Ex Parte Ouziel et al

Board of Patent Appeals and Interferences

Sep 17, 2011

11660533 (B.P.A.I. Sep. 17, 2011)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte PHILIPPE OUZIEL and TORSTEN KULKE
__________

Appeal 2010-008324
Application 11/660,533
Technology Center 1600
__________

Before TONI R. SCHEINER, FRANCISCO C. PRATS, and
JEFFREY N. FREDMAN, Administrative Patent Judges.

PRATS, Administrative Patent Judge.

DECISION ON APPEAL
This appeal under 35 U.S.C. § 134 involves claims to a derivatized
cyclodextrin compound and a method of its preparation. The Examiner
entered a rejection for obviousness.
We have jurisdiction under 35 U.S.C. § 6(b). We reverse.

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Application 11/660,533

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STATEMENT OF THE CASE
Claims 1-5, 7-9, and 11-13 stand rejected and appealed (App. Br. 2).
Claim 1, the only independent claim, is directed to a “reactive
polysaccharide” (id. at 12) of formula

in which “Z1”and “B” can be a variety of different substituents, and “PS” is
cyclodextrin or a cyclodextrin derivative (id. at 12-13). Claim 5 recites a
process of making the compound of claim 1 and appears in Appellants‟
Claims Appendix (id. at 19-20).
In response to a species election requirement, Appellants elected the
following compound for prosecution on the merits:

in which “CD” represents cyclodextrin (see App. Br. 7; see also Ans. 4; also
Spec. 25). Accordingly, we limit our analysis to the patentability of the
elected compound, and the extent to which the appealed claims read on it.
See Ex parte Ohsaka, 2 USPQ2d 1460, 1461 (Bd. Pat. App. Int. 1987).
The sole rejection before us for review is the Examiner‟s rejection of
claims 1-5, 7-9, and 11-13 under 35 U.S.C. § 103(a) as obvious over Kulke,
1

Lewis,
2
Tang,
3
and Tzikas
4
(Ans. 3-7).
5

1
WO 03/093325 A1 (published November 13, 2003).
2
U.S. Patent No. 4,563,189 (filed February 6, 1984).
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OBVIOUSNESS
The Examiner found that Kulke taught reactive cyclodextrin
derivatives useful for treating textile fiber materials, the cyclodextrins‟
reactive groups preferably containing triazine rings (Ans. 4). The Examiner
found, however, that while the reactive groups of Kulke‟s compounds were
similar to the reactive group of the elected species, “Kulke does not teach
the reactive group of the elected species, which contains two phenyl rings
attached to the triazine ring, and each phenyl being substituted with a
sulfatoethylsulfonyl radical” (id. at 5).
To address that deficiency, the Examiner cited Lewis as teaching a
compound, termed “BAB,” that was useful for attaching dyes to textile
fibers in a manner analogous to the way Kulke attached cyclodextrins to
textile fibers (id. at 6). The Examiner also cited Tang as disclosing the use
of “the compound described above by Lewis” as a crosslinking agent for
fixing a polymeric dye to cotton and silk, and Tzikas as teaching conversion
of sulfatoethylsulfonyl radicals on reactive dyes to vinylsulfonyl radicals,
thus allowing the dyes to react with the textile fiber (id.).
Based on the cited teachings, the Examiner concluded that an ordinary
artisan would have considered it obvious to make a reactive cyclodextrin
derivative “using the reactive compound taught by Lewis or Tang, and to use
it for textile finishing. Kulke teaches that reactive cyclodextrin derivatives
are useful for textile finishing, and that all fiber reactive groups known in the

3
Bingtao Tang et al., Synthesis and dyeing performance of a novel yellow
crosslinking polymeric dye, 120 COLOR. TECHNOL. 180-83 (2004).
4
U.S. Patent No. 5,597,904 (filed March 12, 1996).
5
The Examiner included claim 6 in this rejection; however, claim 6 has been
canceled (see App. Br. 2).
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field of reactive dyestuffs, especially those having a triazine ring, are
suitable” (id.).
The Examiner reasoned:
Both Lewis and Tang teach the compound shown above, which
has a triazine ring, for use in textile treatments to improve dye
fixation. The Lewis/Tang compound is known for reacting with
fibers, contains the triazine ring substituted with Cl and N-
phenyl, and has the vinylsulfonyl anchor, which are all taught
by Kulke. Thus, it would have been obvious to prepare a
reactive cyclodextrin derivative using that compound as the
reactive group.

(Id.)
The Examiner further reasoned that the synthesis required to arrive at
the elected species of compound from the components described in the cited
references, and also required by claim 5, would have been obvious to an
ordinary artisan:
[I]n order to assemble the reactive cyclodextrin derivative using
Lewis‟ compound, three segments must react to form the final
product: cyclodextrin, formula (VII), and formula (VI). It
would have been obvious to assemble the cyclodextrin
derivative by first reacting Lewis‟ formula (VII) compound
with the cyclodextrin and then attaching the triazine portion
(Lewis‟ formula (VI) compound), or by assembling Lewis‟
molecule and then reacting it with cyclodextrin. In order to
attach Lewis‟ molecule to cyclodextrin, it would have been
obvious to use the vinylsulfonyl derivative, as taught by Tzikas.
Attachment of the Lewis/Tang compound to cyclodextrin using
methods known in the art would result in the elected species.

(Id. at 7.)
Appellants argue, for a number of reasons, that although “the
examiner has identified various fiber reactive structures within the literature
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such as the fiber reactive reagent identified Tang and Lewis, there is no
motivation in any of the above identified references to alter a cyclodextrin
molecule as presently claimed” (App. Br. 9; see also id. at 9-11).
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.

While this is arguably a very close case, we find that a preponderance
of the evidence does not support the Examiner‟s position.
We acknowledge that, generally, substitution of one equivalent
element for another is considered obvious. See KSR Int’l v. Teleflex Inc.,
550 U.S. 398, 421 (2007):
When there is a design need or market pressure to solve
a problem and there are a finite number of identified,
predictable solutions, a person of ordinary skill has good reason
to pursue the known options within his or her technical grasp.
If this leads to the anticipated success, it is likely the product
not of innovation but of ordinary skill and common sense. In
that instance the fact that a combination was obvious to try
might show that it was obvious under § 103.

Here, however, as the Examiner concedes (see Ans. 7), preparation of
the elected species of compound requires more than the mere substitution of
one equivalent fiber-reactive radical for another onto a cyclodextrin
molecule. Rather, preparation of a cyclodextrin derivative with the structure
of the elected species necessitates a sequential reaction scheme in which
cyclodextrin is first reacted with one segment of Lewis‟ BAB compound,
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followed by reacting the resulting construct with the second segment of the
BAB compound (see id., see also Lewis, col. 5, ll. 45-65 (preparation of
Lewis‟ compounds by reacting compounds VI and VII)).
We see nothing in any of the cited references specifically suggesting
involvement of a cyclodextrin molecule in such a synthesis scheme. Instead,
Lewis teaches that the fabrics are simply pretreated with the dye-enhancing
compounds, and the dyes applied thereafter (see id. at col. 9, l. 59, through
col. 10, l. 2 (using BAB)), or else the fabric, dye-enhancer, and dye are
simply placed into a single dye bath (id. at col. 8, ll. 23-38 (Example 4)).
Somewhat similarly, Tang applies the dye, and then uses the reactive
compound as a crosslinking agent to fix the dye to the fiber (Tang 181
(“After the dyed fibre had dried at room temperature, it was dipped into the
fixing bath containing 6% (wt/wt) crosslinking agent (DAST) . . . .”)). We
are not persuaded that an ordinary artisan viewing these teachings would
have been prompted to link Lewis‟ BAB compound to cyclodextrin via the
required sequential series of steps, before linking BAB to the fabric,
particularly given no specific suggestion in the art as to the methodology and
structure by which the cyclodextrin would be linked to either of the two
precursors of the BAB compound.
We acknowledge Kulke‟s disclosure that cyclodextrins derivatized
with fabric-bonding, triazine-containing reactive moieties can be “applied to
the goods in aqueous solution, in analogy to the dyeing processes known for
reactive dyes” (Kulke 9). Thus, functionalities carried by, or inherent to,
cyclodextrins, such as antimicrobial or deodorizing properties, can be
imparted to fabrics (id. at 9-10).
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However, as discussed above, Lewis teaches that, to use BAB to
impart a functionality, such as a dye, to a fabric, one applies the BAB to the
fabric and then applies the functionality-imparting compound. The
Examiner has not provided a clear fact-based explanation as to why an
ordinary artisan would have diverged from Lewis‟ explicit teachings in this
regard, and instead used a sequential synthesis scheme described nowhere in
the cited references to link Lewis‟ BAB to cyclodextrin to achieve the
elected species of compound.
We acknowledge, as the Examiner argues, that “although the cited
references do not exemplify reaction of cyclodextrin with vinylsulfone or
sulfatoethylsulfonyl radical, the skilled artisan would expect that
cyclodextrin could be derivatized with a reactive compound in this way”
(Ans. 9; see also Tzikas, col. 5, ll. 1-5).
We are not persuaded, however, that the mere fact that a particular
linkage between Lewis‟ BAB and cyclodextrin might be possible
demonstrates that an ordinary artisan would have been prompted to make
that modification, absent some suggestion to do so. Cf. Transocean
Offshore Deepwater Drilling, Inc. v. Maersk Contractors USA, Inc., 617
F.3d 1296, 1303 (Fed. Cir. 2010) “([I]t is not enough to simply show that the
references disclose the claim limitations; in addition, „it can be important to
identify a reason that would have prompted a person of ordinary skill in the
art to combine the elements as the new invention does.‟”) (quoting KSR, 550
U.S. at 401 (emphasis added)).
Thus, the fact that an ordinary artisan might have been aware that
cyclodextrin could be linked to other radicals using the linkage in the elected
species would not, in our view, have suggested to an ordinary artisan that it
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would be desirable, or even suitable, to diverge from the methodology
explicitly taught by Lewis as the technique by which functional compounds
should be linked to fabric using BAB.
Accordingly, while the Examiner has done an admirable job in finding
the most relevant prior art, we are not persuaded that the combined
disclosures of Kulke, Lewis, Tang, and Tzikas suggest modifying their
teachings in a manner that would result in Appellants‟ elected species of
compound. We therefore reverse the Examiner‟s obviousness rejection of
claims 1-5, 7-9, and 11-13 over those references.

REVERSED

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