DSM IP ASSETS B.V.

Patent Trials and Appeals Board

Mar 26, 2021

2020002148 (P.T.A.B. Mar. 26, 2021)

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.
15/518,080 04/10/2017 Werner BONRATH BHD-4662-3387 1047
23117 7590 03/26/2021
NIXON & VANDERHYE, PC
901 NORTH GLEBE ROAD, 11TH FLOOR
ARLINGTON, VA 22203
EXAMINER
KEYS, ROSALYND ANN
ART UNIT PAPER NUMBER
1699
NOTIFICATION DATE DELIVERY MODE
03/26/2021 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):
PTOMAIL@nixonvan.com
pair_nixon@firsttofile.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
_________________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
_________________

Ex parte WERNER BONRATH, JAN SCHUETZ, THOMAS NETSCHER,
and BETTINA WUESTENBERG
_________________

Appeal 2020-002148
Application 15/518,080
Technology Center 1600
_________________

Before RICHARD M. LEBOVITZ, RAE LYNN P. GUEST, and
DEBORAH KATZ, Administrative Patent Judges.

KATZ, Administrative Patent Judge.

DECISION ON APPEAL
Appellant1 seeks our review,2 under 35 U.S.C. § 134(a), of the
Examiner’s decision to reject claims 1 and 3–11. We have jurisdiction under
35 U.S.C. § 6(b). We AFFIRM.

1 We use the word “Appellant” as defined in 37 C.F.R. § 1.42. Appellant
identifies the real party-in-interest as DSM IP Assets B.V. (Appeal Br. 2.)
2 We consider the Final Office Action issued September 14, 2018 (“Final
Act.”), the Appeal Brief filed October 15, 2019 (“Appeal Br.”), and the
Examiner’s Answer issued on November 22, 2019 (“Ans.”) in reaching our
decision.
Appeal 2020-002148
Application 15/518,080

2
The Examiner rejects claims 1 and 3–11 under 35 U.S.C. § 103 as
being unpatentable over Bonrath3 and Organon.4 Appellant does not argue
that any of the rejected claims are separately patentable. Accordingly, we
focus on claim 1 in our analysis. See 37 C.F.R. § 41.37(c)(1)(iv).
Appellant’s specification is directed to a catalytic process for the
ethynylation of specific poly-unsaturated aldehydes and ketones. (Spec. 1.)
Appellant’s claim 1 recites:
A catalytic ethynylation process which comprises
conducting a catalytic ethinylation reaction of a compound of
formula (I):

, wherein

R1 signifies -H or -CH3,
R2 signifies -H, and
R3 signifies a moiety selected from the group consisting of:

with ethyne in NH3 as a solvent and in the presence of a
catalyst of formula ROH,

3 International Patent Application Publication WO 2004/018400 A1,
published March 4, 2004.
4 British Patent GB 634,924, published March 29, 1950.
Appeal 2020-002148
Application 15/518,080

3
wherein R signifies K or Cs at a catalytic ethinylation
reaction temperature between -40 °C to 10 °C.

(Appeal Br. 7.)
As the Examiner finds, and Appellant does not dispute, Bonrath
teaches a process for manufacturing acetylenically unsaturated alcohol by
reacting a ketone with acetylene in the presence of ammonia and an alkali
metal hydroxide. (See Final Act. 5; see Bonrath abstract.) Bonrath provides
examples of this process using potassium hydroxide (KOH) in aqueous
solution along with ammonia in an ethynylation process (See, e.g., Bonrath
5:19–6:1, see Final Act. 5.) Bonrath also teaches that the temperature for
this reaction is from about 0o C to about 40o C. (Bonrath 4; see Final Act.
5.)
The Examiner finds that Bonrath does not teach the ketones of
formula I recited in claim 1 in its disclosed ethynylation process. (See Final
Act. 6.) But, as the Examiner finds, Bonrath teaches
The nature of any other aldehyde or of the ketone which can be
reacted with acetylene in accordance with the process of the
present invention is not critical, and any aldehyde or ketone
with which acetylene is known to react to form an
acetylenically unsaturated alcohol may be used, i.e. according
to the equation

, the unspecified moieties attached to the “central” carbon atom
by the dotted lines being those featured in known aldehydes and
ketones or in any other aldehydes and ketones which can be
produced analogously to the known ones.
Appeal 2020-002148
Application 15/518,080

4

(Bonrath 2:21–28.) Thus, Bonrath teaches that the nature of the aldehyde or
ketone is not critical. (See Ans. 6–7.)
The Examiner finds that Organon teaches a compound of formula (I)
recited in Appellant’s claims. (See Final Act. 6, citing Organon 2:35–38.)
Appellant does not dispute this finding.
The Examiner finds that one of ordinary skill in the art would have
had a reasonable expectation of success using the ketone of Organon in
Bonrath because Bonrath teaches that any ketone could be used in its
process. (See Final Act. 6.) The Examiner finds further that one of ordinary
in the art would have had a reason to use the ketone of Organon in Bonrath’s
process because Bonrath demonstrates the ethynylation process works and,
thus, substituting one element for another would have been obvious. Cf.
KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (“[I]f a technique
has been used to improve one device, and a person of ordinary skill in the art
would recognize that it would improve similar devices in the same way,
using the technique is obvious unless its actual application is beyond his or
her skill.”).
Appellant argues that the C-C double bond of formula (I) of claim 1 is
conjugated and that “[t]hose ordinarily skilled in this art know that such
specific (at least α, β-unsaturated) polyunsaturated aldehydes and ketones
are difficult to produce and that until the presently claimed invention were
only produced by stoichiometric processes, such as by a Grignard reaction.”
(Appeal Br. 5.) Appellant does not direct us to evidence in support of this
assertion. (See Ans. 5.) Thus, we are not persuaded that the difficulty in
Appeal 2020-002148
Application 15/518,080

5
producing the ketone taught in Organon is a factor in determining the
obviousness of the claimed process.
Appellant acknowledges that Bonrath teaches a “very broad definition
of the substituents of formula (I),” but argues that no α, β-unsaturated
aldehydes or ketones are specifically taught to be ethynylated in Bonrath.
(Appeal Br. 5.) According to Appellant,
[t]he present Applicant has made a very specific selection of a
group of aldehydes and ketones and have developed the herein
claimed process in order to overcome the deficiencies of the
prior art processes. Thus, the fact that Organon may disclose
the compounds of formula (I), as well as those of compounds
(lb) and (le), would not prompt an ordinarily skilled person to
employ such compounds in the process of Bonrath et al.
(Appeal Br. 5–6.)
This argument is unpersuasive because it fails to provide a reason why
those in the art would not have used the ketones of Organon in the process of
Bonrath, particularly when Bonrath teaches any ketone known to react with
acetylene to form an acetylenically unsaturated alcohol may be used. (See
Bonrath 2:22–24.) Appellant does not dispute that the ketones taught in
Organon were known by those in the art to react to form an acetylenically
unsaturated alcohol. Nor does Appellant argue there was anything
unexpected about using the claimed ketone in the process taught in Bonrath
or that there are any other secondary considerations to be evaluated.
Because Organon demonstrates ketones within the scope of the genus
recited in Appellant’s claim 1 were known to those of ordinary skill in the
art and Appellant fails to direct us to evidence why one would not have
considered using these ketones in the claimed process, we are not persuaded
the Examiner erred in rejecting Appellant’s claims as being obvious.
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Application 15/518,080

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Conclusion
Upon consideration of the record and for the reasons given, we affirm
the Examiner’s rejection.
In summary:
Claim(s)
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
1, 3–11 103 Bonrath, Organon 1, 3–11

No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136.

AFFIRMED