Ex Parte Lubowitz et al

Patent Trial and Appeal Board

May 17, 2017

11755790 (P.T.A.B. May. 17, 2017)

United States Patent and Trademark Office
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.
11/755,790 05/31/2007 Hyman Ralph Lubowitz 038190/318605 9731
120226 7590 05/19/2017
Patterson & Sheridan - The Boeing Company
c/o Patterson & Sheridan, LLP
24 GREENWAY PLAZA, SUITE 1600
Houston, TX 77046
EXAMINER
KAHN, RACHEL
ART UNIT PAPER NUMBER
1766
NOTIFICATION DATE DELIVERY MODE
05/19/2017 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):
PAIR_eofficeaction@pattersonsheridan.com
PatentAdmin@boeing.com
PS Docketing @ pattersonsheridan .com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte HYMAN RALPH LUBOWITZ and THOMAS KARL
TSOTSIS
Appeal 2015-006503
Application 11/755,7901
Technology Center 1700
Before CATHERINE Q. TIMM, MONTE T. SQUIRE, and BRIAN D.
RANGE, Administrative Patent Judges.
RANGE, Administrative Patent Judge.
DECISION ON APPEAL
SUMMARY
Appellants appeal under 35 U.S.C. § 134(a) from the Examiner’s
decision rejecting claims 30-33 and 42—50. We have jurisdiction. 35
U.S.C. § 6(b). An oral hearing was held on May 9, 2017.2 We AFFIRM.
1 According to the Appellants, the real party in interest is The Boeing
Company. Appeal Br. 3.
2 A written transcript of the oral hearing will be entered into the record when
the transcript is made available.
Appeal 2015-006503
Application 11/755,790
STATEMENT OF THE CASE3
Appellants describe the invention as relating to “dinadic phenyl amine
endcap monomers” where the endcap can be reacted with chemicals to form
polyimide oligomers suitable for high-temperature composites such as resins
“ideal for high performance composites as presently needed by the
aerospace industry.” Spec. 14. Claim 30, reproduced below with emphasis
added to certain key recitations, is illustrative of the claimed subject matter:
30. A polyimide oligomer of Formula:
phenyl amine endcap
G
wherein:
each dinadic phenyl amine endcap is selected from the group
consisting of
R is selected from the group consisting of
3 In this decision, we refer to the Non-Final Office Action dated June 8,
2014 (“Non-Final Act.”), Final Office Action dated September 19, 2014
(“Final Act.”), the Appeal Brief filed February 9, 2015 (“Appeal Br.”), the
Examiner’s Answer dated May 6, 2015 (“Ans.”), and the Reply Brief filed
June 19,2015 (“Reply Br.”).
2
Appeal 2015-006503
Application 11/755,790
I
OH,
■ v._
0
L /VV.
0—7: 'ft-®'
-- iVi ■ ■ ■' ^ ------'X,■ ■' '■■■ ■: '■ ■ Vi---
..o-
:v,vO, o
i"»0'--4 |y,,
'•'v. N .< w
and
— CH, — > ■....— ................... 0....-......SO; — • —eo:
wherein L is
wherein y is —$o*--------S-— —{CFi&c—»—o—> or —(CMj)gC™-;
and n is selected such that the molecular weight of the polyimide
oligomer is between 1000 and 3000.
Appeal Br. 16—17 (Claims App’x).
REFERENCES
The Examiner relies upon the prior art below in rejecting the claims
on appeal:
Lubowitz US 3,528,950
(hereinafter “Lubowitz ’950”)
DAlelio US 4,517,354
Lubowitz et al. US 5,654,396
(hereinafter “Lubowitz ’396”)
Sep. 15, 1970
May 14, 1985
Aug. 5, 1997
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Appeal 2015-006503
Application 11/755,790
G. W. Meyer et al., New high-performance thermosetting polymer matrix
material systems, 36 Polymer 11, 2303 (1995) (hereinafter “Meyer”)
REJECTIONS
The Examiner maintains the following rejections on appeal:
Rejection 1. Claims 30-33 under 35 U.S.C. § 103 as unpatentable
over Lubowitz ’950 in view of Lubowitz ’396. Ans. 2.
Rejection 2. Claims 42-45 and 47 under 35 U.S.C. § 103 as
unpatentable over Lubowitz ’950 in view of Lubowitz ’396 and Meyer. Id.
Rejection 3. Claims 42-46 and 48—50 under 35 U.S.C. § 103 as
unpatentable over Lubowitz ’950 in view of Lubowitz ’396 and D’Alelio.
Id.
ANALYSIS
We review the appealed rejections for error based upon the issues
identified by the Appellants and in light of the arguments and evidence
produced thereon. Cf. Ex parte Frye, 94 USPQ2d 1072, 1075 (BPAI 2010)
(precedential) (cited with approval in In re Jung, 637 P.3d 1356, 1365 (Led.
Cir. 2011) (“it has long been the Board’s practice to require an applicant to
identify the alleged error in the examiner’s rejections”)). After considering
the evidence presented in this Appeal and each of Appellants’ arguments, we
are not persuaded that Appellants identify reversible error. Thus, we affirm
the Examiner’s rejections for the reasons expressed in the June 18, 2014,
Non-Pinal Office Action, the September 19, 2014, Pinal Office Action, and
the Answer. We add the following primarily for emphasis.
Appellants argue all rejections and argue all claims as a group. See
Appeal Br. 14. Therefore, consistent with the provisions of 37 C.P.R.
§ 41.37(c)(l)(iv) (2013), we limit our discussion to claim 30, and all other
claims on appeal stand or fall together with claim 30.
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Appeal 2015-006503
Application 11/755,790
The Examiner finds that Lubowitz ’950 teaches a polyimide
prepolymer having the structure reproduced below. Non-Final Act. 2.
The structure above is the polyimide prepolymer taught by Lubowitz ’950
where R represents hydrogen or a lower alkyl group and Ri and R2 represent
an aliphatic or aromatic hydrocarbon group. Lubowitz’950 2:35—51. The
Examiner finds that the Lubowitz ’950 teaches a multitude of effective
polyanhydride structures including bis(3,4-dicarboxyphenyl) ether
dianhydride) and bis(3,4-dicarboxyphenyl) sulfone dianhydride. Non-Final
Act. 4 (providing citations to Lubowitz ’950). The Examiner also finds that
the nadic endcaps taught by Lubowtiz ’950 are linked to the polyanhydride
residue via a polyfimctional amine that “can include a diamine or
triamine . . . .” Id.
The Examiner finds that the Lubowitz ’950 prepolymer has only one
nadic anhydride residue at each end (as compared to claim l’s recitation of
dinadic phenyl amine endcaps). Id. The Examiner finds, however, that
Lubowitz ’396 teaches polyimide oligomers having difunctional end caps
and teaches that the use of difimctional end caps promotes crosslinking upon
curing. Id. at 4—5; see also Lubowitz ’396 14:9—15. Based on these and the
Examiner’s other findings, the Examiner determines:
In view of the teachings of ’396, a person having ordinary skill in the
art at the time of the invention would have been motivated to prepare
a difimctional analog of the prepolymer drawn in col 2 of ’950 in
order to build in redundancy at each weak crosslinking point, and to
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Appeal 2015-006503
Application 11/755,790
thereby improve the thermooxidative stability and solvent resistance
of the resulting cured macromolecule. Given that the preparation of
the difunctional imidophenylamine end cap is disclosed by ’396 (col
14, lines 2—5), and further given that the difimctional endcap of ’396
is prepared using monoanhydride and polyamine reactants named in
’950 (nadic anhydride and triaminobenzene), such a modification to
the prepolymer of ’950 would have been within the skill level of the
ordinary artisan at the time of the invention. As shown in ’396 (col 26,
lines 54—67), the free amine group on the difunctional
imidophenylamine endcap reacts with a free anhydride group on the
dianhydride reagent. Therefore, it would have been within the level of
ordinary skill in the art to have determined an appropriate synthetic
strategy to prepare a difunctional analog of the bisnadimide
prepolymer disclosed by ’950. . . .
Non-Final Act. 6. The Examiner concludes that
it would have been obvious to the person having ordinary skill
in the art to have prepared the polyimide oligomer suggested by
’950 and ’396 with endcaps having any of the limited possible
arrangements of the two nadimide groups on the phenyl ring,
including [the arrangements] recited in present claims 30-33.
Non-Final Act. 8. A preponderance of the evidence supports the Examiner’s
findings and conclusion.
Appellants argue that the Examiner erred by asserting that Lubowitz
’950 patent fails to specifically disclose the structure of a prepolymer
prepared from a triamine reactant. Appeal Br. 11—13; Reply Br. 2—3. This
argument misapprehends the Examiner’s position. The Examiner found,
both in the Office Actions and in the Answer, that Lubowitz ’950 “discloses
that the polyfimctional amine used to prepare the prepolymer can include
diamines or triamines. . . .” Non-Final Act. 4; see also Ans. 4. The
Examiner’s statement that underlies Appellants’ argument is not
inconsistent; it merely states that Lubowitz ’950 “fails to specifically
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Appeal 2015-006503
Application 11/755,790
disclose (e.g., by chemical drawing) the structure of a prepolymer prepared
from a triamine reactant.” Non-Final Act. 4 (emphasis added). Appellants’
argument thus fails to demonstrate harm fill error.
Appellants also argue that that there is no suggestion in Lubowitz
’950 that its free amine may be reacted to form a prepolymer having two
dinadic end caps. Appeal Br. 5—6. The argument fails to fairly take into
account the teachings of Lubowitz ’396 and the finding of a suggestion to
modify the teachings of Lubowitz ’950 based on the teachings of Lubowitz
’396 recited in the Examiner’s rejection. Ans. 5—6. The Examiner’s
rejection is based upon a finding that a person of skill in the art would have
been inclined to modify Lubowitz ’950 by including dinadic end caps (as in
claim 1) in order to reach the benefits of such end caps as taught by
Lubowitz ’396. Non-Final Act. 2—8; Ans. 5 (“in view of the cited
motivation in ’396 to build in redundancy at weak crosslinking points, it
would have been obvious to have prepared a difimctional analog of the
polyimide prepolymer shown in ’950 by having a second nadimide group on
each ‘Rf. . . .”). Appellants’ arguments do not persuasively rebut or
demonstrate error in this position. In re Merck & Co., 800 F.2d 1091, 1097
(Fed. Cir. 1986) (“Non-obviousness cannot be established by attacking
references individually where the rejection is based upon the teachings of a
combination of references.”).
Appellants also argue that a person of ordinary skill would not have
reason to modify the teachings of Lubowitz ’950 because it already teaches a
“very stable complex macromolecule of outstanding physical and thermal
properties.” Reply Br. 4—5, emphasis omitted, (quoting Lubowitz ’950
3:20-4:4). Appellants, however, fail to persuasively dispute the Examiner’s
finding that Lubowitz ’396 teaches that it improves upon prior art (such art
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Application 11/755,790
would include Lubowitz ’950) by building in redundancy at weak
crosslinking points. Ans. 5; see also Non-Final Act. 4—5; Lubowitz ’396
1:29—31 (“Cured composites of these oligomers display improved toughness,
and thermal stability.”), 4:23—25 (“Because the crosslinks were generally the
weakest portions of the resulting composite, we improved thermooxidative
stability of the composites by including two crosslinks at each junction.”),
14:9—15 (“Difunctional crosslinkable oligomers exhibit better
thermomechanical properties than conventional capped or uncapped
polymides of the LARC type.”). The preponderance of the evidence
therefore supports the Examiner’s stated motivation to combine.
Appellants do not directly argue a lack of reasonable expectation of
success in modifying the structure of the Lubowitz ’950 polyimide by
including dinadic end caps as taught by Lubowitz ’396. Because this point
is not argued, we are not persuaded that Appellants have identified error
with respect to this point. See Ex parte Yamaguchi, 88 USPQ2d 1606, 1614
(BPAI 2008) (on appeal, applicant must show error by the Examiner); In re
Chapman, 595 F.3d 1330, 1338 (Fed. Cir. 2010), quoting Shinseki v.
Sanders, 556 U.S. 396, 409 (2009) (“the burden of showing that an error is
harmful normally falls upon the party attacking the agency’s
determination.”).
To the extent Appellants have implicitly raised such a reasonable
expectation of success argument (see Reply Br. 2 disagreeing that
“combination of the references enables the pending claims”), we also
disagree on the merits. Lubowitz ’950 seeks to rapidly cure polyimide
polymers and achieves its goal by end-capping low molecular weight
polyimide molecules. Lubowitz ’950 1:12, 1:66—2:3; Non-Final Act. 3.
Lubowitz ’396 teaches that “the thermosetting character of the material is
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Appeal 2015-006503
Application 11/755,790
increased” for low molecular weight oligomers. Lubowitz ’396 10:26—39.
Thus, Lubowitz ’396 is consistent with Lubowitz ’950 in teaching low
molecular weight oligomers for rapid curing applications.4
Lubowitz ’950 also does not suggest that dinadic end caps are
inappropriate or will not work for such materials. Rather, Lubowitz ’396
teaches, for example, that dinadic end caps will “improve thermo-oxidative
stability of the composites” and lead to oligomers with “improved toughness
and thermos stability.” Lubowitz ’396 1:29—31, 4:23—25; see also Non-
Final Act. 7.
Moreover, Lubowitz ’950 teaches that its prepolymer is made by
dissolving [1] an amine, [2] an anhydride (for example, bis(3,4-
dicarboxylphenyl)ether dianhydride, and [3] a special monoanhydride for the
end cap. See, e.g., Lubowitz ’950 2:23—25; see also Non-Final Act. 2—5.
The process of Lubowitz ’396 similarly (or identically) forms a prepolymer
by combining [1] an amine (e.g., “a diamine having terminal amino
groups”), [2] an anhydride (e.g., “n moles of an ether dianhydride”), and [3]
a monoanhydride end cap. Lubowitz ’396 9:33—53. Thus, a preponderance
of the evidence supports the Examiner’s position that a person having
ordinary skill in the art would have been able to prepare “a difunctional
analog of the polyimide prepolymer disclosed by the ’950” based upon the
teachings of the two references. Non-Final Act. 7.
4 To the extent Appellants argued at the May 9, 2017, hearing that Lubowitz
’396 at column 10 teaches away from applying dinandic end caps to low
weight oligomers, we note that this argument was not presented in the
Appeal Brief, and, thus, we do not consider it. See 41 C.F.R. § 41.47 (2014)
(“At the oral hearing, appellant may only . . . present argument that has been
relied upon in the brief or reply brief [subject to exceptions not relevant
here].”).
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Application 11/755,790
DECISION
For the above reasons, we affirm the Examiner’s rejection of claims
30-33 and 42-50.
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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