Ex Parte Gessner et al

Board of Patent Appeals and Interferences

Sep 22, 2010

10584631 (B.P.A.I. Sep. 22, 2010)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte THOMAS GESSNER and SOPHIA EBERT
__________

Appeal 2010-007368
Application 10/584,631
Technology Center 1600
__________

Before DONALD E. ADAMS, LORA M. GREEN, and
STEPHEN WALSH, Administrative Patent Judges.

WALSH, Administrative Patent Judge.

DECISION ON APPEAL1
This is an appeal under 35 U.S.C. § 134(a) involving claims to a
process for preparing metal-free phthalocyanine. The Patent Examiner

1 The two-month time period for filing an appeal or commencing a civil
action, as recited in 37 C.F.R. § 1.304, or for filing a request for rehearing,
as recited in 37 C.F.R. § 41.52, begins to run from the “MAIL DATE”
(paper delivery mode) or the “NOTIFICATION DATE” (electronic delivery
mode) shown on the PTOL-90A cover letter attached to this decision.

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rejected the claims as obvious. We have jurisdiction under 35 U.S.C. § 6(b).
We affirm.

STATEMENT OF THE CASE
The invention concerns a process of converting an ortho-
phtalodinitrile to a metal-free phthalocyanine in the presence of an alkali
metal hydroxide. (Spec. p. 1, ll. 5-24).
Claims 1-9 and 11-17 are on appeal.2 Claim 1 is representative and
reads as follows:
1. A process for the preparation of a metal-free phthalocyanine of
formula I

the process comprising,
converting an ortho-phthalodinitrile of formula Ia

to the metal-free phthalocyanine of formula I in an inert solvent with a
boiling point of at least 120°C (at standard pressure) in the presence of
ammonia and an alkali metal hydroxide,
wherein, in formula I or Ia, the variable n can adopt values of 1, 2, 3
or 4,
wherein in formula I or Ia, the R radicals denote a five- or six-
membered saturated heterocyclic ring comprising nitrogen,

2 We note from the Examiner’s Answer that claim 10 is pending but does not
appear to be subject to a ground of rejection. (See Ans. 12-13).
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wherein the five- or six-membered saturated heterocyclic ring
comprising nitrogen is bonded via a ring nitrogen atom to the benzene ring,
wherein the five- or six-membered saturated heterocyclic ring
comprising nitrogen can, optionally, comprise one or two additional nitrogen
atoms or an additional oxygen or sulfur atom, and
wherein the five- or six-membered saturated heterocyclic ring
comprising nitrogen can be, optionally, substituted by one or two C1-C8-
alkyl groups.

The Examiner rejected the claims as follows:
• claims 1-8 and 11-17 under 35 U.S.C. § 103(a) as unpatentable over
Branch3 and Tamura,4 and Paidi;5 and
• claims 8 and 9 under 35 U.S.C. § 103(a) as unpatentable over
Branch, Tamura, Paidi, and Rintelman.6
Claims 2-9 and 11-17 have not been argued separately and therefore
stand or fall with claim 1. 37 C.F.R. § 41.37(c)(1)(vii).

OBVIOUSNESS
The Issue
The Examiner’s position is Brach disclosed “a similar process to that
of the claimed invention for preparing unsubstituted or substituted metal-free
phthalocyanines.” (Ans. 5). The Examiner found that Brach taught that

3 Paul J. Brach et al., Improved Synthesis of Metal-free Phthalocyanines,
7 HETEROCYCLIC CHEM., 1403-1405 (1970).
4 Patent Application Publication No. EP 0663427 A3 by Shinichi Tamura et
al., published Jul. 19, 1995.
5 Patent Application Publication No. JP 2003040892 A by Paidi et al.,
published Feb. 13, 2003.
6 US Patent No. 2,485,168 issued to William L. Rintelman, Oct. 18, 1949.

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metal-free phthalocyanines are prepared by heating a phthalodinitrile and
ammonia in an inert organic solvent with a boiling point of at least 120° C.
(Id.). However, the Examiner found that Brach did not disclose
incorporating an alkali metal hydroxide in its process. (Id.).
The Examiner found that Tamura disclosed a method of synthesizing
high purity metal-free phthalocyanines wherein partially hydrogenated alkali
metal phthalocyanines are obtained by heating a phthalodinitrile in an inert
organic solvent in the presence of amines such as ammonia and an alkali
metal source such as sodium or potassium hydroxide. (Id.). The Examiner
also found that Tamura disclosed that the phthalocyanines are subsequently
contacted with a hydrogen-substituting agent such as methanol or water to
provide the metal-free compound. (Id.). Additionally, the Examiner found
that Tamura taught that “if the reaction was carried out under conditions
wherein the phthalocyanine was partially metallated (due to the presence of
the alkali metal), a rapid equilibrium existed which resulted in the
dissolution of unwanted impurities; affording high purity phthalocyanines.”
(Id. at 6). The Examiner also found that Tamura disclosed ultimately
obtaining a high yield of the metal-free phthalocyanines, e.g., >90%. (Id.).
The Examiner found that Paidi taught the preparation of ruthenium
phthalocyanines containing 6-membered heterocycles. (Non-Final Rej. 4).
Based upon these disclosures, the Examiner determined that a person
of ordinary skill in the art at the time the invention was made would have
found it obvious and would have been motivated to modify Brach’s process
by introducing an alkali metal hydroxide into the process with a reasonable
expectation of successfully achieving an improved process for the synthesis
of high purity unsubstituted or substituted phthalocyanines. (Ans. 6). The
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Examiner relied upon Paidi to evidence that attachment of a 5 or 6
membered saturated heterocycle to a phthalocyanine ring was known at the
time of the invention. (Non-Final Rej. 6).
Appellants challenge the Examiner’s combination of Brach and
Tamura by asserting that (a) there is no motivation to combine the
references, (b) Tamura taught away from the combination, and (c) the
Examiner relied upon impermissible hindsight in combining the references.
(App. Br. 5). Specifically, Appellants argue that Tamura’s “dealkalizing
agent [] is a necessary component in the process of Tamura and thus, may
not be dispensed with in order to obtain Tamura’s et al.’s metal free
phthalocyanine.” (App. Br. 6). According to Appellants, if Tamura is
combined with Brach, then “all required elements of Tamura et al. must be
combined with Brach et al., as opposed to merely selecting individual
components such as Tamura’s et al.’s [alkali metal component].” (Id.).
Appellants assert that this deficiency is not cured by Paidi or
Rintelman. (Id.) Further, Appellants assert that combining Tamura and
Paidi “is problematic” because Paidi is concerned with metal, i.e.,
ruthenium, phthalocyanines while Tamura is concerned with metal-free
phthalocyanines. (Id. at 7). According to Appellants, “it is well known to a
person of ordinary skill in the art that the synthesis of metal-free
phthalocyanine[e]s is often different from the synthesis of metal containing
phthalocyanin[e]s.” (Id.).
The issue with respect to this rejection is whether the record supports
the Examiner’s conclusion that the cited references would have made the
claimed process obvious.

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Findings of Fact
1. We agree with the Examiner’s explicit findings regarding the scope
and content of the prior art references. (See Ans. 3-7; Non-Fin. Rej. 3-7).

Principles of Law
“The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results.”
KSR Int’l. Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007).

Analysis
We are not persuaded by Appellants’ contention that the combination
of Brach and Tamura was improper as the basis for this contention is not
supported by the record. Appellants challenge the Examiner’s combination
by asserting that it fails to include Tamura’s use of a dealkalizing agent.
(See App. Br. 6). However, as the Examiner explained (see Ans. 7) the
combination does include this step, which both Brach and Tamura disclosed.
Appellants do not dispute that Brach disclosed using a dealkalizing agent.
Therefore, we do not find that Appellants have established that the
combination of Brach and Tamura was improper. We find the Examiner’s
reasoning was in compliance with obviousness precedent. See KSR,
550 U.S. at 416.
Further, to the extent that Appellants challenge the inclusion of Paidi
in the combination, we are unpersuaded. The Examiner’s combination did
not include any processing step disclosed in Paidi. (See Fin. Rej. 6). Rather,
the Examiner relied upon Paidi merely to evidence that attaching a 5 or 6
membered saturated heterocycle to a phthalocyanine ring was known in the
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art at the time of the invention. (Id.). Therefore, we find that Appellants’
assertion that the “synthesis” of metal-free phthalocyanines is “often
different” from the synthesis of metal phthalocyanine (App. Br. 7) is
misdirected.
Accordingly, we affirm the Examiner’s obviousness rejections.

CONCLUSION OF LAW
The record supports the Examiner’s conclusion that the cited
references would have made the claimed process obvious.

SUMMARY
We affirm the rejection of claims 1-8 and 11-17 under 35 U.S.C.
§ 103(a) as unpatentable over Branch, Tamura, and Paidi; and
we affirm the rejection of claims 8 and 9 under 35 U.S.C. § 103(a) as
unpatentable over Branch, Tamura, Paidi, and Rintelman.

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

AFFIRMED

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