Ex parte Neumann

Board of Patent Appeals and Interferences

Mar 29, 2001

08493571 (B.P.A.I. Mar. 29, 2001)

The opinion in support of the decision being entered today was not
written for publication and is not binding precedent of the Board

Paper No. 22

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
_____________

Ex parte UWE NEUMANN

_____________

Appeal No. 1998-0472
Application No. 08/493,571
_____________

HEARD: February 21, 2001
_____________

Before GARRIS, TIMM and PAWLIKOWSKI, Administrative Patent
Judges.

PAWLIKOWSKI, Administrative Patent Judge.

Decision on Appeal

This is a decision on appeal from the final rejection
of claims 1-12 and 19-21. Claim 13 has been withdrawn from
consideration.

The subject matter on appeal relates to a process for
the preparation of an alkylated or aralkylated polyhydroxy
compound. This compound is prepared by reacting (A) a
polyhydroxy aromatic compound with (B) an alkene or aralkene
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Application No. 08/493,571

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compound in the presence of a (C) a mixture of oxalic acid
and boric acid in a molar ratio of 1:5 to 1:0.1, at a
temperature above room temperature. Further details of this
appealed subject matter are set forth in claim 1 which reads
as follows:

1. A process for the preparation of an alkylated
or aralkylated polyhydroxy aromatic compound comprising
reacting a polyhydroxy aromatic compound (A) with an
alkene or aralkene compound (B) at a temperature above
room temperature in the presence of a mixture (C) of
oxalic acid and boric acid in a molar ratio of oxalic
acid to boric acid of from 1:5 to 1:0.1.

The references relied upon by the examiner are as
follows:
Rothrock 2,079,633 May 11, 1937
Gobran 4,039,724 Aug. 2, 1977
Oppenlaender et al. 4,189,445 Feb. 19, 1980
(Oppenlaender)
McAllister et al. 4,275,170 Jun. 23, 1981
(McAllister)
Hoggins et al. 4,359,438 Nov. 16, 1982
(Hoggins)
Nelson 4,390,680 Jun. 28, 1983
Durairaj 5,300,618 Apr. 5, 1994

German Patent 1,543,512 Jul. 31, 1969
(Dorogomilovsky Khimicheskiiy zavod im. Frunze, Moscow)

We note that the Japanese reference 59-65034 has been
withdrawn from use as a reference against appellant’s claims
because the examiner did not list or mention it in his
Answer.

Claims 1-12 and 21 are rejected under 35 U.S.C. § 103
as being unpatentable over German Patent Nos. 1,543,512 and
2,330,850, Oppenlaender, Nelson, and Durairaj in view of
Appeal No. 1998-0472
Application No. 08/493,571

3
Hoggins, McAllister, and Rothrock. We note that with
respect to German Patent No. 2,330,850, the examiner has
issued a new ground of rejection because this is a newly
cited reference. (Answer, page 4).

Claims 19 and 20 are rejected under 35 U.S.C. § 103 as
being unpatentable over German Patent Nos. 1,543,512 and
2,330,850, Oppenlaender, Nelson, and Durairaj in view of
Hoggins, McAllister, and Rothrock, and further in view of
Gobran. We note that with respect to German Patent
No. 2,330,850, the examiner has issued a new ground of
rejection because this is a newly cited reference. (Answer,
page 4).
Opinion
For the reasons set forth below, we will reverse each
of the above noted rejections.

The pivotal consideration for each of the examiner's
§ 103 rejections concerns the limitation found in claim 1 of
preparing an alkylated or aralkylated polyhydroxy aromatic
compound in the presence of a mixture of oxalic acid and
boric acid.

Appellant argues that the primary references of German
Patent No. 1,543,512, Oppenlaender, Nelson, and Durairaj do
not disclose a mixture of oxalic acid and boric acid.
(Brief, pages 4-7). Appellant also argues that German
Patent No. 2,330,850 also does not teach a mixture of oxalic
acid and boric acid. (Reply Brief, page 2). The examiner
admits that these primary references do not disclose a
mixture of oxalic acid and boric acid in a molar ratio of
Appeal No. 1998-0472
Application No. 08/493,571

4
from 1:5 to 1:0.1. (Answer, page 5).

The examiner relies upon Nelson for teaching the use of
a mixture of acid catalysts in an alkylation process,
including Lewis acids (boric acid is a Lewis acid). (Answer,
pages 6 and 8).

Appellant argues that a mixture of oxalic acid and
boric acid is not specifically disclosed in Nelson. (Brief,
page 6, Reply Brief, page 2). Upon our review of Nelson, we
find that Nelson discloses "[s]uitable acid catalysts which
can be employed herein include, for example, Lewis Acids,
alkyl, aryl and aralkyl sulfonic acids and disulfonic acids
or diphenyloxide and alkylated diphenyloxide, sulfuric acid,
mixtures thereof and the like" (col. 3, lines 31-35).
Hence, we agree with appellant that a mixture of oxalic acid
and boric acid is not specifically disclosed in Nelson.
Nelson simply suggests that a mixture of suitable acid
catalysts can be used.

The examiner then relies upon Hoggins for teaching the
alkylation of phenol with styrene "using the same or
different acid catalyst as used for the reaction of phenol
with formaldehyde". Such an acid catalyst can be oxalic
acid. (Answer, page 6). Appellant rightly argues that
Hoggins does not teach use of a mixture of oxalic acid and
boric acid.

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The examiner next relies upon McAllister for teaching
the reaction of phenol with formaldehyde in the presence of
a Lewis acid, such as boric acid. In the same manner, the
examiner relies upon Rothrock for teaching the use of boric
acid in a reaction of phenol with formaldehyde. (Answer,
page 6). The examiner concludes that it would have been
obvious to conduct an aralkylation of a polyhydroxy aromatic
phenol with the oxalic acid of the German patents,
Oppenlaender, Nelson, and Durairaj, in combination with the
boric acid of McAllister and Rothrock.

Appellant argues that McAllister is directed to a
condensation reaction rather than an addition product as in
the present invention. Appellant also argues that
McAllister is concerned with polyhydric phenols and Hoggins
is concerned with phenols, and therefore no logical nexus
exists between these 2 references. (Brief, page 8). The
examiner rebuts and states that McAllister and Rothrock
disclose the reaction of polyhydric phenols and phenols, and
that therefore, boric acid catalyzes the reaction regardless
of the quantitative phenolic functionality. The examiner
also states that he has relied upon Hoggins for establishing
equivalency of boric acid to catalyze either phenol-
formaldehye reactions or arylkalation reactions, and that
therefore it is a matter of ordinary skill in the art to
employ the boric acid of McAllister and Rothrock together
with the oxalic acid of the German patents, Oppenlaender,
Nelson, and Durairaj, in view of the teaching of Nelson that
mixtures of acid catalysts are suitable in alkylation
reactions. (Answer, page 11).

Appeal No. 1998-0472
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We must agree with the examiner that McAllister and
Rothrock do establish that boric acid can catalyze phenols,
whether polyhydric or not polyhydric. However, we note that
this is in the context of a reaction between phenol with
formaldehyde, not in the context of a reaction between a
polyhydroxy aromatic compound with an alkene or aryalkene,
as recited in appellant's claim 1.

Also, although the examiner attempts to establish an
equivalency between acid catalysts used for phenol-
formaldehyde reactions and acid catalysts used for the
reaction concerning alkylation of phenol, based upon the
disclosure of Hoggins, we note that Hoggins is in the
context of phenol only, not a polyhydroxy aromatic compound.

Furthermore, we question the examiner's reasons to
combine the teachings of McAllister and Rothrock with the
primary references. The examiner states that it would have
been obvious to combine oxalic acid with boric acid in order
to achieve improvements from the use of boric acid, such as
enhanced fire retardancy, reduced combustion gases,
oxidation protection as taught in McAllister, and oil
solubility as taught in Rothrock. (Answer, pages 6-7).
However, we again note that these improvements taught in
McAllister and Rothrock are in the context of a resultant
polymer resin of a phenol-formaldehyde type reaction. It is
difficult to know whether such improvements would be
obtained for polymers resulting from a polyhydric phenol-
alkene/aralkene type reaction as claimed in appellant's
claim 1, and the examiner has not explained why one skilled
in the art would reasonably believe that the same results
Appeal No. 1998-0472
Application No. 08/493,571

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would be obtained or whether one skilled in the art would
have expected to achieve the same results or additive
results. Listing several compounds as interchangeable for
one purpose will not establish their equivalency for all
purposes, In re Jezl, 396 F.2d 1009, 1012, 158 USPQ 98, 100
(CCPA 1968). Moreover, appellant’s invention is concerned
with modification of polyhydric aromatic compounds in such a
way that the solubility in aromatic solvents of the
polycondensation products prepared therefrom is improved.
(specification, page 3, lines 14-16).

We note that “[o]bviouness cannot be established by
combining the teachings of the prior art to produce the
claimed invention, absent some teaching, suggestion or
incentive supporting the combination.” In re Geiger, 815
F.2d 686, 688, 2 USPQ2d 1276, 1278 (Fed. Cir. 1987). Here,
absent hindsight, the skilled artisan would not have found
it obvious to conduct appellant’s claimed reaction in the
presence of both oxalic acid and boric acid for the reasons
discussed above. Combining the two acids may have been
obvious to try, but this does not constitute the standard
for combining references under § 103. Id. at In re Geiger
815 F.2d at 687, 2 USPQ at 1278; cf. In re Wesslau, 353 F.2d
238, 241, 147 USPQ 391, 393 (CCPA 1965).

Hence, we reverse the rejection of claims 1-12 and 21
under 35 U.S.C. § 103 as being unpatentable over German
Patent Nos. 1,543,512 and 2,330,850, Oppenlaender, Nelson,
and Durairaj in view of Hoggins, McAllister, and Rothrock.
We also reverse the rejection of claims 19 and 20 under
35 U.S.C. § 103 as being unpatentable over German Patent
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Nos. 1,543,512 and 2,330,850, Oppenlaender, Nelson, and
Durairaj in view of Hoggins, McAllister, and Rothrock, and
further in view of Gobran.

REVERSED

BRADLEY R. GARRIS )
Administrative Patent Judge )
)
)
) BOARD OF PATENT
CATHERINE TIMM ) APPEALS AND
Administrative Patent Judge ) INTERFERENCES
)
)
)
BEVERLY A. PAWLIKOWSKI )
Administrative Patent Judge )

BAP/sld
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