bar to 13 bar, the Examiner cited
Wescott and Nagao as describing the performance of the type of reaction
claimed in an autoclave, and found therefore that "conducting the reaction in
water in sealed vessels is a known standard protocol." Id. at 8.
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.
In KSR Int 'l Co. v. Teleflex Inc., 550 U.S. 398 (2007), although the
Supreme Court emphasized "an expansive and flexible approach" when
analyzing the issue of obviousness, id. at 415, the Court also reaffirmed the
importance of determining "whether there was an apparent reason to
combine the known elements in the fashion claimed by the patent at issue."
Id. at 418.
Thus, even under the flexible analysis outlined in KSR, "[ o ]bviousness
requires more than a mere showing that the prior art includes separate
references covering each separate limitation in a claim under examination."
Unigene Laboratories, Inc. v. Apotex, Inc., 655 F.3d 1352, 1360 (Fed. Cir.
2011).
Rather, "[i]n determining whether obviousness is established by
combining the teachings of the prior art, the test is what the combined
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teachings of the references would have suggested to those of ordinary skill
in the art." In re GPAC Inc., 57 F.3d 1573, 1581 (Fed. Cir. 1995) (internal
quotations omitted).
In other words, even post-KSR, "obviousness concerns whether a
skilled artisan not only could have made but would have been motivated to
make the combinations or modifications of prior art to arrive at the claimed
invention." Belden Inc. v. Berk-TekLLC, 805 F.3d 1064, 1073 (Fed. Cir.
2015).
In the present appeal, having carefully considered all of the arguments
and evidence advanced by Appellants and the Examiner, Appellants
persuade us that the preponderance of the evidence does not support the
Examiner's conclusion of obviousness. In particular, Appellants persuade us
that the Examiner has not shown, by a preponderance of the evidence, that
the cited combination of references would have suggested performing the
reaction recited in Appellants' independent claims 1, 8, and 15, in the
aqueous medium required by those claims.
Spietschka discloses
an improved process for the preparation of arylimides of
perylene-3,4,9, 10-tetracarboxylic acid by use of compounds
which act to increase the reaction rate of the condensation,
which is known per se, ofperylene-3,4,9,10-tetracarboxylic
dianhydride or a perylene-3,4,9,10-tetracarboxylic
monoanhydride monoimide with a primary arylamine and, at
the same time, avoid the disadvantages associated with the
condensation auxiliaries hitherto used.
Spietschka 1:6-14.
In particular, Spietschka discloses that condensation auxiliaries that
had been previously used to drive the condensation reaction by eliminating
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water from the reaction milieu suffered from a number of disadvantages. Id.
at 1:30-52.
Spietschka discloses, however, that using dialkylamines, such as
diethanolamine, as catalysts in the condensation reaction overcomes the
disadvantages of previously used condensation auxiliaries. Id. at 2:48.
Spietschka discloses that the reaction of the perylene-3,4,9,10-
tetracarboxylic dianhydride, primary arylamine, and dialkylamine catalyst
can be carried out under pressure in the presence of inert organic diluents;
"[h ]owever, the reaction is preferably carried out without the addition of
further diluents in the relevant mixture of arylamine (formula 3) and
dialkylamine (formula 4). The reaction time is about 0.5-12 hours." Id. at
3:50-54.
The Examiner cited Examples 1 and 11 of Spietschka to support the
conclusion of obviousness. See Ans. 3.
As required by each of Appellants' independent claims 1, 8, and 15,
Examples 1 and 11 of Spietschka both disclose reactions of perylene-
3 ,4,9, 10-tetracarboxylic dianhydride, 3,5-dimethylaniline, and a secondary
amine catalyst, providing nearly 100% yields. See id. at 4:36-62
(Spietschka's Example 1 disclosing "a yield of97.5% of theory"); id. at 7:1-
17 (Spietschka's Example 4 disclosing "a yield of 99.4% of theory").
As Appellants contend, Examples 1 and 11 of Spietschka both
disclose continuous removal of water from the reaction. See id. at 4:41--42
(Spietschka's Example 1 disclosing "continuously driving off the water of
reaction with a slow stream of nitrogen"); id. at 7:6-7 (Spietschka's
Example 4 disclosing "continuously removing the water eliminated in the
reaction by distillation in a slow stream of nitrogen").
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As Appellants contend, Spietschka's claim 1 describes performing the
claimed reaction "with continuous removal [ of] the water of reaction and
substantially in the absence of water as an inert diluent." Id. at 12:3-5.
Thus, as Appellants contend, Spietschka discloses performing its
reaction, when under pressure, either in the presence of organic diluents, or
preferably only in the presence of the dianhydride, arylamine, and secondary
amine catalyst, and repeatedly discloses that water should be continuously
eliminated from the reaction. In response to Appellants' arguments that,
given the teachings in Spietschka, an ordinary artisan would not have
modified Spietschka's condensation reaction and performed it in an aqueous
medium as recited in Appellants' independent claims 1, 8, and 15, the
Examiner contends:
A number of other references show that reactions in water
under pressure became standard conditions for the formation of
these dye compounds. Spietschka was the state of the art on
April 11, 1986 (US filing date) when his invention was made,
however Spietschka and all the prior art is evaluated at the time
the present invention was made which is filing date of the
instant application, August 19, 2009 or if priority were
perfected February 19, 2007. In the intervening 20 years or so
between Spietschka and the filing of the instant application,
substantial improvements were made to the reaction conditions.
The rejection cites six supporting references including a
standard industrial dye textbook, each of which are summarized
in the rejection statement.
Ans. 10.
Therefore, the Examiner contends, the rejection "establishes that
conducting the reaction in water under pressure is a known standard protocol
that evolved subsequent to Spietschka but prior to the time the present
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invention was made. Rather than teaching away, the prior art teaches toward
conducting the reactions in water under pressure." Id. at 11.
We are not persuaded. The Examiner does not identify in any of
Herbst, Wiirthner, Schulz, Wolska, Wescott, or Nagao any advantages that
might be gained by performing Spietschka's condensation reaction in an
aqueous medium. See id. at 10-12. Accordingly, as we understand it, the
Examiner's position is not that the prior art suggests some type of desirable
benefit that would have motivated a skilled artisan to deviate from
Spietschka's teachings to perform its condensation reaction in an aqueous
medium; rather, the Examiner's position is that it would have been obvious
to perform Spietschka's condensation reaction in an aqueous medium
because it was a "known standard protocol" (id. at 11) in the prior art for
that type of reaction.
As noted above, however, our reviewing court has explained
specifically that, even post-KSR, "obviousness concerns whether a skilled
artisan not only could have made but would have been motivated12 to make
the combinations or modifications of prior art to arrive at the claimed
invention." Belden v. Berk-Tek, 805 F.3d at 1073 (emphasis in original);
accord Personal Web Technologies, LLC v. Apple, Inc., 848 F.3d 987, 994
(Fed. Cir. 2017) (citing Belden).
Thus, even if it were true that it was standard protocol to perform
condensation reactions of the type described in Spietschka in an aqueous
12 We appreciate that KSR rejected a rigid application of the "TSM" test, but
KSR did maintain a requirement for "a reason that would have prompted a
person of ordinary skill in the relevant field to combine the elements in the
way the claimed new invention does." KSR, 550 U.S. at 418. No such
reason is presented in this case.
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medium, that would show, at best, that a skilled artisan could have
performed Spietschka' s reaction in an aqueous medium. We are not
persuaded that the Examiner has explained sufficiently why an ordinary
artisan would have been motivated to deviate from the non-aqueous
processes taught in Spietschka, which provide nearly 100% yields, based
solely on the fact that an alternative aqueous process was a known standard
protocol. That is, we are not persuaded that the Examiner's reliance on the
prior art to show the existence of a standard prior art protocol is sufficient to
meet the standard of obviousness outlined by our reviewing court in Belden
and Personal Web.
We are not persuaded, moreover, that the references cited by the
Examiner support the Examiner's contention that it was known standard
prior art protocol to perform condensation reactions of the type described in
Spietschka in an aqueous medium. Nor are we persuaded that the references
cited by the Examiner would have motivated a skilled artisan to deviate from
the non-aqueous processes taught in Spietschka, which provide nearly 100%
yields.
In particular, rather than stating that the process was standard in the
prior art, the textbook cited by the Examiner, Herbst, states only that, in
addition to organic syntheses, "[p ]igment synthesis through condensation in
aqueous medium has also been described." Herbst 4 7 5. And in addition to
making no statement to the effect that an aqueous medium was a standard
protocol, the cited pages of Herbst provide no citations to the literature
describing the use of an aqueous medium. See id. at 4 7 4--4 77.
We are not persuaded that the mere mention of performing pigment
synthesis by condensation in an aqueous medium, establishes that procedure
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as a standard protocol in the art. Nor are we persuaded that Herbst's mere
mention of such a process would have motivated a skilled artisan to deviate
from the non-aqueous processes taught in Spietschka, which provide nearly
100% yields.
Similarly, Wolska, the only reference cited by the Examiner
describing a condensation reaction that uses a secondary amine catalyst as
required by Appellants' independent claims 1, 8, and 15, makes no mention
of the aqueous medium as a standard protocol, and discloses only a 67%
yield. See Wolska translation at 10. We are not persuaded, therefore, that
Wolska establishes the use of an aqueous medium as a standard protocol in
the art. Nor are we persuaded that Wolska would have motivated a skilled
artisan to deviate from the non-aqueous processes taught in Spietschka,
which provide nearly 100% yields.
Wiirthner similarly makes no mention of an aqueous medium as a
standard protocol, and is directed to reactions that do not involve the use of a
secondary amine catalyst, unlike the reactions in Spietschka and recited in
Appellant's claims. See Wiirthner 7934--35. Indeed, Wiirthner uses an
aqueous medium because the reference involves brominated perylene
bisanhydride derivatives which are insoluble in organic solvents (see id.),
thus further differing from the reactions described in Spietschka. We are not
persuaded, therefore, that Wiirthner establishes the use of an aqueous
medium as a standard protocol in the art. Moreover, given the significant
differences between the processes in Wiirthner and Spietschka, we are not
persuaded that Wiirthner would have motivated a skilled artisan to deviate
from the non-aqueous processes taught in Spietschka.
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Schulz similarly makes no mention of an aqueous medium as a
standard protocol, and is directed to reactions that do not involve the use of a
secondary amine catalyst, unlike the reactions in Spietschka and as recited in
Appellant's claims. See Schulz, generally. In particular, unlike Spietschka's
procedure, Schulz is directed to a two-step process that produces an
intermediate product without the use of a secondary amine catalyst. See id.
at 3 :21--4: 10. Thus, although Schulz describes water as a preferred solvent
(see id. at 7:37), given the significant differences between the processes in
Schulz and Spietschka, we are not persuaded that Schulz would have
motivated a skilled artisan to deviate from the non-aqueous processes taught
in Spietschka.
Nagao similarly makes no mention of an aqueous medium as a
standard protocol, and like the other references cited by the Examiner ( with
the exception of Wolska), is directed to reactions that do not involve the use
of a secondary amine catalyst, unlike the reactions of Spietschka and
Appellants' claims. See generally Nagao. Again, therefore, we are not
persuaded that Nagao establishes the use of an aqueous medium as a
standard protocol in the art for the secondary amine-catalyzed process taught
in Spietschka. The Examiner, moreover, points to no evidence suggesting
that Nagao's process would provide results similar to those described in
Spietschka in the presence of a secondary amine catalyst. To the contrary,
as noted above, Wolska discloses only a 67% yield when using a secondary
amine catalyst in an aqueous medium. See Wolska translation at 10.
In addition, Nagao involves alkylamines rather than the 3,5-
dimethylaniline of Spietschka and Appellants' claims, and the highest yields
taught in Nagao (85-89%) are significantly lower than the near 100% yields
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disclosed in Spietschka. See id. at 1191. Accordingly, given the significant
differences between the processes in Nagao and Spietschka, and the lower
yields, we are not persuaded that Nagao would have motivated a skilled
artisan to deviate from the non-aqueous processes taught in Spietschka.
Wescott similarly makes no mention of an aqueous medium as a
standard protocol, and like the other references cited by the Examiner (with
the exception of Wolska), is directed to reactions that do not involve the use
of a secondary amine catalyst, unlike the reactions of Spietschka and
Appellants' claims. See generally Wescott. Although Wescott cites Nagao
in stating that, "[ a ]ccording to the literature, symmetrical 3 's can be obtained
by autoclaving an aqueous solution of the dianhydride 1 and a primary
amine" (id. at 10059 (footnote omitted)), we are not persuaded that the mere
mention of a previous synthesis establishes that method as a standard
protocol. Moreover, given the significant differences between the processes
in Wescott and Spietschka, we are not persuaded that Wescott would have
provided a reason for a skilled artisan to deviate from the non-aqueous
processes taught in Spietschka.
In sum, for the reasons discussed, we agree with Appellants that,
when the relevant cited prior art is viewed individually and for its teachings
as a whole, we are not persuaded that the Examiner has shown by a
preponderance of the evidence that an ordinary artisan would have had
reason to perform the reaction taught in Spietschka in the aqueous medium
required by each of Appellants' independent claims 1, 8, and 15.
Accordingly, we reverse the Examiner's rejections of those claims, and their
dependents, over the cited references.
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SUMMARY
For the reasons discussed, we reverse the Examiner's rejection of
claims 1-5, 7-9, 11, 13, 15, 17, 20, and 21 under 35 U.S.C. § 103(a), for
obviousness over Spietschka, Paul, Dalziel, Urban, Herbst, Wiirthner,
Schulz, Wolska, Wescott, and Nagao.
REVERSED
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