Ex Parte Watanabe et al

Patent Trial and Appeal Board

Dec 10, 2014

13081353 (P.T.A.B. Dec. 10, 2014)

UNITED STATES PATENT AND TRADEMARKOFFICE
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.
13/081,353 04/06/2011 Masafumi WATANABE 396.45067CX1 3759
20457 7590 12/10/2014
ANTONELLI, TERRY, STOUT & KRAUS, LLP
1300 NORTH SEVENTEENTH STREET
SUITE 550
ARLINGTON, VA 22209-3873
EXAMINER
O DELL, DAVID K
ART UNIT PAPER NUMBER
1625
MAIL DATE DELIVERY MODE
12/10/2014 PAPER
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.
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte MASAFUMI WATANABE, JUNICHI AMEMIYA,
IKUTARO KUZUHARA
__________

Appeal 2012-011503
Application 13/081,353
Technology Center 1600
__________

Before DONALD E ADAMS, DEMETRA J. MILLS, and
CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.

MILLS, Administrative Patent Judge.

DECISION ON APPEAL

This is an appeal under 35 U.S.C. § 134. The Examiner has rejected
the claims for obviousness. We have jurisdiction under 35 U.S.C. § 6(b).
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STATEMENT OF CASE
According to the Specification, “Spiroglycol is produced, for example,
through the steps of conducting an acetalization reaction of
hydroxypivalaldehyde (… ‘HPA’) and pentaerythritol … in water in the
presence of an acid catalyst, neutralizing with alkali, removing spiroglycol
crystals precipitated during the reaction by filtration, washing with water and
drying (JP 59-148776A).” (Spec. 1).
Since the acetalization reaction is generally an equilibrium reaction
under acidic conditions, the produced SPG undergoes decomposition reaction
(reverse reaction). To avoid the decomposition of SPG, the acetalization
reaction has been conducted in a solvent having a low dissolving power to
SPG so as to allow the produced SPG to rapidly crystallize, thereby shifting
the equilibrium to the product side. (Id.)

The following claim is representative.
1. A process for producing 3,9-bis(1,1-dimethyl-2-hydroxyethyl)-2,4,8,
10- tetraoxypivalaldehyde [5.5] undecane (spiroglycol), comprising reacting
pentaerythritol and hydroxypivalaldehyde in water in the presence of an acid
catalyst, wherein:
(A) a total content of amines and amine salts in the
hydroxypivalaldehyde is reduced to 0.31% by weight or lower;
(B) seed crystals are added to a reaction system before initiating the
reaction and/or during the reaction in an amount from 1.5 to 30% by
weight on the basis of a total amount of pentaerythritol,
hydroxypivalaldehyde, water, the acid catalyst and the seed crystals, each
being fed into the reaction system;
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(C) a pH of the reaction system is kept from 0.1 to 4.0 from initiation
of the reaction to completion of the reaction; and
(D) a sum of a maximum theoretical amount of spiroglycol to be
synthesized from pentaerythritol and hydroxypivalaldehyde to be fed
into the reaction system and an amount of spiroglycol contained in the seed
crystals to be added to the reaction system is controlled within a range from 5
to 35% by weight on the basis of the total amount of pentaerythritol,
hydroxypivalaldehyde, water, the acid catalyst and the seed crystals, each
being fed into the reaction system.

Cited References

Ruskin US 2,853,495 Sept. 23, 1958
Mantell US 3,092,640 June 4, 1963
Iyama US 5,698,717A Dec. 16, 1997
Honda JP 07-215980 Aug. 15, 1995
Shu Yoshida JP 2000-044569 Feb. 15, 2000
Nuno and Tanaka JP 2001055388A Feb. 27, 2001

Kubota et al., Seeding Effect on Product Crystal Size in Batch
Crystallization, J. OF CHEMICAL ENGINEERING OF JAPAN, 35 (11),
1063-1071 (2002).

P.N. Sharratt, Handbook of Batch Process Design, CHAPMAN
AND HALL, 295-296 (1997).

Van Zyl et al., Synthesis of a Series of Derivatives of Ethyl 2-
Pyridylacetate, JOURNAL OF ORGANIC CHEMISTRY, 26, 3373-
3375 (1961).
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Grounds of Rejection
Claims 1–12 are rejected under 35 U.S.C. § 103(a) as being
unpatentable over Mantell, Yoshida Shu (machine translation), Iyama,
Kubota, Nuno and Tanaka (machine translation)), Honda (machine
translation), and Sharratt, Ruskin and Van Zyl.

FINDINGS OF FACT
The Examiner’s findings of fact are set forth in the Answer at pages
5–12.

Discussion
ISSUE
The issue is: Does the cited prior art support the Examiner’s finding
that the claimed subject matter is obvious? Does the cited prior art disclose
claim 1, step (A), wherein “a total content of amines and amine salts in the
hydroxypivalaldehyde is reduced to 0.31% by weight or lower” (in other
words, an active process step of reducing the total content of amines and
amine salts in the hydroxypivalaldehyde to 0.31% by weight or lower)?

PRINCIPLES OF LAW
In making our determination, we apply the preponderance of the
evidence standard. See, e.g., Ethicon, Inc. v. Quigg, 849 F.2d 1422, 1427
(Fed. Cir. 1988) (explaining the general evidentiary standard for proceedings
before the Office). The Board “determines the scope of claims in patent
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applications not solely on the basis of the claim language, but upon giving
claims their broadest reasonable construction ‘in light of the specification as
it would be interpreted by one of ordinary skill in the art.’” Phillips v. AWH
Corp., 415 F.3d 1303, 1316 (Fed. Cir. 2005) (quoting In re Am. Acad. of Sci.
Tech. Ctr., 367 F.3d 1359, 1364 (Fed. Cir. 2004).
“In rejecting claims under 35 U.S.C. § 103, the examiner bears the
initial burden of presenting a prima facie case of obviousness. Only if that
burden is met, does the burden of coming forward with evidence or
argument shift to the applicant.” In re Rijckaert, 9 F.3d 1531, 1532 (Fed.
Cir. 1993) (citations omitted). In order to determine whether a prima facie
case of obviousness has been established, we consider the factors set forth in
Graham v. John Deere Co., 383 U.S. 1, 17 (1966): (1) the scope and content
of the prior art; (2) the differences between the prior art and the claims at
issue; (3) the level of ordinary skill in the relevant art; and (4) objective
evidence of nonobviousness, if present.
“[O]bviousness requires a suggestion of all limitations in a claim.”
CFMT, Inc. v. Yieldup Intern. Corp., 349 F.3d 1333, 1342 (Fed. Cir. 2003)
(citing In re Royka, 490 F.2d 981, 985 (CCPA 1974)).

ANALYSIS
We do not find that the Examiner has provided evidence to support a
prima facie case of obviousness of the claimed process.
The Examiner argues that, “With respect to ‘Step (A)’ the reference to
the amount of amines is shown by Mantell and Shu as their materials have
no amines thus meet the limitation of less than 0.31%.” (Ans. 10.)
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Appellants argue, among other things,
An important feature of the present invention is that (A) a
total content of amines and amine salts in the hydroxypival-
aldehyde is reduced to 0.31% by weight or lower. It is
emphasized that the present claims recite a reduction of the
amines and amine salts in the hydroxypivalaldehyde, to a level
of 0.31% by weight or lower. Where the total content of
amines and amine salts is more than 0.31% by weight, the
amount of the acid catalyst required for the synthesis of the
spiroglycol increases, the purity of the spiroglycol is reduced
(because of the salting-out effect), and particle size of the
spiroglycol crystals becomes small.

(Br. 11–12.) Appellants contend that

even if Mantell, et al. were interpreted as having no amines,
then there would be no need to reduce a total content of amines
and amine salts in the hydroxypivalaldehyde to 0.31% by
weight or lower. There is simply no basis in the teachings of the
applied references, including Mantell, et al. and Shu, et al.,
disclosing or suggesting the feature (A) of claim 1, that is, that
the total content of amines and amine salts in the hydroxyl-
pivalaldehyde is reduced to 0.31% by weight or lower.

(Br. 13–14, emphasis added.)

We interpret process claim 1, step (A) before us, as requiring an active
process step of reducing the total content of amines and amine salts in the
hydroxypivalaldehyde to 0.31% by weight or lower. We do not find that the
Examiner has provided sufficient evidence in the prior art of a step
equivalent to that of claim 1, step (A).
While the Examiner finds that Mantell and Shu Yoshida are silent as
to the content of amine salt in the HPA, thus assuming that there are no
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amines disclosed in either reference, we do not find that the Examiner has
provided evidence in either Mantell or Shu Yoshida of an active process step
of reducing the amine salts to 0.31% by weight or lower from some higher
amount, as required by the claims. Because each and every claimed process
step must be found in the prior art, and the Examiner has not provided
evidence in the prior art of claim 1, step (A), we reverse the obviousness
rejection.

CONCLUSION OF LAW
The cited references do not support the Examiner’s obviousness
rejection, which is reversed.

REVERSED

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