Ex Parte Nefzger et al

Patent Trial and Appeal Board

May 3, 2016

13322989 (P.T.A.B. May. 3, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
13/322,989 01/20/2012
157 7590 05/05/2016
Covestro LLC
1 Covestro Circle
PITTSBURGH, PA 15205
FIRST NAMED INVENTOR
Hartmut Nefzger
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.
BMS091109 8373
EXAMINER
W ASHVILLE, JEFFREY D
ART UNIT PAPER NUMBER
1766
NOTIFICATION DATE DELIVERY MODE
05/05/2016 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):
veronica. thompson@covestro.com
US-IPR@covestro.com
laura.finnell@covestro.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte HARTMUT NEFZGER, ERIKA BAUER,
JOHANNES VAN DE BRAAK, JURGEN
SCHLOSSMACHER, and SIL VIA KASPEREK 1
Appeal2014-008066
Application 13/322,989
Technology Center 1700
Before TERRY J. OWENS, CHRISTOPHER C. KENNEDY, and DEBRA
L. DENNETT, Administrative Patent Judges.
DENNETT, Administrative Patent Judge.
DECISION ON APPEAL
STATEMENT OF THE CASE
Appellants appeal under 35 U.S.C. § 134 from a rejection of claims 1-
11, 13, and 14. We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.
1 According to Appellants, the real party in interest is Bayer Intellectual
Property GmbH. Appeal Brief (App. Br.) 1.
Appeal2014-008066
Application 13/322,989
The Invention
The claims are directed to a process for producing polyester polyols.
Claim 1, reproduced below, is exemplary of the claimed subject matter:
1. A process for producing a polyester polyol with a
concentration of ether groups in the range of between 9.0
mol/kg polyester polyol and 22 mol/kg polyester polyol,
compnsmg
(i) reacting in a first step
(A) a component selected from the group consisting of
isophthalic acid, a C1-C4 alkyl ester of isophthalic acid,
terephthalic acid, and a C1-C4 alkyl ester of terephthalic acid,
with
(B) an oligoethylene glycol of the formula
H-(OCH2CH2)nOH in which the number-average number of
oxyethylene groups n is in the range of between 3.0 and 9.0 in
the presence of at least one catalyst selected from the group
consisting of tin(ll) salts, bismuth(ll) salts and titanium
tetraalkoxvlates at a temnerature in the ram!e of between 160°C
~ ~ .__,
and 240°C and a pressure in the range of between 1 and 1013
mbar for a period in the range of between 7 and 100 hours, and
(ii) reacting in a second step the reaction mixture resulting from
step (i) with
(C) phthalic acid and/or phthalic anhydride.
Appeal Brief 12 (Claims App'x). The claims as provided in Appellants'
Claims Appendix accurately state the pending claims.
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Application 13/322,989
Londrigan
The References
us 4,753,967
The Rejections
June 28, 1988
Claims 1-11, 13, and 14 stand rejected under 35 U.S.C §103(a) as
being unpatentable over Londrigan.
OPINION
We affirm the rejection under 35 U.S.C. §103(a). We need address
only the sole independent claim 1, as Appellants have not argued for
separate patentability of other claims.
Londrigan teaches reacting a polycarboxylic acid component with a
polyol component which consists solely or partially of at least one
oxyalkylated polyol having at least one primary and at least one secondary
hydroxyl group in the same molecule. Londrigan 2:51-57 (emphasis
added).
Polycarboxylic acid components specifically taught in Londrigan
include isophthalic acid and terephthalic acid (id. at 5:11-17). Both of these
molecules are identified as members of the Markush group in step (i)(A) of
claim 1 of Appellants' application. App. Br. 12 (Claims App'x).
The polyol component in Londrigan is designated a "compatibilizing
polyol mixture" and is formed by:
an oxyalkylation reaction wherein one or more alkylene oxides
are reacted with an organic active hydrogen initiator(s), the
alkylene oxide( s) and initiator( s) and amounts thereof being
chosen so that, when these ingredients are reacted together, they
form polyol molecules having both primary and secondary
hydroxyl groups. The reaction typically yields the latter
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Appeal2014-008066
Application 13/322,989
molecules as well as polyol molecules having only primary
hydroxyl groups and others having only secondary hydroxyl
groups.
Id. at 2:61-3:3. Further according to Londrigan, the compatibilizing polyol
mixture is generally used in toto in preparing the polyester polyols. Id. at
3 :3---6. The alkylene oxides disclosed in Londrigan include ethylene oxide,
propylene oxide, butylene oxide, amylene oxide, and mixture of them. Id. at
3:67--4:3. The initiators used in preparing the compatibilizing polyol
mixtures are compounds capable of initiating the polymerization of an
alkylene oxide; preferred initiators are stated as including glycols such as
ethylene glycol and propylene glycol, and oxyalkylene glycols such as
diethylene glycol and dipropylene glycol and higher oxyalkylene glycols.
Id. 3: 18-21, 62---66. Londrigan teaches that the equivalent ratio of alkylene
oxide to active hydrogen-containing initiator is preferably about 0.2: 1 to 1.5:
1, more preferably about 0.5: 1 to 1.2: 1, and most preferably about 0.9: 1 to
1.1: 1. Id. 4:34--38.
The Examiner found that synthesizing the teachings of Londrigan by
using ethylene oxide as an alkylene oxide and diethylene glycol as an
initiator at a ratio of alkylene oxide:hydrogen initiator of a range of 0.2: 1 to
1.5: 1 for n=3--4, would produce a polyol mixture that substantially overlaps
the oligoethylene glycol of the formula where n = 3-9 oxyethylene groups,
which is element (i) (B) of claim 1. Ans. 2. Appellants do not dispute the
Examiner's finding, but contend that "the Londrigan reference clearly
requires the compatibilizing polyols to include secondary OH groups," and
therefore "one would not react diethylene glycol solely with ethylene oxide"
because products with only primary OH groups would result. App. Br. 5.
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Appeal2014-008066
Application 13/322,989
However, Londrigan teaches that mixtures of alkylene oxides may be
used. Londrigan 4: 19--24. Moreover, Londrigan teaches an especially
preferred compatibilizing polyol mixture is formed in a known manner by
reacting a glycol containing two primary hydroxyl groups (e.g., ethylene
glycol and/or diethylene glycol) with propylene oxide. Id. 4:39--44. The
resultant compatibilizing glycol mixture then has a composition consisting
of (a) about 5 to 70%, preferably about 8 to 50%, by weight, of primary OH
group-containing glycol. Id. 4:51-55. This meets the limitations of the
oligoethylene glycol in step (i)(B) of claim 1.
Appellants argue that the compatibilizing pol yo ls of Londrigan always
have a mixture of primary and secondary OH groups. Reply Br. 4. If
Appellants contend that the compatibilizing pol yo ls of Londrigan always
have both primary and secondary OH groups on each molecule, they are
incorrect; Londrigan teaches that the reaction of one or more alkylene oxides
with organic active hydrogen initiators yields, inter alia, polyol molecules
having only primary hydroxyl groups. Londrigan 2:61-3:3. If, on the other
hand, Appellants contend that the compatibilizing polyols of Londrigan
always have a mixture of pol yo ls, some of which have primary OH groups,
some of which have secondary OH groups, and some of which have both
primary and secondary OH groups, it does not aid their case, because claim
1 does not exclude the presence of pol yo ls with secondary OH groups, it
merely requires the presence of pol yo ls with primary OH groups.
As the Examiner pointed out, Appellants' argument that the
oligoethylene glycol of claim 1 (having the formula H-(OCH2CH2)nOH in
which the number-average number of oxyethylene groups n is in the range
of between 3.0 and 9.0) requires "only primary OH groups" is wrong based
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Appeal2014-008066
Application 13/322,989
on the "comprising" language in the claim. While the claimed process for
polyester polyols requires primary OH groups present in the oligoethylene
glycol, it does not prohibit the presence of molecules with secondary OH
groups, such as those taught by Londrigan.
The Examiner found that Londrigan also taught the other limitations
in step (i)(B) of claim 1, specifically the catalyst, the temperature of the
reaction, the pressure at which the reaction takes place, and the duration of
the reaction. Ans. 3. Appellants have not disputed these findings.
The polyester polyols useful in Londrigan can be prepared by known
procedures from a polycarboxylic acid or acid derivative, such as an
anhydride or ester of the polycarboxylic acid, and a mixture of polyols
containing the compatibilizing polyol(s). Londrigan 4:67-5:3. With respect
to step 2 of claim 1 ((ii) reacting in a second step the reaction mixture
resulting from step (i) with (C) phthalic acid and/or phthalic anhydride),
Londrigan teaches that, while the polyester polyols can be prepared from
substantially pure reactant materials, more complex ingredients are
advantageously used, such as side-stream, waste or scrap residue from the
manufacture of phthalic acid. Id. 6:23-27. Polyester polyols derived from
raw materials containing compounds having the above defined phthalic acid
residues constitute a preferred embodiment of the invention. Id. 6:36-39.
Modifying Londrigan to employ pure phthalic acid and/or phthalic
anhydride in the final step is well within the ability of one of ordinary skill
in the art, and would produce polyester polyols with lower viscosities.
Appellants attempt to distinguish the teachings of Londrigan from
their claims by asserting that the polyester polyols resulting from the
claimed process unexpectedly have substantially lower viscosity. App. Br.
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Application 13/322,989
5---6; Reply Br 9. As evidence, Appellants compare the viscosity of
Polyester Polyol C in Table III ofLondrigan with Examples A-1 through A-
4 in Appellants' Specification. App. Br. 7. Appellants argue that Polyester
Polyol C of Londrigan has a higher hydroxyl number, thus a lower
molecular weight, and that generally means a lower viscosity. Polyester
Polyol C has a viscosity of 20,600, which is substantially higher than the
viscosities of Examples A-1 through A-4 of Appellants' Specification.
App. Br. 7-8. However, as Appellants point out, Polyester Polyol C a
"clearly a comparison example to the invention of the Londrigan reference
as the specified polyol was not used on Polyester Polyol C." Id. 7.
Therefore, one can draw no conclusions about viscosities of the process
taught by Londrigan from this comparison.
Londrigan teaches that lower viscosities are desirable. Londrigan
2:11-12, 4:31, 10:1. "The properties of the polyesterpolyol mixtures of the
present invention fall within rather broad ranges. The viscosities
(Brookfield) of the polyol mixtures measured in cps. at 25° C fall with in
rather broad range from about 500 to about 500,000." Id. 9: 13-17. The
range disclosed in Appellants' Specification is 400 mPas to 10,000 mPas at
25° C. Spec. 6. The ranges in Londrigan significantly overlap those
disclosed by Appellants. Appellants have not shown that their results are
"unexpected."
Moreover, Appellants have provided viscosity data for only four
examples, yet the claims cover hundreds of potential polyester polyols
produced by the claimed process. Where Appellants are relying on
unexpected results to rebut a prima facie case of obviousness, Appellants
must show results that are commensurate in scope with the claims. See In re
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Application 13/322,989
Peterson, 315 F.3d 1325, 1329--31 (Fed. Cir. 2003). Appellants have not
attempted to do that. Thus, Appellants have neither explained why data
from only four examples covers the scope of the claims sought nor have
explained why the results are unexpected.
Appellants argue that the Examiner erred in stating "Londrigan ...
teaches each and every element of claim 1." Reply Br. 3 (citing Ans. 3). In
part, § 103(a) states:
A patent may not be obtained though the invention is not
identically disclosed or described as set forth in section 102 of
this title, if the differences between the subject matter sought to
be patented and the prior art are such that the subject matter as a
whole would have been obvious at the time the invention was
made to a person having ordinary skill in the art to which said
subject matter pertains.
Section 103 merely references "the prior art" rather than "plural
prior art references." Thus,§ 103 authorizes a rejection where to
meet the claim, it is necessary to modify a single reference or to
combine it with one or more others.
Modifying Londrigan to employ pure phthalic acid and/or phthalic
anhydride in the final step is well within the ability of one of ordinary skill
in the art, and should produce polyester polyols with lower viscosities, as it
would then follow each step of Appellants' claim 1.
On this record, Appellants have not identified reversible error in the
Examiner's findings.
DECISION/ORDER
For the above reasons, the Examiner's rejection of claims 1-11, 13,
and 14 is AFFIRMED.
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Appeal2014-008066
Application 13/322,989
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a) (1) (iv) (2009).
AFFIRMED
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