Ex Parte Ding et al

Patent Trial and Appeal Board

Sep 7, 2017

14047056 (P.T.A.B. Sep. 7, 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.
14/047,056 10/07/2013 Xin Ding ARC920130112US1 7172
93453 7590 09/11/2017
Mi ch a el R Roberts
EXAMINER
4912 Buckline Crossing
Atlanta, GA 30338
HIRT, ERIN E
ART UNIT PAPER NUMBER
1616
NOTIFICATION DATE DELIVERY MODE
09/11/2017 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):
MRobert s @ MRRPatents. com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte XIN DING, JAMES L. HEDRICK, CHUAN YANG, and
YI YAN YANG
Appeal 2016-006471
Application 14/047,0561
Technology Center 1600
Before RICHARD M. LEBOVITZ, FRANCISCO C. PRATS, and
DAVID COTTA, Administrative Patent Judges.
COTTA, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134 involving claims to a
polycarbonate. The Examiner rejected the claims on appeal as obvious
under 35 U.S.C. § 103(a).
We affirm.
1 According to Appellants, the real parties in interest are International
Business Machines Corporation and the Agency for Science, Technology,
and Research. App. Br. 3.
Appeal 2016-006471
Application 14/047,056
STATEMENT OF THE CASE
Claims 1—4, 7—10, 13—16, 18, and 19 are on appeal. Claim 1, the
only independent claim, is illustrative and reads as follows:
1. A polycarbonate, comprising:
a catechol repeat unit comprising i) an aliphatic
carbonate backbone portion and ii) a side chain linked to
the backbone portion, the side chain comprising a catechol
group of formula (A-l):
(A-!),
wherein
a' is an integer of 0 to 3, and
each R' is an independent monovalent radical
selected from the group consisting of halogens, methyl,
and ethyl.
App. Br. 23.
The Examiner rejected claims 1, 3, 7, 8, 13, 15, 16, 18, and 19 under
35 U.S.C. § 103(a) as obvious over the combination of Ding,2 Tan,3 and
2 Ding et al., Antibacterial and Antifouling Catheter Coatings Using Surface
Grafted PEG-b-Cationic Polycarbonate Diblock Copolymers, 33
Biomaterials 6593—6603 (2012) (“Ding”).
3 Liu et al., Chinese Patent Publication No. 102702539A, published Oct. 3,
2012 (“Tan”). Both the Examiner and Appellants refer to this publication by
the name of its fifth listed inventor, Tan. For consistency and to avoid
confusion, we also refer to this publication as “Tan.” Citations to Tan’s
Abstract are to the Abstract filed by the Appellants on June 17, 2015.
Citations to other portions of Tan are to the machine translation filed by the
Examiner on May, 14, 2015.
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Application 14/047,056
Han.4 In the Examiner’s Answer (“Ans.”) the Examiner indicated that
claims 2, 4, 9, 10, 14, and 17 were objected to as being dependent upon a
rejected base claim, but would otherwise be allowable if rewritten in
independent form. Ans. 2. These claims are thus no longer part of this
appeal.
FINDINGS OF FACT
1. Ding discloses: “PEG-6-cationic polycarbonates with optimal
compositions are effective antifouling and antibacterial coatings for the
prevention of intravascular CAIs [catheter-associated infections].” Ding
Abstract.
2. Scheme 1 of Ding is reproduced below.
HS" ■■■•" 'ton•113
0
*
O '"' ' o
o
0'"^"0
Kftv 't>
T3
f"A f f T
,:ii__i±.j±___
\ A,J.CHaCl2
'Bt
potymes'3; m=18,
poiymer 3' m~18, n-0
Schcnrc 1. oi amiritJtc-d aoivvidjonilt'-;.
Scheme 1 depicts, the “synthesi[s] through metal-free organocatalytic ring­
opening polymerization of MTC-OPrBr and MTC-OEt monomers using HS-
4 Han et al., Immobilization of Amphiphilic Polycations by Catechol
Functionality for Antimicrobial Coatings, 27(7) Fangmuir 4010-4019
(2011) (“Han”).
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Appeal 2016-006471
Application 14/047,056
PEG-OH as the macroinitiator in the presence of TU and DBU catalysts.”
Ding 6594.
3. The Examiner finds that Ding “does not teach forming the
polycarbonate first and then adding the catechol amine functional groups to
the sidechain, but instead teaches adding the sidechain to cyclic carbonates
which are what form each monomer of the polymer and are then
polymerized.” Ans. 2—3.
4. Pratt5 discloses methods of incorporating “a range of functional
groups” into ring-opening polymerization monomers “offering opportunities
for couplings via substitution, cycloaddition, and amide or disulfide
linkages, or for introducing strongly hydrophilic or hydrophobic groups.”
Pratt 114.
5. The Examiner finds that methods of adding functional groups to
cyclic carbonate monomers were “known in the art to be amenable to reaction
with amines as is evidenced by Pratt.” Ans. 2—3.
6. Han discloses:
The catechol derivative is a synthetic mimic of the natural amino
acid 3,4-dihydroxyphenylalanine (DOPA) found in the mussel
adhesive protein. It is generally accepted that the catechol group
can form covalent bonds, hydrogen bonds, or strong physical
interactions with surfaces, as well as can cross-link polymer
chains, affording robust coatings. Synthetic polymers containing
DOPA and DOPA analogues have shown strong interfacial
adhesion strength for a variety of material surfaces and
conditions including wet surfaces.
5 Pratt et al., Tagging Alcohols with Cyclic Carbonate: A Versatile
Equivalent of (Meth)Acrylate for Ring-Opening Polymerization, Chem.
Comm. 114—116 (2008) (“Pratt”). Pratt was cited by the Examiner in
response to Appellants’ arguments. App. Br. 2—3.
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Application 14/047,056
Han 2.
7. Han discloses:
In this study, amphiphilic polycations containing catechol
adhesive groups were synthesized and used to prepare biocidal
coatings by a simple one-step coating procedure. The catechol
groups promoted the immobilization of the hydrophilic
polymers onto glass surfaces. The incorporation of hydrophilic
comonomers enhanced the antimicrobial activity of the
coatings, possibly due to tuning the amphiphilic balance to
facilitate the interactions of polymer chains with bacterial cells,
leading to efficient bacteria killing. The coatings prevented
biofilm development of E. coli. S. aureus, and A. baumannii for
up to 96 hours. These results support our hypotheses that the
catechol adhesive groups prevent leaching of hydrophilic
polymers from the surface coatings, allowing tuning
amphiphilic balance of polycations for potent biocidal activity
of the coatings. In this study, only glass slides were tested as a
coating substrate. It would be of great interest to investigate the
properties and antimicrobial activity of polymer coatings on
different substrates including plastics and titanium oxide. As
future perspectives, this new approach for preparing polycations
with the catechol adhesive groups may be useful for permanent
antimicrobial coatings on many materials. The one-step coating
method without any surface modification, as demonstrated in
this study, will facilitate applications of antimicrobial polymers
for coatings on existing biomedical devices.
Id. at 10.
8. Tan discloses: “The method comprises the steps of introducing
dopamine element on a hyaluronic acid main chain by amidation so as to
provide certain amphipathy to the hyaluronic acid, so assembling. . . . The
adhesiveness of the dopamine provides excellent interface property, and the
micelle can be applied to the fields such as emulsion food, cosmetic and the
like as emulsifier.” Tan Abstract.
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Application 14/047,056
9. The Examiner finds:
[Sjcheme 1 in Ding . . . shows that the carbonate containing
monomer units can be modified with nucleophiles, e.g. oxygens
and nitrogens, and as such would likely be amenable to reaction
with nucleophilic nitrogen atoms such as primary or secondary
nitrogen atoms contrary to applicant’s assertion that nitrogens
would break down the polymer as is taught by Bolgiano, the
background of Ding teaches that the synthesis of these cyclic
carbonates with side chain alcohols was previously known in the
art and as is evidenced by Pratt[,] the reference which reports the
synthesis of these cyclic carbonates, amines and alcohols can be
added to the cyclic carbonates (See Pratt citation above).
Ans. 5.
10. Tan discloses: “Dopamine is preferably hydrophilic, and has
an important characteristic — adhesion, such a strong interfacial adhesion.”
Tan | 8.
ANALYSIS
In rejecting claims 1, 3, 7, 8, 13, 15, 16, 18, and 19 as obvious, the
Examiner found that Ding described the claimed “an aliphatic carbonate
backbone portion” of claim 1, but acknowledged that Ding did not disclose
that its polycarbonate polymers comprise a catechol containing side chain as
recited in the claim. Final Act. 4.6 The Examiner also found that Ding
disclosed “polycarbonate polymers comprising the cationic sidechain of
claim 13, specifically a quaternary amine side chain that is linked to the
aliphatic carbonate backbone.” Id. The Examiner further found that Ding’s
cationic repeat unit “has the same structure as is instantly claimed in claims
15 and 16, specifically wherein L3-Q'(Ra)u" is a C6 cationic moiety
comprising a quaternary ammonium group.” Id.
6 Office Action mailed Oct. 8, 2015 (“Final Act.”).
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Application 14/047,056
The Examiner found that Tan disclosed “modifying hyaluronic
polymers with dopamine groups/catechol groups, which are linked to the
polymer by a divalent linking group or a single bond, and which provide
excellent adhesion properties of the polymer to surfaces.” Id. The Examiner
found that Han similarly disclosed “a polymer comprising dopamine/
catechol sidechains.” Id. Han also disclosed a “PEG sidechain, which has
only 1 PEG group, and a quaternary amine side chain similar to that
instantly claimed which is useful in antimicrobial coatings.” Id. at 4—5.
With respect to claim 1, based on the combined teachings of Ding,
Tan, and Han, the Examiner concluded that it would have been obvious to
“add a catechol containing sidechain to the polycarbonate backbone because
both Tan and Han teach adding catechol/dopamine groups to the side chain
of other polymers to provide crosslinking properties which permit good
attachment of the polymers to surfaces as an antimicrobial coating.” Id. at 5.
With respect to claim 13 and claims depending therefrom, each of
which require a “polyethylene oxide) chain (PEG chain) having a degree of
polymerization of about 5 to about 30,” the Examiner concluded:
While Han only teaches polymer side chains having 1 PEG
unit, it would have been obvious to an ordinary skilled artisan
to optimize the number of PEG groups in the instantly claimed
polymers to the instantly claimed range of 5-30 because Han
expressly teaches that these methoxyethyl (PEG) side chains
enable one of ordinary skill in the art to tune the hydrophobic/
hydrophilic balance of the polymer to that which is
necessary/desired.
Id. (citing Han Abstract).
We adopt the Examiner’s findings of fact and reasoning to the extent
they are consistent with the scope and content of the prior art (Ans. 2—8;
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Final Act. 3—7) and agree that the claims are obvious over Ding, Tan, and
Han. We address Appellants’ arguments below.
Claim 1
Appellants contend that “polycarbonates are known to be susceptible
to chain scission nucleophilic attack by primary and secondary amine groups
and/or nucleophilic alcohol groups under basic conditions.” App. Br. 12
(citing Bolgiano7 and Collins8). Appellants thus assert that the prior art does
not teach that “a catechol compound such as dopamine can be covalently
linked to a carbonate repeat unit of a polycarbonate chain without attacking
and/or degrading the polycarbonate backbone and/or crosslinking the
polycarbonate.” Id. at 14. We are not persuaded.
Ding teaches adding a side chain to carbonate monomers before
polymerization. FF3. The Examiner’s conclusion of obviousness thus
posits that the skilled artisan would add a catechol group to carbonate
monomers before polymerization. Ans. 2—3; see also FF2.9 Appellants
have not provided persuasive evidence or argument that the catechol group
would attack or degrade a polycarbonate chain when the chain is formed in
the manner posited by the Examiner. Appellants, therefore, did not
7 Bolgiano, US Patent No. 3,223,678, issued Dec. 14, 1965 (“Bolgiano”).
Bolgiano was cited by Appellants as evidence that “polycarbonate resins can
be chain shortened by treatment with a monoethanolamine or morpholine.”
App. Br. 12.
8 Collins, US Patent No. 4,443,593, issued Apr. 17, 1984 (“Collins”).
Collins was cited by Appellants as evidence of “the high susceptibility of the
polycarbonate backbone to attack by secondary amines or primary amines
and alcohols.” App. Br. 13.
9 As the Examiner points out, the method of adding a functional group to a
cyclic carbonate was known in the art as evidenced by Pratt (FF4, FF5),
which is cited for this proposition in Ding. See Ding at 6594 n. 28.
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establish, based on the evidence, that the Examiner erred in finding that the
skilled artisan would reasonably expect that adding a catechol group to
carbonate monomers prior to polymerization would address any potential
problems regarding the catechol group attacking or degrading the
polycarbonate backbone.
Appellants object to the machine translation of Tan as evidence of the
content of the Tan reference. App. Br. 14. We are not persuaded at least
because the disclosure from Tan that the Examiner relied upon — i.e., its
disclosure of “modifying hyaluronic polymers with dopamine
groups/catechol groups, which are linked to the polymer by a divalent
linking group or a single bond, and which provide excellent adhesion
properties of the polymer to surfaces” (Final Act. 4) — is consistent with the
English language Abstract provided by Appellants and with the disclosure of
Han that catechol side chains have adhesive properties. See FF6—FF8.
Accordingly, we find that the machine translation provides adequate
evidence of the contents of Tan, at least with respect to the portions relied
upon by the Examiner. See In re Orbital Technologies Corporation, 603 F.
App’x 924, 932 (Fed. Cir. 2015).
Appellants argue that Tan “contains no catechol repeat unit
comprising an aliphatic carbonate backbone portion” and that “Han is also
silent with respect to carbonates, polycarbonates and catechol repeat units
comprising an aliphatic carbonate backbone portion.” App. Br. 15—16. We
are not persuaded because the Examiner relied on the combination of Ding,
Han, and Tan, not on Han or Tan alone. One cannot show nonobviousness
by attacking references individually when the rejection is based on a
combination of references. In re Keller, 642 F.2d 413, 425 (CCPA 1981).
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Appellants argue that “[t]he success by TAN in attaching dopamine to
HA and/or by HAN in polymerizing a catechol-containing methacrylate
monomer is not evidence of a reasonable expectation that a polycarbonate
can be modified with dopamine or another catechol bearing group.” App.
Br. 16. As discussed above, Ding discloses adding sidechains to carbonate
monomers prior to polymerization (see FF2 and FF3) using methods known
in the art. See FF4 and FF5. Appellants do not explain why the skilled
artisan would not reasonably expect to be able to similarly add a catechol
group to carbonate monomers and then polymerize.
Appellants argue that “the combination of references provides no
reasonable expectation that a polycarbonate comprising the instant catechol
repeat unit, assuming it can be formed, would possess the beneficial
solution, film-forming, anti-microbial, and biodegradable properties of
Applicants’examples.” App. Br. 16. We are not persuaded because
Appellants do not provide comparative evidence to support a finding of
unexpected results. In re Baxter Travenol Labs., 952 F.2d 388, 392 (Fed.
Cir. 1991) (“[W]hen unexpected results are used as evidence of
nonobviousness, the results must be shown to be unexpected compared with
the closest prior art.”). Moreover, based on the combined disclosure of
Ding, Han, and Tan, the skilled artisan would reasonably expect to obtain a
polycarbonate with antifouling and antibacterial properties (see FF1) and
enhanced adhesive properties. See FF6—FF10. Accordingly, we affirm the
Examiner’s rejection of claim 1.
Claims 3, 7, 8, 13, 15, 16, 18, and 19
Claims 3, 7, 8, 13, 15, 16, 18, and 19 depend from claim 1 and add
further limitations regarding a cationic repeat unit, PEG repeat units, and the
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structure of the catechol repeat unit. Appellants argue each of these claims
under separate headings, but the only argument made with respect to each
claim is to assert, without explanation, either that the cited art does not
disclose the additional limitation, and/or that the Final Office Action
“provides no evidence” that the cited art discloses the additional limitation.
App. Br. 18—22.
Appellants’ arguments are insufficient to properly raise an issue on
appeal. In re Lovin, 652 F.3d 1349, 1357 (Fed. Cir. 2011) (“The Board
reasonably interpreted Rule 41.37 to require more substantive arguments in
an appeal brief than a mere recitation of the claim elements and a naked
assertion that the corresponding elements were not found in the prior art.
Because Lovin did not provide such arguments, the Board did not err in
refusing to separately address claims 2-15, 17-24, and 31-34.”).
Moreover, contrary to Appellants’ assertions, the Examiner did, in
fact, provide evidence that the additional limitations recited in the dependent
claims were taught or suggested by the cited art. See Final Act. 4—5 (finding
that Ding disclosed elements recited in claims 13, 15, and 16, further finding
that Tan and Han disclosed elements recited in claims 3, 7, 8, 18, and 19,
and providing rationale for optimizing PEG chain in the manner recited in
the dependent claims); see also Ans. 6-7 (further detailing findings with
respect to dependent claims). Accordingly, we affirm the Examiner’s
rejection of claims 3, 7, 8, 13, 15, 16, 18, and 19 as obvious over Ding, Han,
and Tan.
SUMMARY
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Application 14/047,056
For these reasons and those set forth in the Examiner’s Answer and
Final Office Action, we affirm the Examiner’s rejection of claims 1, 3, 7, 8,
13, 15, 16, 18, and 19.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(1).
AFFIRMED
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