Ex Parte Matsuoka et al

Patent Trial and Appeal Board

Sep 21, 2016

12577785 (P.T.A.B. Sep. 21, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR
12/577,785 10/13/2009 Yasuhiko MATSUOKA
22850 7590 09/23/2016
OBLON, MCCLELLAND, MAIER & NEUSTADT, LLP,
1940 DUKE STREET
ALEXANDRIA, VA 22314
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.
348777USOCONT 5012
EXAMINER
BUIE-HATCHER, NICOLE M
ART UNIT PAPER NUMBER
1767
NOTIFICATION DATE DELIVERY MODE
09/23/2016 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
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PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE
THE PA TENT TRIAL AND APPEAL BOARD
Ex parte Y ASUHIKO MATSUOKA, 1
Kunio Watanabe, and Hiroki Kamiya
Appeal2014-0083352
Application 12/577,785
Technology Center 1700
Before CATHERINE Q. TIMM, MARK NAGUMO, and
JEFFREY R. SNAY, Administrative Patent Judges.
NAGUMO, Administrative Patent Judge.
DECISION ON APPEAL
Y asuhiko Matsuoka, Kunio Watanabe, and Hiroki Kamiya
("Matsuoka") timely appeal under 35 U.S.C. § 134(a) from the Final
Rejection 3 of claims 1, 3, 5, 7, 9-11, and 13-1 7, which are all of the pending
claims. We have jurisdiction. 35 U.S.C. § 6. We affirm.
1 The real party in interest is identified as Asahi Glass Company, Ltd.
(Appeal Brief, filed 24 April 2014 ("Br."), 1.)
2 Heard 15 September 2016. Counsel's clear and vigorous advocacy at Oral
Argument is noted with appreciation.
3 Office action mailed 13 November 2013 ("Final Rejection").
Appeal2014-008335
Application 12/577,785
A. Introduction4
OPINION
The subject matter on appeal relates to a method of making
fluoropolymers by emulsion polymerization in the presence of a
fluorocarboxylic acid as the emulsifier, at a pH of 1 to 3.0. (Spec. 1, 11. 7-9.)
The Specification reveals that the present reagent of choice for emulsifiers
for such polymerization reactions is ammonium perfluoro-octanoate, which
is said not to hinder polymerization to high molecular weights by chain
transfer reactions. (Id. at 11. 12-16.) The '785 Specification discloses,
however, that there are concerns about the accumulation of this emulsifier in
the environment as well as adverse health effects. (Id. at 11. 20-22.) As a
consequence, alternatives are being sought, but, according to the
Specification, the yield of polymer per unit time is not improved.
(Id. at 11. 22-23, citing prior art patent documents at 11. 26-27.)
The claimed process is said to provide improved yields of polymer per
unit time, as well as high molecular weight. (Id. at 3, 11. 10-12.) The etheric
oxygen content, fluorine content, and chain length of the fluorocarboxylic
acid may be adjusted to modify the surface activity and emulsion
stabilization properties. (Id. at 4, 11. 14-26.) Moreover, the Specification
teaches that using the fluorocarboxylic acid, rather than its salt, means it is
not necessary to add a mineral acid or strong organic acid to the salt to adjust
4 Application 12/577,785, Method for producingfluoropolymer using
fluorocarboxylic acid compound, filed 13 October 2009 as a continuation
under 35 U.S.C. § 371 of PCT/JP08/56699, filed 3 April 2008, claiming the
benefit of an application filed in Japan on 13 April 2007. We refer to the
'"785 Specification," which we cite as "Spec."
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Application 12/577,785
the pH. (Id. at 5, 11. 3-6.) "Accordingly," in the words of the Specification,
"the fluorocarboxylic acid is superior to the alkali metal or the ammonium
salt of the same fluorocarboxylic acid, since some steps can be omitted in
the production and the production is easy." (Id. at 5, 11. 8-10.)
Fluorinated polymer products are said to include high molecular
weight modified polytetrafluoroethylene ("PTFE") that is not melt-
processable, melt-processable fluoropolymers, and fluoroelastomers.
(Id. at 1, 11. 12-14) The emulsion polymerization provides fine powders
(id. at 9, 11. 14-16) with very low amounts of residual fluorinated emulsifier
(id. at 11. 1-3), which can be recovered and re-used (id. at 11. 6-9).
The Specification teaches that the product powder may be used, e.g., as a
raw material for molded products, dispersed as an emulsion useful as a
coating material, or as a binder or additive. (Id. at 13, 11. 4-10.)
Sole independent claim 1 is representative and reads:
A method for producing a fluoropolymer, which comprises
mixing an aqueous medium with
a fluoromonomer and
a polymerization catalyst,
polymerizing the fluoromonomer by emulsion polymerization
in the presence of the polymerization catalyst in the
aqueous medium containing a fluorocarboxylic acid
compound having at most 6 carbon atoms and
at most 3 etheric oxygen atoms per molecule,
wherein the aqueous medium has a pH of 1 to 3.0
during a period beginning before the polymerization
catalyst and the fluoromonomer are mixed with the
aqueous medium through the end of the polymerizing, and
wherein the fluorocarboxylic acid compound is in the acid form.
(Claims App., Br. 36; some indentation, paragraphing, and emphasis added.)
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Application 12/577,785
The Specification states expressly that "the time period of 'during the
polymerization' is a period of from the beginning to the end of the
polymerization," and "[t]he pH at the [beginning] of the polymerization
means a pH of an aqueous medium before the polymerization catalyst and
the fluoromonomer are introduced thereto." (Spec. 4, 11. 7-10.)
The Examiner maintains the following grounds of rejection: 5
A. Claims 1, 3, 7, 9-11, and 13-17 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of
Nomura6 and Hintzer. 7
Al. Claims 1, 3, 5, 11, 13, and 14 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of
Nomura and Funaki.8
B. Claims 1, 3, 7, 9-11, and 13-17 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of
Tanaka9 and Hintzer.
5 Examiner's Answer mailed 23 May 2014 ("Ans.").
6 Junpei Nomura et al., Process for producing elastic fluorocopolymer and
crosslinkedfluororubber, U.S. Patent Application Publication
2007/0167581 Al (19 July 2007), based on an application filed 3 January
2007; assigned to Asahi Glass Co., Ltd.; H. Kamiya is a common inventor.
7 Klaus Hintzer et al., Method of makingfluoropolymer dispersion, U.S.
Patent Application Publication 2007 /0015864 Al (18 January 2007), based
on an application filed 25 May 2006.
8 Hiroshi Funaki et al., Process for the recovery of fluorine-containing
emulsifiers, EP 1514848 Al (2005); assigned to Asahi Glass Co., Ltd.;
H. Kamiya is a common inventor.
9 Hiroyuki Tanaka et al., Fluorine-containing elastomer composition
excellent in plasma-aging prevention effect and shaped article made thereof,
U.S. Patent Application Publication 2006/0235140 Al (19 October 2006),
based on a PCT application filed 21 April 2004.
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Application 12/577,785
B 1. Claims 1, 3, 5, 9-11, 13, and 14 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of
Tanaka and Funaki.
B. Discussion
Findings of fact throughout this Opinion are supported by a
preponderance of the evidence of record.
Briefly, the Examiner finds that Nomura and Tanaka disclose
emulsion polymerization of fluorinated monomers at acidic pH ranges that
overlap (Ans. 2, citing Nomura 3 [0052]) or that meet (Ans. 6, citing
Tanaka 6 [0097]) the range of pH 1-3.0 required by the claims before and
during polymerization. The Examiner finds that neither Nomura nor Tanaka
discloses a fluorocarboxylic acid as required by claim 1, but finds that both
Hintzer (Ans. 2, citing Hintzer [O 114 ], [O 117] and [0085]) and Funaki
(Ans. 4, citing Funaki [0049]-[0052]) disclose using such fluorinated
carboxylic acids as emulsifiers in the emulsion polymerization of fluorinated
monomers. The Examiner reasons that it would have been obvious to use
disclosed materials for their designated purposes.
Rejections A (Nomura)
Matsuoka urges that although Nomura teaches that the pH for
emulsion polymerization is adjusted within a broad range (pH 1 to 9) (Br. 6,
11. 4-7), those broad teachings do not include a teaching or suggestion that
the pH be maintained in the range of pH 1 to 3.0 throughout the entire
polymerization (id. at 11. 16-1 7). In particular, Matsuoka points out, the pH
described in the Examples varies greatly during polymerization.
(Id. at 11. 17-18, and at para. bridging 15-16, citing Nomura 6 [0089]-
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Application 12/577,785
[0090], Example 1, "Acidic Polymerization," starting at pH 7.0 and ending
at pH 2.0.) Moreover, as Matsuoka argues, although Nomura does disclose
fluorocarboxylic acids as emulsifiers, Nomura "clearly prefers ammonium
salts, listing no acids but several salts .... " (Br. 18, 1st para., citing
Nomura [0038] and [0039].)
Matsuoka urges that Hintzer treats carboxylic acids and their salts as
interchangeable. (Br. 16, last para, citing Hintzer [0017].) Moreover,
Matsuoka points out, Hintzer exemplifies only the use of ammonium salts.
(Br. 16, last para., citing Hintzer 10-11 [0170] (Table 1).) Accordingly, in
Matsuoka's view, the Examiner erred in holding that Hintzer would have
suggested using fluorocarboxylic acids within the scope of the appealed
claims in the processes taught by Nomura.
These arguments are not persuasive of harmful error. As the
Examiner points out repeatedly (Ans. 10-12 10), all of the teachings of a
reference, including non-preferred embodiments, must be considered. As
for the silence of Nomura on maintaining the pH below 3.0 throughout the
polymerization, Nomura's teachings that the pH at the time of the emulsion
polymerization is adjusted from 1 to 7, preferably from 1 to 5
(Nomura 3 [0052]) would have suggested starting the polymerization in the
range of pH 1 to 3. Because the evidence of record indicates that the change
in hydrogen ion concentration is not large compared to the hydrogen ion
concentration in the pH range of 1 to 3, 11 we conclude that the pH would,
10 We caution that constant repetition of a principal may diminish the impact
of the underlying fact-finding, analysis and reasoning.
11 In the examples in Nomura as well as in the comparative examples of
the '785 Specification, the pH tends to fall by several pH units, e.g.,
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Application 12/577,785
more likely than not, remain within that range during polymerization, and
the Examiner's holding of prima facie obviousness therefore is supported by
a preponderance of the evidence of record.
Matsuoka urges further that the artisan would not have expected any
difference between using an ammonium salt emulsifier and an acid
emulsifier in a fluoropolymer production process. (Br. 18, 11. 10-13.)
Indeed, Hintzer states, "[f]or the sake of convenience, the term 'fluorinated
carboxylic acid' is hereinafter used to indicate the free acid as well as salts
thereof." (Hintzer 2 [0017].) In contrast, according to Matsuoka, the acid
emulsifiers of Examples 1 and 2 show superior results compared to the
corresponding ammonium salt emulsifiers of Comparative Examples 1 and 2
reported in the Specification at pages 11-13 and in Table 1. (Id. at 18,
11. 13-18; Table 1 is reproduced on the following page.) In particular,
Matsuoka urges that the polymerization rate is substantially higher (about
25% higher for Example 1, about 22% higher for Example 2) than the
polymerization rates of the comparative examples. (Br. 19, 1. 8.) Similarly,
Matsuoka urges that the standard specific gravities ("SSG") (2.163
compared to 2.173, and 2.167 compared to 2.171) are substantially lower,
and indicate high molecular weight and excellence in physical properties.
(Id. at 20, 11. 20-24.)
from 6.69 to 2.94 (corresponding to an increase in H+ concentration from
about 2 x 10-7 (log-1(-6.69)) to about 4 x 10-3 (log-1(-2.94)) mol/l.
In Example 2 in the Specification, the pH drops from about 2.41
(H+ concentration of 3.9 x 10-3) to about 2.08 (H+ concentration
of 8.3 x l0-3). (See Table 1, reproduced infra.)
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Application 12/577,785
TABLE 1
{Table 1 is shown below}
The difficulty with these arguments is that, based on only two
Examples and two Comparative Examples, we have little evidence to
support the conclusion that the differences are significant (in particular, we
have no way to assess the scatter in the data), let alone to determine if the
results are unexpected. \Veighed against the suggestions by Nomura that
acidic emulsion polymerizations in the range of pH 1 to 3 would be useful,
discussed supra, we find the weight of the evidence insufficient to carry
Matsuoka's arguments for unexpected results.
Matsuoka's further arguments for the patentability of dependent
claims 5, 7, 10, and 13 rely on the arguments for unexpected results, which,
in Matsuoka's view, "unquestionably show unexpected results." (Br. 29,
11. 11-12; 30, 1. 12; 31, 11. 12-13; 32, 1. 17.) As indicated supra, however,
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Application 12/577,785
the quantity of the data are not such that the significance of the better results
can be assessed as unquestionably showing unexpected results. 12
Matsuoka urges that the Examiner errs in finding that the fluorine-
containing acids listed in Funaki paragraph [0051] are emulsifiers. Rather,
according to Matsuoka, "it is the salts of those listed acids that are the
emulsifiers for polymerization." (Br. 22, last two lines.) On this point, the
weight of the evidence supports Matsuoka. The grammatical subject of the
first sentence of Funaki [0050] is "the fluorine-containing emulsifier," which
is described as "preferably a salt of a perfluoroalkanoic acid,
a co-hydroperfluoroalkanoic acid, .... " The subject of each of the
remaining sentences of Funaki [0050] is the salt. Thus, the acids named in
paragraphs [0050], [0051] and [0052] are most naturally read as the acids
used to form the salts named in paragraphs [0053]-[006 l].
It has not escaped our notice that Funaki is primarily concerned with
recovering fluorine-containing emulsifiers (see the title), after coagulation of
an emulsion-polymerization product. Thus, the teachings of Funaki are not
directed towards the conditions of the emulsion polymerization. We have
also noted that Funaki teaches that, "[i]n the present invention, the fluorine-
12 In the event of further examination, we remind the Examiner of a caution
issued long ago by our reviewing court: "Prima facie obviousness is a legal
conclusion, not a fact. Facts established by rebuttal evidence must be
evaluated along with the facts on which the earlier conclusion was reached,
not against the conclusion itself. ... [A] final finding of obviousness may of
course be reached, but such finding will rest upon evaluation of all facts in
evidence, uninfluenced by any earlier conclusion reached by an earlier board
upon a different record." In re Rinehart, 531 F.2d 1048, 1052
(CCPA 1976), quoted in In re Piasecki, 745 F.2d 1468, 1472-73 (Fed.
Cir. 1984).
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Application 12/577,785
containing emulsifier highly concentrated in the aqueous solution (B) can be
precipitated in the form of a free acid by adjusting the pH of the aqueous
solution (B) to an acidity of at most pH 4." (Funaki col. 8 [0045].)
On the present record, the weight of the evidence is that the Examiner
erred in finding that Funaki teaches free fluorinated acids as emulsifiers, or
that Funaki would have suggested that free fluorinated acids be used as
emulsifiers. However, the evidence of record indicates that at some pH
below pH 4 and above pH 1, the salts would convert to free acids. Thus, the
"condition" recited in claim 1, that "the fluorocarboxylic acid compound is
in the acid form" is not an independent condition, but merely a statement of
fact for that pH range. In particular, claim 1 does not require that the pH be
obtained by any particular route. The pH may be obtained by adding an
appropriate amount of strong mineral acid to ammonium salts of
fluorocarboxylic acids, as well as by adding only fluorinated carboxylic
acids. As long as either addition is done before the introduction of the
initiator and the fluoromonomer, the conditions defining the period recited in
claim 1 would be met.
Rejections B (Tanaka)
Matsuoka urges that Tanaka discloses salts of fluorocarboxylic acids
as emulsifiers, not the acids themselves. (Br. 8, 1st full para., and 23, last
para., both citing Tanaka 6 [0095].) Matsuoka quotes (Br. 25) the most
relevant part of Tanaka [0097] cited by the Examiner, which reads,
[ o ]ther polymerization conditions are not specifically limited,
but it is preferable that the pH of polymerization solution is
set as strongly acidic of less than 3 in order to obtain the
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Application 12/577,785
polymer product having a carboxyl group at the end and/or a
branched chain without acid treatment described later."
(Tanaka 6 [0097].) However, Matsuoka urges that the following two
paragraphs, [0098] and [0099], show that "the pH of the polymerization
reaction mixture is not maintained at not more than 3 during the entire
polymerization process. Rather, the pH must be adjusted to at most 3 by
acid treatment in order for coagulation, after the polymerization." (Br. at
para. bridging 25-26.)
Read in context, we find it more plausible to read Tanaka [0098]
and [0099] as describing the alternative acid treatment method "described
later" in Tanaka [0097]. Thus, Tanaka [0097] describes a process in which a
carboxylic acid group is added to the end of the emulsion-polymerized
elastomeric fluoropolymer during polymerization, rather than a terminal
ammonium or metallic salt is converted to a carboxyl group by an acid
treatment following the polymerization.
Matsuoka's arguments regarding the combinations of the teachings of
Hintzer and the teachings of Funaki with the teachings of Tanaka parallel the
arguments regarding Nomura, and we find them unpersuasive for the same
reasons.
C. Order
It is 0 RD ERED that the rejection of claims 1, 3, 7, 9-11, and 13-1 7
under 35 U.S.C. § 103(a) in view of the combined teachings of Nomura and
Hintzer is affirmed.
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Application 12/577,785
It is ORDERED that the rejection of claims 1, 3, 5, 11, 13, and 14
under 35 U.S.C. § 103(a) in view of the combined teachings of Nomura and
Funaki is affirmed.
It is ORDERED that the rejection of claims 1, 3, 7, 9-11, and 13-17
under 35 U.S.C. § 103(a) in view of the combined teachings of Tanaka and
Hintzer is affirmed.
It is ORDERED that the rejection of claims 1, 3, 5, 9-11, 13, and 14
under 35 U.S.C. § 103(a) in view of the combined teachings of Tanaka and
Funaki is affirmed.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § l.136(a).
AFFIRMED
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