Lawrence Livermore National Security, LLC

Patent Trials and Appeals Board

Dec 15, 2020

2020000614 (P.T.A.B. Dec. 15, 2020)

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.
15/253,640 08/31/2016 Patrick Campbell LLNLP154/IL-13076B 7535
78980 7590 12/15/2020
LLNL/Zilka-Kotab
Lawrence Livermore National Laboratory
L-703, P.O. Box 808
Livermore, CA 94551
EXAMINER
ANGEBRANNDT, MARTIN J
ART UNIT PAPER NUMBER
1737
NOTIFICATION DATE DELIVERY MODE
12/15/2020 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):
llnl-docket@llnl.gov
zk-uspto@zilkakotab.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte PATRICK CAMPBELL,
ERIC DUOSS, and JAMES OAKDALE
Appeal 2020-000614
Application 15/253,640
Technology Center 1700
Before CATHERINE Q. TIMM, GEORGE C. BEST, and
LILAN REN, Administrative Patent Judges.
REN, Administrative Patent Judge.
DECISION ON APPEAL
STATEMENT OF THE CASE
Pursuant to 35 U.S.C. § 134(a), Appellant1 appeals from the
Examiner’s decision to reject claims 5, 7–10, 14, 16, 17, 20, and 22–27. See
Final Act. 1. We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM IN PART.

1 We use the word Appellant to refer to “applicant” as defined in 37 C.F.R.
§ 1.42. Appellant identifies the real party in interest as Lawrence Livermore
National Security, LLC. Appeal Br. 2.
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CLAIMED SUBJECT MATTER
The claims seek “to provide techniques and suitable materials that are
capable of generating structures with the precise control afforded by
photoactivation-based additive manufacturing, while also enabling the
resulting structure to have further functionality that is chemically- and/or
biologically relevant to a variety of industrial, pharmaceutical, etc.
applications.” Spec. ¶ 5. Claims 5 and 16, reproduced below, illustrate the
claimed subject matter:
5. An additive manufacturing resin suitable for fabricating a
click-chemistry compatible composition of matter, the resin
comprising:
a photo polymerizable compound comprising a
polyethylene-glycol backbone functionalized with at least one
epoxide functional group; and
a click-chemistry compatible compound.
16. An additive manufacturing resin, comprising:
a photo polymerizable compound;
a click-chemistry compatible compound comprising a
terminal azide group having a protecting group functionalized
thereto, wherein the protecting group is selected from a group
consisting of: a trimethylsilyl, a triethylsilyl, a t-butyl
dimethylsilyl, a triisopropylsilyl, and a 2-(2-
hydroxypropyl)alkyne; and
a pore-forming compound.
Claims Appendix (Appeal Br. 33, 34–35).
REFERENCES
The prior art references relied upon by the Examiner are:
Name Reference Date
Bai CN 103408746 July 23, 2013
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Name Reference Date
Mizuno Masanori Mizuno &
Takayuki Shioiri, Ring
opening reaction of
epoxides with diphenyl
phosphorazidate,
Tetrahedron Letters 40
(1999) 7105–7108
July 21, 1999
Durmaz Yasemin Yuksel Durmaz
et al., Surface
Modification of UV-Cured
Epoxy Resins by Click
Chemistry, Journal of
Polymer Science: Part A:
Polymer Chemistry, Vol.
48, 2862–2868 (2010).
April 6, 2010
REJECTIONS
The Examiner rejects claims 22–27 “under 35 U.S.C. § 112(b) or 35
U.S.C. 112 (pre-AIA) as being indefinite.” Final Act. 6.
The Examiner rejects claims 22–27 “under 35 U.S.C. § 112(d) or pre-
AIA 35 U.S.C. 112, 4th paragraph as being of improper dependent form.”
Final Act. 7.
Claims 5, 7, 8, 10, 17, and 20 are rejected under 35 U.S.C. § 102(a)(l)
as being fully anticipated by Bai. Final Act. 9.
Claims 5, 7–10, 14, 17, and 20 are rejected under 35 U.S.C. § 103 as
being unpatentable over Bai and Mizuno. Final Act. 9.
Claim 16 is rejected under 35 U.S.C. § 103 as being unpatentable over
Durmaz and Mizuno. Final Act. 10.
Claims Rejected 35 U.S.C. § Reference(s)/Basis
22–27 112(b) or 112, second
paragraph
Indefiniteness
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22–27 112(d) or 112, fourth
paragraph
Improper dependence
5, 7, 8, 10, 17, 20 102(a)(1) Bai
5, 7–10, 14, 17, 20 103 Bai, Mizuno
16 103 Durmaz, Mizuno
OPINION
Indefiniteness
Claim 22 depends from claim 5 and further requires the photo
polymerizable compound be characterized by a partial structure selected
from a group of structures recited in claim 22. Claims Appendix (Appeal Br.
35). Claims 23–27 further depend from claim 22 and each recites a particular
partial structure for the photo polymerizable compound. Id.
The Examiner rejects claims 22–27 as indefinite finding that “the
partial structures do not include the ‘polyethylene glycol backbone’ recited
in claim 5 or clearly indicate how these partial structures are attached to the
‘polyethylene glycol backbone’ recited in claim 5.” Final Act. 7. The
Examiner states that “[t]he rejection has nothing to do with breadth of the
claims, but rather how the very specific structure of a polyethylene-glycol
backbone functionalized with at least one epoxide functional group is
connected/bonded to the very specific formulae of claims 22–27.” Ans. 9.
“The definiteness inquiry focuses on whether those skilled in the art
would understand the scope of the claim when the claim is read in light of
the rest of the specification.” Union Pac. Res. Co. v. Chesapeake Energy
Corp., 236 F.3d 684, 692 (Fed. Cir. 2001) (citation omitted). “The purpose
of claims is not to explain the technology or how it works, but to state the
legal boundaries of the patent grant. A claim is not ‘indefinite’ simply
because it is hard to understand when viewed without benefit of the
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specification.” S3 Inc. v. NVidia Corp., 259 F.3d 1364, 1369 (Fed. Cir.
2001).
[W]hen the USPTO has initially issued a well-grounded rejection
that identifies ways in which language in a claim is ambiguous,
vague, incoherent, opaque, or otherwise unclear in describing
and defining the claimed invention, and thereafter the applicant
fails to provide a satisfactory response, the USPTO can properly
reject the claim as failing to meet the statutory requirements of
§ 112(b).
In re Packard, 751 F.3d 1307, 1311 (Fed. Cir. 2014).
Because claim 22 depends from claim 5, claim 22 requires the photo
polymerizable compound have the polyethylene-glycol backbone
functionalized with at least one epoxide functional group specified by claim
5, and it additionally requires the photopolymerizable compound to be
characterized by a partial structure selected from one of the groups
enumerated in claim 22. Although—as found by the Examiner—claim 22
does not specify the bonding position of the partial structure, that merely
renders the claim broad, not indefinite.
In this case, the Examiner reasons that claims 22–27 are indefinite
because their language does not describe a complete molecular structure
(Final Act. 7; Ans. 9) but § 112(b) does not require a complete structure. The
Examiner’s reasoning is insufficient to show that, “when read in light of the
specification, [the claim language] does not reasonably apprise those skilled
in the art of the scope of the invention.” See Amgen, Inc. v. Hoechst Marion
Roussel, Inc., 314 F.3d 1313, 1342 (Fed. Cir. 2003) (“The standard of
indefiniteness is somewhat high; a claim is not indefinite merely because its
scope is not ascertainable from the face of the claims.”). The indefiniteness
rejection is not sustained.
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Improper Dependence
The Examiner rejects claims 22–27 “under 35 U.S.C. § 112(d) as
being of improper dependent form based on the same finding with regard to
the indefiniteness rejection. Final Act. 7. Final Act. 8 (finding that “the
partial structures do not include the ‘polyethylene glycol backbone’ recited
in claim 5 or clearly indicate how these partial structures are attached to the
‘polyethylene glycol backbone’ recited in claim 5”). According to the
Examiner, the rejection is not based on a finding that the claims “are
[simply] broad, but rather [that] their connection to the other recited element
is not clear and therefore it is not clear how they further modify the
epoxidized polyethylene glycol backbone, particularly in the case where the
structures lack an epoxide.” Id.
Claim 22 can be read in a way that narrows rather than contradicts
claim 5. Thus, the rejection is not sustained.
Anticipation2
Claim 5
The Examiner finds that Bai discloses “a terminally epoxidized
polyethylene glycol monomethyl ether which is then combined with sodium
azide (click compatible compound).” Final Act. 9. Appellant does not
dispute this finding and only argues that Bai is distinguishable from claim 5
because the compounds in Bai are chemically combined as opposed to
physically combined. Appeal Br. 13 (“Appellant submits Bai teaches a

2 Appellant argues claims 5, 7, 17, and 20 as a group with claim 5 being the
representative claim. See Appeal Br. 11–16. These claims stand or fall
together with regard to the anticipation rejection. See id.; see also 37 C.F.R.
§ 41.37(c)(1)(iv).
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method for making a single compound.”), 15 (arguing that the compounds in
Bai undergo various reaction steps). Appellant’s argument is unpersuasive
because Bai teaches an intermediate mixture, present before reaction. This
intermediate mixture contains both a photo polymerizable compound
(terminally epoxidized polyethylene glycol monomethyl ether) and another
compound (sodium azide). Thus, the intermediate has two compounds as
required by claim 5.
Appellant next argues that sodium azide disclosed in Bai is not a
“click-chemistry compatible compound” as recited in claim 5. Appeal Br.
15. Appellant acknowledges that “sodium azide may be a suitable reagent
for generating click-chemistry compatible compounds” but argues that “this
does not establish that sodium azide itself is click-chemistry compatible.” Id.
at 16.
We are not persuaded by this argument first and foremost because it is
not supported by the Specification which provides that “‘click-chemistry
compatible’ structures, functional groups, monomers, oligomers, etc., refer
to compounds, materials, etc. that are structurally characterized by including
one or more chemical moieties suitable for participation in a click-chemistry
reaction.” Spec. ¶ 32. Moreover, the Specification provides that, to form the
recited resin, “a compound comprising a terminal alkyne group or a terminal
azide group” is reacted with “protecting reagent to form a protected reactive
diluent precursor,” the precursor is subsequently reacted with “a compound
comprising a photo polymerizable group to form a protected reactive
diluent,” and the final resin is formed by “mixing the protected reactive
diluent with a photo polymerizable compound.” Spec. ¶ 38. Appellant’s
argument that the recited “click-chemistry compound” excludes a compound
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that may be used to produce a click-chemistry compound (Appeal Br. 16) is
therefore unsupported by the Specification.
On the other hand, Appellant’s acknowledgment that sodium azide
may generate click-chemistry compatible compounds (Appeal Br. 16) is
consistent with the Specification which provides that “‘click-chemistry
compatible’ compounds include a terminal alkyne and/or terminal azide
functional group.” Id. As Appellant acknowledges in the Reply Brief: “the
Examiner’s Answer asserts sodium azide inherently has a terminal azide
group as apparent from the structure thereof. Appellant agrees.” Reply Br. 8.
The Examiner’s finding that sodium azide meets the “click-chemistry
compound” recited in claim 1 is therefore supported by the record.
The anticipation rejection of claim 5 is sustained because no
reversible error has been identified.
Claim 8
Claim 8 depends from claim 5 and further recites: “the click-
chemistry compatible compound comprising a terminal azide group.”
As Appellant acknowledges in the Reply Brief: “the Examiner’s
Answer asserts sodium azide inherently has a terminal azide group as
apparent from the structure thereof. Appellant agrees.” Reply Br. 8; see also
Ans. 17 (“The sodium azide inherently has a terminal azide group as the
azide group is at the end of the molecule no matter how you look at it.”).
Appellant’s argument that the sodium azide is eventually dissolved (id.) does
not structurally distinguish the recited structure. We sustain the anticipation
rejection of claim 8 as a result.3

3 Our affirmance of the Examiner’s rejection is based on Appellant’s
agreement with the Examiner’s finding. We decline to construe the term “a
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Claim 10
Claim 10 depends from claim 5 and further recites: “wherein the
click-chemistry compatible compound is a monomer.”
The Examiner does not rely on sodium azide as a monomer, but
instead finds that “the terminally epoxidized monomethyl ether is both
polymerizable and click-compatible” and therefore meets the limitation of a
“monomer” as recited in claim 10. Ans. 17; Final Act. 9–10. Where a claim
lists elements separately, the clear implication of the claim language is that
those elements are distinct components of the claimed invention. Becton
Dickinson & Co. v. Tyco Healthcare Grp., LP, 616 F.3d 1249, 1254 (Fed.
Cir. 2010). The Examiner’s finding that the prior art polyethylene glycol
ether meets both the recited “photo polymerizable compound” and “click-
chemistry compound” is therefore error. The anticipation rejection of claim
10 is reversed as a result.
Obviousness4
Claim 5
In support of the obviousness rejection of claim 5, the Examiner finds
that “the ring opening of epoxides with azide compounds such as
trimethylsilylazide or sodium azide is known.” Final Act. 9. Appellant does
not dispute this finding but instead argues that the Examiner erred here
because “modifying Bai to use trimethylsilylazide instead of sodium azide

terminal azide group,” as claim construction is unnecessary for an
undisputed issue.
4 Appellant argues against the rejection of claims 5, 7–10, 14, 17, and 20 as a
group with claim 5 being the representative claim. See Appeal Br. 18–24.
These claims stand or fall together with regard to the obviousness rejection.
See id.; see also 37 C.F.R. § 41.37(c)(1)(iv).
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has no impact on the conclusion that Bai teaches a reaction scheme that
yields a series of single products.” Appeal Br. 19. As we noted with regard
to the anticipation rejection of claim 5, claim 5 is a composition claim which
cannot be distinguished based on reaction steps of Bai. As the Examiner
points out, the rejection is not based on a final product of the prior art
reaction and claim 5 does not exclude the prior art compounds which may be
intermediates in a particular reaction. Ans. 19–20 (“The examiner does not
rely upon any intermediate, but only considers the purified terminal
epoxidized polyethylene glycol monomethyl ether, the sodium azide and
terminal azidized polyethylene glycol monomethyl ether in the solution as
being relevant.”).
Appellant next argues that a skilled artisan would not have combined
Bai and Mizuno because the skilled artisan “would not find any reasonable
motivation to experiment with the intermediate compounds thereof in order
to obtain an additive manufacturing resin having different uses” and that
“Bai does not teach combining the various intermediates, nor does Bai place
any importance on photopolymerizable functionality or mention additive
manufacturing in any capacity.” Appeal Br. 22 (also arguing that a skilled
artisan would not have combined the references because the recited resin
“has different uses and capabilities than Bai’s materials”). Appellant’s
arguments are unpersuasive because they do not address the Examiner’s
findings and rationale in support of the rejection based on the intermediate
mixture. Specifically, the Examiner concludes that, based on Mizuno’s
teaching “that the ring opening of epoxides with azide compounds such as
trimethylsilylazide or sodium azide is known,” a skilled artisan would
replace the sodium azide with trimethylsilylazide. Final Act. 9–10 (citing
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Mizuno 7105); see also Ans. 21 (“The position of the examiner is that the
purified terminal epoxidized polyethylene glycol monomethyl ether, the
sodium azide and terminal azidized polyethylene glycol monomethyl ether
in the solution are relevant.”). Appellant does not dispute the Examiner’s
finding with regard to Mizuno’s teaching and does not address the
Examiner’s rationale to combine the references. No reversible error has
therefore been identified here.
Appellant also argues that a skilled artisan would not have considered
the compounds in Bai for the Examiner’s proposed modification as such
modification would render Bai’s invention unsatisfactory for its intended
purpose. Appeal Br. 22–23. Appellant argues that “to substitute
trimethylsilylazide for sodium azide[] would yield a final product with
‘protected’ terminal azides, which is unable to participate in click chemistry
for further modification/polymerization.” Id. at 23. Although not clearly
stated, Appellant appears to argue that such a protected compound is not the
additive “resin suitable for fabricating a click-chemistry compatible
composition” as recited in claim 5. Appeal Br. 23 (arguing that “substituting
sodium azide for trimethylsilylazide would result in a final product not
having any bis-azido terminal groups, but rather terminal trimethylsilyl
groups” whereas the Specification describes “functionalizing a click-
chemistry compatible compound including a terminal azide with
trimethylsilyl ‘protects’ the compound from spontaneous participation in
click-chemistry reactions, and must be removed to allow such reactions to
proceed”). Appellant, however, acknowledge that Bai teaches “compounds
suitable for regulated polymerization/functionalization via click chemistry.”
Appeal Br. 20. As the Examiner points out, claim 5 does not exclude such a
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composition having a protected terminal azide and that Appellant does not
structurally distinguish such a product from the recited additive resin. Ans.
21–22 (further pointing out that dependent claim 14 in fact recites that the
resin includes a protecting agent “configured to protect the click-chemistry
compatible compound from participating in a click-chemistry compatible
reaction” and that “claim 16 also recites a click compatible compound with a
protecting group bonded to it”). Appellant’s argument is unpersuasive also
because of a lack of evidence showing that Bai’s intended purpose is limited
to the production of such a protected compound only. See id. (arguing only
that “[o]ne of the primary advantages of Bai’s invention is formation of
structures including multiple terminal azides” indicative of “[Bai’s] intended
purpose of regulated polymer synthesis”). The obviousness rejection of
claim 5 is sustained because no reversible error has been identified in the
Examiner’s findings in support of the rejection.
Claim 16
Among other limitations, the Examiner finds that Durmaz teaches the
use of water in a particular reaction and considers water to be the recited
“pore-forming compound.” Final Act. 11. The Examiner states, without
citing to the record, that “[w]ater is present and is considered a pore former
as it occupies space between reactive moieties.” Ans. 23. Because the record
lacks evidence supporting the Examiner’s finding—that water “occupies
space between reactive moieties” (id.), we do not sustain the rejection.
The obviousness rejection of claim 16 is reversed.
CONCLUSION
The Examiner’s rejections are affirmed in part and reversed in part.
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More specifically,
DECISION SUMMARY
Claims
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
22–27 112(b) Indefiniteness 22–27
22–27 112(d) Improper Dependency 22–27
5, 7, 8, 10,
17, 20 102 Bai 5, 7, 8, 17, 20 10
5, 7–10, 14,
17, 20 103 Bai, Mizuno
5, 7–10, 14,
17, 20
16 103 Durmaz, Mizuno 16
Overall
Outcome
5, 7–10, 14,
17, 20
16, 22–
27
TIME PERIOD FOR RESPONSE
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)(iv).
AFFIRMED IN PART